JP2003505378A5 - - Google Patents
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- Publication number
- JP2003505378A5 JP2003505378A5 JP2001511433A JP2001511433A JP2003505378A5 JP 2003505378 A5 JP2003505378 A5 JP 2003505378A5 JP 2001511433 A JP2001511433 A JP 2001511433A JP 2001511433 A JP2001511433 A JP 2001511433A JP 2003505378 A5 JP2003505378 A5 JP 2003505378A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- het
- halo
- optionally substituted
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 description 135
- 125000003118 aryl group Chemical group 0.000 description 69
- 125000005843 halogen group Chemical group 0.000 description 38
- 229910052739 hydrogen Inorganic materials 0.000 description 29
- 229910052799 carbon Inorganic materials 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 23
- 125000002252 acyl group Chemical group 0.000 description 21
- BKAWJIRCKVUVED-UHFFFAOYSA-N 5-(2-hydroxyethyl)-4-methylthiazole Chemical compound CC=1N=CSC=1CCO BKAWJIRCKVUVED-UHFFFAOYSA-N 0.000 description 17
- 125000005842 heteroatom Chemical group 0.000 description 17
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000004043 oxo group Chemical group O=* 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 102000003952 Caspase 3 Human genes 0.000 description 7
- 108090000397 Caspase 3 Proteins 0.000 description 7
- 230000001404 mediated effect Effects 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 6
- -1 hydroxy C1-3 alkyl Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 102000011727 Caspases Human genes 0.000 description 2
- 108010076667 Caspases Proteins 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 229940124101 Caspase 3 inhibitor Drugs 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 206010027202 Meningitis bacterial Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 201000009904 bacterial meningitis Diseases 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 208000033065 inborn errors of immunity Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000008816 organ damage Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 208000028529 primary immunodeficiency disease Diseases 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14446699P | 1999-07-19 | 1999-07-19 | |
| US60/144,466 | 1999-07-19 | ||
| US17061499P | 1999-12-14 | 1999-12-14 | |
| US60/170,614 | 1999-12-14 | ||
| PCT/CA2000/000833 WO2001005772A1 (en) | 1999-07-19 | 2000-07-17 | Pyrazinones, compositions containing such compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003505378A JP2003505378A (ja) | 2003-02-12 |
| JP2003505378A5 true JP2003505378A5 (https=) | 2007-05-24 |
| JP4749640B2 JP4749640B2 (ja) | 2011-08-17 |
Family
ID=26842025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001511433A Expired - Lifetime JP4749640B2 (ja) | 1999-07-19 | 2000-07-17 | ピラジノン、このような化合物を含む組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6444811B1 (https=) |
| EP (1) | EP1202976B1 (https=) |
| JP (1) | JP4749640B2 (https=) |
| AT (1) | ATE344249T1 (https=) |
| AU (1) | AU773317B2 (https=) |
| CA (1) | CA2378834C (https=) |
| DE (1) | DE60031686T2 (https=) |
| ES (1) | ES2274795T3 (https=) |
| WO (1) | WO2001005772A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2274795T3 (es) * | 1999-07-19 | 2007-06-01 | Merck Frosst Canada Ltd. | Pirazinonas, composiciones que contienen tales compuestos. |
| US20020155172A1 (en) * | 2000-04-07 | 2002-10-24 | Junying Yuan | Methods and compounds for decreasing cell toxicity or death |
| PE20011350A1 (es) | 2000-05-19 | 2002-01-15 | Vertex Pharma | PROFARMACO DE UN INHIBIDOR DE ENZIMA CONVERTIDORA DE INTERLEUCINA-1ß (ICE) |
