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US 11,952,387 B2Granted
Bicyclic heteroaromatic ring derivative
AssigneeKyorin Pharmaceutical Co., Ltd.
InventorsMasahiko Kinebuchi, Takekazu Kondou, Koji Ochiai, Yosuke Nishigaya
Life of this patent
Estimating the term…
Abstract
[Problem] To provide a compound having an antiviral action on a virus belonging to the picornavirus genus, specifically, a rhinovirus. [Solution] Provided are a compound represented by general formula (1), a pharmaceutically acceptable salt thereof, or a hydrate thereof.
Claims14
A compound represented by Formula (1):
- wherein
- X represents N or CH;
- Q1 represents N or CH;
- Q2 represents N or CR3;
- L represents —SO2—, —SO2C(R8)2—, or —SO2NR8—;
- R1 represents H;
- a C1-C6 alkyl group, wherein the alkyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a haloC1-C6 alkyl group, a cyano group, a carboxy group, a C3-C10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, a C3-C10 cycloalkyloxy group, a 3- to 10-membered heterocycloalkyloxy group, —C(O)R9, and —C(O)NR10R11;
- a C3-C6 cycloalkyl group, wherein the cycloalkyl group is optionally substituted with one or more substituents selected from the group consisting of a haloC1-C6 alkyl group, a C1-C6 alkoxy group, a hydroxy group, and a cyano group;
- or a C2-C6 alkenyl group, wherein the alkenyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C1-C6 alkoxy group, a cyano group, a carboxy group, a C3-C10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, a C3-C10 cycloalkyloxy group, a 3- to 10-membered heterocycloalkyloxy group, —C(O)R9, and —C(O)NR10R11;
- R2 represents a C1-C6 alkyl group;
- R3 represents H;
- a C1-C6 alkyl group, wherein the alkyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, a haloC1-C6 alkyl group, a cyano group, a C3-C10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, a C3-C10 cycloalkyloxy group, a 3- to 10-membered heterocycloalkyloxy group, —C(O)R9, and —C(O)NR10R11;
- a hydroxy group;
- a C1-C6 alkoxy group;
- a haloC1-C6 alkyl group;
- a cyano group;
- a C3-C10 cycloalkyl group;
- a 3- to 10-membered heterocycloalkyl group;
- a C3-C10 cycloalkyloxy group;
- a 3- to 10-membered heterocycloalkyloxy group;
- —C(O)R9;
- —C(O)NR10R11;
- or a halogen atom;
- R4 represents H, a halogen atom, a C1-C6 alkoxy group, a deuterated C1-C6 alkoxy group, a C1-C6 alkyl group, a haloC1-C6 alkyl group, a haloC1-C6 alkoxy group, a hydroxyC1-C6 alkyl group, a hydroxy group, a cyano group, —C(O)R9, —C(O)NR10R11, or NR10R11;
- when Q2 is CR3, R3 and R4 may be joined together to form a ring;
- G represents —R5—R6—R7;
- a hydroxyC1-C6 alkyl group, wherein the hydroxyC1-C6 alkyl group is optionally substituted with W1 and W2, wherein W1 and W2 are each independently selected from the group consisting of hydrogen, a C1-C6 alkyl group, a deuterated C1-C6 alkyl group, a haloC1-C6 alkyl group, and a hydroxyC1-C6 alkyl group, wherein W1 and W2 may be joined together to form a ring, and the ring formed by W1 and W2 is optionally substituted with one or more halogen atoms;
- a C3-C6 cycloalkyl group, wherein the C3-C6 cycloalkyl group is optionally substituted with W3 and W4, wherein W3 and W4 are each independently selected from the group consisting of hydrogen, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C1-C6 acyl group, a hydroxyC1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, —SO2R12, and an oxo group, and W3 and W4 may be joined together to form a ring;
- a C5-C8 bicycloalkyl group, wherein the C5-C8 bicycloalkyl group is optionally substituted with W3 and W4, wherein W3 and W4 are each independently selected from the group consisting of hydrogen, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C1-C6 acyl group, a hydroxyC1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, —SO2R12, and an oxo group, and W3 and W4 may be joined together to form a ring;
- a 3- to 10-membered heterocycloalkyl group, wherein the 3- to 10-membered heterocycloalkyl group is optionally substituted with W3 and W4, wherein W3 and W4 are each independently selected from the group consisting of hydrogen, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C1-C6 acyl group, a hydroxyC1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, —SO2R12, —C(O)N(R13)2, and an oxo group, and W3 and W4 may be joined together to form a ring;
- a C1-C6 alkyl group, wherein the C1-C6 alkyl group is optionally substituted with W5 and W6, wherein W5 and W6 are each independently selected from the group consisting of H, a cyano group, a hydroxyC1-C6 alkyl group, a C1-C6 alkyl group, a C1-C6 alkoxycarbonyl group, a carboxy group, and —C(O)N(R13)2, and W5 and W6 may be joined together to form a ring;
- a phenyl group, wherein the phenyl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a hydroxyC1-C6 alkyl group, a C1-C6 acyl group, a carboxy group, a hydroxy group, a haloC1-C6 alkyl group, a cyano group, a C3-C10 cycloalkyl group, a 3-, to 10-membered heterocycloalkyl group, —NR10R11, —C(O)R9, —C(O)NR10R11, a C1-C6 alkoxycarbonyl group, —SO2R12, and a C1-C6 alkoxy group;
- or a heteroaryl group, wherein the heteroaryl group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a hydroxyC1-C6 alkyl group, a C1-C6 acyl group, a carboxy group, a hydroxy group, a haloC1-C6 alkyl group, a cyano group, a C3-C10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR10R11, —C(O)R9, —C(O)NR10R11, a C1-C6 alkoxycarbonyl group, —SO2R12, and a C1-C6 alkoxy group;
- R5 represents a hydroxyC1-C6 alkylene group, wherein the hydroxyC1-C6 alkylene group is optionally substituted with W1 and W2, wherein W1 and W2 are each independently selected from the group consisting of H, a C1-C6 alkyl group, a deuterated C1-C6 alkyl group, a haloC1-C6 alkyl group, and a hydroxyC1-C6 alkyl group, and W1 and W2 may be joined together to form a ring, and the ring formed by W1 and W2 is optionally substituted with one or more halogen atoms;
- a C3-C6 cycloalkylene group, wherein the C3-C6 cycloalkylene group is optionally substituted with W3 and W4, wherein W3 and W4 are each independently selected from the group consisting of H, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C1-C6 acyl group, a hydroxyC1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, —SO2R12, and an oxo group, and W3 and W4 may be joined together to form a ring;
- a C5-C8 bicycloalkylene group, wherein the C5-C8 bicycloalkylene group is optionally substituted with W3 and W4, wherein W3 and W4 are each independently selected from the group consisting of H, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C1-C6 acyl group, a hydroxyC1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, —SO2R12, and an oxo group, and W3 and W4 may be joined together to form a ring;
- a 3- to 10-membered heterocycloalkylene group, wherein the 3- to 10-membered heterocycloalkylene group is optionally substituted with W3 and W4, wherein W3 and W4 are each independently selected from the group consisting of H, a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C3-C10 cycloalkyl group, a C1-C6 acyl group, a hydroxyC1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxycarbonyl group, —SO2R12, —C(O)N(R13)2, and an oxo group, and W3 and W4 may be joined together to form a ring;
- a C1-C6 alkylene group, wherein the C1-C6 alkylene group is optionally substituted with W5 and W6, wherein W5 and W6 are each independently selected from the group consisting of H, a cyano group, a hydroxyC1-C6 alkyl group, a C1-C6 alkyl group, a C1-C6 alkoxycarbonyl group, a carboxy group, and —C(O)N(R13)2, and W5 and W6 may be joined together to form a ring;
- a phenylene group, wherein the phenylene group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a hydroxyC1-C6 alkyl group, a C1-C6 acyl group, a carboxy group, a hydroxy group, a haloC1-C6 alkyl group, a cyano group, a C3-C10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR10R11, —C(O)R9, —C(O)NR10R11, a C1-C6 alkoxycarbonyl group, —SO2R12, and a C1-C6 alkoxy group;
- or a heteroarylene group, wherein the heteroarylene group is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a hydroxyC1-C6 alkyl group, a C1-C6 acyl group, a carboxy group, a hydroxy group, a haloC1-C6 alkyl group, a cyano group, a C3-C10 cycloalkyl group, a 3- to 10-membered heterocycloalkyl group, —NR10R11, —C(O)R9, —C(O)NR10R11, a C1-C6 alkoxycarbonyl group, —SO2R12, and a C1-C6 alkoxy group;
- R6 represents a bond or a C3-C6 cycloalkylene group;
- R7 represents H or a hydroxy group;
- each R8 independently represents H or a C1-C6 alkyl group;
- R9 represents H, a hydroxy group, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C3-C6 cycloalkoxy group;
- R10 represents H or a C1-C6 alkyl group;
- R11 represents H or a C1-C6 alkyl group;
- R12 represents H or a C1-C6 alkyl group;
- and
- each R13 independently represents H, a C1-C6 alkyl group, or a hydroxyC1-C6 alkyl group,
- a pharmacologically acceptable salt of the compound, a hydrate of the compound or a hydrate of the salt.
47 more elements
Dependencies are inferred from the claim text.