[특허]Compounds and methods for synthesis of bicyclic nucleic acid analogs

Compounds and methods for synthesis of bicyclic nucleic acid analogs 원문보기

IPC분류정보
국가/구분	United States(US) Patent 등록
국제특허분류(IPC7판)	C07H-021/00
출원번호	UP-0747042 (2007-05-10)
등록번호	US-7569686 (2009-08-24)
발명자 / 주소	Bhat, Balkrishen Xia, Jie Seth, Punit P. Vasquez, Guillermo Migawa, Michael T. Allerson, Charles Prakash, Thazha P. Swayze, Eric E.
출원인 / 주소	Isis Pharmaceuticals, Inc.
대리인 / 주소	Day, Jones
인용정보	피인용 횟수 : 113 인용 특허 : 121

초록 ▼

The present invention provides compounds and methods of using them for preparing bicyclic nucleosides. The bicyclic nucleosides are useful for preparing chemically modified oligomeric compounds. Oligomeric compounds comprising these bicyclic nucleosides have enhanced properties such as increased nu

대표청구항 ▼

What is claimed is: 1. A compound having formula I: wherein: R1 is H or a hydroxyl protecting group; R2 is H or a hydroxyl protecting group; R3 and R4 are each independently C1-C6 alkyl or substituted C1-C6 alkyl; and Q is an optionally substituted polycyclylic aromatic or heteroaromatic radical. 2. The compound of claim 1 wherein said optionally substituted polycyclylic aromatic or heteroaromatic radical comprises from 2 to about 5 fused rings. 3. The compound of claim 2 wherein Q comprises two fused rings. 4. The compound of claim 2 wherein Q comprises at least one heteroaromatic ring. 5. The compound of claim 3 wherein Q includes only carbon and hydrogen atoms. 6. The compound of claim 5 wherein Q is 2-naphthalenyl. 7. The compound of claim 1 wherein Q is pyrenyl, purinyl, acridinyl, xanthenyl, fluorenyl, phenanthrenyl, anthracenyl, quinolinyl, isoquinolinyl, naphthalenyl, perylenyl, phenanthridinyl, phenazinyl, anthraquinonyl, azulenyl or dibenzofuranyl. 8. The compound of claim 1 wherein R1 and R2 are each H. 9. The compound of claim 1 wherein R1 and R2 are each, independently, a hydroxyl protecting group. 10. The compound of claim 1 wherein one of R1 and R2 is H and the other of R1 and R2 is a hydroxyl protecting group. 11. The compound of claim 1 wherein R3 and R4 are each, independently, C1-C6 alkyl. 12. The compound of claim 11 wherein R3 and R4 are each methyl. 13. The compound of claim 1 wherein: R1 is a hydroxyl protecting group; R2 is H; and R3 and R4 are each methyl. 14. The compound of claim 13 wherein Q is 2-napthalenyl. 15. The compound of claim 1 having the configuration: 16. The compound of claim 15 having the formula: 17. The compound of claim 1 having the configuration: 18. The compound of claim 17 having the formula: 19. A method of preparing a bicyclic nucleoside comprising a bridge between the 4' and 2' ring carbons using the compound of claim 1. 20. The method of claim 19 wherein said bridge comprises from 2 to 3 bivalent subunits. 21. The method of claim 20 wherein said bivalent subunits are each, independently, selected from--CR5R6--,--C(═O)--,--NR5, and--O--, wherein each R5 and R6 is, independently, H, C1-C6 alkyl, substituted C1-C6 alkyl, a substituted heteroatom (O, S or N) or a protecting group. 22. The method of claim 21 wherein said bivalent subunits form a bridge having the formula: --CH2--O--,--(CH2)2--O--,--CH2--O--N(R5)--,--CH2--N(R5)--O--, CH2--N(R5)--CH2--,--CH(R5)--O--,--CH2--N(R5)--N(R5)--or--C(═O)--N(R5)--CH2--. 23. The method of claim 19 wherein said compound has the configuration: 24. The method of claim 23 wherein said compound has the formula: 25. The method of claim 19 wherein said compound has the configuration: 26. The method of claim 25 wherein said compound has the formula:

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Compounds and methods for synthesis of bicyclic nucleic acid analogs 원문보기

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