US 11,447,466 B2Granted

Substituted indole compounds useful as inhibitors of TLR7/8/9

AssigneeBristol-Myers Squibb Company

InventorsAlaric J. Dyckman, Dharmpal S. Dodd, Tasir Shamsul Haque, Brian K. Whiteley, John L. Gilmore

Life of this patent

Estimating the term…

Abstract

Disclosed are compounds of Formula (I) or a salt thereof, wherein: Y is Formula (II), or Formula (III); R1, R2, R2a, R2b, R2c, R3, R4, R5, m, and n are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.

Claims7

Dependent claims

A compound of Formula (I)

or a salt thereof, wherein:
Y is
R1 is —CH2CH3 or —CH(CH3)2;
R2 is —CH3, —CH2CH3, —CH(CH3)2, —CH2CH(CH3)2, —CH2CH2OH, —CH2CH2CH2OH, —CH2C(CH3)2OH, —CH2CHF2, —CH2CF3, —CH2CH2OCH3, —CH2(cyclopropyl), —CH2(phenyl), —CH2C(O)NH2, tetrahydrofuranyl, or phenyl;
each R2a is independently H, F, Cl, —CN, —NH2, C1-5 alkyl, —CF3, —CH2OH, —OCH3, —CH2OCH3, —CH2CH2(cyclopropyl), —C(O)OCH3, —C(O)N(CH3)2, —C(O)NH(CH2CH2CH3), —CH═CH2, —C(CH3)═CH2, —CH═CH(cyclopropyl), —C(O)(pyrrolidinyl), or a cyclic group selected from pyrrolidinyl, pyrazolyl, phenyl, pyridinyl, and pyrimidinyl, each substituted with zero, 1, or 2 Ry;
each Ry is independently F, —CN, —CH3, —CF3, —OCH3, —NHC(O)CH3, —C(O)NH2, —C(O)NH(CH3), cyclopropyl, or morpholinyl;
R3 is H, —CH3, —CH2CH2CH3, —CH(CH3)2, —CH2CH2CH2CH3, —CH2CH(CH3)2, —CH2CH2CH(CH3)2, —CH2CH2CF3, —CH2CH2CH2CF3, —CH2CH2CH(CF3)2, —CH2CH2OH, —CH2CH2CH2OH, —C(CH3)2OH, —CH2C(CH3)2OH, —CH2CH2C(CH3)2OH, —CH2CH(OH)CH(CH3)2, —CH2CH(OH)CH2OH, —CH(CH2CH2OH)2, —CH2CN, —CH2CH2CN, —CH2CH2OCH3, —CH2CH2CH2OCH3, —(CH2CH2O)2-3OCH3, —CH2CH2NH(CH3), —C(CH3)2C(O)OH, —CH2C(O)NH2, —CH2C(O)NH(CH3), —CH2C(O)N(CH3)2, —CH2C(O)NH(CH2CH3), —CH2C(O)NH(CH2CH(CH3)OH), —CH2C(O)NH(CH2C(CH3)2OH), —CH(CH3)C(O)NH2, —C(CH3)2C(O)NH2, —CH2CH2C(O)NH2, —CH2CH2S(O)2CH3, —C(O)CH3, —C(O)CF3, —C(O)CH2N(CH3)2, —C(O)C(CH3)2NH2, —C(O)CH(CH3)NH(CH3), —C(O)C(CH3)2NH(CH3), —C(O)CH2CH(CH3)OH, —C(O)CH2C(CH3)2OH, —C(O)C(CH3)2CH2OH, —NHC(O)CH3, —CH2(methyl triazolyl), —CH2(trifluoromethyl phenyl), —CH2(difluoromethyl, fluorophenyl), —CH2(fluoro, chlorophenyl), —CH2(difluorocyclopropyl), —CH2CH2(pyrrolidin-dionyl), —CH2(oxetanyl), —CH2(tetrahydropyranyl), —CH2C(O)(hydroxypyrrolidinyl), —CH2C(O)(pyrazolidinonyl), —CH2C(O)(pyrrolidinyl), —CH2(dimethyl pyrazolyl), —CH2(methyl pyrazolyl), —CH2(pyrazolyl), —CH2(cyclopropyl), —CH2(tetrahydrofuranyl), —CH2(i-propyl pyrazolyl), —CH2(n-propyl pyrazolyl), —CH(CH3)(methyl pyrazolyl), —C(O)(aminocyclopropyl), —C(O)(hydroxypyrrolidinyl), —C(O)(methyl, hydroxypyrrolidinyl), —C(O)CH2(pyrrolidinonyl), —C(O)CH2(pyrrolidinyl), —C(O)O(methyl pyrrolidinyl), —S(O)2CH2CH2(pyrrolidinyl), —CH2(hydroxytetrahydropyranyl), or a cyclic group selected from cyclopentyl, cyclohexyl, oxetanyl, azetidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrofuranonyl, tetrahydropyranyl, piperidinyl, and dioxotetrahydrothiophenyl, each substituted with zero, 1, or 2 R3a;
each R3a is independently F, —OH, —CH3, —CH(CH3)2, —CF3, or —C(O)NH2;
R5 is F;
m is zero;
and
n is zero or 1.

