2,4-Pyrimidinediamine compounds and their uses

A 2,4 pyrimidinediamine compound according to structure (I):

• including salts, hydrates, solvates and N-oxides thereof, wherein:
• X is selected from the group consisting of N and CH;
• Y is selected from the group consisting of O, S, SO, SO2, SONR36, NH, NR35 and NR37;
• Z is selected from the group consisting of O, S, SO, SO2, SONR36, NH, NR35 and NR37;
• R2 is selected from the group consisting of (C1-C6) alkyl optionally substituted with one or more of the same or different R8 groups, (C3-C8) cycloalkyl optionally substituted with one or more of the same or different R8 groups, cyclohexyl optionally substituted with one or more of the same or different R8 groups, 3-8 membered cycloheteroalkyl optionally substituted with one or more of the same or different R8 groups, (C5-C15) aryl optionally substituted with one or more of the same or different R8 groups, phenyl optionally substituted with one or more of the same or different R8 groups and 5-15 membered heteroaryl optionally substituted with one or more of the same or different R8 groups;
• R5 is selected from the group consisting of R6, (C1-C6) alkyl optionally substituted with one or more of the same or different R8 groups, (C1-C4) alkanyl optionally substituted with one or more of the same or different R8 groups, (C2-C4) alkenyl optionally substituted with one or more of the same or different R8 groups and (C2-C4) alkynyl optionally substituted with one or more of the same or different R8 groups;
• R6 is independently selected from the group consisting of hydrogen, an electronegative group, —ORd, —SRd, (C1-C3) haloalkyloxy, (C1-C3) perhaloalkyloxy, —NRcRc, halogen, (C1-C3) haloalkyl, (C1-C3) perhaloalkyl, —CF3, —CH2CF3, —CF2CF3, —CN, —NC, —OCN, —SCN, —NO, —NO2, —N3, —S(O)Rd, —S(O)2Rd, —S(O)2ORd, —S(O)NRcRc;
• —S(O)2NRcRc, —OS(O)Rd, —OS(O)2Rd, —OS(O)2ORd, —OS(O)NRcRc, —OS(O)2NRcRc, —C(O)Rd, —C(O)ORd, —C(O)NRcRc, —C(NH)NRcRc, —OC(O)Rd, —SC(O)Rd, —OC(O)ORd, —SC(O)ORd, —OC(O)NRcRc, —SC(O)NRcRc, —OC(NH)NRcRc, —SC(NH)NRcRc, —[NHC(O)]nRd, —[NHC(O)]nORd, —[NHC(O)]nNRcRc and —[NHC(NH)]nNRcRc, (C5-C10) aryl optionally substituted with one or more of the same or different R8 groups, phenyl optionally substituted with one or more of the same or different R8 groups, (C6-C16) arylalkyl optionally substituted with one or more of the same or different R8 groups, 5-10 membered heteroaryl optionally substituted with one or more of the same or different R8 groups and 6-16 membered heteroarylalkyl optionally substituted with one or more of the same or different R8 groups;
• R8 is selected from the group consisting of Ra, Rb, Ra substituted with one or more of the same or different Ra or Rb, —ORa substituted with one or more of the same or different Ra or Rb, —B(ORa)2, —(NRc)2, —(CH2)m—Rb, —(CHRa)m—Rb, —O—(CH2)m—Rb, —S—(CH2)m—Rb, —O—CHRaRb, —O—CRa(Rb)2, —O—(CHRa)m—Rb, —O—(CH2)m—CH[(CH2)mRb]Rb, —S—(CHRa)m—Rb, —C(O)NH—(CH2)m—Rb, —C(O)NH—(CHRa)m—Rb, —O—(CH2)m—C(O)NH—(CH2)m—Rb, —S—(CH2)m—C(O)NH—(CH2)m—Rb, —O—(CHRa)m—C(O)NH—(CHRa)m—Rb, —S—(CHRa)m—C(O)NH—(CHRa)m—Rb, NH—(CH2)m—Rb, —NH—(CHRa)m—Rb, NH[(CH2)mRb], —N[(CH2)mRb]2, —NH—C(O)—NH—(CH2)m—Rb, —NH—C(O)—(CH2)m—CHRbRb and —NH—(CH2)m—C(O)—NH—(CH2)m—Rb;
• each R35 is, independently of the others, selected from the group consisting of hydrogen and R8, or, alternatively, two R35 bonded to the same carbon atom are taken together to form an oxo (═O), NH or NR38 group and the other two R35 are each, independently of one another, selected from the group consisting of hydrogen and R8;
• each R36 is independently selected from the group consisting of hydrogen and (C1-C6) alkyl;
• each R37 is independently selected from the group consisting of hydrogen and a progroup;
• R38 is selected from the group consisting of (C1-C6) alkyl and (C5-C14) aryl;
• each Ra is independently selected from the group consisting of hydrogen, (C1-C6) alkyl, (C3-C8) cycloalkyl, cyclohexyl, (C4-C11) cycloalkylalkyl, (C5-C10) aryl, phenyl, (C6-C16) arylalkyl, benzyl, 2-6 membered heteroalkyl, 3-8 membered cycloheteroalkyl, morpholinyl, piperazinyl, homopiperazinyl, piperidinyl, 4-11 membered cycloheteroalkylalkyl, 5-10 membered heteroaryl and 6-16 membered heteroarylalkyl;
• each Rb is a suitable group independently selected from the group consisting of ═O, —ORd, (C1-C3) haloalkyloxy, —OCF3, ═S, —SRd, ═NRd, ═NORd, —NRcRc, halogen, —CF3, —CN, —NC, —OCN, —SCN, —NO, —NO2, ═N2, —N3, —S(O)Rd, —S(O)2Rd, —S(O)2ORd, —S(O)NRcRc, —S(O)2NRcRc, —OS(O)Rd, —OS(O)2Rd, —OS(O)2ORd, —OS(O)2NRcRc, —C(O)Rd, —C(O)ORd, —C(O)NRcRc, —C(NH)NRcRc, —C(NRa)NRcRc, —C(NOH)Ra, —C(NOH)NRcRc, —OC(O)Rd, —OC(O)ORd, —OC(O)NRcRc, —OC(NH)NRcRc, —OC(NRa)NRcRc, —[NHC(O)]nRd, —[NRaC(O)]nRd, —[NHC(O)]nORd, —[NRaC(O)]nORd, —[NHC(O)]nNRcRc, [NRaC(O)]nNRcRc, —[NHC(NH)]nNRcRc and —[RaC(NRa)]nNRcRc;
• each Rc is independently a protecting group or Ra, or, alternatively, each Rc is taken together with the nitrogen atom to which it is bonded to form a 5 to 8-membered cycloheteroalkyl or heteroaryl which may optionally include one or more of the same or different additional heteroatoms and which may optionally be substituted with one or more of the same or different Ra or suitable Rb groups;
• each Rd is independently a protecting group or Ra;
• each m is independently an integer from 1 to 3;
• and
• each n is independently an integer from 0 to 3.