Patent ID: 11878976
Assignee: ELI LILLY AND COMPANY
Field: Organic fine chemistry (Chemistry)
Classification: CPC C  A | IPC C

Claim 0:
1. A compound of the formula:, wherein
A is pyrazole, triazole, thiadiazole or oxadiazole, substituted with R1 and R1A;
R1 is hydrogen or C1-C3 alkyl;
R1A is hydrogen, halo, CN, or C1-C3 alkyl optionally substituted with one or more substituents independently selected from halo, OH, and OCH3;
X1 and X2 are independently selected from N and C, wherein when one of X1 or X2 is N the other is C;
X3 is N or CH;
X4 is N or C—R9;
Y is NH, O, S or a bond;
Y1 is a bond, CHR7, CH2—CHR7, CHR7—CH2, CF2, CH2—CF2 or CF2—CH2;
Y2 is a bond, CHR3, CH2—CHR3, CHR3—CH2, CF2, CH2—CF2 or CF2—CH2;
Y3 is CR4R5 or CF2;
Y4 is CR3R4, or CF2;
Z is a bond, CHR9A, CR4R4A, CR4R4A—CH2, CH2—CR4R4A, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo(1.1.1)pentane, bicyclo(2.1.1)hexane, azetidine, pyrrolidine or piperidine;
Z1 is a bond when Z is a bond, CR4R4A, CR4R4A—CH2, CH2—CR4R4A, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo(1.1.1)pentane, bicyclo(2.1.1)hexane, azetidine, pyrrolidine or piperidine, or Z1 is CH2 or CH2—CH2 when Z is CHR9A;
Z2 is a bond, C(O), SO2 or —NR4C(O);
Z3 is a bond, C(O), SO2 or —NR4C(O);
R2 is C1-C5 alkyl or R8, wherein C1-C5 alkyl is optionally substituted with one or more substituents independently selected from halo, OH, CN, oxo, —OC1—C4 alkyl, —OC3—C5 cycloalkyl, —Z2—R11 and R10, wherein C1-C4 alky and C3-C5 cycloalkyl are optionally substituted with one or more substituents independently selected from halo, OH, OCH3, methylamine, N,N-dimethylamine and CN;
R3 is hydrogen, F, OH, OCH3, C1-C3 alkyl, cyclopropyl, or one R3 is fused with R5 or R7 to form CH2, CH2—CH2 or CH2OCH2;
R4 is hydrogen or C1-C3 alkyl;
R4A is hydrogen, halo, OH, or C1-C3 alkyl;
R5 is hydrogen, F, OH, OCH3, C1-C3 alkyl, cyclopropyl, or is fused with one R3 to form CH2, CH2—CH2 or CH2OCH2;
R6 is hydrogen, halo, C1-C5 alkyl, CN, 3-6 membered cycloalkyl, 4-6 membered heterocycloalkyl, 5-6 membered aryl or 5-6 membered heteroaryl, wherein 3-6 membered cycloalkyl, 4-6 membered heterocycloalkyl, 5-6 membered aryl and 5-6 membered heteroaryl are optionally substituted with one or more substituents independently selected from halo, methyl, halomethyl, OH or OCH3 and wherein C1-C5 alkyl is optionally substituted with one or more substituents independently selected from halo, OH and OCH3;
R7 is hydrogen, F, OH, OCH3, C1-C3 alkyl or is fused with one R3 to form CH2, CH2—CH2 or CH2OCH2;
R8 is 3-6 membered cycloalkyl, 4-6 membered heterocycloalkyl, 5-6 membered aryl or 5-6 membered heteroaryl, optionally fused or substituted with R8A;
R8A is 3-6 membered cycloalkyl, 4-6 membered heterocycloalkyl, 5-6 membered aryl or 5-6 membered heteroaryl;
R9 is hydrogen, C1-C3 alkyl, or is fused with R9A to form CH2 or CH2—CH2;
R10 is 3-6 membered cycloalkyl, 4-6 membered heterocycloalkyl, 5-6 membered aryl or 5-6 membered heteroaryl, optionally fused or substituted with R8A;
R11 is C1-C4 alkyl, NH2, NHC1—C3 alkyl, NHC3-C5 cycloalkyl or N(C1-C3 alkyl)2, wherein C1-C4 alkyl, C1-C3 alkyl and C3-C5 cycloalkyl are optionally substituted with one or more substituents independently selected from halo, OH, OCH3, methylamine, N,N-dimethylamine and CN;
R12 is C1-C4 alkyl, C3-C5 cycloalkyl, NH2, NHC1—C3 alkyl, NHC3-C5 cycloalkyl or N(C1-C3 alkyl)2, wherein C1-C4 alky, C1-C3 alkyl and C3-C5 cycloalkyl are optionally substituted with one or more substituents independently selected from halo, OH, OCH3, methylamine, N,N-dimethylamine and CN; and
R8, R10 and R8A are optionally substituted with one or more substituents independently selected from halo, OH, CN, —OC1—C4 alkyl, —OC3—C5 cycloalkyl and —Z3—R12 wherein C1-C4 alky and C3-C5 cycloalkyl are optionally substituted with one or more substituents independently selected from halo, OH, OCH3, methylamine, N,N-dimethylamine and CN;
or a pharmaceutically acceptable salt thereof.