(-)-3-(-hydroxyphenul)-n-n-propylpiperidine and derivatives...

C - Chemistry – Metallurgy – 07 – D

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260/278, 260/292

C07D 211/18 (2006.01) C07D 211/22 (2006.01) C07D 401/12 (2006.01)

Patent

CA 1202307

ABSTRACT The pure enantiomeric form of a compound of the formula Image I wherein Y is OH, R1COO, R2R3NCOO- or R4O whereby R1 is an aliphatic hydrocarbon residue having 1-17 carbon atoms, a phenyl, 2,6-dimethylphenyl or 3- or 4-hydroxyphenyl group or a 3- or 4-alkanoyloxyphenyl group with the formula Image wherein R5 is an alkyl group having 1-6 carbon atoms, or R1 is a group Image wherein R6 is hydrogen, an alkyl group having 1 to 5 carbon atoms or a phenyl group, R7 is hydrogen, an alkyl group having 1 to 5 carbon atoms or an acyl group and R8 is hydrogen or an alkyl group having 1 to 5 carbon atoms, R2 is hydrogen, an alkyl group having 1-5 carbon atoms, a phenethyl, benzyl or phenyl group which may be mono- or disubstituted in the aromatic part with a methyl, methoxy, hydroxy, nitro or cyano group or a halogen, R3 is H, an alkyl group having 1 to 5 carbon atoms or a phenyl group or R2 and R3 together with the nitrogen atom form a 5, 6 or 7 membereo ring that may contain 1 to 3 double bonds and/or 1 or 2 further heteroatoms selected from N, D and S, and R4 is an allyl or benzyl group, said enantiomer having the same absolute configuration at the asymmetric carbon atom (x) as that of the (-)-enantiomer of the compound of formula I wherein Y is OH, as bases and pharmaceutically acceptable acid addition salts thereof, processes for their preparation and pharmaceutical preparations and methods of treatment employing such compounds. The compounds are useful for treatment of dis- orders in the central nervous system.

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