1-aminocyclohexanecarboxylic acid benzyl ester p-toluenesulfonate | 102373-24-0

• 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: 1-aminocyclohexanecarboxylic acid benzyl ester p-toluenesulfonate
• 英文别名: Phenylmethyl 1-aminocyclohexanecarboxylate-p-toluenesulfonate；benzyl 1-aminocyclohexane-1-carboxylate;4-methylbenzenesulfonic acid
• CAS: 102373-24-0
• 化学式: C₇H₈O₃S*C₁₄H₁₉NO₂
• 分子量: 405.515
• InChiKey: HLLZQWQFBKVLBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-aminocyclohexanecarboxylic acid benzyl ester p-toluenesulfonate 在 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以97%的产率得到1-aminocyclohexanecarboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis, Selective Aldose Reductase Inhibitory Profile and Antihyperglycaemic Potential of Certain Parabanic Acid Derivatives

  摘要：

  描述了某些对二氨基甲酸衍生物1a-p的合成和醛糖还原酶抑制剖面。此外，研究了这些化合物的抗高血糖潜力。在这个系列中，最活跃的抑制剂是化合物1g、1p和10，它们在浓度为1 x 10−4时分别显示出36.6%、90%和91%的抑制活性。它们的IC50分别为2 x 10−6、7.5 x 10-8和5 x 10-8。化合物10表现出明显的抗高血糖效果。

  DOI：

  10.3797/scipharm.aut-01-204
• 作为产物：
  描述：

  1-氨基-1-环己基甲酸 、 对甲苯磺酸 、 苯甲醇 以 甲苯 为溶剂， 生成 1-aminocyclohexanecarboxylic acid benzyl ester p-toluenesulfonate
  参考文献：
  名称：

  Synthesis, Selective Aldose Reductase Inhibitory Profile and Antihyperglycaemic Potential of Certain Parabanic Acid Derivatives

  摘要：

  描述了某些对二氨基甲酸衍生物1a-p的合成和醛糖还原酶抑制剖面。此外，研究了这些化合物的抗高血糖潜力。在这个系列中，最活跃的抑制剂是化合物1g、1p和10，它们在浓度为1 x 10−4时分别显示出36.6%、90%和91%的抑制活性。它们的IC50分别为2 x 10−6、7.5 x 10-8和5 x 10-8。化合物10表现出明显的抗高血糖效果。

  DOI：

  10.3797/scipharm.aut-01-204

文献信息

• Epoxycarboxamide compound, azide compound, and amino alcohol compound, and process for preparing alpha-keto amide compound using them
  申请人：Seikagaku Corporation

  公开号：US20030153788A1

  公开（公告）日：2003-08-14

  The present invention is to provide manufacturing intermediates which can be led to useful &agr;-ketoamide compounds having protease-inhibiting activity extremely economically and stereoselectively, and to provide epoxycarboxamide compounds, azide compounds and amino alcohol compounds represented by the following formulae: 1 wherein R 1 and R 2 each represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R 3 represents alkyl group, alkenyl group, aromatic hydrocarbon group, heterocyclic group, R 6 —O— or R 7 —N(R 8 )—; where R 6 represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R 7 and R 8 each represents hydrogen atom, alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group, and, R 4 and R 5 represent the same groups as R 7 and R 8 , respectively, and R 4 and R 5 optionally form a ring together; and X represents —O— or —N(R 9 )—, where R 9 represents hydrogen atom or alkyl group, and X optionally forms a ring together with R 4 or R 5 , and processes for preparing &agr;-keto amide compound using the same.

