15-aza-3,6,9,12-tetraoxa-pentadecanoyl-ε-[D-(+)-biotinyl]-L-lysine | 894427-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 15-aza-3,6,9,12-tetraoxa-pentadecanoyl-ε-[D-(+)-biotinyl]-L-lysine
• 英文别名: (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-[[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]acetyl]amino]hexanoic acid
• CAS: 894427-98-6
• 化学式: C₂₆H₄₇N₅O₉S
• 分子量: 605.753
• InChiKey: QHJFCLXORJAVSC-CIEVZJJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  41
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  225
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  15-aza-3,6,9,12-tetraoxa-pentadecanoyl-ε-[D-(+)-biotinyl]-L-lysine 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.75h， 以27%的产率得到benzyl N-<3-{[-ε-(D-(+)-biotinyl)-Z-lysine-15-aza-3,6,9,12-tetraoxa-pentadecanoyl]-carbonyl}-benzenesulfonyl>-4-O-{4-(N-benzyloxycarbonyl-4-piperidinyl)-butyl}-L-tyrosine
  参考文献：
  名称：

  WO2007/42469

  摘要：

  公开号：
• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以100%的产率得到15-aza-3,6,9,12-tetraoxa-pentadecanoyl-ε-[D-(+)-biotinyl]-L-lysine
  参考文献：
  名称：

  WO2007/42469

  摘要：

  公开号：

文献信息

• WO2006/67173
  申请人：——

  公开号：——

  公开（公告）日：——
• Antithrombotic Dual Inhibitors Comprising A Biotin Residue
  申请人：De Kort Martin

  公开号：US20100004186A1

  公开（公告）日：2010-01-07

  The present invention relates compounds of the formula (I) oligosaccharide-spacer-A (1), wherein the oligosaccharide is a negatively charged oligosaccharide residue comprising two to twenty five monosaccharide units, the charge being compensated by positively charged counterions, and wherein the oligosaccharide residue is derived from an oligosaccharide which has (AT-III mediated) anti-Xa activity per se; the spacer is an essentially pharmacologically inactive flexible linking residue having a chain length of 10 to 70 atoms; A is the residue —CH[NH—SO 2 —R 1 ][CO—NR 2 —CH(4-benzamidine)-CO—NR 3 R 4 ], wherein R1 is phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, (iso)quinolinyl, tetrahydro(iso)quinolinyl, 3,4-dihydro-1H-isoquinolinyl, chromanyl or the camphor group, which groups may optionally be substituted with one or more substituents selected from (1-8C)alkyl or (1-8C)alkoxy; and wherein R 2 and R 3 are independently H or (1-8C)alkyl; R 4 is (−8C)alkyl or (3-8C)cycloalkyl; or R 3 and R 4 together with the nitrogen atom to which they are bonded are a nonaromatic (4-8) membered ring optionally containing another heteroatom, the ring optionally being substituted with (1-8C)alkyl or SO2-(1-8C)alkyl; or a pharmaceutically acceptable salt thereof a prodrug or solvate thereof; wherein the compound of formula I further comprises at least one covalent bond with a biotin residue or an analogue thereof. The compounds of the invention have antithrombotic activity and can be used in treating or preventing thrombosis or other thrombin-related diseases. The antithrombotic activity of the compound of this invention can be neutralized in case of emergency upon administration of avidin, streptavidin and analogues thereof having high biotin affinity.
• Anticoagulant Antithrombotic Dual Inhibitors Comprising a Biotin Label
  申请人：De Kort Martin

  公开号：US20100029582A1

  公开（公告）日：2010-02-04

  The present invention relates compounds of the formula: oligosaccharide-spacer-(GpIIb/IIIa antagonist), wherein the oligosaccharide is a negatively charged oligosaccharide residue comprising four to twenty five monosaccharide units, the charge being compensated by positively charged counterions, and wherein the oligosaccharide residue is derived from an oligosaccharide which has (AT-II mediated) anti-Xa activity per se; the spacer is a bond or an essentially pharmacologically inactive linking residue; the GpIIb/IIIa antagonist is a residue mimicking the RGD and/or K(QA)GD fragment of fibrinogen, comprising a carboxylate moiety and a basic moiety located within the residue at a distance of 10-20 Å from each other; or a pharmaceutically acceptable salt thereof or a prodrug or a solvate thereof; wherein the compound of formula I further comprises at least one covalent bond with a biotin label or an analogue thereof. The compounds of the invention have antithrombotic activity and can be used in treating or preventing thrombotic diseases. The antithrombotic activity of the compound of this invention can be neutralized in case of emergency upon administration of avidin, streptavidin and analogues thereof having high biotin affinity.
• ANTITHROMBOTIC DUAL INHIBITORS COMPRISING A BIOTIN RESIDUE
  申请人：De Kort Martin

  公开号：US20120238512A1

  公开（公告）日：2012-09-20

  The present invention relates compounds of the formula (I) oligosaccharide-spacer-A (I), wherein the oligosaccharide is a negatively charged oligosaccharide residue comprising two to twenty five monosaccharide units, the charge being compensated by positively charged counterions, and wherein the oligosaccharide residue is derived from an oligosaccharide which has (AT-III mediated) anti-Xa activity per se; the spacer is an essentially pharmacologically inactive flexible linking residue having a chain length of 10 to 70 atoms; A is the residue —CH[NH—SO 2 —R 1 ] [CO—NR 2 —CH(4-benzamidine)-CO—NR 3 R 4 ], wherein R1 is phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, (iso)quinolinyl, tetrahydro(iso)quinolinyl, 3,4-dihydro-1H-isoquinolinyl, chromanyl or the camphor group, which groups may optionally be substituted with one or more substituents selected from (1-8C)alkyl or (1-8C)alkoxy; and wherein R 2 and R 3 are independently H or (1-8C)alkyl; R 4 is (-8C)alkyl or (3-8C)cycloalkyl; or R 3 and R 4 together with the nitrogen atom to which they are bonded are a nonaromatic (4-8)membered ring optionally containing another heteroatom, the ring optionally being substituted with (1-8C)alkyl or SO2-(I-8C)alkyl; or a pharmaceutically acceptable salt thereof a prodrug or solvate thereof; wherein the compound of formula I further comprises at least one covalent bond with a biotin residue or an analogue thereof. The compounds of the invention have antithrombotic activity and can be used in treating or preventing thrombosis or other thrombin-related diseases. The antithrombotic activity of the compound of this invention can be neutralized in case of emergency upon administration of avidin, streptavidin and analogues thereof having high biotin affinity.
• US8168595B2
  申请人：——

  公开号：US8168595B2

  公开（公告）日：2012-05-01