9 more elements

A compound selected from:

5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-on (1);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (2);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (3);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,6-dimethylpyridin-2(1H)-one (6);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (8);
3-amino-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (9);
3-fluoro-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (13);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (14);
1-ethyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (15);
1-isopropyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)pyridin-2(1H)-one (16);
3-amino-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (19);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1-methylpyridin-2(1H)-one (20);
3-chloro-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (22);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (23);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (24);
3-ethyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,6-dimethylpyridin-2(1H)-one (25);
1-ethyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3,4-dimethylpyridin-2(1H)-one (26);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1,6-dimethylpyridin-2(1H)-one (28);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1,4-dimethylpyridin-2(1H)-one (29);
1-(2-hydroxyethyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (30);
3-chloro-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (31);
3-chloro-1-ethyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)pyridin-2(1H)-one (32);
3-chloro-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,6-dimethylpyridin-2(1H)-one (33);
1-(cyclopropylmethyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (34);
1,3-diethyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-6-methylpyridin-2(1H)-one (35);
1-isobutyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (36);
methyl 5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (37);
1-(3-hydroxypropyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (38);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-(2-methoxyethyl)-3-methylpyridin-2(1H)-one (39);
1-(2,2-difluoroethyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (40);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(trifluoromethyl)pyridin-2(1H)-one (41);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methyl-1-(tetrahydrofuran-3-yl) pyridin-2(1H)-one (42);
1-(2-hydroxy-2-methylpropyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (43);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methyl-1-phenylpyridin-2(1H)-one (44);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methyl-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one (45);
1-benzyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (46);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (47);
1-(2-hydroxy-2-methylpropyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)pyridin-2(1H)-one (48);
2-(5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-2-oxopyridin-1(2H)-yl)acetamide (49);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-[3,3′-bipyridin]-2(1H)-one (50);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(prop-1-en-2-yl)pyridin-2(1H)-one (51);
(E)-3-(2-cyclopropylvinyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (52);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-phenylpyridin-2(1H)-one (53);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (54);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(p-tolyl)pyridin-2(1H)-one (55);
3-(5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)benzonitrile (56);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-2′-methoxy-1-methyl-[3,3′-bipyridin]-2(1H)-one (57);
3-(5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)benzamide (58);
3-(5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)-N-methylbenzamide (59);
N-(3-(5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)phenyl)acetamide (60);
3-(3,3-dimethylbutyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (61);
3-(2-cyclopropylethyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (62);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-N,N,1-trimethyl-2-oxo-1,2-dihydropyridine-3-carboxamide (63);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-2-oxo-N-propyl-1,2-dihydropyridine-3-carboxamide (64);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethyl-[3,3′-bipyridin]-2(1H)-one (65);
3-isopropyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (66);
3-ethyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (67);
1,3-diethyl-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)pyridin-2(1H)-one (68);
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrrolidine-1-carbonyl) pyridin-2(1H)-one (69);
3-(hydroxymethyl)-5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (70);
2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (71);
