5-(2-Bromoethoxy)-2-methylquinoline | 420786-70-5

• 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: 5-(2-Bromoethoxy)-2-methylquinoline
• CAS: 420786-70-5
• 化学式: C₁₂H₁₂BrNO
• 分子量: 266.13
• InChiKey: JAIIDDLFCCFGFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(Piperidin-4-ylidenemethyl)-1,3-dihydroindol-2-one 、 5-(2-Bromoethoxy)-2-methylquinoline 生成 6-{-[2-(2-Methylquinolin-5-oxy)ethyl]piperidin-4-ylidenemethyl}-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Heterocyclic compounds possessing affinity at 5HT1 -type receptors and use thereof in therapy

  摘要：

  本文披露了化合物(I)的公式及其药学上可接受的盐：其中A为可选取的取代苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；b为1、2或3，c为1、2或3，其中b+c为2、3、4或5；X为碳，Y为CH，为双键，e为0；或X为碳，Y为CH2或氧，为单键，e为1；或X为氮，Y为CH2，为单键，e为0；R1为氢、氰基、卤素、C1-6烷基、C1-6烷氧基、C1-6烷氧基C1-6烷基、NHCOCH3或OCONR5R6，其中R5和R6独立地为氢或C1-6烷基；R2为卤素、氰基或C1-6烷氧基；d为0、1、2或3；R3为氢、C1-6烷基、C1-6酰基、氟C1-6酰基、C1-6烷基磺酰基、氟C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；而R4与其连接的氮原子形成一个可选的取代的5到7成员杂环基团融合到苯环上，但当化合物(I)具有以下结构时：其中A、b、c、R1、e、X、Y、R2和d如上定义，而R3为氢、C1-6烷基或芳基C1-6烷基，则(i)X为碳，Y为CH，为双键；或(ii)b和c都为1；或(iii)在哌嗪环中氧代取代的碳原子相邻的碳原子，标记为“★”，被取代。本文还披露了制备这些化合物的方法以及这些化合物在治疗中的用途，特别是用于中枢神经系统障碍，如抑郁症或焦虑症。

  公开号：

  US07244726B2
• 作为产物：
  描述：

  2-甲基喹啉-5-醇 、 1,2-二溴乙烷 生成 5-(2-Bromoethoxy)-2-methylquinoline
  参考文献：
  名称：

  Heterocyclic compounds possessing affinity at 5HT1 -type receptors and use thereof in therapy

  摘要：

  本文披露了化合物(I)的公式及其药学上可接受的盐：其中A为可选取的取代苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；b为1、2或3，c为1、2或3，其中b+c为2、3、4或5；X为碳，Y为CH，为双键，e为0；或X为碳，Y为CH2或氧，为单键，e为1；或X为氮，Y为CH2，为单键，e为0；R1为氢、氰基、卤素、C1-6烷基、C1-6烷氧基、C1-6烷氧基C1-6烷基、NHCOCH3或OCONR5R6，其中R5和R6独立地为氢或C1-6烷基；R2为卤素、氰基或C1-6烷氧基；d为0、1、2或3；R3为氢、C1-6烷基、C1-6酰基、氟C1-6酰基、C1-6烷基磺酰基、氟C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；而R4与其连接的氮原子形成一个可选的取代的5到7成员杂环基团融合到苯环上，但当化合物(I)具有以下结构时：其中A、b、c、R1、e、X、Y、R2和d如上定义，而R3为氢、C1-6烷基或芳基C1-6烷基，则(i)X为碳，Y为CH，为双键；或(ii)b和c都为1；或(iii)在哌嗪环中氧代取代的碳原子相邻的碳原子，标记为“★”，被取代。本文还披露了制备这些化合物的方法以及这些化合物在治疗中的用途，特别是用于中枢神经系统障碍，如抑郁症或焦虑症。

  公开号：

  US07244726B2

文献信息

• [EN] BENZOXAZINONE DERIVATIVES HAVING AFFINITY FOR 5- HT RECEPTORS, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE BENZOXAZINONE POSSEDANT UNE AFFINITE AVEC DES RECEPTEURS 5-HT, PREPARATION ET UTILISATION DE CEUX-CI
  申请人：GLAXO GROUP LTD

  公开号：WO2004099198A1

  公开（公告）日：2004-11-18

  Benzoxazinone derivatives, their preparation and use Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: (I) wherein R1 is hydrogen or C1-6alkyl; R2 is fluoro or chloro; R3 is hydrogen, fluoro or chloro; and X is nitrogen or CH. Methods of preparation and uses thereof in treatment of CNS disorders, such as depression or anxiety, are also disclosed.

  苯并噁唑酮衍生物，它们的制备和用途是公开的：其中R1是氢或C1-6烷基；R2是氟或氯；R3是氢、氟或氯；X是氮或CH。还公开了其制备方法和在治疗中枢神经系统疾病，如抑郁症或焦虑症中的用途。
• [EN] HETEROCYCLIC COMPOUNDS POSSESSING AFFINITY AT 5HT1-TYPE RECEPTORS AND USE THEREOF IN THERAPY<br/>[FR] COMPOSES PRESENTANT UNE AFFINITE AVEC DES RECEPTEURS DE TYPE 5HT1 ET LEUR UTILISATION THERAPEUTIQUE
  申请人：GLAXO GROUP LTD

  公开号：WO2003068772A1

  公开（公告）日：2003-08-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed:(I)wherein A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; b is 1, 2 or 3 and c is 1, 2 or 3, wherein b + c is 2, 3, 4 or 5; X is carbon, Y is CH, is a double bond and e is 0; or X is carbon, Y is CH2 or oxygen, is a single bond and e is 1; or X is nitrogen, Y is CH2, is a single bond and e is 0; R1 is hydrogen, cyano, halogen, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, NHCOCH3 or OCONR5R6, wherein R5 and R6 are independently hydrogen or C1-6alkyl; R2 is halogen, cyano or C1-6alkoxy; d is 0, 1, 2 or 3; R3 is hydrogen, C1-6alkyl, C1-6alkanoyl, fluoroC1-6alkanoyl, C1-6alkylsulfonyl, fluoroC1-6alkylsulfonyl, carbamoyl, C1-6alkylcarbamoyl or arylC1-6alkyl; and R4, together with the nitrogen atom to which it is attached, forms an optionally substituted 5 to 7 membered heterocyclic group fused to the benzene ring, provided that when a compound of formula (I) has the following structure: wherein A, b, c, R1, e, X, Y, R2 and d are as defined above and R3 is hydrogen, C1-6alkyl or arylC1-6alkyl, then (i) X is carbon, Y is CH and is a double bond; or (ii) b and c are both 1; or (iii) the carbon atom adjacent to the oxo-substituted carbon atom in the morpholinyl ring, marked ' * ', is substituted. Methods of preparing the compounds and uses of the compounds in therapy, in particular for a CNS disorder such as depression or anxiety, are also disclosed.

  公开了式(I)的化合物及其药学上可接受的盐： (I)其中A是可选择取代的苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；b为1、2或3，c为1、2或3，其中b+c为2、3、4或5；X为碳，Y为CH，为双键，e为0；或X为碳，Y为CH2或氧，为单键，e为1；或X为氮，Y为CH2，为单键，e为0；R1为氢、氰基、卤素、C1-6烷基、C1-6烷氧基、C1-6烷氧基C1-6烷基、NHCOCH3或OCONR5R6，其中R5和R6各自独立地为氢或C1-6烷基；R2为卤素、氰基或C1-6烷氧基；d为0、1、2或3；R3为氢、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；而当式(I)的化合物具有以下结构时：其中A、b、c、R1、e、X、Y、R2和d如上定义，而R3为氢、C1-6烷基或芳基C1-6烷基时，(i) X为碳，Y为CH，为双键；或(ii) b和c均为1；或(iii)在吗啉环中氧代取代的碳原子相邻的碳原子，标记为'*'，被取代。还公开了制备这些化合物的方法以及这些化合物在治疗中的用途，特别是在中枢神经系统紊乱如抑郁症或焦虑症中的用途。
• [EN] PIPERIDINE AND PIPERAZINE DERIVATIVES POSSESSING AFFINITY AT 5HT-1 TYPE RECEPTORS<br/>[FR] DERIVES DE PIPERIDINE ET DE PIPERAZINE POSSEDANT UNE AFFINITE POUR LES RECEPTEURS DE TYPE 5HT-1
  申请人：GLAXO GROUP LTD

  公开号：WO2003068236A1

  公开（公告）日：2003-08-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed:wherein A is optionally substituted phenyl, indolyl, quinolinyl, quinazolinyl, indazolyl or isoquinolinyl; X is carbon, Y is CH and is a double bond; or X is CH, Y is CH2 or oxygen and is a single bond; or X is nitrogen, Y is CH2 and is a single bond; R1 is halogen, cyano, nitro, C1-6 alkyl, haloC1-6 alkyl, C1-6 alkoxy, C3-7 heterocyclylC1-6 alkyl, C3-7 heterocyclyl C1-6 alkoxy; a is 0, 1, 2, 3 or 4; R2 is either: halogen, -CN, an optionally substituted C3-7 cycloalkyl, an optionally substituted aryl or an optionally substituted C-linked 3-7 membered heterocyclic group; or a group -(Z)b-B wherein: (i) Z is oxygen, CH2, C=O, SO2 or C=N-OR3 wherein R3 is hydrogen or C1-6 alkyl; b is 1, 2, or 3; and B is hydrogen, C1-6 alkyl, C3-7 cycloalkyl, C1-6 alkoxy or NR4R5 wherein R4 and R5 are independently hydrogen, C1-6 alkyl, C3-7 cycloalkyl, C1-6 alkanoyl, fluoroC1-6 alkanoyl, C1-6 alkylsulfonyl, fluoroC¿1-6 alkylsulfonyl, carbamoyl or C1-6 alkylcarbamoyl, or R4 and R5, together with the nitrogen atom to which they are attached, form part of an optionally substituted 3 to 7 membered heterocyclic group; or (ii) Z is oxygen, CH or CH2, b is 1, and B forms the rest of an aryl or a C3-7 heterocyclic group fused to the phenyl ring; excluding 1-[2-[2-(phenylmethyl)phenoxy]ethyl]-4-[(2,3,4-trimethoxyphenyl)methyl]-piperazine and pharmaceutically acceptable salts thereof, and N-[4-[2-[4-[(3,4-dimethoxyphenyl)methyl]-1-piperazinyl]ethoxy]phenyl]-ethanesulfonamide and pharmaceutically acceptable salts thereof. Methods of preparing the compounds and uses of the compounds in therapy, in particular for CNS disorders such as depression and anxiety, are also disclosed.

  公开了公式（I）的化合物及其药学上可接受的盐：其中A是可选择取代的苯基、吲哚基、喹啉基、喹唑啉基、吲唑基或异喹啉基；X是碳，Y是CH且为双键；或X是CH，Y是CH2或氧且为单键；或X是氮，Y是CH2且为单键；R1是卤素、氰基、硝基、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、C3-7杂环基C1-6烷基、C3-7杂环基C1-6烷氧基；a为0、1、2、3或4；R2为：卤素、-CN、可选择取代的C3-7环烷基、可选择取代的芳基或可选择取代的C-连接的3-7成员杂环基；或者为一个组-(Z)b-B，其中：（i）Z为氧、CH2、C=O、SO2或C=N-OR3，其中R3为氢或C1-6烷基；b为1、2或3；B为氢、C1-6烷基、C3-7环烷基、C1-6烷氧基或NR4R5，其中R4和R5独立地为氢、C1-6烷基、C3-7环烷基、C1-6烷酰基、氟代C1-6烷酰基、C1-6烷基磺酰基、氟代C¿1-6烷基磺酰基、氨基或C1-6烷基氨基；或R4和R5连同它们所连接的氮原子形成可选择取代的3至7成员杂环基的一部分；或（ii）Z为氧、CH或CH2，b为1，B形成与苯环融合的芳基或C3-7杂环基的其余部分；不包括1-[2-[2-(苯甲基)苯氧基]乙基]-4-[(2,3,4-三甲氧基苯基)甲基]-哌嗪和药学上可接受的盐，以及N-[4-[2-[4-[(3,4-二甲氧基苯基)甲基]-1-哌嗪基]乙氧基]苯基]-乙烷磺酰胺和药学上可接受的盐。还公开了制备这些化合物的方法以及这些化合物在治疗中的用途，特别是用于中枢神经系统疾病如抑郁症和焦虑症。
• Heterocyclic compounds possessing affinity at 5ht1-type receptors and use thereof in therapy
  申请人：Harrington P Frank

  公开号：US20050085458A1

  公开（公告）日：2005-04-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; b is 1, 2 or 3 and c is 1, 2 or 3, wherein b+c is 2, 3, 4 or 5; X is carbon, Y is CH, is a double bond and e is 0; or X is carbon, Y is CH 2 or oxygen, is a single bond and e is 1; or X is nitrogen, Y is CH 2 , is a single bond and e is 0; R1 is hydrogen, cyano, halogen, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, NHCOCH 3 or OCONR5R6, wherein R5 and R6 are independently hydrogen or C 1-6 alkyl; R2 is halogen, cyano or C 1-6 alkoxy; d is 0, 1, 2 or 3; R3 is hydrogen, C 1-6 alkyl, C 1-6 alkanoyl, fluoroC 1-6 alkanoyl, C 1-6 alkylsulfonyl, fluoroC 1-6 alkylsulfonyl, carbamoyl, C 1-6 alkylcarbamoyl or arylC 1-6 alkyl; and R4, together with the nitrogen atom to which it is attached, forms an optionally substituted 5 to 7 membered heterocyclic group fused to the benzene ring, provided that when a compound of formula (I) has the following structure: wherein A, b, c, R1, e, X, Y, R2 and d are as defined above and R3 is hydrogen, C 1-6 alkyl or arylC 1-6 alkyl, then (i) X is carbon, Y is CH and is a double bond; or (ii) b and c are both 1; or (iii) the carbon atom adjacent to the oxo-substituted carbon atom in the morpholinyl ring, marked “*”, is substituted. Methods of preparing the compounds and uses of the compounds in therapy, in particular for a CNS disorder such as depression or anxiety, are also disclosed.

  公开了式（I）的化合物及其药学上可接受的盐：其中，A是可选择取代的苯基，萘基，吲哚基，喹啉基，喹唑啉基，吲唑基，异喹啉基或苯并呋喃基；b为1、2或3，c为1、2或3，其中b+c为2、3、4或5；X为碳，Y为CH，为双键，e为0；或X为碳，Y为CH2或氧，为单键，e为1；或X为氮，Y为CH2，为单键，e为0；R1为氢、氰、卤素、C1-6烷基、C1-6烷氧基、C1-6烷氧基C1-6烷基、NHCOCH3或OCONR5R6，其中R5和R6独立地为氢或C1-6烷基；R2为卤素、氰或C1-6烷氧基；d为0、1、2或3；R3为氢、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；而R4与其连接的氮原子形成一个可选择取代的5到7元杂环基，与苯环融合，但当式（I）的化合物具有以下结构时，则需满足以下条件：其中，A、b、c、R1、e、X、Y、R2和d如上所定义，而R3为氢、C1-6烷基或芳基C1-6烷基，那么（i）X为碳，Y为CH，为双键；或（ii）b和c均为1；或（iii）在吗啉环中与氧代取代碳原子相邻的碳原子，标记为“*”，被取代。还公开了制备这些化合物的方法以及这些化合物在治疗中的用途，特别是在治疗中枢神经系统疾病如抑郁症或焦虑症中的用途。
• Compound possessing affinity at 5ht1-type receptors and use thereof in therapy of cns disorders
  申请人：Smith W Paul

  公开号：US20050107410A1

  公开（公告）日：2005-05-19

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein: A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; X is carbon, Y is CH and is a double bond; or X is CH, Y is CH 2 or oxygen and is a single bond; or X is nitrogen, Y is CH 2 and is a single bond; is halogen, hydroxy, cyano, C 1-6 alkyl, haloC 1-6 alkyl or C 1-6 alkoxy; a is 0, 1, 2, 3 or 4; R2 and R3, together with the nitrogen atom to which they are attached, form a nitro group or an optionally substituted 3 to 7 membered heterocyclic group, or R2 and R3 are independently hydrogen, aroyl, C 1-6 alkyl, C 1-6 alkanoyl, fluoroC 1-6 alkanoyl, C 1-6 alkylsulfonyl, fluoroC 1-6 alkylsulfonyl, carbamoyl, C 1-6 alkylcarbamoyl, arylC 1-6 alkyl or a group CO(CH 2 )bNR4R5 wherein b is 1, 2, 3 or 4; and R4 and R5 are independently hydrogen or C 1-6 alkyl, or R4 and R5, together with the nitrogen atom to they are attached, form part of an optionally substituted 3 to 7 membered heterocyclic group. Methods of preparing the compounds and uses of the compounds in therapy, in particular for CNS disorders such as depression and anxiety, are also disclosed.

  公开了式（I）的化合物及其药学上可接受的盐：其中，A是可选取的取代苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；X是碳，Y是CH且为双键；或X是CH，Y是CH2或氧且为单键；或X是氮，Y是CH2且为单键；R1是卤素、羟基、氰基、C1-6烷基、卤代C1-6烷基或C1-6烷氧基；a是0、1、2、3或4；R2和R3与它们所连接的氮原子一起形成硝基基团或可选取的取代的3到7元杂环基团，或R2和R3分别是氢、芳香基、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基、C1-6烷基氨基、芳基C1-6烷基或CO(CH2)bNR4R5基团，其中b是1、2、3或4；R4和R5分别是氢或C1-6烷基，或R4和R5与它们所连接的氮原子一起形成可选取的取代的3到7元杂环基团。还公开了制备该化合物的方法以及该化合物在治疗中的用途，特别是在中枢神经系统疾病如抑郁症和焦虑症方面的用途。