US4156733A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-(2-Aminocyclopentyl) alkanoylanilides
Assignee: Pharmacia and Upjohn Co
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Filing: 1978-02-21
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Granted: 1979-05-29
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Expires: 1998-02-21
Abstract
Abstract N-(2-Aminocyclopentyl)N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(dimethylamino)cyclopentyl]propionanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System anti-depressant properties. Many of them are new. These compounds are promising anti-depressant drugs which are characterized by a better therapeutic ratio than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.
Inventors
- 👤 Jacob Szmuszkovicz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 21:48
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/16; C07C233/02; C07C271/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
220 words
A process for treating depression which comprises administering to a depressed human a compound of the formula ##STR43## wherein the wavy line (˜) in the 1-position of the cyclopentyl ring indicates cis or trans configuration of the substituents in the 1- and 2-positions of the cyclopentyl ring; p is zero or 1; Q is oxygen or sulfur; R is C 1 to C 3 -alkyl R 1 and R 2 are taken together with the nitrogen to which they are bonded they complete an N-pyrrolidinyl or N-piperidinyl ring; each of Y and Z is selected from the group consisting of hydrogen, a halogen having an atomic number of from 9 to 35, trifluoromethyl, C 1 to C 2 -alkyl and C 1 to C 2 -alkyloxy and when Y is trifluoromethyl Z is hydrogen, when Y is C 1 to C 2 -alkyloxy and Z is hydrogen the C 1 to C 2 -alkyloxy is in the 3-position, when Y and Y and Z are both halogens or C 1 to C 2 -alkyloxy they are present in the 3- and 4- or 3- and 5-positions, or a pharmacologically acceptable salt thereof, in an amount in the range from about 1 to about 100 mg. per dosage unit to alleviate the conditions of depression, in association with a pharmaceutical carrier.
Claim 2
Dependent Claim
220 words
A process for treating depression which comprises administering to a depressed human a compound of the formula ##STR43## wherein the wavy line (˜) in the 1-position of the cyclopentyl ring indicates cis or trans configuration of the substituents in the 1- and 2-positions of the cyclopentyl ring; p is zero or 1; Q is oxygen or sulfur; R is C 1 to C 3 -alkyl R 1 and R 2 are taken together with the nitrogen to which they are bonded they complete an N-pyrrolidinyl or N-piperidinyl ring; each of Y and Z is selected from the group consisting of hydrogen, a halogen having an atomic number of from 9 to 35, trifluoromethyl, C 1 to C 2 -alkyl and C 1 to C 2 -alkyloxy and when Y is trifluoromethyl Z is hydrogen, when Y is C 1 to C 2 -alkyloxy and Z is hydrogen the C 1 to C 2 -alkyloxy is in the 3-position, when Y and Y and Z are both halogens or C 1 to C 2 -alkyloxy they are present in the 3- and 4- or 3- and 5-positions, or a pharmacologically acceptable salt thereof, in an amount in the range from about 1 to about 100 mg. per dosage unit to alleviate the conditions of depression, in association with a pharmaceutical carrier.
Claim 3
Dependent Claim
77 words
A process according to claim 1 wherein the formula I compound is one in which R is C 1 to C 3 -alkyl, R 1 and R 2 are taken together with the nitrogen to which they are bonded to complete an N-pyrrolidinyl or N-piperidinyl moiety, and at least one of Y and Z is a halogen having an atomic number of from 9 to 35, in the 3- or 4-position, or a pharmacologically acceptable salts thereof.
Claim 4
Dependent Claim
17 words
A process according to claim 1 wherein the compound is 3,4-dichloro-N-[2-(N-pyrrolidinyl)cyclopentyl]propionanilide, or a pharmacologically acceptable salt thereof.
