1,7-diaryl-1,6-heptadiene-3,5-dione derivatives, methods for the production and use thereof

A compound with formula (1):

• wherein the residues Q1 and Q2, respectively independently of each other, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,
• wherein the compound with formula (1) does not contain an OH group which is bonded directly to the organic residue Q1 or Q2, and
• wherein K represents hydrogen or a cation, and wherein
• (a) at least one of the residues Q1 and Q2, respectively independently of each other, is substituted with at least one organic residue W1a, wherein
• the at least one organic residue W1a has the general formula (5a), (6a), (7a), (8a), or (9a):
• -A-(C(D)(E))h-Xa, (5a)
• —(C(D)(E))k-aryl-(C(D)(E))l-Xa, (6a)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-Xa, (7a)
• —((C(D)(E))m-A)p-(C(D)(E))n-Xa, (8a)
• -A-((C(D)(E))m-A)p-(C(D)(E))n-Xa, (9a)
• wherein h represents a whole number from 1 to 20, wherein k represents a whole number from 0 to 10, wherein 1 represents a whole number from 0 to 10, and wherein m, n and p, respectively independently of each other, represent a whole number from 1 to 6, and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom,
• wherein Xa, respectively independently of each other, represents a residue with formula (20c), (20d), or (21):
• wherein each of the residues R(VII), R(VIII), and R(IX), respectively independently of each other, represents hydrogen, an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing 1 to 8 C atoms, and
• wherein the residues R1, R2, R3, R4 and R5, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, cycloalkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms,
• or wherein
• (b) the residue R3 is an organic residue W2a which contains at least one neutral nitrogen atom which can be protonated, and/or at least one positively charged nitrogen atom and/or at least one positively charged phosphorus atom, wherein
• the one organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b), or (9b):
• —(C(D)(E))h-Xb, (4b)
• -A-(C(D)(E))h-Xb, (5b)
• —(C(D)(E))k-aryl-(C(D)(E))l-Xb, (6b)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-Xb, (7b)
• —[(C(D)(E))m-A]p—(C(D)(E))n-Xb, (8b)
• -A-[(C(D)(E))m-A]p—(C(D)(E))n-Xb, (9b)
• and
• wherein, optionally, at least one of the residues Q1 and Q2, respectively independently of each other, is substituted with at least one organic residue W1b which has the general formula (4b), (5b), (6b), (7b), (8b), or (9b),
• wherein h represents a whole number from 1 to 20, wherein k represents a whole number from 0 to 10, wherein 1 represents a whole number from 0 to 10, and wherein m, n and p, respectively independently of each other, represent a whole number from 1 to 6, and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom,
• wherein Xb, respectively independently of each other, is an organic residue which (i) contains at least one neutral nitrogen atom which can be protonated, or (ii) contains at least one positively charged nitrogen atom, or (iii) contains at least one positively charged phosphorus atom, and
• wherein the residues R1, R2, R4 and R5, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms.

A compound with formula (3):

• wherein Mz+ represents a cation of a metal, wherein z is the formal oxidation number of the metal M and is a whole number from 1 to 7 and
• wherein Q1 and Q2, respectively independently of each other, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and
• wherein the residues Q1a and Q2a, respectively independently of each other, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue,
• and wherein
• (a) at least one of the residues Q1 and Q2, respectively independently of each other, is substituted with at least one organic residue W1a which has the general formula (5a), (6a), (7a), (8a), or (9a):
• -A-(C(D)(E))h-Xa, (5a)
• —(C(D)(E))k-aryl-(C(D)(E))l-Xa, (6a)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-Xa, (7a)
• —((C(D)(E))m-A)p-(C(D)(E))n-Xa, (8a)
• -A-((C(D)(E))m-A)p-(C(D)(E))n-Xa, (9a)
• wherein at least one of the residues Q1a and Q2a, respectively independently of each other, is substituted with at least one organic residue W1c which has the general formula (5c), (6c), (7c), (8c), or (9c):
• -A-(C(D)(E))h-Xc, (5c)
• —(C(D)(E))k-aryl-(C(D)(E))l-Xc, (6c)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-Xc, (7c)
• —((C(D)(E))m-A)p-(C(D)(E))n-Xc, (8c)
• -A-((C(D)(E))m-A)p-(C(D)(E))n-Xc, (9c)
• wherein h represents a whole number from 1 to 20, wherein k represents a whole number from 0 to 10, wherein 1 represents a whole number from 0 to 10, and wherein m, n and p, respectively independently of each other, represent a whole number from 1 to 6, and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom, and
• wherein Xa, respectively independently of each other, represents a residue with formula (20c), (20d), (21), or (24):
• wherein each of the residues R(VII), R(VIII), and R(IX), respectively independently of each other, represents hydrogen, an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing 1 to 8 C atoms, and wherein each of the residues R(XV), R(XVI), and R(XVII), respectively independently of each other, represents an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing 1 to 8 C atoms, and
• wherein Xc, respectively independently of each other, is an organic residue which (i) contains at least one neutral nitrogen atom which can be protonated, or (ii) contains at least one positively charged nitrogen atom, or (iii) contains at least one positively charged phosphorus atom, and
• wherein the residues R1, R1a, R2, R2a, R3, R3a, R4, R4a, R5 and R5a, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, cycloalkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms,
• or wherein
• (b) the residue R3 or R3a, respectively independently of each other, is an organic residue W2a, wherein
• the one organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b), or (9b):
• —(C(D)(E))h-Xb, (4b)
• -A-(C(D)(E))h-Xb, (5b)
• —(C(D)(E))k-aryl-(C(D)(E))l-Xb, (6b)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-Xb, (7b)
• —[(C(D)(E))m-A]p—(C(D)(E))n-Xb, (8b)
• -A-[(C(D)(E))m-A]p—(C(D)(E))n-Xb, (9b)
• and
• wherein, optionally, at least one of the residues Q1, Q1a, Q2 and Q2a, respectively independently of each other, is substituted with at least one organic residue W1b which has the general formula (4b), (5b), (6b), (7b), (8b), or (9b),
• wherein h represents a whole number from 1 to 20, wherein k represents a whole number from 0 to 10, wherein l represents a whole number from 0 to 10, and wherein m, n, p, and r, respectively independently of each other, represent a whole number from 1 to 6, and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom,
• wherein Xb, respectively independently of each other, is an organic residue which (i) contains at least one neutral nitrogen atom which can be protonated, (ii) contains at least one positively charged nitrogen atom, or (iii) contains at least one positively charged phosphorus atom, and
• wherein the residues R1, R1a, R2, R2a, R4, R4a, R5 and R5a, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms.

A compound with formula (100):

• and/or with formula (101):
• or respectively a pharmacologically acceptable salt and/or ester and/or complex thereof, for use as a photosensitizer in the medical treatment for the inactivation of microorganisms,
• wherein Q3, Q3a, Q4 and Q4a, respectively independently of each other, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue,
• wherein K represents hydrogen or a cation, and
• wherein Mz+ represents a cation of a metal, wherein z is the formal oxidation number of the metal M and z represents a whole number from 1 to 7, and wherein
• (a1) at least one of the residues Q3, Q3a, Q4 and Q4a, respectively independently of each other, is an unsubstituted, monocyclic or polycyclic heteroaromatic residue, which has at least 5 ring atoms, wherein the ring atoms contain at least one carbon atom and at least one nitrogen atom which preferably-optionally can be protonated, or
• (a2) at least one of the residues Q3, Q3a, Q4 and Q4a, respectively independently of each other, is substituted with at least one organic residue W1, wherein the at least one organic residue W1 has the general formula (4), (5), (6), (7), (8):
• —(C(D)(E))h-X, (4)
• -A-(C(D)(E))h-X, (5)
• —(C(D)(E))k-aryl-(C(D)(E))l-X, (6)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-X, (7)
• —((C(D)(E))m-A)p-(C(D)(E))n-X, (8)
• -A-((C(D)(E))m-A)p-(C(D)(E))n-X, (9)
• wherein h represents a whole number from 1 to 20, wherein k and l, respectively independently of each other, represents a whole number from 0 to 10, and wherein m, n and p, respectively independently of each other, represent a whole number from 1 to 6 and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom,
• wherein X, respectively independently of each other, is an organic residue which (i) contains at least one neutral nitrogen atom which can be protonated, or (ii) at least one positively charged nitrogen atom or (iii) at least one positively charged phosphorus atom, and
• wherein the residues R1, R2, R3, R4 and R5, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, cycloalkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms,
• or wherein
• (b) the residue R3 is an organic residue W2, wherein the one organic residue W2 has the general formula (4), (5), (6), (7), (8), (9), or (10):
• —(C(D)(E))h-X, (4)
• -A-(C(D)(E))h-X, (5)
• —(C(D)(E))k-aryl-(C(D)(E))l-X, (6)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-X, (7)
• —[(C(D)(E))m-A]p—(C(D)(E))n-X, (8)
• -A-[(C(D)(E))m-A]p—(C(D)(E))n-X, (9)
• -(-C(D)=C(E)-)r-X, (10)
• and
• wherein, optionally, at least one of the residues Q3, Q3a, Q4 and Q4a, respectively independently of each other, is substituted with at least one organic residue W1 which has the general formula (4), (5), (6), (7), (8), or (9),
• wherein h represents a whole number from 1 to 20, wherein k and l, respectively independently of each other, represents a whole number from 0 to 10 and wherein m, n, p, and r, respectively independently of each other, represent a whole number from 1 to 6, and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom,
• wherein X, respectively independently of each other, is an organic residue which (i) contains at least one neutral nitrogen atom which can be protonated, (ii) contains at least one positively charged nitrogen atom or (iii) contains at least one positively charged phosphorus atom, and
• wherein the residues R1, R2, R4 and R5, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms.