Amide derivative having antiviral activity

Inventors

OKANO, Azusa • TATENO, Yusuke • NODU, Kouhei • Suzuki, Shinji • Akiyama, Toshiyuki • MATOYAMA, Masaaki • AKAZA, Hiroto • Fukuda, Takashi

Assignees

Shionogi and Co Ltd • Ube Corp

Abstract

The present invention provides a compound represented by formula (I): wherein the dashed line indicates the presence or absence of a bond; R1 is carboxy or the like; L is substituted or unsubstituted non-aromatic carbocyclyldiyl or the like; R2 is substituted or unsubstituted alkyl; R3 is a hydrogen atom or the like; X is ═CRX— or ═N—; Y is ═CRY— or ═N—; U is —CRU═ or —N═; V is —CRV═ or —N═; W is ═CRW— or ═N—; ZA is —C═ or —N—; ZB is —CR5R6— or the like; ZC is —CR7R8— or the like; RX, RY, RV and RW are each independently a hydrogen atom or the like; RU is a hydrogen atom or the like; R5 and R6 are each independently a hydrogen atom or the like; R7 and R8 are each independently a hydrogen atom or the like; R4 is substituted or unsubstituted alkyloxy or the like, or a pharmaceutically acceptable salt thereof, having an antiviral activity; and a pharmaceutical composition comprising the same.

Core Innovation

The disclosure defines a compound of the formula (I), including pharmaceutically acceptable salts thereof, wherein the dashed line indicates the presence or absence of a bond. The structure is defined by variable substituents R1, R1B, R1C, L, R2, R3, X, Y, U, V, W, ZA, ZB, ZC, and additional R substituents, with options that include carboxy, cyano, substituted or unsubstituted aromatic heterocyclyl, alkyl, aminosulfonyl, heterocyclylsulfonyl, carbocyclyl, heterocyclyl, alkylene, alkyloxy, amino, carbamoyl, halogen, hydroxy, and ring-forming combinations.

R1 is selected from carboxy, cyano, substituted or unsubstituted aromatic heterocyclyl, —C(=O)NR1B R1C, or —CH=CHC(=O)OH, and R1B and R1C are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aminosulfonyl, or substituted or unsubstituted non-aromatic heterocyclylsulfonyl. L is substituted or unsubstituted non-aromatic carbocyclyldiyl, substituted or unsubstituted non-aromatic heterocyclyldiyl, or substituted or unsubstituted alkylene; R2 is substituted or unsubstituted alkyl; and R3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkyloxy, substituted or unsubstituted amino, or substituted or unsubstituted carbamoyl.

X, Y, U, V, and W are each —CR— or —N— positions, and ZA, ZB, and ZC provide additional carbon or nitrogen variation, with R5, R6, R7, R8, and R4 providing further substituent variability. The provided examples describe numbered compound series with stereochemical designations and LC/MS retention time or [M+H] data, together with chemical structure depictions, including fluorinated substituents, heteroaromatic or polycyclic scaffolds, and carboxylic acid motifs.

Claims Coverage

The consolidated claims cover one broad independent compound claim for formula (I) with extensive substituent variability and explicit coverage of pharmaceutically acceptable salts. A further independent method claim is present for treating and/or preventing RSV infection by administering the claimed compound or salt. In total, the claims capture two inventive features: the broad formula (I) compound genus and the RSV treatment/prevention use.

The claims cover a structurally broad formula (I) compound class with multiple independently variable positions, explicit bond-presence flexibility, ring-forming alternatives, and pharmaceutically acceptable salts. The consolidated input also includes claim coverage for treating and/or preventing RSV infection by administering the compound or its salt.

Stated Advantages

Documented Applications