A Year In Review — Curia's (formerly AMRI) Contributions to Science in 2020

040E93C7-D189-4233-A102-58C0580BE529 publications patents

 Curia (formerly AMRI) Research Publications 

The following research articles appeared in peer-reviewed scientific journals that described innovations conceived by Curia scientists. In most of these cases, these manuscripts were written by Curia lead authors to communicate independent research, or were co-authored with customers to communicate research in collaboration with Curia. Below are the bibliographies for these publications, including the abstracts, as they appeared with the original documents. The lead author name(s) are indicated. 

1. “Optimized plant compound with potent anti-biofilm activity across gram-negative species,” Bioorganic & Medicinal Chemistry 2020, 28(5), 115229.
https://doi.org/10.1016/j.bmc.2019.115229
Julie A. Lawrence,1 Zhongping Huang,2 Sivaprakash Rathinavelu,1 Jin-Feng Hu,1 Eliane Garo,1 Michael Ellis,2 Vanessa L. Norman,1 Ronald Buckle,2 Russell B. Williams,1 Courtney M. Starks1,* and Gary R.Eldridge1
1Sequoia Sciences, Inc., St. Louis, Missouri, USA
2Medicinal Chemistry, AMRI Albany and AMRI Buffalo

2. “CSTI-300 (SMP-100): A Novel 5-HT3 receptor partial agonist with potential to treat patients with irritable bowel syndrome or carcinoid syndrome,” Journal of Pharmacology and Experimental Therapeutics 2020, 373(1), 122- 134.
https://doi.org/10.1124/jpet.119.261008
Alexander Roberts,1 Gillian Grafton,1 Andrew D. Powell,4 Kristian Brock,3 Chunlin Chen,5 Dejian Xie,6 Jinkun Huang,6 Shuang Liu,7 Alison J. Cooper,1 Catherine A. Brady,1 Omar Qureshi,1 Zania Stamataki,2 David D. Manning,8 Nicholas A. Moore,8 Bruce J. Sargent,9 Peter R. Guzzo7 and Nicholas M. Barnes1,*
1Neuropharmacology Research Group, Institute of Clinical Sciences, College of Medical and Dental Sciences, University of Birmingham, Birmingham, UK
2Institute of Immunology and Immunotherapy, College of Medical and Dental Sciences, University of Birmingham, Birmingham, UK
3Diagnostics, Drugs, Devices and Biomarkers, Cancer Research UK Clinical Trials Unit, University of Birmingham, Birmingham, UK
4Department of Life Science, School of Health Sciences, Birmingham City University, Birmingham, UK
5Shanghai Medicilon Inc., Shanghai, China
6Chengdu SciMount Pharmatech Co. Ltd., Chengdu, China
7ConSynance Therapeutics, Inc., Rensselaer, New York, USA
8AMRI Albany
9Sargent Consulting, Hendersonville, North Carolina, USA

CSTI-300 (SMP-100)

3. “Readily accessible sp3-rich cyclic hydrazine frameworks exploiting nitrogen fluxionality,” Chemical Science 2020, 11(6), 1636-1642.
https://doi.org/10.1039/C9SC04849A
Conor Dean, 1 Sundaram Rajkumar, 1 Stefan Roesner, 1 Nessa Carson, 2 Guy J. Clarkson, 1 Martin Wills, 1 Matthew Jones 3 and Michael Shipman1,*
1Department of Chemistry, University of Warwick, Coventry, UK
2AMRI UK
3Eli Lilly & Company, Erl Wood Manor, Surrey, UK

4. “Discovery of [1,2,4]triazolo[1,5-a]pyridine derivatives as potent and orally bioavailable RORyt inverse agonists,” ACS Medicinal Chemistry Letters 2020, 11(4), 528-534.
https://doi.org/10.1021/acsmedchemlett.9b00649
Ryota Nakajima,1,* Hiroyuki Oono,1 Sakae Sugiyama,1 Yohei Matsueda,1 Tomohide Ida,1 Shinji Kakuda,1 Jun Hirata,1 Atsushi Baba,1 Akito Makino,1 Ryo Matsuyama,1 Ryan D. White,2 Ryan P. Wurz,3 Youngsook Shin,3 Xiaoshan Min,4 Angel Guzman-Perez,2 Zhulun Wang,5 Antony Symons,6 Sanjay K. Singh,7 Srinivasa Reddy Mothe,7 Sergei Belyakov,7 Anjan Chakrabarti7 and Satoshi Shuto8,9,*
1Teijin Institute for Bio-medical Research, Teijin Pharma Limited, Tokyo, Japan
2Department of Medicinal Chemistry, Amgen Discovery Research, Amgen Inc., Cambridge, Massachusetts, USA
3Department of ‡Medicinal Chemistry, Amgen Discovery Research, Amgen Inc., Thousand Oaks, California, USA Departments of
4Biologics
5Inflammation & Oncology Research and
6Molecular Engineering, Amgen Discovery Research, Amgen Inc., South San Francisco, California, USA
7AMRI Singapore Research Centre
8Faculty of Pharmaceutical Sciences and 9Center for Research and Education on Drug Discovery, Hokkaido University, Sapporo, Japan

