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Isoniazid thiadiazine thione derivative

A technology of thiadiazinethione and isoniazid, which is applied in the direction of organic chemistry, organic active ingredients, antibacterial drugs, etc., can solve the problems of ineffective delivery of drugs, achieve effective anti-tuberculosis, reduce drug resistance, and good The effect of antibacterial activity

Inactive Publication Date: 2012-05-30
成都格蓝洋生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Insoluble, fat-soluble drugs cannot be effectively delivered if they cannot be dissolved or are highly dispersed

Method used

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  • Isoniazid thiadiazine thione derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0072] Synthesis of N,N'-[ethane-1,2-diyl(6-thio-1,3,5-thiadiazine-5,3-diyl)]bisisonicotinamide, structure diagram of the compound as follows:

[0073]

[0074] Figure 7N, N'-[ethane-1,2-bisyl (6-thio-1,3,5-thiadiazine-5,3-diyl)] bisisonicotinamide

[0075] The chemical name of this product is: N, N'-[ethane-1,2-diylbis(6-thioxo-1,3,5-thiadiazinane-5,3-diyl)]diisonicotinamide, and the molecular formula is C 20 h 22 N 8 S 4 o 2 , referred to as ETTD. The molecular weight is 534. The specific synthesis steps are as follows: put 1.5g (25mmol) ethylenediamine in a flask, add 75mL of toluene, heat to dissolve at 35°C, add 7mL (20%, 25mmol) KOH solution and stir for about 2 minutes, then drop 12mL (200mmol) ) carbon disulfide, reacted at 35°C for 8 hours, cooled to room temperature, added 13.6mL (150mmol) formaldehyde, and continued to stir for 3 hours. 6.86g (50mmol) of isoniazid was dissolved in 12.5mL of pH7.8 phosphate buffer solution and 25mL of absolute ethanol, dro...

Embodiment 2

[0077] Synthesis of N,N'-[butane-1,4-diyl(6-thio-1,3,5-thiadiazine-5,3-diyl)]bisisonicotinamide, structure diagram of the compound as follows:

[0078]

[0079] Figure 8N, N'-[butane-1,4-bisyl (6-thio-1,3,5-thiadiazine-5,3-diyl)] bisisonicotinamide

[0080] The chemical name of this product is: N, N'-[butane-1,4-diylbis(6-thioxo-1,3,5-thiadiazinane-5,3-diyl)]diisonicotinamide, and the molecular formula is C 22 h 26 N 8 S 4 o 2 , referred to as BTTD. The molecular weight is 562. The specific synthesis steps are as follows: put 2.2g (25mmol) of butanediamine in a flask, add 75mL of toluene, heat and dissolve at 35°C, add 7mL (20%, 25mmol) of KOH solution and stir for about 2 minutes, then drop 12mL (200mmol) of ) carbon disulfide, reacted at 35°C for 8 hours, cooled to room temperature, added 13.6mL (150mmol) formaldehyde, and continued to stir for 3 hours. 6.86g (50mmol) of isoniazid was dissolved in 12.5mL of pH7.8 phosphate buffer solution and 25mL of absolute etha...

Embodiment 3

[0082] Synthesis of N,N'-[butane-1,3-diyl(6-thio-1,3,5-thiadiazine-5,3-diyl)]bisisonicotinamide, structure diagram of the compound as follows:

[0083]

[0084] Figure 9N, N'-[isobutane-1,3-bisyl (6-thio-1,3,5-thiadiazine-5,3-diyl)] bisisonicotinamide

[0085] The chemical name of this product is: N,N'-[isobutane-1,12-diylbis(6-thioxo-1,3,5-thiadiazinane-5,3-diyl)]diisonicotinamide, the molecular formula is C 22 h 26 N 8 S 4 o 2 , referred to as ITTD. The molecular weight is 562. The specific synthesis steps are as follows: put 2.2g (25mmol) of isobutylene diamine in a flask, add 75mL of toluene, heat to dissolve at 35°C, add 7mL (20%, 25mmol) of KOH solution and stir for about 2 minutes, then drop into 12mL ( 200mmol) of carbon disulfide, reacted at 35°C for 8 hours, cooled to room temperature, added 13.6mL (150mmol) of formaldehyde, and continued to stir for 3 hours. 6.86g (50mmol) of isoniazid was dissolved in 12.5mL of pH7.8 phosphate buffer solution and 25mL of...

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Abstract

The invention discloses an isoniazid thiadiazine thione derivative, which solves the problem that the existing derivative has poor lipid solubility of active ingredient, and can not dissolve in water or can not highly disperse. The structure of the derivative can be presented by INH-THTT-R-THTT-INH, wherein ING represents the structure of isoniazid of antitubercular drug, THTT is a ring structure, and R is linear chain, non-linear chain or annular alkyl compound containing two primary amines (including alkyl structures of different substituent groups). The derivative can be prepared into highly-dispersed drug delivery system, including the dosage form of liposome, solid lipid nanospheres, niosomes, micro emulsion and the like. The derivative can not only improve the lipid solubility of isoniazid, but also hydrolyze and release isoniazid active compound in vivo, increases the penetrability of isoniazid cell, reduces the tolerance of isoniazid during therapy and improves the curative effect.

Description

Technical field: [0001] The present invention relates to the fields of chemistry and medical biology, in particular to isoniazid thiadiazine thioketated derivatives, which can be prepared into highly dispersed drug delivery systems such as liposomes, nanoparticles, liposomes and microemulsions . technical background: [0002] Tuberculosis (TB) is an ancient disease caused by Mycobacterium tuberculosis (MTB). Together with AIDS and hepatitis B, it has become the three major infectious diseases that threaten human health in China today. Therefore, the research and treatment of tuberculosis is a major public health problem and social issues. In 2009, statistics on the incidence and death of statutory Class A and Class B infectious diseases in China showed that tuberculosis ranked second. At present, the tuberculosis infection rate of my country's population is 44.5%. About 400 million people have been infected with tuberculosis, and about 10% of those who have been infected w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14A61K31/549A61P31/04A61K9/10A61K9/127
Inventor 陈书峰杨放田生云李蔷薇胡杨洋
Owner 成都格蓝洋生物医药科技有限公司
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