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Imocitrelvir

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Imocitrelvir

CAS 343565-99-1

MFC26H29N5O7 MW523.5 g/mol

ethyl (2E,4S)-4-{(2S)-2-[3-(5-methyl-1,2-oxazole-3-carboxamido)-2-oxopyridin-1(2H)-yl]pent-4-ynamido}-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate

ethyl (E,4S)-4-[[(2S)-2-[3-[(5-methyl-1,2-oxazole-3-carbonyl)amino]-2-oxo-1-pyridinyl]pent-4-ynoyl]amino]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
protease inhibitor, antiviral, AG-7404, V-7404, AG 7404, V 7404, VQ1AN3OO42

Imocitrelvir is an investigational new drug that is being evaluated for the treatment of viral infections. It is a 3C protease inhibitor in picornaviruses. Originally developed by Pfizer for treating human rhinovirus infections,^[1] this small molecule has shown promise against a broader range of viruses, including polioviruses.^[2][3]

SYN

Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 8. Pharmacological Optimization of Orally Bioavailable 2-Pyridone-Containing Peptidomimetics

Publication Name: Journal of Medicinal Chemistry

Publication Date: 2003-09-17

PMID: 14521419

DOI: 10.1021/jm030166l

PAT

WO-2016044656

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016044656&_cid=P21-MHBDH2-20719-1

PAT

WO-2022235874

PAT

WO-2024206284

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2001040189&_cid=P21-MHBDI9-21481-1

EXAMPLE 21
Preparation of Compound 22: tra«5-(4S,3″”S)-4-(2′-{3″-[(5′”-Methylisoxazole-3′”-carbonyl)amino]-2″-oxo-2″H-pyridin- 1 “-yl} acetylamino)-5-(2″”-oxopyrrilidin-3″”-yl)pent-2-enoic Acid Ethyl Ester

Preparation of Intermediate {3-[(5′-Methylisoxazole-3′-carbonyl)amino]-2-oxo-2H-pyridin-l-yl} acetic Acid tert-Butyl Ester
To a solution of 5-methylisoxazole-3-carboxylic acid (2′-hydroxy-4′-methylpyridin-3′-yl)amide (F2, Example 19) (0.520 g, 2.37 mmol, 1 equiv) in TΗF (20 mL) at 0 °C was added NaΗ (0.095 g, 2.37 mmol, 1.0 equiv). The resulting mixture was stirred at 0 °C for 20 min, and then t-butyl bromoacetate (0.385 mL, 2.61 mmol, 1.1 equiv) was added. The reaction mixture was stirred and warmed to room temperature for 30 min, then was partitioned between 0.5 N ΗC1 (100 mL) and EtOAc (2 x 100 mL). The combined organic layers were dried over Na₂SO and were concentrated. Purification of the residue by flash column chromatography (30% EtOAc in hexanes) provided the title intermediate (0.628 g, 79%) as a white solid: IR (cm-¹) 3343, 1743, 1651, 1581, 1156; Η NMR (CDC1₃) δ 1.52 (s, 9H), 2.53 (s, 3H), 4.65 (s, 2H), 6.32 (t, 1H, 7= 7.2), 6.51 (s, IH), 7.01 (dd, 1H, 7= 6.9, 1.8), 8.50 (dd, 1H, 7= 7.5, 1.8), 9.63 (s, br. IH); Anal. C16H19N3O5: C, H, N.

Preparation of Compound 22
The preceding intermediate was transformed into Compound 22 by a process that was analogous to that described in Example 25 for the transformation of V3 to product R3: mp = 102-106 °C; IR (cm”¹) 3336, 1684, 1534, 1457; ^JH NMR (CDCI3) δ 1.27 (t, 3H, 7= 7.2), 1.67-1.75 (m, IH), 1.98-2.09 (m, IH), 2.37-2.49 (m, IH), 2.53 (s, 3H), 2.55-2.61 (m, IH), 3.34-3.46 (m, 2H), 3.51-3.52 (m, IH), 4.17 (q, 2H, 7= 7.2), 4.61-4.78 (m, 3H), 5.98 (dd, IH, 7 = 15.6, 1.5), 6.20 (s, br. IH), 6.35 (t, 1H, 7= 7.8), 6.51 (s, IH), 6.85 (dd, IH, 7= 15.6, 5.1), 7.17 (d, IH, 7= 7.2), 8.33 (d, IH, 7= 7.2), 8.49 (d, IH, 7= 7.5), 9.57 (s, br. IH); Anal.
C₂3H27N₅O₇: C, H, N.

