cas 1206799-15-6, LY2801653 | Articles data

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Small-Volume Continuous Manufacturing of Merestinib. Part 2. Technology Transfer and cGMP Manufacturing
Technology transfer of a small volume continuous (SVC) process and Current Good Manufacturing Practices (cGMP) manufacturing of merestinib are described. A hybrid batch-SVC campaign was completed at a contract manufacturing organization under cGMP. The decision process by which unit operations were selected for implementation in flow for the cGMP campaign is discussed. The hybrid process comprised a Suzuki-Miyaura cross-coupling reaction, a nitro-group hydrogenolysis, a continuous amide bond formation, and a continuous deprotection. A continuous crystallization using two mixed suspension, mixed product removal (MSMPR) crystallizers and a filtration with in situ dissolution were employed for purification between the two SVC steps. Impurity levels were monitored using both online process analytical technology (PAT) and offline measurements. The continuous processing steps operated uninterrupted for 18 days to yield the drug substance in solution at a throughput of 12.5 kg/day. Crystallization in batch mode afforded 183 kg of the drug substance in specification. Success of the campaign was attributed to robustness of the control strategy and to the multiyear partnership in continuous manufacturing between the development organization and the contract manufacturer. Key learnings are offered from the perspectives of both the development organization and the contract manufacturer.
Reizman, Brandon J.,Cole, Kevin P.,Hess, Molly,Burt, Justin L.,Maloney, Todd D.,Johnson, Martin D.,Laurila, Michael E.,Cope, Richard F.,Luciani, Carla V.,Buser, Jonas Y.,Campbell, Bradley M.,Forst, Mindy B.,Mitchell, David,Braden, Timothy M.,Lippelt, Christopher K.,Boukerche, Moussa,Starkey, Derek R.,Miller, Richard D.,Chen, Jing,Sun, Baoquan,Kwok, Martin,Zhang, Xin,Tadayon, Sam,Huang, Ping
p. 870 - 881
(2019)
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Development of an NH4Cl-Catalyzed Ethoxy Ethyl Deprotection in Flow for the Synthesis of Merestinib
An NH4Cl-catalyzed ethoxy ethyl deprotection was developed for the synthesis of merestinib, a MET inhibitor. Alternative reactor technologies using temperatures above the solvent boiling point are combined with this mild catalyst to promote the deprotection reaction. The reaction is optimized for flow and has been used to synthesize over 100 kg of the target compound. The generality of the reaction conditions is also demonstrated with other compounds and protecting groups.
Frederick, Michael O.,Calvin, Joel R.,Cope, Richard F.,Letourneau, Michael E.,Lorenz, Kurt T.,Johnson, Martin D.,Maloney, Todd D.,Pu, Yangwei John,Miller, Richard D.,Cziesla, Lauren E.
p. 1411 - 1417
(2015/11/02)

Route design and development of a MET kinase inhibitor: A copper-catalyzed preparation of an N 1 - Methylindazole
The synthesis of a MET kinase inhibitor in an overall yield of 22% was achieved over eight steps starting with 3-hydroxybenzaldehyde, an improvement from the initial 12-step process with a 5.4% yield. Highlights of the process chemistry design and development are a Cu-catalyzed cyclization to form an important N1-methylindazole ring, a selective nitro reduction in the presence of an aryl bromide, a late-stage Suzuki cross-coupling, and a base-promoted Boc deprotection to form the desired drug candidate.
Kallman, Neil J.,Liu, Chin,Yates, Matthew H.,Linder, Ryan J.,Ruble, J. Craig,Kogut, Eugene F.,Patterson, Lawrence E.,Laird, Dana L. T.,Hansen, Marvin M.
p. 501 - 510
(2014/05/06)

AMIDOPHENOXYINDAZOLES USEFUL AS INHIBITORS OF C-MET
The present invention provides amidophenoxyindazole compounds useful in the treatment of cancer.
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Page/Page column 19

(2010/02/17)

Chemical Properties

Boiling Point: 795.3±60.0 °C(Predicted)
Density: 1.42±0.1 g/cm3(Predicted)
Solubility:≥27.65 mg/mL in DMSO; insoluble in H2O; ≥5.02 mg/mL in EtOH with gentle warming and ultrasonic
PKA: 10.83±0.70(Predicted)
PSA: 106.83000
LogP: 5.81850

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Chemical Properties

Boiling Point: 795.3±60.0 °C(Predicted)

Density: 1.42±0.1 g/cm3(Predicted)

Solubility:≥27.65 mg/mL in DMSO; insoluble in H2O; ≥5.02 mg/mL in EtOH with gentle warming and ultrasonic

PKA: 10.83±0.70(Predicted)

PSA: 106.83000

LogP: 5.81850

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