4-(tert-butylsulfonylamino)cyclohexane-1-carboxylic acid | 342578-12-5

• 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: 4-(tert-butylsulfonylamino)cyclohexane-1-carboxylic acid
• CAS: 342578-12-5
• 化学式: C₁₁H₂₁NO₄S
• 分子量: 263.358
• InChiKey: YGQHGJMTFCIGEP-KYZUINATSA-N

物化性质

• 沸点：
  418.9±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 溶解度：
  二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.47
• 氢给体数：
  2.0
• 氢受体数：
  3.0

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-(tert-butylsulfonylamino)cyclohexane-1-carboxylic acid 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 4-(tert-butylsulfonylamino)-N-[5-(trifluoromethyl)pyridin-2-yl]cyclohexane-1-carboxamide
  参考文献：
  名称：

  Development of an Optimized Synthetic and Purification Process of S-2367 (Velneperit), a Novel Neuropeptide Y (NPY) Y5 Receptor Antagonist

  摘要：

  We developed a simple synthetic route to S-2367 (Velneperit) (1) using trans-1-ethoxycarbonyl-4-aminocyclohexane hydrochloride salt (12) as a starting material. The key step was Na2WO4/H2O2 oxidation, and we found that it was accelerated in weakly basic conditions. The finding was useful to control one of the critical impurities: 14 in 10. The new process was more efficient than the early process from the viewpoint of the number of reactions, yield, throughput, and EHS (environment, health, and safety) but a quality deviation occurred in the pilot manufacturing: 10 content in 1 was over the upper limit. The cause was presumed to be hydrolysis of 1 during the recrystallization step. After finding it, we developed two reliable purification processes. The first was slurry washing including clever polymorphic control using only acetone and water. The second was salt formation of 10 and rational building of the recrystallization procedure based on solubility to improve removal rate.

  DOI：

  10.1021/acs.oprd.5b00023
• 作为产物：
  描述：

  4-氨基环己羧酸 在 氯化亚砜 、 hexaammonium heptamolybdate tetrahydrate 、 水 、 双氧水 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-(tert-butylsulfonylamino)cyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Development of an Optimized Synthetic and Purification Process of S-2367 (Velneperit), a Novel Neuropeptide Y (NPY) Y5 Receptor Antagonist

  摘要：

  We developed a simple synthetic route to S-2367 (Velneperit) (1) using trans-1-ethoxycarbonyl-4-aminocyclohexane hydrochloride salt (12) as a starting material. The key step was Na2WO4/H2O2 oxidation, and we found that it was accelerated in weakly basic conditions. The finding was useful to control one of the critical impurities: 14 in 10. The new process was more efficient than the early process from the viewpoint of the number of reactions, yield, throughput, and EHS (environment, health, and safety) but a quality deviation occurred in the pilot manufacturing: 10 content in 1 was over the upper limit. The cause was presumed to be hydrolysis of 1 during the recrystallization step. After finding it, we developed two reliable purification processes. The first was slurry washing including clever polymorphic control using only acetone and water. The second was salt formation of 10 and rational building of the recrystallization procedure based on solubility to improve removal rate.

  DOI：

  10.1021/acs.oprd.5b00023

文献信息

• [EN] PROCESS FOR THE PREPARATION OF TRANS-4-AMINO-1-CYCLOHEXANECARBOXILIC ACID AND ITS DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE L'ACIDE TRANS-4-AMINO-1-CYCLOHEXANE CARBOXYLIQUE ET SES DÉRIVÉS
  申请人：SIEGFRIED AG

  公开号：WO2017134212A1

  公开（公告）日：2017-08-10

  The present invention relates to a one-pot process for the preparation of trans-4-amino-l-cyclohexanecarboxylic acid derivatives where the trans ratio is more than 75% by reaction of a 4-aminobenzoic acid derivative using an appropriate catayst and an appropriate solvent or solvent mixture under basic conditions. The process uses low hydrogen pressure and is therefore suitable for industrial application.

