OA10368A - Bicyclic finbrinogen antagonists - Google Patents

Bicyclic finbrinogen antagonists Download PDF

Info

Publication number: OA10368A
Authority: OA; OAPI
Prior art keywords: carbonyl; oxo; tetrahydro; methyl; mmol
Prior art date: 1994-01-07

Application number

OA60858A

Other languages

English (en)

Inventor

William Edward Bondinell

James Francis Callahan

William Francis Huffman

Richard Mcculloch Keenan

Thomas Wen-Fu Ku

Kenneth Allen Newlander

James Martin Samanen

Irene Nijole Uzinskas

Original Assignee

Smithkline Beecham Corp

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.)

1994-01-07

Filing date

1996-07-05

Publication date

2001-11-15

1996-07-05 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

2001-11-15 Publication of OA10368A publication Critical patent/OA10368A/en

Links

125000002619 bicyclic group Chemical group 0.000 title description 6
239000005557 antagonist Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 316
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 112
-1 [[2-(4-piperidinyl)ethyl] (N-methyl)amino] carbonyl Chemical group 0.000 claims abstract description 78
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims abstract description 43
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 36
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 6
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 6
125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 72
238000000034 method Methods 0.000 claims description 68
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000011734 sodium Substances 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
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229910052708 sodium Inorganic materials 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 10
125000003386 piperidinyl group Chemical group 0.000 claims description 9
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GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
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PYZOVVQJTLOHDG-FQEVSTJZSA-N 2-[(2s)-4-methyl-3-oxo-7-(4-piperidin-4-ylpiperidine-1-carbonyl)-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid Chemical compound O=C([C@H](CC(O)=O)NC1=CC=2)N(C)CC1=CC=2C(=O)N(CC1)CCC1C1CCNCC1 PYZOVVQJTLOHDG-FQEVSTJZSA-N 0.000 claims description 3
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235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229960005076 sodium hypochlorite Drugs 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229940083599 sodium iodide Drugs 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
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238000001356 surgical procedure Methods 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
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238000010189 synthetic method Methods 0.000 description 1
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KCHBQCNVPWUARJ-AWEZNQCLSA-N tert-butyl (2s)-2-(2-methoxy-2-oxoethyl)-4-methyl-3-oxo-2,5-dihydro-1h-1,4-benzodiazepine-8-carboxylate Chemical compound C1N(C)C(=O)[C@H](CC(=O)OC)NC2=CC(C(=O)OC(C)(C)C)=CC=C21 KCHBQCNVPWUARJ-AWEZNQCLSA-N 0.000 description 1
VLZMWNAJSJVDTH-QFIPXVFZSA-N tert-butyl (4s)-4-(2-methoxy-2-oxoethyl)-3-oxo-2-(2-phenylethyl)-4,5-dihydro-1h-2-benzazepine-7-carboxylate Chemical compound C([C@H](C1=O)CC(=O)OC)C2=CC(C(=O)OC(C)(C)C)=CC=C2CN1CCC1=CC=CC=C1 VLZMWNAJSJVDTH-QFIPXVFZSA-N 0.000 description 1
NQWHKWUEZNJEBZ-UHFFFAOYSA-N tert-butyl 3-(bromomethyl)-4-nitrobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C([N+]([O-])=O)C(CBr)=C1 NQWHKWUEZNJEBZ-UHFFFAOYSA-N 0.000 description 1
XBIIKDVOUWNBDK-UHFFFAOYSA-N tert-butyl 3-(methylaminomethyl)-4-nitrobenzoate Chemical compound CNCC1=CC(C(=O)OC(C)(C)C)=CC=C1[N+]([O-])=O XBIIKDVOUWNBDK-UHFFFAOYSA-N 0.000 description 1
QLNWKIRBORTUEG-UHFFFAOYSA-N tert-butyl 3-[[(2-methylpropan-2-yl)oxycarbonyl-(2-phenylethyl)amino]methyl]-4-nitrobenzoate Chemical compound C=1C(C(=O)OC(C)(C)C)=CC=C([N+]([O-])=O)C=1CN(C(=O)OC(C)(C)C)CCC1=CC=CC=C1 QLNWKIRBORTUEG-UHFFFAOYSA-N 0.000 description 1
NFURUMIPKUUZKP-UHFFFAOYSA-N tert-butyl 3-bromo-4-(bromomethyl)benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(CBr)C(Br)=C1 NFURUMIPKUUZKP-UHFFFAOYSA-N 0.000 description 1
BEJDZRSESCFJSU-UHFFFAOYSA-N tert-butyl 3-bromo-4-[(2-phenylethylamino)methyl]benzoate Chemical compound BrC1=CC(C(=O)OC(C)(C)C)=CC=C1CNCCC1=CC=CC=C1 BEJDZRSESCFJSU-UHFFFAOYSA-N 0.000 description 1
RZOLYFYFBRHPQS-UHFFFAOYSA-N tert-butyl 3-bromo-4-methylbenzoate Chemical compound CC1=CC=C(C(=O)OC(C)(C)C)C=C1Br RZOLYFYFBRHPQS-UHFFFAOYSA-N 0.000 description 1
SWAVZCKLGYSSQN-UHFFFAOYSA-N tert-butyl 3-methyl-4-nitrobenzoate Chemical compound CC1=CC(C(=O)OC(C)(C)C)=CC=C1[N+]([O-])=O SWAVZCKLGYSSQN-UHFFFAOYSA-N 0.000 description 1
HSQTYEUTILRRAO-UHFFFAOYSA-N tert-butyl 4-(bromomethyl)-3-nitrobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(CBr)C([N+]([O-])=O)=C1 HSQTYEUTILRRAO-UHFFFAOYSA-N 0.000 description 1
IMOHPVDDNISLPY-UHFFFAOYSA-N tert-butyl 4-fluoro-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC(C)(C)C)=CC=C1F IMOHPVDDNISLPY-UHFFFAOYSA-N 0.000 description 1
ZFTSLXLCLAWXOF-UHFFFAOYSA-N tert-butyl 4-nitro-3-[(2-phenylethylamino)methyl]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C([N+]([O-])=O)C(CNCCC=2C=CC=CC=2)=C1 ZFTSLXLCLAWXOF-UHFFFAOYSA-N 0.000 description 1
NERBLCVCQKXTEP-UHFFFAOYSA-N tert-butyl 4-piperidin-4-ylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCNCC1 NERBLCVCQKXTEP-UHFFFAOYSA-N 0.000 description 1
MZFOSWHOVPVFSL-UHFFFAOYSA-N tert-butyl n-methyl-n-(2-piperidin-4-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)N(C)CCC1CCNCC1 MZFOSWHOVPVFSL-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
229960005001 ticlopidine Drugs 0.000 description 1
229960000187 tissue plasminogen activator Drugs 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
230000008733 trauma Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
229960005356 urokinase Drugs 0.000 description 1
108010047303 von Willebrand Factor Proteins 0.000 description 1
102100036537 von Willebrand factor Human genes 0.000 description 1
229960001134 von willebrand factor Drugs 0.000 description 1
229960005080 warfarin Drugs 0.000 description 1
PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/02—Heterocyclic 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
- C07D401/12—Heterocyclic 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/14—Heterocyclic 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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Hydrogenated Pyridines (AREA)

OA60858A 1994-01-07 1996-07-05 Bicyclic finbrinogen antagonists OA10368A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US17901194A	1994-01-07	1994-01-07

Publications (1)

Publication Number	Publication Date
OA10368A true OA10368A (en)	2001-11-15

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ID=22654859

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60858A OA10368A (en)	1994-01-07	1996-07-05	Bicyclic finbrinogen antagonists

Country Status (26)

