2-acetyl-6-bromo-4H-1,2,4-triazine-3,5-dione | 20028-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-acetyl-6-bromo-4H-1,2,4-triazine-3,5-dione
• 英文别名: 2-acetyl-6-bromo-1,2,4-triazine-3,5-dione；1-Acetyl-5-brom-6-azauracil；2-acetyl-6-bromo-2H-[1,2,4]triazine-3,5-dione；2-acetyl-6-bromo-3,5-dioxo-(2H,4H)-1,2,4-triazine；2-acetyl-6-bromo-1,2,4-triazine-3,5(2H,4H)-dione；2-acetyl-6-bromo-2H-[1,2,4]triazine-3,5-dione
• CAS: 20028-51-7
• 化学式: C₅H₄BrN₃O₃
• 分子量: 234.009
• InChiKey: YWRVDAAKFPRDHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苄基氯甲基醚 、 2-acetyl-6-bromo-4H-1,2,4-triazine-3,5-dione 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 4-((benzyloxy)methyl)-6-bromo-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  [EN] MODULATORS OF THR-β AND METHODS OF USE THEREOF
  [FR] MODULATEURS DE THR-β ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2020227549A8
• 作为产物：
  描述：

  5-溴-6-氮尿嘧啶 、 乙酸酐 反应 2.0h， 以96%的产率得到2-acetyl-6-bromo-4H-1,2,4-triazine-3,5-dione
  参考文献：
  名称：

  [EN] AZABICYCLO [3. 1. 0] HEXYL DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS
  [FR] NOUVEAUX COMPOSÉS

  摘要：

  本发明涉及式(I)的新化合物或其盐，其中G选自以下组成的一组：苯基，5-或6-成员单环杂环基，或8-至11-成员杂环双环基；p是一个从0到5的整数；R1是卤素，羟基，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4烷酰基和SF5；或对应于一个R6基团；当p是一个从2到5的整数时，每个R1可以相同也可以不同；R2是氢或C1-4烷基；n是3、4、5或6；R6是从以下组成的基团中选择的一个：异噁唑基，-CH2-N-吡咯基，1,1-二氧化-2-异噻唑啉基，噻吩基，噻唑基，吡啶基，2-吡咯烷基，以及这样的R6基团可以选择地被来自以下组成的一个或两个取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4烷酰基；R4在以下组成的基团中选择：氢，卤素，羟基，氰基，C1-4烷基，C3-7环烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4烷酰基和NR'R'；或R4是一个苯基，一个5-14成员杂环基；和任何这样的苯基或杂环基可以选择地被来自以下组成的1、2、3或4个取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4烷酰基，卤代C1-4烷氧基和SF5；R7是氢或C1-2烷基；R'是H，C1-4烷基或C1-4烷酰基；R'被定义为R'；R'和R'连同相互连接的氮原子可以形成一个5-、6-成员饱和或不饱和杂环环；它们的制备方法，用于这些方法的中间体，含有它们的药物组合物以及它们在治疗中的用途，作为多巴胺D3受体调节剂，例如用于治疗药物依赖，作为抗精神病药物，用于治疗强迫症谱系障碍，或早泄。

  公开号：

  WO2009043884A1

文献信息

• [EN] AZABICYCLO [3. 1. 0] HEXYL DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2009043884A1

  公开（公告）日：2009-04-09

  The present invention relates to novel compounds of formula (I) or a salt thereof, wherein G is selected from a group consisting of: phenyl, a 5- or 6-membered monocyclic heteroaryl group, or a 8- to 11-membered heteroaryl bicyclic group; p is an integer ranging from 0 to 5; R1 is halogen, hydroxy, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and SF5; or corresponds to a group R6; and when p is an integer ranging from 2 to 5, each R1 may be the same or different; R2 is hydrogen or C1-4alkyl; n is 3, 4, 5 or 6; R6 is a moiety selected from the group consisting of: isoxazolyl, -CH2-N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl, 2-pyrrolidinonyl, and such R6 group is optionally substituted by one or two substituents selected from: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, C1-4alkanoyl; R4 is selected in the group consisting of: hydrogen, halogen, hydroxy, cyano, C1-4alkyl, C3-7 cycloalkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and NR'R'; or R4 is a phenyl group, a 5-14 membered heterocyclic group; and any of such phenyl or heterocyclic group is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, C1-4alkanoyl, haloC1-4alkoxy and SF5; R7 is hydrogen or C1-2alkyl; R' is H, C1-4 alkyl or C1-4 alkanoyl; R' is defined as R'; R' and R' taken together with the interconnecting nitrogen atom may form a 5-, 6-membered saturated or unsaturated heterocyclic ring; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D3 receptors, e.g. to treat drug dependency, as antipsychotic agents, to treat obsessive compulsive spectrum disorders, or premature ejaculation.

