Patent CA-1037479-A (CA)
Title: .alpha.-SUBSTITUTED BENZHYDROL DERIVATIVES AND A PROCESS FOR THE PREPARATION THEREOF
Inventor: TOTH EDIT
IPC: C07C255/53
Filed: 1974-08-14
Granted: 1978-08-29
Abstract: ABSTRACT OF THE DISCLOSURE           The invention relates to new .alpha.-substituted benzhydrols of the general formula (I) and pharmaceuti-cally acceptable acid addition salts or quaternary ammonium salts thereof.                                            (I) In this formula Z stands for ethyl or vinyl group, and when Z stands for ethyl, R1 and R2 each stand for hydrogen, a halogen, straight--chained or branched, saturated or unsaturated lower aliphatic hydrocarbon group, a trihalo-methyl, nitro, nitrile group, an optionally etherified, or esterified hydroxy or hydroxy-alkyl group, an optionally esterified carboxy group, an optionally acylated amino or lower aminoalkyl group, a lower alkylamino group or an optionally esterified or etherified mercapto group, R3 and R4 each stand for hydrogen, halogen, a straight--chained or branched, saturated or unsaturated lower aliphatic hydrocarbon group or cycloalkyl group, an aralkyl or aryl group, a trihalomethyl group, nitro group, nitrile group, an optionally etherified or esterified hydroxy or hydroxyalkyl group, an optionally esterified carboxy group, an optionally acylated amino or lower aminoalkyl group, a mono- or di-lower alkylamino group forming optionally a ring through a carbon, nitrogen or oxygen atom, a lower alkylamino--mono- or di-lower alkyl group, forming optionally a ring through a carbon, nitrogen or oxygen atom, or an optionally esterified or etherified mercapto group, and R5     stands for halogen, a straight-chained or branched, saturated or unsaturated C2-6 aliphatic hydrocarbon group or cycloalkyl group, an ar-alkyl or aryl group, a trihalomethyl group, nitro group, nitrile group, an optionally etherified or esterified hydroxy or hydroxy-alkyl group, an optionally esterified carboxy group, an optionally acylated amino or lower aminoalkyl group, a mono- or di-lower alkylamino group forming optionally a ring throgh a carbon, nitrogen or oxygen atom, a lower alkylamino--mono or di-lower alkyl group forming optionally a ring through a carbon, nitrogen or oxygen atom, or an optionally esterified or etherified mercapto group, with the proviso that (i)    when R1, R2, R3 and R4 each stand for hydrogen, R5 may not stand for an amino or dimethylamino group attached to position 2 or 4, a 1-pyrrolidinyl group attached to position 2, or a methyl or methoxy group or bromine atom attached to position 4, or (ii)  when R1, R2 and R3 each stand for hydrogen, R4 and R5 may not represent a 2,4-dimethoxy or 3,4-dimethoxy group, or (iii) when R1 and R2 each stand for hydrogen, R3, R4 and R5 may not represent a 2,3,4-trimethoxy, a 2,4,6-trimethoxy, a 4-methoxy-3,5-dimethyl or a 2-amino-3,5-dibromo group, or when Z stands for vinyl R1 and R2 each stand for hydrogen a halogen, straight--chained or branched, saturated or unsaturated lower aliphatic hydrocarbon group, a trihalomethyl nitro, nitrile group, an optionally etherified or esterified hydroxy or hydroxyalkyl group, an optionally esterified carboxy group, an optionally acylated amino or lower aminoalkyl group, a lower alkylamino group or an optionally esterified or etherified mercapto group, R3, R4 and R5 each stand for hydrogen, halogen, a straight--chained or branched, saturated or unsaturated or lower aliphatic hydrocarbon group or cyclo-alkyl group, an aralkyl or aryl group, a trihalo-methyl group, nitro group, nitrile group, an optionally etherified or esterified hydroxy or hydroxyalkyl group, an optionally esterified carboxy group, an optionally acylated amino or lower aminoalkyl group, a mono- or di-lower alkylamino group forming optionally a ring through a carbon, nitrogen or oxygen atom, a lower alkylamino-mono- or di-lower alkyl group, forming optionally a ring through a carbon, nitrogen or oxygen atom, or an optionally esterified or etheri fied mercapto group, with the proviso that if R1, R2 and R4 each stand for hydrogen, R5 may not stand for hydrogen or 4-methyl group.         These compounds exert an inhibiting or inducing effect, respectively, on the liver microsomal enzyme system, and can be used as medicines.         The compounds of the general formula (I) can be prepared as follows: a) a benzophenone of the general formula (II)                 (II) is reacted with a metalorganic compound containing ethyl or vinyl groups; or b) a propiophenone of the general formula (III)                 (III) is reacted with a phenyl magnesium halide; or c) a Grignard compound of the general formula (IV)       (IV) wherein X stands for halogen, is reacted with propio-phenone; or d) a compound of the general formula (VI)        (VI) is reduced; or e) a compound of the general formula (I) is converted into another compound of the general formula (I).