Pyrrolopyridine derivative, method for producing same, and use thereof
Inventors
Kim, Bong Jin • Lee, Ill Young • Kim, Jae Hak • SHIN, Hong Suk • Son, Jong Chan • Lee, Chong-Kyo • Kim, Kyungjin • KIM, Uk-Il • NAM, Hwa Jung
Assignees
Interested in licensing this patent?
MTEC can help explore whether this patent might be available for licensing for your application.
Publication Number
US-11214570-B2
Publication Date
2022-01-04
Expiration Date
Abstract
Provided is a novel pyrrolopyridine compound represented by Chemical Formula I, a racemate or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof; and to a method for preparing the same. A compound represented by Chemical Formula I shows high selectivity and antiviral activity against human immunodeficiency virus (HIV), with low toxicity; therefore, it is useful as a therapeutic agent for viral infection, in particular, HIV infection.
Core Innovation
The invention relates to pyrrolopyridine Chemical Formula I antivirals. The compounds are represented by Chemical Formula I, including a racemate or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. The substituents are defined so that R1 is a C1-6 alkyl, and R2 and R3 are each independently hydrogen.
The invention addresses inhibiting HIV-1 proliferation. The compounds inhibit HIV-1 proliferation by targeting HIV-1 integrase, and are described as having high selectivity and low toxicity. The document frames this activity in the context of AIDS and antiviral therapy, including HAART.
The invention further includes a chemical preparation pathway to obtain the Chemical Formula I compounds. A two-step approach is described in which Chemical Formula II is coupled with Chemical Formula III to give Chemical Formula IV, and then Chemical Formula IV is hydrolyzed to obtain the Chemical Formula I acid.
The invention is supported by biological and safety-related evaluation results reported in the document. The document describes in vitro HIV-1 wild-type EC50/IC50 data for examples, and pharmacokinetic parameters in male rats after IV and PO administration. It also reports metabolic stability, CYP450 inhibition results, and hERG K+ channel cardiotoxicity assay outcomes, for use in characterizing the compounds.
Claims Coverage
The partial content provides one independent compound claim and one independent method-of-use claim focus. Across the independent claims, the coverage centers on the Chemical Formula I compound definition with specific substituent constraints and its use in treating HIV infection via administering the compound.
Chemical Formula I pyrrolopyridine antiviral compound definition
A compound represented by Chemical Formula I, a racemate or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein R1 is a C1-6 alkyl, and R2 and R3 are each independently hydrogen.
Treating HIV infection by administering Chemical Formula I compound
A method of treating an HIV infection comprising administering the compound of Chemical Formula I, a racemate, stereoisomer or a pharmaceutically acceptable salt thereof, to a subject in need thereof.
Overall, the claim coverage is directed to Chemical Formula I pyrrolopyridine antivirals with R1 constrained to C1-6 alkyl and R2/R3 set as hydrogen, including racemate, stereoisomer, and salts, and to a method of treating HIV infection by administering those compounds to a subject in need.
Stated Advantages
Inhibits HIV-1 proliferation by targeting HIV-1 integrase.
High selectivity.
Low toxicity.
Documented Applications
Treating an HIV infection by administering the Chemical Formula I compound, including racemate, stereoisomer, or pharmaceutically acceptable salt, to a subject in need.
Antiviral composition use is described, including oral administration and injection.
Interested in licensing this patent?