IP Library Granted Patent US 7,777,057
Granted Patent B2
US 7,777,057 · App. 12/510,326 · Granted Aug 17, 2010

Derivatives of dioxan-2-alkyl carbamates, preparation thereof and application thereof in therapeutics

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Quick Facts
Patent No.
US 7,777,057
App. No.
12/510,326
Granted
Aug 17, 2010
Kind
B2
Abstract

A compound corresponding to general formula (I): in which R 1 represents a phenyl or naphthalenyl group optionally substituted with one or more halogen atoms or hydroxyl, cyano, nitro, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, trifluoromethyl, trifluoromethoxy, benzyloxy, (C 3 -C 6 )cycloalkyl-O— or (C 3 -C 6 )cycloalkyl(C 1 -C 3 )alkoxy groups; R 2 represents either a group of general formula CHR 3 CONHR 4 in which R 3 represents a hydrogen atom or a methyl group and R 4 represents a hydrogen atom or a (C 1 -C 3 )alkyl, (C 3 -C 5 )cycloalkyl or (pyridin-4-yl)methyl group; or a 2,2,2-trifluoroethyl group; or an (imidazol-2-yl)methyl group; or a (benzimidazol-2-yl)methyl group; or a phenyl group optionally substituted with one or more halogen atoms or cyano, nitro, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, trifluoromethyl or trifluoromethoxy groups; and n represents a number ranging from 1 to 3; in the form of a base, of an addition salt with an acid, of a hydrate or of a solvate. Also disclosed and claimed are the pharmaceutical compositions derived therefrom and their therapeutic use in treating a wide variety of diseases.

Claims (24)

1. A method for preparing a compound of formula (I):

wherein

R 1 represents a phenyl or naphthalenyl group optionally substituted with one or more halogen atoms or hydroxyl, cyano, nitro, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, trifluoromethyl, trifluoromethoxy, benzyloxy, (C 3 -C 6 )cycloalkyl-O— or (C 3 -C 6 )cycloalkyl(C 1 -C 3 )alkoxy groups;

R 2 represents

either a group of general formula CHR 3 CONHR 4 ,

or a 2,2,2-trifluoroethyl group,

or an (imidazol-2-yl)methyl group,

or a (benzimidazol-2-yl)methyl group,

or a phenyl group optionally substituted with one or more halogen atoms or cyano, nitro, (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, trifluoromethyl or trifluoromethoxy groups; and

wherein

R 3 represents a hydrogen atom or a methyl group and

R 4 represents a hydrogen atom or a (C 1 -C 3 )alkyl, (C 3 -C 5 )cycloalkyl or (pyridin-4-yl)methyl group;

n represents a number ranging from 1 to 3;

comprising:

reacting the amine of formula (II):

wherein

R 1 and n are as defined above for formula (I), with a carbonate of formula (III):

wherein U represents a hydrogen atom or a nitro group and R 2 is as defined above for formula (I).

2. A compound of formula (III):

wherein

R 2 represents a group of general formula CHR 3 CONHR 4 wherein

R 3 represents a hydrogen atom or a methyl group and

R 4 represents a hydrogen atom or a (C 1 -C 3 )alkyl, (C 3 -C 5 )cycloalkyl or (pyridin-4-yl)methyl group; and

U represents a hydrogen atom or a nitro group.

Assignments (2)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2010
From: ABOUABDELLAH, AHMED; BAS, MICHELE; DARGAZANLI, GIHAD; HOORNAERT, CHRISTIAN; LI, ADRIEN TAK; MEDAISKO, FLORENCE
To: SANOFI-AVENTIS
Reel/Frame 023866/0660 →