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US 6,172,112 B2Granted
Retinoids and use thereof
AssigneeThe UAB Research Foundation
InventorsWayne J. Brouillette, Donald D. Muccio
Life of this patent
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Abstract
The present invention provides new retinoid compounds and uses of the compounds in humans and animals for chemoprevention of skin and/or breast cancer and for therapy of leukemia.
Claims26
A retinoid compound having a structure selected from the group consisting of:
- wherein when said compound has a structure selected from the group consisting of I(a) and I(b) and wherein R1 is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, t-butyl, phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl;
- R2 is selected from the group consisting of cyclohexyl, 3-cyclohexenyl, benzyl, C3-C8 cyclic alkyls, and arylalkyl,
- wherein when said compound has a structure selected from the group consisting of I(a) and I(b) and wherein R2 is 2-methylpropyl, R1 is selected from the group consisting of phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl,
- wherein when said compound has a structure selected from the group consisting of I(a) and I(b) and R2 is n-butyl, R1 is selected from the group consisting of phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl;
- and
- wherein when said compound has a structure selected from the group consisting of II(a) and II(b), R1 is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, t-butyl, phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl;
- and R2 is selected fiom the group consisting of 2-methylpropyl, n-butyl, cyclohexyl, 3-cyclohexenyl, benzyl, C3-C8 cyclic alkyls, and arylalkyl.
4 more elements
Retinoid compounds having the structure selected from the group consisting of:
- wherein R1 is selected from the group consisting of phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl;
- and R2 is selected from the group consisting of H, ethyl, methyl, n-propyl, and i-propyl.
Retinoid compounds having the structure selected from the group consisting of:
- wherein said R1 represents one or two substituents on the aryl ring and is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, t-butyl, phenyl, benzyl, chloro, fluoro, methoxy, ethoxy, benzyloxy, C1-C8 cyclic alkyls, aryl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, and halogen;
- wherein R2 is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, 2-methylpropyl, n-butyl, cyclohexyl, 3-cyclohexenyl, benzyl, methoxy, ethoxy, benzyloxy, C1-C8 cyclic alkyls, aryl, arylalkyl, alkyloxy, aryloxy and arylalkyloxy;
- and wherein n=0-3.
A retinoid compound selected from the group consisting of (9Z)-UAB20, (all E)-UAB20, and (9Z)-UAB21, said (all E)-UAB20 has the structure:
- wherein said (all E)-UAB20 has a Ph group as R;
- and,
- and wherein said (9Z)-UAB20 and (9Z)-UAB21 have the structure:
- wherein said (9Z)-UAB20 has a Ph group as R and (9Z)-UAB21 has a CH2CH(CH3)2 group as R.
1 more element
A method of treating an individual having a neoplastic condition selected from the group consisting of brest cancer, prostate cancer, lung cancer, colon cancer, and leukemia, comprising the step of administering to said individual an effective dose of UAB8.
A method of treating an individual having a neoplastic condition, comprising the step of:
- administering to said individual a combination of two or more retinoid compounds selected from the group consisting of UAB8/analogs and UAB30/analogs;
- wherein said UAB8/analogs arc selected from compounds having structures selected from the group consisting of:
- wherein when said compound has structure selected from the group consisting of I(a) and I(b), R1 is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, t-butyl, phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl;
- and, R2 is selected from the group consisting of 2-methylpropyl, cyclohexyl, 3-cyclohexenyl, benzyl, C3-C8 cyclic alkyls, and arylalkyl,
- wherein when said compound has structure selected from the group consisting of I(a) and I(b) and R2 is n-butyl, R1 is selected from the group consisting of phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl;
- wherein when said compound has a structure selected from the group consisting of II(a) and II(b), R1 is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, t-butyl, phenyl, benzyl, C3-C8 cyclic alkyls, aryl, and arylalkyl;
- and R2 is selected from the group consisting of 2-methylpropyl, n-butyl, cyclohexyl, 3-cyclohexenyl, benzyl, C3-C8 cyclic alkyls, and arylalkyl;
- wherein said UAB30/analogs are selected from compounds having the structure selected from the group consisting of:
- wherein said R1 represents one or two substituents on the aryl ring and is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, t-butyl, phenyl, benzyl, chloro, fluoro, methoxy, ethoxy, benzyloxy, C1-C8 cyclic alkyls, aryl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, and halogen, R2 is selected from the group consisting of H, ethyl, methyl, n-propyl, i-propyl, 2-methylpropyl, n-butyl, cyclohexyl, 3-cyclohexenyl, benzyl, methoxy, ethoxy, benzyloxy, C1-C8 cyclic alkyls, aryl, arylalkyl, alkyloxy, aryloxy and arylalkyloxy;
- and n=0-3.
7 more elements
Dependencies are inferred from the claim text.