3-(hexyloxy)-4-(1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole | 131986-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(hexyloxy)-4-(1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole
• 英文别名: 1,2,5,6-Tetrahydro-3-(3-hexyloxy-1,2,5-thiadiazol-4-yl)pyridine；N-Desmethylxanomeline；3-hexoxy-4-(1,2,3,6-tetrahydropyridin-5-yl)-1,2,5-thiadiazole
• CAS: 131986-96-4
• 化学式: C₁₃H₂₁N₃OS
• 分子量: 267.395
• InChiKey: CSFYOLMLLRWDAE-UHFFFAOYSA-N

物化性质

• 沸点：
  398.3±42.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(hexyloxy)-4-(1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole 以 甲醇 、 乙腈 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  [EN] XANOMELINE DERIVATIVES AND METHODS FOR TREATING NEUROLOGICAL DISORDERS
  [FR] DÉRIVÉS DE XANOMÉLINE ET MÉTHODES DE TRAITEMENT DE TROUBLES NEUROLOGIQUES

  摘要：

  本文提供的是含有式(I)化合物和/或其盐的化合物；其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13中至少有一个为氟，其余独立地选择氢和氟；而R14、R15、R16、R17、R18、R19、R20、R21、R22和R23独立地选择氢和氘；但是当R1、R2和R3为氟时，那么R4、R5、R6、R7、R8、R9、R10、R11、R12和R13中至少有一个为氟或R14、R15、R16、R17、R18、R19、R20、R21、R22和R23中至少有一个为氘。此外，本文还提供了包含这些化合物的药物和使用这些化合物和药物治疗中枢神经系统疾病的方法。

  公开号：

  WO2021097427A1

文献信息

• Method for treating anxiety using a tetrahydropyridine or azabicyclic oxadiazole or thiadiazole compound
  申请人：ELI LILLY AND COMPANY

  公开号：EP0709095A2

  公开（公告）日：1996-05-01

  The present invention provides a method for treating anxiety in humans using heterocyclic compounds as listed in Claim 1.

  本发明提供了一种使用权利要求 1 所列杂环化合物治疗人类焦虑症的方法。
• Method for treating anxiety using a tetrahydropyridine oxadiazole or thiadiazole compound
  申请人：ELI LILLY AND COMPANY

  公开号：EP0709094A2

  公开（公告）日：1996-05-01

  The present invention provides the use of a compound wherein Z1 is oxygen or sulphur; R is hydrogen, halogen, amino, -NHCO-R, C₃₋₇-cycloalkyl, C₄₋₁₀-(cycloalkylalkyl), -Z-C₃₋₇-cycloalkyl optionally substituted with C₁₋₆-alkyl, -Z-C₄₋₁₀-(cycloalkylalkyl), -Z-C₄₋₁₀-(cycloalkenylalkyl), -Z-C₄₋₁₀-(methylenecycloalkyl-alkyl), -NH-R2, -NR2R3, -NH-OR2, phenyl, phenoxy, benzoyl, benzyloxycarbonyl, tetrahydronaphtyl, indenyl, X, R, -ZR, -SOR, -SO₂R, -Z-R-Z³-R³, -Z-R-Z³-R³-Z⁴-R⁴, -Z-RCO-R³, -Z-R-CO₂-R³, Z-R-O₂C-R³, -Z-R-CONH-R³, -Z-R-NHCOR³, -Z-R-X, -Z-R-Z³-X, wherein Z, Z³, and Z⁴ independently are oxygen or sulphur, and R, R³ and R⁴ independently are straight or branched C₁₋₁₅-alkyl, straight or branched C₂₋₁₅-alkenyl, straight or branched C₂₋₁₅-alkynyl, each of which is optionally substituted with halogen(s), -OH, -CN, -CF₃, -SH, -COOH, -NH-R, -NRR³, C₁₋₆alkyl ester, one or two phenyl, phenoxy, benzoyl or benzyloxycarbonyl wherein each aromatic group is optionally substituted with one or two halogen, -CN, C₁₋₄-alkyl or C₁₋₄-alkoxy, and X is a 5 or 6 membered heterocyclic group containing one to four N, O or S atom(s) or a combination thereof, which heterocyclic group is optionally substituted at carbon or nitrogen atom(s) with straight or branched C₁₋₆-alkyl, phenyl, benzyl or pyridine, or a carbon atom in the heterocyclic group together with an oxygen atom form a carbonyl group, or which heterocyclic group is optionally fused with a phenyl group; and R⁵ and R⁶ may be present at any position, including the point of attachment of the thiadiazole or oxadiazole ring, and independently are hydrogen, straight or branched C₁₋₅-alkyl, straight or branched C₂₋₅-alkenyl, straight or branched C₂₋₅-alkynyl, straight or branched C₁₋₁₀-alkoxy, straight or branched C₁₋₅-alkyl substituted with -OH, -OH, halogen, -NH₂ or carboxy; R¹ is hydrogen, straight or branched C₁₋₅-alkyl, straight or branched C₂₋₅-alkenyl or straight or branched C₂₋₅-alkynyl; or a pharmaceutically acceptable salt or solvate thereof; for the manufacture of a medicament for the treatment of anxiety.

  本发明提供了一种化合物的用途 其中 Z1 是氧或硫； R是氢、卤素、氨基、-NHCO-R、C₃₋₇-环烷基、C₄₋₁₀-(环烷基烷基)、-Z-C₃₋₇-环烷基任选被C₁₋₆-烷基取代、-Z-C₄₋₁₀-(环烷基烷基)、-Z-C₄₋₁₀-(环烯基)、-Z-C₄₋₁₀-(亚甲基环烷基)、-NH-R2、-NR2R3、-NH-OR2、苯基、苯氧基、苯甲酰基、苄氧羰基、四氢萘基、茚基、X、R、-ZR、-SOR、-SO₂R、-Z-R-Z³-R³、-Z-R-Z³-R³-Z⁴-R⁴、-Z-RCO-R³、-Z-R-CO₂-R³、Z-R-O₂C-R³、-Z-R-CONH-R³、-Z-R-NHCOR³、-Z-R-X、-Z-R-Z³-X，其中 Z、Z³、和 Z⁴ 独立地为氧或硫，而 R、R³ 和 R⁴ 独立地为直链或支链 C₁₋₁₅-烷基、直链或支链 C₂₋₁₅- 烷基、直链或支链 C₂₋₁₅- 烷炔基、其中每个都可选地被卤素、-OH、-CN、-CF₃、-SH、-COOH、-NH-R、-NRR³、C₁₋₆烷基酯、一个或两个苯基、苯氧基、苯甲酰基或苄氧基取代、苯甲酰基或苄氧羰基，其中每个芳香基团可任选被一个或两个卤素、-CN、C₁₋₄-烷基或 C₁₋₄-烷氧基取代，且 X 是含有 1 至 4 个 N、O 或 S 原子的 5 或 6 位杂环基团、O 或 S 原子或其组合，该杂环基团的碳原子或氮原子可选择被直链或支链 C₁₋₆-烷基、苯基、苄基或吡啶取代，或该杂环基团中的碳原子与氧原子一起形成羰基，或该杂环基团可选择与苯基融合；和 R⁵ 和 R⁶ 可出现在任何位置，包括噻二唑或噁二唑环的连接点，且各自为氢、直链或支链 C₁₋₅-烷基、直链或支链 C₂₋₅- 烷基、直链或支链 C₂₋₅- 烷炔基、直链或支链 C₁₋₁₀-烷氧基、被 -OH、-OH、卤素、-NH₂ 或羧基取代的直链或支链 C₁₋₅ 烷基；R¹ 是氢、直链或支链 C₁₋₅-烷基、直链或支链 C₂₋₅-烯基或直链或支链 C₂₋₅-炔基；或 其药学上可接受的盐或溶液；用于制造治疗焦虑症的药物。
• Xanomeline derivatives and methods for treating neurological disorders
  申请人：Karuna Therapeutics, Inc.

  公开号：US11534434B2

  公开（公告）日：2022-12-27

  Provided herein are compounds comprising compounds of formula I and/or salts thereof; wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 is fluorine, and the remainder are independently chosen from hydrogen and fluorine; and R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 are independently chosen from hydrogen and deuterium; with the proviso that when R 1 , R 2 , and R 3 are fluorine, then at least one of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 is fluorine or at least one of R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 is deuterium. Also provided are medicaments comprising these compounds and methods for treating central nervous system disorders with the compounds and medicaments described herein.

  本文提供的化合物包括式 I 化合物 和/或其盐； 其中 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 和 R 13 是氟，其余独立地选自氢和氟；以及 R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 和 R 23 独立地选自氢和氘；但当 R 1 , R 2 和 R 3 为氟，则 R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 和 R 13 是氟或 R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 和 R 23 为氘。此外，还提供了包含这些化合物的药物，以及用本文所述化合物和药物治疗中枢神经系统疾病的方法。
• Tetrahydropyridine oxadiazole or thiadiazole compound for treating anxiety
  申请人：ELI LILLY AND COMPANY

  公开号：EP0709094B1

  公开（公告）日：2000-04-05
• Use of piperidine compounds in the treatment of schizophrenia
  申请人：NOVO NORDISK A/S

  公开号：EP0734259B1

  公开（公告）日：2002-06-12