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 (https=) | 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 (https=) |
| EP (1) | EP2655399B1 (https=) |
| JP (1) | JP5923110B2 (https=) |
| CN (1) | CN103403018B (https=) |
| AU (1) | AU2011349022B2 (https=) |
| CA (1) | CA2822350A1 (https=) |
| ES (1) | ES2654440T3 (https=) |
| NO (1) | NO2655399T3 (https=) |
| WO (1) | WO2012083436A1 (https=) |
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 |
| EP2590945B1 (en) | 2010-07-07 | 2014-04-30 | The Medicines Company (Leipzig) GmbH | Serine protease inhibitors |
| GB201311888D0 (en) * | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| WO2017189294A1 (en) * | 2016-04-25 | 2017-11-02 | Instrumentation Laboratory Company | Method and kit for identifying lupus anticoagulant (la) associated with antiphospholipid syndrome |
| EP3541381B1 (en) * | 2016-11-18 | 2022-12-28 | Merck Sharp & Dohme LLC | Inhibitors of factor xiia |
| 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 |
| EP3939968A4 (en) * | 2019-03-29 | 2022-12-14 | Medicinal Bioconvergence Research Center | NOVEL COMPOUND WITH ANTI-CANCER ACTIVITIES AND METHOD FOR PRODUCTION THEREOF |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3163469D1 (en) * | 1980-05-12 | 1984-06-14 | Choay Sa | 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 |
| ATE181334T1 (de) * | 1993-02-12 | 1999-07-15 | Corvas Int Inc | Inhibitoren gegen thrombose |
| 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 |
| WO1997049722A1 (en) * | 1996-06-25 | 1997-12-31 | Nisshin Flour Milling Co., Ltd. | Depsipeptides and drugs containing the same as the active ingredient |
| TWI222441B (en) | 1997-11-26 | 2004-10-21 | Dimensional Pharm Inc | Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors |
| 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 |
| JP2004516286A (ja) | 2000-12-18 | 2004-06-03 | メルク エンド カムパニー インコーポレーテッド | ベンジルアミン誘導体およびそれのトロンビン阻害薬としての使用 |
| DE10102878A1 (de) * | 2001-01-23 | 2002-08-01 | Haemosys Gmbh | Oligo- oder Polyalkylengekoppelte Thrombininhibitoren |
| US7838560B2 (en) | 2002-03-11 | 2010-11-23 | The Medicines Company (Leipzig) Gmbh | 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 |
| WO2008056207A1 (en) * | 2006-11-08 | 2008-05-15 | Chongxi Yu | Transdermal delivery systems of peptides and related compounds |
| EP2590945B1 (en) | 2010-07-07 | 2014-04-30 | The Medicines Company (Leipzig) GmbH | Serine protease inhibitors |
-
2011
- 2011-12-21 EP EP11850640.1A patent/EP2655399B1/en not_active Not-in-force
- 2011-12-21 CA CA2822350A patent/CA2822350A1/en not_active Abandoned
- 2011-12-21 US US13/332,900 patent/US8497245B2/en not_active Expired - Fee Related
- 2011-12-21 ES ES11850640.1T patent/ES2654440T3/es active Active
- 2011-12-21 WO PCT/CA2011/001398 patent/WO2012083436A1/en not_active Ceased
- 2011-12-21 AU AU2011349022A patent/AU2011349022B2/en not_active Ceased
- 2011-12-21 NO NO11850640A patent/NO2655399T3/no unknown
- 2011-12-21 JP JP2013544981A patent/JP5923110B2/ja not_active Expired - Fee Related
- 2011-12-21 CN CN201180065191.4A patent/CN103403018B/zh not_active Expired - Fee Related
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