8-nitro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 8-nitro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine
• 英文别名: 8-nitro-6-(o-chlorophenyl)-1-(chloromethyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine；1-(chloromethyl)-6-(2-chlorophenyl)-8-nitro-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
• 化学式: C₁₇H₁₁Cl₂N₅O₂
• 分子量: 388.213
• InChiKey: MHPJBWVUKLHMDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-nitro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine 、 N,N-二丙基羟胺 以 dimethylformimide 为溶剂， 生成 8-nitro-1-[(dipropylamino)methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine
  参考文献：
  名称：

  1-[(Aminooxy)-methyl]-6-substituted-4H-s-triazolo[4,3-a][1,4]

  摘要：

  分子式为：##STR1## 其中R'o和R"o为氢或1至3个碳原子的烷基；R.sub.1为氢、氟、氯、溴、硝基、三氟甲基或烷基硫醚，其中烷基部分为1至3个碳原子；R.sub.2为苯基、邻氯苯基、邻氟苯基、2,6-二氟苯基和2-吡啶基，是由分子式I的化合物经多步反应制备而成：##STR2## 其中R.sub.1和R.sub.2如上所定义，X为氯或溴。分子式III的化合物，其制备中间体，化合物IIIA（III中R'o和R"o为氢的席夫碱）以及药理学上可接受的酸加成盐在鸟类和哺乳动物，包括人类中，可用作镇静剂、抗焦虑、抗抑郁、抗癫痫和肌肉松弛剂。

  公开号：

  US04009175A1

文献信息

• 1-[(Allylamino)-methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines
  申请人：The Upjohn Company

  公开号：US04021441A1

  公开（公告）日：1977-05-03

  Compounds of the formula II: ##STR1## wherein R is cyclopropyl, cyclopropylmethyl, or allyl; wherein R', R", and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms inclusive; and wherein R.sub.2, R.sub.3, and R.sub.4 are hydrogen, alkyl as defined above, fluoro, chloro, bromo, nitro, trifluoromethyl, or alkylthio in which alkyl is defined as above, are prepared by reacting a compound of the formula I. ##STR2## wherein R", R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are defined as above, and wherein X is chlorine or bromine, with an amine of the formula ##STR3## wherein R and R' are defined as above. The compounds of formula II and the pharmacologically acceptable acid salts thereof have tranquilizing, sedative, antianxiety, and anticonvulsant activity and can be used in animals and birds.

  公式II的化合物：其中R为环丙基、环丙基甲基或烯丙基；其中R'、R"和R₁为氢或1至3个碳原子的烷基；其中R₂、R₃和R₄为氢、如上所定义的烷基、氟、氯、溴、硝基、三氟甲基或烷基硫，其中烷基如上定义，通过将公式I的化合物与上述定义的R"、R₁、R₂、R₃和R₄，并且其中X为氯或溴的胺反应制备。公式II的化合物及其药理学上可接受的酸盐具有镇定、镇静、抗焦虑和抗惊厥活性，可用于动物和鸟类。
• [3-Substituted-5-[(di-methylamino)methyl]-4H-1,2,4-triazol-
  申请人：The Upjohn Company

  公开号：US04010177A1

  公开（公告）日：1977-03-01

  Compounds of the formula I: ##STR1## wherein R.sub.1 is hydroxymethyl, or -CH.sub.2 NR.sub.6 R.sub.7, in which R.sub.6 is -CH.sub.2 -C.tbd.CH, -CH.sub.2 -CH=CH.sub.2, ##STR2## or alkyl of 1 to 3 carbon atoms, inclusive; R.sub.7 is hydrogen or alkyl of 1 to 3 carbon atoms, or together ##STR3## is pyrrolidino, piperidino or morpholino; wherein R.sub.2 is hydrogen, chlorine or fluorine; wherein R.sub.3 is hydrogen, or fluorine if R.sub.2 is fluorine; wherein R.sub.4 is hydrogen, fluorine, chlorine, bromine, nitro, or trifluoromethyl; and wherein R.sub.5 is hydrogen, methyl or ethyl. These compounds, except those in which R.sub.7 is hydrogen, are produced by heating a compound of formula II: ##STR4## wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are defined as hereinabove, and wherein R'.sub.1 is the same as R.sub.1 except that in defining R'.sub.1,R.sub.7 may not be hydrogen, with aqueous formaldehyde in formic acid solution at reflux temperature (about 100.degree. C.). Compounds in which R.sub.7 are hydrogen require steps further shown in the specification. The compounds of formula I and their pharmacologically acceptable acid addition salts thereof have tranquilizing, anti-anxiety and anti-convulsant activity useful for the treatment of animals and man.

  公式I的化合物：##STR1## 其中R.sub.1是羟甲基或-CH.sub.2 NR.sub.6 R.sub.7，其中R.sub.6是-CH.sub.2 -C.tbd.CH，-CH.sub.2 -CH=CH.sub.2，##STR2##或包括1至3个碳原子的烷基; R.sub.7是氢或包括哒啶基，哌啶基或吗啡啶基; R.sub.2是氢，氯或氟; R.sub.3是氢，如果R.sub.2为氟，则为氟; R.sub.4是氢，氟，氯，溴，硝基或三氟甲基; R.sub.5是氢，甲基或乙基。除了R.sub.7为氢的化合物外，这些化合物是通过将公式II的化合物加热而产生的：##STR4##其中R.sub.2，R.sub.3，R.sub.4和R.sub.5的定义如上所述，而R'.sub.1与R.sub.1相同，但在定义R'.sub.1时，R.sub.7可能不是氢，在甲酸溶液中以回流温度（约100°C）与水甲醛反应。其中R.sub.7为氢的化合物需要在规范中进一步步骤。公式I的化合物及其药理学上可接受的酸加盐具有镇静，抗焦虑和抗惊厥活性，可用于动物和人的治疗。
• 1-[(Dialkylamino)met
  申请人：The Upjohn Company

  公开号：US04226772A1

  公开（公告）日：1980-10-07

  The compound of the formula ##STR1## wherein R' and R" are alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.1 is hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl or alkylthio in which the alkyl moiety is of 1 to 3 carbon atoms, inclusive; and wherein R.sub.2 is phenyl, o-chlorophenyl, o-fluorophenyl, or 2,6-difluorophenyl, is prepared by reacting a 1-halomethyl-6-phenyl-4H-s-triazo[4,3-a][1,4]-benzodiazepine with N,N-dimethylhydroxylamine and a strong base. The compound II and its pharmacologically acceptable acid addition salts have sedative and tranquilizing activity.

  化学式为##STR1##的化合物，其中R'和R"是1到3个碳原子的烷基；R.sub.1是氢、氟、氯、溴、硝基、三氟甲基或烷基硫基，其中烷基部分为1到3个碳原子；R.sub.2是苯基、邻氯苯基、邻氟苯基或2,6-二氟苯基。该化合物是通过将1-卤代甲基-6-苯基-4H-s-三唑[4,3-a][1,4]-苯并二氮平与N,N-二甲基羟胺和强碱反应制备而成。化合物II及其药学上可接受的酸盐具有镇静和安眠作用。
• 1-[(Hydroxyamino)methyl]-6-aryl-4H-s-triazolo[4,3-a][1,4]benzodiazepines
  申请人：The Upjohn Company

  公开号：US04039551A1

  公开（公告）日：1977-08-02

  Compounds of the formula ##STR1## wherein R.sub.o is hydrogen or alkyl of 1-3 carbon atoms, inclusive; wherein R.sub.1 is hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl or alkylthio in which the alkyl moiety is of 1 to 3 carbon atoms, inclusive; and wherein R.sub.2 is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl or 2-pyridyl, or the pharmaceutically acceptable acid addition salts thereof. The compounds are useful as sedatives, antianxiety agents, antidepressants, anticonvulsives and muscle-relaxing agents.

  化合物的公式为##STR1##其中R.sub.o是氢或1-3个碳原子的烷基; R.sub.1是氢、氟、氯、溴、硝基、三氟甲基或烷硫基，其中烷基部分为1至3个碳原子，包括; R.sub.2是苯基、o-氯苯基、o-氟苯基、2,6-二氟苯基或2-吡啶基，或其药学上可接受的酸盐。这些化合物可用作镇静剂、抗焦虑剂、抗抑郁剂、抗癫痫药和肌肉松弛剂。
• Novel derivatives of 4H-s-triazolo[4,3-.alpha.][1,4]benzodiazepines
  申请人：The Upjohn Company

  公开号：US04081452A1

  公开（公告）日：1978-03-28

  Compounds of the formula: ##STR1## wherein R'.sub.o and R".sub.o are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; R.sub.1 is hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, or alkylthio in which the alkyl moiety is of 1 to 3 carbon atoms, inclusive; R.sub.2 is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl and 2-pyridyl are prepared by multistep reactions from compounds of formula I: ##STR2## wherein R.sub.1 and R.sub.2 are defined as above and X is chlorine or bromine. Compounds of formula III, intermediates in the preparation thereof, Schiff's bases of compounds IIIA (III in which R'.sub.o and R".sub.o are hydrogen), and the pharmacologically acceptable acid addition salts are useful in birds and mammals, including man, as sedatives, antianxiety, antidepressant, anticonvulsive, and muscular relaxing agents.

  化合物的公式为：##STR1##其中R'.sub.o和R".sub.o是氢或1至3个碳原子的烷基，包括；R.sub.1是氢，氟，氯，溴，硝基，三氟甲基或烷基硫醚，其中烷基基团是1至3个碳原子，包括；R.sub.2是苯基，邻氯苯基，邻氟苯基，2,6-二氟苯基和2-吡啶基，通过从公式I的化合物进行多步反应制备：##STR2##其中R.sub.1和R.sub.2如上所定义，X是氯或溴。公式III的化合物，其制备的中间体，化合物IIIA的席夫碱（其中R'.sub.o和R".sub.o是氢），以及药理学上可接受的酸盐，在鸟类和哺乳动物中，包括人类，作为镇静剂，抗焦虑，抗抑郁，抗惊厥和肌肉松弛剂有用。