exo-3-Oxabicyclo[3.1.0]hexane-6-methanamine | 909406-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: exo-3-Oxabicyclo[3.1.0]hexane-6-methanamine
• 英文别名: (exo)-C-[1-(3-oxabicyclo[3.1.0]hex-6-yl)]methylamine
• CAS: 909406-64-0
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: AWZIRBSKQVRHQS-STNDOWJSSA-N

物化性质

• 沸点：
  181.8±13.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  exo-3-Oxabicyclo[3.1.0]hexane-6-methanamine 、 4-chloro-N-(4-ethylphenyl)-N-isobutyl-3-nitrobenzenesulfonamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到4-((((1R,5S,6S)-3-axabicyclo[3.1.0]hexan-6-yl)methyl)amino)-N-(4-ethylphenyl)-N-isobutyl-3-nitrobenzenesulfonamide
  参考文献：
  名称：

  发现和表征CD12681，一种有效的RORγ反向激动剂，用于牛皮癣局部治疗的临床前候选药物

  摘要：

  视黄酸受体相关的孤儿受体RORγ可能对多种自身免疫性疾病有潜在影响，已成为制药行业的抢手目标。本文描述了鉴定与局部应用治疗皮肤疾病相容的有效RORγ反向激动剂的努力。这些努力最终导致发现了N-（2,4-二甲基苯基）-N-异丁基-2-氧代-1-[[（四氢-2 H-吡喃-4-基）甲基] -2,3-二氢-1 H-苯并[ d ]咪唑-5-磺酰胺（CD12681），一种有效的反向激动剂，在IL-23诱导的小鼠皮肤炎症模型中具有体内活性。

  DOI：

  10.1002/cmdc.201700758
• 作为产物：
  描述：

  (exo)-3-oxabicyclo[3.1.0]hexane-6-carboxamide 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 exo-3-Oxabicyclo[3.1.0]hexane-6-methanamine
  参考文献：
  名称：

  WO2007/31558

  摘要：

  公开号：

文献信息

• 5-Amino-4-Hydroxy-7-(Imidazo [1,2-A] Pyridin-6-Ylmethyl)-8-Methyl-Nonamide Derivatives and Related Compounds as Renin Inhibitors for the Treatment of Hypertension
  申请人：HEROLD Peter

  公开号：US20100063087A1

  公开（公告）日：2010-03-11

  Compounds of the general formula (I) or its salt or a compound in which one or more atoms are replaced by their stable, nonradio-active isotopes, in particular its pharmaceutically acceptable salt; in which X is —CH 2 —; R is a mono- to tetra-substituted, mono- or bicyclic, unsaturated heterocyclic radical having 1 to 4 nitrogen atoms, R 2 is C 1-6 alkyl or C 3-6 cycloalkyl; R 3 is independently of one another H, C 1-6 alkyl, C 1-6 alkoxycarbonyl or C 1-6 alkanoyl; R 4 is C 2-6 alkenyl, C 1-6 alkyl, unsubstituted or substituted aryl-C 1-6 alkyl or C 3-8 cycloalkyl; R 5 is -L m -R ; L is C 1-6 alkylene which is optionally substituted by 1-4 halogen, or a linker: formula (II) n=0, 1 or 2; m=0 or 1; R 6 is a radical composed of 2 cyclic systems selected from bicyclo[x.y.z]alkyl, spiro[o.p]alkyl, mono- or bioxabicyclo[x.y.z]alkyl or mono- or bioxaspiro[o.p]alkyl, all of which may be substituted by 1-3 substituents selected from C 1-6 alkyl, C 1-6 alkoxy, cyano, halogen, C 1-6 alkoxy- C 1-6 alkyl, hydroxy-C 1-6 alkyl or dialkylamino, or if m=0: is also saturated C 3-8 heterocyclyl which comprises 1-2 oxygen atoms, substituted by 1-3 substituents selected from C 1-6 alkyl, C 1-6 alkoxy, cyano, halogen, C 1-6 alkoxy-C 1-6 alkyl, hydroxy-C 1-6 alkyl or dialkylamino, or if m=1: is also saturated C 3-8 heterocyclyl which comprises 1-2 oxygen atoms, optionally substituted by 1-3 substituents selected from C 1-6 alkyl, C 1-6 alkoxy, cyano, halogen, C 1-6 -alkoxy-C 1-6 alkyl, hydroxy-C 1-6 alkyl or dialkylamino; have renin-inhibiting properties and can be used as medicines for the treatment of hypertension.

  通式（I）的化合物或其盐或其中一个或多个原子被其稳定的非放射性同位素替换的化合物，特别是其药学上可接受的盐；其中X为-CH2-；R为1至4个氮原子的单取代、双取代、三取代或四取代的单环或双环不饱和杂环基，R2为C1-6烷基或C3-6环烷基；R3独立地为H、C1-6烷基、C1-6烷氧羰基或C1-6酰基；R4为C2-6烯基、C1-6烷基、未取代或取代的芳基-C1-6烷基或C3-8环烷基；R5为-Lm-R；L为C1-6烷基，可选地被1-4个卤素取代，或为连接基：通式（II）n=0、1或2；m=0或1；R6为由自行选择的2个环系统组成的基，所述环系统选择自双环[x.y.z]烷基、螺[O.P]烷基、单环或双氧杂双环[x.y.z]烷基或单环或双氧杂螺[O.P]烷基，所有这些基都可以被1-3个取代基所取代，所述取代基选择自C1-6烷基、C1-6烷氧基、氰基、卤素、C1-6烷氧基-C1-6烷基、羟基-C1-6烷基或二烷基氨基，或如果m=0：还是饱和的C3-8杂环基，其中包括1-2个氧原子，被1-3个取代基所取代，所述取代基选择自C1-6烷基、C1-6烷氧基、氰基、卤素、C1-6烷氧基-C1-6烷基、羟基-C1-6烷基或二烷基氨基，或如果m=1：还是饱和的C3-8杂环基，其中包括1-2个氧原子，可选地被1-3个取代基所取代，所述取代基选择自C1-6烷基、C1-6烷氧基、氰基、卤素、C1-6烷氧基-C1-6烷基、羟基-C1-6烷基或二烷基氨基；具有抑制肾素的性质，可用作治疗高血压的药物。
• 5-AMINO-4-HYDROXY-7- (IMIDAZO [1,2-A] PYRIDIN-6- YLMETHYL)-8-METHYL-NONAMIDE DERIVATIVES AND RELATED COMPOUNDS AS RENIN INHIBITORS FOR THE TREATMENT OF HYPERTENSION
  申请人：Novartis AG

  公开号：EP1948654B1

  公开（公告）日：2009-06-24
• US8071651B2
  申请人：——

  公开号：US8071651B2

  公开（公告）日：2011-12-06
• [EN] 5-AMINO-4-HYDROXY-7- (IMIDAZO [1,2-A] PYRIDIN-6- YLMETHYL)-8-METHYL-NONAMIDE DERIVATIVES AND RELATED COMPOUNDS AS RENIN INHIBITORS FOR THE TREATMENT OF HYPERTENSION<br/>[FR] AMIDES D'ACIDE ALCANOÏQUE BICYCLO- OU SPIRO-SUBSTITUÉS
  申请人：SPEEDEL EXPERIMENTA AG

  公开号：WO2007031558A1

  公开（公告）日：2007-03-22

  [EN] Compounds of the general formula (I) or its salt or a compound in which one or more atoms are replaced by their stable, nonradio-active isotopes, in particular its pharmaceutically acceptable salt; in which X is -CH₂-; R¹ is a mono- to tetrasubstituted, mono- or bicyclic, unsaturated heterocyclic radical having 1 to 4 nitrogen atoms, R² is C_1-6alkyl or C_3-6cycloalkyl; R³ is independently of one another H, C_1-6alkyl, C_1-6alkoxycarbonyl or C_1-6alkanoyl; R⁴ is C_2-6alkenyl, C_1-6alkyl, unsubstituted or substituted aryl- C_1-6alkyl or C_3-8cycloalkyl; R⁵ is -L_m-R⁶; L is C_1-6alkylene which is optionally substituted by 1-4 halogen, or a linker: formula (II) n = 0, 1 or 2; m = 0 or 1; R⁶ is a radical composed of 2 cyclic systems selected from bicyclo[x.y.z]alkyl, spiro[o.p]alkyl, mono- or bioxabicyclo[x.y.z]alkyl or mono- or bioxaspiro[o.p]alkyl, all of which may be substituted by 1-3 substituents selected from C_1-6alkyl, C_1-6alkoxy, cyano, halogen, C_1-6alkoxy- C_1-6alkyl, hydroxy-C_1-6alkyl or dialkylamino, or if m = 0: is also saturated C_3-8heterocyclyl which comprises 1-2 oxygen atoms, substituted by 1-3 substituents selected from C_1-6alkyl, C_1-6alkoxy, cyano, halogen, C_1-6alkoxy- C_1-6alkyl, hydroxy- C_1-6alkyl or dialkylamino, or if m = 1: is also saturated C_3-8heterocyclyl which comprises 1-2 oxygen atoms, optionally substituted by 1-3 substituents selected from C_1-6alkyl, C_1-6alkoxy, cyano, halogen, C_1-6-alkoxy-C_1-6alkyl, hydroxy-C_1-6alkyl or dialkylamino; have renin- inhibiting properties and can be used as medicines for the treatment of hypertension.
  [FR] Selon l'invention, des composés de formule générale (I) ou leurs sels ou composés, dans lesquels un ou plusieurs atomes sont remplacés par leurs isotopes stables, non radioactifs, notamment, par leur sel acceptable pharmaceutiquement et dans lesquels les significations des substituants R¹, R², R³, R⁴, R⁵ et X sont telles qu'indiquées dans la revendication 1, présentent des propriétés de ré-inhibition et peuvent être utilisés comme des médicaments.