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Compound used as IDO (Indoleamine-2,3-dioxygenase) regulator and application thereof

A compound and mixture technology, applied in the field of medicine, can solve problems such as no clinical development

Active Publication Date: 2018-11-23
TETRANOV PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the activity is basically in μmol·L -1 level, so far there is no clinical development information
[0008] Although there are many reports on IDO inhibitor research as an anti-tumor target, and considerable progress has been made, there are still very few compounds that have entered the clinical stage, and there is an urgent need for research and development. Small IDO inhibitors have entered clinical research and are eventually used in the treatment of human tumors and other diseases

Method used

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  • Compound used as IDO (Indoleamine-2,3-dioxygenase) regulator and application thereof
  • Compound used as IDO (Indoleamine-2,3-dioxygenase) regulator and application thereof
  • Compound used as IDO (Indoleamine-2,3-dioxygenase) regulator and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0267]

[0268] The synthesis steps are as follows:

[0269] Synthesis of Intermediate 3-1:

[0270] Intermediate 1-1 (2g) was dissolved in tetrahydrofuran, then 80% hydrazine hydrate (1mL) was added, and then the reaction was reacted at room temperature for 2 hours, TLC showed that the raw material was completely reacted, and then 100ml of hydrazine hydrate was added to the reaction system Ethyl acetate was washed with saturated brine, the organic phase was dried and spin-dried, and passed through a column to obtain intermediate 3-1 (1.1 g, 57%). MS(M+H) + :m / z=356.9, 358.9; 1 HNMR (400MHz, CDCl 3 ): 7.64-7.62 (m, 1H), 7.34-7.27 (m, 2H), 6.54 (br, 1H), 4.02 (br, 2H).

[0271] The synthesis of embodiment 1:

[0272] Dissolve intermediate 3-1 (200 mg) in tetrahydrofuran, then add 4 equivalents of hydrazine hydrate at 0°C, and then slowly raise the temperature to room temperature for reaction. After TLC shows that intermediate 3-1 disappears, adjust the pH of the reactio...

Embodiment 12

[0278]

[0279] The synthesis steps of the target compound Example 12 are as follows.

[0280] Synthesis of compound 15:

[0281] Dissolve chlorosulfonic acid isocyanate (compound 14, 14.1g, 0.1mol) in 100ml of dry dichloromethane, then add tert-butanol (7.4g, 0.2mol) in dichloromethane dropwise under the protection of argon under ice-water bath cooling (10ml) solution, stirred in an ice-water bath for 30min to form solution A. Triethylamine (20.2 g, 0.2 mol) was added dropwise to a suspension of glycine ethyl ester hydrochloride (14 g, 0.1 mol) in DCM (200 ml) under cooling in an ice-water bath, followed by stirring for 15 min to form solution B. Under an ice-water bath, solution A was added dropwise to solution B, then naturally warmed to room temperature and stirred overnight. The reaction solution was diluted with 100ml of dichloromethane, then added with 100ml of saturated ammonium chloride solution and stirred for 5min, separated, the organic phase was dried over an...

Embodiment 13

[0292]

[0293] The synthesis steps of the target compound Example 13 are specifically referred to in Example 12, and the characterization information of the final product Example 13 is as follows: 1 HNMR(MeOD,400MHz)δ=7.22-7.20(q,1H),7.12-7.08(t,1H),6.93-6.89(m,1H),3.68(s,2H),3.21(s,3H).MS [M+H]481.0.

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Abstract

The invention belongs to the technical field of medicines and in particular discloses a compound shown as a formula I or a formula II. Each symbol is defined as claims. The compound shown as the formula I or the formula II, provided by the invention, can be used as an IDO (Indoleamine-2,3-dioxygenase) regulator; the invention specifically discloses application of the compound to preparation of a medicine for treating IDO-mediated diseases with tryptophan metabolic pathway pathologic features. The formula I and the formula II are shown in the description.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a compound used as an IDO modulator and its application in the preparation of medicines for treating diseases characterized by the pathology of the IDO-mediated tryptophan metabolic pathway. Background technique [0002] Tumor is a major disease that seriously endangers human life and health. With the growth and aging of the population, it is expected that tumor-related diseases will increase globally. Tumor has become a common disease. Due to the unrestricted growth, invasion and metastasis of malignant tumors, three conventional treatment methods, surgery, radiotherapy and chemotherapy, are currently used. However, these three treatments cannot completely remove or completely kill tumor cells, so tumor metastasis or relapse. Therefore, immunotherapy has become a hot spot in current research, which obtains anti-tumor effects by mobilizing the host's natural defense mechanism (...

Claims

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Application Information

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IPC IPC(8): C07D271/08C07D413/12C07F9/6584C07F9/6571C07F9/653A61K31/4245A61K31/664A61K31/665A61K31/675A61K31/4523A61P35/00A61P35/02A61P19/00A61P25/28A61P37/00A61P25/24A61P25/22A61P27/12A61P31/18
CPCA61P19/00A61P25/22A61P25/24A61P25/28A61P27/12A61P31/18A61P35/00A61P35/02A61P37/00C07D271/08C07D413/12C07F9/65306C07F9/657154C07F9/65842C07F9/65848
Inventor 吴豫生梁阿朋郭中伟王国辉郑茂林杨挺耿阳牛成山陈其雨
Owner TETRANOV PHARMA CO LTD
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