5-(3-isopropyl-5-(1-((1-methyl-1H-1,2,4-triazol-3-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (72);
5-(5-(1-(3-hydroxy-3-methylbutyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (73);
5-(5-(1-(3-hydroxy-3-methylbutyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (74);
5-(5-(1-isobutylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (75);
3-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)propanenitrile (76);
5-(3-isopropyl-5-(1-(4-(trifluoromethoxy) benzyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (77);
5-(5-(1-(5-(difluoromethoxy)-2-fluorobenzyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (78);
5-(3-isopropyl-5-(1-(4,4,4-trifluorobutyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (79);
5-(5-(1-(5-chloro-2-fluorobenzyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (80);
5-(5-(1-(1,1-dioxidotetrahydrothiophen-3-yl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (81);
3-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)propanamide (82);
5-(5-(1-((2,2-difluorocyclopropyl)methyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (83);
1-(2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)ethyl)pyrrolidine-2,5-dione (84);
5-(5-(1-(3-hydroxypropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (85);
5-(5-(1-isopentylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (86);
5-(5-(1-cyclohexylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (87);
5-(3-isopropyl-5-(1-(4,4,4-trifluoro-3-(trifluoromethyl)butyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (88);
5-(5-(1-isobutylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-methyl-3-phenylpyridin-2(1H)-one (89);
5-(5-(1-isopentylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-methyl-3-phenylpyridin-2(1H)-one (90);
3-chloro-5-(5-(1-isopentylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (91);
3-chloro-5-(3-isopropyl-5-(1-(oxetan-3-ylmethyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (92);
3-chloro-5-(3-isopropyl-5-(1-((tetrahydro-2H-pyran-4-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (93);
5-(3-isopropyl-5-(1-(oxetan-3-ylmethyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (94);
3-chloro-5-(3-isopropyl-5-(1-(2-methoxyethyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (95);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)acetonitrile (96);
3-chloro-5-(5-(1-cyclopentylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (97);
3-chloro-5-(3-isopropyl-5-(1-(2-(2-(2-methoxyethoxy)ethoxy)ethyl) piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (98);
3-chloro-5-(3-isopropyl-5-(1-(3-methoxypropyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (99);
5-(3-isopropyl-5-(1-((tetrahydro-2H-pyran-4-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (100);
3-chloro-5-(3-isopropyl-5-(1-(2-(2-methoxyethoxy)ethyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (101);
3-chloro-5-(3-isopropyl-5-(1-(3,3,3-trifluoropropyl) piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (102);
5-(3-isopropyl-5-(1-(2-methoxyethyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (103);
5-(3-isopropyl-5-(1-(4,4,4-trifluorobutyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (104);
3-chloro-5-(3-isopropyl-5-(1-(4,4,4-trifluorobutyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (105);
3-chloro-5-(5-(1-isobutylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (106);
3-chloro-5-(3-isopropyl-5-(1-(2-(methylsulfonyl)ethyl) piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (107);
5-(3-isopropyl-5-(1-(2-(methylsulfonyl)ethyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl) pyridin-2(1H)-one (108);
5-(5-(1-isobutylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-(2-methoxyethyl)-3-methylpyridin-2(1H)-one (109);
1-isobutyl-5-(3-isopropyl-5-(1-(4,4,4-trifluorobutyl)piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (110);
1-benzyl-5-(3-isopropyl-5-(1-(4,4,4-trifluorobutyl)piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (111);
1-isobutyl-5-(5-(1-isobutylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (112);
1-benzyl-5-(5-(1-isobutylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (113);
2-(4-(3-isopropyl-2-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (114);
2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N-methylacetamide (117);
(S)-5-(5-(1-(2-(3-hydroxypyrrolidin-1-yl)-2-oxoethyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (119);
(R)-5-(5-(1-(2-(3-hydroxypyrrolidin-1-yl)-2-oxoethyl) piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (120);
5-(3-isopropyl-5-(1-(2-oxo-2-(3-oxopyrazolidin-1-yl)ethyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (121);
5-(3-isopropyl-5-(1-(2-oxo-2-(pyrrolidin-1-yl)ethyl) piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (122);
(R)-5-(3-isopropyl-5-(1-(2-oxopyrrolidin-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (123);
2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N-(2-hydroxy-2-methylpropyl)acetamide (124);
