AU747690B2 - Naphthyl intermediates - Google Patents
Naphthyl intermediates Download PDFInfo
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- AU747690B2 AU747690B2 AU32579/00A AU3257900A AU747690B2 AU 747690 B2 AU747690 B2 AU 747690B2 AU 32579/00 A AU32579/00 A AU 32579/00A AU 3257900 A AU3257900 A AU 3257900A AU 747690 B2 AU747690 B2 AU 747690B2
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- AU
- Australia
- Prior art keywords
- 6alkyl
- phenyl
- oco
- substituted phenyl
- ocoar
- Prior art date
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- Ceased
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- 239000000543 intermediate Substances 0.000 title description 4
- 125000001624 naphthyl group Chemical group 0.000 title description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 101710150115 Sensory rhodopsin-2 Proteins 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 210000000988 bone and bone Anatomy 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 208000001132 Osteoporosis Diseases 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- -1 C1.3alkoxy Chemical group 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KSRYRFVUQXCXBG-UHFFFAOYSA-N 2,4-bis(3-methoxyphenyl)butanoic acid Chemical compound COC1=CC=CC(CCC(C(O)=O)C=2C=C(OC)C=CC=2)=C1 KSRYRFVUQXCXBG-UHFFFAOYSA-N 0.000 description 2
- FAURBSHOCYRGEO-UHFFFAOYSA-N 6-methoxy-2-(3-methoxyphenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound COC1=CC=CC(C2C(C3=CC=C(OC)C=C3CC2)=O)=C1 FAURBSHOCYRGEO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WLGUOPJCFSEDOP-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl] acetate Chemical compound COC1=CC=CC(C=2CCC3=CC(OC)=CC=C3C=2OC(C)=O)=C1 WLGUOPJCFSEDOP-UHFFFAOYSA-N 0.000 description 2
- DOHDMNAJBCAOJS-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl] acetate Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)OC(C)=O)=C1 DOHDMNAJBCAOJS-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- LQDHVNHVHAYANB-UHFFFAOYSA-N 1-(2-bromoethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCBr)=C1 LQDHVNHVHAYANB-UHFFFAOYSA-N 0.000 description 1
- HMZFNJNARQIWIJ-UHFFFAOYSA-N 2-(3-methoxyphenyl)naphthalen-1-ol Chemical compound COC1=CC=CC(C=2C(=C3C=CC=CC3=CC=2)O)=C1 HMZFNJNARQIWIJ-UHFFFAOYSA-N 0.000 description 1
- LEGPZHPSIPPYIO-UHFFFAOYSA-N 3-Methoxyphenylacetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1 LEGPZHPSIPPYIO-UHFFFAOYSA-N 0.000 description 1
- PRCYTOLMCWNPDO-UHFFFAOYSA-N 6-methoxy-2-(3-methoxyphenyl)naphthalen-1-ol Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)O)=C1 PRCYTOLMCWNPDO-UHFFFAOYSA-N 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 208000035474 group of disease Diseases 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 210000004914 menses Anatomy 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
S&F Ref: 447377D1
AUSTRALIA
PATENTS ACT 1990 COMPLETE SPECIFICATION FOR A STANDARD PATENT
ORIGINAL
.*ew
S
S
t
S.
*SS*
Name and Address of Applicant: Actual Inventor(s): Address for Service: Invention Title: Eli Lilly and Company Lilly Corporate Center Indianapolis Indiana 46285 United States of America Henry U Bryant Thomas A Crowell Charles D Jones Alan D Palkowitz Spruson Ferguson St Martins Tower 31 Market Street Sydney NSW 2000 Naphthyl Intermediates The following statement is a full description of this invention, including the best method of performing it known to me/us:- 5845c Naphthyl Intermediates Osteoporosis describes a group of diseases which arises from diverse aetiologies, but which are characterised by the net loss of bone mass per unit volume. The consequence of this loss of bone mass and resulting bone fracture is the failure of the skeleton to provide adequate support for the body. One of the most common types of osteoporosis is associated with menopause. Most women lose from about 20% to about 60% of the bone mass in the trabecular compartment of the bone within 3 to 6 years after the cessation of menses. This rapid loss is generally associated with an increase of bone resorption and formation. However, the resorptive cycle is more dominant and the result is a net loss of bone mass. Osteoporosis is a common and serious disease among postmenopausal women.
This invention relates to novel intermediates in the manufacture of the naphthyl compounds of application 43284/97 which are useful in the treatment of osteoporosis. The disclosure of application 43284/97 is incorporated herein in its entirety.
The invention provides compounds of the formula I which are useful for preparing the pharmaceutically active compounds of application 43284/97:
R
2 a R3a la/R
S
R
I
wherein: R l a is -H or -OR 5 in which R 5 is a hydroxy protecting group; R 2 a is H, OH, O(C14alkyl), OCOAr where Ar is phenyl or substituted phenyl, OCO(Ci.alkyl), O(CO)O(Ci.alkyl), or OSO 2
(C
4 6. alkyl); R 3a is H, or OR 7 in which R 7 is a hydroxy protecting group; R 4a is H, CH3, OH, O(C14alkyl), S. 20 OCOAr where Ar is phenyl or substituted phenyl, O(CO)OAr where Ar is phenyl or substituted phenyl, OCO(Ci.alkyl), O(CO)O(Ci-6alkyl), or OSO2(C46alkyl); with the proviso that both R 3 a and
R
4 a cannot be hydrogen.
The invention also provides compounds of the formula II which are useful for preparing the pharmaceutically active compounds of application 43284/97:
R
2 a R R 3 a RA la V V 3 [R:\LIBVVI02528speci.doc:NJC 1la wherein: Ria is H or OR 6 in which R 6 is a hydroxy protecting group; R 2 a is H, OH, O(Cl.~alkyI), OCOAr where Ar is phenyl or substituted phenyl, OCO(C.6alkyl), O(CO)O(Ci-6alkyI), or 0S0 2
(C
4 6alkyl); R 3 a is H, or OR 7 in which R 7 is a hydroxy protecting group; R 4 a is H, CH 3 OH, O(C,4.alkyl), OCOAr where Ar is phenyl or substituted phenyl, OCO(Ci.6alkyl), O(CO)O(Ci-6alkyI), or 0S0 2
(C
4 6alkyl), with the proviso that only one of R 2 a, RUa and R 4 a can be hydrogen; R 8 is OH or OCO(CI.
6alkyl); wherein the dotted line represents optional unsaturation; or a pharmaceutically acceptable salt or solvate thereof.
[R:\LIBVV]02528speci.doc:NJC General terms used in the description of compounds herein described bear their usual meanings. For example, "Ci.4alkyl" refers to straight or branched aliphatic chains of 1 to 4 carbon atoms including methyl, ethyl, propyl, iso-propyl, n-butyl, and the like; and "Cl-6alkyl" encompasses the groups included in the definition of "Ci-4alkyl" in addition to groups such as pentyl, iso-pentyl, hexyl, and the like.
The term "substituted phenyl" refers to a phenyl group having one or more substituents selected from the group consisting of C1-4alkyl, C1.3alkoxy, hydroxy, nitro, chloro, fluoro, tri(chloro or fluoro)methyl, and the like. "C-4alkoxy" refers to a C-4alkyl group attached through an oxygen bridge, such as methoxy, ethoxy, n-propoxy, and isopropoxy, butoxy, and the like. Of these C14alkoxy groups, methoxy is highly preferred.
Compounds of formula I where at least two of the R 2 a, R3a, and R 4 a substituents are hydrogen are well known in the art and are prepared essentially as described by Boyle et al., in US. 4 910 212 which is herein incorporated by reference. See, also, Collins, et al., Aust. Chem., 41:745-756 (1988); and Collins, et al., Aust. J. Chem., 37:2279-2294 (1984).
15 The following examples are provided to better elucidate the practice of the present invention and should not be interpreted in any way as to limit the scope 25 of same. Those skilled in the art will recognise that various modifications may be made while not departing from the spirit and scope of the invention. All publications and patent applications mentioned in the specification are indicative of the S level of those skilled in the art to which this invention pertains.
Examples NMR data for the following Examples were generated on a GE 300 MHz NMR instrument, and anhydrous d-6 DMSO was used as the solvent unless otherwise indicated.
Preparation 1 2,4-di-(3-methoxyphenyl) butyric acid A solution of 50.68g (305mmol) of 3-methoxyphenylacetic acid in 1.4L of anhydrous THF was prepared and cooled to -70 0 C under a nitrogen atmosphere. Slowly, 400mL of 1.6M (640mmol) of nbutyl lithium was added and the solution was allowed to stir for two hours at -70 0 C. A solution of 72.1g (335mmol) of 2-(3-methoxyphenyl)ethylbromide in 100mL of THF was added and the reaction was allowed to proceed for sixteen hours, while slowly warming to ambient temperature. The solvent was removed by evaporation in vacuo. The residue was dissolved in a solution of 50mL of 5N NaOH and 450mL of water and stirred for one hour. The aqueous solution was extracted three times with ether. The aqueous solution was acidified with the addition of 150mL of 5N HCI and the product extracted three times with CHCI 3 The organic extracts were combined, washed with brine and dried by filtration through anhydrous Na 2
SO
4 The solvent was removed by evaporation. This yielded of the title compound as a clear oil.
Example 1 2-(3-methoxyphenyl)-6-methoxy-1 -tetralone A solution of 90g (300mmol) of 2,4-di-(3-methoxyphenyl)butyric acid in 1.5L of CH 2
CI
2 was prepared and 62.4g (300mmol) of PC15 was slowly added. The reaction mixture was refluxed under a nitrogen atmosphere for four hours. The solvent was removed by evaporation. The residue was C08226 slurried with 100mL of aqueous NaHCO3 and the slurry extracted three times with CHCI 3 The combined organic extracts was washed with brine, dried with Na 2 SO4, and evaporated to dryness.
The product was crystallised from 2-propanol at -700C and then twice from MeOH at -70 0 C. This yielded 65g of the title compound as a tan solid, mp 81-82 0
C.
Example 2 1-Acetyloxy-2-(3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalene A suspension was prepared of 47g (167mmol) of 2-(3-methoxyphenyl)-6-methoxy-1-tetralone and 4.7g of p-toluenesulfonic acid mono-hydrate in 470mL of isopropenylacetate. The reaction mixture was refluxed for 48 hours under a nitrogen atmosphere. The reaction was allowed to cool and 10g of NaHCO 3 was added, the solution was poured into 500mL of an aqueous solution of NaHCO 3 The aqueous solution was extracted three times with 200mL portions of EtOAc. The combined organic extract was washed with brine, dried with Na2SO4, and evaporated to a dark oil. This yielded 52.7g of the title compound.
Example 3 1-Acetyloxy-2-(3-methoxyphenyl)-6-methoxynaphthalene A solution was prepared of 52.7g (162mmol) of 1-acetyloxy-2-(3-methoxyphenyl)-6-methoxy- 3,4-dihydronaphthalene and 36.9g (162mmol) of DDQ in 500mL of p-dioxane. The solution was heated to reflux for two hours under a nitrogen atmosphere. The reaction was allowed to cool and the solvent removed by evaporation. The residue was extracted by stirring in CHCI 3 for sixteen hours, then filtering to remove the insoluble material. The CHCI 3 extract was further purified by chromatography on a silica gel column eluted with CHCI 3 This resulted in a red oil, which was suspended in MeOH and crystallised at -70 0 C. This yielded 46.5g of the title compound as a low melting solid.
Example 4 25 1-Hydroxy-2-(3-methoxyphenyl)-6-methoxynaphthalene A suspension was prepared of 46.5g of 1-acetyloxy-2-(3-methoxyphenyl)-6methoxynaphthalene and 40mL of 5N HCI in 400mL of MeOH. The reaction mixture was heated to reflux for eleven hours. The reaction mixture was evaporated to a clear oil. This yielded 38.6g of the title compound. PMR: (CDCI 3 8.19ppm J=9.1Hz, 1H); 7.51-6.94ppm 5 8H); 5.91ppm 1H); 3.94ppm 3H) MS: mle=280 FD EA: Calc. for C 18
H
16 0 3 C, 77.12; H, 5.75 Found: C, 76.91; H, 5.81.
