1-acyl-4-aliphatylaminopiperidine compounds

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

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5142315, 514255, 514311, 514312, 514330, 544 60, 544129, 544360, 546192, 546196, 546204, 546208, 546209, 546212, 546213, 546216, 546219, 546220, 5462784, 5462787, A61K 3154, A61K 3143, C07D41760, C07D21108

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059359510

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel 1-acyl-4-aliphatylaminopiperidine compounds of the formula I ##STR2## in which R.sub.1 is a benzoyl, naphthoyl or cycloalkanoyl radical which is unsubstituted or substituted by lower alkyl, lower alkoxy, halogen and/or trifluoromethyl; unsubstituted or substituted by lower alkyl, lower alkoxy, halogen, nitro, cyano and/or trifluoromethyl; alkylene; or alkyl or a radical of the formula --(CH.sub.2).sub.n --(.dbd.O)--R.sub.5 (Ia); and R.sub.4 is hydrogen, lower alkyl or a radical of the formula --(CH.sub.2).sub.n --C(.dbd.O)--R.sub.5 (Ia); lower alkoxy, amino or amino substituted by lower alkyl, amino-lower alkyl, mono- or di-lower alkylaminoalkyl, lower alkanoyl, lower alkoxearbonyl or lower alkylene or aza-, oxa- or thia-lower alkylene, (ii) hydroxyl, cycloalkoxy, lower alkoxy or lower alkoxy which is substituted by lower alkoxy, amino or amino substituted by lower alkyl, amino-lower alkyl, mono- or di-lower alkylamino-alkyl, lower alkanoyl, lower alkoxycarbonyl or lower alkylene or aza-, oxa- or thia-lower alkylene, or (iii) amino or amino substituted by lower alkyl, cycloalkyl, amino-lower alkyl, mono- or di-lower alkylaminoalkyl, lower alkanoyl, lower alkoxycarbonyl or lower alkylene or aza-, oxa- or thia-lower alkylene; group or a free or etherified hydorowcymethylene group; and n-4-yl!acetamide; process for the preparation of the compounds according to the invention, pharmaceutical preparations containing these, and their use as pharmaceutical active ingredients.
Cycloalkyl and radicals derived therefrom have, for example, 3 to 8, in particular 5 to 7, primarily 5 or 6, ring members and are, for example, cyclopentyl, cyclohexyl or cycloheptyl.
Alkyl which is substituted by halogen, lower alkoxy, amino or amino substituted by lower alkyl, amino-lower alkyl, mono- or di-lower alkylaminoalkyl, lower alkanoyl, lower alkoxycarbonyl or lower alkylene or aza-, oxa-, or thia-lower alkylene is, for example, haloalkyl, in particular halo-lower alkyl, lower alkoxyalkyl, in particular lower alkoxy-lower alkyl, aminoalkyl, in particular amino-lower alkyl, mono- or di-lower alkylaminoalkyl, in particular mono- or di-lower alkylamino-lower alkyl, lower alkanoylaminoalkyl, in particular lower alkanoylamino-lower alkyl, lower alkoxycarbonylaminoalkyl, in particular lower alkoxycarbonylamino-lower alkyl, pyrrolidinoalkyl, in particular pyrrolidino-lower alkyl, piperidinoalkyl, in particular piperidino-lower alkyl, free or N'-lower alkylated or N'-lower alkanoylated piperazinoalkyl, in particular the corresponding piperazino-lower alkyl, morpholino alkyl, in particular morpholino-lower alkyl, or free or S-oxidized thiomorpholinoalkyl, in particular the corresponding thiomorpholino-lower alkyl.
Amino substituted by lower alkyl, (3- to 8-membered) cycloalkyl, amino-lower alkyl, mono- or di-lower alkylaminoalkyl, lower alkanoyl, lower alkoxycarbonyl or lower alkylene or aza-, oxa- or thia-lower alkylene is, for example, mono- or di-lower alkylamino, (3- to 8-membered) cycloalkylamino, amino-lower alkylamino, mono- or di-lower alkylamino-lower alkylamino, lower alkanoylamino, lower-alkoxycarbonylamino, pyrrolidino, piperidino, free or N'-lower alkylated or N'-lower alkanoylated piperazino, morpholino or free or S-oxidized thiomorpholino.
Lower alkoxy which is substituted by lower alkoxy, amino or amino substituted by lower alkyl, amino-lower alkyl, mono- or di-lower alkylaminoalkyl, lower alkanoyl, lower alkoxycarbonyl or lower alkylene or aza-, oxa- or thia-lower alkylene is, for example, lower alkoxy-lower alkoxy, amino-lower alkoxy, mono- or di-lower alkylamino-lower alkoxy, lower alkanoylamino-lower alkoxy, lower alkoxycarbonylamino-lower alkoxy, pyrrolidino-lower alkoxy, piperidino-lower alkoxy, free or N'-lower alkylated or N'-lower alkanoylated piperazino-lower alkoxy, morpholino-lower alkoxy, or free or S-oxidized thiomorpholino-lower alkoxy.
Alkyl is, for example, straight-chain or branched C.sub.1 -C.sub.14 -alkyl, in particular C.sub.1 -C.sub.10 -alkyl, preferably lower alkyl.
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REFERENCES:
patent: 5310743 (1994-05-01), Schilling et al.
patent: 5459270 (1995-10-01), Williams et al.
Schilling et al. Chemical abstract vol. 119 No. 271005 "Prep of 1-acylpiperdation and their use as substance of P Antagonists" 1993.

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