DE1470017

Halogenated products are obtained by reacting a 1,2-dihydroquinoline having an aliphatic substituent in the 4-position with a halogenating agent. The invention also comprises 4-halogeno-aliphatic-2,2-dialiphatic-1,2-dihydroquinolines and their salts. Suitable halogenating agents are the free halogens, sulphuryl halides, and N-halo compounds such as N-bromosuccinimide; preferably the halogen introduced is chlorine or bromine. Preferred starting materials are those of the formula: where R1 is hydrogen or a hydrocarbon or acyl group (especially aliphatic carboxylic acid of up to 4 carbon atoms or aromatic sulphonic acyl), R2 and R3 are aliphatic hydrocarbon groups, R4 is an aliphatic group, R5 is halogen, alkyl, aryl, alkoxy or other inert group, and n is 0-4. The first halogen atom introduced normally enters the a -position of the 4-substituent; the second and third halogen atoms, if introduced, normally enter the dihydroquinoline nucleus; further halogenation can saturate the double bonds of the dihydroquinoline nucleus or can produce N-halogenation: up to 10 halogen atoms can be introduced. An N-carboxylic acyl group is generally removed during the halogenation. The products of the invention are mycobacteriostats (see Division A5). The Provisional Specification refers generally to the halogenation of 1,2-dihydroquinolines, including -isoquinolines.ALSO:Mycobacteriostatic compositions comprise an inert diluent and a product obtained by halogenating a 1,2-dihydroquinoline having an aliphatic substituent in the 4-position, especially a 4-halogenoaliphatic-2,2-dialiphatic-1,2-dihydroquinoline, particularly those of wherein R1 is hydrogen, alkyl or aromatic acyl, R2 and R3 are alkyl, n is 0 or 1 to 4, R5 is alkoxy, alkyl or halogen, R6 is halogeno aliphatic and y is hydrogen or halogen, or a salt thereof (see Division C2). The compositions may comprise the active ingredient in an aqueous medium stabilized by a surface-active agent, or in an organic solvent, and the solution can then be emulsified in an aqueous medium; suitable solvents are toluene, cyclohexane, petroleum ether, chloroform, chlorobenzene, and vegetable and animal oils; the emulsions may be lotions, pastes, creams or ointments. Solid compositions may be prepared using an inert solid such as talc. Specified salts are the oxalates, sulphates, hydrochloride, hydrobromides and quaternary ammonium halides. The active ingredients are also added to soaps, waxes