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Ritonavir analogous compound useful as retroviral protease inhibitor, preparation of the ritonavir analogous compound and pharmaceutical composition for the ritonavir analogous compound.

A compound and prodrug technology, applied in the field of ritonavir analogs, can solve the problem of lack of antiviral activity

Inactive Publication Date: 2007-06-13
CRISTALIA PROD QUI FARM LTDA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The antiviral activity of several analogous compounds with respect to ritonavir (in which substitution of the B group with an A group or substitution of the A group with a B group was performed, or even in which the A group and the B group are identical) had no antiviral activity. full references

Method used

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  • Ritonavir analogous compound useful as retroviral protease inhibitor, preparation of the ritonavir analogous compound and pharmaceutical composition for the ritonavir analogous compound.
  • Ritonavir analogous compound useful as retroviral protease inhibitor, preparation of the ritonavir analogous compound and pharmaceutical composition for the ritonavir analogous compound.
  • Ritonavir analogous compound useful as retroviral protease inhibitor, preparation of the ritonavir analogous compound and pharmaceutical composition for the ritonavir analogous compound.

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] compound (2S, 3S, 5S)-2,5-bis-[N-[N-[[N-methyl-N-[(2-isopropyl-4- Thiazolyl)methyl]amino]carbonyl]valyl]amino-1,6-diphenyl-3-hydroxyhexane preparation of

[0063] a. (2S, 3S, 5S)-2-[N-[N-[[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl Base]amino]carbonyl]valyl]amino]-5-(tert-butoxycarbonylamine)-1,6-diphenyl-3-hydroxyl Hexane

[0064] With stirring system and in N 2 In a 6.0L spherical flask under atmosphere, add (2S, 3S, 5S)-2-amino-3-hydroxyl-5-(tert-butoxycarbonylamine)-1,6-diphenylhexane (100g, 0.26mol ) and chloroform (1.9 L). After the solid had completely dissolved, N-[[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]L-valyl hydroxysuccinimide ester (107 g , 0.26mol) in chloroform (630mL). The reaction was monitored by thin layer chromatography and 10% sodium carbonate solution (1.9 L) was added at the end of the reaction. The phases were separated and the organic phase was used directly in the next step without prior purification.

[0065]...

Embodiment 2

[0074] compound (2S, 3S, 5S)-2-[N-[N-[[N-methyl-N-[(2-isopropyl-4-thiazolyl) Methyl]amino]carbonyl]valyl]amino]-5-(N-((5-thiazolyl)methoxycarbonyl)ammonia base)-1,6-diphenyl-3-hydroxyhexane preparation of

[0075] With stirring system and in N 2 In the 4.0L reactor under atmosphere, add THF (2.9L) solution containing the compound obtained in Example 1B and (N-(5-thiazolyl)methyl)-(4-nitrophenyl)carbonate (76g, 0.27mol). The reaction was kept stirring at ambient temperature and the reaction was monitored by TLC. The solvent was removed under reduced pressure, the crude product was dissolved in ethyl acetate (2.0 L), the organic phase was washed with 1N sodium hydroxide solution (8x500 mL) and saturated sodium chloride solution, and dried over sodium sulfate. The product was concentrated under reduced pressure until it reached 1 / 3 of the volume, then hexane was added to crystallize the product. The white solid was dried in a 40°C oven. Yield: 141 g.

[0076] RMN- 1 H...

Embodiment 3

[0079] compound (2S, 3S, 5S)-2,5-bis-(N-((5-thiazolyl)methoxycarbonyl)ammonia base)-1,6-diphenyl-3-hydroxyhexane preparation of

[0080] a. (2S, 3S, 5S)-2-(N-((5-thiazolyl)methoxycarbonyl)amino-5-(tert-butoxycarbonyl Amino)-1,6-diphenyl-3-hydroxyhexane

[0081] With stirring system and in N 2 In a 6.0L spherical flask under atmosphere, add (2S, 3S, 5S)-2-amino-3-hydroxyl-5-(tert-butoxycarbonylamine)-1,6-diphenylhexane (100g, 0.26 mol) in THF (1.9 L) and (N-(5-thiazolyl)methyl)-(4-nitrophenyl) carbonate (76 g, 0.27 mol) in THF (630 mL). The reaction was monitored by thin-layer chromatography, the solvent was removed under reduced pressure, the crude product was dissolved in ethyl acetate (2.0 L), the organic phase was washed with 1N sodium hydroxide solution (8x500 mL) and saturated sodium chloride solution, and dried over sodium sulfate product. The phases were separated and the crude product was concentrated and used directly in the next step without prior purifica...

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Abstract

The present invention describes a new one ritonavir analogous compound that presents significantly superior activity in inhibition of HIV protease. There are also described the usage of the ritonavir analogous compound of the present invention or salt, ester or prodrug thereof as well as the usage of the compound and its pharmaceutical compositions in medicine, particularly, in the treatment of HIV infection, by itself or in combination with others anti-HIV drugs.

Description

technical field [0001] The present invention relates to novel HIV protease inhibitor compounds or salts or prodrugs or esters thereof, processes for the preparation of such novel compounds, pharmaceutical compositions thereof and therapeutic uses of such compounds. [0002] Specifically, the compound of the present invention is a ritonavir analog that has the activity of inhibiting the HIV protease, which is required for the HIV replication process, as shown below. Therefore, the compounds of the present invention can be used in the treatment of HIV infection, either by themselves or in combination with other anti-HIV drugs. Background technique [0003] Human Immunodeficiency Virus (HIV) is a retrovirus (composed of RNA) belonging to the Lentiviridae subfamily, which is capable of sponging up the human immune system, causing an infectious disease known simply as AIDS (Acquired Immunodeficiency Syndrome) [Pecanha, E.P.; Antunes, O.A.C; Tanuri, A.; Quim Nova, Vol. 25, No. 6B...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/24C07D277/28
CPCC07D277/24C07D277/28A61P31/18A61P43/00
Inventor M·A·伯克曼S·S·罗萨托C·R·弗泽托T·B·维努西D·C·巴雷尔K·M·G·D·奥利维拉M·P·D·弗雷塔斯
Owner CRISTALIA PROD QUI FARM LTDA
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