HRP20020441A2 - 1-oxa-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof - Google Patents
1-oxa-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof Download PDFInfo
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- HRP20020441A2 HRP20020441A2 HR20020441A HRP20020441A HRP20020441A2 HR P20020441 A2 HRP20020441 A2 HR P20020441A2 HR 20020441 A HR20020441 A HR 20020441A HR P20020441 A HRP20020441 A HR P20020441A HR P20020441 A2 HRP20020441 A2 HR P20020441A2
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- 238000002360 preparation method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000003112 inhibitor Substances 0.000 title claims description 7
- YFWSSFNTRGQIHS-UHFFFAOYSA-N 5-oxatetracyclo[12.4.0.02,6.08,13]octadeca-1(18),2,6,8,10,12,14,16-octaene Chemical compound O1CC=C2C3=C(C4=C(C=C12)C=CC=C4)C=CC=C3 YFWSSFNTRGQIHS-UHFFFAOYSA-N 0.000 title claims description 6
- 108060008682 Tumor Necrosis Factor Proteins 0.000 title description 39
- 102000003390 tumor necrosis factor Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 95
- -1 C1-C4-alkoxycarbonyl Chemical group 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000003435 aroyl group Chemical group 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
- CLINQEWDDDRRPF-UHFFFAOYSA-N 11-chloro-2-methyl-1,8-dioxa-dibenzo[e,h]azulene Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(C)=C2 CLINQEWDDDRRPF-UHFFFAOYSA-N 0.000 claims description 6
- QFZOVBJSRWVQNL-UHFFFAOYSA-N 2-methyl-1,8-dioxa-dibenzo[e,h]azulene Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(C)=C2 QFZOVBJSRWVQNL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- RROOAGSDDXQRDC-UHFFFAOYSA-N 1,8-dioxa-dibenzo[e,h]azulene-2-carbaldehyde Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(C=O)=C2 RROOAGSDDXQRDC-UHFFFAOYSA-N 0.000 claims description 5
- 102000004127 Cytokines Human genes 0.000 claims description 5
- 108090000695 Cytokines Proteins 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000001575 pathological effect Effects 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- NLARBPLKQPGUTD-UHFFFAOYSA-N 11-chloro-1,8-dioxa-dibenzo[e,h]azulene-2-carbaldehyde Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(C=O)=C2 NLARBPLKQPGUTD-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- AYDWNSJCXKHELQ-UHFFFAOYSA-N 3,13-dioxatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-ylmethanol Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(CO)=C2 AYDWNSJCXKHELQ-UHFFFAOYSA-N 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- QTALJSHNNYKGRL-UHFFFAOYSA-N 2-[(17-chloro-3,13-dioxatetracyclo[12.4.0.02,6.07,12]octadeca-1(14),2(6),4,7,9,11,15,17-octaen-4-yl)methoxy]-N,N-dimethylethanamine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(COCCN(C)C)=C2 QTALJSHNNYKGRL-UHFFFAOYSA-N 0.000 claims description 2
- YRXGPWHDJIJWDY-UHFFFAOYSA-N 3-(3,13-dioxatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-ylmethoxy)-N,N-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1OC(COCCCN(C)C)=C2 YRXGPWHDJIJWDY-UHFFFAOYSA-N 0.000 claims description 2
- HFCYFKOJNVVKJN-UHFFFAOYSA-N 3-[(17-chloro-3,13-dioxatetracyclo[12.4.0.02,6.07,12]octadeca-1(14),2(6),4,7,9,11,15,17-octaen-4-yl)methoxy]-N,N-dimethylpropan-1-amine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(COCCCN(C)C)=C2 HFCYFKOJNVVKJN-UHFFFAOYSA-N 0.000 claims description 2
- CTUIGBYLDNOGTA-UHFFFAOYSA-N C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(COCCCN)=C2 Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(COCCCN)=C2 CTUIGBYLDNOGTA-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- OJXHWRBJNVMNFI-UHFFFAOYSA-N C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(CO)=C2 Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1OC(CO)=C2 OJXHWRBJNVMNFI-UHFFFAOYSA-N 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 38
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 30
- 108010002352 Interleukin-1 Proteins 0.000 description 25
- 102000000589 Interleukin-1 Human genes 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000002158 endotoxin Substances 0.000 description 16
- 230000028327 secretion Effects 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 11
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- 125000000217 alkyl group Chemical group 0.000 description 10
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- 238000012360 testing method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 125000002252 acyl group Chemical group 0.000 description 8
