碘甲基舒巴坦 | 76247-39-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 碘甲基舒巴坦
• 英文名称: iodomethyl 1,1-dioxopenicillanate
• 英文别名: iodomethyl penicillanate 1,1-dioxide；iodomethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide；iodomethyl 4,4-dioxopenicillanate；Iodomethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide；iodomethyl (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 76247-39-7
• 化学式: C₉H₁₂INO₅S
• 分子量: 373.168
• InChiKey: OLTVXWRKDHZFFR-RQJHMYQMSA-N

物化性质

• 沸点：
  535.9±50.0 °C(Predicted)
• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  氯甲基(2S,5R)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸酯4,4-二氧化物	Chloromethyl 1,1-dioxopenicillanate	76247-40-0	C9H12ClNO5S	281.717
  舒巴坦酸	sulbactum	68373-14-8	C8H11NO5S	233.245

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	{[6-(benzyloxy)adipoyl]oxy}methyl penicillanate sulfone	87343-31-5	C22H27NO9S	481.524
  ——	<<5-(benzyloxy)glutaryl>oxy>methyl penicillanate sulfone	87343-26-8	C21H25NO9S	467.497
  舒他西林	sultamicillin T	76497-13-7	C25H30N4O9S2	594.667
  ——	6'-(alpha-carbobenzyloxyamino-p-hydroxyphenylacetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide	84519-02-8	C33H36N4O12S2	744.8
  ——	6'-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanoyloxymethyl penicillanate 1,1-dioxide	84519-06-2	C28H34N4O9S2	634.731

反应信息

• 作为反应物：
  描述：

  碘甲基舒巴坦 在 N-氯-N-吡啶基乙酰肼 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 舒他西林
  参考文献：
  名称：

  Synthesis of 1,1-dioxopenicillanoyloxymethyl 6-[d-α-(benzylideneaminophenylacetamido)]penicillanate and analogs. New intermediates in the preparation of sultamicillin

  摘要：

  The synthesis of benzylidene imines of sultamicillin and analogs 1 is described. These new compounds showed high stability and were prepared under very mild conditions and high yields. Furthermore, they are convenient starting materials for the preparation of sultamicillin 5 (important prodrug of ampicillin and sulbactam) as its base form, by deprotection of the amino group with Girard reagents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00599-3
• 作为产物：
  描述：

  舒巴坦酸 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 19.5h， 生成 碘甲基舒巴坦
  参考文献：
  名称：

  一种阿莫西林-舒巴坦杂合分子的合成方法及应用

  摘要：

  本发明公开了一种阿莫西林‑舒巴坦杂合分子的合成方法及其应用，属于有机合成技术领域。本发明通过以氯溴甲烷作为舒巴坦酸的氯甲基试剂，有效提高了关键中间体舒巴坦氯甲酯的产率，并通过以舒巴坦氯甲酯和(Z)‑6‑(2‑(4‑羟基苯基)‑2‑((4‑甲氧基‑4‑氧代丁‑2‑烯‑2‑基)氨基)乙酰氨基)‑3,3‑二甲基‑7‑氧代‑4‑硫‑1‑氮杂双环[3.2.0]庚烷‑2‑羧酸为原料，经缩合反应并用强酸脱去保护基后，制得阿莫西林‑舒巴坦杂合分子。本发明的合成方法反应条件温和，原料廉价易得，制备成本低，安全性好，工艺简单易行，产物收率高。

  公开号：

  CN112724162B

文献信息

• 1,1-Alkanediol dicarboxylate linked antibacterial agents
  申请人：Pfizer, Inc.

  公开号：US04457924A1

  公开（公告）日：1984-07-03

  Useful antibacterial agents in which a penicillin and/or a beta-lactamase inhibitor are linked via 1,1-alkanediol dicarboxylates are of the formula ##STR1## where A is the residue of certain dicarboxyic acids, R.sup.3 is H or (C.sub.1 -C.sub.3), n is zero or 1 such that when n is zero R is P or B and R.sup.1 is the residue of certain esters, H or a salt thereof; and when n is 1, one of R and R.sup.1 is P and the other is B, and P is ##STR2## where R.sup.2 is H or certain acyl groups, and B is the residue of a beta-lactamase inhibiting carboxylic acid; a method for their use, pharmaceutical compositions thereof and intermediates useful in their production.

  有用的抗菌剂，其中通过1,1-烷二醇二羧酸酯连接了青霉素和/或β-内酰胺酶抑制剂，其化学公式为##STR1##，其中A是某些二羧酸的残基，R.sup.3是H或(C.sub.1-C.sub.3)，n是0或1，当n为0时，R是P或B，R.sup.1是某些酯的残基，H或其盐；当n为1时，R和R.sup.1中的一个为P，另一个为B，P为##STR2##，其中R.sup.2是H或某些酰基团，B是β-内酰胺酶抑制羧酸的残基；其使用方法、药物组合物及其生产中有用的中间体。
• Bis-esters of dicarboxylic acids with amoxicillin and certain
  申请人：Pfizer Inc.

  公开号：US04462934A1

  公开（公告）日：1984-07-31

  Antibacterial bis-esters of 1,4-cyclohexanedicarboxylic acids and alkane dicarboxylic acids wherein the ester moieties are derived from different alcohols; one alcohol being hydroxymethylpenicillanate 1,1-dioxide, or the 6-beta-hydroxymethyl or the 6-alpha-aminomethyl derivative thereof; and the other being 6-[D-(2-amino-2-(p-hydroxyphenyl)acetamido)]penicillanic acid (amoxicillin); and pharmaceutically acceptable salts thereof; a method for the use of said esters and their salts, and methods for their preparation.

  1,4-环己二羧酸和烷二羧酸的抗菌双酯，其中酯基来源于不同的醇类；一种醇为羟甲基青霉素酸1,1-二氧化物，或其6-β-羟甲基或6-α-氨基甲基衍生物；另一种为6-[D-(2-氨基-2-(对羟基苯基)乙酰基)]青霉素酸（阿莫西林）；及其药用可接受盐；一种使用所述酯及其盐的方法，以及其制备方法。
• 6-Amidinopenicillanic acid derivatives including the radical of a
  申请人：Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik

  公开号：US04325960A1

  公开（公告）日：1982-04-20

  The present invention relates to hitherto unknown compounds of the general formula I: ##STR1## in which R.sub.1 stands for a five- to ten-membered azacycloalkyl or azabicycloalkyl residue attached via the nitrogen atom and optionally being substituted by one or two, the same or different, lower alkyl groups; R.sub.2 represents a hydrogen atom or a lower alkyl, aryl, or aralkyl radical; and A represents a radical of a .beta.-lactamase inhibitor containing a .beta.-lactam ring as well as a carboxy group, A being connected via the carboxy group. The present compounds are useful in the treatment of bacterial infections. The new compounds are in particular strongly active against .beta.-lactamase producing bacteria.

  本发明涉及到迄今为止未知的一般式I的化合物： 其中R.sub.1代表通过氮原子连接的五元至十元的氮杂环烷基或氮杂双环烷基残基，并且可选择地被一个或两个、相同或不同的较低烷基基团取代；R.sub.2代表氢原子或较低烷基、芳基或芳基烷基基团；A代表含有β-内酰胺酶抑制剂的基团，该基团包含一个β-内酰胺环以及一个羧基，A通过羧基连接。这些化合物在治疗细菌感染中非常有用。这些新化合物特别对产生β-内酰胺酶的细菌具有强烈的抗活性。
• Process for the preparation of penicillanic acid esters
  申请人：Pfizer Inc.

  公开号：US04381263A1

  公开（公告）日：1983-04-26

  A process for the preparation of chloromethyl esters of penicillanic acids, using iodochloromethane or bromochloromethane and a tetraalkylammonium salt of the penicillanic acid, and their use in processes for the synthesis of penicillanic acid esters, using a halomethyl ester and the tetraalkylammonium salt of the penicillanic acid, which readily hydrolyze in vivo to antibacterial penicillins and the beta-lactamase inhibitor penicillanic acid sulfone.

  一种制备青霉素酸氯甲酯的方法，使用碘氯甲烷或溴氯甲烷和青霉素酸四烷基铵盐，以及它们在合成青霉素酸酯的过程中的应用，使用卤代甲酯和青霉素酸四烷基铵盐，这些酯在体内容易水解成抗菌青霉素和β-内酰胺酶抑制剂青霉素酸磺酮。
• Process for 6'-amino-penicillanoyloxymethyl penicillanate 1,1-dioxide
  申请人：Pfizer Inc.

  公开号：US04375434A1

  公开（公告）日：1983-03-01

  6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is prepared by a two-step procedure. The first step consists of coupling a salt of a 6-(protected amino)penicillanic acid with a halomethyl, an alkylsulfonyloxymethyl or an arylsulfonyloxymethyl ester of penicillanic acid 1,1-dioxide, to give a 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide, wherein the protection at the 6-position has been achieved by coupling the 6-aminopenicillanic acid with a beta-dicarbonyl compound. The second step consists of removal of the protecting group on the 6'-amino group, using aqueous acid. 6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is a chemical intermediate for preparing antibacterial agents. Also claimed are the 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds used as intermediates in the process of this invention.

  6'-氨基青霉素酰氧甲基青霉素酯1,1-二氧化物是通过两步法制备的。第一步包括将6-(保护氨基)青霉素酸的盐与青霉素酸1,1-二氧化物的卤甲基、烷基磺酰氧甲基或芳基磺酰氧甲基酯偶联，得到6'-(保护氨基)青霉素酰氧甲基青霉素酯1,1-二氧化物，其中6-位置的保护是通过将6-氨基青霉素酸与β-二羰基化合物偶联实现的。第二步包括使用水溶酸去除6'-氨基基团的保护基。6'-氨基青霉素酰氧甲基青霉素酯1,1-二氧化物是制备抗菌药物的化学中间体。还声明了作为本发明过程中间体使用的6'-(保护氨基)青霉素酰氧甲基青霉素酯1,1-二氧化物化合物。