AF 102A | 107220-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: AF 102A
• 英文别名: (-)-trans-2-methylspiro(1,3-oxathiolan-5,3')quinuclidine；Cevimeline cis-sulfoxide；(2S,5R)-2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane]
• CAS: 107220-27-9
• 化学式: C₁₀H₁₇NOS
• 分子量: 199.317
• InChiKey: WUTYZMFRCNBCHQ-WCBMZHEXSA-N

物化性质

• 沸点：
  308.5±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  3

文献信息

• Process for the preparation and purification of cis-2-methylspiro(1,3-oxathiolane-5,3')quiniclidine hydrochloride
  申请人：Bratovanov Svetoslav S.

  公开号：US20090182146A1

  公开（公告）日：2009-07-16

  An industrially acceptable process for the preparation and purification of cis-2-methylspiro(1,3-oxathiolane-5,3′)quiniclidine from a cisitrans mixture of isomers. Treatment of the mixture with an organic sulfonice acid generates a less soluble acid addition salt that is enriched in the cis-isomer. Recrystallization or pulping using various organic solvents allows for enrichment of the cis-isomer by filtration. These new sulfonic acid salts of the cis-isomer of 2-methylspiro(1,3-oxathiolane-5,3′)quiniclidine prepared according to the present invention could be further converted into the hydrochloride salt by any known procedures such as treatment with a base and then hydrochloric acid salt formation or exchange of the sulfonic acid salt with hydrochloric acid.

  一种工业上可接受的过程，用于从顺式/反式异构体的混合物中制备和纯化cis-2-甲基螺(1,3-噻吩环-5,3′)喹诺啉。用有机磺酸处理混合物会产生一种溶解性较低的酸加合盐，其中富集了顺式异构体。通过结晶再结晶或使用各种有机溶剂进行过滤，可以实现对顺式异构体的富集。根据本发明制备的cis-异构体2-甲基螺(1,3-噻吩环-5,3′)喹诺啉的这些新磺酸盐可以通过任何已知的程序进一步转化为盐酸盐，例如用碱处理然后形成盐酸盐，或者用盐酸交换磺酸盐。
• [EN] PROCESS FOR PRODUCING ENANTIOMERICALLY ENRICHED ISOMER OF 3-(1-AMINOETHYL) PHENYL DERIVATIVE AND EMPLOYING THE SAME TO PRODUCE RIVASTIGMINE OR ITS PHARMACEUTICALLY ACCEPTABLE SALT<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN ISOMÈRE ÉNANTIOMÉRIQUEMENT ENRICHI D'UN DÉRIVÉ DU 3-(1-AMINOÉTHYLE) PHÉNYLE ET SON UTILISATION POUR PRODUIRE DE LA RIVASTIGMINE OU SON SEL PHARMACEUTIQUEMENT ACCEPTABLE
  申请人：JUBILANT LIFE SCIENCES LTD

  公开号：WO2011151669A1

  公开（公告）日：2011-12-08

  The present invention relates to an economic and efficient process for producing enatiomerically enriched 3-(1-aminoethyl)phenyl derivative and employing the same to produce Rivastigmine or its pharmaceutically acceptable salt.

  本发明涉及一种经济高效的生产富含对映体的3-(1-氨基乙基)苯基衍生物的过程，并利用该衍生物生产利伐替林或其药用可接受盐。
• PROCESS FOR THE PREPARATION OF CIS-2-METHYLSPIRO (1, 3-OXATHIOLANE 5-3') QUINUCLIDINE
  申请人：Kovi Ravishanker

  公开号：US20110301352A1

  公开（公告）日：2011-12-08

  Methods are provided for making pharmaceutical-grade cis-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine and pharmaceutically acceptable salts thereof by isomerizing racemic 2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine to cis-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine and subsequent purification of the C-MSOQ by salt formation with inexpensive and commercially available material such as sulfuric acid. Purification methods are disclosed which employ an organic solvent/water system and recrystallization with an organic solvent such as acetone.

  提供了一种制备医药级顺式-2-甲基螺(1,3-噁唑烷-5,3')喹啉及其药学上可接受的盐的方法，包括将外消旋的2-甲基螺(1,3-噁唑烷-5,3')喹啉异构化为顺式-2-甲基螺(1,3-噁唑烷-5,3')喹啉，并通过与廉价和商业化的材料（如硫酸）形成盐来纯化C-MSOQ。还揭示了采用有机溶剂/水系统和有机溶剂（如丙酮）再结晶的纯化方法。
• CIS-2-METHYLSPIRO 1, 3-OXATHIOLANE 5-3 QUINUCLIDINE
  申请人：APICORE, LLC

  公开号：US20130237707A1

  公开（公告）日：2013-09-12

  Pharmaceutical-grade compounds containing cis-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine having a purity >99.0% by HPLC with less than 0.5% of trans-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine are provided.

  提供含有cis-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine的药品级化合物，其纯度通过HPLC大于99.0％，且trans-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine含量不到0.5％。
• Optical isomers of a spiroquinuclidine derivative
  申请人：State of Israel Represented by the Prime Minister's Office The Israel Institute for Biological Research

  公开号：EP0303391A2

  公开（公告）日：1989-02-15

  The (+)-cis-, (-)-cis-, (+)-trans- and (-)-trans- forms of 2-methylspiro(1,3-oxathiolan-5,3′)quinuclidine are prepared by optical resolution of each of the (±)-cis- and (±)-trans-isomers. These compounds find application in treating diseases of the central nervous system in mammals, especially diseases due to a deficiency in the central cholinergic system. Biological tests indicate that the (-)-cis-form, as well as the (±)-cis-isomer, shows particular promise for treating senile dementia of Alzheimer's type.

  (+)-顺式、(-)-顺式、(+)-反式和(-)-反式形式的 2-甲基螺(1,3-氧硫杂环戊烷-5,3′)奎宁环是通过光学分解(±)-顺式和(±)-反式异构体制备的。这些化合物可用于治疗哺乳动物的中枢神经系统疾病，特别是由于中枢胆碱能系统缺乏引起的疾病。生物测试表明，(-)-顺式异构体和(±)-顺式异构体尤其有望治疗阿尔茨海默型老年痴呆症。