AT398425B - Neue tricyclische lactame - Google Patents
Neue tricyclische lactame Download PDFInfo
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- AT398425B AT398425B AT0269187A AT269187A AT398425B AT 398425 B AT398425 B AT 398425B AT 0269187 A AT0269187 A AT 0269187A AT 269187 A AT269187 A AT 269187A AT 398425 B AT398425 B AT 398425B
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- Prior art keywords
- compound according
- formula
- compounds
- acid
- hydrogen
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- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 33
- -1 perfluoroalkyl sulfonic acid Chemical compound 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 150000003951 lactams Chemical class 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000005544 phthalimido group Chemical group 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 5
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- 239000002220 antihypertensive agent Substances 0.000 claims description 5
- 125000005982 diphenylmethyl 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] 0.000 claims description 5
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
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- 239000000376 reactant Substances 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
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- 125000000217 alkyl group Chemical group 0.000 claims 1
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- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
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- 239000002585 base Substances 0.000 description 7
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- 238000010917 Friedel-Crafts cyclization Methods 0.000 description 6
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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- 239000003765 sweetening agent Substances 0.000 description 6
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- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 5
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- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 3
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- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229950003137 tiapamil Drugs 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000539111A CA1337654C (en) | 1986-06-13 | 1987-06-08 | Fused tricyclic lactams as antihypertensive agents |
| ZA874107A ZA874107B (2) | 1986-06-13 | 1987-06-08 | |
| AU74022/87A AU601433B2 (en) | 1986-06-13 | 1987-06-09 | Novel antihypertensive agent |
| AR87307816A AR247213A1 (es) | 1986-06-13 | 1987-06-09 | Preparacion de acido 7-¡(1-carboxi-3-fenilpropil)amino¿-3,4,6,7,8,12b-octahidro-6-oxopirido ¡2,1-a¿ o hexahidro-6-oxo-1h(1,4-tiazino¡3,4-a¿¡2¿-benzazepin-4-carboxilico, agentes hipertensivos. |
| KR1019870005908A KR950014572B1 (ko) | 1986-06-13 | 1987-06-11 | 융합된 트리사이클릭 락탐 및 이의 제조방법 |
| IE154787A IE61476B1 (en) | 1986-06-13 | 1987-06-11 | Novel antihypertensive agent |
| ES87108410T ES2044870T3 (es) | 1986-06-13 | 1987-06-11 | Un procedimiento para la preparacion de nuevos agentes antihipertensivos. |
| EP87108410A EP0249223B1 (en) | 1986-06-13 | 1987-06-11 | Novel antihypertensive agent |
| DK300487A DK170840B1 (da) | 1986-06-13 | 1987-06-12 | Tricycliske lactamer indeholdende en benzazepingruppe, lægemiddel indeholdende sådanne lactamer samt anvendelse deraf til fremstilling af et lægemiddel til behandling af hypertension |
| JP62145419A JP2542213B2 (ja) | 1986-06-13 | 1987-06-12 | 抗高血圧剤として有用な新規化合物とその製法 |
| AT0269187A AT398425B (de) | 1986-06-13 | 1987-10-12 | Neue tricyclische lactame |
| US07/352,675 US4973585A (en) | 1986-06-13 | 1989-05-10 | Tricyclic lactams active as antihypertensive agents |
| GR930400057T GR3006802T3 (2) | 1986-06-13 | 1993-01-14 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87375486A | 1986-06-13 | 1986-06-13 | |
| AT0269187A AT398425B (de) | 1986-06-13 | 1987-10-12 | Neue tricyclische lactame |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA269187A ATA269187A (de) | 1994-04-15 |
| AT398425B true AT398425B (de) | 1994-12-27 |
Family
ID=25598925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0269187A AT398425B (de) | 1986-06-13 | 1987-10-12 | Neue tricyclische lactame |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0249223B1 (2) |
| JP (1) | JP2542213B2 (2) |
| KR (1) | KR950014572B1 (2) |
| AR (1) | AR247213A1 (2) |
| AT (1) | AT398425B (2) |
| AU (1) | AU601433B2 (2) |
| CA (1) | CA1337654C (2) |
| DK (1) | DK170840B1 (2) |
| ES (1) | ES2044870T3 (2) |
| GR (1) | GR3006802T3 (2) |
| IE (1) | IE61476B1 (2) |
| ZA (1) | ZA874107B (2) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4824832A (en) * | 1987-12-30 | 1989-04-25 | Merrell Dow Pharmaceuticals Inc. | Sulfhydryl containing tricyclic lactams and their pharmacological methods of use |
| CA2053340C (en) * | 1990-10-18 | 2002-04-02 | Timothy P. Burkholder | Mercaptoacetylamide derivatives useful as inhibitors of enkephalinase and ace |
| US5208230A (en) * | 1990-12-21 | 1993-05-04 | Merrell Dow Pharmaceuticals | Amino and nitro containing tricyclic compounds useful as inhibitors of ACE |
| ATE158303T1 (de) * | 1990-12-21 | 1997-10-15 | Merrell Pharma Inc | Neue trizyklische amino- und nitro verbindungen mit ace-hemmenden eigenschaften |
| US5457196A (en) * | 1991-09-27 | 1995-10-10 | Merrell Dow Pharmaceuticals Inc. | 2-substituted indane-2-carboxyalkyl derivatives useful as inhibitors of enkephalinase and ACE |
| AU657793B2 (en) * | 1991-09-27 | 1995-03-23 | Merrell Pharmaceuticals Inc. | Novel 2-substituted indane-2-carboxyalkyl derivatives useful as inhibitors of enkephalinase and ACE |
| US5455242A (en) * | 1991-09-27 | 1995-10-03 | Merrell Dow Pharmaceuticals Inc. | Carboxyalkyl tricyclic derivatives useful as inhibitors of enkephalinase and ace |
| CA2078758C (en) * | 1991-09-27 | 2003-12-09 | Alan M. Warshawsky | 2-substituted indane-2-mercaptoacetylamide derivatives useful as inhibitors of enkephalinase and ace |
| ZA927211B (en) * | 1991-09-27 | 1993-03-24 | Merrell Dow Pharma | Novel carboxyalkyl derivatives useful as inhibitors of enkephalinase and ACE. |
| DE69317764T2 (de) * | 1992-02-14 | 1998-07-30 | Merrell Pharmaceuticals Inc., Cincinnati, Ohio | Aminoacetylmercaptoacetylamid derivate mit enkephalinase- und ace-hemmwirkung |
| US5552397A (en) * | 1992-05-18 | 1996-09-03 | E. R. Squibb & Sons, Inc. | Substituted azepinone dual inhibitors of angiotensin converting enzyme and neutral exdopeptidase |
| DK0640086T3 (da) * | 1992-05-15 | 1999-12-06 | Merrell Pharma Inc | Mercaptoacetylamido-pyridazo[1,2-a][1,2]diazepin-derivateranvendelige som enkephalinase- og ACE-inhibitorer |
| US5238932A (en) * | 1992-05-20 | 1993-08-24 | Merrell Dow Pharmaceuticals Inc. | Mercaptoacetylamide tricyclic derivatives useful as inhibitors of enkephalinase |
| PT669936E (pt) * | 1992-10-30 | 2001-04-30 | Merrell Pharma Inc | Derivados de lactama biciclica de mercaptoacetilamida uteis como inibidores de encefalinase e de ace |
| US5654294A (en) * | 1993-05-13 | 1997-08-05 | Bristol-Myers Squibb | Spiro lactam dual action inhibitors |
| US5362727A (en) * | 1993-07-26 | 1994-11-08 | Bristol-Myers Squibb | Substituted azepino[2,1-a]isoquinoline compounds |
| CN1041627C (zh) * | 1993-11-19 | 1999-01-13 | 默里尔药物公司 | (s)－2,2,2－三氯－n－(2－氯环己－2－烯基)－乙酰胺和(s)－2－氯环己－2－烯胺 |
| CA2183313C (en) * | 1994-02-14 | 2001-01-02 | Gary A. Flynn | Novel indane-2-mercaptoacetylamide disulfide derivatives useful as inhibitors of enkephalinase |
| CA2183314C (en) * | 1994-02-14 | 1999-08-31 | Gary A. Flynn | Novel 2-substituted indane-2-mercaptoacetylamide disulfide derivatives useful as inhibitors of enkephalinase and ace |
| JPH09508906A (ja) * | 1994-02-14 | 1997-09-09 | メレル ファーマスーティカルズ インコーポレーテッド | エンケファリナーゼ及びａｃｅの阻害剤として有用な新規なメルカプトアセチルアミド１，３，４，５−テトラヒドロベンゾ［ｃ］アゼピン−３−オンジスルフィド誘導体類 |
| WO1995021839A1 (en) * | 1994-02-14 | 1995-08-17 | Merrell Pharmaceuticals Inc. | Novel mercaptoacetylamide disulfide derivatives useful as inhibitors of enkephalinase and ace |
| US5530013A (en) * | 1994-02-14 | 1996-06-25 | American Home Products Corporation | Venlafaxine in the inducement of cognition enhancement |
| US5484783A (en) * | 1994-03-24 | 1996-01-16 | Merrell Dow Pharmaceuticals Inc. | Hypocholesterolemic, antiatherosclerotic and hypotriglyceridemic mercaptoacetylamide and benzazapine derivatives |
| NZ282568A (en) * | 1994-03-24 | 1997-07-27 | Merrell Pharma Inc | Use of condensed aminoacetylmercaptobenzazepines in treating elevated cholesterol levels, atherosclerosis, and hypotriglyceridemia |
| FI963784A0 (fi) * | 1994-03-24 | 1996-09-23 | Merrell Pharma Inc | Hypokolesteroleemisiä, antiateroskleroottisia ja hypotriglyserideemisiä merkaptoasetyyliamididisulfidijohdannaisia |
| DK0800527T3 (da) * | 1994-12-21 | 2000-06-05 | Aventis Pharma Inc | Nye fremgangsmåder til fremstilling af mellemprodukter for inhibitorer af enkephalinase og angiotensinomdannende enzym og m |
| US5641880A (en) * | 1994-12-21 | 1997-06-24 | Hoechst Marion Roussel, Inc. | Processes for preparing intermediates of inhibitors of enkephalinase and angiotensin converting enzyme and intermediates thereof |
| 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 |
| GB0119305D0 (en) | 2001-04-12 | 2001-10-03 | Aventis Pharma Gmbh | Mercaptoacetylamide derivatives,a process for their preparation and their use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0107095A1 (en) * | 1982-09-30 | 1984-05-02 | Merck & Co. Inc. | 1-N-alkylcarboxy-benzofused lactams useful as antihypertensive agents |
| EP0166357A2 (en) * | 1984-06-26 | 1986-01-02 | Merck & Co. Inc. | Benzofused lactams and pharmaceutical compositions containing them |
-
1987
- 1987-06-08 CA CA000539111A patent/CA1337654C/en not_active Expired - Lifetime
- 1987-06-08 ZA ZA874107A patent/ZA874107B/xx unknown
- 1987-06-09 AR AR87307816A patent/AR247213A1/es active
- 1987-06-09 AU AU74022/87A patent/AU601433B2/en not_active Expired
- 1987-06-11 ES ES87108410T patent/ES2044870T3/es not_active Expired - Lifetime
- 1987-06-11 KR KR1019870005908A patent/KR950014572B1/ko not_active Expired - Lifetime
- 1987-06-11 EP EP87108410A patent/EP0249223B1/en not_active Expired - Lifetime
- 1987-06-11 IE IE154787A patent/IE61476B1/en not_active IP Right Cessation
- 1987-06-12 DK DK300487A patent/DK170840B1/da not_active IP Right Cessation
- 1987-06-12 JP JP62145419A patent/JP2542213B2/ja not_active Expired - Lifetime
- 1987-10-12 AT AT0269187A patent/AT398425B/de not_active IP Right Cessation
-
1993
- 1993-01-14 GR GR930400057T patent/GR3006802T3/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0107095A1 (en) * | 1982-09-30 | 1984-05-02 | Merck & Co. Inc. | 1-N-alkylcarboxy-benzofused lactams useful as antihypertensive agents |
| EP0166357A2 (en) * | 1984-06-26 | 1986-01-02 | Merck & Co. Inc. | Benzofused lactams and pharmaceutical compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA269187A (de) | 1994-04-15 |
| GR3006802T3 (2) | 1993-06-30 |
| AU7402287A (en) | 1987-12-17 |
| AU601433B2 (en) | 1990-09-13 |
| IE871547L (en) | 1987-12-13 |
| ES2044870T3 (es) | 1994-01-16 |
| KR880000399A (ko) | 1988-03-25 |
| CA1337654C (en) | 1995-11-28 |
| KR950014572B1 (ko) | 1995-12-08 |
| DK300487D0 (da) | 1987-06-12 |
| IE61476B1 (en) | 1994-11-02 |
| EP0249223B1 (en) | 1992-10-14 |
| JP2542213B2 (ja) | 1996-10-09 |
| EP0249223A2 (en) | 1987-12-16 |
| ZA874107B (2) | 1987-12-09 |
| AR247213A1 (es) | 1994-11-30 |
| DK300487A (da) | 1987-12-14 |
| JPS62298591A (ja) | 1987-12-25 |
| EP0249223A3 (en) | 1989-01-25 |
| DK170840B1 (da) | 1996-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |