New modulators of dopamine neurotransmission

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 211/18 (2006.01) A61K 31/451 (2006.01) A61P 25/00 (2006.01)

Patent

CA 2394606

New substituted 4-(phenyl N-alkyl)-piperazine and 4-(phenyl-N-alkyl)-piperidine compounds of Formula (1) wherein X is N, CH, or C, however X may only be C when the compound comprises a double bind at the dotted line; R1 is CF3, OSO2CF3, OSO2CH3, SOR7, SO2R7, COR7, CN, OR3, NO2, CONHR3, 3-thiophene, 2-thiophene, 3-furane, 2-furane, F, Cl, Br, or I; R2 is F, Cl, Br, I, CN, CF3, CH3, OCH3, OH, and NH2; R3 and R4 are independently H or a C1-C4 alkyl; R5 is a C1-C4 alkyl, an allyl, CH2SCH3, CH2CH2OCH3, CH2CH2CH2F, CH2CF3, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, or -(CH2)-R6; R6 is a C3-C6 cycloalkyl, 2-tetrahydrofurane, or 3-tetrahydrofurane; R7 is a C1-C3 alkyl, CF3, or N(R4)2, and pharmaceutically acceptable salts thereof are disclosed. Also pharmaceutical compositions comprising the above compounds and methods wherein the above compounds are used for treatment of disorders in the central nervous system are disclosed.

La présente invention concerne de nouveaux composé de 4-(phényl N-alkyl)-pipérazine et 4-(phényl-N-alkyl)-pipéridine substituées de la formule (1) dans laquelle X est N, CH, or C, X ne pouvant cependant être C que lorsque le composé comprend une liaison double sur la ligne en pointillé ; R1 est CF3, OSO2CF3, OSO2CH3, SOR7, SO2R7, COR7, CN, OR3, NO2, CONHR3, 3-thiophène, 2-thiophène, 3-furane, 2-furane, F, Cl, Br, ou I; R2 est F, Cl, Br, I, CN, CF3, CH3, OCH3, OH, et NH2; R3 et R4 sont indépendamment H ou un alkyle en C1-C4 ; R5 est un alkyle en C1-C4, un allyle, CH2SCH3, CH2CH2OCH3, CH2CH2CH2F, CH2CF3, 3,3,3-trifluoropropyle, 4,4,4-trifluorobutyle, ou -(CH2)-R6; R6 est un cycloalkyle en C3-C6, 2-tétrahydrofurane, ou 3-tétrahydrofurane ; R7 est un alkyle en C1-C3, CF3, ou N(R4)2, et des sels pharmaceutiquement acceptables de ces derniers. L'invention se rapporte également à des compositions pharmaceutiques comprenant les composés précités et à des procédés selon lesquels on utilise les composés précités dans le traitement de troubles du système nerveux central.

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