CA2124169A1 - Composes chimiques - Google Patents

Composes chimiques

Info

Publication number: CA2124169A1
Authority: CA; Canada
Prior art keywords: compound according; compound; independently; aminoiminomethyl; acid
Prior art date: 1994-05-24
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.): Abandoned

Application number

CA002124169A

Other languages

English (en)

Inventor

Richard Mcculloch Keenan

William Henry Miller

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.)

SmithKline Beecham Corp

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.)

1994-05-24

Filing date

1994-05-24

Publication date

1995-11-25

1994-05-24 Application filed by SmithKline Beecham Corp filed Critical SmithKline Beecham Corp

1994-05-24 Priority to CA002124169A priority Critical patent/CA2124169A1/fr

1995-11-25 Publication of CA2124169A1 publication Critical patent/CA2124169A1/fr

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 194
238000000034 method Methods 0.000 claims abstract description 79
208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 15
230000002401 inhibitory effect Effects 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
-1 -OR12 Chemical group 0.000 claims description 48
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 19
239000003527 fibrinolytic agent Substances 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
150000001413 amino acids Chemical class 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
125000000524 functional group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
206010038563 Reocclusion Diseases 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
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239000003937 drug carrier Substances 0.000 claims description 4
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125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
208000028867 ischemia Diseases 0.000 claims description 3
125000006362 methylene amino carbonyl group Chemical group [H]N(C([*:2])=O)C([H])([H])[*:1] 0.000 claims description 3
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230000001052 transient effect Effects 0.000 claims description 3
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229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
125000006360 carbonyl amino methylene group Chemical group [H]N(C([*:1])=O)C([H])([H])[*:2] 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
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239000002253 acid Substances 0.000 description 20
150000004702 methyl esters Chemical class 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
239000000203 mixture Substances 0.000 description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
235000002639 sodium chloride Nutrition 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
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159000000021 acetate salts Chemical group 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 13
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
230000027455 binding Effects 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
239000000047 product Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
238000001802 infusion Methods 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
108090000373 Tissue Plasminogen Activator Proteins 0.000 description 9
102000003978 Tissue Plasminogen Activator Human genes 0.000 description 9
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
102000004169 proteins and genes Human genes 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
229960000187 tissue plasminogen activator Drugs 0.000 description 9
IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical group NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
102000001938 Plasminogen Activators Human genes 0.000 description 7
108010001014 Plasminogen Activators Proteins 0.000 description 7
230000002776 aggregation Effects 0.000 description 7
238000004220 aggregation Methods 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
125000002619 bicyclic group Chemical group 0.000 description 7
239000000872 buffer Substances 0.000 description 7
238000007796 conventional method Methods 0.000 description 7
229940127126 plasminogen activator Drugs 0.000 description 7
108090000765 processed proteins & peptides Proteins 0.000 description 7
238000000746 purification Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
230000003480 fibrinolytic effect Effects 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
238000002560 therapeutic procedure Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
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239000008273 gelatin Substances 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
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238000010992 reflux Methods 0.000 description 5
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FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
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Classifications

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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002124169A 1994-05-24 1994-05-24 Composes chimiques Abandoned CA2124169A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002124169A CA2124169A1 (fr)	1994-05-24	1994-05-24	Composes chimiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002124169A CA2124169A1 (fr)	1994-05-24	1994-05-24	Composes chimiques

Publications (1)

Publication Number	Publication Date
CA2124169A1 true CA2124169A1 (fr)	1995-11-25

Family

ID=4153659

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002124169A Abandoned CA2124169A1 (fr)	1994-05-24	1994-05-24	Composes chimiques

Country Status (1)

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CA (1)	CA2124169A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6448281B1 (en)	2000-07-06	2002-09-10	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
US7576079B2 (en)	2001-07-25	2009-08-18	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
US7582770B2 (en)	2004-02-20	2009-09-01	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7838537B2 (en)	2003-01-22	2010-11-23	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7888363B2 (en)	2003-01-22	2011-02-15	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US8076365B2 (en)	2005-08-12	2011-12-13	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors

1994
- 1994-05-24 CA CA002124169A patent/CA2124169A1/fr not_active Abandoned

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6448281B1 (en)	2000-07-06	2002-09-10	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
US6479508B1 (en)	2000-07-06	2002-11-12	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
US6794404B2 (en)	2000-07-06	2004-09-21	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
US7439258B2 (en)	2000-07-06	2008-10-21	Boehringer Ingelheim (Canada) Ltd	Viral polymerase inhibitors
US7803944B2 (en)	2001-07-25	2010-09-28	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7576079B2 (en)	2001-07-25	2009-08-18	Boehringer Ingelheim (Canada) Ltd.	Viral polymerase inhibitors
US7893084B2 (en)	2001-07-25	2011-02-22	Boehringer Ingelheim Canada Ltd.	Viral polymerase inhibitors
US7838537B2 (en)	2003-01-22	2010-11-23	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7888363B2 (en)	2003-01-22	2011-02-15	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7582770B2 (en)	2004-02-20	2009-09-01	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7879851B2 (en)	2004-02-20	2011-02-01	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US8030309B2 (en)	2004-02-20	2011-10-04	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US8076365B2 (en)	2005-08-12	2011-12-13	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors

Legal Events

Date	Code	Title	Description
1998-05-25	FZDE	Discontinued

Publication	Publication Date	Title
US5741804A (en)	1998-04-21	Substituted benzimazoles which inhibit platelet aggrecation
US5602145A (en)	1997-02-11	Bicyclic fibrinogen antagonists
US6117910A (en)	2000-09-12	Bicyclic fibrinogen antagonists
WO1996026190A1 (fr)	1996-08-29	Antagonistes des recepteurs a l'integrine
EP0593603B1 (fr)	2002-11-20	Antagonistes bicycliques de fibrinogene
US6008214A (en)	1999-12-28	Bicyclic compounds
CA2192764C (fr)	2008-03-11	Antagonistes de recepteurs de l'integrine
US6069143A (en)	2000-05-30	Fibrinogen receptor antagonists
WO1999006049A1 (fr)	1999-02-11	Antagonistes du recepteur de l'integrine
WO1996000574A1 (fr)	1996-01-11	Antagonistes du recepteur de la vibronectine
NZ259802A (en)	1997-10-24	Bicyclic derivatives and pharmaceutical compositions
US6037343A (en)	2000-03-14	Fibrinogen receptor antagonists
US5726192A (en)	1998-03-10	Platelet aggregation inhibiting compounds
US5939412A (en)	1999-08-17	Bicyclic fibrinogen antagonists
EP0796252A1 (fr)	1997-09-24	Antagonistes du fibrinogene a cycle double
CA2304117A1 (fr)	1999-03-11	Antagonistes des recepteurs d'integrines
CA2124169A1 (fr)	1995-11-25	Composes chimiques
US6028087A (en)	2000-02-22	Platelet aggregation inhibiting compounds
US5900422A (en)	1999-05-04	Fibrinogen receptor antagonists
NZ260576A (en)	1996-11-26	Benzimidazole or indole derivatives, preparation and pharmaceutical compositions thereof
US6403578B1 (en)	2002-06-11	Bicyclic fibrinogen antagonists
US6458784B1 (en)	2002-10-01	Vitronectin receptor antagonists
WO1994022440A1 (fr)	1994-10-13	Composes bicycliques inhibant l'agregation plaquettaire
EP0677041A1 (fr)	1995-10-18	Composes chimiques
US20020055499A1 (en)	2002-05-09	Integrin receptor antagonists