GB1205638A - 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them - Google Patents

Abstract

1,205,638. Quinoline-3-carboxylic acids and their derivatives. CIBA Ltd. 25 Sept., 1967 [29 Sept., 1966; 7 April, 1967; 3 July, 1967; 18 August, 1967], No. 43549/67. Heading C2C. [Also in Division A5] Novel compounds of formulµ and 3-esters, 3-amides, 3-hydrazides and 3- nitriles thereof, and 4-esters of the compounds of the second formula, wherein R represents a cycloalkyl or cycloalkenyl radical optionally substituted by aliphatic, aromatic or araliphatic residues or etherified or esterified hydroxyl groups, A represents a direct bond or a C 1- 7 alkylene group, X is O or S, R 2 is H or C 1-7 alkyl, R 3 is H, C 1-7 alkyl, C 1-7 alkenyl, a free, etherified or esterified hydroxy-C 1-7 alkyl, a free or esterified carboxy-C 1-7 alkyl, amino-C 1-7 alkyl, or aryl-C 1-7 alkyl, or a group of the formula R-A-, R and A having the previous significance, and each of the symbols R b and R c represent H, C 1-7 alkyl, a free, etherified or esterified hydroxy or mercapto group, CF 3 , NO 2 , an amino group, or aryl-C 1-7 alkyl, are prepared (a) by ring closing a di-C 1-7 -alkyl ester or a nitrile-C 1-7 -alkyl half ester of an [optionally substituted 1-(cycloaliphatyloxy- or cycloaliphatylthio - phenylamino) alkylmalonic acid which is unsubstituted in one of the positions of the phenyl residue adjacent to the amino group, or a tautomer thereof in which the amino group contains a hydrogen atom, by intramolecular condensation; (b) by converting in an optionally substituted -cycloaliphatyloxy or cycloaliphatylthio - 4 - Y 1 - quinoline - 3 - carboxylic acid or a 3-ester, 3-amide, 3-hydrazide or 3- nitrile of such a compound, in which Y 1 is halo or in a 1-substituted tautomer thereof Y 1 is a functionally converted oxo group capable of being liberated by hydrolysis, the group Y 1 into a hydroxy or an oxo group by hydrolysis; or (c) ring-closing an optionally substituted - cycloaliphatyloxy- or cycloaliphatylthio-oaminobenzoylacetic acid or an amide, ester, hydrazide or nitrile thereof, in which the amino group or the α-position of the acetic acid residue carries a C 1-7 alkanoyl group, by intramolecular condensation and then if desired the functional group in the 3-position can be converted into the free acid, ester, amide, hydrazide, nitrile or salt by conventional methods. Compounds prepared by any of these methods can be converted into other novel compounds defined above by standard methods, for example, by etherification, hydrolysis or transesterification, or by reaction with amines, ammonia, hydrazines or reactive esters. Ethyl 4 - chloro - 6,7 - bis - cyclopropyl - methoxy - quinoline - 3 - carboxylate is formed as a by-product when diethyl (3,4-bis-cyclopropylmethoxy - phenylamino) methylmalonate is reacted with phosphorus oxychloride.