Acid addition salts of synthetic intermediates for carbapenem antibiotics and processes for preparing the same

A technology for acid addition salts and compounds, which is applied in the field of preparing carbapenem antibiotics, can solve the problems of intractable treatment, unsuitable for large-scale production on an industrial scale, low product yield and the like, and achieves the effect of easy treatment

Inactive Publication Date: 2010-09-29
KUKJE PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, since the column chromatography must be used for purification to obtain the compound of formula 10 from the compound of formula 9 in the work-up period, the yield of the product is low, and the method is not suitable for large-scale production on an industrial scale
In addition, since the obtained compound of formula 2 is in liquid form, it is difficult to handle

Method used

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  • Acid addition salts of synthetic intermediates for carbapenem antibiotics and processes for preparing the same
  • Acid addition salts of synthetic intermediates for carbapenem antibiotics and processes for preparing the same
  • Acid addition salts of synthetic intermediates for carbapenem antibiotics and processes for preparing the same

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preparation example Construction

[0048] The present invention includes a method for preparing an acid addition salt of a compound of formula 3, the method comprising: (a) reacting a compound of formula 1 with a compound of formula 2; (b) adding water and an organic compound to the reaction mixture prepared in step (a) A mixed solution of solvents, acidifying the resulting mixture to a pH range between 1-5, and then separating the organic layer; (c) crystallization by adding an organic solvent to the organic layer obtained in step (b) or its concentrate:

[0049]

[0050] Among them, R 1 and R 2 are independently hydrogen, C 1 -C 3 Alkyl, C 1 -C 3 Alkoxy, halogen, hydroxyl, amino or trifluoromethyl; R 3 is hydrogen or C 1 -C 3 Alkyl; R 4 is hydrogen or a hydroxyl protecting group; R 5 is a carbonyl protecting group.

[0051] In the preparation method of the acid addition salt of the compound of formula 3 of the present invention, the hydroxyl protecting group can be a general hydroxyl protecting g...

Embodiment 1

[0094] Example 1: 1-Chloro-3-(4-fluorobenzylamine)propan-2-ol

[0095] 35Kg of 4-fluorobenzylamine was added to 500Kg of pure water, and the reaction mixture was cooled to 5°C or lower. 38.8 Kg of epichlorohydrin was slowly added to the reaction mixture while maintaining the temperature of the reaction mixture at 5°C or below. The reaction mixture was gradually heated to 20°C, stirred for 12 hours, then filtered. The obtained solid was washed with hexane and dried under reduced pressure to obtain 54.5 Kg of 1-chloro-3-(4-fluorobenzylamine)propan-2-ol (yield: 89.5%).

[0096] 1 H NMR (300MHz, CDCl 3 ) δ 2.78 (m.2H), 3.57 (d, J=5.3Hz, 2H), 3.79 (s, 2H), 3.90 (m, 1H), 7.01 (m, 2H), 7.29 (m, 2H).

Embodiment 2

[0098] Example 2: 1-Chloro-3-benzylaminopropan-2-ol

[0099] Yield: 83%: 1 H NMR (300MHz, CDCl 3 ) δ 2.72 (m, 2H), 3.56 (d, 2H), 3.80 (s, 2H), 3.86 (m, 1H), 7.32 (m, 5H).

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Abstract

The present invention provides a process for preparing an acid addition salt of a synthetic intermediate for carbapenem antibiotics and a novel acid addition salt of a synthetic intermediate for carbapenem antibiotics obtained from the process. The present invention also provides a process for preparing a carbapenem antibiotic using the acid addition salt. According to the process of the present invention, an acid addition salt of a synthetic intermediate for carbapenem antibiotics can be prepared in a high yield and high purity, without conducting column chromatography. Thus, the process of the present invention can be applied to mass production with an industrial scale. Furthermore, since the acid addition salts have solid forms, they are easy to handle and keep in a manufacturing site.

Description

technical field [0001] The invention relates to an acid addition salt of a synthetic intermediate of carbapenem antibiotics and a preparation method thereof. The present invention also relates to a method for preparing carbapenem antibiotics by using the acid addition salt. Background technique [0002] With the increase of infectious diseases worldwide, the use of antibiotics for the treatment of infectious diseases is increasing significantly. Since the clinical application of multiple antibiotics in the 1980s, penicillin-resistant Streptococcus pneumoniae (PRSP), methicillin-resistant Staphylococcus aureus (methicillin-resistant Staphylococcus aureus, MRSA) and other antibiotic-resistant bacteria caused many global problems. Since the emergence of vancomycin-resistant Enterococci (VRE) in the 1990s, antibiotic-resistant bacteria have begun to threaten human health. Therefore, there is a need to develop novel antibiotics that can effectively suppress antibiotic-resistan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/20
CPCC07D205/04C07C213/04C07D477/20C07C215/08
Inventor 金昌燮李东宇李在祐郑美兰郑永澈金时敏崔茔鲁徐东槿李周姬安弼祥
Owner KUKJE PHARMA IND CO LTD
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