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Compounds and pharmaceutical compositions for the treatment of viral infections

A technology of compounds and solvates, applied in the field of compounds and pharmaceutical compositions for the treatment of viral infections, can solve problems such as poor ability of hepatitis C virus to grow effectively

Inactive Publication Date: 2014-06-04
INDENIX PHARM LLC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because of the similarities between pestiviruses and HCV, and because of the poor ability of HCV to grow efficiently in cell culture, bovine viral diarrhea virus (BVDV) is often studied as a surrogate HCV virus

Method used

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  • Compounds and pharmaceutical compositions for the treatment of viral infections
  • Compounds and pharmaceutical compositions for the treatment of viral infections
  • Compounds and pharmaceutical compositions for the treatment of viral infections

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0687] Preparation of compound 3

[0688]

[0689] Synthesis of Compound 1:

[0690]

[0691] To a stirred suspension of 2-amino-6-chloro-purine (1.8g, 1.2eq) in dry toluene (86ml) was added N,O-bis(trimethylsilyl)acetamide (8.4ml, 4eq ). The mixture was stirred at 120°C for 30 minutes (complete dissolution). 1,2,3,4-Tetra-O-benzoyl-2-C-methyl-D-ribofuranose (5 g, 1 equiv) and trimethylsilyltrifluoromethanesulfonic acid were then added at room temperature ester (3.9ml, 2.5eq) and the reaction mixture was stirred at 120°C for 3 hours. The mixture was then diluted in DCM and washed with saturated NaHCO 3 The solution was washed twice with NaCl solution and purified by silica gel chromatography (petroleum ether / EtOAc) to give compound 1 in 45% yield. MS (ESI, EI + )m / z=628(MH + ).

[0692] Synthesis of compound 2:

[0693]

[0694] To a stirred solution of compound 1 (17 g, 1 equiv) in MeOH (270 ml, 10 ml / mol) was added NaOCH at room temperature 3 (64g, 4.4 equiv...

Embodiment 2

[0699] Preparation of Compound 4

[0700]

[0701] Carbonyldiimidazole (10 mg, 2 equiv) was poured onto a solution of compound 3 (20 mg, 1 equiv) in anhydrous DMF (400 µl) at 0°C. The reaction mixture was stirred: 15 minutes at 0 °C and 2 hours at room temperature. Then by silica gel chromatography (C 18 , H 2 O / MeOH) to purify the crude material to give compound 4 as a white solid in 62% yield. MS (ESI, EI + )m / z=673(MH + ).

Embodiment 3

[0703] Preparation of compound 6

[0704]

[0705] Synthesis of compound 5:

[0706]

[0707] To a stirred solution of compound 1 (1 g, 1 equiv) in EtOH (13 ml) was added cyclopropylamine (1.1 ml, 10 equiv) at room temperature. The reaction mixture was refluxed for 16 hours, cooled to room temperature and concentrated under reduced pressure. The crude material was used as such in the next step.

[0708] The crude product from the previous step (1 eq) was dissolved in MeOH (32 ml). Then NaOMe (290 mg, 3.3 equiv) was added to the mixture at room temperature. The reaction mixture was stirred at room temperature for 2 h, neutralized to pH 7 with AcOH and chromatographed on silica gel (C 18 DCM / MeOH) to give compound 5 as a white solid in 93% yield. MS (ESI, EI + )m / z=337(MH + ).

[0709] Synthesis of Compound 6:

[0710]

[0711] Following the procedure as described for compound 3, compound 6 was prepared from compound 5 (300 mg, 1 equiv) and L-leucine ethyl este...

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Abstract

Provided herein are compounds, compositions and methods for the treatment of liver disorders, including HCV infections. In one embodiment, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents.

Description

[0001] This application claims U.S. Provisional Patent Application No. 61 / 470,334, entitled "Compounds and Pharmaceutical Compositions for the Treatment of Viral Infections," filed March 31, 2011 priority. The entire content of the above application is incorporated herein by reference. technical field [0002] Provided herein are compounds, methods and pharmaceutical compositions for treating viral infections, including hepatitis C virus infections, in a host in need thereof. In one embodiment, phosphoramidate nucleoside compounds are provided that enable concentration of the drug in the liver. Background technique [0003] Flaviviridae [0004] The Flaviviridae family of viruses includes at least three distinct genera: pestiviruses, which cause disease in cattle and pigs; flaviviruses, which are the main cause of diseases such as dengue and yellow fever; and the genus hepaciviruses, the only member of which is HCV. The Flavivirus genus includes more than 68 members, whi...

Claims

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Application Information

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IPC IPC(8): C07H19/167C07H19/20C07H21/02A61K31/708A61K31/7105A61P31/12
CPCC07H19/167C07H21/02C07H19/20A61K31/706A61K31/7076A61K31/7052A61K31/7064A61K31/7042A61K31/708A61P1/16A61P31/12A61P31/14A61P43/00
Inventor 多米尼克·苏拉劳克斯吉尔斯·格索林
Owner INDENIX PHARM LLC
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