RU2781292C1 - Derivatives of 1,7-diaryl-1,6-heptadiene-3,5-dione, method for production thereof and use thereof - Google Patents

Abstract

FIELD: medicine.

SUBSTANCE: invention relates to photosensitizers for inactivation of microorganisms. Disclosed are compounds (derivatives) of 1,7-diaryl-1,6-heptadiene-3,5-dione, used as a photosensitizer in medical treatment for inactivating microorganisms, as well as for surface cleaning, coating products, disinfection of liquids and food products. Method of inactivating microorganisms involves bringing microorganisms into contact with at least one photosensitizer and irradiating said microorganisms with electromagnetic radiation.

EFFECT: invention increases efficiency of inactivation of microorganisms.

24 cl, 33 dwg, 5 tbl, 2 ex

Description

The present invention relates to 1,7-diaryl-1,6-heptadiene-3,5-dione derivatives for their preparation and use.

The emergence of an increasing number of bacterial isolates with multiple resistance has led to the fact that it has become more difficult to treat bacterial diseases. Increasingly stringent hygiene standards and a worldwide increase in nosocomial infections have generated interest in new drugs, methods and applications to inhibit the proliferation of multi-resistant strains.

The search for alternatives to antibiotic therapeutics is vital for the treatment of infections caused by bacteria, for example, in particular due to the increase in the occurrence of vancomycin-resistant bacterial strains (VRSA) in 2002 in Japan and the USA. In Europe, the first VRSA isolate from a patient was reported in Portugal in 2013.

The growing resistance of fungal infections to antifungal drugs further increases the difficulty in treating superficial infections. The clinical consequences of antifungal resistance are manifested in treatment failures, especially in immunosuppressed patients.

Accordingly, new approaches to the control of disease-causing pathogens with resistance or multi-resistance consist, on the one hand, in the search for new antidotes, for example, antibiotics or antimycotics, and, on the other hand, in the search for alternative options for inactivation.

It has been shown that one of the alternative methods is photodynamic inactivation of microorganisms. The photooxidative process plays a crucial role in the photodynamic inactivation of microorganisms.

The photosensitizer is excited by light with a specific wavelength. The excited sensitizer can trigger the formation of reactive oxygen species (ROS, ROS), after which, on the one hand, radicals, such as superoxide anions, hydrogen peroxide radicals and hydroxyl radicals, and/or, on the other hand, excited molecular oxygen can be formed, for example, singlet oxygen.

Both reactions are dominated by photooxidation of certain biomolecules that are in close proximity to active forms (ROS). Accordingly, in particular, lipids and proteins are oxidized, for example, they are components of the cell membrane of microorganisms. The destruction of the cell membrane, in turn, leads to the inactivation of the microorganisms that it affects. A similar process of destruction takes place in viruses and bacteria.

As an example, singlet oxygen attacks preferentially oxidation-sensitive molecules. Examples of oxidation sensitive molecules are molecules that contain double bonds or oxidation sensitive groups such as phenols, sulfides or thiols. Unsaturated fatty acids in bacterial membranes are particularly susceptible to damage.

Many sensitizers are known from the prior art, which, for example, originate from the groups of porphyrins and their derivatives, or phthalocyanines and their derivatives, or fullerenes and their derivatives, or are derivatives with a phenolthiazinium structure, such as methylene blue or toluidine blue, for example, or representatives phenoxazinium series, like Nile blue. The photodynamics of methylene blue or toluidine blue against bacteria is already used in dentistry.

Most of the photosensitizers known in the art are substances with a relatively complex molecular structure, which makes them difficult to obtain.

Curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) is one of the most important turmeric curcuminoids. Turmeric (Curcuma longa) is a plant in the ginger family. The yellow color is mainly due to curcumin, demethoxycurcumin, and bisdemethoxycurcumin.

Natural curcumin is characterized by low photostability. For example, in daylight, a curcumin solution clears up within 30 minutes.

Natural curcumin is also characterized by low stability in water. In many cases, to enable its use in the aquatic environment requires the use of solubilizers such as DMSO or other non-biocompatible substances. In addition, its activity against gram-negative bacteria is limited, since the structure of the cell wall of such microorganisms prevents the absorption of curcumin.

Accordingly, one of the objectives of the present invention is to provide new photosensitizers that more effectively inactivate microorganisms.

Another object of the present invention is to provide new photosensitizers that allow photodynamic disinfection of objects and/or fluids and/or patients during therapy and/or prophylaxis.

The object of the present invention is achieved by the proposed method for inactivating microorganisms, which preferably include viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, bloodborne parasites, and combinations thereof, comprising the following steps:

(A) contacting microorganisms with at least one photosensitizer, said sensitizer being at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100):

and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (101):

or a pharmaceutically acceptable salt and/or ester and/or complex of said compound,

where Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue,

where K is hydrogen or a cation, and

where M ^z+ is a metal cation, where z is the formal oxidation state (oxidation number) of the specified metal M, and z is an integer from 1 to 7, preferably from 2 to 5, and where

(a1) at least one of the residues Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, is an unsubstituted, monocyclic or polycyclic heteroaromatic residue that contains at least 5 ring atoms, where the specified ring atoms comprise at least one carbon atom and at least one nitrogen atom, which may preferably be protonated, or

(a2) at least one of Q ³ , Q ^3a , Q ⁴ and Q ^4a , preferably each of Q ³ and Q ⁴ , preferably each of Q ³ and Q ^3a , preferably each of Q ³ , Q ^3a and Q ⁴ , preferably each of the residues Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7 , more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 W1 organic residues of the general formula (4), (5), (6), (7), (8) or (9), preferably (5), (7) or (9):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, are hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, where phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X, respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, nitrogen atom , or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and

where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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 where

(b) R3 is an organic residue W2 having the general formula (4), (5), (6), (7), (8), (9) or (10), preferably (4):

and

where optionally at least one of Q ³ , Q ^3a , Q ⁴ and Q ^4a , preferably each of Q ³ and Q ⁴ , preferably each of Q ³ and Q ^3a , preferably each of Q ³ , Q ^3a and Q ⁴ , preferably each of the residues Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7 , more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3, organic solvents W1 having the general formula (4), (5), (6), (7), (8 ) or (9), preferably (5), (7) or (9),

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n, p and r, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X, respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and

where the residues R1, R2, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing from 2 to 12 C atoms, or a glycol containing from 2 to 12 C atoms, and (B) irradiating said microorganisms and at least one photosensitizer with electromagnetic radiation at a suitable wavelength and energy density.

