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A kind of preparation method of cefcapene hydrochloride

A technology for cefcapine hydrochloride and cefcapine axetil, which is applied in the field of preparing monohydrate hydrochloride, can solve problems such as industrial scale-up production, difficult handling, unstable materials, etc., and achieves reduction of long-term storage and high conversion rate , the effect of rapid response

Active Publication Date: 2016-08-10
SHENZHEN SALUBRIS PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Most of the existing processes use formula (II) as an intermediate, use trifluoroacetic acid to remove the Boc protecting group, and then form a salt, which has disadvantages such as difficult handling and unstable materials, which plague industrial scale-up production

Method used

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  • A kind of preparation method of cefcapene hydrochloride
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  • A kind of preparation method of cefcapene hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add ethyl acetate (1500mL) and aluminum trichloride (75g) to the reactor, stir to dissolve and cool down to -5~5°C, add compound of formula (II) (75g), and stir at -5~5°C React for 45 minutes. Water (1500 mL) was then quickly added to the reactor, stirred for 30 minutes, allowed to stand for 30 minutes, and the aqueous layer was drained. Wash with 10% sodium chloride solution (750mL), drain the water layer, control the temperature at 15-25°C, add 4mol / L hydrochloric acid (56.3mL) into the reactor, stir for 30 minutes, add acetonitrile (300mL), and stir for 3 hours . After centrifugation, the crude product was washed with water (500 mL×3), and dried for 16 hours to obtain the fine product of cefcapene hydrochloride monohydrate (60 g).

[0022] 1 H NMR (400MHz, d 6 -DMSO, 25°C): δ: 1.022 (t, 3H), 1.157 (s, 9H), 2.192-2.266 (m, 2H), 3.445-3.501 (d-d, 1H), 3.563-3.628 (d-d, 1H), 4.597(d, 1H), 4.828(d, 1H), 5.231(d, 1H), 5.783-5.811(m, 2H), 5.891(d, 1H), 6.353(t, 1H), 6...

Embodiment 2

[0024] Add ethyl acetate (1500mL) and aluminum trichloride (100g) into the reactor, stir to dissolve and cool down to -5~5°C, add the compound of formula (II) (75g), control the temperature at -5~5°C and stir React for 45 minutes. Water (1500 mL) was quickly added to the reactor, stirred for 30 minutes, left to stand for 30 minutes, and the water layer was drained. Wash with 10% sodium chloride solution (750mL), drain the water layer, control the temperature at 15-25°C, add 4mol / L hydrochloric acid (56.3mL) into the reactor, stir for 30 minutes, add acetonitrile (300mL), and stir for 3 hours . After centrifugation, the crude product was washed with water (500 mL×3), and dried for 16 hours to obtain the fine product of cefcapene hydrochloride monohydrate (55 g).

Embodiment 3

[0026] Add dichloromethane (1500mL) and aluminum trichloride (75g) into the reactor, stir to dissolve and cool down to -5~5°C, add the compound of formula (II) (75g), control the temperature and stir at -5~5°C React for 45 minutes. Water (1500 mL) was quickly added to the reactor, stirred for 30 minutes, left to stand for 30 minutes, and the water layer was drained. Wash with 10% sodium chloride solution (750mL), drain the water layer, control the temperature at 15-25°C, add 4mol / L hydrochloric acid (56.3mL) into the reactor, stir for 30 minutes, add acetonitrile (300mL), and stir for 3 hours . After centrifugation, the crude product was washed with water (500 mL×3), and dried for 16 hours to obtain the fine product of cefcapene hydrochloride monohydrate (55 g).

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Abstract

The invention relates to a method for preparing cefcapene pivoxil hydrochloride shown as a formula (I). By the method, the reaction time is shortened, the yield is improved, and the safety is high, so that the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method for removing a Boc protecting group in the production process of cefcapene hydrochloride and a method for preparing monohydrate hydrochloride. Background technique [0002] The chemical name of cefcapene pivoxil hydrochloride is 2,2-dimethylpropionyloxymethyl(6R,7R)-7-[(2Z)-2-(2-aminooxythiazol-4-yl)pentyl-2 -enoyloxy]-3-carbamoyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.4.0]oct-2-ene-2-carboxylate hydrochloride Monohydrate, its chemical structure is as shown in formula (I), [0003] [0004] Cefcapene pivoxil hydrochloride (Cefcapene pivoxil hydrochloride) is a third-generation cephalosporin antibiotic, which belongs to a broad-spectrum antibiotic. Pharmacological studies have shown that the MIC80 of MSSA against aerobic G+ bacteria is 3.13 μg / ml, and it is comparable to cefotiam and cefaclor Similarly, the MIC80 for Streptococcus pneumoniae is less than or equal to 0.1 μg / ml, which is better than cefaclo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/34C07D501/04
Inventor 朱强刘建平杜祖银肖军杨金光董月光
Owner SHENZHEN SALUBRIS PHARMA CO LTD
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