2,5-substituted pyrimidines

A 2,5-substituted pyrimidine having the following general formula (I)

• wherein
• A, B, C each independently of each other stands for N or CH;
• R1 stands for (C1-C6)-alkyl, (C1-C6)-hydroxyalkyl, (C3-C6)-cycloalkyl, or SOx—(C1-C6)-alkyl;
• x is 0, 1 or 2;
• G is an optionally with at least one substituent Y substituted phenyl or 5- or 6-membered heteroaryl which comprises at least one oxygen, sulfur or nitrogen atom, whereas the nitrogen atoms present in the heteroaryl can be substituted with R4;
• R4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, CO—(C1-C6)-alkyl, SO(C1-C6)-alkyl, SO2(C1-C6)-alkyl;
• Y is OH, CN, SH, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkinyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-thioalkyl, (C1-C6)-haloalkyl, (C1-C6)-thiohaloalkyl, (C1-C6)-haloalkoxy, CO2H, CO2(C1-C6)-alkyl, CHO, CO(C1-C6)-alkyl, OCO(C1-C6)-alkyl, CONH2, CONH—(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, OCO—NH(C1-C6)-alkyl, OCO—N((C1-C6)-alkyl)2, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, NH—CO—(C1-C6)alkyl, NH—CO2 (C1-C6)-alkyl, N(C1-C6)-alkyl-CO2 (C1-C6)-alkyl, NH—CO—NH2, NH—CO—NH(C1-C6)-alkyl, NH—CO—N(C1-C6)-alkyl)2, N(C1-C6)-alkyl-CO—NH2, N(C1-C6)alkyl-CO—NH(C1-C6)-alkyl, N(C1-C6)-alkyl-CO—N((C1-C6)-alkyl)2, NH—SO2—(C1-C6)-alkyl, N(C1-C6)alkyl-SO2—(C1-C6)-alkyl, S—(C1-C6)-alkyl, SO(C1-C6)-alkyl, SO2—(C1-C6)-alkyl, SO2H, SO2OH, SO2NH2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, C(═N)—NH, NHC(═N)—NH2, —N═C═O, or —S—CN, wherein the aforementioned alkyl chains may be substituted with at least one of the following substituents OH, CN, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, CO2H, CO2(C1-C6)-alkyl or —NH2;
• R2 and R3′
• independently of one another stand for hydrogen or optionally substituted (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-alkoxy(C1-C6)-alkylen, (C1-C6)-alkylen-CO2H, (C1-C6)-alkylen-CO2(C1-C6)-alkyl, (C1-C6)-alkylen-CONH2, (C1-C6)-alkylen-CONH(C1-C6)-alkyl, (C1-C6)-alkylen-CON((C1-C6)-alkyl)2, (C1-C6)-alkylen-(C3-C6)-cycloalkyl, (C1-C6)-hydroxyalkyl-(C3-C6)-cycloalkylen, a group L1V, a group L2W, or
• together with the nitrogen atom to which they are attached form an optionally with at least one substituent XQ substituted 3- to 12-membered mono- or bicyclic heteroaliphatic residue Q which may additionally contain at least one oxygen, sulfur or further nitrogen atom, whereas these one or more additional nitrogen atoms are substituted with R5;
• XQ independently of each other stand for ═O(carbonyl), halogen, OH, CN, SH, (C1-C6)-alkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-cyanoalkyl, (C2-C6)-alkenyl, (C2-C6)-alkinyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy(C1-C6)-alkylen, (C1-C6)-thioalkyl, (C1-C6)-haloalkyl, (C1-C6)-thiohaloalkyl, (C1-C6)-haloalkoxy, —NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, (C1-C6)-alkylen-NH(C1-C6)-alkyl, (C1-C6)-alkylen-N((C1-C6)-alkyl)2 NH—CHO, NH—CO(C1-C6)-alkyl, N(C1-C6)-alkyl-CO(C1-C6)-alkyl, NH—CO—O(C1-C6)-alkyl, N(C1-C6)-alkyl-CO—O(C1-C6)-alkyl, NH—CO—NH2, NH—CO—NH(C1-C6)-alkyl, NH—CO—N((C1-C6)-alkyl)2, N(C1-C6)-alkyl-CO—NH2, N(C1-C6)-alkyl-CO—NH(C1-C6)-alkyl, N(C1-C6)-alkyl-CO—N((C1-C6)-alkyl)2, NH—SO2—(C1-C6)-alkyl, N(C1-C6)-alkyl-SO2—(C1-C6)-alkyl, CO2H, CO2(C1-C6)-alkyl, CHO, CO(C1-C6)-alkyl, O—CO(C1-C6)-alkyl, CO—NH2, CO—NH(C1-C6)-alkyl, CO—N((C1-C6)-alkyl)2, O—CO—NH(C1-C6)-alkyl, O—CO—N((C1-C6)-alkyl)2, S—(C1-C6)-alkyl, SO(C1-C6)-alkyl, SO2—(C1-C6)-alkyl, SOOH, SO2OH, SO2NH2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, C(═N)—NH, NHC(═N)—NH2, —N═C═O, or —S—CN, wherein the aforementioned alkyl chains may be substituted with at least one of the following substituents OH, CN, (C3-C6)-cycloalkyl, (Cr C6)-alkoxy, CO2H, CO2(C1-C6)-alkyl or —NH2;
• R5 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, CO—(C1-C6)-alkyl, SO—(C1-C6)-alkyl, SO2—(C1-C6)-alkyl;
• L1 is a bond or a branched or straight-chain optionally substituted (C1-C6)-alkylene group connected to the amide nitrogen;
• V is an optionally with at least one substituent Xv substituted 3- to 12-membered mono- or bicyclic aliphatic or heteroaliphatic residue, whereas if one or more nitrogen atoms are present in the mono- or bicyclic heteroaliphatic residue, then at least one of these nitrogen atoms is substituted with R6;
• XV independently of each other stand for ═O (carbonyl), halogen, OH, CN, SH, (C1-C6)-alkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-cyanoalkyl, (C2-C6)-alkenyl, (C2-C6)-alkinyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy(C1-C6)-alkylen, (C1-C6)-thioalkyl, (C1-C6)-haloalkyl, (C1-C6)-thiohaloalkyl, (C1-C6)-haloalkoxy, —NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, (C1-C6)-alkylen-NH(C1-C6)-alkyl, (C1-C6)-alkylen-N((C1-C6)-alkyl)2 NH—CHO, NH—CO(C1-C6)-alkyl, N(C1-C6)-alkyl-CO(C1-C6)-alkyl, NH—CO—O(C1-C6)-alkyl, N(C1-C6)-alkyl-CO—O(C1-C6)-alkyl, NH—CO—NH2, NH—CO—NH(C1-C6)-alkyl, NH—CO—N((C1-C6)-alkyl)2, N(C1-C6)-alkyl-CO—NH2, N(CO—NH(C1-C6)-alkyl, N(C1-C6)-alkyl-CO—N((C1-C6)-alkyl)2, NH—SO2—(C1-C6)-alkyl, N(C1-C6)-alkyl-SO2—(C1-C6)-alkyl, CO2H, CO2(C1-C6)-alkyl, CHO, CO(C1-C6)-alkyl, O—CO(C1-C6)-alkyl, CO—NH2, CO—NH(C1-C6)-alkyl, CO—N((C1-C6)-alkyl)2, O—CO—NH(C1-C6)-alkyl, O—CO—N((C1-C6)-alkyl)2, S—(C1-C6)-alkyl, SO(C1-C6)-alkyl, SO2—(C1-C6)-alkyl, SOOH, SO2OH, SO2NH2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6)-alkyl)2, C(═N)—NH, NHC(═N)—NH2, —N═C═O, or —S—CN, wherein the aforementioned alkyl chains may be substituted with at least one of the following substituents OH, CN, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, CO2H, CO2(C1-C6)-alkyl or —NH2;
• R6 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, CO—(C1-C6)-alkyl, SO(C1-C6)-alkyl, or SO2(C1-C6)-alkyl;
• L2 is a bond or a branched or straight-chain optionally substituted (C1-C6)-alkylene group connected to the amide nitrogen;
• W is an optionally with at least one substituent Z substituted phenyl or 5- or 6-membered heteroaryl which comprises at least one oxygen, sulfur or nitrogen atom;
• and
• Z independently of each other stand for halogen, OH, CN, SH, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkinyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-thioalkyl, (C1-C6)-haloalkyl (C1-C6)-thiohaloalkyl, (C1-C6)-haloalkoxy, —NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, NH—CHO, NH—CO(C1-C6)-alkyl, N(C1-C6)-alkyl-CO(C1-C6)-alkyl, NH—CO2(C1-C6)-alkyl, N(C1-C6)-alkyl-CO2(C1-C6)-alkyl, NH—CO—NH2, NH—CO—NH(C1-C6)-alkyl, NH—CO—N((C1-C6)-alkyl)2, N(C1-C6)-alkyl-CO—NH2, N(C1-C6)-alkyl-CO—NH(C1-C6)-alkyl, N(C1-C6)-alkyl-CO—N((C1-C6)-alkyl)2, NH—SO2—(C1-C6)-alkyl, N(C1-C6)-alkyl-SO2—(C1-C6)-alkyl, CO2H, CO2(C1-C6)-alkyl, CHO, CO(C1-C6)-alkyl, O—CO(C1-C6)-alkyl, CO—NH2, CO—NH(C1-C6)-alkyl, CO—N((C1-C6)-alkyl)2, O—CO—NH(C1-C6)-alkyl, O—CO—N((C1-C6)-alkyl)2, S—(C1-C6)-alkyl, SO(C1-C6)-alkyl, SO2—(C1-C6)-alkyl, SO2H, SO2OH, SO2NH2, SO2NH(C1-C6)-alkyl, SO2N((C1-C6) alkyl)2, C(═N)—NH, NHC(═N)—NH2, —N═C═O, or —S—CN, wherein the aforementioned alkyl chains may be substituted with at least one of the following substituents OH, CN, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, CO2H, CO2(C1-C6)-alkyl or —NH2.