2,3,4,5-Tetrahydro-3-(Phenylmethyl)-1H-[1,2,5]Triazepino[1,2-a][1,2,4]-Benzotriazine-7(8H)-Thione | 125605-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,5-Tetrahydro-3-(Phenylmethyl)-1H-[1,2,5]Triazepino[1,2-a][1,2,4]-Benzotriazine-7(8H)-Thione
• 英文别名: 3-benzyl-2,4,5,8-tetrahydro-1H-[1,2,5]triazepino[1,2-a][1,2,4]benzotriazine-7-thione
• CAS: 125605-26-7
• 化学式: C₁₈H₂₀N₄S
• 分子量: 324.45
• InChiKey: YIUWDCKPAFXGNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  53.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Hexahydro-1-(2-nitrophenyl)-5-(phenylmethyl)-1H-1,2,5-triazepine 、 N,N'-硫羰基二咪唑 在 氯仿 、 Heptane chloroforme 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 以gave pure titled product, mp=125°-127°的产率得到2,3,4,5-Tetrahydro-3-(Phenylmethyl)-1H-[1,2,5]Triazepino[1,2-a][1,2,4]-Benzotriazine-7(8H)-Thione
  参考文献：
  名称：

  2,3,4,5-tetrahyd

  摘要：

  本文披露了新型的1,2,3,4,5,6-六氢[1,3,6]三唑环[1,2-a]苯并咪唑的I和II式：其中R.sup.1可能是苯基，m-或p-硝基苯基，m-或p-甲基磺酰氨基苯基，萘基，萘单取代硝基或甲基磺酰氨基，苯并呋喃基，2-嘧啶基，2-或4-吡啶基，2-或4-萘啉基，吡嗪基，异喹啉基或喹啉基；R.sup.2可能是氢；C.sub.1-C.sub.8烷基；苯基(C.sub.1-C.sub.4)烷基或取代的苯基(C.sub.1-C.sub.4)烷基，其中苯基可以有一到三个来自C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，氟，氯或溴的取代基；苯基或取代苯基，其中苯基取代基与取代苯基(C.sub.1-C.sub.4)烷基相同；2-或4-嘧啶基；吡嗪基；咪唑基；C.sub.1-C.sub.4烷酰基；卤代或二卤代-(C.sub.1-C.sub.4)烷酰基，其中卤是氟或氯；苯甲酰基或在苯环上被一或两个C.sub.1-C.sub.4烷基取代的苯甲酰基；C.sub.1-C.sub.4烷酰氧基；C.sub.1-C.sub.4烷基氨基(C.sub.1-C.sub.4烷酰基；C.sub.1-C.sub.4烷氧羰基；C.sub.1-C.sub.4烷基氨基羰基；苯基氨基羰基，其中苯基可能有一到三个C.sub.1-C.sub.4烷基取代基；苯氧基或萘氧基-(C.sub.1-C.sub.4)烷基，其中苯基或萘基环可能被一到三个C.sub.1-C.sub.4烷基取代基取代；C.sub.1-C.sub.4烷基磺酰基；(C.sub.1-C.sub.4)烷基-或N-二(C.sub.1-C.sub.4烷基)羧酰胺基(C.sub.1-C.sub.4)烷基；N-苯基或取代苯基-羧酰胺-(C.sub.1-C.sub.4)烷基，其中苯基可以像上述的C.sub.1-C.sub.4烷基取代苯基一样被取代；氰基；两个N原子被C.sub.1-C.sub.4烷基取代的氨基甲酸酰基；和C.sub.1-C.sub.4烷基脲基；以及R.sup.3和R.sup.4独立地选自氢，C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，氟和氯，或它们的酸加成盐。具有特定R.sup.2值的I和II式化合物是抗心律失常或抗缺血剂。其余的R.sup.2值提供了I和II式中间体化合物。本文还披露了一种新型的四氢-3-取代-7-取代-1H[1,2,5]三唑环[1,2-a][1,2,4]苯并三嗪，其中7取代基可以是--SMe，--Cl或Br，而3取代基与上述I和II式中的R.sup.2相同。这些化合物也用作上述II式抗心律失常剂的中间体。

  公开号：

  US04935515A1

文献信息

• 1,4-SUBSTITUTED-2,3,5,6-TETRAHYDRO 1,3,6]TRIAZOCINO 1,2-a]BENZIMIDAZOLES AND INTERMEDIATES THEREFOR
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0358749A1

  公开（公告）日：1990-03-21
• US4882323A
  申请人：——

  公开号：US4882323A

  公开（公告）日：1989-11-21
• US4935515A
  申请人：——

  公开号：US4935515A

  公开（公告）日：1990-06-19
• [EN] 1,4-SUBSTITUTED-2,3,5,6-TETRAHYDRO[1,3,6]TRIAZOCINO[1,2-a]BENZIMIDAZOLES AND INTERMEDIATES THEREFOR
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：WO1989008111A1

  公开（公告）日：1989-09-08

  (EN) Disclosed herein are novel 1,4-substituted-2,3,5,6-tetrahydro[1,3,6]triazocino[1,2-a]benzimidazole of formulae (I) and (II), wherein R1 may be phenyl, m- or p-nitrophenyl, m- or p-methylsulfonylaminophenyl, naphthyl, naphthyl mono-substituted by nitro or methylsulfonylamino, benzofurazanyl, 2-pyrimidinyl, 2- or 4-pyridinyl, 2- or 4-naphthyridinyl, pyrazinyl, isoquinolinyl, or quinolinyl; R2 may be hydrogen; C1-C8 alkyl; C1-C4 alkylphenyl or C1-C4 alkyl-substituted-phenyl, in which phenyl may have one to three substituents selected from C1-C4 alkyl, C1-C4 alkoxy, fluorine, chlorine or bromine; phenyl or substituted-phenyl in which the phenyl substituents are the same as for C1-C4 alkyl-substituted-phenyl; 2- or 4-pyrimidinyl; pyrazinyl; imidazinyl; C1-C4 alkanoyl; halo or dihalo-(C1-C4)alkanoyl, in which halo is fluoro or chloro; benzoyl or benzoyl substituted on the phenyl ring by one or two C1-C4 alkyl groups; C1-C4 alkanoyloxy; C1-C4 alkylamino(C1-C4)alkanoyl; C1-C4 alkyloxycarbonyl; C1-C4 alkylaminocarbonyl; phenylaminocarbonyl in which phenyl may have one to three C1-C4 alkyl groups; phenyloxy or naphthyloxy(C1-C4)alkyl in which the phenyl or naphthyl ring may be substituted by one to three C1-C4 alkyl groups; C1-C4 alkylsulfonyl; N-(C1-C4)alkyl- or N-(C1-C4)dialkylcarboxamido(C1-C4)alkyl; N-phenyl or substituted phenyl-carboxamido(C1-C4)alkyl in which phenyl may be substituted as above for C1-C4 alkyl-substituted phenyl; cyano; amidino in which each N atom is substituted by a C1-C4 alkyl group; and C1-C4 alkylguanidino; and R3 and R4 are, independently, selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, fluorine and chlorine, or acid addition salts thereof. Compounds of formulae (I) and (II) having certain values of R2 are antiarrhythmic or antiischaemic agents. The remaining values of R2 provide intermediate compounds of formulae (I) and (II). Also disclosed herein a novel tetrahydro-3-substituted-7-substituted-1H-[1,2,5]triazepino[1,2-a][1,2,4]benzotriazines, wherein the 7 substituent may be -SMe, =S, =O, Cl or Br and the 3 substituent is the same as R2 in formulae (I) and (II) above. These compounds also serve as intermediates for the production of the antiarrhythmic agents of formula (II) above.(FR) On a mis au point de nouvelles tétrahydro[1,3,6]-2,3,5,6 triazocino[1,2-a] substituées en position 1,4 des formules (I) et (II), dans lesquelles R1 peut représenter du phényle, m- ou p- nitrophényle, m- ou p- méthylsulfonylaminophényle, naphtyle, naphtyle mono substitué par du nitro ou du méthylsulfonylamino, benzofurazanyle, 2-pyrimidinyle, 2- ou 4-pyridinyle, 2- ou 4- naphthyridinyle, pyrazinyle, isoquinolinyle, ou quinolinyle. R2 peut représenter de l'hydrogène; alkyle C1-C8; alkylphényle C1-C4 ou phényle à substitution d'alkyle C1-C4, dans lesquels le phényle peut comporter un à trois substituants choisis parmi alkyle C1-C4, alkoxy C1-C4, fluor, chlore, brome, phényle ou phényle substitué dans lequel les substituants du phényle sont identiques à ceux du phényle à substitution d'alkyle C1-C4; 2- ou 4-pyrimidinyle; pyrazinyle; imidazynyle; alkanoyle C1-C4; halo ou dihalo-(C1-C4)alkanoyle, dans lequel halo représente fluoro ou chloro; benzoyle ou benzoyle substitué dans l'anneau de phényle par un ou deux groupes d'alkyle C1-C4; alkanoyloxy C1-C4; C1-C4 alkylamino(C1-C4)alkanoyle; alkyloxycarbonyle C1-C4; alkylaminocarbonyle C1-C4; phénylaminocarbonyle dans lequel le phényle peut avoir un à trois groupes d'alkyle C1-C4; phényloxy ou naphthyloxy(C1-C4)alkyle dans lequel l'anneau de phényle ou de naphthyle peut être substitué par un à trois groupes d'alkyle C1-C4; alkylsulfonyle C1-C4; N-(C1-C4)alkyl- ou N-(C1-C4) dialkylcarboxamido (C1-C4) alkyle; N-phényle ou phényl-carboxamido-(C1-C4)alkyle substitué dans lequel le phényle peut être substitué comme ci-dessus pour du phényle à substitution d'alkyle C1-C4; cyano; amidino dans lequel chaque atome N est substitué par un groupe alkyle C1-C4; et alkylguanidino C1-C4; R3 et R4 sont indépendamment choisis parmi hydrogène, alkyle C1-C4, alkoxy C1-C4, fluor et chlore, ou des sels d'addition acides de ceux-ci. Des composés des formules (I) et (II) ayant certaines valeurs de R2 sont des agents antiarythmiques ou antiischémiques. Les valeurs restantes de R2 fournissent des composés intermédiaires des formules (I) et (II). On a également mis au point de nouvelles têtrahydro - 1H-[1,2,5] triazepinol[1,2-a][1,2,4] benzotriazines à substitution en position 3 et 7, dans lesquelles le substituant en position 7 peut être -SMe, =S, =O, C1 ou Br, et le substituant en position 3 est identique à R2 dans les formules (I) et (II) précitées. Ces composés servent également d'intermédiaires pour la production des agents antiarythmiques de la formule (II) précitée.
• 2,3,4,5-tetrahyd
  申请人：American Home Products Corporation

  公开号：US04935515A1

  公开（公告）日：1990-06-19

  Disclosed herein are novel 1,2,3,4,5,6-hexahydro[1,3,6]triazocino[1,2-a]benzimidazole of Formulas I and II: ##STR1## wherein R.sup.1 may be phenyl, m- or p-nitrophenyl, m- or p-methylsulfonylaminophenyl, napthtyl, naphthyl mono-substituted by nitro or methylsulfonylamino, benzofurazanyl, 2-pyrimidinyl, 2- or 4-pyridinyl, 2- or 4-naphthyridinyl, pyrazinyl, isoquinolinyl, or quinolinyl; R.sup.2 may be hydrogen; C.sub.1 -C.sub.8 alkyl; phenyl(C.sub.1 -C.sub.4)alkyl or substituted-phenyl(C.sub.1 -C.sub.4)alkyl, in which phenyl may have one to three substituents selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine, chlorine or bromine; phenyl or substituted-phenyl in which the phenyl substituents are the same as for substituted-phenyl (C.sub.1 -C.sub.4)alkyl; 2- or 4-pyrimidinyl; pyrazinyl; imidazolyl; C.sub.1 -C.sub.4 alkanoyl; halo or dihalo-(C.sub.1 -C.sub.4)alkanoyl, in which halo is fluoro or chloro; benzoyl or benzoyl substituted on the phenyl ring by one or two C.sub.1 -C.sub.4 alkyl groups; C.sub.1 -C.sub.4 alkanoyloxy; C.sub.1 -C.sub.4 alkylamino(C.sub.1 -C.sub.4 alkanoyl; C.sub.1 -C.sub.4 alkyloxycarbonyl; C.sub.1 -C.sub.4 alkylaminocarbonyl; phenylaminocarbonyl in which phenyl may have one to three C.sub.1 -C.sub.4 alkyl groups; phenyloxy or naphthyloxy-(C.sub.1 -C.sub.4)alkyl in which the phenyl or naphthyl ring may be substituted by one to three C.sub.1 -C.sub.4 alkyl groups; C.sub.1 -C.sub.4 alkylsulfonyl; (C.sub.1 -C.sub.4)alkyl- or N-di-(C.sub.1 -C.sub.4 alkyl)carboxamido(C.sub.1 -C.sub.4)alkyl; N-phenyl or substituted phenyl-carboxamido-(C.sub.1 -C.sub.4)alkyl in which phenyl may be substituted as above for C.sub.1 -C.sub.4 alkyl-substituted phenyl; cyano; amidino in which each N atom is substituted by a C.sub.1 -C.sub.4 alkyl group; and C.sub.1 -C.sub.4 alkylguanidino; and R.sup.3 and R.sup.4 are, independently, selected from hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluorine and chlorine, or acid addition salts thereof. Compounds of formulas I and II having certain values of R.sup.2 are antiarrhythmic or antiischaemic agents. The remaining values of R.sup.2 provide intermediate compounds of formulas I and II. Also disclosed herein a novel tetrahydro-3-substituted-7-substituted-1H[1,2,5]triazepino[1,2-a][1,2,4]be nzotriazines, wherein the 7 substituent may be --SMe, --Cl or Br and the 3 substituent is the same as R.sup.2 in formulas I and II above. These compounds also serve as intermediates for the production of the antiarrhythmic agents for formula II above.

  本文披露了新型的1,2,3,4,5,6-六氢[1,3,6]三唑环[1,2-a]苯并咪唑的I和II式：其中R.sup.1可能是苯基，m-或p-硝基苯基，m-或p-甲基磺酰氨基苯基，萘基，萘单取代硝基或甲基磺酰氨基，苯并呋喃基，2-嘧啶基，2-或4-吡啶基，2-或4-萘啉基，吡嗪基，异喹啉基或喹啉基；R.sup.2可能是氢；C.sub.1-C.sub.8烷基；苯基(C.sub.1-C.sub.4)烷基或取代的苯基(C.sub.1-C.sub.4)烷基，其中苯基可以有一到三个来自C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，氟，氯或溴的取代基；苯基或取代苯基，其中苯基取代基与取代苯基(C.sub.1-C.sub.4)烷基相同；2-或4-嘧啶基；吡嗪基；咪唑基；C.sub.1-C.sub.4烷酰基；卤代或二卤代-(C.sub.1-C.sub.4)烷酰基，其中卤是氟或氯；苯甲酰基或在苯环上被一或两个C.sub.1-C.sub.4烷基取代的苯甲酰基；C.sub.1-C.sub.4烷酰氧基；C.sub.1-C.sub.4烷基氨基(C.sub.1-C.sub.4烷酰基；C.sub.1-C.sub.4烷氧羰基；C.sub.1-C.sub.4烷基氨基羰基；苯基氨基羰基，其中苯基可能有一到三个C.sub.1-C.sub.4烷基取代基；苯氧基或萘氧基-(C.sub.1-C.sub.4)烷基，其中苯基或萘基环可能被一到三个C.sub.1-C.sub.4烷基取代基取代；C.sub.1-C.sub.4烷基磺酰基；(C.sub.1-C.sub.4)烷基-或N-二(C.sub.1-C.sub.4烷基)羧酰胺基(C.sub.1-C.sub.4)烷基；N-苯基或取代苯基-羧酰胺-(C.sub.1-C.sub.4)烷基，其中苯基可以像上述的C.sub.1-C.sub.4烷基取代苯基一样被取代；氰基；两个N原子被C.sub.1-C.sub.4烷基取代的氨基甲酸酰基；和C.sub.1-C.sub.4烷基脲基；以及R.sup.3和R.sup.4独立地选自氢，C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，氟和氯，或它们的酸加成盐。具有特定R.sup.2值的I和II式化合物是抗心律失常或抗缺血剂。其余的R.sup.2值提供了I和II式中间体化合物。本文还披露了一种新型的四氢-3-取代-7-取代-1H[1,2,5]三唑环[1,2-a][1,2,4]苯并三嗪，其中7取代基可以是--SMe，--Cl或Br，而3取代基与上述I和II式中的R.sup.2相同。这些化合物也用作上述II式抗心律失常剂的中间体。