JP2005508955A - ヘルペスウイルス感染の治療で使用されるためのイミダゾ−ピリジン誘導体 - Google Patents
ヘルペスウイルス感染の治療で使用されるためのイミダゾ−ピリジン誘導体 Download PDFInfo
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- JP2005508955A JP2005508955A JP2003534429A JP2003534429A JP2005508955A JP 2005508955 A JP2005508955 A JP 2005508955A JP 2003534429 A JP2003534429 A JP 2003534429A JP 2003534429 A JP2003534429 A JP 2003534429A JP 2005508955 A JP2005508955 A JP 2005508955A
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- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 201000002341 thymus lymphoma Diseases 0.000 description 1
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
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- 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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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
- 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)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (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)
- Public Health (AREA)
- Veterinary Medicine (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 |
|---|---|---|---|
| US32770501P | 2001-10-05 | 2001-10-05 | |
| PCT/US2002/030056 WO2003031446A1 (en) | 2001-10-05 | 2002-09-23 | Imidazo-pyridine derivatives for use in the treatment of herpes viral infection |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005508955A true JP2005508955A (ja) | 2005-04-07 |
| JP2005508955A5 JP2005508955A5 (enExample) | 2005-12-22 |
Family
ID=23277681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003534429A Pending JP2005508955A (ja) | 2001-10-05 | 2002-09-23 | ヘルペスウイルス感染の治療で使用されるためのイミダゾ−ピリジン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7244740B2 (enExample) |
| EP (1) | EP1432712B1 (enExample) |
| JP (1) | JP2005508955A (enExample) |
| AT (1) | ATE326466T1 (enExample) |
| DE (1) | DE60211539T2 (enExample) |
| ES (1) | ES2262893T3 (enExample) |
| WO (1) | WO2003031446A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008059714A1 (en) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Novel compounds with affinity for amyloid |
| WO2009057577A1 (ja) * | 2007-10-30 | 2009-05-07 | Nihon Medi-Physics Co., Ltd. | 新規アミロイド親和性化合物の使用及び製造方法 |
| JP2020505419A (ja) * | 2017-02-01 | 2020-02-20 | オーセントラ セラピュティクス ピーティーワイ エルティーディーＡｕｃｅｎｔｒａ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｐｔｙ Ｌｔｄ | 治療薬としてのＮ−シクロアルキル／ヘテロシクロアルキル−４−（イミダゾ［１，２−ａ］ピリジン）ピリミジン−２−アミン誘導体 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0400266A2 (hu) * | 2001-06-21 | 2004-08-30 | Smithkline Beecham Corp. | Imidazo[1,2-a]piridin-származékok, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk herpeszvírus-fertőzések megelőzésére vagy kezelésére |
| EP1485385B1 (en) | 2002-03-07 | 2005-08-17 | SmithKline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
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| JP2005524672A (ja) | 2002-03-09 | 2005-08-18 | アストラゼネカ アクチボラグ | Ｃｄｋ阻害活性を有するイミダゾリル置換ピリミジン誘導体 |
| EP1603900A4 (en) * | 2003-03-06 | 2008-08-20 | Merck & Co Inc | IMIDAZOPYRIDIN COMPOUNDS WITH EFFECT AGAINST PROTOZOEN |
| GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
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| AU2009271003A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Sciences, Inc. | Imidazolylpyrimidine compounds as HDAC and/or CDK inhibitors |
| CA2728228A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
| AU2009276699A1 (en) | 2008-07-28 | 2010-02-04 | Gilead Sciences, Inc. | Cycloalkylidene and heterocycloalkylidene histone deacetylase inhibitor compounds |
| ES2463826T3 (es) | 2009-06-08 | 2014-05-29 | Gilead Sciences, Inc. | Compuestos inhibidores de HDAC de cicloalquilcarbamato benzamida anilina |
| KR20120031170A (ko) | 2009-06-08 | 2012-03-30 | 길리애드 사이언시즈, 인코포레이티드 | 알카노일아미노 벤즈아미드 아닐린 ｈｄａｃ 저해제 화합물 |
| CA2778949C (en) | 2009-10-30 | 2018-02-27 | 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 |
| RU2657540C2 (ru) | 2012-06-26 | 2018-06-14 | Янссен Фармацевтика Нв | Комбинации, содержащие ингибиторы pde 2, такие как 1-арил-4-метил-[1,2,4]триазоло[4,3-а]хиноксалиновые соединения, и ингибиторы pde 10, для применения в лечении неврологических или метаболических расстройств |
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| CN120829428A (zh) * | 2024-04-18 | 2025-10-24 | 中国医学科学院药物研究所 | 咪唑并吡啶衍生物及其用途 |
Family Cites Families (49)
| 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 |
| 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 |
| 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 |
| 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 |
