JP2933962B2 - Sugar-related compounds - Google Patents
Sugar-related compoundsInfo
- Publication number
- JP2933962B2 JP2933962B2 JP1344683A JP34468389A JP2933962B2 JP 2933962 B2 JP2933962 B2 JP 2933962B2 JP 1344683 A JP1344683 A JP 1344683A JP 34468389 A JP34468389 A JP 34468389A JP 2933962 B2 JP2933962 B2 JP 2933962B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tri
- cdcl
- nmr
- anhydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- -1 for example Chemical group 0.000 description 46
- NNVZFQBAFJAZKU-UHFFFAOYSA-M pyridin-1-ium-1-ylmethanamine;chloride Chemical compound [Cl-].NC[N+]1=CC=CC=C1 NNVZFQBAFJAZKU-UHFFFAOYSA-M 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 17
- 239000007858 starting material Substances 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 239000012156 elution solvent Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- NLTUKAPLELRUAZ-UHFFFAOYSA-M pyridin-1-ium-1-ylmethanamine;iodide Chemical compound [I-].NC[N+]1=CC=CC=C1 NLTUKAPLELRUAZ-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 150000001720 carbohydrates Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012148 binding buffer Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000005949 ozonolysis reaction Methods 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JVOHXPRICXIUJD-LOFWALOHSA-N (3r,4s,5r,6r)-6-(hydroxymethyl)-3,4,5-trimethoxyoxan-2-ol Chemical compound CO[C@H]1C(O)O[C@H](CO)[C@@H](OC)[C@@H]1OC JVOHXPRICXIUJD-LOFWALOHSA-N 0.000 description 1
- HZQLUIZFUXNFHK-UHFFFAOYSA-N 1-(bromomethyl)-4-phenylbenzene Chemical compound C1=CC(CBr)=CC=C1C1=CC=CC=C1 HZQLUIZFUXNFHK-UHFFFAOYSA-N 0.000 description 1
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108010003541 Platelet Activating Factor Proteins 0.000 description 1
- 108700023400 Platelet-activating factor receptors Proteins 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 206010049771 Shock haemorrhagic Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- RAFKCLFWELPONH-UHFFFAOYSA-N acetonitrile;dichloromethane Chemical compound CC#N.ClCCl RAFKCLFWELPONH-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- OXQKEKGBFMQTML-UHFFFAOYSA-N alpha-Glucoheptitol Chemical compound OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229960002246 beta-d-glucopyranose Drugs 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 102000030769 platelet activating factor receptor Human genes 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 201000005060 thrombophlebitis Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、医薬として優れた作用を有する新規な糖類
縁化合物及びその薬理学的に許容できる塩に関する。Description: TECHNICAL FIELD The present invention relates to a novel saccharide-related compound having excellent action as a medicament and a pharmacologically acceptable salt thereof.
血小板活性化因子〔PAF…Platelet Activating Facto
r〕（以下単にPAFと略称する）は近年著しく注目されて
おり、最近では種々の疾病との関連性が明らかになりつ
つある。即ち、炎症をはじめとしてDIC、エンドトキシ
ンショック、喘息、消化管潰瘍、腎炎、肝炎及び臓器移
植時の拒絶反応などに関与していることが推定されてい
る。Platelet activating factor [PAF… Platelet Activating Facto
r] (hereinafter simply abbreviated as PAF) has attracted considerable attention in recent years, and recently its association with various diseases has been clarified. That is, it is presumed to be involved in inflammation, DIC, endotoxin shock, asthma, gastrointestinal ulcer, nephritis, hepatitis, and rejection at the time of organ transplantation.
このような状況において、PAF抑制作用を有する化合
物の探索が行われており、その中でも、例えば特開昭60
-158172号、特開昭61-293954号、特開昭60-243047号な
どで示される如くグリセリン誘導体がある。しかしなが
ら、現在のところ、抗PAF剤としては満足すべきものは
出現していない。In such a situation, a search for a compound having a PAF inhibitory action has been conducted.
-158172, JP-A-61-293954, JP-A-60-243047 and the like. However, at present, no satisfactory anti-PAF agent has emerged.
このような状況に鑑みて、本発明者等は優れたPAF抑
制作用を有するのみならず、作用の持続性、化合物の安
定性においても優れている糖類縁化合物について長年に
わたって探索研究を続けてきた。In view of such a situation, the present inventors have been exploring for many years a saccharide-related compound having not only an excellent PAF inhibitory action but also an excellent sustainability of action and stability of the compound. .
本発明者等は、前記に示した目的で長年鋭意研究を重
ねてきた結果、次に示す糖類縁化合物又はその薬理学的
に許容できる塩が目的を達成できることを見出し、本発
明を完成した。The present inventors have made intensive studies for many years for the above-mentioned objects, and as a result, have found that the following saccharide-related compounds or pharmacologically acceptable salts thereof can achieve the object, and have completed the present invention.
即ち本発明化合物は、次の一般式（Ｉ）で示される糖
類縁化合物又はその薬理学的に許容できる塩である。That is, the compound of the present invention is a saccharide-related compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof.
〔式中、R1,R2,R3は同一又は相異なる低級アルキル基
を意味し、R4はアシル基を意味する。 [In the formula, R 1 , R 2 , and R 3 represent the same or different lower alkyl groups, and R 4 represents an acyl group.
ｍ及びｎは１〜３の整数を意味する。 m and n each represent an integer of 1 to 3.
Ａは （式中R7は水素原子又は低級アルキル基を意味し、Ｘ
は薬理学的に許容できるアニオンを意味する）で示され
る基を意味する〕 即ち、上記の一般式（Ｉ）で表される糖類縁化合物
は、優れたPAF抑制作用を有し、更に作用の持続性を有
し、しかも化合物自体が安定性が高いという特徴を有し
ている。A is (Wherein R 7 represents a hydrogen atom or a lower alkyl group;
Means a group represented by a pharmacologically acceptable anion). That is, the saccharide-related compound represented by the general formula (I) has an excellent PAF inhibitory action, It has a long-lasting property and the compound itself has high stability.
従って本発明の目的は、優れた抗PAF作用を有する新
規な糖類縁化合物又はその薬理学的に許容できる塩を提
供することであり、更に本発明の目的は、それらの製造
方法を提供することであり、更に本発明の目的はそれを
含有する医薬を提供するにある。Accordingly, an object of the present invention is to provide a novel saccharide-related compound having excellent anti-PAF activity or a pharmacologically acceptable salt thereof, and a further object of the present invention is to provide a method for producing the same. Another object of the present invention is to provide a medicament containing the same.
R1,R2,R3,R7の定義にみられる低級アルキル基とは、
炭素数１〜６の直鎖もしくは分枝状のアルキル基、例え
ばメチル、エチル、ｎ−プロピル、ｎ−ブチル、イソプ
ロピル、イソブチル、ｎ−ヘプチル、１−エチルプロピ
ル、イソアミル、ｎ−ヘキシルなどをあげることができ
る。これらのうち、R1,R2,R3として最も好ましい基はメ
チル基である。A lower alkyl group found in the definitions of R 1 , R 2 , R 3 and R 7 is
A straight-chain or branched alkyl group having 1 to 6 carbon atoms, for example, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, n-heptyl, 1-ethylpropyl, isoamyl, n-hexyl, etc. be able to. Among them, the most preferred group as R 1 , R 2 and R 3 is a methyl group.
R5,R6の定義にみられるアルキル基とは、炭素数１〜3
0の直鎖状もしくは分枝状のアルキル基をいう。具体的
には、上記に示した低級アルキル基、即ち炭素数１〜６
の直鎖もしくは分枝状のアルキル基、例えばメチル、エ
チル、ｎ−プロピル、ｎ−ブチル、イソプロピル、イソ
ブチル、ｎ−ヘプチル、１−エチルプロピル、イソアミ
ル、ｎ−ヘキシルなどに加えて、ヘプチル、オクチル、
ノニル、デシル、ウンデシル、ドデシル、トリデシル、
テトラデシル、ペンタデシル、ヘキサデシル、ヘプタデ
シル、オクタデシル、ノナデシル、エイコサニル、ヘネ
イコサニル、ドコサニル、トリコサニル、テトラコサニ
ル、ペンタコサニル、ヘキサコサニル、ヘプタコサニ
ル、オクタコサニル、ノナコサニル、トリアコンタニル
などのアルキル基をあげることができるが、炭素数10〜
22程度のアルキル基が好ましい。The alkyl group found in the definition of R 5 and R 6 has 1 to 3 carbon atoms.
Refers to 0 linear or branched alkyl groups. Specifically, the lower alkyl group shown above, that is, 1 to 6 carbon atoms
Linear or branched alkyl groups such as methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, n-heptyl, 1-ethylpropyl, isoamyl, n-hexyl, etc., as well as heptyl, octyl ,
Nonyl, decyl, undecyl, dodecyl, tridecyl,
Alkyl groups such as tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosanyl, heneicosanyl, docosanil, tricosanil, tetracosanil, pentacosanil, hexacosanyl, heptacosanyl, octacosanil, nonacosanyl, triacontanyl and the like can be mentioned.
About 22 alkyl groups are preferred.
R4の定義におけるアシル基とは、脂肪族飽和カルボン
酸、脂肪族不飽和カルボン酸、炭素環式カルボン酸又は
複素環式カルボン酸のような有機酸の残基があげられる
が、具体的には、例えばホルミル、アセチル、プロピオ
ニル、ブチリル、イソブチル、バレリル、イソバレリ
ル、ピバロイルなどの低級アルカノイル基、置換もしく
は無置換のベンゾイル、トルオイル、ナフトイルなどの
アロイル基、フロイル、ニコチノイル、イソニコチノイ
ルなどのヘテロアロイル基、シクロヘキシルカルボニル
基などをあげることができる。こられのうち好ましいも
のをあげれば、アセチル、プロピオニルなどの低級アル
カノイル基、置換もしくは無置換のベンゾイル基であ
り、最も好ましいものとしては、例えばアセチル基、o,
m,p−メトキシベンゾイル基などをあげることができ
る。The acyl group in the definition of R 4 includes a residue of an organic acid such as an aliphatic saturated carboxylic acid, an aliphatic unsaturated carboxylic acid, a carbocyclic carboxylic acid or a heterocyclic carboxylic acid. For example, lower alkanoyl groups such as formyl, acetyl, propionyl, butyryl, isobutyl, valeryl, isovaleryl, pivaloyl, substituted or unsubstituted benzoyl, toluoyl, aroyl groups such as naphthoyl, heteroyl groups such as furoyl, nicotinoyl, isonicotinoyl, cyclohexyl And a carbonyl group. Among these, preferred are lower alkanoyl groups such as acetyl and propionyl, and substituted or unsubstituted benzoyl groups.The most preferred are, for example, acetyl group, o,
m, p-methoxybenzoyl group and the like.
本発明化合物は、式（Ｉ）で表される糖類縁化合物又
はその薬理学的に許容できる塩である。The compound of the present invention is a saccharide-related compound represented by the formula (I) or a pharmacologically acceptable salt thereof.
これらの塩としてはいかなる塩でも良いが、例えば上
記糖類縁化合物（Ｉ）の塩酸塩、臭化水素塩、ヨウ化水
素塩、硫酸塩、リン酸塩などの酸付加塩などのほか、本
発明においては、Ｇの定義におけるピリジン環の窒素原
子が四級化された四級塩が最も好ましい。四級塩であれ
ばいかなる塩でも良いが、これら四級塩の中でも、四級
化された塩が、 （式中R7は水素原子又は低級アルキル基を意味し、Ｘは
薬理学的に許容できるアニオンである）で示される基で
ある場合が最も好ましい。As these salts, any salts may be used. For example, in addition to the hydrochloride, hydrogen bromide, hydrogen iodide, sulfate, phosphate and the like of the above sugar-related compound (I), the present invention Is most preferably a quaternary salt in which the nitrogen atom of the pyridine ring in the definition of G is quaternized. Any salt may be used as long as it is a quaternary salt. Among these quaternary salts, a quaternized salt is (Wherein R 7 represents a hydrogen atom or a lower alkyl group, and X is a pharmacologically acceptable anion).
上記の定義において、R7は炭素数１〜３程度が好まし
く、更にはエチル基の場合が最も好ましい。In the above definition, R 7 preferably has about 1 to 3 carbon atoms, and is most preferably an ethyl group.
Ｘはいかなるアニオンでもよいが、代表的なものをあ
げれば、塩素イオン、臭素イオン、ヨウ素イオン、硫酸
イオン、硝酸イオン、リン酸イオン、酢酸イオンなどの
酸のアニオン、水酸イオンなどをあげることができる。
最も好ましいアニオンは塩素イオンなどのハロゲンイオ
ンである。X may be any anion, but typical examples include anions of acids such as chloride ion, bromine ion, iodine ion, sulfate ion, nitrate ion, phosphate ion, acetate ion, and hydroxyl ions. Can be.
Most preferred anions are halogen ions such as chloride ions.
本発明の化合物は、分子内に不斉炭素を有し、種々の
立体異性体が存在するが、本発明においては、その各々
あるいはその混合物のいずれもが本発明に包含されるこ
とは言うまでもない。The compound of the present invention has an asymmetric carbon in the molecule and has various stereoisomers, and it goes without saying that in the present invention, each of them or a mixture thereof is included in the present invention. .
次に本発明化合物の代表的な製造方法を示す。 Next, a typical method for producing the compound of the present invention will be described.
製造方法 （一連の式中R1,R2,R3,A,m,n,R4,R7及びＸは前記の意
味を有する） （第一工程） 本工程は、一般式（II）で表される化合物を常法によ
りアシル化して対応する一般式（III）で表される化合
物を得る工程である。Production method (In the series of formulas, R 1 , R 2 , R 3 , A, m, n, R 4 , R 7 and X have the same meanings as described above.) (First Step) In which the compound represented by formula (III) is acylated by a conventional method to obtain the corresponding compound represented by the general formula (III).
アシル化は、例えばR4-OH（式中R4はアシル基を意味
する）で表されるカルボン酸の反応性誘導体、例えば酸
無水物、酸ハロゲン化物などを一般式（II）で表される
化合物と反応させて、目的物質の一つである一般式（II
I）で表される化合物とする。Acylation is performed by reacting a reactive derivative of a carboxylic acid represented by, for example, R 4 —OH (wherein R 4 represents an acyl group), for example, an acid anhydride, an acid halide, and the like, by the general formula (II). Reacting with a compound of formula (II)
The compound represented by I).
アセチル基を導入する場合は、無水酢酸を用いること
が好ましい結果を与える。When an acetyl group is introduced, it is preferable to use acetic anhydride.
本反応は塩基の存在下に反応を行うことが好ましい。 This reaction is preferably performed in the presence of a base.
塩基としては、例えば水素化カリウム、水素化ナトリ
ウムのような水素化アルカリ金属類、金属ナトリウムの
ようなアルカリ金属、ナトリウムメトキシドのようなナ
トリウムアルコラート、水酸化ナトリウム、水酸化カリ
ウムのような水酸化アルカリ、ピリジン、トリエチルア
ミンなどの有機塩基、炭酸カリウム、炭酸ナトリウムな
どの炭酸アルカリなどがあげられる。Examples of the base include alkali metals such as potassium hydride and sodium hydride, alkali metals such as sodium metal, sodium alcoholate such as sodium methoxide, and hydroxides such as sodium hydroxide and potassium hydroxide. Examples include alkali, organic bases such as pyridine and triethylamine, and alkali carbonates such as potassium carbonate and sodium carbonate.
本反応は、無溶媒、又は例えばテトラヒドロフラン、
ジエチルエーテルなどのエーテル類、アセトン、メチル
エチルケトンのようなケトン類、ベンゼン、トルエンな
どのベンゼン系溶媒、アセトニトリル、ジメチルホルム
アミド、ジメチルスルホキシド、ヘキサメチルリン酸ト
リアミドなどから選択された溶媒中で行われる。This reaction is carried out without solvent, or for example, tetrahydrofuran,
The reaction is carried out in a solvent selected from ethers such as diethyl ether, ketones such as acetone and methyl ethyl ketone, benzene solvents such as benzene and toluene, acetonitrile, dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide and the like.
反応温度は約−78℃乃至溶媒沸点まで適宜選ばれる。 The reaction temperature is appropriately selected from about -78 ° C to the boiling point of the solvent.
（第二工程） 本反応は、第一工程で得られた一般式（III）で表さ
れる化合物を常法により四級塩化し、本発明化合物（V
I）を得る工程である。即ち、一般式（III）で表される
化合物を一般式R7-X（式中R7,Xは前記の意味を有する）
で表される化合物と反応させることにより、容易に目的
物質である本発明化合物（IV）を得る。ハロゲン化水素
塩とする際はR7-Halと反応させる。(Second Step) In this reaction, the compound represented by the general formula (III) obtained in the first step is quaternarily salified by a conventional method, and the compound of the present invention (V
This is the step of obtaining I). That is, the compound represented by the general formula (III) is converted to a compound represented by the general formula R 7 -X (where R 7 and X have the above-mentioned meanings)
The compound of the present invention (IV), which is the target substance, is easily obtained by reacting with the compound represented by When converting to a hydrogen halide salt, it is reacted with R 7 -Hal.
本反応は好ましくは窒素中遮光して行われ、無溶媒、
又は例えばメタノール、エタノールなどのアルコール
類、テトラヒドロフラン、ジエチルエーテルなどのエー
テル類、アセトン、メチルエチルケトンのようなケトン
類、ベンゼン、トルエンなどのベンゼン系溶媒、アセト
ニトリル、ジメチルホルムアミド、ジメチルスルホキシ
ド、ヘキサメチルリン酸トリアミドなどから選択された
溶媒中で行われる。This reaction is preferably performed in a light-shielded atmosphere in nitrogen, without solvent,
Or, for example, alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and diethyl ether, ketones such as acetone and methyl ethyl ketone, benzene solvents such as benzene and toluene, acetonitrile, dimethylformamide, dimethyl sulfoxide, and hexamethylphosphoric triamide The reaction is performed in a solvent selected from the above.
反応温度は氷冷下乃至溶媒沸点まで適宜選ばれる。 The reaction temperature is appropriately selected from under ice-cooling to the boiling point of the solvent.
なお、本製造方法において、出発物質として用いられ
る一般式（II）で表される化合物は、下記に示した実施
例に記載されている方法に準じて製造できる。In this production method, the compound represented by the general formula (II) used as a starting material can be produced according to the method described in the following Examples.
次に本発明の効果を詳述するために、実験例を以下に
示す。Next, experimental examples will be described below in order to explain the effects of the present invention in detail.
実験例１ ヒト血小板PAF惹起凝集に対する作用 ＜方法＞ ２週間以上薬物を服用していない健常成人男子の前腕
静脈から採血し、これに3.8％クエン酸ナトリウム溶液
を1/9容添加した。遠心法により多血小板血漿（PRP）を
調製した。血小板能の測定はボーン（Born）らの光学的
方法に準じて血小板凝集メーターヘマトレーサーII
（二光バイオサイエンス社）を用いて測定した。PAFはT
yrode溶液（Ca++（＋））に溶解し、最大凝集を起こす
最低の濃度を用いた。被験化合物は生理食塩水に溶解し
た。Experimental Example 1 Effect on human platelet PAF-induced aggregation <Method> Blood was collected from the forearm vein of a healthy adult male who had not taken the drug for more than 2 weeks, and 1/9 volume of a 3.8% sodium citrate solution was added thereto. Platelet-rich plasma (PRP) was prepared by centrifugation. The platelet activity was measured according to the optical method of Born et al.
(Nikko Bioscience). PAF is T
The lowest concentration that dissolved in yrode solution (Ca ++ (+)) and caused maximum aggregation was used. The test compound was dissolved in physiological saline.
