ES2271273T3 - Derivados imidazo-1,2-aipiridina para la profilaxis y tratamiento de las infecciones del virus del herpres. - Google Patents
Derivados imidazo-1,2-aipiridina para la profilaxis y tratamiento de las infecciones del virus del herpres. Download PDFInfo
- Publication number
- ES2271273T3 ES2271273T3 ES02739833T ES02739833T ES2271273T3 ES 2271273 T3 ES2271273 T3 ES 2271273T3 ES 02739833 T ES02739833 T ES 02739833T ES 02739833 T ES02739833 T ES 02739833T ES 2271273 T3 ES2271273 T3 ES 2271273T3
- Authority
- ES
- Spain
- Prior art keywords
- imidazo
- pyridin
- het
- cyclopentylamino
- pyrimidinyl
- 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
Links
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- 208000015181 infectious disease Diseases 0.000 title description 22
- 241000700605 Viruses Species 0.000 title description 16
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- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 77
- 125000005843 halogen group Chemical group 0.000 claims abstract description 69
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 125000004429 atom Chemical group 0.000 claims abstract description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 33
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 225
- 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 197
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 183
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
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- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 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
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- 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
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (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 |
|---|---|---|---|
| US30000901P | 2001-06-21 | 2001-06-21 | |
| US300009P | 2001-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2271273T3 true ES2271273T3 (es) | 2007-04-16 |
Family
ID=23157269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02739833T Expired - Lifetime ES2271273T3 (es) | 2001-06-21 | 2002-06-10 | Derivados imidazo-1,2-aipiridina para la profilaxis y tratamiento de las infecciones del virus del herpres. |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7186714B2 (https=) |
| EP (1) | EP1401836B1 (https=) |
| JP (1) | JP2005500315A (https=) |
| KR (1) | KR20040018281A (https=) |
| CN (1) | CN1518550A (https=) |
| AT (1) | ATE337316T1 (https=) |
| BR (1) | BR0210464A (https=) |
| CA (1) | CA2451008A1 (https=) |
| CO (1) | CO5540312A2 (https=) |
| CZ (1) | CZ20033518A3 (https=) |
| DE (1) | DE60214179T2 (https=) |
| ES (1) | ES2271273T3 (https=) |
| HU (1) | HUP0400266A2 (https=) |
| IL (1) | IL158667A0 (https=) |
| MX (1) | MXPA03011906A (https=) |
| NO (1) | NO20035583D0 (https=) |
| PL (1) | PL366827A1 (https=) |
| WO (1) | WO2003000689A1 (https=) |
| ZA (1) | ZA200308726B (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6977574B1 (en) * | 1997-02-14 | 2005-12-20 | Denso Corporation | Stick-type ignition coil having improved structure against crack or dielectric discharge |
| WO2003000689A1 (en) * | 2001-06-21 | 2003-01-03 | Smithkline Beecham Corporation | Imidazo`1,2-a!pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| AU2003217712A1 (en) | 2002-03-07 | 2003-09-22 | Smithkline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| US7718801B2 (en) | 2004-08-31 | 2010-05-18 | Banyu Pharmaceutical Co., Ltd. | Substituted imidazole derivative |