[1,2,4]triazolo[1,5-a]pyridine

5. “Imaging mutant Huntingtin aggregates: Development of a potential PET ligand,” Journal of Medicinal Chemistry 202063(15), 8608-8633.
https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c00955
Longbin Liu,1,* Michael E. Prime,2,* Matt R. Lee,1 Vinod Khetarpal,1 Christopher J. Brown,2 Peter D. Johnson,2 Patricia Miranda-Azpiazu,3 Xuemei Chen,4 Daniel Clark-Frew,2 Samuel Coe,2 Randall Davis,4 Anthony Dickie,2 Andreas Ebneth,2 Simone Esposito,5 Elise Gadouleau,2 Xinjie Gai,2 Sebastien Galan,2 Samantha Green,2 Catherine Greenaway,2 Paul Giles,2 Christer Halldin,3 Sarah Hayes,2 Todd Herbst,1 Frank Herrmann,6 Manuela Heßmann,6 Zhisheng Jia,3 Alexander Kiselyov,1 Adrian Kotey,2 Thomas Krulle,2 John E. Mangette,4 Richard W. Marston,2 Sergio Menta,5 Matthew R. Mills,2 Edith Monteagudo,5 Sangram Nag,3 Martina Nibbio,5 Laura Orsatti,5 Sabine Schaertl,6 Christoph Scheich,6 Joanne Sproston,2 Vladimir Stepanov,3 Marie Svedberg,3 Akihiro Takano,3 Malcolm Taylor,2 Wayne Thomas,2 Miklós Toth,3 Darshan Vaidya,2 Katarina Vanräs,3 Derek Weddell,2 Ian Wigginton,2 John Wityak,1 Ladislav Mrzljak,1 Ignacio Munoz-Sanjuan,1 Jonathan A. Bard1 and Celia Dominguez1,*
1CHDI Foundation, Los Angeles, California, USA
2Evotec UK Ltd, Abingdon, UK
3Department of Clinical Neuroscience, Centre for Psychiatric Research, Karolinska Hospital, Karolinska Institutet, Stockholm, Sweden
4AMRI Albany, USA
5IRBM, IRBM Science Park S.p.A., Pomezia, Italy
6Evotec AG, Hamburg, Germany

PET ligand

6. “Design and synthesis of novel methoxypyridine-derived gamma-secretase modulators,” Bioorganic & Medicinal Chemistry 2020, 28(22), 115734.
https://doi.org/10.1016/j.bmc.2020.115734
Kevin D. Rynearson,1,* Ronald N. Buckle,2 R. Jason Herr,2 Nicholas J. Mayhew,2, Xinchao Chen,2 William D. Paquette,2 Samuel A. Sakwa,2 Jinhai Yang,2 Keith D. Barnes,2 Phuong Nguyen,1 William C. Mobley,1 Graham Johnson,3 Juinn H. Lin,4 Rudolph E. Tanzi5 and Steven L. Wagner1,6
1Department of Neurosciences, University of California, San Diego, La Jolla, California, USA
2Department of Medicinal Chemistry, AMRI Albany
3NuPharmAdvise, Sanbornton, New Hampshire, USA
4Biopharm Consulting Partners, Ambler, Pennsylvania, USA
5Genetics and Aging Research Unit, Department of Neurology, Massachusetts General Hospital, Charlestown, Massachusetts, USA
6Veterans Administrative San Diego Healthcare System, La Jolla, California, USA

methoxypyridine-derived gamma-secretase modulators

7. “Design, synthesis and biological evaluation of novel Pseudomonas aeruginosa DNA gyrase B inhibitors,” Bioorganic Chemistry 2020, 100, 103905.
https://doi.org/10.1016/j.bioorg.2020.103905
Sridhar Jogula,1 Vagolu Siva Krishna,1 Nikhila Meda,1 Vadla Balraju2 and Dharmarajan Sriram1,*
1Department of Pharmacy, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, India
2Albany Molecular Research Hyderabad Research Centre

Pseudomonas aeruginosa DNA gyrase B inhibitors

8. “Structural analysis of the catalytic domain of Artemis endonuclease/SNM1C reveals distinct structural features,” The Journal of Biological Chemistry 2020, 295(35), 12368-12377.
https://doi.org/10.1074/jbc.RA120.014136
Md Fazlul Karim,1 Shanshan Liu,1 Adrian R. Laciak,1 Leah Volk,1 Mary Koszelak-Rosenblum,1 Michael R. Lieber,2 Mousheng Wu,3 Rory Curtis,1 Nian N. Huang,1 Grant Carr1,* and Guangyu Zhu1,*
1Discovery Biology, Albany Molecular Research Inc., Buffalo
2USC Norris Comprehensive Cancer Center, Departments of Pathology, Biochemistry & Molecular Biology, and Molecular Microbiology & Immunology, and the Molecular and Computational Biology Section of the Department of Biological Sciences, University of Southern California Keck School of Medicine, Los Angeles, California, USA
3Chemistry Department, Drug Discovery Division, Southern Research, Birmingham, Alabama, USA

9. “Towards developing discriminating dissolution methods for formulations containing nano-particulates in solution; The impact of particle drift and drug activity in solution,” Molecular Pharmaceutics 2020, 17(11), 4125-4140.
https://doi.org/10.1021/acs.molpharmaceut.0c00599
Freddy A. Arce,1 Nico Setiawan,2 Heather R. Campbell,1 Xingyu Lu,3,4 Matthew J. Nethercott,5 Paul Bummer,1 Yongchao Su3,6,7 and Patrick J. Marsac1,*
1Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, USA
2Albany Molecular Research Inc., West Lafayette
3Pharmaceutical Sciences, Merck & Co., Kenilworth, New Jersey, USA
4Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, Hangzhou, Zhejiang, China
5Kansas Analytical Services, LLC, Loveland, Colorado, USA
6Division of Molecular Pharmaceutics and Drug Delivery, College of Pharmacy, The University of Texas at Austin, Austin, Texas, USA
7Department of Industrial and Physical Pharmacy, College of Pharmacy, Purdue University, West Lafayette, Indiana, USA

10. “In situ XRPD study of the ambient-pressure synthesis of nonstoichiometric Ag3O from Ag-Ag2O thin films: Phase abundance, unit-cell parameters, and c/a as a function of temperature and time,” Powder Diffraction 2020, 35(4), 247-261.
https://doi.org/10.1017/S0885715620000561
Paul J. Schields,* Nicholas Dunwoody, David Field and Zachary Wilson
AMRI West Lafayette

In situ XRPD study of the ambient-pressure synthesis of nonstoichiometric Ag3O from Ag-Ag2O thin films

