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Synthesis of 2'-deoxy-l-nucleosides

A nucleoside and cyclic nucleoside technology, applied in the field of medicinal chemistry, can solve problems that cannot be used to treat disseminated tumor diseases, cell replication or cell metabolism interruption, and cannot be used to treat tumors, etc.

Inactive Publication Date: 2007-02-28
法玛赛特有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Surgical excision is sometimes effective for tumors located in certain areas such as the breast, colon, and skin, but not in other areas such as the spine, nor is it used to treat disseminated neoplastic diseases such as leukemia
[0027] Chemotherapy causes disruption of cell replication or cell metabolism

Method used

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  • Synthesis of 2'-deoxy-l-nucleosides
  • Synthesis of 2'-deoxy-l-nucleosides
  • Synthesis of 2'-deoxy-l-nucleosides

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preparation example Construction

[0064] The present invention herein discloses the preparation method of the compound of formula (A).

[0065]

[0066] in

[0067] X and Y are independently hydrogen, OH, OR 1 , SH, SR 1 , NH 2 , NHR 1 or NR 1 R 2 ;

[0068] Z is hydrogen, halogen, CN or NH 2 ;

[0069] R is hydrogen, lower alkyl, aralkyl, halogen, NO 2 , NH 2 , NHR 3 , NR 3 R 4 , OH, OR 3 , SH, SR 3 , CN, CONH 2 , CSNH 2 , CO 2 H, CO 2 R 3 , CH 2 CO 2 H, CH 2 CO 2 R 3 , CH=CHR 3 , CH 2 CH=CHR 3 or C=CR 3 ;

[0070] R 1 , R 2 , R 3 and R 4 independently lower alkyl groups such as methyl, ethyl, propyl, butyl, and alkyl groups having 6 or fewer carbons, including cyclic, branched or straight chain, unsubstituted or substituted alkyl groups, wherein Alkyl groups may be substituted with one, two or more groups including but not limited to amino, carboxyl, hydroxyl and phenyl;

[0071] R 13 Is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate or stabi...

Embodiment 1

[0619] 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (1,R 1 =Ac, R 2 =Bz)

[0620] 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (1,R) was prepared from D-ribose as described by Recondo and Rinderknecht (loc. cit.) 1 =Ac, R 2 =Bz), the compound is prepared from L-ribose. A mixture of L-ribose (150 g, 1.0 mol) in methanol (2.5 L) containing 1% hydrochloric acid was stirred for 2 hours and then neutralized with pyridine (250 mL). The mixture was concentrated in vacuo and the residue was dissolved in pyridine (1 L). Benzoyl chloride (385 mL, 3.3 mol) was added dropwise to the solution while cooling to 0 °C. After overnight at room temperature, the mixture was concentrated in vacuo at 35-40 °C, and the residue was dissolved in ethyl acetate (1.5 L). Use cold water (2×0.5L), 1N H 2 SO 4 (3 × 0.5 mL), water (0.5 L) and saturated sodium bicarbonate (2 × 0.5 mL), the organic solution was washed successively, dried over magnesium sulfate, concentrated in vacuo to a slurry, ...

Embodiment 2

[0622] 2,3,5-Tri-O-benzoyl-D-ribofuranosyl bromide (2,X'=Br,R 2 =Bz)

[0623] Hydrogen bromide was bubbled into a solution of compound 1 (25.2 g, 0.05 mol) in ice-cold dichloromethane (150 mL) over 15 minutes. After 1 hour at 0°C and 15 minutes at room temperature, the solution was concentrated in vacuo. Continuous azeotropic distillation with toluene (25 mL×5) removed traces of hydrogen bromide. The syrupy residue (2) is immediately condensed with the appropriate purine or pyrimidine. of the slurry 1 The H-NMR spectrum includes a singlet δ6.5 (H-1, β-anomer) and a doublet 6.9 (H-1α-anomer, J 1，2 = 4.4 Hz). α / β is about 3:2.

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Abstract

This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH2, NHR', or NR'R'' Z is H, F, Cl, Br, I, CN, or NH2. R is hydrogen, halogen, lower alkyl of C1-C6 or aralkyl, NO2, NH2, NHR', NR'R'', OH, OR, SH, SR, CN, CONH2, CSNH2, CO2H, CO2R', CH2CO2H, CH2CO2R', CH-CHR, CH2CH-CHR, or C-CR. R' and R'' are same or different, and lower alkyl of C1-C6. R13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

Description

Background of the Invention [0001] The application belongs to the field of medicinal chemistry, and in particular relates to a preparation method of 2'-deoxy-L-nucleosides and products and compositions prepared according to the method, and said 2'-deoxy-L-nucleosides have anti-human immunity Activity of defective virus, hepatitis B virus, hepatitis C virus and abnormal cell proliferation. [0002] This application claims priority to U.S.S.N. 60 / 165,087, filed November 12, 1999, by Woo-Baeg Choi and Kyoihi A. Watanabe, entitled "Synthesis of 2'-Deoxy-L-Nucleosides." [0003] human immunodeficiency virus [0004] Human immunodeficiency virus (HIV) is a virus that can cause serious health problems in humans. In 1981, Acquired Immune Deficiency Syndrome (AIDS) was recognized as a disease that seriously compromises the human immune system and almost all causes death. In 1983, the cause of AIDS was determined to be caused by the human immunodeficiency virus (HIV). In 1985, it wa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/00A61P31/12C07H19/067C07F7/18C07H1/06C07H19/06C07H19/073C07H19/09C07H19/16C07H19/167C07H19/173C07H19/19C12N15/10
CPCC12N15/1003C07H19/16C07H19/06C07H1/06A61P31/12A61P35/00C07H19/00
Inventor 清一·A·渡边崔宇方
Owner 法玛赛特有限公司
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