In a preferred embodiment, the method according to the present invention is carried out to inactivate microorganisms by photodynamic therapy of the patient or by photodynamic disinfection (decontamination) of the surface of the product or liquid, preferably by photodynamic disinfection (decontamination) of the surface of the product or liquid.

The object of the present invention is also achieved by providing at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100)

and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (101):

or a pharmaceutically acceptable salt and/or ester and/or complex of said compound, for use as a photosensitizer in medical treatment to inactivate microorganisms, which are preferably selected from the group consisting of viruses, archaea, bacteria, bacterial spores, fungi, spores fungi, protozoa, algae and blood-borne parasites,

where Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue,

where K is hydrogen or a cation, and

where M ^z+ is a metal cation, where z is the formal oxidation state of said metal M, and z is an integer from 1 to 7, preferably from 2 to 5, and where

(a1) at least one of the residues Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, is an unsubstituted, monocyclic or polycyclic heteroaromatic residue that contains at least 5 ring atoms, where the specified ring atoms comprise at least one carbon atom and at least one nitrogen atom, which may preferably be protonated, or

(a2) at least one of Q ³ , Q ^3a , Q ⁴ and Q ^4a , preferably each of Q ³ and Q ⁴ , preferably each of Q ³ and Q ^3a , preferably each of Q ³ , Q ^3a and Q ⁴ , preferably each of the residues Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3, W1 organic substituents of the general formula (4), (5), (6), (7), (8) or (9); preferably (5), (7) or (9):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X, respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, nitrogen atom , or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and

where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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 where

(b) the residue R3 is an organic residue W2, where the organic residue W2 has the general formula (4), (5), (6), (7), (8), (9) or (10), preferably (4) :

and

where optionally at least one of Q ³ , Q ^3a , Q ⁴ and Q ^4a , preferably each of Q ³ and Q ⁴ , preferably each of Q ³ and Q ^3a , preferably each of Q ³ , Q ^3a and Q ⁴ , preferably each of the residues Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7 , more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3, W1 organic substituents with the general formula (4), (5), (6), (7), (8) or (9), preferably (5), (7) or (9),

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, and where I is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, and where m, n, p and r, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X, respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and

where the residues R1, R2, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing from 2 to 12 C atoms, or a glycol containing from 2 to 12 C atoms.

Preferably, said microorganisms and at least one photosensitizer are irradiated with electromagnetic radiation at a suitable wavelength and energy density.

In one of the preferred embodiments of the invention, in the compound of formula (100), K is a cation M ^z+ metal M, where z is the formal oxidation state of the specified metal M, and where z is an integer from 1 to 7, preferably from 2 up to 3, and where the specified compound has the formula (102):

where L ¹ and L ² , respectively, independently of the others, represent water, fluorine, chloride, bromide, iodide, phosphate, hydrogen phosphate, dihydrogen phosphate, sulfate, hydrogen sulfate, tosylate, mesylate, or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms and/or mixtures thereof. In a preferred embodiment, the carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms is formate, acetate, n-propionate, lactate, oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate, citrate and/or mixtures thereof.

Suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivatives of formula (100) and their preparation are described, for example, in document CA 2 888 140 A1, the contents of which are incorporated herein by reference.

In a preferred embodiment, a suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) is at least one compound of formula (111), (112), (114), (115), (122)-(125) or (137)-(138), preferably at least one compound of formula (114) or (115):

Suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivatives of formula (100) and their preparation are described in EP 2 698 368 A1, the contents of which are incorporated herein by reference.

In a preferred embodiment, a suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) is at least one compound of formula (150), (177), (178), (202), (205) or (209), preferably at least one compound of formula (150) or (177):

A suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) and its preparation are also described in Taka et al. (Bioorg. Med. Chem. Lett. 24, 2014, pp. 5242 - 5246), the contents of which are incorporated herein by reference. In a preferred embodiment, a suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) is a compound of formula (228):

A suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) and its preparation are described in CN 103952008 A1, the contents of which are incorporated herein by reference.

In a preferred embodiment, a suitable 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) is a compound of formula (229):

The object of the present invention is also achieved by providing a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1):

where the residues Q ¹ and Q ² , respectively, independently of the others, represent (one, number = 1) substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

where K is hydrogen or a cation, and

wherein said 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1) does not contain an OH group which is directly linked to the organic residue Q ¹ or Q ² , and where

(a) at least one of the residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably, 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1a with the general formula (5a), (6a), (7a), (8a) or (9a), preferably (5a), (7a) or (9a):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently, represents a residue of formula (20c), (20d), (21) or (24), preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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 where

(b) R3 is an organic residue W2a, where said organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (4b):

and

where, optionally, at least one of the residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably , 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1b with the general formula (4b), (5b), (6b), (7b) , (8b) or (9b), preferably (5b), (7b) or (9b),

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom, which can be protonated, where X ^b is preferred, respectively, independently of the others, represents a residue of formula (20c), (20d), (21) or (24), more preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R2, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing from 2 to 12 C atoms, or a glycol containing from 2 to 12 C atoms.

In one of the preferred embodiments of the invention, in the compound of formula (1), K is a cation M ^z+ metal M, where z is the formal oxidation state of the specified metal M, and where z is an integer from 1 to 7, preferably from 2 up to 3, and where the specified connection has the formula (2):

where L ¹ and L ² , respectively, independently of the others, represent water, fluorine, chloride, bromide, iodide, phosphate, hydrogen phosphate, dihydrogen phosphate, sulfate, hydrogen sulfate, tosylate, mesylate, or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms and/or mixtures thereof. In a preferred embodiment, the carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms is formate, acetate, n-propionate, lactate, oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate, citrate and/or mixtures thereof.

The object of the present invention is also achieved by providing a compound of formula (3):

where M ^z+ is a metal cation, where z is the formal oxidation state of said metal M, and where z is an integer from 1 to 7, preferably from 2 to 5, and

where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

where the residues Q ^1a and Q ^2a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue, preferably one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

and where

(a) at least one of the residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably, 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1a with the general formula (5a), (6a), (7a), (8a) or (9a), preferably (5a), (7a) or (9a):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably, the residue formulas (24):

where each of the residues R ^(VII) , R ^(VIII) , and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms , an alkyl radical which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the radicals R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, preferably an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, or an alkyl residue that may be linear or branched, containing from 1 to 8 C atoms, and

where at least one of the residues Q ^1a and Q ^2a , preferably each of the residues Q ^1a and Q ^2a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 up to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 W1c organic residues with the general formula (4c), (5c), (6c), (7c), (8c ) or (9s), preferably (5s), (7s) or (9s):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) and GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^c , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^c , respectively, independently, represents a residue of the formula (20c), (20d), (21) or (24) , more preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms,

where the residues R1, R1 ^a , R2, R2 ^a , R3, R3 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl, containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms, or where

(b) R3 or R3 ^a , respectively, independently of the others, is an organic residue W2a, wherein said single organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (4b):

and

where optionally at least one of Q ¹ , Q ^1a , Q ² and Q ^2a , preferably each of Q ¹ and Q ² , preferably each of Q ¹ and Q ^1a , preferably each of Q ¹ , Q ¹³ and Q ² , preferably each of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7 , more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 W1b organic residues of the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (5b), (7b) or (9b),

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^b , respectively, independently, represents the residue of the formula (20c), (20d), (21) or (24) , more preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R1 ^a , R2, R2 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 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.

In a preferred embodiment, in the compound of formula (3), the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

(a) at least one of Q ¹ , Q ^1a , Q ² and Q ^2a , preferably each of Q ¹ and Q ² , preferably each of Q ¹ and Q ^1a , preferably each of Q ¹ , Q ^1a and Q ² , preferably each of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 W1a organic residues of the general formula (5a), (6a), (7a), (8a) or (9a), preferably (5a), (7a) or (9a):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably, the residue formulas (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R1 ^a , R2, R2 ^a , R3, R3 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl, containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms,

or where

(b) R3 or R3 ^a , respectively, independently of the others, is an organic residue W2a, wherein said single organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (4b):

and

where optionally at least one of Q ¹ , Q ^1a , Q ² and Q ^2a , preferably each of Q ¹ and Q ² , preferably each of Q ¹ and Q ^1a , preferably each of Q ¹ , Q ^1a and Q ³ , preferably each of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7 , more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 W1b organic residues of the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (5b), (7b) or (9b),

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^b , respectively, independently, represents the residue of the formula (20c), (20d), (21) or (24) , more preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R1 ^a , R2, R2 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 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.

Compounds according to the present invention of formula (1), formula (2) and formula (3), respectively, are a derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione, which is described as follows.

Any suitable anion may be used as a counterion to a positively charged nitrogen atom, eg a protonated nitrogen atom or a quaternary nitrogen atom, or a positively charged phosphorus atom, eg a quaternary phosphorus atom. In a preferred embodiment, the anions used as counterions to the positively charged nitrogen atom or phosphorus atom are atoms that make it possible to obtain pharmacologically acceptable salts.

In one of the preferred embodiments of the present invention, X, X ^a , X ^b and/or X ^c in the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), formula (2 ) and/or formula (3), as well as a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100), formula (101) and/or formula (102) for use in accordance with the present invention is an organic residue containing at least one protonated nitrogen atom or at least one quaternary phosphorus residue, preferably an organic residue with the general formula (20b), (20d), (21) or (24), which contains fluoride, chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms and/or mixtures thereof as a counterion. In a preferred embodiment, the carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms is formate, acetate, n-propionate, lactate, oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate, citrate and/or mixtures thereof.

Additional preferred embodiments of the present invention are described in the dependent claims.

In a more preferred embodiment, the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), formula (2) and/or formula (3), as well as the 1,7- diaryl-1,6-heptadiene-3,5-dione of formula (100), formula (101) and/or formula (102) for use in accordance with the present invention does not contain a neutral nitrogen atom that can be protonated, for example, as in the case of an amino residue, a methylamino residue or a dimethylamino residue and does not contain a positively charged, preferably quaternary nitrogen atom, as in the case of a pyridin-1-ium-1-yl trimethylammonium residue, and also does not contain a positively charged, preferably quaternary, a phosphorus atom that is associated with an organic residue Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^4a .

The term "direct"("directly","directly","directly") should be understood in the sense that the nitrogen atom and/the phosphorus atom is directly bonded to the aromatic residue Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^4a .

The inventors unexpectedly found that the placement of a nitrogen atom and/or a phosphorus atom directly on the aromatic ring system of residues Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ⁴ leads to a significant decrease in the yield of active forms oxygen, for example.

The antimicrobial efficacy of photodynamic therapy or photodynamic cleaning of surfaces or liquids requires the highest possible yield of reactive oxygen species. When the nitrogen atom and/or the phosphorus atom is located directly on the aromatic ring system of the Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^{4a residue} , the absorbed energy is dissipated mainly due to fluorescent effects. This leads to a significant decrease in the efficiency of the photodynamic action, i.e., to a decrease in the amount of reactive oxygen species (ROS, ROS) formed due to photodynamic processes and/or excited molecular oxygen formed in photodynamic processes.

In addition, the inventors surprisingly found that the placement of at least one neutral nitrogen atom, which can be protonated and/or at least one positively charged, preferably quaternary nitrogen atom and/or at least one positively charged, preferably quaternary phosphorus atom on at least one carbon atom, for example in the form of a methylene group, which is thus separated from the aromatic residue Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^4a , does not adversely influencing the photodynamic properties of a compound of formula (1) and/or a compound of formula (2) and/or a compound of formula (3) and/or a compound of formula (100) and/or a compound of formula (101) and/or a compound formulas (102).

The positive charge on the nitrogen atom and/or the phosphorus atom also allows efficient attachment of a compound according to the present invention of formula (1), formula (2), and/or formula (3), and/or a compound for use in accordance with the present invention of formula (100), formulas (101) and/or formulas (102) to negatively charged components of the cell wall of microorganisms. Accordingly, at least one carbon atom, e.g. in the form of a methylene group, also acts as a spacer to effectively position the bulky structure of the compound of formula (1) and/or the compound of formula (2) and/or the compound of formula (3) , and/or compounds of formula (100), and/or compounds of formula (101), and/or compounds of formula (102) on the cell walls of microorganisms.

Further, the inventors surprisingly found that, by arranging at least one neutral nitrogen atom that can be protonated and/or at least one positively charged, preferably quaternary, nitrogen atom and/or at least one positively charged, preferably quaternary phosphorus atom, the solubility of the compound according to the present invention of formula (1), formula (2), and/or formula (3), and/or the compound to be used according to the present invention of formula (100), formula (101 ) and/or formula (102), in polar solvents such as water.

In a more preferred embodiment, the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), formula (2) and/or formula (3), as well as the 1,7- diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100), formula (101) and/or formula (102) does not contain an OH group, which is directly linked to the organic residue Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^4a .

The term "direct"("directly","directly","directly") should be understood in the sense that the OH group is directly linked to the aromatic residue Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or ^Q4a .

The inventors unexpectedly found that the direct location of the OH on group on the aromatic ring system of residues Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^4a leads to a significant violation of the photostability of the photosensitizer. Violation of photostability leads to faster discoloration and, accordingly, to faster inactivation of the photosensitizer when irradiated with electromagnetic radiation with the appropriate wavelength.

Preferably, said at least one neutral nitrogen atom which can be protonated and said at least one positively charged, preferably quaternary nitrogen atom is not a carboxylic acid amide.

In a more preferred embodiment, the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), formula (2) and/or formula (3), as well as the 1,7- diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100), formula (101) and/or formula (102) is not a carbamate residue, which is preferably associated directly with the organic residue Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^4a .

The authors of the present invention found that the location of the carbamate residue directly on the aromatic ring system of residues Q ¹ , Q ^1a , Q ² , Q ^2a , Q ³ , Q ^3a , Q ⁴ or Q ^4a leads to a significant violation of the photostability of the photosensitizer. Violation of photostability leads to faster discoloration and, accordingly, to faster inactivation of the photosensitizer when irradiated with electromagnetic radiation with the appropriate wavelength.

The term "photosensitizer" in the context of the present invention should be understood as meaning compounds that absorb electromagnetic radiation, preferably visible light, UV light and/or infrared light, and thereby form reactive oxygen species (ROS, ROS), preferably free radicals and /or singlet oxygen from triplet oxygen.

The term "photodynamic therapy" in the context of the present invention should be understood to mean the light-induced inactivation of microbial cells, preferably including viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, algae, blood-borne parasites, or combinations thereof, on and/or in the patient's body.

The term "photodynamic disinfection (cleaning)" in the context of the present invention should be understood as meaning light-induced inactivation of microorganisms, preferably including viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, algae, blood-borne parasites, or combinations thereof, on the surfaces of articles and/or foodstuffs and/or in liquids.

The term "inactivation" in the context of the present invention should be understood as meaning the reduction in viability or destruction of the microorganism, preferably its destruction. Light-induced inactivation can, for example, be determined by the decrease in the number of microorganisms after inactivation by cpof a predefined starting quantity of said microorganisms in the presence of at least one compound according to the present invention of formula (1), formula (2) and/or formula (3 ) and/or compounds for use in accordance with the present invention of formula (100), formula (101) and/or formula (102).

In accordance with the present invention, the term "decrease in viability" should be understood to mean that the number of microorganisms is reduced by at least 80.0%, preferably at least 99.0%, preferably at least 99.9%, more preferably at least 99.99% , more preferably at least 99.999%, even more preferably at least 99.9999%. In the most preferred embodiment, the number of microorganisms is reduced by more than 99.9% - 100%, preferably by more than 99.99% 100%.

Preferably, microorganism reduction is carried out in accordance with the guidelines of Boyce, JM, Pittet, D. ("Guidelines for hand hygiene in healthcare settings. Recommendations of the Healthcare Infection Control Practices Advisory Committee and the HIPAC/SHEA/APIC/IDSA Hand Hygiene Task Force", Am. J. Infect. Control 30 (8), 2002, pp. 1-46) as a log ₁₀ attenuation (reduction) factor.

In accordance with the present invention, the term "log ₁₀ attenuation factor" should be understood as meaning the difference between the base 10 logarithm of the number of microorganisms before and the base 10 logarithm of the number of microorganisms after irradiating said microorganisms with electromagnetic radiation in the presence of at least one compound in accordance with the present invention. the invention of formula (1), formula (2) and/or formula (3) and/or a compound for use in accordance with the present invention of formula (100), formula (101) and/or formula (102).

der Viruskrankheiten (DVV) e. V. und der Robert Koch-lnstituts (RKI) zur

von chemischen Desinfektionsmittein auf Wirksamkeit gegen Viren in der Humanmedizin" Bundesgesundheitsblatt, Gesundheitsforschung, Gesundheitsschutz 51(8), (2008), стр. 937-945).Examples of suitable methods for determining the log ₁₀ attenuation factor are described in DIN EN 14885:2007-01 "Chemical disinfectants and antiseptics. Application of European standard for chemical disinfectants and antiseptics" or in Rabenau, HF, Schwebke, I. ("Leitlinie der Deutschen Vereinigung zur

der Viruskrankheiten (DVV) e. V. und der Robert Koch-lnstituts (RKI) zur

von chemischen Desinfektionsmittein auf Wirksamkeit gegen Viren in der Humanmedizin" Bundesgesundheitsblatt, Gesundheitsforschung, Gesundheitsschutz 51(8), (2008), pp. 937-945).

Preferably log ₁₀ is the attenuation coefficient after irradiation of microorganisms with electromagnetic radiation in the presence of at least one compound according to the present invention of formula (1), formula (2) and/or formula (3) and/or a compound for use in accordance with the present formula (100), formula (101) and/or formula (102) is at least 2 log ₁₀ , preferably at least 3 log ₁₀ , more preferably at least 4 log ₁₀ , more preferably at least 4.5 log ₁₀ , more preferably at least 5 log ₁₀ , more preferably at least 6 log ₁₀ , even more preferably at least 7 log ₁₀ , even more preferably at least 7.5 log ₁₀ .

As an example, "the reduction in the number of microorganisms after irradiation of microorganisms with electromagnetic radiation in the presence of at least one compound in accordance with the present invention of formula (1), formula (2) and/or formula (3), and/or a compound for use in accordance with by the present invention of formula (100), formula (101) and/or formula (102) by 2 percentage points relative to the initial number of these microorganisms " denotes a log ₁₀ attenuation factor of 2 log ₁₀ .