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- 238000009835 boiling Methods 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 230000006433 tumor necrosis factor production Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
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- BIQKMIYHLQKJDX-UHFFFAOYSA-N 6-(2-oxopropyl)-6h-benzo[b][1]benzothiepin-5-one Chemical compound O=C1C(CC(=O)C)C2=CC=CC=C2SC2=CC=CC=C21 BIQKMIYHLQKJDX-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical group C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
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- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20020441A HRP20020441A2 (en) | 2002-05-21 | 2002-05-21 | 1-oxa-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof |
| US10/515,678 US20050209214A1 (en) | 2002-05-21 | 2003-05-20 | 1-oxa-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| PL03374398A PL374398A1 (en) | 2002-05-21 | 2003-05-20 | 1-oxa-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof |
| AU2003232371A AU2003232371A1 (en) | 2002-05-21 | 2003-05-20 | 1-oxa-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof |
| PCT/HR2003/000024 WO2003097649A2 (en) | 2002-05-21 | 2003-05-20 | 1-oxa-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof |
| JP2004505381A JP2005532327A (ja) | 2002-05-21 | 2003-05-20 | 腫瘍壊死因子産生の阻害剤として１−オキサ−ジベンゾアズレン及びその製造用中間体 |
| CNB038161079A CN1315838C (zh) | 2002-05-21 | 2003-05-20 | 作为肿瘤坏死因子产生的抑制剂的1－氧杂－二苯并薁类和制备该类化合物的中间体 |
| HK06102100.7A HK1081950B (en) | 2002-05-21 | 2003-05-20 | 1-oxa-dibenzoazulenes as inhibitors of thmour necrosis factor production and intermediates for the preparation thereof |
| EP03752867A EP1506204A2 (en) | 2002-05-21 | 2003-05-20 | 1-oxa-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof |
| CA002485214A CA2485214A1 (en) | 2002-05-21 | 2003-05-20 | 1-oxa-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof |
| YU99404A RS99404A (sr) | 2002-05-21 | 2003-05-20 | 1-oksa-dibenzoazuleni kao inhibitori stvaranja faktora tumorske nekroze i međuproizvodi za njihovo pripremanje |
| ARP030101759A AR040087A1 (es) | 2002-05-21 | 2003-05-21 | Derivados de 1-oxa-dibenzoazulenos para la inhibicion de la produccion del factor de necrosis tumoral, procedimiento para su preparacion e intermediarios para su sintesis |
| US10/995,954 US20050148577A1 (en) | 2002-05-21 | 2004-11-22 | 1-oxa-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof |
| IS7567A IS7567A (is) | 2002-05-21 | 2004-11-29 | 1-oxa-díbensóasúlen sem latar æxlisdrepþáttar framleiðslu og milliefni til framleiðslu á þeim |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20020441A HRP20020441A2 (en) | 2002-05-21 | 2002-05-21 | 1-oxa-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020441A2 true HRP20020441A2 (en) | 2003-12-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020441A HRP20020441A2 (en) | 2002-05-21 | 2002-05-21 | 1-oxa-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediate for preparation thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20050209214A1 (sr) |
| EP (1) | EP1506204A2 (sr) |
| JP (1) | JP2005532327A (sr) |
| CN (1) | CN1315838C (sr) |
| AR (1) | AR040087A1 (sr) |
| AU (1) | AU2003232371A1 (sr) |
| CA (1) | CA2485214A1 (sr) |
| HR (1) | HRP20020441A2 (sr) |
| IS (1) | IS7567A (sr) |
| PL (1) | PL374398A1 (sr) |
| RS (1) | RS99404A (sr) |
| WO (1) | WO2003097649A2 (sr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| HRP20020304B1 (en) * | 2002-04-10 | 2008-04-30 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | 1-oxa-3-aza-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the production thereof |
| HRP20030160A2 (en) * | 2003-03-06 | 2005-04-30 | Pliva-Istra�iva�ki institut d.o.o. | 1-thiadibenzoazulene derivatives and biological action thereof |
| HRP20030955A2 (en) * | 2003-11-21 | 2005-08-31 | Pliva-Istra�iva�ki institut d.o.o. | USE OF 1-OXADIBENZO[e,h]AZULENES FOR THE MANUFACTURE OF PHARMACEUTICAL FORMULATIONS FOR THE TREATMENT AND PREVENTION OF CENTRAL NERVOUS SYSTEM DISEASES AND DISORDERS |
| EP1761545A2 (en) * | 2004-06-23 | 2007-03-14 | Janssen Pharmaceutica N.V. | Novel unsaturated tetracyclic tetrahydrofuran derivatives |
| EP1844053A2 (en) * | 2005-01-13 | 2007-10-17 | GlaxoSmithKline istrazivacki centar Zagreb d.o.o. | Anti-inflammatory macrolide conjugates |
