ES2286272T3 - Pirizolo-piridinas para el tratamiento de infecciones por herpes. - Google Patents
Pirizolo-piridinas para el tratamiento de infecciones por herpes. Download PDFInfo
- Publication number
- ES2286272T3 ES2286272T3 ES02759464T ES02759464T ES2286272T3 ES 2286272 T3 ES2286272 T3 ES 2286272T3 ES 02759464 T ES02759464 T ES 02759464T ES 02759464 T ES02759464 T ES 02759464T ES 2286272 T3 ES2286272 T3 ES 2286272T3
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- Prior art keywords
- formula
- compound
- group
- het
- cycloalkyl
- 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 - Lifetime
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- 238000011282 treatment Methods 0.000 title claims description 46
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 title claims description 12
- 208000015181 infectious disease Diseases 0.000 title description 17
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 128
- 125000000217 alkyl group Chemical group 0.000 claims description 125
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 57
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
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- 125000000304 alkynyl group Chemical group 0.000 claims description 10
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- HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 claims description 8
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 8
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 7
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- 241001529453 unidentified herpesvirus Species 0.000 claims description 7
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- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- 208000007514 Herpes zoster Diseases 0.000 claims description 6
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- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
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- VLFRCSMLQCOKRA-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-7-methylsulfanylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C=1C2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C(SC)=CC=1NC1CCCC1 VLFRCSMLQCOKRA-UHFFFAOYSA-N 0.000 claims description 4
- RYKRWMFYUZRWPQ-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-7-propan-2-ylsulfanylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C=1C2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C(SC(C)C)=CC=1NC1CCCC1 RYKRWMFYUZRWPQ-UHFFFAOYSA-N 0.000 claims description 4
- LPGJSRBABAPYJC-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)-7-methylsulfanylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(SC)=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 LPGJSRBABAPYJC-UHFFFAOYSA-N 0.000 claims description 4
- RZIGATPYRQFVTC-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)-7-phenylsulfanylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(SC=2C=CC=CC=2)=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RZIGATPYRQFVTC-UHFFFAOYSA-N 0.000 claims description 4
- OZNIETFZYQCVHB-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-7-ethoxy-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=1C2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C(OCC)=CC=1NC1CCCC1 OZNIETFZYQCVHB-UHFFFAOYSA-N 0.000 claims description 4
- JVEIELHGIPHJFL-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-7-ethylsulfanyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=1C2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C(SCC)=CC=1NC1CCCC1 JVEIELHGIPHJFL-UHFFFAOYSA-N 0.000 claims description 4
- NUNVURGNVQIZTL-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-7-ethylsulfanyl-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=1C2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(OC)=CC=3)=NN2C(SCC)=CC=1NC1CCCC1 NUNVURGNVQIZTL-UHFFFAOYSA-N 0.000 claims description 4
- VCIZRSUVLUDTDN-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-7-(2-methoxyethoxy)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=1C2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C(OCCOC)=CC=1NC1CCCC1 VCIZRSUVLUDTDN-UHFFFAOYSA-N 0.000 claims description 3
- SASXWATUGFXBFI-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)-7-propan-2-ylsulfanylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(SC(C)C)=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 SASXWATUGFXBFI-UHFFFAOYSA-N 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
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- 238000005481 NMR spectroscopy Methods 0.000 description 41
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- 239000004480 active ingredient Substances 0.000 description 8
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- 208000037803 restenosis Diseases 0.000 description 8
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- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
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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 description 5
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- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 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
- 238000010561 standard procedure Methods 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
- 239000008117 stearic acid Substances 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
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl 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
- 150000003457 sulfones Chemical class 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
- 235000012222 talc Nutrition 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
- 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
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000009466 transformation Effects 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
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229940108442 valtrex Drugs 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
- 230000008673 vomiting Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 229960002555 zidovudine Drugs 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31820301P | 2001-09-07 | 2001-09-07 | |
| US318203P | 2001-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2286272T3 true ES2286272T3 (es) | 2007-12-01 |
Family
ID=23237109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02759464T Expired - Lifetime ES2286272T3 (es) | 2001-09-07 | 2002-08-27 | Pirizolo-piridinas para el tratamiento de infecciones por herpes. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20040214834A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1423389B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2005507878A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE364043T1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60220525T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2286272T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2003022845A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005525382A (ja) | 2002-03-07 | 2005-08-25 | スミスクライン ビーチャム コーポレーション | ピラゾロピリミジンおよびピラゾロトリアジン誘導体ならびにそれを含む医薬組成物 |
| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease 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 |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20170145025A1 (en) | 2015-11-19 | 2017-05-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| LT3394033T (lt) | 2015-12-22 | 2021-03-10 | Incyte Corporation | Heterocikliniai junginiai, kaip imunomoduliatoriai |
| US20170320875A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HRP20221030T1 (hr) | 2016-06-20 | 2022-11-11 | Incyte Corporation | Heterociklički spojevi kao imunomodulatori |
| WO2018013789A1 (en) | 2016-07-14 | 2018-01-18 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MA46045A (fr) | 2016-08-29 | 2021-04-28 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| JP7149276B2 (ja) | 2016-12-22 | 2022-10-06 | インサイト・コーポレイション | Ｐｄ－ｌ１内在化誘導物質としてのテトラヒドロイミダゾ［４，５－ｃ］ピリジン誘導体 |
| BR112019012993A2 (pt) | 2016-12-22 | 2019-12-03 | Incyte Corporation | derivados de benzo-oxazol como imunomoduladores |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| MY210070A (en) | 2018-03-30 | 2025-08-25 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| PT3790877T (pt) | 2018-05-11 | 2023-05-10 | Incyte Corp | Derivados de tetrahidro-imidazo[4,5-c]piridina como imunomoduladores pd-l1 |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| BR112022005826A2 (pt) | 2019-09-30 | 2022-06-21 | Incyte Corp | Compostos de pirido[3,2-d]pirimidina como imunomoduladores |
| BR112022009031A2 (pt) | 2019-11-11 | 2022-10-11 | Incyte Corp | Sais e formas cristalinas de um inibidor de pd-1/pd-l1 |
| 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 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | 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. |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4925849A (en) * | 1987-06-15 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | Pharmaceutically useful pyrazolopyridines |
| 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 |
| 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 |
| GB9015764D0 (en) * | 1990-07-18 | 1990-09-05 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| 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 |
| US5552422A (en) * | 1995-01-11 | 1996-09-03 | Merck Frosst Canada, Inc. | Aryl substituted 5,5 fused aromatic nitrogen compounds as anti-inflammatory agents |
| 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 |
| CA2224517A1 (en) * | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor |
| FR2757166B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US20020156104A1 (en) * | 1997-06-13 | 2002-10-24 | Jerry L. Adams | Novel pyrazole and pyrazoline substituted compounds |
| NZ511349A (en) * | 1998-11-03 | 2003-10-31 | Glaxo Group Ltd | Pyrazolopyridine derivatives useful as selective COX-2 inhibitors |
| ES2216631T3 (es) * | 1999-02-27 | 2004-10-16 | Glaxo Group Limited | Pirazolpiridinas. |
| ES2245380T3 (es) * | 2000-12-15 | 2006-01-01 | Glaxo Group Limited | Pirazolopiridinas. |
| DE60112330T2 (de) * | 2000-12-15 | 2006-04-13 | Glaxo Group Ltd., Greenford | Pyrazolopyridinderivate |
| US7153855B2 (en) * | 2001-03-08 | 2006-12-26 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyrimidine therapeutic compounds |
| EP1372642A1 (en) * | 2001-03-30 | 2004-01-02 | SmithKline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
| ATE332301T1 (de) * | 2001-04-10 | 2006-07-15 | Smithkline Beecham Corp | Antivirale pyrazolopyridin verbindungen |
| US6962914B2 (en) * | 2001-04-27 | 2005-11-08 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyridine and pyrimidine therapeutic compounds |
-
2002
- 2002-08-27 US US10/487,968 patent/US20040214834A1/en not_active Abandoned
- 2002-08-27 JP JP2003526920A patent/JP2005507878A/ja active Pending
- 2002-08-27 DE DE60220525T patent/DE60220525T2/de not_active Expired - Fee Related
- 2002-08-27 AT AT02759464T patent/ATE364043T1/de not_active IP Right Cessation
- 2002-08-27 WO PCT/US2002/027251 patent/WO2003022845A1/en not_active Ceased
- 2002-08-27 ES ES02759464T patent/ES2286272T3/es not_active Expired - Lifetime
- 2002-08-27 EP EP02759464A patent/EP1423389B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60220525T2 (de) | 2008-02-07 |
| ATE364043T1 (de) | 2007-06-15 |
| EP1423389B1 (en) | 2007-06-06 |
| WO2003022845A1 (en) | 2003-03-20 |
| JP2005507878A (ja) | 2005-03-24 |
| EP1423389A1 (en) | 2004-06-02 |
| DE60220525D1 (de) | 2007-07-19 |
| US20040214834A1 (en) | 2004-10-28 |
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