PIKfyve kinase inhibitors

A compound of the formula (XIII):

• or a tautomer or pharmaceutically acceptable salt thereof, wherein
• each occurrence of R2 is, independently, hydrogen, nitro, cyano, hydroxyl, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted carboxy, substituted or unsubstituted mercaptane, or substituted or unsubstituted heterocyclyl;
• R3 is a nitrogen- and/or oxygen-containing moiety;
• each occurrence of R4 is, independently, hydrogen, nitro, hydroxyl, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted carboxy, substituted or unsubstituted mercaptane, or substituted or unsubstituted heterocyclyl;
• L1 is absent, C1-C4 alkylene, —NRc—, —O—, —S—, —C(O)—, —NRcC(O)—, —C(O)NRc—, or —NRcC(O)(CRaRb)m—;
• -L2-R is
• L3 is absent, optionally substituted C1-C7 alkylene, —NRc—, —O—, —S—, —C(O)—, —NRcC(O)—, —C(O)NRc—, —NRcC(O)—, or —NRcC(O)(CRaRb)m—;
• X is N or CRc;
• Ring A is (i) a 5 or 6-membered heteroaryl, a 5-6, 6-5 or 6-6 membered bicyclic heteroaryl, or a heterocyclyl, each having at least one nitrogen or oxygen ring atom, or (ii) aryl;
• Ring B is absent, or (i) a 5 or 6-membered heteroaryl, a 5-6, 6-5 or 6-6 membered bicyclic heteroaryl or a heterocyclyl, each having at least one nitrogen, oxygen or sulfur ring atom, or (ii) aryl;
• each occurrence of Ra and Rb are independently hydrogen, hydroxy, hydroxy(C1-4)alkyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl, halogen, nitro, —ORd, —SRd, —NRdRe, —C(O)Rd, —C(S)Rd, —OC(O)Rd, —SC(O)Rd, OC(S)Rd, SC(S)Rd, —NRcC(O)Rd, —NRcC(S)Rd, —SO2Rc, —S(O)Re, —NRcSO2Rd, —OS(O)2Rd, —OP(O)RdRc, or —P(O)RdRe;
• Rc is hydrogen or C1-6 alkyl;
• each occurrence of Rd and Rc are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl;
• each occurrence of m is independently 0, 1, 2, 3, 4, 5, 6 or 7;
• p is 0, 1, 2, 3 or 4;
• and
• q is 0, 1, or 2.

A compound of the formula (XIII-A):

• or a tautomer or pharmaceutically acceptable salt thereof, wherein
• Ring A is a 5 or 6-membered heteroaryl, a 5-6, 6-5 or 6-6 membered bicyclic heteroaryl, or a heterocyclyl, each having at least one nitrogen or oxygen ring atom;
• Ring B is (i) a 5 or 6-membered heteroaryl, a 5-6, 6-5 or 6-6 membered bicyclic heteroaryl or a heterocyclyl, each having at least one nitrogen, oxygen or sulfur ring atom, or (ii) aryl;
• each occurrence of R2 is, independently, hydrogen, nitro, cyano, hydroxyl, halogen, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted carboxy, substituted or unsubstituted mercaptane, or substituted or unsubstituted heterocyclyl;
• each occurrence of R4 is, independently, hydrogen, nitro, hydroxyl, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted carboxy, substituted or unsubstituted mercaptane, or substituted or unsubstituted heterocyclyl;
• -L2-R′ is
• L3 is absent, optionally substituted C1-C7 alkylene, —NRc—, —O—, —S—, —C(O)—, —NRcC(O)—, —C(O)NRc—, —NRcC(O)—, or —NRcC(O)(CRaRb)m—;
• each occurrence of Ra and Rb are independently hydrogen, hydroxy, hydroxy(C1-4)alkyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl, halogen, nitro, —ORd, —SRd, —NRdRe, —C(O)Rd, —C(S)Rd, —OC(O)Rd, —SC(O)Rd, OC(S)Rd, SC(S)Rd, —NRcC(O)Rd, —NRcC(S)Rd, —SO2Rc, —S(O)Re, —NRcSO2Rd, —OS(O)2Rd, —OP(O)RdRc, or —P(O)RdRe;
• Rc is hydrogen or C1-6 alkyl;
• each occurrence of Rd and Rc are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocyclyl;
• m is 0, 1, 2, 3, 4, 5, 6 or 7;
• p is 0, 1, 2, 3 or 4;
• and
• q is 0, 1, or 2.

A compound of the formula (XVII):

• or a tautomer or pharmaceutically acceptable salt thereof, wherein
• R1 is
• wherein R3 is C1-6 alkyl, optionally containing one or more heteroatoms, and A is —CH2—, —CHMe-, —C(Me2)-, —O—, —S—, —NH—, or —N(C1-4 alkyl)-;
• and
• R2 is