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Thioamide compound or its salt and cytokine production inhibitor containing the same

A thioamide and cytokine technology, which is used in the preparation of organic compounds, active ingredients of heterocyclic compounds, and medical preparations containing active ingredients, etc., can solve problems such as worsening diseases, abnormal balance, and abnormal immune function.

Inactive Publication Date: 2007-02-21
ISHIHARA SANGYO KAISHA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is known that when the control of the prevention mechanism of these organisms is lost or lowered for some reason, it is known to cause abnormal hyperactivity or abnormal balance of immune function, and to induce or aggravate various diseases

Method used

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  • Thioamide compound or its salt and cytokine production inhibitor containing the same
  • Thioamide compound or its salt and cytokine production inhibitor containing the same
  • Thioamide compound or its salt and cytokine production inhibitor containing the same

Examples

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Embodiment

[0107] Hereinafter, examples (synthesis examples and test examples) of the present invention will be described, but the present invention is not limited to these examples.

Synthetic example 1

[0109] Synthesis of N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-2-chloro-5-nitrothiobenzamide (Compound No.1)

[0110] 410mg of N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-2-chloro-5-nitrobenzamide and 452mg of Lawson The 10m toluene solution of the reagent was stirred overnight. After the reaction, it was cooled, and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, the insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by column chromatography to obtain 312 mg of N-(4-(3-chloro-5- Trifluoromethyl-2-pyridyloxy)phenyl)-2-chloro-5-nitrothiobenzamide (Compound No. 1).

[0111] The following compound can be synthesized by the same method as in Synthesis Example 1.

[0112] ·Compound No. 2: N-(4-(6-chloro-4-trifluoromethyl-2-pyridyloxy)phenyl)-2-chloro-5-nitrothiobenzamide (melting point 186 -187℃)

[0113] ·Compound No. 3: N-(3-(6...

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PUM

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Abstract

The invention provides cytokine production inhibitors useful as preventive or therapeutic agents for diseases accompanied with abnormally enhanced immune function. Cytokine production inhibitors containing as the active ingredient thioamides represented by the general formula (I) or salts thereof: wherein A is N, NO, C-NO2, or C-CN; Hal is halogeno; M<1> is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, a heterocycle, amino, O, S, SO, or SO2; M<2> is amino, O, S, or a single bond; R<1> is halogeno, alkyl, or the like; R<2> R<3>, R<4> and R<5> are each independently H, alkyl, or the like; R<6> is halogeno, alkyl, or the like; Cy is cycloalkyl, cycloalkenyl, aryl, or a heterocycle; k, p and q are each independently an integer of 0 to 3; and r is an integer of 0 to 5.

Description

Technical field [0001] The present invention relates to a thioamide compound or a salt thereof useful as a therapeutic or preventive drug for diseases accompanied by abnormally increased immune function. Background technique [0002] In the immune response of an organism, cytokines produced by various immune cells control the directionality of the immune response. In the immune response control, helper T cells play a central role, which can be divided into subsets of Th1 and Th2 according to the types of cytokines produced. It is known that Th1 type cells mainly produce interleukin 2 (IL-2), interferon gamma (IFN- gamma), etc., and participate in cellular immunity such as infection prevention of viruses and bacteria. It is known that Th2 cells mainly produce interleukin 4 (IL-4), interleukin 5 (IL-5), interleukin 6 (IL-6), interleukin 10 (IL-10), interleukin 13 (IL-13), etc., and participate in Humoral immunity such as the prevention of parasite infection and the production of an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C327/48A61K31/166A61K31/325A61K31/275A61K31/41A61K31/4164A61K31/4192A61K31/426A61K31/428A61K31/44A61K31/4409A61K31/4412A61K31/4439A61K31/444A61K31/4545A61K31/455A61K31/47A61K31/4709A61K31/4965A61K31/505A61K31/5377A61P3/10A61K31/541A61P5/14A61P11/02A61P11/06A61P17/00A61P17/04A61P19/02A61P21/04A61P25/00A61P27/14A61P29/00A61P37/02A61P37/08A61P43/00C07D237/20A61K31/18A61K31/352A61K31/401A61K31/404A61K31/4045A61K31/415A61K31/423A61K31/425A61K31/437A61K31/50A61K31/517A61K31/538A61P27/16A61P37/00A61P37/06C07C233/66C07C233/69C07C233/71C07C233/78C07C311/17C07C323/42C07D207/09C07D209/04C07D209/08C07D209/42C07D213/64C07D213/69C07D213/70C07D213/74C07D213/81C07D213/82C07D213/83C07D215/20C07D215/22C07D231/18C07D231/20C07D235/08C07D237/04C07D239/30C07D239/34C07D239/42C07D239/60C07D241/12C07D241/18C07D249/18C07D257/04C07D263/58C07D277/20C07D277/36C07D277/74C07D311/08C07D311/46C07D401/12C07D471/04
CPCC07C327/48C07C233/71C07D239/42C07C2103/74C07D239/34C07C233/66C07C233/69C07C323/42C07D213/83C07C233/78C07C2603/74A61P11/02A61P11/06A61P17/00A61P17/04A61P19/02A61P21/04A61P25/00A61P27/14A61P27/16A61P29/00A61P3/10A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00A61P5/14
Inventor 加藤文法木村博彦玉井清山元一浩佐野光夫森新家冈田隆士植木寿彦东久美子
Owner ISHIHARA SANGYO KAISHA LTD
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