Title:
CLASS A GPCR-BINDING COMPOUND MODIFIER
Document Type and Number:
WIPO Patent Application WO/2018/207950
Kind Code:
A1
Abstract:
Provided are a novel class A GPCR antagonist, a production method for same, and a novel compound which interacts with the binding site of a class A GPCR Na+- water molecule cluster. A compound, or a salt thereof, having a structure in which are bonded a class A GPCR-binding compound and a functional group that binds to a class A GPCR Na+- water molecule cluster binding site. A class A GPCR antagonist production method comprising a step for binding, to another compound, a compound that binds to a class A GPCR Na+- water molecule cluster binding site.
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Inventors:
YOKOYAMA SHIGEYUKI (JP)
HORI TETSUYA (JP)
HORI TETSUYA (JP)
Application Number:
PCT/JP2018/018621
Publication Date:
November 15, 2018
Filing Date:
May 14, 2018
Export Citation:
Assignee:
YOKOYAMA SHIGEYUKI (JP)
International Classes:
A61K31/4192; C07D403/12; A61K31/7076; A61K39/395; A61K45/00; A61P43/00; C07H19/167; C07K16/40
Foreign References:
| US20160068512A1 | 2016-03-10 | |||
| JP2007528856A | 2007-10-18 | |||
| JP2000502333A | 2000-02-29 | |||
| JP2004513100A | 2004-04-30 | |||
| JP2001500146A | 2001-01-09 | |||
| JP2001509787A | 2001-07-24 | |||
| JP2001502655A | 2001-02-27 | |||
| JP2013536173A | 2013-09-19 | |||
| JP4334016B2 | 2009-09-16 | |||
| JP4288299B2 | 2009-07-01 | |||
| JP4215278B2 | 2009-01-28 | |||
| JP4047275B2 | 2008-02-13 | |||
| JP3917516B2 | 2007-05-23 | |||
| JP2931410B2 | 1999-08-09 | |||
| JP2007536299A | 2007-12-13 | |||
| JP2007513068A | 2007-05-24 | |||
| JP2006508992A | 2006-03-16 | |||
| JP2005529085A | 2005-09-29 | |||
| JP2005502630A | 2005-01-27 | |||
| JP2004513100A | 2004-04-30 | |||
| US4816567A | 1989-03-28 |
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CANALS, M. ET AL., TRENDS BIOCHEM. SCI., vol. 36, 2011, pages 663 - 672
MAHONEY, J. P ET AL., CURR. OPIN. STRUCT. BIOL., vol. 41, 2016, pages 247 - 254
GAO, Z. G. ET AL., BIOCHEM. PHARMACOL., vol. 65, 2003, pages 525 - 534
FREDRIKSSON, R. ET AL., MOL. PHARMACOL., vol. 63, 2003, pages 1256 - 1272
CERESA, B. P. ET AL., J. BIOL. CHEM., vol. 269, 1994, pages 29557 - 29564
WILSON, M. H. ET AL., MOL. PHARMACOL., vol. 59, 2001, pages 929 - 938
HORSTMAN, D. A. ET AL., J. BIOL. CHEM., vol. 265, 1990, pages 21590 - 21595
ARDATI, A. ET AL., MOL. PHARMACOL., vol. 51, 1997, pages 816 - 824
SELLEY, D. E. ET AL., BR. J. PHARMACOL., vol. 130, 2000, pages 987 - 996
KLEEMANN, P. ET AL., NAUNYN SCHMIEDEBERGS ARCH PHARMACOL., vol. 378, 2008, pages 261 - 274
VOSAHLIKOVA, M. ET AL., NAUNYN SCHMIEDEBERGS ARCH PHARMACOL., vol. 387, 2014, pages 487 - 502
NICKL, K. ET AL., NEUROSCI. LETT., vol. 447, 2008, pages 68 - 72
SCHNELL, D. ET AL., NEUROSCI. LETT., vol. 472, 2010, pages 114 - 118
BALLESTEROS, J. A. ET AL.: "Methods in Neurosciences", 1995, ACADEMIC PRESS, article "Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G protein-coupled receptors", pages: 366 - 428
KARPLUS, P. A. ET AL., SCIENCE, vol. 336, 2012, pages 1030 - 1033
MILLER-GALLACHER, J. L. ET AL., PLOS ONE, vol. 9, 2014, pages e92727
THOMPSON, A. A. ET AL., NATURE, vol. 485, 2012, pages 395 - 399
FENALTI, G. ET AL., NATURE, vol. 506, 2014, pages 191 - 196
ROSENBAUM, D. M. ET AL., NATURE, vol. 469, 2011, pages 236 - 240
CARPENTER, B. ET AL., NATURE, vol. 531, 2016, pages 335 - 340
KRUSE, A. C. ET AL., NATURE, vol. 482, 2013, pages 552 - 556
HUANG, W. ET AL., NATURE, vol. 524, 2015, pages 315 - 321
BIRKE, F. W. ET AL., J. PHARMACOL. EXP. THER., vol. 297, 2001, pages 458 - 466
YOKOMIZO, T. ET AL., NATURE, vol. 387, 1997, pages 620 - 624
GUTIERREZ-DE-TERAN, H. ET AL., STRUCTURE, vol. 21, 2013, pages 2175 - 2185
ROSENBAUM, D. M. ET AL., SCIENCE, vol. 318, 2007, pages 1266 - 1273
FREDERIKSSON, R. ET AL., MOL PHARMACOL, vol. 63, 2003, pages 1256 - 1272
SEIFERT, R. ET AL., NAUNYN-SCHMIEDEBERG'S ARCH PHARMACOL, 2002, pages 381 - 416
KHILNANI, G. ET AL., INDIAN J PHARMACOL, 2011, pages 492 - 501
STOY, H. ET AL., GENES & DISEASES, 2015, pages 108 - 132
BALLESTEROS, J. A. ET AL., METHODS NEUROSCI, 1995, pages 366 - 428
HOU J ET AL., EXPERT OPIN DRUG DISCOV., vol. 7, no. 6, June 2012 (2012-06-01), pages 489 - 501
BONNET D ET AL., BIOCONJUG CHEM., vol. 17, no. 6, November 2006 (2006-11-01), pages 1618 - 23
NAKAYAMA ET AL., BIOORG MED CHEM., vol. 5, no. 5, May 1997 (1997-05-01), pages 971 - 85
MARIE ET AL., J BIOL CHEM., vol. 276, no. 44, 2 November 2001 (2001-11-02), pages 41100 - 11
ANAT ET AL., PLOS ONE, vol. 6, no. 11, 2011, pages e27990
KRUSE ET AL., MOL PHARMACOL., vol. 84, no. 4, October 2013 (2013-10-01), pages 528 - 40
BERGE SM ET AL., J PHARM SCI., vol. 6, no. 1, 6 January 1977 (1977-01-06), pages 1 - 19
LAM, P. Y ET AL., J. MED. CHEM., vol. 46, 2003, pages 4405 - 4418
KOHLER GMILSTEIN C., NATURE, vol. 256, no. 5517, 7 August 1975 (1975-08-07), pages 495 - 497
CLACKSON ET AL., NATURE, vol. 352, no. 6336, 15 August 1991 (1991-08-15), pages 624 - 628
MARKS ET AL., J MOL BIOL., vol. 222, no. 3, 5 December 1991 (1991-12-05), pages 581 - 597
DARMOSTUK M ET AL., BIOTECHNOL ADV., vol. 33, no. 6, 1 November 2015 (2015-11-01), pages 1141 - 61
REVERDATTO S ET AL., CURR TOP MED CHEM., vol. 15, no. 12, 2015, pages 1082 - 101
HORI, T. ET AL., PROTEIN EXPR. PURIF., vol. 72, 2010, pages 66 - 74
HORI, T. ET AL., BIOCHEM. BIOPHYS. REP., vol. 4, 2015, pages 243 - 249
INOUE, A. ET AL.: "TGFa shedding assay: an accurate and versatile method for detecting GPCR activation", NAT. METHODS, vol. 9, 2012, pages 1021 - 1029, XP055220986, DOI: 10.1038/nmeth.2172
CHRISTOPOULOS, A. ET AL., PHARMACOL. REV., vol. 54, 2002, pages 323 - 374
LEACH, K. ET AL., TRENDS PHARMACOL. SCI., vol. 28, 2007, pages 382 - 389
HATO, M. ET AL., J. PHYS. CHEM. B, vol. 113, 2009, pages 10196 - 10209
HATO, M. ET AL., J. STRUCT. FUNCT. GENOMICS, vol. 15, 2014, pages 165 - 171
ADAMS, P. D. ET AL., ACTA CRYSTALLOGR. D BIOL. CRYSTALLOGR., vol. 66, 2010, pages 486 - 501
EVANS, P. R., ACTA CRYSTALLOGR. D BIOL. CRYSTALLOGR., vol. 67, 2011, pages 282 - 292
EVANS, P. R. ET AL., ACTA CRYSTALLOGR. D BIOL. CRYSTALLOGR., vol. 69, 2013, pages 1204 - 1214
BRUNGER, A. T. ET AL., ACTA CRYST., vol. D54, 1998, pages 905 - 921
BRUNGER, A. T., NATURE PROTOCOLS, vol. 2, 2007, pages 2728 - 2733
WU, B. ET AL., SCIENCE, vol. 330, 2010, pages 1066 - 1071
TAN, Q. ET AL., SCIENCE, vol. 341, 2013, pages 1387 - 1390
MANGLIK, A. ET AL., CELL, vol. 161, 2015, pages 1101 - 1111
KATRITCH, V ET AL., TRENDS BIOCHEM. SCI., vol. 39, 2014, pages 233 - 244
BASU, S. ET AL., J. BIOL. CHEM., vol. 282, 2007, pages 10005 - 10017
SABIRSH, A. ET AL., BIOCHEMISTRY, vol. 45, 2006, pages 5733 - 5744
MASSINK, A. ET AL., MOL. PHARMACOL., vol. 87, 2015, pages 305 - 313
AIGLSTORFER, I. ET AL.: "NPY Y1 antagonists: structure-activity relationships of arginine derivatives and hybrid compounds with arpromidine- like partial structures", REGULATORY PEPTIDES, vol. 75/76, 1998, pages 9 - 21, XP001010840, ISSN: 0167-0115, DOI: 10.1016/S0167-0115(98)00048-2
HICKS, ALEXANDRA ET AL.: "Leukotriene B4 receptor antagonists as therapeutics for inflammatory disease: preclinical and clinical developments", EXPERT OPINION ON INVESTIGATIONAL DRUGS, vol. 16, no. 12, 2007, pages 1909 - 1920, XP002726575, ISSN: 1354-3784, DOI: 10.1517/13543784.16.12.1909
NAKAYAMA, Y. ET AL.: "New serine protease inhibitors with leukotriene B4 (LTB4) receptor binding affinity", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 5, no. 5, 1997, pages 971 - 985, XP001181712, ISSN: 0968-0896, DOI: 10.1016/S0968-0896(97)00036-9
MARIE, J. ET AL.: "Control of conformational equilibria in the human B2 bradykinin receptor: Modeling of nonpeptidic ligand action and comparison to the rhodopsin structure", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 276, no. 44, 2001, pages 41100 - 41111, XP055613107, ISSN: 0021-9258
LUPALA, C. S. ET AL.: "New insights into the stereochemical requirements of the bradykinin B2 receptor antagonists binding", JOURNAL OF COMPUTER- AIDED MOLECULAR DESIGN, vol. 30, no. 1, 2016, pages 85 - 101, XP035913023, ISSN: 0920-654X, DOI: 10.1007/s10822-015-9890-z
LEVIT, A. ET AL.: "Modeling of human Prokineticin receptors: interactions with novel small-molecule binders and potential off-target drugs", PLOS ONE, vol. 6, no. 11, e27990, November 2011 (2011-11-01), pages 1 - 17, XP055613106, ISSN: 1932-6203
KRUSE, ANDREW C. ET AL.: "Muscarinic Receptors as Model Targets and Anti targets for Structure-Based Ligand Discovery", MOLECULAR PHARMACOLOGY, vol. 84, no. 4, 1 October 2013 (2013-10-01), pages 528 - 540, XP009518097, ISSN: 1521-0111, DOI: 10.1124/mol.113.087551
DATABASE CAS [online] 6 March 2014 (2014-03-06), retrieved from STN Database accession no. 1563162-34-4
DATABASE CAS [online] 5 March 2014 (2014-03-05), retrieved from STN Database accession no. 1562462-15-0
KATRITCH, VSEVOLOD ET AL.: "Allosteric sodium in class A GPCR signaling", TRENDS IN BIOCHEMICAL SCIENCES, vol. 39, no. 5, 2014, pages 233 - 244, XP055613105, ISSN: 0968-0004
HORI, TETSUYA ET AL.: "Na+-mimicking ligands stabilize the inactive state of leukotriene B4 receptor BLT1", NATURE CHEMICAL BIOLOGY, vol. 14, no. 3, 8 January 2018 (2018-01-08), pages 262 - 269, XP055613102, ISSN: 1552-4450
CANALS, M. ET AL., TRENDS BIOCHEM. SCI., vol. 36, 2011, pages 663 - 672
MAHONEY, J. P ET AL., CURR. OPIN. STRUCT. BIOL., vol. 41, 2016, pages 247 - 254
GAO, Z. G. ET AL., BIOCHEM. PHARMACOL., vol. 65, 2003, pages 525 - 534
FREDRIKSSON, R. ET AL., MOL. PHARMACOL., vol. 63, 2003, pages 1256 - 1272
CERESA, B. P. ET AL., J. BIOL. CHEM., vol. 269, 1994, pages 29557 - 29564
WILSON, M. H. ET AL., MOL. PHARMACOL., vol. 59, 2001, pages 929 - 938
HORSTMAN, D. A. ET AL., J. BIOL. CHEM., vol. 265, 1990, pages 21590 - 21595
ARDATI, A. ET AL., MOL. PHARMACOL., vol. 51, 1997, pages 816 - 824
SELLEY, D. E. ET AL., BR. J. PHARMACOL., vol. 130, 2000, pages 987 - 996
KLEEMANN, P. ET AL., NAUNYN SCHMIEDEBERGS ARCH PHARMACOL., vol. 378, 2008, pages 261 - 274
VOSAHLIKOVA, M. ET AL., NAUNYN SCHMIEDEBERGS ARCH PHARMACOL., vol. 387, 2014, pages 487 - 502
NICKL, K. ET AL., NEUROSCI. LETT., vol. 447, 2008, pages 68 - 72
SCHNELL, D. ET AL., NEUROSCI. LETT., vol. 472, 2010, pages 114 - 118
BALLESTEROS, J. A. ET AL.: "Methods in Neurosciences", 1995, ACADEMIC PRESS, article "Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G protein-coupled receptors", pages: 366 - 428
KARPLUS, P. A. ET AL., SCIENCE, vol. 336, 2012, pages 1030 - 1033
MILLER-GALLACHER, J. L. ET AL., PLOS ONE, vol. 9, 2014, pages e92727
THOMPSON, A. A. ET AL., NATURE, vol. 485, 2012, pages 395 - 399
FENALTI, G. ET AL., NATURE, vol. 506, 2014, pages 191 - 196
ROSENBAUM, D. M. ET AL., NATURE, vol. 469, 2011, pages 236 - 240
CARPENTER, B. ET AL., NATURE, vol. 531, 2016, pages 335 - 340
KRUSE, A. C. ET AL., NATURE, vol. 482, 2013, pages 552 - 556
HUANG, W. ET AL., NATURE, vol. 524, 2015, pages 315 - 321
BIRKE, F. W. ET AL., J. PHARMACOL. EXP. THER., vol. 297, 2001, pages 458 - 466
YOKOMIZO, T. ET AL., NATURE, vol. 387, 1997, pages 620 - 624
GUTIERREZ-DE-TERAN, H. ET AL., STRUCTURE, vol. 21, 2013, pages 2175 - 2185
ROSENBAUM, D. M. ET AL., SCIENCE, vol. 318, 2007, pages 1266 - 1273
FREDERIKSSON, R. ET AL., MOL PHARMACOL, vol. 63, 2003, pages 1256 - 1272
SEIFERT, R. ET AL., NAUNYN-SCHMIEDEBERG'S ARCH PHARMACOL, 2002, pages 381 - 416
KHILNANI, G. ET AL., INDIAN J PHARMACOL, 2011, pages 492 - 501
STOY, H. ET AL., GENES & DISEASES, 2015, pages 108 - 132
BALLESTEROS, J. A. ET AL., METHODS NEUROSCI, 1995, pages 366 - 428
HOU J ET AL., EXPERT OPIN DRUG DISCOV., vol. 7, no. 6, June 2012 (2012-06-01), pages 489 - 501
BONNET D ET AL., BIOCONJUG CHEM., vol. 17, no. 6, November 2006 (2006-11-01), pages 1618 - 23
NAKAYAMA ET AL., BIOORG MED CHEM., vol. 5, no. 5, May 1997 (1997-05-01), pages 971 - 85
MARIE ET AL., J BIOL CHEM., vol. 276, no. 44, 2 November 2001 (2001-11-02), pages 41100 - 11
ANAT ET AL., PLOS ONE, vol. 6, no. 11, 2011, pages e27990
KRUSE ET AL., MOL PHARMACOL., vol. 84, no. 4, October 2013 (2013-10-01), pages 528 - 40
BERGE SM ET AL., J PHARM SCI., vol. 6, no. 1, 6 January 1977 (1977-01-06), pages 1 - 19
LAM, P. Y ET AL., J. MED. CHEM., vol. 46, 2003, pages 4405 - 4418
KOHLER GMILSTEIN C., NATURE, vol. 256, no. 5517, 7 August 1975 (1975-08-07), pages 495 - 497
CLACKSON ET AL., NATURE, vol. 352, no. 6336, 15 August 1991 (1991-08-15), pages 624 - 628
MARKS ET AL., J MOL BIOL., vol. 222, no. 3, 5 December 1991 (1991-12-05), pages 581 - 597
DARMOSTUK M ET AL., BIOTECHNOL ADV., vol. 33, no. 6, 1 November 2015 (2015-11-01), pages 1141 - 61
REVERDATTO S ET AL., CURR TOP MED CHEM., vol. 15, no. 12, 2015, pages 1082 - 101
HORI, T. ET AL., PROTEIN EXPR. PURIF., vol. 72, 2010, pages 66 - 74
HORI, T. ET AL., BIOCHEM. BIOPHYS. REP., vol. 4, 2015, pages 243 - 249
INOUE, A. ET AL.: "TGFa shedding assay: an accurate and versatile method for detecting GPCR activation", NAT. METHODS, vol. 9, 2012, pages 1021 - 1029, XP055220986, DOI: 10.1038/nmeth.2172
CHRISTOPOULOS, A. ET AL., PHARMACOL. REV., vol. 54, 2002, pages 323 - 374
LEACH, K. ET AL., TRENDS PHARMACOL. SCI., vol. 28, 2007, pages 382 - 389
HATO, M. ET AL., J. PHYS. CHEM. B, vol. 113, 2009, pages 10196 - 10209
HATO, M. ET AL., J. STRUCT. FUNCT. GENOMICS, vol. 15, 2014, pages 165 - 171
ADAMS, P. D. ET AL., ACTA CRYSTALLOGR. D BIOL. CRYSTALLOGR., vol. 66, 2010, pages 486 - 501
EVANS, P. R., ACTA CRYSTALLOGR. D BIOL. CRYSTALLOGR., vol. 67, 2011, pages 282 - 292
EVANS, P. R. ET AL., ACTA CRYSTALLOGR. D BIOL. CRYSTALLOGR., vol. 69, 2013, pages 1204 - 1214
BRUNGER, A. T. ET AL., ACTA CRYST., vol. D54, 1998, pages 905 - 921
BRUNGER, A. T., NATURE PROTOCOLS, vol. 2, 2007, pages 2728 - 2733
WU, B. ET AL., SCIENCE, vol. 330, 2010, pages 1066 - 1071
TAN, Q. ET AL., SCIENCE, vol. 341, 2013, pages 1387 - 1390
MANGLIK, A. ET AL., CELL, vol. 161, 2015, pages 1101 - 1111
KATRITCH, V ET AL., TRENDS BIOCHEM. SCI., vol. 39, 2014, pages 233 - 244
BASU, S. ET AL., J. BIOL. CHEM., vol. 282, 2007, pages 10005 - 10017
SABIRSH, A. ET AL., BIOCHEMISTRY, vol. 45, 2006, pages 5733 - 5744
MASSINK, A. ET AL., MOL. PHARMACOL., vol. 87, 2015, pages 305 - 313
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