1,1-双(2-丙炔基)肼 | 7422-83-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,1-双(2-丙炔基)肼
• 英文名称: 1,1-bis(2-propynyl)hydrazine
• 英文别名: 1,1-bis-(2-propynyl)hydrazine；1,1-Di-(2-propinyl)-hydrazin；1,1-Di(prop-2-inyl)hydrazin；gauche-Dipropargylhydrazin；1,1-bis(prop-2-ynyl)hydrazine
• CAS: 7422-83-5
• 化学式: C₆H₈N₂
• 分子量: 108.143
• InChiKey: FLCVMSCBIOSEIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.57
• 重原子数：
  8.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-丙炔-1-基肼 、 1,1-双(2-丙炔基)肼 、 2-甲基苯乙醛 以 甲醇 为溶剂， 反应 2.0h， 以15%的产率得到(E)-N-bis(2-propynyl)-N'-[2-(2-methylphenyl)ethylidene]hydrazine
  参考文献：
  名称：

  ß-PHENYLETHYLIDENEHYDRAZINE DERIVATIVES

  摘要：

  本发明提供了新的β-苯乙烯基肼衍生物，其制备过程以及作为药物组合物的用途。根据本发明，β-苯乙烯基肼衍生物通常符合以下一般式：

  公开号：

  US20110009492A1
• 作为产物：
  描述：

  Di-(prop-2-inyl)nitrosamin 、 氢化铝锂 以28%的产率得到
  参考文献：
  名称：

  VILENCHIK, YA. M.;PITIRIMOVA, S. G.;VORONTSOVA, P. A.;KOSVINTSEVA, L. S., XIMIYA ORGAN. SOEDIN. AZOTA, PERM, 1981, 42-46

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-丙炔-1-基肼 、 3-氟苯乙醛 在 1,1-双(2-丙炔基)肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (Z)-N-(2-propynyl)-N'-[2-(3-fluorophenyl)ethylidene]hydrazine 、 (E)-N-(2-propynyl)-N'-[2-(3-fluorophenyl)ethylidene]hydrazine
  参考文献：
  名称：

  N-Propynyl analogs of β-phenylethylidenehydrazines: Synthesis and evaluation of effects on glycine, GABA, and monoamine oxidase

  摘要：

  A group of beta-phenylethylidenehydrazines possessing a variety of substituents ( Me, OMe, Cl, F, and CF(3)) at the ortho-, meta-, or para- positions of the phenyl ring, in conjunction with either a N-bis-(2-propynyl) or a N-mono-(2-propynyl) moiety, were synthesized and compared to the novel neuroprotective drug beta-phenylethylidenehydrazine (PEH) with regard to their ability to inhibit the enzymes GABA- transaminase ( GABA- T) and monoamine oxidase (MAO)-A and -B in vitro in brain tissue. Two of the analogs synthesized (mono- and bis-N-propynylPEH) were also studied ex vivo in rats to compare their effects to those of PEH with regard to ability to inhibit GABA- T and MAO and to change brain levels of several important amino acids. Unlike PEH, none of the new drugs inhibited GABA- T in vitro at 10 or 100 mu M, and all of the drugs ( including PEH) were poor inhibitors ( at 10 mu M) of MAO-A and -B in vitro. The two analogs studied ex vivo inhibited GABA- T to a lesser extent than PEH, unlike PEH that did not elevate brain levels of GABA, and inhibited MAO-A and -B more potently than PEH. Interestingly, unlike PEH, the two analogs caused marked increases in brain levels of glycine; because of the current interest in drugs that increase glycine availability in the brain as potential antipsychotic drugs, these two analogs now warrant further investigation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.027

