Vasoconstrictive substituted dihydropyranopyridines

C - Chemistry – Metallurgy – 07 – D

Patent

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Details

C07D 491/052 (2006.01) A61K 31/495 (2006.01) A61K 31/506 (2006.01) A61K 31/53 (2006.01) C07D 491/04 (2006.01)

Patent

CA 2168022

The present invention is concerned with compounds of formula (I), the pharmaceutically acceptable acid addition salts thereof, the N-oxides thereof and the stereochemically isomeric forms thereof, wherein =a1- a2=a3-a4= is a bivalent radical of formula: =N-CH=CH-CH= (a); =CH-N=CH-CH= (b); =CH-CH=N-CH= (c); ~H-CH=CH-N= (d), wherein in said bivalent radicals one or two hydrogen atoms can be substituted by halo, hydroxy, C1-6 alkyl or C1-6 alkyloxy; R1 is hydrogen or C1-6 alkyl; R2 is hydrogen or C1-6 alkyl; R3 is hydrogen or C1-6 alkyl; Alk1 is C1-5 alkanediyl; Alk2 is C2-15 alkanediyl; Q is a five- or six-membered heterocyclic ring containing at least one nitrogen atom or a radical of formula (aa), wherein R4 is hydrogen, cyano, aminocarbonyl or C1-6 alkyl; R5 is hydrogen, C1-6 alkyl, C3-6 alkenyl or C3-6 alkynyl; R6 is hydrogen or C1-6 alkyl; or R5 and R6 taken together may form a bivalent radical of formula -(CH2)4- or -(CH2)5-, Pharmaceutical compositions, preparations and use as medicine are described.

Composés répondant à la formule (I), leurs sels d'addition d'acide pharmaceutiquement acceptables, leurs N &cir& _-oxydes et leurs formes stéréochimiquement isomères. Dans ladite formule =a1-a2=a3-a4= représente un radical bivalent répondant aux formules: =N-CH=CH-CH=(a); =CH-N=CH-CH=(b); =CH-CH=N-CH=(c); =CH-CH=CH-N=(d), où dans lesdits radicaux bivalents un ou deux atomes d'hydrogène sont éventuellement substitués par halo, hydroxy, alkyle C1-6 ou alkyloxy C1-6; R<1> représente hydrogène ou alkyle C<1-6>; R<2> représente hydrogène ou alkyle C1-6; R<3> représente hydrogène ou alkyle C1-6; Alk<1> représente alcanediyle C1-5; Alk<2> représente alcanediyle C2-15; Q représente un hétérocycle à 5 ou 6 chaînons renfermant au moins un atome d'azote ou un radical répondant à la formule (aa), dans laquelle R<4> représente hydrogène, cyano, aminocarbonyle ou alkyle C1-6; R<5> représente hydrogène, alkyle C1-6, alcényle C3-6 ou alcynyle C3-6; R<6> représente hydrogène ou alkyle C1-6; ou R<5> et R<6>, pris ensemble, forment un radical bivalent répondant à la formule -(CH2)4- ou -(CH2)5-. On décrit également des compositions pharmaceutiques, leurs préparations et leur utilisation comme médicament.

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