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Anti-heparin compounds

A compound, an independent technology, applied in the preparation of organic compounds, drug combinations, organic chemistry, etc., can solve the problems of lack of effective antagonists, limitations, etc., to achieve the effect of eliminating anticoagulant effects

Inactive Publication Date: 2012-09-19
CELLCEUTIX CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lack of effective antagonists limits the clinical use of LMWH and fondaparinux, especially in bypass surgery procedures and when near-term surgical procedures may be required

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0674] Embodiment 1: synthesis

[0675] Synthesis of compound 1

[0676]

[0677] Step 1: The diacid and dianiline (2 equivalents) are mixed in pyridine and EDCI is added. The reaction mixture was stirred at room temperature for 24 h before the solvent was removed. The resulting solid was washed with water and recrystallized from DCM / hexanes.

[0678] Step 2: The product of Step 1 is mixed with 5-bisBocguanidino pentoic acid and dissolved in pyridine. After the solution was cooled to 0°C, POCl was added to the mixture 3 . The reaction mixture was stirred at 0 °C for 2 h and then quenched with ice water. The product was purified by column chromatography.

[0679] Step 3: The product of step 2 was treated with HCl in ethyl acetate for 6h. The product was collected by filtration. Purification was accomplished by reverse phase column chromatography.

[0680] Compounds 6, 87 and 88 were prepared in the first step by a similar procedure using different diacids.

[0681]...

Embodiment 2

[0755] Example 2: Evaluation of compounds as anti-heparin agents

[0756] Exemplary compounds (and / or salts thereof) in Table 1 below are published by publications such as U.S. Patent Application Publication No. U.S. 2005 / 0287108, U.S. / 093813 and those methods reported in US patent application SN 12 / 510,593 filed on July 28, 2009.

[0757] Table 1

[0758]

[0759]

[0760]

[0761]

[0762]

[0763]

[0764]

[0765]

[0766]

[0767]

[0768]

[0769]

[0770]

[0771]

[0772]

[0773]

[0774]

[0775]

[0776]

[0777]

[0778]

Embodiment 3

[0779] Example 3: FXa Chromogenic Assay (Lack of Plasma)

[0780] Human antithrombin was mixed with the anticoagulant (LMWH or fondaparinux); the final concentration was 0.22 μg / mL for LMWH and 0.07 μg / mL for fondaparinux. Add different concentrations of test compounds (generally in the range of 0.07-9 μg / mL), followed by factor Xa and substrate (S-2765). Absorbance was read every 30 s over a period of 4 min on a SpectraMax 250 instrument (Molecular Devices, Inc.). EC 50 Values ​​were determined by a curve fitting program (SoftMax Pro) using the following formula:

[0781] P(C p )=1 / [1+(K / C p ) n ]

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PUM

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Abstract

The present invention provides compounds and methods for antagonizing the anticoagulant effect of an anticoagulant agent that is selected from UFH, LMWH, and a heparin / LMWH derivative in a patient comprising administering to the patient a compound of the invention or a salt thereof, or a composition comprising the same.

Description

[0001] Government Funded References [0002] This invention was made with U.S. Government funding (NIH / NHLBI SBIR Grant Nos. (Grant Nos) 1R43HL090113-01 and 2R44HL090113-02 and NHLBI SBIR Phase 2 Grant #5R44HL090113) and the U.S. Government thus has certain rights in this invention. technical field [0003] The present invention relates in part to compounds or pharmaceutically acceptable salts thereof, and compositions containing said compounds and / or salts, and the use of one or more of said compounds or pharmaceutically acceptable salts thereof or combinations containing these compounds or pharmaceutically acceptable salts thereof Anticoagulants such as unfractionated heparin (unfractionated heparin), low molecular weight heparin, and / or heparin or low molecular weight heparin derivatives. Background technique [0004] Treatment and prevention of thrombosis are major clinical problems for patients treated with medical therapy and surgery. Heparin, a highly sulfated polysa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/727
CPCC07D211/58C07D403/12C07C235/62C07D207/16C07D239/28C07D277/56C07C323/63A61K31/505C07D209/20A61K31/167C07C2101/14C07C279/08A61K31/195C07D213/82C07C279/14C07D209/18C07D211/26C07C237/42C07C235/60A61K31/445C07C235/64A61K31/4545A61K31/455A61K31/4045C07C279/16C07D209/42A61P7/02A61P7/04A61P43/00C07C2601/14A61K31/727
Inventor 理查德·W·斯科特刘大慧罗伯特·W·卡沃什特雷弗·扬卡罗尔·穆鲁尼迈克尔·J·科斯坦佐
Owner CELLCEUTIX CORP
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