  本发明旨在提供制造中间体，以极其经济和立体选择性地导向有蛋白酶抑制活性的有用α-酮酰胺化合物，并提供由以下式表示的环氧羧酰胺化合物，叠氮化合物和氨基醇化合物：其中R1和R2分别表示烷基，烯基，芳香族烃基或杂环基；R3表示烷基，烯基，芳香族烃基，杂环基，R6-O-或R7-N（R8）-；其中R6表示烷基，烯基，芳香族烃基或杂环基；R7和R8分别表示氢原子，烷基，烯基，芳香族烃基或杂环基，而R4和R5分别表示与R7和R8相同的基团，R4和R5可选择性地共同形成环；X表示-O-或-N（R9）-，其中R9表示氢原子或烷基，X可选择性地与R4或R5共同形成环，以及使用它们制备α-酮酰胺化合物的方法。
• Cyclic amide derivatives
  申请人：Fujirebio Kabushiki Kaisha

  公开号：US06117870A1

  公开（公告）日：2000-09-12

  A cyclic amide derivative of formula (I): ##STR1## wherein R.sup.1 represents a substituted alkyl group, a substituted alkenyl group, a substituted amino group, a substituted alkoxyl group, a substituted alkylthio group, a substituted carbamoyl group, a substituted sulfonamide group or a substituted amide group; the ring A represents a saturated cyclic alkyl group with 5 to 7 carbon atoms or a hetero-atom-containing saturated heterocyclic group with 3 to 6 carbon atoms; R.sup.2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group; R.sup.3 represents a hydrogen atom, a group represented by the general formula R.sup.4 O-- or a group represented by the general formula R.sup.5 (R.sup.6)N-- wherein R.sup.4 represents hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group; R.sup.5 and R.sup.6 may be the same or different and each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group. The cyclic amide derivative of formula (I) have a strong and selective inhibitory action of a cathepsin K and a clinical efficacy when administered orally.

  公式（I）的环酰胺衍生物：##STR1## 其中R.sup.1表示取代的烷基，取代的烯基，取代的氨基，取代的烷氧基，取代的烷硫基，取代的氨基甲酰基，取代的磺酰胺基或取代的酰胺基；环A表示具有5到7个碳原子的饱和环烷基或具有3到6个碳原子的含杂原子的饱和杂环基；R.sup.2表示氢原子，取代或未取代的烷基，取代或未取代的芳香族碳氢基或取代或未取代的杂环基；R.sup.3表示氢原子，由一般式R.sup.4 O--表示的基团或由一般式R.sup.5（R.sup.6）N--表示的基团，其中R.sup.4表示氢原子，取代或未取代的烷基，取代或未取代的芳香族碳氢基或取代或未取代的杂环基；R.sup.5和R.sup.6可以相同也可以不同，且每个表示氢原子，取代或未取代的烷基，取代或未取代的芳香族碳氢基或取代或未取代的杂环基。公式（I）的环酰胺衍生物具有强大且选择性的抑制猫hepsin K的作用，且口服时具有临床疗效。
• EPOXYCARBOXAMIDE COMPOUND, AZIDE COMPOUND, AND AMINO ALCOHOL COMPOUND, AND PROCESS FOR PREPARING a-KETO AMIDE COMPOUND USING THEM
  申请人：KOBAYASHI Nobuo

  公开号：US20120197015A1

  公开（公告）日：2012-08-02

  The present invention is directed to providing epoxycarboxamide compounds, azide compounds and amino alcohol compounds which serve as manufacturing intermediates that can lead to useful α-ketoamide compounds, and the present invention is also is directed to processes for preparing α-ketoamide compounds using the intermediates. The epoxycarboxamide compounds, azide compounds and amino alcohol compounds are represented by the following formulae: wherein R 1 , R 2 , R 3 , R 4 and R 5 , as well as subvariables for one or more of R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein.

  本发明旨在提供作为制造中间体的环氧羧酰胺化合物、叠氮化合物和氨基醇化合物，这些中间体可以导致有用的α-酮酰胺化合物，并且本发明还旨在提供使用这些中间体制备α-酮酰胺化合物的过程。环氧羧酰胺化合物、叠氮化合物和氨基醇化合物由以下式表示：其中R1、R2、R3、R4和R5以及R1、R2、R3、R4和R5中一个或多个的子变量如本文所定义。
• N-substituted mercaptopropanamide derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0318859A2

  公开（公告）日：1989-06-07

  Novel N-substituted mercaptopropanamide derivatives of the formula: wherein R₁ is mercapto or a group convertible into mercapto when cleaved within the biobody, W is hydrogen atom, an alkyl or an aralkyl, R₂ is an aryl which may optionally have substituent(s), a heterocyclic group which may optionally have substituent(s), or an alkyl which may optionally have substituent(s), X is a cycloalkylene, a cycloalkylidene, or a phenylene which may optionally have substituent(s) or may optionally be fused with other ring, and R₃ is carboxyl or a group convertible into carboxyl when cleaved within the biobody, or a pharmaceutically acceptable salt thereof, and a solid solution of said N-substituted mercaptopropanamide derivative with an amino acid, which have excellent enkephalinase inhibitory activity and are useful for the treatment of mild to moderate pain, and a pharmaceutical composition containing said compounds as an active ingredient, and processes for preparing these compounds.

  式中的新型 N-取代巯基丙酰胺衍生物： 其中 R₁ 是巯基或在生物体内裂解时可转化为巯基的基团，W 是氢原子、烷基或芳烷基，R₂ 是芳基（可选择具有取代基）、杂环基（可选择具有取代基）或烷基（可选择具有取代基），X 是环亚烷基、亚环烷基或亚苯基（可选择具有取代基）或可选择与其他环融合、和 R₃ 是羧基或在生物体内裂解时可转化为羧基的基团，或其药学上可接受的盐，以及所述 N-取代巯基丙酰胺衍生物与氨基酸的固溶体，它们具有优异的脑啡肽酶抑制活性，可用于治疗轻度至中度疼痛，以及含有所述化合物作为活性成分的药物组合物，以及制备这些化合物的工艺。
• Cyclic amide derivatives which inhibit cathepsin K
  申请人：Fujirebio Kabushiki Kaisha

  公开号：EP1008592A2

  公开（公告）日：2000-06-14

  A cyclic amide derivative of formula (I) : wherein R1 represents a substituted alkyl group, a substituted alkenyl group, a substituted amino group, a substituted alkoxyl group, a substituted alkylthio group, a substituted carbamoyl group, a substituted sulfonamide group or a substituted amide group; the ring A represents a saturated cyclic alkyl group with 5 to 7 carbon atoms or a hetero-atom-containing saturated heterocyclic group with 3 to 6 carbon atoms; R2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group; R3 represents a hydrogen atom, a group represented by the general formula R4O- or a group represented by the general formula R5(R6)N-wherein R4 represents hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group; R5 and R6 may be the same or different and each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group. The cyclic amide derivative of formula (I) have a strong and selective inhibitory action of a cathepsin K and a clinical efficacy when administered orally.

  式(I)的环酰胺衍生物： 其中 R1 代表取代的烷基、取代的烯基、取代的氨基、取代的烷氧基、取代的烷硫基、取代的氨基甲酰基、取代的磺酰胺基或取代的酰胺基；环 A 代表具有 5 至 7 个碳原子的饱和环状烷基或具有 3 至 6 个碳原子的含有杂原子的饱和杂环基团； R2 代表氢原子、取代或未取代的烷基、取代或未取代的芳香烃基团或取代或未取代的杂环基团；R3 代表氢原子、通式 R4O- 所代表的基团或通式 R5(R6)N- 所代表的基团，其中 R4 代表氢原子、取代或未取代的烷基、取代或未取代的芳烃基团或取代或未取代的杂环基团；R5 和 R6 可以相同或不同，各自代表氢原子、取代或未取代的烷基、取代或未取代的芳烃基团或取代或未取代的杂环基团。 式(I)的环酰胺衍生物对酪蛋白酶 K 具有很强的选择性抑制作用，口服具有临床疗效。