In a more preferred embodiment, the number of microorganisms after irradiation of microorganisms with electromagnetic radiation in the presence of at least one compound in accordance with the present invention of formula (1), formula (2) and/or formula (3) and/or a compound for use in accordance with the present invention formula (100), formula (101) and/or formula (102) is reduced by at least 1 percentage point, more preferably at least 2 percentage points, preferably at least 4 percentage points, more preferably at least 5 percentage points, more preferably at least 6 percentage points, even more preferably at least 7 percentage points, relative to the initial number of said microorganisms.

The term "microorganisms" in the context of the present invention should be understood to refer in particular to viruses, archaea, prokaryotic microorganisms such as fungi, protozoa, fungal spores, unicellular algae. Microorganisms can be unicellular or multicellular, such as fungal mycelium.

The 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention has the formula (1):

where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

wherein said 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1) does not contain an OH group which is directly linked to the organic residue Q ¹ or Q ² , and

wherein K represents hydrogen or a cation.

In embodiment (a) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, a monocyclic or polycyclic aromatic residue, K is hydrogen or a cation, and at least one of the residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably 1 to 9, more preferably 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1a with the general formula (5a), (6a ), (7a), (8a) or (9a), preferably (5a), (7a) or (9a):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably, the residue formulas (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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.

In embodiment (b) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, a monocyclic or polycyclic aromatic residue, K is hydrogen or a cation, and R3 is an organic residue W2a having the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (4b ):

and

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged , preferably quaternary, nitrogen atom, where, more preferably, X ^b , respectively, independently, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R2, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing from 2 to 12 C atoms, or a glycol containing from 2 to 12 C atoms.

Optionally, in embodiment (b) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), at least one of Q ¹ and Q ² , preferably each of Q ¹ and Q ² , respectively, independently of the others, has as substituents at least one, preferably 1 to 9, more preferably 1 to 7, more preferably 1 to 5, more preferably 1 to 4 , more preferably 2 to 3 organic residues W1b with the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (5b), (7b) or (9b) :

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged , preferably quaternary, nitrogen atom, where, more preferably, X ^b , respectively, independently, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which May be linear or branched, containing 1 to 8 C atoms.

In one preferred embodiment of the compound of formula (1), K is the cation M ^z+ of the metal M, where z is the formal oxidation state of said metal M, and where z is an integer from 1 to 7, preferably from 2 to 5, more preferably 2 to 3, and wherein said compound has the formula (2):

where L ¹ and L ² , respectively, independently of the others, represent water, fluorine, chloride, bromide, iodide, cyanide, carbonyl, thiocyanate, phosphate, hydrogen phosphate, dihydrogen phosphate, sulfate, hydrogen sulfate, acetylacetonate, acetic acid ester, acetonitrile, tosylate, mesylate or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms, and/or combinations thereof. In a preferred embodiment, the carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms is formate, acetate, n-propionate, lactate, oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate, citrate and/or combinations thereof.

In a more preferred embodiment, L1 and L2 are identical, for example, they are a polydentate ligand. Suitable polydentate ligands contain two or more focal points that can bind to the M ²⁺ cation. Examples of suitable polydentate ligands are ethylenediamine, nitrilotriacetic acid (NTA), ethylenediaminetetraacetate salts (EDTA), acetylacetonate, acetic acid esters, citrate, bis(2-methoxyethyl)ether (diglyme), 8-hydroxyquinolinyl, 2,2'-bipyridine, 1,10-phenanthroline (fen), dimercaptosuccinic acid, tartrate or oxalate.

The 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention also has the formula (3):

In embodiment (a) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (3), M ^z+ is a metal cation M, where z is the formal oxidation state of said metal M and where z is an integer from 1 to 7, preferably from 2 to 3, and

where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

where the residues Q ^1a and Q ^2a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue, preferably one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

and where at least one of the residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1a with the general formula (5a), (6a), (7a), (8a) or ( 9a), preferably (5b), (7b) or (9b):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably, the residue formulas (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where at least one of the residues Q ^1a and Q ^2a , preferably each of the residues Q ^1a and Q ^2a , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 up to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 W1c organic residues with the general formula (4c), (5c), (6c), (7c), (8c ) or (9s), preferably (5s), (7s) or (9s):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^c , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^c , respectively, independently, represents a residue of the formula (20c), (20d), (21) or (24) , more preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms,

where the residues R1, R1 ^a , R2, R2 ^a , R3, R3 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl, containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms.

In embodiment (b) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (3), M ^z+ is a metal cation M, where z is the formal oxidation state of said metal M, and where z is an integer from 1 to 7, preferably from 2 to 5, and

where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

where the residues Q ^1a and Q ^2a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue, preferably one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

and where the residue R3 or R3 ^a , preferably the residues R3 and R3 ^a , respectively, independently of the others, represent an organic residue W2a with the general formula (4b), (5b), (6b), (7b), (8b) or ( 9b), preferably (4b):

and

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom , or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably a quaternary nitrogen atom, where more preferably X ^b , respectively, independently, represents a residue of formula (20c), (20d), (21) or (24), more preferably a residue of formula (20c), ( 20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R1 ^a , R2, R2 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 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.

Optionally, in variant (b) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (3), at least one of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , preferably each of residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ^1a , preferably each of the residues Q ¹ , Q ^1a and Q ² , preferably each of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently from others, has as substituents at least one, preferably 1 to 9, more preferably 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1b with the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (5b), (7b) or (9b):

and

where h is an integer from 1 to 20, preferably from 1 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 1 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom , or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably a quaternary nitrogen atom, where more preferably X ^b , respectively, independently, represents a residue of formula (20c), (20d), (21) or (24), more preferably a residue of formula (20c), ( 20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or alkyl residue, which May be linear or branched, containing 1 to 8 C atoms.

In one preferred embodiment of a compound of formula (3), said compound has formula (3a):

In embodiment (a) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (3a), M ^z+ is a metal cation M, where z is the formal oxidation state of said metal M, and where z is an integer from 1 to 7, preferably from 2 to 3, and where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

where at least one of the residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 up to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1a with the general formula (5a), (6a), (7a), (8a) or (9a ), preferably (5a), (7a) or (9a):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably, the residue formulas (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 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, preferably an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, or an alkyl the remainder, which No be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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.

