NO316650B1 - Nye bicykliske amino-pyrazinonforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem - Google Patents
Nye bicykliske amino-pyrazinonforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem Download PDFInfo
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- NO316650B1 NO316650B1 NO20002941A NO20002941A NO316650B1 NO 316650 B1 NO316650 B1 NO 316650B1 NO 20002941 A NO20002941 A NO 20002941A NO 20002941 A NO20002941 A NO 20002941A NO 316650 B1 NO316650 B1 NO 316650B1
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- 238000002360 preparation method Methods 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 57
- -1 bicyclic amino-pyrazinone compounds Chemical class 0.000 title claims description 44
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 108010022999 Serine Proteases Proteins 0.000 claims description 8
- 102000012479 Serine Proteases Human genes 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 108090000631 Trypsin Proteins 0.000 claims description 3
- 102000004142 Trypsin Human genes 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 239000012588 trypsin Substances 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 239000003868 thrombin inhibitor Substances 0.000 claims description 2
- 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 claims 1
- 229940122388 Thrombin inhibitor Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 28
- 229910052739 hydrogen Inorganic materials 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 108090000190 Thrombin Proteins 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 229960004072 thrombin Drugs 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015271 coagulation Effects 0.000 description 8
- 238000005345 coagulation Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical class CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VVTAUYUSSABNDB-UHFFFAOYSA-N 2,2-bis(4-methoxyphenyl)ethanamine Chemical compound C1=CC(OC)=CC=C1C(CN)C1=CC=C(OC)C=C1 VVTAUYUSSABNDB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000003527 fibrinolytic agent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000014508 negative regulation of coagulation Effects 0.000 description 3
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
- RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 2
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 2
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- NVKOCDGGRHAHOJ-JTQLQIEISA-N benzyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound O=C([C@H]1NC(=O)CC1)OCC1=CC=CC=C1 NVKOCDGGRHAHOJ-JTQLQIEISA-N 0.000 description 2
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Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9907538A FR2795072B1 (fr) | 1999-06-15 | 1999-06-15 | Nouveaux derives bicycliques d'amino-pyrazinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20002941D0 NO20002941D0 (no) | 2000-06-08 |
| NO20002941L NO20002941L (no) | 2000-12-18 |
| NO316650B1 true NO316650B1 (no) | 2004-03-22 |
Family
ID=9546789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20002941A NO316650B1 (no) | 1999-06-15 | 2000-06-08 | Nye bicykliske amino-pyrazinonforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6277851B1 (ja) |
| EP (1) | EP1069132B1 (ja) |
| JP (1) | JP3364472B2 (ja) |
| KR (1) | KR100456796B1 (ja) |
| CN (1) | CN1147489C (ja) |
| AT (1) | ATE251177T1 (ja) |
| AU (1) | AU766194B2 (ja) |
| BR (1) | BR0002643A (ja) |
| CA (1) | CA2312206C (ja) |
| DE (1) | DE60005609T2 (ja) |
| DK (1) | DK1069132T3 (ja) |
| EA (1) | EA003209B1 (ja) |
| ES (1) | ES2208239T3 (ja) |
| FR (1) | FR2795072B1 (ja) |
| HK (1) | HK1032236A1 (ja) |
| HU (1) | HUP0002277A3 (ja) |
| NO (1) | NO316650B1 (ja) |