(R)-2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N-(2-hydroxypropyl)acetamide (125);
(S)-2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N-(2-hydroxypropyl)acetamide (126);
5-(3-isopropyl-5-(1-(1-methyl-2-oxopyrrolidin-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (127);
2-(4-(3-isopropyl-2-(5-methoxy-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl) piperidin-1-yl)-N,N-dimethylacetamide (128);
2-(4-(3-isopropyl-2-(5-methoxy-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl) piperidin-1-yl)-N-methylacetamide (129);
2-(4-(2-(1-ethyl-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N-methylacetamide (132);
2-(4-(2-(1-ethyl-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N,N-dimethylacetamide (133);
2-(4-(3-isopropyl-2-(1,4,5-trimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl) piperidin-1-yl)-N,N-dimethylacetamide (134);
2-(4-(3-isopropyl-2-(1,4,5-trimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl) piperidin-1-yl)-N-methylacetamide (135);
2-(4-(2-(1-ethyl-4,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N,N-dimethylacetamide (136);
2-(4-(2-(1-ethyl-4,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N-methylacetamide (137);
2-(4-(3-isopropyl-2-(1,2,5-trimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (138);
2-(4-(3-isopropyl-2-(1,2,5-trimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl) piperidin-1-yl)-N-methylacetamide (139);
2-(4-(3-isopropyl-2-(5-methoxy-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N-methylacetamide (140);
2-(4-(3-isopropyl-2-(5-methoxy-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (141);
2-(4-(3-isopropyl-2-(5-methoxy-1,2-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N-methylacetamide (142);
2-(4-(3-isopropyl-2-(5-methoxy-1,2-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (143);
2-(4-(2-(5-cyano-1,2-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N-methylacetamide (144);
2-(4-(2-(5-cyano-1,2-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (145);
2-(4-(2-(5-cyano-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N-methylacetamide (146);
2-(4-(2-(5-cyano-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (147);
2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-2-methylpropanoic acid (148);
5-(3-isopropyl-5-(1-(5-methyl-2-oxotetrahydrofuran-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (149);
2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)acetamide (150);
2-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-2-methylpropanamide (151);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (152);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N-methylacetamide (153);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-2-methylpropanamide (154);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N-ethylacetamide (155);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)propanamide (156);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-ethyl-1H-indol-5-yl) piperidin-1-yl)-N,N-dimethylacetamide (157);
2-(4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (158);
2-(4-(3-isopropyl-2-(1-(2-methoxyethyl)-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (159);
2-(4-(3-isopropyl-2-(1-(2-methoxyethyl)-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N-methylacetamide (160);
2-(4-(2-(1-isobutyl-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N-methylacetamide (161);
2-(4-(2-(1-benzyl-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N-methylacetamide (162);
2-(4-(2-(1-isobutyl-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N,N-dimethylacetamide (163);
2-(4-(2-(1-benzyl-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl) piperidin-1-yl)-N,N-dimethylacetamide (164);
2-(4-(3-isopropyl-2-(5-methyl-6-oxo-1-(2,2,2-trifluoroethyl)-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (165);
2-(4-(2-(1-(2,2-difluoroethyl)-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (166);
2-(4-(2-(1-(2-hydroxyethyl)-5-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (167);
2-(4-(2-(5-ethyl-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (168);
2-(4-(3-isopropyl-2-(1-methyl-2-oxo-1,2-dihydro-[3,3′-bipyridin]-5-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (169);
2-(4-(3-isopropyl-2-(1-methyl-6-oxo-5-phenyl-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (170);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (171);
5-(3-isopropyl-5-(1-(2-(methylamino)ethyl)piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (172);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(piperidin-1-yl) pyridin-2(1H)-one (173);
5-(5-(1-(1-acetylazetidin-3-yl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-chloro-1,4-dimethylpyridin-2(1H)-one (174);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (175);
5-(3-isopropyl-5-(1-(2-(methylamino)ethyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (176);
5-(3-isopropyl-5-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (177);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl) piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (178);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (179);
5-(3-isopropyl-5-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (180);
5-(3-isopropyl-5-(1-methylpiperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (181);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (182);
5-(3-isopropyl-5-(1-((1-methyl-1H-pyrazol-3-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (195);
5-(3-isopropyl-5-(1-((1-methyl-1H-pyrazol-4-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (196);
5-(3-isopropyl-5-(1-((1-methyl-1H-pyrazol-5-yl) methyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (197);
5-(3-isopropyl-5-(1-((1-methyl-1H-1,2,4-triazol-5-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (198);
5-(5-(1-(4,4-difluorocyclohexyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (199);
5-(5-(1-((4H-pyrazol-3-yl)methyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (200);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1-methylpyridin-2(1H)-one (201);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1-methylpyridin-2(1H)-one (202);
1-ethyl-5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (204);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (206);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (207);
1-ethyl-5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-3,4-dimethylpyridin-2(1H)-one (208);
1-ethyl-5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-3,4-dimethylpyridin-2(1H)-one (209);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl) piperidin-4-yl)-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (210);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (211);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (212);
1-ethyl-5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-3,4-dimethylpyridin-2(1H)-one (213);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (214);
5-(3-isopropyl-5-(1-(oxetan-3-yl) piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1,4-dimethylpyridin-2(1H)-one (215);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1,4-dimethylpyridin-2(1H)-one (216);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1,6-dimethylpyridin-2(1H)-one (217);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methoxy-1,6-dimethylpyridin-2(1H)-one (218);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (219);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (220);
5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (221);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (222);
5-(5-(1-(cyclopropylmethyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (223);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (224);
5-(3-isopropyl-5-(1-((tetrahydrofuran-3-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (225);
3-chloro-5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (226);
3-chloro-5-(3-isopropyl-5-(1-((1-isopropyl-1H-pyrazol-4-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (227);
5-(3-isopropyl-5-(1-((1-propyl-1H-pyrazol-4-yl)methyl) piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (228);
N-(4-(4-(2-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidin-1-yl) cyclohexyl)acetamide (229);
5-(3-isopropyl-5-(1-(4-(trifluoromethyl)cyclohexyl) piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (230);
5-(3-isopropyl-5-(1-(4-(trifluoromethyl)cyclohexyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (231);
5-(5-(1-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (232);
5-(3-isopropyl-5-(1-(4-isopropylcyclohexyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (233);
5-(3-isopropyl-5-(1-(4-isopropylcyclohexyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (234);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-[3,3′-bipyridin]-2(1H)-one (235);
5-(5-(1-(2-hydroxyethyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-methyl-[3,3′-bipyridin]-2(1H)-one (236);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1,4-dimethyl-[3,3′-bipyridin]-2(1H)-one (237);
3-chloro-5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (238);
3-chloro-5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (241);
3-chloro-5-(3-isopropyl-5-(1-methylpiperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (240);
5-(5-(1-acetylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-chloro-1,4-dimethylpyridin-2(1H)-one (241);
3-chloro-5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (242);
3-chloro-5-(5-(1-(1,5-dihydroxypentan-3-yl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (243);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (244);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-[3,3′-bipyridin]-2(1H)-one (245);
5-(3-isopropyl-5-(1-methylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl) pyridin-2(1H)-one (246);
5-(3-isopropyl-5-(1-methylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-[3,3′-bipyridin]-2(1H)-one (247);
