Substituted phenylpyrrolecarboxamides with therapeutic activity in HIV
Inventors
Debnath, Asim Kumar • Curreli, Francesca • Kwong, Peter D. • Kwon, Young Do
Assignees
New York Blood Center Inc • Government of the United States of America
Publication Number
US-11571409-B2
Publication Date
2023-02-07
Expiration Date
2035-09-18
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Abstract
Substituted phenylpyrrolecarboxamide compounds such as those represented by Formula A can be used in the treatment of HIV infection and related conditions.
Core Innovation
The invention disclosed relates to substituted phenylpyrrolecarboxamide compounds represented by Formula A, which have therapeutic utility in treating HIV infection and related conditions. These compounds are part of pharmaceutical compositions that can be used as antiviral agents, particularly targeting and inhibiting HIV-1 infection.
The problem addressed concerns the lack of existing drugs targeting the HIV-1 gp120 protein. HIV-1 infection begins with the virus's envelope glycoproteins gp120 binding to the host cell's primary receptor CD4, followed by binding to a co-receptor CCR5 or CXCR4. The Phe43 cavity of HIV-1 gp120 is recognized as a potential target for entry inhibitors, yet no drug has been available to exploit this target.
The compounds described aim to inhibit the binding of gp120 to the host cell receptor CD4, thereby preventing viral entry into cells. The detailed description elaborates on the structures of these compounds, their substituents, and provides methods for synthesis and administration. Various embodiments include pharmaceutical compositions comprising these compounds, formulations for different routes of administration, and methods for treating HIV infection by administering these compounds.
Claims Coverage
The patent includes two independent claims defining novel compounds with specific structural representations, covering substituted phenylpyrrolecarboxamides and specific related chemical formulas, with multiple dependent claims further detailing substituent variations.
Compounds represented by Formula A
A compound defined by a structural formula A, comprising substituted phenyl and pyrrolyl groups with various possible substitutions at positions R1, A, and B, providing specific chemical variants capable of inhibiting HIV.
Compounds represented by Formula 1
A compound represented by Formula 1 with substituents R4 through R28 having defined possible substitutions including hydrogen, halides, and a range of chemical groups, providing a broad class of substituted phenylpyrrolecarboxamide derivatives with antiviral activity against HIV.
The claims cover substituted phenylpyrrolecarboxamide compounds characterized by their chemical structures as defined in Formula A and Formula 1, including a wide range of substituents that tailor the compounds' properties for antiviral efficacy against HIV infection.
Stated Advantages
The compounds provide anti-HIV activity by inhibiting HIV-1 gp120 binding to CD4, representing a novel mechanism for HIV entry inhibition.
Pharmaceutical compositions containing these compounds can be formulated for various administration routes, allowing flexibility in therapeutic use.
Compounds exhibit inhibitory activity against multiple HIV-1 strains, including laboratory-adapted and primary isolates, demonstrating broad antiviral potential.
Documented Applications
Treatment and prevention of HIV infection in humans.
Use in pharmaceutical compositions for administration via oral, parenteral, intravenous, intradermal, subcutaneous, inhalative, transdermal, topical, transmucosal, rectal, intravaginal, intraperitoneal, buccal, and intraocular routes.
Use as inhibitors of the HIV-1 gp120 binding to the host cell receptor CD4 to prevent viral entry.
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