In embodiment (b) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (3a), M ^z+ is a metal cation M, where z is the formal oxidation state of said metal M, and where z is an integer from 1 to 7, preferably from 2 to 5, and

where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue,

and where the residue R3 respectively represents an organic residue W2a, where the organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (4b):

and

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom , or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably a quaternary nitrogen atom, where more preferably X ^b , respectively, independently, represents a residue of formula (20c), (20d), (21) or (24), more preferably a residue of formula (20c), ( 20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) ), respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, preferably an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, or an alkyl residue that can may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R2, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing from 2 to 12 C atoms, or a glycol containing from 2 to 12 C atoms.

Optionally, in embodiment (b) of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (3a), at least one of Q ¹ and Q ² , preferably each of Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably from 1 to 7, more preferably from 1 to 5, more preferably from 1 to 4, more preferably, 2 to 3 organic residues W1b with the general formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably (5b), (7b) or (9b):

and

where h is an integer from 1 to 20, preferably from 1 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 1 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom , or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably a quaternary nitrogen atom, where more preferably X ^b , respectively, independently, represents a residue of formula (20c), (20d), (21) or (24), more preferably a residue of formula (20c), ( 20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) ), respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, preferably an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, or an alkyl residue that May be linear or branched, containing 1 to 8 C atoms.

In one preferred embodiment of a compound of formula (2) and/or a compound of formula (3) and/or a compound of formula (3a) and/or a compound of formula (101) and/or a compound of formula (102), the metal M selected from the group consisting of alkali metals, alkaline earth metals, transition metals, metals and metalloids from the third, fourth, fifth and sixth main groups of the periodic table of elements and combinations thereof; in a preferred embodiment, the metal M is selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Tc, Rh, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au, Zn, B, Al, Ga, In, Si, Ge, Sn, Bi, Se, Te and combinations thereof.

More preferably, the metal M is selected from the group consisting of B, Al, Zn, Cu, Mg, Ca, Fe, Si, Ga, Sn, Rh, Co, Ti, Zr, V, Cr, Mo, Mn, Ru , Pd, Ir, Ni and their combinations. More preferably, M ^z+ is Mg ²⁺ , Ca ²⁺ , Fe ²⁺ , Fe ³⁺ , Zn ²⁺ , Cu ²⁺ , B ³⁺ or Si ⁴⁺ .

According to the present invention, in a compound of formula (1), or a compound of formula (2), or a compound of formula (3a), residues Q ¹ and Q ² , or in a compound of formula (3) residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, which preferably, respectively, independently of the others, is a phenyl residue, naphthyl residue, azulene residue, phenalene residue, acenaphthyl residue, fluorene residue, phenanthrene residue, anthracene residue, fluoranthene residue, pyrene residue, benzo[a]anthracene residue, chrysene residue, a benzo[b]fluoranthene residue, benzo[h]fluoranthene residue, a benzo[a]pyrene residue, dibenzo[a, h] an anthracene residue, a tetracene residue, a triphenylene residue, a pentacene residue, or a hexacene residue, more preferably a phenyl residue, a naphthyl residue, a phenalene residue, or anthracene residue.

In accordance with the present invention, in a compound of formula (100) or a compound of formula (102), residues Q ³ and Q ⁴ , or in a compound of formula (101), residues Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, regardless of others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, which preferably, respectively, independently of the others, represent a phenyl residue, a naphthyl residue, an azulene residue, a phenalene residue, an acenaphthyl residue, a fluorene residue, a phenanthrene residue, an anthracene residue, a fluoranthene residue , pyrene residue, benzo[a]anthracene residue, chrysene residue, benzo[b]fluoranthene residue, benzo[h]fluoranthene residue, benzo[a]pyrene residue, dibenzo[a,h]anthracene residue, tetracene residue, triphenylene a residue, a pentacene residue or a hexacene residue, more preferably a phenyl residue, a naphthyl residue, a phenalene residue or an anthracene residue, or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue, which preferably contains at least 5 ring atoms, where these ring atoms include at least one carbon atom and at least one nitrogen atom, which in the preferred embodiment can be protonated, where, more preferably, said one substituted or unsubstituted monocyclic or polycyclic heteroatomic residue, respectively, independently of the others, is a pyrrole residue, a pyridine residue, a quinolinyl residue, an isoquinoline residue, an indole residue, an isoindole residue, a pyrimidine residue, a pyrazine residue, an imidazole residue, or an actidine residue , more preferably a pyridine residue, a quinolinyl residue, an isoquinoline residue, or an indole residue.

In a preferred embodiment, said one substituted or unsubstituted, monocyclic or polycyclic, heteroatomic residue contains from 5 to 14, more preferably from 6 to 10 ring atoms, where said ring atoms include at least 1 carbon atom or at least 1 nitrogen atom , which can preferably be protonated. More preferably, the ring atoms comprise from 1 to 3 nitrogen atoms, which preferably can be protonated, and which, even more preferably, are not adjacent to each other.

In embodiment (a1) of a compound of formula (100), a compound of formula (101), and/or a compound of formula (102), at least one of Q ³ , Q ^3a , Q ⁴ and Q ^4a , respectively, independently of the others, is an unsaturated monocyclic or polycyclic heteroaromatic residue which contains at least 5, preferably 5 to 14, more preferably 6 to 10 ring atoms, wherein said ring atoms comprise at least one carbon atom and at least one nitrogen atom, which may preferably be protonated. More preferably, said ring atoms comprise from 1 to 3, preferably 1 or 2, nitrogen atoms, which can preferably be protonated. In an even more preferred embodiment, these nitrogen atoms are not located in adjacent positions.

In a preferred embodiment, said substituted monocyclic or polycyclic aromatic residues or substituted monocyclic or polycyclic, heteroatomic residues, with at least one organic residue W1, or one organic residue W1a or one organic residue W1b, or one organic residue W1c, and/or with a halogen , nitro, carboxylate, aldehyde containing from 1 to 8 C atoms, ketone containing from 2 to 8 C atoms, O-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, O -aryl containing from 5 to 20 C atoms, an ester containing from 2 to 12 C atoms, a carboxylic acid ester containing from 1 to 12 C atoms, a carboxylic acid amide containing from 1 to 12 C atoms, where preferably the C atom of the carboxamide group is linked to the indicated substituted monocyclic or polycyclic aromatic residues or substituted monocyclic or polycyclic, hetero-atomic residues, alkyl containing 1 to 12 C atoms, alkenyl containing 2 to 12 C atoms, cycloalkyl containing 3 to 12 C atoms, cycloalkenyl containing 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, or heteroaryl, which does not contain a nitrogen atom, contain substituents from 4 to 40 C atoms.

