capecitabine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: capecitabine
• 英文别名: capetabine；pentyl N-[5-fluoranyl-1-[(3R,4S,5R)-5-methyl-3,4-bis(oxidanyl)oxolan-2-yl]-2-oxidanylidene-pyrimidin-4-yl]carbamate；pentyl N-[1-[(3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
• 化学式: C₁₅H₂₂FN₃O₆
• 分子量: 359.355
• InChiKey: GAGWJHPBXLXJQN-LXGADPQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 以 吡啶 为溶剂， 以81.9%的产率得到capecitabine
  参考文献：
  名称：

  一种卡培他滨中间体

  摘要：

  本发明属于医药合成领域，公开了一种卡培他滨中间体(Ⅴ)，还公开了其制备方法，该制备方法为：用Fmoc‑保护的2，3位羟基的5‑脱氧‑D‑核糖的衍生物(Ⅲ)和活化的5‑氟胞嘧啶(Ⅳ)在催化剂的作用下，偶联得到卡培他滨中间体(Ⅴ)。该方法操作简便，后处理简单，产品纯度高，适合工业化生产。

  公开号：

  CN111377988B

文献信息

• NOVEL SYNTHESIS OF 5-DEOXY-5'-FLUOROCYTIDINE COMPOUNDS
  申请人：PharmaEssentia Corp.

  公开号：US20130184451A1

  公开（公告）日：2013-07-18

  This invention relates to a process of synthesizing a β-nucleoside compound of formula (I): wherein R 1 is alkyl, aryl, cycloalkyl, heteroaryl, or heterocycloalkyl. The process includes reacting a compound of formula (II): with a compound of formula (III): wherein R 1 is as defined above and X is chloride, bromide, iodide, methanesulfonate, triflate, p-toluenesulfonate, trifluoroacetate, 4-nitrophenoxy, or N-succinimidyloxy, in a solvent and in the presence of a base.

  这项发明涉及一种合成β-核苷类化合物的方法，其化学结构如下所示：其中R1为烷基、芳基、环烷基、杂芳基或杂环烷基。该方法包括将化合物(II)：与化合物(III)：反应，其中R1如上所定义，X为氯化物、溴化物、碘化物、甲磺酸甲酯、三氟甲磺酸盐、对甲苯磺酸盐、三氟乙酸盐、4-硝基苯氧基或N-琥珀酰亚乙氧基，反应溶剂和碱的存在下进行。
• Process for Producing Fluorocytidine Derivatives
  申请人：Hu Tsung-Cheng

  公开号：US20110021769A1

  公开（公告）日：2011-01-27

  A process for making a capecitabine or its derivative comprising (a) reacting a compound of the formula (II): wherein each of R 1 and R 2 independently represents a hydroxyl protecting group, with an acylating agent of formula (III): X—C(═O)—R 3 , wherein X is an acyl activating group in an organic solvent to produce an acylated compound; (b) deprotecting the acylated compound to obtain the compound of formula (I); and (c) purifying the compound of formula (I) with a solvent.

  一种制备卡培他滨或其衍生物的方法，包括(a)将化合物（II）的反应式：其中R1和R2分别表示羟基保护基，与化合物（III）的酰化试剂反应：X—C(═O)—R3，其中X是有机溶剂中的酰基活化基团，以产生酰化化合物；(b)去保护酰化化合物以获得式（I）的化合物；(c)用溶剂对式（I）的化合物进行纯化。
• [EN] PROCESS FOR PRODUCING FLUROCYTIDINE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS DE LA FLUOROCYTIDINE
  申请人：SCINOPHARM TAIWAN LTD

  公开号：WO2011010967A1

  公开（公告）日：2011-01-27

  A process for making a capecitabine or its derivative comprising (a) reacting a compound of the formula (II): wherein each of R1 and R2 independently represents a hydroxyl protecting group, with an acylating agent of formula (III): X-C(=O)-R3, wherein X is an acyl activating group in an organic solvent to produce an acylated compound; (b) deprotecting the acylated compound to obtain the compound of formula (I); and (c) purifying the compound of formula (I) with a solvent.

  一种制备卡培他滨或其衍生物的方法，包括(a)将式（II）的化合物与式（III）的酰化试剂反应：其中R1和R2各自独立地表示羟基保护基，X是有机溶剂中的酰基活化基团，以产生酰化化合物; (b)去保护酰化化合物以获得式（I）的化合物; 以及（c）用溶剂纯化式（I）的化合物。
• PROCESS FOR PRODUCTION OF RIBOFURANOSE DERIVATIVES
  申请人：Maeda Tomoko

  公开号：US20100298550A1

  公开（公告）日：2010-11-25

  It is an object of the present invention to provide a process for producing 1,2,3-tri-O-acetyl-5-deoxy-ribofuranose in an industrially appropriate manner. The present invention provides a process for producing a 1,2,3-tri-O-acetyl-5-deoxy-ribofuranose which comprises hydrogenating a compound represented by the formula (1) or formula (2) in the presence of a metal catalyst: wherein P 1 and P 2 independently represent a hydrogen atom or an acyl group, OP 1 and OP 2 may together form an acetal group, and R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, or an acyl group; wherein X 1 represents Br or I, P 3 and P 4 independently represent a hydrogen atom or an acyl group, and R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, or an acyl group.

  本发明的目的是以适合工业生产的方式提供生产1,2,3-三-O-乙酰-5-去氧核糖的方法。本发明提供了一种生产1,2,3-三-O-乙酰-5-去氧核糖的方法，该方法包括在金属催化剂存在下，对式（1）或式（2）所表示的化合物进行氢化：其中P1和P2分别表示氢原子或酰基，OP1和OP2可以结合形成缩醛基团，R表示氢原子、烷基、芳基、芳烷基或酰基；其中X1表示Br或I，P3和P4分别表示氢原子或酰基，R表示氢原子、烷基、芳基、芳烷基或酰基。
• METHODS OF TREATING METASTATIC BREAST CANCER WITH TRASTUZUMAB-MCC-DM1
  申请人：Agresta Samuel

  公开号：US20110165155A1

  公开（公告）日：2011-07-07

  Methods of treating patients having metastatic or unresectable locally advanced HER2 positive cancer, e.g., breast cancer, with the antibody-drug conjugate trastuzumab-MCC-DM1 are provided, wherein the patients have received extensive prior treatment, e.g., with an anthracycline, a taxane, capecitabine, lapatinib, and trastuzumab.