Country	Link
US (1)	US6117866A (fr)
EP (1)	EP0738150B1 (fr)
JP (1)	JPH09508620A (fr)
KR (1)	KR100388772B1 (fr)
CN (1)	CN1117569C (fr)
AP (1)	AP542A (fr)
AT (1)	ATE238993T1 (fr)
AU (1)	AU699186B2 (fr)
BG (2)	BG62844B1 (fr)
BR (1)	BR9506499A (fr)
CZ (1)	CZ292323B6 (fr)
DE (1)	DE69530571T2 (fr)
DK (1)	DK0738150T3 (fr)
ES (1)	ES2197914T3 (fr)
HU (1)	HUT76282A (fr)
IL (1)	IL112243A (fr)
MA (1)	MA23420A1 (fr)
NO (1)	NO962859L (fr)
NZ (1)	NZ279394A (fr)
OA (1)	OA10368A (fr)
PT (1)	PT738150E (fr)
SG (1)	SG64884A1 (fr)
SK (1)	SK86996A3 (fr)
TW (1)	TW420682B (fr)
WO (1)	WO1995018619A1 (fr)
ZA (1)	ZA9545B (fr)

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1995
- 1995-01-02 MA MA23747A patent/MA23420A1/fr unknown
- 1995-01-04 IL IL11224395A patent/IL112243A/xx not_active IP Right Cessation
- 1995-01-05 ZA ZA9545A patent/ZA9545B/xx unknown
- 1995-01-06 AP APAP/P/1995/000710A patent/AP542A/en active
- 1995-01-09 NZ NZ279394A patent/NZ279394A/en not_active IP Right Cessation
- 1995-01-09 CN CN95191991A patent/CN1117569C/zh not_active Expired - Fee Related
- 1995-01-09 JP JP7518646A patent/JPH09508620A/ja not_active Ceased
- 1995-01-09 WO PCT/US1995/000248 patent/WO1995018619A1/fr not_active Ceased
- 1995-01-09 AT AT95908006T patent/ATE238993T1/de not_active IP Right Cessation
- 1995-01-09 AU AU16001/95A patent/AU699186B2/en not_active Ceased
- 1995-01-09 EP EP95908006A patent/EP0738150B1/fr not_active Expired - Lifetime
- 1995-01-09 US US08/875,359 patent/US6117866A/en not_active Expired - Fee Related
- 1995-01-09 CZ CZ19961981A patent/CZ292323B6/cs not_active IP Right Cessation
- 1995-01-09 PT PT95908006T patent/PT738150E/pt unknown
- 1995-01-09 SK SK869-96A patent/SK86996A3/sk unknown
- 1995-01-09 ES ES95908006T patent/ES2197914T3/es not_active Expired - Lifetime
- 1995-01-09 SG SG1996004249A patent/SG64884A1/en unknown
- 1995-01-09 DK DK95908006T patent/DK0738150T3/da active
- 1995-01-09 HU HU9601849A patent/HUT76282A/hu unknown
- 1995-01-09 BR BR9506499A patent/BR9506499A/pt not_active Application Discontinuation
- 1995-01-09 DE DE69530571T patent/DE69530571T2/de not_active Expired - Fee Related
- 1995-01-09 KR KR1019960703660A patent/KR100388772B1/ko not_active Expired - Fee Related
- 1995-02-16 TW TW084101430A patent/TW420682B/zh not_active IP Right Cessation
1996
- 1996-07-05 NO NO962859A patent/NO962859L/no unknown
- 1996-07-05 BG BG100698A patent/BG62844B1/bg unknown
- 1996-07-05 OA OA60858A patent/OA10368A/en unknown
1998
- 1998-10-22 BG BG102863A patent/BG102863A/xx unknown

Also Published As

Publication number	Publication date
NZ279394A (en)	1998-05-27
KR100388772B1 (ko)	2003-11-20
CN1143323A (zh)	1997-02-19
WO1995018619A1 (fr)	1995-07-13
CZ198196A3 (en)	1997-06-11
TW420682B (en)	2001-02-01
IL112243A (en)	1999-12-31
JPH09508620A (ja)	1997-09-02
AU1600195A (en)	1995-08-01
BG62844B1 (bg)	2000-09-29
ZA9545B (en)	1996-01-23
DE69530571T2 (de)	2004-03-04
HK1014668A1 (en)	1999-09-30
US6117866A (en)	2000-09-12
HUT76282A (en)	1997-07-28
EP0738150B1 (fr)	2003-05-02
SG64884A1 (en)	1999-05-25
DE69530571D1 (de)	2003-06-05
BG102863A (en)	1999-05-31
SK86996A3 (en)	1997-02-05
BR9506499A (pt)	1997-09-09
AU699186B2 (en)	1998-11-26
HU9601849D0 (en)	1996-09-30
WO1995018619A9 (fr)	2004-10-21
CN1117569C (zh)	2003-08-13
ES2197914T3 (es)	2004-01-16
EP0738150A4 (fr)	1997-03-19
IL112243A0 (en)	1995-03-30
PT738150E (pt)	2003-08-29
BG100698A (bg)	1997-02-28
ATE238993T1 (de)	2003-05-15
AP542A (en)	1996-10-01
NO962859L (no)	1996-09-05
NO962859D0 (no)	1996-07-05
AP9500710A0 (en)	1995-01-31
EP0738150A1 (fr)	1996-10-23
CZ292323B6 (cs)	2003-09-17
DK0738150T3 (da)	2003-08-25
MA23420A1 (fr)	1995-10-01

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OA10368A (en)	2001-11-15	Bicyclic finbrinogen antagonists
AU689762B2 (en)	1998-04-09	Bicyclic fibrinogen antagonists
NZ332173A (en)	2000-06-23	N-(amidinophenyl)-n'-(subst.)-3h-2,4-benzodiazepin-3-one derivatives as factor xa inhibitors
JP2000502664A (ja)	2000-03-07	アルファ―ｖ―インテグリン阻害剤としてのチロシン誘導体
KR20150018788A (ko)	2015-02-24	혈전색전성 질환의 치료를 위한 인자 ｘｉａ 억제제로서 치환된 피롤리딘
CA2121112A1 (fr)	1994-10-14	Nouveaux derives benzamide, procedes pour leur preparation et composition pharmaceutique en contenant
JPH08301857A (ja)	1996-11-19	接着性レセプター拮抗化合物
RU2234505C2 (ru)	2004-08-20	Производные хроменона и хроманона в качестве ингибиторов интегринов
US20050043304A1 (en)	2005-02-24	Novel amine derivative having human beta-tryptase inhibitory activity and drugs containing the same
Bondinell et al.	1994	Design of a potent and orally active nonpeptide platelet fibrinogen receptor (GPIIb/IIIa) antagonist
US6403578B1 (en)	2002-06-11	Bicyclic fibrinogen antagonists
HK1014668B (en)	2003-12-24	Bicyclic fibrinogen antagonists
CA2180441A1 (fr)	1995-07-13	Antagonistes de fibrinogene bicycliques
JPH08231516A (ja)	1996-09-10	ジアザ環式化合物
JP2009517351A (ja)	2009-04-30	化学物質
FR2967412A1 (fr)	2012-05-18	Nouveaux derives d'indolizine, leur preparation et leur application en therapeutique
BR112019027678A2 (pt)	2020-09-15	derivados de benzazepina
MXPA01005347A (en)	2002-05-09	Isonipecotamides for the treatment of integrinmediated disorders
MXPA98004971A (en)	1998-11-16	Tyrosin derivatives as inhibitors of alpha-v-integr
AU4380301A (en)	2001-07-26	Bicyclic fibrinogen antagonists
MXPA01004272A (en)	2001-12-13	Chromenone and chromanone derivatives as integrin inhibitors