Aromatic compounds

A pharmaceutical composition, comprising

• a) an active agent selected from the group consisting of
• (i) a compound of formula I,
• wherein X is CH or N,
• R1=C2-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C4-C12 bicycloalkyl, C6-C12 bicycloalkenyl, C5-C14 tricycloalkyl,
• wherein all alkyl, alkenyl and alkynyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl and tricycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS;
• and C1-C3 alkyl optionally halogenated or perhalogenated, and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl and tricycloalkyl residues can be perhalogenated;
• R2=H, C1-C6 alkyl, C3-C6 cycloalkyl,
• wherein all alkyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl and cycloalkyl residues can be perhalogenated;
• or a salt or solvate thereof,
• (ii) a compound of formula II,
• wherein X is defined as in formula I,
• R1=C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C4-C12 bicycloalkyl, C6-C12 bicycloalkenyl, C5-C14 tricycloalkyl, wherein all alkyl, alkenyl and alkynyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• F, Cl, Br, I, CN, NCO, NCS;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl and tricycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• F, Cl, Br, I, CN, NCO, NCS;
• and C1-C3 alkyl optionally halogenated or perhalogenated, and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl and tricycloalkyl residues can be perhalogenated;
• R3=H, C1-C6 alkyl, or C3-C6 cycloalkyl,
• wherein all alkyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated, and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl and cycloalkyl residues can be perhalogenated;
• R4=C1-C6 alkyl, C3-C6 cycloalkyl, OH or OC1-C6 alkyl,
• wherein all alkyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl and cycloalkyl residues can be perhalogenated;
• or a salt or solvate thereof,
• wherein when R4 is C1-C6 alkyl, the alkyl residues can be linear or branched, and are substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• (iii) a compound of formula III,
• wherein X, R1 and R2 are defined as in formula I,
• or a salt or solvate thereof,
• (iv) a compound of formula IV,
• wherein X is defined as in formula I, and
• R1 and R3 are defined as in formula II, and
• R4=H, C1-C6 alkyl, C3-C6 cycloalkyl, OH or OC1-C6 alkyl,
• wherein all alkyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl
• optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl and cycloalkyl residues can be perhalogenated,
• or a salt or solvate thereof,
• (v) a compound of formula V,
• wherein n=0-5, which comprises cyclopropyl (n=0), cyclobutyl (n=1), cyclopentyl (n=2), cyclohexyl (n=3), cycloheptyl (n=4) and cyclooctyl (n=5),
• wherein the said cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl groups can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein the said cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl groups can be perhalogenated;
• R5=C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl,
• wherein all alkyl, alkenyl and alkynyl residues can be linear or branched, and are perhalogenated,
• and wherein all cycloalkyl and cycloalkenyl residues are perhalogenated,
• or wherein all alkyl, alkenyl and alkynyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• and wherein all cycloalkyl and cycloalkenyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I, —CN, —NCO, —NCS;
• and C1-C3 alkyl optionally halogenated or perhalogenated, and OC1-C3 alkyl optionally halogenated or perhalogenated,
• R6-R9 are independently from each other selected from —H, —F, —Cl, —Br, —I, linear or branched C1-C4 alkyl, linear or branched C2-C4 alkenyl, C2-C4 alkynyl, C3-C5 cycloalkyl, and wherein all alkyl, alkenyl, alkynyl and cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated, and OC1-C3 alkyl optionally halogenated or perhalogenated,
