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Novel compound with blood coagulation resisting function

A compound, C1-C6 technology, applied in the field of medicine

Active Publication Date: 2010-03-31
GUANGZHOU HEERSHI PHARMA DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are some defects in these compounds that have been disclosed at present, mainly that these compounds need to show activity for a long time after administration, therefore, it is necessary to seek some new compounds, which can quickly show the ability of high activity

Method used

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  • Novel compound with blood coagulation resisting function
  • Novel compound with blood coagulation resisting function
  • Novel compound with blood coagulation resisting function

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] 5-N-[(1RS)-2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothiophene[3,2-c Preparation of ]pyridin-2-yl acetylsalicylate

[0061]

[0062] Compound 1

[0063] 368 mg of 5-[(1RS)-2-cyclopropyl-1-(2-fluorophenyl 1)-2-oxoethyl]-4,5,6,7-tetrahydrothiophene[3,2 -c] Pyridin-2(4H)-one hydrochloride and 100mg of sodium hydride (52%, dispersed in mineral oil) were added to a 25ml reaction flask, then 2ml of anhydrous tetrahydrofuran was added, stirred for 30 minutes, and then added 200 mg of salicyloyl chloride was stirred and reacted for 2 hours, the reaction was stopped, and 57.9 mg of a yellowish solid was obtained by column chromatography, with a yield of 11.7%.

[0064] 1 H-NMR (400MHz, CDCl 3 ): δ8.11(d, 1H), 7.58(t, 1H), 7.28(m, 2H), 7.02-7.06(m, 2H), 6.85-6.91(m, 2H), 5.45(s, 1H), 4.77(s, 1H), 3.06(t, 2H), 2.55(t, 2H), 2.10(s, 3H), 1.86(m, 2H), 1.08(m, 1H), 0.55-0.77(m, 4H) .

[0065] ESI-MS: m / z 494 (MH + ).

Embodiment 2

[0067] S(+)-2-(2-chlorophenyl)-2-(2-acetylsalicylate-4,5,6,7-tetrahydrothiophene[3,2-c]pyridine)-5 - Preparation of methyl acetate

[0068]

[0069] Compound 2

[0070] 337 mg of S(+)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothiophene[3,2-c]pyridin-2(4H)-one-5 - Add methyl acetate and 100mg of sodium hydride (52%, dispersed in mineral oil) to a 25ml reaction flask, then add 2ml of anhydrous tetrahydrofuran, stir for 30 minutes, then add 200mg of salicyloyl chloride, continue stirring for 2 hours , the reaction was stopped, and 61.2 mg of off-white solid was obtained by separation by column chromatography, with a yield of 12.2%.

[0071] 1 H-NMR (400MHz, CDCl 3 ): δ8.10(d, 1H), 7.55(t, 1H), 7.26(m, 2H), 7.13(m, 1H), 7.00-7.06(m, 3H), 6.85-6.91(m, 2H), 5.45(s, 1H), 4.77(s, 1H), 3.68(s, 3H), 3.06(t, 2H), 2.55(t, 2H), 2.10(s, 3H), 1.86(m, 2H).

[0072] ESI-MS: m / z 500 (MH + ).

Embodiment 3

[0074] S(+)-2-(2-chlorophenyl)-2-nicotinate-4,5,6,7-tetrahydrothiophene[3,2-c]pyridine)-5-methyl acetate preparation

[0075]

[0076] Compound 3

[0077] 337 mg of S(+)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothiophene[3,2-c]pyridin-2(4H)-one-5 - Methyl acetate and 100mg of sodium hydride (52%, dispersed in mineral oil) were added to a 25ml reaction flask, then 2ml of anhydrous tetrahydrofuran was added, after stirring for 30 minutes, 150mg of nicotinoyl chloride was added, and the reaction was continued for 2 hours, The reaction was stopped, and 75.6 mg of off-white solid was separated by column chromatography, with a yield of 17.1%.

[0078] 1 H-NMR (400MHz, CDCl 3 ): δ9.12(s, 1H), 8.79(d, 1H), 8.17(d, 1H), 7.49(t, 1H), 7.15(m, 1H), 7.02-7.06(m, 3H), 6.85- 6.91 (m, 2H), 5.48 (s, 1H), 4.75 (s, 1H), 3.67 (s, 3H), 3.06 (t, 2H), 2.53 (t, 2H), 1.83 (m, 2H).

[0079] ESI-MS: m / z 443 (MH + ).

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Abstract

The invention discloses a compound with a general formula (1) disclosed as follow, or salt thereof, or a stereo isomer thereof and a preparation method as well as a medicinal composition which at least comprises at least one compound with the general formula (1), or salt thereof, or a stereo isomer thereof as an active component. The definitions of R1, R2 and R3 are disclosed in the specification. The compound has the function of suppressing platelet coagulation and is used for preventing and treating thrombus or embolism class diseases.

Description

technical field [0001] The invention belongs to the field of medicine, more specifically, the present invention relates to novel compounds with anticoagulant effect and salts thereof, stereoisomers and preparation methods thereof, and at least one compound of formula (1) shown below or A pharmaceutical preparation of its salt or its stereoisomer as an active ingredient, and its application in the prevention and treatment of thrombosis or embolism diseases. Background technique [0002] Anticoagulant drugs refer to drugs that can prevent blood coagulation by interfering with certain aspects of the body's physiological coagulation process, and are used to inhibit the formation and expansion of thrombus. Clinically, they are mainly used for atrial fibrillation, coronary heart disease, heart valve disease, For cardiovascular and cerebrovascular diseases such as pulmonary embolism, it is also used for other cardiovascular and cerebrovascular diseases that require anticoagulant th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/4365A61P7/02
Inventor 王振赵蕾
Owner GUANGZHOU HEERSHI PHARMA DEV
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