TWI222441B - Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors - Google Patents

Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors Download PDF

Info

Publication number
TWI222441B
TWI222441B TW087119488A TW87119488A TWI222441B TW I222441 B TWI222441 B TW I222441B TW 087119488 A TW087119488 A TW 087119488A TW 87119488 A TW87119488 A TW 87119488A TW I222441 B TWI222441 B TW I222441B
Authority
TW
Taiwan
Prior art keywords
methyl
amino
pyridone
aminocarbonylmethyl
ministry
Prior art date
Application number
TW087119488A
Other languages
English (en)
Chinese (zh)
Inventor
Tianbao Lu
Bruce E Tomczuk
Thomas P Markotan
Colleen Siedem
Original Assignee
Dimensional Pharm Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dimensional Pharm Inc filed Critical Dimensional Pharm Inc
Application granted granted Critical
Publication of TWI222441B publication Critical patent/TWI222441B/zh

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72Nitrogen atoms
    • C07D213/74Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06139Dipeptides with the first amino acid being heterocyclic
TW087119488A 1997-11-26 1998-11-25 Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors TWI222441B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6647597P 1997-11-26 1997-11-26
US6732497P 1997-12-05 1997-12-05
US7910798P 1998-03-23 1998-03-23

Publications (1)

Publication Number Publication Date
TWI222441B true TWI222441B (en) 2004-10-21

Family

ID=27370979

Family Applications (1)

Application Number Title Priority Date Filing Date
TW087119488A TWI222441B (en) 1997-11-26 1998-11-25 Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors

Country Status (14)

Country Link
US (8) US6037356A (US06566379-20030520-C00022.png)
EP (1) EP1036063B1 (US06566379-20030520-C00022.png)
JP (1) JP2001524467A (US06566379-20030520-C00022.png)
AR (1) AR016702A1 (US06566379-20030520-C00022.png)
AT (1) ATE344246T1 (US06566379-20030520-C00022.png)
AU (1) AU751412B2 (US06566379-20030520-C00022.png)
BR (1) BR9815325A (US06566379-20030520-C00022.png)
CA (1) CA2311969A1 (US06566379-20030520-C00022.png)
DE (1) DE69836346T2 (US06566379-20030520-C00022.png)
EA (1) EA004180B1 (US06566379-20030520-C00022.png)
ES (1) ES2274587T3 (US06566379-20030520-C00022.png)
PL (1) PL340560A1 (US06566379-20030520-C00022.png)
TW (1) TWI222441B (US06566379-20030520-C00022.png)
WO (1) WO1999026926A1 (US06566379-20030520-C00022.png)

Families Citing this family (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1036063B1 (en) * 1997-11-26 2006-11-02 Ortho-McNeil Pharmaceuticals, Inc. Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors
IL139162A0 (en) * 1998-04-24 2001-11-25 Dimensional Pharm Inc Amidinohydrazone, alkoxyguanidine and aminoguanidine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same
AU759427B2 (en) * 1998-06-11 2003-04-17 3-Dimensional Pharmaceuticals, Inc. Pyrazinone protease inhibitors
US6653316B1 (en) 1999-05-19 2003-11-25 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
US6716838B1 (en) 1999-05-19 2004-04-06 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl uracils as anticoagulative agents
US6458952B1 (en) * 1999-05-19 2002-10-01 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl uracils useful for selective inhibition of the coagulation cascade
US6664255B1 (en) * 1999-05-19 2003-12-16 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyrazinones useful for selective inhibition of the coagulation cascade
US7015230B1 (en) 1999-05-19 2006-03-21 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl uracils useful for selective inhibition of the coagulation cascade
CA2373509A1 (en) * 1999-05-19 2000-11-23 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyridones useful for selective inhibition of the coagulation cascade
US6906068B1 (en) 1999-05-19 2005-06-14 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl 1,2,4 - triazinones useful as anticoagulants
US6750342B1 (en) * 1999-05-19 2004-06-15 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
US6867217B1 (en) * 1999-05-19 2005-03-15 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyridones useful for selective inhibition of the coagulation cascade
US6908919B2 (en) * 1999-05-19 2005-06-21 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyrazinones useful for selective inhibition of the coagulation cascade
CA2372234A1 (en) 1999-05-27 2000-12-07 3-Dimensional Pharmaceuticals, Inc. Oxazaheterocycles as protease inhibitors
WO2001004117A1 (en) * 1999-07-09 2001-01-18 3-Dimensional Pharmaceuticals, Inc. Heteroaryl protease inhibitors and diagnostic imaging agents
KR20020027639A (ko) 1999-09-13 2002-04-13 3-디멘져널 파마슈티칼즈 인코오포레이티드 아자시클로알카논 세린 프로테아제 억제제
EP1127884A1 (en) * 2000-02-26 2001-08-29 Aventis Pharma Deutschland GmbH Novel malonic acid derivatives, processes for their preparation, their use as inhibitor of factor XA activity and pharmaceutical compositions containing them
WO2001068605A1 (en) * 2000-03-13 2001-09-20 Pharmacia Corporation Polycyclic aryl and heteroaryl substituted benzenes useful for selective inhibition of the coagulation cascade
ATE289299T1 (de) 2000-04-05 2005-03-15 Pharmacia Corp Polyzyclisch aryl und heteroaryl substituierte 4- pyronen verwendbar als selektive hemmung von dem koagulationsprozess
EP1268428A2 (en) * 2000-04-05 2003-01-02 Pharmacia Corporation Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the coagulation cascade
EP1274676A2 (en) * 2000-04-17 2003-01-15 Pharmacia Corporation Polycyclic aryl and heteroaryl substituted 1,4-quinones useful for selective inhibition of the coagulation cascade
AU2001217827A1 (en) * 2000-05-18 2001-11-26 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyridones useful for selective inhibition of the coagulation cascade
CA2415932A1 (en) 2000-07-17 2002-01-24 3-Dimensional Pharmaceuticals, Inc. Cyclic oxyguanidine pyrazinones as protease inhibitors
CA2417914A1 (en) 2000-08-04 2002-02-14 3-Dimensional Pharmaceuticals, Inc. Cyclic oxyguanidine protease inhibitors
US20020037897A1 (en) * 2000-08-07 2002-03-28 3-Dimensional Pharmaceuticals, Inc. Tetrahydroisoquinoline-3-carboxylic acid alkoxyguanidines as integrin antagonists
US6486174B2 (en) 2000-08-07 2002-11-26 3-Dimensional Pharmaceuticals, Inc. Tetrahydroisoquinoline-3-carboxylic acid alkoxyguanidines as integrin antagonists
UA75093C2 (en) * 2000-10-06 2006-03-15 Dimensional Pharm Inc Aminopyridinyl-,aminoguanidinyl-, and alkoxyguanidinesubstituted phenylsubstituted phenylacetamides as protease inhibitors
WO2002042272A2 (en) 2000-11-20 2002-05-30 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyridines useful for selective inhibition of the coagulation cascade
US7119094B1 (en) 2000-11-20 2006-10-10 Warner-Lambert Company Substituted polycyclic aryl and heteroarpyl pyrazinones useful for selective inhibition of the coagulation cascade
US7015223B1 (en) 2000-11-20 2006-03-21 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl 1,2,4-triazinones useful for selective inhibition of the coagulation cascade
US20030236257A1 (en) * 2001-04-04 2003-12-25 South Michael S. Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the cogulation cascade
DE10133786A1 (de) * 2001-07-16 2003-02-06 Boehringer Ingelheim Pharma Verwendung von Thrombin-Inhibitoren zur Behandlung von Arthritis
CA2462647A1 (en) * 2001-10-03 2003-04-10 Michael S. South 6-membered unsaturated heterocyclic compounds useful for selective inhibition of the coagulation cascade
CA2462305A1 (en) * 2001-10-03 2003-04-10 Michael S. South 6-membered heterocyclic compounds useful for selective inhibition of the coagulation cascade
CA2462645A1 (en) * 2001-10-03 2003-11-13 Pharmacia Corporation Substituted 5-membered polycyclic compounds useful for selective inhibition of the coagulation cascade
US20040082585A1 (en) * 2001-10-03 2004-04-29 Pharmacia Corporation Prodrugs of substituted polycyclic compounds useful for selective inhibition of the coagulation cascade
US7262211B2 (en) 2001-12-04 2007-08-28 Dendreon Corporation Aromatic heterocyclic non-covalent inhibitors of urokinase and blood vessel formation
WO2004050637A2 (en) 2002-12-03 2004-06-17 Axys Pharmaceuticals, Inc. 2-(2-hydroxybiphenyl-3-yl)-1h-benzoimidazole-5-carboxamidine derivatives as factor viia inhibitors
ATE432703T1 (de) 2003-04-10 2009-06-15 Ortho Mcneil Pharm Inc Substituierte phenylacetamide und ihre anwendung als protease inhibitoren
US7087622B2 (en) 2004-05-07 2006-08-08 Janssen Pharmaceutica N.V. Pyridone compounds as inhibitors of bacterial type III protein secreation systems
US20050281740A1 (en) * 2004-06-16 2005-12-22 Glen Gong Imaging damaged lung tissue
US20050281739A1 (en) * 2004-06-16 2005-12-22 Glen Gong Imaging damaged lung tissue using compositions
US7553810B2 (en) * 2004-06-16 2009-06-30 Pneumrx, Inc. Lung volume reduction using glue composition
US7678767B2 (en) 2004-06-16 2010-03-16 Pneumrx, Inc. Glue compositions for lung volume reduction
US20050281798A1 (en) * 2004-06-16 2005-12-22 Glen Gong Targeting sites of damaged lung tissue using composition
US20050281800A1 (en) * 2004-06-16 2005-12-22 Glen Gong Targeting sites of damaged lung tissue
US7608579B2 (en) * 2004-06-16 2009-10-27 Pneumrx, Inc. Lung volume reduction using glue compositions
EP1781182B1 (en) 2004-07-08 2019-11-13 PneumRx, Inc. Pleural effusion treatment device
US20070255177A1 (en) * 2006-04-27 2007-11-01 Pronovost Allan D Devices and methods for collecting oral samples of enriched serous fluid
US7758001B2 (en) * 2006-09-13 2010-07-20 Premier Mounts Mount with magnetic attachment and automatic safety latching
US20100297218A1 (en) * 2006-09-20 2010-11-25 Pneumrx, Inc. Tissue adhesive compositions and methods thereof
EP2160392A2 (en) 2007-05-03 2010-03-10 Intermune, Inc. Novel macrocyclic inhibitors of hepatitis c virus replication
WO2008150470A1 (en) 2007-05-31 2008-12-11 Shionogi & Co., Ltd. Oxyimino compounds and the use thereof
JP5501983B2 (ja) 2008-06-11 2014-05-28 塩野義製薬株式会社 オキシカルバモイル化合物およびその使用
JPWO2010134345A1 (ja) * 2009-05-20 2012-11-08 積水メディカル株式会社 血液凝固時間延長剤
US8349832B2 (en) * 2009-09-02 2013-01-08 Canthera Therapeutics Compounds and compositions for treating cancer
US8318737B2 (en) 2009-09-02 2012-11-27 Canthera Therapeutics Inc. Compounds and compositions for treating cancer
ES2654440T3 (es) 2010-12-21 2018-02-13 The Medicines Company (Leipzig) Gmbh Inhibidores de serina proteasa de tipo tripsina, su preparación y uso como inhibidores selectivos de los factores de coagulación IIa y Xa
US8894970B2 (en) 2010-12-31 2014-11-25 Corridor Pharmaceuticals, Inc. Arginase inhibitors and methods of use thereof
CA2835434A1 (en) 2011-05-17 2012-11-22 Velico Medical, Inc. Improved platelet storage using a sialidase inhibitor
US9788539B2 (en) 2011-05-17 2017-10-17 Velico Medical, Inc. Platelet protection solution having beta-galactosidase and sialidase inhibitors
EP2903430A1 (en) 2012-10-05 2015-08-12 Velico Medical, Inc. Platelet additive solution having a beta-galactosidase inhibitor
WO2014120886A1 (en) 2013-01-30 2014-08-07 Velico Medical, Inc. Platelet additive solution having a self-assembling hydrogel-forming peptide
US20150365084A1 (en) * 2014-06-13 2015-12-17 Infineon Technologies Austria Ag Circuits and methods for operating a circuit

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097472A (en) 1974-11-08 1978-06-27 Mitsubishi Chemical Industries Limited N2 -arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof
SU328634A1 (ru) 1971-01-05 1978-01-05 Butyrin V G Устройство дл забора проб крови у животных
SU938739A3 (ru) 1977-01-19 1982-06-23 Мицубиси Кемикал Индастриз Лимитед(Фирма) Способ получени N -арилсульфонил-L-аргининамидов или их солей
US4418052A (en) * 1980-08-12 1983-11-29 Wong Dennis W Diagnostic compositions and method for radiologic imaging of fibrinogen deposition in the body
US4980148A (en) * 1985-02-06 1990-12-25 Mallinckrodt, Inc. Methods for enhancing magnetic resonance imaging
US5011686A (en) * 1987-09-21 1991-04-30 Creative Biomolecules, Inc. Thrombus specific conjugates
ZA897514B (en) * 1988-10-07 1990-06-27 Merrell Dow Pharma Novel peptidase inhibitors
US5024829A (en) * 1988-11-21 1991-06-18 Centocor, Inc. Method of imaging coronary thrombi
US5656600A (en) * 1993-03-25 1997-08-12 Corvas International, Inc. α-ketoamide derivatives as inhibitors of thrombosis
US5658885A (en) * 1993-04-27 1997-08-19 The Dupont Merck Pharmaceutical Company Amidino and guanidino substituted boronic acid inhibitors of trypsin-like enzymes
GB9318637D0 (en) 1993-09-08 1993-10-27 Ferring Res Ltd Enzyme inhibitors
US5466811A (en) * 1994-07-18 1995-11-14 Merck & Co., Inc. Dioxolenylmethyl carbamates pro moieties for amine drugs
US5656645A (en) * 1994-12-13 1997-08-12 Corvas International, Inc. Aromatic heterocyclic derivatives as enzyme inhibitors
BR9509994A (pt) * 1994-12-13 1997-12-30 Corvas Int Inc Derivados heterocíclicos aromáticos como inibidores de enzimas
US5658930A (en) * 1994-12-13 1997-08-19 Corvas International, Inc. Aromatic heterocyclic derivatives as enzyme inhibitors
JPH11508558A (ja) * 1995-06-27 1999-07-27 メルク エンド カンパニー インコーポレーテッド ピリジノン トロンビン阻害剤
AU720616B2 (en) * 1996-02-22 2000-06-08 Merck & Co., Inc. Pyridinone thrombin inhibitors
JP2000507588A (ja) 1996-03-29 2000-06-20 3―ディメンショナル ファーマシュウティカルズ,インコーポレイテッド プロテアーゼインヒビターとしてのアミジノヒドラゾン
TW499412B (en) 1996-11-26 2002-08-21 Dimensional Pharm Inc Aminoguanidines and alkoxyguanidines as protease inhibitors
EP1036063B1 (en) * 1997-11-26 2006-11-02 Ortho-McNeil Pharmaceuticals, Inc. Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors
AU759427B2 (en) * 1998-06-11 2003-04-17 3-Dimensional Pharmaceuticals, Inc. Pyrazinone protease inhibitors
CA2372234A1 (en) 1999-05-27 2000-12-07 3-Dimensional Pharmaceuticals, Inc. Oxazaheterocycles as protease inhibitors
WO2001004117A1 (en) 1999-07-09 2001-01-18 3-Dimensional Pharmaceuticals, Inc. Heteroaryl protease inhibitors and diagnostic imaging agents
US6236492B1 (en) * 1999-08-03 2001-05-22 Crystal Corporation Electrode with a balanced centroid, soft edges and an apodization ratio greater than one

Also Published As

Publication number Publication date
US6350764B2 (en) 2002-02-26
EA004180B1 (ru) 2004-02-26
US20020086872A1 (en) 2002-07-04
EA200000578A1 (ru) 2001-02-26
AU751412B2 (en) 2002-08-15
US6245763B1 (en) 2001-06-12
JP2001524467A (ja) 2001-12-04
US20040106633A1 (en) 2004-06-03
EP1036063A1 (en) 2000-09-20
PL340560A1 (en) 2001-02-12
ATE344246T1 (de) 2006-11-15
DE69836346D1 (de) 2006-12-14
US20020007070A1 (en) 2002-01-17
US7402586B2 (en) 2008-07-22
US6566379B1 (en) 2003-05-20
AR016702A1 (es) 2001-07-25
EP1036063B1 (en) 2006-11-02
WO1999026926A1 (en) 1999-06-03
US20060211719A1 (en) 2006-09-21
US7029654B2 (en) 2006-04-18
CA2311969A1 (en) 1999-06-03
ES2274587T3 (es) 2007-05-16
US20030087921A1 (en) 2003-05-08
BR9815325A (pt) 2001-12-26
US6037356A (en) 2000-03-14
US6472399B2 (en) 2002-10-29
US20030225115A1 (en) 2003-12-04
AU1799199A (en) 1999-06-15
DE69836346T2 (de) 2007-05-24
US6706021B2 (en) 2004-03-16

Similar Documents

Publication Publication Date Title
TWI222441B (en) Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors
AU759427B2 (en) Pyrazinone protease inhibitors
CN105228982A (zh) 用于治疗过度增殖性病症的3-乙酰基氨基-1-(苯基-杂芳基-氨基羰基或苯基-杂芳基-羰基氨基)苯衍生物
TW499412B (en) Aminoguanidines and alkoxyguanidines as protease inhibitors
JP2003500376A (ja) Xa因子の阻害剤
AU2019203282A1 (en) Dipeptide and tripeptide epoxy ketone protease inhibitors
JP2003500385A (ja) Xa因子阻害剤
JP2017523995A (ja) Metap−2阻害剤としてのピロリジノン誘導体
CA3024071C (en) Libraries of diverse macrocyclic compounds and methods of making and using the same
TW415940B (en) Condensed cyclic carboxylic acid compound or salt thereof, and medical composition containing which
US6326492B1 (en) Heterocyclic protease inhibitors
US6420397B1 (en) Heteroaryl protease inhibitors and diagnostic imaging agents
TW407155B (en) Novel piperazine derivatives having GPIIb/IIIa antagonistic activity and pharmaceutical compositions containing them
JP3574455B2 (ja) 抗ウイルス剤として有用なマクロ環式ジフルオロスタトン誘導体類
MXPA00011612A (en) Pyrazinone protease inhibitors
MXPA00005055A (en) Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors
AU2003213524A1 (en) Thromboresistant materials incorporating pyrazinone protease inhibitors as thromboresistant surfaces and for medical devices

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees