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US 8,772,478 B2Granted
Benzenesulfonamide compounds, method for synthesizing same, and use thereof in medicine as well as in cosmetics
AssigneeGalderma Research & Development
InventorsLaurence Clary, Sandrine Chambon, Laurent Chantalat, Pascale Mauvais, Olivier Roye, Marlène Schuppli
Life of this patent
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Abstract
Benzenesulfonamide compounds having a structure of the following general formula (I) are described. Also described, are methods for synthesizing the compounds, and to the use thereof in pharmaceutical compositions for human or veterinary medicine and in cosmetic compositions.
Claims20
A compound of formula (I) below:
- in which:
- R1 and R2 are identical or different and represent alkyl radicals or else they form a ring with the nitrogen atom to which they are attached, said ring being represented by the formula below:
- X, m, and n having the meanings given hereinafter;
- R3 is a hydrogen atom or a lower alkyl radical;
- R4 is an alkyl radical, a substituted alkyl radical, an alkenyl radical, a substituted alkenyl radical, an alkynyl radical, a substituted alkynyl radical, an aryl radical, a substituted aryl radical, an aralkyl radical, a substituted aralkyl radical, a heterocyclic radical, a substituted heterocyclic radical, a cycloalkyl radical, a substituted cycloalkyl radical, a heteroaryl radical, a substituted heteroaryl radical, a heteroaralkyl radical, or a substituted heteroaralkyl radical;
- X represents an oxygen atom, a —CH2— radical, a —CH—(CH2)p-NR5R6 radical, a sulfur atom, an SO radical, or an SO2 radical, with R5, R6, and p having the meanings given hereinafter;
- R5 and R6, which are identical or different, represent a hydrogen atom, an alkyl radical, a substituted alkyl radical, an aryl radical, or a substituted aryl radical;
- m can take the values of 0 or 1;
- n can take the values of 0, 1, 2, or 3;
- and
- p can take the values of 0, 1, or 2;
- and also addition salts of the compound of formula (I) with a pharmaceutically acceptable acid, addition salts of the compound of formula (I) with a pharmaceutically acceptable base, and enantiomers of the compound of formula (I).
9 more elements
A compound, addition salts of the compound with a pharmaceutically acceptable acid, addition salts of the compound with a pharmaceutically acceptable base, and enantiomers of the compound, wherein the compound is selected from the group consisting of:
- 1) (S)-3-(4-benzyloxybenzenesulfonylamino)-N-hydroxy-2-piperidin-1-ylpropionamide;
- 2) (S)-3-(4-benzyloxybenzenesulfonylamino)-N-hydroxy-2-pyrrolidin-1-ylpropionamide;
- 3) (S)-3-[4-(4-fluorobenzyloxy)benzenesulfonylamino]-N-hydroxy-2-piperidin-1-ylpropionamide;
- 4) (S)-3-[(4-benzyloxybenzenesulfonyl)methylamino]-N-hydroxy-2-piperidin-1-ylpropionamide;
- 5) (S)—N-hydroxy-3-[4-(naphthalen-2-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-ylpropionamide;
- 6) (S)-3-[4-(3,4-dichlorobenzyloxy)benzenesulfonylamino]-N-hydroxy-2-piperidin-1-ylpropionamide;
- 7) (S)-3-(4-benzyloxybenzenesulfonylamino)-N-hydroxy-2-morpholin-4-ylpropionamide;
- 8) (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino)-2-piperidin-1-ylpropionamide;
- 9) (S)-3-(4-(3,5-dichlorobenzyloxy)benzenesulfonylamino]-N-hydroxy-2-piperidin-1-ylpropionamide;
