tert-butyl (R)-(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate | 883994-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: tert-butyl (R)-(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate
• 英文别名: ((R)-5-bromo-indan-2-yl)-carbamic acid tert-butyl ester；tert-butyl N-[(2R)-5-bromo-2,3-dihydro-1H-inden-2-yl]carbamate
• CAS: 883994-17-0
• 化学式: C₁₄H₁₈BrNO₂
• 分子量: 312.206
• InChiKey: OZFRRBAQUPMUJA-GFCCVEGCSA-N

物化性质

• 沸点：
  396.6±42.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.67h， 生成 methyl (R)-2-((tert-butoxycarbonyl)(methyl)amino)-2,3-dihydro-1H-indene-5-carboxylate
  参考文献：
  名称：

  2-Amino-2,3-dihydro-1H-indene-5-carboxamide-Based Discoidin Domain Receptor 1 (DDR1) Inhibitors: Design, Synthesis, and in Vivo Antipancreatic Cancer Efficacy

  摘要：

  A series of 2-amino-2,3-dihydro-1H-indene-5-carboxamides were designed and synthesized as new selective discoidin domain receptor 1 (DDR1) inhibitors. One of the representative compounds, 7f, bound with DDR1 with a K-d value of 5.9 nM and suppressed the kinase activity with an half-maximal (50%) inhibitory concentration value of 14.9 nM. 7f potently inhibited collagen-induced DDR1 signaling and epithelial-mesenchymal transition, dose-dependently suppressed colony formation of pancreatic cancer cells, and exhibited promising in vivo therapeutic efficacy in orthotopic mouse models of pancreatic cancer.

  DOI：

  10.1021/acs.jmedchem.9b00365
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (R)-5-bromo-2-aminoindan 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 tert-butyl (R)-(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate
  参考文献：
  名称：

  [EN] 6-AMINO(AZA)INDANE COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECPTOR
  [FR] COMPOSES DE 6-AMINO(AZA)INDANE PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE

  摘要：

  本发明涉及公式(I)的6-氨基(氮)茚化合物，其中Ar为苯基或芳香5-或6-成员C-键合杂芳基，其中Ar可能携带1个基团Ra，Ar还可能携带1或2个基团Rb；X为N或CH；E为CR6R7或NR3；R1为C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟化的C1-C4-烷基，氟化的C3-C4-环烷基，氟化的C3-C4-环烷基甲基，氟化的C3-C4-烯基，甲酰基或C1-C3-烷基羰基；R1a为H或R1a和R2或R1a和R2a一起为(CH2)n，其中n为1、2、3或4；R2和R2a各自独立地为H、CH3、CH2F、CHF2或CF3；R3为H或C1-C4-烷基；以及这些化合物的生理耐受性酸盐。该发明还涉及包含至少一种公式(I)化合物或其药学上可接受的盐的制药组合物，以及用于治疗可通过多巴胺D3受体配体治疗的医疗疾病的方法，该方法包括给予至少一种公式(I)化合物或其药学上可接受的盐的有效量。

  公开号：

  WO2006040177A1

文献信息

• [EN] 6-AMINO(AZA)INDANE COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECPTOR<br/>[FR] COMPOSES DE 6-AMINO(AZA)INDANE PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040177A1

  公开（公告）日：2006-04-20

  The present invention relates to 6-amino(aza)indane compound of the formula (I) Wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry I or 2 radicals Rb; X is N or CH; E is CR6R7 or NR 3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4-alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H or R1a and R2 or R1a and R2a together are (CH2)n with n being 1, 2, 3 or 4; R2 and R2a each independently are H, CH3, CH2F, CHF2 or CF3; R3 is H or C,-C4-alkyl; and the physiologically tolerated acid addition salts of these compounds. The invention also relates to pharmaceutical compositions comprising at least one compound of the formula (I) or a pharmaceutically acceptable salt thereof and to a method for treating a medical disorder susceptible to treatment with a dopamine D3 receptor ligand, said method comprising administering an effective amount of at least one compound of the formula (I) or a pharmaceutically acceptable salt thereof.

  本发明涉及公式(I)的6-氨基(氮)茚化合物，其中Ar为苯基或芳香5-或6-成员C-键合杂芳基，其中Ar可能携带1个基团Ra，Ar还可能携带1或2个基团Rb；X为N或CH；E为CR6R7或NR3；R1为C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟化的C1-C4-烷基，氟化的C3-C4-环烷基，氟化的C3-C4-环烷基甲基，氟化的C3-C4-烯基，甲酰基或C1-C3-烷基羰基；R1a为H或R1a和R2或R1a和R2a一起为(CH2)n，其中n为1、2、3或4；R2和R2a各自独立地为H、CH3、CH2F、CHF2或CF3；R3为H或C1-C4-烷基；以及这些化合物的生理耐受性酸盐。该发明还涉及包含至少一种公式(I)化合物或其药学上可接受的盐的制药组合物，以及用于治疗可通过多巴胺D3受体配体治疗的医疗疾病的方法，该方法包括给予至少一种公式(I)化合物或其药学上可接受的盐的有效量。
• 6-Amino(Aza)Indane Compounds Suitable for Treating Disorders that Respond to Modulation of the Dopamine D3 Receptor
  申请人：Drescher Karla

  公开号：US20080318996A1

  公开（公告）日：2008-12-25

  The present invention relates to 6-amino(aza)indane compound of the formula (I) Wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical R 6 and wherein Ar may also carry I or 2 radicals R b ; X is N or CH; E is CR 6 R 7 or NR 3 ; R 1 is C 1 -C 4 -alkyl, C 3 -C4-cycloalkyl, C 3 -C 4 -cycloalkylmethyl, C 3 -C 4 -alkenyl, fluorinated C 1 -C 4 -alkyl, fluorinated C 3 -C 4 -cycloalkyl, fluorinated C 3 -C 4 -cycloalkylmethyl, fluorinated C 3 -C 4 -alkenyl, formyl or C 1 -C 3 -alkylcarbonyl; R 1a is H or R 1a and R 2 or R 1a and R 2a together are (CH 2 ) n with n being 1, 2, 3 or 4; R 2 and R 2a each independently are H, CH 3 , CH 2 F, CHF 2 or CF 3 ; R 3 is H or C,-C4-alkyl; and the physiologically tolerated acid addition salts of these compounds. The invention also relates to pharmaceutical compositions comprising at least one compound of the formula (I) or a pharmaceutically acceptable salt thereof and to a method for treating a medical disorder susceptible to treatment with a dopamine D3 receptor ligand, said method comprising administering an effective amount of at least one compound of the formula (I) or a pharmaceutically acceptable salt thereof.

  本发明涉及式（I）的6-氨基（氮）吲哚化合物，其中Ar是苯或芳香5-或6-成员C-连接的杂环芳基，其中Ar可以携带1个基团R6，Ar还可以携带1或2个基团Rb；X是N或CH；E是CR6R7或NR3；R1是C1-C4烷基、C3-C4环烷基、C3-C4环烷基甲基、C3-C4烯基、氟代C1-C4烷基、氟代C3-C4环烷基、氟代C3-C4环烷基甲基、氟代C3-C4烯基、甲酰基或C1-C3烷基羰基；R1a是H或R1a和R2或R1a和R2a一起是（CH2）n，其中n为1、2、3或4；R2和R2a各自独立地是H、CH3、CH2F、CHF2或CF3；R3是H或C1-C4烷基；以及这些化合物的生理上耐受的酸加成盐。该发明还涉及包含式（I）的至少一种化合物或其药学上可接受的盐的制药组合物，以及一种用于治疗对多巴胺D3受体配体敏感的医学疾病的方法，该方法包括给予至少一种式（I）的化合物或其药学上可接受的盐的有效量。
• 6-amino(aza)indane compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor
  申请人：Abbott GmbH & Co. KG

  公开号：US07759397B2

  公开（公告）日：2010-07-20

  The present invention relates to 6-amino(aza)indane compound of the formula (I) Wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry I or 2 radicals Rb; X is N or CH; E is CR6R7 or NR3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4-alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H or R1a and R2 or R1a and R2a together are (CH2)n with n being 1, 2, 3 or 4; R2 and R2a each independently are H, CH3, CH2F, CHF2 or CF3; R3 is H or C,-C4-alkyl; and the physiologically tolerated acid addition salts of these compounds. The invention also relates to pharmaceutical compositions comprising at least one compound of the formula (I) or a pharmaceutically acceptable salt thereof and to a method for treating a medical disorder susceptible to treatment with a dopamine D3 receptor ligand, said method comprising administering an effective amount of at least one compound of the formula (I) or a pharmaceutically acceptable salt thereof.

  本发明涉及一种式为(I)的6-氨基(氮)吲哚化合物，其中Ar是苯基或芳香性5或6元C-杂环芳基，其中Ar可以携带1个基团Ra，Ar也可以携带1或2个基团Rb；X是N或CH；E是CR6R7或NR3；R1是C1-C4烷基，C3-C4环烷基，C3-C4环烷基甲基，C3-C4烯基，氟代C1-C4烷基，氟代C3-C4环烷基，氟代C3-C4环烷基甲基，氟代C3-C4烯基，甲酰基或C1-C3烷基羰基；R1a是H或R1a和R2，或R1a和R2a一起是(CH2)n，其中n为1、2、3或4；R2和R2a各自独立地是H、CH3、CH2F、CHF2或CF3；R3是H或C,-C4-烷基；以及这些化合物的生理耐受酸盐。本发明还涉及包含至少一种式为(I)的化合物或其药学上可接受的盐的制药组合物，以及一种用于治疗可通过多巴胺D3受体配体治疗的医疗障碍的方法，该方法包括给予至少一种式为(I)的化合物或其药学上可接受的盐的有效量。
• 6-amino(aza)indane compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor
  申请人：Abbott GmbH & Co. KG

  公开号：EP2311801A1

  公开（公告）日：2011-04-20

  The present invention relates to 6-amino(aza)indane compound of the formula I and the physiologically tolerated acid addition salts of these compounds. The invention also relates to pharmaceutical compositions comprising at least one compound of the formula I or a pharmaceutically acceptable salt thereof and to a method for treating a medical disorder susceptible to treatment with a dopamine D3 receptor ligand, said method comprising administering an effective amount of at least one compound of the formula I or a pharmaceutically acceptable salt thereof.

  本发明涉及式 I 的 6-氨基（氮杂）茚满化合物 以及这些化合物的生理上可耐受的酸加成盐。 本发明还涉及包含至少一种式 I 的化合物或其药学上可接受的盐的药物组合物，以及一种治疗易受多巴胺 D3 受体配体治疗的内科疾病的方法，所述方法包括施用有效量的至少一种式 I 的化合物或其药学上可接受的盐。
• 6-AMINO(AZA)INDANE COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECPTOR
  申请人：Abbott GmbH & Co. KG

  公开号：EP1807392A1

  公开（公告）日：2007-07-18