• Y=a six-membered aromatic ring selected from benzene, pyridine, pyrimidine, pyridazine or pyrazine;
• wherein the benzene ring is not substituted, or it is substituted with one to four of the substituents independently selected from R10-R13,
• and wherein the pyridine ring is not substituted, or it is substituted at the carbon positions with one to three of the substituents independently selected from R10-R12, and wherein the N-atom of the pyridine ring may be in ortho-position relative to the ether bond,
• and wherein the pyrimidine ring is not substituted, or it is substituted at the carbon positions with one or two of the substituents independently selected from R10-R11, and wherein the N-atoms of the pyrimidine ring may be in ortho-position relative to the ether bond,
• and wherein the pyridazine ring is not substituted, or it is substituted at the carbon positions with one or two of the substituents independently selected from R10-R11, and wherein an N-atom of the pyridazine ring may be in ortho-position relative to the ether bond,
• and wherein the pyrazine ring is not substituted, or it is substituted at the carbon positions with one or two of the substituents independently selected from R10-R11, and wherein an N-atom of the pyrazine ring may be in ortho-position relative to the ether bond,
• R10-R13 are independently from each other selected from —F, —Cl, —Br, —I, linear or branched C1-C4 alkyl, linear or branched C2-C4 alkenyl, C2-C4 alkynyl, C3-C5 cycloalkyl, and wherein all alkyl, alkenyl, alkynyl and cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• Z=O or S,
• R14=OR2 or NR3R4
• wherein R2 is defined as in formula I,
• and wherein R3=H, C1-C6 alkyl, or C3-C6 cycloalkyl,
• wherein all alkyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated, and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl and cycloalkyl residues can be perhalogenated;
• and wherein R4=H, C1-C6 alkyl, C3-C6 cycloalkyl, OH or OC1-C6 alkyl,
• wherein all alkyl residues can be linear or branched, and can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all cycloalkyl residues can be unsubstituted or substituted with one or more substituents independently selected from:
• —F, —Cl, —Br, —I;
• and C1-C3 alkyl optionally halogenated or perhalogenated;
• and OC1-C3 alkyl optionally halogenated or perhalogenated,
• wherein all alkyl and cycloalkyl residues can be perhalogenated;
• or a salt or solvate thereof;
• and wherein compounds as indicated below are excluded:
• TABLE Ia
• Compound
• R1
• R2
• X
• I-A
• tert-butyl
• H
• CH
• I-B
• tert-butyl
• ethyl
• CH
• I-C
• tert-pentyl
• H
• CH
• I-D
• tert-pentyl
• ethyl
• CH
• I-E
• cyclo-hexyl
• H
• CH
• I-F
• cyclo-hexyl
• ethyl
• CH
• I-G
• adamant-1-yl
• H
• CH
• I-H
• adamant-1-yl
• ethyl
• CH
• I-I
• methyl
• H
• N
• I-J
• methyl
• ethyl
• N
• I-K
• tert-butyl
• H
• N
• I-L
• tert-butyl
• ethyl
• N
• I-M
• tert-pentyl
• H
• N
• I-N
• tert-pentyl
• ethyl
• N
• I-O
• cyclo-hexyl
• H
• N
• I-P
• cyclo-hexyl
• ethyl
• N
• I-Q
• isopropyl
• H
• CH
• I-R
• phenyl
• H
• CH
• I-S
• methyl
• H
• CH
• I-T
• tert-butyl
• methyl
• N
• I-U
• methyl
• methyl
• N
• I-V
• methyl
• methyl
• CH
• I-W
• methyl
• ethyl
• CH
• I-X
• n-hexyl
• H
• CH
• I-Y
• n-octyl
• H
• CH
• I-Z
• n-dodecyl
• H
• CH
• I-AA
• iso-propyl
• H
• N
• TABLE IIa
• Compound
• R1
• R3
• R4
• X
• II-A
• tert-butyl
• H
• H
• N
• II-B
• methyl
• H
• methyl
• CH
• II-C
• methyl
• methyl
• methyl
• CH
• TABLE IIIa
• Compound
• R1
• R2
• X
• III-A
• tert-butyl
• H
• CH
• III-B
• tert-butyl
• ethyl
• CH
• III-C
• phenyl
• H
• CH
• and
• b) carriers, diluents and/or adjuvants suitable for administration to patients.