EXAMPLE 24
Preparation of Compound 25: trans-(2’S,3″”‘S,4S)-4-(3^,-(4″-Fluorophenyl)-2′-{3″‘-[(5″”-methylisoxazole-3″”-carbonyl)amino]-2′”-oxo-2′”H-pyridin- “-yl}propionylamino)-5-(2″ oxopyrrolidin-3′””-yl)pent-2-enoic Acid Ethyl Ester

The title compound was prepared from F2 (Example 19) in a manner analogous to that described for the conversion of U2 to 13 in Example 23 utilizing intermediate Y2 (Example 25) where appropriate: IR (cm-¹) 3331, 1690, 1590, 1531, 1455; ^!H NMR (CDCI3) δ 1.30 (t, 3H, 7= 7.0), 1.45-1.55 (m, IH), 1.64-1.75 (m, IH), 2.03-2.31 (m, 3H), 2.49 (s, 3H), 3.10 (dd, IH, 7= 13.7, 7.9), 3.20-3.46 (m, 3H), 4.20 (q, 2H, 7= 7.0), 4.36-4.47 (m, IH), 5.67 (dd, IH, 7 = 15.7, 1.4), 5.85-5.92 (m, IH), 6.29 (t, 1H, 7= 7.2), 6.45 (s, IH), 6.70 (dd, IH, 7= 15.7, 5.7), 6.86 (s, IH), 6.90-6.97 (m, 2H), 7.10-7.16 (m, 2H), 7.60 (dd, IH, 7= 7.2, 1.6), 8.37 (dd, IH, 7 = 7.2, 1.6), 8.51 (d, IH, 7= 6.6), 9.47 (s, IH).

EXAMPLE 25
Preparation of Compound 26: tr_.«5-(2’S,3″”S,4S)-4-(2′-{3″-[(5″‘-Methyl-isoxazole-3′”-carbonyl)amino]-2″-oxo-2″H-pyridin-l”-yl}butyrylamino)-5-(2″”-oxopyrrolidin-3″”-yl)pent-2-enoic Acid Ethyl Ester (R3)

Preparation of Intermediate (2R)-2-Trifluoromethanesulfonyl-oxybutyric acid tert-butyl ester (U3)
Commercially available T3 (0.575 g, 3.59 mmol, 1 equiv) was dissolved in CH2CI2 (25 mL) and cooled in an ice bath. 2,6-Lutidine (0.836 mL, 7.18 mmol, 2 equiv) and trifluoromethanesulfonic anhydride (1.15 mL, 6.84 mmol, 1.9 equiv) were added and the reaction mixture was stirred 30 min. It was then diluted with MTBE (400 mL), washed with a mixture of brine and 1 N HCl (2:1, 100 mL) and brine (100 mL), dried over Na2SO4 and evaporated to provide the title intermediate which was used without further purification.

Preparation of Intermediate (2S)-2- {3′-[(5″-Methylisoxazole-3″-carbonyl)amino]-2′-oxo-2’H-pyri din- l’-yl} butyric Acid tert-Butyl Ester (V3)
Intermediate F2 from above (0.200 g, 0.912 mmol, 1.1 equiv) was suspended in TΗF (6 mL). Sodium hydride (60% dispersion in mineral oil, 0.0332 g, 0.830 mmol, 1 equiv) was added in one portion. After stirring 30 min, a solution of intermediate U3 (0.830 mmol, 1 equiv, based on T3) in TΗF (7 mL) was added dropwise. The resulting mixture was stirred 2 hours, then diluted with EtOAc (200 mL) and washed with brine (2 x 50 mL). The organic phase was dried over MgSO₄ and evaporated. The residue was purified by flash column chromatography (25% EtOAc in hexanes) to provide the title intermediate (0.178 g, 59%) as an oil: R/= 0.30 (25% EtOAc in hexanes); IR (cm”¹) 3331, 1731, 1690, 1649, 1602, 1531 ; *Η NMR (CDCI3) δ 0.93 (t, 3H, 7= 7.3), 1.45 (s, 9H), 1.83-2.01 (m, IH), 2.17-2.31 (m, IH), 2.50 (s, 3H), 5.44-5.51 (m, IH), 6.32 (t, IH, 7= 7.2), 6.48 (s, IH), 7.10 (dd, IH, 7= 7.2, 1.8), 8.45 (dd, 1H, 7= 7.2, 1.8), 9.64 (s, IH); Anal. C₁8H23N3O5: C, H, N.

Preparation of Intermediate (2S)-2- {3′-[(5″-Methylisoxazole-3″-carbonyl)amino]-2′-oxo-2’H-pyridin-l’-yl}butyric Acid (W3)
Intermediate V3 from above (0.143 g, 0.397 mmol, 1 equiv) was stirred for 1 h in a solution of TFA (2 mL) in CΗ2CI2 (3 mL). The volatiles were evaporated. The residue was suspended in toluene (10 mL) and concentrated to dryness, providing the title intermediate which was used without further purification.

Preparation of Intermediate trα«5-(3’S,4S)-4-Amino-5-(2′-oxopyrrolidin-3′-yl)pent-2-enoic Acid Ethyl Ester (Y2)
Intermediate X2, prepared according to the method disclosed in the co-pending application, U.S. Provisional Patent Application No. 60/150,358, filed August 24, 1999(0.130 g, 0.398 mmol, 1 equiv), was stirred for 30 min in a solution of TFA (2 mL) in CH2CI2 (3 mL). The volatiles were evaporated. The residue was suspended in toluene (10 mL) and concentrated to dryness, providing the title intermediate which was used without further purification.

Preparation of Product R3 (Compound 26)
Intermediates W3 and Y2 (as prepared above) were combined in CH2CI2 (7 mL) and cooled in an ice bath. HOBt (0.064 g, 0.47 mmol, 1.2 equiv), iP^NEt (0.484 mL, 2.78 mmol, 7 equiv) and EDC (0.084 g, 0.44 mmol, 1.1 equiv) were added sequentially. The reaction mixture was allowed to warm to 23 °C overnight, then diluted with EtOAc (500 mL) and washed with 5% KHSO₄ , half saturated NaHCO3, and brine (100 mL each). The organic phase was dried over MgSO₄ and evaporated. The residue was purified by flash column chromatography (gradient elution, 2→3% CH3OH in CH2CI2) to provide the title intermediate (0.119 g, 58%) as a white foam: IR (cm”¹) 3331, 1684, 1649, 1590, 1531; ^JH NMR (CDCI3) δ 0.92 (t, 3H, J = 7.3), 1.29 (t, 3H, J = 7.1), 1.47-1.58 (m, IH), 1.62-1.77 (m, IH), 1.85-2.00 (m, IH), 2.08-2.33 (m, 4H), 2.49 (s, 3H), 3.25-3.42 (m, 2H), 4.19 (q, 2H, J = 7.1), 4.39-4.50 (m, IH), 5.73 (dd, IH, J = 8.8, 6.8), 5.97 (dd, IH, J = 15.7, 1.4), 6.34 (t, IH, J = 7.2), 6.46 (s, IH), 6.86 (dd, IH, J = 15.7, 5.9), 7.18 (s, IH), 7.59 (dd, IH, J = 7.2, 1.8), 8.42 (dd, IH, J = 7.2, 1.8), 8.58-8.62 (m, IH), 9.56 (s, 1); Anal. C25H31N5O7O.5OH2O: C, H, N.

PAT

Treatment of infection by human enterovirus d68Publication Number: US-2020016243-A1Priority Date: 2014-09-17
Treatment of infection by human enterovirus d68Publication Number: WO-2016044656-A1Priority Date: 2014-09-17
Treatment of infection by human enterovirus d68Publication Number: US-2021052708-A1Priority Date: 2014-09-17
Treatment of infection by human enterovirus D68Publication Number: US-11191817-B2Priority Date: 2014-09-17Grant Date: 2021-12-07
Therapeutic compounds and methodsPublication Number: US-2025051283-A1
Protease Inhibitors for Treatment or Prevention of Coronavirus DiseasePublication Number: US-2023192660-A1Priority Date: 2020-05-08
Composition and combined medication method for treating enterovirus infectionPublication Number: US-2019030027-A1Priority Date: 2016-01-29
Composition and combined medication method for treating enterovirus infectionPublication Number: US-10864210-B2Priority Date: 2016-01-29Grant Date: 2020-12-15
Treatment of infection by human enterovirus D68Publication Number: US-10328128-B2Priority Date: 2014-09-17Grant Date: 2019-06-25
Treatment of infection by human enterovirus d68Publication Number: US-2017290893-A1Priority Date: 2014-09-17
Nucleotide and nucleoside therapeutic compositions, combinations and related uses thereofPublication Number: CN-117881402-APriority Date: 2021-05-05
Nucleotide and nucleoside therapeutic compositions, combinations and uses related theretoPublication Number: EP-4333859-A1Priority Date: 2021-05-05
Nucleotide and nucleoside therapeutic compositions, combinations, and related usesPublication Number: JP-2024517807-APriority Date: 2021-05-05
Nucleotide and nucleoside therapeutic compositions, combinations and uses related theretoPublication Number: WO-2022235874-A1Priority Date: 2021-05-05
Protease inhibitors for treatment or prevention of coronavirus diseasePublication Number: EP-4146267-A1Priority Date: 2020-05-08
4′-substituted nucleosides and nucleotides as antiviral agentsPublication Number: WO-2024227159-A2Priority Date: 2023-04-28
Therapeutic compoundsPublication Number: WO-2024206284-A2Priority Date: 2023-03-27
Antibody molecules binding to sars-cov-2Publication Number: WO-2024168061-A2Priority Date: 2023-02-07
Predictive model for variants associated with drug resistance and theranostic applications thereofPublication Number: WO-2023172635-A1Priority Date: 2022-03-08
Nucleotide and nucleoside therapeutic compositions, combinations and uses related theretoPublication Number: CA-3216679-A1Priority Date: 2021-05-05

LIT

Structure and inhibition of SARS-CoV-1 and SARS-CoV-2 main proteases by oral antiviral compound AG7404Publication Name: Antiviral ResearchPublication Date: 2022-12PMCID: PMC9632241PMID: 36336176DOI: 10.1016/j.antiviral.2022.105458
Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug DesignPublication Name: Journal of Medicinal ChemistryPublication Date: 2021-09-30PMID: 34591488DOI: 10.1021/acs.jmedchem.1c01215
In Vitro Antiviral Activity of New Oxazoline Derivatives as Potent Poliovirus InhibitorsPublication Name: Journal of Medicinal ChemistryPublication Date: 2018-12-04PMCID: PMC9169555PMID: 30512950DOI: 10.1021/acs.jmedchem.8b01482
A Novel Series of Highly Potent Small Molecule Inhibitors of Rhinovirus ReplicationPublication Name: Journal of Medicinal ChemistryPublication Date: 2017-06-15PMID: 28581749DOI: 10.1021/acs.jmedchem.7b00175
Anti-poliovirus activity of protease inhibitor AG-7404, and assessment of in vitro activity in combination with antiviral capsid inhibitor compoundsPublication Name: Antiviral ResearchPublication Date: 2013-05PMID: 23499651DOI: 10.1016/j.antiviral.2013.03.003

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Clinical data

Other names	AG-7404, V-7404
Identifiers
IUPAC name
CAS Number	343565-99-1
PubChem CID	5280053
IUPHAR/BPS	13223
UNII	VQ1AN3OO42
ChEMBL	ChEMBL141157
Chemical and physical data
Formula	C₂₆H₂₉N₅O₇
Molar mass	523.546 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

“Imocitrelvir”. PatSnap.
Xie H, Rhoden EE, Liu HM, Ogunsemowo F, Mainou BA, Burke RM, et al. (November 2024). “Antiviral Development for the Polio Endgame: Current Progress and Future Directions”. Pathogens. 13 (11). Basel, Switzerland: 969. doi:10.3390/pathogens13110969. PMC 11597170. PMID 39599522.
Bandyopadhyay AS, Burke RM, Hawes KM (June 2024). “Polio Eradication: Status, Struggles and Strategies”. The Pediatric Infectious Disease Journal. 43 (6): e207-211. doi:10.1097/INF.0000000000004330. PMID 38564755.

////////Imocitrelvir, protease inhibitor, antiviral, AG-7404, V-7404, AG 7404, V 7404, VQ1AN3OO42

Tags: AG 7404, AG-7404, antiviral, Imocitrelvir, protease inhibitor, V 7404, V-7404

By DR ANTHONY MELVIN CRASTO Ph.D in Uncategorized on October 29, 2025.

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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