  本发明涉及一种一锅法制备trans-4-氨基-1-环己基甲酸衍生物的方法，其中通过在适当的催化剂和适当的溶剂或溶剂混合物的基础条件下，通过对4-氨基苯甲酸衍生物进行反应，使trans比例高于75%。该方法使用低氢压力，因此适用于工业应用。
• AMINE-DERIVATIVES HAVING NPY Y5 RECEPTOR ANTAGONISTIC ACTIVITY AND THE USES THEREOF
  申请人：OKUNO Takayuki

  公开号：US20100273841A1

  公开（公告）日：2010-10-28

  This invention provides an anorectic or anti-obesity composition comprising a compound of the formula (I): formula (I): a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is optionally substituted lower alkyl, Y is —S(O)n- wherein n is 1 or 2, or —CO—, R 2 is hydrogen or lower alkyl, R 7 is hydrogen or lower alkyl, X is lower alkylene, lower alkenylene, arylene, cycloalkylene or the like, and Z is lower alkyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl or the like.

  本发明提供了一种厌食剂或抗肥胖组合物，包括公式(I)的化合物： 公式(I)： 其药用可接受的盐或溶剂化物， 其中 R1是可选地取代的低级烷基， Y是—S(O)n—，其中n是1或2，或者—CO—， R2是氢或低级烷基， R7是氢或低级烷基， X是低级亚烷基，低级亚烯基，芳基，环烷基或类似物， Z是低级烷基，可选地取代的碳环烷基，可选地取代的杂环烷基或类似物。
• COMPOUNDS HAVING NPY Y5 RECEPTOR ANTAGONISTIC ACTIVITY
  申请人：Sakagami Masahiro

  公开号：US20110028468A1

  公开（公告）日：2011-02-03

  This invention provides a compound of the formula (I): a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is substituted or unsubstituted alkyl or the like, R 2 is hydrogen or substituted or unsubstituted alkyl, Ring A is monocyclic or bicyclic aromatic heterocycle, R 3 is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted heterocycle, R 4 is halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl or the like, m is an integer between 0 and 2, n is an integer between 0 and 5, R is halogen, oxo, cyano, nitro, substituted or unsubstituted alkyl or the like, and p is an integer between 0 and 2 as novel compounds having NPY Y5 antagonistic activity.

  这项发明提供了式(I)的化合物： 其药学上可接受的盐或溶剂化合物， 其中 R1为取代或未取代的烷基或类似物， R2为氢或取代或未取代的烷基， 环A为单环或双环芳香杂环， R3为取代或未取代的芳基，取代或未取代的杂芳基或取代或未取代的杂环， R4为卤素，氰基，取代或未取代的烷基，取代或未取代的环烷基或类似物， m为0到2之间的整数， n为0到5之间的整数， R为卤素，氧代，氰基，硝基，取代或未取代的烷基或类似物，以及 p为0到2之间的整数 作为具有NPY Y5拮抗活性的新化合物。
• METHOD FOR PRODUCING SALT OF 4-SULFINYLAMINO-1-CYCLOHEXANECARBOXYLIC ACID
  申请人：Omura Sohei

  公开号：US20100076081A1

  公开（公告）日：2010-03-25

  Disclosed is a salt of trans-4-sulfinylamino-1-cyclohexanecarboxylic acid. Also disclosed is a method for producing a salt of trans-4-sulfinylamino-1-cyclohexanecarboxylic acid.

  本发明公开了一种trans-4-亚磺酰基氨基-1-环己烷羧酸的盐。本发明还公开了一种制备trans-4-亚磺酰基氨基-1-环己烷羧酸盐的方法。
• PROCESS FOR PRODUCTION OF COMPOUND HAVING ANTAGONISTIC ACTIVITY ON NPYY5 RECEPTOR, AND USEFUL CRYSTAL
  申请人：Sugata Yoshihide

  公开号：US20110060145A1

  公开（公告）日：2011-03-10

  Disclosed are process for producing a compound having NPYY5 receptor antagonism and useful crystals. A process for producing a compound represented by the formula (IV): wherein R 1 is substituted or unsubstituted alkyl, R 2 is substituted or unsubstituted alkyl, and n is 1 or 2, or the like, which comprises reacting a compound represented by the formula (II): wherein R 1 and n are as defined above, and X is a leaving group, or the like and a compound represented by formula (III): wherein R 2 is as defined above, or the like.

  本发明涉及一种具有NPYY5受体拮抗作用且有用的晶体的化合物制备过程。一种制备由公式(IV)表示的化合物的方法：其中R1是取代或未取代的烷基，R2是取代或未取代的烷基，n为1或2，或类似物，包括将由公式(II)表示的化合物：其中R1和n如上所定义，X是离去基团，或类似物，和由公式(III)表示的化合物反应：其中R2如上所定义，或类似物。