Example 1-Hydroxy-2-(3-methoxyphenyl)naphthalene In a manner analogous to Preparation 1 and Examples 1 to 4, the title compound was prepared.
PMR: 8.30ppm 1H); 7.80ppm 1H); 7.57-7.45ppm 4H); 7.40ppm J=7.1Hz, 1H); 7.35ppm J=6.0Hz, 1H); 7.06ppm 1H); 6.97ppm (dd, J=6.0Hz, 1H); 6.00ppm 1H); 3.90ppm 1H) MS: m/e=250 FD EA: Calc. for C 1 7
H
1 4 0 2 -0.21mol EtOAc: C, 79.52; H, 5.93 Found: C, 79.72; H, 5.63 C08226
Claims (4)
1. A compound of formula I: R 2 a R R 3 a a R 4 a wherein: R la is -H or -OR 5 in which R 5 is a hydroxy protecting group; R 2a is H, OH, O(C-4alkyl), OCOAr where Ar is phenyl or substituted phenyl, OCO(Ci-6alkyl), O(CO)O(Ci-6alkyl), or OS0
2 (C 4 6alkyl); R3a is H, or OR 7 in which R 7 is a hydroxy protecting group; R 4 a is H, CH 3 OH, O(Cl-alkyl), OCOAr where Ar is phenyl or substituted phenyl, O(CO)OAr where Ar is phenyl or substituted phenyl, OCO(Ci.alkyl), O(CO)O(Ci-6alkyl), or OSO2(C 4 6alkyl); with the proviso that both R 3 a and R 4 a cannot be hydrogen. t10 2. A compound of formula I, substantially as hereinbefore described with reference to any one of the examples.
3. A compound of formula II: R2a R 8 R 3 a O R4a SRla R SR II C wherein: Ria is H or OR 6 in which R 6 is a hydroxy protecting group; R 2a is H, OH, O(Ci4alkyl), 15 OCOAr where Ar is phenyl or substituted phenyl, OCO(Ci-6alkyl), O(CO)O(Ci-6alkyl), or OS0 2 (C 4 e•6alkyl); R 3 a is H, or OR 7 in which R 7 is a hydroxy protecting group; R 4 a is H, CH 3 OH, O(C-4alkyl), OCOAr where Ar is phenyl or substituted phenyl, OCO(Ci-6alkyl), O(CO)O(C1.6alkyl), or OS0 2 (C 4 6alkyl), with the proviso that only one of R 2a R 3 a and R 4 a can be hydrogen; R 8 is OH or OCO(C1. 6alkyl); wherein the dotted line represents optional unsaturation; or a pharmaceutically acceptable salt or solvate thereof.
4. A compound of formula II, substantially as hereinbefore described with reference to any one of the examples. Dated 4 March 2002 ELI LILLY AND COMPANY -Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON [R:\LIBVV]02528speci.doc:NJC
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU32579/00A AU747690B2 (en) | 1996-08-29 | 2000-05-08 | Naphthyl intermediates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60/025125 | 1996-08-29 | ||
| AU32579/00A AU747690B2 (en) | 1996-08-29 | 2000-05-08 | Naphthyl intermediates |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU43284/97A Division AU721467B2 (en) | 1996-08-29 | 1997-08-22 | Naphthyl compounds, intermediates, compositions, and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3257900A AU3257900A (en) | 2000-07-13 |
| AU747690B2 true AU747690B2 (en) | 2002-05-16 |
Family
ID=3720096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU32579/00A Ceased AU747690B2 (en) | 1996-08-29 | 2000-05-08 | Naphthyl intermediates |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU747690B2 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277106A (en) * | 1964-01-23 | 1966-10-04 | Ciba Geigy Corp | Tetrahydronaphthalene and benzosuberane compounds |
-
2000
- 2000-05-08 AU AU32579/00A patent/AU747690B2/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277106A (en) * | 1964-01-23 | 1966-10-04 | Ciba Geigy Corp | Tetrahydronaphthalene and benzosuberane compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3257900A (en) | 2000-07-13 |
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