Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors

An enantiomerically pure compound of formula 1

• wherein:
• Y is CR12;
• R1 is 5-12 membered heteroaryl;
• and each hydrogen in R1 is optionally replaced by one or more R3 groups;
• R2 is hydrogen;
• each R3 is independently halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-12 cycloalkyl, C6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, —S(O)mR4, —SO2NR4R5, —S(O)2OR4, —NO2, —NR4R5, —(CR6R7)nOR4, —CN, —C(O)R4, —OC(O)R4, —O(CR6R7)nR4, —NR4C(O)R5, —(CR6R7)nC(O)OR4, —(CR6R7)nC(O)NR4R5, —(CR6R7)nNCR4R5, —C(═NR6)NR4R5, —NR4C(O)NR5R6, or —NR4S(O)pR5, each hydrogen in R3 is optionally replaced by R8, and R3 groups on adjacent atoms may combine to form a C6-12 aryl, 5-12 membered heteroaryl, C3-12 cycloalkyl or 3-12 membered heteroalicyclic group;
• each R4, R5, R6 and R7 is independently hydrogen, halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-12 cycloalkyl, C6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl;
• or any two of R4, R5, R6 and R7 bound to the same nitrogen atom may, together with the nitrogen to which they are bound, be combined to form a 3 to 12 membered heteroalicyclic or 5-12 membered heteroaryl group optionally containing 1 to 3 additional heteroatoms selected from N, O, and S;
• or any two of R4, R5, R6 and R7 bound to the same carbon atom may be combined to form a C3-12 cycloalkyl, C6-12 aryl, 3-12 membered heteroalicyclic or 5-12 membered heteroaryl group;
• and each hydrogen in R4, R5, R6 and R7 is optionally replaced by R8;
• each R8 is independently halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-12 cycloalkyl, C6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, —NH2, —CN, —OH, —O—C1-12 alkyl, —O—(CH2)nC3-12 cycloalkyl, —O—(CH2)nC6-12 aryl, —O—(CH2)n(3-12 membered heteroalicyclic) or —O—(CH2)n(5-12 membered heteroaryl);
• and each hydrogen in R8 is optionally replaced by R11;
• each R11 is independently halogen, C1-12 alkyl, C3-12 cycloalkyl, C6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, —O—C1-12 alkyl, —O—(CH2)nC3-12 cycloalkyl, —O—(CH2)nC6-12 aryl, —O—(CH2)n(3-12 membered heteroalicyclic), —O—(CH2)n(5-12 membered heteroaryl) or —CN, and each hydrogen in R11 is optionally substituted by halogen, —OH, —CN, —C1-12 alkyl which may be partially or fully halogenated, or —O—C1-12 alkyl which may be partially or fully halogenated;
• R12 is hydrogen;
• each m is independently 0, 1 or 2;
• each n is independently 0, 1, 2, 3 or 4;
• and
• each p is independently 1 or 2;
• or a pharmaceutically acceptable salt thereof.