tetra-O-acetyl-1-amino-3,5-bis-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodobenzene | 76801-94-0

• 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: tetra-O-acetyl-1-amino-3,5-bis-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodobenzene
• 英文别名: 5-amino-N,N-bis<2,3-bis(acetyloxy)propyl>-2,4,6-triiodo-1,3-benzenedicarboxamide；5-amino-2,4,6-triiodo-N,N'-bis-(2,3-diacetoxypropyl)isophthalamide；N,N'-bis(2,3-diacetoxypropyl)-5-amino-2,4,6-triiodoisophthalamide；5-amino-N,N'-bis[2,3-bis(acetyloxy)propyl]2,4,6-triiodo-1,3-benzenedicarboxamide；N,N'-bis[2,3-bis (acetyloxy)propyl]-5-amino-2,4, 6-triiodo-1,3-benzenedicarboxamide；5-Amino-2,4,6-triiodoisophthalic acid mono-(2,3-diacetoxy-propyl) amide；5-amino-1,3-N,N'-bis-(2,3-diacetoxypropyl)-2,4,6-triiodoisophtalamide；5-amino-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamide；3,5-Bis(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline；acetic acid 1-acetoxymethyl-2-[3-amino-5-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-benzoylamino]-ethyl ester；acetic acid 2-acetoxy-3-[3-amino-5-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-benzoylamino]-propyl ester；5-amino-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide；5-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide Tetraacetate；[2-acetyloxy-3-[[3-amino-5-(2,3-diacetyloxypropylcarbamoyl)-2,4,6-triiodobenzoyl]amino]propyl] acetate
• CAS: 76801-94-0
• 化学式: C₂₂H₂₆I₃N₃O₁₀
• 分子量: 873.176
• InChiKey: SHUOZUDQONPJGS-UHFFFAOYSA-N

物化性质

• 沸点：
  713.4±60.0 °C(Predicted)
• 密度：
  1.934±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  189
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tetra-O-acetyl-1-amino-3,5-bis-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodobenzene 以 N,N'-dimethylacetamide (DMA) 、 乙酸乙酯 为溶剂， 生成 N,N'-Bis[2,3-bis(acetyloxy)-1-propyl]-5-[(2,6-dibromo-1-oxo-hexyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide
  参考文献：
  名称：

  Nonionic radiographic contrast agents

  摘要：

  新的非离子X线造影剂具有以下结构式：##STR1## 其中Y是单键，--CH.sub.2 CH.sub.2 --，--CH.sub.2 O--，--OCH.sub.2 --，##STR2## --CH.sub.2 --，--CH.sub.2 --CH.sub.2 --CH.sub.2 --，--O--或##STR3## R.sub.1，R.sub.1'和R.sub.2相同或不同，可以是氢，烷基或羟基烷基。羟基烷基指的是具有1个或更多羟基的烷基基团。首选的羟基烷基基团包括：##STR4## R.sub.3和R.sub.4相同或不同，可以是氢，甲基或--CH.sub.2 CH.sub.2 OH；R.sub.5是氢，烷基，--CH.sub.2 CH.sub.2 OH，CH.sub.2 OH或OH，R.sub.6是烷基，--CH.sub.2 CH.sub.2 OH，CH.sub.2 OH，OH或氢，可能与R.sub.5不同，m为零或一，但条件是杂环环的亚甲基或亚甲烷碳原子不同时连接到氮和氧原子，另外条件是当Y是单键时，m不为零。这些新的造影剂可溶于水，具有理想的低渗透压和抗凝血性能。

  公开号：

  US05614638A1
• 作为产物：
  描述：

  5-氨基间苯二甲酸 在 吡啶 、 氯化亚砜 、 potassium dichloroiodate 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 40.0h， 生成 tetra-O-acetyl-1-amino-3,5-bis-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodobenzene
  参考文献：
  名称：

  Heterocyclic Nonionic X-ray Contrast Agents. III. The Synthesis of 5-[4-(Hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide Derivatives

