Iminosugar compounds with antiflavirus activity
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IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C12N-009/99
A61P-031/14
C07D-211/40
출원번호
US-0112694
(2008-04-30)
등록번호
US-8097728
(2012-01-17)
발명자
/ 주소
Gu, Baohua
Block, Timothy M.
Moriarty, Robert M.
Deshpande, Mahendra N.
Shah, Rajendra C.
출원인 / 주소
Philadelphia Health & Education Corporation
대리인 / 주소
Woodcock Washburn, LLP
인용정보
피인용 횟수 :
22인용 특허 :
31
초록▼
An anti-viral compounds effective against viruses belonging to the Flaviviridae family, wherein the anti-viral compounds are 1,5-dideoxy-1,5-imino-D-glucitol derivative compounds having the general formula (I) wherein R2, R3, R4 and R5 are the same or different and are selected from the group consi
An anti-viral compounds effective against viruses belonging to the Flaviviridae family, wherein the anti-viral compounds are 1,5-dideoxy-1,5-imino-D-glucitol derivative compounds having the general formula (I) wherein R2, R3, R4 and R5 are the same or different and are selected from the group consisting of hydrogen, acyl, benzyl, alkyl, aryl, sulfonyl, phosphonyl, silyl, R6 is at least one of alkyl or branched alkyl, heteroalkyl or aryl, R6′ is a bridging group selected from at least one of bicycle2.2.1heptyl, bicycle3.2.1octyl, oxa analogs, admonyl and cubyl, n′=2-10, n″=1-10, enantiomers and stereoisomers of said compounds and physiologically acceptable salts or solvates of said compounds, enantiomer or stereoisomer.
대표청구항▼
1. A 1,5-dideoxy-1,5-imino-D-glucitol derivative compound having the general formula (I) wherein R2, R3, R4 and R5 are the same or different and are selected from the group consisting of hydrogen, acyl, benzyl, alkyl, aryl, sulfonyl, phosphonyl, silyl, R6 is at least one of alkyl or branched alkyl,
1. A 1,5-dideoxy-1,5-imino-D-glucitol derivative compound having the general formula (I) wherein R2, R3, R4 and R5 are the same or different and are selected from the group consisting of hydrogen, acyl, benzyl, alkyl, aryl, sulfonyl, phosphonyl, silyl, R6 is at least one of alkyl or branched alkyl, heteroalkyl, hydrogen, or aryl,R6′ is hydrogen,n′=2-10,n″=4-6or an enantiomers or stereoisomer of said compound and physiologically acceptable salts of said compound, enantiomer or stereoisomer. 2. The compound of claim 1, wherein n′ is 4, 5, or 6. 3. The compound of claim 1, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound is N-pentyl(1-hydroxycyclohexyl)-1,5-dideoxy-1,5-imino-D-glucitol and has the general formula (III): 4. The compound of claim 1, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound is N-butyl(1-hydroxycyclohexyl)-1,5-dideoxy-1,5-imino-D-glucitol and has the general formula (IV): 5. The compound of claim 1, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound is N-hexyl(1-hydroxycyclohexyl)-1,5-dideoxy-1,5-imino-D-glucitol and has the general formula (V): 6. An anti-viral composition comprising a 1,5-dideoxy-1,5-imino-D-glucitol derivative compound having the general formula (I) wherein R2, R3, R4 and R5 are the same or different and are selected from the group consisting of hydrogen, acyl, benzyl, alkyl, aryl, sulfonyl, phosphonyl, silyl,R6 is at least one of alkyl or branched alkyl, heteroalkyl, hydrogen, or aryl,R6′ is hydrogen,n′=2-10,n″=4-6,or an enantiomers or stereoisomer of said compound and physiologically acceptable salts of said compound, enantiomer or stereoisomer. 7. The anti-viral compound of claim 6, wherein n′ is 4, 5, or 6. 8. A method for inhibiting production of a virus belonging to the Flaviviridae family comprising contacting a mammalian cell infected by said virus with an effective amount of an anti-viral composition comprising the anti-viral compound of claim 6. 9. The method of claim 8, wherein in the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound, R7 is a C4-C6 alkyl moiety. 10. The method of claim 8, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound is N-pentyl(1-hydroxycyclohexyl)-1,5-dideoxy-1,5-imino-D-glucitol and has the general formula (III): 11. The method of claim 8, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound is N-butyl(1-hydroxycyclohexyl)-1,5-dideoxy-1,5-imino-D-glucitol and has the general formula (IV): 12. The method of claim 8, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound is N-hexyl(1-hydroxycyclohexyl)-1,5-dideoxy-1,5-imino-D-glucitol and has the general formula (V): 13. The method of claim 8, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound, enantiomer, or stereoisomer, or physiologically acceptable salt of said compound, enantiomer, or stereoisomer is administered to a mammal. 14. The method of claim 8, wherein the 1,5-dideoxy-1,5-imino-D-gucitol derivative compound, enantiomer, or stereoisomer, or physiologically acceptable salt of said compound, enantiomer, or stereoisomer is administered to a human. 15. The method of claim 8, wherein the 1,5-dideoxy-1,5-imino-D-glucitol derivative compound, enantiomer, or stereoisomer, or physiologically acceptable salt of said compound, enantiomer, or stereoisomer is administered to said mammalian cell in vivo. 16. The method of claim 8, wherein said virus is at least one of West Nile fever virus, dengue virus, bovine viral diarrhea virus, and hepatitis B virus. 17. The method of claim 11, wherein said virus is a flavivirus. 18. The method of claim 17, wherein the flavivirus is selected from the group consisting of yellow fever virus, Japanese encephalitis virus, Murray Valley encephalitis, Rocio virus, St. Louis encephalitis virus, tick-borne encephalitis virus, Louping ill virus, Powassan virus, Omsk hemorrhagic fever virus and Kyasanur forest disease virus. 19. The method of claim 17, said virus is a pestivirus. 20. The method of claim 17, said virus is at least one of bovine diarrhea virus or hepatitis C virus.
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이 특허에 인용된 특허 (31)
Partis Richard A. (Evanston IL) Koszyk Francis J. (Chicago IL) Mueller Richard A. (Glencoe IL), 1,5-dideoxy-1,5-imino-D-glucitol derivatives.
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Scudder Peter R. (Oxford GBX) Dwek Raymond A. (Oxford GBX) Rademacher Thomas W. (Oxford GBX) Jacob Gary S. (Oxford GBX), Compound, N-butyl-deoxynojirimycin-6-phosphate.
Timothy M. Block ; Raymond A. Dwek GB; Baruch S. Blumberg ; Anand Mehta ; Frances Platt GB; Terry D. Butters GB; Nicole Zitzmann DE, Inhibition of membrane-associated viral replication.
Bryant Martin L. (Chesterfield MO) Koszyk Francis J. (Prospect Heights IL) Mueller Richard A. (Glencoe IL) Partis Richard A. (Evanston IL), Method for treating a mammal infected with respiratory syncytial virus.
Jacob Gary S. (Oxford GBX) Tyms A. Stanley (London GBX) Rademacher Thomas W. (Oxford GBX) Dwek Raymond A. (Oxford GBX), Method of treating herpesviruses.
Jacob, Gary S.; Block, Timothy M.; Dwek, Raymond A., Methods of Treating hepatitis virus infections with N-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds in combination therapy.
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Behling James R. (Lindenhurst IL) Farid Payman (Deerfield IL) Khanna Ish (Vernon Hills IL) Medich John R. (Des Plaines IL) Prunier Mike (Vernon Hills IL) Scaros Mike G. (Arlington Heights IL) Weier R, Process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-glucitol and derivatives thereof.
Kinast Gnther (Wuppertal DEX) Schedel Michael (Wuppertal DEX) Koebernick Wolfgang (Wuppertal DEX), Production of N-substituted derivatives of 1-desoxynojirimicin.
Mueller, Richard A.; Bryant, Martin L.; Partis, Richard A.; Jacob, Gary S.; Block, Timothy M.; Dwek, Raymond A., Use of N-substituted-1, 5-dideoxy-1, 5-imino-D-glucitol compounds for treating hepatitis virus infections.
Mueller, Richard A.; Bryant, Martin L.; Partis, Richard A., Use of substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds for treating hepatitis virus infections.
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