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Uracil or thymine derivative for treating hepatitis c

一种化合物、选自的技术，应用在药物组合、含有效成分的医用配制品、有机化学等方向，能够解决患者没有完成治疗等问题

Inactive Publication Date: 2012-10-24
ABBVIE BAHAMAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Some patients did not complete treatment due to the severe side effects discussed above; others (non-responders) continued to have measurable HCV levels despite treatment; Repeated at a certain time after completion of the treatment program

Method used

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  • Uracil or thymine derivative for treating hepatitis c
  • Uracil or thymine derivative for treating hepatitis c
  • Uracil or thymine derivative for treating hepatitis c

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A

[1351] Example A. Preparation of (E)-N-(3-tert-butyl-5-iodo-4-methoxyphenylcarbamoyl)-3-methoxyacrylamide.

[1352]

[1353] Part A. Preparation of 2-tert-butyl-4-nitrophenol.

[1354] To a vigorously stirred solution of 2-tert-butylphenol (10 g, 66.6 mmol) in heptane (67 ml) was quickly added dropwise a solution of 70% nitric acid (4.25 ml, 66.6 mmol) diluted with water (4.25 ml). The resulting dark red / brown mixture was stirred vigorously for 2h. The suspended solid was collected by filtration, washed with hexane (300 mL), water (200 mL), and again with hexane (200 mL) to obtain cocoa powder, which was dried to constant weight (4.65 g, 35.6%).

[1355] Part B. Preparation of 2-tert-butyl-6-iodo-4-nitrophenol.

[1356] To the product of Part A (4.5 g, 23.05 mmol) dissolved in MeOH (120 ml) and water (30 mL), iodine monochloride (1.155 ml, 23.05 mmol) was added dropwise within 10 min. The mixture was stirred for 2h, diluted into 1L of water, and left overnight. The solid material w...

Embodiment B

[1363] Example B. Preparation of 1-(3-tert-butyl-5-iodo-4-methoxyphenyl)dihydropyrimidine-2,4(1H,3H)-dione.

[1364]

[1365] To the product of Example A (2.46g, 5.69mmol) in ethanol (50ml) was added 5.5mLH 2 SO 4 The mixture was heated at 110°C for 2.5h to obtain a transparent solution. The solution was cooled and diluted with 50 mL of water under stirring to obtain an off-white solid, which was collected by filtration, washed with water, and dried (2.06 g, 90%).

Embodiment C

[1366] Example C. Preparation of 1-(3-tert-butyl-5-iodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione.

[1367]

[1368] Part A. Preparation of 2-tert-butyl-4,6-diiodophenol.

[1369] A solution of 2-tert-butylphenol (20.0 g, 133 mmol) in methanol (266 mL) was treated with sodium hydroxide pellets (6.39 g, 160 mmol). The mixture was stirred until all the sodium hydroxide was dissolved, and then cooled to -2°C in an ice-salt bath. Sodium iodide (15.0 g, 100 mmol) was added, and then a 10% sodium hypochlorite solution (45 mL, 73.3 mmol) was added dropwise at a rate that the temperature of the solution rose to no higher than 1.3°C. Repeat this process (3×) until a total of 60 g (400 mmol) of sodium iodide is added, and sodium hypochlorite solution is added, until the color of the solution changes from a light green-yellow color to a light ice tea color. This requires a ration of 16 mL of 180 mL of total sodium hypochlorite solution. Continue to cool at about 2°C, and add dropwise a s...

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Abstract

Present application relates to the compounds of formula I useful to treat hepatitis C (HCV) infections. In the structure of the disclosed compounds is the uracil or thymine derivative linked via a phenylene into either fused 2-ring cyclic system (R6) or alternatively via additional two-atom linker (L) to a 5-6 membered monocycle (R6). Application further discloses polymorphs and pseudopolymorphs of two specific compounds: N-(6(3-t-butyl-5-(2>4-dioxo-3,4-dihydropyrimidin-1 (2H)- y!)2-methoxy-phenyl)naphthalen-2-yl)methanesulfonamide and (E)-N-(4(3-t- butyl-5-(2,4-dioxo-3)4-dihydropyrimidin-1 (2H)-yl)2-methoxy-styryl- phenyl)methanesulfonamide.

Description

[0001] This application is a division of a Chinese invention patent application with the filing date of September 17, 2008, the application number of 200880107764.3, and the title of "Uracil or Thymine Derivatives for the Treatment of Hepatitis C". [0002] Cross reference to related patent applications [0003] This patent application claims the priority of U.S. Provisional Patent Application No. 60 / 972,877 (filed on September 17, 2007) and U.S. Provisional Patent Application No. 61 / 096,791 (filed on September 13, 2008). The entire contents of these two provisional patent applications are incorporated into this application for reference. Technical field [0004] The present invention relates to: (a) compounds and their salts, especially useful as inhibitors of hepatitis C virus (HCV); (b) intermediates for preparing the compounds and salts; (c) containing the compounds and Salt compositions; (d) methods for preparing the intermediates, compounds, salts, and compositions; (e) method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54A61K31/513A61P31/14
CPCC07D239/54C07D417/14C07D413/10A61K31/513C07D239/22C07D403/10C07D405/10A61K31/5377C07D401/10C07D417/10C07D409/10A61P1/16A61P31/12A61P31/14A61P43/00
Inventor R·瓦格纳M·D·图法诺K·D·斯特沃特T·W·罗克威J·T·兰多尔夫J·K·普拉特C·E·莫特C·J·马林K·L·朗格尼克Y·刘D·刘A·C·克鲁格W·M·卡蒂D·K·赫琴森P·P·黄C·A·弗伦特奇P·L·唐纳D·A·德戈伊D·A·贝特本纳D·M·巴恩斯S·陈T·S·弗兰齐克二世Y·高A·R·海格特J·E·亨格维尔德R·F·亨里B·J·科特克基X·楼K·萨里斯G·G·Z·张
Owner ABBVIE BAHAMAS
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