Histone deacetylase inhibitors

A compound of formula (I):

• wherein
• A is a cyclic moiety selected from the group consisting of aryl and heteroaryl;
• the cyclic moiety being optionally substituted with alkyl, alkenyl, alkynyl, hydroxylalkyl, or amino;
• each of X1 and X2, independently, is O or S;
• Y is —CH2—, —O—, —S—, —N(Ra)—, —N(Ra)—C(O)—O—, —O—C(O)—N(Ra)—, —N(Ra)—C(O)—N(Rb)—, —O—C(O)—O—, or a bond;
• each of Ra and Rb, independently, being hydrogen, alkyl, hydroxylalkyl, or haloalkyl;
• Y2 is CH2;
• L is an unsaturated C4-8 hydrocarbon chain containing at least one double bond;
• said unsaturated-hydrocarbon chain being substituted with C3-5 cycloalkyl, 3-5 membered heterocycloalkyl, monocyclic aryl, 5-6 membered heteroaryl, C1-4 alkylcarbonyloxy, C1-4 alkylcarbonyl, or formyl, —NH2, —NH(C1-2 alkyl), or —N(C1-2 alkyl)2, or —N(C1-2 alkyl)2;
• provided that when L contains two or more double bonds, the double bonds are not adjacent to each other;
• or a salt thereof, wherein the compound is not 8-phenyl-5-octenoic acid, 6-phenyl-5-hexenoic acid, 5,5-diphenylpent-4-enoic acid, 2,2-dichloro-12-phenyl-11-dodecenoic acid, 8-phenyl-6-octenoic acid or 13-phenyl-11-triedecenoic acid.

A pharmaceutical composition, comprising compound of formula (I):

• wherein
• A is a cyclic moiety selected from the group consisting of C3-14 cycloalkyl, 3-14 membered heterocycloalkyl, C4-14 cycloalkenyl, 3-14 membered heterocycloalkenyl, aryl, and heteroaryl;
• the cyclic moiety being optionally substituted with 1-3 substituents, each of which is independently selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, hydroxyl, hydroxylalkyl, halo, haloalkyl, amino, alkylcarbonyloxy, alkyloxycarbonyl, alkylcarbonyl, alkylsulfonylamino, aminosulfonyl, and alkylsulfonyl;
• each of X1 and X2, independently, is O or S;
• Y1 is —CH2—, —O—, —S—, —N(Ra)—, —N(Ra)—C(O)—O—, —O—C(O)—N(Ra)—, —N(Ra)—C(O)—N(Rb)—, —O—C(O)—O—, or a bond;
• each of Ra and Rb independently, being hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylalkyl, hydroxyl, or haloalkyl;
• Y2 is CH2;
• L is an unsaturated C4-8 hydrocarbon chain containing at least one double bond;
• said hydrocarbon unsaturated chain being substituted with C3-5 cycloalkyl, 3-5 membered heterocycloalkyl, monocyclic aryl, 5-6 membered heteroaryl, C1-4 alkylcarbonyloxy, C1-4 alkyloxycarbonyl, C1-4 alkylcarbonyl, or formyl —NH(C1-2 alkyl), or —N(C1-2 alkyl)2, or —N(C1-2 alkyl)2;
• and further being optionally interrupted by —N(Rc)—C(O)—O—, —O—C(O)—N(Rc)—, —N(Rc)—C(O)—N(Rd)—, or —O—C(O)—O—;
• each of Rc and Rd, independently, being hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylalkyl, hydroxyl, or haloalkyl;
• or a salt thereof;
• and
• a pharmaceutically acceptable carrier, wherein the compound is not 8-phenyl-5-octenoic acid, 6-phenyl-5-hexenoic acid, 5,5-diphenylpent-4-enoic acid, 2,2-dichloro-12-phenyl-11-dodecenoic acid, 8-phenyl-6-octenoic acid or 13-phenyl-11-triedecenoic acid.

A compound of formula (I):

• wherein
• A is a cyclic moiety selected from the group consisting of C3-14 cycloalkyl, 3-14 membered heterocycloalkyl, C4-14 cycloalkenyl, 3-14 membered heterocycloalkenyl, aryl, and heteroaryl;
• the cyclic moiety being optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, hydroxyl, hydroxylalkyl, halo, haloalkyl, amino, alkylcarbonyloxy, alkyloxycarbonyl, alkylcarbonyl, alkylsulfonylamino, aminosulfonyl, or alkylsulfonyl;
• each of X1 and X2, independently, is O or S;
• Y1 is —CH2—, —S—, —N(Ra)—, —N(Ra)—C(O)—O—, —O—C(O)—N(Ra)—, —N(Ra)—C(O)—N(Rb)—, —O—C(O)—O—, or a bond;
• each of Ra and Rb, independently, being hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylalkyl, hydroxyl, or haloalkyl;
• Y2 is —CH2—;
• L is an unsaturated C4-8 hydrocarbon chain containing at least one double bond;
• said unsaturated hydrocarbon chain being substituted with C3-5 cycloalkyl, 3-5 membered heterocycloalkyl, monocyclic aryl, 5-6 membered heteroaryl, C1-4 alkylcarbonyloxy, C1-4 alkylcarbonyl, or formyl;
• and further being optionally interrupted by —N(Rc)—C(O)—O—, —O—C(O)—N(Rc)—, N(Rc)—C(O)—N(Rd)—, or —O—C(O)—O—;
• each of Rc and Rd, independently, being hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylalkyl, hydroxyl, or haloalkyl;
• or a salt thereof, wherein the compound is not 5,5-diphenylpent-4-enoic acid, 8-phenyl-6-octenoic acid or 13-phenyl-11-triedecenoic acid.

A compound of formula (I):

• wherein
• A is a cyclic moiety selected from the group consisting of C3-14 cycloalkyl, 3-14 membered heterocycloalkyl, C4-14 cycloalkenyl, 3-14 membered heterocycloalkenyl, aryl, a heteroaryl;
• the cyclic moiety being optionally substituted with alkyl, alkenyl, alkynyl, alkoxy, hydroxyl, hydroxylalkyl, halo, haloalkyl, amino, alkylcarbonyloxy, alkyloxycarbonyl, alkylcarbonyl, alkylsulfonylamino, aminosulfonyl, or alkylsulfonyl;
• each of X1 and X2, independently, is O or S;
• Y1 is —CH2—, —O—, —S—, —N(Ra)—, —N(Ra)—C(O)—O—, —O—C(O)—N(Ra)—, —N(Ra)—C(O)—N(Rb)—, —O—C(O)—O—, or a bond;
• each of Ra and Rb, independently being hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylalkyl, hydroxyl, or haloalkyl;
• Y2 is CH2;
• L is an unsaturated C4-8 hydrocarbon chain containing at least one double bond;
• said unsaturated-hydrocarbon chain being substituted with C3-5 cycloalkyl, 3-5 membered heterocycloalkyl, monocyclic aryl, 5-6 membered heteroaryl, C1-4 alkylcarbonyloxy, C1-4 alkylcarbonyl, or formyl;
• provided that when L contains two or more double bonds, the double bonds are not adjacent to each other;
• or a salt thereof, wherein the compound is not 8-phenyl-5-octenoic acid, 6-phenyl-5-hexenoic acid, or 5,5-diphenylpent-4-enoic acid.

A compound of formula (I):

• wherein
• A is phenyl, naphthyl, indanyl, or tetrahydronaphthyl;
• each of X1 and X2, independently, is O or S;
• Y1 is —CH2—, —S—, —N(Ra)—C(O)—O—, —O—C(O)—N(Ra)—, —N(Ra)—C(O)—N(Rb)—, —O—C(O)—O—, or a bond;
• each of Ra and Rb, independently, being hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylalkyl, hydroxyl, or haloalkyl;
• Y2 is —CH2 —;
• L is an unsaturated C4-8 hydrocarbon chain containing at least one double bond;
• said unsaturated hydrocarbon chain being substituted with C3-5 cycloalkyl, 3-5 membered heterocycloalkyl, monocyclic aryl, 5-6 membered heteroaryl, C1-4 alkylcarbonyloxy, C1-4 alkyloxycarbonyl, C1-4 alkylcarbonyl, or formyl;
• or a salt thereof, wherein the compound is not 8-phenyl-5-octenoic acid or 5,5-diphenylpent-4-enoic acid.