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Heterocyclic compound as well as preparation method and application thereof

A technology of heterocyclic compounds and compounds, applied in organic chemistry, measuring devices, instruments, etc., can solve problems affecting the quality of raw materials and finished products

Active Publication Date: 2021-01-08
JUMPCAN (SHANGHAI) MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In fact, some process impurities may be passed downstream through the synthetic route, or by participating in subsequent reactions, affecting the quality of the finished drug substance

Method used

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  • Heterocyclic compound as well as preparation method and application thereof
  • Heterocyclic compound as well as preparation method and application thereof
  • Heterocyclic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment 1: Preparation contains the crude product of compound I:

[0088]

[0089]Take a 5L four-necked flask, blow nitrogen flow into it for 5 minutes, add compound 1 (0.76mol, 150.00g) into the reaction flask, add THF (0.75L), turn on the nitrogen protection, turn on the stirring, and wait until the internal temperature drops to 10 At ~15°C, start to add EtMgBr solution (2.28mol, 1.14L) dropwise. During the dropping process, keep the internal temperature below 20°C. After the dropwise addition, start heating, control the internal temperature at 60-65°C, and react for 1.5-2.0 hours , turn on the cooling, and when the internal temperature drops to 10-15°C, start to add 3-chloro-2-methylpropene (3.04mol, 275g) dropwise, keep the internal temperature below 40°C during the dropwise addition, within 20-30 minutes After the dropwise addition is completed, turn on the heating device and maintain the reaction at 60-65° C. for 2 hours. After the reaction is complete, tur...

Embodiment 2

[0090] Embodiment 2: the preparation separation and purification method of compound I

[0091] Step 1: Solution preparation of intermediate 2 crude product

[0092] Take the crude product of intermediate 2 in Example 1, add tetrahydrofuran, deionized water and acetonitrile (about 2:1:1 ratio) and dissolve to 20mg / ml, use a syringe filter (nylon NY 0.45μm-25mm) to filter and set aside.

[0093] Step 2: Optimization of the solution separation and purification method for the crude intermediate 2

[0094] The separation degree of the solution of the crude product of intermediate 2 was investigated respectively under neutral, acidic and alkaline conditions, wherein: under neutral conditions, mobile phase A was purified water; under acidic conditions, mobile phase A was purified water containing 0.1% trifluoro Purified water of acetic acid; under alkaline conditions, mobile phase A is purified water containing 0.1% ammonia 10mM ammonium bicarbonate;

[0095] Other analysis conditi...

Embodiment 3

[0114] Embodiment 3: Compound 1 is used for the quality control detection of intermediate 2

[0115] Take an appropriate amount of intermediate 2 crude product prepared in Example 1, add methanol to dissolve and dilute to make a solution containing about 1 mg per 1 ml, as the test solution; in addition, take an appropriate amount of Compound I reference substance prepared in Example 2, add methanol Dissolve and dilute to make a solution containing about 2 μg per 1 ml, as the reference solution. According to high performance liquid chromatography (Chinese Pharmacopoeia 2015 edition four general rules 0512), with octadecylsilane bonded silica gel as filler (YMC-Triart C 18 , 4.6×250mm, 5μm, or other chromatographic columns with equivalent performance); use 10mmol / L dipotassium hydrogen phosphate solution (adjust the pH value to 7.5 with phosphoric acid) aqueous solution-acetonitrile (95:5) as mobile phase A, and use 10mmol / L L dipotassium hydrogen phosphate solution (adjust the...

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PUM

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Abstract

The invention discloses a heterocyclic compound as well as a preparation method and application thereof. The invention provides a heterocyclic compound shown as a formula I or salt thereof. The heterocyclic compound is an intermediate process impurity of olprinone hydrochloride, and can be used as a reference substance for quality control of an olprinone hydrochloride synthesis intermediate.

Description

technical field [0001] The present invention relates to a heterocyclic compound, its preparation method and application. Background technique [0002] Oprinone hydrochloride is a typical selective phosphodiesterase III inhibitor, which improves hemodynamic parameters and exercise tolerance through the upstream mechanism of the heart, and is used for the treatment of congestive heart failure. It has the effects of enhancing myocardial contractility, dilating blood vessels, and improving cardiac insufficiency, and has obvious curative effects on reducing cardiac morbidity and mortality. In addition, Oprinone Hydrochloride is also used in the treatment of stroke, and has the functions of protecting liver and spleen and relaxing bronchial smooth muscle. The structure of Oprinone Hydrochloride is as follows: [0003] [0004] Document Chem.Pharm.Bull., 39 (6), 1556-1567 (1991) discloses the synthetic method of Oprinone Hydrochloride, and its synthetic route is as follows: ...

Claims

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Application Information

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IPC IPC(8): C07D471/04G01N30/02
CPCC07D471/04G01N30/02
Inventor 周春东张梓桐夏荣杨飞张勇
Owner JUMPCAN (SHANGHAI) MEDICAL TECH CO LTD
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