| US7662824B2 (en) | 2005-03-18 | 2010-02-16 | Janssen Pharmaceutica Nv | Acylhydrazones as kinase modulators |
| CN117304166A (zh) * | 2023-09-20 | 2023-12-29 | 贵州农业职业学院 | 一种新的扎托布洛芬衍生物及其制备方法和应用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CH532038A (de) * | 1970-05-25 | 1972-12-31 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Cycloheptenderivaten |
| US3859439A (en) * | 1970-05-26 | 1975-01-07 | Ciba Geigy Corp | 2,3-dihydro-5 -trifluoromethyl-1h-dibenzo(2,3:6,7) thiepino (4,5-c) pyrroles as cns-depressants |
| US3711489A (en) * | 1971-03-31 | 1973-01-16 | Pfizer | Certain 8,9-dihydro(3,4,7,8)cycloocta(1,2-d)imidazoles |
| US4112110A (en) * | 1974-02-22 | 1978-09-05 | Ciba-Geigy Corporation | Oxygenated azatetracyclic compounds |
| US3974285A (en) * | 1974-04-10 | 1976-08-10 | Merck & Co., Inc. | 10,11-Furo-derivatives of cyproheptadine |
| US3894032A (en) * | 1974-04-10 | 1975-07-08 | Merck & Co Inc | 10,11-Furo derivatives of cyproheptadine |
| US4044143A (en) * | 1975-01-30 | 1977-08-23 | Merck & Co., Inc. | 10,11-Bis-(hydroxyalkyl) derivatives of cyproheptadine |
| US4271179A (en) * | 1976-05-24 | 1981-06-02 | Akzona Incorporated | 1,2,3,3a,8,12b-Hexahydro-dibenzo[1,2;5,6]cyclohepta[3,4-C]pyrroles and pharmaceutical use thereof |
| NL7605526A (nl) * | 1976-05-24 | 1977-11-28 | Akzo Nv | Nieuwe tetracyclische derivaten. |
| US4198421A (en) * | 1978-11-30 | 1980-04-15 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2-substituted-dibenzo[2,3:6,7]oxepino[4,5-d]imidazoles |
| US4267184A (en) * | 1979-02-08 | 1981-05-12 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-(substituted-thio)pyrroles and their corresponding sulfoxides and sulfones |
| US4267190A (en) * | 1980-04-18 | 1981-05-12 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-α,α-bis(polyfluoromethyl)-1H-pyrrole-2-methanethiols |
| US5840749A (en) * | 1989-08-25 | 1998-11-24 | Hoechst Marion Roussel, Inc. | N-hydroxy-dibenz b,e!oxepinalkylamines, N-hydroxy-dibenz b,e!oxepinalkanoic acid amides and related heterocyclic analogues |
| EP0887339A1 (de) * | 1997-06-27 | 1998-12-30 | Boehringer Mannheim Gmbh | Neue Azulenderivate und diese enthaltende Arzneimittel |
| UA52778C2 (uk) * | 1997-10-10 | 2003-01-15 | Янссен Фармацевтика Н.В. | Галогенозаміщені тетрациклічні похідні тетрагідрофурану, спосіб їх отримання та композиція на їх основі |
| HRP20000310A2 (en) * | 2000-05-17 | 2002-02-28 | Pliva Farmaceutska Ind Dioniko | New dibenzoazulene compounds as tumor necrosis factor inhibitors |
| HRP20020440B1 (en) * | 2002-05-21 | 2008-02-29 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | 1-aza-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof |
-
2002
- 2002-05-21 HR HR20020441A patent/HRP20020441A2/hr not_active Application Discontinuation
-
2003
- 2003-05-20 RS YU99404A patent/RS99404A/sr unknown
- 2003-05-20 CA CA002485214A patent/CA2485214A1/en not_active Abandoned
- 2003-05-20 WO PCT/HR2003/000024 patent/WO2003097649A2/en not_active Ceased
- 2003-05-20 US US10/515,678 patent/US20050209214A1/en not_active Abandoned
- 2003-05-20 AU AU2003232371A patent/AU2003232371A1/en not_active Abandoned
- 2003-05-20 CN CNB038161079A patent/CN1315838C/zh not_active Expired - Fee Related
- 2003-05-20 JP JP2004505381A patent/JP2005532327A/ja active Pending
- 2003-05-20 EP EP03752867A patent/EP1506204A2/en not_active Withdrawn
- 2003-05-20 PL PL03374398A patent/PL374398A1/xx not_active Application Discontinuation
- 2003-05-21 AR ARP030101759A patent/AR040087A1/es not_active Application Discontinuation
-
2004
- 2004-11-22 US US10/995,954 patent/US20050148577A1/en not_active Abandoned
- 2004-11-29 IS IS7567A patent/IS7567A/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IS7567A (is) | 2004-11-29 |
| US20050148577A1 (en) | 2005-07-07 |
| CN1665821A (zh) | 2005-09-07 |
| JP2005532327A (ja) | 2005-10-27 |
| RS99404A (sr) | 2006-10-27 |
| US20050209214A1 (en) | 2005-09-22 |
| WO2003097649A3 (en) | 2004-04-29 |
| AU2003232371A8 (en) | 2003-12-02 |
| CN1315838C (zh) | 2007-05-16 |
| EP1506204A2 (en) | 2005-02-16 |
| HK1081950A1 (en) | 2006-05-26 |
| CA2485214A1 (en) | 2003-11-27 |
| AR040087A1 (es) | 2005-03-16 |
| PL374398A1 (en) | 2005-10-17 |
| WO2003097649A2 (en) | 2003-11-27 |
| AU2003232371A1 (en) | 2003-12-02 |
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