Pyrrolopyrimidine nucleosides and analogs thereof

A compound of Formula IA:

• or a pharmaceutically acceptable salt, solvate, enantiomer, diastereomer, racemate or mixture thereof, wherein:
• A is:
• X1 is —CR11R12— or —OCH2CH2— wherein the oxygen atom is distal to the RIA moiety in A;
• R11 and R12 are independently hydrogen or C1-C4 alkyl, wherein the alkyl is optionally substituted with one or more halogen, —OH, —SH, or —NH2;
• X2 is absent, —O—, —C(O)O—, or —OCH2— wherein the oxygen atom is distal to the RIA moiety in A;
• X3 is independently —O— or —NH—;
• B is independently —C(O)NH2, aryl, or heteroaryl;
• C is independently —OR, —NHR, or —N═CHN(R)2;
• each RIA is independently is hydrogen, —C1-C6 alkyl, wherein the alkyl is optionally substituted with one or more —OH, —SH, or —NH2, oxo, Ra, or —ORa, or
• or RIA is an amino acid residue bound via the carbonyl group;
• v is 0 or 1;
• n is 0, 1, 2, or 3 and when X2 is —C(O)O—, n is 0;
• p is 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11;
• q is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18;
• Rz is hydrogen, halogen, —C1-C4 alkylthio, —C1-C4 alkoxy, —C1-C4 alkyl, —C2-C4 alkenyl, —C2-C4 alkynyl, aryl, heteroaryl, —C3-C8 cycloalkyl, —C4-C8 cycloalkenyl, or 3- to 5-membered nonaromatic heterocycle, wherein each alkylthio, alkoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl,or heterocycle is optionally substituted with one or more halogen, —OH, —SH, or —NH2;
• Ra, Rb, Rx, and Ry are each independently selected from the group consisting of hydrogen, halogen, —OH, —SH, —C1-C6 alkoxy, aryloxy, —C1-C6 alkylthio, arylthio, —OC(O)C1-C6 alkyl, —OC(O)aryl, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, aryl, heteroaryl, —C3-C8 cycloalkyl, and —C4-C8 cycloaklenyl, wherein each alkoxy, aryloxy, alkylthio, arylthio, alkyl, aryl, alkenyl, alkynyl, heteroaryl, cycloalkyl, or cycloalkenyl is optionally substituted with one or more halogen, —OR11, —SR11, or —NR11R12;
• or any two Ra or Rb, together with the atom to which they are both attached, can combine to form a C3-C8 spirocycloalkyl or 3- to 8-membered spiroheterocycle;
• or any two Ra or Rb, when on adjacent atoms, can combine to form a cis- or trans-carbon-carbon double bond or a carbon-carbon triple bond;
• or any two Ra or Rb, when on adjacent atoms, can combine to form an oxo, aryl, heteroaryl, —C3-C10cycloalkyl, —C4-C10cycloalkenyl, or 5-to 10-membered ring heterocycle;
• or any CRaRb can be replaced by —O—, —S—, —S(O)—, or —SO2—;
• or any two Rx or Ry, together with the atom to which they are both attached, can combine to form a —C3-C8 spirocycloalkyl or 3- to 8-membered spiroheterocycle;
• or any two Rx or Ry, when on adjacent atoms, can combine to form a cis- or trans-carbon-carbon double bond or a carbon-carbon triple bond;
• or any two Rx or Ry, when on adjacent atoms, can combine to form an oxo, aryl, heteroaryl, —C3-C10cycloalkyl, —C4-C10cycloalkenyl, or 5-to 10-membered ring heterocycle;
• or any CRxRy can be replaced by —O—, —S—, —S(O)—, or —SO2—;
• R1 and R45 are each independently hydrogen, halogen, —N3, —OH, —NH2, —SH, —C1-C6 alkyl, —C3-C6 cycloalkyl, —C2-C6 alkenyl, —C4-C8 cycloalkenyl, —C2-C6 alkynyl, —C8-C12 cycloalkynyl, —C1-C6 alkoxy, or —C1-C6 alkylthio wherein each alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkoxy or alkylthio is independently substituted with one or more halogen, —N3, —OH, —NH2, or —SH;
• R2, R3, R4 and R44 are each independently hydrogen, halogen, —N3, —OH, —NH2, —SH, —C1-C6 alkyl, —C1-C6 alkoxy, or —C1-C6 alkylthio, wherein each alkyl, alkoxy, or alkylthio is optionally substituted with one or more halogen, oxo, —N3, —OH, —NH2, or —SH;
• or R3 and one of R4 and R44, together with the atoms to which they are attached, can form a carbon-carbon double bond;
• or R3 and one of R4 and R44, together with the atoms to which they are attached, can combine to form a 4- to 8-membered cycloalkyl or heterocycle optionally substituted with C1-C6 alkyl;
• R5 is independently hydrogen, —RIA, M+, aryl, aralkyl, —C1-C6 alkyl, —C1-C6 heteroalkyl, cycloalkyl, non-aromatic heterocyclic ring, or heteroaryl, wherein M+ is a cation and wherein each aryl, aralkyl, alkyl, heteroalkyl, cycloalkyl, heterocycle, or heteroaryl is optionally substituted with one or more halogen, —N3, —OH, —NH2, or —SH, and wherein R5 is not an amino acid;
• and
• Rc is —C1-C6 alkyl, —C3-C6 cycloalkyl, —C2-C6 alkenyl, —C4-C8 cycloalkenyl, —C2-C6 alkynyl, —C8-C12 cycloalkynyl, or aryl, wherein each alkyl, cycloalkyl, alkenyl, cycloalkenyl, or aryl is optionally substituted with one or more halogen, —N3, —OH, —NH2, or —SH;
• wherein any of the nitrogen atoms in the fused pyrimidine ring can be oxidized.