IP Library Granted Patent US 8,188,133
Granted Patent B2
US 8,188,133 · App. 12/298,757 · Granted May 29, 2012

Imidazole derivatives, preparation and user thereof as medicine

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Quick Facts
Patent No.
US 8,188,133
App. No.
12/298,757
Granted
May 29, 2012
Kind
B2
Abstract

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.

Claims (20)

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.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR NAME PREVIOUSLY RECORDED ON REEL 296336 FRAME 0777. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jan 5, 2016
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES, S.A.S.
To: IPSEN PHARMA S.A.S.
Reel/Frame 037430/0194 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ADDRESS PREVIOUSLY RECORDED ON REEL 023034 FRAME 0251. ASSIGNOR(S) HEREBY CONFIRMS THE ADDRESS SHOULD BE 65 QUAI GEORGES GORSE, 92100 BOULOGNE-BILLANCOURT, FRANCE. Recorded Jan 16, 2013
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATION SCIENTIFIQUES (S.C.R.A.S.)
To: IPSEN PHARMA S.A.S.
Reel/Frame 029636/0777 →
CHANGE OF NAME Recorded Jul 31, 2009
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATION SCIENTIFIQUES (S.C.R.A.S.)
To: IPSEN PHARMA S.A.S.
Reel/Frame 023034/0251 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 10, 2009
From: LIBERATORE, ANNE-MARIE; BIGG, DENNIS; PONS, DOMINIQUE; PREVOST, GREGOIRE
To: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)
Reel/Frame 022370/0893 →