6-(3-Ethylaminopropoxy)carbostyril | 189362-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(3-Ethylaminopropoxy)carbostyril
• 英文别名: 6-[3-(ethylamino)propoxy]-1H-quinolin-2-one
• CAS: 189362-44-5
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: PHACUFZJVWJWDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-N-methylcarbamoyl chloride 、 6-(3-Ethylaminopropoxy)carbostyril 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57%的产率得到1-Cyclohexyl-3-ethyl-1-methyl-3-[3-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-urea
  参考文献：
  名称：

  2(1H)-Quinolinone derivatives as novel anti-arteriostenotic agents showing anti-thrombotic and anti-hyperplastic activities

  摘要：

  In order to search for anti-arteriostenotic agents, a series of 2(1H)-quinolinone derivatives was synthesized and evaluated for anti-thrombotic activity and for anti-hyperplastic activity. From this series, (-)-6-[3-[3-cyclopropyl-3-[(1R,2R)-2-hydroxycyclohexyl]ureido] propoxy]-2(1H)-quinolinone (1p, OPC-33509) was selected as the best candidate by balancing the efficacy on anti-thrombosis and anti-hyperplasia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00246-7
• 作为产物：
  描述：

  6-羟基-2(1H)-喹啉酮 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-(3-Ethylaminopropoxy)carbostyril
  参考文献：
  名称：

  2(1H)-Quinolinone derivatives as novel anti-arteriostenotic agents showing anti-thrombotic and anti-hyperplastic activities

  摘要：

  In order to search for anti-arteriostenotic agents, a series of 2(1H)-quinolinone derivatives was synthesized and evaluated for anti-thrombotic activity and for anti-hyperplastic activity. From this series, (-)-6-[3-[3-cyclopropyl-3-[(1R,2R)-2-hydroxycyclohexyl]ureido] propoxy]-2(1H)-quinolinone (1p, OPC-33509) was selected as the best candidate by balancing the efficacy on anti-thrombosis and anti-hyperplasia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00246-7

文献信息

• [EN] CARBOSTYRIL DERIVATIVES AS ANTITHROMBOTIC AGENTS<br/>[FR] DERIVES DE CARBOSTYRYLE EN TANT QU'AGENTS ANTITHROMBOTIQUES
  申请人：OTSUKA PHARMACEUTICAL COMPANY, LIMITED

  公开号：WO1997012869A1

  公开（公告）日：1997-04-10

  (EN) A carbostyril derivative of formula (1), wherein A is lower alkylene, R is H, halogen or lower alkoxy, R1 and R2 are each lower alkyl being optionally substituted by OH, lower alkoxy, phenyl-lower alkoxy or lower alkanoyloxy; cycloalkyl being optionally substituted by OH, hydroxy-lower alkoxy or lower alkanoyloxy; or amino being optionally substituted by lower alkyl or cycloalkyl, R3 is H, lower alkyl, lower alkenyl or hydroxy-lower alkyl, and the bond between 3- and 4-positions of the carbostyril nucleus is single or double, provided that when R and R3 are H, R1 and R2 should not be either unsubstituted lower alkyl or unsubstituted cycloalkyl, or a salt thereof, which shows antithrombotic activities, intima thickening inhibitory activity, the platelet mass dissociating activity and increasing activity of the blood flow in the brain and the peripheral vessel, and hence, is useful as medicines in the prophylaxis or treatment of various ischemic diseases.(FR) La présente invention concerne un dérivé de carbostyryle de formule (1), dans laquelle A est un alkylène inférieur, R est H, halogène ou un alcoxy inférieur, R1 et R2 sont chacun un alkyle inférieur, éventuellement substitué par OH, un alcoxy inférieur, un phényle-alcoxy inférieur ou un alcanoyloxy inférieur; le cycloalkyle est facultativement substitué par OH, un hydroxy-alcoxy inférieur ou un alcanoyloxy inférieur; ou l'amino est facultativement substitué par un alkyle inférieur ou un cycloalkyle; R3 est H, un alkyle inférieur, un alkényle inférieur ou un hydroxy-alkyle inférieur, et la liaison entre les positions 3 et 4 du noyau de carbostyryle est simple ou double, à condition que, quand R et R3 sont H, R1 et R2 ne soient pas soit un alkyle inférieur non substitué, soit un cycloalkyle non substitué ou un sel d'un de ces composés. Le dérivé selon l'invention manifeste des propriétés antithrombotiques, inhibitrices de l'épaississement de l'intima, de dissociation des amas de plaquettes et d'accroissement du débit sanguin dans le cerveau et dans les vaisseaux périphériques. Par conséquent, il est utile comme médicament dans la prophylaxie ou le traitement de diverses affections ischémiques.

  本发明涉及一种式样为(1)式、具有取代基如下所述的碳扼基衍生物，其中A为下端烷二元基，R为氢、卤素或下端烷氧基，R1和R2均为下端烷基和选代羟基、下端烷氧基、苯-烷氧基或烷基酰氧基；6-环烷基可选地被羟基、羟基-烷氧基或烷基酰氧基取代；氨基可选地被下端烷基或环烷基取代，R3为氢、下端烷基、烯基或羟基-烷基，且碳扼基核中3-位和4-位的键为单键或双键，其条件是：当R和R3为氢时，R1和R2不应分别为未取代的下端烷基或未取代的环烷基，或分别为它们的盐，该衍生物具有抗血小板凝聚作用、抑制内膜增厚作用、防止血小板膜离解作用，以及增加脑部和周围血管血液流量的作用。因此，该衍生物可用于预防或治疗各种缺血性疾病。
• CARBOSTYRIL DERIVATIVES AS ANTITHROMBOTIC AGENTS
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0796248A1

  公开（公告）日：1997-09-24
• US6143763A
  申请人：——

  公开号：US6143763A

  公开（公告）日：2000-11-07
• 2(1H)-Quinolinone derivatives as novel anti-arteriostenotic agents showing anti-thrombotic and anti-hyperplastic activities
  作者：Yasuo Koga、Yoshito Kihara、Minoru Okada、Yoshihiro Inoue、Shirou Tochizawa、Kazuyuki Toga、Kazue Tachibana、Yukio Kimura、Takao Nishi、Hiroyoshi Hidaka

  DOI：10.1016/s0960-894x(98)00246-7

  日期：1998.6

  In order to search for anti-arteriostenotic agents, a series of 2(1H)-quinolinone derivatives was synthesized and evaluated for anti-thrombotic activity and for anti-hyperplastic activity. From this series, (-)-6-[3-[3-cyclopropyl-3-[(1R,2R)-2-hydroxycyclohexyl]ureido] propoxy]-2(1H)-quinolinone (1p, OPC-33509) was selected as the best candidate by balancing the efficacy on anti-thrombosis and anti-hyperplasia. (C) 1998 Elsevier Science Ltd. All rights reserved.