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)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (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)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Oncology (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 (https=) |
| EP (1) | EP1423389B1 (https=) |
| JP (1) | JP2005507878A (https=) |
| AT (1) | ATE364043T1 (https=) |
| DE (1) | DE60220525T2 (https=) |
| ES (1) | ES2286272T3 (https=) |
| WO (1) | WO2003022845A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003217712A1 (en) | 2002-03-07 | 2003-09-22 | Smithkline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| 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 |
| EP2402336A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| EP2402335A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| EP3365340B1 (en) | 2015-10-19 | 2022-08-10 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20170145025A1 (en) | 2015-11-19 | 2017-05-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2916874T3 (es) | 2015-12-17 | 2022-07-06 | Incyte Corp | Derivados de N-fenil-piridina-2-carboxamida y su uso como moduladores de la interacción proteína/proteína PD-1/PD-L1 |
| AU2016379372A1 (en) | 2015-12-22 | 2018-08-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2906460T3 (es) | 2016-05-06 | 2022-04-18 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| ES2905980T3 (es) | 2016-05-26 | 2022-04-12 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| BR112018076534A2 (pt) | 2016-06-20 | 2019-04-02 | Incyte Corporation | compostos heterocíclicos como imunomoduladores |
| MA45669A (fr) | 2016-07-14 | 2019-05-22 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| ES2941716T3 (es) | 2016-08-29 | 2023-05-25 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| ES2899402T3 (es) | 2016-12-22 | 2022-03-11 | Incyte Corp | Derivados de piridina como inmunomoduladores |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| EP3558990B1 (en) | 2016-12-22 | 2022-08-10 | Incyte Corporation | Tetrahydro imidazo[4,5-c]pyridine derivatives as pd-l1 internalization inducers |
| AU2017382870B2 (en) | 2016-12-22 | 2022-03-24 | Incyte Corporation | Benzooxazole derivatives as immunomodulators |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| CR20200520A (es) | 2018-03-30 | 2021-03-09 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| WO2019217821A1 (en) | 2018-05-11 | 2019-11-14 | Incyte Corporation | Tetrahydro-imidazo[4,5-c]pyridine derivatives as pd-l1 immunomodulators |
| EP4010342A1 (en) | 2019-08-09 | 2022-06-15 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
| WO2021067217A1 (en) | 2019-09-30 | 2021-04-08 | Incyte Corporation | Pyrido[3,2-d]pyrimidine compounds as immunomodulators |
| 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 |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
| US11866434B2 (en) | 2020-11-06 | 2024-01-09 | Incyte Corporation | Process for making a PD-1/PD-L1 inhibitor and salts and crystalline forms thereof |
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 |
| GB8404586D0 (en) * | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| GB8404584D0 (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 |
| DE69635048T2 (de) * | 1995-06-12 | 2006-02-16 | G.D. Searle & Co. | Mittel, enthaltend einen cyclooxygenase-2 inhibitor und einen 5-lipoxygenase inhibitor |
| 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 |
| FR2757166B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| CA2294057A1 (en) * | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
| HUP0104204A3 (en) * | 1998-11-03 | 2002-06-28 | Glaxo Group Ltd | Pyrazolopyridine derivatives as cox-2 inhibitors, process for their preparation and pharmaceutical compositions thereof |
| US6498166B1 (en) * | 1999-02-27 | 2002-12-24 | Smithkline Beecham Corporation | Pyrazolopyridines |
| DE60112330T2 (de) * | 2000-12-15 | 2006-04-13 | Glaxo Group Ltd., Greenford | Pyrazolopyridinderivate |
| EP1341788B1 (en) * | 2000-12-15 | 2005-08-10 | Glaxo Group Limited | Pyrazolopyridines |
| EP1366048B1 (en) * | 2001-03-08 | 2004-08-25 | SmithKline Beecham Corporation | Pyrazolopyridine derivatives |
| WO2002078701A1 (en) * | 2001-03-30 | 2002-10-10 | Smithkline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
| JP4219171B2 (ja) * | 2001-04-10 | 2009-02-04 | スミスクライン ビーチャム コーポレーション | 抗ウイルス性ピラゾロピリジン化合物 |
| ATE296826T1 (de) * | 2001-04-27 | 2005-06-15 | Smithkline Beecham Corp | Pyrazolo(1,5)pyridinderivate |
-
2002
- 2002-08-27 DE DE60220525T patent/DE60220525T2/de not_active Expired - Fee Related
- 2002-08-27 ES ES02759464T patent/ES2286272T3/es not_active Expired - Lifetime
- 2002-08-27 JP JP2003526920A patent/JP2005507878A/ja active Pending
- 2002-08-27 EP EP02759464A patent/EP1423389B1/en not_active Expired - Lifetime
- 2002-08-27 US US10/487,968 patent/US20040214834A1/en not_active Abandoned
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| ATE364043T1 (de) | 2007-06-15 |
| US20040214834A1 (en) | 2004-10-28 |
| DE60220525D1 (de) | 2007-07-19 |
| WO2003022845A1 (en) | 2003-03-20 |
| EP1423389A1 (en) | 2004-06-02 |
| DE60220525T2 (de) | 2008-02-07 |
| JP2005507878A (ja) | 2005-03-24 |
| EP1423389B1 (en) | 2007-06-06 |
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