头孢呋辛杂质7 | 37051-07-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 头孢呋辛杂质7
• 英文名称: (6R,7R)-3-carbamoyloxymethyl-7-aminoceph-3-em-4-carboxylic acid
• 英文别名: (6R,7R)-7-Amino-3-carbamoyloxymethylceph-3-em-4-carboxylic acid；7-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid；(7R)-7-Amino Cefoxitin(Cefoxitin Impurity J)；(6R,7R)-7-amino-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 37051-07-3
• 化学式: C₉H₁₁N₃O₅S
• 分子量: 273.269
• InChiKey: ZJIANJKJAAXAOC-CLZZGJSISA-N

物化性质

• 沸点：
  681.2±55.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  161
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(furan-2-yl)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]cyclopropyl]oxyiminoacetic acid 、 头孢呋辛杂质7 生成 (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(1-carboxycyclopropyl)oxyimino-2-(furan-2-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  BRADSHAW, J.;COOK, M. C.;GREGORY, G. I.

  摘要：

  DOI：
• 作为产物：
  描述：

  7-氨基头孢烷酸 在 水 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 头孢呋辛杂质7
  参考文献：
  名称：

  一种盐酸头孢卡品酯的合成方法

  摘要：

  本发明盐酸头孢卡品酯的合成方法，步骤为：以7-氨基头孢烷酸（7-ACA）为原料，经“一锅法”3-位酯水解及7-位氨基保护，“一锅法”3-位酰胺化及7-位脱保护两步反应得到头孢卡品酯重要中间体，然后与头孢卡品酯侧链酸氨缩合，最后4-位酸经酯化并与酸成盐得到成品盐酸头孢卡品酯。本发明充分利用原子经济性原则缩短了反应路线，提高了反应的总收率，利于合成盐酸头孢卡品酯的工艺改良和优化。

  公开号：

  CN103848851B

文献信息

• [EN] CEPHEM COMPOUND<br/>[FR] COMPOSE DE CEPHEM
  申请人：DSM IP ASSETS BV

  公开号：WO2004106347A1

  公开（公告）日：2004-12-09

  The present invention is concerned with a novel cephem compound, with a process for the production of this compound, which process may contain or consist of fermentative steps, chemical steps, and/or biotransformation steps. A cephem compound according to the present invention characterised by formula (I) or a salt or ester thereof, wherein R is selected from the group consisting of (carboxymethylthio)propionyl (carboxyethylthio)propionyl Y- CH2-CO15 wherein Y is phenyl, phenoxy or tetrazolyl HOOC-X-CO wherein X is defined as (CH2)4 or wherein X is defined as (CH2)P-A-(CH2)q, wherein p and q each individually are 0, 1, 2, 3 or 4, and A is CH=CH, C-=C, CHB, C=O, O, S, NH, the nitrogen optionally being substituted or the sulfur optionally being oxidized, and B is hydrogen, halogen, C1-3 alkoxy, hydroxyl, or optionally substituted methyl, with the proviso that p+q should be 2 or 3, when A is CH=CH or C=-C, or p+q should be 3 or 4, when A is CHB, C=O, 0, S or NH or wherein X is (CH2)m-CH=A-(CH2)n or (CH2)m-C=-C-(CH2)n, wherein m and n each individually are 0, 1, 2 or 3 and m+n = 2 or 3, and A is CH or N, or wherein X is (CH2)p-CH=CH-C H=C-(CH2)q wherein p and q each individually are 0 or 1 and p+q = 0 or 1 and wherein R' is selected from the group consisting of OH O-(alkyl 1-6C) wherein the alkyl can be straight or branched and O-C(alkyl 1-6C)-O-(alkyl 1-6C) wherein the alkyl groups can be straight or branched can inter alia be prepared by fermentative techniques according to the invention and in particular using a suitable microorganism possessing or being transformed with the genes needed for conversion of an appropriate acyl-6-aminopenicillanic acid into the desired compound.

  本发明涉及一种新型头孢菌素化合物，以及用于生产该化合物的方法，该方法可以包含或由发酵步骤、化学步骤和/或生物转化步骤构成。根据本发明的头孢菌素化合物的特征是其具有以下式（I）或其盐或酯，其中R选自以下组：（羧甲基硫）丙酰基（羧乙基硫）丙酰基Y- CH2-CO15，其中Y是苯基、苯氧基或四氮唑基HOOC-X-CO，其中X定义为（CH2）4或其中X定义为（CH2）P-A-（CH2）q，其中p和q各自独立地为0、1、2、3或4，A为CH=CH、C-=C、CHB、C=O、O、S、NH，氮原子可选择性地被取代或硫原子可选择性地被氧化，B为氢、卤素、C1-3烷氧基、羟基或可选择性取代的甲基，但要求当A为CH=CH或C=-C时p+q应为2或3，或当A为CHB、C=O、O、S或NH时p+q应为3或4，或其中X为（CH2）m-CH=A-（CH2）n或（CH2）m-C=-C-（CH2）n，其中m和n各自独立地为0、1、2或3且m+n=2或3，A为CH或N，或其中X为（CH2）p-CH=CH-C H=C-（CH2）q，其中p和q各自独立地为0或1且p+q=0或1，且其中R'选自以下组：OH、O-（烷基1-6C），其中烷基可以是直链或支链，或O-C（烷基1-6C）-O-（烷基1-6C），其中烷基可以是直链或支链，可以通过本发明的发酵技术之一制备，特别是使用适当的微生物，该微生物具有或被转化为需要将适当的酰-6-氨基青霉酸转化为所需化合物所需的基因。
• 7-Hydrocarbonoxy imino-acetamido-3-carbamoyloxy methylceph-3-em-4
  申请人：Glaxo Laboratories Limited

  公开号：US03974153A1

  公开（公告）日：1976-08-10

  Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##EQU1## where R.sup.1 is a furyl, thienyl or phenyl group and R.sup.2 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 C.sub.7 cycloalkyl or phenyl group and in which the 3-position substituent is a carbamoyloxymethyl group possess a particularly valuable combination of properties, exhibiting high antibacterial activity against a broad range of gram positive and gram negative organisms, particularly high stability to .beta.-lactamases produced by various organisms, and stability in vivo. The compounds are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer. Particularly important compounds of this type are (6R,7R)-3-carbamoyloxymethyl -7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (syn isomer) and its non-toxic derivatives, e.g. the sodium salt.

  7-β-酰胺基头孢菌素，其中7-β-酰胺基团的结构为##EQU1##其中R.sup.1是呋喃基，噻吩基或苯基，R.sup.2是C.sub.1-C.sub.4烷基，C.sub.3-C.sub.7环烷基或苯基，且3-位置取代基为羰酰氧甲基基团，具有特别有价值的性质组合，对广泛的革兰氏阳性和革兰氏阴性微生物表现出高抗菌活性，特别是对由各种微生物产生的β-内酰胺酶具有高稳定性，且在体内稳定。这些化合物是同构体或存在于至少90％为同构体的同构体和反构体混合物中。这类特别重要的化合物包括(6R,7R)-3-羰酰氧甲基-7-[2-(呋喃-2-基)-2-甲氧基亚胺基]头孢-3-酮-4-羧酸（同构体）及其非毒性衍生物，例如钠盐。
• Cephalosporin antibiotics
  申请人：Glaxo Group Limited

  公开号：US04560683A1

  公开（公告）日：1985-12-24

  Cephalosporin antibiotics of general formula ##STR1## (wherein R.sup.1 represents a hydrogen atom or a methyl or 2-chloroethyl group) and non-toxic salts and non-toxic metabolically labile esters thereof. The compounds exhibit broad spectrum antibiotic activity and have high activity against both Gram-positive and Gram-negative organisms, including many .beta.-lactamase producing strains. Processes for the preparation of the compounds and pharmaceutical compositions containing them are described.

  通式为## STR1##（其中R.sup.1代表氢原子或甲基或2-氯乙基基团）的头孢菌素类抗生素及其非毒性盐和非毒性代谢易降解酯。这些化合物展示了广谱抗生素活性，并且对革兰氏阳性和革兰氏阴性菌，包括许多β-内酰胺酶产生菌株具有高活性。本文描述了制备这些化合物的方法和含有它们的制药组合物。
• Cephem compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04861769A1

  公开（公告）日：1989-08-29

  A compound of the formula: ##STR1## wherein R.sup.1 is lower alkyl, lower alkanoyl, aryl, ar(lower)alkyl or a heterocyclic group, each of which may have suitable substituent(s), R.sup.2 is carboxy or protected carboxy, R.sup.3 is hydrogen, halogen, hydroxy, lower alkoxy, acyloxy, lower alkylthio, lower alkenyl, lower alkenylthio, lower alkynyl, heterocyclicthio or a heterocyclic group, in which lower alkylthio, lower alkenyl, lower alkenylthio, heterocyclicthio and a heterocyclic group may have suitable substituent(s), R.sup.4 and R.sup.5 are each hydrogen, halogen or arylthio, A is lower alkylene, and n is an integer of 0 or 1, and a pharmaceutically acceptable salt thereof, processes for preparation thereof and pharmaceutical composition comprising the same.

  一种化合物的公式：##STR1## 其中R.sup.1是低碳基，低烷酰基，芳香族，芳基（低）烷基或杂环基，每个基团可能具有适当的取代基，R.sup.2是羧基或保护羧基，R.sup.3是氢，卤素，羟基，低烷氧基，酰氧基，低硫代烷基，低烯基，低烯基硫代基，低炔基，杂环硫代基或杂环基，在其中低硫代烷基，低烯基，低烯基硫代基，杂环硫代基和杂环基可能具有适当的取代基，R.sup.4和R.sup.5分别是氢，卤素或芳基硫代基，A是低碳基亚烷基，n是0或1的整数，以及其药学上可接受的盐，其制备过程和包含其的制药组合物。
• (6R,7R)-7-[2-aryl-2-(etherified
  申请人：Glaxo Laboratories, Limited

  公开号：US04138555A1

  公开（公告）日：1979-02-06

  Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## where R.sup.1 is a furyl, thienyl or phenyl group and R.sup.2 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl or phenyl group and in which the 3-position substituent is a carbamoyloxymethyl group possess a particularly valuable combination of properties, exhibiting high antibacterial activity against a broad range of gram positive and gram negative organisms, paticularly high stablity to .beta.-lactamases produced by various organisms, and stability in vivo. The compounds are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer. Particularly important compounds of this type are (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph- 3-em-4-carboxylic acid (syn isomer) and its non-toxic derivatives, e.g. the sodium salt.

  具有以下结构的头孢菌素抗生素，其中7.beta.-acylamido基团的结构为##STR1##其中R.sup.1是呋喃基、噻吩基或苯基，R.sup.2是C.sub.1-C.sub.4烷基、C.sub.3-C.sub.7环烷基或苯基，且3-位置取代基为羰酰氧甲基基团，具有特别有价值的性质组合，对广泛的革兰氏阳性和革兰氏阴性微生物表现出高抗菌活性，特别是对由各种微生物产生的β-内酰胺酶具有高稳定性和体内稳定性。这些化合物是同构体或存在至少90％的同构体和反构体混合物。这种类型的特别重要的化合物是(6R,7R)-3-羰酰氧甲基-7-[2-(呋喃-2-基)-2-甲氧基亚氨基]头孢-3-酮-4-羧酸（同构体）及其非毒性衍生物，例如钠盐。