Patents

  1. Krasutsky, S.; Tweedie, S.; Ramamoorthy, G. Process for preparing 1,4-dihydro-4-oxoquinoline-2-carboxylates and 4-aminoquinoline compounds therefrom. U.S. Patent 10,875,831, December 29, 2020.
  2. Smith, A.; White, H. S.; Tavares, F. X.; Krasutsky, S.; Chen, J.; Dorrow, R. L.; Zhong, H. Synthesis of n-(heteroaryl)- pyrrolo[3,2-d]pyrimidin-2-amines. U.S. Patent 10,865,210, December 15, 2020.
  3. Mehta, S. V.; Teng, J.; Selbo, J. Polymorphs of cocrystals of epigallocatechin gallate and caffeine. U.S. Patent 10,813,938, October 27, 2020.
  4. Petrukhin, K.; Cioffi, C.; Johnson, G.; Dobri, N.; Freeman, E.; Chen, P.; Conlon, M.; Zhu, L. Octahydropyrrolopyrroles their preparation and use. U.S. Patent 10,787,453, September 29, 2020.
  5. Quinn, J. F.; Duffy, B. C.; Liu, S.; Wang, R.; Jiang, M. X.; Martin, G. S.; Wagner, G. S.; Young, P. R. Bicyclic bromodomain inhibitors. U.S. Patent 10,772,892, September 15, 2020.
  6. Grisenti, P.; Argese, M.; Pengo, D.; Grilli, M. D.; Fumagalli, E.; Motta, G. Polymorphic mixture of Rifaximin and its use for the preparation of solid formulations. U.S. Patent 10,745,415, August 18, 2020.
  7. DeCrescenzo, G.; Welsch, D.; Vlahova, P. I.; Boerrigter, S. X. M.; Aronov, A.; Keshavarz-Shokri, A.; Scangas, A. N.; Stavropoulos, K.; Littler, B.; Kadiyala, I. N.; Alargova, R. G. Crystalline forms of C.sub.21H.sub.22Cl.sub.2N.sub.4O- sub.2. U.S. Patent 10,738,027, August 11, 2020.
  8. Jiang, X.; Walling, J. A.; Bevill, M. J.; Seadeek, C. S.; Smit, J. P. Co-crystal forms of a novobiocin analog and proline. U.S. Patent 10,717,755, July 21, 2020.
  9. Jiang, M. X.; Molino, B. F.; Liu, S.; Wang, R.; Duffy, B. C.; Quinn, J. F.; Wagner, G. S. Substituted pyridinones as bromodomain inhibitors. U.S. Patent 10,710,992, July 14, 2020.
  10. Greer, E.; Anderson, S.; Maloney, M.; Yu, S.; Albert, E.; Rigsbee, E. Solid state forms of (S)-2-(((S)-6,8-difluoro- 1,2,3,4-tetrahydronaphthalen-2-yl)amino)-N-(1-(2- -methyl-1-(neopentylamino)propan-2-yl)-1H-imidazol-4-yl)-pentanamide and uses thereof. U.S. Patent 10,710,966, July 14, 2020.
  11. Surman, M.; Thottathil, J. K.; Golden, K.; Pasetto, P.; Jin, X.; Jiang, X.; Camara, F. Methods and compositions for preventing opioid abuse. U.S. Patent 10,695,342, June 30, 2020.
  12. Cacatian, S.; Claremon, D. A.; Dillard, L. W.; Dong, C.; Fan, Y.; Jia, L.; Lotesta, S. D.; Marcus, A.; Morales-Ramos, A.; Singh, S. B.; Venkatraman, S.; Yuan, J.; Zheng, Y.; Zhuang, L.; Parent, S. D.; Houston, T. L. Inhibitors of the menin-MLL interaction. U.S. Patent 10,683,302, June 16, 2020.
  13. Emanuele, R. M.; Shattock-Gordon, T.; Williford, T.; Andres, M.; Andres, P. Solid forms of cannabidiol and uses thereof. U.S. Patent 10,604,467, March 31, 2020.
  14. Herr, R. J.; Gregg, B. T.; Geiss, W. B. Methods and intermediates for the preparation of omacetaxine and cephalotaxine derivatives thereof. U.S. Patent 10,597,401, March 24, 2020.
  15. Perez Encabo, A.; Turiel Hernandez, J.; Fernandez Sainz, Y.; Lorente Bonde-Larsen, A. Process and intermediates for the preparation of benzo[b]thiophene compounds. U.S. Patent 10,597,386, March 24, 2020.
  16. Greer, E.; Anderson, S.; Maloney, M.; Yu, S.; Albert, E.; Rigsbee, E. Solid state forms of (S)-2-(((S)-6,8-difluoro- 1,2,3,4-tetrahydronaphthalen-2-yl)amino)-N-(1-(2- -methyl-1-(neopentylamino)propan-2-yl)-1H-imidazol-4-yl)-pentanamide and uses thereof. U.S. Patent 10,590,087, March 17, 2020.
  17. Petrukhin, K.; Cioffi, C.; Johnson, G.; Dobri, N.; Freeman, E.; Chen, P.; Conlon, M.; Zhu, L. N-alkyl-2- phenoxyethanamines, their preparation and use. U.S. Patent 10,570,148, February 25, 2020.
  18. Grisenti, P.; Argese, M.; Pengo, D.; Grilli, M. D.; Fumagalli, E.; Motta, G. Polymorphic mixture of Rifaximin and its use for the preparation of solid formulations. U.S. Patent 10,556,915, February 11, 2020.
  19. Statler, J. A.; Shaw, A. A.; Imbert, D. C.; Nelson, J. L.; Andres, P.; McQueen, L. L.; Boerrigter, S. X. M.; Selbo, J. G.; Andres, M. C. Glycopyrrolate salts. U.S. Patent 10,548,875, February 4, 2020.
  20. Statler, J. A.; Shaw, A. A.; Imbert, D. C.; Nelson, J. L.; Andres, P.; McQueen, L. L.; Boerrigter, S. X. M.; Selbo, J. G.; Andres, M. C. Glycopyrrolate salts. U.S. Patent 10,543,192, January 28, 2020.

Compiled by R. Jason Herr, Ph.D. and Wendy Quinn, AMRI

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