GB1371056A - 1,3-aminoalcohol benzoates - Google Patents

Abstract

1371056 1,3 - Aminoalcohol benzoates RICHTER GEDEON VEGYESZETI GYAR RT 19 Oct 1971 [19 Oct 1970] 48593/71 Heading C2C Novel compounds of Formula I and their salts of Formula II and acid addition salts in which R 1 , R 2 and R 3 are H, alkyl, alkenyl, cycloalkyl or phenyl; R 4 is H, 1-6 C alkyl, alkenyl or benzyl; Z is -O- or -CH 2 -; Y is a mineral or organic acid residue; X 1 , X 2 and X 3 are H, halo, alkoxy, phenoxy, or 1-6 C alkyl or two of them may form -OCH 2 O-; with the provisos: (i) if the benzoyl group is monosubstituted and X 2 is H in the para position, R 1 and R2 are CH 3 or R 1 is CH 3 or isopropyl while R 2 is H and Z is CH 2 ; then R 3 may only represent alkyl, alkenyl, cycloalkyl or phenyl; (ii) if the benzoyl group is monosubstituted (i.e. X 1 and X 3 are H), X 2 is p-ethoxy, p-nbutoxy or p-isobutoxy, and R 1 and R 2 are CH 3 ; then R 3 may only represent alkyl, alkenyl, cycloalkyl or phenyl; (iii) if the benzoyl group is monosubstituted (i.e. X 1 and X 3 are H) X 2 is primary n-butoxy, R 1 and R 2 are H and Z is CH 2 ; then R 3 may only represent alkyl, alkenyl, cycloalkyl or phenyl; (iv) if X 1 is H; then X 2 and X 3 do not both represent halogen atoms; (v) if the benzoyl group is trisubstituted by OCH 3 in the 3<SP>1</SP>, 4<SP>1</SP> and 51-positions, R 1 and R 2 are H or R 1 is ethyl while R 2 is ethyl or phenyl; then R 3 may only represent alkyl, alkenyl, cycloalkyl or phenyl; are described. They may be prepared by the following methods: (i) by reaction of a compound III with a reactive derivative of a compound IV (ii) by reaction of a compound IV with a compound V (iii) by reaction of morpholine or piperidine with a compound VI (iv) by reaction of a compound VII with morpholine or piperidine followed where necessary in any of (i)-(iv) by salt formation. Intermediates isolated are 3-hydroxypropyl 3<SP>1</SP> - trifluoromethylbenzoate, prepared from trimethylene glycol and the appropriate acid halide and 3-chloropropyl 3<SP>1</SP>-trifluoromethylbenzoate, prepared by reaction of the first intermediate with SOCl 2 . Pharmaceutical compositions useful as local anaesthetics comprise a compound I or II together with a suitable carrier or diluent.