文献信息

• Methods for isolating propargylated aminoindans
  申请人：Frenkel Anton

  公开号：US20070112217A1

  公开（公告）日：2007-05-17

  Disclosed is a process for isolating from a reaction mixture a salt of a mono-propargylated aminoindan having the structure wherein R 1 is H, hydroxyl, alkoxy or wherein Y is O or S; R 2 and R 3 is each, independently, C 1-8 alkyl, C 6-12 aryl, C 6-12 aralkyl, each optionally halo substituted, or hydrogen; where the reaction mixture further comprises a solvent, a primary aminoindan having the structure wherein R 1 is defined as above, and a tertiary aminoindan having the structure the process comprising d) adding an acid to the reaction mixture; e) crystallizing the mono-propargylated aminoindan under conditions suitable for the formation of a crystalline salt of the mono-propargylated aminoindan; and f) recovering the crystalline salt of the mono-propargylated aminoindan, wherein the process is performed without addition of an organic solvent. Also disclosed are the crystalline diastereomeric salts produced by the process and pharmaceutical compositions containing the salts.

  公开了一种从反应混合物中分离出一种单丙炔基氨基间醚盐的方法，其具有以下结构：其中R1为H、羟基、烷氧基或；其中Y为O或S；R2和R3分别独立地为C1-8烷基、C6-12芳基、C6-12芳基烷基，每种均可选择地取代卤素，或氢；其中反应混合物进一步包括溶剂、具有以下结构的初级氨基间醚和具有以下结构的三级氨基间醚；所述方法包括d)向反应混合物中加入酸；e)在适合形成单丙炔基氨基间醚的结晶盐的条件下结晶化单丙炔基氨基间醚；和f)回收单丙炔基氨基间醚的结晶盐，其中该方法在不添加有机溶剂的情况下执行。还公开了该方法产生的晶体对映异构盐以及含有这些盐的药物组合物。
• R-Enantiomer of N-propargyl-1-aminoindan, its preparation and pharmaceutical compositions containing it
  申请人：Teva Pharmaceutical Industries Limited

  公开号：EP0436492A2

  公开（公告）日：1991-07-10

  R(+)-N-propargyl-1-aminoindan, its preparation and use and pharmaceutical compositions containing it. The novel compound was found to be useful for the treatment of human patients for Parkinson's disease, memory disorders, dementia of the Alzheimer type (DAT), depression and the hyperactive syndrome.

  R(+)-N-丙炔基-1-氨基茚烷，其制备、使用和含有该化合物的制药组合物。这种新型化合物被发现可用于治疗帕金森病、记忆障碍、阿尔茨海默病（DAT）、抑郁症和多动症等人类病患。
• [EN] R-ENANTIOMER OF N-PROPARGYL-1-AMINOINDAN, SALTS, COMPOSITIONS AND USES THEREOF<br/>[FR] R-ENANTIOMERE DE N-PROPARGYL-1-AMINO-INDANE, SELS, COMPOSITIONS ET UTILISATION DE CE COMPOSE
  申请人：TEVA PHARMACEUTICAL INDUSTRIES LTD.

  公开号：WO1995011016A1

  公开（公告）日：1995-04-27

  (EN) The subject invention provides R(+)-N-propargyl-1-aminoindan and pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions containing same. The subject invention also provides methods of treating a subject afflicted with Parkinson's disease, a memory disorder, dementia, depression, hyperactive syndrome, an affective illness, a neurodegenerative disease, a neurotoxic injury, brain ischemia, a head trauma injury, a spinal trauma injury, schizophrenia, an attention deficit disorder, multiple sclerosis, or withdrawal symptoms, using R(+)-N-propargyl-1-aminoindan or the pharmaceutically acceptable salt of the subject invention. The subject invention further provides a method of preventing nerve damage in a subject. Finally, the subject invention provides methods of preparing R(+)-N-propargyl-1-aminoindan, a salt thereof, and racemic N-propargyl-1-aminoindan.(FR) L'invention se rapporte à un composé R(+)-N-propargyl-1-amino-indane et à des sels pharmaceutiquement acceptables de ce composé ainsi qu'à des compositions pharmaceutiques le contenant. La présente invention se rapporte également à des procédés de traitement d'un sujet souffrant de la maladie de Parkinson, d'un trouble de la mémoire, de démence, de dépression, du syndrome d'hyperactivité, d'une maladie affective, d'une maladie neurodégénérative, d'une blessure neurotoxique, d'ischémie cérébrale, d'une blessure traumatique à la tête, d'une blessure traumatique rachidienne, de schizophrénie, d'un désordre de l'attention, de la sclérose en plaque, ou de symptômes de manque, à l'aide de R(+)-N-propargyl-1-amino-indane ou de sels pharmaceutiquement acceptables de ce composé. De plus, la présente invention se rapporte à un procédé permettant d'éviter les lésions des nerfs chez un sujet. Enfin l'invention se rapporte à des procédés de préparation de R(+)-N-propargyl-1-amino-indane, d'un sel de celui-ci et de N-propargyl-1-amino-indane racémique.

