Patent ID: 11945822
Assignee: LEAD DISCOVERY CENTER GMBH
Field: Pharmaceuticals (Chemistry)
Classification: CPC C  A | IPC A  C

Claim 0:
1. A compound having general formula I, wherein
X is, independently at each occurrence, selected from CH and N;
L1 is either absent or independently, at each occurrence, selected from the group consisting of —NH—, —NH(CH2)—, —NH(C═O)—, —NHSO2—, —O—, —O(CH2)—, —(C═O)—, —(C═O)NH— and —(C═O)(CH2)—;
Q is, independently at each occurrence, selected from the group consisting of C3-C8 cycloalkyl, aryl, heteroaryl, heterocyclyl, and C1-C6 alkyl, wherein C1-C6 alkyl is substituted with one or two of —OR5, —N(R5)R5, aryl, heteroaryl and heterocyclyl,
C3-C8 cycloalkyl can be substituted with one or two of R3 and R4 and —(C═O)R5, heterocyclyl can be substituted with one or two of R3 and R4 and —(C═O)R5, aryl or heteroaryl can be substituted with one or two of C1-C6 alkyl, —OR5, —N(R5)R5, —(C═O)R5, halogen, heteroaryl and heterocyclyl;

R1 is hydrogen;
R2 is, at each occurrence, independently selected from the group consisting of C1-C6 alkyl, C3-C10 cycloalkyl, —CN, —(C═O)CH3, —NR9R12 and C1-C3 haloalkyl, any of which is optionally substituted;
R3 is independently, at each occurrence, selected from the group consisting of hydrogen, —OR5, halogen, —N(R5)R5, —NR9R12, —NH(C═O)R5, —(C═O)NH2, aryl, heteroaryl, heterocyclyl, C1-C6 alkyl and C1-C6 alkyl substituted with —OH or —NH2;
R4 is, independently, at each occurrence, selected from the group consisting of hydrogen, halogen, —OR5, —N(R5)R5, (═O), aryl, heteroaryl, heterocyclyl, C1-C6 alkyl and C1-C6 alkyl substituted with —OH or —NH2;
R5 is, at each occurrence, independently selected from the group consisting of hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C3 haloalkyl, heteroaryl optionally substituted with one or two of halogen, —OR11, —N(R11)R11, and C1-C6 alkyl optionally substituted with —OH or —NH2, heterocyclyl optionally substituted with one or two of halogen, —OR11, —N(R11)R11, C1-C6 alkyl and C1-C6 alkyl substituted with —OH or —NH2;
Z is, wherein
X1 is CR24;
X2 is CR25;
R6 is, at each occurrence, independently selected from hydrogen, and any structure of the following group B;, R7 is, at each occurrence, independently selected from the group consisting of hydrogen, C1-C6 alkyl, and any structure of the following group C;, R8 and R10 are, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C3 haloalkyl, —NH2, —OH, —OR5, —CN, —(C═O)R5, —(C═O)OR5, —(C═O)NH2, —(C═O)NHR21, —CH2(C═O)NHR21, —NH(C═O)R13, —NHS(═O)2R5, —S(═O)2NH2, —S(═O)2NHR21, and C1-C6 alkyl substituted with —OH, —OR5 or —NHR9;
R9 is, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C3 haloalkyl, —OR5, —CN, C3-C10 cycloalkyl, C3-C10 heterocyclyl and C1-C6 alkyl substituted with —OH or —OR5;
R11 is, at each occurrence, independently selected from the group consisting of hydrogen, C1-C6 alkyl and C3-C10 cycloalkyl;
R12 is, at each occurrence, absent or independently selected from the group consisting of C1-C6 alkyl optionally substituted with —OR5 or —N(R5)R5, benzyl optionally substituted with one to four halogens or C1-C3 alkyls, C3-C9 heteroaryl optionally substituted with one to four halogens or C1-C3 alkyls, C3-C6 heterocyclyl optionally substituted with C1-C3 alkyl, and C6-C10 aryl optionally substituted with one to four halogens and/or one to four —NH(C═O)R13;
R13 is, at each occurrence, independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkyl substituted with —CN, —OH, —OR5, —NH2, —NHR5 or —N(R5)R5 and C3-C10 cycloalkyl;
R14 and R15 are, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkyl substituted with —OH or —NH2, C3-C10 cycloalkyl, —(C═O)R5, —(C═O)NHR21, —C(R9)(R11)OR21, —NH(C═O)R21, —NR9R21, —OR21, —OC(R9)(R11)(R21), C3-C10 heterocyclyl, C3-C10 heterocyclyl substituted with R4, C3-C10 heteroaryl substituted with one to four halogens or C1-C3 alkyl, C6-C10 aryl, and aryl substituted with —(C═O)R5, —(C═O)OR5, —(C═O)NH2, —(C═O)NHR21, —CH2(C═O)NHR21, —NH(C═O)R13, —NHS(═O)2R5, —S(═O)2NH2 or —S(═O)2NHR21;
R16 is, at each occurrence, independently selected from the group consisting of hydrogen, C1-C6 alkyl, —(C═O)R13 and C1-C6 alkyl substituted with —OR5;
R17, R18, R19 and R20 are, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C3 haloalkyl, C6-C10 aryl, —CN, —CHCF3NR9R11, —OH, —OR21, —NO2, —(C═O)R5, —(C═O)OR5, —(C═O)NH2, —(C═O)NHR21, —NH(C═O)R13, —NHR5, —NHS(═O)2R5, —S(═O)2NH2, —S(═O)2NHR21 and C1-C6 alkyl substituted with —CN, —OH, —OR5, —(C═O)NHR5, —NH2, —NH(C═O)R5, —NHR5 or —N(R5)R5;
R21 is, at each occurrence, independently selected from the group consisting of C3-C10 cycloalkyl, C1-C3 haloalkyl, benzyl, C1-C6 alkyl optionally substituted with —CN, —OH, —OR5, —NH2, —NHR5 or —N(R5)R5, aryl optionally substituted with halogen or C1-C3 haloalkyl, C3-C10 heteroaryl substituted with one to four halogens or C1-C3 alkyl and C3-C10 heterocyclyl optionally substituted with R4;
R22 and R23 are, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C3 haloalkyl, —OH, —OR5, —CN and C1-C6 alkyl substituted with —OH, —OR5 or —NHR9;
R24 and R25 are, at each occurrence, independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C3 haloalkyl, —NH2, —OH, —OR5, —CN, —(C═O)R5, —(C═O)OR5, —(C═O)NH2, —(C═O)NHR21, —CH2(C═O)NHR21, —NH(C═O)R13, —NHS(═O)2R5, —S(═O)2NH2 or —S(═O)2NHR21 and C1-C6 alkyl substituted with —OH, —OR5 or —NHR9;
with the proviso that when Z is, then one of R6 and R7 is not H;
with the proviso that when Z is, then one of R6 and R22 is not H;
with the proviso that when R6 is, then one of R14 and R15 is not H, and if R14 is H, then R15 is not Cl;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is absent, Q is heterocycyl substituted with R3 and R4, R3 is N(R5)R5, R4 is H, R5 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is O, Q is heterocycyl substituted with R3 and R4, R3 is CH3, R4 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is 1H-pyrazole;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is —(C═O)—, Q is heterocycyl substituted with R3 and R4, R4 is H, X is N, Z is phenyl, R6 is 1H-pyrazole, R7 is H, R8 is H, R9 is H and R10 is H, then R3 is not H;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is —(C═O)—, Q is heterocycyl substituted with R3 and R4, R3 is N(R5)R5, R4 is H, R5 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole,
wherein, if R1 is H, R2 is CH(CH3)2, L1 is O, Q is heterocycyl substituted with R3 and R4, R3 is H, R4 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is O, Q is C3-C8 cycloalkyl substituted with R3 and R4, R3 is N(R5)R5, R4 is H, R5 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is NH, Q is heterocycyl substituted with R3 and R4, R3 is H, R4 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is NH, Q is C3-C8 cycloalkyl substituted with R3 and R4, R3 is N(R5)R5, R4 is H, R5 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is O, Q is heterocycyl substituted with R3 and R4, R3 is H, R4 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is F, then R6 is not 1H-pyrazole;
wherein, if R1 is CH3, R2 is CH(CH3)2, L1 is O, Q is heterocycyl substituted with R3 and R4, R3 is H, R4 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole;
wherein, if R1 is H, R2 is CH(CH3)2, L1 is O, Q is heterocycyl substituted with R3 and R4, R3 is CH3, R4 is H, X is N, Z is phenyl, R7 is H, R8 is H, R9 is H and R10 is H, then R6 is not 1H-pyrazole;
wherein, if R1 is CH3, R2 is CH(CH3)2, L1 is O, Q is heterocycyl substituted with R3 and R4, R3 is H, R4 is H, X is N, Z is phenyl, R6 is H, R7 is OR12, R8 is H, R9 is H and R10 is H, then R12 is not CH3;
or an enantiomer, stereoisomeric form, mixture of enantiomers, diastereomer, mixture of diastereomers, racemate of the above compounds, or a pharmaceutically acceptable salt thereof.