2-propylene-1-ones as hsp70 inducer

A CH2, drug technology, applied in the field of 2-propen-1-one as HSP 70 inducer, can solve the problem of slow wound healing and the like

Inactive Publication Date: 2007-05-16
TORRENT PHARMA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0064] (c) slow wound healing

Method used

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  • 2-propylene-1-ones as hsp70 inducer
  • 2-propylene-1-ones as hsp70 inducer
  • 2-propylene-1-ones as hsp70 inducer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0839] 3-(3-Hydroxy-quinoxalin-2-yl)-1-[4-(4-methyl-piperazine-1-carbonyl-phenyl)-propenone (Compound No. 37)

[0840] Step A: Preparation of 3-Hydroxy-quinoxaline-2-carboxaldehyde

[0841] To 3-methyl-quinoxalin-2-ol (1 g, 6.2 mmol) in 1,4-dioxane (30 mL) was added selenium dioxide (2 g, 18.7 mmol) and refluxed for 4 hours. The reaction mixture was then cooled, filtered through celite and partitioned between water and ethyl acetate. The combined organic layers were washed successively with water (50ml x 2) and brine (50ml x 2), dried over anhydrous sodium sulfate and evaporated under vacuum to give 0.58g of the title compound as a brown solid. This compound was used in the next step without purification.

[0842] 1 H NMR (400 MHz, DMSOd 6 ) δ 7.63-7.69 (2H, m), 7.84-8.38 (2H, m), 10.19 (IH, s), 12.84 (IH, bs).

[0843] Step B: Preparation of 4-[3-(3-Hydroxy-quinoxalin-2-ylacryloyl)benzoic acid

[0844] A solution of 0.58 g (3.3 mmol) of the product from Example 1, Step ...

Embodiment 2

[0851] 1-[4-(4-Methyl-piperazine-1-carbonyl)-phenyl-3-(6-trifluoromethyl-quinolin-2-yl)-propenone (compound number 32)

[0852] Step A: Preparation of 2-methyl-6-trifluoromethylquinoline

[0853] Add sodium m-nitrobenzenesulfonate (7g, 31mmol), ferrous sulfate (8.62g, 31mmol) and boric acid ( 7.7 g, 124 mmol). The reaction mixture was refluxed for 1 hour with vigorous stirring. Crotonaldehyde (3.25 g, 46 mmol) was then added dropwise thereto and the mixture was refluxed for 8 hours. After cooling to 60°C, methanol (10ml) was added and filtered through celite. The pH of the filtrate was adjusted to 7 with aqueous sodium hydroxide solution (1 N). Volatile materials were evaporated in vacuo. The reaction mixture was partitioned between water and ethyl acetate. The combined organic layers were washed successively with water (100ml x 2) and brine (50ml x 2), dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by silica gel column chromat...

Embodiment 3

[0866] 2-{3-[4-(3-Dimethylamino-pyrazole-1-carbonyl)-phenyl]-3-oxo-propenyl}-quinoline-6-sulfonamide (Compound No. 46)

[0867] Step A: Preparation of 2-methyl-quinoline-6-sulfonamide (sulphonamide)

[0868]Add m-nitrobenzenesulfonate sodium (1.3g, 5.8mmol), ferrous sulfate (1.6g, 5.8mmol) ) and boronic acid (1.4 g, 23 mmol). The reaction mixture was refluxed for 1 hour with vigorous stirring. Crotonaldehyde (0.7 g, 8.7 mmol) was then added dropwise thereto and the mixture was refluxed for 8 hours. After cooling to 60°C, methanol (2ml) was added and filtered through celite. The pH of the filtrate was adjusted to 7 with 1N aqueous sodium hydroxide solution. The reaction mixture was partitioned between water and ethyl acetate. The combined organic layers were washed successively with water (10ml x 2) and brine (5ml x 2), dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by silica gel column chromatography using 30% ethyl acetate in h...

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Abstract

The present invention relates to novel compounds of 2-propene-1-one series, of general formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them, wherein R5, R6, Q and Y are as defined in the specification. The present invention also relates to a process for preparing such compounds, compositions containing such compounds, and use of such compound and composition in medicine. The compounds of the general formula (I) induce HSP-70 and are useful for the treatment of diseases accompanying pathological stress in a living mammalian organism, including a human being, such as stroke, myocardial infarction, inflammatory disorder, hepatotoxicity, sepsis, diseases of viral origin, allograft rejection, tumourous diseases, gastric mucosal damage, brain haemorrhage, endothelial dysfunctions, diabetic complications, neuro-degenerative diseases, post-traumatic neuronal damage, acute renal failure, glaucoma and aging related skin degeneration.

Description

field of invention [0001] The present invention relates to novel compounds of 2-propen-1-one series represented by general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their Polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them, wherein R 5 , R 6 , Q and Y have the meanings described below. [0002] [0003] The present invention also relates to the aforementioned novel compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their Pharmaceutically acceptable solvates of and pharmaceutically acceptable compositions containing them. [0004] The compound represented by the general formula (I) can be used for the treatment and / or prevention of local ischemia-related injury, such as stroke, myocardial infarction, inflammatory diseases, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/14C07D215/42C07D213/72C07D401/10C07D241/18C07D409/12C07D401/04C07D403/10C07D403/12C07D405/12C07D241/12C07D409/14C07D401/14C07D417/04C07D413/12
CPCC07D403/12C07D405/12C07D409/12C07D241/12C07D409/14C07D401/10C07D413/12C07D401/14C07D215/14C07D403/10C07D215/42C07D417/12C07D241/18C07D241/44C07D213/72C07D401/04A61P1/04A61P1/16A61P13/12A61P17/16A61P25/00A61P25/14A61P25/16A61P25/28A61P27/06A61P29/00A61P31/04A61P31/12A61P35/00A61P37/06A61P43/00A61P9/00A61P9/10C07D403/04C07D413/14C07D417/04
Inventor P·库马尔U·R·曼尼R·C·古普塔S·S·那卡尼A·莫汉纳R·坦登S·孟希
Owner TORRENT PHARMA LTD
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