1-(3-diethylaminopropyl)-3-aminoindazole | 88836-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-(3-diethylaminopropyl)-3-aminoindazole
• 英文别名: 1H-Indazole-1-propanamine, 3-amino-N,N-diethyl-；1-[3-(diethylamino)propyl]indazol-3-amine
• CAS: 88836-66-2
• 化学式: C₁₄H₂₂N₄
• 分子量: 246.355
• InChiKey: CSNYVGAJMYXMFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 1-(3-diethylaminopropyl)-3-aminoindazole 、 3-溴-N,N-二乙基丙氨氢溴酸盐 、 potassium carbonate 在 乙醚 、 盐酸 、 氯仿 、 Sodium sulfate-III 作用下， 以 氯仿 、 水 为溶剂， 反应 12.0h， 以to give 3.05 g of 1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)indazole in a yield of 52%的产率得到1-(3-diethylaminopropyl)-3-(3-diethylaminopropylamino)indazole
  参考文献：
  名称：

  3-Aminoindazole derivatives

  摘要：

  化合物的化学式（I）：##STR1## 其中W.sub.1是氢原子或##STR2##其中Y是C.sub.1-6烷基或具有C.sub.1-6烷基取代基的C.sub.1-6烷基；R.sub.1和R.sub.2各自独立地是氢原子或C.sub.1-6烷基，并且R.sub.1和R.sub.2可以与相邻的氮原子一起形成C.sub.4-6杂环环或含氮的C.sub.4-6杂环环，C.sub.4-6杂环环可以具有至少一个C.sub.1-6烷基，羟基或卤素原子；W.sub.2是氢原子或##STR3##其中Z是C.sub.1-6烷基或具有C.sub.1-6烷基取代基的C.sub.1-6烷基；R.sub.3和R.sub.4各自独立地是氢原子或C.sub.1-6烷基，并且R.sub.3和R.sub.4可以与相邻的氮原子一起形成C.sub.4-6杂环环或含氮的C.sub.4-6杂环环，C.sub.4-6杂环环可以具有至少一个C.sub.1-6烷基，羟基或卤素原子；当W.sub.1是氢原子时，W.sub.2是##STR4##当W.sub.2是氢原子时，W.sub.1是##STR5##以及其药学上可接受的酸加盐。

  公开号：

  US04549023A1
• 作为产物：
  描述：

  3-氨基吲唑 、 3-氯-1-二乙氨基丙烷 以20%的产率得到
  参考文献：
  名称：

  KAWAKUBO HIROMU; FUKUZAKI KENTARO; SONE TAKANORI, CHEM. AND PHARM. BULL., 35,(1987) N 6, 2292-2299

  摘要：

  DOI：

文献信息

• Studies on 3-aminoindazoles. I. Synthesis of 1- or 3-(substituted 3-amino)indazoles.
  作者：HIROMU KAWAKUBO、KENTARO FUKUZAKI、TAKANORI SONE

  DOI：10.1248/cpb.35.2292

  日期：——

  Various 1-or 3- (substituted 3-amino) indazoles with anti-inflammatory effects were synthesized by means of three methods, as follows. 1) Reactions of 3-aminoindazole (1) with acrylamides (2a and 2b) gave amide derivatives (3a and 3b) having a carbamoylethylamino group at the 3-position of 3a and 3b. The amide derivatives (3a and 3b) were converted to thioamide derivatives (4a and 4b) by treatment with P2S5. Electrode reduction of 4a and 4b gave 3- (substituted 3-amino) indazoles (5a and 5b). 2) The reaction of 1 with aminoalkyl. halides (6c-r) gave 3- (substituted 3-amino) indazoles (5c-r) and 1- (substituted 3-amino) indazoles (7c-r) in a ratio of 3 : 1. 3) The reaction of 1 with phthalic anhydride (8) gave 3-phthalimidoindazole (9). Compound 9 was allowed to react with aminoalkyl halides (6o-r) to give 1-substituted derivatives (10s-z) of 9, Reactions of 10a-z with hydrazine hydrate gave 1- (substituted 3-amino) indazole derivatives (5s-z).

  通过以下三种方法合成了各种具有消炎作用的 1-或 3-（取代的 3-氨基）吲唑。1) 3-氨基吲唑（1）与丙烯酰胺（2a 和 2b）反应，得到酰胺衍生物（3a 和 3b），3a 和 3b 的 3 位上有氨基甲酰乙氨基。酰胺衍生物（3a 和 3b）经 P2S5 处理后转化为硫代酰胺衍生物（4a 和 4b）。电极还原 4a 和 4b，得到 3-（取代的 3-氨基）吲唑（5a 和 5b）。2) 1 与氨基烷基卤化物（6c-r）反应，得到 3-（取代的 3-氨基）吲唑（5c-r）和 1-（取代的 3-氨基）吲唑（7c-r），比例为 3 : 1。化合物 9 与氨基烷基卤化物 (6o-r) 反应，得到 9 的 1-取代衍生物 (10s-z)，10a-z 与水合肼反应，得到 1-（取代的 3-氨基）吲唑衍生物 (5s-z)。
• 3-Aminoindazole derivatives
  申请人：Asahi, Kasei, Kogyo, Kabushiki, Kaisha

  公开号：US04474964A1

  公开（公告）日：1984-10-02

  A compound of the formula (I): ##STR1## wherein W.sub.1 is a hydrogen atom or a ##STR2## group wherein Y is a C.sub.1-6 alkylene group or a C.sub.1-6 alkylene group having a C.sub.1-6 alkyl group substituent; and R.sub.1 and R.sub.2 each independently is a hydrogen atom or a C.sub.1-6 alkyl group and R.sub.1 and R.sub.2 may form a C.sub.4-6 heterocyclic ring or a nitrogen-containing C.sub.4-6 heterocyclic ring together with the adjacent nitrogen atom and the C.sub.4-6 heterocyclic rings may have at least one C.sub.1-6 alkyl group, hydroxyl group or halogen atom; W.sub.2 is a hydrogen atom or a ##STR3## group wherein Z is a C.sub.1-6 alkylene group or a C.sub.1-6 alkylene group having a C.sub.1-6 alkyl group substituent; and R.sub.3 and R.sub.4 each independently is a hydrogen atom or a C.sub.1-6 alkyl group and R.sub.3 and R.sub.4 may form a C.sub.4-6 heterocyclic ring or a nitrogen-containing C.sub.4-6 heterocyclic ring together with the adjacent nitrogen atom and the C.sub.4-6 heterocyclic rings may have at least one C.sub.1-6 alkyl group, hydroxyl group or halogen atom; when W.sub.1 is a hydrogen atom, W.sub.2 is the ##STR4## group; and when W.sub.2 is a hydrogen atom, W.sub.1 is the ##STR5## group; and the pharmaceutically acceptable acid addition salt thereof having antiinflammatory, analgesic and digestive tract ulcer suppressing activity.

  化合物的式子(I)：##STR1## 其中W.sub.1是氢原子或##STR2##基团，其中Y是C.sub.1-6烷基链或具有C.sub.1-6烷基链取代基的C.sub.1-6烷基链; R.sub.1和R.sub.2各自独立地是氢原子或C.sub.1-6烷基链，且R.sub.1和R.sub.2可以与相邻的氮原子一起形成C.sub.4-6杂环环或含氮的C.sub.4-6杂环环，且C.sub.4-6杂环环可以具有至少一个C.sub.1-6烷基链、羟基或卤原子；W.sub.2是氢原子或##STR3##基团，其中Z是C.sub.1-6烷基链或具有C.sub.1-6烷基链取代基的C.sub.1-6烷基链; R.sub.3和R.sub.4各自独立地是氢原子或C.sub.1-6烷基链，且R.sub.3和R.sub.4可以与相邻的氮原子一起形成C.sub.4-6杂环环或含氮的C.sub.4-6杂环环，且C.sub.4-6杂环环可以具有至少一个C.sub.1-6烷基链、羟基或卤原子；当W.sub.1是氢原子时，W.sub.2是##STR4##基团; 当W.sub.2是氢原子时，W.sub.1是##STR5##基团; 以及其药学上可接受的酸盐，具有抗炎、镇痛和消化道溃疡抑制活性。
• Aminoindazole derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04533731A1

