US3974280A
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US
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Benzothiophenes
Assignee: Novartis Corp
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Filing: 1974-12-03
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Granted: 1976-08-10
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Expires: 1994-12-03
Abstract
Abstract The invention relates to a process for the production of new benzo[b]thiophenes of formula I ##SPC1## wherein PH is optionally substituted o-phenylene, one of the radicals R 1 and R 2 is hydrogen or lower alkyl, and the other of the radicals R 1 and R 2 is optionally C-substituted piperidyl which optionally carries hydroxy on the ring-C-atom bound to the benzo[b]thienyl radical, or which optionally contains a C-C-double bond emanating from this C-atom, and which optionally carries on the N-atom a hydrocarbon radical of aliphatic character, which radical is optionally substituted in a position higher than the 1-position, and of their acid addition salts. These new compounds possess valuable pharmacological properties. In particular they inhibit mono-amine oxidase and further inhibit the absorption of noradrenaline and serotonine in the brain. They are useful as active substances for pharmaceutical preparations for the treatment of mental depressions and psychoses.
Inventors
- 👤 Raymond Bernasconi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:31
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/38; A61K31/395; A61K31/435; A61K31/44; A61K31/445; C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/10; C07D295/00; C07D295/04; C07D295/08; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/56; C07D333/58; C07D409/00; C07D409/02; C07D409/04
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
157 words
A benzo[b]thiophene of the formula ##SPC9## wherein Ph is o-phenylene unsubstituted or at most di-substituted by C 1 -C 4 -lower alkyl, C 1 -C 4 -lower alkoxy, chlorine or hydroxy, R 1 or R 2 is piperidyl which is saturated or contains a C-C-double bond emanating from the ring-C-atom bound to the benzo[b]thienyl radical, and, if saturated, at this C-atom is unsubstituted or substituted by hydroxy, and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -lower alkyl, benzyl, C 1 -C 4 -lower alkylbenzyl, C 1 -C 4 -lower alkoxybenzyl, halobenzyl, 2-phenethyl or α-methyl-2-phenethyl, and R 2 or R 1 is hydrogen or C 1 -C 4 -lower alkyl, and its pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
157 words
A benzo[b]thiophene of the formula ##SPC9## wherein Ph is o-phenylene unsubstituted or at most di-substituted by C 1 -C 4 -lower alkyl, C 1 -C 4 -lower alkoxy, chlorine or hydroxy, R 1 or R 2 is piperidyl which is saturated or contains a C-C-double bond emanating from the ring-C-atom bound to the benzo[b]thienyl radical, and, if saturated, at this C-atom is unsubstituted or substituted by hydroxy, and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -lower alkyl, benzyl, C 1 -C 4 -lower alkylbenzyl, C 1 -C 4 -lower alkoxybenzyl, halobenzyl, 2-phenethyl or α-methyl-2-phenethyl, and R 2 or R 1 is hydrogen or C 1 -C 4 -lower alkyl, and its pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
153 words
A compound according to claim 1 having the formula I given in claim 1, wherein Ph is o-phenylene unsubstituted or at most di-substituted by C 1 -C 4 -lower alkyl, C 1 -C 4 -lower alkoxy, chlorine or hydroxy, R 1 or R 2 is piperidyl which optionally contains a C-C-double bond emanating from the ring-C-atom bound to the benzo[b] thienyl radical, and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -lower alkyl, benzyl, C 1 -C 4 -lower alkyl benzyl, C 1 -C 4 -lower alkoxybenzyl, halobenzyl, 2-phenethyl or α-methyl-2-phenethyl, and R 2 or R 1 is hydrogen or C 1 -C 4 -lower alkyl, and its pharmaceutically acceptable acid addition salts.
Claim 4
Dependent Claim
99 words
A compound according to claim 1 having the formula I given in claim 1, wherein Ph is o-phenylene, R 1 or R 2 is piperidyl which optionally contains a C-C-double bond emanating from the ring-C-atom bound to the benzo[b]thienyl radical, and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, cyclopropylmethyl or benzyl, and R 2 or R 1 is hydrogen, and its pharmaceutically acceptable acid addition salts.
Claim 5
Dependent Claim
69 words
A compound according to claim 1 having the formula I given in claim 1, wherein Ph is o-phenylene, R 1 or R 2 is 4-piperidyl or 1,2,3,6-tetrahydro-4-pyridyl, which is unsubstituted or substituted in the 3-position by methyl, and which is unsubstituted or substituted at its N-atom by methyl, allyl, 2-propynyl or cyclopropylmethyl or benzyl, and R 2 or R 1 is hydrogen, and its pharmaceutically acceptable acid addition salts.
Claim 6
Dependent Claim
16 words
A compound according to claim 1 which is 1-methyl-4-(benzo[b]thien-2-yl)-1,2,3,6-tetrahydropyridine, and its pharmaceutically acceptable acid addition salts.
Claim 7
Dependent Claim
16 words
A compound according to claim 1 which is 1-methyl-4-(benzo[b]thien-2-yl)-piperidine, and its pharmaceutically acceptable acid addition salts.
Claim 8
Dependent Claim
16 words
A compound according to claim 1 which is 4-(benzo[b]thien-2-yl)-piperidine, and its pharmaceutically acceptable acid addition salts.
Claim 9
Dependent Claim
16 words
A compound according to claim 1 which is 1-(2-propinyl)-4-(benzo[b]thien-2-yl)-piperidine, and its pharmaceutically acceptable acid addition salts.
Claim 10
Dependent Claim
16 words
A compound according to claim 1 which is 1,3-dimethyl-4-(benzo[b]thien-2-yl)-4-piperidinol, and its pharmaceutically acceptable acid addition salts.
Claim 11
Dependent Claim
16 words
A compound according to claim 1 which is 1-methyl-4-(benzo[b]thien-3-yl)-1,2,3,6-tetrahydropyridine, and its pharmaceutically acceptable acid addition salts.
Claim 12
Dependent Claim
16 words
A compound according to claim 1 which is 1-methyl-4-benzo[b]thien-3-yl)-piperidine, and its pharmaceutically acceptable acid addition salts.
Claim 13
Dependent Claim
16 words
A compound according to claim 1 which is 4-(benzo[b]thien-3-yl)-piperidine, and its pharmaceutically acceptable acid addition salts.
Claim 14
Dependent Claim
9 words
A compound according to claim 1 which is 1,3-dimethyl-4-(benzo[b]thien-2-yl)-1,2,3,6-tetrahydro-pyridine.
Claim 15
Dependent Claim
16 words
A compound according to claim 1 which is 1,3-dimethyl-4-(benzo[b]thien-2-yl)-piperidine, and its pharmaceutically acceptable acid addition salts.
Claim 16
Dependent Claim
16 words
A compound according to claim 1 which is 3-methyl-4-(benzo[b]thien-2-yl)-piperidine, and its pharmaceutically acceptable acid addition salts.
Claim 17
Dependent Claim
188 words
A pharmaceutical preparation for the treatment of mental depression and psychoses comprising a therapeutically effective amount of a compound according to claim 1 which corresponds to the formula ##SPC10## wherein Ph is o-phenylene unsubstituted or at most di-substituted by C 1 -C 4 -lower alkyl, C 1 -C 4 -lower alkoxy, chlorine or hydroxy, R 1 or R 2 is piperidyl which is saturated or contains a C-C-double bond emanating from the ring-C-atom bound to the benzo[b]thienyl radical, and, if saturated, at this C-atom is unsubstituted or substituted by hydroxy and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -lower alkyl, benzyl, C 1 -C 4 -lower alkylbenzyl, C 1 -C 4 -lower alkoxybenzyl, halobenzyl, 2-phenethyl or α-methyl-2-phenethyl, and R 2 or R 1 is hydrogen or C 1 -C 4 -lower alkyl, or of a pharmaceutically acceptable acid addition salt thereof together with a pharmaceutical carrier material.
Claim 18
Dependent Claim
178 words
A pharmaceutical preparation for the treatment of mental depression and psychoses according to claim 16, in which a therapeutically effective amount of a compound of formula I given in claim 16, wherein Ph is o-phenylene unsubstituted or at most di-substituted by C 1 -C 4 -lower alkyl, C 1 -C 4 -lower alkoxy, chlorine or hydroxy, R 1 or R 2 is piperidyl which is saturated or contains a C-C-double bond emanating from the ring-C-atom bound to the benzy[b]thienyl radical, and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -lower alkyl, benzyl, C 1 -C 4 -lower alkylbenzyl, C 1 -C 4 -lower alkoxybenzyl, halobenzyl, 2-phenethyl or α-methyl-2-phenethyl, and R 2 or R 1 is hydrogen or C 1 -C 4 -lower alkyl, or of a pharmaceutically acceptable acid addition salt thereof together with a pharmaceutical carrier material.
Claim 19
Dependent Claim
126 words
A pharmaceutical preparation for the treatment of mental depression and psychoses according to claim 16, in which a therapeutically effective amount of a compound of formula I given in claim 16, wherein Ph is o-phenylene, R 1 or R 2 is piperidyl which is saturated or contains a C-C-double bond emanating from the ring-C-atom bound to the benzy[b]thienyl radical, and which at its other ring-C-atom is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, cyclopropylmethyl or benzyl, and R 2 or R 1 is hydrogen, or of a pharmaceutically acceptable acid addition salt thereof together with a pharmaceutical carrier material.
Claim 20
Dependent Claim
94 words
A pharmaceutical preparation for the treatment of mental depression and psychoses according to claim 16, in which a therapeutically effective amount of a compound of formula I given in claim 16, wherein Ph is o-phenylene, R 1 or R 2 is 4-piperidyl or 1,2,3,6-tetrahydro-4-pyridyl, which is unsubstituted or substituted in the 3-position by methyl, and which is unsubstituted or substituted at its N-atom by methyl, allyl, 2-propynyl or cyclopropylmethyl or benzyl, and R 2 or R 1 is hydrogen, or of a pharmaceutically acceptable acid addition salt thereof together with a pharmaceutical carrier material.
Claim 21
Dependent Claim
189 words
A method for the treatment of mental depression in a warm-blooded animal comprising administration to said animal of a therapeutically effective amount of a compound according to claim 1, which corresponds to the formula I, ##SPC11## wherein Ph is o-phenylene unsubstituted or at most di-substituted by C 1 -C 4 -lower alkyl, C 1 -C 4 -lower alkoxy, chlorine or hydroxy, R 1 or R 2 is piperidyl which is saturated or contains a C-C-double bond emanating from the ring-C-atom bound to the benzo[b]thienyl radical, and, if saturated, at this C-atom is unsubstituted or substituted by hydroxy, and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -lower alkyl, benzyl, C 1 -C 4 -lower alkylbenzyl, C 1 -C 4 -lower alkoxybenzyl, halobenzyl, 2-phenethyl or α-methyl-2-phenethyl, and R 2 or R 1 is hydrogen or C 1 -C 4 -lower alkyl, or of a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
160 words
A method according to claim 20, wherein a compound of the formula I given in claim 20, in which Ph is o-phenylene unsubstituted or at most di-substituted by C 1 -C 4 -lower alkyl, C 1 -C 4 -lower alkoxy, chlorine or hydroxy, R 1 or R 2 is piperidyl which is saturated or contains a C-C-double bond emanating from the ring-C-atom bound to the benzo[b]thienyl radical, and which at its other ring-C-atoms is unsubstituted or substituted by one methyl, and which at its N-atom is unsubstituted or substituted by C 1 -C 4 -lower alkyl, C 3 -C 4 -lower alkenyl, C 3 -C 4 -lower alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -lower alkyl, benzyl, C 1 -C 4 -lower alkylbenzyl, C 1 -C 4 -lower alkoxybenzyl, halobenzyl, 2-phenethyl or α-methyl-2-phenethyl, and R 2 or R 1 is hydrogen or C 1 -C 4 -lower alkyl, or a pharmaceutically acceptable acid addition salt thereof is used.
References Cited (Backward Citations)
US3070606A
Cited
US3855242A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-10 | 1980-02-09 | 1980-08-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-10 | 1984-02-09 | 1984-08-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-10 | 1988-02-09 | 1988-08-10 | $7700.00 | Window Closed / Lapsed |