GB1425293A - Carbamate derivatives of 2-nitro-1-imidazol-alkanols-, emthods for their preparation and compositions containing them - Google Patents

Abstract

1425293 Carbamates of 2-nitro-1-imidazolylalkanols F HOFFMANN-LA ROCHE & CO AG 17 Jan 1974 02203/74 Heading C2C Novel compounds I: in which A is a group (CH 2 ) m (where m is 2 to 6), a group CH 2 -CHOH-(CH 2 ) n (where n is 1 to 4) or a group CH 2 -CH(R) (where R is C 1-7 alkyl, halo C 1-7 alkyl, halo-C 1-7 alkoxy-C 1-7 alkyl, C 1-7 alkoxy-C 1-7 alkyl or 2-chlorophenoxymethyl) and X is amino optionally mono- or di-C 1-7 alkylated, hydroxy C 1-7 alkylamino, cycloalkylamino, furfurylamino, arylamino or aralkylamino (where aryl denotes phenyl, substituted phenyl or a 5- or 6-membered nitrogen containing heterocyclic ring which may be substituted by halogen, C 1-7 alkyl, CF 3 , NH 2 or NO 2 ; the five-membered heterocycles may further contain an oxygen or nitrogen atom and the six-membered heterocycles may further contain an oxygen, nitrogen or sulphur atom) or a 5- or 6-membered ring represented by -N#Z (where Z is an alkylene, azaalkylene, N-C 1-7 alkyl-azaalkylene, or oxaalkylene chain of 4 or 5 members) and their acid addition salts, are prepared by (4) reacting 2-nitroimidazole with either (i) an #-halogenated alkanol (ii) an epoxy compound or (iii) an epoxy compound reacting the alkanol formed with 2,2,2-trichloroethyl chlorocarbonate and reacting the carbonate derivative formed with the appropriate amine HX. Compounds I (A = (CH 2 ) m ; X=phenylamino or m-chlorophenylamino) are also prepared by reacting 2-nitroimidazole with followed by reaction with phenylisocyanate or m-chlorophenylisocyanate. Compounds I [A= CH 2 -CH(R) where R is methyl or 2-chlorophenoxymethyl; X is NH 2 ] are prepared by reacting 2-nitroimidazole with the appropriate epoxide followed by reaction with phosgene and ammonia. Novel compound IV: 2<SP>1</SP>,2<SP>1</SP>,2<SP>1</SP>-trichloroethyl N - [2 - (2 - nitro - 1 - imidazolyl)- ethyl]-carbamate is prepared by reacting ethylenimine with 2-nitro-imidazole and reacting the #-aminoethyl derivative with 2,2,2-trichloroethyl chlorocarbonate. Compounds I and IV have anti-protozoal and anti-bacterial activity and form with a carrier a pharmaceutical composition which may be administered parenterally or topically.