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- Nachgewiesen in: USPTO Patent Applications
- Sprachen: English
- Document Number: 20110118219
- Publication Date: May 19, 2011
- Appl. No: 12/934135
- Application Filed: March 19, 2009
- Assignees: UNIVERSITY OF MARYLAND, BALTIMORE (Baltimore, MD, US)
- Claim: 1. A C-17 heteroaryl steroid compound of formula I: [chemical expression included] wherein: the ABC ring structure is the A, B and C ring portions of a steroid or analog thereof; which are optionally substituted; the bond at the 16,17 position is a double bond or, when the compound is 17-(1H-benzimidiazol-1-yl)-androst-3-one, a single bond; X is an optionally substituted benzimidazole, benzotriazole, pyrimidinoimidazole, pyrimidinotriazole, diazole, triazole, or diazine; the benzimidazole, benzotriazole, and pyrimidinoimidazole groups being bonded to the steroid residue through a nitrogen atom on the 5-membered ring; and, the diazole, triazole, or diazine groups being bonded to the steroid residue through a carbon atom or nitrogen on the diazole, triazole, or diazine ring; and Y is an amino acid group, a succinate group, a phosphate group, or a sulfamate group; or a pharmaceutically acceptable salt of one of these compounds.
- Claim: 2. The C-17 heteroaryl steroid compound of claim 1, wherein the optional substituents for the ABC ring structure are selected from one or more of: alkyl and halogenated alkyl; alkenyl and halogenated alkenyl; halogen; amino; aminoalkylene; hydroxyimino; and hydroxy; optionally, hydrogen substituents on adjacent carbon atoms of the ABC ring structure are removed and replaced by an additional bond between the adjacent carbon atoms to result in a double bond between these carbons in the ring structure; and the optional substituents for the benzimidazole, benzotriazole, pyrimidinoimidazole, pyrimidinotriazole, diazole, triazole, or diazine structures are selected from: halogen, amino, aminoalkylene, hydroxy, —SH, —S-alkyl, alkyl and halogenated alkyl; these optional substituents being on ring carbon atoms of the benzimidazole, benzotriazole, pyrimidinoimidazole, pyrimidinotriazole, diazole, triazole, or diazine structures.
- Claim: 3. The C-17 heteroaryl steroid compound of claim 1 or 2, wherein the benzimidazole, benzotriazole, pyrimidinoimidazole, pyrimidinotriazole, diazole, triazole, or diazine structures are of the following formulae, respectively: [chemical expression included] wherein the * indicates the point of attachment to the steroid residue.
- Claim: 4. (canceled)
- Claim: 5. The C-17 heteroaryl steroid compound of claim 3, wherein each of the amino acid group, the succinate group or the phosphate group is connected to the A ring by an ester linkage.
- Claim: 6. The C-17 heteroaryl steroid compound of claim 5, wherein the amino acid group comprises an amino acid selected from alanine, arginine, aspartic acid, glutamic acid, histidine, isoleucine, leucine, proline, serine, tyrosine, glycine, aspartic acid, valine, lysine, phenylalanine and combinations thereof.
- Claim: 7. The C-17 heteroaryl steroid compound of claim 6, wherein the amino acid group comprises a dipeptide including an amino acid selected from alanine, arginine, aspartic acid, glutamic acid, histidine, isoleucine, leucine, proline, serine, tyrosine, glycine, aspartic acid, valine, lysine, phenylalanine and combinations thereof.
- Claim: 8. The C-17 heteroaryl steroid compound of claim 7, wherein X is selected such that the compound comprises one of the following structures: [chemical expression included] [chemical expression included] and pharmaceutically acceptable salts thereof
- Claim: 9. The C-17 heteroaryl steroid compound of claim 8, comprising a prodrug of a compound of one of the following structures: [chemical expression included] [chemical expression included]
- Claim: 10. The C-17 heteroaryl steroid compound of claim 9, which is a compound of one of the following structures: [chemical expression included] [chemical expression included]
- Claim: 11. A pharmaceutical composition comprising one or more compounds of claim 10 and a pharmaceutically acceptable excipient, carrier or diluent.
- Claim: 12. A method of treating cancer, a disease or a condition in a subject in need thereof, comprising: administering to a patient in need thereof an effective amount of a composition of claim 10.
- Claim: 13. The method of claim 12, further comprising administering to a patient in need thereof an effective amount of an anti-androgonen, a CYP17 inhibitor, a luteinizing hormone-releasing hormone agonist, a drug for preventing androgen production, an estrogen, or a chemotherapy drug.
- Claim: 14. The method of claim 12, wherein the composition is administered to the subject in combination with a hormone therapy, a chemotherapy, a radiation therapy, an immunotherapy, or surgery.
- Claim: 15. The method of claim 14, wherein the cancer, the disease or the condition is selected from prostate cancer, breast cancer, ovarian cancer, urogenital cancer, or prostate hyperplasia.
- Claim: 16. (canceled)
- Claim: 17. (canceled)
- Claim: 18. The method of claim 14 wherein the compound or composition comprises a pro drug of 3β-Hydroxy-17-(1H-benzimidazole-1-yl)androsta-5,16-diene; 17-(1H-Benimidazole-1-yl)androsta-4,16-diene-3-one; 3-Hydroxy-17-(benzo-1H-1,2,3-triazole-1-yl))androsta-5,16-diene; 17-(Benzo-1H-1,2,3-triazol-1-yl)androsta-4,16-diene-3-one; 3β-Hydroxy-17-(1H-1,2,4-triazol-1-yl)androsta-5,16-diene; or 3β-Hydroxy-17-(1H-imidazol-1-yl)androsta5,16-diene.
- Claim: 19. (canceled)
- Current U.S. Class: 514/170
- Current International Class: 61; 07; 07; 07; 07; 07; 61
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