2-(2-amino-4-thiazolyl)-2-[[(Z)-(t-butoxycarbonyl)methoxy]imino]-acetic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-amino-4-thiazolyl)-2-[[(Z)-(t-butoxycarbonyl)methoxy]imino]-acetic acid
• 英文别名: 2-(2-aminothiazol-4-yl)-2-syn-(2-tert-butoxy-2-oxoethoxyimino)acetic acid；2-(2-aminothiazol-4-yl)-(Z)-2-(t-butoxycarbonylmethoxyimino)-acetic acid；2-(2-aminothiazol-4-yl)-2-(Z)-tert-butoxycarbonylmethoxyiminoacetic acid；(2-Aminothiazol-4-yl)-tert-butoxycarbonylmethoxyimino acetic acid；(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]iminoacetic acid
• 化学式: C₁₁H₁₅N₃O₅S
• 分子量: 301.323
• InChiKey: XSQPXYAKVKORFJ-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2-amino-4-thiazolyl)-2-[[(Z)-(t-butoxycarbonyl)methoxy]imino]-acetic acid 生成 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid
  参考文献：
  名称：

  Cephem compounds

  摘要：

  这项发明涉及具有高抗微生物活性的新型化合物，其化学式为：##STR1## 其中R.sup.1是羧基(较低)烷基或保护羧基(较低)烷基，R.sup.2是羧基或保护羧基，R.sup.3是氢或较低烷基，R.sup.4是较低烷基、较低烷氧基、乙酰氧甲基、较低硫代甲基、较低烷氧甲基、卤素、较低烯基或氢，以及其药用可接受盐。

  公开号：

  US04515788A1
• 作为产物：
  描述：

  2-(2-Formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetic acid 生成 2-(2-amino-4-thiazolyl)-2-[[(Z)-(t-butoxycarbonyl)methoxy]imino]-acetic acid
  参考文献：
  名称：

  Cephem compounds

  摘要：

  这项发明涉及具有高抗微生物活性的新型化合物，其化学式为：##STR1## 其中R.sup.1是羧基(较低)烷基或保护羧基(较低)烷基，R.sup.2是羧基或保护羧基，R.sup.3是氢或较低烷基，R.sup.4是较低烷基、较低烷氧基、乙酰氧甲基、较低硫代甲基、较低烷氧甲基、卤素、较低烯基或氢，以及其药用可接受盐。

  公开号：

  US04515788A1

文献信息

• Process for the manufacture of 1-sulpho-2-oxoazetidine carboxylic acid
  申请人：Hoffmann-La Roche Inc.

  公开号：US04652651A1

  公开（公告）日：1987-03-24

  The manufacture of 1-sulpho-2-oxazetidine derivatives of the formula ##STR1## in which Het is an optionally amino-substituted, 5- or 6-membered, aromatic heterocycle containing 1 or 2 nitrogen atoms and optionally also an oxygen or sulphur atom, R.sup.1 is hydrogen, lower alkyl, phenyl-lower alkyl, lower alkanoyl, lower alkoxycarbonyl, lower alkenyl-lower alkyl, lower alkoxycarbonyl-lower alkyl, phenyl-lower-alkoxycarbonyl-lower alkyl, nitrophenyl-lower-alkoxycarbonyl-lower alkyl or carboxy-lower alkyl and R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxycarbonyl, lower alkanoyloxy-lower alkyl, lower alkoxycarbonyl-lower alkenyl, hydroxyiminomethyl, lower alkoxyiminomethyl, carbamoyl, carbamoyl-lower alkenyl or carbamoyloxy-lower alkyl, the group .dbd.NOR.sup.1 being present at least partially in the syn-form, in racemic form or in the form of the 3S-enantiomer, and of readily hydrolyzable esters and pharmaceutically compatible salts of these compounds, by acylating a compound of the formula ##STR2## in which R.sup.20 equals R.sup.2 or can also represent a 2,2-dimethyl-1,3-dioxolan-4-yl group and R.sup.3 is hydrogen or sulpho, or a salt thereof with a thioester of the formula ##STR3## in which Het is as above and R.sup.10 has any of the values of R.sup.1 except carboxy-lower alkyl, and can also represent a tri-lower alkyl-silyl-lower-alkoxycarbonyl-lower alkyl group or a carboxy-lower alkyl group converted into a readily hydrolyzable ester group, and the group .dbd.NOR.sup.10 is present at least partially in the syn-form, and carrying out subsequent steps (N-sulphonation, conversion of R.sup.20 into R.sup.2, R.sup.10 into R.sup.1), some of which are optional. The invention also provides certain novel products of formula I and benzthiazolyl thioesters of formula III per se and the preparation of the benzthiazolyl thioesters by esterifying corresponding carboxylic acids. Finally, the invention provides a process for the preparation of carboxylic acids in which R.sup.1 is t-alkoxycarbonylmethyl. The compounds of formula I have antimicrobial activity.

  该专利描述了一种制备1-磺酸-2-噁唑环丙烷衍生物的方法，其化学式为##STR1##其中Het是一个含有1或2个氮原子和可能还有一个氧原子或硫原子的可选氨基取代的5或6元芳香杂环，R.sup.1是氢、低烷基、苯基-低烷基、低烷酰、低烷氧羰基、低烯基-低烷基、低烷氧羰基-低烷基、苯基-低烷氧羰基-低烷基、硝基苯基-低烷氧羰基-低烷基或羧基-低烷基，R.sup.2是氢、低烷基、低烯基、低炔基、低烷氧羰基、低烷酰氧基-低烷基、低烷氧羰基-低烯基、羟基亚胺甲基、低烷氧亚胺甲基、氨甲酰基、氨甲酰基-低烯基或氨甲酰氧基-低烷基，.dbd.NOR.sup.1基团至少部分以syn-形式存在，是外消旋形式或3S-对映体形式，以及这些化合物的易水解酯和药用兼容盐的制备方法。
• Cephalosporin compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04788185A1

  公开（公告）日：1988-11-29

  A compound of the formula; ##STR1## wherein R.sup.0 stands for hydrogen atom, nitrogen-containing heterocyclic group, acyl group or esterified carboxyl group, Z stands for S, S.fwdarw.O, O or CH.sub.2, R.sup.4 stands for hydrogen atom, methoxy group or formamido group, R.sup.13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a physiologically or pharmaceutically acceptable salt or ester thereof. This compound is novel and has excellent antibacterial activity.

  该化合物的化学式为; ##STR1## 其中R.sup.0代表氢原子、含氮杂环基团、酰基或酯化羧基，Z代表S、S.fwdarw.O、O或CH.sub.2，R.sup.4代表氢原子、甲氧基或甲酰氨基，R.sup.13代表氢原子、甲基、羟基或卤原子，A代表在2,3-或3,4-位置形成的一个可选取代的咪唑-1-基团，或其生理学或药学上可接受的盐或酯。该化合物是新颖的，并具有优良的抗菌活性。
• Thiazole derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04695639A1

  公开（公告）日：1987-09-22

  A novel aminothiazoleacetic acid derivative which is an advantageous synthetic intermediate for .beta.-lactam antibiotics, and its production method and use. Starting with diketene, the production method comprises the following squence of steps. ##STR1## (In the above formulas, R is lower alkyl or phenyl; R.sub.1 and R.sub.2 each are hydrogen or lower alkyl; X and X' each are halogen; W is S or SO.sub.2 ; and W' is OH or ##STR2##

  一种新的氨基噻唑乙酸衍生物，是β-内酰胺类抗生素的有利合成中间体，以及其生产方法和用途。该生产方法从二酮开始，包括以下步骤。 ##STR1## （在上述公式中，R是较低的烷基或苯基；R.sub.1和R.sub.2每个都是氢或较低的烷基；X和X'每个都是卤素；W是S或SO.sub.2；W'是OH或##STR2##）
• [EN] A PROCESS FOR THE PREPARATION OF CEFIXIME VIA ALKYL-OR ARYL-SULFONATES<br/>[FR] PROCEDE DE PREPARATION DE CEFIXIME VIA DES ALKYLSULFONATES OU ARYLSULFONATES
  申请人：ANTIBIOTICOS SPA

  公开号：WO2003040148A1

  公开（公告）日：2003-05-15

  A process for the preparation Cefixime, namely 7-[2-(2-aminothiazol-4-yl)-2-(carboxymethoxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid, via alkyl- or aryl- sulfonates, of general formula (IA).

  一种制备头孢克肟的方法，即通过烷基或芳基磺酸盐的通用公式（IA）制备7-[2-(2-氨基噻唑-4-基)-2-(羧甲氧亚氨基)乙酰氨基]-3-乙烯基-3-头孢烯-4-羧酸。
• Novel c-3 s/o-and s/n formaldehe acetal derivatives of cephalosporins and their use as antibotics
  申请人：——

  公开号：US20040260084A1

  公开（公告）日：2004-12-23

  The compounds of the general formula (I) wherein R 1 denotes a pharmaceutically acceptable side chain radical as used conventionally in the field of cephalosporins and wherein R 2 denotes a pharmaceutically acceptable group which is bonded to the remaining part of the molecule by an oxygen-carbon single bond or a nitrogen-carbon single bond, and their pharmaceutically acceptable salts, esters and amide derivatives are effective antibiotics. 1

  通式（I）的化合物，其中R1表示在头孢菌素领域中惯常使用的药用可接受的侧链基团，而R2表示通过氧-碳单键或氮-碳单键与分子的其余部分连接的药用可接受的基团，以及它们的药用可接受的盐、酯和酰胺衍生物是有效的抗生素。