Phenylpropylamine derivatives

C - Chemistry – Metallurgy – 07 – D

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260/390, 260/603

C07D 295/06 (2006.01) C07D 295/073 (2006.01) C07D 295/084 (2006.01) C07D 295/108 (2006.01)

Patent

CA 1045137

ABSTRACT OF THE DISCLOSURE Compounds having useful psychostimulant, anti- spasmodic, hypotensive and analgesic properties are disclosed. The compounds have the formula: Image (I) in which R2 is selected from the group consisting of a hydrogen atom and a halogen atom; is selected from the group consisting of q cyclohexyl group and a phenyl group, and is a cyclohexyl group when R2 is a halogen atom; A is selected from the group consisting of CH2CH2 and CH=CH groups; and is selected from the group consisting of an alkylamino group, a dialkylamino group and a heterocyclic ring containing from 5 to 7 atoms in the ring, said ring optionally having one or more substituents and optionally containing a second hetero-atom; and acid addition salts of said compound. Theymay be prepared by condensing an acetophenone in a Mannich reaction with formaldehyde and a primary or secondary amine, reducing the amino-ketone thus formed to a 3-amino- 1-phenyl-propan-1-ol, subsequently dehydrating the 3-amino-4-phenyl propan-1-ol to give a compound of formula (I) in which A is CH=CH which may if desired be hydrogenated to a compound of formula (I) in which A is CH2-CH2 and/or converted to an acid addition salt.

211894

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