被験化合物の凝集抑制活性は、対照PRPにおけるPAFに
よる最大の光透過度（最大凝集率）に対する抑制率から
求めた。その抑制曲線よりIC50を求めた。結果を表１に
示す。The aggregation inhibitory activity of the test compound was determined from the inhibition rate against the maximum light transmittance (maximum aggregation rate) by PAF in the control PRP. The IC 50 was determined from the inhibition curve. Table 1 shows the results.
被験化合物の欄の番号は下記に示す実施例番号の化合
物である。The numbers in the column of the test compound are the compounds of the example numbers shown below.
＜結果＞ 実験例２ ヒト血小板を用いたPAF receptor binding assay （受
容体拮抗活性） ＜方法＞ 男子健常人より常法に従って血小板を得、バインディ
ングバッファー（Binding Buffer）（10mM phosphate-b
ufferes saline（pH7.0）,0.1％（w/v）BSA,0.9mM CaCl
2を含む）に108ケ/460μｌとなるように懸濁する。ポリ
プロピレンチューブに被験化合物のバインディングバッ
ファー溶液20μｌを加え、血小板液460μｌをさらに加
えて、Vortex後37℃で６分間インキュベート（incubat
e）する。次いで3H-PAFのバインディングバッファー溶
液20μｌ（final 3H-PAF濃度0.6〜1nM）を加え、６分間
インキュベートし、氷冷した洗浄溶液（0.1％（W/V）の
BSAを含むSaline）3mlを加え反応を停止し、ガラスフィ
ルター（Whatman GF/C）上で吸引濾過する。ガラスフィ
ルターを乾燥後、液体シンチレーションカウンターにて
放射能を測定する。<Result> Experimental Example 2 PAF receptor binding assay (receptor antagonist activity) using human platelets <Method> Platelets were obtained from a healthy male subject according to an ordinary method, and a binding buffer (10 mM phosphate-b) was obtained.
ufferes saline (pH 7.0), 0.1% (w / v) BSA, 0.9 mM CaCl
Suspended in including 2) so as to be 10 8 Ke / 460μl. 20 μl of the test compound binding buffer solution was added to a polypropylene tube, 460 μl of platelet solution was further added, and the mixture was incubated at 37 ° C. for 6 minutes after Vortex (incubat).
e) Yes. Next, 20 μl of a 3 H-PAF binding buffer solution (final 3 H-PAF concentration: 0.6 to 1 nM) was added, incubated for 6 minutes, and washed with an ice-cooled washing solution (0.1% (W / V)).
The reaction is stopped by adding 3 ml of Saline containing BSA, followed by suction filtration on a glass filter (Whatman GF / C). After drying the glass filter, the radioactivity is measured with a liquid scintillation counter.
Inhibition％は下記の式に従って計算し、IC50は図よ
り内挿して求めた。Inhibition% was calculated according to the following formula, and IC 50 was obtained by interpolation from the figure.
Inhibition％＝ (total binding)-(total binding with compound) (total binding)-(non-specific binding) total binding;薬物あるいはPAF濃度０の時のdpm. non−specific binding;cold PAF 10-5M加えた時のdp
m. 結果を表２に示す。Inhibition% = (total binding)-(total binding with compound) (total binding)-(non-specific binding) total binding; dpm when drug or PAF concentration is 0; non-specific binding; cold PAF 10 -5 M added Dp when
m. The results are shown in Table 2.
＜結果＞ 上記の実験例により本発明化合物は、優れたPAF抑制
作用を有することが明らかである。<Result> The above experimental examples clearly show that the compound of the present invention has an excellent PAF inhibitory action.
更に、本発明化合物は、抗PAF作用の持続性に優れ、
かつ安定性においても優れていることが判明しており、
本発明の価値は高い。Furthermore, the compound of the present invention has excellent anti-PAF action persistence,
It has also been found to be excellent in stability,
The value of the present invention is high.
従って、本発明化合物は、PAFに起因するあらゆる疾
患の治療・予防に有効である。Therefore, the compound of the present invention is effective for treating / preventing any disease caused by PAF.
代表的な疾患をあげれば、血栓症、脳卒中（脳出血、
脳血栓）、心筋梗塞、狭心症、ヒトの血管内凝固症候群
（DIC）、血栓性静脈炎、糸球体腎炎、アナフィラキシ
ーショック、出血性ショック、アレルギー疾患などの治
療・予防剤として有用である。Representative diseases include thrombosis, stroke (cerebral hemorrhage,
It is useful as a therapeutic / prophylactic agent for cerebral thrombosis), myocardial infarction, angina pectoris, intravascular coagulation syndrome (DIC) in humans, thrombophlebitis, glomerulonephritis, anaphylactic shock, hemorrhagic shock, allergic diseases and the like.
本発明化合物を抗PAF剤として投与する場合、散剤、
顆粒剤、カプセル剤、シロップ剤などとして経口的に投
与してもよいし、また坐剤、注射剤、外用剤、点滴剤と
して非経口的に投与してもよいが、本発明の場合は、通
常は注射剤又は点滴剤として投与することが好ましい。When the compound of the present invention is administered as an anti-PAF agent, a powder,
Granules, capsules, may be administered orally as a syrup or the like, or may be administered parenterally as a suppository, injection, external preparation, or infusion, in the case of the present invention, Usually, administration as an injection or infusion is preferred.
投与量は、疾患の種類、症状の程度、年令などにより
著しく異なるが、点滴注射剤として投与する場合は、約
0.01〜10mg/kg/hr、好ましくは0.03〜5mg/kg/hrを投与
する。The dosage varies significantly depending on the type of disease, degree of symptoms, age, etc.
The dose is 0.01 to 10 mg / kg / hr, preferably 0.03 to 5 mg / kg / hr.
また、静脈注射剤として投与する場合は、通常成人１
日あたり約0.001〜50mg/kg、好ましくは0.001〜30mg/k
g、更に好ましくは約0.001〜5mg/kg、更に好ましくは約
0.003〜3mg/kgを１日１〜数回にわけて投与する。When administered as an intravenous injection, the dosage is usually 1 adult.
About 0.001 to 50 mg / kg per day, preferably 0.001 to 30 mg / k
g, more preferably about 0.001-5 mg / kg, more preferably about
0.003 to 3 mg / kg is administered once to several times a day.
注射剤、点滴剤などを調製する場合は、主薬に必要に
よりpH調整剤、緩衝剤、安定化剤、可溶化剤などを添加
し、必要ならば凍結乾燥などを行って、常法により皮下
・筋肉内・静脈内用注射剤、点滴注射剤とする。When preparing injections, infusions, etc., add pH adjusters, buffers, stabilizers, solubilizers, etc. as necessary to the base drug, freeze-dry if necessary, and subcutaneously Intramuscular and intravenous injections and drip injections.
次に本発明の代表的な実施例を掲げるが、本発明がそ
れらにのみ限定されることがないことは言うまでもな
い。Next, typical examples of the present invention will be described. However, it is needless to say that the present invention is not limited thereto.
なお、実施例における化学構造式において、Meはメチ
ル基を意味し、Etはエチル基を意味し、THPはテトラヒ
ドロピラン残基を意味する。In the chemical structural formulas in the examples, Me means a methyl group, Et means an ethyl group, and THP means a tetrahydropyran residue.
実施例１ １−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−アン
ヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ−オクタデ
シルカルバモイル−Ｌ−グリセロ−Ｌ−グロ−ヘプチト
ロキシ｝カルボニル〕アミノメチルピリジニウムヨージ
ド （１）１−デオキシ−2,3,4−トリ−Ｏ−メチル−１−
（1'−プロペニル）−６−Ｏ−（テトラヒドロピラン−
２−イル）−β−Ｄ−グリコピラノース １−デオキシ−１−（1'−プロペニル）−６−Ｏ−
（テトラヒドロピラン−２−イル）−β−Ｄ−グルコピ
ラノース513mgをジメチルホルムアミド30ml−テトラヒ
ドロフラン15mlに溶かし、室温にて60％水素化ナトリウ
ム337mgを加え、ヨウ化メチル700μｌを更に加えた。反
応終了後、酢酸エチルを加え、水洗した後、減圧下溶媒
を留去した。残渣をカラムクロマトグラフィー（溶出溶
媒；ヘキサン：酢酸エチル）を用い精製し、標記化合物
360mgを得た。1 H-NMR(CDCl3)δ； 1.40〜1.94（m,6H）,2.16〜2.34（m,1H）,2.44〜2.60
（m,1H）,2.88（t,1H,J＝8Hz）,2.96〜3.36（m,4H）,3.
37〜4.00（m,4H）,3.58（s,3H）,3.60（s,3H）,3.68
（s,3H）,4.64〜4.76（m,1H）,5.06（d,1H,J＝10Hz）,
5.12（d,1H,J＝16Hz）,5.80〜6.00（m,1H）， （２）１−デオキシ−１−（1'−ヒドロキシエチル）−
2,3,4−トリ−Ｏ−メチル−６−Ｏ−（テトラヒドロピ
ラン−２−イル）−β−Ｄ−グルコピラノース 出発物質360mgをメタノール15mlに溶かし、−78℃に
てオゾンを導入した後、過剰の水素化ホウ素ナトリウム
を加え、反応終了後、1gの塩化アンモニウムを加えた。
反応液を濾過し、減圧下濃縮し、得られた残渣をカラム
クロマトグラフィー（溶出溶媒；塩化メチレン：酢酸エ
チル）を用い精製し、標記化合物296mgを得た。1 H-NMR(CDCl3)δ； 1.42〜1.92（m,8H）,1.96〜2.12（m,1H）,2.89（t,1H,J
＝9Hz）,3.03（t,1H,J＝9Hz）,3.20（t,1H,J＝9Hz）,3.
24〜4.00（m,8H）,3.54（s,3H）,3.60（s,3H）,3.69
（s,3H）,4.59〜4.64,4.65〜4.70（m,1H） （３）１−デオキシ−2,3,4−トリ−Ｏ−メチル−６−
Ｏ−（テトラヒドロピラン−２−イル）−１−ビニル−
β−Ｄ−グルコピラノース 出発物質296mgをベンゼン6mlに溶かし、２−ニトロフ
ェニルゼレニウムサイアナイド307mg、トリブチルホス
フィン272mgを加え、室温にて30分間攪拌した。次に塩
化メチレン2ml、メタクロル過安息香酸341mgを加え、更
に室温にて30分間攪拌した後、トリエチルアミン2.5ml
を加え、一昼夜室温にて攪拌した。反応終了後、水、飽
和食塩水にて洗い、減圧下濃縮した。得られた残渣をカ
ラムクロマトグラフィー（溶出溶媒；ヘキサン：酢酸エ
チル）を用い精製し、標記化合物246mgを得た。1 H-NMR(CDCl3)δ； 1.40〜1.92（m,6H）,2.86（t,1H,J＝9Hz）,3.00〜3.76
（m,7H）,3.52（s,3H）,3.60（s,3H）,3.68（s,3H）,3.
80〜4.02（m,2H）,4.62〜4.76（m,1H）,5.23（d,1H,J＝
10Hz）,5.38（d,1H,J＝16Hz）,5.83〜6.00（m,1H） （４）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７
−Ｏ−（テトラヒドロピラン−２−イル）−Ｄ−グリセ
ロ−Ｄ−グロ−ヘプチトール 出発物質240mgを用い、前述の方法に従いオゾン分解
を行った。得られた残渣をカラムクロマトグラフィー
（溶出溶媒；ヘキサン：酢酸エチル）を用い精製し、標
記化合物212mgを得た。1 H-NMR(CDCl3)δ； 1.44〜1.72（m,6H）,2.22〜2.34（m,1H）,3.04〜3.42
（m,5H）,3.48〜3.74（m,3H）,3.52（s,3H）,3.58（s,3
H）,3.65（s,3H）,3.80〜3.96（m,3H）,4.60〜4.64（m,
1H） （５）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−オクタデシルカルバモイル−７−Ｏ−（テトラヒ
ドロピラン−２−イル）−Ｄ−グリセロ−Ｄ−グロ−ヘ
プチトール 出発物質210mgをベンゼン5mlに溶かし、ピリジンを数
滴加え、更にオクタデシルイソシアナート690μｌを加
え、一昼夜加熱還流した。反応終了後、酢酸エチルで抽
出し、減圧下濃縮し、得られた残渣をカラムクロマトグ
ラフィー（溶出溶媒；塩化メチレン：酢酸エチル）を用
い精製し、標記化合物390mgを得た。1 H-NMR(CDCl3)δ； 0.87（t,3H,J＝7.2Hz）,1.18〜1.36（m,32H）,1.40〜1.
88（m,6H）,2.76〜3.76（m,9H）,3.53（s,3H）,3.58
（s,3H）,3.66（s,3H）,3.80〜4.02（m,2H）,4.06〜4.3
6（m,2H）,4.60〜4.86（m,2H） （６）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−オクタデシルカルバモイル−Ｄ−グリセロ−Ｄ−
グロ−ヘプチトール 出発物質390mgをエタノール5mlに溶かし、ピリジニウ
ム・パラ−トルエンスルホン酸80mgを加え、30分間還流
した。反応終了後、残渣にエーテルを加え、不溶物を濾
過し、濾液を減圧下濃縮した。得られた残渣をカラムク
ロマトグラフィー（溶出溶媒；ヘキサン：酢酸エチル）
を用い精製し、標記化合物289mgを得た。1 H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.14〜1.52（m,32H）,2.10〜2.
18（m,1H）,2.94〜3.88（m,9H）,3.52（s,3H）,3.56
（s,3H）,3.66（s,3H）,4.12〜4.36（m,2H）,4.70〜4.8
4（m,1H） （７）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−オクタデシルカルバモイル−７−Ｏ−〔Ｎ−（ピ
リジン−２−イル）メチルカルバモイル〕−Ｄ−グリセ
ロ−Ｄ−グロ−ヘプチトール 出発物質280mgを塩化メチレン5mlに溶かし、ピリジン
167mg、クロル炭酸フェニル165mgを加え、０℃にて攪拌
した。次に２−アミノピリジン570mgを加え、塩化メチ
レンを留去した後、クロロホルムを加え、一昼夜加熱還
流した。反応終了後、エーテルを加え不溶物を除き、濾
液を濃縮し、得られた残渣をカラムクロマトグラフィー
（溶出溶媒；クロロホルム：メタノール）を用い精製
し、標記化合物289mgを得た。1 H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.16〜1.50（m,32H）,2.96〜3.
42（m,7H）,3.52（s,6H）,3.65（s,3H）,4.12〜4.42
（m,4H）,4.49（d,2H,J＝6Hz）,4.78〜4.92（m,1H）,5.
80〜5.94（m,1H）,7.17〜7.40（m,2H）,7.64（t,1H,J＝
7Hz）,8.54（d,1H,J＝5Hz） （８）７−Ｏ−〔Ｎ−アセチル−Ｎ−｛（ピリジン−２
−イル）メチル｝〕カルバモイル−2,6−アンヒドロ−
3,4,5−トリ−Ｏ−メチル−１−Ｏ−オクタデシルカル
バモイル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトール 出発物質270mgに無水酢酸3.8ml、ピリジン4.0mlを加
え、110℃にて18時間加熱した。反応終了後、減圧下溶
媒を留去し、得られた残渣をカラムクロマトグラフィー
（溶出溶媒；ヘキサン：酢酸エチル）を用いて精製し、
標記化合物218mgを得た。1 H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.14〜1.36（m,32H）,2.66（s,
3H）,2.86（dd,1H,J＝9Hz,9Hz）,3.00〜3.24（m,5H）,
3.40（s,3H）,3.50（s,3H）,3.60（s,3H）,4.00〜4.42
（m,5H）,5.04（d,1H,J＝18Hz）,5.16（d,1H,J＝18H
z）,5.78〜5.88（m,1H）,7.10（d,1H,J＝7Hz）,7.18
（t,1H,J＝7Hz）,7.66（t,1H,J＝7Hz）,8.52（d,1H,J＝
5Hz） （９）１−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−
アンヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ−オク
タデシルカルバモイル−Ｌ−グリセロ−Ｌ−グロ−ヘプ
チトロキシ｝カルボニル〕アミノメチルピリジニウムヨ
ージド 出発物質70mgにヨードエタン2.5mlを加え一昼夜加熱
還流した。反応終了後、ヨードエタンを留去し、得られ
た残渣をカラムクロマトグラフィー（溶出溶媒；クロロ
ホルム：メタノール）を用い精製し、標記化合物60mgを
得た。1 H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.16〜1.56（m,32H）,1.74（t,
3H,J＝7.2Hz）,2.64（s,3H）,2.80（t,1H,J＝9Hz）,3.0
0〜3.40（m,6H）,3.50（s,3H）,3.56（s,3H）,3.65（s,
3H）,4.06〜4.56（m,4H）,5.06〜5.26（m,2H）,5.36〜
5.48（m,3H）,6.77（d,1H,J＝7Hz）,7.03（t,1H,J＝7H
z）,7.42（t,1H,J＝7Hz）,9.98（d,1H,J＝5Hz） 実施例１（４）で得られた2,6−アンヒドロ−3,4,5−
トリ−Ｏ−メチル−７−Ｏ−（テトラヒドロピラン−２
−イル）−Ｄ−グリセロ−Ｄ−グロ−ヘプチトールは以
下に示すルートによっても合成できる。Example 1 1-ethyl-2- [N-acetyl-N- {2,6-anhydro-3,4,5-tri-O-methyl-7-O-octadecylcarbamoyl-L-glycero-L-glo- Heptitroxy｝ carbonyl] aminomethylpyridinium iodide (1) 1-deoxy-2,3,4-tri-O-methyl-1-
(1′-propenyl) -6-O- (tetrahydropyran-
2-yl) -β-D-glycopyranose 1-deoxy-1- (1'-propenyl) -6-O-
513 mg of (tetrahydropyran-2-yl) -β-D-glucopyranose was dissolved in 30 ml of dimethylformamide-15 ml of tetrahydrofuran, 337 mg of 60% sodium hydride was added at room temperature, and 700 μl of methyl iodide was further added. After completion of the reaction, ethyl acetate was added, and the mixture was washed with water, and then the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent; hexane: ethyl acetate) to give the title compound
360 mg were obtained. 1 H-NMR (CDCl 3 ) δ; 1.40 to 1.94 (m, 6H), 2.16 to 2.34 (m, 1H), 2.44 to 2.60
(M, 1H), 2.88 (t, 1H, J = 8Hz), 2.96 to 3.36 (m, 4H), 3.
37 ~ 4.00 (m, 4H), 3.58 (s, 3H), 3.60 (s, 3H), 3.68
(S, 3H), 4.64 ~ 4.76 (m, 1H), 5.06 (d, 1H, J = 10Hz),
5.12 (d, 1H, J = 16 Hz), 5.80-6.00 (m, 1H), (2) 1-deoxy-1- (1'-hydroxyethyl)-
2,3,4-tri-O-methyl-6-O- (tetrahydropyran-2-yl) -β-D-glucopyranose After 360 mg of the starting material was dissolved in 15 ml of methanol and ozone was introduced at -78 ° C, excess sodium borohydride was added. After the reaction was completed, 1 g of ammonium chloride was added.
The reaction solution was filtered and concentrated under reduced pressure, and the obtained residue was purified by column chromatography (elution solvent: methylene chloride: ethyl acetate) to obtain 296 mg of the title compound. 1 H-NMR (CDCl 3) δ; 1.42~1.92 (m, 8H), 1.96~2.12 (m, 1H), 2.89 (t, 1H, J
= 9Hz), 3.03 (t, 1H, J = 9Hz), 3.20 (t, 1H, J = 9Hz), 3.
24-4.00 (m, 8H), 3.54 (s, 3H), 3.60 (s, 3H), 3.69
(S, 3H), 4.59 to 4.64, 4.65 to 4.70 (m, 1H) (3) 1-deoxy-2,3,4-tri-O-methyl-6-
O- (tetrahydropyran-2-yl) -1-vinyl-
β-D-glucopyranose 296 mg of the starting material was dissolved in 6 ml of benzene, 307 mg of 2-nitrophenyl zelenium cyanide and 272 mg of tributylphosphine were added, and the mixture was stirred at room temperature for 30 minutes. Next, 2 ml of methylene chloride and 341 mg of metachloroperbenzoic acid were added, and the mixture was further stirred at room temperature for 30 minutes.
And stirred at room temperature for 24 hours. After the completion of the reaction, the mixture was washed with water and saturated saline, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (elution solvent; hexane: ethyl acetate) to obtain 246 mg of the title compound. 1 H-NMR (CDCl 3 ) δ; 1.40 to 1.92 (m, 6H), 2.86 (t, 1H, J = 9 Hz), 3.00 to 3.76
(M, 7H), 3.52 (s, 3H), 3.60 (s, 3H), 3.68 (s, 3H), 3.
80 ~ 4.02 (m, 2H), 4.62 ~ 4.76 (m, 1H), 5.23 (d, 1H, J =
10 Hz), 5.38 (d, 1H, J = 16 Hz), 5.83 to 6.00 (m, 1H) (4) 2,6-Anhydro-3,4,5-tri-O-methyl-7
-O- (tetrahydropyran-2-yl) -D-glycero-D-glo-heptitol Using 240 mg of the starting material, ozonolysis was performed according to the method described above. The obtained residue was purified by column chromatography (elution solvent; hexane: ethyl acetate) to obtain 212 mg of the title compound. 1 H-NMR (CDCl 3 ) δ; 1.44 to 1.72 (m, 6H), 2.22 to 2.34 (m, 1H), 3.04 to 3.42
(M, 5H), 3.48 to 3.74 (m, 3H), 3.52 (s, 3H), 3.58 (s, 3
H), 3.65 (s, 3H), 3.80 to 3.96 (m, 3H), 4.60 to 4.64 (m,
1H) (5) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O-octadecylcarbamoyl-7-O- (tetrahydropyran-2-yl) -D-glycero-D-glo-heptitol 210 mg of the starting material was dissolved in 5 ml of benzene, several drops of pyridine were added, 690 μl of octadecyl isocyanate was further added, and the mixture was heated and refluxed overnight. After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated under reduced pressure, and the obtained residue was purified by column chromatography (elution solvent: methylene chloride: ethyl acetate) to obtain 390 mg of the title compound. 1 H-NMR (CDCl 3) δ; 0.87 (t, 3H, J = 7.2Hz), 1.18~1.36 (m, 32H), 1.40~1.
88 (m, 6H), 2.76 to 3.76 (m, 9H), 3.53 (s, 3H), 3.58
(S, 3H), 3.66 (s, 3H), 3.80 to 4.02 (m, 2H), 4.06 to 4.3
6 (m, 2H), 4.60 to 4.86 (m, 2H) (6) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O-octadecylcarbamoyl-D-glycero-D-
Glow heptitol The starting material (390 mg) was dissolved in ethanol (5 ml), and pyridinium para-toluenesulfonic acid (80 mg) was added, followed by refluxing for 30 minutes. After completion of the reaction, ether was added to the residue, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue is subjected to column chromatography (elution solvent; hexane: ethyl acetate).
The residue was purified using to give 289 mg of the title compound. 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.14~1.52 (m, 32H), 2.10~2.
18 (m, 1H), 2.94 to 3.88 (m, 9H), 3.52 (s, 3H), 3.56
(S, 3H), 3.66 (s, 3H), 4.12 to 4.36 (m, 2H), 4.70 to 4.8
4 (m, 1H) (7) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O-octadecylcarbamoyl-7-O- [N- (pyridin-2-yl) methylcarbamoyl] -D-glycero-D-glo-heptitol Dissolve 280 mg of the starting material in 5 ml of methylene chloride and add pyridine
167 mg and 165 mg of phenyl chlorocarbonate were added, and the mixture was stirred at 0 ° C. Next, 570 mg of 2-aminopyridine was added, and after methylene chloride was distilled off, chloroform was added, and the mixture was heated and refluxed for one day. After completion of the reaction, ether was added to remove insolubles, the filtrate was concentrated, and the obtained residue was purified by column chromatography (elution solvent: chloroform: methanol) to obtain 289 mg of the title compound. 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.16~1.50 (m, 32H), 2.96~3.
42 (m, 7H), 3.52 (s, 6H), 3.65 (s, 3H), 4.12 to 4.42
(M, 4H), 4.49 (d, 2H, J = 6 Hz), 4.78 to 4.92 (m, 1H), 5.
80 to 5.94 (m, 1H), 7.17 to 7.40 (m, 2H), 7.64 (t, 1H, J =
7 Hz), 8.54 (d, 1H, J = 5 Hz) (8) 7-O- [N-acetyl-N-｛(pyridine-2
-Yl) methyl}] carbamoyl-2,6-anhydro-
3,4,5-tri-O-methyl-1-O-octadecylcarbamoyl-D-glycero-D-glo-heptitol 3.8 ml of acetic anhydride and 4.0 ml of pyridine were added to 270 mg of the starting material, and the mixture was heated at 110 ° C. for 18 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the obtained residue was purified using column chromatography (elution solvent; hexane: ethyl acetate).
218 mg of the title compound were obtained. 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.14~1.36 (m, 32H), 2.66 (s,
3H), 2.86 (dd, 1H, J = 9Hz, 9Hz), 3.00-3.24 (m, 5H),
3.40 (s, 3H), 3.50 (s, 3H), 3.60 (s, 3H), 4.00 to 4.42
(M, 5H), 5.04 (d, 1H, J = 18Hz), 5.16 (d, 1H, J = 18H
z), 5.78 to 5.88 (m, 1H), 7.10 (d, 1H, J = 7 Hz), 7.18
(T, 1H, J = 7Hz), 7.66 (t, 1H, J = 7Hz), 8.52 (d, 1H, J =
5Hz) (9) 1-ethyl-2- [N-acetyl-N- ｛2,6-
Anhydro-3,4,5-tri-O-methyl-7-O-octadecylcarbamoyl-L-glycero-L-glo-heptitroxy {carbonyl] aminomethylpyridinium iodide 2.5 mg of iodoethane was added to 70 mg of the starting material, and the mixture was heated under reflux overnight. After the completion of the reaction, iodoethane was distilled off, and the obtained residue was purified by column chromatography (elution solvent: chloroform: methanol) to obtain 60 mg of the title compound. 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.16~1.56 (m, 32H), 1.74 (t,
3H, J = 7.2Hz), 2.64 (s, 3H), 2.80 (t, 1H, J = 9Hz), 3.0
0 to 3.40 (m, 6H), 3.50 (s, 3H), 3.56 (s, 3H), 3.65 (s,
3H), 4.06 to 4.56 (m, 4H), 5.06 to 5.26 (m, 2H), 5.36 to
5.48 (m, 3H), 6.77 (d, 1H, J = 7Hz), 7.03 (t, 1H, J = 7H
z), 7.42 (t, 1H, J = 7 Hz), 9.98 (d, 1H, J = 5 Hz) 2,6-Anhydro-3,4,5- obtained in Example 1 (4)
Tri-O-methyl-7-O- (tetrahydropyran-2
-Yl) -D-glycero-D-glo-heptitol can also be synthesized by the following route.
（１）2,3,4−トリ−Ｏ−メチル−Ｄ−グルコピラノー
ス 2,3,4−トリ−Ｏ−メチル−1,6−アンヒドロ−β−Ｄ
−グルコース60.3gに2N−塩酸800mlを加え、90℃にて一
昼夜攪拌した。反応終了後、減圧下溶媒を留去し、得ら
れた残渣をカラムクロマトグラフィー（溶出溶媒；クロ
ロホルム：メタノール）を用い精製し、標記化合物64.0
gを得た。1 H-NMR(CDCl3)δ； 3.07〜3.3（m,2H）,3.4〜3.65（m,14H）,3.65〜3.8（m,
2H）,4.65（d,1H）,5.3（d,1H） （２）６−Ｏ−（ｔ−ブチルジメチルシリル）−2,3,4
−トリ−Ｏ−メチル−Ｄ−グルコピラノース 出発物質65.9gをジメチルホルムアミド400mlに溶か
し、ｔ−ブチルジメチルシリルクロリド44g、イミダゾ
ール50.3gを加え30分間室温にて攪拌した。反応終了
後、反応液に酢酸エチルを加え、水洗をした。減圧下溶
媒を留去し、得られた残渣をカラムクロマトグラフィー
（溶出溶媒；ヘキサン：酢酸エチル）を用いて精製し、
標記化合物75.0gを得た。1 H-NMR(CDCl3)δ； 0.09（s,6H）,0.9（s,9H）,1.7（br s,1H）,2.8〜3.0
（m,2H）,3.1〜3.9（m,12H）,4.65（m,1H）,5.25（br
s,1H） （３）６−Ｏ−（ｔ−ブチルジメチルシリル）−2,3,4
−トリ−Ｏ−メチル−Ｄ−グルコノ−1,5−ラクトン シュウ酸クロリド85mlを塩化メチレン800mlに溶か
し、−70℃にてジメチルスルホキシド138mlをゆっくり
滴下した。更にアルコール体65gを塩化メチレン200mlに
溶かしゆっくり滴下した。最後にトリエチルアミン400m
lを滴下し、室温まで昇温した。反応終了後、水にあ
け、クロロホルムで抽出し、減圧下溶媒を留去した。得
られた残渣をカラムクロマトグラフィー（溶出溶媒；ヘ
キサン：酢酸エチル）を用いて精製し、標記化合物61.4
gを得た。1 H-NMR(90MHz,CDCl3)δ； 0.09（s,6H）,0.9（s,9H）,3.50,3.52,3.56（each s,ea
ch 3H）,3.5〜3.9（m,4H）,4.0〜4.3（m,1H） （４）６−Ｏ−（ｔ−ブチルジメチルシリル）−１−
（1'−ヘプチニル）−2,3,4−トリ−Ｏ−メチル−Ｄ−
グルコ−１−ヘキスロース １−ヘキシン32mlをテトラヒドロフラン300mlに溶か
し、−70℃にてｎ−ブチルリチウム（2.5M/l）86mlをゆ
っくり滴下した。次にケトン体51.5gをテトラヒドロフ
ラン200mlに溶かしたものをゆっくり滴下した。反応終
了後、飽和塩化アンモニウム水溶液を加え、塩化メチレ
ンで抽出し、減圧下溶媒を留去した。得られた残渣をカ
ラムクロマトグラフィー（溶出溶媒；ヘキサン：酢酸エ
チル）を用い精製し、標記化合物87.3gを得た。1 H-NMR(90MHz,CDCl3)δ； 0.09（s,6H）,0.9（s,9H）,0.8〜0.9（m,3H）,1.1〜1.7
（m,4H）,2.0〜2.4（m,2H）,3.50,3.60,3.64（each s,e
ach 3H）,3.0〜3.9（m,6H） （５）１−デオキシ−１−（1'−ヘプチニル）−2,3,4
−トリ−Ｏ−メチル−Ｄ−グルコピラノース 出発物質56gをアセトニトリル−塩化メチレン（17:
3）800mlに溶かし、トリエチルシリルヒドリド81gを加
え、次に−10℃にてボロントリフルオライド・エーテラ
ート30mlをゆっくり滴下した。反応終了後、飽和炭酸水
素をナトリウム水溶液を加え、酢酸エチルで抽出し、減
圧下溶媒を留去した。得られた残渣をカラムクロマトグ
ラフィー（溶出溶媒；ヘキサン：酢酸エチル）を用い精
製し、標記化合物33.2gを得た。1 H-NMR(90MHz,CDCl3)δ； 0.7〜1.0（m,3H）,1.2〜1.6（m,4H）,2.05〜2.35（m,2
H）,2.9〜3.2（m,4H）,3.50（s,3H）,3.60（s,6H）,3.4
〜3.95（m,4H） （６）１−デオキシ−１−（1'−ヘプテニル）−2,3,4
−トリ−Ｏ−メチル−Ｄ−グルコピラノース 出発物質28.1gをメタノール300mlに溶かし、パラジウ
ム−硫酸バリウム5.0g、キノリン0.9mlを加え、水素添
加を行った。反応終了後、セライト濾過し、濾液を希塩
酸、炭酸水素ナトリウム水溶液で洗い、減圧下溶媒を留
去し、標記化合物26.0gを得た。1 H-NMR(90MHz,CDCl3)δ； 0.7〜1.1（m,3H）,1.1〜1.6（m,4H）,1.8〜2.3（m,2
H）,2.6〜3.35（m,4H）,3.42,3.50,3.62（each s,each
3H）,3.3〜4.05（m,4H）,6.1〜6.8（m,2H） （７）１−デオキシ−１−（1'−ヘプテニル）−2,3,4
−トリ−Ｏ−メチル−６−Ｏ−（テトラヒドロフラン−
２−イル）−Ｄ−グルコピラノース 出発物質32.0gを塩化メチレン500mlに溶かし、ジヒド
ロピラン32ml、ピリジニウムｐ−トルエンスルホン酸6.
0gを加え、室温にて攪拌した。反応終了後水にあけ、酢
酸エチルで抽出し、減圧下溶媒を留去した。得られた残
渣をカラムクロマトグラフィー（溶出溶媒；ヘキサン：
酢酸エチル）を用い精製し、標記化合物43.3gを得た。1 H-NMR(90MHz,CDCl3)δ； 0.7〜1.1（m,3H）,1.1〜1.9（m,10H）,2.0〜2.3（m,2
H）,2.6〜4.05（m,19H）,4.65（br ,1H）,5.2〜5.8（m,
2H） （８）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７
−Ｏ−（テトラヒドロフラン−２−イル）−Ｄ−グリセ
ロ−Ｄ−グロ−ヘプチトール 出発物質43gをメタノール600mlに溶かし、オゾン分解
を行い、ソディウムボロヒドリド9.1gを用い還元した。
反応終了後水、溶媒を留去し、得られた残渣をカラムク
ロマトグラフィー（溶出溶媒；ヘキサン：酢酸エチル）
を用い精製し、標記化合物34.5gを得た。(1) 2,3,4-tri-O-methyl-D-glucopyranose 2,3,4-tri-O-methyl-1,6-anhydro-β-D
-800 ml of 2N-hydrochloric acid was added to 60.3 g of glucose, and the mixture was stirred at 90 ° C for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (elution solvent: chloroform: methanol) to give the title compound 64.0.
g was obtained. 1 H-NMR (CDCl 3 ) δ; 3.07 to 3.3 (m, 2H), 3.4 to 3.65 (m, 14H), 3.65 to 3.8 (m,
2H), 4.65 (d, 1H), 5.3 (d, 1H) (2) 6-O- (t-butyldimethylsilyl) -2,3,4
-Tri-O-methyl-D-glucopyranose The starting material (65.9 g) was dissolved in dimethylformamide (400 ml), t-butyldimethylsilyl chloride (44 g) and imidazole (50.3 g) were added, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, ethyl acetate was added to the reaction solution, which was washed with water. The solvent was distilled off under reduced pressure, and the obtained residue was purified using column chromatography (elution solvent; hexane: ethyl acetate).
75.0 g of the title compound were obtained. 1 H-NMR (CDCl 3 ) δ; 0.09 (s, 6H), 0.9 (s, 9H), 1.7 (brs, 1H), 2.8 to 3.0
(M, 2H), 3.1 to 3.9 (m, 12H), 4.65 (m, 1H), 5.25 (br
s, 1H) (3) 6-O- (t-butyldimethylsilyl) -2,3,4
-Tri-O-methyl-D-glucono-1,5-lactone 85 ml of oxalic acid chloride was dissolved in 800 ml of methylene chloride, and 138 ml of dimethyl sulfoxide was slowly added dropwise at -70 ° C. Further, 65 g of the alcohol compound was dissolved in 200 ml of methylene chloride and slowly added dropwise. Finally, triethylamine 400m
l was added dropwise and the temperature was raised to room temperature. After completion of the reaction, the mixture was poured into water, extracted with chloroform, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (elution solvent; hexane: ethyl acetate) to give the title compound 61.4.
g was obtained. 1 H-NMR (90 MHz, CDCl 3 ) δ; 0.09 (s, 6H), 0.9 (s, 9H), 3.50, 3.52, 3.56 (each s, ea
ch 3H), 3.5-3.9 (m, 4H), 4.0-4.3 (m, 1H) (4) 6-O- (t-butyldimethylsilyl) -1-
(1′-heptynyl) -2,3,4-tri-O-methyl-D-
Gluco-1-hexulose 32 ml of 1-hexyne was dissolved in 300 ml of tetrahydrofuran, and 86 ml of n-butyllithium (2.5 M / l) was slowly added dropwise at -70 ° C. Next, a solution in which 51.5 g of a ketone body was dissolved in 200 ml of tetrahydrofuran was slowly dropped. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with methylene chloride, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (elution solvent; hexane: ethyl acetate) to obtain 87.3 g of the title compound. 1 H-NMR (90 MHz, CDCl 3 ) δ; 0.09 (s, 6H), 0.9 (s, 9H), 0.8 to 0.9 (m, 3H), 1.1 to 1.7
(M, 4H), 2.0 ~ 2.4 (m, 2H), 3.50,3.60,3.64 (each s, e
ach 3H), 3.0-3.9 (m, 6H) (5) 1-deoxy-1- (1'-heptynyl) -2,3,4
-Tri-O-methyl-D-glucopyranose 56 g of the starting material was treated with acetonitrile-methylene chloride (17:
3) Dissolved in 800 ml, added 81 g of triethylsilyl hydride, and then slowly dropped 30 ml of boron trifluoride etherate at -10 ° C. After completion of the reaction, a saturated aqueous solution of hydrogencarbonate was added to a sodium aqueous solution, and the mixture was extracted with ethyl acetate. The solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (elution solvent; hexane: ethyl acetate) to obtain 33.2 g of the title compound. 1 H-NMR (90 MHz, CDCl 3 ) δ; 0.7 to 1.0 (m, 3H), 1.2 to 1.6 (m, 4H), 2.05 to 2.35 (m, 2
H), 2.9-3.2 (m, 4H), 3.50 (s, 3H), 3.60 (s, 6H), 3.4
To 3.95 (m, 4H) (6) 1-deoxy-1- (1'-heptenyl) -2,3,4
-Tri-O-methyl-D-glucopyranose 28.1 g of the starting material was dissolved in 300 ml of methanol, and 5.0 g of palladium-barium sulfate and 0.9 ml of quinoline were added, followed by hydrogenation. After completion of the reaction, the mixture was filtered through celite, and the filtrate was washed with dilute hydrochloric acid and aqueous sodium hydrogen carbonate solution, and the solvent was distilled off under reduced pressure to obtain 26.0 g of the title compound. 1 H-NMR (90 MHz, CDCl 3 ) δ; 0.7 to 1.1 (m, 3H), 1.1 to 1.6 (m, 4H), 1.8 to 2.3 (m, 2
H), 2.6-3.35 (m, 4H), 3.42,3.50,3.62 (each s, each
3H), 3.3 to 4.05 (m, 4H), 6.1 to 6.8 (m, 2H) (7) 1-deoxy-1- (1'-heptenyl) -2,3,4
-Tri-O-methyl-6-O- (tetrahydrofuran-
2-yl) -D-glucopyranose The starting material (32.0 g) was dissolved in methylene chloride (500 ml), dihydropyran (32 ml), and pyridinium p-toluenesulfonic acid (6.
