Anti-infective compounds
Inventors
No, Zaesung • Kim, Jaeseung • Brodin, Priscille • Seo, Min Jung • Kim, Young Mi • Cechetto, Jonathan • Jeon, Heekyoung • Genovesio, Auguste • Lee, Saeyeon • Kang, Sunhee • Ewann, Fanny Anne • Nam, Ji Youn • Christophe, Thierry • Fenistein, Denis Philippe Cedric • Heo, Jamung • Jiyeon, Jang
Assignees
Institut National de la Sante et de la Recherche Medicale INSERM • Institut Pasteur Korea
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Publication Number
US-8865734-B2
Publication Date
2014-10-21
Expiration Date
Abstract
The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.
Core Innovation
The invention relates to substituted imidazo[1,2-a]pyridine carboxamide derivatives defined by general formulae Ia and Ib and pharmaceutically acceptable salts thereof. The compounds share an imidazo[1,2-a]pyridine fused bicyclic heteroaromatic core with a carboxamide moiety, variable ring positions m, n, o, X, Y and Z defined as CH, and broad substituent selections at R1, R2, R3, R4 and the additional Ib variables A, W, R10, R11, R12, R13 and R14. The scope includes optional substitution, aryl, benzyl, heteroaryl and heterocyclyl groups, and optional connectivity of two R3 groups to form a five- or six-membered cyclic or heterocyclic ring.
The disclosure further enumerates numerous specific compounds and structural examples within the imidazo[1,2-a]pyridine carboxamide family, including selected formulae 5, 8, 13, 14, 17, 18, 20, 21, 23-43, 46, 48, 50, 51, 53, 59, 68, 69, 74, 79, 80, 89-91, 142, 143, 161, 196, 211-213, 219, 221, 222, 239-247, 264, 313-329 and 331, together with named example compounds. The examples include substituted structures with chloro, bromo, fluoro, methoxy, cyano, trifluoromethyl, trifluoromethoxy, phenoxy, benzyloxy, piperidine, piperazine, morpholine, azepanyl and oxadiazole motifs.
The provided material also includes characterization data for selected example compounds, including 1H NMR, 13C NMR, LCMS and melting point data. The compound-linked functional framing is directed to treating bacterial infection in a person, including tuberculosis, by administering a compound that competitively inhibits the specific binding of a compound from the claims to a target protein, and the claim set also includes a pharmaceutical composition that includes a compound and a pharmaceutically acceptable carrier.
Claims Coverage
The provided independent claims cover two broad compound genera, one of general formula Ia and one of general formula Ib. Each independent claim recites extensive substituent scope, includes pharmaceutically acceptable salts, and is further limited by enumerated formula selections and named example compounds; additional dependent claims add bacterial infection and tuberculosis treatment, competitive inhibition of specific binding to a target protein, and pharmaceutical composition language. There are two inventive features in the main compound claims.
Imidazo[1,2-a]pyridine-3-carboxamide compounds of general formula Ia
A compound having general formula Ia, with m, n, X, Y and Z defined as in the claims; R1, R2, R3 and R4 selected from the listed substituent groups; R5, R6 and R7 independently selected from the listed substituent groups; a compound formula selected from the enumerated formulae and named examples; and pharmaceutically acceptable salts thereof.
Imidazo[1,2-a]pyridine compounds of general formula Ib
A compound having general formula Ib, with o, n, m, X, Y and Z defined as in the claims; A selected as C(O) or C(S); W selected as NR11; R2, R3, R5, R6, R10, R11, R12, R13 and R14 selected from the listed substituent groups; optional connectivity of two R3 groups to form a cyclic or heterocyclic ring; and pharmaceutically acceptable salts thereof.
Overall, the claim coverage centers on broadly defined imidazo[1,2-a]pyridine carboxamide-related compound genera, defined by general formula Ia and general formula Ib with extensive substituent variability and explicit enumerated compound selections. The dependent claim language links the compounds to treatment of bacterial infection and tuberculosis, competitive inhibition of binding to a target protein, and pharmaceutical compositions containing a pharmaceutically acceptable carrier.
Stated Advantages
Documented Applications
Treating a bacterial infection in a person by administering a suitable amount of a compound that competitively inhibits the specific binding of a compound to a target protein.
Treating tuberculosis by administering a suitable amount of a compound.
A pharmaceutical composition including a compound and a pharmaceutically acceptable carrier.
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