2-(isoindolin-2-ylmethyl)-5-((1-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one | 2231294-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(isoindolin-2-ylmethyl)-5-((1-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one
• 英文别名: Opevesostat；2-(1,3-dihydroisoindol-2-ylmethyl)-5-[(1-methylsulfonylpiperidin-4-yl)methoxy]pyran-4-one
• CAS: 2231294-96-3
• 化学式: C₂₁H₂₆N₂O₅S
• 分子量: 418.514
• InChiKey: LHVKCOBGLZGRQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(isoindolin-2-ylmethyl)-5-((1-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one 在 盐酸 作用下， 以 乙醚 、 异丙醇 为溶剂， 以87 %的产率得到2-(isoindolin-2-ylmethyl)-5-((1-(methylsulfonyl)piperidin-4-yl)-methoxy)-4H-pyran-4-one hydrochloric acid salt
  参考文献：
  名称：

  WO2022/184978

  摘要：

  公开号：
• 作为产物：
  描述：

  曲酸 在 氯化亚砜 、 三(3,6-二氧杂庚基)胺 、 caesium carbonate 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 7.0h， 生成 2-(isoindolin-2-ylmethyl)-5-((1-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF A CYP11A1 INHIBITOR AND INTERMEDIATES THEREOF
  [FR] PROCÉDÉ DE PRÉPARATION D'UN INHIBITEUR DE CYP11A1 ET DE SES INTERMÉDIAIRES

  摘要：

  The present invention relates to an improved process for the preparation of 4H-pyranone structured CYP11A1 inhibitors such as 2-(isoindolin-2-ylmethyl)-5- (( 1 -(methylsulfonyl)piperidin-4-y l)methoxy)-4H-pyran-4-one (1A) and key intermediates thereof such as 2-(chloromethyl)-5-hydroxy-4H-pyran-4-one (II), 5- hydroxy-2-(isoindolin-2-ylmcthyl)-4H-pyran-4-onc (III), (1- (methylsulfonyl)piperidin-4-yl)methyl methane sulfonate (V') and (l-(methyl- sulfonyl)piperidin-4-yl)methyl 4-methylbenzene sulfonate (V"). CYP11A1 inhibitors are useful in the treatment of hormonally regulated cancers, such as prostate cancer and breast cancer.

  公开号：

  WO2022184975A1

文献信息

• [EN] PYRAN DERVATIVES AS CYP11A1 (CYTOCHROME P450 MONOOXYGENASE 11A1) INHIBITORS<br/>[FR] DÉRIVÉS DE PYRANE EN TANT QU'INHIBITEURS DE CYP11A1 (CYTOCHROME P450 MONOOXYGÉNASE 11A1)
  申请人：ORION CORP

  公开号：WO2018115591A1

  公开（公告）日：2018-06-28

  Compounds of formula (I) wherein R1, R2,R3,R4,R5,R23,R24,L, A and Bare as defined in claim 1, or pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as cytochrome P450 monooxygenase 11A1(CYP11A1) inhibitors. The compounds are useful as medicaments in the treatment of steroidreceptor, particularly androgen receptor,dependent diseases and conditions, such asprostate cancer.

  公式(I)的化合物，其中R1、R2、R3、R4、R5、R23、R24、L、A和B如权利要求1中定义，或其药用可接受的盐被披露。公式(I)的化合物具有作为细胞色素P450单加氧酶11A1（CYP11A1）抑制剂的使用价值。这些化合物作为药物用于治疗激素受体，尤其是雄激素受体相关的疾病和状况，如前列腺癌。
• Pyran dervatives as CYP11A1 (cytochrome P450 monooxygenase 11A1) inhibitors
  申请人：Orion Corporation

  公开号：US10717726B2

  公开（公告）日：2020-07-21

  Compounds of formula (I) wherein R1, R2, R3, R4, R5, R23, R24, L, A and B are as defined in claim 1, or pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as cytochrome P450 monooxygenase 11A1 (CYP11A1) inhibitors. The compounds are useful as medicaments in the treatment of steroid receptor, particularly androgen receptor, dependent diseases and conditions, such as prostate cancer.

  式(I)化合物 其中 R1、R2、R3、R4、R5、R23、R24、L、A 和 B 如权利要求 1 所定义，或公开了其药学上可接受的盐。式（I）化合物具有细胞色素 P450 单氧化酶 11A1 (CYP11A1) 抑制剂的作用。这些化合物可用作治疗类固醇受体，特别是雄激素受体依赖性疾病和病症，如前列腺癌的药物。
• PYRAN DERVATIVES AS CYP11A1 (CYTOCHROME P450 MONOOXYGENASE 11A1) INHIBITORS
  申请人：Orion Corporation

  公开号：EP3558981A1

  公开（公告）日：2019-10-30
• PYRAN DERIVATIVES AS CYP11A1 (CYTOCHROME P450 MONOOXYGENASE 11A1) INHIBITORS
  申请人：Orion Corporation

  公开号：EP3558981B1

  公开（公告）日：2021-05-26
• [EN] SOLID FORMS OF A 4H-PYRAN-4-ONE STRUCTURED CYP11A1 INHIBITOR<br/>[FR] FORMES SOLIDES D'UN INHIBITEUR DE CYP11A1 À STRUCTURE 4H-PYRAN-4-ONE
  申请人：[en]ORION CORPORATION

  公开号：WO2022184977A1

  公开（公告）日：2022-09-09

  The present invention relates to novel solid forms, particularly crystalline forms, of 2-(isoindolin-2-ylmethyl)-5-((1-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one (I). Compound (I) is a selective inhibitor of CYP11A1 enzyme and is useful in the treatment of hormonally regulated cancers, such as prostate cancer and breast cancer.