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Amorphism of compound A benzoate, preparation method thereof, and amorphism-containing medicinal composition

A technology of benzoate and benzoate chemistry, applied to the amorphous form of compound A benzoate and its preparation, and the field of pharmaceutical compositions containing the amorphous form, which can solve the problem of lack of hydrophobic transmembrane domains and other problems , to achieve the effect of being conducive to preparation and use, simple method and high stability

Active Publication Date: 2017-01-25
SHENZHEN SALUBRIS PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A soluble protein form of DPP-IV exists in serum that is structurally and functionally identical to the membrane-bound protein form but lacks the hydrophobic transmembrane domain

Method used

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  • Amorphism of compound A benzoate, preparation method thereof, and amorphism-containing medicinal composition
  • Amorphism of compound A benzoate, preparation method thereof, and amorphism-containing medicinal composition
  • Amorphism of compound A benzoate, preparation method thereof, and amorphism-containing medicinal composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation of embodiment 1 compound A

[0041] According to the methods of Examples 2 and 3 of WO2011079778 specification, compound A was prepared using the following technical synthesis route:

[0042] The obtained compound A, 1 H-NMR (400MHz, DMSO, ppm): δ7.96(m,1H),7.36(br,1H),7.29(d,1H),5.23(s,2H),3.15(m,3H),2.72( m,2H),2.23(s,3H),1.78(d,1H),1.64(d,1H),1.47(m,1H),1.12(m,1H).MS: m / z,343(100% ,M+1).

[0043]

[0044] Concrete preparation steps are as follows:

[0045] Step A. 1-Bromo-4-fluoro-2-(methylisothiocyanate)benzene (2)

[0046]To a solution of 1-bromo-2-(bromomethyl)-4-fluorobenzene (1,5.36 g, 20.0 mmol) in DMF (20 mL) was added sodium iodide (1.20 g, 8.00 mmol) and potassium thiocyanate (3.88g, 40.0mmol). The mixture was heated to 80° C. for 12 h under a nitrogen atmosphere, cooled to room temperature, 100 mL of water was added thereto, and extracted with ethyl acetate (50 mL×2), the combined organic layers were washed with saturated brine, a...

Embodiment 2

[0062] The preparation of embodiment 2 compound A benzoate

[0063] Prepare 95% ethanol solution: add 228mL ethanol to a 500mL beaker, add 12mL water, stir evenly, set aside.

[0064] Take 2.14g of benzoic acid, add 10mL of 95% ethanol at room temperature and stir to dissolve, and set aside; add 60g of compound A refined product and 120mL of 95% ethanol to a 500mL reaction bottle, stir, dissolve, filter, and wash with 18ml of 95% ethanol; The ethanol solution of benzoic acid was added dropwise at 15 °C. After the dropwise addition was completed, the mixture was washed with 95% ethanol and dried under reduced pressure to constant weight to obtain 42.4 g of compound A benzoate.

[0065] 1 HNMR (DMSO-d 6 ,400MHz,ppm)δ7.96-7.88(m,3H),7.45-7.26(m,5H),6.80(brs,3H),5.21(q,2H),3.41(d,1H),3.11-3.08( m,2H),2.91-2.79(m,2H),2.23(s,3H),1.95-1.91(m,1H),1.78-1.74(m,1H),1.57-1.42(m,2H).MS: m / z,341(100%,M-1),343(100%,M+1).

Embodiment 3

[0066] The amorphous preparation of embodiment 3 compound A benzoate

[0067] Put 5.0 g of compound A benzoate in 25 mL of dichloromethane solvent, stir to dissolve, and concentrate to dryness at 20°C to 30°C to obtain a bubble-like product, which is vacuum-dried at room temperature to prepare an amorphous form of compound A benzoate .

[0068] The amorphous X-ray diffraction pattern of gained compound A benzoate is as figure 1 As shown, the DSC spectrum is as image 3 As shown, the TG spectrum is as Figure 5 shown.

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Abstract

The invention belongs to the field of preparation of medicinal compositions, and particularly relates to an amorphism of compound A benzoate, a preparation method thereof and an amorphism-containing medicinal composition.

Description

technical field [0001] The invention belongs to the field of preparation of pharmaceutical compounds, in particular to an amorphous compound A benzoate, a preparation method thereof, and a pharmaceutical composition containing the amorphous. Background technique [0002] Dipeptidyl peptidase IV (Dipeptidyl peptidase IV, DPP-IV) is a serine protease that can specifically hydrolyze the Xaa-Pro or Xaa-Ala dipeptide at the N-terminal of a polypeptide or protein. DPP-IV is an atypical serine protease, and the Ser-Asp-His catalytic triad in the C-terminal region is different from typical serine proteases, and is arranged in reverse order. DPP-IV is a type II membrane integral protein, which is widely distributed in various tissues of mammals. DPP-IV is expressed on the surface of differentiated epithelial cells such as intestine, liver, renal proximal tubules, prostate, corpus luteum, and leukocyte subtypes such as lymphocytes and macrophages. A soluble protein form of DPP-IV ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A61K31/53A61P3/10
CPCC07D401/04
Inventor 谭颂德张昌中黄群辉邓运植建琼
Owner SHENZHEN SALUBRIS PHARMA CO LTD
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