6-(4-苄基氨基-3-硝基苯基)-5-甲基-2,3,4,5-四氢哒嗪-3-酮 | 77469-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-(4-苄基氨基-3-硝基苯基)-5-甲基-2,3,4,5-四氢哒嗪-3-酮
• 英文名称: 6-(4-benzylamino-3-nitro-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one
• 英文别名: 5-methyl-6-[3'-nitro-4'-benzylamino-phenyl]-4,5-dihydro-3(2H)-pyridazinone；6-(4-(Benzylamino)-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one；3-[4-(benzylamino)-3-nitrophenyl]-4-methyl-4,5-dihydro-1H-pyridazin-6-one
• CAS: 77469-62-6
• 化学式: C₁₈H₁₈N₄O₃
• 分子量: 338.366
• InChiKey: YFJQPSKUCIGNDT-UHFFFAOYSA-N

物化性质

• 密度：
  1.33

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-(4-苄基氨基-3-硝基苯基)-5-甲基-2,3,4,5-四氢哒嗪-3-酮 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydrogensulfite 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-methyl-6-<2-(2-pyrrolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one
  参考文献：
  名称：

  Synthesis and biological activities of meribendan and related heterocyclic benzimidazolo-pyridazinones

  摘要：

  The synthesis of new heterocyclic benzimidazolo-pyridazinones is described. The new compounds were evaluated as inotropic agents with 'calcium-sensitizing' effects. 5-Methyl-6-[2-(3-pyrazolyl)-5-benzimidazolyl]-2,3,4,5-tetrahydro-pyridazin-3-one hydrochloride (meribendan) turned out to be the most interesting compound and was chosen for development as a positive inotrope.

  DOI：

  10.1016/0223-5234(93)90005-y
• 作为产物：
  描述：

  ethyl 4-(4-(benzylamino)-3-nitrophenyl)-3-methyl-4-oxo-butanoate 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以53.5%的产率得到6-(4-苄基氨基-3-硝基苯基)-5-甲基-2,3,4,5-四氢哒嗪-3-酮
  参考文献：
  名称：

  [EN] PIMOBENDAN MANUFACTURING PROCESS
  [FR] PROCÉDÉ DE FABRICATION DE PIMOBENDANE

  摘要：

  本发明通常涉及一种改进的制造公式(I)的非溶剂晶体化合物的工艺。本发明进一步涉及一种新的有价值的中间体化合物，用于商业合成哌莫苯丹，该化合物符合公式(I)nMeOH，其中n为1至2摩尔当量。此外，本发明还涉及使用该中间体化合物或通过本发明工艺获得的符合公式(I)的化合物，用于制造药物组成物。

  公开号：

  WO2011124638A1

文献信息

• [EN] PYRIDINONES<br/>[FR] PYRIDINONES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2015022332A1

  公开（公告）日：2015-02-19

  The present invention encompasses compounds of general formula (I) wherein the groups R1 to R3 and X1 through X6 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

  本发明涵盖了一般式(I)中的化合物，其中基团R1到R3和X1到X6的含义如权利要求和说明书中所述。本发明的化合物适用于治疗以细胞过度或异常增殖为特征的疾病，包括含有这些化合物的药物制剂及其用作药物的用途。
• PYRIDINONES
  申请人：ENGELHARDT Harald

  公开号：US20150051208A1

  公开（公告）日：2015-02-19

  The present invention encompasses compounds of general formula (I) wherein the groups R 1 to R 3 and X 1 through X 6 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

  本发明涵盖了一般式（I）的化合物，其中基团R1到R3和X1到X6具有权利要求和说明书中给定的含义。本发明的化合物适用于治疗以细胞过度或异常增殖为特征的疾病，包括含有这些化合物的药物制剂以及它们作为药物的用途。
• Benzotriazolyl-4,5-dihydro-3(2H)-pyridazinones
  申请人：Karl Thomae GmbH

  公开号：US04616018A1

  公开（公告）日：1986-10-07

  Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen; alkyl of 1 to 7 carbon atoms; cycloalkyl of 3 to 7 carbon atoms; monosubstituted alkyl of 1 to 3 carbon atoms, where the substituent is pyridyl, methylpyridyl, phenyl, mono-, di- or trisubstituted phenyl, where the substituents on the phenyl ring, which may be identical to or different from each other, are selected from the group consisting of one amino, one dimethylamino, one to two hydroxyls, one to three methoxys and one to three halogens; .omega.-monosubstituted alkyl of 2 to 4 carbon atoms, where the substituent is hydroxyl or di(alkyl of 1 to 3 carbon atoms)amino; phenyl; monohalo-phenyl; unsubstituted or monosubstituted straight or branched alkanoyl of 1 to 6 carbon atoms, where the substituent is phenyl, methoxyphenyl or cycloalkyl of 3 to 7 carbon atoms; or unsubstituted or monosubstituted phenylsulfonyl, where the substituent is methyl or methoxy; and, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as cardiotonics, hypotensives and antithrombotics.