  公开（公告）日：1985-08-06

  A compound of the formula (I): ##STR1## wherein W.sub.1 and W.sub.2 each independently is a hydrogen atom or a ##STR2## group wherein Y is a n-C.sub.1-6 alkylene group or a n-C.sub.1-6 alkylene group having a C.sub.1-6 alkyl group substituent; and R.sub.1 and R.sub.2 each independently is a hydrogen atom or a C.sub.1-6 alkyl group, and ##STR3## group in ##STR4## group may form a saturated heterocyclic ring selected from the group consisting of morpholino, pyrrolidino, piperidino, homopiperidino and piperazino groups, and the saturated heterocyclic ring except the morpholino group may have at least one C.sub.1-4 alkyl group, hydroxyl group or halogen atom as a substituent; Z.sub.1 is a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, an amino group, a C.sub.1-3 alkyl group or a methoxy group; Z.sub.2 is a hydrogen atom or an amino group; when W.sub.1 and W.sub.2 are both hydrogen atoms, Z.sub.1 is a hydroxyl group or an iodine atom and Z.sub.2 is hydrogen atom, or Z.sub.1 and Z.sub.2 are both amino groups; when Z.sub.1 and Z.sub.2 are both hydrogen atoms, the ##STR5## group in either W.sub.1 or W.sub.2 is a morpholino group; when Z.sub.1 is a chlorine atom, a hydroxyl group, an iodine atom, a methyl group or a methoxy group, Z.sub.2 is a hydrogen atom; when Z.sub.1 is an amino group, Z.sub.2 is a hydrogen atom or an amino group; when Z.sub.1 is a methyl group, a methoxy group or an amino group, Z.sub.1 is in the 5-position; when Z.sub.1 is an iodine atom, Z.sub.1 is in the 5- or 7-position; and when Z.sub.1 and Z.sub.2 are both amino groups, Z.sub.1 and Z.sub.2 are in the 5- and 7-positions; and the physiologically acceptable acid addition salt thereof which compounds have pharmaceutical utility, e.g.: treating inflammation.

  化合物的式子（I）：##STR1## 其中W.sub.1和W.sub.2各自独立地是氢原子或##STR2##基团，其中Y是n-C.sub.1-6烷基或具有C.sub.1-6烷基取代基的n-C.sub.1-6烷基；R.sub.1和R.sub.2各自独立地是氢原子或C.sub.1-6烷基，并且##STR3##在##STR4##基团中可以形成选择自吗啡啶，吡咯烷，哌啶，同哌啶和哌嗪基团的饱和杂环环，除了吗啡啶基团的饱和杂环环可以具有至少一个C.sub.1-4烷基，羟基或卤素原子作为取代基；Z.sub.1是氢原子，氯原子，溴原子，碘原子，羟基，氨基，C.sub.1-3烷基或甲氧基；Z.sub.2是氢原子或氨基；当W.sub.1和W.sub.2都是氢原子时，Z.sub.1是羟基或碘原子，Z.sub.2是氢原子，或者Z.sub.1和Z.sub.2都是氨基；当Z.sub.1和Z.sub.2都是氢原子时，W.sub.1或W.sub.2中的##STR5##基团是吗啡啶基团；当Z.sub.1是氯原子，羟基，碘原子，甲基或甲氧基时，Z.sub.2是氢原子；当Z.sub.1是氨基时，Z.sub.2是氢原子或氨基；当Z.sub.1是甲基，甲氧基或氨基时，Z.sub.1在5位；当Z.sub.1是碘原子时，Z.sub.1在5-或7-位置；当Z.sub.1和Z.sub.2都是氨基时，Z.sub.1和Z.sub.2在5-和7-位置；以及其生理上可接受的酸加成盐，这些化合物具有药用价值，例如：用于治疗炎症。
• 3-aminoindazole derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04585869A1

  公开（公告）日：1986-04-29

  A compound of the formula (I): ##STR1## wherein W.sub.1 is a hydrogen atom or a ##STR2## wherein Y is a C.sub.1-6 alkylene group or a C.sub.1-6 alkylene group having a C.sub.1-6 alkyl group substituent; and R.sub.1 and R.sub.2 each independently is a hydrogen atom or a C.sub.1-6 alkyl group and R.sub.1 and R.sub.2 may form a C.sub.4-6 heterocyclic ring or a nitrogen-containing C.sub.4-6 heterocyclic ring together with the adjacent nitrogen atom and the C.sub.4-6 heterocyclic rings may have at least one C.sub.1-6 alkyl group, hydroxyl group or halogen atom; W.sub.2 is a hydrogen atom or a ##STR3## wherein Z is a C.sub.1-6 alkylene group or a C.sub.1-6 alkylene group having a C.sub.1-6 alkyl group substituent; and R.sub.3 and R.sub.4 each independently is a hydrogen atom or a C.sub.1-6 alkyl group and R.sub.3 and R.sub.4 may form a C.sub.4-6 heterocyclic ring or a nitrogen-containing C.sub.4-6 heterocyclic ring together with the adjacent nitrogen atom and the C.sub.4-6 heterocyclic rings may have at least one C.sub.1-6 alkyl group, hydroxyl group or halogen atom; when W.sub.1 is a hydrogen atom, W.sub.2 is the ##STR4## and when W.sub.2 is a hydrogen atom, W.sub.1 is the ##STR5## and the pharmaceutically acceptable acid addition salt thereof having antiinflammatory, analgesic and digestive tract ulcer suppressing activity.

  化合物的公式(I)：##STR1## 其中W.sub.1为氢原子或##STR2##其中Y是C.sub.1-6烷基或具有C.sub.1-6烷基取代基的C.sub.1-6烷基；R.sub.1和R.sub.2各自独立地为氢原子或C.sub.1-6烷基，且R.sub.1和R.sub.2可以与相邻氮原子一起形成C.sub.4-6杂环或含氮C.sub.4-6杂环，而C.sub.4-6杂环可以具有至少一个C.sub.1-6烷基，羟基或卤素原子；W.sub.2为氢原子或##STR3##其中Z是C.sub.1-6烷基或具有C.sub.1-6烷基取代基的C.sub.1-6烷基；R.sub.3和R.sub.4各自独立地为氢原子或C.sub.1-6烷基，且R.sub.3和R.sub.4可以与相邻氮原子一起形成C.sub.4-6杂环或含氮C.sub.4-6杂环，而C.sub.4-6杂环可以具有至少一个C.sub.1-6烷基，羟基或卤素原子；当W.sub.1为氢原子时，W.sub.2为##STR4##当W.sub.2为氢原子时，W.sub.1为##STR5##以及其药学上可以接受的酸加成盐，具有抗炎，镇痛和消化道溃疡抑制活性。
• 3-Aminoindazole derivatives and process for preparation thereof
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0049779A1

  公开（公告）日：1982-04-21

  A compound of the formula (I): wherein W, is a hydrogen atom or a group wherein Y is a C1-6 alkylene group or a C1-6 alkylene group having a C1-6 alkyl group substituent; and R, and R2 each independently is a hydrogen atom or a C1-6 alkyl group and R,, R2 and the adjacent nitrogen atom may form a C4-6 heterocyclic ring or a C4-6 heterocyclic ring containing an additional nitrogen atom and the C4-6 heterocyclic rings may have at least one C1-6 alkyl group, hydroxyl group or halogen atom; W2 is a hydrogen atom or a group wherein Z is a C1-6 alkylene group or a C1-6 alkylene group having a C1-6 alkyl group substituent; and R3 and R4 each independently is a hydrogen atom or a C1-6 alkyl group and R3, R4 and the adjacent nitrogen atom may form a C4-6 hetercyclic ring or a C4-6 heterocyclic ring containing an additional nitrogen atom and the C4-6 heterocyclic rings may have at least one C1-6 alkyl group, hydroxyl group or halogen atom; when W, is a hydrogen atom, W2 is the group; and when W2 is a hydrogen atom, W, is the group; and the pharmaceutically acceptable acid addition salt thereof.

  式 (I) 的化合物： 其中 W，是氢原子或 其中 Y 是 C1-6 亚烷基或具有 C1-6 烷基取代基的 C1-6 亚烷基；R 和 R2 各自独立地是氢原子或 C1-6 烷基，且 R、R2 和相邻的氮原子可形成 C4-6 杂环或含有额外氮原子的 C4-6 杂环，且 C4-6 杂环可具有至少一个 C1-6 烷基、羟基或卤素原子； W2 是氢原子或 其中 Z 为 C1-6 亚烷基或具有 C1-6 烷基取代基的 C1-6 亚烷基；以及 R3 和 R4 各自独立地为氢原子或 C1-6 烷基，且 R3、R4 和相邻氮原子可形成 C4-6 杂环或含有额外氮原子的 C4-6 杂环，且 C4-6 杂环可具有至少一个 C1-6 烷基、羟基或卤素原子； 当 W 是氢原子时，W2 是 基团；以及 当 W2 是氢原子时，W, 是基团；及 基团；及其药学上可接受的酸加成盐。