SK283922B6 - 2,3-Diarylpyrazolo[1,5-b]pyridazínové zlúčeniny, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents
2,3-Diarylpyrazolo[1,5-b]pyridazínové zlúčeniny, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie Download PDFInfo
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- SK283922B6 SK283922B6 SK294-2000A SK2942000A SK283922B6 SK 283922 B6 SK283922 B6 SK 283922B6 SK 2942000 A SK2942000 A SK 2942000A SK 283922 B6 SK283922 B6 SK 283922B6
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- SK
- Slovakia
- Prior art keywords
- formula
- alkyl
- pyridazine
- alkoxy
- compounds
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- 150000004892 pyridazines Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000003112 inhibitor Substances 0.000 title description 4
- 108010037462 Cyclooxygenase 2 Proteins 0.000 title description 3
- 102000010907 Cyclooxygenase 2 Human genes 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 120
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 31
- -1 C1-6alkylsulphonyl Chemical group 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- 230000004054 inflammatory process Effects 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 206010061218 Inflammation Diseases 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 208000002193 Pain Diseases 0.000 claims abstract description 4
- 206010037660 Pyrexia Diseases 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- WENBZMSCUCYCFV-UHFFFAOYSA-N 6-(difluoromethoxy)-2-(3-fluorophenyl)-3-(4-methylsulfonylphenyl)pyrazolo[1,5-b]pyridazine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C2C=CC(OC(F)F)=NN2N=C1C1=CC=CC(F)=C1 WENBZMSCUCYCFV-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 231100000504 carcinogenesis Toxicity 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
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- 206010061289 metastatic neoplasm Diseases 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 7
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 5
- 229940124639 Selective inhibitor Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- 239000007787 solid Substances 0.000 description 37
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 239000011541 reaction mixture Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 239000000284 extract Substances 0.000 description 10
- XQLBZTCUEJYJOB-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-methylsulfonyl-3-(4-methylsulfonylphenyl)pyrazolo[1,5-b]pyridazine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C2C=CC(S(C)(=O)=O)=NN2N=C1C1=CC=C(F)C=C1 XQLBZTCUEJYJOB-UHFFFAOYSA-N 0.000 description 9
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- 230000005764 inhibitory process Effects 0.000 description 8
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- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000012267 brine Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 4
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Classifications
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9718792.6A GB9718792D0 (en) | 1997-09-05 | 1997-09-05 | Chemical compounds |
| GBGB9727116.7A GB9727116D0 (en) | 1997-12-23 | 1997-12-23 | Chemical compounds |
| PCT/EP1998/005558 WO1999012930A1 (en) | 1997-09-05 | 1998-09-03 | 2,3-diaryl-pyrazolo[1,5-b]pyridazines derivatives, their prepa ration and their use as cyclooxygenase 2 (cox-2) inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK2942000A3 SK2942000A3 (en) | 2001-03-12 |
| SK283922B6 true SK283922B6 (sk) | 2004-05-04 |
Family
ID=26312181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK294-2000A SK283922B6 (sk) | 1997-09-05 | 1998-09-03 | 2,3-Diarylpyrazolo[1,5-b]pyridazínové zlúčeniny, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie |
Country Status (28)
| Country | Link |
|---|---|
| US (4) | US6451794B1 (pt) |
| EP (3) | EP1032575B1 (pt) |
| KR (1) | KR100382619B1 (pt) |
| CN (1) | CN1155600C (pt) |
| AP (1) | AP1354A (pt) |
| AT (3) | ATE317845T1 (pt) |
| AU (1) | AU744997B2 (pt) |
| BG (1) | BG64420B1 (pt) |
| BR (1) | BR9812046A (pt) |
| CA (1) | CA2303152A1 (pt) |
| DE (3) | DE69816651T2 (pt) |
| DK (1) | DK1032575T3 (pt) |
| EA (1) | EA002775B1 (pt) |
| EE (1) | EE04617B1 (pt) |
| ES (3) | ES2256817T3 (pt) |
| HR (1) | HRP20000122B1 (pt) |
| HU (1) | HUP0003644A3 (pt) |
| IL (1) | IL134688A (pt) |
| IS (1) | IS5389A (pt) |
| NO (1) | NO315559B1 (pt) |
| NZ (1) | NZ502985A (pt) |
| PL (1) | PL194557B1 (pt) |
| PT (1) | PT1032575E (pt) |
| SK (1) | SK283922B6 (pt) |
| TR (1) | TR200000595T2 (pt) |
| TW (1) | TW570922B (pt) |
| WO (1) | WO1999012930A1 (pt) |
| YU (1) | YU11900A (pt) |
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU11900A (sh) * | 1997-09-05 | 2002-11-15 | Glaxo Group Limited | Derivati 2,3-diaril-pirazolo (1,5-b) piridazina, njihovo dobijanje i njihova upotreba kao inhibitora ciklooksigenaze 2(cox-2) |
| CZ20011556A3 (cs) * | 1998-11-03 | 2001-11-14 | Glaxo Group Limited | Pyrazolopyridinové deriváty |
| US6833373B1 (en) | 1998-12-23 | 2004-12-21 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| ATE261444T1 (de) | 1999-02-27 | 2004-03-15 | Glaxo Group Ltd | Pyrazolopyridine |
| GB9929039D0 (en) * | 1999-12-08 | 2000-02-02 | Glaxo Group Ltd | Medicaments |
| GB9930358D0 (en) * | 1999-12-22 | 2000-02-09 | Glaxo Group Ltd | Process for the preparation of chemical compounds |
| CN100486573C (zh) | 1999-12-23 | 2009-05-13 | 硝化医药股份有限公司 | 硝基化的和亚硝基化的环加氧酶-2抑制剂、组合物及其用途 |
| GB0002312D0 (en) * | 2000-02-01 | 2000-03-22 | Glaxo Group Ltd | Medicaments |
| DE60129330T2 (de) | 2000-07-20 | 2008-04-10 | Lauras As | Verwendung von cox-2 inhibitoren als immunostimulantien zur behandlung von hiv oder aids |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| GB0021494D0 (en) * | 2000-09-01 | 2000-10-18 | Glaxo Group Ltd | Chemical comkpounds |
| GB0025449D0 (en) * | 2000-10-17 | 2000-11-29 | Glaxo Group Ltd | Chemical compounds |
| ES2243579T3 (es) | 2000-12-15 | 2005-12-01 | Glaxo Group Ltd | Derivados de pirazolopirideno. |
| WO2002048147A2 (en) | 2000-12-15 | 2002-06-20 | Glaxo Group Limited | Pyrazolopyridines |
| ES2227451T3 (es) | 2001-03-08 | 2005-04-01 | Smithkline Beecham Corporation | Derivados de pirazolopiridina. |
| US7034030B2 (en) | 2001-03-30 | 2006-04-25 | Smithkline Beecham Corporation | Pyralopyridines, process for their preparation and use as therapeutic compounds |
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- 1998-09-03 WO PCT/EP1998/005558 patent/WO1999012930A1/en not_active Application Discontinuation
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- 1998-09-03 DK DK98947502T patent/DK1032575T3/da active
- 1998-09-03 KR KR10-2000-7002322A patent/KR100382619B1/ko not_active IP Right Cessation
- 1998-09-03 AP APAP/P/2000/001753A patent/AP1354A/en active
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- 1998-09-03 EA EA200000188A patent/EA002775B1/ru not_active IP Right Cessation
- 1998-09-03 EP EP03077298A patent/EP1369421B1/en not_active Expired - Lifetime
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- 1998-09-03 ES ES98947502T patent/ES2203985T3/es not_active Expired - Lifetime
- 1998-09-03 CA CA002303152A patent/CA2303152A1/en not_active Abandoned
- 1998-09-03 CN CNB988108763A patent/CN1155600C/zh not_active Expired - Fee Related
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