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Tumor immune compounds and their applications

A compound and composition technology applied in the application field of STING agonist

Active Publication Date: 2021-06-04
浙江杭煜制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But if the DNA leaks into the cytoplasm, it activates STING, triggering an immune response

Method used

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  • Tumor immune compounds and their applications
  • Tumor immune compounds and their applications
  • Tumor immune compounds and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Embodiment 1: the preparation of compound 1A, compound 1B

[0140] Step 1: Preparation of Compound 1-2

[0141]

[0142] Under the protection of argon, the compound 4-chloro-5-fluoro-7H-pyrrolo[2,3-D]-pyrimidine (1.03g, 6.0mmol) was dissolved in acetonitrile (40mL) solution, and BSA (1.76mL, 7.2 mmol), the reaction system was stirred for 5 min and then added 1-1 (3.0 g, 6.0 mmol) and trimethylsilyl trifluoromethanesulfonate (1.32 mL, 7.2 mmol). After reacting at 25°C for 30min, the temperature was raised to 80°C for 3h. Add water (100mL) to quench the reaction, extract with ethyl acetate (100mL x 3), combine the organic phases, wash with saturated brine (100mL), dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure. The crude product is subjected to silica gel column chromatography Purification (petroleum ether / ethyl acetate (v / v)=5 / 1) gave compound 1-2.

[0143] MS(ESI)m / z(M+H) + =616.1

[0144] 1 H NMR (400MHz, CDCl 3...

Embodiment 2

[0223] Embodiment 2: the preparation of compound 2A, 2B, 2C, 2D

[0224] Step 1: Preparation of compound 2-3

[0225]

[0226] Compound 2-2 (1g, 3.91mmol) was dissolved in acetonitrile (20mL) solution, BSA (0.8mL, 7.1mmol) was added, and the reaction system was stirred for 5min, followed by adding 2-1 (2.0g, 5.88mmol) and trifluoroform Trimethylsilyl sulfonate (0.6 mL, 7.1 mmol). After reacting at 25°C for 5min, the temperature was raised to 80°C for 3h. Add water (50mL) to quench the reaction, extract with ethyl acetate (50mL x3), combine the organic phases, wash with saturated brine (50mL), dry over anhydrous sodium sulfate, filter, concentrate the filtrate under reduced pressure, and purify the crude product by silica gel column chromatography (petroleum ether / ethyl acetate (v / v)=1 / 1), to obtain compound 2-3.

[0227] MS(ESI)m / z(M+H) + =536.2

[0228] 1 H NMR (400MHz, DMSO-d 6 )δ8.57(s,1H),8.08–8.04(m,3H),7.70(dd,J=11.4,18.8Hz,2H),7.58(t,J=7.7Hz,3H),7.51(t,J =7.8...

Embodiment 3

[0292] Embodiment 3: the preparation of compound 3A, 3B

[0293] Step 1: Preparation of compound 3-2

[0294]

[0295] Compound 3-1 (7.5g, 48.65mmol) was dissolved in methanol (2400mL), benzophenone (1.45g, 7.93mmol) was added, the reaction mixture was bubbled with argon for 1.5h, and then protected with argon, at 25°C Under these conditions, the reaction was stirred for 24 hours while irradiating with a mercury lamp. The reaction solution was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v)=3 / 2) to obtain compound 3-2.

[0296] 1 H NMR (400MHz, CDCl 3 )δ4.73(d, J=5.4Hz, 1H), 4.31(d, J=5.4Hz, 1H), 3.94-3.83(m, 1H), 3.76-3.63(m, 1H), 2.81-2.74(m ,1H),2.61-2.47(m,1H),2.20-2.13(m,1H),1.44(s,3H),1.36(s,3H).

[0297] Step 2: Preparation of compound 3-3

[0298]

[0299] Under nitrogen protection, compound 3-2 (3.3g, 17.72mmol) was dissolved in pyridine (50mL), tert-butyldimet...

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Abstract

Tumor immune compounds and their applications. The invention discloses the compound represented by formula (I), its optical isomer and its pharmaceutically acceptable salt, and the application of the compound as STING agonist. .

Description

technical field [0001] The present invention relates to the compound represented by formula (I), its optical isomer and its pharmaceutically acceptable salt, and the application of the compound as STING agonist. Background technique [0002] For a long time, researchers have been trying to completely eliminate tumor cells by activating the patient's immune system so that their own immune system can effectively fight tumors. However, the probability of spontaneous tumor remission is extremely low, so most patients cannot benefit from it. In the 1960s and 1970s, treatment methods such as BCG injection and non-specific strengthening of the immune system appeared. In the 1980s, interferon and IL-2, which can activate T cells and NK cells, were also tried to be used in the treatment of cancer, but these methods still have many limitations, such as the half-life of exogenous cytokines in the blood Very short, which must be compensated with frequent dosing and high doses. Non-sp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H23/00A61P35/00A61P35/02A61K31/7084A61K31/7076
CPCA61P35/00A61P35/02C07H23/00
Inventor 彭建彪郭淑春刘洋叶艳郭海兵
Owner 浙江杭煜制药有限公司
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