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US 2021/0070747 A1Published application
2(1h)-quinolinone derivative
AssigneeTaisho Pharmaceutical Co., Ltd.
InventorsHideaki AMADA, Norikazu OTAKE, Fumihito USHIYAMA, Chunhae KIM, Tomoki TAKEUCHI, Nozomi TANAKA
Life of this patent
Estimating the term…
Abstract
Provided are: useful novel compounds that exhibit antibacterial activity based on their actions for inhibiting GyrB of DNA gyrase and ParE of topoisomerase IV; and 2(1H)-quinolinone derivatives represented by formula [1]: or pharmaceutically acceptable salts thereof.
Claims21
A compound represented by formula [1]:
- {wherein
- Z represents NH—R1, a C1-4 alkyl group (said C1-4 alkyl group may be substituted with an amino group or a hydroxy group) or a hydroxy group;
- R1 represents a hydrogen atom or a C1-4 alkyl group;
- T, U, V and W all represent C—R2 or either one of them represents N while the other represent C—R2;
- each R2 independently represents a hydrogen atom, a halogen atom, a hydroxy group, a C1-6alkyl group, a C1-6 alkoxy group (said C1-6 alkyl group and said C1-6alkoxy group may be substituted with —N(R21)(R22)) or an amino group [said amino group may be substituted with a C1-6 alkyl group (said C1-6 alkyl group may be substituted with a piperidin-4-yl group, a pyrrolidin-3-yl group, an azetidin-3-yl group, a 1-amino-cyclobutan-3-yl group, a morpholinyl group or —N(R23)(R24)), a 1-amino-cyclobutan-3-yl group or any of the substituents described by formula [2]]:
- R21, R22, R23 and R24 are the same or different and each represents a hydrogen atom or a C1-6alkyl group;
- L1 represents —CONR3—, —COO—, —(CH2)nNR3— or —NR3CO—;
- R3 represents a hydrogen atom or a C1-6 alkyl group;
- n represents an integer of 1 to 4;
- L2 represents a group selected from the group consisting of a bond, a C1-6 alkylene group, a piperidinediyl group, a pyrrolidinediyl group and an azetidinediyl group (said C1-6 alkylene group, said piperidinediyl group, said pyrrolidinediyl group and said azetidinediyl group may be substituted with a carboxy group or an oxo group);
- A represents an aryl group, a heterocyclic group or a C3-8 cycloalkyl group (said aryl group, said heterocyclic group and said C3-8cycloalkyl group may be substituted with one to four substituents which are the same or different and are each selected from the following substituent group Ra);
- the substituent group Ra represents a C1-6alkyl group (said C1-6 alkyl group may be substituted with one or two substituents selected from the group consisting of a carboxy group, a hydroxy group, a C3-8cycloalkyl group, a carbamoyl group and —N(R11)(R12)), a carboxy group, a hydroxy group, a heterocyclic group, an amidino
- group, —N(R13)(R14), —CON(R15)(R16), a C1-6alkoxy group (said C1-6alkoxy group may be substituted with one or two substituents selected from the group consisting of an amino group, an N-methylpiperazinyl group and a morpholinyl group), a C2-6alkenyl group (said C2-6alkenyl group may be substituted with a hydroxy group or —N(R17)(R18)), —COOR19, a 3-aminoazetidinyl group, a piperazinyl group (said piperazinyl group may be substituted with one methyl group), a 4-aminopiperidinyl group or any of the substituents described by formula [3]:
- R11 and R12 are the same or different and each represents a hydrogen atom, a C1-12alkyl group, a C3-8cycloalkyl group, a hydroxyethyl group, an N-methylpiperidin-4-yl group, a carboxymethyl group, an N,N-dimethylaminopropyl group or an aminoethyl group;
- or alternatively
- R11 and R12, when taken together with the nitrogen atom to which they bind, may form a saturated 3- to 7-membered ring, where said saturated 3- to 7-membered ring may further contain one or more nitrogen atoms, oxygen atoms or sulfur atoms in the ring, and said saturated 3- to 7-membered ring may be substituted with an amino group;
- R13 and R14 are the same or different and each represents a hydrogen atom, a C1-6alkoxy carbonyl group, a C3-8cycloalkyl group, —CONHSO2Me, a C1-6 alkyl group [said C1-6 alkyl group may be substituted with one or two substituents selected from among an amino group, an N-methylpiperazinyl group, a morpholinyl group, —N(CH2CH2OH)2 and a heterocyclic group (said heterocyclic group may be substituted with an amino group)];
- R15 and R16 are the same or different and each represents a hydrogen atom, a hydroxy group, a 1,3-dihydroxypropan-2-yl group, a methanesulfonyl group, an N,N-dimethylsulfamoyl group and a C1-6 alkyl group (said C1-6 alkyl group may be substituted with one or two substituents which are the same or different and are each selected from the group consisting of an amino group, a morpholinyl group, a piperidinyl group, a carboxy group, a hydroxy group and the substituent described by formula [4]):
- R15 and R16, when taken together with the nitrogen atom to which they bind, may form a saturated 3- to 7-membered ring, where said saturated 3- to 7-membered ring may further contain one or more nitrogen atoms, oxygen atoms or sulfur atoms in the ring;
- R17 and R18 are the same or different and each represents a hydrogen atom or a C1-6 alkyl group;
- R19 represents a C1-6 alkyl group;
- and
- R20 represents a hydrogen atom or a C1-6 alkyl group}
- or a pharmaceutically acceptable salt thereof.
21 more elements
Dependencies are inferred from the claim text.