3-chloro-5-(3-isopropyl-5-(1-(oxetan-3-yl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (248);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (249);
3-chloro-5-(3-isopropyl-5-(1-((tetrahydrofuran-2-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (250);
5-(5-(1-butylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-chloro-1,4-dimethylpyridin-2(1H)-one (251);
3-chloro-5-(3-isopropyl-5-(1-((tetrahydrofuran-3-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (252);
3-chloro-5-(5-(1-(2,3-dihydroxypropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (253);
3-chloro-5-(3-isopropyl-5-(1-((tetrahydrofuran-3-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (254-255);
5-(5-(1-isobutylpiperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (256);
5-(3-isopropyl-5-(1-((tetrahydrofuran-3-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (257);
5-(4-fluoro-3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (258);
5-(4-fluoro-3-isopropyl-5-(1-((tetrahydrofuran-3-yl)methyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (259);
1-ethyl-5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-3-(pyrimidin-5-yl)pyridin-2(1H)-one (260);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-1-(2-methoxyethyl)-3-methylpyridin-2(1H)-one (261);
1-isobutyl-5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (262);
1-benzyl-5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (263);
1-(2-hydroxyethyl)-5-(3-isopropyl-5-(1-methylpiperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (264);
5-(3-isopropyl-5-(1-methylpiperidin-4-yl)-1H-indol-2-yl)-3-methyl-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one (265);
1-(2,2-difluoroethyl)-5-(3-isopropyl-5-(1-methylpiperidin-4-yl)-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (266);
5-(5-(1-(4-(2-hydroxypropan-2-yl)cyclohexyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (267-268);
5-(3-isopropyl-5-(1-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (269);
5-(5-(1-(4-(2-hydroxypropan-2-yl)cyclohexyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (270);
5-(5-(1-(2-(dimethylamino)acetyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (271);
5-(5-(1-(1-aminocyclopropanecarbonyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (272);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (273);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (274);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methoxy-1,6-dimethylpyridin-2(1H)-one (275);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methoxy-1,4-dimethylpyridin-2(1H)-one (276);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-(methoxymethyl)-1-methylpyridin-2(1H)-one (277);
3-chloro-5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (278);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (279);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (280);
5-(5-(1-(dimethylglycyl) piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-ethyl-3,4-dimethylpyridin-2(1H)-one (281);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-ethyl-3-methylpyridin-2(1H)-one (282);
1-benzyl-5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (284);
5-(5-(1-(dimethylglycyl) piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-isobutyl-3-methylpyridin-2(1H)-one (285);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methoxy-1-methylpyridin-2(1H)-one (286);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-(2-methoxyethyl)-3-methylpyridin-2(1H)-one (287);
5-(5-(1-((2R,4S)-4-hydroxypyrrolidine-2-carbonyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (288);
5-(5-(1-((2S,4R)-4-hydroxy-1-methylpyrrolidine-2-carbonyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (289);
5-(5-(1-((2S,4R)-4-hydroxypyrrolidine-2-carbonyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (290);
5-(5-(1-((2S,3S)-3-hydroxypyrrolidine-2-carbonyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (291);
5-(5-(1-((2R,4S)-4-hydroxypyrrolidine-2-carbonyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (292);
5-(5-(1-((2S,4R)-4-hydroxypyrrolidine-2-carbonyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (293);
5-(5-(1-(2-amino-2-methylpropanoyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (296);
5-(3-isopropyl-5-(1-(methyl-L-alanyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (297);
5-(3-isopropyl-5-(1-(2-methyl-2-(methylamino)propanoyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (298);
5-(3-isopropyl-5-(1-(methyl-D-alanyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (299);
5-(3-isopropyl-5-(1-(2-(2-oxopyrrolidin-1-yl)acetyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (300);
5-(5-(1-(dimethylglycyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (301);
3-chloro-5-(3-isopropyl-5-(1-(2,2,2-trifluoroacetyl) piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (302);
5-(5-(1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (303);
5-(5-(1-(3-hydroxy-2,2-dimethylpropanoyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (304);
