2-氨基-2-[2-[2-氯-4-[[3-(苄氧基)苯基]硫]苯基]乙基]-1,3-丙二醇盐酸盐 | 509088-69-1

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-氨基-2-[2-[2-氯-4-[[3-(苄氧基)苯基]硫]苯基]乙基]-1,3-丙二醇盐酸盐
• 中文别名: N-芴甲氧羰基-L-3,3-二苯基丙氨酸
• 英文名称: KRP203
• 英文别名: 2-amino-2-[2-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)ethyl]propane-1,3-diol hydrochloride；2-Amino-2-(4-((3-(benzyloxy)phenyl)thio)-2-chlorophenethyl)propane-1,3-diol hydrochloride；2-amino-2-[2-[2-chloro-4-(3-phenylmethoxyphenyl)sulfanylphenyl]ethyl]propane-1,3-diol;hydrochloride
• CAS: 509088-69-1
• 化学式: C₂₄H₂₆ClNO₃S*ClH
• 分子量: 480.455
• InChiKey: MYIFLDFUXIHOCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 ºC (DEC.)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Carbamic acid, N-[3-[2-chloro-4-[[3-(phenylmethoxy)phenyl]thio]phenyl]-1,1-bis(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester 生成 2-氨基-2-[2-[2-氯-4-[[3-(苄氧基)苯基]硫]苯基]乙基]-1,3-丙二醇盐酸盐
  参考文献：
  名称：

  Diaryl sulfide derivative, addition salt thereof, and immunosuppressant

  摘要：

  本发明提供了一种二芳基硫化物衍生物，其具有显著的免疫抑制作用，副作用较少。本发明的二芳基衍生物由以下通式（1）表示：其中一种例子是2-氨基-2-[4-(3-苄氧基苯基硫基)-2-氯苯基]丙基-1,3-丙二醇。

  公开号：

  US06960692B2

文献信息

• [EN] A NOVEL PROCESS FOR THE PREPARATION OF 3-(BENZYLOXY)- BENZENETHIOL, A KEY INTERMEDIATE FOR THE PREPARATION OF PHARMACEUTICAL DRUGS.<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE 3-(BENZYLOXY)-BENZÈNETHIOL, UN INTERMÉDIAIRE CLÉ POUR LA PRÉPARATION DE MÉDICAMENTS PHARMACEUTIQUES
  申请人：ARCH PHARMALABS LTD

  公开号：WO2012073249A1

  公开（公告）日：2012-06-07

  Disclosed herein is an efficient and economical process for the preparation of 3-Benzyloxybenzenethiol of formula-I which is a key intermediate for the preparation of pharmaceutical drugs. R' is hydrogen, halogen, trihalomethyl, lower alkoxy having 1-4 carbon atoms, lower alkyl having 1-7 carbon atoms, substituted or unsubstituted arylalkyl or substituted or arylloxy and the like. R" is hydrogen, halogen, trihalomethyl, lower alkoxy having 1-4 carbon atoms, lower alkyl having 1-7 carbon atoms, substituted or unsubstituted arylalkyl or substituted or arylloxy and the like.

  本文揭示了一种高效且经济的过程，用于制备公式I中的3-苄氧基苯硫醇，该化合物是制备药物的关键中间体。R'代表氢、卤素、三卤甲基、含有1-4个碳原子的低烷氧基、含有1-7个碳原子的低烷基、取代或未取代的芳基烷基或取代或芳基氧基等。R"代表氢、卤素、三卤甲基、含有1-4个碳原子的低烷氧基、含有1-7个碳原子的低烷基、取代或未取代的芳基烷基或取代或芳基氧基等。
• Process for Producing 2-Amino-2-[2-[4-(3-Benzyloxyphenylthio)-2-Chlorophenyl]Ethyl]-1,3-Propanediol Hydrochloride and Hydrates Thereof, and Intermediates in the Production Thereof
  申请人：Tsubuki Takeshi

  公开号：US20080207941A1

  公开（公告）日：2008-08-28

  A process for the industrial production of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride (Compound I), an effective immunosuppressant. The process for producing 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride or a hydrate thereof includes the steps of reacting 4-(3-benzyloxyphenylthio)-2-chlorobenzaldehyde with ethyl diethylphosphonoacetate in a solvent in the presence of a base to form ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate; reducing the resulting ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate, followed by mesylation, iodination and nitration, to form 1-benzyloxy-3-[3-chloro-4-(3-nitropropyl)phenylthio]benzene; forming 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol using a formaldehyde solution; and reducing the resulting 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol to form the desired product.