  本发明涉及式(I)的新化合物或其盐，其中G选自以下组成的一组：苯基，5-或6-成员单环杂环基，或8-至11-成员杂环双环基；p是一个从0到5的整数；R1是卤素，羟基，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4烷酰基和SF5；或对应于一个R6基团；当p是一个从2到5的整数时，每个R1可以相同也可以不同；R2是氢或C1-4烷基；n是3、4、5或6；R6是从以下组成的基团中选择的一个：异噁唑基，-CH2-N-吡咯基，1,1-二氧化-2-异噻唑啉基，噻吩基，噻唑基，吡啶基，2-吡咯烷基，以及这样的R6基团可以选择地被来自以下组成的一个或两个取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4烷酰基；R4在以下组成的基团中选择：氢，卤素，羟基，氰基，C1-4烷基，C3-7环烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4烷酰基和NR'R'；或R4是一个苯基，一个5-14成员杂环基；和任何这样的苯基或杂环基可以选择地被来自以下组成的1、2、3或4个取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4烷酰基，卤代C1-4烷氧基和SF5；R7是氢或C1-2烷基；R'是H，C1-4烷基或C1-4烷酰基；R'被定义为R'；R'和R'连同相互连接的氮原子可以形成一个5-、6-成员饱和或不饱和杂环环；它们的制备方法，用于这些方法的中间体，含有它们的药物组合物以及它们在治疗中的用途，作为多巴胺D3受体调节剂，例如用于治疗药物依赖，作为抗精神病药物，用于治疗强迫症谱系障碍，或早泄。
• 1,2,4-Triazine Derivatives, Preparation and Use Thereof in Human Therapy
  申请人：Dupont-Passelaigue Elisabeth

  公开号：US20080167313A1

  公开（公告）日：2008-07-10

  The invention concerns 3,5-dioxo-(2H,4H)-1,2,4-triazine derivatives of general formula (I), wherein: R 1 and R 2 , identical or different, represent a branched or linear C 1 -C 7 alkyl or alkenyl radical, a C 1 -C 6 alkyl radical substituted by groups such as trifluoromethyl, C 5 -C 6 cycloalkyl, nitrile, C 1 -C 4 alkoxycarbonylvinyl, hydroxycarbonylvinyl, C 1 -C 4 alkoxycarbonyl, carboxylate, benzyloxy or phenyl (for which the phenyl ring is optionally substituted by one or more groups such as C 1 -C 4 alkoyl, C 1 -C 4 alkoxy, nitro, halogen, trifluoromethyl); YR 3 represents oxygen or NR 3 for which R 3 represents hydrogen, a linear or branched C 1 -C 7 alkyl or alkenyl radical, a C 1 -C 6 alkyl radical substituted by groups such as trifluoromethyl or phenyl (for which the phenyl ring is optionally substituted by one or more groups such as C 1 -C 4 alkoyl, C 1 -C 4 alkoxy, nitro, halogen, trifluoromethyl); Z represents an oxygen atom or a carbon atom capable of being bound to the ortho, meta or para positions of the phenyl group of formula I; n can be 0 to 5 when Z=C or 2 to 4 when Z=O; X represents oxygen or sulphur; R 4 , R 5 , R 6 , R 7 and R 8 represent hydrogen or fluorine; R 9 , R 10 and R 11 represent hydrogen or a linear or branched C 1 -C 5 alkyl group as well as the pharmaceutically acceptable base addition salts, and the various enantiomers of compounds having asymmetric carbons, and their mixtures in all proportions including in particular the racemic mixtures.

  该发明涉及一般式（I）的3,5-二氧代-(2H,4H)-1,2,4-三嗪衍生物，其中：R1和R2，相同或不同，代表分支或直链的C1-C7烷基或烯基基团，被三氟甲基、C5-C6环烷基、腈基、C1-C4烷氧羰基乙烯基、羟基羰基乙烯基、C1-C4烷氧羰基、羧酸酯、苄氧基或苯基等基团取代的C1-C6烷基基团（其中苯环可选择地被一个或多个基团如C1-C4烷酰基、C1-C4烷氧基、硝基、卤素、三氟甲基取代）；YR3代表氧或NR3，其中R3代表氢、直链或分支的C1-C7烷基或烯基基团，被三氟甲基或苯基等基团取代的C1-C6烷基基团（其中苯环可选择地被一个或多个基团如C1-C4烷酰基、C1-C4烷氧基、硝基、卤素、三氟甲基取代）；Z代表一氧原子或一碳原子，能够与一般式I的苯基的邻位、间位或对位结合；当Z=C时，n可以为0至5，当Z=O时，n可以为2至4；X代表氧或硫；R4、R5、R6、R7和R8代表氢或氟；R9、R10和R11代表氢或直链或分支的C1-C5烷基基团，以及药学上可接受的碱盐，以及具有不对称碳的化合物的各种对映体以及它们在所有比例中的混合物，包括特别是消旋混合物。
• [EN] DERIVATIVES OF TRIAZINES AND URACILS, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPEUTICS<br/>[FR] DÉRIVÉS DE TRIAZINES ET D'URACILES, LEUR PRÉPARATION ET LEURS APPLICATIONS EN THÉRAPEUTIQUE HUMAINE
  申请人：PF MEDICAMENT

  公开号：WO2010006962A1

  公开（公告）日：2010-01-21

  The present invention relates to derivatives of general formula I wherein : - W represents nitrogen, - R1 represents: • a hydrogen or a linear or branched C1-C5 alkyl radical or, • a C1-C3 alkyl radical substituted with groups such as trifluoromethyl, nitrile, hydroxy, C1-C3 alcoxy, C3-C6 alkoxyalkoxy, indolyl, thiophenyl, oxothiophenyl, C1-C3 N-alkylcarbamoyl groups or, • a phenyl or pyridyl or naphthyl, or thiophenyl group optionally substituted with one or more groups such as halogen atoms, nitro, nitrile, trifluoromethyl, vinyl, methylsulfanyl, linear branched C1-C4 alkyl, linear or branched C1-C3 alkoxy groups, • a C6 2-oxocycloalkyl radical - R2 represents a methyl or heptyl, - m, n are equal to 1, - V represents CH2, - X-Y represents -N- (C=O) -, -CH-O-, - Z represents a phenyl group substituted with one or more trifluoromethyl groups, halogen atoms or linear C1-C4 alkyl groups.

  本发明涉及一般式I的衍生物，其中： - W代表氮， - R1代表： • 氢或直链或支链C1-C5烷基基团，或者 • 被三氟甲基、腈、羟基、C1-C3烷氧基、C3-C6烷氧基烷氧基、吲哚基、噻吩基、氧硫吩基、C1-C3 N-烷基氨基羰基基团取代的C1-C3烷基基团，或者 • 苯基或吡啶基或萘基，或者选择性地被一个或多个卤素原子、硝基、腈、三氟甲基、乙烯、甲硫基、直链或支链C1-C4烷基、直链或支链C1-C3烷氧基基团取代的噻吩基， • C6 2-氧代环烷基基团 - R2代表甲基或庚基， - m，n等于1， - V代表CH2， - X-Y代表-N- (C=O) -，-CH-O-，- Z代表被一个或多个三氟甲基基团、卤素原子或直链C1-C4烷基基团取代的苯基。
• [EN] 1,2,4-TRIAZINES DERIVATIVES, PREPARATION THEREOF AND USE THEREOF IN HUMAN THERAPEUTICS<br/>[FR] DERIVES DE 1,2,4-TRIAZINES, PREPARATION DE CEUX-CI ET UTILISATION DE CEUX-CI DANS DES AGENTS THERAPEUTIQUES HUMAINS
  申请人：PF MEDICAMENT

