| 摘要 |
<p>1,249,148. Benzyl alcohol derivatives. BOEHRINGER INGELHEIM G.m.b.H. 23 Dec., 1968 [22 Dec., 1967], No. 61120/68. Heading C2C. Novel compounds I (including salts and optical isomers thereof) wherein R 1 signifies H or C 1-4 alkyl, R 2 signifies H, C 1-4 alkyl, acyl or alkoxycarbonyl, R 3 signifies H, C 1-5 alkyl, C 1-5 hydroxyalkyl, aminoalkyl, alkyl- or dialkylaminoalkyl, acylaminoalkyl, acylalkylaminoalkyl, N-alkyl- or N,N- dialkyl-hydrazinoalkyl, cycloalkyl or benzyl, R 4 signifies H, alkyl, alkoxycarbonyl or acyl, Z signifies R 5 ,R 6 -disubstituted phenyl (wherein R 5 signifies H, halogen or CF 3 and R 6 signifies H, halogen, Me or MeS), cyclohexenyl, benzyl or halo-substituted benzyl, R 7 signifies H or Me, R 8 signifies H, halogen or MeO and x is 1 or 2, are obtained: (a) by reacting a phthalide II with an amine, NHR<SP>1</SP> 2 R 3 , to give an intermediate amide IV and subsequently reducing IV (R<SP>1</SP> 2 signifies C 1-4 alkyl); (b) by sequentially reducing and hydrolysing compounds IVa (c) by ring opening an isoindoline V utilizing an acyl anhydride and, if desired, saponifying the resulting diacyl compound (R<SP>1</SP> 3 has the same significance as R 3 except that it is not H); (d) by reducing a nitrile VI (VI is itself obtained from the corresponding amino compound utilizing a Sandmeyer reaction); and (e) compound I wherein R 1 , R 2 , R 4 , R 7 and R 8 are H, R 3 is Me and Z is 4-chlorophenyl is also made by LiAlH 4 reduction ofα- (2 - ethoxy carbonylaminomethyl phenyl) - 4- chlorobenzyl ethyl carbonate. Compounds I may be converted one into the other by standard methods, e.g. alkylation, acylation, etherification, esterification or the reverse of such procedures, and compounds I in which R 3 is a benzyl group may be hydrogenated to remove the benzyl group; compounds I in which R 2 and R 4 represent alkoxycarbonyl groups may be prepared utilizing a haloformic ester. 1 - (4 - Chlorophenyl) - 1,2 - dimethyl - 3 - oxoisoindoline is prepared by treating 2-(N-methylcarbamoyl) -α- (4 - chlorophenyl) -α- methylbenzyl alcohol with anhydrous CF 3 .CO 2 H. Pharmaceutical preparations capable of curbing appetite contain as active ingredient compounds I optionally in association with other compounds showing pharmacological activity, e.g. a laxative. Administration is orally, rectally or parenterally.</p> |
