Patent US4576279A successfully refreshed from Google Patents.
Patent US4288442A successfully refreshed from Google Patents.
US4288442A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Inhibiting adrenergic β-receptors with piperidinopropyl derivatives
Assignee: Roche Diagnostics GmbH
•
Filing: 1980-01-31
•
Granted: 1981-09-08
•
Expires: 2000-01-31
Abstract
Abstract A piperidinopropyl derivative of the formula <IMAGE> in which R1 and R2 each independently is hydrogen or a lower alkyl radical, or together are an alkylene radical, R3 is hydrogen, hydroxy, or acyloxy, R4 is hydrogen or formyl, A together with the adjacent benzene ring and N-R4 forms a benzimidazolin-2-one, benzimidazoline-2-thione, oxindole, indazole carbazole, benztriazole, benzimidazole, indoline or indole moiety, and B is a heterocyclic radical or, under certain circumstances, a phenyl radical, either of which is optionally substituted by halogen, hydroxy, lower alkyl, hydroxy-lower alkyl, carboxamido-lower alkyl, lower alkoxy, amino, carboxamido, lower alkyl-carbonylamino, acyl or lower alkylsulphonylamino, or a pharmacologically acceptable salt thereof. The compounds inhibit adrenergic beta -receptors and lower blood pressure.
Inventors
- 👤 Walter-Gunar Friebe
- 👤 Helmut Michel
- 👤 Carl H. Ross
- 👤 Fritz Wiedemann
- 👤 Gisbert Sponer
- 👤 Wolfgang Schaumann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:03
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/20; C07D211/22; A; A61; A61P; A61P25/00; A61P25/02; A61P9/00; A61P9/08; A61P9/12; C07C; C07C205/00; C07C205/49; C07C205/56
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
243 words
A piperidinopropyl derivative of the formula ##STR12## in which R 1 and R 2 each independently is hydrogen or a lower alkyl radical, or together are a C 2-4 -alkylene radical, R 3 is hydrogen, hydroxy, or lower alkanoyloxy, R 4 is hydrogen or formyl, A is (a) --X 1 ═Y 1 in which (i) X 1 and Y 1 each independently is a nitrogen atom or --C(R 6 )═, in which (A)R 6 is hydrogen, a lower alkyl radical optionally substituted by hydroxy or lower alkanoyloxy, a carboxyl radical or an alkoxycarbonyl radical, or (b)--X 2 --Y 2 in which (i) X 2 is --CH 2 -- or --N(R 7 )--, in which (A)R 7 is hydrogen or lower alkyl, and (ii) Y 2 is --CH 2 -- or --C(═Z)--, in which (A)Z is oxygen or sulfur, or (c)--CR 8 ═CR 9 -- in which (i) R 8 and R 9 together are a --CH═CH--CH═CH--bridge, with the proviso that when present, it is Y 1 or Y 2 which is connected to N--R 4 , and B is a pyridyl, primidyl, benzimidazolinonyl, benzimidazolinyl, benztriazolyl, indazolyl, benzodioxolanyl or carbazolyl radical or, if A is --X 2 --Y 2 -- or --CR 8 ═CR 9 , may also be a phenyl radical, either of which is optionally substituted by halogen, hydroxyl, lower alkyl, hydroxy-lower alkyl, carboxamido-lower alkyl, lower alkoxy, amino, carboxamido, lower alkyl-carbonylamino, lower alkanoyloxy or lower alkylsulphonylamino, or a pharmacologically acceptable salt thereof.
Claim 2
Dependent Claim
243 words
A piperidinopropyl derivative of the formula ##STR12## in which R 1 and R 2 each independently is hydrogen or a lower alkyl radical, or together are a C 2-4 -alkylene radical, R 3 is hydrogen, hydroxy, or lower alkanoyloxy, R 4 is hydrogen or formyl, A is (a) --X 1 ═Y 1 in which (i) X 1 and Y 1 each independently is a nitrogen atom or --C(R 6 )═, in which (A)R 6 is hydrogen, a lower alkyl radical optionally substituted by hydroxy or lower alkanoyloxy, a carboxyl radical or an alkoxycarbonyl radical, or (b)--X 2 --Y 2 in which (i) X 2 is --CH 2 -- or --N(R 7 )--, in which (A)R 7 is hydrogen or lower alkyl, and (ii) Y 2 is --CH 2 -- or --C(═Z)--, in which (A)Z is oxygen or sulfur, or (c)--CR 8 ═CR 9 -- in which (i) R 8 and R 9 together are a --CH═CH--CH═CH--bridge, with the proviso that when present, it is Y 1 or Y 2 which is connected to N--R 4 , and B is a pyridyl, primidyl, benzimidazolinonyl, benzimidazolinyl, benztriazolyl, indazolyl, benzodioxolanyl or carbazolyl radical or, if A is --X 2 --Y 2 -- or --CR 8 ═CR 9 , may also be a phenyl radical, either of which is optionally substituted by halogen, hydroxyl, lower alkyl, hydroxy-lower alkyl, carboxamido-lower alkyl, lower alkoxy, amino, carboxamido, lower alkyl-carbonylamino, lower alkanoyloxy or lower alkylsulphonylamino, or a pharmacologically acceptable salt thereof.
Claim 3
Dependent Claim
136 words
A compound or salt according to claim 1, in which R 1 and R 2 each independently is hydrogen or C 1-4 -alkyl, or together are C 2-4 -alkylene, R 3 is hydrogen, hydroxy, or C 2-6 -alkanoyloxy or benzoyloxy optionally substituted by halogen, lower alkyl or lower alkoxy, A together with the adjacent benzene ring and >N--R 4 forms a benzimidazolin-2-one, benzimidazoline-2-thione, oxindole, indazole, carbazole, benztriazole, benzimidazole, indoline or indole moiety, and B is a pyridyl, pyrimidyl, benzimidazolinonyl, or benzodioxolanyl radical or, if A is --X 2 --Y 2 -- or --CR 8 ═CR 9 --, may also be a phenyl radical, any of which is optionally substituted by halogen, hydroxy, C 1-4 -alkyl, hydroxy-C 1-4 -alkyl, carboxamido-C 1-4 , C 1-4 -alkoxy, amino, carboxamido, C 1-4 -alkylcarbonylamino, C 2-6 -alkanoyl or C 1-4 -alkylsulphonylamino.
Claim 4
Dependent Claim
15 words
A compound or salt according to claim 1, in which said compound is 4-{2-hydroxy-3-[4-(2-methoxy-phenoxymethyl)-piperidino]-propoxy}-2-benzimidazolinone hydrochloride.
Claim 5
Dependent Claim
14 words
A compound or salt according to claim 1, in which said compound is 4-{2-hydroxy-3-[4-(3-methylphenoxymethyl)-piperidino]-propoxy}-2-benzimidazoline.
Claim 6
Dependent Claim
14 words
A compound or salt according to claim 1, in which said compound is 4-{2-hydroxy-3-[4-(4-2-benzimidazolinonyloxymethyl)-piperidino]-propoxy}-2-benzimidazolinone.
Claim 7
Dependent Claim
15 words
A compound or salt according to claim 1, in which said compound is 4-{2-hydroxy-3-[4-(4-hydroxyphenoxymethyl)-piperidino]-propoxy}-oxindole acetate.
Claim 8
Dependent Claim
14 words
A compound or salt according to claim 1, in which said compound is 4-{2-hydroxy-3-[4-(3-methylphenoxymethyl)-piperidino]-propoxy}-carbazole.
Claim 9
Dependent Claim
36 words
An andrenergic β-receptor-inhibitory and blood pressure lowering composition of matter comprising an adrenergic β-receptor-inhibiting or blood pressure lowering effective amount of a compound or salt according to claim 1 in admixture with a pharmacologically acceptable diluent.
Claim 10
Dependent Claim
37 words
A method of inhibiting adrenergic β-receptors and lowering blood pressure in a patient which comprises administering to such patient an adrenergic β-receptor-inhibiting or blood pressure lowering effective amount of a compound or salt according to claim 1.
Claim 11
Dependent Claim
24 words
The method according to claim 9 in which said compound is 4-{2-hydroxy-3-[4-(2-methoxy-phenoxymethyl)-piperidino]-propoxy}-2-benzimidazolinone hydrochloride, 4-{2-hydroxy-3-[4-(3-methylphenoxymethyl)-piperidino]-propoxy}-2-benzimidazolinone, 4-{2-hydroxy-3-[4-(4-2-benzimidazolinonyloxymethyl)-piperidino]-propoxy}-2-benzimidazolinone, 4-{2-hydroxy-3-[4-(4-hydroxyphenoxymethyl)-piperidino]-propoxy}-oxindole acetate, 4-{2-hydroxy-3-[4-(3-methylphenoxymethyl)-piperidino]-propoxy}-carbazole, or a pharmacologically acceptable salt thereof.
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) | 1984-09-07 | 1985-03-09 | 1985-09-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-07 | 1989-03-09 | 1989-09-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-07 | 1993-03-09 | 1993-09-08 | $7700.00 | Window Closed / Lapsed |