NOVEL COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, AND METHODS OF USE FOR SAME
The class compounds of the present invention may be represented by Formula (I), wherein X may be O, S, or N. R 1 and R 2 are independently either H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl. R 3 and R 4 are independently either H, an aryl group, a heteroaryl group, and a heterocyclic ring group having 4 to 6 carbon atoms, wherein the aryl, heteroaryl, and heterocyclic moieties are optionally substituted with one or more of a first substitution group defined herein. In a further embodiment, R 3 and R 4 along with the atoms and bonds to which they are attached, form an optionally substituted 5-7 membered ring having at least one nitrogen atom within the ring structure.
1 . A compound comprising the formula:
wherein X is a heteroatom selected from the group consisting of O, S, and N;
R 1 and R 2 are independently selected from the group consisting of H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; and
R 3 and R 4 are independently a hydrogen or a member of a substituted or unsubstituted ring having 4-6 carbon atoms, provided that both R 3 and R 4 are not hydrogens and further that, if neither R 3 and R 4 are hydrogens, then R 3 and R 4 are members of the same substituted or unsubstituted ring having 4-6 carbon atoms.
2 - 77 . (canceled)
78 . The compound of claim 1 , wherein X is either an oxygen or sulfur.
79 . The compound of claim 1 , wherein R 3 is a hydrogen and R 4 is selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heterocyclic ring group each having 4-6 carbon atoms.
80 . The compound of claim 79 , wherein R 4 is substituted with one or more of a first substituent group selected from the group consisting of a halogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, —OR 5 , —SR 5 , —CN, —CONH 2 , —SO 2 NH 2 , —C(O)OR 6 —CONHR 7 and a cycloalkyl or a heterocyclic ring, wherein the cycloalkyl or heterocyclic ring of the first substituent group is optionally aromatic, is optionally fused to two adjacent atoms of R 4 , and is optionally substituted with at least one substituent group comprised of R 5 ,
wherein R 5 is selected from the group consisting of a C 1 -C 8 alkyl, C 1 -C 8 alkoxy, aryl, alkylaryl, and arylalkyl, and is optionally substituted with one or more of a second substituent group selected from the group consisting of a halogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy group, a C 1 -C 3 haloalkyl group, and a C 1 -C 3 haloalkoxy group,
wherein R 6 is comprised of a C 1 -C 8 alkyl group and R 7 is selected from the group consisting of a C 1 -C 8 alkyl group, an allyl group, a morpholine, a piperazine, an N-substituted piperazine with R 5 , and a 5- or 6-membered heterocycle containing N, O, S or any combination thereof.
81 . The compound of claim 80 , wherein R 3 is a hydrogen and R 4 is an aryl group optionally substituted with one or more of the first substituent group.
82 . The compound of claim 1 , wherein R 1 is a straight or branched chain C 6 -C 8 alkyl group.
83 . The compound of claim 1 , wherein R 1 is a straight or branched chain C 8 alkyl group.
84 . The compound of claim 1 , wherein R 2 is a straight or branched chain C 1 -C 3 alkyl group.
85 . The compound of claim 1 , wherein R 2 is a methyl group.
86 . A compound comprising the formula:
wherein R 1 and R 2 are independently selected from the group consisting of H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; and
R 3 and R 4 are independently a hydrogen or a member of a substituted or unsubstituted ring having 4-6 carbon atoms, provided that both R 3 and R 4 are not a hydrogen and further that, if neither R 3 and R 4 are hydrogens, then R 3 and R 4 are members of the same substituted or unsubstituted ring having 4-6 carbon atoms.
87 . A compound of claim 86 , wherein said compound is selected from the group consisting of
88 . A pharmaceutical composition comprising a pharmaceutical diluent and a compound according to claim 1 .
89 . The pharmaceutical composition of claim 88 , wherein X is sulfur.
90 . The pharmaceutical composition of claim 88 , wherein R 1 is a straight or branched chain C 6 -C 8 alkyl group and R 2 is a straight or branched chain C 1 -C 3 alkyl.
91 . The pharmaceutical composition of claim 88 , wherein R 3 is a hydrogen and R 4 is an aryl group optionally substituted with one or more of the first substitution group.
92 . The pharmaceutical composition of claim 89 , wherein the compound is selected from the group consisting of
93 . A method of treating cancer, inducing weight loss, inhibiting growth of invasive microbial cells, or inhibiting fatty acid synthase activity in a subject, comprising administering to the subject an effective amount of a pharmaceutical composition according to claim 88 .
94 . The method of claim 93 , wherein the method comprises treating cancer.
95 . The method of claim 93 , wherein the subject is an animal.
96 . The method of claim 95 , wherein the subject is a human.
97 . The method of claim 93 , wherein X is sulfur.
98 . The method of claim 93 , wherein R 1 is a straight or branched chain C 6 -C 8 alkyl group and R 2 is a straight or branched chain C 1 -C 3 alkyl.
99 . The method of claim 93 , wherein R 3 is a hydrogen and R 4 is an aryl group optionally substituted with one or more of the first substituent group.
100 . The method of claim 93 , wherein the pharmaceutical composition includes one or more compounds selected from the group consisting of: