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Aryl Sulfonic Pyridoxines as Antiplatelet Agents

a technology of aryl sulfonic pyridoxines and antiplatelet agents, which is applied in the direction of leech-based protease inhibitors, peptide sources, cyclic peptide ingredients, etc., can solve the problems of inappropriate reaction initiation and propagation

Inactive Publication Date: 2007-06-21
HAQUE WASIMUL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The invention provides a new group of compounds called aryl sulfonic pyridoxines that can be used to treat cardiovascular, cerebovascular, or related diseases and symptoms. These compounds have specific formulas and can be used alone or in combination with other compounds to create pharmaceutical compositions. The technical effect of this invention is the discovery of new compounds that can be used to treat these diseases and symptoms."

Problems solved by technology

The pathways involved normally inhibit blood loss after vessel injury, but in thrombosis and related conditions, these reactions are inappropriately initiated and propagated.

Method used

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  • Aryl Sulfonic Pyridoxines as Antiplatelet Agents
  • Aryl Sulfonic Pyridoxines as Antiplatelet Agents
  • Aryl Sulfonic Pyridoxines as Antiplatelet Agents

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 4-[(2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide (1)

[0089]

[0090] To a 250 mL three neck flask fitted with a condenser and Dean-Stark apparatus was added 4′-amino-biphenyl-2-sulfonic acid tert-butylamide (1.22 g, 4.0 mmol), p-toluenesulfonic acid monohydrate (152 mg, 0.8 mmol), 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carbaldehyde (995 mg, 4.8 mmol, see Korytnyk et al., Methods Enzymol. 1970; 18A: 524-566) and toluene (120 ml). The reaction mixture was stirred at 120° C. under nitrogen atmosphere for 7 h before concentrating to dryness. The resulting solid was then dissolved in acetic acid (20 mL), cooled to 0° C., and sodium borohydride (529 mg, 14 mmol) was added slowly. After the addition of sodium borohydride was complete, dichloromethane (30 mL) was added to the reaction mixture and stirring was continued at room temperature for an additional 3 h. Sodium hydroxide (5 N) was added to neutralize the...

example 2

Synthesis of 4′-[(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl) -amino]-biphenyl-2-sulfonic acid tert-butylamide (2)

[0092]

[0093] To a solution of 10% formic acid in water (50 mL) was added 3-[(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl)-amino]-benzonitrile (1) (336 mg, 0.7 mmol) and the reaction mixture was heated at 100° C. under nitrogen atmosphere. The reaction mixture was then concentrated to dryness. The resulting pale yellow solid was dissolved in small amount of dichloromethane and diethyl ether was added to induce precipitation of a yellow solid. The pale yellow 4′-[(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide (2) (215 mg, 70% yield) was collected by filtration.

[0094]1H-NMR (DMSO-d6): δ 8.70 (s, 1H), 8.07 (d, 1H), 7.77 (s, 1H), 7.60 (m, 2H), 7.43 (s, 4H), 7.33 (d, 1H), 5.14 (s, 2H), 4.77 (s, 2H), 2.33 (s, 3H), 0.98 (s, 9H).

example 3

Synthesis of 4′-[(5-Hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid amide (3)

[0095]

[0096] Hydrogen chloride gas was bubbled into a suspension of 4′-[(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid tert-butylamide (2) (160 mg, 0.36 mmol) in methyl alcohol (20 mL) at 0° C. for 10 min. The solvent was evaporated and the products were purified on a silica gel column using a mixture of methyl alcohol:dichloromethane (1:9) as eluant to give 4′-[(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amino]-biphenyl-2-sulfonic acid amide (3) (139 mg, 25% yield).

[0097]1H-NMR (CD3OD): δ 8.08 (d, 1H), 7.92 (s, 1H), 7.59 (t, 1H), 7.47 (t, 1H), 7.33 (d, 1H), 7.24 (d, 2H), 6.74 (d, 2H), 4.99 (s, 2H), 4.36 (s, 2H), 2.43 (s, 3H). MS m / z (ES+): 400.22 (M+H+).

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Abstract

Aryl sulfonic pyridoxine compounds with inhibition of serine protease activity and antiplatelet aggregation characteristics for the treatment of cardiovascular and cardiovascular related diseases are described. The methods are directed to administering pharmaceutical compositions comprising aryl sulfonic pyridoxines.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation-in-part of U.S. application Ser. No. 10 / 974,707, filed Oct. 28, 2004, the entire disclosure of which is hereby incorporated by reference.FIELD OF THE INVENTION [0002] This invention relates to aryl sulfonic pyridoxines and methods of treating cardiovascular, cerebrovascular, and cardiovascular related diseases or symptoms by administering pharmaceutical compositions comprising an aryl sulfonic pyridoxine. BACKGROUND [0003] Thrombosis, the development of blood clots within arterial vessels, is due to a complex mechanism involving the activation of both platelet aggregation and the coagulation protease cascade (Ann. Intern Med. (2001) 134: 224-38; N. Engl. J. Med. (2002) 347: 5-12; Thromb. Haemost. (2002) 86: 51-6). The pathways involved normally inhibit blood loss after vessel injury, but in thrombosis and related conditions, these reactions are inappropriately initiated and propagated. [0004] On the mo...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K38/12A61K31/519A61K31/60A61K31/4743A61K31/4741A61K31/4415A61K31/727
CPCC07D213/66C07D491/04A61P11/00A61P31/04A61P43/00A61P7/02A61P7/10A61P9/00A61P9/06A61P9/10A61P9/12
Inventor HAQUE, WASIMULDIAKUR, JAMES
Owner HAQUE WASIMUL
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