0 g was added and the mixture was stirred at room temperature. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, and the solvent was distilled off under reduced pressure. The obtained residue was subjected to column chromatography (eluent: hexane:
Purification using ethyl acetate) gave 43.3 g of the title compound. 1 H-NMR (90 MHz, CDCl 3 ) δ; 0.7 to 1.1 (m, 3H), 1.1 to 1.9 (m, 10H), 2.0 to 2.3 (m, 2
H), 2.6 ~ 4.05 (m, 19H), 4.65 (br, 1H), 5.2 ~ 5.8 (m,
2H) (8) 2,6-anhydro-3,4,5-tri-O-methyl-7
-O- (tetrahydrofuran-2-yl) -D-glycero-D-glo-heptitol 43 g of the starting material was dissolved in 600 ml of methanol, subjected to ozonolysis, and reduced with 9.1 g of sodium borohydride.
After completion of the reaction, water and the solvent are distilled off, and the obtained residue is subjected to column chromatography (elution solvent: hexane: ethyl acetate).
The residue was purified using to give 34.5 g of the title compound.
実施例２ １−エチル−２−〔Ｎ−｛2,6−アンヒドロ−７−Ｏ
−（4'−ビフェニルメチル）−3,4,5−トリ−Ｏ−メチ
ル−Ｌ−グリセロ−Ｌ−グロ−ヘプトロキシ｝カルボニ
ル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチルピ
リジニウムヨージド （１）2,6−アンヒドロ−１−Ｏ−（4'−ビフェニルメ
チル）−3,4,5−トリ−Ｏ−メチル−７−Ｏ−（テトラ
ヒドロピラン−２−イル）−Ｄ−グリセロ−Ｄ−グロ−
ヘプチトール 2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ
−（テトラヒドロピラン−２−イル）−Ｄ−グリセロ−
Ｄ−グロ−ヘプチトール1.75gをジメチルホルムアミ
ド、テトラヒドロフラン25mlに溶かし、水素化ナトリウ
ム0.39gを室温にて加え、４−ビフェニルメチルブロマ
イド2.0gを加え、一晩攪拌した。反応終了後、水を加
え、エーテルで抽出し、減圧下溶媒を留去した。得られ
た残渣をカラムクロマトグラフィー（溶出溶媒；ヘキサ
ン：酢酸エチル）を用い精製し、標記化合物2.61gを得
た。1 H-NMR(CDCl3)δ； 1.20〜1.74（m,6H）,2.82〜3.58（m,9H）,3.32（s,3
H）,3.40（s,3H）,3.47（s,3H）,3.62〜3.83（m,2H）,
4.33〜4.60（m,3H）,7.08〜7.43（m,9H） 以下前述の方法に従い、下記の化合物を得た。Example 2 1-ethyl-2- [N- {2,6-anhydro-7-O
-(4'-biphenylmethyl) -3,4,5-tri-O-methyl-L-glycero-L-glo-heptrooxy {carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium iodide (1) 2,6-Anhydro-1-O- (4'-biphenylmethyl) -3,4,5-tri-O-methyl-7-O- (tetrahydropyran-2-yl) -D-glycero- D-glo-
Heptitol 2,6-anhydro-3,4,5-tri-O-methyl-7-O
-(Tetrahydropyran-2-yl) -D-glycero-
1.75 g of D-glo-heptitol was dissolved in 25 ml of dimethylformamide and tetrahydrofuran, 0.39 g of sodium hydride was added at room temperature, 2.0 g of 4-biphenylmethyl bromide was added, and the mixture was stirred overnight. After completion of the reaction, water was added, the mixture was extracted with ether, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (eluent: hexane: ethyl acetate) to give 2.61 g of the title compound. 1 H-NMR (CDCl 3) δ; 1.20~1.74 (m, 6H), 2.82~3.58 (m, 9H), 3.32 (s, 3
H), 3.40 (s, 3H), 3.47 (s, 3H), 3.62 to 3.83 (m, 2H),
4.33 to 4.60 (m, 3H), 7.08 to 7.43 (m, 9H) The following compounds were obtained according to the method described above.
（２）１−エチル−２−〔Ｎ−｛2,6−アンヒドロ−７
−Ｏ−（4'−ビフェニルメチル）−3,4,5−トリ−Ｏ−
メチル−Ｌ−グリセロ−Ｌ−グロ−ヘプトロキシ｝カル
ボニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチ
ルピリジニウムヨージド 1H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,2.70（t,1H,J＝8Hz）,3.02〜3.
40（m,4H）,3.57（s,3H）,3.67（s,3H）,3.80（s,3H）,
4.05（s,3H）,4.20〜4.38（m,1H）,4.48〜4.64（d,1H,J
＝13Hz）,4.68〜4.88（m,2H）,5.12〜5.30（m,2H）,5.4
4〜5.68（m,2H）,7.08（d,1H,J＝8Hz）,7.22（t,1H,J＝
8Hz）,7.44〜7.92（m,11H）,8.18〜8.36（m,2H）,8.60
（t,1H,J＝8Hz）,10.28（d,1H,J＝5Hz） 実施例３ １−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−アン
ヒドロ−７−Ｏ−（3',4',5'−トリメトキシベンジル）
−3,4,5−トリ−Ｏ−メチル−Ｌ−グリセロ−Ｌ−グロ
−ヘプチトロキシ｝カルボニル〕アミノメチルピリジニ
ウムヨージド 1H-NMR(CDCl3)δ； 1.68（t,3H,J＝7.2Hz）,2.62（s,3H）,2.88（t,1H,J＝1
0Hz）,3.07（t,1H,J＝10Hz）,3.28（t,1H,J＝10Hz）,3.
34〜3.75（m,4H）,3.50（s,3H）,3.52（s,3H）,3.64
（s,3H）,3.82（s,3H）,3.85（s,6H）,4.34〜4.60（m,4
H）,5.00（q,2H,J＝7.2Hz）,5.27〜5.40（m,2H）,6.60
（s,2H）,7.69（d,1H,J＝8Hz）,7.94（t,1H,J＝8Hz）,
8.26（t,1H,J＝8Hz）,9.67（d,1H,J＝5Hz） 2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ
−（テトラヒドロピラン−２−イル）−Ｄ−グリセロ−
Ｄ−グロ−ヘプチトールを出発物質として実施例１で示
した反応を利用することにより、次の化合物を得た。(2) 1-ethyl-2- [N- {2,6-anhydro-7
-O- (4'-biphenylmethyl) -3,4,5-tri-O-
Methyl-L-glycero-L-glo-heptroxy {carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium iodide 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 2.70 (t, 1H, J = 8Hz), 3.02~3.
40 (m, 4H), 3.57 (s, 3H), 3.67 (s, 3H), 3.80 (s, 3H),
4.05 (s, 3H), 4.20 to 4.38 (m, 1H), 4.48 to 4.64 (d, 1H, J
= 13Hz), 4.68-4.88 (m, 2H), 5.12-5.30 (m, 2H), 5.4
4 to 5.68 (m, 2H), 7.08 (d, 1H, J = 8 Hz), 7.22 (t, 1H, J =
8Hz), 7.44 to 7.92 (m, 11H), 8.18 to 8.36 (m, 2H), 8.60
(T, 1H, J = 8 Hz), 10.28 (d, 1H, J = 5 Hz) Example 3 1-ethyl-2- [N-acetyl-N-Ｎ2,6-anhydro-7-O- (3 ′ , 4 ', 5'-trimethoxybenzyl)
-3,4,5-Tri-O-methyl-L-glycero-L-glo-heptitrooxydicarbonyl] aminomethylpyridinium iodide 1 H-NMR (CDCl 3) δ; 1.68 (t, 3H, J = 7.2Hz), 2.62 (s, 3H), 2.88 (t, 1H, J = 1
0 Hz), 3.07 (t, 1H, J = 10 Hz), 3.28 (t, 1H, J = 10 Hz), 3.
34 to 3.75 (m, 4H), 3.50 (s, 3H), 3.52 (s, 3H), 3.64
(S, 3H), 3.82 (s, 3H), 3.85 (s, 6H), 4.34 to 4.60 (m, 4
H), 5.00 (q, 2H, J = 7.2 Hz), 5.27 to 5.40 (m, 2H), 6.60
(S, 2H), 7.69 (d, 1H, J = 8 Hz), 7.94 (t, 1H, J = 8 Hz),
8.26 (t, 1H, J = 8 Hz), 9.67 (d, 1H, J = 5 Hz) 2,6-anhydro-3,4,5-tri-O-methyl-7-O
-(Tetrahydropyran-2-yl) -D-glycero-
The following compound was obtained by utilizing the reaction shown in Example 1 using D-glo-heptitol as a starting material.
実施例４ １−エチル−２−〔Ｎ−（2,6−アンヒドロ−７−Ｏ
−デシルカルバモイル−3,4,5−トリ−Ｏ−メチル−Ｄ
−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボニル−
Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチルピリジ
ニウムクロリド 1H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.04〜1.08（m,16H）,1.75（t,
3H,J＝7.2Hz）,2.36〜3.40（m,7H）,3.36（s,3H）,3.48
（s,3H）,3.56（s,3H）,3.84（s,3H）,3.76〜4.38（m,4
H）,4.96〜5.80（m,5H）,6.80〜7.12（m,2H）,7.28〜7.
56（m,2H）,7.80〜8.12（m,2H）,8.16〜8.46（m,1H）,1
0.25〜10.40（m,1H） 実施例５ １−エチル−２−〔Ｎ−（2,6−アンヒドロ−3,4,5−
トリ−Ｏ−メチル−７−Ｏ−ウンデシルカルバモイル−
Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボニル
−Ｎ−（Ｏ−メトキシベンゾイル〕アミノメチルピリジ
ニウムクロリド 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.02〜1.90（m,18H）,1.74（t,
3H,J＝7.2Hz）,2.30〜3.44（m,7H）,3.34（s,3H）,3.46
（s,3H）,3.58（s,3H）,3.84（s,3H）,3.92〜4.40（m,4
H）,4.90〜5.84（m,5H）,6.78〜7.08（m,2H）,7.30〜7.
58（m,2H）,7.80〜8.08（m,2H）,8.15〜8.42（m,1H）,1
0.28〜10.38（m,1H） 実施例６ １−エチル−２−〔Ｎ−（2,6−アンヒドロ−７−Ｏ
−ドデシルカルバモイル−3,4,5−トリ−Ｏ−メチル−
Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボニル
−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチルピリ
ジニウムクロリド 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.02〜1.94（m,20H）,1.76（t,
3H,J＝7.2Hz）,2.34〜3.42（m,7H）,3.36（s,3H）,3.46
（s,3H）,3.56（s,3H）,3.82（s,3H）,3.70〜4.40（m,4
H）,4.76〜5.82（m,5H）,6.78〜7.12（m,2H）,7.30〜7.
55（m,2H）,7.78〜8.10（m,2H）,8.16〜8.44（m,1H）,1
0.24〜10.40（m,1H） 実施例７ １−エチル−２−〔Ｎ−（2,6−アンヒドロ−3,4,5−
トリ−Ｏ−メチル−７−Ｏ−トリデシルカルバモイル−
Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボニル
−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチルピリ
ジニウムクロリド 1H-NMR(CDCl3)δ； 0.87（t,3H,J＝7.2Hz）,1.04〜1.98（m,22H）,1.80（t,
3H,J＝7.2Hz）,2.33〜3.42（m,7H）,3.35（s,3H）,3.48
（s,3H）,3.58（s,3H）,3.84（s,3H）,3.94〜4.38（m,4
H）,4.97〜5.82（m,5H）,6.78〜7.14（m,2H）,7.24〜7.
54（m,2H）,7.82〜8.14（m,2H）,8.16〜8.48（m,1H）,1
0.23〜10.42（m,1H） 実施例８ １−エチル−２−〔Ｎ−（2,6−アンヒドロ−3,4,5−
トリ−Ｏ−メチル−７−Ｏ−テトラデシルカルバモイル
−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボニ
ル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチルピ
リジニウムクロリド （１）2,6−アンヒドロ−１−Ｏ−〔Ｎ−（Ｏ−メトキ
シベンゾイル）−Ｎ−（ピリジン−２−イル）メチル〕
カルバモイル−3,4,5−トリ−Ｏ−メチル−７−Ｏ−テ
トラデシルカルバモイル−Ｄ−グリセロ−Ｄ−グロ−ヘ
プチトール 1H-NMR(CDCl3)δ； 0.92（t,3H,J＝7.2Hz）,1.10〜1.80（m,24H）,2.40〜3.
60（m,7H）,3.35（s,3H）,3.50（s,3H）,3.58（s,3H）,
3.88（s,3H）,4.00〜4.36（m,4H）,5.15〜5.35（m,2
H）,5.70〜6.15（br,1H）,6.80〜7.80（m,7H）,8.40〜
8.60（m,1H） （２）１−エチル−２−〔Ｎ−（2,6−アンヒドロ−3,
4,5−トリ−Ｏ−メチル−７−Ｏ−テトラデシルカルバ
モイル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カ
ルボニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメ
チルピリジニウムクロリド 1H-NMR(CDCl3)δ； 0.90（t,3H,J＝7.2Hz）,1.10〜1.70（m,24H）,1.80（t,
3H,J＝7.2Hz）,2.40〜3.40（m,8H）,3.40（s,3H）,3.52
（s,3H）,3.60（s,3H）,3.90（s,3H）,4.00〜4.40（m,4
H）,5.25（q,2H,J＝7.2Hz）,5.50（d,2H,J＝4Hz）,6.92
（d,1H,J＝9Hz）,7.05（d,1H,J＝7.0Hz）,7.30〜7.60
（m,2H）,7.90〜8.20（m,2H）,8.40（t,1H,J＝7.2Hz）,
10.2（d,1H,J＝5Hz） MS;m/z772(M+-Cl) 実施例９ １−エチル−２−〔Ｎ−（2,6−アンヒドロ−3,4,5−
トリ−Ｏ−メチル−７−Ｏ−ペンタデシルカルバモイル
−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボニ
ル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチルピ
リジニウムクロリド 1H-NMR(CDCl3)δ； 0.85（t,3H,J＝7.2Hz）,1.00〜2.08（m,26H）,1.74（t,
3H,J＝7.2Hz）,2.32〜3.40（m,7H）,3.34（s,3H）,3.47
（s,3H）,3.54（s,3H）,3.84（s,3H）,3.70〜4.38（m,4
H）,4.92〜5.60（m,5H）,6.76〜7.10（m,2H）,7.14〜7.
56（m,2H）,7.80〜8.10（m,2H）,8.16〜8.46（m,1H）,1
0.25〜10.38（m,1H） 実施例10 １−エチル−２−〔Ｎ−（2,6−アンヒドロ−７−Ｏ
−ヘキサデシルカルバモイル−3,4,5−トリ−Ｏ−メチ
ル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボ
ニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチル
ピリジニウムクロリド （２）2,6−アンヒドロ−７−Ｏ−ヘキサデシルカルバ
モイル１−Ｏ−〔Ｎ−（Ｏ−メトキシベンゾイル）−Ｎ
−（ピリジン−２−イル）メチルカルバモイル−3,4,5
−トリ−Ｏ−メチル−Ｄ−グリセロ−Ｄ−グロ−ヘプチ
トール 1H-NMR(CDCl3)δ； 0.92（t,3H,J＝7.2Hz）,1.05〜1.80（m,28H）,2.40〜3.
40（m,7H）,3.36（s,3H）,3.50（s,3H）,3.58（s,3H）,
3.88（s,3H）,4.00〜4.38（m,4H）,5.15〜5.30（m,2
H）,5.90〜6.15（br,1H）,6.80〜7.75（m,7H）,8.40〜
8.55（m,1H） （２）１−エチル−２−〔Ｎ−（2,6−アンヒドロ−７
−Ｏ−ヘキサデシルカルバモイル−3,4,5−トリ−Ｏ−
メチル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カ
ルボニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメ
チルピリジニウムクロリド 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,0.90〜1.80（m,28H）,1.78（t,
3H,J＝7.2Hz）,2.30〜3.40（m,8H）,3.38（s,3H）,3.50
（s,3H）,3.58（s,3H）,3.88（s,3H）,3.90〜4.40（m,4
H）,5.20（q,2H,J＝7.2Hz）,5.45（d,2H,J＝4Hz）,6.90
（d,1H,J＝9Hz）,7.05（d,1H,J＝7.2Hz）,7.25〜7.60
（m,2H）,7.88〜8.10（m,2H）,8.38（t,1H,J＝7.2Hz）,
10.2（d,1H,J＝5Hz） MS;m/z800(M+-Cl) 実施例11 １−エチル−２−〔Ｎ−（2,6−アンヒドロ−７−Ｏ
−ヘプタデシルカルバモイル−3,4,5−トリ−Ｏ−メチ
ル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボ
ニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチル
ピリジニウムクロリド （１）2,6−アンヒドロ−７−Ｏ−ヘキサデシルカルバ
モイル１−Ｏ−〔Ｎ−（ｐ−メトキシベンゾイル）−Ｎ
−（ピリジン−２−イル）メチル〕カルバモイル−3,4,
5−トリ−Ｏ−メチル−Ｄ−グリセロ−Ｄ−グロ−ヘプ
チトール 1H-NMR(CDCl3)δ； 0.90（t,3H,J＝7.2Hz）,1.00〜1.70（m,30H）,2.40〜3.
40（m,7H）,3.35（s,3H）,3.48（s,3H）,3.56（s,3H）,
3.84（s,3H）,4.00〜4.30（m,4H）,5.10〜5.30（m,2
H）,5.90〜6.10（br,1H）,6.78〜7.74（m,7H）,8.40〜
8.56（m,1H） （２）１−エチル−２−〔Ｎ−（2,6−アンヒドロ−７
−Ｏ−ヘプタデシルカルバモイル−3,4,5−トリ−Ｏ−
メチル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カ
ルボニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメ
チルピリジニウムクロリド 1H-NMR(CDCl3)δ； 0.92（t,3H,J＝7.2Hz）,1.00〜1.70（m,30H）,1.80（t,
3H,J＝7.2Hz）,2.30〜3.40（m,8H）,3.40（s,3H）,3.52
（s,3H）,3.60（s,3H）,3.90（s,3H）,3.98〜4.40（m,4
H）,5.25（q,2H,J＝7.2Hz）,5.50（d,2H,J＝4Hz）,6.90
（d,1H,J＝9Hz）,7.05（d,1H,J＝7.2Hz）,7.30〜7.60
（m,2H）,7.90〜8.10（m,2H）,8.40（t,1H,J＝7.2Hz）,
10.2（d,1H,J＝5Hz） MS;m/z814(M+-Cl) 実施例12 １−エチル−２−〔Ｎ−（2,6−アンヒドロ−3,4,5−
トリ−Ｏ−メチル−７−Ｏ−オクタデシルカルバモイル
−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カルボニ
ル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメチルピ
リジニウムクロリド （１）2,6−アンヒドロ−１−Ｏ−〔Ｎ−（Ｏ−メトキ
シベンゾイル）−Ｎ−（ピリジン−２−イル）メチル〕
カルバモイル−3,4,5−トリ−Ｏ−メチル−７−Ｏ−オ
クタデシルカルバモイル−Ｄ−グリセロ−Ｄ−グロ−ヘ
プチトール 1H-NMR(CDCl3)δ； 0.92（t,3H,J＝7.2Hz）,1.05〜2.70（m,32H）,2.40〜3.