Claim 5
Dependent Claim
218 words
A pharmaceutical preparation in dosage unit form adapted for administration to obtain an anti-depression effect comprising per dosage unit, an anti-depressant effective, non-toxic amount in the range from about 1 to about 100 mg. of a compound of the formula ##STR44## wherein the wave line (˜) in the 1-position of the cyclopentyl ring indicates cis or trans configuration of the substituents in the 1- and 2-positions of the cyclopentyl ring; p is zero or 1; Q is oxygen or sulfur; R is C 1 to C 3 -alkyl; R 1 and R 2 are taken together with the nitrogen to which they are bonded they complete an N-pyrrolidinyl or N-piperidinyl ring; each of Y and Z is selected from the group consisting of hydrogen, a halogen having an atomic number of from 9 to 35, trifluoromethyl, C 1 to C 2 -alkyl and C 1 to C 2 -alkyloxy and when Y is trifluoromethyl Z is hydrogen, when Y is C 1 to C 2 -alkyloxy and Z is hydrogen the C 1 to C 2 -alkyloxy is in the 3-position, when Y and and Z are both halogens or C 1 to C 2 -alkyloxy they are present in the 3- and 4- or 3- and 5-positions, or a pharmacologically acceptable salt thereof, and a pharmaceutical diluent.
Claim 6
Dependent Claim
218 words
A pharmaceutical preparation in dosage unit form adapted for administration to obtain an anti-depression effect comprising per dosage unit, an anti-depressant effective, non-toxic amount in the range from about 1 to about 100 mg. of a compound of the formula ##STR44## wherein the wave line (˜) in the 1-position of the cyclopentyl ring indicates cis or trans configuration of the substituents in the 1- and 2-positions of the cyclopentyl ring; p is zero or 1; Q is oxygen or sulfur; R is C 1 to C 3 -alkyl; R 1 and R 2 are taken together with the nitrogen to which they are bonded they complete an N-pyrrolidinyl or N-piperidinyl ring; each of Y and Z is selected from the group consisting of hydrogen, a halogen having an atomic number of from 9 to 35, trifluoromethyl, C 1 to C 2 -alkyl and C 1 to C 2 -alkyloxy and when Y is trifluoromethyl Z is hydrogen, when Y is C 1 to C 2 -alkyloxy and Z is hydrogen the C 1 to C 2 -alkyloxy is in the 3-position, when Y and and Z are both halogens or C 1 to C 2 -alkyloxy they are present in the 3- and 4- or 3- and 5-positions, or a pharmacologically acceptable salt thereof, and a pharmaceutical diluent.
Claim 7
Dependent Claim
18 words
A pharmaceutical preparation according to claim 4 wherein the compound of formula I is in the trans configuration.
Claim 8
Dependent Claim
18 words
A pharmaceutical preparation according to claim 5 wherein the compound of formula I is in the cis configuration.
Claim 9
Dependent Claim
75 words
A pharmaceutical preparation according to claim 4 wherein in the formula I compound R is C 1 to C 3 -alkyl, R 1 and R 2 are taken together with the nitrogen to which they are bonded to complete an N-pyrrolidinyl or N-piperidinyl moiety, and at least one of Y and Z is a halogen having an atomic number of from 9 to 35, in the 3- or 4-position, or a pharmacologically acceptable salt thereof.
Claim 10
Dependent Claim
20 words
A pharmaceutical preparation according to claim 7 wherein the formula I compound is 3,4-dichloro-N-[2-(N-pyrrolidinyl)cyclopentyl]propionanilide, or a pharmacologically acceptable salt thereof.
Claim 11
Dependent Claim
7 words
3,4-Dichloro-N-[2-(N-pyrrolidinyl)cyclopentyl]propionanilide, and the pharmacologically acceptable salts thereof.
Claim 12
Dependent Claim
7 words
3,4-Dichloro-N-[2-(N-pyrrolidinyl)cyclopentyl]propionanilide, and the pharmacologically acceptable salts thereof.
References Cited (Backward Citations)
US3510492A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-28 | 1982-11-27 | 1983-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-28 | 1986-11-27 | 1987-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-28 | 1990-11-27 | 1991-05-29 | $7700.00 | Window Closed / Lapsed |