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Preparation method of deferasirox and intermediate compound of deferasirox

A technology of compounds and catalysts, applied in the field of preparation methods of deferasirox and related intermediate compounds, can solve the problems of strict and cumbersome reaction process and reaction temperature control, unfavorable industrial production, etc., and achieve simple post-treatment, preparation and separation Simple operation effect

Active Publication Date: 2015-02-04
NANJING HAIRUN PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] 3) WO2010023685 discloses a method for preparing benzoxazinone intermediates by reacting salicylamide and salicyloyl chloride, but this method requires strict and cumbersome reaction process and reaction temperature control, which is not conducive to industrial production

Method used

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  • Preparation method of deferasirox and intermediate compound of deferasirox
  • Preparation method of deferasirox and intermediate compound of deferasirox
  • Preparation method of deferasirox and intermediate compound of deferasirox

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: Preparation of o-benzyloxyphenyliminoacid methyl ester hydrochloride

[0045] Dissolve o-benzyloxybenzonitrile (31.4g, 0.15mol) in methanol (150mL), cool down to 0°C, flow HCl gas for about 2-3 hours, keep warm overnight, concentrate, add ether to the obtained solid, and obtain a white solid 39.4g, yield 90%. MS(ESI)m / z278.7(M+H) +

[0046] 1 H NMR (DMSO-d 6 ,500MHz)δ12.8(br,1H),12.2(br,1H),7.41-7.22(m,7H),6.98-7.03(m,2H),5.11(s,2H),4.45(s,3H) .

Embodiment 2

[0047] Embodiment 2: Preparation of o-benzyloxyphenyliminoacid ethyl ester hydrochloride

[0048] Dissolve o-benzyloxybenzonitrile (31.4g, 0.15mol) in absolute ethanol (150mL), cool down to 0°C, flow HCl gas for about 3-4 hours, keep warm overnight, concentrate, and add ether to the obtained solid to obtain White solid 41.3g, yield 94.7%. MS(ESI)m / z292.6(M+H) + .

[0049] 1 H NMR (DMSO-d 6,500MHz)δ12.8(br,1H),12.1(br,1H),7.38-7.18(m,7H),6.97-7.02(m,2H),5.13(s,2H),4.40(q,J= 7.0Hz,2H),1.27(t,J=7.0Hz,3H).

Embodiment 3

[0050] Embodiment 3: the preparation of formula IV compound

[0051] Add water (250mL) to o-benzyloxyphenylimidomethyl ester hydrochloride (30g, 0.11mmol), cool down to 10-20°C, add solid sodium bicarbonate (11.0g, 0.13mmol) in batches, and add the resulting mixture Dichloromethane (200 mL×3) was extracted, and the combined organic layers were dried by adding anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain 25 g of o-benzyloxyphenylimidomethyl ester with a yield of 96%. MS(ESI)m / z242.5(M+H) +

[0052] 1 H NMR (DMSO-d 6 ,500MHz)δ8.78(br,1H),7.36-7.20(m,7H),6.95-7.00(m,2H),5.06(s,2H),4.41(s,3H).

[0053] Ethyl o-benzyloxyphenyliminoate can be prepared by a similar method, MS (ESI) m / z256.6 (M+H) + .

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Abstract

The invention belongs to the field of pharmaceutical chemicals, provides a preparation method of deferasirox which is an iron-overloaded medicament and particularly provides a method for preparing deferasirox mainly from salicyloyl chloride, o-benzyloxy cyanophenyl, p-hydrazinobenzoic acid (or hydrochlorides thereof) under mild conditions. The method for preparing the deferasirox is mild in condition and simple to operate; the deferasirox product is high in purity.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and more specifically relates to a preparation method of deferasirox and related intermediate compounds. Background technique [0002] The chemical name of deferasirox is: 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid (I), and its structure is shown in the following formula: [0003] [0004] Deerasirox is currently the only oral iron ion chelator developed by Novartis, which was approved by the FDA in November 2005 for patients with chronic iron overload caused by blood transfusions aged 2 and over. In December 2012, deferasirox was approved by the European Commission for non-transfusion-dependent thalassemia aged 10 and over who require chelation therapy due to contraindication or insufficiency of deferoxamine therapy Treatment of chronic iron overload in patients with non-transfusion-dependent thalassemia (NTDT) syndrome. On January 23, 2013, the FDA approved th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08C07C257/08C07D265/22
Inventor 陈庆财陈祥峰赵宇蔡开明吴晨晖
Owner NANJING HAIRUN PHARM CO LTD
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