N-(o-Chlorbenzoyl)-N-methylcarbamoylchlorid | 55248-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(o-Chlorbenzoyl)-N-methylcarbamoylchlorid
• 英文别名: N-(o-chlorobenzoyl)-N-(chloroformyl)methylamine；N-chlorocarbonyl-N-methyl-2-chlorobenzamide；N-(2-chlorobenzoyl)-N-methylcarbamoyl chloride
• CAS: 55248-82-3
• 化学式: C₉H₇Cl₂NO₂
• 分子量: 232.066
• InChiKey: JQZOWMZABYXALC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(D-α-aminophenylacetamido)-3-(5-methyl-1,3,4-thiadiazole-2-yl)thiomethyl-3-cephem-4-carboxylic acid 、 N-(o-Chlorbenzoyl)-N-methylcarbamoylchlorid 以31.8%的产率得到Sodium 7-[D-α-[3-(2-chlorobenzoyl)-3-methylureido]phenylacetamido]-3-(2-methyl-1,3,4-thiadiazol-5-ylthio)methylceph-3-em-4-carboxylate
  参考文献：
  名称：

  .alpha.-Acylureidocephalosporins and salts and esters thereof

  摘要：

  这是一段医学方面的内容，翻译如下： 这些化合物是临床上重要的头孢菌素，它们的盐和酯具有广谱的抗菌活性，对革兰氏阳性菌尤其有效，但对革兰氏阴性菌如假单胞菌等也具有活性，而商业上可获得的头孢菌素通常无法对其产生作用。该发明的首选化合物也对产生头孢菌素酶的革兰氏阴性菌如肠杆菌属、沙雷氏菌属和靛阳性变形菌等具有活性；同时，还描述了制备方法。

  公开号：

  US04312982A1

文献信息

• Cephalosporin compounds
  申请人：Eli Lilly and Company

  公开号：US04329454A1

  公开（公告）日：1982-05-11

  Compounds of the formula ##STR1## in which R is hydrogen or an acyl group, R.sub.1 is hydrogen or lower alkyl, and R.sub.2 is hydrogen, an alkali metal cation, or a readily removable ester forming group, are active antibiotics or intermediates thereto.

  公式为##STR1##的化合物，其中R为氢或酰基，R.sub.1为氢或低碳烷基，R.sub.2为氢、碱金属阳离子或易于去除的酯基团，是活性抗生素或其中间体。
• Bis-tetrazolemethyl substituted beta-lactam antibiotics, their preparation and pharmaceutical formulations containing them
  申请人：ELI LILLY AND COMPANY

  公开号：EP0048165A1

  公开（公告）日：1982-03-24

  Broad spectrum β-lactam antibiotics are described. They are represented by the formula wherein R is hydrogen or an acyl group of the formula wherein R° is an aryl or aralkyl group of the formula wherein R' is phenyl or phenyl substituted by halogen, hydroxy amino, acetamido, C,-C4 alkyl, C1-C4 alkoxy, cyano, carboxy, carboxamido, carboxymethyl, C,-C4 alkoxycarbony-Imethyl, hydroxymethyl, or aminomethyl; or R' is a di- or tri-substituted phenyl group of the formula wherein each of a, a', and a" are independently hydrogen, halogen, hydroxy, C1-C4 alkyl or C1-C4 alkoxy; and or R° is an aryloxymethyl or arylthiomethyl group of the formula wherein R' has the same meanings as defined above. and z is O or S; or R° is a heterocyclic methyl group of the formula wherein R2 is thienyl, furyl, 1H-tetrazol-1-yl, 1H-tetrazol-5-yl, wherein each b is hydrogen, amino, protected-amino, C1-C3 alkyl or phenyl; or R° is a group of the formula wherein R3 is R' as defined above and in addition 1,4-cyclohexadienyl, thienyl or furyl, and Q is hydroxy, carboxy, sulfo, or amino; or R° is an oximino substituted group represented by the formula wherein R4 is R' as defined above and in addition thienyl, furyl, or wherein b has the same meanings as defined above and R5 is hydrogen, or C1-C4 alkyl; or R° is a group of the formula wherein R3 is as defined above and R6 is phenyl substituted by 1-3 hydroxy groups or pyridyl substituted with from 1-3 hydroxy groups; or R6 is a group of the formula wherein R' is C1-C4 alkylamino, phenyl, chlorophenyl, furyl, styrryl, chlorostyrryl, or nitrostyrryl; or R6 is a group of the formula wherein n' is 1 or 2 and m is 2 or 3 with the limitation that when n' is 2, m is 2; and R8 is hydrogen, C1-C3 alkyl, C2-C4 alkanoyl, or C1-C3 alkylsulfonyl; R, is hydrogen or a carboxy protecting group; R2 is hydrogen or methoxy; R3 is a bis-tetrazolemethyl group of the formula wherein R4 is hydrogen or C1-C3 alkyl; and when R, is hydrogen, the pharmaceutically acceptable salts thereof. The compounds are obtained by reacting a 7-acylamino-3-halomethyl-1-oxa-β-lactam ester with the desired 1- or 2-tetrazolemethyl substituted 1H or 2H tetrazole-5-thiol, or alternatively by reacting a 7-amino-3-halomethyl-1-oxa-b-lactam ester with the bis-tetrazole thiol and then N-acylating with the desired carboxylic acid.

  描述了广谱β-内酰胺类抗生素。它们由式 其中 R 是氢或式中的酰基 其中 R°为式中的芳基或芳烷基 其中 R' 是苯基或被卤素、羟基氨基、乙酰氨基、C,-C4 烷基、C1-C4 烷氧基、氰基、羧基、羧氨基、羧甲基、C,-C4 烷氧基羰基甲基、羟甲基或氨基甲基取代的苯基；或 R' 是式中的二取代或三取代苯基。 其中 a、a'和 a "各自独立地为氢、卤素、羟基、C1-C4 烷基或 C1-C4 烷氧基；以及 或 R° 是式中的芳氧基甲基或芳硫甲基基团 其中 R'的含义与上式定义相同，z 为 O 或 S；或 R°为式中的杂环甲基 其中 R2 是噻吩基、呋喃基、1H-四唑-1-基、1H-四唑-5-基、 其中每个 b 是氢、氨基、受保护氨基、C1-C3 烷基或苯基；或 R° 是式中的基团 其中 R3 是如上定义的 R'，此外是 1,4-环己二烯基、噻吩基或呋喃基，而 Q 是羟基、羧基、磺基或氨基；或 R°是由式所代表的草酰亚胺取代的基团 其中 R4 是如上定义的 R'，此外是噻吩基、呋喃基，或 其中 b 的含义与上式所定义的相同，R5 为氢或 C1-C4 烷基；或 R°为式中的基团 其中 R3 如上定义，R6 是被 1-3 个羟基取代的苯基或被 1-3 个羟基取代的吡啶基；或 R6 是式中的基团 其中 R'是 C1-C4 烷基氨基、苯基、氯苯基、呋喃基、苯乙烯基、氯代苯乙烯基 或硝基苯乙烯基；或 R6 是式中的基团 其中 n' 为 1 或 2，m 为 2 或 3，但当 n' 为 2 时，m 为 2；以及 R8 为氢、C1-C3 烷基、C2-C4 烷酰基或 C1-C3 烷基磺酰基；R，为氢或羧基保护基团；R2 为氢或甲氧基；R3 为式中的双四唑甲基。 其中 R4 为氢或 C1-C3 烷基；当 R 为氢时，为其药学上可接受的盐。 这些化合物是通过 7-酰氨基-3-卤甲基-1-氧杂-β-内酰胺酯与所需的 1-或 2-四唑甲基取代的 1H 或 2H 四唑-5-硫醇反应，或通过 7-氨基-3-卤甲基-1-氧杂-b-内酰胺酯与双四唑硫醇反应，然后与所需的羧酸发生 N-酰化反应而得到的。
• Bis-tetrazoylmethyl substituted cephalosporin antibiotics, their preparation and pharmaceutical formulations containing them
  申请人：ELI LILLY AND COMPANY

