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New compound having anti-blood coagulation effect

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

Active Publication Date: 2014-07-23
亳州市君臣佐使药业有限公司
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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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  • New compound having anti-blood coagulation effect
  • New compound having anti-blood coagulation effect
  • New compound having anti-blood coagulation effect

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] 5-N-[(1RS)-2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothiophene[3,2-c Preparation of ]pyridin-2-yl acetylsalicylate

[0062]

[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 579 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), 702-706(m, 2H), 685-691(1n, 2H), 5.45(s, iH), 477(s, 1H), 3.06(t, 2H), 255(t, 2H), 210(s, 3H), 186(m, 2H), 108(m, 1H), 0.55-077(m, 4H) .

[0065] ESI-MS: m / z494 (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] 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 612 mg of off-white solid was obtained by separation by column chromatography, with a yield of 122%.

[0070] 1 H-NMR (400MHz, CDCl 3 ): δ8.10(d, 1H), 7.55(t, 1H), 7.26(m, 2H), 7.13(m, 1H), 700-706(m, 3H), 685-6.91(m, 2H), 5.45 (s, 1H), 4.77 (s, 1H), 3.68 (s, 3H), 306 (t, 2H), 2.55 (t, 2H), 210 (s, 3H), 1.86 (m, 2H).

[0071] ESI-MS: m / z500 (MH + ).

Embodiment 3

[0073] S(+)-2-(2-chlorophenyl)-2-nicotinate-4,5,6,7-tetrahydrothiophene[3,2-c]pyridine)-5-methyl acetate to prepare

[0074]

[0075] 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 756 mg of off-white solid was obtained by separation by column chromatography, with a yield of 17.1%.

[0076] 1 H-NMR (400MHz, CDCl 3 ): δ9.12(s, 1H), 8.79(d, 1H), 8.17(d, 1H), 7.49(t, 1H), 715(m, / H), 702-706(m, 3H), 6.85 -691 (m, 2H), 5.48 (s, 1H), 475 (s, 1H), 367 (s, 3H), 306 (t, 2H), 2.53 (t, 2H), 183 (m, 2H).

[0077] ESI-MS: m / z443 (MH + ).

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Abstract

The invention discloses a compound represented by a general formula (1) or a salt or a stereoisomer and a preparation method thereof, and a medicinal combination at least comprising at least one compound represented by the general formula (1) or the salt or the stereoisomer thereof as an active ingredient, wherein R1, R2 and R3 are defined in the specification. The compound has the function of inhibition of platelet aggregation, and is used for prevention and treatment of thrombus or embolism disease.

Description

[0001] This application is a divisional application of the Chinese invention application (name of invention: new compound with anticoagulant effect; application number: 200810211286.2; filing date: September 22, 2008). technical field [0002] 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 [0003] 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, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/625A61K31/444A61K31/455A61P7/02A61P9/10
CPCC07D495/04
Inventor 王振赵蕾
Owner 亳州市君臣佐使药业有限公司