  摘要：

  The syntheses of 2,4,6-triiodo-1,3-benzenedicarboxamide analogs, 12c, 12e, and 17c, of interest as X-ray diagnostic agents and in which the 5 position is linked to the N atom of a 4-(hydroxymethyl)-oxazolidin-2-one moiety, are described. The heterocycle was built from suitably protected 5-amino-2, 4,6-triiodo-1,3-benzenedicarboxylic acid derivatives by a three-step procedure consisting of (1) phosgene treatment to obtain the corresponding isocyanates, (2) phenylmercuric chloride-catalyzed addition of glycidol (10) resulting in glycidyl carbamates, and (3) pyridine-catalyzed intramolecular N-alkylation, followed by deprotection, to obtain the oxazolidin-2-ones. The intramolecular N-alkylation reaction was highly regioselective and was not appreciably accompanied by O-alkylation products under the experimental conditions employed. The two carboxamide nitrogen atoms in the intermediates and end products carry either 2,3-dihydroxypropyl or 1,3-dihydroxypropyl residues. These highly congested benzenoid compounds exhibited interesting NMR spectral features due to atropisomerism arising from hindrance to free rotation about the three single bonds that link the aromatic moiety to the N-containing functionalities.

  DOI：

  10.1021/jo00085a023

文献信息

• 신규 중간체 화합물 및 이를 이용한 이오메프롤의 제조방법
  申请人：UK Chemipharm Co. ,Ltd (주)유케이케미팜(119990486345) Corp. No ▼ 110111-0826234BRN ▼213-81-60675

  公开号：KR20170123748A

  公开（公告）日：2017-11-09

  본 발명은 이오메프롤의 신규 중간체 화합물 및 이의 제조방법과 이를 이용한 이오메프롤의 제조방법에 관한 것이다. 더욱 구체적으로는 X-선 혈관 조영제로서 사용되는 이오메프롤을 보다 경제적이고 고순도로 제조하기 위하여, 신규 중간체 N,N'-비스(2,3-디아세틸레이트프로필)-5-(2-아세톡시-N-메틸아세토아마이도)-2,4,6-트리아이오도이소프탈아마이드를 이용한 제조 방법에 관한 것이며 그 정제 방법을 포함한다.

  本发明涉及奥美拉唑的新中间体化合物及其制备方法以及利用该中间体化合物制备奥美拉唑的制备方法。具体而言，涉及利用新中间体N，N'-双(2,3-二乙酰基丙基)-5-(2-乙酰氧基-N-甲基乙酰胺基)-2,4,6-三碘异丁酰胺的制备方法，用于更经济、高纯度地制备奥美拉唑作为X射线血管造影剂，并包括其纯化方法。
• Contrast media
  申请人：Amersham Health AS

  公开号：US06448442B1

  公开（公告）日：2002-09-10

  The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents of formula I wherein n is 0 or 1, and where n is 1 each C6R5 moiety may be the same or different; X denotes a bond or a group providing a 1 to 7 atom chain linking two C6R5 moieties or, where n is 0, X denotes a group R; each group R is a hydrogen atom, an iodine atom or a hydrophilic moiety M or M1, two or three non-adjacent R groups in each C6R5 moiety being iodine and at least one R group in each C6R5 moiety being an M or M1 moiety; each M which may be the same or different, is a non-ionic hydrophilic moiety; and each M1 independently represents a —CHOHCON(R1)2 group wherein each R1, which may be the same or different, is a hydrogen atom, an OH group or a C1-6 alkoxy or optionally hydroxylated C1-5 alkyl group; at least one R group in the molecule being an M1 moiety; and isomers thereof.

  该发明提供了低粘度碘化芳基化合物，作为公式I的X射线造影剂，其中n为0或1，当n为1时，每个C6R5基团可以相同也可以不同；X表示连接两个C6R5基团的1至7个原子链的键或基团，或者当n为0时，X表示基团R；每个基团R是氢原子、碘原子或亲水基团M或M1，每个C6R5基团中的两个或三个非相邻的R基团为碘，且每个C6R5基团中至少一个R基团为M或M1基团；每个M可以相同也可以不同，是非离子性亲水基团；每个M1独立地表示一个—CHOHCON(R1)2基团，其中每个R1可以相同也可以不同，是氢原子、羟基或C1-6烷氧基或选择性羟基化的C1-5烷基基团；分子中至少一个R基团为M1基团；以及其异构体。
• Heterocyclic nonionic X-ray contrast agents V: A facile conversion of 2-tetrahydrofuroamides into α-hydroxy-δ-valerolactams and a general synthesis of lactams conjugated to 2,4,6-triiodoisophthalamides
  作者：E.R. Marinelli、T. Arunachalam、G. Diamantidis、J. Emswiler、H. Fan、R. Neubeck、K.M.R. Pillai、T.R. Wagler、C.-K. Chen、K. Natalie、N. Soundararajan、R.S. Ranganathan

