Piperidine derivatives
AssigneeNovo Nordisk A/S
InventorsJohn B. Hansen, Frederik C. Gronvald, John P. Mogensen
Life of this patent
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Abstract
Piperidine derivatives of formula ##STR1## wherein A is straight or branched alkyl, alkoxy-alkyl, or alkenyl; X is O or NH; Y is O, S, NH, NCN, or N-alkyl; R.sup.1 is 6-fluoro-1,2-benzisoxazol-3-yl, 6-fluoro-1H-indazol-3-yl, or 6-fluoro-1-methyl-1H-indazol-3-yl; R.sup.2 is alkyl or phenyl; and R.sup.3 is phenyl optionally substituted, or R.sup.3 is ##STR2## wherein Z represents a 5- or 6-membered heterocyclic ring; or R.sup.2 and R.sup.3 together with the nitrogen atom form a fused heterocyclic ring system; or pharmaceutically acceptable salts thereof are useful in the treatment of indications related to the CNS-system, cardiovascular system or to gastrointestinal disorders.
Claims30
A compound of formula I ##STR14## wherein A is a straight or branched saturated hydrocarbon chain having 1-6 carbon atoms which is optionally substituted by C.sub.1-6 -alkoxy, or an unsaturated hydrocarbon chain having 2-6 carbon atoms and one double bond, or when R.sup.1 is 6-fluoro-1-methyl-1H-indazol-3-yl, then A is also a straight or branched saturated hydrocarbon chain having 1-6 carbon atoms which is substituted with phenyl;
- X is O or NH;
- Y is O, S, NH or N--C.sub.1-6 -alkyl;
- R.sup.1 is 6-fluoro-1,2-benzisoxazol-3-yl, 6-fluoro-1H-indazol-3-yl, or 6-fluoro-1-methyl-1H-indazol-3-yl;
- R.sup.2 is C.sub.1-6 -alkyl or phenyl;
- or, when R.sup.1 is 6-fluoro-1-methyl-1H-indazol-3-yl, then R.sup.2 is also hydrogen;
- and
- R.sup.3 is phenyl optionally substituted with C.sub.1-6 -alkyl, halogen, C.sub.1-6 -alkoxy, or perhalomethyl, or R.sup.3 is ##STR15## wherein Z represents a 5- or 6-membered heterocyclic ring comprising one or more nitrogen, oxygen, or sulphur atoms;
- or
- R.sup.2 and R.sup.3 together with the nitrogen atom form a dibenzazepine ring system;
- or
- a pharmaceutically acceptable salt thereof.
A compound which is
- 4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-(3-((5,6-methylenedioxyindolin-1-yl)ca rbonyloxy)-2-phenylpropyl)piperidine;
- or a pharmaceutically acceptable salt thereof.
A compound of formula I ##STR16## wherein A is a straight or branched saturated hydrocarbon chain having 1-6 carbon atoms which is optionally substituted by C.sub.1-6 -alkoxy, or an unsaturated hydrocarbon chain having 2-6 carbon atoms and one double bond, or when R.sup.1 is 6-fluoro-1-methyl-1H-indazol-3-yl, then A is also a straight or branched saturated hydrocarbon chain having 1-6 carbon atoms which is substituted with phenyl;
- X is O or NH;
- Y is O, S, NH or N--C.sub.1-6 -alkyl;
- R.sup.1 is 6-fluoro-1,2-benzisoxazol-3-yl, 6-fluoro-1H-indazol-3-yl, or 6-fluoro -1-methyl-1H-indazol-3-yl;
- R.sup.2 and R.sup.3 together with the nitrogen atom form an indoline, 1,2,3,4-tetrahydroquinoline, methylenedioxyindoline, methylenedioxy-1,2,3,4-tetrahydroquinoline or a 3,4-dihydro-2H-1,4-benzoxazine ring system;
- or
- a pharmaceutically acceptable salt thereof.
A compound which is
- 1-[2((10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)carbamoyloxy)propyl]-4-(6-flu oro-1,2-benzisoxazol-3-yl)piperidine;
- 1-[3-((10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)carbonyloxy)propyl]-4-(6-flu oro-1,2-benzisoxazol-3-yl)piperidine;
- or
- a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.