(R)-(+)-3-amino-8-fluorochromane-5-carboxamide | 214823-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R)-(+)-3-amino-8-fluorochromane-5-carboxamide
• 英文别名: (3R)-3-amino-8-fluorochromane-5-carboxamide；(R)-3-Amino-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxamide；(3R)-3-amino-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
• CAS: 214823-10-6
• 化学式: C₁₀H₁₁FN₂O₂
• 分子量: 210.208
• InChiKey: CQZHUEJNSOTLNG-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-3-amino-8-fluorochromane-5-carboxamide 、 3-((苄氧基)甲基)环丁酮 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (3R)-3-({3-benzyloxymethyl-cyclobutyl}amino)-8-fluorochromane-5-carboxamide
  参考文献：
  名称：

  [EN] 3-AMINO CHOMAN AND 2-AMINO TETRALIN DERIVATIVES
  [FR] DERIVES 3-AMINO CHOMANE ET 2-AMINO TETRALINE

  摘要：

  揭示了3-氨基色苷和2-氨基四氢萘衍生物以及含有这些化合物的组合物。还揭示了在治疗血清素失调症，如抑郁症和焦虑症中使用3-氨基色苷和2-氨基四氢萘化合物以及含有这些化合物的组合物的方法。

  公开号：

  WO2005012291A1
• 作为产物：
  描述：

  3-amino-8-fluorochromane-5-carboxamide 在 L-酒石酸 作用下， 生成 (R)-(+)-3-amino-8-fluorochromane-5-carboxamide 、 (S)-(-)-3-amino-8-fluorochromane-5-carboxamide
  参考文献：
  名称：

  Advances toward New Antidepressants with Dual Serotonin Transporter and 5-HT_1A Receptor Affinity within a Class of 3-Aminochroman Derivatives. Part 2

  摘要：

  Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through,a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affinity at both the 5-HT reuptake site and the 5-HT1A receptor. Compounds of most interest were found to have a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran linked to a 3-alkylindole (straight chain), more specifically substituted with a 5-fluoro ((R)-(-)-35c), 5-cyano ((-)-52a), or 5,7-difluoro ((-)-52g). Several factors contributed to 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonism in vitro. Although most of our analogues showed good to excellent affinities at both targets, specific features such as cyclobutyl substitution on the basic nitrogen and stereochemistry at the 3-position of the chroman moiety seemed necessary for antagonism at the 5-HT1A receptor. Branched linkers seemed to impart antagonism even as racemates, however, potency of these analogues in the functional assay was not desirable enough to further pursue these compounds.

  DOI：

  10.1021/jm8007097

文献信息

• Process for the manufacture of 3-N-N-dicyclobutylamino-8-fluoro-3, 4-dihydro-2H-1-benzopyran-5-carboxamide
  申请人：Astra Aktiebolag

  公开号：US06197978B1

  公开（公告）日：2001-03-06

  A process for the manufacture of the racemic compound of the formula (I), its R-enantiomer (formula R-(I)) and its S-enantiomer (formula S-(I)), and pharmaceutically acceptable salts and/or solvates thereof, as well as new intermediates obtained and used in the process.

  一种用于制造式(I)的外消旋化合物、其R-对映体（式R-(I)）和其S-对映体（式S-(I)）以及其药用可接受的盐和/或溶剂合物的方法，以及在该过程中获得并使用的新中间体。
• [EN] A NEW PROCESS<br/>[FR] NOUVEAU PROCEDE
  申请人：ASTRA AKTIEBOLAG

  公开号：WO1998046586A1

  公开（公告）日：1998-10-22

  (EN) A process for the manufacture of the racemic compound of formula (I), its $i(R)-enantiomer (formula $i(R)-(I)) and its $i(S)-enantiomer (formula $i(S)-(I)), and pharmaceutically acceptable salts and/or solvates thereof, as well as new intermediates obtained and used in the process.(FR) L'invention concerne un procédé permettant de préparer le composé racémique de formule (I), son énantiomère $i(R) (formule $i(R)-(I)) et son énantiomère $i(S) (formule $i(S)-(I)) et leurs sels et/ou solvats pharmaceutiquement tolérables, ainsi que de nouveaux produits intermédiaire obtenus et utilisés dans ce procédé.

  一种制备式(I)的外消旋化合物及其$i(R)-对映体(式$i(R)-(I))和$i(S)-对映体(式$i(S)-(I))，以及其药学上可接受的盐和/或溶剂化物的方法，以及在该过程中获得和使用的新中间体。
• 3-Amino chroman and 2-amino tetralin derivatives
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20050032873A1

  公开（公告）日：2005-02-10

  3-Amino chroman and 2-amino tetralin derivatives and compositions containing such compounds are disclosed. Methods of using the 3-amino chroman and 2-amino tetralin compounds and compositions containing such compounds in the treatment of serotonin disorders, such as depression and anxiety, are also disclosed.

  本文披露了3-氨基色满和2-氨基四氢萘衍生物及含有这些化合物的组合物。还披露了使用3-氨基色满和2-氨基四氢萘化合物及含有这些化合物的组合物治疗血清素失调症，如抑郁和焦虑的方法。
• A NEW PROCESS
  申请人：Astra Aktiebolag

  公开号：EP0975618A1

  公开（公告）日：2000-02-02
• a new process for the preparation of 3-N,N-dicycobutylamino-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxamide
  申请人：AstraZeneca AB

  公开号：EP0975618B1

  公开（公告）日：2001-10-24