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Betuin derivatives for preventing or treating HIV infections

A compound, CH2 technology, applied in the field of compounds, can solve problems such as reduction and low load

Inactive Publication Date: 2018-05-11
GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO 2) LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Bevirimat users with Gag polymorphisms at Q369, V370, or T371 showed significantly lower load reductions compared to patients without Gag polymorphisms at these sites

Method used

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  • Betuin derivatives for preventing or treating HIV infections
  • Betuin derivatives for preventing or treating HIV infections
  • Betuin derivatives for preventing or treating HIV infections

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0556] Example 1: Compound 15

[0557] 4-((3aR,5aR,5bR,7aR,11aS,11bR,13aS)-3a-((R)-2-(N-(cyclopropylmethyl)-2-(dimethylamino base)acetamido)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b , 6,7,7a,8,11,11a,11b,12,13,13a-Hexadecahydro-2H-cyclopenta[a]penta-9-yl)benzoic acid

[0558] Step A: Intermediate 13

[0559] 4-((3aR,5aR,5bR,7aR,11aS,11bR,13aS)-3a-((R)-2-((cyclopropylmethyl)amino)-1-hydroxyethyl base)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,11, 11a, 11b, tert-butyl 12,13,13a-hexadecahydro-2H-cyclopentadien[a]-9-yl)benzoate

[0560] A mixture of Intermediate 12 (250 mg, 0.39 mmol) and cyclopropanecarbaldehyde (27.2 mg, 0.39 mmol) in MeOH (5 mL) and DCE (0.5 mL) was stirred at room temperature for 2 hours. The resulting mixture was cooled in an ice bath, and NaBH was added dropwise by 4 (14.7 mg, 0.39 mmol) to deal with. After stirring at room temperature for 30 min, the reaction was washed with s...

Embodiment 2

[0569] Example 2: Compound 16

[0570] 4-((3aR,5aR,5bR,7aR,11aS,11bR,13aS)-3a-((R)-2-(N-(cyclopropylmethyl)-2-methoxyethyl Amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6, 7, 7a,8,11,11a,11b,12,13,13a-Hexadecahydro-2H-cyclopenta[a]penta-9-yl)benzoic acid

[0571] The title compound was prepared in a similar manner to Example 1 to give (13 mg, 28%) as a white powder.

[0572]

Embodiment 3

[0573] Example 3: Compound 17

[0574] 4-((3aR,5aR,5bR,7aR,11aS,11bR,13aS)-3a-((R)-2-(N-(cyclopropylmethyl)-2-(pyrrolidine- 1-yl)acetamido)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a , 5b, 6, 7, 7a, 8, 11, 11a, 11b, 12, 13, 13a-Hexadecahydro-2H-cyclopenta[a] (9-yl)benzoic acid hydrochloride

[0575] The title compound was prepared in a similar manner to Example 1 and after purification the product was treated with a few drops of HCl / dioxane to afford (30 mg, 59.8%) as a white powder of the HCl salt.

[0576]

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Abstract

The present invention relates to compounds characterized by having a structure according to the following Formula (I), or a pharmaceutically acceptable salt thereof. Compounds of the present inventionare useful for the treatment or prevention of HIV.

Description

field of invention [0001] The present invention relates to compounds, pharmaceutical compositions and methods of use thereof for (i) inhibiting HIV replication in an HIV-infected subject, or (ii) treating an HIV-infected subject by administering such compounds. Background of the invention [0002] Human immunodeficiency virus type 1 (HIV-1) causes the disease of acquired immunodeficiency disease (AIDS). The number of HIV cases continues to rise, and more than 25 million individuals worldwide are currently afflicted by the virus. Currently, long-term suppression of viral replication with antiretroviral drugs is the only option for treating HIV-1 infection. In fact, the US Food and Drug Administration has approved twenty-five drugs within six different inhibitor classes that have been shown to greatly increase patient survival and quality of life. However, additional treatments are required due to undesired drug-drug interactions; drug-food interactions; nonadherence to ther...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/58A61K31/575A61P31/18
Inventor B.A.约翰斯
Owner GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO 2) LTD