Patent GB-825016-A (GB)
Title: Therapeutic derivatives of aryl-benzthiazoles
Inventor: STEPHENS FRANCIS FREDERICK
IPC: C07D277/66
Filed: 1956-11-02
Abstract: The invention comprises compounds of the formula <FORM:0825016/IV (b)/1> and their acid addition and quaternary ammonium salts (wherein X is a hydrogen or halogen atom, or an amino, dialkylamino or alkoxy group, R is a hydrogen or halogen atom or an alkoxy group, R1 and R11 represent a hydrogen atom or alkyl group, A is an alkyl group or AA may be part of a ring such that NAA is, for example, a piperidino or morpholino residue, and the substituents X and <FORM:0825016/IV (b)/2> may be interchanged), and the preparation thereof by: (a) condensing an o-aminothiophenol or its hydrochloride with basic ethers of hydroxy benzaldehydes; (b) condensing an oaminophenyl-thiosulphuric acid with the basic ether of a hydroxybenzaldehyde; (c) dealkylating suitable 2-phenylbenzthiazole alkyl ethers and condensing the resulting hydroxyphenyl-benzthiazoles with basically substituted alkyl chlorides <FORM:0825016/IV (b)/3> these processes being followed, if necessary and desired, by conversion into an acid addition salt or alkylation to form a quaternary ammonium salt.  In the acid addition and quaternary ammonium salts, the anion may be derived from an inorganic or organic acid (e.g. hydrohalic, acetic, citric, oxalic, sulphuric, tartaric, undecylenic or p-toluenesulphonic acid).  Examples describe the preparation of: 2-(p-dimethylaminoethoxyphenyl)benzthiazole, 5-chloro-2-(p - diethylaminoethoxyphenyl)benzthiazole and its hydrochloride, citrate, oxalate and tartrate; 5 - chloro - 2 - (o - diethylaminoethoxyphenyl)benzthiazole and its hydrochloride; 5-chloro-2-(m - diethylaminoethoxyphenyl)benzthiazole hydrochloride; 6 - ethoxy - 2 - (p - diethylaminoethoxyphenyl)benzthiazole and its hydrochloride; 2 - (p - diethylaminoethoxyphenyl)benzthiazole and its tartrate; 2-(p-dimethylaminoisopropoxyphenyl)benzthiazole and its hydrochloride; 5-chloro-2-(p-4-morpholinoethoxyphenyl)benzthiazole and its hydrochloride and tartrate; 5-chloro-2-(m-bromo-p-diethylaminoethoxyphenyl)benzthiazole hydrochloride; 6 - dimethylamino - 2 - (p - diethylaminoethoxyphenyl)benzthiazole and its tartrate; 2-(p - triethylammoniumethoxyphenyl)benzthiazole iodide; 2-(p-trimethylammoniumisopropoxyphenyl)benzthiazole iodide; 2-(m-methoxy-p - trimethylammoniumethoxyphenyl)benzthiazole iodide; 6 - chloro - 2 - (p - diethylaminoethoxyphenyl)benzthiazole and its tartrate; 6-diethylaminoethoxy - 2 - (p - chlorophenyl)benzthiazole and its tartrate; 1:10-bis-(5-chloro-2-p - dimethylammoniumethoxyphenyl - benzthiazole) - n - decane dibromide; 5 - chloro - 2 -(p p  - diethylaminoethoxyphenyl)benzthiazole undecylenate.  Other specified products are: 2-(p - trimethylammoniumethoxyphenyl)benzthiazole iodide; 5 - chloro - 2 - (p - trimethylammoniumethoxyphenyl)benzthiazole iodide; 5 - chloro - 2 - (p - trimethylammoniumisopropoxyphenyl)benzthiazole iodide; 5-chloro-2-(p - triethylammoniumethoxyphenyl)benzthiazole iodide; 6-chloro-2-(p-triethylammoniumethoxyphenyl)benzthiazole iodide; 5-chloro-2-(p - diethylaminoethoxyphenyl)benzthiazole methiodide; 5 - chloro - 2 - (p - dimethylaminoethoxyphenyl)benzthiazole and its hydrochloride and tartrate; 5-chloro-2-(p-dimethylaminoisopropoxyphenyl)benzthiazole and its hydrochloride and tartrate; 5-chloro-2-(p-di-n-butyl-aminoethoxyphenyl)benzthiazole and its tartrate; 6 - amino - 2 - (p - diethylaminoethoxyphenyl)benzthiazole tartrate.