| DE50212934D1 (de) * | 2001-01-26 | 2008-12-04 | Evotec Ag | Verfahren und mittel zur detektion enzymatischer spalt- und verknüpfungsreaktionen |
| FR2827288B1 (fr) * | 2001-07-12 | 2003-10-31 | Servier Lab | Nouveaux derives d'octahydro-2h-pyrido[1,2-a]pyrazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US7410956B2 (en) | 2002-02-11 | 2008-08-12 | Vertex Pharmaceuticals Incorporated | Caspase inhibitor prodrugs |
| US7960398B2 (en) | 2002-04-19 | 2011-06-14 | Vertex Pharmaceuticals Incorporated | Regulation of TNF-alpha |
| WO2004104790A2 (en) * | 2003-05-20 | 2004-12-02 | Kagutech Ltd. | Digital backplane |
| SG150547A1 (en) * | 2004-03-12 | 2009-03-30 | Vertex Pharma | Processes and intermediates |
| CA2567080A1 (en) | 2004-05-27 | 2005-12-15 | Vertex Pharmaceuticals Incorporated | Ice inhibitors for the treatment of autoinflammatory diseases |
| KR20080038369A (ko) | 2005-07-28 | 2008-05-06 | 버텍스 파마슈티칼스 인코포레이티드 | 카스파제 억제제 프로드럭 |
| KR20080042286A (ko) * | 2006-11-09 | 2008-05-15 | 주식회사 엘지생명과학 | 피리다지논 구조를 포함하는 캐스파제 저해제 |
| WO2009019115A1 (en) | 2007-08-03 | 2009-02-12 | Sanofi-Aventis | Caspase imaging probes |
| WO2009103432A2 (en) * | 2008-02-21 | 2009-08-27 | Sanofi-Aventis | Covalently binding imaging probes |
| US9116157B2 (en) | 2010-11-05 | 2015-08-25 | Brandeis University | Ice-cleaved alpha-synuclein as a biomarker |
| CN109180690A (zh) * | 2018-10-15 | 2019-01-11 | 烟台显华化工科技有限公司 | 一类用作蓝色荧光材料的氮杂芳香化合物及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5716929A (en) * | 1994-06-17 | 1998-02-10 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
| JP3140790B2 (ja) * | 1996-04-23 | 2001-03-05 | メルク エンド カンパニー インコーポレーテッド | ピラジノン系トロンビン阻害薬 |
| WO1998008840A1 (en) | 1996-08-29 | 1998-03-05 | Merck & Co., Inc. | Integrin antagonists |
| US5981546A (en) * | 1996-08-29 | 1999-11-09 | Merck & Co., Inc. | Integrin antagonists |
| BR9712000A (pt) * | 1996-09-06 | 1999-08-24 | Nippon Kayaku Kk | Derivados de acetamida sais dos mesmos composi-Æo farmac-utica inibidores de protease de quimase de desgranula-Æo de mastÄcitos ou de libera-Æo de histamina de mastÄcitos e de ativa-Æo de eosinÄfilo ou de libera-Æo de oxig-nio ativo de eosinÄfilo e processo para produzir os dervados de acetamida |
| CA2283704A1 (en) | 1997-03-24 | 1998-10-01 | Merck & Co., Inc. | Thrombin inhibitors |
| US5866573A (en) | 1997-04-21 | 1999-02-02 | Merck & Co., Inc. | Pyrazinone thrombin inhibitors |
| JP2001514227A (ja) | 1997-09-05 | 2001-09-11 | メルク エンド カムパニー インコーポレーテッド | ピラジノン系トロンビン阻害薬 |
| ES2274795T3 (es) * | 1999-07-19 | 2007-06-01 | Merck Frosst Canada Ltd. | Pirazinonas, composiciones que contienen tales compuestos. |
-
2000
- 2000-07-17 ES ES00947711T patent/ES2274795T3/es not_active Expired - Lifetime
- 2000-07-17 JP JP2001511433A patent/JP4749640B2/ja not_active Expired - Lifetime
- 2000-07-17 WO PCT/CA2000/000833 patent/WO2001005772A1/en not_active Ceased
- 2000-07-17 EP EP00947711A patent/EP1202976B1/en not_active Expired - Lifetime
- 2000-07-17 CA CA002378834A patent/CA2378834C/en not_active Expired - Lifetime
- 2000-07-17 DE DE60031686T patent/DE60031686T2/de not_active Expired - Lifetime
- 2000-07-17 AT AT00947711T patent/ATE344249T1/de not_active IP Right Cessation
- 2000-07-17 AU AU61432/00A patent/AU773317B2/en not_active Expired
- 2000-07-19 US US09/618,875 patent/US6444811B1/en not_active Expired - Lifetime
-
2002
- 2002-07-25 US US10/202,817 patent/US6699856B2/en not_active Expired - Lifetime
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