Inhibitors of KRAS G12C mutant proteins

A compound having one of the following structures (Ia′), (Ib′), (Ic′), (Id′), (Ie′), (If′) or (Ig′):

• or a pharmaceutically acceptable salt, tautomer, stereoisomer or prodrug thereof, wherein:
• X is NH or O when L2 is a bond or alkylene optionally substituted with C1-C6 alkyl or oxo;
• or X is absent when L2 is alkylene optionally substituted with C1—C alkyl;
• G1, G2, G3 and G4 are each independently N or CR, where R is H, cyano, halo or C1-C6 alkyl;
• R1 is halo, hydroxyl, cyano, aminocarbonyl, formyl, C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 hydroxylalkyl, C1-C6 alkoxyalkyl, C1-C6 aminoalkyl, heterocyclyl, heteroaryl or aryl;
• R2 is H, halo, hydroxyl, cyano, aminocarbonyl, formyl, C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 hydroxylalkyl, C1-C6 alkoxyalkyl, C1-C6 aminoalkyl, heterocyclyl, heteroaryl or aryl;
• R3a and R3b are, at each occurrence, independently H, —OH, —NH, —CO2H, halo, cyano, C1-C6 alkyl, C1-C6 alkynyl, hydroxylalkyl, aminylalkyl, alkylaminylalkyl, cyanoalkyl, carboxyalkyl, aminocarbonylalkyl or aminocarbonyl;
• or one R3a and one R3b join to form a carbocyclic or heterocyclic ring, and each remaining R3a and R3b are, at each occurrence, independently H, —OH, —NH, —CO2H, halo, cyano, C1-C6 alkyl, C1-C6 alkynyl, hydroxylalkyl, aminylalkyl, alkylaminylalkyl, cyanoalkyl, carboxyalkyl, aminocarbonylalkyl or aminocarbonyl, or one R3b joins with one R4b to form a carbocyclic or heterocyclic ring, and each R3a and each remaining R3b are, at each occurrence, independently H, —OH, —NH2, —CO2H, halo, cyano, C1-C6 alkyl, C1-C6 alkynyl, hydroxylalkyl, aminylalkyl, alkylaminylalkyl, cyanoalkyl, carboxyalkyl, aminylcarbonylalkyl or aminylcarbonyl;
• R4a and R4b are, at each occurrence, independently H, —OH, —NH, —CO2H, halo, cyano, C1-C6 alkyl, C1-C6 alkynyl, hydroxylalkyl, aminylalkyl, alkylaminylalkyl, cyanoalkyl, carboxyalkyl, aminocarbonylalkyl or aminocarbonyl;
• or one R4a and one R4b join to form a carbocyclic or heterocyclic ring, and each remaining R4a and R4b are, at each occurrence, independently H, —OH, —NH, —CO2H, halo, cyano, C1-C6 alkyl, C1-C6 alkynyl, hydroxylalkyl, aminylalkyl, alkylaminylalkyl, cyanoalkyl, carboxyalkyl, aminocarbonylalkyl or aminocarbonyl;
• or one R4b joins with one R3b to form a carbocyclic or heterocyclic ring, and each R4a and each remaining R4b are, at each occurrence, independently H, —OH, —NH2, —CO2H, halo, cyano, C1-C6 alkyl, C2-C6 alkynyl, hydroxylalkyl, aminylalkyl, alkylaminylalkyl, cyanoalkyl, carboxyalkyl, aminylcarbonylalkyl or aminylcarbonyl;
• L1 is a bond or alkylene;
• L2 is a bond or an alkylene optionally substituted C1-C6 alkyl or oxo when X is NH or O;
• or L2 is alkylene optionally substituted with C1-C6 alkyl when X is absent;
• m1, m2, m3 and m4 are each independently 1, 2 or 3;
• represents a double or triple bond;
• Q is —C(═O)—, —C(═NR7)—, —NR8C(═O)—, —S(═O)2— or —NR8S(═O)2—;
• R7 is H, —OH, —CN or C1-C6alkyl;
• R8 is H, C1-C6 alkyl or hydroxylalkyl;
• when is a double bond then R9 and R10 are each independently H, cyano, carboxyl, C1-C6 alkyl, alkoxycarbonyl, aminylalkyl, alkylaminylalkyl, heteroaryl or hydroxylalkyl or R9 and R10 join to form a carbocyclic or heterocyclic ring;
• and when is a triple bond then R9 is absent and R10 is H, aminylalkyl, alkylaminylalkyl or hydroxylalkyl.