| JPH04506215A (ja) | 1989-06-13 | 1992-10-29 | スミスクライン・ビーチャム・コーポレイション | モノカイン活性干渉 |
| WO1991000092A1 (en) | 1989-06-13 | 1991-01-10 | 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 |
| AU8205991A (en) | 1990-06-12 | 1992-01-07 | 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 |
| GB9026926D0 (en) | 1990-12-12 | 1991-01-30 | Smith Kline French Lab | Novel process |
| ZA919797B (en) | 1990-12-13 | 1992-10-28 | Smithkline Beecham Corp | Bicyclo-5,6-dihydro-7h-pyrrolo-1,20-imidazol-7-ols and 7-ones |
| WO1992010190A1 (en) | 1990-12-13 | 1992-06-25 | Smithkline Beecham Corporation | Novel csaids |
| CA2060138A1 (en) | 1991-01-29 | 1992-07-30 | Youichi Shiokawa | New use of the adenosine antagonist |
| 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 |
| CN1088062C (zh) | 1994-11-23 | 2002-07-24 | 纽罗根公司 | 某些4－氨基甲基－2－取代的咪唑衍生物2－氨基甲基－4－取代的咪唑衍生物新的一族多巴胺受体亚型特异性配体 |
| US5552422A (en) | 1995-01-11 | 1996-09-03 | Merck Frosst Canada, Inc. | Aryl substituted 5,5 fused aromatic nitrogen compounds as anti-inflammatory agents |
| KR19980703559A (ko) | 1995-04-04 | 1998-11-05 | 그레이엄브레레톤 | 이미다조［1,2-ａ］피리딘 유도체 |
| 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 |
| WO1996041626A1 (en) | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 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 |
| CA2224563A1 (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 |
| FR2757059B1 (fr) | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Nouvelle application therapeutique des derives du pyrrole |
| FR2757166B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| WO1998056377A1 (en) | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
| ES2203985T3 (es) | 1997-09-05 | 2004-04-16 | Glaxo Group Limited | Derivados de 2,3-diaril-pirazolo(1,5)piridazina, su preparacion y su uso como inhibidores de la ciclooxigenasa 2(cox-2)`. |
| JP2002514640A (ja) | 1998-05-14 | 2002-05-21 | ジー・ディー・サール・アンド・カンパニー | ｐ３８キナーゼ阻害剤としての１，５−ジアリール置換ピラゾール類 |
| 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 |
| CN1263755C (zh) | 1998-11-03 | 2006-07-12 | 葛兰素集团有限公司 | 作为选择性cox－2抑制剂的吡唑并吡啶衍生物 |
| ATE261444T1 (de) | 1999-02-27 | 2004-03-15 | Glaxo Group Ltd | Pyrazolopyridine |
| JP4032566B2 (ja) | 1999-06-21 | 2008-01-16 | 東レ株式会社 | 発光素子 |
| EP1400519B1 (en) | 1999-06-28 | 2007-03-07 | Janssen Pharmaceutica N.V. | Respiratory syncytial virus replication inhibitors |
| 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 |
| WO2002048148A2 (en) | 2000-12-15 | 2002-06-20 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| ATE301653T1 (de) | 2000-12-15 | 2005-08-15 | Glaxo Group Ltd | Pyrazolopyridine |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| CA2450555A1 (en) | 2001-06-25 | 2003-01-03 | Merck & Co., Inc. | (pyrimidyl)(phenyl)substituted fused heteroaryl p38 inhibiting and pkg kinase inhibiting compounds |
-
2002
- 2002-09-23 WO PCT/US2002/030056 patent/WO2003031446A1/en not_active Ceased
- 2002-09-23 DE DE60211539T patent/DE60211539T2/de not_active Expired - Fee Related
- 2002-09-23 AT AT02800844T patent/ATE326466T1/de not_active IP Right Cessation
- 2002-09-23 EP EP02800844A patent/EP1432712B1/en not_active Expired - Lifetime
- 2002-09-23 JP JP2003534429A patent/JP2005508955A/ja active Pending
- 2002-09-23 US US10/489,056 patent/US7244740B2/en not_active Expired - Fee Related
- 2002-09-23 ES ES02800844T patent/ES2262893T3/es not_active Expired - Lifetime
-
2006
- 2006-05-03 US US11/381,422 patent/US20080139594A1/en not_active Abandoned
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008059714A1 (en) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Novel compounds with affinity for amyloid |
| JPWO2008059714A1 (ja) * | 2006-11-17 | 2010-03-04 | 日本メジフィジックス株式会社 | 新規アミロイド親和性化合物 |
| WO2009057577A1 (ja) * | 2007-10-30 | 2009-05-07 | Nihon Medi-Physics Co., Ltd. | 新規アミロイド親和性化合物の使用及び製造方法 |
| JP2020505419A (ja) * | 2017-02-01 | 2020-02-20 | オーセントラ セラピュティクス ピーティーワイ エルティーディーＡｕｃｅｎｔｒａ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｐｔｙ Ｌｔｄ | 治療薬としてのＮ−シクロアルキル／ヘテロシクロアルキル−４−（イミダゾ［１，２−ａ］ピリジン）ピリミジン−２−アミン誘導体 |
| JP7113528B2 (ja) | 2017-02-01 | 2022-08-05 | オーセントラ セラピュティクス ピーティーワイ エルティーディー | 治療薬としてのＮ－シクロアルキル／ヘテロシクロアルキル－４－（イミダゾ［１，２－ａ］ピリジン）ピリミジン－２－アミン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60211539D1 (de) | 2006-06-22 |
| US7244740B2 (en) | 2007-07-17 |
| ATE326466T1 (de) | 2006-06-15 |
| EP1432712B1 (en) | 2006-05-17 |
| EP1432712A1 (en) | 2004-06-30 |
| US20080139594A1 (en) | 2008-06-12 |
| DE60211539T2 (de) | 2006-09-21 |
| US20040248917A1 (en) | 2004-12-09 |
| WO2003031446A1 (en) | 2003-04-17 |
| ES2262893T3 (es) | 2006-12-01 |
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