7-amino-3-[((1H-1,2,3-triazol-5-yl)thio)methyl]ceph-3-em-4-carboxylic acid | 37539-03-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 英文名称: 7-amino-3-[((1H-1,2,3-triazol-5-yl)thio)methyl]ceph-3-em-4-carboxylic acid
• 英文别名: 7-Amino-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid；7-Amino-3-(1H-1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid；7-amino-3-(1,2,3-triazol-5-yl-thiomethyl)-3-cephem-4-carboxylic acid；3-(1,2,3-Triazol-5-ylthiomethyl)-7-amino-3-cephem-4-carboxylic acid；7-Amino-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid；7-amino-3-[1,2,3-triazol-5-yl]thiomethylceph-3-em-4-carboxylic acid；(6R,7R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid；(6R)-7-amino-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 37539-03-0
• 化学式: C₁₀H₁₁N₅O₃S₂
• 分子量: 313.361
• InChiKey: MLOZJRLUNNFSGD-IOJJLOCKSA-N

物化性质

• 熔点：
  >158°C (Subl.)
• 沸点：
  723.3±60.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)
• 溶解度：
  加热、超声处理轻微溶于甲醇、轻微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  176
• 氢给体数：
  3
• 氢受体数：
  8

制备方法与用途

7-氨基-3-(1,2,3-三唑-4-硫代)甲基-头孢环-4-羧酸常用于制备三唑类半合成头孢菌素。

反应信息

• 作为反应物：
  描述：

  7-amino-3-[((1H-1,2,3-triazol-5-yl)thio)methyl]ceph-3-em-4-carboxylic acid 生成 7-[D-α-Amino-α-(4'-carboxymethoxyphenyl)acetamido]-3-(1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Substituted phenylglycylcephalosporins

  摘要：

  具有在7位处带有取代苯基甘氨酰基取代基和3位处的各种基团的头孢菌素化合物，是通过对7-氨基头孢菌烷酸进行酰化制备的。这些化合物具有抗菌活性。

  公开号：

  US03953439A1
• 作为产物：
  描述：

  3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid 、 5-mercapto-1H-1,2,3-triazole 、 三氟化硼 、 乙醚 生成 7-amino-3-[((1H-1,2,3-triazol-5-yl)thio)methyl]ceph-3-em-4-carboxylic acid
  参考文献：
  名称：

  SAIKAWA, ISAMU;TAKANO, SHUNTARO;MOMONOI, KAISHU;TAKAKURA, ISAMU;KURODA, S+

  摘要：

  DOI：

文献信息

• Syn isomer of 7-[2-cyclo(lower) alkoxyimino-2-(2-amino-or substituted
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04331664A1

  公开（公告）日：1982-05-25

  Syn isomers of 3-substituted 7-[2-substituted imino-2-substituted acetamido]-3-cephem-4-carboxylic acid and salt bacteriostatic-compounds and pharmaceutical compositions thereof and processes for preparing same.

  3-取代基7-[2-取代基亚胺基-2-取代基乙酰胺基]-3-头孢烯-4-羧酸的同分异构体及其盐、抑菌化合物和药物组合物以及其制备方法。
• Cephalosporin derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US04492692A1

  公开（公告）日：1985-01-08

  A cephalosporin derivative of the formula: ##STR1## in which R.sup.0 is a hydrogen atom or a methyl radical, R.sup.1 is any one of the C-3 substituents from antibacterially-active cephalosporins known in the art; R.sup.2 is any one of the C-4 substituents from antibacterially-active cephalosporins known in the art; R.sup.3 is a hydrogen atom or a 1-6C alkoxy or 1-6C alkylthio radical; X.sup.1 is a sulphur or oxygen atom, a CH.sub.2 radical or a radical of the formula NR.sup.7 in which R.sup.7 is a hydrogen atom, a 1-6C alkyl, formyl or benzyl radical; X.sup.2 is a nitrogen atom or a radical of the formula N.sup..sym. -R.sup.7 ; R.sup.4 and R.sup.7, and R.sup.5 and R.sup.6 are a variety of substituents which are described in the specification; and the pharmaceutically-acceptable acid- or base-addition salts thereof. Pharmaceutical compositions, manufacturing processes and intermediates are also described.