  本发明提供了R(+)-N-丙炔基-1-氨基茚及其医药上可接受的盐，以及包含其的制药组合物。本发明还提供了使用R(+)-N-丙炔基-1-氨基茚或本发明的医药上可接受的盐治疗帕金森病、记忆障碍、痴呆、抑郁症、多动症、情感疾病、神经退行性疾病、神经毒性损伤、脑缺血、头部创伤、脊髓创伤、精神分裂症、注意力缺陷障碍、多发性硬化症或戒断症状的方法。本发明还提供了一种预防主体神经损伤的方法。最后，本发明提供了制备R(+)-N-丙炔基-1-氨基茚、其盐和外消旋N-丙炔基-1-氨基茚的方法。
• Use of R-enantiomer of N-propargyl-1-aminoindan, salts, compositions and uses thereof
  申请人：Youdim B.H. Moussa

  公开号：US20070100001A1

  公开（公告）日：2007-05-03

  The subject invention provides methods of treating a subject afflicted with Parkinson's disease, memory disorder, depression, hyperactive syndrome, Attention Deficit Disorder, dementia, brain ischemia, stroke, head trauma injury, spinal trauma injury, neurotrauma, neurodegenerative disease, neurotoxic injury, multiple sclerosis, nerve damage, affective illness, schizophrenia or symptoms of withdrawal from an addictive substance, using the mesylate salt of R(+)-N-propargyl-1-aminoindan.

  该发明提供了使用R(+)-N-丙炔基-1-氨基茚的甲磺酸盐治疗帕金森病、记忆障碍、抑郁症、多动症、注意力缺陷障碍、痴呆症、脑缺血、中风、头部创伤、脊髓创伤、神经创伤、神经退行性疾病、神经毒性损伤、多发性硬化症、神经损伤、情感疾病、精神分裂症或从成瘾物质中戒断症状的方法。
• Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof
  申请人：Teva Pharmaceutical Industries, Ltd.

  公开号：US20030212145A1

  公开（公告）日：2003-11-13

  The subject invention provides R(+)-N-propargyl-1-aminoindan and pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions containing same. The subject invention also provides methods of treating a subject afflicted with Parkinson's disease, a memory disorder, dementia, depression, hyperactive syndrome, an effective illness, a neurodegenerative disease, a neurotoxic injury, stroke, brain ischemia, a head trauma injury, a spinal trauma injury, neurotrauma, schizophrenia, an attention deficit disorder, multiple sclerosis, or withdrawal symptoms, using R(+)-N-propargyl-1-aminoindan or the pharmaceutically acceptable salt of the subject invention. The subject invention further provides a method of preventing nerve damage in a subject. Finally, the subject invention provides methods of preparing R(+)-N-propargyl-1-aminoindan, a salt thereof, and racemic N-propargyl-1-aminoindan.

  本发明提供了R（+）-N-丙炔基-1-氨基茚和其药学上可接受的盐，以及含有它们的制药组合物。本发明还提供了使用R（+）-N-丙炔基-1-氨基茚或本发明的药学上可接受的盐治疗帕金森病、记忆障碍、痴呆症、抑郁症、多动症、有效疾病、神经退行性疾病、神经毒性损伤、中风、脑缺血、头部创伤、脊髓创伤、神经创伤、精神分裂症、注意力缺陷障碍、多发性硬化症或戒断症状的方法。本发明还提供了一种预防受试者神经损伤的方法。最后，本发明提供了制备R（+）-N-丙炔基-1-氨基茚、其盐和外消旋N-丙炔基-1-氨基茚的方法。