Anticoagulant diamine derivative

A technology of oxalamide, compounds, applied in the field of new compounds

Inactive Publication Date: 2012-06-27
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 10 mL of 5 g (1S, 3S, 6R)-N, N-dimethyl-7-oxabicyclo[4.1.0] heptane-3-carboxamide in ethanol, add 30 mL of 28% ammonia water at room temperature, and raise the temperature Stirring at 40°C for 24 hours, the reaction was complete; the reaction mixture was concentrated under reduced pressure to obtain (1S,3R,4R)-3-amino-4-hydroxy-N,N-dimethylcyclohexylformamide crude product 5.9g, the crude product Dissolve in 25mL of water, add 9.65g of di-tert-butyl dicarbonate and 7g of sodium bicarbonate at room temperature, stir and react at 40°C for 2 hours, the reaction is complete, extract 3 times with 25mL 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 (CDCl...

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 methyl isobutyl ketone Add 17g of triethylamine and 16g of methanesulfonyl chloride in sequence, stir at room temperature for 1 hour, and the reaction is complete; add water to the reaction solution, separate the liquids, and concentrate the organic phase under reduced pressure to obtain a crude product. Add 75 mL of methyl isobutyl ketone to the crude product , 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,...

Embodiment 3

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

[0047]

[0048] At room temperature, 20 g of (1S, 3R, 4R)-3-[(tert-butoxycarbonyl)amino]-4-methanesulfonyloxy-N, N-dimethylcyclohexylformamide was dissolved in 100 mL of toluene, Add 7.14g of sodium azide and 6.5g of benzyltriethylammonium chloride in turn, 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, wash the organic phase with saturated brine and water successively, and 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...

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PUM

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Abstract

The invention discloses an anticoagulant diamine derivative. The anticoagulant diamine derivative can effectively inhibit activated blood coagulation factors (FXa for short), and can be used for preparing anticoagulants for preventing or treating thrombus formation or embolism.

Description

technical field [0001] The present invention relates to a new compound, which can effectively inhibit activated blood coagulation factor X (abbreviated as "FXa"), and can be used to prepare an 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,...

Claims

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Application Information

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IPC IPC(8): C07D487/04A01P7/02
Inventor 王颖黄青春闫革新
Owner CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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