40（m,7H）,3.36（s,3H）,3.58（s,3H）,3.85（s,3H）,
4.00〜4.40（m,4H）,5.10〜5.30（m,2H）,6.80〜7.75
（m,7H）,8.40〜8.55（m,1H） （２）１−エチル−２−〔Ｎ−（2,6−アンヒドロ−3,
4,5−トリ−Ｏ−メチル−７−Ｏ−オクタデシルカルバ
モイル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ）カ
ルボニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノメ
チルピリジニウムクロリド 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.00〜1.70（m,32H）,1.78（t,
3H,J＝7.2Hz）,2.40〜3.40（m,8H）,3.36（s,3H）,3.50
（s,3H）,3.56（s,3H）,3.88（s,3H）,3.95〜4.38（m,4
H）,5.20（q,2H,J＝7.2Hz）,5.48（d,2H,J＝4Hz）,6.90
（d,1H,J＝7Hz）,7.05（d,1H,J＝7.2Hz）,7.30〜7.56
（m,2H）,7.90〜8.20（m,2H）,8.40（t,1H,J＝8Hz）,1
0.2（d,1H,J＝5Hz） MS;m/z828(M+-Cl) 実施例13 １−エチル−２−〔Ｎ−｛2,6−アンヒドロ−3,4,5−
トリ−Ｏ−メチル−７−Ｏ−（４−テトラデシルカルバ
モイルオキシ）ピペリジノカルボニル−Ｄ−グリセロ−
Ｄ−グロ−ヘプチトロキシ｝−Ｎ−（Ｏ−メトキシベン
ゾイル）〕アミノメチルピリジニウムクロリド （１）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−（ピリジン−２−イル）メチルカルバモイル−７
−Ｏ−テトラヒドロピラン−２−イル−Ｄ−グリセロ−
Ｄ−グロ−ヘプチトール 1H-NMR(CDCl3)δ； 1.30〜1.90（m,6H）,2.90〜4.10（m,9H）,3.52（s,3
H）,3.58（s,3H）,3.66（s,3H）,4.18〜4.40（m,2H）,
4.48（d,2H,J＝5.4Hz）,4.50〜4.70（m,1H）,5.70〜6.0
0（br,1H）,7.05〜7.30（m,2H）,7.62（t,1H,J＝7.5H
z）,8.48（d,1H,J＝5Hz） （２）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−（ピリジン−２−イル）メチルカルバモイル−Ｄ
−グリセロ−Ｄ−グロ−ヘプチトール 1H-NMR(CDCl3)δ； 2.80〜4.00（m,8H）,3.52（s,3H）,3.58（s,3H）,3.66
（s,3H）,4.15〜4.35（m,2H）,4.46（d,2H,J＝5.4Hz）,
6.10〜6.40（br,1H）,7.00〜7.30（m,2H）,7.60（t,1H,
J＝8Hz）,8.46（d,1H,J＝5Hz） （３）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７
−Ｏ−フェノキシカルボニル−１−Ｏ−（ピリジン−２
−イル）メチルカルバモイル−Ｄ−グリセロ−Ｄ−グロ
−ヘプチトール 1H-NMR(CDCl3)δ； 3.00〜3.80（m,5H）,3.56（s,3H）,3.62（s,3H）,3.70
（s,3H）,4.28〜4.64（m,6H）,5.80〜6.08（br,1H）,7.
10〜7.58（m,7H）,7.70（t,1H,J＝8Hz）,8.58（d,1H,J
＝5Hz） （４）2,6−アンヒドロ−７−Ｏ−〔（4'−ヒドロキ
シ）ピペリジノカルボニル〕−3,4,5−トリ−Ｏ−メチ
ル−１−Ｏ−（ピリジン−２−イル）メチルカルバモイ
ル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトール 1H-NMR(CDCl3)δ； 1.20〜2.10（m,4H）,2.60〜4.60（m,15H）,3.50（s,3
H）,3.54（s,3H）,3.66（s,3H）,4.40（d,2H,J＝7.2H
z）,6.10〜6.60（dr,1H）,7.00〜7.30（m,2H）,7.62
（t,1H,J＝8Hz）,8.42（b,1H,J＝5Hz） （５）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−（ピリジン−２−イル）メチルカルバモイル−７
−Ｏ−（4'−テトラデシルカルバモイルオキシ）ピペリ
ジノカルボニル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトー
ル 1H-NMR(CDCl3)δ； 0.90（t,3H,J＝7.2Hz）,1.10〜2.00（m,28H）,2.80〜4.
00（m,11H）,3.50（s,3H）,3.52（s,3H）,3.66（s,3
H）,4.05〜4.45（m,4H）,4.45（d,2H,J＝5.4Hz）,4.60
〜5.30（m,2H）,5.76〜6.00（m,1H）,7.05〜7.32（m,2
H）,7.62（t,1H,J＝7.2Hz）,8.40〜8.56（m,1H） （６）2,6−アンヒドロ−１−Ｏ−〔Ｎ−（Ｏ−メトキ
シベンゾイル）−Ｎ−（ピリジン−２−イル）メチル〕
カルバモイル−3,4,5−トリ−Ｏ−メチル−７−Ｏ−
（4'−テトラデシルカルバモイルオキシ）ピペリジノカ
ルボニル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトール 1H-NMR(CDCl3)δ； 0.90（t,3H,J＝7.2Hz）,1.06〜2.05（m,28H）,2.50〜4.
00（m,11H）,3.32（s,3H）,3.50（s,3H）,3.60（s,3
H）,3.82（s,3H）,4.00〜4.38（m,4H）,4.60〜5.00（m,
2H）,5.10〜5.28（m,2H）,6.76〜7.70（m,7H）,8.44〜
8.54（m,1H） （７）１−エチル−２−〔Ｎ−｛2,6−アンヒドロ−3,
4,5−トリ−Ｏ−メチル−７−Ｏ−（４−テトラデシル
カルバモイルオキシ）ピペリジノカルボニル−Ｄ−グリ
セロ−Ｄ−グロ−ヘプチトロキシ｝−Ｎ−（Ｏ−メトキ
シベンゾイル）〕アミノメチルピリジニウムクロリド 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.00〜2.00（m,28H）,1.78（t,
3H,J＝7.2Hz）,2.20〜3.60（m,11H）,3.40（s,3H）,3.5
0（s,3H）,3.58（s,3H）,3.86（s,3H）,3.90〜4.20（m,
4H）,4.60〜5.00（m,2H）,5.20（q,2H,J＝7.2Hz）,5.45
（d,2H,J＝2Hz）,6.90（d,1H,J＝9Hz）,7.04（d,1H,J＝
7.2Hz）,7.30〜7.50（m,2H）,7.86〜8.10（m,2H）,8.40
（t,1H,J＝7.2Hz）,10.2（d,1H,J＝5Hz） MS;m/z899(M+-Cl) 実施例14 １−エチル−２−〔Ｎ−｛2,6−アンヒドロ−７−Ｏ
−（4'−ヘキサデシルカルバモイルオキシ）ピペリジノ
カルボニル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロキシ
カルボニル−Ｎ−（Ｏ−メトキシベンゾイル）〕アミノ
メチルピリジニウムクロリド （１）2,6−アンヒドロ−７−Ｏ−（4'−ヘキサデシル
カルバモイルオキシ）ピペリジノカルボニル−3,4,5−
トリ−Ｏ−メチル−１−Ｏ−（ピリジン−２−イル）メ
チルカルバモイル−Ｄ−グリセロ−Ｄ−グロ−ヘプチト
ール 1H-NMR(CDCl3)δ； 0.90（t,3H,J＝7.2Hz）,1.00〜2.05（m,32H）,2.80〜4.
00（m,11H）,3.50（s,3H）,3.52（s,3H）,3.65（s,3
H）,4.00〜4.50（m,4H）,4.45（d,2H,J＝5.4Hz）,4.60
〜5.30（m,2H）,5.70〜6.00（m,1H）,7.00〜7.40（m,2
H）,7.60（t,1H,J＝7.2Hz）,8.36〜8.54（m,1H） （２）2,6−アンヒドロ−７−Ｏ−（4'−ヘキサデシル
カルバモイルオキシ）ピペリジノカルボニル−１−Ｏ−
〔Ｎ−（Ｏ−メトキシベンゾイル）−Ｎ−（ピリジン−
２−イル）メチル〕カルバモイル−3,4,5−トリ−Ｏ−
メチル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトール 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,0.90〜2.00（m,32H）,2.50〜3.
90（m,11H）,3.30（s,3H）,3.50（s,3H）,3.58（s,3
H）,3.80（s,3H）,4.40〜4.34（m,4H）,4.60〜5.00（m,
2H）,5.10〜5.28（m,2H）,6.70〜7.70（m,7H）,8.40〜
8.52（m,1H） （３）１−エチル−２−〔Ｎ−｛2,6−アンヒドロ−７
−Ｏ−（4'−ヘキサデシルカルバモイルオキシ）ピペリ
ジノカルボニル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトロ
キシカルボニル−Ｎ−（Ｏ−メトキシベンゾイル）〕ア
ミノメチルピリジニウムクロリド 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.05〜2.00（m,32H）,1.78（t,
3H,J＝7.2Hz）,2.40〜3.60（m,11H）,3.40（s,3H）,3.5
0（s,3H）,3.58（s,3H）,3.88（s,3H）,3.90〜4.35（m,
4H）,4.60〜5.00（m,2H）,5.20（q,2H,J＝7.2Hz）,5.45
（d,2H,J＝3Hz）,6.88（d,1H,J＝9Hz）,7.06（d,1H,J＝
7.2Hz）,7.28〜7.60（m,2H）,7.90〜8.14（m,2H）,8.38
（t,1H,J＝7.2Hz）,10.2（d,1H,J＝5Hz） MS;m/z927(M+-Cl) 実施例15 １−エチル−２−〔Ｎ−｛2,6−アンヒドロ−3,4,5−ト
リ−Ｏ−メチル−７−Ｏ−（4'−オクタデシルカルバモ
イルオキシ）ピペリジノカルボニル−Ｄ−グリセロ−Ｄ
−グロ−ヘプチトロキシ｝−Ｎ−（Ｏ−メトキシベンゾ
イル）〕アミノメチルピリジニウムクロリド （１）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７
−Ｏ−（4'−オクタデシルカルバモイルオキシ）ピペリ
ジノカルボニル−１−Ｏ−（ピリジン−２−イル）メチ
ルカルバモイル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトー
ル 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.05〜2.06（m,36H）,2.80〜4.
00（m,11H）,3.50（s,3H）,3.52（s,3H）,3.64（s,3
H）,4.00〜4.40（m,4H）,4.45（d,2H,J＝5.4Hz）,4.60
〜5.25（m,2H）,5.90〜6.00（m,1H）,7.05〜7.30（m,2
H）,7.60（t,1H,J＝7.2Hz）,8.40〜8.56（m,1H） （２）2,6−アンヒドロ−１−Ｏ−〔Ｎ−（Ｏ−メトキ
シベンゾイル）−Ｎ−（ピリジン−２−イル）メチル〕
カルバモイル−3,4,5−トリ−Ｏ−メチル−７−Ｏ−
（4'−オクタデシルカルバモイルオキシ）ピペリジノカ
ルボニル−Ｄ−グリセロ−Ｄ−グロ−ヘプチトール 1H-NMR(CDCl3)δ； 0.90（t,3H,J＝7.2Hz）,1.00〜2.10（m,36H）,2.50〜4.
00（m,11H）,3.32（s,3H）,3.50（s,3H）,3.60（s,3
H）,3.82（s,3H）,4.00〜4.37（m,4H）,4.60〜5.00（m,
2H）,5.10〜5.30（m,2H）,6.75〜7.70（m,7H）,8.40〜
8.54（m,1H） （３）１−エチル−２−〔Ｎ−｛2,6−アンヒドロ−3,
4,5−トリ−Ｏ−メチル−７−Ｏ−（4'−オクタデシル
カルバモイルオキシ）ピペリジノカルボニル−Ｄ−グリ
セロ−Ｄ−グロ−ヘプチトロキシ｝−Ｎ−（Ｏ−メトキ
シベンゾイル）〕アミノメチルピリジニウムクロリド 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.20〜2.00（m,36H）,1.80（t,
3H,J＝7.2Hz）,2.40〜3.40（m,11H）,3.40（s,3H）,3.4
8（s,3H）,3.60（s,3H）,3.88（s,3H）,3.90〜4.40（m,
4H）,4.60〜5.00（m,2H）,5.25（q,2H,J＝7.2Hz）,5.45
（d,2H,J＝3Hz）,6.90（d,1H,J＝9Hz）,7.05（d,1H,J＝
7.2Hz）,7.30〜7.60（m,2H）,7.90〜8.20（m,2H）,8.36
（t,1H,J＝7.2Hz）,10.2（d,1H,J＝5Hz） MS;m/z955(M+-Cl) 実施例１（２）で得た１−デオキシ−１−（1'−ヒド
ロキシエチル）−2,3,4−トリ−Ｏ−メチル−６−Ｏ−
（テトラヒドロピラン−２−イル）−β−Ｄ−グルコピ
ラノースを用い、側鎖の伸長を行うことにより、以下の
化合物を得た。Example 4 1-ethyl-2- [N- (2,6-anhydro-7-O
-Decylcarbamoyl-3,4,5-tri-O-methyl-D
-Glycero-D-glo-heptitroxy) carbonyl-
N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.04~1.08 (m, 16H), 1.75 (t,
3H, J = 7.2Hz), 2.36 to 3.40 (m, 7H), 3.36 (s, 3H), 3.48
(S, 3H), 3.56 (s, 3H), 3.84 (s, 3H), 3.76 to 4.38 (m, 4
H), 4.96-5.80 (m, 5H), 6.80-7.12 (m, 2H), 7.28-7.
56 (m, 2H), 7.80 ~ 8.12 (m, 2H), 8.16 ~ 8.46 (m, 1H), 1
0.25 to 10.40 (m, 1H) Example 5 1-ethyl-2- [N- (2,6-anhydro-3,4,5-
Tri-O-methyl-7-O-undecylcarbamoyl-
D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl) aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.02~1.90 (m, 18H), 1.74 (t,
3H, J = 7.2Hz), 2.30 to 3.44 (m, 7H), 3.34 (s, 3H), 3.46
(S, 3H), 3.58 (s, 3H), 3.84 (s, 3H), 3.92 to 4.40 (m, 4
H), 4.90-5.84 (m, 5H), 6.78-7.08 (m, 2H), 7.30-7.
58 (m, 2H), 7.80 ~ 8.08 (m, 2H), 8.15 ~ 8.42 (m, 1H), 1
0.28-10.38 (m, 1H) Example 6 1-ethyl-2- [N- (2,6-anhydro-7-O
-Dodecylcarbamoyl-3,4,5-tri-O-methyl-
D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.02~1.94 (m, 20H), 1.76 (t,
3H, J = 7.2Hz), 2.34-3.42 (m, 7H), 3.36 (s, 3H), 3.46
(S, 3H), 3.56 (s, 3H), 3.82 (s, 3H), 3.70 ~ 4.40 (m, 4
H), 4.76-5.82 (m, 5H), 6.78-7.12 (m, 2H), 7.30-7.
55 (m, 2H), 7.78 ~ 8.10 (m, 2H), 8.16 ~ 8.44 (m, 1H), 1
0.24 to 10.40 (m, 1H) Example 7 1-ethyl-2- [N- (2,6-anhydro-3,4,5-
Tri-O-methyl-7-O-tridecylcarbamoyl-
D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.87 (t, 3H, J = 7.2Hz), 1.04~1.98 (m, 22H), 1.80 (t,
3H, J = 7.2Hz), 2.33-3.42 (m, 7H), 3.35 (s, 3H), 3.48
(S, 3H), 3.58 (s, 3H), 3.84 (s, 3H), 3.94 to 4.38 (m, 4
H), 4.97-5.82 (m, 5H), 6.78-7.14 (m, 2H), 7.24-7.
54 (m, 2H), 7.82 ~ 8.14 (m, 2H), 8.16 ~ 8.48 (m, 1H), 1
0.23 to 10.42 (m, 1H) Example 8 1-ethyl-2- [N- (2,6-anhydro-3,4,5-
Tri-O-methyl-7-O-tetradecylcarbamoyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride (1) 2,6-Anhydro-1-O- [N- (O-methoxybenzoyl) -N- (pyridin-2-yl) methyl]
Carbamoyl-3,4,5-tri-O-methyl-7-O-tetradecylcarbamoyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.92 (t, 3H, J = 7.2 Hz), 1.10 to 1.80 (m, 24H), 2.40 to 3.
60 (m, 7H), 3.35 (s, 3H), 3.50 (s, 3H), 3.58 (s, 3H),
3.88 (s, 3H), 4.00 to 4.36 (m, 4H), 5.15 to 5.35 (m, 2
H), 5.70-6.15 (br, 1H), 6.80-7.80 (m, 7H), 8.40-
8.60 (m, 1H) (2) 1-ethyl-2- [N- (2,6-anhydro-3,
4,5-tri-O-methyl-7-O-tetradecylcarbamoyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3 ) δ; 0.90 (t, 3H, J = 7.2 Hz), 1.10 to 1.70 (m, 24H), 1.80 (t,
3H, J = 7.2Hz), 2.40 to 3.40 (m, 8H), 3.40 (s, 3H), 3.52
(S, 3H), 3.60 (s, 3H), 3.90 (s, 3H), 4.00 to 4.40 (m, 4
H), 5.25 (q, 2H, J = 7.2 Hz), 5.50 (d, 2H, J = 4 Hz), 6.92
(D, 1H, J = 9Hz), 7.05 (d, 1H, J = 7.0Hz), 7.30 ~ 7.60
(M, 2H), 7.90 ~ 8.20 (m, 2H), 8.40 (t, 1H, J = 7.2Hz),
10.2 (d, 1H, J = 5 Hz) MS; m / z 772 (M + -Cl) Example 9 1-ethyl-2- [N- (2,6-anhydro-3,4,5-
Tri-O-methyl-7-O-pentadecylcarbamoyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.85 (t, 3H, J = 7.2Hz), 1.00~2.08 (m, 26H), 1.74 (t,
3H, J = 7.2Hz), 2.32 ~ 3.40 (m, 7H), 3.34 (s, 3H), 3.47
(S, 3H), 3.54 (s, 3H), 3.84 (s, 3H), 3.70-4.38 (m, 4
H), 4.92 to 5.60 (m, 5H), 6.76 to 7.10 (m, 2H), 7.14 to 7.
56 (m, 2H), 7.80 to 8.10 (m, 2H), 8.16 to 8.46 (m, 1H), 1
0.25 to 10.38 (m, 1H) Example 10 1-ethyl-2- [N- (2,6-anhydro-7-O
-Hexadecylcarbamoyl-3,4,5-tri-O-methyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride (2) 2,6-anhydro-7-O-hexadecylcarbamoyl 1-O- [N- (O-methoxybenzoyl) -N
-(Pyridin-2-yl) methylcarbamoyl-3,4,5
-Tri-O-methyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.92 (t, 3H, J = 7.2 Hz), 1.05 to 1.80 (m, 28H), 2.40 to 3.
40 (m, 7H), 3.36 (s, 3H), 3.50 (s, 3H), 3.58 (s, 3H),
3.88 (s, 3H), 4.00 to 4.38 (m, 4H), 5.15 to 5.30 (m, 2
H), 5.90-6.15 (br, 1H), 6.80-7.75 (m, 7H), 8.40-
8.55 (m, 1H) (2) 1-ethyl-2- [N- (2,6-anhydro-7
-O-hexadecylcarbamoyl-3,4,5-tri-O-
Methyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 0.90~1.80 (m, 28H), 1.78 (t,
3H, J = 7.2Hz), 2.30-3.40 (m, 8H), 3.38 (s, 3H), 3.50
(S, 3H), 3.58 (s, 3H), 3.88 (s, 3H), 3.90 ~ 4.40 (m, 4
H), 5.20 (q, 2H, J = 7.2 Hz), 5.45 (d, 2H, J = 4 Hz), 6.90
(D, 1H, J = 9 Hz), 7.05 (d, 1H, J = 7.2 Hz), 7.25 to 7.60
(M, 2H), 7.88 ~ 8.10 (m, 2H), 8.38 (t, 1H, J = 7.2Hz),
10.2 (d, 1H, J = 5 Hz) MS; m / z 800 (M + -Cl) Example 11 1-ethyl-2- [N- (2,6-anhydro-7-O
-Heptadecylcarbamoyl-3,4,5-tri-O-methyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride (1) 2,6-Anhydro-7-O-hexadecylcarbamoyl 1-O- [N- (p-methoxybenzoyl) -N
-(Pyridin-2-yl) methyl] carbamoyl-3,4,
5-tri-O-methyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.90 (t, 3H, J = 7.2 Hz), 1.00 to 1.70 (m, 30H), 2.40 to 3.
