Imidazole derivatives, preparation and user thereof as medicine
View Patent ↗The invention concerns novel imidazole derivatives of general formula (I), wherein Z′ and Z represent different variable groups. Said products have an antitumoral activity. The invention also concerns pharmaceutical compositions containing said products and their use for preparing antitumoral medicine.
1. A compound of formula (I)
in which:
Z′ represents a hydrogen atom or a halo radical;
Z represents a radical of formula —NH—SO 2 —NR 1 R 2 ;
R 1 and R 2 represent, independently, a hydrogen atom, a (C 1 -C 6 )alkyl radical, phenyl optionally substituted by a (C 1 -C 6 )alkyl radical, or benzyl optionally substituted on the ring by a (C 1 -C 6 )alkyl radical; or
a pharmaceutically acceptable salt of said compound.
2. The compound according to claim 1 , wherein R 1 and R 2 represent, independently, a hydrogen atom or a (C 1 -C 6 )alkyl radical.
3. The compound according to claim 1 wherein R 1 represents a hydrogen atom and R 2 represents a hydrogen atom or a (C 1 -C 6 )alkyl radical.
4. The compound according to claim 1 wherein Z is in para position.
5. The compound according to claim 1 wherein Z′ is in meta position.
6. The compound according to claim 5 , wherein Z′ represents a halo radical.
7. The compound according to claim 1 wherein said compound is:
N-(2-fluoro-4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}phenyl)sulfamide hydrochloride; or
a pharmaceutically acceptable salt of said compound.
8. A process for the preparation of a compound of formula (I) according to claim 1 in which R 1 represents a hydrogen atom, R 2 represents a hydrogen atom or an alkyl radical, and X represents an —SO 2 — radical, said process comprising the steps of:
(a) reacting a compound of formula (I′)
in which Z′ is a hydrogen atom or a halo radical
with a sulfonyl halide of formula GpNR 2 —SO 2 -Hal wherein Gp is a protecting group for the amine function and Hal represents a halo radical, thereby forming a compound of formula (V)
(b) deprotecting said compound (V) to form compound (I).
9. A pharmaceutical composition comprising a compound according to claim 1 as active ingredient, in combination with a pharmaceutically acceptable support.