| RU2008150377A (ru) | 2006-05-19 | 2010-06-27 | Нихон Меди-Физикс Ко., Лтд. (Jp) | Новое соединение, обладающее сродством к амилоиду |
| KR20090091287A (ko) * | 2006-11-17 | 2009-08-27 | 니혼 메디피직스 가부시키가이샤 | 신규 아밀로이드 친화성 화합물 |
| EP2098522B1 (en) | 2006-11-30 | 2011-10-19 | Nihon Medi-Physics Co., Ltd. | Compounds having affinity for amyloid |
| TWI406674B (zh) | 2007-02-13 | 2013-09-01 | 日本藥學物理公司 | Method for manufacturing diagnostic radiographic diagnostic agents |
| EP1964840A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]pyridines and their use as pharmaceuticals |
| TW200918102A (en) * | 2007-10-24 | 2009-05-01 | Nihon Mediphysics Co Ltd | Novel compound having affinity for amyloid |
| CN101909658A (zh) * | 2007-10-30 | 2010-12-08 | 日本医事物理股份有限公司 | 对淀粉样蛋白具有亲和性的新化合物的应用及制备方法 |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| JP5640005B2 (ja) | 2008-07-14 | 2014-12-10 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｄａｃおよび／またはｃｄｋ阻害剤としてのイミダゾシルピリジン化合物 |
| WO2010009166A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Oxindolyl inhibitor compounds |
| NZ602832A (en) | 2008-07-14 | 2014-04-30 | Gilead Sciences Inc | Fused heterocyclic hdac inhibitor compounds |
| JP2011529504A (ja) | 2008-07-28 | 2011-12-08 | ギリアード サイエンシーズ， インコーポレイテッド | シクロアルキリデンヒストン脱アセチル化酵素阻害剤化合物およびヘテロシクロアルキリデンヒストン脱アセチル化酵素阻害剤化合物 |
| US20100204265A1 (en) * | 2009-02-09 | 2010-08-12 | Genelabs Technologies, Inc. | Certain Nitrogen Containing Bicyclic Chemical Entities for Treating Viral Infections |
| WO2010144378A2 (en) | 2009-06-08 | 2010-12-16 | Gilead Colorado, Inc. | Cycloalkylcarbamate benzamide aniline hdac inhibitor compounds |
| KR20120031170A (ko) | 2009-06-08 | 2012-03-30 | 길리애드 사이언시즈, 인코포레이티드 | 알카노일아미노 벤즈아미드 아닐린 ｈｄａｃ 저해제 화합물 |
| WO2011041713A2 (en) * | 2009-10-02 | 2011-04-07 | Glaxosmithkline Llc | Piperazinyl antiviral agents |
| PH12012500778A1 (en) | 2009-10-30 | 2012-11-26 | Janssen Pharmaceutica Nv | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| BR112013033375B1 (pt) | 2011-06-27 | 2022-05-10 | Janssen Pharmaceutica N.V | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| WO2014009305A1 (en) | 2012-07-09 | 2014-01-16 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
| US9776997B2 (en) * | 2013-06-04 | 2017-10-03 | Bayer Pharma Aktiengesellschaft | 3-aryl-substituted imidazo[1,2-A]pyridines and their use |
| JP6642942B2 (ja) | 2013-12-30 | 2020-02-12 | アレイ バイオファーマ、インコーポレイテッド | セリン／トレオニンキナーゼ阻害剤 |
| US9688699B2 (en) | 2014-02-19 | 2017-06-27 | Bayer Pharma Aktiengesellschaft | 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines |
| US11071745B2 (en) * | 2014-07-07 | 2021-07-27 | Elian Llc | Viral prophylaxis treatment methods and pre-exposure prophylaxis kits |
| US10292970B2 (en) | 2014-12-02 | 2019-05-21 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituted imidazo[1,2-A]pyridines and their use |
| US11111245B2 (en) | 2017-02-01 | 2021-09-07 | Aucentra Therapeutics Pty Ltd | Derivatives of N-cycloalkyl/heterocycloalkyl-4-(imidazo[1,2-a]pyridine)pyrimidin-2-amine as therapeutic agents |
| CN110483504B (zh) * | 2019-08-02 | 2022-04-26 | 桂林理工大学 | 以DMF为甲酰化试剂构建2-(2-萘基)咪唑[1,2-a]吡啶-3-醛的新方法 |
| CN110483506B (zh) * | 2019-08-02 | 2022-04-19 | 桂林理工大学 | 以DMF为甲酰化试剂构建2-(2-噻吩基)咪唑[1,2-a]吡啶-3-醛的新方法 |