(S)-5-(5-(1-(3-hydroxybutanoyl) piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (305);
(R)-5-(3-isopropyl-5-(1-(2-(pyrrolidin-2-yl)acetyl)piperidin-4-yl)-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (306);
(S)-1-methylpyrrolidin-3-yl 4-(2-(5-chloro-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidine-1-carboxylate (307);
3-chloro-5-(3-isopropyl-5-(1-((2-(pyrrolidin-1-yl)ethyl)sulfonyl) piperidin-4-yl)-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (308);
3-chloro-5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (309);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (310);
5-(5-(1-((3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (313);
5-(5-(1-((3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (314);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (315);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (316);
5-(5-(1-(2-hydroxy-2-methylpropyl) piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methoxy-1,4-dimethylpyridin-2(1H)-one (317);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methoxy-1,6-dimethylpyridin-2(1H)-one (318);
5-(5-(1-((4-hydroxytetrahydro-2H-pyran-4-yl)methyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,4-trimethylpyridin-2(1H)-one (319);
5-(5-(1-((4-hydroxytetrahydro-2H-pyran-4-yl)methyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3,6-trimethylpyridin-2(1H)-one (320);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (321);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (322);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-(methoxymethyl)-1-methylpyridin-2(1H)-one (323);
5-(5-(1-(2-hydroxy-3-methylbutyl) piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (324);
5-(5-(1-(2-hydroxy-3,3-dimethylbutyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,3-dimethylpyridin-2(1H)-one (325);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-methyl-3-(pyrimidin-5-yl)pyridin-2(1H)-one (326);
3-chloro-5-(4-fluoro-5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1,4-dimethylpyridin-2(1H)-one (327);
5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-1-isobutyl-3-methylpyridin-2(1H)-one (328);
1-benzyl-5-(5-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)-3-isopropyl-1H-indol-2-yl)-3-methylpyridin-2(1H)-one (329);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-6′-morpholino-[3,3′-bipyridin]-2(1H)-one (330);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-3-(2-methoxypyrimidin-5-yl)-1-methylpyridin-2(1H)-one (331);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1,5′-dimethyl-[3,3′-bipyridin]-2(1H)-one (332);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1,4-dimethyl-3-(1-methyl-1H-pyrazol-4-yl)pyridin-2(1H)-one (333);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(1-methyl-1H-pyrazol-4-yl) pyridin-2(1H)-one (334);
N-(5′-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1′-methyl-2′-oxo-1′,2′-dihydro-[3,3′-bipyridin]-6-yl)acetamide (335);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-[3,4′-bipyridin]-2(1H)-one (336);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(2-methylpyrimidin-5-yl)pyridin-2(1H)-one (337);
3-(2-cyclopropylpyrimidin-5-yl)-5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methylpyridin-2(1H)-one (338);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(2-(trifluoromethyl)pyrimidin-5-yl) pyridin-2(1H)-one (339);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-3-(3-methoxyphenyl)-1-methylpyridin-2(1H)-one (340);
6′-fluoro-5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-[3,3′-bipyridin]-2(1H)-one (341);
6′-fluoro-5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1-methyl-[3,3′-bipyridin]-2(1H)-one (342);
6′-fluoro-5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1,5′-dimethyl-[3,3′-bipyridin]-2(1H)-one (343);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-1,2′-dimethyl-[3,3′-bipyridin]-2(1H)-one (244);
5-(3-isopropyl-5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-1H-indol-2-yl)-3-(methoxymethyl)-1-methylpyridin-2(1H)-one (345);
5-(3-isopropyl-5-(1-(oxetan-3-yl) piperidin-4-yl)-1H-indol-2-yl)-3-(methoxymethyl)-1-methylpyridin-2(1H)-one (346);
5-(3-isopropyl-5-(1-isopropylpiperidin-4-yl)-1H-indol-2-yl)-3-(methoxymethyl)-1-methylpyridin-2(1H)-one (347);
5-(3-isopropyl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl)-3-(methoxymethyl)-1-methylpyridin-2(1H)-one (348);
5-(3-isopropyl-5-(1-(2-methoxyethyl)piperidin-4-yl)-1H-indol-2-yl)-1,6′-dimethyl-[3,3′-bipyridin]-2(1H)-one (349);
5-(3-isopropyl-5-(1-(2-methoxyethyl)piperidin-4-yl)-1H-indol-2-yl)-1-methyl-3-(1-methyl-1H-pyrazol-4-yl)pyridin-2(1H)-one (350);
2-(4-(3-isopropyl-2-(5-(methoxymethyl)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (351);
2-(4-(3-isopropyl-2-(1-methyl-6-oxo-5-vinyl-1,6-dihydropyridin-3-yl)-1H-indol-5-yl)piperidin-1-yl)-N,N-dimethylacetamide (352);
and
5-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-3-(methoxymethyl)-1-methylpyridin-2(1H)-one (353).

