IL113073A - Hypocholesterolemic and hypotriglyceridemic preparations of mercaptoacetylamide containing a history of disulfide of -N (tricyclic benzazinyl) azamide - Google Patents
Hypocholesterolemic and hypotriglyceridemic preparations of mercaptoacetylamide containing a history of disulfide of -N (tricyclic benzazinyl) azamideInfo
- Publication number
- IL113073A IL113073A IL11307395A IL11307395A IL113073A IL 113073 A IL113073 A IL 113073A IL 11307395 A IL11307395 A IL 11307395A IL 11307395 A IL11307395 A IL 11307395A IL 113073 A IL113073 A IL 113073A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- alkyl
- oxo
- group
- amino
- Prior art date
Links
- -1 benzazepinyl Chemical group 0.000 title claims abstract description 75
- 230000000871 hypocholesterolemic effect Effects 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 title claims description 21
- 230000000999 hypotriglyceridemic effect Effects 0.000 title claims description 7
- 150000002019 disulfides Chemical class 0.000 title description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title description 4
- GYXHHICIFZSKKZ-UHFFFAOYSA-N 2-sulfanylacetamide Chemical compound NC(=O)CS GYXHHICIFZSKKZ-UHFFFAOYSA-N 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 6
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims abstract description 6
- 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 abstract description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract 34
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 90
- 239000002253 acid Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 22
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 19
- CMIRWXFQPVROKZ-UHFFFAOYSA-N 5h-2-benzazepine-4-carboxylic acid Chemical compound C1C(C(=O)O)=CN=CC2=CC=CC=C21 CMIRWXFQPVROKZ-UHFFFAOYSA-N 0.000 claims description 18
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 18
- 150000003626 triacylglycerols Chemical class 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- NQPIQAOGGAHLAA-UHFFFAOYSA-N 1-oxo-2h-pyrido[2,1-a][2]benzazepine-4-carboxylic acid Chemical compound C1=CN2C(C(=O)O)=CCC(=O)C2=C2C=CC=CC2=C1 NQPIQAOGGAHLAA-UHFFFAOYSA-N 0.000 claims 1
- YICDOLUTZGYHEZ-UHFFFAOYSA-N 1h-1-benzazepine-2-carboxylic acid Chemical compound N1C(C(=O)O)=CC=CC2=CC=CC=C21 YICDOLUTZGYHEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 238000003756 stirring Methods 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000011282 treatment Methods 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 14
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
- 208000029078 coronary artery disease Diseases 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 235000012000 cholesterol Nutrition 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- 108010007622 LDL Lipoproteins Proteins 0.000 description 8
- 102000007330 LDL Lipoproteins Human genes 0.000 description 8
- 239000012467 final product Substances 0.000 description 8
- 125000004344 phenylpropyl group Chemical group 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 201000001320 Atherosclerosis Diseases 0.000 description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 7
- WLPPCFGXINTUNZ-UHFFFAOYSA-N 5h-1-benzazepine-4-carboxylic acid Chemical compound C1C(C(=O)O)=CC=NC2=CC=CC=C21 WLPPCFGXINTUNZ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 150000002632 lipids Chemical group 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- 108010010234 HDL Lipoproteins Proteins 0.000 description 5
- 102000015779 HDL Lipoproteins Human genes 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000008214 LDL Cholesterol Methods 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PWNUBDVZGJEXRA-UHFFFAOYSA-N pyrido[2,1-a][2]benzazepine-4-carboxylic acid Chemical compound C1=CN2C(C(=O)O)=CC=CC2=C2C=CC=CC2=C1 PWNUBDVZGJEXRA-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 4
- CYWHLOXWVAWMFO-UHFFFAOYSA-N 3-sulfanyl-1h-pyridine-2-thione Chemical compound SC1=CC=CN=C1S CYWHLOXWVAWMFO-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 239000012141 concentrate Substances 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 108010004103 Chylomicrons Proteins 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 108010046315 IDL Lipoproteins Proteins 0.000 description 3
- 108010013563 Lipoprotein Lipase Proteins 0.000 description 3
- 102000043296 Lipoprotein lipases Human genes 0.000 description 3
- 102000004895 Lipoproteins Human genes 0.000 description 3
- 108090001030 Lipoproteins Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 206010033645 Pancreatitis Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
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- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 2
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 206010014476 Elevated cholesterol Diseases 0.000 description 2
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- 239000002585 base Substances 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P9/10—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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21747194A | 1994-03-24 | 1994-03-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL113073A0 IL113073A0 (en) | 1995-06-29 |
| IL113073A true IL113073A (en) | 2001-03-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11307395A IL113073A (en) | 1994-03-24 | 1995-03-22 | Hypocholesterolemic and hypotriglyceridemic preparations of mercaptoacetylamide containing a history of disulfide of -N (tricyclic benzazinyl) azamide |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6013645A (no) |
| EP (1) | EP0751774B1 (no) |
| JP (1) | JPH10503468A (no) |
| CN (1) | CN1144482A (no) |
| AT (1) | ATE246927T1 (no) |
| AU (1) | AU688012B2 (no) |
| CA (1) | CA2184692C (no) |
| DE (1) | DE69531489T2 (no) |
| DK (1) | DK0751774T3 (no) |
| ES (1) | ES2201100T3 (no) |
| FI (1) | FI963784A0 (no) |
| HU (1) | HUP9774624A2 (no) |
| IL (1) | IL113073A (no) |
| NO (1) | NO963988L (no) |
| NZ (1) | NZ282565A (no) |
| PT (1) | PT751774E (no) |
| WO (1) | WO1995025519A1 (no) |
| ZA (1) | ZA952289B (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6667299B1 (en) * | 2000-03-16 | 2003-12-23 | Hollis-Eden Pharmaceuticals, Inc. | Pharmaceutical compositions and treatment methods |
| GB0119305D0 (en) * | 2001-04-12 | 2001-10-03 | Aventis Pharma Gmbh | Mercaptoacetylamide derivatives,a process for their preparation and their use |
Family Cites Families (29)
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| US3334095A (en) * | 1965-02-16 | 1967-08-01 | Sandoz Ag | Novel pyrrolo-oxazines and pyrrolo-oxazoles |
| US3334091A (en) * | 1965-03-25 | 1967-08-01 | Sandoz Ag | Sedatives |
| GB1525845A (en) * | 1976-07-30 | 1978-09-20 | Ucb Sa | 1,2,4,5-tetrahydro-3h-2-benzazepin-3-ones |
| IE50839B1 (en) * | 1980-02-26 | 1986-07-23 | Wyeth John & Brother Ltd | Novel processes for preparing proline derivatives and analogous compounds |
| EP0042100A1 (de) * | 1980-06-13 | 1981-12-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyrazolopyridazin-Derivate, Zwischenprodukte und Verfahren zu deren Herstellung, sowie diese enthaltende Arzneimittel |
| US4320057A (en) * | 1980-06-23 | 1982-03-16 | American Home Products Corporation | Aryl--pyrrolo--thiazepin--diones and aryl--piperidino--thiazepin--diones |
| US4415496A (en) * | 1981-03-23 | 1983-11-15 | Merck & Co., Inc. | Bicyclic lactams |
| GB2128984B (en) * | 1982-05-12 | 1985-05-22 | Hoffmann La Roche | Diaza-bicyclic compounds |
| ZA833214B (en) * | 1982-05-12 | 1983-12-28 | Hoffmann La Roche | Bicyclic compounds |
| US4552889A (en) * | 1983-06-09 | 1985-11-12 | Eli Lilly And Company | 3-Mercaptomethyl-2-oxo-1-pyrrolidine acetic acids and use for hypertension |
| US4692438A (en) * | 1984-08-24 | 1987-09-08 | Hoffmann-La Roche Inc. | Pyridazo-diazepines, diazocines, and -triazepines having anti-hypertensive activity |
| US4584294A (en) * | 1984-11-07 | 1986-04-22 | Merck & Co., Inc. | Fused tricyclic lactams as angiotensin converting enzyme inhibitors and as antihypertensive agents |
| HUT40660A (en) * | 1985-04-30 | 1987-01-28 | Lilly Co Eli | Process for production of derivatives of 7-substituated bicyclic pirasilididone |
| ZA874106B (en) * | 1986-06-13 | 1987-12-08 | Merrell Dow Pharmaceuticals Inc. | Novel antihypertensive agent |
| US4973585A (en) * | 1986-06-13 | 1990-11-27 | Merrell Dow Pharmaceuticals | Tricyclic lactams active as antihypertensive agents |
| ZA874107B (no) * | 1986-06-13 | 1987-12-09 | ||
| GB8629875D0 (en) * | 1986-12-15 | 1987-01-28 | Hoffmann La Roche | Pyridazodiazepine derivatives |
| US4824832A (en) * | 1987-12-30 | 1989-04-25 | Merrell Dow Pharmaceuticals Inc. | Sulfhydryl containing tricyclic lactams and their pharmacological methods of use |
| US4902684A (en) * | 1988-06-20 | 1990-02-20 | E. R. Squibb & Sons, Inc. | Benzazepine and benzothiazepine derivatives |
| GB8926512D0 (en) * | 1989-11-23 | 1990-01-10 | Pfizer Ltd | Therapeutic agents |
| AU7168091A (en) * | 1989-12-22 | 1991-07-24 | Schering Corporation | Mercaptocycloacyl aminoacid endopeptidase inhibitors |
| EP0459432B1 (en) * | 1990-06-01 | 2000-08-23 | Korth, Ruth, Dr. med. | Treatment of diseases with paf-antagonists and procedure for determining their efficacy |
| 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 |
| CA2057786C (en) * | 1990-12-21 | 2002-06-18 | Gary A. Flynn | Amino and nitro containing tricyclic compounds useful as inhibitors or ace |
| FR2679564A1 (fr) * | 1991-07-23 | 1993-01-29 | Inst Nat Sante Rech Med | Nouveaux acylmercaptoalcanoldipeptides, leur preparation et les compositions qui les contiennent. |
| SG48855A1 (en) * | 1992-04-20 | 1998-05-18 | Takeda Chemical Industries Ltd | 4,1-benzoxazepin derivatives and their use |
| RU2124503C1 (ru) * | 1992-05-18 | 1999-01-10 | И.Р.Сквибб энд Санз, Инк. | Гетероциклические азотсодержащие производные карбоновой кислоты, способ их получения и фармацевтическая композиция |
| US5238932A (en) * | 1992-05-20 | 1993-08-24 | Merrell Dow Pharmaceuticals Inc. | Mercaptoacetylamide tricyclic derivatives useful as inhibitors of enkephalinase |
-
1995
- 1995-02-28 NZ NZ282565A patent/NZ282565A/xx unknown
- 1995-02-28 CA CA002184692A patent/CA2184692C/en not_active Expired - Fee Related
- 1995-02-28 EP EP95912630A patent/EP0751774B1/en not_active Expired - Lifetime
- 1995-02-28 DE DE69531489T patent/DE69531489T2/de not_active Expired - Fee Related
- 1995-02-28 US US08/913,006 patent/US6013645A/en not_active Expired - Fee Related
- 1995-02-28 ES ES95912630T patent/ES2201100T3/es not_active Expired - Lifetime
- 1995-02-28 AT AT95912630T patent/ATE246927T1/de not_active IP Right Cessation
- 1995-02-28 PT PT95912630T patent/PT751774E/pt unknown
- 1995-02-28 AU AU19720/95A patent/AU688012B2/en not_active Ceased
- 1995-02-28 WO PCT/US1995/002448 patent/WO1995025519A1/en active IP Right Grant
- 1995-02-28 CN CN95192241A patent/CN1144482A/zh active Pending
- 1995-02-28 JP JP7524645A patent/JPH10503468A/ja not_active Ceased
- 1995-02-28 DK DK95912630T patent/DK0751774T3/da active
- 1995-02-28 HU HU9602602A patent/HUP9774624A2/hu unknown
- 1995-03-20 ZA ZA952289A patent/ZA952289B/xx unknown
- 1995-03-22 IL IL11307395A patent/IL113073A/en not_active IP Right Cessation
-
1996
- 1996-09-23 NO NO963988A patent/NO963988L/no not_active Application Discontinuation
- 1996-09-23 FI FI963784A patent/FI963784A0/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0751774T3 (da) | 2003-12-08 |
| EP0751774A1 (en) | 1997-01-08 |
| PT751774E (pt) | 2003-11-28 |
| DE69531489T2 (de) | 2004-04-08 |
| FI963784A (fi) | 1996-09-23 |
| CA2184692C (en) | 2001-01-02 |
| WO1995025519A1 (en) | 1995-09-28 |
| HUP9774624A2 (en) | 1997-01-28 |
| DE69531489D1 (de) | 2003-09-18 |
| AU688012B2 (en) | 1998-03-05 |
| US6013645A (en) | 2000-01-11 |
| NO963988L (no) | 1996-11-22 |
| NZ282565A (en) | 1999-11-29 |
| ZA952289B (en) | 1996-01-09 |
| IL113073A0 (en) | 1995-06-29 |
| ATE246927T1 (de) | 2003-08-15 |
| EP0751774B1 (en) | 2003-08-13 |
| HU9602602D0 (en) | 1996-11-28 |
| FI963784A0 (fi) | 1996-09-23 |
| NO963988D0 (no) | 1996-09-23 |
| CA2184692A1 (en) | 1995-09-28 |
| CN1144482A (zh) | 1997-03-05 |
| JPH10503468A (ja) | 1998-03-31 |
| ES2201100T3 (es) | 2004-03-16 |
| AU1972095A (en) | 1995-10-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees | ||
| HC | Change of name of proprietor(s) |
Owner name: AVENTIS INC. Free format text: FORMER NAME:MERRELL PHARMACEUTICALS INC. |