  一种头孢菌素衍生物的化学式：##STR1## 其中 R.sup.0 是氢原子或甲基基团，R.sup.1 是来自已知具有抗菌活性的头孢菌素的C-3取代基之一；R.sup.2 是来自已知具有抗菌活性的头孢菌素的C-4取代基之一；R.sup.3 是氢原子或1-6C烷氧基或1-6C烷硫基团；X.sup.1 是硫或氧原子，CH.sub.2基团或化学式NR.sup.7中的基团，其中R.sup.7是氢原子，1-6C烷基，甲酰基或苄基基团；X.sup.2 是氮原子或化学式N.sup..sym. -R.sup.7的基团；R.sup.4和R.sup.7，以及R.sup.5和R.sup.6是说明书中描述的各种取代基；以及其药学上可接受的酸盐或碱盐。还描述了制药组合物、制造过程和中间体。
• Process for the manufacture of cephalosporin derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US04497949A1

  公开（公告）日：1985-02-05

  The invention relates to a process for the manufacture of a cephalosporin derivative of the formula I: ##STR1## in which X is a sulphur or oxygen atom or a sulphinyl radical, R.sup.1 is any one of the C-3 substituents from antibacterially-active cephalosporins known in the art, R.sup.2 is a hydrogen atom or a 1-6C alkyl or 2-6C alkenyl radical, R.sup.3 is a hydrogen atom or one of a variety of radicals defined in the specification, and the pharmaceutically-acceptable acid- and base-addition salts thereof, characterized by reaction of a compound of the formula IX: ##STR2## in which R.sup.16 and R.sup.17 individually have one of the values given above for R.sup.2 and R.sup.3, or a derivative thereof in which the carbonyl group is masked, with a compound of the formula X: ##STR3## in which R.sup.18 is a hydrogen atom or any one of the cephalosporin 3-carboxylic acid protecting groups known in the art; whereafter, when R.sup.18 is other than a hydrogen atom, the protecting group R.sup.18 is replaced by hydrogen by conventional means.

  该发明涉及一种制备化学式I的头孢菌素衍生物的方法：其中X是硫或氧原子或磺基，R.sup.1是来自已知抗菌活性头孢菌素的C-3取代基中的任何一个，R.sup.2是氢原子或1-6C烷基或2-6C烯基基团，R.sup.3是氢原子或规范中定义的各种基团之一，以及其药学上可接受的酸盐和碱盐，其特征在于将化合物IX的反应物进行反应：其中R.sup.16和R.sup.17分别具有R.sup.2和R.sup.3给定的上述值中的一个，或者它们的衍生物，其中羰基基团被掩蔽，与化合物X的反应物进行反应：其中R.sup.18是氢原子或已知的头孢菌素3-羧基保护基中的任何一个；之后，当R.sup.18不是氢原子时，通过常规手段将保护基R.sup.18替换为氢。
• Derivatives of 7-(cyclized)phenylglycyl-3-triazolo-thio methyl
  申请人：Bristol-Myers Company

  公开号：US04061862A1

  公开（公告）日：1977-12-06

  Compounds of the formula ##STR1## wherein A is hydrogen, hydroxy, methyl or methoxy, R.sup.1 is hydrogen, sodium or potassium, and R.sup.2 is 1,2,3-triazol-5-yl, such group being unsubstituted or substituted with one or two lower alkyl groups of one to four carbon atoms are prepared by reacting the appropriate aldehyde with the corresponding amphoteric cephalosporin. A preferred product has the structure ##STR2##

  式为##STR1##的化合物，其中A为氢、羟基、甲基或甲氧基，R.sup.1为氢、钠或钾，R.sup.2为1,2,3-三唑-5-基，该基团未取代或取代为一个或两个碳原子数为一至四的较低烷基基团，通过将适当的醛与相应的两性头孢菌素反应制备而成。首选产物具有结构##STR2##
• Cephalosporin compounds and processes for the preparation thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04242510A1

  公开（公告）日：1980-12-30

  Cephalosporin compounds of the formula (I): ##STR1## wherein R.sup.1 is a group of the formula: ##STR2## in which X is sulfur, oxygen or substituted or unsubstituted imino, M is sulfur or oxygen, R.sup.2 is hydrogen, or a saturated or unsaturated aliphatic hydrocarbon residue, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is hydrogen, halogen, lower alkyl, acyloxymethyl or heterocyclic-thiomethyl which may be substituted with lower alkyl, and R.sup.5 is carboxy or its derivative, and nontoxic, pharmaceutically salt thereof.

  头孢菌素化合物的化学式（I）：其中R.sup.1是以下化学式的基团：其中X是硫、氧或取代或未取代的亚胺，M是硫或氧，R.sup.2是氢，或饱和或不饱和的脂肪烃基，R.sup.3是氢或较低的烷基，R.sup.4是氢、卤素、较低烷基、乙酰氧甲基或杂环硫甲基，可以用较低烷基取代，R.sup.5是羧基或其衍生物，以及其无毒、药用盐。