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Octahydropyrrolo[3,4-c]pyrrole derivatives and uses thereof

A drug and compound technology, applied in the field of octahydropyrrolo[3,4-c]pyrrole derivatives, can solve problems such as safety refusal

Active Publication Date: 2022-02-01
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently the only drug related to orexin receptors on the market is Suvorexant, an anti-insomnia drug developed by Merck of the United States, which is an orexin receptor antagonist. was rejected by the US FDA

Method used

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  • Octahydropyrrolo[3,4-c]pyrrole derivatives and uses thereof
  • Octahydropyrrolo[3,4-c]pyrrole derivatives and uses thereof
  • Octahydropyrrolo[3,4-c]pyrrole derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0198] Example 1 (5-(5-fluoro-benzo[d]oxazol-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-(2,2 , Synthesis of 2-trifluoroethoxy)pyridin-3-yl)methanone

[0199]

[0200] Step 1) Synthesis of 2-(2,2,2-trifluoroethoxy)nicotinic acid

[0201] In a 50mL three-neck flask, N,N-dimethylformamide (10mL), 2,2,2-trifluoroethanol (435μL, 6mmol) were added under nitrogen protection, and sodium hydride (180mg, 60% dispersion in liquid paraffin, 4.5 mmol), and kept stirring at 0°C for 0.5 hours. Sodium hydride (180 mg, 60% dispersed in liquid paraffin, 4.5mmol) and 2-fluoropyridine-3-carboxylic acid (423mg, 3mmol) were dissolved in N,N-dimethylformamide (5mL) (turbid solution ), added dropwise to the reaction system at 0°C, and after the dropwise addition was completed, it was raised to room temperature and stirred overnight. Stop the reaction after TLC detects that the reaction is complete, slowly add water to quench, add 1N HCl to pH = 2, use ethyl acetate to extract (3*30mL), co...

Embodiment 2

[0218] Example 2 (5-(5-chloro-benzo[d]oxazol-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-(2,2 , Synthesis of 2-trifluoroethoxy)pyridin-3-yl)methanone

[0219]

[0220]The title compound of this step was prepared by referring to the method described in Step 4 of Example 1, that is, weighed 2-(2,2,2-trifluoroethoxy)nicotinic acid (184 mg, 0.83 mmol) into a 50 mL one-mouth bottle, and added Dichloromethane (5 mL), triethylamine (0.35 mL, 2.5 mmol), dissolved. Then HATU (318 mg, 0.836 mmol) was added, and after stirring for twenty minutes, 5-chloro-2-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)benzo[d]oxazole was added Hydrochloride (200mg, 0.758mmol) and stirred at room temperature overnight. Stop the reaction, add sodium bicarbonate solution to quench the reaction, extract with dichloromethane (3*15mL), dry the organic phase with anhydrous sodium sulfate, spin to dry the solvent, column chromatography (dichloromethane / methanol (v / v)=30 / 1) The title compound was obtained as...

Embodiment 3

[0225] Example 3 (2-(2,2-difluoroethoxy)pyridin-3-yl)(5-(5-fluorobenzo[d]oxazol-2-yl)hexahydropyrrolo[3,4 -c] Synthesis of pyrrole-2(1H)-yl)methanone

[0226]

[0227] Step 1) Synthesis of 2-(2,2-difluoroethoxy)nicotinic acid

[0228] The title compound of this step was prepared by referring to the method described in step 1 of Example 1. In a 50mL three-necked flask, N,N-dimethylformamide (20mL) and 2,2-difluoroethanol (0.9mL , 14mmol), sodium hydride (425mg, 60% dispersed in liquid paraffin, 10.6mmol) was added at 0°C, and stirred at 0°C for 0.5 hours. Sodium hydride (425 mg, 60% dispersed in liquid paraffin, 10.6 mmol) and 2-fluoropyridine-3-carboxylic acid (1 g, 7.1 mmol) were dissolved in N,N-dimethylformamide (10 mL) (turbid liquid), added dropwise to the reaction system at 0°C, and after the dropwise addition was completed, it was raised to room temperature and stirred overnight. Stop the reaction after TLC detects that the reaction is complete, slowly add water...

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Abstract

The present invention relates to octahydropyrrolo[3,4-c]pyrrole derivatives and uses thereof. The compound of the present invention and the pharmaceutical composition comprising the compound are used for antagonizing orexin receptors. The present invention also relates to methods for preparing these compounds and pharmaceutical compositions, and their use in treating or preventing diseases related to orexin receptors.

Description

[0001] field of invention [0002] The invention belongs to the technical field of medicines, and specifically relates to a class of octahydropyrrolo[3,4-c]pyrrole derivatives, a pharmaceutical composition containing such compounds, and their use methods and purposes. More specifically, the compounds and pharmaceutical compositions of the present invention can be used as orexin receptor antagonists to treat, prevent or alleviate diseases related to orexin receptors. [0003] Background of the invention [0004] Orexin, also known as hypocretin and orexin, includes orexin A and orexin B (or hypocretin-1 and hypocretin-2), which are secreted by the hypothalamus Its main physiological functions are as follows: 1. Regulating food intake, orexin can significantly promote food intake, and it shows a dose-dependent response, and activates the neurons that regulate food intake; 2. Participates in the regulation of energy metabolism, orexin can significantly promote Increase metabolic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/506A61K31/517A61K31/4439A61P25/20A61P25/24A61P25/22A61P25/00A61P25/18A61P25/28A61P25/30A61P25/16A61P25/14A61P25/06A61P25/04A61P1/00A61P29/00A61P25/08A61P9/00A61P3/10A61P3/00A61P37/02A61P9/12A61P5/00
CPCC07D487/04
Inventor 金传飞许腾飞梁海平
Owner SUNSHINE LAKE PHARM CO LTD
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