Claims
- 1. A compound of formula (I): ##STR37## or a pharmaceutically acceptable salt or solvate thereof. wherein
- R has the formula ##STR38## wherein Ar' represents a phenyl group; X.sup.1 and Y each independently represent hydrogen; C.sub.1-12 alkyl; phenyl, phenyl(C.sub.1-12)alkyl, naphthyl or naphthyl-(C.sub.1-12)alkyl unsubstituted or substituted in the phenyl or naphthyl moiety by halogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, halo(C.sub.1-6)alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-6 -alkoxycarbonyl, C.sub.1-6 alkoxycarbonyl-C.sub.1-6 alkoxycarbonyl-(C.sub.1-6)-alkyl, C.sub.1-6 alkylcarbonyloxy or C.sub.1-6 alkylcarbonyl; hydroxy; C.sub.1-12 -alkoxy; halogen; trifluoromethyl; nitro; cyano; or --SO.sub.3 H, --SO.sub.2 NR.sup.7 R.sup.8, CO.sub.2 R.sup.7, --COR.sup.7 or --CONR.sup.7 R.sup.8, wherein R.sup.7 and R.sup.8 are independently hydrogen, C.sub.1-12 alkyl, unsubstituted phenyl or naphthyl or phenyl or naphthyl substituted by halogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, halo(C.sub.1-6) alkyl, hydroxy, amino, nitro carboxy, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkoxycarbonyl-(C.sub.1-6)-alkyl, C.sub.1-6 alkylcarbonyloxy or C.sub.1-6 alkylcarbonyl; or X.sup.1 together with Y form a cycloalkylene ring of up to 12 carbon atoms; and a represents an integer 1, 2, or 3;
- R.sup.1 together with R.sup.2 forms pyrrolidinyl;
- R.sup.3 represents hydrogen or C.sub.1-12 alkyl;
- R.sup.4 represents hydrogen, halogen, C.sub.1-12 alkyl, hydroxy, C.sub.1-12 alkoxy, nitrile, nitro or amino; and
- n represents 0.
- 2. A compound according to claim I, wherein a is 1 and Ar.sup.1, X.sup.1 and Y are ##STR39##
- 3. A compound according to claim 1, wherein X' and Y each independently represent hydrogen, halogen, trifluoromethyl or nitro;
- R.sup.3 represents hydrogen or C.sub.1-6 alkyl;
- R.sup.4 represents hydrogen, halogen, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy, nitrile or amino; and
- n is O.
- 4. A compound selected from the group consisting
- (S) N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-3,4-dichlorophenylacetamide hydrochloride;
- (S) N-methyl-N-[[1-(pyrrolidin-1-yl)-3-phenyl]prop-2-yl]-3,4-dichlorophenylacetamide hydrochloride;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-o-nitrophenylacetamide hydrochloride hemihydrate;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-m-nitrophenylacetamide hydrochloride;
- (S) N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-p-nitrophenylacetamide hydrochloride;
- (S) N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-p-trifluoromethylphenylacetamide hydrochloride;
- (S) N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-m-trifluoromethylphenylacetamide hydrochloride.
- 5. An analgesic pharmaceutical composition, which comprises an analgesically effective amount of a compound of formula (I): ##STR40## or a pharmaceutically acceptable salt or solvate thereof, wherein R has the formula ##STR41## wherein Ar' represents a phenyl group; X.sup.1 and Y each independently represent hydrogen; C.sub.1-12 alkyl; phenyl, phenyl(C.sub.1-12)alkyl, naphthyl or naphthyl-(C.sub.1-12)alkyl unsubstituted or substituted in the phenyl or naphthyl moiety by halogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, halo(C.sub.1-6)alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-6 -alkoxycarbonyl, C.sub.1-6 alkoxycarbonyl-(C.sub.1-6)-alkyl, C.sub.1-6 alkylcarbonyloxy or C.sub.1-6 alkylcarbonyl; hydroxy; C.sub.1-12 -alkoxy; halogen; trifluoromethyl; nitro; cyano; or --SO.sub.3 H, --SO.sub.2 NR.sup.7 R.sup.8, --CO.sub.2 R.sup.7, COR.sup.7 or --CONR.sup.7 R.sup.8, wherein R.sup.7 and R.sup.8 are independently hydrogen, C.sub.1-12 alkyl, unsubstituted phenyl or naphthyl or phenyl or naphthyl substituted by halogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, halo(C.sub.1-6) alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkoxycarbonyl-(C.sub.1-6)-alkyl, (C.sub.1-6)-alkylcarbonyloxy or C.sub.1-6 alkylcarbonyl; or X.sup.1 together with Y form a cycloakylene ring of up to 12 carbon atoms; and a represents an integer 1, 2, or 3;
- R.sup.1 together with R.sup.2 forms pyrrolidinyl;
- R.sup.3 represents hydrogen or C.sub.1-12 alkyl;
- R.sup.4 represents hydrogen, halogen, C.sub.1-12 alkyl, hydroxy, C.sub.1-12 alkoxy, nitrile, nitro or amino; and
- n represents O; in combination with a pharmaceutically acceptable carrier.
- 6. The composition according to claim 5, in unit dosage form.
- 7. The composition according to claim 5, wherein a is 1 and Ar.sup.1, X.sup.1 and Y are ##STR42##
- 8. The composition according to claim 5, wherein X.sup.1 and Y each independently represent hydrogen, halogen, trifluoromethyl or nitro;
- R.sup.3 represents hydrogen or C.sub.1-6 alkyl;
- R.sup.4 represents hydrogen, halogen, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy, nitrile or amino; and
- n is O.
- 9. The composition according to claim 5, wherein said compound is selected from the group consisting of:
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-3,4-dichlorophenylacetamide hydrochloride;
- (S)-N-methyl-N-[[1-(pyrrolidin-1yl)-3-phenyl]prop-2-yl]-3,4-dichlorophenylacetamide hydrochloride;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-o-nitrophenylacetamide hydrochloride hemihydrate;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-m-nitrophenylacetamide hydrochloride;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-p-nitrophenylacetamide hydrochloride;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-p-trifluoromethylphenylacetamide hydrochloride; and
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-m-trifluoromethylphenylacetamide hydrochloride.
- 10. A method of treating pain in mammals, which comprises administering to a mammal in need thereof an analgesically effective amount of a compound of formula (I): ##STR43## or a pharmaceutically acceptable salt or solvate thereof, wherein R has the formula ##STR44## wherein Ar' represents a phenyl group; X.sup.1 and Y each independently represent hydrogen; C.sub.1-12 alkyl; phenyl, phenyl(C.sub.1-12)alkyl, naphthyl or naphthyl (C.sub.1-12)alkyl unsubstituted or substituted in the phenyl or naphthyl moiety by halogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, halo(C.sub.1-6)alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-6 -alkoxycarbonyl, C.sub.1-6 alkoxycarbonyl-(C.sub.1-6)-alkyl, C.sub.1-6 alkylcarbonyloxy or C.sub.1-6 alkylcarbonyl; hydroxy; C.sub.1-12 -alkoxy; halogen; trifluoromethyl; nitro; cyano; or --SO.sub.3 H, --SO.sub.2 NR.sup.7 R.sup.8, --CO.sub.2 R.sup.7, --COR.sup.7 or --CONR.sup.7 R.sup.8, wherein R.sup.7 and R.sup.8 are independently hydrogen, C.sub.1-12 alkyl, unsubstituted phenyl or naphthyl or phenyl or naphthyl substituted by halogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, halo(C.sub.1-6) alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkoxycarbonyl-(C.sub.1-6)-alkyl, C.sub.1-6 alkylcarbonyloxy or C.sub.1-6 alkylcarbonyl; or X.sup. 1 together with Y form a cycloakylene ring of up to 12 carbon atoms; and a represents an integer 1, 2, or 3;
- R.sup.1 together with R.sup.2 forms pyrrolidinyl;
- R.sup.3 represents hydrogen or C.sub.1-12 alkyl;
- R.sup.4 represents hydrogen, halogen, C.sub.1-12 alkyl, hydroxy, C.sub.1-12 alkoxy, nitrile, nitro or amino; and
- n represents O.
- 11. A method according to claim 10, wherein a is 1 and Ar.sup.1, X.sup.1 and Y are ##STR45##
- 12. A method according to claim 10, wherein X.sup.1 and Y each independently represent hydrogen, halogen, trifluoromethyl or nitro;
- R.sup.3 represents hydrogen or C.sub.1-6 alkyl;
- R.sup.4 represents hydrogen, halogen, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy, nitrile or amino; and
- n is O.
- 13. A method according to claim 10, wherein said compound is selected from the group consisting of:
- (S)-N methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-3,4-dichlorophenylacetamide hydrochloride;
- (S)-N-methyl-N-[[1-(pyrrolidin-1yl)-3-phenyl]prop-2-yl]-3,4-dichlorophenylacetamide hydrochloride;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-o-nitrophenylacetamide hydrochloride hemihydrate;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-m-nitrophenylacetamide hydrochloride;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-p-nitrophenylacetamide hydrochloride;
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-p-trifluoromethylphenylacetamide hydrochloride; and
- (S)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)]ethyl-m-trifluoromethylphenylacetamide hydrochloride.
Priority Claims (2)
Number |
Date |
Country |
Kind |
8622352 |
Sep 1986 |
GBX |
|
8630113 |
Dec 1986 |
GBX |
|
Parent Case Info
This application is a continuation of U.S. application Ser. No. 07/098,327, filed on 09-17-87, now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3103516 |
Schmitt et al. |
Sep 1963 |
|
4753952 |
Vecchietti et al. |
Jun 1988 |
|
4801585 |
Vecchietti et al. |
Jan 1989 |
|
Foreign Referenced Citations (8)
Number |
Date |
Country |
0017376 |
Oct 1980 |
EPX |
0122018 |
Oct 1984 |
EPX |
0176309 |
Apr 1986 |
EPX |
0254545 |
Jan 1988 |
EPX |
254545 |
Jan 1988 |
EPX |
1112514 |
Aug 1961 |
DEX |
2091250 |
Jul 1982 |
GBX |
2096607 |
Oct 1982 |
GBX |
Non-Patent Literature Citations (1)
Entry |
Aboskalova et al, Chem. Abstr. 91 (1979), 56751s. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
98327 |
Sep 1987 |
|