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Benzothiazinone and benzoxazinone compounds

A compound, unsubstituted technology, used in active ingredients of heterocyclic compounds, digestive system, organic chemistry, etc.

Inactive Publication Date: 2005-07-06
KNOLL GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Direct evidence for a fundamental role of KDR in VEGF-mediated vascular permeability is still lacking to date

Method used

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  • Benzothiazinone and benzoxazinone compounds
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  • Benzothiazinone and benzoxazinone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0651] Example 1: Synthesis of (Z)-2[(pyrrol-2-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one:

[0652] To 2H-1,4-benzothiazin-3(4H)-one (0.60g, 4mmol) and pyrrole-2-carbaldehyde (0.49g, 5.2mmol) in anhydrous N,N-dimethylformamide ( 3.5ml) (hereinafter referred to as "DMF") was added sodium methoxide (0.28g, 5.2mmol). The mixture was heated at 120°C for 6.5 hours, then cooled and poured into water (60ml). The precipitate was collected by filtration and washed with water. The precipitate was dissolved in ethyl acetate, and the black insoluble residue was filtered off. The filtrate was concentrated and then subjected to silica gel column chromatography using a 100% dichloromethane-(100:1) dichloromethane:ethanol gradient as the mobile phase. The first eluting product was the (E)-isomer.

Embodiment 12

[0653]Example 12: Synthesis of (Z)-7-amino-2-[(pyrrol-2-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one:

[0654] Under stirring, to (Z)-7-nitro-2-[(pyrrol-2-yl) methylene]-2H-1,4-benzothiazin-3(4H)-one (Example 5) To a mixture of (0.43g, 1.5mmol) and hydrazine hydrate (98%) (0.8ml) in ethanol (20ml) was added a catalytic amount of Raney nickel in portions. The reaction mixture was heated to reflux for 5.5 hours, then filtered and the solvent removed in vacuo. The product was purified by silica gel chromatography using a (98:2)-(95:5) toluene:ethanol gradient as mobile phase.

Embodiment 13

[0655] Example 13: Synthesis of 2-[(4,5-dimethylpyrrol-2-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one:

[0656] 4,5 - Dimethylpyrrole-2-carbaldehyde (0.27 g, 2.19 mmol). The mixture was heated at 120°C for 48 hours, then cooled and poured into ice water (50ml). The precipitate was collected by filtration, washed with water, and then dissolved in ethanol. The black insoluble residue was filtered off, then concentrated to dryness under reduced pressure. The product was purified by silica gel chromatography using (98:2) dichloromethane:methanol as mobile phase.

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PUM

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Abstract

The present invention provides a compound of formula (I), wherein Q is -N= or CR2; X is S, O or NOR3; Y is -O-, S-, -SO- or -SO2-; R and R1 are independently is H, substituted or unsubstituted aliphatic, aromatic, heteroaromatic or aralkyl-yl; group; R2 is H or a substituent; R3 is H, or -C(O)R4; R4 is substituted or unsubstituted Substituted aliphatic or aromatic groups; n is an integer 0-1. Compounds of formula (I) and their physiologically acceptable salts are inhibitors of serine / threonine and tyrosine kinase activity. Several tyrosine kinases whose activity can be inhibited by these compounds are involved in the angiogenic process. Thus, these chemical compounds are able to ameliorate disease states in which angiogenesis or endothelial cell proliferation is a factor. These compounds are useful in the treatment of cancer and hyperproliferative diseases.

Description

[0001] Related applications: [0002] This application claims the benefit of US Provisional Application No. 60 / 137,410, filed June 3, 1999, which is hereby incorporated by reference in its entirety. [0003] The present invention relates to certain benzothiazinones and benzoxazinones, which are inhibitors of protein kinases, especially tyrosine kinases and serine / threonine kinases, some of which are novel compounds; It also relates to pharmaceutical compositions containing these benzothiazinones or benzoxazinone compounds, processes for preparing these benzothiazinones and benzoxazinone compounds. Background of the invention [0004] At least 400 enzymes have been identified as protein kinases. These enzymes catalyze the phosphorylation of target protein substrates. Phosphorylation generally refers to the transfer of a phosphate group from ATP to a protein substrate. The specific structure of the transferred phosphate group in the target substrate is a tyrosine, serine or t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/42C07D265/36A61K31/425A61K31/437A61K31/538A61K31/5383A61K31/5415A61P1/00A61P3/10A61P5/14A61P9/00A61P9/10A61P11/16A61P15/00A61P17/02A61P17/06A61P19/02A61P21/04A61P25/00A61P27/02A61P29/00A61P35/00A61P37/02A61P37/06A61P43/00C07DC07D279/16C07D413/06C07D413/12C07D413/14C07D417/00C07D417/06C07D417/12C07D417/14C07D471/04C07D498/04C07D513/04
CPCC07D265/36C07D413/06C07D417/06C07D471/04A61P1/00A61P11/16A61P15/00A61P17/02A61P17/06A61P19/02A61P21/04A61P25/00A61P27/02A61P29/00A61P35/00A61P37/02A61P37/06A61P43/00A61P5/14A61P9/00A61P9/10A61P3/10A61K31/542
Inventor P·拉菲蒂D·卡尔德伍德L·D·阿诺B·贡扎莱茨帕斯库尔J·L·奥尔特戈马蒂尼茨M·J·佩雷茨德维加I·F·菲尔南德茨
Owner KNOLL GMBH
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