More preferably, said substituted monocyclic or polycyclic aromatic residues or substituted monocyclic or polycyclic, heteroatomic residues containing at least one W1 organic residue, or one W1a organic residue, or one W1b organic residue, or one W1c organic residue, and/or containing halogen, nitro, aldehyde containing from 1 to 8 C atoms, ketone containing from 2 to 8 C atoms, O-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, O -aryl containing from 5 to 20 C atoms, ester containing from 2 to 12 C atoms, carboxylic acid ester containing from 1 to 12 C atoms, alkyl containing from 1 to 12 C atoms, alkenyl,

containing from 2 to 12 C atoms, cycloalkyl containing from 3 to 12 C atoms, cycloalkenyl containing from 3 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, or heteroaryl, which does not contain a nitrogen atom, contain from 4 to 40 C atoms in the substituents.

In a preferred embodiment, said one substituted or unsubstituted monocyclic or polycyclic aromatic residue contains at least 5 ring atoms, preferably 5 to 16, more preferably 6 to 14, more preferably 6 to 10, which respectively contain at least at least 1 carbon atom and at least one, preferably 1 to 2, oxygen atoms, which are more preferably not in adjacent positions.

Preferably in a compound of formula (1) and/or a compound of formula (2) and/or a compound of formula (3a), a Q ¹ moiety, or in a compound of formula (100) and/or a compound of formula (102), a Q ³ moiety is an aromatic residue with the general formula (11a), (12a), (13a), (14a), (15a), (16a), (17a), (18a) or (19a):

where in the compound of formula (1) and/or the compound of formula (2) and/or the compound of formula (3a), the residue Q ² or in the compound of formula (100) and/or in the compound of formula (102), the residue Q ⁴ is aromatic residue with the general formula (11b), (12b), (13b), (14b), (15b), (16b), (17b), (18b) or (19b):

where respectively at least 1, preferably from 1 to 9, more preferably from 1 to 7, more preferably from 1 to 5, more preferably from 1 to 4, more preferably from 2 to 3 residues R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^25a - R ^33a , R ^34a - R ^42a , R ^43a - R ^51a R ^52a - R ^60a , R ^61a - R ^69a , R ^70a - R ^78a , R ^6b - R ^10b , R ^11b - R ^17b , R ^18b - R ^24b , R ^25b - R ^33b , R ^34b - R ^42b , R ^43b - R ^51b , R ^52b - R ^60b , R ^61b - R ^69b or R ^70b - R ^78b , respectively, independently of the others, are an organic residue W1 or an organic residue W1 a, an organic residue W1b, or an organic residue W1c, and

where the residues are R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^25a - R ^33a , R ^34a - R ^42a , R ^43a - R ^51a , R ^52a -R ^60a R ^61a - R ^69a , R ^70a - R ^78a , R ^6b - R ^10b , R ^11b - R ^17b R ^18b - R ^24b , R ^25b - R ^33b R ^34b - R ^42b , R ^43b - R ^51b , R ^52b - R ^60b , R ^61b - R ^69b or R ^70b - R ^78b which is not an organic residue W1, o or an organic residue W1a, or an organic residue W1b, or an organic residue W1c, respectively, independently of the others, are identical or different and represent hydrogen, halogen, nitro, carboxylate, aldehyde , containing from 1 to 8 C atoms, a ketone containing from 2 to 8 C atoms, O-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, O-aryl containing from 5 up to 20 C atoms, an ester containing from 2 to 12 C atoms, a carboxylic acid ester containing from 1 to 12 C atoms, a carboxylic acid amide containing from 1 to 12 C atoms, where, preferably, respectively, the C atom of the carboxamide group is bonded to one of the tkov Q ¹ - Q ⁴ , alkyl containing from 1 to 12 C atoms, alkenyl containing from 2 to 12 C atoms, cycloalkyl containing from 3 to 12 C atoms, cycloalkenyl containing from 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, or heteroaryl which does not contain a nitrogen atom containing 4 to 20 C atoms, preferably hydrogen, halogen, nitro, carboxylate, aldehyde containing 1 to 8 C atoms, ketone containing 2 to 8 C atoms, O-alkyl containing 1 to 12 C atoms, O-alkenyl containing 2 to 12 C atoms, O-aryl containing 5 to 20 C atoms, ester of 2 to 12 C atoms, carboxylic ester of 1 to 12 C atoms, alkyl of 1 to 12 C atoms, alkenyl of 2 to 12 C atoms, cycloalkyl of 3 to 12 atoms C, cycloalkenyl containing 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, or heteroaryl which does not contain a nitrogen atom, c containing from 4 to 20 C atoms.

More preferably, the Q ¹ residue or the Q ³ residue is an aromatic residue with the general formula (11a), (12a) or (13a)

and the Q ² residue or the Q ⁴ residue is an aromatic residue with the general formula (11b), (12b) or (13b),

where, respectively, at least 1, preferably from 1 to 9, more preferably from 1 to 7, more preferably from 1 to 5, more preferably from 1 to 4, more preferably from 2 to 3 residues R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^6b - R ^10b , R ^11b - R ^17b or R ^18b - R ^24b , respectively, independently of the others, represents an organic residue W1, or an organic residue W1a , or an organic residue W1b, or an organic residue W1c, and and where the residues R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^6b - R ^10b , R ^11b - R ^17b and R ^18b - R ^24b , which are not organic residue W1, or organic residue W1a, or organic residue W1b, or organic residue W1c, respectively, independently of others, are identical or different and represent hydrogen, halogen, nitro, carboxylate, aldehyde containing from 1 to 8 C atoms, ketone , containing from 2 to 8 C atoms, O-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, O-aryl containing from 5 to 20 C atoms, ester containing from 2 to 12 C atoms, carboxylic acid ester containing from 1 to 12 C atoms, carboxylic acid amide containing from 1 to 12 C atoms, where , preferably, respectively, the C atom of the carboxamide group is bonded to one of the residues Q ¹ - Q ⁴ , alkyl containing from 1 to 12 C atoms, alkenyl containing from 2 to 12 C atoms, cycloalkyl containing from 3 to 12 C atoms, cycloalkenyl containing from 3 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, or heteroaryl which does not contain a nitrogen atom, containing from 4 to 20 C atoms, preferably hydrogen , halogen, nitro, carboxylate, aldehyde containing 1 to 8 C atoms, ketone containing 2 to 8 C atoms, O-alkyl containing 1 to 12 C atoms, O-alkenyl containing 2 to 12 C atoms , O-aryl containing from 5 to 20 C atoms, ester containing from 2 to 12 C atoms, carboxylic acid ester containing from 1 to 12 C atoms, alkyl, c containing from 1 to 12 C atoms, alkenyl containing from 2 to 12 C atoms, cycloalkyl containing from 3 to 12 C atoms, cycloalkenyl containing from 3 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl, containing from 5 to 20 C atoms, or heteroaryl, which does not contain a nitrogen atom, containing from 4 to 20 C atoms.