Family Cites Families (52)
| 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 |
| US4719218A (en) * | 1985-12-12 | 1988-01-12 | Smithkline Beckman Corporation | Pyrrolo[1,2-a]imidazole and pyrrolo[1,2-a]pyridine derivatives and their use as 5-lipoxygenase pathway inhibitor |
| US5145858A (en) * | 1985-12-12 | 1992-09-08 | Smithkline Beecham Corp. | Pyrrolo [1,2-a] imidazole and imidazo [1,2a] pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
| 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 |
| US4794114A (en) * | 1986-08-19 | 1988-12-27 | Smithkline Beckman Corporation | Inhibition of interleukin-1 production by monocytes and/or macrophages |
| 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 |
| KR920702621A (ko) * | 1989-06-13 | 1992-10-06 | 스튜어트 알. 슈터 | 단핵세포 및/또는 마크로파지에 의한 인터루킨-1 또는 종양회사인자 생성의 억제 |
| KR920702606A (ko) | 1989-06-13 | 1992-10-06 | 스튜어트 알. 슈터 | 모노킨(Monokine)의 활성저해 |
| 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 |
| KR930700104A (ko) * | 1990-06-12 | 1993-03-13 | 원본미기재 | 5-리프옥시게나제 및 사이클로옥시게나제 경로 개재된 질병의 억제 |
| GB9015764D0 (en) | 1990-07-18 | 1990-09-05 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
| GB9026926D0 (en) | 1990-12-12 | 1991-01-30 | Smith Kline French Lab | Novel process |
| JPH06504779A (ja) | 1990-12-13 | 1994-06-02 | スミスクライン・ビーチャム・コーポレイション | 新規ｃｓａｉｄｓ |
| IE914327A1 (en) | 1990-12-13 | 1992-06-17 | Smithkline Beecham Corp | Novel csaids |
| DE69232323T2 (de) | 1991-01-29 | 2002-08-08 | Fujisawa Pharmaceutical Co., Ltd. | Verwendung von Adenosinantagonisten zur Vorbeugung und Behandlung von Pankreatitis und Ulcera |
| 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 |
| US5521213A (en) | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
| AU4368996A (en) | 1994-11-23 | 1996-06-17 | Neurogen Corporation | Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands |
| 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 |
| AU5348396A (en) | 1995-05-01 | 1996-11-21 | Fujisawa Pharmaceutical Co., Ltd. | Imidazo 1,2-a pyridine and imidazo 1,2-a pyridezine derivati ves and their use as bone resorption inhibitors |
| 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 |
| WO1996041645A1 (en) | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Combination of a cyclooxygenase-2 inhibitor and a leukotriene b4 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 |
| CA2294057A1 (en) | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
| ES2256817T3 (es) | 1997-09-05 | 2006-07-16 | Glaxo Group Limited | Composiciones farmaceuticas que comprenden derivados de 2,3-diaril-pirazolo(1,5-b)piridazina. |
| WO1999058523A1 (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 |
| 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 |
| JP4032566B2 (ja) | 1999-06-21 | 2008-01-16 | 東レ株式会社 | 発光素子 |
| EE04592B1 (et) | 1999-06-28 | 2006-02-15 | Janssen Pharmaceutica N.V. | Respiratoorse süntsütiaalviiruse replikatsiooni inhibiitorid, nende valmistamismeetod, kasutamine ja vaheühendid, farmatseutiline kompositsioon ja selle valmistamismeetod ning produkt |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| CA2311483A1 (en) | 2000-06-12 | 2001-12-12 | Gregory N Beatch | IMIDAZO [1,2-A] PYRIDINIC ETHERS AND USES THEREOF |
| 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 |
| EP1341788B1 (en) | 2000-12-15 | 2005-08-10 | Glaxo Group Limited | Pyrazolopyridines |
