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Crystal forms of thiazole compounds and their applications

A compound and crystal form technology, which is applied to the crystal form of thiazole compounds and its application field, can solve the problems of damage to host cell DNA replication and decreased therapeutic effect

Active Publication Date: 2022-03-29
PHAENO THERAPEUTICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these treatments have considerable side effects as they impair host cell DNA replication or are only effective in a limited number of viral infections
In addition, viruses are known to develop resistance to treatments, making them increasingly less effective

Method used

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  • Crystal forms of thiazole compounds and their applications
  • Crystal forms of thiazole compounds and their applications
  • Crystal forms of thiazole compounds and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: the preparation of formula (I) compound

[0086]

[0087] Step 1: Synthesis of compound 2

[0088] NBS (57.70 g, 324.22 mmol) and AIBN (5.32 g, 32.42 mmol) were added to a solution of compound 1 (30.00 g, 162.11 mmol) in carbon tetrachloride (400.00 mL), and the system was stirred at 80° C. for 2 hours. After the reaction was completed, it was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain Compound 2 as a colorless oil. 1 H NMR (400MHz, CDCl 3 )δ7.55 (s, 1H), 7.47-7.45 (m, 1H), 7.28-7.25 (m, 1H), 4.62 (s, 1H), 4.60 (s, 2H).

[0089] Step 2: Synthesis of Compound 3

[0090] Sodium hydrogen (9.60g, 240.02mmol, content 60%) was slowly added to a solution of ethanol (144.00mL) and tetrahydrofuran (432.00mL), stirred at room temperature for 5 minutes, and then diethyl malonate (18.22g, 113.75mmol ) and compound 2 (39.00g, 113.75mmol), the system was stirred at room temperature for 30 minutes. After t...

Embodiment 2

[0101] Embodiment 2: Preparation of the A crystal form of the compound of formula (I)

[0102]Weigh about 20 g of the compound of formula (I), add 800 mL of ethanol, and stir overnight with a magnetic stirrer. The mixture was filtered, the filter cake was rinsed with a small amount of ethanol, and the obtained solid was dried under reduced pressure. XRPD detection, the A crystal form of the compound of formula (I) was obtained.

Embodiment 3

[0103] Embodiment 3: Preparation of the B crystal form of the compound of formula (II)

[0104]

[0105] Weigh the compound of formula (I) (56.5g, 131.85mmol) into a 3L round bottom flask, add 2L of anhydrous tetrahydrofuran, and heat to 50-55°C to dissolve it completely. After filtration, methanesulfonic acid (12.67 g, 131.85 mmol) diluted with 50 mL of anhydrous tetrahydrofuran was added dropwise to the filtrate at 55° C., a solid precipitated out, and stirring was continued for 2 hours. After filtering, the filter cake was dried under reduced pressure, and the resulting solid was added to a round bottom flask, and 1 L of absolute ethanol was added, heated to 40°C and stirred for 14 hours. After filtration, the filter cake was vacuum-dried, and detected by XRPD, the crystal form B of the compound of formula (II) was obtained.

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Abstract

The invention discloses the A crystal form of the compound of formula (I), the compound of the formula (II) and its B crystal form, and the A crystal form of the formula (I) compound, the formula (II) compound and its B crystal form in the preparation and treatment of simple Use of drugs for herpes virus-related diseases.

Description

[0001] This application claims the following priority: [0002] CN201810738963.X, application date: 2018.07.06. technical field [0003] The present invention relates to the crystal form A of the compound of formula (I), the compound of formula (II) and the crystal form B thereof, and the crystal form A of the compound of formula (I), the compound of formula (II) and the crystal form B thereof in the preparation and treatment of herpes simplex Application of drugs for virus-associated diseases. Background technique [0004] There is a great need for new therapeutic approaches in the treatment of viral diseases. While great strides have been made in developing treatments for various bacterial infections, few viable treatments are available for the treatment of viruses. Zidovudine is the main species approved for the treatment of HIV. Ganciclovir, aciclovir, and foscarnet are currently used to treat herpes virus infections. However, these treatments have considerable side ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12C07D277/54A61K31/426A61P31/22
CPCA61P31/22C07D417/12A61K31/4439A61K31/426C07D277/54C07B2200/13
Inventor 石卫华江志赶贺海鹰
Owner PHAENO THERAPEUTICS CO LTD