Adenosine derivative and pharmaceutical composition comprising the same
Inventors
Assignees
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Publication Number
US-12390484-B2
Publication Date
2025-08-19
Expiration Date
Abstract
Disclosed herein are adenosine derivative prodrugs and compositions thereof that can be used for the treatment of HIV infection or RNA virus infection.
Core Innovation
The invention relates to an adenosine derivative having a structure of formula (I) or a pharmaceutically acceptable salt thereof. The structure includes linkage variables A and E, each independently selected from a bond, —(CO)—, —(CO)-G-, —(CO)-G-(C1-10 alkylene)-J-, —(CO)-G-(C2-10 alkenylene)-J-, and —(CO)-G-(C2-10 alkynylene)-J-, with G selected from a bond, O, NH, and S, and J selected from a bond, O, NH, S, and —(CO)-G-.
The formula (I) further defines substituents R1, R2, and R3. R1 is selected from H, C1-5 alkyl, C1-5 haloalkyl, or C1-5 alkoxy. R2 is selected from H, C1-20 alkyl, C1-20 haloalkyl, C1-20 alkoxy, C2-20 alkenyl, C2-20 alkynyl, C3-20 cycloalkyl, 3- to 20-membered heterocycloalkyl, aryl, and heteroaryl, and R3 is selected from H, —(CO)-G-C1-10 alkyl, C1-10 alkyl, C1-10 haloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-12 cycloalkyl, 3- to 12-membered heterocycloalkyl, aryl, and heteroaryl.
The disclosure also specifies related formula instances, pharmaceutically acceptable salts, tautomers, solvates, and hydrates. It links these adenosine-derivative embodiments to in vivo reverse transcriptase-related inhibition and chain-termination-related activity, including DNA translocation inhibitor activity in vivo, and to therapeutic use for treating HIV by administering an effective dosage of a pharmaceutical composition.
Claims Coverage
The independent claim coverage centers on an adenosine derivative of formula (I) or a pharmaceutically acceptable salt thereof. The inventive features are the constrained scaffold defined by A, E, G, J, R1, R2, and R3, with dependent refinements that add in vivo reverse transcriptase-related inhibition/chain termination limitations and HIV treatment use.
Adenosine derivative defined by formula (I)
An adenosine derivative or pharmaceutically acceptable salt thereof having a structure of formula (I), with A and E each independently selected from a bond, —(CO)—, —(CO)-G-, —(CO)-G-(C1-10alkylene)-J-, —(CO)-G-(C2-10alkenylene)-J-, and —(CO)-G-(C2-10alkynylene)-J-; G selected from a bond, O, NH, and S; and J selected from a bond, O, NH, S, and —(CO)-G-.
Substituent selection for R1, R2, and R3
R1 is selected from H, C1-5 alkyl, C1-5 haloalkyl, or C1-5 alkoxy; R2 is selected from H, C1-20 alkyl, C1-20 haloalkyl, C1-20 alkoxy, C2-20 alkenyl, C2-20 alkynyl, C3-20 cycloalkyl, 3- to 20-membered heterocycloalkyl, aryl, and heteroaryl; and R3 is selected from H, —(CO)-G-C1-10alkyl, C1-10alkyl, C1-10haloalkyl, C2-10alkenyl, C2-10alkynyl, C3-12cycloalkyl, 3- to 12-membered heterocycloalkyl, aryl, and heteroaryl.
In vivo reverse transcriptase-related inhibition and chain termination activity
The adenosine derivative or pharmaceutically acceptable salt thereof is defined by one or more in vivo reverse transcriptase-related activities, including reverse transcriptase chain terminator activity in vivo and DNA translocation inhibitor activity in vivo.
Treating HIV infection by administering an effective dosage
A method of treating HIV infection by administering an effective dosage of the pharmaceutical composition to a subject in need thereof.
The claim set covers a formula (I) adenosine derivative with defined linkage and substituent selections, and further includes functional activity limitations and a therapeutic use directed to HIV infection.
Stated Advantages
In vivo reverse transcriptase-related inhibition and in vivo chain-termination-related activity.
Can be metabolized in vivo to generate EFdA-like reverse transcriptase inhibitors and reverse transcriptase chain terminators.
Can be metabolized in vivo to generate EFdA-like DNA translocation inhibitor activity.
Includes pharmaceutical compositions comprising the adenosine derivatives with pharmaceutically acceptable carriers.
Includes isomer and stereoisomer embodiments, including enantiomer and diastereomer forms, as well as tautomer, solvate, and hydrate forms.
Treatment of HIV infection by administration of the pharmaceutical composition.
Documented Applications
Treating HIV infection by administering an effective dosage of the pharmaceutical composition to a subject in need thereof.
Treatment of HIV by administering a pharmaceutical composition including the formula (I) derivatives to a subject in need.
Treatment of HIV/AIDS by administering a pharmaceutical composition to a subject in need.
Treatment or prevention of HIV/AIDS by administering a pharmaceutical composition to a subject in need.
Anti-HIV use including AIDS, including HIV-1 resistance settings and HIV-2 use settings.
Targeting HIV, AIDS, and other RNA infections.
Treatment of other disclosed infections.
A target drug monitoring method embodiment linked to the described adenosine-derivative compounds.
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