New 3-oxo-1-propenyl azo compounds useful as 5-HT receptor antagonists e.g. for treating psychoses, neurological disorders, amyotrophic lateral sclerosis and eating disorders

摘要

3-Oxo-1-propenyl azo compounds (I) and their salts, solvates and isomers are new. 3-Oxo-1-propenyl azo compounds of formula (I) and their salts, solvates, diastereoisomers, enantiomers, racemates and mixtures of their enantiomers are new: R1, R2aryl or heteroaryl optionally substituted with Q, A, halo, 3-7C cycloalkyl, CF3, NO2, CN, C(NH)NOH, OCF3, OA, NHA, NAA or NH2; Q : aryl or heteroaryl optionally substituted with Ar, A, halo, 3-7C cycloalkyl, CF3, NO2, CN, C(NH)NOH, OCF3, OA, NHA, NAA or NH2; R3H or an organic group, especially (CH2)nCO2R5, (CH2)nCOHet, (CH2)nOR5, (CH2)nHet, (CH2)nN(R5)2, CH=N-OA, CH2CH=N-OA, (CH2)nNHOA, (CH2)n(R5)Het, (CH2)nCH=N-Het, (CH2)nOCOR5, (CH2)nN(R5)CH2CH2OR5, (CH2)nN(R5)CH2CH2OCF3, (CH2)nN(R5)C(R5)COOR5, (CH2)nN(R5)CH2COHet, (CH2)nN(R5)CH2Het, (CH2)nN(R5)CH2CH2Het, (CH2)nN(R5)CH2CH2N(R5)CH2COOR5, (CH2)nN(R5)CH2CH2N(R5)2, CH=CHCOOR5, CH=CHCH2NR5Het, CH=CHCH2N(R5)2, CH=CHCH2OR5 or (CH2)nN(R5)Ar; A : 1-10C alkyl or alkoxy or 2-10C alkenyl or alkenyloxyalkyl; Het : a saturated, unsaturated or aromatic, mono or bicyclic heterocyclic group, or linear or branched organic group containing one or more heteroatoms (all optionally substituted with one or more A and/or halo); Ar : phenyl optionally substituted by one or more A and/or halo, OR5, OOCR5, COOR5, CON(R5)2, CN, NO2, NH2, NHCOR5, CF3 or SO2CH3; R5 : H or A; halo = F, Cl, Br or I; and provided that when X = CH, then R2 and R4 are not both H An independent claim is also included for the preparation of (I). [Image] ACTIVITY : Neuroleptic; Neuroprotective; Eating-Disorders-Gen.; Tranquilizer; CNS-Gen.; Antiinflammatory; Cerebroprotective; Antiparkinsonian; Antidepressant; Hypotensive; Antimigraine; Nootropic; Antiaddictive; Antialcoholic; Antismoking; Antianginal; Vasotropic; Analgesic; Anticoagulant; Thrombolytic; Gastrointestinal-Gen.; Cardiovascular-Gen.; Ophthalmological; Gynecological. MECHANISM OF ACTION : 5-HT receptor antagonist.