Title:
METHOD FOR PRODUCING SPIROOXINDOLE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2015/033974
Kind Code:
A1
Abstract:
Provided is a method with which it is possible to efficiently manufacture a compound having a spirooxindole structure, for example a compound having a spirooxindole structure and having antitumor activity which inhibits the interaction between Mdm2 protein and p53 protein, or an intermediate of of said compound, using an asymmetric catalyst. By performing a catalytic asymmetric 1,3-bipolar cyclic addition using a chiral ligand and Lewis acid, with ketimine as a reaction substrate, a compound having an optically active tricyclic dispiroindole structure is obtained efficiently.
More Like This:
Inventors:
YAMAUCHI MOTOSHI (JP)
NAKAYAMA KEIJI (JP)
NAKAYAMA KEIJI (JP)
Application Number:
PCT/JP2014/073233
Publication Date:
March 12, 2015
Filing Date:
September 03, 2014
Export Citation:
Assignee:
DAIICHI SANKYO CO LTD (JP)
International Classes:
C07D487/10; B01J23/72; B01J27/122; B01J31/02; B01J31/04; B01J31/22; C07B53/00; C07D491/20; C07B61/00
Domestic Patent References:
| WO2012121361A1 | 2012-09-13 | |||
| WO2012155066A2 | 2012-11-15 | |||
| WO2012121361A1 | 2012-09-13 | |||
| WO2006091646A2 | 2006-08-31 |
Foreign References:
| US20120071499A1 | 2012-03-22 | |||
| JP2013142071A | 2013-07-22 |
Other References:
SHU,L. ET AL.: "SYNTHESIS OF A SPIROINDOLINONE PYRROLIDINECARBOXAMIDE MDM2", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 17, no. 2, AN, 15 January 2013 (2013-01-15), pages 247 - 256, XP055277896, DOI: TAGONIST
ANTONCHICK,A.P. ET AL.: "HIGHLY ENANTIOSELECTIVE SYNTHESIS AND CELLULAR EVALUATION OF", NATURE CHEMISTRY, vol. 2, no. 9, SP, 11 July 2010 (2010-07-11), pages 735 - 740, XP009145349, DOI: IROOXINDOLES INSPIRED BY NATURAL PRODUCTS
LIU,T-L. ET AL., ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9, 2011, pages 1980 - 1986, XP008182907
LIU,J. ET AL.: "DIRECT CONSTRUCTION OF NOVEL EXO'-SELECTIVE SPIROPYRROLIDINE", TETRAHEDRON LETTERS, vol. 53, no. 18, BI, 2012, pages 2336 - 2340, XP055140710, DOI: SOXINDOLES VIA A THREE-COMPONENT 1,3-DIPOLAR
JORGENSEN, K. A. ET AL., ORG. LETT., vol. 21, 2005, pages 4569
JORGENSEN, K. A. ET AL., CHEM. REV., vol. 98, 1998, pages 863
GRIGG, R. ET AL., TETRAHEDRON, vol. 48, 1992, pages 10431
SCHREIBER, S. L. ET AL., J. AM. CHEM. SOC., vol. 125, 2003, pages 10174
CARRETERO, J. C. ET AL., TETRAHEDRON, vol. 63, 2007, pages 6587
WANG, S. ET AL., J. AM. CHEM. SOC., vol. 127, 2005, pages 10130
WANG, S. ET AL., J. MED. CHEM., vol. 49, 2006, pages 3432
WILLIAMS, R. M. ET AL., J. AM. CHEM. SOC., vol. 122, 2000, pages 5666
GONG, L.-Z. ET AL., J. AM. CHEM. SOC., vol. 131, 2009, pages 13819
GONG, L.-Z. ET AL., ORG. LETT., vol. 13, 2011, pages 2418
GONG, L.-Z. ET AL., CHEM. EUR. J., vol. 18, 2012, pages 6885
WALDMANN, H. ET AL., NAT. CHEM., vol. 2, 2010, pages 735
WALDMANN, H. ET AL., TETRAHEDRON, vol. 67, 2011, pages 10195
WANG, C.-J. ET AL., ORG. BIOMOL. CHEM., vol. 9, 2011, pages 1980
ARAI, T. ET AL., CHEM. EUR. J., vol. 18, 2012, pages 8287
AMEDOHKOUH, M. ET AL., TETRAHEDRON ASYMMETRY, vol. 8, 2005, pages 1411
CORDOVA, A. ET AL., CHEM. COMM., 2006, pages 460
MA, J. A. ET AL., ORG. LETT., vol. 9, 2007, pages 923
T.W. GREENE; P.G.M. WUTS: "Protective Groups in Organic Synthesis", 2006, JOHN WILEY & SONS, INC.
See also references of EP 3042906A4
ANTONCHICK,A.P. ET AL.: "HIGHLY ENANTIOSELECTIVE SYNTHESIS AND CELLULAR EVALUATION OF", NATURE CHEMISTRY, vol. 2, no. 9, SP, 11 July 2010 (2010-07-11), pages 735 - 740, XP009145349, DOI: IROOXINDOLES INSPIRED BY NATURAL PRODUCTS
LIU,T-L. ET AL., ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9, 2011, pages 1980 - 1986, XP008182907
LIU,J. ET AL.: "DIRECT CONSTRUCTION OF NOVEL EXO'-SELECTIVE SPIROPYRROLIDINE", TETRAHEDRON LETTERS, vol. 53, no. 18, BI, 2012, pages 2336 - 2340, XP055140710, DOI: SOXINDOLES VIA A THREE-COMPONENT 1,3-DIPOLAR
JORGENSEN, K. A. ET AL., ORG. LETT., vol. 21, 2005, pages 4569
JORGENSEN, K. A. ET AL., CHEM. REV., vol. 98, 1998, pages 863
GRIGG, R. ET AL., TETRAHEDRON, vol. 48, 1992, pages 10431
SCHREIBER, S. L. ET AL., J. AM. CHEM. SOC., vol. 125, 2003, pages 10174
CARRETERO, J. C. ET AL., TETRAHEDRON, vol. 63, 2007, pages 6587
WANG, S. ET AL., J. AM. CHEM. SOC., vol. 127, 2005, pages 10130
WANG, S. ET AL., J. MED. CHEM., vol. 49, 2006, pages 3432
WILLIAMS, R. M. ET AL., J. AM. CHEM. SOC., vol. 122, 2000, pages 5666
GONG, L.-Z. ET AL., J. AM. CHEM. SOC., vol. 131, 2009, pages 13819
GONG, L.-Z. ET AL., ORG. LETT., vol. 13, 2011, pages 2418
GONG, L.-Z. ET AL., CHEM. EUR. J., vol. 18, 2012, pages 6885
WALDMANN, H. ET AL., NAT. CHEM., vol. 2, 2010, pages 735
WALDMANN, H. ET AL., TETRAHEDRON, vol. 67, 2011, pages 10195
WANG, C.-J. ET AL., ORG. BIOMOL. CHEM., vol. 9, 2011, pages 1980
ARAI, T. ET AL., CHEM. EUR. J., vol. 18, 2012, pages 8287
AMEDOHKOUH, M. ET AL., TETRAHEDRON ASYMMETRY, vol. 8, 2005, pages 1411
CORDOVA, A. ET AL., CHEM. COMM., 2006, pages 460
MA, J. A. ET AL., ORG. LETT., vol. 9, 2007, pages 923
T.W. GREENE; P.G.M. WUTS: "Protective Groups in Organic Synthesis", 2006, JOHN WILEY & SONS, INC.
See also references of EP 3042906A4
Attorney, Agent or Firm:
ISHIBASHI Koki et al. (JP)
Kimiki Ishibashi (JP)
Kimiki Ishibashi (JP)
Download PDF: