Novel benzenesulfonamide compounds, method for synthesizing same, and use thereof in medicine as well as in cosmetics
AssigneeGalderma Research & Development
InventorsCarine MOUNIER, Isabelle Carlavan, Jerome Aubert, André Jomard, Patricia Rossio
Life of this patent
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Abstract
Provided herein are novel benzenesulfonamide compounds having a structure of formula (I) below: as well as to the method for synthesizing same and to the use thereof in pharmaceutical compositions to be used in human or veterinary medicine, as well as to the use thereof. Also provided herein are methods of using the disclosed pharmaceutical compositions for the treatment of neuroinflammatory skin diseases such as acne.
Claims25
A method of treating acne, the method comprising administering a pharmaceutical composition comprising an effective amount of a compound, a salt thereof, or an enantiomer thereof to a subject in need thereof, wherein the compound has a structure of formula (I)
- in which:
- R1 is a hydrogen, an alkyl radical, a substituted alkyl radical, an alkenyl radical, a substituted alkenyl radical, an alkynyl radical, a substituted alkynyl radical, an aralkyl radical, a substituted aralkyl radical, a heteroaralkyl radical, a substituted heteroaralkyl radical, a —C(O)—R4 radical, a —SO2—R4 radical, or a —C(O)OR4 radical, wherein R4 is as defined below;
- R2 is a hydrogen atom or a lower alkyl radical;
- R3 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;
- 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, or a substituted aralkyl radical;
- and
- n can take the values of 0, 1, 2, or 3.
A method of inhibiting inflammation induced by P. acnes, the method comprising administering a pharmaceutical composition comprising an effective amount of a compound, a salt thereof, or an enantiomer thereof to a subject infected with P. acnes, wherein the compound has a structure of formula (I)
- in which:
- R1 is a hydrogen, an alkyl radical, a substituted alkyl radical, an alkenyl radical, a substituted alkenyl radical, an alkynyl radical, a substituted alkynyl radical, an aralkyl radical, a substituted aralkyl radical, a heteroaralkyl radical, a substituted heteroaralkyl radical, a —C(O)—R4 radical, a —SO2—R4 radical, or a —C(O)OR4 radical, wherein R4 is as defined below;
- R2 is a hydrogen atom or a lower alkyl radical;
- R3 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;
- 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, or a substituted aralkyl radical;
- and
- n can take the values of 0, 1, 2, or 3.
A method of treating acne, the method comprising administering a pharmaceutical composition comprising an effective amount of a compound, a salt thereof, or an enantiomer thereof to a subject in need thereof, wherein the compound is (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-[4-(propane-2-sulfonyl)piperazin-1-yl]propionamide.
A method of inhibiting inflammation induced by P. acnes, the method comprising administering a pharmaceutical composition comprising an effective amount of a compound, a salt thereof, or an enantiomer thereof to a subject infected with P. acnes, wherein the compound is (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-[4-(propane-2-sulfonyl)piperazin-1-yl]propionamide.
A method of inhibiting activation of a transcription factor in an acne lesion comprising applying a pharmaceutical composition comprising an effective amount of a compound, a salt thereof, or an enantiomer thereof, to a skin having acne lesions wherein the compound has a structure of formula (I),
- in which:
- R1 is a hydrogen, an alkyl radical, a substituted alkyl radical, an alkenyl radical, a substituted alkenyl radical, an alkynyl radical, a substituted alkynyl radical, an aralkyl radical, a substituted aralkyl radical, a heteroaralkyl radical, a substituted heteroaralkyl radical, a —C(O)—R4 radical, a —SO2—R4 radical, or a —C(O)OR4 radical, wherein R4 is as defined below;
- R2 is a hydrogen atom or a lower alkyl radical;
- R3 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;
- 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, or a substituted aralkyl radical;
- and
- n can take the values of 0, 1, 2, or 3.
A method of inhibiting production of MMP-12, the method comprising applying a pharmaceutical composition comprising an effective amount of a compound, a salt thereof, or an enantiomer thereof, to a subject in need thereof, wherein the compound has a structure of formula (I),
- in which:
- R1 is a hydrogen, an alkyl radical, a substituted alkyl radical, an alkenyl radical, a substituted alkenyl radical, an alkynyl radical, a substituted alkynyl radical, an aralkyl radical, a substituted aralkyl radical, a heteroaralkyl radical, a substituted heteroaralkyl radical, a —C(O)—R4 radical, a —SO2—R4 radical, or a —C(O)OR4 radical, wherein R4 is as defined below;
- R2 is a hydrogen atom or a lower alkyl radical;
- R3 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;
- 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, or a substituted aralkyl radical;
- and
- n can take the values of 0, 1, 2, or 3.
Dependencies are inferred from the claim text.