- 10) (S)—N-hydroxy-2-piperidin-1-yl-3-(4-propoxybenzenesulfonylamino)propionamide;
- 11) (S)-3-(4-cyclopropylmethoxybenzenesulfonylamino)-N-hydroxy-2-morpholin-4-ylpropionamide;
- 12) (S)-3-[4-(4-tert-butylbenzyloxy)benzenesulfonylamino]-N-hydroxy-2-morpholin-4-ylpropionamide;
- 13) (S)—N-hydroxy-2-morpholin-4-yl-3-(4-phenethyloxybenzenesulfonylamino)propionamide;
- 14) (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-morpholin-4-ylpropionamide;
- 15) (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-ylpropionamide;
- 16) (R)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-pyrrolidin-1-ylpropionamide;
- 17) (R)—N-hydroxy-3-(4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino-2-piperidin-1-yl-propionamide;
- 18) (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-thiomorpholin-4-yl-propionamide;
- 19) (S)-2-(1,1-dioxothiomorpholin-4-yl)-N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 20) (S)-2-diethylamino-N-hydroxy-3-[4-(2-methylpyridin-4-ylmethoxy)benzenesulfonylamino]-propionamide;
- 21) (S)-3-[4-(2,6-dimethylpyridin-4-ylmethoxy)benzenesulfonylamino]-2-(ethylpropylamino)-N-hydroxy-propionamide;
- 22) (S)-2-azepan-1-yl-N-hydroxy-3-[4-(3-methylbenzyloxy)benzenesulfonylamino]propionamide;
- 23) (S)-2-azepan-1-yl-N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-propionamide;
- 24) (S)—N-hydroxy-2-piperidin-1-yl-3-[4-(pyrazolo[1,5-a]pyridin-3-ylmethoxy)benzenesulfonylamino]-propionamide;
- 25) (S)—N-hydroxy-3-[4-(2-methylpyrazolo[1,5-a]pyridin-3-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-ylpropionamide;
- 26) (S)—N-hydroxy-2-piperidin-1-yl-3-[4-(quinolin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 27) (S)—N-hydroxy-2-morpholin-4-yl-3-[4-(quinolin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 28) (S)—N-hydroxy-3-{propyl[4-(quinolin-4-ylmethoxy)benzenesulfonyl]amino}-2-pyrrolidin-1-yl-propionamide;
- 29) (S)-2-diethylamino-N-hydroxy-3-[4-(quinolin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 30) (S)—N-hydroxy-3-[4-(3-methylbenzyloxy)benzenesulfonylamino]-2-[1,4]-oxazocan-4-yl-propionamide;
- 31) (S)-2-azocan-1-yl-N-hydroxy-3-[4-(pyrimidin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 32) (S)—N-hydroxy-2-morpholin-4-yl-3-[4-(pyrazolo[1,5-a]pyridin-3-ylmethoxy)benzenesulfonylamino]-propionamide;
- 33) (S)—N-hydroxy-3-[4-(pyrazolo[1,5-a]pyridin-3-ylmethoxy)benzenesulfonylamino]-2-thiomorpholin-4-ylpropionamide;
- 34) (S)—N-hydroxy-2-piperidin-1-yl-3-[4-(4-propoxybenzyloxy)benzenesulfonylamino]propionamide;
- 35) (R)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-morpholin-4-yl-propionamide;
- 36) (S)-2-(4-ethylaminopiperidin-1-yl)-N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 37) (S)-2-(3-aminopyrrolidin-1-yl)-N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 38) (S)-2-(3-dimethylaminomethylpyrrolidin-1-yl)-N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 39) (S)-2-(4-benzylaminopiperidin-1-yl)-N-hydroxy-3-[4-(2-methylpyridin-4-ylmethoxy)benzenesulfonylamino]propionamide;
- 40) (S)—N-hydroxy-3-[4-(2-methyl-1H-indol-3-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-yl-propionamide;
- 41) (S)—N-hydroxy-3-[4-(2-isopropylbenzofuran-3-ylmethoxy)benzenesulfonylamino]-2-morpholin-4-yl-propionamide;
- and
- 42) (S)-2-azetidin-1-yl-N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-propionamide.
40 more elements
Dependencies are inferred from the claim text.