  该化合物的结构式为##STR1##其中R.sub.1为氢；1至7个碳原子的烷基；3至7个碳原子的环烷基；1至3个碳原子的单取代烷基，其中取代基为吡啶基、甲基吡啶基、苯基、单取代苯基、双取代苯基或三取代苯基，苯环上的取代基（可以相同也可以不同）来自以下组合之一：一个氨基、一个二甲胺基、一个至两个羟基、一个至三个甲氧基和一个至三个卤素；2至4个碳原子的ω-单取代烷基，其中取代基为羟基或二（1至3个碳原子的烷基）氨基；苯基；单卤代苯基；未取代或单取代的直链或支链1至6个碳原子的烷酰基，取代基为苯基、甲氧基苯基或3至7个碳原子的环烷基；或未取代或单取代的苯基磺酰基，其中取代基为甲基或甲氧基；而R.sub.2为氢或1至3个碳原子的烷基；以及其非毒性、药理学上可接受的酸盐。这些化合物及其盐可用作心力衰竭药、降压药和抗血栓药。
• CRYSTALLINE PIMOBENDAN, PROCESS FOR THE PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION AND USE
  申请人：BOEREN Marinus Maria Martinus

  公开号：US20110152283A1

  公开（公告）日：2011-06-23

  The invention relates to a pharmaceutical composition containing pimobendan as an active ingredient. The invention also relates to a crystalline form of pimobendan, as well as to a combination of said crystalline form with at least one other therapeutically active ingredient. Moreover, the invention relates to uses of said crystalline form, as well as to a pharmaceutical composition containing it. Finally, the invention relates to a process for preparing a crystalline form of pimobendan.

  本发明涉及一种含有哌莫奔丹作为活性成分的药物组合物。本发明还涉及哌莫奔丹的晶体形式，以及该晶体形式与至少一种其他治疗活性成分的组合物。此外，本发明还涉及该晶体形式的用途，以及含有它的药物组合物。最后，本发明涉及一种制备哌莫奔丹晶体形式的方法。
• Synthesis of Novel Pyridazinonylbenzotriazoles
  作者：S. Shashidhar Reddy、B. George Vineel、S. Venkataiah、A. Naidu、P.K. Dubey

  DOI：10.14233/ajchem.2015.18894

  日期：——

  4-Chlorobenzaldehyde (1) was reacted with crotononitrile (2) in the presence of sodium cyanide yielding 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile (3) which on refluxing with concentrated HCl gave 4-(4-chlorophenyl)-3-methyl-4-oxobutyric acid (4). The latter, on treatment with fuming nitric acid, yielded 4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid (5), which on treatment with hydrazine hydrate gave 6-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazine-3-one (6). Azidation and reduction of 6 with sodium azide gave the amino derivative 7 which on reductive alkylation gave 10(a-i) followed by reduction with commercially available sodium hydrogen sulphide solution gave the substituted diamine derivative 11(a-i). The compound 7 directly undergoes reduction with sodium hydrogen sulphide yielding (8). Finally, 8 and 11(a-i) was converted into the target compounds by diazotized-cyclization with sodium nitrite giving pyridazinonylbenzotriazoles 9 and 12( a-i).

  在氰化钠存在下，4-氯苯甲醛（1）与巴豆腈（2）反应，生成 4-(4-氯苯基)-3-甲基-4-氧代丁腈（3），用浓盐酸回流，生成 4-(4-氯苯基)-3-甲基-4-氧代丁酸（4）。后者经发烟硝酸处理后得到 4-(4-氯-3-硝基苯基)-3-甲基-4-氧代丁酸（5），经肼水合物处理后得到 6-(4-氯-3-硝基苯基)-5-甲基-4,5-二氢-2H-哒嗪-3-酮（6）。用叠氮化钠对 6 进行叠氮和还原反应，得到氨基衍生物 7，再进行还原烷基化反应，得到 10(a-i)，然后用市售的硫化氢钠溶液进行还原反应，得到取代二胺衍生物 11(a-i)。化合物 7 直接与硫化氢钠发生还原反应，生成 (8)。最后，8 和 11(a-i)通过亚硝酸钠重氮化-环化反应转化为目标化合物，得到哒嗪酮基苯并三唑 9 和 12(a-i)。