New 3H-naphtho(1,2-d)imidazoles, processes for preparing them, compounds for use as antiinflammatory and antimicrobial agents and compositions for that use containing them

Claim 2

2) A process for preparing a compound of formula I wherein R, R 1 , R and A are as defined in claim 1 characterized in that a N-rsubstituted-1-nitrosor-2-naphthalene- amine derivative of formula IV wherein R, R 1 and R 2 are as defined in claim 1, is reduced to the corresponding N 2 -substituted-naphthalen--1,2-diamine of formula II by means of hydrogen in the presence of a hydrogenation catalyst, said intermediate compound is condensed with a suitably selected aldehyde of formula ACHO wherein A is as defined in claim 1, to yield the corresponding imidazoline derivative of formula III which in its turn is transformed into the final compound of formula I by means of a dehydrogenating agent; said process being further characterized in that: a) when a compound of formula I is obtained wherein A stands for a hydroxyphenyl radical, it may be transformed into the corresponding compound of formula I wherein A is phenyl substituted with (C 1-4 )alkoxy, (C 3-4 )alkenylo- x y, (C 3-4 )alkynyloxy, benzyloxy, (C 2-4 )alkanoyloxy, carboxy-methoxy or [carbo(C 1-4 )alkoxy]methoxy, by reaction with suitably agents such as (C 1-4 )alkyl, (C 3-4 )alkenyl, (C 3-4 )alkynyl and benzyl halogenides, tosylates or mesylates, (C 2-4 )alkanoyl halogenides or anhydrides, an α-haloacetic acid and its (C l-4 )alkyl esters, and b) when a compound of formula I is obtained wherein A is phenyl substituted with alkanoylamino or benzoylamino groups, it may be converted into the corresponding compound of formula I wherein A is phenyl substituted with amino by acid hydrolysis, or it may be transformed into the corresponding compound of formula I wherein A is phenyl substituted with mono-(C 1-4 )alkylamino groups by reaction with alkyl halogenides followed by alkaline hydrolysis.

Claim 3

3) The process of claim 9 wherein the intermediates of formula II and III are not isolated from the reaction medium.

Claim 4

4) A process for preparing a compound of formula I wherein R , R 1 , R 2 and A are as defined in claim 1, characterized in that a N 2 -substituted naphthalen-1,2--diamine of formula II wherein R,-R 1 and R 2 are as defined in claim l x is con - densed with an acid derivative of formula wherein A is as defined in claim 1 and X may represent - a chlorine atom - a group -OR 3 wherein R 3 may be the same radical a trifluoroacetyl, ethoxycarbonyl or alkylsulphonyl moiety, or - a group -OR 4 wherein R 4 stands for methyl or ethyl, to yield the corresponding mono-acylated compound of formula V which in its turn is cyclized to the final compound of formula I ; said process being further characterized in that a) when a compound of formula I is obtained wherein A stands for a hydroxyphenyl radical, it may be transformed into the corresponding compound of formula I wherein A is phenyl substituted with (C 1-4 ) alkoxy, (C 3-4 )alkenyloxy, (C 3-4 )al ky n y lox y , benzyloxy, (C 2-4 )alkanoyloxy, carboxy--methoxy or [carbo(C 1-4 )alkoxy]methoxy, by reaction with suitable agents such as (C 1-4 )alkyl, (C 3-4 )alkenyl, (C3-4)alkynyl, and benzyl halogenides, tosylates or mesylates, (C 2-4 )alkanoyl halogenides or anhydrides, an α-haloacetic acid and its (C 1-4 )alkyl esters and b) when a compound of formula I is obtained wherein A is phenyl substituted with alkanoylamino or benzoylamino groups, it may be converted into the corresponding compound of formula I wherein A is phenyl substituted with amino by acid hydrolysis, or it may be transformed into the corresponding compound of formula I wherein A is phenyl substituted with mono-(C 1-4 )alkylamino groups by reaction with alkyl halogenides followed by alkaline hydrolysis.

Claim 5

5) A process according to any of the preceeding claims for preparing 2-(4-methoxyphenyl)-3-(1-methylethyl)-3H--naphtho[1,2-d]imidazole

Claim 6

6) A process according to any of claims 1, 2, 3 and 4 for preparing 2-(4-methoxyphenyl)-3-methyl-3H-naphtho[1,2--d]imidazole

Claim 7

7) A process according to any of claims 1, 2, 3 and 4 for preparing 4-(3-methyl-3H-naphtho[1,2-d]imidazol-2-yl)- -2,N,N-trimethylbenzenamine.