JP2014500280A5 - - Google Patents
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- JP2014500280A5 JP2014500280A5 JP2013544981A JP2013544981A JP2014500280A5 JP 2014500280 A5 JP2014500280 A5 JP 2014500280A5 JP 2013544981 A JP2013544981 A JP 2013544981A JP 2013544981 A JP2013544981 A JP 2013544981A JP 2014500280 A5 JP2014500280 A5 JP 2014500280A5
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- JP
- Japan
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- 125000006239 protecting group Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 32
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 24
- -1 benzylsulfonyl Chemical group 0.000 claims description 24
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 20
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 238000003776 cleavage reaction Methods 0.000 claims description 16
- 230000007017 scission Effects 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 14
- 230000010933 acylation Effects 0.000 claims description 12
- 238000005917 acylation reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 208000005189 Embolism Diseases 0.000 claims description 11
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 108090000190 Thrombin Proteins 0.000 claims description 9
- 229960004072 thrombin Drugs 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 108010074860 Factor Xa Proteins 0.000 claims description 7
- 208000007536 Thrombosis Diseases 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000007675 cardiac surgery Methods 0.000 claims description 5
- 230000002612 cardiopulmonary effect Effects 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 230000010100 anticoagulation Effects 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 230000017531 blood circulation Effects 0.000 claims description 3
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims description 3
- 230000009977 dual effect Effects 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 230000010410 reperfusion Effects 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 206010038563 Reocclusion Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229960003766 thrombin (human) Drugs 0.000 claims description 2
- 230000001732 thrombotic effect Effects 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 6
- 150000007513 acids Chemical class 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 0 **(C*1)CC(C(O)=O)N1C([C@@](C(*)=O)N*)=O Chemical compound **(C*1)CC(C(O)=O)N1C([C@@](C(*)=O)N*)=O 0.000 description 5
- 206010062506 Heparin-induced thrombocytopenia Diseases 0.000 description 2
- 238000002618 extracorporeal membrane oxygenation Methods 0.000 description 2
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 206010051055 Deep vein thrombosis Diseases 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000002615 hemofiltration Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000013146 percutaneous coronary intervention Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061425597P | 2010-12-21 | 2010-12-21 | |
| US61/425,597 | 2010-12-21 | ||
| PCT/CA2011/001398 WO2012083436A1 (en) | 2010-12-21 | 2011-12-21 | Trypsin-like serine protease inhibitors, their preparation and use as selective inhibitors of the clotting factors iia and xa |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014500280A JP2014500280A (ja) | 2014-01-09 |
| JP2014500280A5 true JP2014500280A5 (enExample) | 2015-02-05 |
| JP5923110B2 JP5923110B2 (ja) | 2016-05-24 |
Family
ID=46312955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013544981A Expired - Fee Related JP5923110B2 (ja) | 2010-12-21 | 2011-12-21 | トリプシン様セリンプロテアーゼ阻害剤、その調製、ならびに凝固因子ＩＩａおよびＸａの選択的阻害剤としての使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8497245B2 (enExample) |
| EP (1) | EP2655399B1 (enExample) |
| JP (1) | JP5923110B2 (enExample) |
| CN (1) | CN103403018B (enExample) |
| AU (1) | AU2011349022B2 (enExample) |
| CA (1) | CA2822350A1 (enExample) |
| ES (1) | ES2654440T3 (enExample) |
| NO (1) | NO2655399T3 (enExample) |
| WO (1) | WO2012083436A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10301300B4 (de) | 2003-01-15 | 2009-07-16 | Curacyte Chemistry Gmbh | Verwendung von acylierten 4-Amidino- und 4-Guanidinobenzylaminen zur Inhibierung von Plasmakallikrein |
| WO2012004678A2 (en) | 2010-07-07 | 2012-01-12 | The Medicines Company (Leipzig) Gmbh | Serine protease inhibitors |
| GB201311888D0 (en) * | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| US10935560B2 (en) * | 2016-04-25 | 2021-03-02 | Instrumentation Laboratory Company | Method and kit for identifying lupus anticoagulant (LA) associated with antiphospholipid syndrome |
| US11014920B2 (en) | 2016-11-18 | 2021-05-25 | Merck Sharp & Dohme Corp. | Factor XIIa inhibitors |
| GB201805174D0 (en) * | 2018-03-29 | 2018-05-16 | Univ Leeds Innovations Ltd | Compounds |
| GB201807014D0 (en) * | 2018-04-30 | 2018-06-13 | Univ Leeds Innovations Ltd | Factor xlla inhibitors |
| WO2020204548A1 (ko) * | 2019-03-29 | 2020-10-08 | 재단법인 의약바이오컨버젼스연구단 | 항암활성을 갖는 신규한 화합물 및 이의 제조방법 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040149B1 (en) * | 1980-05-12 | 1984-05-09 | Choay S.A. | Oligopeptides with specific inhibiting properties of collagen induced aggregation, process for preparing the same and pharmaceutical compositions containing them |
| CA1241120A (en) | 1985-10-01 | 1988-08-23 | Sami A. Aly | Alternate mark inversion (ami) receiver |
| US5955576A (en) * | 1992-02-14 | 1999-09-21 | Corvas International, Inc. | Inhibitors of thrombosis |
| JP3466614B2 (ja) * | 1993-02-12 | 2003-11-17 | コルバス・インターナショナル、インコーポレイテッド | 血栓症のインヒビター |
| EP0648780A1 (en) * | 1993-08-26 | 1995-04-19 | Bristol-Myers Squibb Company | Heterocyclic thrombin inhibitors |
| JPH07138298A (ja) * | 1993-11-19 | 1995-05-30 | Japan Energy Corp | ヒルジン類縁体硫酸エステル化体またはその塩の製造方法 |
| AU1025795A (en) * | 1994-01-27 | 1995-08-03 | Mitsubishi Chemical Corporation | Prolineamide derivatives |
| ZA951617B (en) * | 1994-03-04 | 1997-02-27 | Lilly Co Eli | Antithrombotic agents. |
| US5914319A (en) | 1995-02-27 | 1999-06-22 | Eli Lilly And Company | Antithrombotic agents |
| JP3947229B2 (ja) * | 1996-06-25 | 2007-07-18 | 株式会社日清製粉グループ本社 | デプシペプチドおよびこれを有効成分とする医薬 |
| DE69836346T2 (de) | 1997-11-26 | 2007-05-24 | Ortho-Mcneil Pharmaceutical, Inc. | Heteroaryl aminoguanidin- und alkoxyguanidinderivate und ihre verwendung als proteasehemmer |
| DE10029015A1 (de) | 2000-06-15 | 2001-12-20 | Curacyte Ag | Hemmstoffe für den Gerinnungsfaktor Xa |
| DE10029014A1 (de) | 2000-06-15 | 2001-12-20 | Univ Schiller Jena | Urokinase-Hemmstoffe |
| WO2002050056A1 (en) | 2000-12-18 | 2002-06-27 | Merck & Co., Inc. | Benzylamine derivatives and their use as thrombin inhibitors |
| DE10102878A1 (de) * | 2001-01-23 | 2002-08-01 | Haemosys Gmbh | Oligo- oder Polyalkylengekoppelte Thrombininhibitoren |
| AU2003219039A1 (en) | 2002-03-11 | 2003-09-22 | Curacyte Ag | Urokinase inhibitors, production and use thereof |
| DE10227668A1 (de) | 2002-06-20 | 2004-01-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Arzneimittel zur Behandlung des systemic inflammatory response syndrome |
| DE10227666A1 (de) | 2002-06-20 | 2004-01-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | (R)-2-(4-Amidinophenylaminomethyl)-1-methyl-5-[1-(carboxymethylamino)-1-(pyrrolidinocarbonyl)- ethyl]-benzimidazol, dessen Monohydrochlorid, Verfahren zu deren Herstellung sowie Verwendung als Arzneimittel |
| DE10301300B4 (de) | 2003-01-15 | 2009-07-16 | Curacyte Chemistry Gmbh | Verwendung von acylierten 4-Amidino- und 4-Guanidinobenzylaminen zur Inhibierung von Plasmakallikrein |
| DE10322191B4 (de) | 2003-05-16 | 2014-02-27 | The Medicines Company (Leipzig) Gmbh | N-sulfonylierte Aminosäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10342108A1 (de) | 2003-09-11 | 2005-04-14 | Curacyte Chemistry Gmbh | Basisch-substituierte Benzylaminanaloga als Inhibitoren des Gerinnungsfaktors Xa, ihre Herstellung und Verwendung |
| DE102005044319A1 (de) * | 2005-09-16 | 2007-03-22 | Curacyte Chemistry Gmbh | 2-(Aminomethyl)-5-Chlor-Benzylamid-Derivate und ihre Verwendung als Hemmstoffe des Gerinnungsfaktors Xa |
| DE102006050672A1 (de) | 2006-10-24 | 2008-04-30 | Curacyte Discovery Gmbh | Hemmstoffe des Plasmins und des Plasmakallikreins |
| CA2668500C (en) * | 2006-11-08 | 2018-07-31 | Chongxi Yu | Transdermal delivery systems of peptides and related compounds |
| WO2012004678A2 (en) | 2010-07-07 | 2012-01-12 | The Medicines Company (Leipzig) Gmbh | Serine protease inhibitors |
-
2011
- 2011-12-21 NO NO11850640A patent/NO2655399T3/no unknown
- 2011-12-21 CA CA2822350A patent/CA2822350A1/en not_active Abandoned
- 2011-12-21 WO PCT/CA2011/001398 patent/WO2012083436A1/en not_active Ceased
- 2011-12-21 CN CN201180065191.4A patent/CN103403018B/zh not_active Expired - Fee Related
- 2011-12-21 ES ES11850640.1T patent/ES2654440T3/es active Active
- 2011-12-21 EP EP11850640.1A patent/EP2655399B1/en not_active Not-in-force
- 2011-12-21 JP JP2013544981A patent/JP5923110B2/ja not_active Expired - Fee Related
- 2011-12-21 AU AU2011349022A patent/AU2011349022B2/en not_active Ceased
- 2011-12-21 US US13/332,900 patent/US8497245B2/en not_active Expired - Fee Related
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