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Preparation method and application of 2-lactylaminobenzoic acid

A technology of lactylaminobenzoic acid and benzoic acids, which is applied in the field of preparation of -2-lactylaminobenzoic acid and -2-lactylaminobenzoic acid, can solve the problems of narrow therapeutic window bleeding risk, drug resistance, etc. Achieve significant anti-platelet aggregation, low cost, and significant antithrombotic activity

Active Publication Date: 2018-11-27
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned similar drugs have been studied extensively in antithrombotic aspects and have been used clinically for a long time, but they have side effects such as narrow therapeutic window, bleeding risk, drug resistance, and other unexpected drug interactions have always been the focus of attention

Method used

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  • Preparation method and application of 2-lactylaminobenzoic acid
  • Preparation method and application of 2-lactylaminobenzoic acid
  • Preparation method and application of 2-lactylaminobenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1. The chemical synthesis preparation of (S)-2-lactamidobenzoic acid

[0035] 1.1 Reagents: L-lactic acid, methyl anthranilate, acetyl chloride, thionyl chloride, tetrahydrofuran, anhydrous ether, methanol, dichloromethane, ethyl acetate

[0036] 1.2 Synthesis method:

[0037] 1.2.1 Synthesis of intermediate (IVa)

[0038] Take 12.0g (133.3mmol) of L-lactic acid in a 250ml three-necked reaction flask, add 24ml of anhydrous tetrahydrofuran, add 19.2ml (266.6mmol) of acetyl chloride dropwise under stirring at -10~0°C, stir at room temperature for 5h, and depressurize at 35°C Concentrate to obtain 14.6 g of a colorless oily liquid, with a yield of 83.2%.

[0039] 1.2.2 Synthesis of intermediate (Va)

[0040] Take 14.6g (110.6mmol) of intermediate (IVa) in a 250ml reaction flask, add 48ml of thionyl chloride, react at 50°C for 2h, and concentrate under reduced pressure at 40°C to obtain 15.6g of light yellow oily liquid with a yield of 93.7%.

[0041] 1.2.3 S...

Embodiment 2

[0049] Example 2. Preparation of chemical synthesis of (R)-2-lactylaminobenzoic acid

[0050] The method was the same as 1.2 except that L-lactic acid was replaced by D-lactic acid. According to the synthesis method of S-2-lactic aminobenzoic acid, 8.50 g of R-2-lactic aminobenzoic acid was obtained with a total yield of 52.9%.

Embodiment 3

[0051] Example 3. Study on anti-platelet aggregation activity of (R)-2-lactylaminobenzoic acid and (S)-2-lactylaminobenzoic acid

[0052] 3.1 Reagents

[0053] Aspirin (ASP, purity>99.5%), (R)-2-lactylaminobenzoic acid (homemade, optical purity>99.3%), (S)-2-lactylaminobenzoic acid (homemade, optical purity>98.8%) ), dimethyl sulfoxide (DMSO), adenosine diphosphate (ADP), collagen (COLL), arachidonic acid (AA), thromboxane B 2 (TXB 2 ) ELISA kit, 6-keto-prostaglandin F1α (6-keto-PGF1α) ELISA kit, cyclooxygenase-1 (COX-1) ELISA kit, lactate dehydrogenase (LDH) detection kit, sodium carboxymethylcellulose (CMC-Na).

[0054] 3.2 Experimental animals

[0055] Japanese big-eared white rabbit, male, SPF grade, weighing 2-3kg, SCXK2014-0002.

[0056] KM mice, male, SPF grade, body weight 18-22g, SCXK2015-0001.

[0057] SD rats, male, weighing 220-250g, SCXK2015-0001.

[0058] 3.3 Experimental method

[0059] 3.3.1 Anti-platelet aggregation

[0060] Blood was taken from the e...

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Abstract

The preset invention relates to a new medical use of a chiral compound. The chemical name is R- / S-2-lactamide-based benzoic acid, having a structural formula shown below. The compound is originally extracted from a secondary metabolite of microorganisms, and can be obtained by means of chemical synthesis. Initial pharmacological experiments showed that the compound has good analgesic and anti-inflammatory activities, and had less stimulation a gastrointestinal tract. Recent studies show that an enantiomer of the compound has better antiplatelet agglutination and antithrombotic activities, and the compound is expected to become a new nonsteroidal antiplatelet agglutination and antithrombotic drug.

Description

technical field [0001] The invention belongs to the field of drug synthesis and pharmacology, and relates to the preparation method and application of 2-lactylaminobenzoic acid, in particular to (R)-2-lactylaminobenzoic acid (R-HPABA) and (S)-2-milk Preparation method and new medical use of amidobenzoic acid (S-HPABA). Background technique [0002] It is well known that although chiral compounds have the same physical and chemical properties, their pharmacodynamics, pharmacokinetics (absorption, distribution, metabolism and excretion) and even toxicological properties may be different, especially these processes involve interactions with some biological When molecules (enzymes, carriers, receptors, etc.) interact, different enantiomers of chiral compounds may exhibit different characteristics. [0003] At present, many antithrombotic drugs have been developed and applied, which are divided into antiplatelet aggregation drugs, anticoagulant drugs and thrombolytic drugs accor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/16A61K31/196A61P7/02A61P9/10
CPCC07C235/16
Inventor 于治国赵云丽张启丽
Owner SHENYANG PHARMA UNIVERSITY