Piperidylmethyl-substituted chroman derivatives
AssigneeBayer Aktiengesellschaft
InventorsHans-Georg Heine, Bodo Junge, Peter-Rudolf Seidel, Rudolf Schohe-Loop, Thomas Glaser, Jean M. V. De Vry, Wolfgang Dompert, Henning Sommermeyer
Life of this patent
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Abstract
Piperidylmethyl-substituted chroman derivatives can be prepared by first reducing corresponding chromancarboxylic acid derivatives, if appropriate with prior activation, with the cyclic amines and then reducing the carbonyl group, or by reacting chromanmethyl compounds directly with the cyclic amines. The substituted piperidylmethyl-substituted chroman derivatives can be employed as active compounds in medicaments, in particular for the treatment of diseases of the central-nervous system.
Claims15
Piperidylmethyl-substituted chroman derivatives of the general formula (I) ##STR33## in which A, B and D are identical or different and represent hydrogen, halogen, cyano, azido, nitro, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, hydroxyl or carboxyl, or represent straight-chain or branched alkyl, alkenyl, acyl or alkoxycarbonyl having in each case up to 8 carbon atoms, or represent a group of the formula --NR.sup.1 R.sup.2, --NR.sup.3 --L--R.sup.4 or --OR.sup.5, wherein
- R.sup.1, R.sup.2 and R.sup.3 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 8 carbon atoms, phenyl or benzyl,
- L denotes the --CO-- or --SO.sub.2 -- group,
- R.sup.4 denotes straight-chain or branched alkyl having up to 8 carbon atoms or benzyl, or phenyl, which is optionally substituted by halogen, hydroxyl, nitro, cyano, trifluoromethyl, trifluoromethoxy or by straight-chain or branched alkyl or alkoxy having up to 6 carbon atoms,
- R.sup.5 denotes straight-chain or branched alkyl or alkenyl having in each case up to 8 carbon atoms, which are optionally substituted by cycloalkyl having 3 to 6 carbon atoms or phenyl,
- E represents a heterocyclic radical of the formula ##STR34## wherein R.sup.6 denotes hydrogen, hydroxyl, halogen, phenyl or piperidinyl,
- R.sup.7 denotes straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by up to 3 identical or different substituents from the group consisting of hydroxy, straight-chain or branched alkoxy having up to 6 carbon atoms and phenyl, wherein the phenyl ring in turn can be substituted by up to 3 identical or different substituents from the group consisting of halogen, trifluoromethyl, trifluoromethoxy and cyano;
- denotes phenyl, which is optionally substituted by up to 3 identical or different substituents from the group consisting of halogen, trifluoromethyl, trifluoromethoxy, cyano, nitro, hydroxyl and straight-chain or branched alkyl and alkoxy having in each case up to 6 carbon atoms;
- or denotes a group selected from the formula --CO--NR.sup.8 R.sup.9, --CO--R.sup.10 or --OR.sup.11 ;
- wherein
- R.sup.8 and R.sup.9 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or phenyl, and
- R.sup.10 and R.sup.11 are identical or different and denote phenyl, which is optionally substituted by up to 2 identical or different substituents from the group consisting of halogen, cyano, nitro, trifluoromethyl and trifluoromethoxy, and salts thereof, with the proviso that R.sup.6 does not denote hydrogen or hydroxyl if R.sup.7 represents unsubstituted phenyl, and with the further proviso that if R.sup.7 denotes CONR.sup.8 R.sup.9 hydroxylalkyl or alkoxyalkyl then R.sup.6 does not denote hydrogen.
Dependencies are inferred from the claim text.