7-amino-3-[(1-hydroxysulfonyl-methyltetrazol-5-yl)-thiomethyl]-ceph-3-em-4-carboxylic acid

• 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-[(1-hydroxysulfonyl-methyltetrazol-5-yl)-thiomethyl]-ceph-3-em-4-carboxylic acid
• 英文别名: 7-amino-3-(1-sulfomethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid；7-Amino-3-(sulfomethyl-1h-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid；(6R)-7-amino-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 化学式: C₁₀H₁₂N₆O₆S₃
• 分子量: 408.44
• InChiKey: ATMROFNURATUIQ-XCGJVMPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  241
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  7-amino-3-[(1-hydroxysulfonyl-methyltetrazol-5-yl)-thiomethyl]-ceph-3-em-4-carboxylic acid 生成 7-(D-α-Formyloxyphenylacetamido)-3-(1-sulfomethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl

  摘要：

  本发明的化合物是头孢菌素，其在7位具有各种酰基取代基，并且在头孢菌素核的3位有磺酸或磺胺基取代的四唑基硫甲基基团，并提供其制备的中间体。7-酰化化合物具有抗菌活性。

  公开号：

  US04048311A1

文献信息

• Cephalosporins
  申请人：Dr. Karl Thomae Gesellschaft mit beschrankter Haftung

  公开号：US04362725A1

  公开（公告）日：1982-12-07

  Compounds of the formula ##STR1## wherein A is phenyl, 4-hydroxy-phenyl, 2-thienyl, 2-furyl or 3,4-dihydroxy-phenyl; Y is hydrogen or methoxy; Het is 4H-5,6-dioxo-1,2,4-triazin-3-yl, 4-methyl-5,6-dioxo-1,2,4-triazin-3-yl, 2-methyl-5,6-dioxo-1,2,4-triazin-3-yl, 1-vinyl-tetrazol-5-yl, 1-allyl-tetrazol-5-yl or ##STR2## where n is an integer from 1 to 3, inclusive R.sub.1 is hydroxyl, amino, dimethylamino, acetylamino, aminocarbonyl, aminocarbonylamino, aminosulfonyl, aminosulfonylamino, methylcarbonyl, methylsulfonylamino, cyano, hydroxysulfonylamino, methylsulfonyl, methylsulfinyl, a carboxylic acid group or a sulfonic acid group, and --(CH.sub.2).sub.n --R.sub.1 may also be alkyl of 2 to 4 carbon atoms or 2,3-dihydroxy-propyl; R is cyclopropyl, 4'-hydroxycyclohexyl-amino ##STR3## where R.sub.2 is straight or branched, saturated or unsaturated hydrocarbyl of 1 to 4 carbon atoms or cycloalkyl of 3 to 6 carbon atoms; G is hydroxyl, aminocarbonyl, aminosulfonyl, aminocarbonylamino, acetylamino, methylsulfonylamino, methylsulfinyl or methylsulfonyl; m is 0 or 1; and R.sub.3 and R.sub.4, which may be identical to or different from each other, are each hydrogen, chlorine, fluorine, hydroxyl, methoxy, acetylamino, aminocarbonylamino, nitro, acetyl, methylcarbonyloxy, methoxycarbonyl, aminocarbonyl, cyano, methylsulfinyl, methylsulfonyl, aminosulfonyl, methylaminosulfonyl or methyl; and E is hydrogen or a protective group which is easily removable in vitro or in vivo; and, when E is hydrogen, non-toxic, pharmacologically acceptable salts thereof; the compounds as well as their salts are useful as antibiotics.

