3-(N-methyl-N-tetrazol-5-ylamino)aniline | 152813-61-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(N-methyl-N-tetrazol-5-ylamino)aniline
• 英文别名: 3-›(N-methyl-N-(tetrazol-5-yl)amino)aniline；3-N-methyl-3-N-(2H-tetrazol-5-yl)benzene-1,3-diamine
• CAS: 152813-61-1
• 化学式: C₈H₁₀N₆
• 分子量: 190.208
• InChiKey: ARAKJQLREFQVCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1-cyclohexyl-5-(3,3-dimethyl-2-oxo-butyl)-2,4-dioxo-1,2,4,5-tetrahydro-1,3,5-benzotriazepin-3-yl)-acetic acid 、 3-(N-methyl-N-tetrazol-5-ylamino)aniline 生成 2-[1-cyclohexyl-5-(3,3-dimethyl-2-oxo-butyl)-2,4-dioxo-1,2,4,5-tetrahydro-1,3,5-benzotriazepin-3-yl]-N-{3-[methyl-(2H-tetrazol-5-yl)-amino]-phenyl}-acetamide
  参考文献：
  名称：

  Benzotriazepine derivatives and their use as gastrin and cholecystokinin receptor ligands

  摘要：

  本发明涉及一种式（I）的化合物。该化合物可用于治疗胃泌素相关疾病。

  公开号：

  US20070082892A1
• 作为产物：
  描述：

  N-methyl-N-(3-nitrophenyl)cyanamide 在 10% palladium on active carbon sodium azide 、 氯化铵 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.82h， 生成 3-(N-methyl-N-tetrazol-5-ylamino)aniline
  参考文献：
  名称：

  Controlled Modification of Acidity in Cholecystokinin B Receptor Antagonists:  N-(1,4-Benzodiazepin-3-yl)-N ‘-[3-(tetrazol-5-ylamino)phenyl]ureas

  摘要：

  The design, synthesis, and biological activity of a novel series of CCK-B receptor antagonists (1) which incorporate a tetrazol-5-ylamino functionality attached to the phenyl ring of the arylurea moiety of L-365,260 are described. In these compounds, the acidity of the tetrazole was gradually modified by utilization of simple conformational constraints, and X-ray crystallographic data were obtained to support the conformational dependence of the pK(a) of the aminotetrazoles. Compounds to emerge from the present work such as 1f and 2c,d are among the highest affinity and, in the case of 1f, most selective (CCK-A/CCK-B, 37 000) antagonists so far reported for this receptor. The C-5-cyclohexyl compound 2c (L-736,380) dose-dependently inhibited gastric acid secretion in anesthetized rats (ID50, 0.064 mg/kg) and er vivo binding of [I-125]CCK-8S in BKTO mice brain membranes (ED(50), 1.7 mg/kg) and is one of the most potent acidic CCK-B receptor antagonists yet described.

  DOI：

  10.1021/jm9506736

文献信息

• Benzodiazepine derivatives
  申请人：Merck, Sharp & Dohme Ltd.

  公开号：US05681833A1

  公开（公告）日：1997-10-28

  Compounds of Formula (I), and salts and prodrugs thereof, wherein said formula, R.sup.1 represents certain optionally substituted alkyl or C.sub.3-7 cycloalkyl; R.sup.2 represents (II) or (III), where m is 0, 1, 2 or 3; R.sup.9 is H or C.sub.1-6 alkyl; R.sup.10 is imidazolyl, triazolyl or tetrazolyl, and R.sup.11 is H, C.sub.1-6 alkyl or halo; R.sup.3 is C.sub.1-6 alkyl, halo or NR.sup.6 R.sup.7 ; R.sup.4 is C.sub.1-7 alkyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkylC.sub.1-4 alkyl, C.sub.6-10 bicycloalkyl, optionally substituted aryl, or NR.sub.12 R.sub.13 ; R.sup.5 is H or C.sub.1-4 alkyl; n is 0, 1, 2 or 3; which are CCK and/or gastrin antagonists useful in therapy.

  公式(I)的化合物，以及它们的盐和前药，其中所述公式中，R.sup.1代表某些可选地取代的烷基或C.sub.3-7环烷基；R.sup.2代表(II)或(III)，其中m为0、1、2或3；R.sup.9为H或C.sub.1-6烷基；R.sup.10为咪唑基、三唑基或四唑基，且R.sup.11为H、C.sub.1-6烷基或卤素；R.sup.3为C.sub.1-6烷基、卤素或NR.sup.6 R.sup.7；R.sup.4为C.sub.1-7烷基、C.sub.3-10环烷基、C.sub.3-10环烷基C.sub.1-4烷基、C.sub.6-10双环烷基、可选地取代的芳基，或NR.sub.12 R.sub.13；R.sup.5为H或C.sub.1-4烷基；n为0、1、2或3；它们是有用的治疗药物，用作CCK和/或胃泌素拮抗剂。
• Benzotriazepine derivatives and their use as gastrin and cholecystokinin receptor ligands
  申请人：Spencer John

  公开号：US20070082892A1

  公开（公告）日：2007-04-12

  This invention relates to a compound of formula (I). The compound is useful for the treatment of gastrin related disorders.

  本发明涉及一种式（I）的化合物。该化合物可用于治疗胃泌素相关疾病。
• Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion
  作者：Iain M. McDonald、James W. Black、Ildiko M. Buck、David J. Dunstone、Eric P. Griffin、Elaine A. Harper、Robert A. D. Hull、S. Barret Kalindjian、Elliot J. Lilley、Ian D. Linney、Michael J. Pether、Sonia P. Roberts、Mark E. Shaxted、John Spencer、Katherine I. M. Steel、David A. Sykes、Martin K. Walker、Gillian F. Watt、Laurence Wright、Paul T. Wright、Wei Xun

  DOI：10.1021/jm070139l

  日期：2007.6.1

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.
• 3-UREIDO SUBSTITUTED BENZODIAZEPIN-2-ONES HAVING CHOLECYSTOKININ AND/OR GASTRIN ANTAGONISTIC ACTIVITY AND THEIR USE IN THERAPY
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0636123A1

  公开（公告）日：1995-02-01
• US5681833A
  申请人：——

  公开号：US5681833A

  公开（公告）日：1997-10-28