4-(4-Fluorobenzoyl)aminophenylhydrazine | 186544-89-8

• 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: 4-(4-Fluorobenzoyl)aminophenylhydrazine
• 英文别名: 4-fluoro-N-(4-hydrazinylphenyl)benzamide
• CAS: 186544-89-8
• 化学式: C₁₃H₁₂FN₃O
• 分子量: 245.256
• InChiKey: CQNFWPQVHONLMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-二甲氨基戊烷-2-酮 、 4-(4-Fluorobenzoyl)aminophenylhydrazine 在 盐酸 作用下， 以 乙醇 为溶剂， 以82%的产率得到N-[3-(2-dimethylaminoethyl)-2-methyl-1H-indol-5-yl]-4-fluorobenzamide
  参考文献：
  名称：

  N-[3-(2-Dimethylaminoethyl)-2-methyl-1H- indol-5-yl]-4-fluorobenzamide:  A Potent, Selective, and Orally Active 5-HT_1F Receptor Agonist Potentially Useful for Migraine Therapy

  摘要：

  Recent studies have demonstrated that selective 5-HT1F receptor agonists inhibit neurogenic dural inflammation, a model of migraine headache, indicating that these compounds may be effective therapies for the treatment of migraine pain. This communication describes the synthesis and discovery of a novel compound, N-[3-(2-dimethylamino)ethyl)-2-methyl-1H-indol-5-yl]-4-fluorobenzamide (4), which possesses high binding affinity and selectivity at the 5-HT1F receptor relative to more than 40 other serotonergic and nonserotonergic receptors examined.

  DOI：

  10.1021/jm0155190
• 作为产物：
  描述：

  N-(4-Amino-phenyl)-4-fluoro-benzamide 在 盐酸 、 sodium nitrite 、 tin(ll) chloride 作用下， 以60%的产率得到4-(4-Fluorobenzoyl)aminophenylhydrazine
  参考文献：
  名称：

  N-[3-(2-Dimethylaminoethyl)-2-methyl-1H- indol-5-yl]-4-fluorobenzamide:  A Potent, Selective, and Orally Active 5-HT_1F Receptor Agonist Potentially Useful for Migraine Therapy

  摘要：

  Recent studies have demonstrated that selective 5-HT1F receptor agonists inhibit neurogenic dural inflammation, a model of migraine headache, indicating that these compounds may be effective therapies for the treatment of migraine pain. This communication describes the synthesis and discovery of a novel compound, N-[3-(2-dimethylamino)ethyl)-2-methyl-1H-indol-5-yl]-4-fluorobenzamide (4), which possesses high binding affinity and selectivity at the 5-HT1F receptor relative to more than 40 other serotonergic and nonserotonergic receptors examined.

  DOI：

  10.1021/jm0155190

文献信息

• [EN] TREATMENT OF THE COMMON COLD OR ALLERGIC RHINITIS<br/>[FR] TRAITEMENT DU RHUME DE CERVEAU ET DES RHINITES ALLERGIQUES
  申请人：ELI LILLY AND COMPANY

  公开号：WO1998006402A1

  公开（公告）日：1998-02-19

  (EN) This invention provides methods for the treatment or amelioration of the symptoms of the common cold or allergic rhinitis which comprises administering to a mammal in need thereof a serotonin 5-HT1F agonist.(FR) La présente invention concerne une thérapie permettant de traiter le rhume de cerveau ou les rhinites allergiques, ou d'en atténuer les signes cliniques. Cette thérapie consiste en l'administration, à un mammifère le justifiant, d'un agoniste de la sérotonine 5-HTF1.

  这项发明提供了治疗或缓解普通感冒或过敏性鼻炎症状的方法，包括向需要治疗的哺乳动物施用5-羟色胺5-HT1F激动剂。
• Polymer bound carbodiimide coupling reagent
  申请人：Eli Lilly and Company

  公开号：US06126932A1

  公开（公告）日：2000-10-03

  This invention provides novel 5-HT.sub.1F agonists of Formula ##STR1## where X, R.sup.1, R.sup.2, and R.sup.3 are defined in the specification, which are useful for the treatment of migraine and associated disorders.

  这项发明提供了新颖的5-HT.sub.1F激动剂，其化学式为 ##STR1## 其中X、R.sup.1、R.sup.2和R.sup.3在说明书中有定义，可用于治疗偏头痛和相关疾病。
• N-\x9b2-substituted-3-(2-aminoethyl)-1H-indol-5-YL!-Amides: new 5-HT.sub.1F
  申请人：Eli Lilly and Company

  公开号：US05942536A1

  公开（公告）日：1999-08-24

  The invention provides novel 5-HT.sub.1f agonists of formula (I) where X, R.sup.1, R.sup.2, and R.sup.3 are defined in the specification, which are useful for the treatment of migraine and associate disorders. ##STR1##

  本发明提供了式(I)的新型5-HT.sub.1f激动剂，其中X、R.sup.1、R.sup.2和R.sup.3在规范中有定义，可用于治疗偏头痛及相关疾病。 ## STR1 ##
• 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta(7,6-B)indoles
  申请人：ELI LILLY AND COMPANY

  公开号：EP0749962A1

  公开（公告）日：1996-12-27

  The present invention provides novel agonists of the serotonin 5-HT1F receptor of formula I which are useful in a method of inhibiting neuronal protein extravasation without causing vasoconstriction. wherein: R1 and R2are independently hydrogen, C1-C4 alkyl, or -CH2CH2-Aryl where Aryl is phenyl, phenyl monosubstituted with halo, or 1-(C1-C6 alkyl) pyrazol-4-yl; Xis -OH, -NHC(O)R3, -NHC(Y)NHR4, -NHC(O)OR5, -C(O)R6 or -NHSO2R7; R3is C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloakyl, phenyl, substituted phenyl, naphthyl, (C1- C4 alkylene)phenyl, thienylmethyl, or a heterocycle; R4is C1-C6 alkyl, phenyl, or phenyl disubstituted with halo; R5is C1-C6 alkyl, C2-C6 alkenyl, benzyl or phenyl monosubstituted with halo; R6is C1-C6 alkyl, phenyl, or phenyl monosubstituted with halo or C1-C4 alkoxy; R7is dimethylamino, phenyl or phenyl monosubstituted with halo or C1-C4 alkyl; mis 0 or 1; nis 1 or 2; and Yis S or O; and parmaceutically acceptable salts and hydrates thereof, providing: Xis not -OH when m is 0, n is 1, and R1 and R2 are independently hydrogen or C1-C6 alkyl; and R3is not C1-C6 alkyl when m is 0, n is 1, and R1 and R2 are independently hydrogen or C1-C6 alkyl.

  本发明提供了式 I 的新型血清素 5-HT1F 受体激动剂，可用于抑制神经元蛋白外渗而不引起血管收缩的方法。 其中 R1 和 R2 独立地为氢、C1-C4 烷基或-CH2CH2-芳基，其中芳基为苯基、卤代单取代苯基或 1-(C1-C6烷基)吡唑-4-基； X为-OH、-NHC(O)R3、-NHC(Y)NHR4、-NHC(O)OR5、-C(O)R6 或-NHSO2R7； R3 是 C1-C6 烷基、C2-C6 烯基、C3-C8 环烷基、苯基、取代苯基、萘基、（C1-C4 亚烷基）苯基、噻吩甲基或杂环； R4 是 C1-C6 烷基、苯基或与卤代物二取代的苯基； R5 是被卤素单取代的 C1-C6 烷基、C2-C6 烯基、苄基或苯基； R6 是卤代或 C1-C4 烷氧基单取代的 C1-C6 烷基、苯基或苯基； R7 是二甲基氨基、苯基或与卤素或 C1-C4 烷基单取代的苯基； mis为 0 或 1； n 是 1 或 2；以及 Y 是 S 或 O；以及它们的法玛西亚可接受盐和水合物，条件是 当 m 为 0，n 为 1，且 R1 和 R2 独立为氢或 C1-C6 烷基时，X 不是-OH；以及 当 m 为 0，n 为 1，且 R1 和 R2 独立为氢或 C1-C6 烷基时，R3 不是 C1-C6 烷基。
• Use of serotonin 5-HT1F agonists for the prevention of migraine
  申请人：ELI LILLY AND COMPANY

  公开号：EP0832650A2

  公开（公告）日：1998-04-01

  This invention provides methods for the prevention of migraine which comprises administering to a mammal in need thereof a serotonin 5-HT1F agonist.

  本发明提供了预防偏头痛的方法，其中包括向有需要的哺乳动物施用血清素 5-HT1F 激动剂。