Anticoagulation diamine derivative

A compound, tert-butoxycarbonyl technology, applied in the field of new compounds

Inactive Publication Date: 2013-10-02
CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

DVT also puts patients at high risk of developing pulmonary thromboembolism

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxyl-N,N-dimethylcyclohexylformamide

[0037]

[0038] Dissolve 10mL of 5g (1S,3S,6R)-N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide in ethanol, add 30mL of 28% ammonia water at room temperature, and heat up to Stirring at 40°C for 24 hours, the reaction was complete; the reaction mixture was concentrated under reduced pressure to obtain 5.9 g of the crude product of (1S,3R,4R)-3-amino-4-hydroxy-N,N-dimethylcyclohexylformamide, and the crude product was Dissolve in 25 mL of water, add 9.65 g of di-tert-butyl dicarbonate and 7 g of sodium bicarbonate at room temperature, stir and react at 40°C for 2 hours, the reaction is complete, extract 3 times with 25 mL of methyl isobutyl ketone, combine the organic phases, Concentrate under reduced pressure to obtain a crude product, which is recrystallized from methyl isobutyl ketone, filtered, and dried to obtain 6.3 g of the title compound.

[0039] 1 H-NMR (C...

Embodiment 2

[0041] Example 2 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-methanesulfonyloxy-N,N-dimethylcyclohexylformamide

[0042]

[0043] At room temperature, 21.5g (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-N,N-dimethylcyclohexylformamide was dissolved in 200mL methylisobutyl To the ketone, add 17g triethylamine and 16g methanesulfonyl chloride successively, stir at room temperature for 1 hour, and the reaction is complete; after adding water to the reaction solution, separate the liquids, and concentrate the organic phase under reduced pressure to obtain a crude product, to which 75mL methyl isobutyl Ketone, stirred at room temperature for 3 hours, filtered, and dried to obtain 24.3 g of the title compound.

[0044] 1 H-NMR (CDCl 3 )δ:1.45(s,9H),1.59-1.66(m,1H),1.68-1.77(m,1H),1.85-1.96(m,2H),2.04-2.14(m,1H),2.16-2.27( m,1H),2.73-2.79(m,1H),2.93(s,3H),3.02(s,3H),3.08(s,3H),3.98-4.06(m,1H),4.65-4.83(m, 2H).

[0045] [α]=-15°(c=1.0, CHCl 3 ).

Embodiment 3

[0046]Example 3 (1S,3R,4S)-4-amino-3-[(tert-butoxycarbonyl)amino]-N,N-dimethylcyclohexylformamide oxalate

[0047]

[0048] Dissolve 20g of (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-methanesulfonyloxy-N,N-dimethylcyclohexylformamide in 100mL of toluene at room temperature , add 7.14g of sodium azide and 6.5g of benzyltriethylammonium chloride successively, raise the temperature to 60°C and stir for 72 hours, then the reaction is complete; add water to the reaction solution, separate the liquids, and wash the organic phase with saturated brine and water successively, Directly add methanol for dilution, then add 7.5% Pd / C and ammonium formate, stir at 40°C for 1 hour, TLC monitors that the reaction is complete; after filtering to remove Pd / C, the organic phase is concentrated under reduced pressure to obtain a crude product, which is dissolved in 200 mL of aqueous acetonitrile and 4.94 g of oxalic anhydride, stirred at room temperature for 17 hours, filtered to obtain a cry...

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PUM

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Abstract

The invention discloses anticoagulation diamine derivatives. The anticoagulation diamine derivative disclosed by the invention can be used for effectively restraining activated blood coagulation factors X (which are short for FXa) and can be used for preparing an anticoagulant for preventing or treating thrombogenesis or embolism.

Description

technical field [0001] The present invention relates to a new compound, which can effectively inhibit activated blood coagulation factor X ("FXa" for short), and can be used to prepare anticoagulant for preventing or treating thrombosis or embolism. Background technique [0002] In the arterial system, abnormal thrombosis is mainly related to coronary arteries, cerebrovascular and peripheral blood vessels, and diseases related to thrombotic closure of these vessels mainly include acute myocardial infarction (AMI), unstable angina, thromboembolism, and thrombolysis Treatment of acute vessel closure, transient ischemic attack, stroke, intermittent claudication and coronary artery bypass grafting (CABG) or peripheral artery bypass grafting associated with percutaneous transluminal coronary angioplasty (PTCA). As for the venous vessels, pathological thrombosis often occurs in the veins of the lower extremities after abdominal, knee and hip surgery (deep vein thrombosis, DVT). D...

Claims

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Application Information

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IPC IPC(8): C07C271/24C07C269/04C07D487/04A61P7/02
Inventor 王颖
Owner CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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