7-phenylacetamido-3-chloromethyl-cephem-4-carboxylic-acid-p-methoxybenzyl ester | 1214081-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 7-phenylacetamido-3-chloromethyl-cephem-4-carboxylic-acid-p-methoxybenzyl ester
• 英文别名: (6S)-4-Methoxybenzyl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；(4-methoxyphenyl)methyl (6S)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 1214081-14-7
• 化学式: C₂₄H₂₃ClN₂O₅S
• 分子量: 486.976
• InChiKey: KFCMZNUGNLCSJQ-AKRCKQFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

文献信息

• New method for the preparation of ceftiofur sodium and its intermediates
  申请人：ORCHID CHEMICALS AND PHARMACEUTICALS LIMITED

  公开号：US20030216567A1

  公开（公告）日：2003-11-20

  The present invention relates to a new method for the preparation of Ceftiofur acid of formula (I), 1 its pharmaceutically acceptable salt such as sodium or hydrochloride and also provides two new intermediates of formulae (V) and (VI) 2 wherein X represents halogen atom such as chlorine or bromine and R represents p-methoxybenzyl, p-nitrobenzyl or diphenylmethyl group.

  本发明涉及一种制备化学式（I）中的头孢噻呋酸及其药用可接受盐（如钠盐或盐酸盐）的新方法，并提供了两种新的中间体，其化学式分别为（V）和（VI），其中X代表卤素原子，如氯或溴，R代表对甲氧基苯甲基、对硝基苯甲基或二苯甲基基团。
• Orally administrable cephalosporin derivatives, and the production and uses thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0321364A2

  公开（公告）日：1989-06-21

  As new antibacterial compounds are provided a cephalosporin derivative having the general formula (I) wherein R¹ is a lower alkyl group, a lower alkoxymethyl group or a lower alkenyl group, and R² and R³ are each a hydrogen atom or a lower alkyl group, and pharmaceutically acceptable salt thereof. This new cephalosporin derivative of the formula (I) is useful as an orally administrable antibacterial agent which exhibits an excellent antibacterial activity, high absorbability through the digestive tracts of animal and high urinary recovery thereof.

  提供了一种新的头孢菌素衍生物，其具有通式(I)，其中R¹是低级烷基组、低级烷氧甲基组或低级烯基组，R²和R³各自是氢原子或低级烷基组，以及其药学上可接受的盐。这种通式(I)的新头孢菌素衍生物作为口服抗菌剂具有很高的实用性，它显示出优异的抗菌活性，高吸收性通过动物的消化道，以及高尿液回收率。
• BETA-LACTAMASE INHIBITORS
  申请人：SUTTON Larry

  公开号：US20100261700A1

  公开（公告）日：2010-10-14

  Broad spectrum beta-lactamase inhibitors. Certain inhibitors also exhibit potent antibiotic activity in addition to beta-lactamase inhibition. Compounds of the invention are designed such that on cleavage of the beta-lactam ring reactive moieties are generated which can inactivate beta-lactamase. Also provided are methods of making beta-lactamase inhibitors and beta-lactam antibiotics exhibiting such inhibition. Additionally provided are pharmaceutical compositions for treatment or prevention of bacterial infections and methods of treatment of such infections.

  广谱β-内酰胺酶抑制剂。某些抑制剂除了抑制β-内酰胺酶外，还表现出强效的抗生素活性。本发明的化合物设计成在β-内酰胺环裂解时生成可以灭活β-内酰胺酶的反应性基团。还提供了制备β-内酰胺酶抑制剂和表现出这种抑制作用的β-内酰胺类抗生素的方法。此外还提供了用于治疗或预防细菌感染的药物组合物和治疗此类感染的方法。
• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF CHLORO METHYL CEPHEM DERIVATIVES<br/>[FR] PROCEDE AMELIORE DE PREPARATION DE DERIVES DE CHLOROMETHYLCEPHEME
  申请人：ORCHID CHEMICALS & PHARM LTD

  公开号：WO2004039813A1

  公开（公告）日：2004-05-13

  The present invention provides an improved process to produce the chloromethylcephem derivatives of the formula (I), wherein R1 represents a carboxy-protecting group viz., substituted methyl group, which can be deprotected easily, such as t-butyl group, diphenylmethyl, 4-methoxybenzyl, 2-methoxybenzyl, 2-chlorobenzyl or benzyl group; R2 represents hydrogen, (C1-C4)alkyl, substituted or unsubstituted phenyl or substituted or unsubstituted phenoxy group.

  本发明提供了一种改进的方法，用于生产式(I)的氯甲基头孢菌素衍生物，其中R1代表羧基保护基，即，可以轻松去保护的取代甲基基团，例如叔丁基基团，二苯甲基，4-甲氧基苯甲基，2-甲氧基苯甲基，2-氯苯甲基或苄基；R2代表氢，(C1-C4)烷基，取代或未取代的苯基或取代或未取代的苯氧基。
• [EN] PROCESS FOR PREPARATION OF 7-PHENYLACETAMIDO-3-CHLOROMETHYL-3-CEPHEM-4- CARBOXYLIC ACID P-METHOXYBENZYL ESTER<br/>[FR] PROCÉDÉ DE PRÉPARATION DE L'ESTER P-MÉTHOXYBENZYLIQUE DE L'ACIDE 7-PHÉNYLACÉTAMIDO-3-CHLOROMÉTHYL-3-CÉPHÈME-4-CARBOXYLIQUE
  申请人：HNG CHEMBIO PHARMACY CO LTD

  公开号：WO2009129662A1

  公开（公告）日：2009-10-29

  A process for the preparation of 7-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester(GCLE), comprises the steps of: reacting penicillin G potassium salt with 4-methoxybenzyl chloride to obtain penicillin G 4-methoxybenzyl ester; oxidizing with peracetic acid to obtain penicillin G sulfoxide p-methoxybenzyl ester; treating with 2-mercaptobenzothiazole, followed by phenylsulfinic acid, to obtain a ring-opening intermediate; further treating with chlorine gas to obtain a chlorinated product; and ring-closing in the presence of ammonia gas to obtain 7-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (GCLE).

  制备7-苯乙酰氨基-3-氯甲基-3-头孢烯-4-羧酸对甲氧基苯甲基酯（GCLE）的过程包括以下步骤：将青霉素G钾盐与4-甲氧基苯甲基氯反应，得到青霉素G 4-甲氧基苯甲基酯；用过氧乙酸氧化得到青霉素G亚砜对甲氧基苯甲基酯；用2-巯基苯并噻唑处理，然后用苯磺酸处理，得到开环中间体；进一步用氯气处理得到氯化产物；在氨气存在下环合，得到7-苯乙酰氨基-3-氯甲基-3-头孢烯-4-羧酸对甲氧基苯甲基酯（GCLE）。