An azirine solid-state photodegradant of the CCR2/CCR5 dual antagonist BMS-813160

被引：1

作者：

Ayers, Sloan ^{[1
]}

La Cruz, Thomas ^{[1
]}

Park, Hyunsoo ^{[2
]}

Ramirez, Antonio ^{[1
]}

Hritzko, Benjamin ^{[1
]}

Sarjeant, Amy ^{[2
]}

Lin, Ziqing ^{[1
]}

Zaretsky, Serge ^{[1
]}

Huang, Yande ^{[1
]}

Zang, Jia ^{[1
]}

Yuill, Elizabeth M. ^{[1
]}

Fenster, Michael D. B. ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Chem Proc Dev, New Brunswick, NJ 08903 USA

[2] Bristol Myers Squibb Co, Drug Prod Dev, New Brunswick, NJ 08903 USA

来源：

TETRAHEDRON LETTERS | 2022年 / 110卷

关键词：

Azirine; Photodegradation; NMR Spectroscopy; BMS-813160; DEGRADATION; IMPURITIES; CAPTURE;

D O I：

10.1016/j.tetlet.2022.154164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the CCR2/5 dual chemokine antagonist BMS-813160 (1) presented a number of interesting impurity and degradant structure elucidation challenges. This publication will focus on the structure elucidation of the solid-state photodegradant of 1 which produced an unexpected stable azirine species. The structure was elucidated by mass spectrometry and NMR, with confirmation by single-crystal X-ray crystallography. (C) 2022 Elsevier Ltd. All rights reserved.

引用

页数：4

共 50 条

[21] Combination therapy with a dual CCR2/CCR5 antagonist and a FGF21 analogue synergizes in ameliorating steatohepatitis and fibrosis
Puengel, Tobias
Lefere, Sander
Hundertmark, Jana
Penners, Christian
Van de Velde, Frederique
Lapauw, Bruno
Devisscher, Lindsey
Geerts, Anja
Boehm, Stephanie
Zhao Qihong
Krupinski, John
Charles, Edgar
Zinker, Bradley
Tacke, Frank
JOURNAL OF HEPATOLOGY, 2020, 73 : S13 - S13
[22] The dual CCR2/CCR5 inhibitor Cenicriviroc ameliorates murine primary biliary cholangitis
Reuveni, D.
Leung, P.
Vig, P.
Shibolet, O.
Gershwin, E. M.
Zigmond, E.
JOURNAL OF HEPATOLOGY, 2017, 66 (01) : S75 - S76
[23] Elucidation of Binding Sites of Dual Antagonists in the Human Chemokine Receptors CCR2 and CCR5
Hall, Spencer E.
Mao, Allen
Nicolaidou, Vicky
Finelli, Mattea
Wise, Emma L.
Nedjai, Belinda
Kanjanapangka, Julie
Harirchian, Paymann
Chen, Deborah
Selchau, Victor
Ribeiro, Sofia
Schyler, Sabine
Pease, James E.
Horuk, Richard
Vaidehi, Nagarajan
MOLECULAR PHARMACOLOGY, 2009, 75 (06) : 1325 - 1336
[24] CENICRIVIROC MESILATE Chemokine CCR2/CCR5 Receptor Antagonist Anti-HIV Agent
Reviriego, C.
DRUGS OF THE FUTURE, 2011, 36 (07) : 511 - 517
[25] Dual CCR2/CCR5 antagonism as macrophage targeted therapy in experimental hepatocellular carcinoma
Degroote, Helena
Vandierendonck, Astrid
Xavier, Verhelst
Anja, Geerts
Hans, Van Vlierberghe
Devisscher, Lindsey
JOURNAL OF HEPATOLOGY, 2019, 70 (01) : E359 - E359
[26] Cenicriviroc, a CCR2/CCR5 antagonist, promotes the generation of type 1 regulatory T cells
Madan, Upasna
Verma, Bhawna
Awasthi, Amit
EUROPEAN JOURNAL OF IMMUNOLOGY, 2024, 54 (07)
[27] A phase Ib/II study of BMS-813160, a CC chemokine receptor (CCR) 2/5 dual antagonist, in combination with chemotherapy or nivolumab in patients (pts) with advanced pancreatic or colorectal cancer
Le, Dung
Gutierrez, Martin E.
Saleh, Mansoor
Chen, Eric
Mallick, Atrayee Basu
Pishvaian, Michael J.
Krauss, Jurgen
O'Dwyer, Peter
Garrido-Laguna, Ignacio
Zhao, Qihong
Kippel, Anke
Wang, Xiaoli
Liu, Yali
Pollack, Allyson
Sama, Ashwin
Lenz, Heinz-Josef
CANCER RESEARCH, 2018, 78 (13)
[28] CCR2 and CCR5 gene polymorphisms and susceptibility to sarcoidosis.
Wischmeijer, TA
Bombieri, C
Agostini, C
Semenzato, GP
Luisetti, M
Pignatti, PF
AMERICAN JOURNAL OF HUMAN GENETICS, 2002, 71 (04) : 485 - 485
[29] CCR2 and CCR5 expression on monocytes during in vivo culture
Dagkalis, N
Xu, H
Mack, M
Liversidge, J
Crane, IJ
IMMUNOLOGY, 2005, 116 : 75 - 75
[30] Dual CCR2/CCR5 Antagonist Cenicriviroc Leads to Potent and Significant Reduction in Proinflammatory CCR2+Monocyte Infiltration in Experimental Acute Liver Injury
Krenkel, Oliver
Puengel, Tobias
Mossanen, Jana C.
Ergen, Can
Heymann, Felix
Lefebvre, Eric
Trautwein, Christian
Tacke, Frank
HEPATOLOGY, 2015, 62 : 1065A - 1065A

← 1 2 3 4 5 →