Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
A01N-043/16
A01N-043/02
출원번호
US-0695275
(2003-10-28)
등록번호
US-7300954
(2007-11-27)
발명자
/ 주소
Sanders,Bob G.
Kline,Kimberly
Yu,Weiping
출원인 / 주소
Research Development Foundation
대리인 / 주소
Fulbright & Jaworski L.L.P.
인용정보
피인용 횟수 :
4인용 특허 :
29
초록▼
The present invention provides an antiproliferative compound having a structural formula where X and Y independently are oxygen, nitrogen or sulfur; R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, ester, thioamide, thiolacid, thiolester, saccharide, alk
The present invention provides an antiproliferative compound having a structural formula where X and Y independently are oxygen, nitrogen or sulfur; R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, ester, thioamide, thiolacid, thiolester, saccharide, alkoxy-linked saccharide, amine, sulfonate, sulfate, phosphate, alcohol, ethers or nitrites; R2 and R3 are hydrogen or R4; R4 is methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide or amine; and R5 is alkenyl; where when Y is nitrogen, said nitrogen is substituted with R6, wherein R6 is hydrogen or methyl. Also provided are methods for treating a cell proliferative disease and for inducing apoptosis in a cell comprising administering this compound is also provided.
대표청구항▼
What is claimed is: 1. A method for inhibiting the growth of tumor cells in an individual comprising administering to the individual a pharmacologically effective dose of a compound having a structural formula wherein X is oxygen; Y is oxygen, NH or NCH3; R1 is--(CH2)1-5CO2H,--(CH2)7CO2H,--CH2CON
What is claimed is: 1. A method for inhibiting the growth of tumor cells in an individual comprising administering to the individual a pharmacologically effective dose of a compound having a structural formula wherein X is oxygen; Y is oxygen, NH or NCH3; R1 is--(CH2)1-5CO2H,--(CH2)7CO2H,--CH2CONH2,--CH2CO2CH3,--CH2CON(CH2CO2H)2,--(CH2)2OH,--(CH2)3NH3Cl, or--(CH2)2OSO3NHEt3; R2 and R3 are independently hydrogen or R4; R4 is methyl; and R5is 2. The method of claim 1, wherein said compound is α-tocotrienol, γ-tocotrienol or δ-tocotrienol. 3. The method of claim 1, wherein said compound is 2,5,7,8-tetramethyl-2R-(4,8,12-trimethyl-3,7,11 E:Z tridecatrien) chroman-6-yloxy) acetic acid. 4. The method of claim 1, wherein said compound induces apoptosis, DNA synthesis arrest, cell cycle arrest, or cellular differentiation in cells comprising said tumor. 5. The method of claim 1, wherein said compound is administered in a dose of about 1 mg/kg to about 60 mg/kg. 6. The method of claim 5, wherein administration of said composition is oral, topical, liposomal/aerosol, intraocular, intranasal, parenteral, intravenous, intramuscular, or subcutaneous. 7. The method of claim 1, wherein said tumor cells comprise an ovarian cancer, a cervical cancer, an endometrial cancer, a bladder cancer, a lung cancer, a breast cancer, a testicular cancer, a prostate cancer, a glioma, a fibrosarcoma, a retinoblastoma, a melanoma, a soft tissue sarcoma, an osteosarcoma, a leukemia, a colon cancer, a carcinoma of the kidney, a pancreatic cancer, a basel cell carcinoma, or a squamous cell carcinoma. 8. A method of inducing apoptosis of a cell, comprising the step of contacting said cell with a pharmacologically effective dose of a compound having a structural formula wherein X is oxygen; Y is oxygen, NH or NCH3; R1 is--(CH2)1-5CO2H,--(CH2)7CO2H,--CH2CONH2,--CH2CO2CH3,--CH2CON(CH2CO2H)2,--(CH2)2OH,--(CH2)3NH3Cl or--(CH2)2OSO3NHEt3; R2 and R3 are independently hydrogen or R4; R4 methyl; and R5is 9. The method of claim 8, wherein said compound is α-tocotrienol, γ-tocotrienol or δ-tocotrienol. 10. The method of claim 8, wherein said compound is 2,5,7,8-tetramethyl-2R-(4,8,12-trimethyl-3,7,11 E:Z tridecatrien) chroman-6-yloxy) acetic acid. 11. The method of claim 1, wherein R1 is--(CH2)1-5CO2 or--CH2)7CO2H. 12. The method of claim 1, wherein R1 is--CH2CONH2. 13. The method of claim 1, wherein R1 is--CH2CO2CH3. 14. The method of claim 1, wherein R1 is--CH2CON(CH2CO2H)2. 15. The method of claim 1, wherein R1 is--(CH2)2OH. 16. The method of claim 1, wherein R1 is--(CH2)3NH3Cl. 17. The method of claim 1, wherein R1 is--(CH2)2OSO3NHEt3. 18. The method of claim 1, wherein R2 is hydrogen. 19. The method of claim 1, wherein R2 is methyl. 20. The method of claim 1, wherein R3 is hydrogen. 21. The method of claim 1, wherein R3 is methyl. 22. The method of claim 1, wherein R4 is methyl. 23. The method of claim 1, wherein Y is NCH3. 24. The method of claim 1, wherein Y is NH. 25. The method of claim 8, wherein R1 is--(CH2)1-5CO2 or--(CH2)7CO2H. 26. The method of claim 8, wherein R1 is--CH2CONH2. 27. The method of claim 8, wherein R1 is--CH2CO2CH3. 28. The method of claim 8, wherein R1 is--CH2CON(CH2CO2H)2. 29. The method of claim 8, wherein R1 is--(CH2)2OH. 30. The method of claim 8, wherein R1 is--(CH2)3NH3Cl. 31. The method of claim 8, wherein R1 is--(CH2)2OSO3NHEt3. 32. The method of claim 8, wherein R2 is hydrogen. 33. The method of claim 8, wherein R2 is methyl. 34. The method of claim 8, wherein R3 is hydrogen. 35. The method of claim 8, wherein R3 is methyl. 36. The method of claim 8, wherein R4 is methyl. 37. The method of claim 8, wherein Y is NCH3. 38. The method of claim 8, wherein Y is NH. 39. The method of claim 1, wherein the compound has the structural formula wherein X is oxygen; Y is oxygen, NH or NCH3; R1 is--(CH2)1-3CO2H,--CH2CON(CH2CO2H)2,--(CH2)3NH3Cl, or--(CH2)2OSO3NHEt3; R2 and R3 are independently hydrogen or R4; R4 is methyl; and R5 is 40. The method of claim 8, wherein the compound has the structural formula wherein X is oxygen; Y is oxygen, NH or NCH3; R1 is--(CH2)1-3CO2H,--CH2CON(CH2CO2H)2,--(CH2)3NH3Cl, or--(CH2)2OSO3NHEt3; R2 R3 are independently hydrogen or R4; R4 is methyl; and R5 is
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