Patent ID: 11858931
Assignee: PLIANT THERAPEUTICS, INC.
Field: Organic fine chemistry (Chemistry)
Classification: CPC C  A | IPC C

Claim 0:
1. A method of treating a fibrotic disease in an individual in need thereof comprising administering to the individual a compound of formula (A):, , or a pharmaceutically acceptable salt thereof, wherein:
R1 is hydrogen;
R2 is 5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl optionally substituted by R12;
G is —C(O)R3;
R3 is tetrahydropyranyl optionally substituted by R3f;
R5a, R5b, R6a, R6b, R7a, R7b, R8a, R8b, R9a, R9b, R10a, and R19b are each independently hydrogen, deuterium, or halogen;
each R11a and R11b are independently hydrogen, deuterium, or halogen;
n is 0, 1, or 2;
each R3f is independently oxo or R12;
each R12 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C6-C14 aryl, halogen, deuterium, —CN, —OR13, —SR13, —NR14R15, —NO2, —C═NH(OR13), —C(O)R13, —OC(O)R13, —C(O)OR13, —C(O)NR14R15, —NR13C(O)R14, —NR13C(O)OR14, —NR13C(O)NR14R15, —S(O)R13, —S(O)2R13, —NR13S(O)R14, —NR13S(O)2R14, —S(O)NR14R15, —S(O)2NR14R15, or —P(O)(OR13)(OR14), wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, and C6-C14 aryl of R12 are independently optionally substituted by R12a;
each R12a is independently deuterium, halogen, oxo, —OR16, —NR16R17, —C(O)R16, —C(O)OR16, —NR16C(O)OR18, —CN, —S(O)R16, —S(O)2R16, —P(O)(OR16)(OR7), C3-C8 cycloalkyl, C6-C14 aryl, or C1-C6 alkyl, wherein the C6-C14 aryl, and C1-C6 alkyl of R12a are independently optionally substituted by R12b;
each R12b is independently deuterium, oxo, —OH, halogen, or C1-C6 alkyl;
each R13 is independently hydrogen, deuterium, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C6-C14 aryl, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C6-C14 aryl of R13 are each independently optionally substituted by R13a;
each R13a is independently halogen, deuterium, oxo, —CN, —OR18, —NR19R20, —P(O)(OR19)(OR20), or C1-C6 alkyl optionally substituted by deuterium, halogen, —OH, or oxo;
each R14 is independently hydrogen, deuterium, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C6-C14 aryl, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C6-C14 aryl of R14 are independently optionally substituted by deuterium, halogen, oxo, —CN, —OR18, —NR19R20, or C1-C6 alkyl optionally substituted by deuterium, halogen, —OH, or oxo;
each R15 is independently hydrogen, deuterium, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C6-C14 aryl, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C6-C14 aryl of R15 are independently optionally substituted by deuterium, halogen, oxo, —CN, —OR18, —NR19R20, or C1-C6 alkyl optionally substituted by deuterium, halogen, —OH, or oxo;
each R16 is independently hydrogen, deuterium, C1-C6 alkyl optionally substituted by deuterium, halogen, or oxo, C2-C6 alkenyl optionally substituted by deuterium, halogen, or oxo, or C2-C6 alkynyl optionally substituted by deuterium, halogen, or oxo;
each R17 is independently hydrogen, deuterium, C1-C6 alkyl optionally substituted by deuterium, halogen, or oxo, C2-C6 alkenyl optionally substituted by deuterium, halogen, or oxo, or C2-C6 alkynyl optionally substituted by deuterium, halogen, or oxo;
each R18 is independently hydrogen, deuterium, C1-C6 alkyl optionally substituted by deuterium, halogen, or oxo, C2-C6 alkenyl optionally substituted by deuterium, halogen, or oxo, or C2-C6 alkynyl optionally substituted by deuterium, halogen, or oxo;
each R19 is independently hydrogen, deuterium, C1-C6 alkyl optionally substituted by deuterium, halogen, or oxo, C2-C6 alkenyl optionally substituted by deuterium, halogen, or oxo, or C2-C6 alkynyl optionally substituted by deuterium, halogen, or oxo;
each R20 is independently hydrogen, deuterium, C1-C6 alkyl optionally substituted by deuterium, halogen, or oxo, C2-C6 alkenyl optionally substituted by deuterium, halogen, or oxo, or C2-C6 alkynyl optionally substituted by deuterium, halogen, or oxo; and
R21 is hydrogen, deuterium, C1-C6 alkyl optionally substituted by deuterium, halogen, or oxo, C2-C6 alkenyl optionally substituted by deuterium, halogen, or oxo, or C3-C6 cycloalkyl optionally substituted by deuterium, halogen, or oxo.