US 8,674,136 B2Granted

Aromatic butan-2-ol compounds and preparation and uses thereof

AssigneeInstitute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China

InventorsSong Li, Wu Zhong, Ping Liu, Junhai Xiao, Zhibing Zheng, Yunde Xie, Guoming Zhao, Xiaokui Wang, Lili Wang, Xingzhou Li, Xinbo Zhou

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Abstract

Aromatic butan-2-ol compounds, preparation methods for making the compounds, and uses of the compounds are provided. Specifically, the compound of Formula I, or an optical isomer, racemate, diastereomer, pharmaceutically acceptable salt, or solvate thereof, is provided, where each of the substituents is defined. In addition, a pharmaceutical composition containing the compound, and the use of the compound in manufacture of a medicament for the treatment and/or prophylaxis of a disease or disorder caused by tubercle bacillus infection, is provided.

Claims11

Dependent claims

A compound of Formula I,

or an optical isomer, racemate, diastereomer, pharmaceutically acceptable salt, or solvate thereof, wherein
R1 represents hydrogen, fluoro, chloro, bromo, iodo, hydroxy, an alkoxy, methoxy, nitro, amino, or an alkyl;
R2 represents hydrogen, fluoro, chloro, bromo, iodo, an alkyl, nitro, or amino;
R3 represents 1 to 5 substituents independently selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, hydroxy, an alkoxy, methoxy, nitro, amino, and an alkyl;
R4 represents phenyl, naphthyl or a heterocyclic group, wherein the phenyl, naphthyl, or heterocyclic group is optionally substituted with one or more substituents independently selected from the group consisting of fluoro, chloro, bromo, iodo, hydroxy, an alkoxy, methoxy, nitro, amino, and an alkyl;
and
R5 represents hydroxy, thiol, an alkoxy, an alkylthio, or a halogen.

4 more elements

A compound which is selected from the group consisting of

1-phenyl-2-(1-naphthyl)-1-[2-(3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-chlorophenyl)-2-(1-naphthyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-chlorophenyl)-2-(1-naphthyl)-1-[2-(3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-chlorophenyl)-2-(4-bromophenyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-phenyl-2-(4-bromophenyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-phenyl-2-(3-bromophenyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-chlorophenyl)-2-(2,4-difluorophenyl)-1-[2-(3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-chlorophenyl)-2-(3-bromophenyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-chlorophenyl)-2-phenyl-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1,2-diphenyl-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-chlorophenyl)-2-(2-bromophenyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-phenyl-2-(2-bromophenyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-phenyl-2-(1-naphthyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(4-methylphenyl)-2-(1-naphthyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-phenyl-2-(1-naphthyl)-1-[2-(4,7-dibromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1,6-dibromo-3-[1-phenyl-2-(1-naphthyl)-2-hydroxy-4-(N,N-dimethylamino)]butyl-2-naphthol,
1-(3-chlorophenyl)-2-(1-naphthyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(3-methylphenyl)-2-(1-naphthyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
1-(2-methylphenyl)-2-(1-naphthyl)-1-[2-(7-bromo-3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol, and
1-(4-chlorophenyl)-2-(1-naphthyl)-1-[2-(3-methoxy)naphthyl]-4-(N,N-dimethylamino)-butan-2-ol,
or an optical isomer, racemate, diastereomer, pharmaceutically acceptable salt, or solvate thereof.

18 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/698,465Filed 16 May 2011
Priority: CN 2010 1 017378517 May 2010
Published: US 2013/0085183 A14 Apr 2013
Granted: 18 Mar 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 217/72
With singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain: linked by carbon chains having…
A61K 31/137
Having aromatic rings , e.g. ketamine, nortriptyline: arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
A61P 31/06
Antibacterial agents: for tuberculosis
C07C 213/00
Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or