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Details for Patent: 5,137,896

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Details for Patent: 5,137,896

Title: N-(3-hydroxy-4-piperidinyl)benzamide derivatives
Abstract:Novel N-(3-hydroxy-4-piperidinyl)benzamides and derivatives thereof, said compounds being useful as stimulators of the motility of the gastro-intestinal system.
Inventor(s): Van Daele; Georges (Turnhout, BE)
Assignee: Janssen Pharmaceutica N.V. (Beerse, BE)
Filing Date:Aug 20, 1991
Application Number:07/748,227
Claims:1. A compound of the formula: ##STR60## the pharmaceutically acceptable acid addition salts thereof, the stereochemically isomeric forms, and the pharmaceutically acceptable quaternary ammonium salts thereof, wherein:

the substituents in the 3 and 4 positions in the piperidine ring have the cis configuration;

R.sup.1 represents a member selected from the group consisting of hydrogen, lower alkyl, (Ar.sup.1) lower alkyl, and lower alkylcarbonyl;

R.sup.2 represents hydrogen;

R.sup.3, R.sup.4, and R.sup.5 each independently represent hydrogen, lower alkyl, lower alkyloxy, halo, hydroxy, amino, nitro, mono- or di(lower alkyl)amino, lower alkylcarbonylamino, lower alkylcarbonyl, lower alkylcarbonyloxy, aminosulfonyl, and lower alkylsulfonyl; and

L represents hydrogen or lower alkyloxycarbonyl,

wherein in the foregoing Ar.sup.1 represents a member selected from the group consisting of phenyl being optionally substituted with up to 3 substituents each independently selected from the group consisting of halo, hydroxy, lower alkyl, lower alkyloxy, aminosulfonyl, lower alkylcarbonyl, nitro, trifluoromethyl, amino, aminocarbonyl, phenylcarbonyl wherein said phenyl may be optionally substituted with up to 3 halo atoms, and thienyl substituted with halo or lower alkyl.

2. A compound according to claim 1 wherein R.sup.3, R.sup.4, and R.sup.5 are, each independently, selected from the group consisting of halo, amino, mono- and di(lower alkyl)amino, and lower alkyloxy.

3. A compound according to claim 2 wherein R.sup.3 represents methoxy, R.sup.4 represents amino or methylamino, and R.sup.5 represents chloro, wherein said R.sup.3, R.sup.4, and R.sup.5 are attached to the phenyl ring in the 2-, 4-, and 5-positions, respectively.

4. A compound according to claim 3 wherein L represents hydrogen or ethoxycarbonyl.

5. A compound according to claim 1 wherein the compound is a member selected from the group consisting of:

cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)-benzamide; and

cis-ethyl(4-amino-5-chloro-2-methoxybenzoylamino)-3-methoxy-1-piperidinecar boxylate.

6. A pharmaceutical composition in unit dosage form comprising per dosage unit an effective gastro-intestinal motility stimulating amount of a compound as described in claim 1, the pharmaceutically acceptable acid addition salts thereof, the stereochemically isomeric forms, and the pharmaceutically acceptable quaternary ammonium salts thereof.

7. The pharmaceutical composition of claim 6 wherein R.sup.3, R.sup.4, and R.sup.5 are, each independently, selected from the group consisting of halo, amino, mono- and di(lower alkyl)amino, and lower alkyloxy.

8. The pharmaceutical composition of claim 7 wherein R.sup.3 represents methoxy, R.sup.4 represents amino or methylamino, and R.sup.5 represents chloro, wherein said R.sup.3, R.sup.4, and R.sup.5 are attached to the phenyl ring in the 2-, 4-, and 5-positions, respectively.

9. The pharmaceutical composition of claim 8 wherein L represents hydrogen or ethoxycarbonyl.

10. The pharmaceutical composition of claim 6 wherein the compound is a member selected from the group consisting of:

cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)-benzamide; and

cis-ethyl(4-amino-5-chloro-2-methoxybenzoylamino)-3-methoxy-1-piperidinecar boxylate.

11. A method of stimulating the motility of the gastro-intestinal system which comprises the systemic administration to vertebrates of an effective gastro-intestinal motility stimulating amount of a compound as described in claim 1, the pharmaceutically acceptable acid addition salts thereof, the stereochemically isomeric forms, and the pharmaceutically acceptable quaternary ammonium salts thereof.

12. A method according to claim 11 wherein R.sup.3, R.sup.4, and R.sup.5 are, each independently, selected from the group consisting of halo, amino, mono- and di(lower alkyl)amino, and lower alkyloxy.

13. A method according to claim 12 wherein R.sup.3 represents methoxy, R.sup.4 represents amino or methylamino, and R.sup.5 represents chloro, wherein said R.sup.3, R.sup.4, and R.sup.5 are attached to the phenyl ring in the 2-, 4-, and 5-positions, respectively.

14. A method according to claim 13 wherein L represents hydrogen or ethoxycarbonyl.

15. A method according to claim 11 wherein the compound is a member selected from the group consisting of:

cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)-benzamide; and

cis-ethyl(4-amino-5-chloro-2-methoxybenzoylamino)-3-methoxy-1-piperidinecar boxylate.
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