DK169668B1 - Derivater af omega-mercaptopropanamid, fremgangsmåde til deres fremstilling samt lægemidler med indhold deraf - Google Patents
Derivater af omega-mercaptopropanamid, fremgangsmåde til deres fremstilling samt lægemidler med indhold deraf Download PDFInfo
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- DK169668B1 DK169668B1 DK051384A DK51384A DK169668B1 DK 169668 B1 DK169668 B1 DK 169668B1 DK 051384 A DK051384 A DK 051384A DK 51384 A DK51384 A DK 51384A DK 169668 B1 DK169668 B1 DK 169668B1
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- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
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- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
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- 210000000548 hind-foot Anatomy 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
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- 229930182817 methionine Natural products 0.000 description 1
- TVIVLENJTXGRAM-UHFFFAOYSA-N methyl 2-(4-aminophenyl)acetate Chemical compound COC(=O)CC1=CC=C(N)C=C1 TVIVLENJTXGRAM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229950010131 puromycin Drugs 0.000 description 1
- 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 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- SYIWWWZVQZBRJE-UHFFFAOYSA-N s-(2-benzyl-3-chloro-3-oxopropyl) ethanethioate Chemical compound CC(=O)SCC(C(Cl)=O)CC1=CC=CC=C1 SYIWWWZVQZBRJE-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8301862 | 1983-02-07 | ||
| FR8301862A FR2540495B1 (fr) | 1983-02-07 | 1983-02-07 | Nouveaux derives de o-mercaptopropanamide et de ses homologues, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK51384D0 DK51384D0 (da) | 1984-02-06 |
| DK51384A DK51384A (da) | 1984-08-08 |
| DK169668B1 true DK169668B1 (da) | 1995-01-09 |
Family
ID=9285651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK051384A DK169668B1 (da) | 1983-02-07 | 1984-02-06 | Derivater af omega-mercaptopropanamid, fremgangsmåde til deres fremstilling samt lægemidler med indhold deraf |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5098934A (cs) |
| EP (1) | EP0115997B1 (cs) |
| JP (1) | JPS59148759A (cs) |
| KR (1) | KR910008182B1 (cs) |
| AT (1) | ATE28451T1 (cs) |
| AU (1) | AU568628B2 (cs) |
| CA (1) | CA1244029A (cs) |
| DE (1) | DE3464907D1 (cs) |
| DK (1) | DK169668B1 (cs) |
| ES (1) | ES528764A0 (cs) |
| FR (1) | FR2540495B1 (cs) |
| GR (1) | GR81410B (cs) |
| HU (1) | HU193552B (cs) |
| IE (2) | IE57052B1 (cs) |
| NZ (1) | NZ207056A (cs) |
| PT (1) | PT78070B (cs) |
| ZA (1) | ZA84570B (cs) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2540498B1 (fr) * | 1983-02-07 | 1986-02-14 | Roussel Uclaf | Nouveaux medicaments derives d'amides d'acide mercaptoacetique et de l'acide 3-mercaptopropionique et les compositions pharmaceutiques les renfermant |
| US4868310A (en) * | 1986-08-04 | 1989-09-19 | Rohm And Haas Company | Process for preparing isothiazolones |
| FR2611712B1 (fr) * | 1987-02-26 | 1989-06-23 | Roussel Uclaf | Nouveaux derives n-substitues de l'alpha-mercaptomethyl benzene propanamide, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant |
| US5179125A (en) * | 1987-12-03 | 1993-01-12 | Dainippon Pharmaceutical Co., Ltd. | N-substituted mercaptopropanamide derivatives |
| US5210266A (en) * | 1987-12-03 | 1993-05-11 | Dainippon Pharmaceutical Co., Ltd. | N-substituted mercaptopropanamide derivatives |
| EP0318859A3 (en) * | 1987-12-03 | 1990-08-16 | Dainippon Pharmaceutical Co., Ltd. | N-substituted mercaptopropanamide derivatives |
| US4970303A (en) * | 1988-02-03 | 1990-11-13 | Xoma Corporation | Linking agents and methods |
| JPH02209861A (ja) * | 1988-05-06 | 1990-08-21 | Ono Pharmaceut Co Ltd | アミノ酸誘導体及び該誘導体を有効成分として含有するエンケファリナーゼ阻害剤 |
| US5202340A (en) * | 1988-05-06 | 1993-04-13 | Ono Pharmaceutical Co., Ltd. | Amino acid derivatives |
| US4879309A (en) * | 1988-09-27 | 1989-11-07 | Schering Corporation | Mercapto-acylamino acids as antihypertensives |
| EP0361365A1 (en) * | 1988-09-30 | 1990-04-04 | E.R. SQUIBB & SONS, INC. | Aminobenzoic and aminocyclohexane-carboylic acid compounds, compositions, and their method of use |
| US5223516A (en) * | 1990-03-22 | 1993-06-29 | E. R. Squibb & Sons, Inc. | 3,3,3-trifluoro-2-mercaptomethyl-N-tetrazolyl substituted propanamides and method of using same |
| WO1992009572A1 (en) * | 1990-11-26 | 1992-06-11 | Taisho Pharmaceutical Co., Ltd. | Anilide derivative |
| ES2106162T3 (es) * | 1991-11-01 | 1997-11-01 | Ciba Geigy Ag | Derivados del acido butirico, procedimiento para su preparacion y su empleo como pesticidas. |
| GB9123353D0 (en) * | 1991-11-04 | 1991-12-18 | Fujisawa Pharmaceutical Co | New mercapto-amide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
| FR2683817B1 (fr) * | 1991-11-18 | 1994-02-25 | Upsa Laboratoires | Nouveaux derives d'alpha-amino n-pyridyl benzene propanamide, leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| FR2687147A1 (fr) * | 1992-02-11 | 1993-08-13 | Union Pharma Scient Appl | Nouveaux derives d'alpha-amino n-pyridyl benzene propanamide, leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| US5552397A (en) * | 1992-05-18 | 1996-09-03 | E. R. Squibb & Sons, Inc. | Substituted azepinone dual inhibitors of angiotensin converting enzyme and neutral exdopeptidase |
| US5654294A (en) * | 1993-05-13 | 1997-08-05 | Bristol-Myers Squibb | Spiro lactam dual action inhibitors |
| US5508272A (en) * | 1993-06-15 | 1996-04-16 | Bristol-Myers Squibb Company | Compounds containing a fused bicycle ring and processes therefor |
| US5362727A (en) * | 1993-07-26 | 1994-11-08 | Bristol-Myers Squibb | Substituted azepino[2,1-a]isoquinoline compounds |
| IT1266571B1 (it) * | 1993-07-30 | 1997-01-09 | Zambon Spa | Derivati della beta-mercapto-propanammide utili nel trattamento delle malattie cardiovascolari |
| CN1035252C (zh) * | 1993-11-23 | 1997-06-25 | 王桂英 | 氨甲基甲酸-1,1,1-三氯-2-(2,4-二氯硫酚基) 乙基酯及其制备方法 |
| US5616775A (en) * | 1994-05-05 | 1997-04-01 | Bristol-Myers Squibb Co. | Process for preparing homocystein analogs useful as intermediates for compounds containing a fused bicyclic ring |
| US5587375A (en) * | 1995-02-17 | 1996-12-24 | Bristol-Myers Squibb Company | Azepinone compounds useful in the inhibition of ACE and NEP |
| US5877313A (en) | 1995-05-17 | 1999-03-02 | Bristol-Myers Squibb | Benzo-fused azepinone and piperidinone compounds useful in the inhibition of ACE and NEP |
| US5650408A (en) * | 1995-06-07 | 1997-07-22 | Karanewsky; Donald S. | Thiazolo benzazepine containing dual action inhibitors |
| US5635504A (en) * | 1995-06-07 | 1997-06-03 | Bristol-Myers Squibb Co. | Diazepine containing dual action inhibitors |
| DE69800800T2 (de) * | 1997-03-18 | 2001-10-04 | Ceca S.A., Puteaux | Zusammensetzungen auf der basis von salzen von mercaptosäuren und imidazolinen als kohlensäure-korrosionsinhibitoren für eisen und eisenlegierungen |
| US7195284B2 (en) * | 2004-07-19 | 2007-03-27 | Snyder Industries, Inc. | Flexible synthetic resin coupling |
| CH706854A2 (de) | 2012-08-21 | 2014-02-28 | Dr Rer Nat Lisseth Sandoval Soto | Verfahren und Vorrichtung zur Bestimmung der elektrischen Eigenschaften von Materialien. |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2184495A (en) * | 1939-12-26 | Printing assistant | ||
| US2535875A (en) * | 1947-09-03 | 1950-12-26 | Goodrich Co B F | Plant growth regulants |
| US2709706A (en) * | 1950-05-06 | 1955-05-31 | Goodrich Co B F | Preparation of beta-dithiocarbamyl and beta-mercapto carboxylic acid amides and the corresponding hydrazides |
| US2614095A (en) * | 1951-06-15 | 1952-10-14 | Goodrich Co B F | Heat stabilization of a chlorine containing polymer with a mercapto acid amide |
| US2792307A (en) * | 1953-07-20 | 1957-05-14 | Universal Oil Prod Co | Stabilization of organic compounds |
| US3228832A (en) * | 1962-01-30 | 1966-01-11 | Geigy Chem Corp | Anthelmintic compositions and methods of using same |
| US4055599A (en) * | 1967-06-23 | 1977-10-25 | Ciba-Geigy Corporation | N-(Alkylhydrobenzyl)-alkylthio- and mercapto-acetamides |
| DE1770481C3 (de) * | 1968-05-22 | 1980-03-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 33-disubstituierten ß -Lactamen |
| US3590083A (en) * | 1969-02-28 | 1971-06-29 | Geigy Chem Corp | Alkylthioalkanoylaminophenol antioxidants |
| SU472933A1 (ru) * | 1973-03-19 | 1975-06-05 | Предприятие П/Я В-8585 | Способ получени меркаптоамидов |
| US4053651A (en) * | 1976-05-10 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Compounds and method for alleviating angiotensin related hypertension |
| ZA774041B (en) * | 1976-08-09 | 1978-05-30 | Goodyear Tire & Rubber | Age-resisting polymers and their preparation by reactions involving use of certain aminomercaptans |
| JPS53141217A (en) * | 1977-05-13 | 1978-12-08 | Nippon Carbide Ind Co Ltd | New gamma-mercaptopropyl compound |
| US4148815A (en) * | 1977-09-08 | 1979-04-10 | Kennecott Copper Corporation | Amino-thiol nickel and cobalt solvent extraction |
| US4216160A (en) * | 1977-10-25 | 1980-08-05 | Merck & Co., Inc. | Substituted mercapto acid amides and their use |
| AU4091178A (en) * | 1977-10-25 | 1980-04-24 | Merck & Co Inc | Substituted mercapto acid amides |
| US4248958A (en) * | 1979-05-23 | 1981-02-03 | Hoechst Aktiengesellschaft | Photopolymerizable mixture containing polyurethanes |
| FR2480747A1 (fr) * | 1980-04-17 | 1981-10-23 | Roques Bernard | Derives d'acides amines et leur application therapeutique |
| GB2076809B (en) * | 1980-05-30 | 1984-03-14 | Squibb & Sons Inc | N-substituted mercapto propionamides |
| US4329495A (en) * | 1981-05-18 | 1982-05-11 | Pfizer Inc. | Enkephalinase enzyme inhibiting compounds |
| EP0100172B1 (en) * | 1982-07-23 | 1987-08-12 | Imperial Chemical Industries Plc | Amide derivatives |
| FR2540498B1 (fr) * | 1983-02-07 | 1986-02-14 | Roussel Uclaf | Nouveaux medicaments derives d'amides d'acide mercaptoacetique et de l'acide 3-mercaptopropionique et les compositions pharmaceutiques les renfermant |
| US4879309A (en) * | 1988-09-27 | 1989-11-07 | Schering Corporation | Mercapto-acylamino acids as antihypertensives |
-
1983
- 1983-02-07 FR FR8301862A patent/FR2540495B1/fr not_active Expired
-
1984
- 1984-01-10 ES ES528764A patent/ES528764A0/es active Granted
- 1984-01-25 ZA ZA84570A patent/ZA84570B/xx unknown
- 1984-02-01 DE DE8484400216T patent/DE3464907D1/de not_active Expired
- 1984-02-01 AT AT84400216T patent/ATE28451T1/de not_active IP Right Cessation
- 1984-02-01 EP EP84400216A patent/EP0115997B1/fr not_active Expired
- 1984-02-06 AU AU24201/84A patent/AU568628B2/en not_active Ceased
- 1984-02-06 DK DK051384A patent/DK169668B1/da not_active IP Right Cessation
- 1984-02-06 HU HU84482A patent/HU193552B/hu not_active IP Right Cessation
- 1984-02-06 JP JP59018510A patent/JPS59148759A/ja active Granted
- 1984-02-06 CA CA000446816A patent/CA1244029A/fr not_active Expired
- 1984-02-06 PT PT78070A patent/PT78070B/pt not_active IP Right Cessation
- 1984-02-06 GR GR73711A patent/GR81410B/el unknown
- 1984-02-07 IE IE279/84A patent/IE57052B1/en not_active IP Right Cessation
- 1984-02-07 IE IE278/84A patent/IE57391B1/en not_active IP Right Cessation
- 1984-02-07 KR KR1019840000559A patent/KR910008182B1/ko not_active Expired
- 1984-02-07 NZ NZ207056A patent/NZ207056A/en unknown
-
1990
- 1990-06-22 US US07/542,731 patent/US5098934A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HU193552B (en) | 1987-10-28 |
| DK51384A (da) | 1984-08-08 |
| CA1244029A (fr) | 1988-11-01 |
| NZ207056A (en) | 1987-09-30 |
| US5098934A (en) | 1992-03-24 |
| KR910008182B1 (ko) | 1991-10-10 |
| GR81410B (cs) | 1984-12-11 |
| FR2540495A1 (fr) | 1984-08-10 |
| ATE28451T1 (de) | 1987-08-15 |
| AU2420184A (en) | 1984-08-16 |
| ZA84570B (en) | 1985-02-27 |
| IE57052B1 (en) | 1992-04-08 |
| IE57391B1 (en) | 1992-08-26 |
| EP0115997A3 (en) | 1985-05-29 |
| IE840278L (en) | 1984-08-07 |
| ES8407017A1 (es) | 1984-08-16 |
| EP0115997A2 (fr) | 1984-08-15 |
| JPS59148759A (ja) | 1984-08-25 |
| IE840279L (en) | 1984-08-07 |
| PT78070B (fr) | 1986-06-11 |
| AU568628B2 (en) | 1988-01-07 |
| DK51384D0 (da) | 1984-02-06 |
| ES528764A0 (es) | 1984-08-16 |
| KR850001162A (ko) | 1985-03-16 |
| PT78070A (fr) | 1984-03-01 |
| DE3464907D1 (en) | 1987-08-27 |
| JPH0518823B2 (cs) | 1993-03-15 |
| FR2540495B1 (fr) | 1986-02-14 |
| EP0115997B1 (fr) | 1987-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |