Patent US4512924A successfully refreshed from Google Patents.
US4512924A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pyridazo[1,2-a][1,2]diazepines
Assignee: Hoffmann La Roche Inc
•
Filing: 1983-05-12
•
Granted: 1985-04-23
•
Expires: 2003-05-12
Abstract
Abstract Novel compounds of the formula <IMAGE> I wherein B represents a methylene, ethylene or vinylene group, R1 represents a hydrogen atom or an alkyl, aralkyl, amino-alkyl, mono-alkylamino-alkyl, dialkylaminoalkyl, acylamino-alkyl, phthalimido-alkyl, alkoxycarbonylamino-alkyl, aryloxycarbonylamino-alkyl, aralkoxycarbonylamino-alkyl, alkylaminocarbonylamino-alkyl, arylaminocarbonylamino-alkyl, aralkylaminocarbonylamino-alkyl, alkylsulphonylamino-alkyl or arylsulphonylamino-alkyl group, R2 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group or a group of the formula <IMAGE> R3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R4 and R5 each represent a hydrogen atom or R4 and R5 together represent an oxo group, R6 and R7 each represent a hydrogen atom or an alkyl or aralkyl group or R6 and R7 together with the nitrogen atom to which they are attached represent a 5-membered or 6-membered heteromonocyclic ring which may contain a further nitrogen atom or an oxygen or sulphur atom, and n stands for zero, 1 or 2, and pharmaceutically acceptable salts thereof have antihypertensive activity and can be used as medicaments in the form of pharmaceutical preparations.
Inventors
- 👤 Michael R. Attwood
- 👤 Cedric H. Hassall
- 👤 Robert W. Lambert
- 👤 Geoffrey Lawton
- 👤 Sally Redshaw
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 13:23
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D231/00; C07D231/02; C07D231/04; C07D237/00; C07D237/02; C07D237/04; C07D403/00; C07D403/02; C07D403/06; C07D487/00; C07D487/02; C07D487/04; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3886; C07F9/40; C07F9/4071; C07F9/409; C07F9/547; C07F9/645; C07F9/6509; C07F9/650905; C07F9/650947; C07F9/6561; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06139
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
143 words
Compounds of the formula ##STR26## wherein B represents an ethylene group, R 1 represents a hydrogen atom or an alkyl, aralkyl, amino-alkyl, monoalkylamino-alkyl, dialkylamino-alkyl, acylamino-alkyl, phthalimido-alkyl, alkoxycarbonylamino-alkyl, aryloxycarbonylamino-alkyl, aralkoxycarbonylamino-alkyl, alkylaminocarbonylamino-alkyl, arylaminocarbonyl-aminoalkyl, aralkylaminocarbonylamino-alkyl, alkylsulphonylamino-alkyl or arylsulphonylamino-alkyl group, R 2 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group or a group of the formula ##STR27## R 3 represents a carboxyl, alkoxy-carbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group, R 6 and R 7 each represent a hydrogen atom or an alkyl or aralkyl group or R 6 and R 7 together with the nitrogen atom to which they are attached represent a 5-membered or 6-membered heteromonocyclic ring which may contain a further nitrogen atom or an oxygen or sulphur atom, and n is 2, and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
143 words
Compounds of the formula ##STR26## wherein B represents an ethylene group, R 1 represents a hydrogen atom or an alkyl, aralkyl, amino-alkyl, monoalkylamino-alkyl, dialkylamino-alkyl, acylamino-alkyl, phthalimido-alkyl, alkoxycarbonylamino-alkyl, aryloxycarbonylamino-alkyl, aralkoxycarbonylamino-alkyl, alkylaminocarbonylamino-alkyl, arylaminocarbonyl-aminoalkyl, aralkylaminocarbonylamino-alkyl, alkylsulphonylamino-alkyl or arylsulphonylamino-alkyl group, R 2 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group or a group of the formula ##STR27## R 3 represents a carboxyl, alkoxy-carbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group, R 6 and R 7 each represent a hydrogen atom or an alkyl or aralkyl group or R 6 and R 7 together with the nitrogen atom to which they are attached represent a 5-membered or 6-membered heteromonocyclic ring which may contain a further nitrogen atom or an oxygen or sulphur atom, and n is 2, and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
53 words
Compounds as claimed in claim 1, wherein R 1 represents a hydrogen atom or an alkyl, aralkyl, amino-alkyl, monoalkylamino-alkyl, dialkylamino-alkyl, acylamino-alkyl, alkoxycarbonylamino-alkyl, aryloxycarbonylamino-alkyl, aralkoxycarbonylamino-alkyl, alkylaminocarbonylamino-alkyl, arylaminocarbonylamino-alkyl, aralkylaminocarbonylamino-alkyl, alkylsulphonylamino-alkyl or arylsulphonylamino-alkyl, R 2 represents a carboxyl or alkoxycarbonyl group or a group of formula (i) and R 3 represents a carboxyl or alkoxycarbonyl group.
