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US 5,364,866 AGranted
Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics
AssigneeHoechst-Roussel Pharmaceuticals Inc.
InventorsJoseph T. Strupczewski, Grover C. Helsley, Yulin Chiang, Kenneth J. Bordeau, Edward J. Glamkowski
Life of this patent
Estimating the term…
Abstract
Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. The compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.
Claims86
A compound of the formula:
- ##STR163## wherein X is --O-- or --S--;
- p is 1 or 2;
- Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1;
- Y is lower alkoxy, hydroxy and halogen when p is 2 and X is --O--;
- (R.sub.1) is R.sub.20, R.sub.21, or R.sub.22, wherein:
- R.sub.20 is --(CH.sub.2).sub.n -- where n is 2, 3, 4 or 5;
- R.sub.21 is
- --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,
- --CH.sub.2 --C.ident.C--CH.sub.2 --,
- --CH.sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2,
- --CH.sub.2 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,
- --CH.sub.2 C.ident.C--CH.sub.2 --CH.sub.2 --, or
- --CH.sub.2 --CH.sub.2 --C.ident.C--CH.sub.2 --,
- the --CH.dbd.CH-- bond being cis or trans;
- R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1 -C.sub.6 linear alkyl group, phenyl group or ##STR164## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen;
- R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl, ##STR165## alkyl is lower alkyl;
- aryl is phenyl or ##STR166## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy;
- heteroaryl is ##STR167## Q.sub.3 is --O--, ##STR168## --CH.dbd.N--;
- W is CH.sub.2 or CHR.sub.8 or N--R.sub.9 ;
- R.sub.7 is hydrogen, lower alkyl, or acyl;
- R.sub.8 is lower alkyl;
- R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10 ;
- and
- R.sub.10 is hydrogen, lower alkyl, C.sub.1 -C.sub.3 acyl, aryl, ##STR169## where aryl and heteroaryl are as defined above;
- and m is 1, 2, or 3;
- all geometric, optical and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
23 more elements
A compound of the formula:
- ##STR171## wherein p is 1 or 2;
- Y is hydrogen, Cl, Br, or F, when p is 1;
- Y is lower alkoxy, hydroxy, or halogen when p is 2;
- n is 2, 3, or 4;
- R is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, hydroxyl, alkanoyl, Cl, F, Br, I, amino, C.sub.1 -C.sub.3 mono or dialkyl amino, acylamino, --NO.sub.2, --OCF.sub.3, --CF.sub.3, ##STR172## alkyl is lower alkyl;
- R.sub.7 is hydrogen, lower alkyl, ##STR173## and m is 1, 2, or 3;
- all geometric, optical and stereoisomers thereof or a pharmaceutically acceptable acid addition salt thereof.
4 more elements
A compound of the formula:
- ##STR174## wherein p is 1 or 2;
- Y is hydrogen, Cl, Br, or F, when p is 1;
- Y is lower alkoxy, hydroxy, or halogen when p is 2;
- n is 2, 3, or 4;
- R is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, hydroxyl, acyl, alkanoyl, Cl, F, Br, I, amino, C.sub.1 -C.sub.3 mono or dialkyl amino, acylamino, --NO.sub.2, --OCF.sub.3, --CF.sub.3, ##STR175## alkyl is lower alkyl;
- R.sub.7 is hydrogen, lower alkyl, or ##STR176## and m is 1, 2, or 3;
- all geometric, optical and stereoisomers thereof or a pharmaceutically acceptable acid addition salt thereof.
4 more elements
A compound of the formula:
- ##STR177## wherein X is --O-- or --S--;
- p is 1 or 2;
- Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1;
- Y is lower alkoxy, hydroxy and halogen when p is 2 and X is --O--,
- is --(CH.sub.2).sub.n -- where n is 2, 3, 4 or 5;
- (R.sub.1) is R.sub.20, R.sub.21, or R.sub.22, wherein:
- R.sub.20 is --(CH.sub.2).sub.n -- where n is 2, 3, 4 or 5;
- R.sub.21 is
- --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,
- --CH.sub.2 --C.ident.C--CH.sub.2 --,
- --CH.sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --,
- --CH.sub.2 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,
- --CH.sub.2 --C.ident.C--CH.sub.2 --CH.sub.2 --, or
- --CH.sub.2 --CH.sub.2 --C.dbd.C--CH.sub.2 --,
- the --CH.dbd.CH-- bond being cis or trans;
- R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1 -C.sub.6 linear alkyl group, phenyl group or ##STR178## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen;
- and R and m are as defined hereinafter;
- m is 1, 2, or 3;
- and
- when m is 1, 2, or 3, R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl, ##STR179## alkyl is lower alkyl;
- aryl is phenyl or ##STR180## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy;
- heteroaryl is ##STR181## Q.sub.3 is --O--, --S--, ##STR182## --CH.dbd.N--;
- W is CH.sub.2 or CHR.sub.8 or N--R.sub.9 ;
- R.sub.7 is hydrogen, lower alkyl, or acyl;
- R.sub.8 is lower alkyl;
- R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10 ;
- and
- R.sub.10 is hydrogen, lower alkyl, C.sub.1 -C.sub.3 acyl, aryl, ##STR183## where aryl and heteroaryl are as defined above;
- and when m is 3, R is not ##STR184## all geometric, optical and stereoisomers thereof, or pharmaceutically acceptable acid addition salt thereof.
26 more elements
Dependencies are inferred from the claim text.