  式为##STR1##的化合物，其中A是苯基、4-羟基苯基、2-噻吩基、2-呋喃基或3,4-二羟基苯基；Y是氢或甲氧基；Het是4H-5,6-二氧杂-1,2,4-三嗪-3-基、4-甲基-5,6-二氧杂-1,2,4-三嗪-3-基、2-甲基-5,6-二氧杂-1,2,4-三嗪-3-基、1-乙烯基-四唑-5-基、1-丙烯基-四唑-5-基或##STR2##其中n为1到3的整数，R.sub.1是羟基、氨基、二甲胺基、乙酰氨基、氨基甲酰基、氨基甲酰氨基、氨基磺酰基、氨基磺酰氨基、甲基羰基、甲基磺酰氨基、氰基、羟基磺酰氨基、甲基磺酰基、甲基亚砜基、羧基或磺酸基，--(CH.sub.2).sub.n --R.sub.1也可以是2到4个碳原子的烷基或2,3-二羟基丙基；R是环丙基、4'-羟基环己基氨基##STR3##其中R.sub.2是1到4个碳原子的直链或支链、饱和或不饱和的烃基或3到6个碳原子的环烷基；G是羟基、氨基甲酰基、氨基磺酰基、氨基甲酰氨基、乙酰氨基、甲基磺酰氨基、甲基亚砜基或甲基磺酰基；m为0或1；R.sub.3和R.sub.4，可以相同也可以不同，分别是氢、氯、氟、羟基、甲氧基、乙酰氨基、氨基甲酰氨基、硝基、乙酰基、甲基羰氧基、甲氧羰基、氨基甲酰基、氰基、甲基亚砜基、甲基磺酰基、氨基磺酰基、甲基氨基磺酰基或甲基；E是氢或易于在体外或体内去除的保护基；当E为氢时，其非毒性、药理学上可接受的盐；这些化合物及其盐可用作抗生素。
• Salts in the Preparation of Cephalosporin Antibiodies
  申请人：Senthilkumar Udayampalayam P.

  公开号：US20080306256A1

  公开（公告）日：2008-12-11

  The present invention relates to an improved process for the preparation of cephalosporin antibiotics of formula (I). The present invention also provides new salts of compound of formula (II) and a process for the preparation of these new salts, where n=0.5 to 2. The present invention also provides a process for the preparation of compound of formula (I) using the new salts of formula (II).

  本发明涉及一种改进的制备式(I)头孢菌素类抗生素的方法。本发明还提供了式(II)化合物的新盐，并提供了制备这些新盐的方法，其中n=0.5至2。本发明还提供了使用式(II)的新盐制备式(I)化合物的方法。
• Salts in the preparation of cephalosporin antibiotics
  申请人：Orchid Chemicals & Pharmaceuticals Limited

  公开号：US07741478B2

  公开（公告）日：2010-06-22

  Compounds of general formula (II), wherein R1 represents R4 represents hydrogen or —CHO group, R5 represents hydrogen or trityl, R2 represents hydrogen or methoxy group, R3 represents —CH═CH2 or and M represents a dialkyl or dicycloalkyl ethylenediamine group selected from N,N′-diisobutylethylenediamine, N,N′-dicyclohexylethylenediamine, and N,N′-dicyclopentylethylenediamine, are useful in a process to make cephalosporin antibiotics of formula (I) wherein R represents hydrogen or pharmaceutically acceptable esters or alkali metals salts.

  通式（II）的化合物，其中R1代表，R4代表氢或—CHO基团，R5代表氢或三苯基甲基，R2代表氢或甲氧基，R3代表—CH═CH2或，M代表选择自N，N′-二异丁基乙二胺，N，N′-二环己基乙二胺和N，N′-二环戊基乙二胺的二烷基或二环烷基乙二胺基团，在制备通式（I）的头孢菌素抗生素的过程中是有用的，其中R代表氢或药学上可接受的酯或碱金属盐。
• NEWS SALTS IN THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS
  申请人：Orchid Chemicals and Pharmaceuticals Limited

  公开号：EP1765833A2

  公开（公告）日：2007-03-28
• Neue Cephalosporine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
  申请人：Dr. Karl Thomae GmbH

  公开号：EP0049814B1

  公开（公告）日：1985-01-09