40 (m, 7H), 3.35 (s, 3H), 3.48 (s, 3H), 3.56 (s, 3H),
3.84 (s, 3H), 4.00 to 4.30 (m, 4H), 5.10 to 5.30 (m, 2
H), 5.90-6.10 (br, 1H), 6.78-7.74 (m, 7H), 8.40-
8.56 (m, 1H) (2) 1-ethyl-2- [N- (2,6-anhydro-7
-O-heptadecylcarbamoyl-3,4,5-tri-O-
Methyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.92 (t, 3H, J = 7.2Hz), 1.00~1.70 (m, 30H), 1.80 (t,
3H, J = 7.2Hz), 2.30-3.40 (m, 8H), 3.40 (s, 3H), 3.52
(S, 3H), 3.60 (s, 3H), 3.90 (s, 3H), 3.98 to 4.40 (m, 4
H), 5.25 (q, 2H, J = 7.2 Hz), 5.50 (d, 2H, J = 4 Hz), 6.90
(D, 1H, J = 9 Hz), 7.05 (d, 1H, J = 7.2 Hz), 7.30 to 7.60
(M, 2H), 7.90 ~ 8.10 (m, 2H), 8.40 (t, 1H, J = 7.2Hz),
10.2 (d, 1H, J = 5 Hz) MS; m / z 814 (M + -Cl) Example 12 1-ethyl-2- [N- (2,6-anhydro-3,4,5-
Tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride (1) 2,6-Anhydro-1-O- [N- (O-methoxybenzoyl) -N- (pyridin-2-yl) methyl]
Carbamoyl-3,4,5-tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.92 (t, 3H, J = 7.2 Hz), 1.05 to 2.70 (m, 32H), 2.40 to 3.
40 (m, 7H), 3.36 (s, 3H), 3.58 (s, 3H), 3.85 (s, 3H),
4.00 to 4.40 (m, 4H), 5.10 to 5.30 (m, 2H), 6.80 to 7.75
(M, 7H), 8.40 to 8.55 (m, 1H) (2) 1-ethyl-2- [N- (2,6-anhydro-3,
4,5-tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-D-glo-heptitroxy) carbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.00~1.70 (m, 32H), 1.78 (t,
3H, J = 7.2Hz), 2.40 to 3.40 (m, 8H), 3.36 (s, 3H), 3.50
(S, 3H), 3.56 (s, 3H), 3.88 (s, 3H), 3.95 to 4.38 (m, 4
H), 5.20 (q, 2H, J = 7.2 Hz), 5.48 (d, 2H, J = 4 Hz), 6.90
(D, 1H, J = 7Hz), 7.05 (d, 1H, J = 7.2Hz), 7.30 ~ 7.56
(M, 2H), 7.90-8.20 (m, 2H), 8.40 (t, 1H, J = 8Hz), 1
0.2 (d, 1H, J = 5 Hz) MS; m / z 828 (M + -Cl) Example 13 1-ethyl-2- [N- ｛2,6-anhydro-3,4,5-
Tri-O-methyl-7-O- (4-tetradecylcarbamoyloxy) piperidinocarbonyl-D-glycero-
D-glo-heptitroxy} -N- (O-methoxybenzoyl)] aminomethylpyridinium chloride (1) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O- (pyridin-2-yl) methylcarbamoyl-7
-O-tetrahydropyran-2-yl-D-glycero-
D-glo-heptitol 1 H-NMR (CDCl 3) δ; 1.30~1.90 (m, 6H), 2.90~4.10 (m, 9H), 3.52 (s, 3
H), 3.58 (s, 3H), 3.66 (s, 3H), 4.18-4.40 (m, 2H),
4.48 (d, 2H, J = 5.4Hz), 4.50-4.70 (m, 1H), 5.70-6.0
0 (br, 1H), 7.05 to 7.30 (m, 2H), 7.62 (t, 1H, J = 7.5H
z), 8.48 (d, 1H, J = 5 Hz) (2) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O- (pyridin-2-yl) methylcarbamoyl-D
-Glycero-D-glo-heptitol 1 H-NMR (CDCl 3) δ; 2.80~4.00 (m, 8H), 3.52 (s, 3H), 3.58 (s, 3H), 3.66
(S, 3H), 4.15-4.35 (m, 2H), 4.46 (d, 2H, J = 5.4Hz),
6.10 to 6.40 (br, 1H), 7.00 to 7.30 (m, 2H), 7.60 (t, 1H,
J = 8Hz), 8.46 (d, 1H, J = 5Hz) (3) 2,6-anhydro-3,4,5-tri-O-methyl-7
-O-phenoxycarbonyl-1-O- (pyridine-2
-Yl) methylcarbamoyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 3.00 to 3.80 (m, 5H), 3.56 (s, 3H), 3.62 (s, 3H), 3.70
(S, 3H), 4.28-4.64 (m, 6H), 5.80-6.08 (br, 1H), 7.
10 ~ 7.58 (m, 7H), 7.70 (t, 1H, J = 8Hz), 8.58 (d, 1H, J
= 5 Hz) (4) 2,6-anhydro-7-O-[(4'-hydroxy) piperidinocarbonyl] -3,4,5-tri-O-methyl-1-O- (pyridine-2- Yl) methylcarbamoyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3) δ; 1.20~2.10 (m, 4H), 2.60~4.60 (m, 15H), 3.50 (s, 3
H), 3.54 (s, 3H), 3.66 (s, 3H), 4.40 (d, 2H, J = 7.2H)
z), 6.10-6.60 (dr, 1H), 7.00-7.30 (m, 2H), 7.62
(T, 1H, J = 8 Hz), 8.42 (b, 1H, J = 5 Hz) (5) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O- (pyridin-2-yl) methylcarbamoyl-7
-O- (4'-tetradecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.90 (t, 3H, J = 7.2 Hz), 1.10 to 2.00 (m, 28H), 2.80 to 4.
00 (m, 11H), 3.50 (s, 3H), 3.52 (s, 3H), 3.66 (s, 3
H), 4.05-4.45 (m, 4H), 4.45 (d, 2H, J = 5.4 Hz), 4.60
~ 5.30 (m, 2H), 5.76 ~ 6.00 (m, 1H), 7.05 ~ 7.32 (m, 2
H), 7.62 (t, 1H, J = 7.2 Hz), 8.40 to 8.56 (m, 1H) (6) 2,6-Anhydro-1-O- [N- (O-methoxybenzoyl) -N- (pyridine -2-yl) methyl]
Carbamoyl-3,4,5-tri-O-methyl-7-O-
(4'-tetradecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.90 (t, 3H, J = 7.2 Hz), 1.06 to 2.05 (m, 28H), 2.50 to 4.
00 (m, 11H), 3.32 (s, 3H), 3.50 (s, 3H), 3.60 (s, 3
H), 3.82 (s, 3H), 4.00 to 4.38 (m, 4H), 4.60 to 5.00 (m,
2H), 5.10-5.28 (m, 2H), 6.76-7.70 (m, 7H), 8.44-
8.54 (m, 1H) (7) 1-ethyl-2- [N- ｛2,6-anhydro-3,
4,5-tri-O-methyl-7-O- (4-tetradecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D-glo-heptitroxy {-N- (O-methoxybenzoyl)] aminomethylpyridinium Chloride 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.00~2.00 (m, 28H), 1.78 (t,
3H, J = 7.2Hz), 2.20-3.60 (m, 11H), 3.40 (s, 3H), 3.5
0 (s, 3H), 3.58 (s, 3H), 3.86 (s, 3H), 3.90 to 4.20 (m,
4H), 4.60-5.00 (m, 2H), 5.20 (q, 2H, J = 7.2Hz), 5.45
(D, 2H, J = 2Hz), 6.90 (d, 1H, J = 9Hz), 7.04 (d, 1H, J =
7.2Hz), 7.30 ~ 7.50 (m, 2H), 7.86 ~ 8.10 (m, 2H), 8.40
(T, 1H, J = 7.2 Hz), 10.2 (d, 1H, J = 5 Hz) MS; m / z 899 (M + -Cl) Example 14 1-ethyl-2- [N- ｛2,6-anhydro -7-O
-(4'-hexadecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D-glo-heptitroxycarbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride (1) 2,6-anhydro-7-O- (4'-hexadecylcarbamoyloxy) piperidinocarbonyl-3,4,5-
Tri-O-methyl-1-O- (pyridin-2-yl) methylcarbamoyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.90 (t, 3H, J = 7.2 Hz), 1.00 to 2.05 (m, 32H), 2.80 to 4.
00 (m, 11H), 3.50 (s, 3H), 3.52 (s, 3H), 3.65 (s, 3
H), 4.00-4.50 (m, 4H), 4.45 (d, 2H, J = 5.4 Hz), 4.60
~ 5.30 (m, 2H), 5.70 ~ 6.00 (m, 1H), 7.00 ~ 7.40 (m, 2
H), 7.60 (t, 1H, J = 7.2 Hz), 8.36 to 8.54 (m, 1H) (2) 2,6-anhydro-7-O- (4'-hexadecylcarbamoyloxy) piperidinocarbonyl- 1-O-
[N- (O-methoxybenzoyl) -N- (pyridine-
2-yl) methyl] carbamoyl-3,4,5-tri-O-
Methyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 0.90~2.00 (m, 32H), 2.50~3.
90 (m, 11H), 3.30 (s, 3H), 3.50 (s, 3H), 3.58 (s, 3
H), 3.80 (s, 3H), 4.40-4.34 (m, 4H), 4.60-5.00 (m,
2H), 5.10-5.28 (m, 2H), 6.70-7.70 (m, 7H), 8.40-
8.52 (m, 1H) (3) 1-ethyl-2- [N-Ｎ2,6-anhydro-7
-O- (4'-hexadecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D-glo-heptitrooxycarbonyl-N- (O-methoxybenzoyl)] aminomethylpyridinium chloride 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.05~2.00 (m, 32H), 1.78 (t,
3H, J = 7.2Hz), 2.40-3.60 (m, 11H), 3.40 (s, 3H), 3.5
0 (s, 3H), 3.58 (s, 3H), 3.88 (s, 3H), 3.90 to 4.35 (m,
4H), 4.60-5.00 (m, 2H), 5.20 (q, 2H, J = 7.2Hz), 5.45
(D, 2H, J = 3Hz), 6.88 (d, 1H, J = 9Hz), 7.06 (d, 1H, J =
7.2Hz), 7.28 to 7.60 (m, 2H), 7.90 to 8.14 (m, 2H), 8.38
(T, 1H, J = 7.2 Hz), 10.2 (d, 1H, J = 5 Hz) MS; m / z 927 (M + -Cl) Example 15 1-ethyl-2- [N-Ｎ2,6-anhydro -3,4,5-Tri-O-methyl-7-O- (4'-octadecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D
-Glu-heptitroxy} -N- (O-methoxybenzoyl)] aminomethylpyridinium chloride (1) 2,6-anhydro-3,4,5-tri-O-methyl-7
-O- (4'-octadecylcarbamoyloxy) piperidinocarbonyl-1-O- (pyridin-2-yl) methylcarbamoyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.05~2.06 (m, 36H), 2.80~4.
00 (m, 11H), 3.50 (s, 3H), 3.52 (s, 3H), 3.64 (s, 3
H), 4.00-4.40 (m, 4H), 4.45 (d, 2H, J = 5.4 Hz), 4.60
~ 5.25 (m, 2H), 5.90 ~ 6.00 (m, 1H), 7.05 ~ 7.30 (m, 2
H), 7.60 (t, 1H, J = 7.2 Hz), 8.40 to 8.56 (m, 1H) (2) 2,6-anhydro-1-O- [N- (O-methoxybenzoyl) -N- (pyridine -2-yl) methyl]
Carbamoyl-3,4,5-tri-O-methyl-7-O-
(4'-octadecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D-glo-heptitol 1 H-NMR (CDCl 3 ) δ; 0.90 (t, 3H, J = 7.2 Hz), 1.00 to 2.10 (m, 36H), 2.50 to 4.
00 (m, 11H), 3.32 (s, 3H), 3.50 (s, 3H), 3.60 (s, 3
H), 3.82 (s, 3H), 4.00 to 4.37 (m, 4H), 4.60 to 5.00 (m,
2H), 5.10-5.30 (m, 2H), 6.75-7.70 (m, 7H), 8.40-
8.54 (m, 1H) (3) 1-ethyl-2- [N- ｛2,6-anhydro-3,
4,5-tri-O-methyl-7-O- (4'-octadecylcarbamoyloxy) piperidinocarbonyl-D-glycero-D-glo-heptitroxy {-N- (O-methoxybenzoyl)] aminomethylpyridinium Chloride 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.20~2.00 (m, 36H), 1.80 (t,
3H, J = 7.2Hz), 2.40-3.40 (m, 11H), 3.40 (s, 3H), 3.4
8 (s, 3H), 3.60 (s, 3H), 3.88 (s, 3H), 3.90 to 4.40 (m,
4H), 4.60-5.00 (m, 2H), 5.25 (q, 2H, J = 7.2Hz), 5.45
(D, 2H, J = 3Hz), 6.90 (d, 1H, J = 9Hz), 7.05 (d, 1H, J =
7.2Hz), 7.30 ~ 7.60 (m, 2H), 7.90 ~ 8.20 (m, 2H), 8.36
(T, 1H, J = 7.2 Hz), 10.2 (d, 1H, J = 5 Hz) MS; m / z 955 (M + -Cl) 1-deoxy-1- (1 ′) obtained in Example 1 (2) -Hydroxyethyl) -2,3,4-tri-O-methyl-6-O-
The following compound was obtained by extending the side chain using (tetrahydropyran-2-yl) -β-D-glucopyranose.
実施例16 ６−Ｏ−〔Ｎ−アセチル−Ｎ−（2'−Ｎ−エチルピリ
ジニオメチル）〕カルバモイル−１−デオキシ−１−
〔1'−（3,4,5−トリメトキシベンジルオキシ）エチ
ル〕−2,3,4−トリ−Ｏ−メチル−Ｏ−グルコピラノー
スヨージド （１）１−デオキシ−１−〔1'−（3,4,5−トリメトキ
シベンジルオキシ）エチル〕−2,3,4−トリ−Ｏ−メチ
ル−６−Ｏ−（ピリジン−２−イル）メチルカルバモイ
ル−Ｄ−グルコピラノース 1H-NMR(CDCl3)δ； 1.52〜1.80（m,1H）,2.08〜2.23（m,1H）,2.83（bt,1H,
J＝8Hz）,3.05（bt,1H,J＝8Hz）,3.12〜3.37（m,3H）,
3.44〜3.70（m,2H）,3.50（s,3H）,3.55（s,3H）,3.65
（s,3H）,3.80（s,3H）,3.88（s,6H）,4.18〜4.57（m,6
H）,5.77〜5.90（m,1H）,6.55（s,2H）,7.12〜7.25（m,
2H）,7.65（t,1H,J＝8Hz）,8.50（d,1H,J＝5Hz） （２）６−Ｏ−〔Ｎ−アセチル−Ｎ−（ピリジン−２−
イル）メチル〕カルバモイル−１−デオキシ−１−〔1'
−（3,4,5−トリメトキシベンジルオキシ）エチル〕−
2,3,4−トリ−Ｏ−メチル−Ｄ−グルコピラノース 1H-NMR(CDCl3)δ； 1.50〜1.72（m,1H）,2.00〜2.20（m,1H）,2.62（s,3
H）,2.70（t,1H,J＝10Hz）,2.80（t,1H,J＝10Hz）,3.03
〜3.23（m,3H）,3.36（s,3H）,3.43〜3.66（m,2H）,3.5
3（s,3H）,3.59（s,3H）,3.82（s,3H）,3.86（s,3H）,
4.17〜4.27（m,1H）,4.32〜4.46（m,3H）,5.08（s,2
H）,6.55（s,2H）,7.05〜7.16（m,2H）,7.60（t,1H,J＝
8Hz）,8.50（d,1H,J＝5Hz） （３）６−Ｏ−〔Ｎ−アセチル−Ｎ−（2'−エチルピリ
ジニオメチル）〕カルバモイル−１−デオキシ−１−
〔1'−（3,4,5−トリメトキシベンジルオキシ）エチ
ル〕−2,3,4−トリ−Ｏ−メチル−Ｄ−グルコピラノー
スヨージド 1H-NMR(CDCl3)δ； 1.58〜1.80（m,1H）,1.73（t,3H,J＝7.2Hz）,2.08〜2.2
8（m,1H）,2.60（s,3H）,2.78〜2.93（m,2H）,3.16〜3.
70（m,5H）,3.53（s,3H）,3.59（s,3H）,3.65（s,3H）,
3.84（s,3H）,3.87（s,6H）,4.27〜4.60（m,4H）,5.07
（q,2H,J＝7.2Hz）,5.30（s,2H）,6.58（s,2H）,7.63
（d,1H,J＝8Hz）,8.00（t,1H,J＝8Hz）,8.32（t,1H,J＝
8Hz）,9.80（d,1H,J＝5Hz） 実施例１（１）で記載した１−デオキシ−１−（1'−
プロペニル）−６−Ｏ−テトラヒドロピラン−２−イ
ル）−β−Ｄ−グルコピラノースの異性体である１−デ
オキシ−１−（1'−プロペニル）−６−Ｏ−（テトラヒ
ドロピラン−２−イル）−α−Ｄ−グルコピラノースを
用い、実施例１で記載した方法に従い、以下の化合物を
合成した。Example 16 6-O- [N-acetyl-N- (2'-N-ethylpyridiniomethyl)] carbamoyl-1-deoxy-1-
[1 '-(3,4,5-trimethoxybenzyloxy) ethyl] -2,3,4-tri-O-methyl-O-glucopyranose iodide (1) 1-deoxy-1- [1 '-(3,4,5-trimethoxybenzyloxy) ethyl] -2,3,4-tri-O-methyl-6-O- (pyridin-2-yl ) Methylcarbamoyl-D-glucopyranose 1 H-NMR (CDCl 3) δ; 1.52~1.80 (m, 1H), 2.08~2.23 (m, 1H), 2.83 (bt, 1H,
J = 8Hz), 3.05 (bt, 1H, J = 8Hz), 3.12 ~ 3.37 (m, 3H),
3.44 to 3.70 (m, 2H), 3.50 (s, 3H), 3.55 (s, 3H), 3.65
(S, 3H), 3.80 (s, 3H), 3.88 (s, 6H), 4.18 to 4.57 (m, 6
H), 5.77 to 5.90 (m, 1H), 6.55 (s, 2H), 7.12 to 7.25 (m,
2H), 7.65 (t, 1H, J = 8 Hz), 8.50 (d, 1H, J = 5 Hz) (2) 6-O- [N-acetyl-N- (pyridine-2-
Yl) methyl] carbamoyl-1-deoxy-1- [1 ′
-(3,4,5-trimethoxybenzyloxy) ethyl]-
2,3,4-tri-O-methyl-D-glucopyranose 1 H-NMR (CDCl 3) δ; 1.50~1.72 (m, 1H), 2.00~2.20 (m, 1H), 2.62 (s, 3
H), 2.70 (t, 1H, J = 10 Hz), 2.80 (t, 1H, J = 10 Hz), 3.03
~ 3.23 (m, 3H), 3.36 (s, 3H), 3.43 ~ 3.66 (m, 2H), 3.5
3 (s, 3H), 3.59 (s, 3H), 3.82 (s, 3H), 3.86 (s, 3H),
4.17 to 4.27 (m, 1H), 4.32 to 4.46 (m, 3H), 5.08 (s, 2
H), 6.55 (s, 2H), 7.05 to 7.16 (m, 2H), 7.60 (t, 1H, J =
8 Hz), 8.50 (d, 1H, J = 5 Hz) (3) 6-O- [N-acetyl-N- (2'-ethylpyridiniomethyl)] carbamoyl-1-deoxy-1-
[1 '-(3,4,5-trimethoxybenzyloxy) ethyl] -2,3,4-tri-O-methyl-D-glucopyranose iodide 1 H-NMR (CDCl 3) δ; 1.58~1.80 (m, 1H), 1.73 (t, 3H, J = 7.2Hz), 2.08~2.2
8 (m, 1H), 2.60 (s, 3H), 2.78 to 2.93 (m, 2H), 3.16 to 3.
70 (m, 5H), 3.53 (s, 3H), 3.59 (s, 3H), 3.65 (s, 3H),
3.84 (s, 3H), 3.87 (s, 6H), 4.27 to 4.60 (m, 4H), 5.07
(Q, 2H, J = 7.2Hz), 5.30 (s, 2H), 6.58 (s, 2H), 7.63
(D, 1H, J = 8Hz), 8.00 (t, 1H, J = 8Hz), 8.32 (t, 1H, J =
8 Hz), 9.80 (d, 1H, J = 5 Hz) 1-deoxy-1- (1'-) described in Example 1 (1)
1-deoxy-1- (1′-propenyl) -6-O- (tetrahydropyran-2-yl) which is an isomer of (propenyl) -6-O-tetrahydropyran-2-yl) -β-D-glucopyranose The following compounds were synthesized according to the method described in Example 1 using-)-α-D-glucopyranose.
実施例17 １−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−アン
ヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ−オクタデ
シルカルバモイル−Ｄ−グリセロ−Ｄ−イド−ヘプチト
ロキシ｝カルボニル〕アミノメチルピリジニウムヨージ
ド （１）１−デオキシ−１−（1'−プロペニル）−６−Ｏ
−（テトラヒドロピラン−２−イル）−α−Ｄ−グルコ
ピラノース 1H-NMR(CDCl3)δ； 1.25〜1.78（m,6H）,2.25〜2.40（m,2H）,2.50〜2.72
（m,1H）,2.90〜3.24（m,1H）,3.32〜4.07（m,10H）,4.
32〜4.40,4.46〜4.54（m,1H）,4.90〜5.10（m,2H）,5.6
0〜5.82（m,1H） （２）１−デオキシ−１−（プロペニル）−2,3,4−ト
リ−Ｏ−メチル−６−（テトラヒドロピラン−２−イ
ル）−α−Ｄ−グルコピラノース 1H-NMR(CDCl3)δ； 1.40〜1.94（m,6H）,2.24〜2.50（m,2H）,3.00〜4.00
（m,8H）,3.45（s,3H）,3.54（s,3H）,3.63（s,3H）,4.
05〜4.20（m,1H）,4.60〜4.70（m,1H）,5.06（d,1H,J＝
10Hz）,5.10（d,1H,J＝16Hz）,5.72〜5.94（m,1H） （３）１−デオキシ−１−（1'−ヒドロキシエチル）−
2,3,4−トリ−Ｏ−メチル−６−Ｏ−（テトラヒドロピ
ラン−２−イル）−α−Ｄ−グルコピラノース 1H-NMR(CDCl3)δ； 1.45〜2.12（m,8H）,2.80〜3.08（m,3H）,3.25〜4.05
（m,8H）,3.50（s,3H）,3.55（s,3H）,3.66（s,3H）,4.
20〜4.34（m,1H）,4.64〜4.70（m,1H） （４）１−デオキシ−１−ビニル−2,3,4−トリ−Ｏ−
メチル−６−Ｏ−（テトラヒドロピラン−２−イル）−
α−Ｄ−グルコピラノース 1H-NMR(CDCl3)δ； 1.44〜1.95（m,6H）,3.08〜3.75（m,6H）,3.48（s,3
H）,3.54（s,3H）,3.64（s,3H）,3.82〜4.00（m,2H）,
4.56〜4.70（m,2H）,5.23（d,1H,J＝10Hz）,5.38（d,1
H,J＝16Hz）,5.94〜6.14（m,1H） （５）１−デオキシ−１−ビニル−2,3,4−トリ−Ｏ−
メチル−α−Ｄ−グルコピラノース 1H-NMR(CDCl3)δ； 2.00（t,1H,J＝7.0Hz）,3.10〜3.90（m,6H）,3.49（s,3
H）,3.57（s,3H）,3.64（s,3H）,4.55〜4.64（m,1H）,
5.44（d,1H,J＝10Hz）,5.46（d,1H,J＝16Hz）,5.98〜6.
18（m,1H） （６）１−デオキシ−１−ビニル−2,3,4−トリ−Ｏ−
メチル−６−Ｏ−オクタデシルカルバモイル−α−Ｄ−
グルコピラノース 1H-NMR(CDCl3)δ； 0.87（t,3H,J＝7.2Hz）,1.10〜1.35（m,32H）,2.96〜3.
22（m,3H）,3.13〜3.44（m,3H）,3.48（s,3H）,3.53
（s,3H）,3.64（s,3H）,4.20〜4.30（m,2H）,4.56〜4.6
4（m,1H）,4.72〜4.82（m,1H）,5.43（d,1H,J＝12Hz）,
5.45（d,1H,J＝16Hz）,5.92〜6.10（m,1H） （７）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７
−Ｏ−オクタデシルカルバモイル−Ｄ−グリセロ−Ｄ−
イド−ヘプチトール 1H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.16〜1.52（m,32H）,2.00〜2.
10（m,1H）,2.92〜3.22（m,3H）,3.00〜3.92（m,5H）,
3.50（s,3H）,3.52（s,3H）,3.62（s,3H）,4.04〜4.28
（m,3H）,4.70〜4.80（m,1H） （８）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７
−Ｏ−オクタデシルカルバモイル−１−Ｏ−〔Ｎ−（ピ
リジン−２−イル）カルバモイル〕−Ｄ−グリセロ−Ｄ
−イド−ヘプチトール 1H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.16〜1.52（m,32H）,3.00〜3.
80（m,6H）,3.49（s,3H）,3.53（s,3H）,3.62（s,3H）,
4.12〜4.60（m,7H）,4.86〜4.96（m,1H）,5.84〜5.92
（m,1H）,7.16〜7.40（m,2H）,7.70（t,1H,J＝8Hz）,8.
55（d,1H,J＝5Hz） （９）１−Ｏ−〔Ｎ−アセチル−Ｎ−（ピリジン−２−
イル）メチル〕カルバモイル−2,6−アンヒドロ−3,4,5
−トリ−Ｏ−メチル−７−Ｏ−オクタデシルカルバモイ
ル−Ｄ−グリセロ−Ｄ−イド−ヘプチトール 1H-NMR(CDCl3)δ； 0.89（t,3H,J＝7.2Hz）,1.16〜1.70（m,32H）,2.67（s,
3H）,3.00（t,1H,J＝8Hz）,3.08〜3.70（m,4H）,3.48
（s,3H）,3.52（s,3H）,3.60（s,3H）,4.00〜4.46（m,6
H）,5.08〜5.18（m,2H）,5.84〜5.96（m,1H）,7.05〜7.
24（m,2H）,7.68（t,1H,J＝8Hz）,8.52（d,1H,J＝5Hz） （10）１−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−
アンヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ−オク
タデシルカルバモイル−Ｄ−グリセロ−Ｄ−イド−ヘプ
チトロキシ｝カルボニル〕アミノメチルピリジニウムヨ
ージド 1H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.12〜1.60（m,32H）,1.74（t,
3H,J＝7.2Hz）,2.68（s,3H）,3.00〜3.20（m,3H）,3.24
（dd,1H,J＝9Hz,7Hz）,3.30〜3.44（m,1H）,3.51（s,3
H）,3.54（s,3H）,3.60（s,3H）,3.66〜3.80（m,1H）,
4.04〜4.46（m,4H）,4.76〜5.12（m,4H）,5.40（d,1H,J
＝18Hz）,5.55（d,1H,J＝18Hz）,7.78（d,1H,J＝8Hz）,
7.96（t,1H,J＝8Hz）,8.45（t,1H,J＝8Hz）,9.38（d,1
H,J＝15Hz） １−デオキシ−１−（プロペニル）−2,3,4−トリ−
Ｏ−メチル−６−（テトラヒドロピラン−２−イル）−
α−Ｄ−グルコピラノースを出発物質として以下の化合
物を合成した。Example 17 1-ethyl-2- [N-acetyl-N-Ｎ2,6-anhydro-3,4,5-tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-D-id- Heptitroxy｝ carbonyl] aminomethylpyridinium iodide (1) 1-deoxy-1- (1′-propenyl) -6-O
-(Tetrahydropyran-2-yl) -α-D-glucopyranose 1 H-NMR (CDCl 3 ) δ; 1.25 to 1.78 (m, 6H), 2.25 to 2.40 (m, 2H), 2.50 to 2.72
(M, 1H), 2.90 to 3.24 (m, 1H), 3.32 to 4.07 (m, 10H), 4.
32 to 4.40, 4.46 to 4.54 (m, 1H), 4.90 to 5.10 (m, 2H), 5.6
0 to 5.82 (m, 1H) (2) 1-deoxy-1- (propenyl) -2,3,4-tri-O-methyl-6- (tetrahydropyran-2-yl) -α-D-glucopyranose 1 H-NMR (CDCl 3 ) δ; 1.40 to 1.94 (m, 6H), 2.24 to 2.50 (m, 2H), 3.00 to 4.00
(M, 8H), 3.45 (s, 3H), 3.54 (s, 3H), 3.63 (s, 3H), 4.
05 to 4.20 (m, 1H), 4.60 to 4.70 (m, 1H), 5.06 (d, 1H, J =
10 Hz), 5.10 (d, 1H, J = 16 Hz), 5.72 to 5.94 (m, 1H) (3) 1-deoxy-1- (1'-hydroxyethyl)-
2,3,4-tri-O-methyl-6-O- (tetrahydropyran-2-yl) -α-D-glucopyranose 1 H-NMR (CDCl 3 ) δ; 1.45 to 2.12 (m, 8H), 2.80 to 3.08 (m, 3H), 3.25 to 4.05
(M, 8H), 3.50 (s, 3H), 3.55 (s, 3H), 3.66 (s, 3H), 4.
20 to 4.34 (m, 1H), 4.64 to 4.70 (m, 1H) (4) 1-deoxy-1-vinyl-2,3,4-tri-O-
Methyl-6-O- (tetrahydropyran-2-yl)-
α-D-glucopyranose 1 H-NMR (CDCl 3 ) δ; 1.44 to 1.95 (m, 6H), 3.08 to 3.75 (m, 6H), 3.48 (s, 3
H), 3.54 (s, 3H), 3.64 (s, 3H), 3.82 ~ 4.00 (m, 2H),
4.56 to 4.70 (m, 2H), 5.23 (d, 1H, J = 10 Hz), 5.38 (d, 1
H, J = 16 Hz), 5.94 to 6.14 (m, 1H) (5) 1-deoxy-1-vinyl-2,3,4-tri-O-
Methyl-α-D-glucopyranose 1 H-NMR (CDCl 3 ) δ; 2.00 (t, 1H, J = 7.0 Hz), 3.10 to 3.90 (m, 6H), 3.49 (s, 3
H), 3.57 (s, 3H), 3.64 (s, 3H), 4.55-4.64 (m, 1H),
5.44 (d, 1H, J = 10 Hz), 5.46 (d, 1H, J = 16 Hz), 5.98-6.
18 (m, 1H) (6) 1-deoxy-1-vinyl-2,3,4-tri-O-
Methyl-6-O-octadecylcarbamoyl-α-D-
Glucopyranose 1 H-NMR (CDCl 3) δ; 0.87 (t, 3H, J = 7.2Hz), 1.10~1.35 (m, 32H), 2.96~3.
22 (m, 3H), 3.13 to 3.44 (m, 3H), 3.48 (s, 3H), 3.53
(S, 3H), 3.64 (s, 3H), 4.20-4.30 (m, 2H), 4.56-4.6
4 (m, 1H), 4.72 ~ 4.82 (m, 1H), 5.43 (d, 1H, J = 12Hz),
5.45 (d, 1H, J = 16 Hz), 5.92 to 6.10 (m, 1H) (7) 2,6-anhydro-3,4,5-tri-O-methyl-7
-O-octadecylcarbamoyl-D-glycero-D-
Id-heptitol 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.16~1.52 (m, 32H), 2.00~2.
10 (m, 1H), 2.92 to 3.22 (m, 3H), 3.00 to 3.92 (m, 5H),
3.50 (s, 3H), 3.52 (s, 3H), 3.62 (s, 3H), 4.04 to 4.28
(M, 3H), 4.70 to 4.80 (m, 1H) (8) 2,6-Anhydro-3,4,5-tri-O-methyl-7
-O-octadecylcarbamoyl-1-O- [N- (pyridin-2-yl) carbamoyl] -D-glycero-D
-Id-Heptitol 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.16~1.52 (m, 32H), 3.00~3.
80 (m, 6H), 3.49 (s, 3H), 3.53 (s, 3H), 3.62 (s, 3H),
4.12 to 4.60 (m, 7H), 4.86 to 4.96 (m, 1H), 5.84 to 5.92
(M, 1H), 7.16 ~ 7.40 (m, 2H), 7.70 (t, 1H, J = 8Hz), 8.
55 (d, 1H, J = 5 Hz) (9) 1-O- [N-acetyl-N- (pyridine-2-
Yl) methyl] carbamoyl-2,6-anhydro-3,4,5
-Tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-D-ido-heptitol 1 H-NMR (CDCl 3) δ; 0.89 (t, 3H, J = 7.2Hz), 1.16~1.70 (m, 32H), 2.67 (s,
3H), 3.00 (t, 1H, J = 8Hz), 3.08-3.70 (m, 4H), 3.48
(S, 3H), 3.52 (s, 3H), 3.60 (s, 3H), 4.00 to 4.46 (m, 6
H), 5.08-5.18 (m, 2H), 5.84-5.96 (m, 1H), 7.05-7.
24 (m, 2H), 7.68 (t, 1H, J = 8 Hz), 8.52 (d, 1H, J = 5 Hz) (10) 1-ethyl-2- [N-acetyl-N-Ｎ2,6-
Anhydro-3,4,5-tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-D-ido-heptitroxy} carbonyl] aminomethylpyridinium iodide 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.12~1.60 (m, 32H), 1.74 (t,
3H, J = 7.2Hz), 2.68 (s, 3H), 3.00 to 3.20 (m, 3H), 3.24
(Dd, 1H, J = 9Hz, 7Hz), 3.30-3.44 (m, 1H), 3.51 (s, 3
H), 3.54 (s, 3H), 3.60 (s, 3H), 3.66 to 3.80 (m, 1H),
4.04 to 4.46 (m, 4H), 4.76 to 5.12 (m, 4H), 5.40 (d, 1H, J
= 18Hz), 5.55 (d, 1H, J = 18Hz), 7.78 (d, 1H, J = 8Hz),
7.96 (t, 1H, J = 8 Hz), 8.45 (t, 1H, J = 8 Hz), 9.38 (d, 1
H, J = 15 Hz) 1-deoxy-1- (propenyl) -2,3,4-tri-
O-methyl-6- (tetrahydropyran-2-yl)-
The following compounds were synthesized using α-D-glucopyranose as a starting material.
実施例18 １−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−アン
ヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ−オクタデ
シルカルバモイル−Ｄ−グリセロ−Ｌ−グロ−ヘプチト
ロキシ｝カルボニル〕アミノメチルピリジニウムヨージ
ド （１）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−オクタデシルカルバモイル−７−Ｏ−（テトラヒ
ドロピラン−２−イル）−Ｄ−グリセロ−Ｄ−イド−ヘ
プチトール 1H-NMR(CDCl3)δ； 0.88（t,3H,J＝7.2Hz）,1.10〜1.90（m,38H）,3.10〜4.
00（m,10H）,3.50（s,3H）,3.54（s,3H）,3.64（s,3
H）,4.20〜4.50（m,3H）,4.60〜4.84（m,2H） （２）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−オクタデシルカルバモイル−Ｄ−グリセロ−Ｄ−
イド−ヘプチトール 1H-NMR(CDCl3)δ； 0.86（t,3H,J＝7.2Hz）,1.08〜1.60（m,32H）,1.92〜2.
06（m,1H）,3.04〜3.88（m,8H）,3.50（s,3H）,3.56
（s,3H）,3.62（s,3H）,4.00〜4.52（m,3H）,4.70〜4.8
8（m,1H） （３）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−１
−Ｏ−オクタデシルカルバモイル−７−Ｏ−〔Ｎ−（ピ
リジン−２−イル）メチルカルバモイル〕−Ｄ−グリセ
ロ−Ｄ−イド−ヘプチトール 1H-NMR(CDCl3)δ； 0.89（t,3H,J＝7.2Hz）,1.10〜1.80（m,32H）,3.00〜3.
80（m,6H）,3.52（s,3H）,3.55（s,3H）,3.64（s,3H）,
4.20〜4.50（m,5H）,4.54（d,2H,J＝7.0Hz）,4.88〜5.8
0（m,1H）,5.84〜5.98（m,1H）,7.16〜7.42（m,2H）,7.
70（t,1H,J＝8Hz）,8.57（d,1H,J＝5Hz） （４）７−Ｏ−〔Ｎ−アセチル−Ｎ−｛（ピリジン−２
−イル）メチル｝〕カルバモイル−2,6−アンヒドロ−
3,4,5−トリ−Ｏ−メチル−１−Ｏ−オクタデシルカル
バモイル−Ｄ−グリセロ−Ｄ−イド−ヘプチトール 1H-NMR(CDCl3)δ； 0.87（t,3H,J＝7.2Hz）,1.00〜1.76（m,32H）,2.68（s,
3H）,3.08〜3.70（m,5H）,3.38（s,3H）,3.48（s,3H）,
3.56（s,3H）,4.14〜4.42（m,6H）,5.08〜5.16（m,2
H）,5.80〜5.96（m,1H）,7.04〜7.24（m,2H）,7.65（t,
1H,J＝8Hz）,8.48〜8.56（m,1H,J＝1Hz） （５）１−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−
アンヒドロ−3,4,5−トリ−Ｏ−メチル−７−Ｏ−オク
タデシルカルバモイル−Ｄ−グリセロ−Ｌ−グロ−ヘプ
チトロキシ｝カルボニル〕アミノメチルピリジニウムヨ
ージド 1H-NMR(CDCl3)δ； 0.87（t,3H,J＝7.2Hz）,1.16〜1.52（m,32H）,1.72（t,
3H,J＝7.2Hz）,2.67（s,3H）,2.82〜2.94（m,1H）,2.98
〜3.16（m,2H）,3.26〜3.40（m,2H）,3.48（s,3H）,3.5
0（s,3H）,3.56（s,3H）,3.88〜4.00（m,1H）,4.06〜4.
