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3-phenyl-cinnoline homologue and antitumor agent containing the same

An anti-tumor agent, analog technology, applied in the field of 3-phenyl-cinnoline analog or its physiologically acceptable salt, anti-tumor agent field, can solve the problem of no description of cinnoline analog, no description of cinnoline analog The anti-tumor activity of the drug, and the anti-tumor effect of cinnoline analogs was not explained.

Inactive Publication Date: 2006-02-15
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these two documents neither describe the cinnoline analog of the present invention represented by the following general formula (1), nor the antitumor activity of the cinnoline analog
[0004] In the following Non-Patent Document 3, the synthesis and reaction of cinnoline derivatives are described, however, the antitumor effect of cinnoline analogues is not described

Method used

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  • 3-phenyl-cinnoline homologue and antitumor agent containing the same
  • 3-phenyl-cinnoline homologue and antitumor agent containing the same
  • 3-phenyl-cinnoline homologue and antitumor agent containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] Synthesis of 7-phenyl-3-(3-trifluoromethylphenyl)-7,8-dihydro-6H-cinnolin-5-one The 7-phenyl-3 obtained in Reference Example 2 A solution of -(3-trifluoromethylphenyl)-4,6,7,8-tetrahydro-1H-cinnolin-5-one in pyridine (5 mL) was stirred at 70°C for 3 days. The residue obtained by concentrating the reaction liquid under reduced pressure was purified using silica gel column chromatography (hexane / ethyl acetate=3 / 1) to obtain a yellow crude product, which was purified by suspension method (hexane / ethyl acetate=3 ml / 0.5ml) was further purified to obtain the title compound (124.0mg, 48.9%, in step 2).

[0154] 1 H-NMR (200MHzFT, TMS, CDCl 3 ) 2.93-3.23 (2H, complex peak), 3.51-3.75 (2H, complex peak), 3.76-3.97 (1H, m), 7.20-7.49 (5H, m), 7.70 (1H, t, J=7.8Hz) , 7.80 (1H, d, J=7.8Hz), 8.31-8.42 (1H, m), 8.46 (1H, brs) MS (ESI)

[0155] m / z 369[M+H] +

Embodiment 2

[0157] Synthesis of 5-oxo-3-(3-trifluoromethylphenyl)-7,8-dihydro-6H-cinnoline-7-carboxylic acid ethyl ester

[0158] Except that ethyl 3-hydroxy-5-oxo-cyclohex-3-enecarboxylate obtained in Reference Example 3 was used instead of 5-phenyl-1,3-cyclohexanedione, by similar reference The reaction in Example 1 was then carried out in a manner similar to that in Reference Example 2 and Example 1 to obtain the target compound.

[0159] 1 H-NMR (200MHzFT, TMS, CDCl 3 )1.26(3H, dt, J=1.8, 7.1Hz), 3.04(2H, d, J=6.4Hz), 3.62-3.87(2H, m), 4.19(1H, q, J=7.1Hz), 7.69( 1H,t,J=7.7Hz), 7.80(1H,d,J=8.0Hz), 8.31(1H,s), 8.34(1H,d,J=7.7Hz), 8.44(1H,s)

[0160] MS (ESI)

[0161] m / z 365[M+H] +

Embodiment 3

[0163] Synthesis of ethyl 5-hydroxy-3-(3-trifluoro-methylphenyl)-5,6,7,8-tetrahydrocinnoline-7-carboxylate

[0164] To ethyl 5-oxo-3-(3-trifluoro-methylphenyl)-7,8-dihydro-6H-cinnoline-7-carboxylate obtained in Example 2 (100 mg, 0.274 mmol) in ethanol (0.5 mL) was added sodium borohydride (10.4 mg, 0.274 mmol), and stirred at room temperature for 1 hour. After the reaction was completed, the reaction liquid was quenched with 1N aqueous potassium hydrogensulfate solution (1 mL), extracted with ethyl acetate (3 ml), then dried over sodium sulfate, the desiccant was filtered, the organic layer was concentrated under reduced pressure, and silica gel column chromatography ( hexane / ethyl acetate=1 / 1 to 1 / 2) to obtain the title compound (65 mg, 64.8%) as a pale yellow solid.

[0165] 1 H-NMR (200MHzFT, TMS, CDCl 3) 1.30 (3H, t, J = 7.1Hz), 2.11 (1H, ddd, J = 8.2, 9.5, 13.5Hz), 2.56 (1H, dq, J = 3.1, 13.5Hz), 3.00-3.18 (2H, complex peak), 3.38-3.63 (2H, m), 4.21 (2H, q, J=7.1Hz),...

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Abstract

A 3-phenyl-cinnoline homologue or a physiologically acceptable salt thereof; and a cytostatic agent or antitumor agent comprising the same as an active constituent.

Description

technical field [0001] The present invention relates to a 3-phenyl-cinnoline analogue or a physiologically acceptable salt thereof, and an antitumor agent comprising the analogue or a physiologically acceptable salt thereof as an active ingredient. Background technique [0002] Malignant tumors are populations of cells that continue to proliferate in vivo contrary to normal biological mechanisms, leading to the death of the host unless properly treated. Malignant tumors are usually treated with surgical resection, radiation irradiation, hormone therapy or chemotherapy, especially surgery is the first choice for the treatment of malignant solid tumors. Radiation therapy, hormonal therapy, and chemotherapy are often used before or as adjunctive therapy after surgery, or in the treatment of malignant solid tumors judged to be impossible to treat with surgery. Hormone therapy and chemotherapy are used to shrink the area of ​​surgical resection, or to regress and disappear tumor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/28C07D471/04A61K31/502A61K31/5025A61P35/00
Inventor 黑岩俊介小田中淳子丸山佐起子佐藤美孝户村有宏佐藤弘铃木良一
Owner NIPPON KAYAKU CO LTD
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