N-[3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide | 208642-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-[3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide
• 英文别名: [3-[3-(1,3-dioxoisoindol-2-yl)oxypropoxy]-5-methylphenyl] 2-methoxybenzenesulfonate
• CAS: 208642-78-8
• 化学式: C₂₅H₂₃NO₈S
• 分子量: 497.526
• InChiKey: DBGIIXANQRWRDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide 在 甲胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Oxyguanidines: application to non-peptidic phenyl-based thrombin inhibitors

  摘要：

  Although thrombin has been extensively researched with many examples of potent and selective inhibitors, the key characteristics of oral bioavailability and long half-life have been elusive. We report here a novel series non-peptidic phenyl-based, highly potent, highly selective and orally bioavailable thrombin inhibitors using oxyguanidines as guanidine-mimetics. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00125-2
• 作为产物：
  描述：

  3-(2-methoxyphenylsulfonyloxy)-5-methylphenol 在 硫氯酚 、 焦磷酸硫胺素 、 1,1'-azodicarbonyl-dipiperidine 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 N-[3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide
  参考文献：
  名称：

  Oxyguanidines: application to non-peptidic phenyl-based thrombin inhibitors

  摘要：

  Although thrombin has been extensively researched with many examples of potent and selective inhibitors, the key characteristics of oral bioavailability and long half-life have been elusive. We report here a novel series non-peptidic phenyl-based, highly potent, highly selective and orally bioavailable thrombin inhibitors using oxyguanidines as guanidine-mimetics. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00125-2

文献信息

• Aminoguanidines and alkoxyguanidines as protease inhibitors
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US06235778B1

  公开（公告）日：2001-05-22

  Aminoguanidine and alkoxyguanidine compounds, including compounds of the formula: wherein X is O or NR9 and R114 R4, R6-R9, R11, R12, Ra, Rb, Rc, Y, Z, n and mare set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit proteolytic enzymes such as thrombin are described. Also described are methods for preparing the compounds of Formula I. The novel compounds of the present invention are potent inhibitors of proteases, especially trypsin-like serine proteases, such as chymotrypsin, trypsin, thrombin, plasmin and factor Xa. Certain of the compounds exhibit antithrombotic activity via direct, selective inhibition of thrombin, or are intermediates useful for forming compounds having antithrombotic activity. The invention includes a composition for inhibiting loss of blood platelets, inhibiting formation of blood platelet aggregates, inhibiting formation of fibrin, inhibiting thrombus formation, and inhibiting embolus formation in a mammal, comprising a compound of the invention in a pharmaceutically acceptable carrier. Other uses of compounds of the invention are as anticoagulants either embedded in or physically linked to materials used in the manufacture of devices used in blood collection, blood circulation, and blood storage, such as catheters, blood dialysis machines, blood collection syringes and tubes, blood lines and stents.

  氨基胍和烷氧基胍化合物，包括以下式的化合物： 其中X为O或NR9，R1、R4、R6-R9、R11、R12、Ra、Rb、Rc、Y、Z、n和m如规范中所述，以及其水合物、溶剂合物或药用可接受的盐，能够抑制蛋白酶酶，如凝血酶。还描述了制备上述式的化合物的方法。本发明的新化合物是蛋白酶的有效抑制剂，特别是类似胰蛋白酶的丝氨酸蛋白酶，如胰蛋白酶、凝血酶、纤溶酶和Xa因子。其中某些化合物通过直接、选择性地抑制凝血酶表现出抗血栓活性，或者是用于形成具有抗血栓活性的化合物的中间体。该发明包括一种用于在哺乳动物中抑制血小板丢失、抑制血小板聚集物形成、抑制纤维蛋白形成、抑制血栓形成和抑制栓塞形成的组合物，包括一种本发明的化合物在药学上可接受的载体中。本发明的化合物的其他用途是作为抗凝剂，嵌入或物理连接到用于制造用于血液采集、血液循环和血液储存的器械中的材料中，如导管、血液透析机、血液采集注射器和管道、血管内支架。
• Process for preparing aminoguanidines and alkoxyguanidines as protease inhibitors
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20040002539A1

  公开（公告）日：2004-01-01

  Aminoguanidine and alkoxyguanidine compounds, including compounds of the formula: 1 wherein X is O or NR 9 and R 1 -R 4 , R 6 -R 9 , R 11 , R 12 , R a , R b , R c , Y, Z, n and m are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit proteolytic enzymes such as thrombin are described. Also described are methods for preparing the compounds of Formula L The novel compounds of the present invention are potent inhibitors of proteases, especially trypsin-like serine proteases, such as chymotrypsin, trypsin, thrombin, plasmin and factor Xa. Certain of the compounds exhibit antithrombotic activity via direct, selective inhibition of thrombin, or are intermediates useful for forming compounds having antithrombotic activity. The invention includes a composition for inhibiting loss of blood platelets, inhibiting formation of blood platelet aggregates, inhibiting formation of fibrin, inhibiting thrombus formation, and inhibiting embolus formation in a mammal, comprising a compound of the invention in a pharmaceutically acceptable carrier. Other uses of compounds of the invention are as anticoagulants either embedded in or physically linked to materials used in the manufacture of devices used in blood collection, blood circulation, and blood storage, such as catheters, blood dialysis machines, blood collection syringes and tubes, blood lines and stents.

  本发明涉及氨基胍和烷氧基胍化合物，包括以下式子的化合物：1其中X为O或NR9，R1-R4、R6-R9、R11、R12、Ra、Rb、Rc、Y、Z、n和m在说明书中给出，以及其水合物、溶剂合物或药学上可接受的盐，其抑制蛋白酶如凝血酶。还描述了制备式L化合物的方法。本发明的新化合物是蛋白酶的强力抑制剂，尤其是类胰蛋白酶，如胰蛋白酶、凝血酶、纤溶酶和Xa因子。其中某些化合物通过直接、选择性抑制凝血酶表现出抗血栓活性，或者是用于形成具有抗血栓活性的化合物的中间体。本发明包括一种用于抑制哺乳动物体内血小板丧失、抑制血小板聚集、抑制纤维蛋白形成、抑制血栓形成和抑制栓塞形成的组合物，其中包括本发明中的化合物和药学上可接受的载体。本发明化合物的其他用途是作为抗凝剂，嵌入或物理链接到用于血液收集、血液循环和血液储存的设备制造中使用的材料中，如导管、血液透析机、血液采集注射器和管道、血液输送管和支架等。
• AMINOGUANIDINES AND ALKOXYGUANIDINES AS PROTEASE INHIBITORS
  申请人：3-DIMENSIONAL PHARMACEUTICALS, INC.

  公开号：EP0944590B1

  公开（公告）日：2002-03-20
• US6235778B1
  申请人：——

  公开号：US6235778B1

  公开（公告）日：2001-05-22
• US6518310B2
  申请人：——

  公开号：US6518310B2

  公开（公告）日：2003-02-11