Heteroaryl compounds as btk inhibitors and uses thereof

A compound of formula I,

• or a tautomer, or a pharmaceutically acceptable salt thereof, wherein:
• Ring A is a 5-6-membered aryl or heteroaryl;
• R1 is H, halo, (C(R5)(R5))mNR2, N(R4)C(O)R, N(R4)C(O)NR2, N(R4)CO2R, N(R4)S(O)2R, N(R4)S(O)R, N(R4)(R4), optionally substituted 3-7-membered heterocylic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or optionally substituted 5-6-membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
• or R1 is absent;
• R2 is H, (C(R5)(R5))mOR4, (C(R5)(R5))mN(R4)COR, (C(R5)(R5))mN(R4)C(O)C(O)NR2, (C(R5)(R5))mN(R4)(R4), optionally substituted 3-7-membered heterocylic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or optionally substituted 5-6-membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
• or R2 is absent;
• or R1 and R2 together with the atoms to which they are connected, form a fused 3-7-membered ring which is optionally substituted;
• wherein R1 and R2 are both not H;
• and wherein R1 and R2 are both not absent;
• each R3 is independently halogen, C1-6 aliphatic, C5-10 aryl, a 3-8-membered saturated or partially unsaturated carbocyclic ring, a 3-7-membered heterocylic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or a 5-6-membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
• each of which is optionally substituted;
• each R4 is independently —R, —SO2R, —SOR, —C(O)R, —CO2R, or —C(O)N(R)2;
• each R5 is independently —R, halogen, —OR, —SR, —CN, —NO2, —SO2R, —SOR, —C(O)R, —CO2R, —C(O)N(R)2, —NRC(O)R, —NRC(O)N(R)2, —NRSO2R, or —N(R)2;
• each R is independently hydrogen, C1-6 aliphatic, C5-10 aryl, a 3-8-membered saturated or partially unsaturated carbocyclic ring, a 3-7-membered heterocylic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or a 5-6-membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
• each of which is optionally substituted;
• or
• two R groups on the same atom are taken together with the atom to which they are attached to form a C5-10 aryl, a 3-8-membered saturated or partially unsaturated carbocyclic ring, a 3-7 membered heterocylic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 5-6-membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
• a 10-15-membered fused aryl ring;
• a 6-15-membered saturated or partially unsaturated fused carbocyclic ring;
• a 10-15-membered fused heteroaryl ring;
• or a 6-15-membered saturated or partially unsaturated fused heterocyclic ring;
• each of which is optionally substituted;
• Ring Z is C5-10 aryl, a 3-8-membered saturated or partially unsaturated carbocyclic ring, a 3-7 membered heterocylic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or a 5-6-membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
• each of which is optionally substituted;
• or Ring Z is absent;
• each Ra is independently —R, halogen, —OR, —SR, —CN, —NO2, —SO2R, —SOR, —C(O)R, —CO2R, —C(O)N(R)2, —NRC(O)R, —NRC(O)N(R)2, —NRSO2R, or —N(R)2;
• m is 1, 2, or 3;
• n is 0, 1, or 2;
• and
• p is 0, 1, 2, or 3.