Novel aromatic molecules

A compound according to general formula (I) as defined herein or a salt or solvate thereof:

• R1═C1-C12 preferably C4-C12 alkyl, C2-C12 preferably C4-C12 alkenyl, C2-C12 preferably C4-C12 alkynyl, C3-C8 cycloalkyl, C5-C8 cycloalkenyl, C5-C12 bicycloalkyl, C7-C12 bicycloalkenyl, C8-C14 tricycloalkyl, —OC1-C12 preferably —OC3-C12 alkyl, —OC2-C12 preferably —OC3-C12 alkenyl, —OC2-C12 preferably —OC3-C12 alkynyl, —OC3-C8 cycloalkyl, —OC5-C8 cycloalkenyl, —OC5-C12 bicycloalkyl, —OC7-C12 bicycloalkenyl, —OC8-C14 tricycloalkyl, —SC1-C12 preferably —SC3-C12 alkyl, —SC2-C12 preferably —SC3-C12 alkenyl, —SC2-C12 preferably —SC3-C12 alkynyl, —SC3-C8 cycloalkyl, —SC5-C8 cycloalkenyl, —SC5-C12 bicycloalkyl, —SC7-C12 bicycloalkenyl, —SC8-C14 tricycloalkyl, —NHR6 or —NR6R7 wherein R6 and R7 are independently from each other selected from:
• C1-C12 preferably C3-C12 alkyl, C2-C12 preferably C3-C12 alkenyl, C2-C12 preferably C3-C12 alkynyl, C3-C8 cycloalkyl, C5-C8 cycloalkenyl, C5-C12 bicycloalkyl, C7-C12 bicycloalkenyl, C8-C14 tricycloalkyl, or wherein R6 can form a ring structure together with R7 wherein the said ring structure including the N-atom is selected from three to eight membered cyclic structures or five to twelve membered bicyclic structures and wherein all said ring structures can additionally contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom contained in the ring structure, and particularly wherein such a replacement results in residues that contain at least twice the number of C atoms than heteroatoms independently selected from O, S and N;
• wherein all alkyl, alkenyl and alkynyl residues contained in the definitions of R1, R6 and R7 are linear or branched, and are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, —NO2, ═O, C3-C8 cycloalkyl, C5-C8 cycloalkenyl, C5-C12 bicycloalkyl, C7-C12 bicycloalkenyl, C8-C14 tricycloalkyl, linear or branched —OC1-C5 alkyl such as —OCH3, —OC3-C5 cycloalkyl such as —O(cyclopropyl), linear or branched —NH(C1-C5 alkyl), linear or branched —N(C1-C5 alkyl)(C1-C5 alkyl), —NH(C3-C5 cycloalkyl) such as —NH(cyclopropyl), —N(C3-C5 cycloalkyl)(C3-C5 cycloalkyl), linear or branched —N(C1-C5 alkyl)(C3-C5 cycloalkyl);
• wherein when an alkyl, alkenyl and alkynyl residue contained in the definitions of R1, R6 and R7 is substituted with one or more substituents being ═O, such substitution with ═O cannot result in one of the groups selected from C═O, S═O and N═O directly bound to an aromatic ring;
• wherein all cyclic structures, bicyclic structures and tricyclic structures including cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl and tricycloalkyl residues contained in the definitions of R1, R6 and R7 are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, —NO2, ═O, linear or branched C1-C5 alkyl such as —CH3, linear or branched —OC1-C5 alkyl such as —OCH3, linear or branched —NH(C1-C5 alkyl), linear or branched —N(C1-C5 alkyl)(C1-C5 alkyl), —NH(C3-C5 cycloalkyl) such as —NH(cyclopropyl), —N(C3-C5 cycloalkyl)(C3-C5 cycloalkyl), linear or branched —N(C1-C5 alkyl)(C3-C5 cycloalkyl);
• wherein all alkyl, alkenyl and alkynyl residues contained in the definitions of R1, R6 and R7 can contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom, and wherein such a replacement results in residues that contain at least twice the number of C atoms than heteroatoms independently selected from O, S and N, and wherein such replacement additionally cannot result in one of the groups selected from C═O, S═O and N═O directly bound to an aromatic ring;
• wherein all cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl and tricycloalkyl residues contained in the definitions of R1, R6 and R7 can contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom, and wherein such a replacement results in residues that contain at least the same number of C atoms than heteroatoms independently selected from O, S and N;
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl and tricycloalkyl residues contained in the definitions of R1, R6 and R7 can be partially or fully halogenated, particularly fluorinated, more particularly perfluorinated;
• wherein bicyclic and tricyclic residues include fused, bridged and spiro systems;
• R2-R5 are independently from each other selected from —H, —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, —NO2, linear or branched C1-C4 alkyl, linear or branched C2-C4 alkenyl, linear or branched C2-C4 alkynyl, C3-C6 cycloalkyl, —CH2(C3-C6 cycloalkyl), linear or branched —OC1-C3 alkyl, —O(cyclopropyl), linear or branched —NH(C1-C3 alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3 alkyl)(cyclopropyl);
• wherein all alkyl, alkenyl, alkynyl and cycloalkyl residues contained in the definitions of R2-R5 are unsubstituted or substituted with one or more substituents independently selected from —F, —Cl, —Br, —I, —CH3, —CF3, —OH and —OCH3, —OCF3, —NH2, —NHCH3, —N(CH3)2;
• wherein all alkyl, alkenyl, alkynyl and cycloalkyl residues contained in the definitions of R2-R5 can contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom, and wherein such a replacement cannot result in one of the groups selected from C═O and S═O directly bound to an aromatic ring;
• X1—X4 are independently from each other selected from N, CR8, CR9, CR10, CR11;
• R8—R11 are independently from each other selected from —H, —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, —NO2, linear or branched C1-C4 alkyl, linear or branched C2-C4 alkenyl, linear or branched C2-C4 alkynyl, C3-C6 cycloalkyl, —CH2(C3-C6 cycloalkyl), linear or branched —OC1-C3 alkyl, —O(cyclopropyl), linear or branched —NH(C1-C3 alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3alkyl)(cyclopropyl);
• wherein all alkyl, alkenyl, alkynyl and cycloalkyl residues contained in the definitions of R8—R11 are unsubstituted or substituted with one or more substituents independently selected from —F, —Cl, —Br, —I, —CH3, —CF3, —OH and —OCH3, —OCF3, —NH2, —NHCH3, —N(CH3)2;
• wherein all alkyl, alkenyl, alkynyl and cycloalkyl residues contained in the definitions of R8—R11 can contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom, and wherein such a replacement cannot result in one of the groups selected from C═O and S═O directly bound to an aromatic ring;
• wherein R8—R11 are preferably selected from —H, —F, —Cl, —Br, —CH3, —CF3, —OH, —OCH3, —OCF3, cyclopropyl, oxiranyl, —C(CH3)3, —N(CH3)2, —NH2, —CN, —CH2OCH3, —OCH(CH3)2, —CH2NH2, —CH2N(CH3)2, —CH2OH, —NO2 or —CH2—N-morpholinyl;
• wherein all alkyl, alkenyl, alkynyl and cycloalkyl residues contained in the definitions of R2-R5 and R8—R11 can be partially or fully halogenated, particularly fluorinated, more particularly perfluorinated;
• Y═—H, —OH, linear or branched —OC1-C6 alkyl, linear or branched —OC2-C6 alkenyl, linear or branched —OC2-C6 alkynyl, —OC3-C6 cycloalkyl, —SH, linear or branched —SC1-C6 alkyl, linear or branched —SC2-C6 alkenyl, linear or branched —SC2-C6 alkynyl, —SC3-C6 cycloalkyl, aromatic and heteroaromatic residues preferably six-membered aromatic cycles and five- to six-membered heteroaromatic cycles;
• wherein all aromatic and heteroaromatic residues contained in the definition of Y are linked through an —O—, or an —S—, or an —O—CH2—, or an —O—CH2—CH2—, or an —S—CH2—, or an —S—CH2—CH2—, or an —O—CH2—O—, or an —S—CH2—O—, or an —O—CH2—NH—, or an —S—CH2—NH—linker to the carbon atom to which Y is bound;
• wherein the said linkers are connected by their heteroatoms to the carbon atom to which Y is bound;
• wherein the said linkers contained in the definition of Y are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, ═O, linear or branched C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, linear or branched —OC1-C3 alkyl such as —OCH3, —O(cyclopropyl), linear or branched —NH(C1-C3 alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3 alkyl)(cyclopropyl);
• wherein all aromatic and heteroaromatic residues contained in the definition of Y are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, —NO2, linear or branched C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, linear or branched —OC1-C3 alkyl such as —OCH3, —O(cyclopropyl), linear or branched —NH(C1-C3alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3 alkyl)(cyclopropyl);
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkenyl residues contained in the definition of Y are linear or branched, and are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, ═O, linear or branched C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, linear or branched —OC1-C3 alkyl such as —OCH3, —O(cyclopropyl), linear or branched —NH(C1-C3 alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3 alkyl)(cyclopropyl);
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and heteroaromatic residues contained in the definition of Y can contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom;
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aromatic and heteroaromatic residues and the said linkers contained in the definition of Y can be partially or fully halogenated, particularly fluorinated, more particularly perfluorinated;
• Z1 and Z2 are selected from the following groups:
• wherein Z1 is —H, and wherein Z2 is —OH, linear or branched —OC1-C6 alkyl, linear or branched —OC2-C6 alkenyl, linear or branched —OC2-C6 alkynyl, —OC3-C6 cycloalkyl, —SH, linear or branched —SC1-C6 alkyl, linear or branched —SC2-C6 alkenyl, linear or branched —SC2-C6 alkynyl, —SC3-C6 cycloalkyl, aromatic and heteroaromatic residues preferably five- to six-membered aromatic cycles and five- to six-membered heteroaromatic cycles, —OS(O)R12 and —OS(O)2R12 wherein R12 is selected from linear or branched C1-C6 alkyl, linear or branched C2-C6 alkenyl, linear or branched C2-C6 alkynyl, C3-C6 cycloalkyl, C5-C6 cycloalkenyl, —CF3, and —C6H4CH3 (general formula Ia);
• wherein all aromatic and heteroaromatic residues contained in the definition of Z2 are linked through an —O—, or an —S—, or an —O—CH2—, or an —O—CH2—CH2—, or an —S—CH2—, or an —S—CH2—CH2—, or an —O—CH2—O—, or an —S—CH2—O—, or an —O—CH2—NH—, or an —S—CH2—NH—linker to the carbon atom to which Z2 is bound;
• wherein the said linkers are connected by their heteroatoms to the carbon atom to which Y is bound;
• wherein the said linkers contained in the definition of Z2 are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, ═O, linear or branched C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, linear or branched —OC1-C3 alkyl such as —OCH3, —O(cyclopropyl), linear or branched —NH(C1-C3 alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3 alkyl)(cyclopropyl);
• wherein all aromatic and heteroaromatic residues contained in the definition of Z2 are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, —NO2, linear or branched C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, linear or branched —OC1-C3 alkyl such as —OCH3, —O(cyclopropyl), linear or branched —NH(C1-C3 alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3 alkyl)(cyclopropyl);
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkenyl residues contained in the definition of Z2 are linear or branched, and are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —NH2, ═O, linear or branched C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, linear or branched —OC1-C3 alkyl such as —OCH3, —O(cyclopropyl), linear or branched —NH(C1-C3 alkyl), linear or branched —N(C1-C3 alkyl)(C1-C3 alkyl), —NH(cyclopropyl), —N(cyclopropyl)2, linear or branched —N(C1-C3 alkyl)(cyclopropyl);
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and heteroaromatic residues contained in the definition of Z2 can contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom;
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aromatic and heteroaromatic residues and the said linkers contained in the definition of Z2 can be partially or fully halogenated, particularly fluorinated, more particularly perfluorinated;
• wherein Z2 is preferably —OH, —OCH3, —OCH2CH3, —O(cyclopropyl), —OC6H5, —OCH2C6H5 and —SCH2CH3;
• or wherein Z1 and Z2 are together ═O or ═S, (general formula Ib);
• or wherein Z1 and Z2 form together a cyclic residue including the carbon atom to which they are bound (general formula Ic);
• wherein the cyclic residue is selected from three-membered rings, four-membered rings five-membered rings and six-membered rings, wherein all rings optionally can contain one or more heteroatoms independently selected from O, S and N in replacement of a carbon atom;
• wherein all rings are unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS, —OH, —OCH3, —NH2, —NHCH3, —N(CH3)2, ═O, —CH3 and —CF3, tert-butyloxycarbonyl, and —CH2C6H5;
• wherein all cyclic residues contained in the definitions of Z1 and Z2 can be partially or fully halogenated, particularly fluorinated, more particularly perfluorinated.