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Record W2084283183 · doi:10.1021/jm401836p

Hepatitis C Virus NS5A Replication Complex Inhibitors: The Discovery of Daclatasvir

2014· article· en· W2084283183 on OpenAlex
Makonen Belema, Van N. Nguyen, Carol Bachand, Dan H. Deon, Jason T. Goodrich, Clint A. James, Rico Lavoie, Omar D. Lopez, Alain Martel, J. Romine, Edward H. Ruediger, Lawrence B. Snyder, Denis R. St. Laurent, Fukang Yang, Juliang Zhu, Henry S. Wong, David R. Langley, Stephen P Adams, Glenn H. Cantor, Anjaneya Chimalakonda, Aberra Fura, Benjamin M. Johnson, Jay O. Knipe, Dawn D. Parker, Kenneth S. Santone, Robert A. Fridell, Julie A. Lemm, Donald R. O’Boyle, Richard J. Colonno, Min Gao, Nicholas A. Meanwell, Lawrence G. Hamann

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueJournal of Medicinal Chemistry · 2014
Typearticle
Languageen
FieldMedicine
TopicHepatitis C virus research
Canadian institutionsBristol-Myers Squibb (Canada)
Fundersnot available
KeywordsNS5ADaclatasvirRepliconChemistryPotencyVirologyHepatitis C virusPharmacologyNS3Protease inhibitor (pharmacology)Drug discoveryHepacivirusVirusBiochemistryBiologyIn vitroGene

Abstract

fetched live from OpenAlex

The biphenyl derivatives 2 and 3 are prototypes of a novel class of NS5A replication complex inhibitors that demonstrate high inhibitory potency toward a panel of clinically relevant HCV strains encompassing genotypes 1-6. However, these compounds exhibit poor systemic exposure in rat pharmacokinetic studies after oral dosing. The structure-activity relationship investigations that improved the exposure properties of the parent bis-phenylimidazole chemotype, culminating in the identification of the highly potent NS5A replication complex inhibitor daclatasvir (33) are described. An element critical to success was the realization that the arylglycine cap of 2 could be replaced with an alkylglycine derivative and still maintain the high inhibitory potency of the series if accompanied with a stereoinversion, a finding that enabled a rapid optimization of exposure properties. Compound 33 had EC50 values of 50 and 9 pM toward genotype-1a and -1b replicons, respectively, and oral bioavailabilities of 38-108% in preclinical species. Compound 33 provided clinical proof-of-concept for the NS5A replication complex inhibitor class, and regulatory approval to market it with the NS3/4A protease inhibitor asunaprevir for the treatment of HCV genotype-1b infection has recently been sought in Japan.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.002
metaresearch head score (Gemma)0.003
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.093
Threshold uncertainty score0.356

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0020.003
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.032
GPT teacher head0.329
Teacher spread0.297 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it