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US 11,479,563 B2Granted
Biphenyl compound or salt thereof
AssigneeTaiho Pharmaceutical Co., Ltd.
InventorsSatoshi Yamashita, Takahiro Ogawa
Life of this patent
Estimating the term…
Abstract
The present invention provides a compound represented by Formula (I) or a salt thereof; an LSD1 inhibitor that contains the compound or a salt thereof as an active ingredient; a pharmaceutical composition that contains the compound or a salt thereof; and an antitumor agent that contains the compound or a salt thereof as an active ingredient.
Claims12
A compound represented by Formula (I) or a salt thereof:
- wherein
- ring A represents a monocyclic, bridged cyclic, or spirocyclic nitrogen-containing saturated heterocyclic group,
- ring B represents monocyclic or bicyclic unsaturated hydrocarbon or a monocyclic or bicyclic unsaturated heterocyclic group that may be substituted with oxo,
- R1 represents nitro or cyano,
- R2 represents halogen,
- R3 represents substituted or unsubstituted amino, C1-C6 alkyl, halogen, cyano, oxo, hydroxy, carbamoyl, sulfo, C1-C6 alkoxy, or amino(C1-C6 alkyl),
- R4 represents halogen, hydroxy, nitro, cyano, amino, carboxy, (C2-C7 acyl)amino, (C2-C7 acyl)oxy, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C3-C7 cycloalkyl, mono- or di(C1-C6 alkyl)amino, substituted or unsubstituted carbamoyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted (C1-C6 alkyl)carbonyl, substituted or unsubstituted 4- to 14-membered nitrogen-containing saturated heterocyclic group, or substituted or unsubstituted C6-C14 aromatic hydrocarbon,
- R5 represents hydrogen or C1-C6 alkyl,
- R6 represents hydrogen,
- l is an integer of 0 to 2,
- m is an integer of 0 to 2, and
- n is an integer of 0 to 5,
- wherein when l is 2, two R2s may be identical or different, when m is 2, two R3s may be identical or different, and when n is 2 to 5, two to five R4s may be identical or different.
10 more elements
A compound according to any one of the following (1) to (19) or a salt of the compound according to any one of the following (1) to (19);
- (1) (S)-5′-((3-aminopyrrolidin-1-yl)methyl)-4″-methyl-[1,1′:2′,1″-terphenyl]-4-carbonitrile,
- (2) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-2″,3-difluoro-4″-methyl-[1,1′:2′,1″-terphenyl]-4-carbonitrile-isomer-X,
- (3) (S)-5′-((3-amino-3-methylpyrrolidin-1-yl)methyl)-2″,3-difluoro-4″-methyl-[1,1′:2′,1″-terphenyl]-4-carbonitrile,
- (4) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-2′-(6,7-difluoro-1-(2-hydroxy-2-methylpropyl)-1H-benzo[d][1,2,3]triazol-5-yl)-3-fluoro-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (5) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-2′-(7-chloro-6-fluoro-1-((1-hydroxycyclobutyl)methyl)-1H-benzo[d][1,2,3]triazol-5-yl)-3-fluoro-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (6) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-3-fluoro-2′-(6-fluoro-1-(2-hydroxy-2-methylpropyl)-1H-indazol-5-yl)-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (7) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-2′-(7-chloro-1-(2-ethyl-2-hydroxybutyl)-6-fluoro-1H-benzo[d][1,2,3]triazol-5-yl)-3-fluoro-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (8) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-3-fluoro-2′-(6-fluoro-1-(2-hydroxy-2-methylpropyl)-1H-indol-5-yl)-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (9) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-2″,3-difluoro-4″-(2-hydroxy-2-methylpropyl)-[1,1′:2′,1″-terphenyl]-4-carbonitrile-isomer-X,
- (10) (S)-5′-((3-aminopyrrolidin-1-yl)methyl)-2″,3-difluoro-4″-(2-hydroxy-2-methylpropyl)-[1,1′:2′,1″-terphenyl]-4-carbonitrile,
- (11) 5′-(1-((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)ethyl)-2″,3-difluoro-4″-methyl-[1,1′:2′,1″-terphenyl]-4-carbonitrile-isomer-X,
- (12) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-2′-(1-(2-ethyl-2-hydroxybutyl)-6,7-difluoro-1H-benzo[d][1,2,3]triazol-5-yl)-3-fluoro-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (13) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7-yl)methyl)-2′-(7-bromo-6-fluoro-1-(2-hydroxy-2-methylpropyl)-1H-benzo[d][1,2,3]triazol-5-yl)-3-fluoro-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (14) 5′-(((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptan-7yl)methyl)-2′-(7-bromo-1-(2-ethyl-2-hydroxybutyl)-6-fluoro-1H-benzo[d][1,2,3]triazol-5-yl)-3-fluoro-[1,1′-biphenyl]-4-carbonitrile-isomer-X,
- (15) (1R,2R,4S)-rel-7-((4-methyl-4″-nitro-[1,1′:2′,1″-terphenyl]-4′-yl)methyl)-7-azabicyclo[2.2.1]heptane-2-amine-isomer-X,
- (16) 3-fluoro-2′-(6-fluoro-1-(2-hydroxy-2-methylpropyl)-1H-indazol-5-yl)-5′-((hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methyl)-[1,1′-biphenyl]-4-carbonitrile,
- (17) 5′-((2,6-diazaspiro[3.5]nonan-2-yl)methyl)-3-fluoro-2′-(6-fluoro-1-(2-hydroxy-2-methylpropyl)-1H-indazol-5-yl)-[1,1′-biphenyl]-4-carbonitrile,
- (18) 5′-(((3-endo)-amino-8-azabicyclo[3.2.1]octan-8-yl)methyl)-3-fluoro-2′-(6-fluoro-1-(2-hydroxy-2-methylpropyl)-1H-indazol-5-yl)-[1,1′-biphenyl]-4-carbonitrile, and
- (19) 5′-((2,6-diazaspiro[3.4]octan-6-yl)methyl)-3-fluoro-2′-(6-fluoro-1-(2-hydroxy-2-methylpropyl)-1H-indazol-5-yl)-[1,1′-biphenyl]-4-carbonitrile.
16 more elements
Dependencies are inferred from the claim text.