315 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/635,593Filed 3 Aug 2018 · us provisional application
Priority: 4 Aug 2017
Published: US 2020/0239437 A130 Jul 2020
Granted: 20 Sep 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
A61P 37/00
Drugs for immunological or allergic disorders
C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…

Family

Application62/541,335Us provisional application · filed 4 Aug 2017
US 2020/0239437 A1Pre-grant publication · published 30 Jul 2020
US 11,447,466 B2This patent

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

Timeline

Citations

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Abstract

A compound of Formula (I)

or a salt thereof, wherein:
Y is
R1 is —CH2CH3 or —CH(CH3)2;
R2 is —CH3, —CH2CH3, —CH(CH3)2, —CH2CH(CH3)2, —CH2CH2OH, —CH2CH2CH2OH, —CH2C(CH3)2OH, —CH2CHF2, —CH2CF3, —CH2CH2OCH3, —CH2(cyclopropyl), —CH2(phenyl), —CH2C(O)NH2, tetrahydrofuranyl, or phenyl;
each R2a is independently H, F, Cl, —CN, —NH2, C1-5 alkyl, —CF3, —CH2OH, —OCH3, —CH2OCH3, —CH2CH2(cyclopropyl), —C(O)OCH3, —C(O)N(CH3)2, —C(O)NH(CH2CH2CH3), —CH═CH2, —C(CH3)═CH2, —CH═CH(cyclopropyl), —C(O)(pyrrolidinyl), or a cyclic group selected from pyrrolidinyl, pyrazolyl, phenyl, pyridinyl, and pyrimidinyl, each substituted with zero, 1, or 2 Ry;
each Ry is independently F, —CN, —CH3, —CF3, —OCH3, —NHC(O)CH3, —C(O)NH2, —C(O)NH(CH3), cyclopropyl, or morpholinyl;
R3 is H, —CH3, —CH2CH2CH3, —CH(CH3)2, —CH2CH2CH2CH3, —CH2CH(CH3)2, —CH2CH2CH(CH3)2, —CH2CH2CF3, —CH2CH2CH2CF3, —CH2CH2CH(CF3)2, —CH2CH2OH, —CH2CH2CH2OH, —C(CH3)2OH, —CH2C(CH3)2OH, —CH2CH2C(CH3)2OH, —CH2CH(OH)CH(CH3)2, —CH2CH(OH)CH2OH, —CH(CH2CH2OH)2, —CH2CN, —CH2CH2CN, —CH2CH2OCH3, —CH2CH2CH2OCH3, —(CH2CH2O)2-3OCH3, —CH2CH2NH(CH3), —C(CH3)2C(O)OH, —CH2C(O)NH2, —CH2C(O)NH(CH3), —CH2C(O)N(CH3)2, —CH2C(O)NH(CH2CH3), —CH2C(O)NH(CH2CH(CH3)OH), —CH2C(O)NH(CH2C(CH3)2OH), —CH(CH3)C(O)NH2, —C(CH3)2C(O)NH2, —CH2CH2C(O)NH2, —CH2CH2S(O)2CH3, —C(O)CH3, —C(O)CF3, —C(O)CH2N(CH3)2, —C(O)C(CH3)2NH2, —C(O)CH(CH3)NH(CH3), —C(O)C(CH3)2NH(CH3), —C(O)CH2CH(CH3)OH, —C(O)CH2C(CH3)2OH, —C(O)C(CH3)2CH2OH, —NHC(O)CH3, —CH2(methyl triazolyl), —CH2(trifluoromethyl phenyl), —CH2(difluoromethyl, fluorophenyl), —CH2(fluoro, chlorophenyl), —CH2(difluorocyclopropyl), —CH2CH2(pyrrolidin-dionyl), —CH2(oxetanyl), —CH2(tetrahydropyranyl), —CH2C(O)(hydroxypyrrolidinyl), —CH2C(O)(pyrazolidinonyl), —CH2C(O)(pyrrolidinyl), —CH2(dimethyl pyrazolyl), —CH2(methyl pyrazolyl), —CH2(pyrazolyl), —CH2(cyclopropyl), —CH2(tetrahydrofuranyl), —CH2(i-propyl pyrazolyl), —CH2(n-propyl pyrazolyl), —CH(CH3)(methyl pyrazolyl), —C(O)(aminocyclopropyl), —C(O)(hydroxypyrrolidinyl), —C(O)(methyl, hydroxypyrrolidinyl), —C(O)CH2(pyrrolidinonyl), —C(O)CH2(pyrrolidinyl), —C(O)O(methyl pyrrolidinyl), —S(O)2CH2CH2(pyrrolidinyl), —CH2(hydroxytetrahydropyranyl), or a cyclic group selected from cyclopentyl, cyclohexyl, oxetanyl, azetidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydrofuranonyl, tetrahydropyranyl, piperidinyl, and dioxotetrahydrothiophenyl, each substituted with zero, 1, or 2 R3a;
each R3a is independently F, —OH, —CH3, —CH(CH3)2, —CF3, or —C(O)NH2;
R5 is F;
m is zero;
and
n is zero or 1.

9 more elements

Facts

Application

16/635,593Filed 3 Aug 2018 · us provisional application

Priority

4 Aug 2017

Published

US 2020/0239437 A130 Jul 2020

Granted

20 Sep 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
A61P 37/00
Drugs for immunological or allergic disorders
C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…