  DOI：10.1016/0040-4020(96)00668-0

  日期：1996.8

  The synthesis of 2,4,6-triiodoisophthalamides substituted by a lactam moiety is described. A tandem ring opening-ring closure methodology consisting of a regiospecific ether cleavage of the tetrahydrofuroanilide 14b, followed by lactamization to α-oxygenated anilides 15b or 16b, gave α-O-functionalized-δ-valerolactams 12b or 13b, respectively. This approach is also compatible with the presence of ester

  描述了被内酰胺​​部分取代的2,4,6-三碘间苯二甲酰胺的合成。串联开环开环方法由四氢呋喃苯胺14b的区域特异性醚裂解，然后内酰胺化为α-氧化的酸酐15b或16b组成，分别得到α-O-官能化的δ-戊内酰胺12b或13b。该方法也与三碘苯基部分上酯和羰基氯官能团的存在兼容。还实现了内酰胺34–39的一般合成。进一步的化学修饰导致了水溶性的未取代内酰胺（34d，35d，37d）和α-羟基内酰胺[ 42（d，e），13（d，e）作为X射线造影剂而感兴趣的是图43和43 ]。
• Dicarboxylic acid-bis(3,5-dicarbamoyl-2,4,6-triiodoanilides) and x-ray
  申请人：Schering Aktiengesellschaft

  公开号：US05073362A1

  公开（公告）日：1991-12-17

  Dicarboxylic acid bis-(3,5-dicarbomoyl-2,4,6-triiodoanilides) of general formula I ##STR1## wherein the amide radicals --CONR.sup.1 R.sup.2 and --CONR.sup.3 R.sup.4 are different from one another and R.sup.1 is a hydrogen, a lower alkyl radical or R.sup.2, R.sup.2 is a straight-chain or branched-chain monohydroxy or polyhydroxy alkyl radical, R.sup.3 is hydrogen, a lower alkyl radical or R.sup.4, R.sup.4 is a straight-chain or branched-chain monohydroxy or polyhydroxy alkyl radical, R.sup.5 is hydrogen, a lower alkyl radical or a monohydroxy or polyhydroxy alkyl radical, X is a straight-chain or branched-chain alkylene with 1 to 6 carbon atoms, which optionally can be substituted by 1 to 6 hydroxy or alkoxy groups or interrupted by one or more oxygen atoms, possess good pharmacological and physicochemical properties rendering them outstandingly suitable as radiopaque substances in X-ray contrast media for use in all fields of application for X-ray contrast media.

  一般式I的二(3,5-二羧酰胺基-2,4,6-三碘苯酰胺基)二羧酸，其中酰胺基团--CONR.sup.1 R.sup.2和--CONR.sup.3 R.sup.4彼此不同，R.sup.1是氢、较低的烷基基团或R.sup.2，R.sup.2是直链或支链的单羟基或多羟基烷基基团，R.sup.3是氢、较低的烷基基团或R.sup.4，R.sup.4是直链或支链的单羟基或多羟基烷基基团，R.sup.5是氢、较低的烷基基团或单羟基或多羟基烷基基团，X是具有1至6个碳原子的直链或支链烷基，可以选择地被1至6个羟基或烷氧基取代，或者被一个或多个氧原子打断，具有良好的药理学和物理化学性质，使其非常适合作为X射线造影介质中的放射性物质，在X射线造影介质的所有应用领域中使用。
• Process for preparation of 2-oxo-1 piperidinyl derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05359077A1

  公开（公告）日：1994-10-25

  The process involves ring opening and ring closure of compounds containing a tetrahydrofuroyl group ##STR1## to provide facile synthesis of compounds containing a piperidin-2-one group of the formula ##STR2##

  该过程涉及含有四氢呋喃基团的化合物的环开合反应，以提供含有式的吡哆啉-2-酮基团的化合物的简便合成。