Patent GB-981952-A (GB)
Title: Monoazo heterocyclic compounds and methods for producing same
IPC: C09B29/06
Filed: 1961-03-09
Abstract: The invention comprises free bases of formula <FORM:0981952/C4-C5/1> and their non-toxic acid-addition salts, where Y is -A-N(R1)R2 or <FORM:0981952/C4-C5/2> A being an alkylene radicle of 2-8 C atoms or an alkylene radicle of 3-6 C atoms in which one of the methylene groups not attached to the N atoms is replaced by an -O-, -S-, =CHOH, =COH (lower alkyl), =N (lower alkyl) or =CH (lower dialkylaminoalkyl) group, R is H, Hlg, or a lower alkyl or lower alkoxy radicle, R1 and R2 are alkyl, alkoxyalkyl, hydroxyalkyl or cycloalkyl radicles having less than 7 C atoms, allyl, methallyl or a lower dialkyl-aminoalkyl radicle of 3-7 C atoms, and may be combined to provide a heterocyclic residue of less than 10 C atoms which may be substituted by lower alkyl, lower hydroxyalkyl, lower alkoxyalkyl, hydroxy, lower alkoxy, amino or lower dialkylaminoalkyl groups, f is 0-3, g and h are integers so that g + h is 3 or 4, R3 is a lower alkyl, lower hydroxyalkyl, lower alkoxyalkyl or a lower dialkylaminoalkyl radicle, and HET is a heterocyclic residue of less than 15 C atoms, a C atom of which is bound to the azo N atom, and may be substituted by keto, hydroxy, lower alkyl, phenyl, lower alkoxy, nitro, amino, lower hydroxyalkyl, lower aminoalkyl, keto, phenoxy, acyl, sulpho, carboxy, thio, sulphonamido, sulphonyl or imino radicles.  The term "lower" describes groups which have not more than 4 carbon atoms, except when used with dialkylaminoalkyl groups where it indicates that the group has 3-7 C atoms.  The compounds may be made, in conventional fashion, by coupling an appropriate a -naphthylamine with the required heterocyclic diazo component; by treating a corresponding compound, in which the group -NHY is -NH-A-Hal, with an amine of formula HN(R1)R2, or by hydrolysing a corresponding compound in which -NH-Y is -N(Y)COR4, where R4 is H or a perhaloalkyl radicle. Hydrolysis is preferably effected under mild conditions with acids when R4 is H, and alkalies when R4 is a perhaloalkyl radicle. Illustrative of specified heterocyclic radicles are furyl, thienyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, thiazinyl, hexamethyleneiminyl, dioxanyl, dithinyl, thiapyranyl, pyrimidyl, pyrazinyl and tetrazolyl radicles and their N-oxides and benzo- and naphtho-condensed ring systems.  The compounds have anti-parasitic, especially anti-schistomiasistic, properties. Representative of specified acids from which salts may be formed are hydrochloric, sulphuric, phosphoric, oxalic, cholic, sulphamic, phenoxyacetic, lactic, alginic, succinic, maleic, mandelic, oleic, tannic, penicillinic, 3-hydroxy-2-naphthoic, 4-biphenylcarboxylic, 8:hydroxy-7-iodo-5-quinoline-sulphonic, cyclohexane carboxylic and arsonic acids.  Salts with inorganic antimony derivatives, e.g. the trichloride, and with compounds possessing anti-schistosomiasistic properties, e.g. phthalic acid mono-4-(31-chloro-41-methylphenyl) - piperazide, N,N1 - [heptamethylene-bis - (oxy - p - phenylene)] - di - b - alanine and 2 - (4,6 - disulpho - 1,3,2 - benzodioxastibiol - 2 - yloxy) - 1 - phenyl - 3,5 - disulphonic acid. Numerous examples are provided of the preparation of the compounds by the process outlined above.  Amongst the compounds made are 5-[4-(2-diethylamino-ethylamino) - 1 - naphthylazo] - uracil and its hydrochloride, 1 - diethylamino - 3 - [4 - (3 - pyridylazo) - 1 - naphthylamino] - 2 - propanol and its trihydrochloride, 1 - { 2 - [ 4 - (2- thiazolylazo) - 1 - naphthylamino) - ethyl} - piperidine, 4 - [4 - (2 - diethylaminoethylamino) - 7 - methoxy - 1 - naphthylazo] - 2,3 - dimethyl - 1 - phenyl - 3 - pyrazolin - 5 - one dihydrochloride, and 6 - [4 - (2 - dimethylamino - 1 - methylethylamino) - 1 - naphthylazo] - 1(H) - benzotriazole.