24（m,2H）,4.32〜4.54（m,3H）,5.00〜5.18（m,3H）,
5.36〜5.48（m,2H）,7.77（d,1H,J＝8Hz）,8.04（t,1H,
J＝8Hz）,8.40（t,1H,J＝8Hz）,9.80（d,1H,J＝5Hz） 実施例19 １−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−アン
ヒドロ−７−Ｏ−（3',4',5'−トリメトキシベンジル）
−3,4,5−トリ−Ｏ−メチル−Ｄ−グリセロ−Ｌ−グロ
−ヘプチトロキシ｝カルボニル〕アミノメチルピリジニ
ウムヨージド （１）2,6−アンヒドロ−3,4,5−トリ−Ｏ−メチル−７
−Ｏ−（テトラヒドロピラン−２−イル）−Ｄ−グリセ
ロ−Ｄ−イド−ヘプチトール 1H-NMR(CDCl3)δ； 1.44〜1.90（m,6H）,2.54〜2.64（m,1H）,3.02（q,2H,J
＝8Hz）,3.32（t,2H,J＝7.5Hz）,3.35〜4.00（m,4H）,
3.50（s,3H）,3.50（s,3H）,3.63（s,3H）,4.12〜4.24
（m,2H）,4.52〜4.60（m,1H）,4.66〜4.74（m,1H） （２）2,6−アンヒドロ−１−Ｏ−（3',4',5'−トリメ
トキシベンジル）−3,4,5−トリ−Ｏ−メチル−７−Ｏ
−（テトラヒドロピラン−２−イル）−Ｄ−グリセロ−
Ｄ−イド−ヘプチトール 1H-NMR(CDCl3)δ； 1.35〜1.90（m,6H）,3.30〜4.00（m,10H）,3.45（s,3
H）,3.50（s,3H）,3.60（s,3H）,3.82（s,3H）,3.85
（s,6H）,4.18〜4.30（m,1H）,4.50（s,2H）,4.58〜4.6
8（m,1H）,6.55（s,2H） （３）2,6−アンヒドロ−１−Ｏ−（3',4',5'−トリメ
トキシベンジル）−3,4,5−トリ−Ｏ−メチル−Ｄ−グ
リセロ−Ｄ−イド−ヘプチトール 1H-NMR(CDCl3)δ； 2.00（t,3H,J＝7Hz）,3.07〜3.17（m,1H）,3.30〜3.42
（m,2H）,3.47（s,3H）,3.52（s,3H）,3.57〜3.90（m,5
H）,3.59（s,3H）,3.82（s,3H）,3.86（s,6H）,4.20〜
4.30（m,1H）,4.48（d,1H,J＝13Hz）,4.52（d,1H,J＝13
Hz） （４）2,6−アンヒドロ−１−Ｏ−（3',4',5'−トリメ
トキシベンジル）−3,4,5−トリ−Ｏ−メチル−６−Ｏ
−〔Ｎ−（ピリジン−２−イル）メチルカルバモイル〕
−Ｄ−グリセロ−Ｄ−イド−ヘプチトール 1H-NMR(CDCl3)δ； 3.09（t,1H,J＝7Hz）,3.30〜3.90（m,5H）,3.47（s,3
H）,3.50（s,3H）,3.60（s,3H）,3.82（s,3H）,3.85
（s,6H）,4.19〜4.35（m,3H）,4.42〜4.56（m,4H）,5.8
0〜5.92（m,1H）,6.58（m,2H）,7.12〜7.25（m,2H）,7.
66（t,1H,J＝8Hz）,8.52（d,1H,J＝5Hz） （５）2,6−アンヒドロ−６−Ｏ−〔Ｎ−アセチル−Ｎ
−（ピリジン−２−イル）メチル〕カルバモイル−１−
Ｏ−（3',4',5'−トリメトキシベンジル）−3,4,5−ト
リ−Ｏ−メチル−Ｄ−グリセロ−Ｄ−イド−ヘプチトー
ル 1H-NMR(CDCl3)δ； 2.60（s,3H）,2.84（t,1H,J＝7Hz）,3.19〜3.90（m,5
H）,3.30（s,3H）,3.42（s,3H）,3.52（s,3H）,3.83
（s,3H）,3.85（s,6H）,4.05〜4.14（m,1H）,4.28（dd,
1H,J＝10Hz,5Hz）,4.40（dd,1H,J＝10Hz,5Hz）,4.45
（s,2H）,5.02（d,1H,J＝18Hz）,5.15（d,1H,J＝18H
z）,6.53（s,2H）,7.05〜7.17（m,2H）,7.59（t,1H,J＝
8Hz）,8.50（d,1H,J＝5Hz） （６）１−エチル−２−〔Ｎ−アセチル−Ｎ−｛2,6−
アンヒドロ−７−Ｏ−（3',4',5'−トリメトキシベンジ
ル）−3,4,5−トリ−Ｏ−メチル−Ｄ−グリセロ−Ｌ−
グロ−ヘプチトロキシ｝カルボニル〕アミノメチルピリ
ジニウムヨージド 1H-NMR(CDCl3)δ； 1.67（t,3H,J＝7.2Hz）,2.64（s,3H）,2.88（t,1H,J＝1
0Hz）,3.06（t,1H,J＝10Hz）,3.27（t,1H,J＝10Hz）,3.
32〜3.74（m,4H）,3.50（s,3H）,3.52（s,3H）,3.62
（s,3H）,3.80（s,3H）,3.84（s,6H）,4.32〜4.58（m,4
H）,5.04（q,2H,J＝7.2Hz）,5.26〜5.42（m,2H）,6.58
（s,2H）,7.70（d,1H,J＝8Hz）,7.92（t,1H,J＝8Hz）,
8.24（t,1H,J＝8Hz）,9.66（d,1H,J＝5Hz）Example 18 1-ethyl-2- [N-acetyl-N-Ｎ2,6-anhydro-3,4,5-tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-L-glo- Heptitroxy｝ carbonyl] aminomethylpyridinium iodide (1) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O-octadecylcarbamoyl-7-O- (tetrahydropyran-2-yl) -D-glycero-D-ido-heptitol 1 H-NMR (CDCl 3) δ; 0.88 (t, 3H, J = 7.2Hz), 1.10~1.90 (m, 38H), 3.10~4.
00 (m, 10H), 3.50 (s, 3H), 3.54 (s, 3H), 3.64 (s, 3
H), 4.20-4.50 (m, 3H), 4.60-4.84 (m, 2H) (2) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O-octadecylcarbamoyl-D-glycero-D-
Id-heptitol 1 H-NMR (CDCl 3) δ; 0.86 (t, 3H, J = 7.2Hz), 1.08~1.60 (m, 32H), 1.92~2.
06 (m, 1H), 3.04 to 3.88 (m, 8H), 3.50 (s, 3H), 3.56
(S, 3H), 3.62 (s, 3H), 4.00 to 4.52 (m, 3H), 4.70 to 4.8
8 (m, 1H) (3) 2,6-anhydro-3,4,5-tri-O-methyl-1
-O-octadecylcarbamoyl-7-O- [N- (pyridin-2-yl) methylcarbamoyl] -D-glycero-D-ido-heptitol 1 H-NMR (CDCl 3) δ; 0.89 (t, 3H, J = 7.2Hz), 1.10~1.80 (m, 32H), 3.00~3.
80 (m, 6H), 3.52 (s, 3H), 3.55 (s, 3H), 3.64 (s, 3H),
4.20 ~ 4.50 (m, 5H), 4.54 (d, 2H, J = 7.0Hz), 4.88 ~ 5.8
0 (m, 1H), 5.84 to 5.98 (m, 1H), 7.16 to 7.42 (m, 2H), 7.
70 (t, 1H, J = 8 Hz), 8.57 (d, 1H, J = 5 Hz) (4) 7-O- [N-acetyl-N-｛(pyridine-2
-Yl) methyl}] carbamoyl-2,6-anhydro-
3,4,5-tri-O-methyl-1-O-octadecylcarbamoyl-D-glycero-D-ido-heptitol 1 H-NMR (CDCl 3) δ; 0.87 (t, 3H, J = 7.2Hz), 1.00~1.76 (m, 32H), 2.68 (s,
3H), 3.08-3.70 (m, 5H), 3.38 (s, 3H), 3.48 (s, 3H),
3.56 (s, 3H), 4.14 to 4.42 (m, 6H), 5.08 to 5.16 (m, 2
H), 5.80-5.96 (m, 1H), 7.04-7.24 (m, 2H), 7.65 (t,
1H, J = 8 Hz), 8.48 to 8.56 (m, 1H, J = 1 Hz) (5) 1-ethyl-2- [N-acetyl-N- ｛2,6-
Anhydro-3,4,5-tri-O-methyl-7-O-octadecylcarbamoyl-D-glycero-L-glo-heptitroxy｝ carbonyl] aminomethylpyridinium iodide 1 H-NMR (CDCl 3) δ; 0.87 (t, 3H, J = 7.2Hz), 1.16~1.52 (m, 32H), 1.72 (t,
3H, J = 7.2Hz), 2.67 (s, 3H), 2.82 to 2.94 (m, 1H), 2.98
Up to 3.16 (m, 2H), 3.26 to 3.40 (m, 2H), 3.48 (s, 3H), 3.5
0 (s, 3H), 3.56 (s, 3H), 3.88 to 4.00 (m, 1H), 4.06 to 4.
24 (m, 2H), 4.32 to 4.54 (m, 3H), 5.00 to 5.18 (m, 3H),
5.36 to 5.48 (m, 2H), 7.77 (d, 1H, J = 8 Hz), 8.04 (t, 1H,
J = 8 Hz), 8.40 (t, 1H, J = 8 Hz), 9.80 (d, 1H, J = 5 Hz) Example 19 1-ethyl-2- [N-acetyl-N-Ｎ2,6-anhydro-7 -O- (3 ', 4', 5'-trimethoxybenzyl)
-3,4,5-Tri-O-methyl-D-glycero-L-glo-heptitrooxy @ carbonyl] aminomethylpyridinium iodide (1) 2,6-anhydro-3,4,5-tri-O-methyl-7
-O- (tetrahydropyran-2-yl) -D-glycero-D-ido-heptitol 1 H-NMR (CDCl 3 ) δ; 1.44 to 1.90 (m, 6H), 2.54 to 2.64 (m, 1H), 3.02 (q, 2H, J
= 8Hz), 3.32 (t, 2H, J = 7.5Hz), 3.35-4.00 (m, 4H),
3.50 (s, 3H), 3.50 (s, 3H), 3.63 (s, 3H), 4.12 to 4.24
(M, 2H), 4.52 to 4.60 (m, 1H), 4.66 to 4.74 (m, 1H) (2) 2,6-anhydro-1-O- (3 ', 4', 5'-trimethoxybenzyl) -3,4,5-tri-O-methyl-7-O
-(Tetrahydropyran-2-yl) -D-glycero-
D-id-heptitol 1 H-NMR (CDCl 3) δ; 1.35~1.90 (m, 6H), 3.30~4.00 (m, 10H), 3.45 (s, 3
H), 3.50 (s, 3H), 3.60 (s, 3H), 3.82 (s, 3H), 3.85
(S, 6H), 4.18-4.30 (m, 1H), 4.50 (s, 2H), 4.58-4.6
8 (m, 1H), 6.55 (s, 2H) (3) 2,6-anhydro-1-O- (3 ', 4', 5'-trimethoxybenzyl) -3,4,5-tri-O -Methyl-D-glycero-D-ido-heptitol 1 H-NMR (CDCl 3 ) δ; 2.00 (t, 3H, J = 7 Hz), 3.07 to 3.17 (m, 1H), 3.30 to 3.42
(M, 2H), 3.47 (s, 3H), 3.52 (s, 3H), 3.57 ~ 3.90 (m, 5
H), 3.59 (s, 3H), 3.82 (s, 3H), 3.86 (s, 6H), 4.20 ~
4.30 (m, 1H), 4.48 (d, 1H, J = 13Hz), 4.52 (d, 1H, J = 13
Hz) (4) 2,6-Anhydro-1-O- (3 ', 4', 5'-trimethoxybenzyl) -3,4,5-tri-O-methyl-6-O
-[N- (pyridin-2-yl) methylcarbamoyl]
-D-glycero-D-id-heptitol 1 H-NMR (CDCl 3) δ; 3.09 (t, 1H, J = 7Hz), 3.30~3.90 (m, 5H), 3.47 (s, 3
H), 3.50 (s, 3H), 3.60 (s, 3H), 3.82 (s, 3H), 3.85
(S, 6H), 4.19 to 4.35 (m, 3H), 4.42 to 4.56 (m, 4H), 5.8
0 to 5.92 (m, 1H), 6.58 (m, 2H), 7.12 to 7.25 (m, 2H), 7.
66 (t, 1H, J = 8 Hz), 8.52 (d, 1H, J = 5 Hz) (5) 2,6-anhydro-6-O- [N-acetyl-N
-(Pyridin-2-yl) methyl] carbamoyl-1-
O- (3 ', 4', 5'-trimethoxybenzyl) -3,4,5-tri-O-methyl-D-glycero-D-ido-heptitol 1 H-NMR (CDCl 3) δ; 2.60 (s, 3H), 2.84 (t, 1H, J = 7Hz), 3.19~3.90 (m, 5
H), 3.30 (s, 3H), 3.42 (s, 3H), 3.52 (s, 3H), 3.83
(S, 3H), 3.85 (s, 6H), 4.05 to 4.14 (m, 1H), 4.28 (dd,
1H, J = 10Hz, 5Hz), 4.40 (dd, 1H, J = 10Hz, 5Hz), 4.45
(S, 2H), 5.02 (d, 1H, J = 18Hz), 5.15 (d, 1H, J = 18H
z), 6.53 (s, 2H), 7.05 to 7.17 (m, 2H), 7.59 (t, 1H, J =
8Hz), 8.50 (d, 1H, J = 5Hz) (6) 1-ethyl-2- [N-acetyl-N- ｛2,6-
Anhydro-7-O- (3 ', 4', 5'-trimethoxybenzyl) -3,4,5-tri-O-methyl-D-glycero-L-
Glo-heptitroxydicarbonyl] aminomethylpyridinium iodide 1 H-NMR (CDCl 3) δ; 1.67 (t, 3H, J = 7.2Hz), 2.64 (s, 3H), 2.88 (t, 1H, J = 1
0Hz), 3.06 (t, 1H, J = 10Hz), 3.27 (t, 1H, J = 10Hz), 3.
32 to 3.74 (m, 4H), 3.50 (s, 3H), 3.52 (s, 3H), 3.62
(S, 3H), 3.80 (s, 3H), 3.84 (s, 6H), 4.32 to 4.58 (m, 4
H), 5.04 (q, 2H, J = 7.2Hz), 5.26-5.42 (m, 2H), 6.58
(S, 2H), 7.70 (d, 1H, J = 8Hz), 7.92 (t, 1H, J = 8Hz),
8.24 (t, 1H, J = 8 Hz), 9.66 (d, 1H, J = 5 Hz)
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｄ 405/14 ２１１ Ｃ０７Ｄ 405/14 ２１１ (72)発明者 川原 哲也 茨城県つくば市天久保２丁目23―５ メ ゾン学園304号 (72)発明者 阿部 信也 茨城県牛久市女化町1083―44 (72)発明者 宮澤 修平 茨城県取手市白山６―８―17 サンラフ ォーレＢ202 (72)発明者 宮本 光明 茨城県土浦市中高津１―４―５ (72)発明者 吉村 寛幸 茨城県つくば市二の宮４丁目４―18 サ ニーヒルテラス301号 (72)発明者 原田 耕吉 茨城県つくば市松代２丁目11―２ グリ ーンハイム３棟２号 (72)発明者 永岡 淳作 茨城県つくば市大字金田1803―１ (72)発明者 川田 力 茨城県土浦市中央２―16―23 亀城ハイ ツ25号 (72)発明者 吉村 勉 茨城県つくば市千現２丁目７―18 細田 住宅４号棟 (72)発明者 鈴木 弘真 茨城県取手市台宿１―３―10 (72)発明者 左右田 茂 茨城県牛久市牛久町972―16 (72)発明者 町田 善正 茨城県つくば市下広岡500―81 (72)発明者 片山 幸一 茨城県つくば市梅園２丁目30―３ (72)発明者 山津 功 茨城県牛久市柏田町3605―669 (58)調査した分野(Int.Cl.6，ＤＢ名) C07D 405/12 C07D 405/14 A61K 31/00 - 31/80 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. 6 Identification symbol FI C07D 405/14 211 C07D 405/14 211 (72) Inventor Tetsuya Kawahara 2-23-5, Akumabo, Tsukuba-shi, Ibaraki 304 Maison Gakuen 304 No. (72) Inventor Shinya Abe 1083-44, Meka-cho, Ushiku City, Ibaraki Prefecture (72) Inventor Shuhei Miyazawa 6-8-17, Shirayama, Tora City, Ibaraki Prefecture Sanrafore B202 (72) Mitsuaki Miyamoto, Tsuchiura City, Ibaraki Prefecture 1-4-5 Takatsu (72) Inventor Hiroyuki Yoshimura 4-4-1, Ninomiya 4-chome, Ninomiya, Tsukuba City, Ibaraki Prefecture (72) Inventor Kokichi Harada 2-1-2 Matsushiro 2-chome, Tsukuba City, Ibaraki Prefecture Greenheim Building No. 2 (72) Inventor Junsaku Nagaoka, 1803-1 Kanada, Tsukuba, Ibaraki Pref. (72) Inventor Riki Kawada 2-16-23, Chuo, Tsuchiura, Ibaraki Pref. 25 Kamejo Heights 25 (72) Invention Tsutomu Yoshimura 2-7-18 Sengen, Tsukuba-shi, Ibaraki Pref.House 4 Building (72) Inventor Hiromasa Suzuki 1-3-10 Daijuku, Toride-shi, Ibaraki Pref. (72) Inventor Shigeru Soda, 972-Ushikucho, Ushiku-shi, Ibaraki 16 (72) Inventor Yoshimasa Machida 500-81 Shimohirooka, Tsukuba City, Ibaraki Prefecture (72) Koichi Katayama 2- 30-3, Umezono, Tsukuba City, Ibaraki Prefecture (72) Isao Yamazu 3605-669, Kashiwadacho, Ushiku City, Ibaraki Prefecture (58) Field surveyed (Int. Cl. 6 , DB name) C07D 405/12 C07D 405/14 A61K 31/00-31/80 CA (STN) REGISTRY (STN)
Claims (2)
意味し、R4はアシル基を意味する。 ｍ及びｎは１〜３の整数を意味する。 Ａは （式中R7は水素原子又は低級アルキル基を意味し、Ｘは
薬理学的に許容できるアニオンを意味する）で示される
基を意味する〕 で表される糖類縁化合物又はその薬理学的に許容できる
塩。(1) General formula [In the formula, R 1 , R 2 , and R 3 represent the same or different lower alkyl groups, and R 4 represents an acyl group. m and n each represent an integer of 1 to 3. A is (Wherein, R 7 represents a hydrogen atom or a lower alkyl group, and X represents a pharmacologically acceptable anion). Acceptable salt.
意味し、R4はアシル基を意味する。 ｍ及びｎは１〜３の整数を意味する。 Ａは （式中R7は水素原子又は低級アルキル基を意味し、Ｘは
薬理学的に許容できるアニオンを意味する）で示される
基を意味する〕 で表される糖類縁化合物又はその薬理学的に許容できる
塩を有効成分とする抗PAF剤が有効な疾患の治療・予防
剤。2. The general formula [In the formula, R 1 , R 2 , and R 3 represent the same or different lower alkyl groups, and R 4 represents an acyl group. m and n each represent an integer of 1 to 3. A is (Wherein, R 7 represents a hydrogen atom or a lower alkyl group, and X represents a pharmacologically acceptable anion). An agent for treating or preventing a disease for which an anti-PAF agent containing an acceptable salt as an active ingredient is effective.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1344683A JP2933962B2 (en) | 1989-12-27 | 1989-12-27 | Sugar-related compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1344683A JP2933962B2 (en) | 1989-12-27 | 1989-12-27 | Sugar-related compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03200779A JPH03200779A (en) | 1991-09-02 |
| JP2933962B2 true JP2933962B2 (en) | 1999-08-16 |
Family
ID=18371173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1344683A Expired - Fee Related JP2933962B2 (en) | 1989-12-27 | 1989-12-27 | Sugar-related compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2933962B2 (en) |
-
1989
- 1989-12-27 JP JP1344683A patent/JP2933962B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03200779A (en) | 1991-09-02 |
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