[3,5-difluoro-4-(methylthio)phenyl]methanol | 473299-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3,5-difluoro-4-(methylthio)phenyl]methanol
• 英文别名: [3,5-difluoro-4-(methylthio)-phenyl]methanol；(3,5-Difluoro-4-(methylthio)phenyl)methanol；(3,5-difluoro-4-methylsulfanylphenyl)methanol
• CAS: 473299-50-2
• 化学式: C₈H₈F₂OS
• 分子量: 190.214
• InChiKey: USFPKNZPHDRFEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3,5-difluoro-4-(methylthio)phenyl]methanol 在 盐酸 、 四溴化碳 、 sodium hydride 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 mineral oil 为溶剂， 反应 49.08h， 生成 4-((1R,2R)-2-(((3,5-difluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl)piperidine hydrochloride
  参考文献：
  名称：

  Design of Potent and Orally Active GPR119 Agonists for the Treatment of Type II Diabetes

  摘要：

  We report herein the design and synthesis of a series of potent and selective GPR119 agonists. Our objective was to develop a GPR119 agonist with properties that were suitable for fixed-dose combination with a DPP4 inhibitor. Starting from a phenoxy analogue (1), medicinal chemistry efforts directed toward reducing half-life and increasing solubility led to the synthesis of a series of benzyloxy analogues. Compound 28 was chosen for further profiling because of its favorable physicochemical properties and excellent GPR119 potency across species. This compound exhibited a clean off-target profile in counterscreens and good in vivo efficacy in mouse oGTT.

  DOI：

  10.1021/acsmedchemlett.5b00207
• 作为产物：
  描述：

  3,4,5-三氟苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.28h， 生成 [3,5-difluoro-4-(methylthio)phenyl]methanol
  参考文献：
  名称：

  [EN] SUBSTITUTED CYCLOPROPYL COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS, AND METHODS OF TREATMENT
  [FR] COMPOSÉS CYCLOPROPYLÉS SUBSTITUÉS, COMPOSITIONS CONTENANT DE TELS COMPOSÉS ET PROCÉDÉS DE TRAITEMENT

  摘要：

  公开了具有以下化学式I的环丙基化合物及其药学上可接受的盐，用于治疗或预防2型糖尿病和类似疾病。这些化合物可用作G蛋白偶联受体GPR-119的激动剂。还包括药物组合物和治疗方法。

  公开号：

  WO2012173917A1

文献信息

• [EN] SUBSTITUTED CYCLOPROPYL COMPOUNDS<br/>[FR] COMPOSÉS DE CYCLOPROPYLE SUBSTITUÉS
  申请人：MERCK SHARP & DOHME

  公开号：WO2014052379A1

  公开（公告）日：2014-04-03

  Substituted cyclopropyl piperidinyl compounds and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing type 2 diabetes and similar conditions. The compounds are useful as agonists of the G-protein coupled receptor GPR-1 19. Pharmaceutical compositions and methods of treatment are also included.

  本文披露了取代环丙基哌啶基化合物及其药用盐，用于治疗或预防2型糖尿病和类似疾病。这些化合物可作为G蛋白偶联受体GPR-119的激动剂。同时还包括药物组合物和治疗方法。
• Fluoro-substituted benzenesulfonyl compounds for the treatment of inflammation
  申请人：Pharmacia Corporation

  公开号：US20030032657A1

  公开（公告）日：2003-02-13

  Methods of treating cyclooxygenase-2 mediated disorders comprising administering to a subject a therapeutically effective amount of one or more fluoro-substituted benzenesulfonyl compounds corresponding to Formula I: 1 wherein A, X, n, R 1 , R 2 , and R 3 are as described in the specification, and novel fluoro-substituted benzenesulfonyl compounds within Formula I.

  治疗环氧合酶-2介导的疾病的方法包括向受试者施用与化学式I:1相对应的一种或多种氟代苯磺酰化合物的治疗有效剂量，其中化学式I中的A、X、n、R1、R2和R3如规范中所述，并且包括化学式I中的新型氟代苯磺酰化合物。
• Substituted cyclopropyl compounds, compositions containing such compounds, and methods of treatment
  申请人：Miller Michael

  公开号：US09006228B2

  公开（公告）日：2015-04-14

  Substituted cyclopropyl compounds of the formula I: and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing type 2 diabetes and similar conditions. The compounds are useful as agonists of the G-protein coupled receptor GPR-119. Pharmaceutical compositions and methods of treatment are also included.

  本发明公开了式I的取代环丙基化合物及其药学上可接受的盐，其可用于治疗或预防2型糖尿病和类似疾病。该化合物可用作G蛋白偶联受体GPR-119的激动剂。本发明还包括药物组合物和治疗方法。
• SUBSTITUTED CYCLOPROPYL COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS, AND METHODS OF TREATMENT
  申请人：Miller Michael

  公开号：US20140128368A1

  公开（公告）日：2014-05-08

  Substituted cyclopropyl compounds of the formula I: and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing type 2 diabetes and similar conditions. The compounds are useful as agonists of the G-protein coupled receptor GPR-119. Pharmaceutical compositions and methods of treatment are also included.

  公开了式I的替代环丙基化合物及其药学上可接受的盐，用于治疗或预防2型糖尿病和类似疾病。这些化合物可用作G蛋白偶联受体GPR-119的激动剂。还包括制药组合物和治疗方法。
• SUBSTITUTED CYCLOPROPYL COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT
  申请人：ACTON John J.

  公开号：US20150274664A1

  公开（公告）日：2015-10-01

  Substituted cyclopropyl piperidinyl compounds and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing type 2 diabetes and similar conditions. The compounds are useful as agonists of the G-protein coupled receptor GPR-119. Pharmaceutical compositions and methods of treatment are also included.

  本发明公开了可用于治疗或预防2型糖尿病和类似疾病的替代环丙基哌啶化合物及其药学上可接受的盐。该化合物可用作G蛋白偶联受体GPR-119的激动剂。本发明还涉及制药组合物和治疗方法。