ES2266487T3 - Compuestos de pirazolopirina antivirales. - Google Patents
Compuestos de pirazolopirina antivirales. Download PDFInfo
- Publication number
- ES2266487T3 ES2266487T3 ES02723554T ES02723554T ES2266487T3 ES 2266487 T3 ES2266487 T3 ES 2266487T3 ES 02723554 T ES02723554 T ES 02723554T ES 02723554 T ES02723554 T ES 02723554T ES 2266487 T3 ES2266487 T3 ES 2266487T3
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- Prior art keywords
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- nhr
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- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 690
- 230000000840 anti-viral effect Effects 0.000 title description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 177
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 168
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 125
- 125000005843 halogen group Chemical group 0.000 claims abstract description 105
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 101
- 125000004429 atom Chemical group 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 49
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 48
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 41
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 37
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 36
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 30
- 239000012453 solvate Substances 0.000 claims abstract description 23
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 270
- 238000000034 method Methods 0.000 claims description 127
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 76
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 65
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- 238000011282 treatment Methods 0.000 claims description 44
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 42
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- 238000005694 sulfonylation reaction Methods 0.000 claims description 17
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 16
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- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 7
- 238000006268 reductive amination reaction Methods 0.000 claims description 7
- 229940093257 valacyclovir Drugs 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
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- 239000003443 antiviral agent Substances 0.000 claims description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
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- RMANLZQDOIEBGU-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC(C)C)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RMANLZQDOIEBGU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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- 229940079593 drug Drugs 0.000 claims description 3
- SQQVANPMGGBYDX-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 SQQVANPMGGBYDX-UHFFFAOYSA-N 0.000 claims description 3
- URUUOQUMOPTRRE-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 URUUOQUMOPTRRE-UHFFFAOYSA-N 0.000 claims description 3
- NLKACQGBKCKERK-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OCC(C)C)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 NLKACQGBKCKERK-UHFFFAOYSA-N 0.000 claims description 3
- FPZNHXIUFKJEHG-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-(2-methoxyethyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(NCCOC)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 FPZNHXIUFKJEHG-UHFFFAOYSA-N 0.000 claims description 2
- FDXDGPUMMWYVHH-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(NC(C)C)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 FDXDGPUMMWYVHH-UHFFFAOYSA-N 0.000 claims description 2
- ZBASGXKVNVIJCM-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-6-amine Chemical compound N=1N2C=C(NC(C)C)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 ZBASGXKVNVIJCM-UHFFFAOYSA-N 0.000 claims description 2
- OUZIVEFGDDPQGR-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(N)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 OUZIVEFGDDPQGR-UHFFFAOYSA-N 0.000 claims description 2
- NUKYEHFDVLNGFZ-UHFFFAOYSA-N 4-[5-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 NUKYEHFDVLNGFZ-UHFFFAOYSA-N 0.000 claims description 2
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- XDGMTTPBMWQFBC-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=C(NC2CCCC2)C=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 XDGMTTPBMWQFBC-UHFFFAOYSA-N 0.000 claims description 2
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- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 208000008732 thymoma Diseases 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940107931 zovirax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28274901P | 2001-04-10 | 2001-04-10 | |
| US282749P | 2001-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2266487T3 true ES2266487T3 (es) | 2007-03-01 |
