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Organic amine salt of aminobenzoic acid derivative and production method thereof

A technology of organic amine salts and amino groups, which is applied in the field of organic amine salts of aminobenzoic acid derivatives and its manufacture, can solve problems such as no examples, and achieve the effect of excellent stability

Inactive Publication Date: 2014-10-08
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, regarding the salt of Compound A, although there are examples of alkali metal salts and the like as pharmaceutically acceptable salts, there are no examples of specific salts.

Method used

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  • Organic amine salt of aminobenzoic acid derivative and production method thereof
  • Organic amine salt of aminobenzoic acid derivative and production method thereof
  • Organic amine salt of aminobenzoic acid derivative and production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0102] Hereinafter, the present invention will be described in more detail by showing synthesis examples, test examples, and formulation examples, but the present invention is not limited to these examples.

[0103] In addition, in the embodiments, LC means liquid chromatography, HPLC means high performance liquid chromatography, MS means mass spectrometry, LC / MS means liquid chromatography-mass spectrometry, LC / MS / MS means liquid chromatography-tandem mass spectrometry, TG means thermogravimetric analysis, Cmax means the maximum concentration in plasma, Tmax means the time to reach the maximum concentration in plasma, and AUC means the area under the concentration-time curve in plasma.

[0104] In addition, machine analysis was performed using the following device conditions, respectively.

[0105] 1 H-NMR was measured at 300 MHz.

[0106] TG was measured with TG8120 (manufactured by Rigaku Corporation).

[0107] Reference Synthesis Example 1

[0108] 3-{[((2E)-2-{1-[5-(4-t...

Synthetic example 1

[0114] 3-{[((2E)-2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-3-thienyl]ethylene}hydrazino)thiocarbonyl]amino} Ethanolamine Benzoate.

[0115] In 3-{[((2E)-2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)thiocarbonyl]amino A methanol solution (24.0 mL) of ethanolamine (1.47 g, 24.07 mmol) was added to an acetonitrile suspension (218 mL) of benzoic acid (10.25 g, 21.92 mmol), and stirred at room temperature for 2 hours and 50 minutes. The generated precipitate was collected by filtration, washed with acetonitrile, and dried under reduced pressure to obtain 10.88 g of the target product (94% yield).

[0116] Appearance: light yellow solid

[0117] 1 H-NMR (300MHz, DMSO-d 6 ):δ1.30(9H,s),2.39(3H,s),2.84(2H,t,J=5.0Hz),3.56(2H,t,J=5.0Hz),7.27(1H,dd,J= 8.0&7.5Hz),7.40(2H,d,J=8.5Hz),7.46(1H,d,J=7.5Hz),7.62(1H,s),7.73(2H,d,J=8.5Hz),7.91 (1H,d,J=8.0Hz),8.50(1H,s)

Synthetic example 2

[0119] 3-{[((2E)-2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-3-thienyl]ethylene}hydrazino)thiocarbonyl]amino} Benzoic acid tromethamine salt

[0120] In 3-{[((2E)-2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)thiocarbonyl]amino } To a tetrahydrofuran solution (100 mL) of benzoic acid (9.4 g, 20.1 mmol) was added tromethamine (2.7 g, 22.3 mmol) aqueous solution (20 mL), followed by acetonitrile (400 mL), and stirred at room temperature for 1 day. The generated precipitate was collected by filtration and dried under reduced pressure to obtain 11.3 g of the target product (95% yield).

[0121] Appearance: white to light yellow-green solid

[0122] 1 H-NMR (300MHz, DMSO-d 6 ):δ1.30(9H,s),2.38(3H,s),3.45(6H,s),7.29(1H,dd,J=8.0&7.5Hz),7.40(2H,d,J=8.5Hz) ,7.47(1H,d,J=7.5Hz),7.64(1H,s),7.72(2H,d,J=8.5Hz),7.89(1H,d,J=8.0Hz),8.51(1H,s)

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Abstract

The object of the present invention is to provide 3-{[((2E)-2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-3-thienyl]ethylene) represented by the following formula }hydrazino) thiocarbonyl] amino} benzoic acid is a new type of organic amine salt or quaternary ammonium salt. The organic amine salt or quaternary ammonium salt has excellent in vivo dynamic properties and stability, and has useful properties as a drug.

Description

technical field [0001] The present invention relates to novel thrombopoietin receptor activator 3-{[((2E)-2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-3-thienyl]ethylene The organic amine salt of base} hydrazino) thiocarbonyl] amino} benzoic acid. The compound of the present invention is particularly useful as a therapeutic agent or a thrombocytopenia agent for diseases accompanied by an abnormal platelet count. Background technique [0002] 3-{[((2E)-2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-3-thienyl]ethylene}hydrazino)thiocarbonyl]amino} Benzoic acid (hereinafter referred to as compound A) is useful as a thrombopoietin receptor activator. International Publication No. 04 / 108683 (Patent Document 1) and Japanese Patent Application Laid-Open No. 2006-527187 (Patent Document 2) disclose compound A and the tautomer of compound A in the form contained in the general formula , a prodrug or a pharmaceutically acceptable salt thereof, or a solvate thereof. In addition, Compound A is di...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/32A61K31/381A61P7/04A61P43/00
CPCA61K47/14A61K9/4866A61K9/1652A61K9/2059C07D333/32A61K9/2018A61K9/1623A61K9/0019A61P43/00A61P7/02A61P7/04A61K31/381
Inventor 岩本俊介中野智石田麻莉子山本正雄竹内和也
Owner NISSAN CHEM IND LTD
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