IL99537A - Fibrinogen receptor antagonists and pharmaceutical preparations containing them - Google Patents
Fibrinogen receptor antagonists and pharmaceutical preparations containing themInfo
- Publication number
- IL99537A IL99537A IL9953791A IL9953791A IL99537A IL 99537 A IL99537 A IL 99537A IL 9953791 A IL9953791 A IL 9953791A IL 9953791 A IL9953791 A IL 9953791A IL 99537 A IL99537 A IL 99537A
- Authority
- IL
- Israel
- Prior art keywords
- propionic acid
- phenyl
- compound
- alkyl
- substituted
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 239000002319 fibrinogen receptor antagonist Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 14
- 108010049003 Fibrinogen Proteins 0.000 claims abstract description 9
- 102000008946 Fibrinogen Human genes 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 229940012952 fibrinogen Drugs 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims description 55
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 210000001772 blood platelet Anatomy 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- -1 di-substituted 1-ethenyl Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 235000019260 propionic acid Nutrition 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 12
- 208000005189 Embolism Diseases 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 239000003146 anticoagulant agent Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000002776 aggregation Effects 0.000 claims description 6
- 238000004220 aggregation Methods 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000003527 fibrinolytic agent Substances 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229960000103 thrombolytic agent Drugs 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
- 150000008574 D-amino acids Chemical class 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 229940127219 anticoagulant drug Drugs 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 230000002744 anti-aggregatory effect Effects 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 229940127090 anticoagulant agent Drugs 0.000 claims description 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000013268 sustained release Methods 0.000 claims description 2
- 239000012730 sustained-release form Substances 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 claims 4
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 2
- MGTWQQAKBKIOJU-UHFFFAOYSA-N 3-[4-(5-bromopentoxy)phenyl]-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C=1C=CC=CC=1COC(=O)NC(C(=O)O)CC1=CC=C(OCCCCCBr)C=C1 MGTWQQAKBKIOJU-UHFFFAOYSA-N 0.000 claims 1
- 125000006550 alkoxycarbonyl aryl group Chemical group 0.000 claims 1
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- 229910052799 carbon Inorganic materials 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- FXSZGKYGUFCBQY-UHFFFAOYSA-N propanoic acid;dihydrochloride Chemical compound Cl.Cl.CCC(O)=O FXSZGKYGUFCBQY-UHFFFAOYSA-N 0.000 claims 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 239000005557 antagonist Substances 0.000 abstract 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- 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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
- C07C325/02—Thioketones; Oxides thereof
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- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C327/00—Thiocarboxylic acids
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- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
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- 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
- C07D211/20—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 singly bound oxygen or sulphur atoms
- C07D211/22—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 singly bound oxygen or sulphur atoms by oxygen atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3882—Arylalkanephosphonic acids
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
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- C07C2601/00—Systems containing only non-condensed rings
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- C07C2601/14—The ring being saturated
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US58929990A | 1990-09-27 | 1990-09-27 | |
US75064591A | 1991-08-30 | 1991-08-30 |
Publications (2)
Publication Number | Publication Date |
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IL99537A0 IL99537A0 (en) | 1992-08-18 |
IL99537A true IL99537A (en) | 1995-11-27 |
Family
ID=27080499
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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IL9953791A IL99537A (en) | 1990-09-27 | 1991-09-20 | Fibrinogen receptor antagonists and pharmaceutical preparations containing them |
Country Status (16)
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US (1) | US5294616A (pt) |
EP (1) | EP0478328B1 (pt) |
JP (1) | JPH0819066B2 (pt) |
KR (1) | KR920006298A (pt) |
AT (1) | ATE132850T1 (pt) |
AU (1) | AU653360B2 (pt) |
CA (1) | CA2052069A1 (pt) |
DE (1) | DE69116285T2 (pt) |
DK (1) | DK0478328T3 (pt) |
ES (1) | ES2083534T3 (pt) |
FI (1) | FI914535A (pt) |
GR (1) | GR3018635T3 (pt) |
IE (1) | IE68955B1 (pt) |
IL (1) | IL99537A (pt) |
NO (1) | NO177703C (pt) |
PT (1) | PT99097B (pt) |
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-
1991
- 1991-09-20 IL IL9953791A patent/IL99537A/en active IP Right Grant
- 1991-09-23 CA CA002052069A patent/CA2052069A1/en not_active Abandoned
- 1991-09-26 KR KR1019910016837A patent/KR920006298A/ko not_active Application Discontinuation
- 1991-09-26 DK DK91308793.8T patent/DK0478328T3/da active
- 1991-09-26 FI FI914535A patent/FI914535A/fi not_active Application Discontinuation
- 1991-09-26 ES ES91308793T patent/ES2083534T3/es not_active Expired - Lifetime
- 1991-09-26 IE IE338291A patent/IE68955B1/en not_active IP Right Cessation
- 1991-09-26 AT AT91308793T patent/ATE132850T1/de not_active IP Right Cessation
- 1991-09-26 PT PT99097A patent/PT99097B/pt not_active IP Right Cessation
- 1991-09-26 NO NO913787A patent/NO177703C/no not_active IP Right Cessation
- 1991-09-26 AU AU84788/91A patent/AU653360B2/en not_active Ceased
- 1991-09-26 DE DE69116285T patent/DE69116285T2/de not_active Expired - Fee Related
- 1991-09-26 EP EP91308793A patent/EP0478328B1/en not_active Expired - Lifetime
- 1991-09-27 JP JP3318723A patent/JPH0819066B2/ja not_active Expired - Lifetime
-
1992
- 1992-03-25 US US07/857,528 patent/US5294616A/en not_active Expired - Fee Related
-
1996
- 1996-01-11 GR GR950403582T patent/GR3018635T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
IE913382A1 (en) | 1992-04-08 |
IL99537A0 (en) | 1992-08-18 |
FI914535A0 (fi) | 1991-09-26 |
AU8478891A (en) | 1992-04-02 |
NO913787D0 (no) | 1991-09-26 |
JPH0819066B2 (ja) | 1996-02-28 |
DK0478328T3 (da) | 1996-02-05 |
JPH05155828A (ja) | 1993-06-22 |
AU653360B2 (en) | 1994-09-29 |
DE69116285T2 (de) | 1996-10-17 |
ATE132850T1 (de) | 1996-01-15 |
NO913787L (no) | 1992-03-30 |
DE69116285D1 (de) | 1996-02-22 |
NO177703C (no) | 1995-11-08 |
FI914535A (fi) | 1992-03-28 |
PT99097A (pt) | 1992-08-31 |
GR3018635T3 (en) | 1996-04-30 |
US5294616A (en) | 1994-03-15 |
ES2083534T3 (es) | 1996-04-16 |
NO177703B (no) | 1995-07-31 |
EP0478328A1 (en) | 1992-04-01 |
PT99097B (pt) | 1999-02-26 |
IE68955B1 (en) | 1996-07-24 |
EP0478328B1 (en) | 1996-01-10 |
KR920006298A (ko) | 1992-04-27 |
CA2052069A1 (en) | 1992-03-28 |
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