Family
ID=23082954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02723554T Expired - Lifetime ES2266487T3 (es) | 2001-04-10 | 2002-03-21 | Compuestos de pirazolopirina antivirales. |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7141569B2 (OSRAM) |
| EP (1) | EP1377575B1 (OSRAM) |
| JP (1) | JP4219171B2 (OSRAM) |
| AT (1) | ATE332301T1 (OSRAM) |
| DE (1) | DE60212949T2 (OSRAM) |
| ES (1) | ES2266487T3 (OSRAM) |
| WO (1) | WO2002083672A1 (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE364043T1 (de) * | 2001-09-07 | 2007-06-15 | Smithkline Beecham Corp | Pyrazolo-pyridine für die behandlung von herpes- ansteckungen |
| AU2003217712A1 (en) | 2002-03-07 | 2003-09-22 | Smithkline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| US7153863B2 (en) * | 2002-10-03 | 2006-12-26 | Smithkline Beecham Corporation | Therapeutic compounds based on pyrazolopyridline derivatives |
| US7812022B2 (en) * | 2004-12-21 | 2010-10-12 | Glaxosmithkline Llc | 2-pyrimidinyl pyrazolopyridine ErbB kinase inhibitors |
| EP1971606B1 (en) * | 2005-12-05 | 2013-04-24 | GlaxoSmithKline LLC | 2-pyrimidinyl pyrazolopyridine erbb kinase inhibitors |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| EP2402335A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| EP2402336A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| RU2021109549A (ru) | 2014-08-29 | 2021-05-13 | Тес Фарма С.Р.Л. | ИНГИБИТОРЫ α-АМИНО-β-КАРБОКСИМУКОНАТ ε-СЕМИАЛЬДЕГИД-ДЕКАРБОКСИЛАЗЫ |
| US9944975B2 (en) | 2015-09-03 | 2018-04-17 | Abbott Molecular Inc. | Hybridization buffers |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| DK3377488T3 (da) | 2015-11-19 | 2022-10-03 | Incyte Corp | Heterocykliske forbindelser som immunomodulatorer |
| MY199705A (en) | 2015-12-22 | 2023-11-20 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| CN108779490A (zh) * | 2016-01-08 | 2018-11-09 | 雅培分子公司 | 包含硫氰酸胍的杂交缓冲液 |
| TW201808950A (zh) | 2016-05-06 | 2018-03-16 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MA46045A (fr) | 2016-08-29 | 2021-04-28 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| KR102641030B1 (ko) | 2016-12-22 | 2024-02-29 | 인사이트 코포레이션 | Pd-l1 내재화 유도제로서의 테트라하이드로 이미다조[4,5-c]피리딘 유도체 |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| US20180179202A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119266A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Benzooxazole derivatives as immunomodulators |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| FI3774791T3 (fi) | 2018-03-30 | 2023-03-21 | Incyte Corp | Heterosyklisiä yhdisteitä immunomodulaattoreina |
| BR112020022936A2 (pt) | 2018-05-11 | 2021-02-02 | Incyte Corporation | derivados de tetra-hidro-imidazo[4,5-c]piridina como imunomoduladores de pd-l1 |
| US11753406B2 (en) | 2019-08-09 | 2023-09-12 | Incyte Corporation | Salts of a PD-1/PD-L1 inhibitor |
| MX2022003578A (es) | 2019-09-30 | 2022-05-30 | Incyte Corp | Compuestos de pirido[3,2-d]pirimidina como inmunomoduladores. |
| BR112022009031A2 (pt) | 2019-11-11 | 2022-10-11 | Incyte Corp | Sais e formas cristalinas de um inibidor de pd-1/pd-l1 |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| MX2023005362A (es) | 2020-11-06 | 2023-06-22 | Incyte Corp | Proceso para hacer un inhibidor de proteina de muerte programada 1 (pd-1)/ligando de muerte programada 1 (pd-l1) y sales y formas cristalinas del mismo. |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5200478A (en) * | 1983-04-04 | 1993-04-06 | Solvay S.A. | Method for activating supported chromium oxide catalysts and olefin polymerization process carried out therewith |
| EP0151962A3 (en) | 1984-01-25 | 1985-10-02 | Beecham Group Plc | Pyrazolopyridine derivatives |
| GB8404584D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| GB8404586D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| US5002941A (en) | 1985-12-12 | 1991-03-26 | Smithkline Beecham Corporation | Pyrrolo(1,2-a)imidazole and imidazo(1,2-a)pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
| US4925849A (en) * | 1987-06-15 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | Pharmaceutically useful pyrazolopyridines |
| US5541188A (en) * | 1987-09-15 | 1996-07-30 | The Rowett Research Institute | Therapeutic applications of beta-adrenergic agonists |
| US5155114A (en) * | 1989-01-23 | 1992-10-13 | Fujisawa Pharmaceutical Company, Ltd. | Method of treatment using pyrazolopyridine compound |
| GB8901423D0 (en) * | 1989-01-23 | 1989-03-15 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| AU6355190A (en) | 1989-06-13 | 1991-01-17 | Smithkline Beecham Corporation | Inhibition of interleukin-1 and tumor necrosis factor production by monocytes and/or macrophages |
| AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
| WO1991019497A1 (en) | 1990-06-12 | 1991-12-26 | Smithkline Beecham Corporation | Inhibition of 5-lipoxygenase and cyclooxygenase pathway mediated diseases |
| GB9015764D0 (en) | 1990-07-18 | 1990-09-05 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| EP0497258B1 (en) | 1991-01-29 | 2002-01-02 | Fujisawa Pharmaceutical Co., Ltd. | Use of adenosine antagonists in the prevention and treatment of pancreatitis and ulcer |
| GB9107513D0 (en) | 1991-04-10 | 1991-05-29 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| US5300478A (en) * | 1993-01-28 | 1994-04-05 | Zeneca Limited | Substituted fused pyrazolo compounds |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| KR100386542B1 (ko) * | 1993-12-29 | 2003-10-11 | 후지사와 야꾸힝 고교 가부시키가이샤 | 피라졸로피리딘아데노신길항제 |
| US5521213A (en) | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
| US5552422A (en) * | 1995-01-11 | 1996-09-03 | Merck Frosst Canada, Inc. | Aryl substituted 5,5 fused aromatic nitrogen compounds as anti-inflammatory agents |
| EA199700209A1 (ru) | 1995-04-04 | 1998-04-30 | Глаксо Груп Лимитед | ПРОИЗВОДНЫЕ ИМИДАЗО[1,2-a]ПИРИДИНА |
| US5700816A (en) * | 1995-06-12 | 1997-12-23 | Isakson; Peter C. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor |
| AU6111796A (en) * | 1995-06-12 | 1997-01-09 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5 -lipoxygenase inhibitor |
| EP0833664A1 (en) | 1995-06-12 | 1998-04-08 | G.D. SEARLE & CO. | Combination of a cyclooxygenase-2 inhibitor and a leukotriene b 4? receptor antagonist for the treatment of inflammations |
| FR2757166B1 (fr) | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2757059B1 (fr) | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Nouvelle application therapeutique des derives du pyrrole |
| WO1998056377A1 (en) | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
| HRP20000122B1 (en) | 1997-09-05 | 2003-06-30 | Glaxo Group Ltd | 2,3-diaryl-pyrazolo/1,5-b/pyridazines derivatives, their preparation and their use as cyclooxygenase 2 (cox-2) |
| CA2331878A1 (en) | 1998-05-14 | 1999-11-18 | G.D. Searle & Co. | 1,5-diaryl substituted pyrazoles as p38 kinase inhibitors |
| US6245789B1 (en) | 1998-05-19 | 2001-06-12 | The Procter & Gamble Company | HIV and viral treatment |
| FR2779724B1 (fr) | 1998-06-10 | 2001-04-20 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| BR9915011A (pt) | 1998-11-03 | 2001-08-07 | Glaxo Group Ltd | Compostos, método para a preparação dos mesmos, composição farmacêutica, métodos de tratamento de um indivìduo humano ou animal sofrendo de uma condição que é mediada pela inibição seletiva de cox-2 e sofrendo de um distúrbio inflamatório, e, uso de um composto |
| JP2002538157A (ja) | 1999-02-27 | 2002-11-12 | グラクソ グループ リミテッド | ピラゾロピリジン |
| ATE259796T1 (de) | 1999-06-28 | 2004-03-15 | Janssen Pharmaceutica Nv | Respiratorisches syncytialvirus replikation inhibitoren |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| AUPQ969800A0 (en) | 2000-08-28 | 2000-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| US7163940B2 (en) | 2000-12-15 | 2007-01-16 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyrimidine therapeutic compounds |
| ES2245380T3 (es) * | 2000-12-15 | 2006-01-01 | Glaxo Group Limited | Pirazolopiridinas. |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| US7034030B2 (en) * | 2001-03-30 | 2006-04-25 | Smithkline Beecham Corporation | Pyralopyridines, process for their preparation and use as therapeutic compounds |
| EP1372642A1 (en) * | 2001-03-30 | 2004-01-02 | SmithKline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
| ES2242028T3 (es) * | 2001-04-27 | 2005-11-01 | Smithkline Beecham Corporation | Derivados de pirazolo(1,5-a)piridina. |
| US7196095B2 (en) | 2001-06-25 | 2007-03-27 | Merck & Co., Inc. | (Pyrimidinyl) (phenyl) substituted fused heteroaryl p38 inhibiting and PKG kinase inhibiting compounds |
-
2002
- 2002-03-21 US US10/473,491 patent/US7141569B2/en not_active Expired - Fee Related
- 2002-03-21 JP JP2002581427A patent/JP4219171B2/ja not_active Expired - Fee Related
- 2002-03-21 WO PCT/US2002/008793 patent/WO2002083672A1/en not_active Ceased
- 2002-03-21 EP EP02723554A patent/EP1377575B1/en not_active Expired - Lifetime
- 2002-03-21 DE DE60212949T patent/DE60212949T2/de not_active Expired - Fee Related
- 2002-03-21 AT AT02723554T patent/ATE332301T1/de not_active IP Right Cessation
- 2002-03-21 ES ES02723554T patent/ES2266487T3/es not_active Expired - Lifetime
-
2006
- 2006-06-06 US US11/422,357 patent/US20060235043A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE60212949D1 (de) | 2006-08-17 |
| EP1377575B1 (en) | 2006-07-05 |
| ATE332301T1 (de) | 2006-07-15 |
| JP4219171B2 (ja) | 2009-02-04 |
| US20040167335A1 (en) | 2004-08-26 |
| DE60212949T2 (de) | 2007-01-04 |
| US7141569B2 (en) | 2006-11-28 |
| EP1377575A1 (en) | 2004-01-07 |
| US20060235043A1 (en) | 2006-10-19 |
| WO2002083672A1 (en) | 2002-10-24 |
| JP2004529926A (ja) | 2004-09-30 |
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