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Substituted aromatic sulfur compounds and methods of use

A compound, drug technology, applied in the field of substituted aromatic sulfur compounds

Inactive Publication Date: 2016-09-28
CEPHALON INC +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This improvement in survival occurred despite the fact that only 42% of patients completed all 6 cycles of chemotherapy

Method used

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  • Substituted aromatic sulfur compounds and methods of use
  • Substituted aromatic sulfur compounds and methods of use
  • Substituted aromatic sulfur compounds and methods of use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] 2-[4-((E)-2-Cyano-vinylsulfonyl)-phenyl]-2-methyl-propionic acid

[0150]

[0151] To a solution of 2-(4-bromophenyl)-2-methylpropanoic acid (2.43g, 10mmol) in anhydrous THF (150ml) was added slowly in toluene under nitrogen at -80°C (ether / dry ice). Phenyllithium (1.8M, 11mmol) in . After 5 min, n-BuLi (2.5M in hexane, 11 mmol) was added to the mixture. A cloudy suspension slowly formed. 20 minutes after the addition of BuLi, the SO 2 Flow was bubbled through the mixture for 15 min. The reaction mixture was then allowed to warm to room temperature and the solvent was removed in vacuo. The sulfinate residue was dissolved in water (15ml), acetic acid (8ml) and MeOH (20ml), then 2-chloroacrylonitrile (18mmol) was added. The resulting mixture was stirred overnight at room temperature. The organic solvent was removed in vacuo and the residue was diluted with 20ml of water. Use saturated K 2 HPO 4 aqueous solution was adjusted to pH 5-6, then extracted with dichl...

Embodiment 2

[0153] 2-[3-((E)-2-Cyano-vinylsulfonyl)-phenyl]-2-methyl-propionic acid

[0154]

[0155] in N 2 To a solution of 2-(3-bromophenyl)-2-methylpropanoic acid (7.3g, 30mmol) in anhydrous THF (300ml) was added slowly in toluene at -80°C (ether / dry ice). Phenyllithium (1.8M, 33mmol). After 5 min, n-BuLi (2.5M in hexane, 33 mmol) was added to the mixture. A cloudy suspension slowly formed. 20 minutes after the addition of BuLi, the SO 2 Flow was bubbled through the mixture for 15 min. The reaction mixture was then allowed to warm to room temperature and the solvent was removed in vacuo. The sulfinate residue was dissolved in water (50ml), acetic acid (25ml) and MeOH (50ml), then 2-chloroacrylonitrile (60mmol) was added. The resulting mixture was stirred overnight at room temperature. The organic solvent was removed in vacuo, and the residue was diluted with 50 ml of water. Use saturated K 2 HPO 4 Aqueous solution was adjusted to pH~5-6, then extracted with dichloromethan...

Embodiment 3

[0157] (E)-3-[4-(1,1-Dimethyl-2-morpholin-4-yl-2-oxo-ethyl)-benzenesulfonyl]-acrylonitrile

[0158]

[0159] 2-[4-((E)-2-cyano-vinylsulfonyl)-phenyl]-2-methyl-propionic acid (50.0mg, 0.179mmol), morpholine (0.0156mL, 0.179mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (34.3 mg, 0.179 mmol) and 1-hydroxybenzotriazole (12.1 mg, 0.0895 mmol) were dissolved in THF (5.0 ml), and the reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was poured on saturated sodium bicarbonate and the organic phase was extracted with dichloromethane / ethyl acetate. The combined extracts were then dried over sodium sulfate, filtered and concentrated. The crude reaction mixture was purified by Gilson reverse phase chromatography. The combined fractions were lyophilized to give (E)-3-[4-(1,1-dimethyl-2-morpholin-4-yl-2-oxo-ethyl)-benzenesulfonyl]- Acrylonitrile (11 mg, 17%). MS:349(M+H); 1H-NMR(DMSO-d6400MHz)δ8.24(d,1H,J=15.7Hz),7.91(d,2H...

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Abstract

The present invention describes compounds of formula II, as well as pharmaceutical compositions and methods of treating or reducing the risk of peritoneal cancer metastasis in patients using compounds of formula II, wherein D, n, R a , R b and R c As defined herein:

Description

technical field [0001] The present invention relates to substituted aromatic sulfur compounds and methods of using them for the treatment and prevention of cancer, particularly peritoneal cancer metastasis. Background technique [0002] Metastases from peritoneal cancer are a deadly form of metastases that occur when intra-abdominal cancer invades into the peritoneal cavity and attaches to the peritoneum, the elastic tissue that lines the abdominal cavity and its internal organs. Peritoneal cancer metastasis may also occur after surgical resection of the intra-abdominal cancer, which releases cancer cells, blood and lymph into the peritoneal cavity. In patients with gastric cancer, the peritoneum and liver are the main sites of recurrence after extended lymphadenectomy (Maruyama et al., World J Surg 1987, 11:418-25; Kaibara et al., Am J Surg 1990, 159:218-21; Korenaga et al., Surg Gynecol Obstet 1992, 174:387-93). After ovarian cancer resection, the most common site of rec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/57C07D213/70C07D215/36C07D223/10C07D231/12C07D235/16C07D263/32C07D263/56C07D309/08C07D309/14C07D333/24C07D271/07C07C317/44A61P35/00A61P35/04
CPCC07C317/14C07C317/44C07D213/40C07D213/57C07D213/70C07D215/36C07D217/06C07D223/10C07D231/12C07D235/16C07D263/32C07D263/56C07D271/07C07D271/10C07D295/18C07D309/08C07D309/14C07D333/20C07D333/24C07C2601/02C07C2601/04C07C2601/14C07D213/71C07D223/12C07D235/06C07D263/57C07D295/185C07D295/192A61P35/00A61P35/04C07C317/32
Inventor 布鲁斯·多尔西斯克特·K·库瓦达杰伊·P·泰洛夫克雷格·A·齐费可萨克
Owner CEPHALON INC
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