(+/-)-3-methyl-5-<4-(1-methylcyclohexylmethoxy)benzyl>-2,4-thiazolidinedione | 96207-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-3-methyl-5-<4-(1-methylcyclohexylmethoxy)benzyl>-2,4-thiazolidinedione
• 英文别名: 3-Methyl-5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 96207-27-1
• 化学式: C₁₉H₂₅NO₃S
• 分子量: 347.478
• InChiKey: PTWGBBSDCWAWPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 酪里达唑 以 乙醚 为溶剂， 反应 0.5h， 以86.5%的产率得到(+/-)-3-methyl-5-<4-(1-methylcyclohexylmethoxy)benzyl>-2,4-thiazolidinedione
  参考文献：
  名称：

  Studies on antidiabetic agents. VI. Asymmetric transformation of (.+-.)-5-(4-(1-methylcyclohexylmethoxy)benzyl)-2,4-thiazolidinedione(ciglitazone) with optically active 1-phenylethylamines.

  摘要：

  在乙酸乙酯中对一种新型抗糖尿病药物(±)-5-[4-(1-甲基环己基甲氧基)苄基]-2, 4-噻唑烷二酮（1, ciglitazone）与(-)-和(+)-1-苯乙胺（PEA）进行光学解析，结果几乎完全不对称转化，分别得到了(-)-1-(-)-PEA和(+)-1-(+)-PEA这两种盐，产量可达定量。通过核磁共振测定了从这些盐中得到的(-)-和(+)-1的光学纯度，并通过化学方法确认了它们的绝对构型。这两种光学异构体显示出基本相同的抗糖尿病和降血脂活性。

  DOI：

  10.1248/cpb.32.4460

文献信息

• [EN] MULTI- API LOADING PRODRUGS<br/>[FR] PROMÉDICAMENTS CHARGÉS DE MULTIPLES PRINCIPES ACTIFS
  申请人：ALKERMES INC

  公开号：WO2012088441A1

  公开（公告）日：2012-06-28

  The present invention accomplishes this by having multiple molecules of parent drugs attached to carrier moieties and by extending the period during which the parent drug is released and absorbed after administration to the patient and providing a longer duration of action per dose than the parent drug itself. Prodrug conjugates are suitable for sustained delivery of heteroaryl, lactam- amide-, imide-, sulfonamide-, carbamate-, urea-, benzamide-, acylaniline-, cyclic amide- and tertiary amine-containing parent drugs that are substituted at the amide nitrogen or oxygen atom with labile aldehyde-linked prodrug moieties. The carrier groups of the prodrugs can be hydrophobic to reduce the polarity and solubility of the parent drug under physiological conditions.

  本发明通过将多个母药分子附着在载体基团上，并延长母药在患者服用后释放和吸收的时间，从而实现此目的，并提供每剂次比母药本身更长的作用时间。前药偶联物适用于异杂环、内酰胺、酰胺、磺酰胺、氨基甲酸酯、脲、苯甲酰胺、酰基苯胺、环状酰胺和三级胺含有母药，该母药在酰胺氮或氧原子处以不稳定的醛类前药基团取代。前药的载体基团可以是疏水性的，在生理条件下降低母药的极性和溶解度。
• SOHDA, TAKASHI;MIZUNO, KATSUTOSHI;KAWAMATSU, YUTAKA, CHEM. AND PHARM. BULL., 1984, 32, N 11, 4460-4465
  作者：SOHDA, TAKASHI、MIZUNO, KATSUTOSHI、KAWAMATSU, YUTAKA

  DOI：——

  日期：——
• Multi-API Loading Prodrugs
  申请人：Alkermes Pharma Ireland Limited

  公开号：US20160024011A1

  公开（公告）日：2016-01-28

  The present invention accomplishes this by having multiple molecules of parent drugs attached to carrier moieties and by extending the period during which the parent drug is released and absorbed after administration to the patient and providing a longer duration of action per dose than the parent drug itself. Prodrug conjugates are suitable for sustained delivery of heteroaryl, lactam-amide-, imide-, sulfonamide-, carbamate-, urea-, benzamide-, acylaniline-, cyclic amide- and tertiary amine-containing parent drugs that are substituted at the amide nitrogen or oxygen atom with labile aldehyde-linked prodrug moieties. The carrier groups of the prodrugs can be hydrophobic to reduce the polarity and solubility of the parent drug under physiological conditions.
• MULTI-API LOADING PRODRUGS
  申请人：Alkermes Pharma Ireland Limited

  公开号：US20180194732A1

  公开（公告）日：2018-07-12

  The present invention accomplishes this by having multiple molecules of parent drugs attached to carrier moieties and by extending the period during which the parent drug is released and absorbed after administration to the patient and providing a longer duration of action per dose than the parent drug itself. Prodrug conjugates are suitable for sustained delivery of heteroaryl, lactam- amide-, imide-, sulfonamide-, carbamate-, urea-, benzamide-, acylaniline-, cyclic amide- and tertiary amine-containing parent drugs that are substituted at the amide nitrogen or oxygen atom with labile aldehyde-linked prodrug moieties. The carrier groups of the prodrugs can be hydrophobic to reduce the polarity and solubility of the parent drug under physiological conditions.
• Studies on antidiabetic agents. VI. Asymmetric transformation of (.+-.)-5-(4-(1-methylcyclohexylmethoxy)benzyl)-2,4-thiazolidinedione(ciglitazone) with optically active 1-phenylethylamines.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.32.4460

  日期：——

  Optical resolution of a new antidiabetic agent, (±)-5-[4-(1-methylcyclohexylmethoxy) benzyl]-2, 4-thiazolidinedione (1, ciglitazone) with (-)-and (+)-1-phenylethylamine (PEA) in ethyl acetate resulted in almost complete asymmetric transformation to give the salts, (-)-1·(-)-PEA and (+)-1·(+)-PEA, respectively, in up to quantitative yields. Optical purities of (-)-and (+)-1 obtained from the salts were determined by nuclear magnetic resonance and their absolute configurations were confirmed chemically. The optical isomers showed essentially the same antidiabetic and hypolipidemic activities.

  在乙酸乙酯中对一种新型抗糖尿病药物(±)-5-[4-(1-甲基环己基甲氧基)苄基]-2, 4-噻唑烷二酮（1, ciglitazone）与(-)-和(+)-1-苯乙胺（PEA）进行光学解析，结果几乎完全不对称转化，分别得到了(-)-1-(-)-PEA和(+)-1-(+)-PEA这两种盐，产量可达定量。通过核磁共振测定了从这些盐中得到的(-)-和(+)-1的光学纯度，并通过化学方法确认了它们的绝对构型。这两种光学异构体显示出基本相同的抗糖尿病和降血脂活性。