US 2019/0292155 A1Published application

Therapeutic inhibitory compounds

AssigneeLifesci Pharmaceuticals, Inc.

InventorsAndrew MCDONALD, Shawn QIAN

Life of this patent

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Abstract

Provided herein are heterocyclic derivative compounds and pharmaceutical compositions comprising said compounds. Said heterocyclic derivative compounds are complement factor D inhibitors. Such compounds are useful for treating complement related disorders including, but are not limited to, autoimmune, inflammatory, and neurodegenerative diseases.

Claims64

Dependent claims

A compound, or a pharmaceutically acceptable salt thereof, having the structure of Formula (I):

wherein
Ring A is an optionally substituted heteroaryl ring;
Ring B is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted 3-, 4-, 5-, or 6-membered cycloalkyl, or optionally substituted 3-, 4-, 5-, or 6-membered heterocyclyl;
X is —CR9R10— or —NR11—;
R1 is optionally substituted alkyl, optionally substituted 3-, 4-, 5-, or 6-membered cycloalkyl, optionally substituted carbocyclylalkyl, optionally substituted 3-, 4-, 5-, or 6-membered heterocyclyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, or optionally substituted dicyclopropylmethyl;
R2, R6, R9, R10, each R7, or each R8, is independently selected from hydrogen, halo, hydroxy, amino, —CO2H, —S(O)—R20, —S—R20, —S(O)2—R20, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted (heterocyclyl)-O—, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkylamino, optionally substituted dialkylamino, —CO—R20, —CO2—R20, —CON(R21)2, —SO2N(R21)2, —C(═NR22)—N(R21)2, optionally substituted alkynyl, —N(R24), —NR24CO—R23, —NR24CO2—R23, —NR24CO—R23, —NR24CO2—R23, —NR24CO—N(R23)2, —NR24SO2—N(R23)2, —NR24CO—R23, —NR24CO2—R23, —NR24CO—N(R24)2, or —NR24SO2—N(R24)2;
each R20 is independently optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R21 is independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R22 is independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl;
R11 is hydrogen, or optionally substituted alkyl;
and
n is 0, 1, 2, or 3.

9 more elements

A compound, or pharmaceutically acceptable salt thereof, chosen from:

(S)-1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-1-cyclopropyl-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
(S)-1-(2-((1-((3-chloro-2-fluorophenyl)amino)-1-oxopropan-2-yl)(methyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
(S)-1-(2-((1-((3-chloro-2-fluorobenzyl)amino)-1-oxopropan-2-yl)(methyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(isopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(ethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorophenyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
3-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-1-carboxamide;
1-(2-(cyclopropyl(2-((5-hydroxy-3,3-dimethylcyclohexyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-(((1S,5S)-5-hydroxy-3,3-dimethylcyclohexyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorophenyl)amino)-2-oxoethyl)(isopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(isopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(2-hydroxyethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(methyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(ethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(piperidin-4-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide hydrochloride;
3-(2-((2-aminoethyl)(2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-1-carboxamide;
3-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(cyclopentyl)amino)-2-oxoethyl)-1H-indazole-1-carboxamide;
3-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(cyclobutyl)amino)-2-oxoethyl)-1H-indazole-1-carboxamide;
3-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(tetrahydro-2H-pyran-4-yl)amino)-2-oxoethyl)-1H-indazole-1-carboxamide;
1-(2-(azetidin-3-yl(2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(2-(methylamino)ethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-acetamidoethyl)(2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(pyridin-4-ylmethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((6-chloropyridin-2-yl)amino)-2-oxoethyl)(pyrrolidin-3-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(thiophen-3-ylmethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclobutyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(tetrahydro-2H-pyran-4-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopentyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-aminoethyl)(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(pyridin-4-ylmethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(methyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(piperidin-4-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(pyridin-3-ylmethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(phenyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(pyrrolidin-3-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
(R)-1-(2-((1-((3-chloro-2-fluorobenzyl)amino)-1-oxopropan-2-yl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
(S)-1-(2-((1-((3-chloro-2-fluorobenzyl)amino)-1-oxopropan-2-yl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-pyrazolo[3,4-c]pyridine-3-carboxamide;
3-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indole-1-carboxamide;
3-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)imidazo[1,5-a]pyridine-1-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide;
3-carbamoyl-1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-pyrazole-5-carboxylic acid;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-pyrazole-3,5-dicarboxamide;
4-bromo-1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-pyrazole-3-carboxamide;
2-(3-acetyl-1H-indazol-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-N-cyclopropylacetamide;
2-(1-acetylimidazo[1,5-a]pyridin-3-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-N-cyclopropylacetamide;
N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-N-cyclopropyl-2-(3-(1-hydroxyethyl)-1H-indazol-1-yl)acetamide;
3-(3-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-3-isopropylureido)-1H-indole-1-carboxamide;
3-(3-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-3-cyclopropylureido)-1H-indole-1-carboxamide;
3-(3-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-3-(pyrrolidin-3-yl)ureido)-1H-indole-1-carboxamide;
1-(3-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-3-cyclopropylureido)imidazo[1,5-a]pyridine-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(3-methylbutan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-cyclopropylethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(sec-butyl(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(4-hydroxybutan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-hydroxypropan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
methyl 2-(2-(3-carbamoyl-1H-indazol-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)acetamido)propanoate;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(4-fluorobutan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-methoxybutan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((1-amino-1-oxopropan-2-yl)(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(2-methylcyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(3,3-dimethylbutan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-phenylethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-fluoropropan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1,1,1-trifluoropropan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-methoxypropan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-cyclopropyl-2-hydroxyethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((2-chloro-3-fluorobenzyl)amino)-2-oxoethyl)(1,3-difluoropropan-2-yl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((4-aminobutan-2-yl)(2-((2-chloro-3-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
ethyl 3-(2-(3-carbamoyl-1H-indazol-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)acetamido)butanoate;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(1-cyclopropyl-3-hydroxypropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
3-(2-(3-carbamoyl-1H-indazol-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)acetamido)butanoic acid;
1-(2-((3-amino-1-cyclopropyl-3-oxopropyl)(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((4-amino-4-oxobutan-2-yl)(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
ethyl 3-(2-(3-carbamoyl-1H-indazol-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)acetamido)-4,4,4-trifluorobutanoate;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-5-fluoro-1H-indazole-3-carboxamide;
3-(2-(3-carbamoyl-1H-indazol-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)acetamido)-4,4,4-trifluorobutanoic acid;
5-chloro-1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
7-chloro-1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2,6-difluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2,4-difluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-6-fluoro-1H-indazole-3-carboxamide;
6-chloro-1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-6-cyano-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-6-cyano-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-7-fluoro-1H-indazole-3-carboxamide;
6-(aminomethyl)-1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-5-cyano-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-(((6-chloro-1H-indazol-4-yl)methyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-5-cyano-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3,5-dicarboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-6-(trifluoromethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-5-(trifluoromethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-4-cyano-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-4-fluoro-1H-indazole-3-carboxamide;
2-(3-(1H-imidazol-2-yl)-1H-indazol-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-N-cyclopropylacetamide;
1-(2-((2-((3-chloro-2-fluoro-4-(hydroxymethyl)benzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3,6-dicarboxamide;
1-(2-((2-((5-(aminomethyl)-3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-(((4-chloro-1H-indazol-6-yl)methyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-5-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((3,4-dichlorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-7-cyano-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((2,3-dichlorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-(((6-chloropyridin-2-yl)methyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-4-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-(((5-chloro-1H-indazol-7-yl)methyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-(((5-chlorobenzofuran-7-yl)methyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-7-(trifluoromethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chlorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-4-methylbenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-(((7-chloro-1H-indazol-5-yl)methyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((2-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-methoxybenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((4-carbamoyl-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-amino-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((3,5-dichlorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-bromo-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((4-amino-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((2-fluoro-3-methoxybenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-cyano-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-5-(trifluoromethyl)benzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-4-methoxybenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((2-fluoro-3-(hydroxymethyl)benzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((3-cyclopropyl-2-fluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((2-fluoro-3-methylbenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-5-methylbenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-(((5-chloropyridin-3-yl)methyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-cyclopropylbenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((2,3-difluorobenzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-5-cyanobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-methylbenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-((2-((3-chloro-2-(trifluoromethyl)benzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
1-(2-(cyclopropyl(2-((2-fluoro-3-(trifluoromethyl)benzyl)amino)-2-oxoethyl)amino)-2-oxoethyl)-1H-indazole-3-carboxamide;
2-(3-acetylimidazo[1,5-a]pyridin-1-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-N-cyclopropylacetamide;
1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)imidazo[1,5-a]pyridine-3-carboxamide;
2-(1-acetylimidazo[1,5-a]pyridin-3-yl)-N-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-N-cyclopropylacetamide;
3-(3-(2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)-3-cyclopropylureido)imidazo[1,5-a]pyridine-1-carboxamide;
or
2-(3-(3-acetylimidazo[1,5-a]pyridin-1-yl)-1-cyclopropylureido)-N-(3-chloro-2-fluorobenzyl)acetamide.

139 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/317,768Filed 14 Jul 2017
Priority: 15 Jul 2016
Published: 26 Sep 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification18 codes

C07D 231/56
Condensed with carbocyclic rings or ring systems: benzopyrazoles; Hydrogenated benzopyrazoles
A61K 9/0053
Galenical forms characterised by the site of application: mouth and digestive tract, i.e. intraoral and peroral administration
A61K 9/2013
Excipients; Inactive ingredients: organic compounds, e.g. phospholipids, fats
A61K 9/2054
Polysaccharides, e.g. alginate, gums; Cyclodextrin: cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Family

Application62/362,795Us provisional application · filed 15 Jul 2016
US 2019/0292155 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound, or a pharmaceutically acceptable salt thereof, having the structure of Formula (I):

wherein
Ring A is an optionally substituted heteroaryl ring;
Ring B is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted 3-, 4-, 5-, or 6-membered cycloalkyl, or optionally substituted 3-, 4-, 5-, or 6-membered heterocyclyl;
X is —CR9R10— or —NR11—;
R1 is optionally substituted alkyl, optionally substituted 3-, 4-, 5-, or 6-membered cycloalkyl, optionally substituted carbocyclylalkyl, optionally substituted 3-, 4-, 5-, or 6-membered heterocyclyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, or optionally substituted dicyclopropylmethyl;
R2, R6, R9, R10, each R7, or each R8, is independently selected from hydrogen, halo, hydroxy, amino, —CO2H, —S(O)—R20, —S—R20, —S(O)2—R20, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted (heterocyclyl)-O—, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkylamino, optionally substituted dialkylamino, —CO—R20, —CO2—R20, —CON(R21)2, —SO2N(R21)2, —C(═NR22)—N(R21)2, optionally substituted alkynyl, —N(R24), —NR24CO—R23, —NR24CO2—R23, —NR24CO—R23, —NR24CO2—R23, —NR24CO—N(R23)2, —NR24SO2—N(R23)2, —NR24CO—R23, —NR24CO2—R23, —NR24CO—N(R24)2, or —NR24SO2—N(R24)2;
each R20 is independently optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R21 is independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R22 is independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl;
R11 is hydrogen, or optionally substituted alkyl;
and
n is 0, 1, 2, or 3.

9 more elements

Facts

Application

16/317,768Filed 14 Jul 2017

Priority

15 Jul 2016

Published

26 Sep 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification18 codes

C07D 231/56
Condensed with carbocyclic rings or ring systems: benzopyrazoles; Hydrogenated benzopyrazoles
A61K 9/0053
Galenical forms characterised by the site of application: mouth and digestive tract, i.e. intraoral and peroral administration
A61K 9/2013
Excipients; Inactive ingredients: organic compounds, e.g. phospholipids, fats
A61K 9/2054
Polysaccharides, e.g. alginate, gums; Cyclodextrin: cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose