CA2136007C - Novel compound with platelet aggregation inhibitor activity - Google Patents

Novel compound with platelet aggregation inhibitor activity

Info

Publication number
CA2136007C
CA2136007C CA002136007A CA2136007A CA2136007C CA 2136007 C CA2136007 C CA 2136007C CA 002136007 A CA002136007 A CA 002136007A CA 2136007 A CA2136007 A CA 2136007A CA 2136007 C CA2136007 C CA 2136007C
Authority
CA
Canada
Prior art keywords
group
brs
nmr
compound
mixture
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.)
Expired - Fee Related
Application number
CA002136007A
Other languages
English (en)
French (fr)
Other versions
CA2136007A1 (en
Inventor
Kiyoaki Katano
Shokichi Ohuchi
Eiki Shitara
Masaro Shimizu
Kazue Yaegashi
Tomoaki Miura
Yasuko Isomura
Hiroyuki Iida
Midori Ishikawa
Kenji Asai
Emiko Hatsushiba
Mami Kawaguchi
Takashi Tsuruoka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Meiji Seika Kaisha Ltd
Original Assignee
Meiji Seika Kaisha Ltd
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 Meiji Seika Kaisha Ltd filed Critical Meiji Seika Kaisha Ltd
Publication of CA2136007A1 publication Critical patent/CA2136007A1/en
Application granted granted Critical
Publication of CA2136007C publication Critical patent/CA2136007C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/16—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CA002136007A 1993-03-17 1994-03-17 Novel compound with platelet aggregation inhibitor activity Expired - Fee Related CA2136007C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP57463/1993 1993-03-17
JP5746393 1993-03-17
JP82145/1993 1993-04-08
JP8214593 1993-04-08
JP265273/1993 1993-10-22
JP26527393 1993-10-22
PCT/JP1994/000437 WO1994021599A1 (en) 1993-03-17 1994-03-17 Novel compound with platelet aggregation inhibitor activity

Publications (2)

Publication Number Publication Date
CA2136007A1 CA2136007A1 (en) 1994-09-29
CA2136007C true CA2136007C (en) 1999-12-14

Family

ID=27296266

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002136007A Expired - Fee Related CA2136007C (en) 1993-03-17 1994-03-17 Novel compound with platelet aggregation inhibitor activity

Country Status (15)

Country Link
US (2) US5594004A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0641770B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JP2680196B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR100196563B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN1045084C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) ATE166047T1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU688756B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA2136007C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE69410193T2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DK (1) DK0641770T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES2117264T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO308607B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NZ (1) NZ262768A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
TW (1) TW269687B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO1994021599A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT656348E (pt) * 1993-12-03 2000-10-31 Hoffmann La Roche Derivados do acido acetico como medicamentos
AU2044297A (en) * 1996-03-29 1997-10-22 Meiji Seika Kaisha Ltd. Novel heterocyclic compounds having platelet aggregation inhibitory effects
US5792761A (en) * 1996-08-12 1998-08-11 Merck & Co., Inc. Thrombin inhibitors
WO2001010844A1 (en) 1999-08-05 2001-02-15 Meiji Seika Kaisha, Ltd. φ-AMINO-α-HYDROXYCARBOXYLIC ACID DERIVATIVES HAVING INTEGRIN αvβ3 ANTAGONISM
TWI290136B (en) 2000-04-05 2007-11-21 Daiichi Seiyaku Co Ethylenediamine derivatives
CN100341506C (zh) 2000-12-25 2007-10-10 三共株式会社 含有阿斯匹林的药用组合物
US7365205B2 (en) 2001-06-20 2008-04-29 Daiichi Sankyo Company, Limited Diamine derivatives
CA2558064A1 (en) * 2004-02-25 2005-09-01 Astellas Pharma Inc. Contrast medium for thrombus formation
DK1778243T3 (da) * 2004-06-30 2013-02-04 Athersys Inc Substituerede azepinderivater som serotoninreceptormodulatorer
US20060019929A1 (en) * 2004-07-07 2006-01-26 Albert Friesen Combination therapies employing platelet aggregation drugs
JP2008517956A (ja) 2004-10-28 2008-05-29 メディキュア・インターナショナル・インコーポレーテッド 二重の抗血小板性／抗凝固性ピリドキシン類似体
US20060094749A1 (en) * 2004-10-28 2006-05-04 Medicure International Inc. Substituted pyridoxines as anti-platelet agents
US7459468B2 (en) * 2004-10-28 2008-12-02 Medicure International, Inc. Aryl sulfonic pyridoxines as antiplatelet agents
WO2012104866A1 (en) 2011-01-31 2012-08-09 Council Of Scientific & Industrial Research Chiral 1-(4-methylphenylmethyl)-5-oxo-{n-[(3-t-butoxycarbonyl- aminomethyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion
CN103351359B (zh) * 2013-07-25 2015-02-25 郑桂富 一种3-苯甲基-5-(2-羟乙基)-4-甲基噻唑啉氯的合成方法
CA2997549C (en) * 2015-09-04 2023-10-03 Shin Poong Pharmaceutical Co., Ltd. Compound having effect of inhibiting platelet aggregation and salt thereof, and composition for preventing or treating thrombotic diseases, containing same

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8528398D0 (en) * 1985-11-19 1985-12-24 Glaxo Group Ltd Chemical compounds
EP0358724A4 (en) * 1987-06-15 1990-06-05 Iraj Lalezari COMPOSITION, COMPOUND AND METHOD FOR REDUCING LIPIDS, MODIFYING THE AFFINITY OF HEMOGLOBIN FOR OXYGEN AND PREVENTING THE BLOOD LEVEL.
US4921997A (en) * 1988-06-15 1990-05-01 Montefiore Medical Center Method of synthesis and novel compounds for pharmaceutical uses
US5084466A (en) * 1989-01-31 1992-01-28 Hoffmann-La Roche Inc. Novel carboxamide pyridine compounds which have useful pharmaceutical utility
DE4010536A1 (de) * 1990-04-02 1991-10-10 Boehringer Mannheim Gmbh Pharmazeutische waessrige loesung von 4-(2-(benzolsulfonylamino)-ethyl)-phenoxyessigsaeure
DE69109871T2 (de) * 1990-10-10 1995-09-14 Schering Corp., Kenilworth, N.J. Pyridin- und pyridin-n-oxid-derivate von diarylmethyl- piperidinen oder piperazinen, deren zusammensetzungen und anwendung.
JP2503797B2 (ja) 1991-03-11 1996-06-05 株式会社セガ・エンタープライゼス 熱変色遊戯機
US5220050A (en) * 1991-05-17 1993-06-15 G. D. Searle & Co. Peptide mimetic compounds useful as platelet aggregation inhibitors

Also Published As

Publication number Publication date
WO1994021599A1 (en) 1994-09-29
CN1045084C (zh) 1999-09-15
EP0641770B1 (en) 1998-05-13
EP0641770A1 (en) 1995-03-08
NZ262768A (en) 1997-03-24
KR100196563B1 (ko) 1999-06-15
EP0641770A4 (en) 1995-06-28
NO944371D0 (no) 1994-11-16
AU6263894A (en) 1994-10-11
KR950701615A (ko) 1995-04-28
AU688756B2 (en) 1998-03-19
DE69410193D1 (de) 1998-06-18
CA2136007A1 (en) 1994-09-29
JP2680196B2 (ja) 1997-11-19
US5594004A (en) 1997-01-14
DK0641770T3 (da) 1998-06-02
TW269687B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1996-02-01
ATE166047T1 (de) 1998-05-15
CN1107277A (zh) 1995-08-23
ES2117264T3 (es) 1998-08-01
NO308607B1 (no) 2000-10-02
US5698692A (en) 1997-12-16
DE69410193T2 (de) 1998-09-03
NO944371L (no) 1995-01-13

Similar Documents

Publication Publication Date Title
CA2136007C (en) Novel compound with platelet aggregation inhibitor activity
AU667107B2 (en) Thiazolylvinylphenyl derivatives
EP0184170B1 (en) Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents
HU201963B (en) Process for producing heterocyclic ketones and pharmaceutical compositions comprising same as active ingredient
BG60404B2 (bg) Аминокиселинни производни
JPS6241600B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP5266053B2 (ja) ＴＡＦＩａのインヒビターとしてのイミダゾール誘導体
WO2005079793A1 (en) Prostaglandin d2 antagonist
JP4680593B2 (ja) アシルアミノチアゾール誘導体、その製造法および治療用途
JPH0759590B2 (ja) 新規なスピロ環式アミノ酸誘導体およびそれらの製造法
JPH01113364A (ja) 非ペプチジルα−コハク酸アミドアシルアミノジオール抗高血圧剤
US5658943A (en) Phenylalanine derivatives as endothelin antagonists
JPWO2002051820A1 (ja) ジヒドロナフタレン誘導体化合物およびその化合物を有効成分とする薬剤
PT87702B (pt) Processo para a preparacao de derivados de oxazolidin-2-ona uteis como agentes hipoglicemicos
JPS6351381A (ja) ベンゾチアゼピン誘導体
ES2328467T3 (es) Derivados heterociclicos de 5 miembros, su preparacion y su aplicacion como medicamentos.
JP2006517589A (ja) セリンプロテアーゼ・インヒビターとして有用なベンゼンアセトアミド化合物
WO2000012491A1 (fr) Derives d'acide carboxylique et medicaments dont ils sont le principe actif
CA1322074C (en) Pharmaceutically useful derivatives of thiazolidine-4- carboxylic acid
JP2023538768A (ja) 緑膿菌病原性因子ＬａｓＢの阻害剤
KR100384261B1 (ko) 나프틸옥시아세트산유도체
US5001140A (en) Cycloalkylthiazoles
AU626308B2 (en) (((Cycloalkylthiazolyl)ethenyl)phenylamino)-oxoalkanoic acid derivatives
AU723180B2 (en) Novel compound with platelet aggregation inhibitor activity
JP2002509128A (ja) アルケニルジアリールメタン非ヌクレオシドｈｉｖ−１逆転写酵素インヒビタ

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed