Title:
GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
Document Type and Number:
WIPO Patent Application WO/2019/133770
Kind Code:
A3
Abstract:
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
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Inventors:
WANG BING (US)
CHAO QI (US)
CHAO QI (US)
Application Number:
PCT/US2018/067784
Publication Date:
August 15, 2019
Filing Date:
December 28, 2018
Export Citation:
Assignee:
BIOMARIN PHARM INC (US)
International Classes:
C07D249/06; A61K31/4192; A61P13/00; C07D401/04; C07D401/06; C07D401/12; C07D403/06; C07D403/12; C07D417/04; C07D417/12
Domestic Patent References:
| WO2017100266A1 | 2017-06-15 |
Foreign References:
| JP2017095366A | 2017-06-01 | |||
| CN105669569A | 2016-06-15 | |||
| CN105541796A | 2016-05-04 | |||
| US20050272789A1 | 2005-12-08 | |||
| US4428956A | 1984-01-31 | |||
| US4431652A | 1984-02-14 | |||
| US20150284343A1 | 2015-10-08 | |||
| US4248879A | 1981-02-03 | |||
| US4349561A | 1982-09-14 | |||
| US4431660A | 1984-02-14 |
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CHAI ET AL.: "One-Pot, Three-Component Reaction Using Modified Julia Reagents: A Facile Synthesis of 4,5-Disubstituted 1,2,3-( NH )-Triazoles in a Wet Organic Solvent", ACS COMBINATORIAL SCIENCE, vol. 17, no. 3, 11 February 2015 (2015-02-11), US, pages 147 - 151, XP055569326, ISSN: 2156-8952, DOI: 10.1021/co5001597
AUGUSTINE ET AL.: "[alpha]-Haloacrylates as acceptors in the [3 + 2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates", ORG. BIOMOL. CHEM., vol. 12, no. 14, 1 January 2014 (2014-01-01), pages 2280 - 2288, XP055569357, ISSN: 1477-0520, DOI: 10.1039/c3ob42276c
BUCKLE ET AL.: "STUDIES ON 1,2,3-TRIAZOLES. 10. SYNTHESIS AND ANTIALLERGIC PROPERTIES OF 9-OXO-1H,9H-BENZOTHIOPYRANO[2,3-D]-1,2,3-TRIAZOLES AND THEIR S-OXIDES", J. MED. CHEM., vol. 27, no. 2, 1 January 1984 (1984-01-01), pages 223 - 227, XP001007181, ISSN: 0022-2623, DOI: 10.1021/JM00368A021
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; NISHINO, SHIGEYOSHI ET AL: "Preparation of 4,5-disubstituted-1,2,3-triazole derivatives by cyclization of 3-halo-2-hydrazono-1-hydroxyiminopropane derivatives", XP002791860, retrieved from STN Database accession no. 2003:389981
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KHALAF ET AL.: "A new flexible strategy for the synthesis of-difluoro-bisarylic derivatives and heterocyclic analogues", TETRAHEDRON, vol. 67, no. 21, 22 March 2011 (2011-03-22), pages 3881 - 3886, XP028384420, ISSN: 0040-4020, [retrieved on 20110330], DOI: 10.1016/J.TET.2011.03.073
CHEN ET AL.: "Discovery and Structure-Activity Relationship Study of 4-Phenoxythiazol-5-carboxamides as Highly Potent TGR5 Agonists", CHEM. PHARM. BULL., vol. 4, no. 4, 1 January 2016 (2016-01-01), JP, pages 326 - 339, XP055594816, ISSN: 0009-2363, DOI: 10.1248/cpb.c15-00905
DATABASE REAXYS [online] Elsevier Life Sciences IP Limited; 1982, XP002791910, Database accession no. 4567854, 4574239, 4587423, 4698190 (XRNs)
WAMHOFF ET AL.: "Heterocyclic [beta]-enamino esters 43-easy13C NMR distinction between aryl-substituted dimroth isomers of the 1,2,3-triazole series", MAGNETIC RESONANCE IN CHEMISTRY, vol. 24, no. 9, 1 September 1986 (1986-09-01), GB, pages 809 - 811, XP055595256, ISSN: 0749-1581, DOI: 10.1002/mrc.1260240914
PIPPIONE ET AL.: "Hydroxytriazole derivatives as potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors discovered by bioisosteric scaffold hopping approach", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 139, 24 August 2017 (2017-08-24), FR, pages 936 - 946, XP055595356, ISSN: 0223-5234, DOI: 10.1016/j.ejmech.2017.08.046
ALIMI ET AL.: "Photochemical C-H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D : Photochemical C-H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D", EUR. J. ORG. CHEM., vol. 2017, no. 22, 5 April 2017 (2017-04-05), DE, pages 3197 - 3210, XP055569093, ISSN: 1434-193X, DOI: 10.1002/ejoc.201700300
LI ET AL.: "Catalytic Intermolecular Cross-Couplings of Azides and LUMO-Activated Unsaturated Acyl Azoliums", ACS CATALYSIS, vol. 7, no. 3, 3 March 2017 (2017-03-03), US, pages 2139 - 2144, XP055569122, ISSN: 2155-5435, DOI: 10.1021/acscatal.6b03674
YUAN ET AL.: "Cycloadduct formation of [alpha],[beta]-unsaturated esters with azides catalyzed by NHC systems", ORG. BIOMOL. CHEM., vol. 15, no. 43, 1 January 2017 (2017-01-01), pages 9066 - 9070, XP055569134, ISSN: 1477-0520, DOI: 10.1039/C7OB02469J
SMALLEY ET AL.: "Novel heterocyclic scaffolds of GW4064 as farnesoid X receptor agonists", BIOORG. MED. CHEM. LETT., vol. 25, no. 2, 1 January 2015 (2015-01-01), AMSTERDAM, NL, pages 280 - 284, XP055569312, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2014.11.050
CHAI ET AL.: "One-Pot, Three-Component Reaction Using Modified Julia Reagents: A Facile Synthesis of 4,5-Disubstituted 1,2,3-( NH )-Triazoles in a Wet Organic Solvent", ACS COMBINATORIAL SCIENCE, vol. 17, no. 3, 11 February 2015 (2015-02-11), US, pages 147 - 151, XP055569326, ISSN: 2156-8952, DOI: 10.1021/co5001597
AUGUSTINE ET AL.: "[alpha]-Haloacrylates as acceptors in the [3 + 2] cycloaddition reaction with NaN3: an expedient approach to N-unsubstituted 1,2,3-triazole-4-carboxylates", ORG. BIOMOL. CHEM., vol. 12, no. 14, 1 January 2014 (2014-01-01), pages 2280 - 2288, XP055569357, ISSN: 1477-0520, DOI: 10.1039/c3ob42276c
BUCKLE ET AL.: "STUDIES ON 1,2,3-TRIAZOLES. 10. SYNTHESIS AND ANTIALLERGIC PROPERTIES OF 9-OXO-1H,9H-BENZOTHIOPYRANO[2,3-D]-1,2,3-TRIAZOLES AND THEIR S-OXIDES", J. MED. CHEM., vol. 27, no. 2, 1 January 1984 (1984-01-01), pages 223 - 227, XP001007181, ISSN: 0022-2623, DOI: 10.1021/JM00368A021
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; NISHINO, SHIGEYOSHI ET AL: "Preparation of 4,5-disubstituted-1,2,3-triazole derivatives by cyclization of 3-halo-2-hydrazono-1-hydroxyiminopropane derivatives", XP002791860, retrieved from STN Database accession no. 2003:389981
DATABASE REAXYS [online] Elsevier Life Sciences IP Limited; 1912, XP002791883, Database accession no. 55780 (XRN)
KHALAF ET AL.: "A new flexible strategy for the synthesis of-difluoro-bisarylic derivatives and heterocyclic analogues", TETRAHEDRON, vol. 67, no. 21, 22 March 2011 (2011-03-22), pages 3881 - 3886, XP028384420, ISSN: 0040-4020, [retrieved on 20110330], DOI: 10.1016/J.TET.2011.03.073
CHEN ET AL.: "Discovery and Structure-Activity Relationship Study of 4-Phenoxythiazol-5-carboxamides as Highly Potent TGR5 Agonists", CHEM. PHARM. BULL., vol. 4, no. 4, 1 January 2016 (2016-01-01), JP, pages 326 - 339, XP055594816, ISSN: 0009-2363, DOI: 10.1248/cpb.c15-00905
DATABASE REAXYS [online] Elsevier Life Sciences IP Limited; 1982, XP002791910, Database accession no. 4567854, 4574239, 4587423, 4698190 (XRNs)
WAMHOFF ET AL.: "Heterocyclic [beta]-enamino esters 43-easy13C NMR distinction between aryl-substituted dimroth isomers of the 1,2,3-triazole series", MAGNETIC RESONANCE IN CHEMISTRY, vol. 24, no. 9, 1 September 1986 (1986-09-01), GB, pages 809 - 811, XP055595256, ISSN: 0749-1581, DOI: 10.1002/mrc.1260240914
PIPPIONE ET AL.: "Hydroxytriazole derivatives as potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors discovered by bioisosteric scaffold hopping approach", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 139, 24 August 2017 (2017-08-24), FR, pages 936 - 946, XP055595356, ISSN: 0223-5234, DOI: 10.1016/j.ejmech.2017.08.046
Attorney, Agent or Firm:
CAMPBELL, A., Patricia et al. (US)
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