N-benzyl-6-(but-3-ynyloxy)hexan-1-amine | 102295-04-5

• 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: N-benzyl-6-(but-3-ynyloxy)hexan-1-amine
• 英文别名: N-[6-[(3-Butynyl)oxy]hexyl]benzenemethanamine；N-Benzyl-6-[(but-3-yn-1-yl)oxy]hexan-1-amine；N-benzyl-6-but-3-ynoxyhexan-1-amine
• CAS: 102295-04-5
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: QIQDCZAWYRKEIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  福莫特罗中间体2 、 N-benzyl-6-(but-3-ynyloxy)hexan-1-amine 反应 2.0h， 以73%的产率得到N-[5-((1R)-2-{benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Long-acting β₂ Adrenergic Receptor Agonists Incorporating Arylsulfonamide Groups

  摘要：

  A series of saligenin alkoxyalkylphenylsulfonamide beta(2) adrenoceptor agonists were prepared by reacting a protected saligenin oxazolidinone with alkynyloxyalkyl bromides, followed by Sonogashira reaction, hydrogenation, and deprotection. The meta-substituted primary sulfonamide was more potent than the para and the ortho-analogues. Primary sulfonamides were more potent than the secondary and tertiary analogues. The onset and duration of action in vitro of selected compounds was assessed on isolated superfused guinea pig trachea. Sulfonamide 29b had the best profile of potency, selectivity, onset, and duration of action on both guinea pig trachea and human bronchus. Furthermore, 29b was found to have low oral bioavailability in rat and dog and also to have long duration of action in an in vivo model of bronchodilation. Crystalline salts of 29b were identified that had suitable properties for inhaled administration. A proposed binding mode for 29b to the beta(2)-receptor is presented.

  DOI：

  10.1021/jm801016j
• 作为产物：
  描述：

  1-bromo-6-(but-3-ynyloxy)hexane 、 苄胺 在 盐酸 、 乙酸乙酯 、 碳酸氢钠 、 水 、 Sodium sulfate-III 、 chloroform methanol 作用下， 反应 2.0h， 以to give the title compound (25.3 g)的产率得到N-benzyl-6-(but-3-ynyloxy)hexan-1-amine
  参考文献：
  名称：

  Formailide derivatives as beta2-adrenoreceptor agonists

  摘要：

  本发明涉及一种新的化合物（I）的公式，其制造过程，包含它们的制药组合物以及它们在治疗中的用途，特别是在预防和治疗呼吸系统疾病中的应用。

  公开号：

  US20040157830A1

文献信息

• Ethanolamine Derivatives
  申请人：GLAXO GROUP LIMITED

  公开号：EP0223410A2

  公开（公告）日：1987-05-27

  The invention provides compounds of the general formula (I) wherein Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms, or the groups C1-6alkyl, C1-6alkoxy, nitro, -(CH2)qR [where R is hydroxy, -NR3R4 (where R3 and R4 each represent a hydrogen atom or a C1-4 alkyl group, or -NR3R4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from -O-or -S-or a group -NH-or -N-(CH3)-), -NR5COR6 (where R5 represents a hydrogen atom or a C1-4 alkyl group, and R6 represents a hydrogen atom or a C1-4 alkyl, C1-4 alkoxy, phenyl or -NR3R4 group), -NR5SO2R7 (where R' represents a C1-4 alkyl, phenyl or -NR3R4 group), -COR8 (where R8 represents hydroxy, C 1-4 alkoxy or -NR3R4), -SR9 (where R' is a hydrogen atom, or a C1-4 alkyl or phenyl group), -SOR9, -SO2R9 or -CN, and q represents an integer from 0 to 3], -(CH2) rR'° (where R10 is a C1-4 alkoxy group and r represents an integer from 1 to 3) or -O(CH2)tR11 (where R" represents a hydroxy or C1-4 alkoxy group and t is an integer 2 or 3), or Ar is a phenyl ring substituted by an alkylenedioxy group of formula -O(CH2)pO-where p represents an integer 1 or 2; Q represents a group of formula where Ra represents a hydrogen atom or a C1-3 alkyl group, Rb represents and Rc represents where R represents a straight or branched C2.3 alkylene chain; R' and R2 each represent a hydrogen atom or a C1-3 alkyl group with the proviso that the sum total of carbon atoms in R' and R2 is not more than 4; X represents a C1-7 alkylene, C2-7 alkenylene or C2.7alkynylene chain; and Y represents a bond or a C1-6 alkylene, C2.6 alkenylene or C26 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is 2-10, and when X represents C 1-7 alkylene and Y represents a bond or C1- 6alkylene, then the group Ar does not represent an unsubstituted phenyl group or a phenyl group substituted by one or two substituents selected solely from halogen atoms or C1-3 alkyl or C1-3 alkoxy groups or an alkylenedioxy group -O(CH2)pO-; and physiologically acceptable salts and solvates e.g. hydrates thereof. The compounds have a selective stimulant action at β2-adrenoreceptors and may be used, inter alia, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.

  本发明提供通式 (I) 的化合物 其中 Ar 代表可任选被一个或多个取代基取代的苯基，这些取代基可选自卤素原子或基团 C1-6烷基、C1-6烷氧基、硝基、-(CH2)qR [其中 R 是羟基、-NR3R4（其中 R3 和 R4 各代表一个氢原子或一个 C1-4 烷基、或 -NR3R4 形成饱和杂环氨基，该氨基有 5-7 个环成员，并可选择在环中包含一个或多个选自 -O- 或 -S- 或基团 -NH- 或 -N-(CH3)- 的原子），-NR5COR6（其中 R5 代表氢原子或 C1-4 烷基，R6 代表氢原子或 C1-4 烷基、C1-4 烷氧基、R'代表 C1-4 烷基、苯基或 -NR3R4 基团）、-COR8（其中 R8 代表羟基、C 1-4 烷氧基或 -NR3R4）、-SR9（其中 R'为氢原子或 C1-4 烷基或苯基）、-SOR9、-SO2R9 或 -CN，q 代表 0 至 3 的整数]、-( )rR'°（其中 R10 是 C1-4 烷氧基，r 代表 1 至 3 的整数）或 -O( )tR11（其中 R "代表羟基或 C1-4 烷氧基，t 代表 2 或 3 的整数），或 Ar 是被式-O( )pO-（其中 p 代表 1 或 2 的整数）的烷二氧基取代的苯基环； Q 代表一个式基团 其中 Ra 代表氢原子或 C1-3 烷基，Rb 代表 和 Rc 代表 其中 R 代表直链或支链 C2.3 烯链；R'和 R2 各自代表氢原子或 C1-3 烷基，但 R' 和 R2 中的碳原子总数不超过 4； X 代表 C1-7 亚烷基、C2-7 烯基或 C2.7 亚炔基链；以及 Y 代表键或 C1-6 亚烷基、C2.6 亚烯基或 C26 亚炔基链，但 X 和 Y 中碳原子的总和为 2-10，当 X 代表 C1-7 亚烷基且 Y 代表键或 C1- 6 亚烷基时，则基团 Ar 不代表未取代的苯基或被一个或两个仅选自卤素原子或 C1-3 烷基或 C1-3 烷氧基或烷二氧基基团-O( )pO-的取代基取代的苯基； 以及生理上可接受的盐和溶液，如其水合物。 这些化合物对 β2-肾上腺素受体具有选择性刺激作用，可用于治疗与可逆性气道阻塞有关的疾病，如哮喘和慢性支气管炎等。
• Aminophenol derivatives
  申请人：GLAXO GROUP LIMITED

  公开号：EP0178919B1

  公开（公告）日：1988-12-21
• FORMANILIDE DERIVATIVES AS BETA2-ADRENORECEPTOR AGONISTS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1370521A1

  公开（公告）日：2003-12-17
• US4730008A
  申请人：——

  公开号：US4730008A

  公开（公告）日：1988-03-08
• US4853382A
  申请人：——

  公开号：US4853382A

  公开（公告）日：1989-08-01