US4251541A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-Substituted-3-arylthio-4-hydroxypyrrolidines
Assignee: Wyeth LLC
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Filing: 1979-01-09
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Granted: 1981-02-17
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Expires: 1999-01-09
Abstract
Abstract Trans isomers of 1-substituted-3-arylthio-4-hydroxypyrrolidines and derivatives thereof having the formula: ##STR1## are disclosed wherein R 1 is hydrogen, lower-alkyl, --C(O)NH-lower-alkyl and --C(O)-NH-phenyl; R 2 is lower-alkyl, cycloalkyl and phenylalkyl; Ar is phenyl and substituted phenyl and the pharmaceutically acceptable addition salts thereof. The compounds have antidepressant activity in animals.
Inventors
- 👤 David A. Walsh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 20:28
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/12; C07D207/18; C07D207/20
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
66 words
A compound selected from 1-substituted-3-arylthio-4-hydroxypyrrolidines and derivatives thereof having the formula: ##STR7## wherein; R 1 is hydrogen, loweralkyl, ##STR8## R 2 is loweralkyl, cycloalkyl and phenylalkyl, Ar is phenyl and phenyl substituted by halogen, O-loweralkyl, --NHC(O)(CH 3 ), CF 3 , --C(O)CH 3 , --CH 2 --CH═CH 2 , alkyl, hydroxy, --OCH 2 -phenyl and --C(O)NH 2 , and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
66 words
A compound selected from 1-substituted-3-arylthio-4-hydroxypyrrolidines and derivatives thereof having the formula: ##STR7## wherein; R 1 is hydrogen, loweralkyl, ##STR8## R 2 is loweralkyl, cycloalkyl and phenylalkyl, Ar is phenyl and phenyl substituted by halogen, O-loweralkyl, --NHC(O)(CH 3 ), CF 3 , --C(O)CH 3 , --CH 2 --CH═CH 2 , alkyl, hydroxy, --OCH 2 -phenyl and --C(O)NH 2 , and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
8 words
The compound of claim 1 which is trans-1-phenylmethyl-4-phenylthio-3-pyrrolidinol.
Claim 4
Dependent Claim
8 words
The compound of claim 1 which is trans-1-ethyl-4-phenylthio-3-pyrrolidinol.
Claim 5
Dependent Claim
9 words
The compound of claim 1 which is trans-1-ethyl-4-phenylthio-3-pyrrolidinol oxalate.
Claim 6
Dependent Claim
9 words
The compound of claim 1 which is trans-4-[(2-chloro phenyl)thio]-1-ethyl-3-pyrrolidinol.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is trans-1-ethyl-4-[(4-methylphenyl)thio]-3-pyrrolidinol.
Claim 8
Dependent Claim
9 words
The compound of claim 1 which is trans-1-ethyl-4[(4-methylphenyl)thio]-3-pyrrolidinoethylcarbamate (ester).
Claim 9
Dependent Claim
10 words
The compound of claim 1 which is trans-1-ethyl-4-[(4-methylphenyl)thio]-3-pyrrolidinolcarbamate (ester) hydrobromide.
Claim 10
Dependent Claim
86 words
A pharmaceutical composition for treating depression in animals in unit dosage form comprising (a) an effective amount of a 1-substituted-3-arylthio-4-hydroxypyrrolidine and derivatives thereof having the formula: ##STR9## wherein R 1 is hydrogen, loweralkyl, ##STR10## R 2 is loweralkyl, cycloalkyl and phenylalkyl, Ar is phenyl and phenyl substituted by halogen, O-loweralkyl, --NHC(O)CH 3 , CF 3 , --C(O)CH 3 , --CH 2 --CH═CH 2 , alkyl, hydroxy, --OCH 2 -phenyl and --C(O)NH 2 , the pharmaceutically acceptable acid addition salts thereof, and (b) a pharmaceutical carrier therefor.
Claim 11
Dependent Claim
86 words
A pharmaceutical composition for treating depression in animals in unit dosage form comprising (a) an effective amount of a 1-substituted-3-arylthio-4-hydroxypyrrolidine and derivatives thereof having the formula: ##STR9## wherein R 1 is hydrogen, loweralkyl, ##STR10## R 2 is loweralkyl, cycloalkyl and phenylalkyl, Ar is phenyl and phenyl substituted by halogen, O-loweralkyl, --NHC(O)CH 3 , CF 3 , --C(O)CH 3 , --CH 2 --CH═CH 2 , alkyl, hydroxy, --OCH 2 -phenyl and --C(O)NH 2 , the pharmaceutically acceptable acid addition salts thereof, and (b) a pharmaceutical carrier therefor.
Claim 12
Dependent Claim
10 words
The composition of claim 9 wherein the compound is trans-1-ethyl-4-phenylthio-3-pyrrolidinol.
Claim 13
Independent Claim
84 words
A method of treating depression in an animal which comprises administrating to an animal in need thereof an effective amount for treating depression of a compound having the formula: ##STR11## wherein R 1 is hydrogen, loweralkyl, ##STR12## R 2 is loweralkyl, cycloalkyl and phenylalkyl, Ar is phenyl and phenyl substituted by halogen, O-lower-alkyl, --NH--C(O)CH 3 , CF 3 , --C(O)CH 3 , --CH 2 --CH═CH 2 , alkyl, hydroxy, --OCH 2 -phenyl and --C(O)NH 2 , and the pharmaceutically acceptable acid addition salts thereof.
Claim 14
Independent Claim
84 words
A method of treating depression in an animal which comprises administrating to an animal in need thereof an effective amount for treating depression of a compound having the formula: ##STR11## wherein R 1 is hydrogen, loweralkyl, ##STR12## R 2 is loweralkyl, cycloalkyl and phenylalkyl, Ar is phenyl and phenyl substituted by halogen, O-lower-alkyl, --NH--C(O)CH 3 , CF 3 , --C(O)CH 3 , --CH 2 --CH═CH 2 , alkyl, hydroxy, --OCH 2 -phenyl and --C(O)NH 2 , and the pharmaceutically acceptable acid addition salts thereof.
Claim 15
Dependent Claim
10 words
The method of claim 11 wherein the compound is trans-1-ethyl-4-phenylthio-3-pyrrolidinol.
References Cited (Backward Citations)
DE2738477A1
Cited
US4160837A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-02-17 | 1984-08-18 | 1985-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-17 | 1988-08-18 | 1989-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-17 | 1992-08-18 | 1993-02-17 | $7700.00 | Window Closed / Lapsed |