Claims
- 1. A compound of Formula I ##STR16## wherein R.sub.1 and R.sub.2 are, independently, (C.sub.1 -C.sub.6)alkyl or (C.sub.3 -C.sub.7)cycloalkyl;
- R.sub.3 is (C.sub.2 -C.sub.10)alkanoyloxy, (C.sub.3 -C.sub.7)cycloalkylcarbonyloxy, (C.sub.3 -C.sub.7)cycloalkyl[(C.sub.1 -C.sub.4)alkyl]carbonyloxy, aroyloxy, aryl(C.sub.1 -C.sub.4)alkylcarbonyloxy, (C.sub.1 -C.sub.10)alkoxycarbonyloxy, (C.sub.3 -C.sub.7)cyclo-alkoxycarbonyloxy, (C.sub.3 -C.sub.7)cycloalkyl[(C.sub.1 -C.sub.4)-alkoxy]carbonyloxy, aryloxycarbonyloxy, aryl(C.sub.1 -C.sub.4)alkyloxycarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, (C.sub.3 -C.sub.7)cycloalkylaminocarbonyloxy, (C.sub.3 -C.sub.7)cycloalkyl[(C.sub.1 -C.sub.4)alkyl]aminocarbonyloxy, arylaminocarbonyloxy, aryl(C.sub.1 -C.sub.4)alkyl-aminocarbonyloxy, (C.sub.1 -C.sub.10)dialkylaminocarbonyloxy, aryl[(C.sub.1 -C.sub.4)alkyl]aminocarbonyloxy, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.4)alkylaminocarbonyloxy, diarylaminocarbonyloxy, and bis[aryl(C.sub.1 -C.sub.4)alkyl]aminocarbonyloxy, in which any aryl group is phenyl, 2-naphthyl or 4-biphenyl, and
- R.sub.4 is hydrogen or (C.sub.1 -C.sub.6)alkyl,
- or a pharmaceutically acceptable salt thereof.
- 2. A compound of Formula I of claim 1 ##STR17## wherein R.sub.1 and R.sub.2 are, independently, (C.sub.1 -C.sub.6)alkyl;
- R.sub.3 is (C.sub.2 -C.sub.10)alkanoyloxy, (C.sub.1 -C.sub.10)alkoxycarbonyloxy, (C.sub.1 -C.sub.10)alkylaminocarbonyloxy, and
- R.sub.4 is hydrogen or (C.sub.1 -C.sub.3)alkyl,
- or a pharmaceutically acceptable salt thereof.
- 3. A compound of claim 1 selected from the group consisting of
- (S)-octanoic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (S)-ethylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (S)-butylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (S)-hexylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (S)-octylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (S)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid ethyl ester;
- (S)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid butyl ester;
- (S)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid hexyl ester;
- (R)-octanoic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (R)-ethylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (R)-butylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (R)-hexylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester;
- (R)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid ethyl ester;
- (R)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid butyl ester;
- (R)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid hexyl ester;
- and a pharmaceutically acceptable salt of these compound esters.
- 4. The compound according to claim 1 which is (S)-octanoic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 5. The compound according to claim 1 which is (S)-ethylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 6. A compound according to claim 1 which is (S)-butylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 7. A compound according to claim 1 which is (S)-hexylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 8. A compound according to claim 1 which is (S)-octylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 9. A compound according to claim 1 which is (S)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid ethyl ester or a pharmaceutically acceptable salt thereof.
- 10. A compound according to claim 1 which is (S)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid butyl ester or a pharmaceutically acceptable salt thereof.
- 11. A compound according to claim 1 which is (S)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid hexyl ester or a pharmaceutically acceptable salt thereof.
- 12. A compound according to claim 1 which is (R)-octanoic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 13. A compound according to claim 1 which is (R)-ethylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 14. A compound according to claim 1 which is (R)-butylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 15. A compound according to claim 1, (R)-hexylcarbamic acid 1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl ester or a pharmaceutically acceptable salt thereof.
- 16. A compound according to claim 1 (which is (R)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid ethyl ester or a pharmaceutically acceptable salt thereof.
- 17. A compound according to claim 1 which is (R)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid butyl ester or a pharmaceutically acceptable salt thereof.
- 18. A compound according to claim 1 which is (R)-1-[4-(dimethylamino)-2-butynyl]-2-oxo-3-pyrrolidinyl carbonic acid hexyl ester or a pharmaceutically acceptable salt thereof.
CONTROL REFERENCE TO RELATED APPLICATIONS
This is a division of application Ser. No. 08/392,436 filed Feb. 22, 1995, now U.S. Pat. No. 5,550,257 which is a CIP of application Ser. No. 274,604 filed Jul. 13, 1994, now U.S. Pat. No. 5,451,685 which is a divisional of 07/690,749 filed Apr. 24, 1991, now U.S. Pat. No. 5,356,885.
US Referenced Citations (4)
Foreign Referenced Citations (2)
Number |
Date |
Country |
9001026 |
Feb 1990 |
WOX |
9004588 |
May 1990 |
WOX |
Non-Patent Literature Citations (6)
Entry |
Levy et al., Therapie, 22(3):671-688(Jan. 1967). |
Ehlert et al., Mol. Pharmacology, 28: 107-119 (1985). |
Ringdahl, Eur. J. Pharmacol., 99:177-184 (1984). |
Ringhdahl, The Humana Press, Clifton, NJ, J.H. Brown, Ed., 1989, 151. |
Lundkvist et al., J. Med. Chem., 32, 863-869 (1989). |
Resul et al., Acta. Pharm. Suec., 16, 13, pp. 161-165 (1979). |
Divisions (2)
|
Number |
Date |
Country |
Parent |
392436 |
Feb 1995 |
|
Parent |
690749 |
Apr 1991 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
274604 |
Jul 1994 |
|