Decaprenylamine derivatives

Details Decaprenylamine derivatives Decaprenylamine derivatives

C - Chemistry, Metallurgy

07

C

260/605.4, 260/6

C07C 87/24 (1980.01) C07C 93/10 (1980.01)

Patent

CA 1155459

ABSTRACT OF THE DISCLOSURE New decaprenylamines having the general formula: Image (I) wherein R1 represents a hydrogen atom, a decaprenyl group, a lower alkyl group or a hydroxy-lower alkyl group, and R2 represents a lower alkyl or alkenyl group optionally sub- stituted with at least one hydroxy, amino or alkylamino group, or a cycloalkyl group, and the pharmaceutically acceptable acid addition salts thereof, are prepared by (a) converting decaprenol of the formula: (II) Image into a corresponding halide or sulfonic acid ester which is thereafter reacted with a primary or secondary amino compound having the general formula: Image (III) wherein R1 and R2 have the aforesaid meanings, in the pre- sence or absence of a base, to obtain the desired decaprenyl- amine of the formula (I), or (b) oxidizing decaprenol to a corresponding aldehyde which is then condensed with a primary amino compound having the general formula: H2N - R2 (III') wherein R2 has the aforesaid meanings, to form a correspond- ing imino compound which in turn is reduced to obtain a decaprenylamine of the formula (I) in which R1 is hydrogen and R2 has the aforesaid meanings. When a pharmaceutically acceptable acid addition salt is desired, the decaprenylamine of the formula (I) thus obtained is further reacted with a pharmaceutically acceptable acid to provide the desired salt. The decaprenylamines of the formula (I) are useful for controlling virus infection of vertebrate animals.

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