  公开号：WO2005080354A1

  公开（公告）日：2005-09-01

  The invention relates to 3,5-dioxo-(2H,4H)-1,2,4-triazine derivatives of general formulae (I or II), in which in particular: R1 represents hydrogen, a linear or branched C1-C6 alkyl or alkoxy radical, a C5-C6 cycloalkyl radical, a phenyl (C1-C2) alkyl radical or a phenyl radical;-R2 represents hydrogen, a linear or branched Cl-C7 alkyl radical, or a C1-C6 alkyl radical substituted with groups such as trifluoromethyl or phenyl;- linker represents a C2-C6 alkyl chain or -(CH2)n-O- (n = 2 to 5), - R3 represents a group of general formula below for which X = O, linker can be connected to the ortho-, meta- or para-positions of the aromatic of the group R3, R4, R5, R6, R7 and R8 represent hydrogen or fluorine, R9, Rio and R11 represent hydrogen or a linear or branched Cl-C5 alkyl group, in particular R9 and Rio represent the methyl group and R11 represents hydrogen or the ethyl group.

  这项发明涉及一般式(I或II)的3,5-二氧代-(2H,4H)-1,2,4-三嗪衍生物，其中特别是：R1代表氢、线性或支链的C1-C6烷基或烷氧基、C5-C6环烷基、苯基(C1-C2)烷基或苯基；-R2代表氢、线性或支链的Cl-C7烷基，或C1-C6烷基，其上带有三氟甲基或苯基等基团；-连接物代表C2-C6烷基链或-(CH2)n-O- (n = 2至5)，- R3代表下述一般式的基团，其中X = O，连接物可以连接到R3基团的芳香环的邻位、间位或对位，R4、R5、R6、R7和R8代表氢或氟，R9、Rio和R11代表氢或线性或支链的Cl-C5烷基，特别是R9和Rio代表甲基，R11代表氢或乙基基团。
• 3,5-dioxo-(2H,4H)-1,2,4-triazine derivatives as 5HT.sub.1A ligands
  申请人：Pierre Fabre Medicament

  公开号：US05591743A1

  公开（公告）日：1997-01-07

  A 3,5-dioxo-(2H,4H)-1,2,4-triazine compounds of formula I ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, represent hydrogen or C.sub.1 -C.sub.6 alkyl, n is 2 to 6, inclusive, A represents aryl piperazino II ##STR2## the Ar grouping representing phenyl, naphthyl, pyrimidyl, or pyridyl, unsubstituted or substituted by C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, hydroxy, trifluoromethyl, or halogen, or III benzodioxanyl-methyl-amino or pyridodioxanyl-methyl-amino ##STR3## in which R represents hydrogen or C.sub.1 -C.sub.3 alkyl and X represents a nitrogen or carbon atom, therapeutically-acceptable salts and enantiomers thereof, pharmaceutical compositions thereof, and method for treatment of diseases requiring a 5HT.sub.1A receptor agonist therewith.

  公式I为3,5-二氧代-(2H,4H)-1,2,4-三嗪化合物，其化学式为##STR1## 其中：R.sub.1和R.sub.2相同或不同，代表氢或C.sub.1-C.sub.6烷基，n为2到6，包括2和6，A代表芳基哌嗪II##STR2## 其中Ar基团代表苯基、萘基、嘧啶基或吡啶基，未取代或取代为C.sub.1-C.sub.3烷基、C.sub.1-C.sub.3烷氧基、羟基、三氟甲基或卤素，或III苯并二氧杂环基-甲基-氨基或吡啶二氧杂环基-甲基-氨基##STR3## 其中R代表氢或C.sub.1-C.sub.3烷基，X代表氮或碳原子，其治疗上可接受的盐和对映体，其制药组合物以及治疗需要5HT.sub.1A受体激动剂的疾病的方法。