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Cell adhesion promoting agent and method of promoting cell adhesion

Foreign code F120006121
File No. S2008-0654
Posted date Jan 6, 2012
Country United States of America
Application number 99980509
Gazette No. 20110117651
Gazette No. 8685976
Date of filing Jun 16, 2009
Gazette Date May 19, 2011
Gazette Date Apr 1, 2014
International application number JP2009060950
International publication number WO2009154201
Date of international filing Jun 16, 2009
Date of international publication Dec 23, 2009
Priority data
  • P2008-159369 (Jun 18, 2008) JP
  • 2009WO-JP60950 (Jun 16, 2009) WO
Title Cell adhesion promoting agent and method of promoting cell adhesion
Abstract (US8685976)
The subject invention discloses an agent for promoting cell adhesion to a support, comprising a dispirotripiperazine derivative represented by Formula I below or a salt thereof; a method for promoting cell adhesion to a support comprising adding the dispirotripiperazine derivative represented by Formula I below or a salt thereof to a culture medium, or applying the same to a support; and an agonist of a heparin sulfate that comprises the dispirotripiperazine derivative represented by Formula I below or a salt thereof, and that promotes cell adhesion and/or cell growth.
Scope of claims [claim1]
1. A dispirotripiperazine derivative represented by Formula I below or a salt thereof,
wherein R1 and R2 are the same or different, and each represent hydrogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, an aryl group, a heteroaryl group, an aryl-substituted alkyl group, a heteroaryl-substituted alkyl group (excluding the case where both R1 and R2 are hydrogen; at least one of R1 and R2 being bonded with a substance having integrin-binding activity, wherein the substance comprises Arg-Gly-Asp amino acid sequence; the alkyl group, the alkenyl group, the alkynyl group, and each alkyl moiety are optionally substituted with at least one atom or one group selected from halogen, hydroxyl (the hydroxy being optionally acylated, carbamated or etherified), cyano, nitro, amino, mono- or di-substituted amino, carbamoyl and sulfamoyl; the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, each alkyl moiety and each cycloalkyl moiety are optionally interrupted by -- O -- , -- S -- , -- SO -- , -- SO2 -- , -- OSO2 -- , -- NH -- , -- CO -- , -- CH.dbd.CH -- , -- C≡C -- , -- CONH -- , -- NHCO -- , -- NHCOO -- , -- OCH2CONH -- , or -- OCH2CO -- ; and the aryl group, each aryl moiety, the heteroaryl group, each heteroaryl moiety, the cycloalkyl group and each cycloalkyl moiety are optionally substituted with at least one atom or one group selected from halogen, hydroxyl, formyl, alkyl, hydroxyalkyl, alkoxy, alkylthio, cyano, nitro, amino, mono- or di-substituted amino, carbamoyl, sulfamoyl, alkyl sulfonyl, alkyl sulfonylamino, alkyl carbonylamino, methylenedioxy, and aryl) or a group represented by Formula II below (excluding the case where both of R1 and R2 are a group represented by Formula II),
wherein R1a represents an alkylene group, an alkenylene group, an alkynylene group, a cycloalkylene group, a cycloalkylalkylene group, an arylene group, a heteroarylene group, an aryl-substituted alkylene group, or a heteroaryl-substituted alkylene group (the alkylene group, the alkenylene group, the alkynylene group, and each alkylene moiety being optionally substituted with at least one atom or one group selected from halogen, hydroxyl (the hydroxy being optionally acylated, carbamated or etherified), cyano, nitro, amino, mono- or di-substituted amino, carbamoyl and sulfamoyl; the alkylene group, the alkenylene group, the alkynylene group, the cycloalkylene group, each alkylene moiety and each cycloalkyl moiety are optionally interrupted by -- O -- , -- S -- , -- SO -- , -- SO2 -- , -- OSO2 -- , -- NH -- , -- CO -- , -- CH.dbd.CH -- , -- C≡C -- , -- CONH -- , -- NHCO -- , -- NHCOO -- , -- OCH2CONH -- , or -- OCH2CO -- ; and the arylene group, each aryl moiety, the heteroarylene group, each heteroaryl moiety, the cycloalkylene group and each cycloalkyl moiety are optionally substituted with at least one atom or one group selected from halogen, hydroxyl, formyl, alkyl, hydroxyalkyl, alkoxy, alkylthio, cyano, nitro, amino, mono- or di-substituted amino, carbamoyl, sulfamoyl, alkyl sulfonyl, alkyl sulfonylamino, alkyl carbonylamino, methylenedioxy, and aryl); and R2a has the same definition as those of R1 and R2.
[claim2]
2. A dispirotripiperazine derivative represented by Formula Ia below or a salt thereof,
wherein R3 represents a monocyclic aryl group or a monocyclic heteroaryl group (R3 being optionally derivatized with dansylhydrazine or bonded with a substance having integrin-binding activity or a Arg-Gly-Asp peptide; and the aryl group and the heteroaryl group are optionally substituted with at least one atom or one group selected from halogen, hydroxyl formyl, alkyl, hydroxyalkyl, alkoxy, alkylthio, cyano, nitro, amino, mono- or di-substituted amino, carbamoyl, sulfamoyl, alkyl sulfonyl, alkyl sulfonylamino, alkyl carbonylamino, methylenedioxy, and aryl); and R4 represents a group represented by Formula IIa below,
wherein R3a represents a monocyclic arylene group or monocyclic heteroarylene group, (the arylene group and heteroarylene group being optionally substituted with at least one atom or one group selected from the group consisting of halogen, hydroxyl, formyl, alkyl, hydroxyalkyl, alkoxy, alkylthio, cyano, nitro, amino, mono- or di-substituted amino, carbamoyl, sulfamoyl, alkyl sulfonyl, alkyl sulfonylamino, alkyl carbonylamino, methylenedioxy, and aryl), and R4a has the same definition as that of R3.
[claim3]
3. A dispirotripiperazine derivative or a salt thereof selected from the groups below:
[claim4]
4. A method for promoting cell adhesion to a support, comprising either adding the dispirotripiperazine derivative or a salt thereof according to claim 1 to a culture medium, or applying the dispirotripiperazine derivative or a salt thereof according to claim 1 to a support.
[claim5]
5. The method according to claim 4, wherein the support is a cell culture vessel.
[claim6]
6. The method according to claim 4, wherein the cell is a nonadherent cell.
[claim7]
7. A method for promoting cell adhesion to a support, comprising either adding the dispirotripiperazine derivative or a salt thereof according to claim 2 to a culture medium, or applying the dispirotripiperazine derivative or a salt thereof according to claim 2 to a support.
[claim8]
8. The method according to claim 7, wherein the support is a cell culture vessel.
[claim9]
9. The method according to claim 7, wherein the cell is a nonadherent cell.
[claim10]
10. A method for promoting cell adhesion to a support, comprising either adding the dispirotripiperazine derivative or a salt thereof according to claim 3 to a culture medium, or applying the dispirotripiperazine derivative or a salt thereof according to claim 3 to a support.
[claim11]
11. The method according to claim 10, wherein the support is a cell culture vessel.
[claim12]
12. The method according to claim 10, wherein the cell is a nonadherent cell.
  • Inventor, and Inventor/Applicant
  • UESUGI MOTONARI
  • YAMAZOE SAYUMI
  • KYOTO UNIVERSITY
IPC(International Patent Classification)
U.S. Cl./(Sub)
  • C07D487/20
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