  一种用于工业生产2-氨基-2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-1,3-丙二醇盐酸盐（化合物I）的免疫抑制剂的方法。生产2-氨基-2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-1,3-丙二醇盐酸盐或其水合物的方法包括以下步骤：在溶剂中，在碱的存在下，将4-(3-苄氧基苯基硫基)-2-氯苯甲醛与乙基二乙基磷酸酯反应，形成乙基3-[4-(3-苄氧基苯基硫基)-2-氯苯基]丙烯酸酯；还原所得的乙基3-[4-(3-苄氧基苯基硫基)-2-氯苯基]丙烯酸酯，随后进行甲磺化、碘化和硝化，形成1-苄氧基-3-[3-氯-4-(3-硝基丙基)苯基硫基]苯；使用甲醛溶液形成2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-2-硝基-1,3-丙二醇；并还原所得的2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-2-硝基-1,3-丙二醇以形成所需的产物。
• 2-Aminobutanol Compound and Use Thereof for Medical Purposes
  申请人：Kiuchi Masatoshi

  公开号：US20090082311A1

  公开（公告）日：2009-03-26

  The present invention provides a novel compound having few side effects such as bradycardia and the like and having superior peripheral blood lymphocyte-decreasing effect. The present invention provides a 2-aminobutanol compound represented by the following formula (I) wherein R 1 is a hydrogen atom or P(═O) (OH) 2 , R 2 is an alkyl having 1 to 4 carbon atoms optionally substituted by hydroxyl group(s) or optionally substituted by halogen atom(s), R 3 is a hydrogen atom; a halogen atom; cyano; an alkyl having 1 to 4 carbon atoms optionally substituted by halogen atom(s); or an acyl having 2 to 5 carbon atoms optionally substituted by halogen atom(s), X is an oxygen atom, a sulfur atom, carbonyl or NR 4 wherein R 4 is a hydrogen atom or an alkyl having 1 to 4 carbon atoms, Ar 1 is an optionally substituted arylene or an optionally substituted heteroarylene, and Ar 2 is an optionally substituted aryl or an optionally substituted heteroaryl, provided that when X is an oxygen atom, Ar 1 is phenylene and Ar 2 is phenyl, then the phenyl for Ar 2 should be substituted, or a pharmaceutically acceptable acid addition salt thereof, or a hydrate thereof, or a solvate thereof, as well as a production method of the above-mentioned 2-aminobutanol compound.

  本发明提供了一种新型化合物，具有较少的副作用，如心动过缓等，并具有优越的外周血淋巴细胞降低作用。本发明提供了一种由以下式（I）表示的2-氨基丁醇化合物，其中R1是氢原子或P（═O）（OH）2，R2是1至4个碳原子的烷基，可选地被羟基或卤原子取代，R3是氢原子，卤原子，氰基，1至4个碳原子的烷基，可选地被卤原子取代，或2至5个碳原子的酰基，可选地被卤原子取代，X是氧原子，硫原子，羰基或NR4，其中R4是氢原子或1至4个碳原子的烷基，Ar1是可选取代的芳烃基或可选取代的杂芳烃基，Ar2是可选取代的芳基或可选取代的杂芳基，但当X为氧原子时，Ar1为苯基，Ar2为苯基，则Ar2的苯基应被取代，或其药学上可接受的酸加盐或其水合物或溶剂化物，以及上述2-氨基丁醇化合物的制备方法。
• METHOD FOR CRYSTALLIZATION OF 2-AMINO-2-[2-[4-(3-BENZYLOXYPHENYLTHIO)-2-CHLOROPHENYL]-ETHYL]-1,3-PROPANEDIOL HYDROCHLORIDE
  申请人：Komatsu Hidetaka

  公开号：US20110021636A1

  公开（公告）日：2011-01-27

  A method for highly efficiently preparing high purity crystals of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chloro-phenyl]-ethyl]-1,3-propanediol hydrochloride. The method involves dissolving 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol in a mixed solvent comprising a solvent in which its hydrochloride is highly soluble and a solvent in which its hydrochloride is less soluble, to prepare a solution of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol; and then adding hydrochloric acid to the resulting solution with stirring, to crystallize the hydrochloride of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chloro-phenyl]ethyl]-1,3-propanediol.

  一种高效制备高纯度2-氨基-2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-1,3-丙二醇盐酸盐晶体的方法。该方法涉及将2-氨基-2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-1,3-丙二醇溶解在混合溶剂中，所述混合溶剂包括一个高度溶解其盐酸盐的溶剂和一个其盐酸盐较不溶的溶剂，以制备2-氨基-2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-1,3-丙二醇的溶液；然后加入盐酸至所得溶液中并搅拌，以结晶2-氨基-2-[2-[4-(3-苄氧基苯基硫基)-2-氯苯基]乙基]-1,3-丙二醇的盐酸盐。
• METHOD OF EFFECTIVELY USING MEDICINE AND METHOD CONCERNING PREVENTION OF SIDE EFFECT
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP1772145A1

  公开（公告）日：2007-04-11

  To provide a medicament which efficiently expresses an immunosuppressive agent or an anti-inflammatory agent and reduces expression of side effect. A medicament includes diaryl sulfide or diaryl ether compound having a 2-amino-1,3-propanediol structure having an activity of reducing lymphocytes circulating peripherally, in combination with an immunosuppressive agent and/or an anti-inflammatory agent.

  提供一种能有效表达免疫抑制剂或抗炎剂并减少副作用的药物。 一种药物包括具有 2-氨基-1,3-丙二醇结构的二芳基硫醚或二芳基醚化合物，该化合物与免疫抑制剂和/或抗炎剂结合使用，具有减少外周循环淋巴细胞的活性。