| DE60112330T2 (de) | 2000-12-15 | 2006-04-13 | Glaxo Group Ltd., Greenford | Pyrazolopyridinderivate |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| WO2003000689A1 (en) * | 2001-06-21 | 2003-01-03 | Smithkline Beecham Corporation | Imidazo`1,2-a!pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| CA2450555A1 (en) * | 2001-06-25 | 2003-01-03 | Merck & Co., Inc. | (pyrimidyl)(phenyl)substituted fused heteroaryl p38 inhibiting and pkg kinase inhibiting compounds |
| ES2262893T3 (es) * | 2001-10-05 | 2006-12-01 | Smithkline Beecham Corporation | Derivados de imidazo-piridina para su uso en el tratamiento de infeccion virica por herpes. |
| US6711762B2 (en) | 2002-01-30 | 2004-03-30 | Ktk Services, Inc. | Method of using a truck cab bridge bed |
-
2002
- 2002-06-10 WO PCT/US2002/018520 patent/WO2003000689A1/en not_active Ceased
- 2002-06-10 MX MXPA03011906A patent/MXPA03011906A/es unknown
- 2002-06-10 KR KR10-2003-7016716A patent/KR20040018281A/ko not_active Withdrawn
- 2002-06-10 PL PL02366827A patent/PL366827A1/xx not_active Application Discontinuation
- 2002-06-10 CZ CZ20033518A patent/CZ20033518A3/cs unknown
- 2002-06-10 ES ES02739833T patent/ES2271273T3/es not_active Expired - Lifetime
- 2002-06-10 US US10/479,526 patent/US7186714B2/en not_active Expired - Fee Related
- 2002-06-10 HU HU0400266A patent/HUP0400266A2/hu unknown
- 2002-06-10 AT AT02739833T patent/ATE337316T1/de not_active IP Right Cessation
- 2002-06-10 CN CNA028124499A patent/CN1518550A/zh active Pending
- 2002-06-10 BR BR0210464-4A patent/BR0210464A/pt not_active Application Discontinuation
- 2002-06-10 EP EP02739833A patent/EP1401836B1/en not_active Expired - Lifetime
- 2002-06-10 DE DE60214179T patent/DE60214179T2/de not_active Expired - Fee Related
- 2002-06-10 IL IL15866702A patent/IL158667A0/xx unknown
- 2002-06-10 CA CA002451008A patent/CA2451008A1/en not_active Abandoned
- 2002-06-10 JP JP2003507092A patent/JP2005500315A/ja active Pending
-
2003
- 2003-11-10 ZA ZA200308726A patent/ZA200308726B/en unknown
- 2003-12-15 NO NO20035583A patent/NO20035583D0/no not_active Application Discontinuation
- 2003-12-16 CO CO03109957A patent/CO5540312A2/es not_active Application Discontinuation
-
2006
- 2006-03-29 US US11/391,867 patent/US20060167252A1/en not_active Abandoned
-
2007
- 2007-01-25 US US11/627,078 patent/US20070135451A1/en not_active Abandoned
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| Publication number | Publication date |
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| WO2003000689A1 (en) | 2003-01-03 |
| MXPA03011906A (es) | 2004-03-26 |
| US7186714B2 (en) | 2007-03-06 |
| DE60214179T2 (de) | 2007-01-04 |
| ZA200308726B (en) | 2005-02-10 |
| CO5540312A2 (es) | 2005-07-29 |
| HUP0400266A2 (hu) | 2004-08-30 |
| US20070135451A1 (en) | 2007-06-14 |
| KR20040018281A (ko) | 2004-03-02 |
| ATE337316T1 (de) | 2006-09-15 |
| NO20035583D0 (no) | 2003-12-15 |
| DE60214179D1 (de) | 2006-10-05 |
| US20060167252A1 (en) | 2006-07-27 |
| US20050228004A1 (en) | 2005-10-13 |
| BR0210464A (pt) | 2004-07-20 |
| CN1518550A (zh) | 2004-08-04 |
| CZ20033518A3 (en) | 2004-05-12 |
| JP2005500315A (ja) | 2005-01-06 |
| PL366827A1 (en) | 2005-02-07 |
| EP1401836A1 (en) | 2004-03-31 |
| IL158667A0 (en) | 2004-05-12 |
| CA2451008A1 (en) | 2003-01-03 |
| EP1401836B1 (en) | 2006-08-23 |
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