(S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)benzoyl)-hydrazinecarbonyl)oxazolidine-3-carboxylate | 1005407-69-1

• 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: (S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)benzoyl)-hydrazinecarbonyl)oxazolidine-3-carboxylate
• 英文别名: 1,1-dimethylethyl (4S)-2,2,4-trimethyl-4-[(2-{[4-(n-octyloxy)-3-(trifluoromethyl)phenyl]carbonyl}hydrazino)carbonyl]-1,3-oxazolidine-3-carboxylate；1,1-dimethylethyl (4S)-2,2,4-trimethyl-4-[(2-{[4-(octyloxy)-3-(trifluoromethyl)phenyl]carbonyl}hydrazino)carbonyl]-1,3-oxazolidine-3-carboxylate；tert-butyl (4S)-2,2,4-trimethyl-4-[[[4-octoxy-3-(trifluoromethyl)benzoyl]amino]carbamoyl]-1,3-oxazolidine-3-carboxylate
• CAS: 1005407-69-1
• 化学式: C₂₈H₄₂F₃N₃O₆
• 分子量: 573.653
• InChiKey: GURUCOJGYSLUEZ-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)benzoyl)-hydrazinecarbonyl)oxazolidine-3-carboxylate 在 劳森试剂 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 1.0h， 生成 1,1-dimethylethyl (4S)-2,2,4-trimethyl-4-{5-[4-(n-octyloxy)-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  [EN] THE HEMI-FUMARATE SALT OF A 1,3,4-THIADIAZOLYL DERIVATIVE AS MODULATOR OF THE SPHINGOSINE 1-PHOSPHATE RECEPTOR
  [FR] SEL HÉMI-FUMARATE D'UN DÉRIVÉ DE 1,3,4-THIADIAZOLYLE COMME MODULATEUR DU RÉCEPTEUR DE LA SPHINGOSINE 1-PHOSPHATE

  摘要：

  该发明涉及化合物（2S）-2-氨基-2-{5-[4-(辛氧基)-3-（三氟甲基）苯基]-1,3,4-噻二唑-2-基}-1-丙醇半富马酸盐，其制备方法，含有该化合物的药物组合物以及其在通过S1 P1受体介导的病症或紊乱的治疗中的用途。

  公开号：

  WO2009098193A1
• 作为产物：
  描述：

  4-氟-3-(三氟甲基)苯甲酸 在 sodium hexamethyldisilazane 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 异丙醇 为溶剂， 反应 28.5h， 生成 (S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)benzoyl)-hydrazinecarbonyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Development of a Fully Telescoped Synthesis of the S1P1 Agonist GSK1842799

  摘要：

  The development of a fully telescoped synthesis of the potent and selective S1P1 agonist GSK1842799 is described. Key features in the synthesis, which has been implemented on a multikilogram scale, include a nucleophilic aromatic substitution to install a lipophilic 1-octyloxy chain, introduction of a chiral quaternary centre, and the use of Lawesson's reagent to form a thiadiazole ring. Due to the lack of crystalline intermediates, workup protocols that took advantage of the lipophilic nature of the compounds were developed. This allowed full combination of the five chemistry stages and a salt formation, with the only isolation being that of the final hemifumarate salt of the drug substance. The synthesis of the O-phosphorylated active metabolite is also described.

  DOI：

  10.1021/op2000095

文献信息

• [EN] THE HEMI-FUMARATE SALT OF A 1,3,4-THIADIAZOLYL DERIVATIVE AS MODULATOR OF THE SPHINGOSINE 1-PHOSPHATE RECEPTOR<br/>[FR] SEL HÉMI-FUMARATE D'UN DÉRIVÉ DE 1,3,4-THIADIAZOLYLE COMME MODULATEUR DU RÉCEPTEUR DE LA SPHINGOSINE 1-PHOSPHATE
  申请人：GLAXO GROUP LTD

  公开号：WO2009098193A1

  公开（公告）日：2009-08-13

  The invention relates to the compound (2S)-2-amino-2-5-[4-(octyloxy)-3- (trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-1-propanol hemi-fumarate, processes for its preparation, pharmaceutical compositions containing them and its use in the treatment of conditions or disorders which are mediated via the S1 P1 receptor.

  该发明涉及化合物（2S）-2-氨基-2-5-[4-(辛氧基)-3-（三氟甲基）苯基]-1,3,4-噻二唑-2-基}-1-丙醇半富马酸盐，其制备方法，含有该化合物的药物组合物以及其在通过S1 P1受体介导的病症或紊乱的治疗中的用途。
• CHEMICAL COMPOUNDS
  申请人：Evindar Ghotas

  公开号：US20100009936A1

  公开（公告）日：2010-01-14

  The invention provides compounds formula I, their preparation, and their use as pharmaceutically active immuno-suppressive agents for the treatment of autoimmune disorders, organ transplant rejection, disorders associated with an activated immune system, as well as other disorders modulated by lymphopenia or SIP receptors.

  该发明提供了化合物I的公式，其制备方法，以及它们作为药物活性的免疫抑制剂用于治疗自身免疫性疾病，器官移植排斥，与激活的免疫系统相关的疾病，以及其他淋巴减少或SIP受体调节的疾病。
• Chemical compounds
  申请人：Evindar Ghotas

  公开号：US20080096938A1

  公开（公告）日：2008-04-24

  The invention provides compounds formula I, their preparation, and their use as pharmaceutically active immunosuppressive agents for the treatment of autoimmune disorders, organ transplant rejection, disorders associated with an activated immune system, as well as other disorders modulated by lymphopenia or S1P receptors.

  本发明提供了化合物I的公式、其制备方法以及其作为药物活性的免疫抑制剂，用于治疗自身免疫性疾病、器官移植排斥、与激活的免疫系统相关的疾病，以及其他受淋巴细胞减少或S1P受体调节的疾病。
• Sphingosine-1-phosphate (SIP) receptor agonists
  申请人：Praecis Pharmaceuticals

  公开号：US07759370B2

  公开（公告）日：2010-07-20

  The invention provides compounds formula I, their preparation, and their use as pharmaceutically active immunosuppressive agents for the treatment of autoimmune disorders, organ transplant rejection, disorders associated with an activated immune system, as well as other disorders modulated by lymphopenia or S1P receptors.

  本发明提供了化合物I的配方、其制备方法以及其作为药理活性免疫抑制剂的用途，用于治疗自身免疫性疾病、器官移植排斥、与激活免疫系统相关的疾病，以及其他由淋巴细胞减少或S1P受体调节的疾病。
• HEMI-FUMARATE SALT OF A 1,3,4-THIADIAZOLYL DERIVATIVE AS MODULATOR OF THE SPHINGOSINE 1-PHOSPHATE RECEPTOR
  申请人：Anson Michael Simon

  公开号：US20110034524A1

  公开（公告）日：2011-02-10

  The invention relates to the compound (2S)-2-amino-2-5-[4-(octyloxy)-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-1-propanol hemi-fumarate, processes for its preparation, pharmaceutical compositions containing them and its use in the treatment of conditions or disorders which are mediated via the S1P1 receptor.

  本发明涉及化合物(2S)-2-氨基-2-5-[4-(辛氧基)-3-(三氟甲基)苯基]-1,3,4-噻二唑-2-基}-1-丙醇半富马酸盐、其制备方法、含有该化合物的药物组合物以及其在治疗通过S1P1受体介导的疾病或疾病中的应用。