Claim 4
Dependent Claim
19 words
Compounds as claimed in claim 1 wherein R 1 represents an alkyl, aralkyl, acylamino-alkyl, phthalimido-alkyl, aralkoxycarbonylamino-alkyl or arylaminocarbonylamino-alkyl group.
Claim 5
Dependent Claim
22 words
Compounds as claimed in claim 1 wherein R 2 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group or a group of formula (ii).
Claim 6
Dependent Claim
13 words
Compounds as claimed in claim 1 wherein R 3 represents a carboxyl group.
Claim 7
Dependent Claim
46 words
Compounds as claimed in claim 1 wherein B represents an ethylene group, R 1 represents an alkyl, aralkyl, acylaminoalkyl, phthalimido-alkyl, aralkoxycarbonylamino-alkyl or arylaminocarbonylamino-alkyl group, R 2 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group or a group of formula (ii), and R 3 represents a carboxyl group.
Claim 8
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Carboxy-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 9
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Ethoxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 10
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Benzyloxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 11
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Carbamoyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 12
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Ethylcarbamoyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 13
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Carboxy-4-phenylbutylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 14
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Carboxy-2-phenylethylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 15
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Carboxy-4-methylpentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 16
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Ethoxycarbonyl-4-methylpentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 17
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-[3-(4-Chlorophenyl)-1-ethoxycarbonylpropylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 18
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-[1-Ethoxycarbonyl-3-(4-methoxyphenyl)propylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 19
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-[3-(4-Biphenylyl)-1-ethoxycarbonylpropylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 20
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Ethoxycarbonyl-5-phthalimidopentylamino)-octa-hydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 21
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(1-Ethoxycarbonyl-3-phenylpropylamino)-octahydro-10-oxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 22
Dependent Claim
9 words
In accordance with claim 1, the compound, 9-(5-Benzyloxyformamido-1-ethoxycarbonylpentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 23
Dependent Claim
36 words
A compound selected from the following: Tert.butyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-benzyloxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, methyl 9-(1-benzyloxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, methyl-9-(1-carboxy-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, methyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, ethyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-carbamoyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-ethylcarbamoyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-ethoxycarbonyl-4-methylpentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-[3-(4-chlorophenyl)-1-ethoxycarbonylpropylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-[1-ethoxycarbonyl-3-(4-methoxyphenyl)propylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-[3-(4-biphenylyl)-1-ethoxycarbonylpropylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-ethoxycarbonyl-5-phthalimidopentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, benzyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-10-oxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate and tert.butyl 9-(5-benzyloxyformamido-1-ethoxycarbonylpentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate.
Claim 24
Dependent Claim
36 words
A compound selected from the following: Tert.butyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-benzyloxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, methyl 9-(1-benzyloxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, methyl-9-(1-carboxy-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, methyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, ethyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-carbamoyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-ethylcarbamoyl-3-phenylpropylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-ethoxycarbonyl-4-methylpentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-[3-(4-chlorophenyl)-1-ethoxycarbonylpropylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-[1-ethoxycarbonyl-3-(4-methoxyphenyl)propylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-[3-(4-biphenylyl)-1-ethoxycarbonylpropylamino]-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, tert.butyl 9-(1-ethoxycarbonyl-5-phthalimidopentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate, benzyl 9-(1-ethoxycarbonyl-3-phenylpropylamino)-octahydro-10-oxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate and tert.butyl 9-(5-benzyloxyformamido-1-ethoxycarbonylpentylamino)-octahydro-6,10-dioxo-6H-pyridazo[1,2-a][1,2]diazepine-1-carboxylate.
Claim 25
Dependent Claim
18 words
A compound as set forth in claim 1 wherein the configuration at each asymmetric carbon atom is (S).
Claim 26
Dependent Claim
18 words
A compound as set forth in claim 22 wherein the configuration at each asymmetric carbon atom is (S).
Claim 27
Dependent Claim
51 words
A compound of the formula ##STR28## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group, Hal represents a halogen atom and n is 2.
Claim 28
Dependent Claim
51 words
A compound of the formula ##STR28## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group, Hal represents a halogen atom and n is 2.
Claim 29
Dependent Claim
46 words
A compound of the formula ##STR29## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent and oxo group and n is 2.
Claim 30
Dependent Claim
46 words
A compound of the formula ##STR29## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent and oxo group and n is 2.
Claim 31
Dependent Claim
46 words
An azide of the formula ##STR30## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group and n is 2.
Claim 32
Dependent Claim
46 words
An azide of the formula ##STR30## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group and n is 2.
Claim 33
Dependent Claim
52 words
A compound of the formula ##STR31## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group, R 8 represents a phthaloylamino group and n is 2.
Claim 34
Dependent Claim
52 words
A compound of the formula ##STR31## wherein B represents an ethylene group, R 3 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group, R 4 and R 5 each represent a hydrogen atom or R 4 and R 5 together represent an oxo group, R 8 represents a phthaloylamino group and n is 2.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-04-22 | 1988-10-22 | 1989-04-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-22 | 1992-10-22 | 1993-04-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-22 | 1996-10-22 | 1997-04-23 | $7700.00 | Window Closed / Lapsed |