Nitrobenzyl derivatives of Anti-cancer agents

A technology of aryl and alkyl, applied in the field of cancer treatment of cancer patients

Active Publication Date: 2018-06-08
SHENZHEN ASCENTAWITS PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

PR l04 is ineffective in clinical trials

Method used

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  • Nitrobenzyl derivatives of Anti-cancer agents
  • Nitrobenzyl derivatives of Anti-cancer agents
  • Nitrobenzyl derivatives of Anti-cancer agents

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0185] Example 1: Synthesis of compounds provided herein

[0186] a.

[0187]

[0188] Compound B

[0189] Compound A (110mg) was dissolved in 5ml SOCl at 90°C 2 The solution in was heated for 3 hours. The solvent was then removed under vacuum. The residue was dissolved in toluene (5ml) and the solvent was removed again to afford compound B (112mg) without further purification.

[0190] Compound D

[0191] A solution of compound B (80 mg), compound C (2 mL) in ACN (acetonitrile, 2 ml) was heated at 80 °C overnight. Solvent was removed under vacuum. The residue was chromatographed on silica gel (ACN:H 2 O=80:20 (V / V)), to obtain 65 mg of compound D.

[0192] TH2995

[0193] Compound D (60mg) was dissolved in 5ml SOCl at 90°C 2 The solution in was heated for 4 hours. The solvent was then removed under vacuum. The residue was chromatographically separated on silica gel (AcOEt:MeOH=90:10 (V / V)) to obtain 50 mg TH2995. 1HNMR (CDCl 3 +CD 3 OD): 7.94(1H), 7.38(2H), 7...

example 2

[0213] Example 2. In Vitro Human Tumor Cell Line Cytotoxicity Analysis

[0214] In vitro proliferation data on the H460 non-cellular lung cancer human tumor cell line was obtained by exposing it to various concentrations of the compound for 2 hours, followed by a washing step and addition of fresh medium, followed by growth and cell viability staining, and compared with the measured IC of the medium-only treated control 50 Determination.

[0215] Specifically, exponentially growing cells were divided into 4 × 10 3 Cells / well were seeded in 96-well plates and incubated at 37°C in 5% CO 2 , 95% air and 100% relative humidity for 24 hours before adding the test compound. Compounds were dissolved in 100% DMSO at 200 times the desired final assay concentration. At the time of drug addition, compounds were further diluted to 4x the desired final concentration with complete medium. Aliquots of 50 μl of compounds at the indicated concentrations were added to microtiter wells alre...

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PUM

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Abstract

Provided herein are compounds of formula I, wherein the variables are defined herein, processes of making them, and methods of treating cancer comprising administering such compounds.

Description

technical field [0001] The present invention provides compounds suitable as therapeutic agents and intermediates thereof, pharmaceutical compositions having these compounds and methods of treating cancer in cancer patients, and thus relates to the fields of biology, chemistry and medicine. Background technique [0002] Cancer is one of the main causes of human morbidity and death. Cancer treatment is challenging because it is difficult to kill cancer cells without damaging or killing normal cells. Damage or killing of normal cells during cancer treatment can cause adverse side effects in the patient and can limit the amount of anticancer drugs administered to the cancer patient. [0003] Aldo-keto reductase family 1 member C3 is an enzyme encoded by the AKR1C3 gene in humans. This gene encodes a member of the aldehyde / ketone reductase superfamily consisting of more than 40 known enzymes and proteins. These enzymes catalyze the conversion of aldehydes and ketones to their ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P35/00A61K31/04A61K31/06C07C205/38
CPCC07D305/14C07H19/06C07H19/073C07H19/10C07H15/252C07H17/04C07H1/00C07D239/553C07D491/22C07C217/58C07C213/02C07K7/06C07D471/04C07D487/04C07D239/94C07D403/06C07K5/0205A61K47/54A61P35/00A61K38/00C07D405/12C07F9/65586A61K47/55A61K47/64A61K31/506C07D405/04
Inventor 段建新曹冶宇蔡晓宏矫海龙马靖原马克·马特西
Owner SHENZHEN ASCENTAWITS PHARM TECH CO LTD
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