Triazine derivatives having virus replication inhibitory activity and pharmaceutical composition comprising the same
Inventors
Tachibana, Yuki • UEHARA, Shota • UNOH, YUTO • Nakahara, Kenji • Taoda, Yoshiyuki • KASAMATSU, Koji • YAMATSU, Yukiko • Ando, Shigeru • SUTO, Takahiro • SASAKI, Michihito
Assignees
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Publication Number
US-12559474-B2
Publication Date
2026-02-24
Expiration Date
Abstract
A compound represented by Formula (I):wherein Y is N or the like; R1 is substituted or unsubstituted aromatic heterocyclyl or the like; R2 is substituted or unsubstituted aromatic carbocyclyl or the like; R3 is substituted or unsubstituted aromatic heterocyclyl or the like; —X— is —NH— or the like; m is 1 or the like; R5a is each independently a hydrogen atom or the like; R5b is each independently a hydrogen atom or the like; n is 1 or the like; R4a is each independently a hydrogen atom or the like; and R4b is each independently a hydrogen atom or the like, or a pharmaceutically acceptable salt thereof.
Core Innovation
The invention relates to a compound represented by Formula (I) and pharmaceutically acceptable salts thereof, with structural definitions governed by Y, R1, R2, R3, X, R6 and R6′, m, n, R5a, R5b, R4a, and R4b. Y is N or CR7, R1 is substituted or unsubstituted aromatic heterocyclyl, substituted or unsubstituted non-aromatic heterocyclyl, or substituted or unsubstituted carbamoyl, and R2 is a 6-membered aromatic carbocyclyl or aromatic heterocyclyl substituted with one halogen or one cyano and further substituted with substituent group G. Substituent group G includes halogen, cyano, alkyl, alkenyl, alkynyl, haloalkyl, alkyloxy, alkenyloxy, alkynyloxy, and haloalkyloxy.
The compound definition further includes R3 as substituted or unsubstituted aromatic carbocyclyl, non-aromatic carbocyclyl, aromatic heterocyclyl, non-aromatic heterocyclyl, or substituted or unsubstituted alkyl, and X as NR6, CR6R6′, O, S, or a single bond. R6 and R6′ are each independently hydrogen or substituted or unsubstituted alkyl, m is 0, 1, or 2, n is 1, and R5a, R5b, R4a, and R4b are each independently hydrogen or substituted or unsubstituted alkyl. The disclosure also includes an alternative scaffold represented by Formula (I′), together with crystallographic and LC/MS characterization entries for multiple compounds.
The invention is positioned around coronavirus 3CL protease inhibition and coronavirus replication inhibition as an antiviral effect, including SARS-CoV-2. The claim family includes compound definitions anchored to Formula (I) and Formula (I′), pharmaceutically acceptable salts, crystalline and cocrystalline forms, pharmaceutical compositions, and a method for inhibiting SARS-CoV-2 by administering the compound or a pharmaceutically acceptable salt of it to a subject.
Claims Coverage
The independent claim defines a compound represented by Formula (I) with multiple structural inventive features and includes pharmaceutically acceptable salts. Dependent claims refine specific parameter choices, include an alternative Formula (I′) definition, and extend to a method for inhibiting SARS-CoV-2 by administration.
Formula (I) compound scaffold
A compound represented by Formula (I) with Y being N or CR7; R1 being substituted or unsubstituted aromatic heterocyclyl, substituted or unsubstituted non-aromatic heterocyclyl, or substituted or unsubstituted carbamoyl; R2 being a 6-membered aromatic carbocyclyl or 6-membered aromatic heterocyclyl substituted with one halogen or one cyano and further substituted with substituent group G; R3 being substituted or unsubstituted aromatic carbocyclyl, non-aromatic carbocyclyl, aromatic heterocyclyl, non-aromatic heterocyclyl, or substituted or unsubstituted alkyl; X being NR6, CR6R6′, O, S, or a single bond; R6 and R6′ each independently being hydrogen or substituted or unsubstituted alkyl; m being 0, 1, or 2; n being 1; R5a, R5b, R4a, and R4b each independently being hydrogen or substituted or unsubstituted alkyl; and pharmaceutically acceptable salts thereof.
Substituent group G limitation
Substituent group G is selected from halogen, cyano, alkyl, alkenyl, alkynyl, haloalkyl, alkyloxy, alkenyloxy, alkynyloxy, and haloalkyloxy.
Alternative Formula (I′) scaffold
The compound of claim 1 wherein Formula (I) is defined as Formula (I′), with corresponding R1′, R2′, and R3′ selected according to the provided formula structures, including pharmaceutically acceptable salts thereof.
SARS-CoV-2 inhibition by administration
A method for inhibiting SARS-CoV-2 by administering the compound of claim 1, or a pharmaceutically acceptable salt of it, to a subject.
Overall, claim coverage centers on a Formula (I) compound scaffold with tightly defined substituent classes and parameter constraints, includes pharmaceutically acceptable salts, and extends to an alternative Formula (I′) definition and a method of inhibiting SARS-CoV-2 by administration.
Stated Advantages
Coronavirus 3CL protease inhibitory activity.
Coronavirus replication inhibitory activity as an antiviral effect.
Crystalline and cocrystalline forms are described.
Pharmaceutical compositions are described.
Documented Applications
Inhibiting SARS-CoV-2 by administering the compound of claim 1, or a pharmaceutically acceptable salt of it, to a subject.
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