Azetidine compounds

C - Chemistry – Metallurgy – 07 – D

Patent

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Details

C07D 417/12 (2006.01) A61K 31/54 (2006.01) A61K 31/541 (2006.01) A61P 9/00 (2006.01) A61P 11/00 (2006.01) A61P 25/00 (2006.01) A61P 25/28 (2006.01) C07D 401/04 (2006.01) C07D 403/04 (2006.01) C07D 403/14 (2006.01) C07D 413/04 (2006.01) C07D 413/14 (2006.01) C07D 417/14 (2006.01)

Patent

CA 2529126

The present invention relates to a compound of the general formula (I) wherein Het is an optionally substituted 4-, 5-, 6- or 7-membered heterocyclic ring having at least one nitrogen atom; R1 is hydrogen, hydroxy, C1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl or C2-C4 alkynyl; R2 and R3 is each and independently selected from hydrogen, C1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen and cyano, provided that R2 and R3 may not both be hydrogen; R4 is C1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl or C2-C4 alkynyl; Ar is an optionally substituted aromatic ring system selected from pyridinyl; 1-naphthyl; 5,6,7,8-tetrahydro-1-naphthyl; quinolinyl; 2,3-dihydro-1,4-benzodioxinyl; 1,3-benzodioxolyl; 5,6,7,8- tetrahydroquinolinyl; 5,6,7,8-tetrahydroisoquinolinyl; 5,6,7,8- tetrahydroquinazolin-4-yl; 1-benzo[b]thiophen-7-yl; 1-benzo[b]thiophen-4-yl; 1- benzo[b]thiophen-3-yl; isoquinolinyl; quinazolinyl; and indan-4-yl; or Ar is substituted phenyl; or an enantiomer thereof or any salt thereof; to a pharmaceutical composition containing said compounds and to the use of said compounds in therapy. The present invention further relates to processes for the preparation of compounds of formula I and to new intermediates used in the preparation thereof.

La présente invention concerne un composé de la formule générale (I) où Het représente un noyau hétérocycle à 4, 5, 6 ou 7 chaînons éventuellement substitué ayant au moins un atome d'azote ; R?1¿ représente un hydrogène, hydroxy, alkyle C¿1?-C¿4?, cycloalkyle C¿3?-C¿4?, alcényle C¿2?-C¿4? ou alkynyle C¿2?-C¿4? ; R2 et R3 représentent respectivement et indépendamment un hydrogène, alkyle C¿1?-C¿4?, cycloalkyle C¿3?-C¿4?, alcényle C¿2?-C¿4? ou alkynyle C¿2?-C¿4,?alcoxy C¿1?-C¿4?, halogène et cyano, à condition que R?2¿ et R?3¿ ne représentent pas ensemble un hydrogène ; R4 représente un alkyle C¿1?-C¿4?, cycloalkyle C¿3?-C¿4?, alcényle C¿2?-C¿4? ou alkynyle C¿2?-C¿4 ;? Ar représente un système noyau aromatique éventuellement substitué sélectionné parmi pyridinyle ; 1-naphthyle ; 5,6,7,8-tétrahydro-1-naphthyle ; quinolinyle ; 2,3-dihydro-1,4-benzodioxinyle ; 1,3-benzodioxolyle ; 5,6,7,8-tétrahydroquinolinyle ; 5,6,7,8 tétrahydroisoquinolinyle ; 5,6,7,8-tétrahydroquinazolin-4-yle ; 1-benzo(b)thiophén-7-yle ; 1-benzo(b)thiophén-4-yle ; 1-benzo(b)thiophén-3-yle ; isoquinolinyle ; quinazolinyle ; et indan-4-yle ; ou Ar représente un phényle substitué. L'invention concerne également un énantiomère ou un sel quelconque de ce composé ; une composition pharmaceutique contenant ces composés et l'utilisation de ces composés en thérapie. La présente invention concerne également des procédés de préparation de composés de la formule I et de nouveaux intermédiaires utilisés dans leur préparation.

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