US 4,906,643 AGranted

Substituted N-(3-hydroxy-4-piperidinyl)benzamides as gastrointestinal agents

AssigneeJanssen Pharmaceutica NV

InventorsGeorges H. P. Van Daele, Freddy F. Vlaeminck, Karel J. Van Loon

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Abstract

N-(3-hydroxy-4-piperidinyl)substituted benzamides, their N-oxide forms and pharmaceutically acceptable acid-addition salts having gastrointestinal motility stimulating properties, compositions containing the same, and methods of treating warm blooded animals suffering from a decreased peristalsis of the gastrointestinal system.

Claims20

Dependent claims

A compound of the formula:

##STR19## an N-oxide form, a pharmaceutically acceptable acid addition salt, or a possible stereoisomeric form thereof, wherein:
R.sup.1 is hydrogen, C.sub.1-6 alkyl, aryl-C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, amino-C.sub.1-6 alkyl, or mono- and di(C.sub.1-6 alkyl)amino-C.sub.1-6 alkyl;
R.sup.2 is hydrogen or C.sub.1-6 alkyl;
R.sup.3, R.sup.4 and R.sup.5 each independently are hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, halo, hydroxy, cyano, nitro, amino, mono- and di(C.sub.1-6 alkyl)amino, aminocarbonyl, arylcarbonylamino, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkylcarbonyloxy, aminosulfonyl, C.sub.1-6 alkylaminosulfonyl, C.sub.1-6 alkylsulfinyl, C.sub.1-6 alkylsulfonyl, C.sub.1-6 alkylthio, mercapto, trifluoromethyl, aryl-C.sub.1-6 alkyloxy, or aryloxy;
Alk is a C.sub.1-6 alkanediyl radical;
X is O, S, NR.sup.6, C(.dbd.O), or C(.dbd.S), said R.sup.6 being hydrogen or C.sub.1-6 alkyl;
and
Het is a five- or six-membered heterocyclic ring containing one N hetero atom, said five- or six membered ring being optionally fused with a six membered carbocyclic ring, and when said Het is a bicyclic ring system it may optionally be substituted with up to 6 substituents, and when said Het is a monocyclic ring system it may optionally be substituted with up to 3 substituents, said substituents being selected from the group consisting of halo, hydroxy, nitro, cyano, trifluoromethyl, C.sub.1-6 alkyl, aryl-C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.1-6 alkylthio, mercapto, amino, mono- and di(C.sub.1-6 alkylamino), aryl-C.sub.1-6 alkylamino, aminocarbonyl, mono- and di(C.sub.1-6 alkylamino)carbonyl, piperidinylcarbonyl, pyrrolidinylcarbonyl, C.sub.1-6 alkyloxycarbonyl, aryl-C.sub.1-6 alkyloxycarbonyl, and a bivalent radical .dbd.O and .dbd.S,
provided that Het is connected to X on a carbon atom;
and
wherein aryl is phenyl being optionally substituted with 1, 2, or 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyl and C.sub.1-6 alkyloxy.

8 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound of the formula:

##STR19## an N-oxide form, a pharmaceutically acceptable acid addition salt, or a possible stereoisomeric form thereof, wherein:
R.sup.1 is hydrogen, C.sub.1-6 alkyl, aryl-C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, amino-C.sub.1-6 alkyl, or mono- and di(C.sub.1-6 alkyl)amino-C.sub.1-6 alkyl;
R.sup.2 is hydrogen or C.sub.1-6 alkyl;
R.sup.3, R.sup.4 and R.sup.5 each independently are hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, halo, hydroxy, cyano, nitro, amino, mono- and di(C.sub.1-6 alkyl)amino, aminocarbonyl, arylcarbonylamino, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkylcarbonyloxy, aminosulfonyl, C.sub.1-6 alkylaminosulfonyl, C.sub.1-6 alkylsulfinyl, C.sub.1-6 alkylsulfonyl, C.sub.1-6 alkylthio, mercapto, trifluoromethyl, aryl-C.sub.1-6 alkyloxy, or aryloxy;
Alk is a C.sub.1-6 alkanediyl radical;
X is O, S, NR.sup.6, C(.dbd.O), or C(.dbd.S), said R.sup.6 being hydrogen or C.sub.1-6 alkyl;
and
Het is a five- or six-membered heterocyclic ring containing one N hetero atom, said five- or six membered ring being optionally fused with a six membered carbocyclic ring, and when said Het is a bicyclic ring system it may optionally be substituted with up to 6 substituents, and when said Het is a monocyclic ring system it may optionally be substituted with up to 3 substituents, said substituents being selected from the group consisting of halo, hydroxy, nitro, cyano, trifluoromethyl, C.sub.1-6 alkyl, aryl-C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.1-6 alkylthio, mercapto, amino, mono- and di(C.sub.1-6 alkylamino), aryl-C.sub.1-6 alkylamino, aminocarbonyl, mono- and di(C.sub.1-6 alkylamino)carbonyl, piperidinylcarbonyl, pyrrolidinylcarbonyl, C.sub.1-6 alkyloxycarbonyl, aryl-C.sub.1-6 alkyloxycarbonyl, and a bivalent radical .dbd.O and .dbd.S,
provided that Het is connected to X on a carbon atom;
and
wherein aryl is phenyl being optionally substituted with 1, 2, or 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyl and C.sub.1-6 alkyloxy.

8 more elements