4-thieno[2,3-D]pyrimidin-4-YL piperazine compounds

A compound of formula II:

• wherein
• the subscript m is an integer of from 0 to 4;
• R5 is selected from the group consisting of H, (C1–C6)alkyl, (C3–C7)cycloalkyl and —(CH2)n1—R11 wherein the subscript n1 is an integer of from 0 to 3 and R11 is selected from the group consisting of (C1–C6)alkoxy, (C1–C6)alkylthio, mono- or di-(C1–C6)alkylamino, amino, phenyl, pyridyl, furanyl, pyrrolyl, imidazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, thiazolyl, pyrazolyl, and thienyl, wherein each of the rings is optionally substituted with from 1 to 3 substituents selected from halogen, N3, NO2, CN, (C1–C6)alkyl, OR12, N(R12)2, CO2R12 and CON(R12)2, wherein each R12 is independently H or (C1–C6)alkyl;
• J is selected from the group consisting of a direct link, C(O), C(S), C(NR9), S(O) and S(O)2, wherein R9 is selected from the group consisting of H, CN, NO2 and (C1–C6)alkyl;
• A is selected from the group consisting of a direct link, O, S, N—R10, C(O) and CH(OH), wherein R10 is selected from the group consisting of H, (C1–C6)alkyl and C(O)—(C1–C6)alkyl;
• R1 is selected from the group consisting of halo, CN, NO2, N3, (C1–C6)alkyl, (C3–C7)cycloalkyl, —C(R13)═C(R13)2, —C≡CR13 and —(CH2)n2—R14;
• wherein each R13 is independently selected from the group consisting of H, F, Cl, Br, CN, (C1–C6)alkyl, (C3–C7)cycloalkyl, (CH2)n2—R14 and C(O)—(CH2)2—R14;
• and wherein each subscript n2 is independently an integer of from 0 to 3 and each R14 is independently selected from the group consisting of (C1–C6)alkoxy, (C1–C6)alkylthio, mono- or di-(C1–C6)alkylamino, amino, phenyl, pyridyl, furanyl, pyrrolyl, imidazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, thiazolyl, pyrazolyl, and thienyl, wherein each of the rings is optionally substituted with from 1 to 3 substituents selected from halogen, NO2, N3, CN, (C1–C6)alkyl, OR15, N(R15)2, CO2R15 and CON(R15)2, wherein each R15 is independently H or (C1–C6)alkyl;
• and wherein any alkyl or cycloalkyl portions of R1 are optionally substituted with from one to five F substituents;
• R2 is selected from the group consisting of H, CN, NO2, N3, (C1–C6)alkyl, (C3–C7)cycloalkyl, —C(R16)═C(R16)2, —C≡R16, —C(O)—(CH2)n3—R17 and —(CH2)n3—R17;
• wherein each R16 is independently selected from the group consisting of H, F, Cl, Br, CN, (C1–C6)alkyl, (CH2)n3—R17 and —(CH2)n3—C(O)—R17;
• wherein the subscript n3 is an integer of from 0 to 3 and R17 is selected from the group consisting of (C1–C6)alkoxy, (C1–C6)alkylthio, mono- or di-(C1–C6)alkylamino, amino, hydroxy, phenyl, pyridyl, furanyl, pyrrolyl, imidazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, thiazolyl, pyrazolyl, and thienyl, wherein each of the rings is optionally substituted with from 1 to 3 substituents selected from halogen, N3, NO2, CN, (C1–C6)alkyl, OR18, N(R18)2, CO2R18 and CON(R18)2, wherein each R18 is independently H or (C1–C6)alkyl;
• and wherein any alkyl or cycloalkyl portions of R2 are optionally substituted with from one to five F substituents;
• each R3 is independently selected from the group consisting of (C1–C6)alkyl, (C3–C7)cycloalkyl, —(CH2)n4—R19 and —C(O)—(CH2)n4—R19;
• wherein the subscript n4 is an integer of from 0 to 4 and R19 is selected from the group consisting of (C1–C6)alkoxy, (C1–C6)alkylthio, mono- or di-(C1–C6)alkylamino, amino, phenyl, pyridyl, furanyl, pyrrolyl, imidazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, thiazolyl, pyrazolyl, and thienyl, wherein each of the rings is optionally substituted with from 1 to 3 substituents selected from halogen, N3, NO2, CN, (C1–C6)alkyl, OR20, N(R20)2, CO2R20 and CON(R20)2, wherein each R20 is independently H or (C1–C6)alkyl;
• and wherein any alkyl or cycloalkyl portions of R3 are optionally substituted with from one to five F substituents;
• L is a direct link or a divalent linking group having a formula selected from the group consisting of
• wherein
• V1 is selected from the group consisting of a direct link, O, S and NR23,
• V2 is selected from the group consisting of a direct link, —(CR24═CR24)n8—, —(C≡C)n8—, C(O), C(S), S(O), S(O)2 and C(NR23);
• V3 is selected from the group consisting of a direct link, O, S and NR23;
• the subscript n5 is an integer of from 0 to 2;
• the subscripts n6 and n7 are each independently an integer of from 0 to 7;
• the subscript n8 is an integer of from 1 to 2;
• each R23 is independently selected from the group consisting of H and (C1–C6)alkyl;
• each R24 independently selected from the group consisting of (C1–C6)alkyl, (C3–C7) cycloalkyl, (CH2)n9—R25 and —(CO)—(CH2)n9—R25 wherein the subscript n9 is an integer of from 0 to 3 and R25 is selected from the group consisting of (C1–C6)alkoxy, (C1–C6)alkylthio, mono- or di-(C1–C6)alkylamino, hydroxy, NH2, phenyl, pyridyl, furanyl, pyrrolyl, imidazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, thiazolyl, pyrazolyl, and thienyl, wherein each of the rings is optionally substituted with from 1 to 3 substituents selected from halogen, N3, NO2, CN, (C1–C6)alkyl, OR26, N(R26)2, CO2R26 and CON(R26)2, wherein each R26 is independently H or (C1–C6)alkyl;
• each R21 and R22 is (i) independently selected from the group consisting of H, (C1–C6)alkyl, phenyl, pyridyl, furanyl, pyrrolyl, imidazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, thiazolyl, pyrazolyl, and thienyl, wherein each of the rings is optionally substituted with from 1 to 3 substituents selected from halogen, N3, NO2, CN, (C1–C6)alkyl, OR29, N(R29)2, CO2R29 and CON(R29)2, wherein each R29 is independently H or (C1–C6)alkyl;
• or (ii) combined to form —CH2—(CH2)n10—CH2—;
• wherein the subscript n10 is an integer of from 0 to 4;
• and
• R4is a member selected from the group consisting of H, F, CF3, CN, N3, NO2, (C1–C6)alkyl, amino, mono- or di-(C1–C6)alkylamino, (C3–C7)cycloalkyl, (C3–C7)heterocycloalkyl, heteroaryl, fused (C8–C10)bicycloalkyl, fused (C8–C10)bicycloalkaryl, aryl and fused bicycloaryl;
• wherein any alkyl group present in R4 are unsubstituted, partially- or fully-substituted with F, and each of the rings is optionally substituted with from one to four substituents selected from halogen, NO2, N3, SO2NH2, CN, (C1–C6)alkyl, OR30, N(R30)2, CO2R30 and CON(R30)2, wherein each R30 is independently H or (C1–C6)alkyl;
• or a pharmaceutically acceptable salt or prodrug thereof.