Pyrrolopyrimidine derivatives useful as inhibitors of influenza virus replication
Inventors
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Assignees
MemberCocrystal PharmaCocrystal PharmaCocrystal Pharma is a clinical-stage biotechnology company specializing in the discovery and development of novel antiviral therapeutics for serious and chronic viral diseases such as influenza, COVID-19, hepatitis C, norovirus, and other respiratory viruses. The company leverages structure-based drug discovery technology and expertise in structural biology to design direct viral replication inhibitors with broad-spectrum activity. Its pipeline includes candidates in preclinical and clinical development, addressing unmet needs in antiviral medicine.
Cocrystal Pharma is a clinical-stage biotechnology company specializing in the discovery and development of novel antiviral therapeutics for serious and chronic viral diseases such as influenza, COVID-19, hepatitis C, norovirus, and other respiratory viruses. The company leverages structure-based drug discovery technology and expertise in structural biology to design direct viral replication inhibitors with broad-spectrum activity. Its pipeline includes candidates in preclinical and clinical development, addressing unmet needs in antiviral medicine.
Publication Number
US-11014941-B2
Publication Date
2021-05-25
Expiration Date
Abstract
Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient a safe and effective amount of a compound represented by any of Formulas I-III, or a pharmaceutically acceptable salt thereof. A pharmaceutical composition comprises a safe and effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
Core Innovation
The invention relates to compounds having a structure of one of the following formulae, including pharmaceutically acceptable salts. The structure includes a dashed line representing either a single or a double bond, and a linker group L selected from H, C1-6 alkyl, substituted alkyl, cycloalkyl, and bicyclooctyl-based options with OCONR2, CONR2, CO2R, COR, NRC(O)NR2, NRC(O)OR, NRC(O)R, and NR2 functionalities.
The substituent framework further defines R as H, C1-6 alkyl, C1-6 alkyl-CO2R1, —CO2R1, CON(R1)2, or C1-6 alkyl-CON(R1)2, with R1 as H or C1-6 alkyl. Each R2 is independently H, halo, —CN, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, CO2R, CONR2, or phenyl, pyridinyl, thiophenyl, furanyl, or imidazolyl, with optional substitution of the aromatic and heteroaromatic groups.
R3 is H or —SO2-phenyl, wherein the phenyl is optionally substituted, and the claims also include optional substitution rules for C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl moieties. Where two alkyl groups reside on an amide moiety, they can optionally together form a 5-7 membered ring with the nitrogen of the amide moiety.
Claims Coverage
The provided claim coverage centers on one broad compound claim and specific table- or structure-based compound claims, together with pharmaceutically acceptable salts. The broad compound claim is driven by four inventive feature groups.
Defined compound structure with linker L
A compound having a structure of one of the following formulae, wherein a dashed line represents either a single or a double bond, and L is selected from H, C1-6 alkyl, substituted alkyl, cycloalkyl, and 2.2.2 bicyclooctyl-based options.
R and R1 definitions for amide and carboxylate-linked substituents
R is H, C1-6 alkyl, C1-6 alkyl-CO2R1, —CO2R1, CON(R1)2, or C1-6 alkyl-CON(R1)2, and R1 is H or C1-6 alkyl.
R2 and R3 substituent sets with optional aromatic substitution
Each R2 is independently H, halo, —CN, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, CO2R, CONR2, phenyl, pyridinyl, thiophenyl, furanyl, or imidazolyl, with optional substitution of the aromatic and heteroaromatic groups; and R3 is H or —SO2-phenyl, with the phenyl optionally substituted.
Optional substitution limits and amide ring formation
A C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl moiety can optionally be substituted with from one to three substituents selected from the stated list, and two alkyl groups on an amide moiety can optionally together form a 5-7 membered ring with the nitrogen of the amide moiety.
Claim scope is defined by the broad formula-based compound claim with linker L and substituent variables R, R1, R2, and R3, together with table-recited compounds and specific structure-defined compounds where present. Pharmaceutically acceptable salts are included in the scope.
Stated Advantages
Inhibits influenza virus replication.
Reduces influenza virus amounts in a biological sample or subject.
Reduces viral titer/titre in biological samples/patients.
Treats or prevents influenza in a patient.
Supports combination therapy by optionally including neuraminidase inhibitors, ion channel inhibitors, or polymerase inhibitors.
Documented Applications
Treating influenza by administering the compound or salt to a subject in need of such treatment.
Reducing influenza virus amounts in a biological sample or a subject by administering the compound or salt.
Treating influenza infection in a subject using a pharmaceutical composition that includes the compound or salt plus a pharmaceutically acceptable carrier, optionally with an additional agent selected from neuraminidase inhibitors, ion channel inhibitors, and polymerase inhibitors.
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