Centrally acting 6,7,8,9-tetrahydro-3h-benz(e)indole...

C - Chemistry – Metallurgy – 07 – D

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C07D 209/58 (2006.01) A61K 31/40 (2006.01) A61K 31/47 (2006.01) C07D 209/66 (2006.01) C07D 401/12 (2006.01) C07D 403/04 (2006.01) C07D 409/12 (2006.01) C07D 413/04 (2006.01) C07D 471/04 (2006.01) C07D 491/04 (2006.01) C07D 491/052 (2006.01) C07D 495/04 (2006.01)

Patent

CA 2073340

A compound of formula (I) or pharmaceutically acceptable slats of formula (I), where R1 is H, C1-C3 alkyl, -(CH2)nCONH2 where n is 2 to 6, (CH2)n-1-(4,4-dimethylpiperidine-2,6-dione-yl), cyclopropylmethyl; R2 is hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl or combined with R1 to form a C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, (CH2)n-X-Ar where X is O, S, or NH, 3,3,3-trifluoropropyl-(CH2)m-R9 where m is 2 or 3 and R9 is phenyl, 2-thiophenyl or 3-thiophenyl; R3 is C1-C3 alky, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, formyl, CN, halogen, CH2OR2, C(O)C(O)Y where Y is OR1 or NR1R2, -(CH2)q-NR1R2 where q is 0 to 5, C=NOR2,2(4,5-dihydro)oxazolyl, or COR10 where R10 is H, R1, NR1R2 or CF3; R4 is C1-C3 alkyl,cyclopropylmethyl, CF3, 2,2,2-trifluoroethyl CN, CONR1R2, =O, 2(4,5-dihydro) imidazolyl, 2(4,5-dihy- dro)oxazolyl, 2-oxazolyl, 3-oxadiazolyl, or 3,3,3-trifluoropropyl; R5 is hydrogen, R1, OCH3, C(O)CH3 or C(O)OR1; X is (a) a valence bond, (b) CH2, (c) O, S or NR5 where R5 is H, C1-C8 alkyl, C3-C8 cycloalkyl, benzyl, COR6 where R6 is a C1-C3 alkyl, phenyl, or CONR7R8 where R7 and R8 are independently H or C1-C3 alkyl; and Z is a hydrogen or halogen. The com- pounds of formula (I) are suitable for treating disorders of the central nervous system, particularly as 5-HT1A receptor agon- ists.

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