US4658024A
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US
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Pyrazolo [1,2-a][1,2]-diazepines useful as antihypertensives
Assignee: Hoffmann La Roche Inc
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Filing: 1985-02-01
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Granted: 1987-04-14
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Expires: 2005-02-01
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, dialkylamino-alkyl, 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
2026-10-29 13:39
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: 22
Claim 1
Independent Claim
143 words
Compounds of the formula ##STR26## wherein B represents a methylene, R 1 represents a hydrogen atom or an alkyl, aralkyl, amino-alkyl, monoalkylamino-alkyl, dialkylamino-alkyl, acylamino-alkyl, phthalimidoalkyl, alkoxycarbonylamino-alkyl, aryloxycarbonylamino-alkyl, aralkoxycarbonylamino-alkyl, alkylaminocarbonylamino-alkyl, arylaminocarbonylamino-alkyl, arakylaminocarbonylamino-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, 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 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 stands for 2, and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
143 words
Compounds of the formula ##STR26## wherein B represents a methylene, R 1 represents a hydrogen atom or an alkyl, aralkyl, amino-alkyl, monoalkylamino-alkyl, dialkylamino-alkyl, acylamino-alkyl, phthalimidoalkyl, alkoxycarbonylamino-alkyl, aryloxycarbonylamino-alkyl, aralkoxycarbonylamino-alkyl, alkylaminocarbonylamino-alkyl, arylaminocarbonylamino-alkyl, arakylaminocarbonylamino-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, 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 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 stands for 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
49 words
Compounds as claimed in claim 1 wherein B represents a methylene, R 1 represents an alkyl, aralkyl, acylamino-alkyl, phthalimido-alkyl, aralkoxycarbonylamino-alkyl or arylaminocarbonylamino-alkyl group, R 2 represents a carboxyl, alkoxycarbonyl or aralkoxycarbonyl group or a group of formula (ii), R 3 represents a carboxyl group and n stands for 2.
Claim 8
Dependent Claim
9 words
In accordance with claim 1, the compound, 8-(1-Carboxy-3-phenylpropylamino)-2,3,7,8,9-hexahydro-5,9-dioxo-1H,5H-pyrazolo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 9
Dependent Claim
9 words
In accordance with claim 1, the compound, 8-(1-Ethoxycarbonyl-3-phenylpropylamino)-2,3,6,7,8,9-hexahydro-5,9-dioxo-1H,5H-pyrazolo[1,2-a][1,2]diazepine-1-carboxylic acid.
Claim 10
Dependent Claim
18 words
A compound as set forth in claim 1 wherein the configuration at each asymmetric carbon atom is (S).
Claim 11
Dependent Claim
84 words
A compound of the formula ##STR28## wherein B represents a methylene, 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 stands for 2, with the proviso that B represents a methylene group when R 4 and R 5 together represent an oxo group, R 3 represents a carboxyl or alkoxycarbonyl group and n stands for 1.
Claim 12
Dependent Claim
84 words
A compound of the formula ##STR28## wherein B represents a methylene, 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 stands for 2, with the proviso that B represents a methylene group when R 4 and R 5 together represent an oxo group, R 3 represents a carboxyl or alkoxycarbonyl group and n stands for 1.
Claim 13
Dependent Claim
46 words
A compound of the formula ##STR29## wherein B represents a methylene, 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 stands for 2.
Claim 14
Dependent Claim
46 words
A compound of the formula ##STR29## wherein B represents a methylene, 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 stands for 2.
Claim 15
Dependent Claim
46 words
An azide of the formula ##STR30## wherein B represents a methylene, 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 gorup and n stands for 2.
Claim 16
Dependent Claim
46 words
An azide of the formula ##STR30## wherein B represents a methylene, 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 gorup and n stands for 2.
Claim 17
Dependent Claim
52 words
A compound of the formula ##STR31## wherein B represents a methylene, 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 stands for 2.
Claim 18
Dependent Claim
52 words
A compound of the formula ##STR31## wherein B represents a methylene, 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 stands for 2.
Claim 19
Dependent Claim
7 words
In accordance with claim 1, tert.butyl 8-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,6,7,8,9-hexahydro-6,9-dioxo-1H,5H-pyrazolo[1,2-a][1,2]-diazepine-1-carboxylate.
Claim 20
Dependent Claim
14 words
The compound of claim 14 wherein each asymmetric carbon atom has the (S) configuration.
Claim 21
Dependent Claim
15 words
A compound in accordance with claim 11, wherein each asymmetric carbon has the (S) configuration.
Claim 22
Dependent Claim
15 words
A compound in accordance with claim 6, wherein each asymmetric carbon has the (S) configuration.
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) | 1990-04-13 | 1990-10-13 | 1991-04-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-04-13 | 1994-10-13 | 1995-04-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-04-13 | 1998-10-13 | 1999-04-14 | $7700.00 | Window Closed / Lapsed |