Patent EP-0678503-B1 (EP)
Inventor: GOESCHKE RICHARD DR
IPC: C07C237/24
Filed: 1995-04-07
Granted: 1999-09-01
Abstract: delta -Amino- gamma -hydroxy- omega -aryl-alkanoic acid amides (I) and their salts are new: R1 = H; OH; lower alkoxy opt. substd. by lower alkoxy or COOH (opt. esterified or amidated); or cycloalkoxy; R2 = H; lower alkyl opt. substd. by lower alkoxy, lower alkoxy-lower alkoxy, cycloalkoxy, amino (opt. substd. by lower alkyl, lower alkanoyl and/or lower alkoxycarbonyl), heteroaryl (opt. hydrogenated), lower alkenyloxy or COOH (opt. esterified or amidated); cycloalkyl; OH; lower alkoxy opt. substd. by hydroxy (opt. lower alkanoylated, halogenated or sulphonylated), amino (opt. substd. by lower alkyl, lower alkanoyl and/or lower alkoxycarbonyl), oxo, cycloalkoxy, lower alkoxy, lower alkenyloxy, lower alkanoyl, lower alkylthio (opt. S-oxidised), lower alkylthio(hydroxy), aryl, heteroaryl (opt. hydrogenated), CN or COOH (opt. esterified or amidated); cycloalkoxy; lower alkoxy-lower alkenyl; or lower alkoxy-lower alkenyloxy; R3 = lower alkyl opt. substd. by halo, lower alkoxy, cycloalkoxy, OH, lower alkylthio (opt. S-oxidised), heteroarylthio (opt. hydrogenated), heteroaryl (opt. hydrogenated), amino (opt. mono- or di-substd. by lower alkyl or mono-substd. by lower alkanoyl or lower alkanesulphonyl or N,N-disubstd. by lower alkylene, opt. N-alkylated or lower alkanoylated aza-lower alkylene, oxa-lower alkylene or opt. S-oxidised thia-lower alkylene) or COOH (opt. esterified or amidated); cycloalkyl; aryl; OH; cycloalkoxy; or lower alkoxy opt. substd. by lower alkoxy, cycloalkoxy, OH, aryl, halo, lower alkylthio (opt. S-oxidised), heteroaryl (opt. hydrogenated), heteroarylthio (opt. hydrogenated), amino (opt. mono- or di-substd. by lower alkyl or mono-substd. by lower alkanoyl or lower alkanesulphonyl or N,N-disubstd. by lower alkylene, opt. N-alkylated or lower alkanoylated aza-lower alkylene, oxa-lower alkylene or opt. S-oxidised thia-lower alkylene), CN or COOH (opt. esterified or amidated); and R4 = H; lower alkyl; OH; lower alkoxy; or cycloalkoxy; or R3 and R4 together form lower alkylenedioxy, a fused benzene or cyclohexane ring; X = CH2 or CH(OH); R5 = lower alkyl or cycloalkyl; R6 = amino opt. mono- or di-substd. by lower alkyl or mono-substd. by lower alkanoyl; R7 = lower alkyl; lower alkenyl; cycloalkyl; or aryl-lower alkyl; R8 = lower alkyl opt. substd. by OH (opt. aliphatically esterified or etherified), amino (opt. mono- or di-substd. by lower alkyl or mono-substd. by lower alkanoyl or lower alkanesulphonyl or N,N-disubstd. by lower alkylene, opt. N-alkylated or lower alkanoylated aza-lower alkylene, oxa-lower alkylene or opt. S-oxidised thia-lower alkylene), opt. esterified or amidated COOH, di-COOH, COOH(OH) or COOH-cycloalkyl, CN, lower alkanesulphonyl, thiocarbamoyl or sulphamoyl (opt. N-mono- or N,N-di-alkylated) or C-bonded opt. hydrogenated and/or oxo-substd. heteroaryl; cycloalkyl; or C-bonded opt. hydrogenated and/or oxo-substd. heteroaryl. Also claimed are starting materials (II) X1 = lower alkyl; lower alkanoyl; or NH2 protecting gp.; X2 = H; X3 = H or OH protecting gp.; X4 = opt. reactive etherified or esterified OH; or X2 and X3 together form a divalent protecting gp. or X3 and X4 together form a direct bond.