7-[3-[4-(2,3-二甲基苯基)哌嗪基]丙氧基]-2(1H)-喹啉酮 | 111073-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 7-[3-[4-(2,3-二甲基苯基)哌嗪基]丙氧基]-2(1H)-喹啉酮
• 英文名称: OPC 4392
• 英文别名: 7-{3-[4-(2,3-Dimethylphenyl)-1-piperazinyl]propoxy}carbostyril；2(1H)-Quinolinone, 7-(3-(4-(2,3-dimethylphenyl)-1-piperazinyl)propoxy)-；7-[3-[4-(2,3-dimethylphenyl)piperazin-1-yl]propoxy]-1H-quinolin-2-one
• CAS: 111073-34-8
• 化学式: C₂₄H₂₉N₃O₂
• 分子量: 391.513
• InChiKey: RRLWEQBPSAFVAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-羟基-2-喹诺酮 在 氢氧化钾 、 三乙胺 、 sodium iodide 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 28.0h， 生成 7-[3-[4-(2,3-二甲基苯基)哌嗪基]丙氧基]-2(1H)-喹啉酮
  参考文献：
  名称：

  Studies on 2(1H)-quinolinone derivatives as neuroleptic agents. I. Synthesis and biological activities of (4-phenyl-1-piperazinyl)-propoxy-2(1H)-quinolinone derivatives.

  摘要：

  为了开发一种新型的神经安定药物，合成了一系列ω-(4-苯基-1-哌嗪基)-烷氧基-2(1H)-喹啉酮衍生物，并测试了它们的抗甲基苯丙胺和抗肾上腺素活性。大多数衍生物在3-(3, 4-二羟基苯基)-L-天冬氨酸（L-DOPA）和甲基苯丙胺处理的小鼠的跳跃行为测试中显示出强效的抗甲基苯丙胺活性，或者在甲基苯丙胺处理的小鼠的致死性测试中表现出显著效果。它们还表现出相对较高的抗肾上腺素效能，这取决于取代基在4-苯基-1-哌嗪基上的性质或数量；其中一些化合物在小鼠中仅引起轻微的强直症。在这些化合物中，7-{3-[4-(2, 3-二甲基苯基)-1-哌嗪基]丙氧基}-2(1H)-喹啉酮（OPC-4392），被认为是一种多巴胺自受体激动剂，已被选定用于进一步研究。同时，本文也讨论了结构-活性关系。

  DOI：

  10.1248/cpb.36.4377

文献信息

• PROCESSES FOR MAKING ALKYLATED ARYLPIPERAZINE AND ALKYLATED ARYLPIPERIDINE COMPOUNDS INCLUDING NOVEL INTERMEDIATES
  申请人：Johnson Matthey Public Limited Company

  公开号：US20150361099A1

  公开（公告）日：2015-12-17

  Novel processes, and intermediates, for making alkylated arylpiperazine and alkylated arylpiperidine compounds of the general formulas (I) and (VII), respectively wherein, R 1 and R 2 are individually selected from hydrogen, alkyl, substituted or alkyl; n=0, 1, or 2; Y=NR 3 R 4 , OR 5 , or SR 5 , where R 3 and R 4 are individually selected from acyl or sulfonyl, and where R 5 is aryl or heteroaryl, or heterocyclic; and Ar is an aryl, heteroaryl, or heterocyclic compound.

  用于制备通式(I)和(VII)中所示的烷基化芳基哌嗪和烷基化芳基哌啶化合物的新工艺和中间体，其中，R1和R2分别选择自氢、烷基、取代基或烷基；n=0、1或2；Y=NR3R4、OR5或SR5，其中R3和R4分别选择自酰基或磺酰基，R5是芳基或杂芳基，或杂环烷基；Ar是芳基、杂芳基或杂环烷基。
• Pharmaceutically useful carbostyril derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04734416A1

  公开（公告）日：1988-03-29

  Carbostyril derivatives having antihistamic action and central nervous controlling action are useful as antihistamic agents or central nervous controlling agents. The derivatives are represented by the general formula, ##STR1## wherein R.sup.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenylalkyl group having an alkylene group containing 1 to 4 carbon atoms; R.sup.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R.sup.3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanolyoxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R.sup.5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group (which may have 1 to 3 substituted groups selected from the group consisting of halogen atoms, alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms), an alkyl group having 1 to 4 carbon atoms (having one substituted group such as a hydroxy group, a phenyl group or an alkanoyloxy group having 1 to 4 carbon atoms), an alkanoyl group having 1 to 4 carbon atoms or benzoyl group; X is a halogen atom; n is 0, or an integer of 1 or 2; Q is an integer of 2 or 3, l and m are respectively an integer of 0 or 1-6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; and the substituted position of the side chain of ##STR2## is any one of the 4-, 5-, 6-, 7- or 8-positions.

  具有抗组胺作用和中枢神经控制作用的羧基苯基丙氨酸衍生物可用作抗组胺剂或中枢神经控制剂。该衍生物由以下通式表示：##STR1##其中R.sup.1是氢原子，具有1至6个碳原子的烷基，具有2至4个碳原子的烯基，具有2至4个碳原子的炔基或具有含有1至4个碳原子的烷基的苯基烷基；R.sup.2是氢原子，具有1至4个碳原子的烷基或苯基；R.sup.3是氢原子，羟基，具有1至4个碳原子的烷基，具有1至4个碳原子的烷氧基或3,4,5-三甲氧基苯甲酰氧基；R.sup.4是氢原子或具有1至4个碳原子的烷基；R.sup.5是具有3至8个碳原子的环烷基，苯基（可以有1至3个取自卤素原子，具有1至4个碳原子的烷基和具有1至4个碳原子的烷氧基的取代基），具有1至4个碳原子的烷基（具有一个取代基，如羟基，苯基或具有1至4个碳原子的烷酰氧基），具有1至4个碳原子的烷酰基或苯甲酰基；X是卤素原子；n为0或1或2的整数；Q为2或3的整数，l和m分别为0或1-6的整数，但l和m的总和不应超过6；羧基苯基丙氨酸骨架中3-和4-位置的碳-碳键为单键或双键；以及##STR2##的侧链的取代位置为4-、5-、6-、7-或8-位置中的任何一个。
• Novel pharmaceutical agents containing carbohydrate moieties and methods of their preparation and use
  申请人：Christian T. Samuel

  公开号：US20060189547A1

  公开（公告）日：2006-08-24

  Hydrophilic N-linked pharmaceutical compositions, methods of their preparation and use in neuraxial drug delivery comprising a glycosyl CNS acting prodrug compound covalently N-linked with a saccharide through an amide or an amine bond and a formulary consisting of an additive, a stabilizer, a carrier, a binder, a buffer, an excipient, an emollient, a disintegrant, a lubricating agent, an antimicrobial agent or a preservative, with the proviso that the saccharide moiety is not a cyclodextrin or a glucuronide.

  亲水性N-连接药物组合物，其制备方法和在神经轴向药物输送中的使用，包括一种糖基中枢神经系统作用前药化合物，通过酰胺或胺键与糖苷共价连接，并且配方包括添加剂、稳定剂、载体、粘合剂、缓冲剂、赋形剂、润肤剂、破碎剂、润滑剂、抗微生物剂或防腐剂，但前提是糖苷基团不是环糊精或葡萄糖醛酸盐。
• Novel Pharmaceutical Agents Containing Carbohydrate Moieties And Methods Of Their Preparation And Use
  申请人：Christian Samuel T.

  公开号：US20110237544A1

  公开（公告）日：2011-09-29

  Hydrophilic N-linked pharmaceutical compositions, methods of their preparation and use in neuraxial drug delivery comprising a glycosyl CNS acting prodrug compound covalently N-linked with a saccharide through an amide or an amine bond and a formulary consisting of an additive, a stabilizer, a carrier, a binder, a buffer, an excipient, an emollient, a disintegrant, a lubricating agent, an antimicrobial agent or a preservative, with the proviso that the saccharide moiety is not a cyclodextrin or a glucuronide.

  亲水性N-连接的药物组成物、其制备方法和在神经轴药物输送中的使用，包括一种糖基CNS作用的前药化合物，通过酰胺或胺键与糖分子共价连接，并由添加剂、稳定剂、载体、粘合剂、缓冲剂、赋形剂、润肤剂、崩解剂、润滑剂、抗微生物剂或防腐剂组成的制剂，前提是糖分子部分不是环糊精或葡糖醛酸盐。
• Preparation of pharmaceutical compositions for the treatment of hypoxia
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0226441A2

  公开（公告）日：1987-06-24

  In the preparation of a pharmaceutical compositions to the treatment of hypoxia there is used, as active ingredient, a compound of the formula: in which R' is a hydrogen atom or a lower alkyl, lower alkenyl, lower alkynyl or phenyl-lower alkyl group. Z is a group of the formula (in which R2 is a hydrogen atom or a lower alkyl group; and the bond is a single or double bond), a group -(CH2)3-, -O-CH2- or -S-CH2-; R3 is a pyridyl group, or a phenyl group optionally substituted with up to three substituents selected from halogen atoms and lower alkyl, lower alkoxy and hydroxy groups: the group is a group and A is a lower alkylene group; provided that when the group is a group then Z is a group of the formula and R3 is neither a pyridyl group nor a phenyl group having a hydroxy group as the substituent; or provided that when R3 is a pyridyl group, then Z is a group of the formula

  在制备治疗缺氧症的药物组合物时，使用式中的化合物作为活性成分： 其中 R'是氢原子或低级烷基、低级烯基、低级炔基或苯基-低级烷基。 Z 是式中的一个基团 (其中 R2 为氢原子或低级烷基；键为单键或双键）、基团-(CH2)3-、-O-CH2-或-S-CH2-； R3 是吡啶基，或最多可被三个取代基取代的苯基，这三个取代基可选 自卤素原子、低级烷基、低级烷氧基和羟基： 该基团 是一个基团 且 A 为低级亚烷基； 但当该基团 是一个基团 则 Z 是式中的一个基团 且 R3 既非吡啶基，也非以羟基为取代基的苯基；或当 R3 为吡啶基时，则 Z 为式中的基团