  公开号：EP0048169A2

  公开（公告）日：1982-03-24

  7β-Acylamino-3-cephem-4-carboxylic acids substituted in the 3-position with a bis-tetrazole-methylthiomethyl group are described. They are represented by the formula wherein R is hydrogen or an acyl group of the formula wherein R1 is C1-C4 alkyl or C1-C4 alkyl substituted by halogen or cyano; or R is an aroyl or aralkanoyl group of the formula wherein R2 is phenyl or a mono-substituted phenyl group substituted by halogen, cyano, amino, hydroxy, C1-C4 alkyl, C1-C4 alkoxy, carboxy, carboxamido, hydroxymethyl, aminomethyl, carboxymethyl, or C1-C4 alkoxycarbony-Imethyl; or R2 is a di- or tri-substituted phenyl group of the formula wherein a, a', and a" independently are hydrogen, halogen, hydroxy, C1-C4 alkoxy, provided that only one of a. a' and a" may be hydrogen, and n is 0 or 1; or R is a heteroarylalkanoyl group of the formula wherein R3 is a group of the formula wherein each b is hydrogen, amino, protected-amino, C1-C3 alkyl or phenyl; or R is an aryloxyacetyl or arylthioacetyl group of the formula wherein R2 has the same meanings as defined above and Z is 0 or S; or R is a substituted aralkanoyl or heteroarylalkanoyl group of the formula wherein R4 is R2 as defined above, and in addition is 1,4-cyclohexadienyl, thienyl or furyl, and Q is hydroxy, formyloxy, carboxy, sulfo, or amino; or R is an oximino-substituted aralkanoyl or heteroarylalkanoyl group of the formula wherein R5 is R2 and R3 as each is defined above, and R6 is hydrogen, or C1-C4 alkyl, or R is a group of the formula wherein R4 has the same meanings defined above and R' is phenyl substituted by from 1 to 3 hydroxy groups, or pyridyl substituted by from 1 to 3 hydroxy groups, or a group of the formula wherein RB is C1-C4 alkylamino, phenyl, halophenyl, furyl, styryl, nitrostyryl or halostyryl; or R7 is a group of the formula wherein n' is 1 or 2 and m is 2 or 3, with the limitation that when n' is 2, m is 2, and R9 is hydrogen, C1-C3 alkyl, C2-C4 alkanoyl, or C1-C3 alkylsulfonyl; R, is hydrogen or a carboxy protecting group; R2 is hydrogen or methoxy; R3 is a bis-tetrazolemethyl group of the formula wherein R4 is hydrogen, or C1-C3 alkyl; and when R, is hydrogen, the pharmaceutically acceptable salts thereof. The compounds are broad spectrum antibiotics useful in the treatment and control of microorganisms pathogenic to man and animals. 7β-Amino nucleus compounds represented when R is hydrogen are intermediates useful in the preparation of the antibiotics where R is acyl. The compounds are prepared by reacting a 7-amino-3- acyloxy or halo-1-oxa-β-lactam acid or ester with the appropriate bis-tetrazolemethyl thiol.

  7β-Acylamino-3-cephem-4-carboxylic acids 的 3 位被双四唑甲硫甲基取代。它们用式表示 其中 R 是氢或式中的酰基 其中 R1 是 C1-C4 烷基或被卤素或氰基取代的 C1-C4 烷基；或 R 是式中的酰基或芳酰基 其中 R2 是苯基或被卤素、氰基、氨基、羟基、C1-C4 烷基、C1-C4 烷氧基、羧基、羧酰胺基、羟甲基、氨甲基、羧甲基或 C1-C4 烷氧基羰基-甲基取代的单取代苯基；或 R2 是式中的二取代或三取代苯基。 其中 a、a'和 a "独立地为氢、卤素、羟基、C1-C4 烷氧基，但 a、a'和 a "中只能有一个为氢，且 n 为 0 或 1；或 R 为式中的杂芳基烷酰基。 其中 R3 是式中的基团 其中每个 b 是氢、氨基、受保护氨基、C1-C3 烷基或苯基；或 R 是式中的芳氧基乙酰基或芳硫基乙酰基。 其中 R2 的含义与上述定义相同，Z 为 0 或 S；或 R 为式中的取代芳烷基或杂芳基芳烷基基团 其中 R4 是如上定义的 R2，此外是 1,4-环己二烯基、噻吩基或呋喃基，且 Q 是羟基、甲酰氧基、羧基、磺基或氨基；或 R 是式中的草酰亚胺取代的假烷酰基或杂芳基假烷酰基。 其中 R5 是如上定义的 R2 和 R3，R6 是氢或 C1-C4 烷基，或 R 是式中的基团 其中 R4 具有与上式相同的定义，R'是被 1 至 3 个羟基取代的苯基，或被 1 至 3 个羟基取代的吡啶基，或一个式中的基团 其中 RB 是 C1-C4 烷基氨基、苯基、卤代苯基、呋喃基、苯乙烯基、硝基或卤代苯乙烯基；或 R7 是式中的基团 其中 n' 为 1 或 2，m 为 2 或 3，但当 n' 为 2 时，m 为 2，R9 为氢、C1-C3 烷基、C2-C4 烷酰基或 C1-C3 烷基磺酰基；R，为氢或羧基保护基；R2 为氢或甲氧基；R3 为式中的双四唑甲基基团 其中 R4 为氢或 C1-C3 烷基；当 R 为氢时，为其药学上可接受的盐。 这些化合物是广谱抗生素，可用于治疗和控制对人类和动物致病的微生物。当 R 为氢时所代表的 7β-氨基核化合物是制备 R 为酰基的抗生素的中间体。 这些化合物是通过 7-氨基-3-酰氧基或卤代-1-氧杂-β-内酰胺酸或酯与适当的双四唑甲基硫醇反应制备的。
• US3936442A
  申请人：——

  公开号：US3936442A

  公开（公告）日：1976-02-03
• US3939149A
  申请人：——

  公开号：US3939149A

  公开（公告）日：1976-02-17