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Synthesis of 2'-deoxy-l-nucleosides

A technology of nucleosides and compounds, applied in the field of medicinal chemistry, can solve problems that cannot be used to treat disseminated neoplastic diseases, can not be used to treat tumors, cell replication or cell metabolism interruption

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
[0028] 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

[0065] The present invention discloses herein a process for the preparation of the compound of formula (A).

[0066]

[0067] in

[0068] X and Y are independently hydrogen, OH, OR 1 , SH, SR 1 , NH 2 , NHR 1 or NR 1 R 2 ;

[0069] Z is hydrogen, halogen, CN or NH 2 ;

[0070] 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 ;

[0071] R 1 , R 2 , R 3 and R 4 independently lower alkyl such as methyl, ethyl, propyl, butyl, and alkyl having 6 or less carbons, including cyclic, branched or linear, unsubstituted or substituted alkyl, wherein Alkyl groups may be substituted by one, two or more groups including, but not limited to, amino, carboxyl, hydroxyl and phenyl;

[0072] R 13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate or stabilized phosphate) or silyl. ...

Embodiment 1

[0628] 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (1,R 1 =Ac, R 2 =Bz)

[0629] 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (1,R 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, 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 during 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). With cold water (2×0.5L), 1N H 2 SO 4 (3×0.5mL), water (0.5L) and saturated sodium bicarbonate (2×0.5mL) washed the organic solution successively, dried over magnesium sulfate, concentrated in vacuo into a slurry, then dissolved in glacial acetic acid (200mL) and acetic anhydride ( 0.5L) in the mixture. C...

Embodiment 2

[0631] 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (2, X'=Br, R 2 =Bz)

[0632] 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 standing at 0°C for 1 hour and at room temperature for 15 minutes, the solution was concentrated in vacuo. Continue azeotropic distillation with toluene (25mL×5) to remove 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 = 4.4Hz). 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): C07H19/00C07H1/00A61P31/12C07H19/067C07F7/18C07H1/06C07H19/06C07H19/073C07H19/09C07H19/16C07H19/167C07H19/173C07H19/19C12N15/10
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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