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Plasmin inhibitor as well as preparation method and application thereof

An unsubstituted and selected technology, applied in the field of medicinal chemistry, can solve the problems of easily causing epilepsy, many adverse reactions, and large dosage of drugs.

Pending Publication Date: 2022-08-05
SCINNOHUB PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In view of the limited choice of clinically available hemostatic drugs, there are more or less deficiencies in dosage, clinical indications, etc., and the existing drugs of the same type are all There are problems such as large dosage, many adverse reactions, and easily causing complications such as epilepsy. It is necessary to develop a new hemostatic drug to better meet clinical needs

Method used

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  • Plasmin inhibitor as well as preparation method and application thereof
  • Plasmin inhibitor as well as preparation method and application thereof
  • Plasmin inhibitor as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1 Preparation of (4-amino-3,4-dihydro-2H-pyrano[2,3-b]pyridin-7-yl)phosphonate hydrochloride

[0062]

[0063] Step 1: Preparation of (3-((tert-butyldimethylsilyl)oxy)propylene)-2-methylpropane-2-sulfinamide

[0064] Weigh 3-((tert-butyldimethylsilyl)oxy)propanal (5.6g), dissolve it in dichloromethane (50mL), add tert-butylsulfinamide (5.4g), anhydrous sulfuric acid Copper (23.8 g) was stirred at room temperature for 48 h. TLC showed that the starting material was consumed, filtered through celite and purified by column chromatography to give the title compound (7.35g).

[0065]

[0066] MS(ESI)m / z(M+H) + = 292.1.

[0067] Step 2: 3-((tert-Butyldimethylsilyl)oxy)-1-(2,6-dichloropyridin-3-yl)propyl)-2-methylpropane-2-sulfinyl Preparation of amides

[0068] Weigh 2,6-dichloropyridine (3.74g) into a 250mL three-necked flask, add tetrahydrofuran (50mL) to dissolve, replace with argon three times, cool to -78°C, and slowly add lithium diisopropylamide with...

Embodiment 2

[0088] Example 2 Preparation of (4-amino-3,4-dihydro-2H-benzopyran-7yl)phosphonate hydrochloride

[0089]

[0090] Step 1: Preparation of N-(7-bromobenzopyran-4-alkylene)-2-methylpropane-2-sulfinamide

[0091] 7-Bromo-4-dihydrochromone (2.5g) was dissolved in tetrahydrofuran (4mL), tert-butylsulfinamide (2.0g) and tetraethyl titanate (4mL) were added successively, and the reaction was carried out at 85°C overnight , TLC showed that the reaction of the starting material was complete. Water was added to quench, filtered, the filter cake was washed with ethyl acetate, the filtrate was backwashed twice with saturated brine (2×15 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain the title compound (2.1 g) ).

[0092]

[0093] MS(ESI)m / z(M+H) + = 329.9.

[0094] Step 2: Preparation of N-(7-bromobenzopyran-4-yl)-2-methylpropane-2-sulfinamide

[0095] Weigh N-(7-bromobenzopyran-4-alkylene)-2-methylpro...

Embodiment 3

[0107] Example 3 Preparation of (4-amino-1,2,3,4-tetrahydroquinolin-7-yl)phosphonate hydrochloride

[0108]

[0109] Step 1: Preparation of methyl 3-((3-bromophenyl)amino)propanoate

[0110] m-bromoaniline (9 g), methyl acrylate (4.6 g) and glacial acetic acid (297 μL) were placed in a sealed tube and reacted at 110° C. for 12 h. After TLC detected that the raw material was consumed, it was diluted with ethyl acetate, washed three times with water, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography to give the title compound (10 g).

[0111]

[0112] MS(ESI)m / z(M+H) + = 257.9.

[0113] Step 2: Preparation of methyl 3-(N-(3-bromophenyl)-4-methylphenylsulfonamido)propanoate

[0114] Methyl 3-((3-bromophenyl)amino)propanoate (10 g) and 4-toluenesulfonyl chloride (8.1 g) were dissolved in pyridine (20 mL) and reacted at room temperature for 2 h. After TLC detected that the raw materials were consumed, the reacti...

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Abstract

The invention relates to a plasmin inhibitor as well as a preparation method and application thereof in the field of pharmacy. The invention further provides a method for preparing the compound, a composition containing the compound, application of the compound serving as a plasmin inhibitor and pharmaceutical application of the compound.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a plasmin inhibitor, its preparation method and its application in the pharmaceutical field. Background technique [0002] Plasmin is a proteolytic enzyme that degrades fibrin. When a blood vessel ruptures due to tissue damage, the hemostatic mechanism is triggered: vasoconstriction, platelet plug formation, initiation of the coagulation process, and eventual formation of stable fibrin. At the same time, due to the deposition of fibrin, the fibrinolytic system is activated, which maintains a balance between the formation and cleavage of fibrin, and plays a role in maintaining vascular patency and remodeling the damaged blood vessel wall in the process of repairing damaged blood vessel walls. damage tissue (Tengborn L, M, Berntorp E. Thromb Res. 2015 Feb;135(2):231-42). [0003] The fibrinolytic system includes plasminogen, tissue-type plasminogen activator (tPA) and urokina...

Claims

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Application Information

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IPC IPC(8): C07F9/6561C07F9/6553C07F9/655C07F9/60C07F9/38A61K31/675A61K31/67A61K31/665A61K31/662A61P7/04A61P41/00
CPCC07F9/6561C07F9/65522C07F9/60C07F9/655372C07F9/3834A61P7/04A61P41/00
Inventor 阳安乐纪森王志王浩张德伟王宵沈欢向杰鲜嘉陵胡晓张晓东唐军苏忠海
Owner SCINNOHUB PHARM CO LTD
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