Patent GB-1298535-A (GB)
Title: New diazole and triazole derivatives, their production and their medicinal use
Inventor: BUECHEL KARL-HEINZ
IPC: C07D233/62
Filed: 1971-04-19
Abstract: 1298535 Diazole and triazole derivatives BAYER AG 19 April 1971 [9 April 1970 15 Feb 1971] 26106/71 Heading C2C The invention comprises diazole and triazole derivatives of the formula in which A and B, which may be identical or different, each are alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxycarbonyl, aryloxycarbonyl, haloalkyl, (alkylthio)carbonyl, (arylthio)alkyl, or #-dialkylamino-alkoxycarbonyl, an optionally substituted aromatic hydrocarbon radical, a 5- or 6-membered heteroaromatic ring comprising as constituents of the ring 1 or 2 nitrogen atoms carrying no substituents and also optionally an oxygen or sulphur atom or a nitrogen atom carrying as substituent an alkyl or aryl group, the said heteroaromatic ring optionally carrying, as substituent on one of the carbon atoms, a halogen atom or an alkyl, alkenyl or optionally substituted aryl group, and being linked to the carbon atom C<SP>*</SP> at one of its carbon atoms; or A and B together with the central carbon atom C<SP>*</SP> forms the group of the formula in which R is H or a substituent; m is 1 or 2 and Y is a direct bond, O, S or alkylene; X is a direct bond or O, S, CH 2 , SO, SO 2  or CO; and E is N or CH; and acid addition salts thereof. The compounds are prepared by reacting azoles of the formula or alkali metal or silver salts thereof with halogen derivatives of the formula or carbinols of the formula with sulphoxides of the formula α - (4 - Phenylyl - α - (2 - chlorophenyl)benzyl alcohol is obtained by a solution of bromobenzene and lithium in ether with a solution of 4<SP>1</SP> - phenyl - 2 - chlorobenzophenone in tetrahydrofuran. Diphenyl - (4 - phenylthiophenyl) - chloromethane is prepared by chlorinating diphenyl- (4 - phenylthiophenyl) - methanol resulting from the Grignard reaction between benzophenone and 4-bromodiphenyl sulphide, which is made by brominating diphenyl sulphide. By a similar process diphenyl - (4 - phenoxyphenyl) - chloromethane, diphenyl - (4 - phenoxyphenyl) methanol, p - bromo - diphenyl ether, 4,4<SP>1</SP> - dichlorobisphenyl (4 - phenoxyphenyl) - chloromethane, 3,4 - dichloro - bisphenyl - (4 - phenoxyphenyl)- chloromethane. and 2 - fluorobisphenyl - (4- phenoxyphenyl) chloromethane are prepared. Diphenyl - (4 - benzoylphenyl) - chloromethane is prepared by reacting a mixture of AlCl 3 , benzene and p-trichloromethylbenzoyl chloride, the latter compound being obtained by chlorinating p-toluoyl chloride. 1,5 - Dimethylpyrozol - 3 - yl - 4 - phenoxyphenyl-methanol is obtained the Grignard reagent obtained by reacting 4-bromodiphenyl ether with 5 - (2,3 - dimethylpyrazolyl) - phenyl ketone. Similarly bis - (4 - phenoxyphenyl)- phenyl methanol is obtained. 4 - t - Butyl - 4<SP>1</SP>- phenylphenyltrityl chloride is obtained by chlorinating the corresponding alcohol. 9 - (4 - Phenoxy) - phenylfluorenol is obtained by the Grignard reagent obtained from 4- bromodiphenyl ether and Mg with fluorenone. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above novel compound or acid addition salts thereof and carriers or diluents. The compounds possess activity against protozoa.