| NZ (1) | NZ505149A (ja) |
| PL (1) | PL199522B1 (ja) |
| PT (1) | PT1069132E (ja) |
| SE (1) | SE1069132T5 (ja) |
| SI (1) | SI1069132T1 (ja) |
| ZA (1) | ZA200003034B (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1261611A2 (en) * | 2000-02-29 | 2002-12-04 | Bristol-Myers Squibb Pharma Company | Inhibitors of hepatitis c virus ns3 protease |
| FR2818277B1 (fr) * | 2000-12-14 | 2003-01-24 | Servier Lab | Nouveaux derives bicycliques d'amino-pyrazinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2004002405A2 (en) * | 2002-06-26 | 2004-01-08 | Bristol-Myers Squibb Company | Amino-bicyclic pyrazinones and pyridinones |
| FR2867780B1 (fr) * | 2004-03-19 | 2006-05-19 | Servier Lab | Nouveaux derives de 4-oxo-4,6,7,8-tetrahydropyrrolo (1,2-a) pyrazine-6-carboxamides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP2807156A1 (en) * | 2012-01-27 | 2014-12-03 | Novartis AG | Aminopyridine derivatives as plasma kallikrein inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05117276A (ja) * | 1991-10-23 | 1993-05-14 | Sumitomo Pharmaceut Co Ltd | 新規な３環性キノキサリンジオン誘導体 |
| SK83897A3 (en) * | 1994-12-22 | 1998-05-06 | Iaf Biochem Int | Low molecular weight bicyclic thrombin inhibitors |
| WO1996030396A1 (en) * | 1995-03-24 | 1996-10-03 | Molecumetics Ltd. | β-SHEET MIMETICS AND USE THEREOF AS PROTEASE INHIBITORS |
| AU720616B2 (en) * | 1996-02-22 | 2000-06-08 | Merck & Co., Inc. | Pyridinone thrombin inhibitors |
| AU3232597A (en) * | 1996-06-18 | 1998-01-07 | Warner-Lambert Company | Pyrrolo{1,2-a}pyrazine-1,4-dione serine protease inhibitors |
| WO1998009987A1 (en) * | 1996-09-06 | 1998-03-12 | Biochem Pharma, Inc. | Lactam inhibitors of thrombin |
| CA2267260A1 (en) * | 1996-10-24 | 1998-04-30 | Merck & Co., Inc. | Thrombin inhibitors |
| US5792779A (en) * | 1997-02-19 | 1998-08-11 | Merck & Co., Inc. | Pyridinone thrombin inhibitors |
| WO1999015169A1 (en) * | 1997-09-23 | 1999-04-01 | Merck & Co., Inc. | Thrombin inhibitors |
-
1999
- 1999-06-15 FR FR9907538A patent/FR2795072B1/fr not_active Expired - Fee Related
-
2000
- 2000-06-08 NO NO20002941A patent/NO316650B1/no not_active IP Right Cessation
- 2000-06-14 NZ NZ505149A patent/NZ505149A/xx not_active IP Right Cessation
- 2000-06-14 EA EA200000527A patent/EA003209B1/ru not_active IP Right Cessation
- 2000-06-14 CA CA002312206A patent/CA2312206C/fr not_active Expired - Fee Related
- 2000-06-15 SE SE00401686T patent/SE1069132T5/xx unknown
- 2000-06-15 SI SI200030218T patent/SI1069132T1/xx unknown
- 2000-06-15 AU AU40865/00A patent/AU766194B2/en not_active Ceased
- 2000-06-15 PL PL340784A patent/PL199522B1/pl not_active IP Right Cessation
- 2000-06-15 CN CNB001183745A patent/CN1147489C/zh not_active Expired - Fee Related
- 2000-06-15 PT PT00401686T patent/PT1069132E/pt unknown
- 2000-06-15 JP JP2000179279A patent/JP3364472B2/ja not_active Expired - Fee Related
- 2000-06-15 BR BR0002643-3A patent/BR0002643A/pt active Search and Examination
- 2000-06-15 ZA ZA200003034A patent/ZA200003034B/xx unknown
- 2000-06-15 EP EP00401686A patent/EP1069132B1/fr not_active Expired - Lifetime
- 2000-06-15 KR KR10-2000-0032945A patent/KR100456796B1/ko not_active IP Right Cessation
- 2000-06-15 DE DE60005609T patent/DE60005609T2/de not_active Expired - Lifetime
- 2000-06-15 AT AT00401686T patent/ATE251177T1/de active
- 2000-06-15 DK DK00401686T patent/DK1069132T3/da active
- 2000-06-15 US US09/594,852 patent/US6277851B1/en not_active Expired - Fee Related
- 2000-06-15 HU HU0002277A patent/HUP0002277A3/hu unknown
- 2000-06-15 ES ES00401686T patent/ES2208239T3/es not_active Expired - Lifetime
-
2001
- 2001-04-23 HK HK01102868A patent/HK1032236A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |