Modified fluorinated nucleoside analogues

C - Chemistry – Metallurgy – 07 – H

Patent

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C07H 19/06 (2006.01) A61K 31/7068 (2006.01) A61P 31/12 (2006.01) C07H 19/14 (2006.01) C07H 19/16 (2006.01)

Patent

CA 2527657

The disclosed invention provides compositions and methods of treating a Flaviviridae infection, including hepatitis C virus, West Nile Virus, yellow fever virus, and a rhinovirus infection in a host, including animals, and especially humans, using (2'R)-2'- doxy-2'-fluoro--2'-C-methyl nucleosides, of the general formula (see above formula) wherein (a) Base is a naturally occurring or modified purine or pyrimidine base; (b) X is O, S, CH2, Se, NH, N-alkyl, CHW (R,S, or racemic), C(W)2, wherein W is F, Cl, Br, or I; (c) R1 and R7 are independently H, phosphate, including 5'- monophosphate, diphosphate, triphosphate, or a stabilized phosphate prodrug, H-phosphonate, including stabilized H-phosphonates, acyl, including optionally substituted phenyl and lower acyl, alkyl, including lower alkyl, O-substituted carboxyalkylamino or its peptide derivatives, sulfonate ester, including alkyl or arylalkyl sulfonyl, including methanesulfonyl and benzyl, wherein the phenyl group is optionally substituted, a lipid, including a phospholipid, an L or D-amino acid, a carbohydrate, a peptide, a cholesterol, or other pharmaceutically acceptable leaving group which when administered in vivo is capable of providing a compound wherein R1 is H or phosphate; R2 is OH or phosphate; R1 and R2 can also be linked with cyclic phosphate group; and (d) R2 and R2' are independently H, C1-4 alkyl, C1-4 alkenyl, C1-4 alkynyl, vinyl, N3, CN, Cl, Br, F, I, NO2, C(O)O(C1-4 alkyl), C(O)O(C1-4 alkyl), C(O)O(C1-4 alkynyl), C(O)O(C1-4 alkenyl), O(C1-4 acyl), O(C1-4 alkyl), O(C1-4 alkenyl), S(C1-4 acyl), S(C1-4 alkyl), S(C1-4 alkynyl), S(C1-4 alkenyl), SO(C1-4 acyl), SO(C1-4 alkyl), SO(C1-4 alkynyl), SO(C1-4 alkenyl), SO2(C1-4 acyl), SO2(C1-4 alkyl), SO2(C1-4 alkynyl), SO2(C1-4 alkenyl), O3S(C1-4 acyl), O3S(C1-4 alkyl), O3S(C1-4 alkenyl), NH2, NH(C1-4 alkyl), NH(C1-4 alkenyl), NH(C1-4 alkynyl), NH(C1-4 acyl), N(C1-4 alkyl)2, N(C1-18 acyl)2, wherein alkyl, alkynyl, alkenyl and vinyl are optinally substituted by N3, CN, one to three halogen (C1-4, Br, F, I), NO2, C(O)O(C1-4 alkyl), C(O)O(C1-4 alkyl), C(O)O(C1-4 alkynyl), C(O)O(C1-4 alkenyl), O(C1-4 acyl), O(C1-4alkyl), O(C1-4 alkenyl), S(C1-4 acyl), S(C1-4 alkyl), S(C1-4 alkynyl), S(C1-4 alkenyl), SO(C1-4 acyl), SO(C1-4 alkyl), SO(C1-4 alkynyl), SO(C1-4 alkenyl), SO2(C1-4 acyl), SO2(C1-4 alkyl), SO2(C1-4 alkynyl), SO2(C1-4 alkenyl), O3S(C1-4 acyl), O3S(C1-4 alkyl), O3S(C1-4 alkenyl), NH2, NH(C1-4 alkyl), NH(C1-4 alkenyl), NH(C1-4 alkynyl), NH(C1-4 acyl), N(C1-4 alkyl)2, N(C 1 -4 acyl)2, R2 and R2' can be together to form a vinyl optionally substituted by one or two of N3, CN, Cl, Br, F, I, NO2 OR7 and (e) R6 is an optionally substituted alkyl (including lower alkyl), cyano (CN), CH3, OCH3, OCH2CH3, hydroxy methyl (CH2OH), fluoromethyl (CH2F), azido (N3), CHCN, CH2N3, CH2NH2, CH2NHCH3, CH2N(CH3)2, alkyne (optionally substituted), or fluoro or a pharmaceutically acceptable salt or prodrug thereof.

L'invention concerne des compositions et des méthodes de traitement d'une infection à <i>Flaviviridae</i>, notamment le virus de hépatite C, le virus du Nil occidental, le virus de la fièvre jaune et une infection à rhinovirus chez un hôte, notamment les animaux, et surtout les êtres humains, au moyen de (2'R)-2'-désoxy-2'-fluoro-2'-C-méthyl nucléosides ou d'un sel acceptable sur le plan pharmaceutique ou d'un promédicament de ceux-ci.

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