Patent ID: 6303790
Filing Date: 2001-10-16
Classification: A61P,C07D

Abstract:
A process for preparing a compound of formula ##STR34##whereinR.sup.1 is lower alkyl or aryl, optionally substituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl;R.sup.2 and R.sup.2' are independently from each other hydrogen, halogen, trifluoromethyl, lower alkoxy or cyano; orR.sup.2 and R.sup.2' may together be --CH.dbd.CH--CH.dbd.CH-- and form a fused ring with the carbon atoms to which they are attached, optionally substituted by lower alkyl or lower alkoxy;R.sup.3 /R.sup.3' are independently from each other hydrogen, lower alkyl, or taken together with the carbon atom to which they are attached, form a cycloalkyl group;R.sup.4 is hydrogen, lower alkyl, --N(R.sup.5).sub.2, --N(R.sup.5)(CH.sub.2).sub.n OH, --N(R.sup.5)S(O).sub.2 -phenyl, --N(R.sup.5)S(O).sub.2 -lower alkyl, --N.dbd.CH--N(R.sup.5).sub.2, --N(R.sup.5)C(O)R.sup.5 or a cyclic tertiary amine of the group ##STR35##R.sup.5 is hydrogen, lower alkyl, or benzyl, which is optionally substituted by lower alkyl;R.sup.6 is hydrogen, hydroxy, lower alkyl, --(CH.sub.2).sub.n COO-lower alkyl, --N(R.sup.5)CO-lower alkyl, hydroxy-lower alkyl, cyano, --(CH.sub.2).sub.n O(CH.sub.2).sub.n OH, --CHO, or a 5- or 6 membered heterocyclic ring, optionally bonded via an alkylene group,X is --C(O)N(R.sup.5)-- or --N(R.sup.5)C(O)--;n is 0-4; andpharmaceutically acceptable acid addition salts thereof, which process comprisesa) reacting a compound of formula ##STR36##wherein A denotes R or R.sup.4, and R is halogen, and R.sup.5' has the same meaning as R.sup.5, wherein R.sup.5 and R.sup.5' may be independent from each other,with a compound of formulaR.sup.1 MgHal Vwherein Hal is a halogen atom,to a mixture of compounds of formulae ##STR37##ora') reacting a compound of formula IV-1, wherein A is R, with a compound of formula V and with a compound of formulaHR.sup.4 VIIin one reaction step, to a compound of formula ##STR38##andb) oxidizing a compound of formulae X-1, XI-1 or VI with an oxidizing agent, to a compound of formula ##STR39##andc) reacting a compound of formula VIII with a compound of formula ##STR40##wherein R is halogen, to a compound of formula ##STR41##wherein X is --CON(R.sup.5)--, orc'i) reacting a compound of formula VIII with a compound of formula IX, to a compound of formula ##STR42##andii) reacting a compound of formula XIII to a compound of formula ##STR43##or ##STR44##andiii) transforming a compound of formulae XIV or XV to a compound of formula ##STR45##wherein R.sup.5 is methyl, andiv) reacting a compound of formula XVI with a compound of formula ##STR46##to a compound of formula ##STR47##wherein X is --N(R.sup.5)C(O)--.