Preferably, in the compound of formula (3), the residues Q ¹ and Q ^1a , or in the compound of formula (101), the residues Q ³ and Q ^3a , respectively, independently of the others, are an aromatic residue with the general formula (11a), ( 12a), (13a), (14a), (15a), (16a), (17a), (18a) or (19a):

and where in the compound of formula (3) the residues Q ² and Q ^2a , or in the compound of formula (101) the residues Q ⁴ and Q ^4a , respectively, independently of the others, represent an aromatic residue with the general formula (11b), (12b), ( 13b), (14b), (15b), (16b), (17b), (18b) or (19b):

where, respectively, at least 1, preferably from 1 to 9, more preferably from 1 to 7, more preferably from 1 to 5, more preferably from 1 to 4, more preferably from 2 to 3 residues R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^25a - R ^33a , R ^34a - R ^42a , R ^43a - R ^51a , R ^52a - R ^60a , R ^61a - R ^69a R ^70a - R ^78a R ^6b - R ^10b , R ^11b - R ^17b , R ^18b - R ^24b , R ^25b - R ^33b , R ^34b - R ^42b , R ^43b - R ^51b , R ^52b - R ^60b , R ^61b - R ^69b or R ^70b - R ^78b , respectively, independently of the others, represents an organic residue W1, or an organic residue W1 a, or an organic residue W1b, or an organic residue W1c, and

where the residues are R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^25a - R ^33a , R ^34a - R ^42a , R ^43a - R ^51a , R ^52a - R ^60a R ^61a - R ^69a , R ^70a - R ^78a , R ^6b - R ^10b R ^11b - R ^17b , R ^18b - R ^24b , R ^25b - R ^33b , R ^34b - R ^42b , R ^43b - R ^51b , R ^52b - R ^60b , R ^61b - R ^69b or R ^70b to R ^78b which are not organic W1 or organic W1a or organic W1b or organic W1c, respectively, are independently identical or different and are hydrogen, halogen, nitro, carboxylate, aldehyde , containing from 1 to 8 C atoms, a ketone containing from 2 to 8 C atoms, O-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, O-aryl containing from 5 up to 20 C atoms, an ester containing from 2 to 12 C atoms, a carboxylic acid ester containing from 1 to 12 C atoms, a carboxylic acid amide containing from 1 to 12 C atoms, where preferably, respectively, the C atom of the carboxamide group is bonded to one of the atkov Q ¹ - Q ^4a , alkyl containing from 1 to 12 C atoms, alkenyl containing from 2 to 12 C atoms, cycloalkyl containing from 3 to 12 C atoms, cycloalkenyl containing from 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms or heteroaryl which does not contain a nitrogen atom containing 4 to 20 C atoms, preferably hydrogen, halogen, nitro, carboxylate, aldehyde containing 1 to 8 atoms C, ketone containing from 2 to 8 C atoms, O-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, O-aryl containing from 5 to 20 C atoms, ether, containing from 2 to 12 C atoms, carboxylic acid ester containing from 1 to 12 C atoms, alkyl containing from 1 to 12 C atoms, alkenyl containing from 2 to 12 C atoms, cycloalkyl containing from 3 to 12 C atoms, cycloalkenyl containing 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, or heteroaryl which does not contain a nitrogen atom, containing from 4 to 20 C atoms.

More preferably, in the compound of formula (3), the residues Q ¹ and Q ^1a , or, in the compound of formula (101), the residues Q ³ and Q ^3a , respectively, independently of the others, are an aromatic residue with the general formula (11a) , (12a) or (13a):

and where in the compound of formula (3), the residues Q ² and Q ^2a , or, in the compound of formula (101), the residues Q ⁴ and Q ^4a , respectively, independently of the others, represent an aromatic residue with the general formula (11b), ( 12b) or (13b):

where, respectively, at least 1, preferably from 1 to 9, more preferably from 1 to 7, more preferably from 1 to 5, more preferably from 1 to 4, more preferably from 2 to 3 residues R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^6b - R ^10b , R ^11b - R ^17b or R ^18b - R ^24b , respectively, independently of the others, represents an organic residue W1, or an organic residue W1a , or organic residue W1b, or organic residue W1c, where

residues R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^6b - R ^10b , R ^11b - R ^17b and R ^18b - R ^24b which are not organic residue W1 or organic residue W1a or organic residue W1b , or an organic residue W1c, respectively, independently of the others, are identical or different and represent hydrogen, halogen, nitro, carboxylate, aldehyde containing from 1 to 8 carbon atoms, ketone containing from 2 to 8 carbon atoms, O-alkyl, containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, O-aryl containing from 5 to 20 C atoms, ester containing from 2 to 12 C atoms, carboxylic acid ester containing from 1 to 12 C atoms, carboxylic acid amide containing from 1 to 12 C atoms, where preferably, respectively, the C atom of the carboxamide group is bonded to one of the residues Q ¹ - Q ^4a , alkyl containing from 1 to 12 C atoms, alkenyl containing from 2 to 12 C atoms, cycloalkyl containing 3 to 12 C atoms, cycloalkenyl containing 3 to 12 C atoms, alkylaryl, containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, or heteroaryl which does not contain a nitrogen atom containing from 4 to 20 C atoms, preferably hydrogen, halogen, nitro, carboxylate, aldehyde containing from 1 to 8 C atoms, ketone containing 2 to 8 C atoms, O-alkyl containing 1 to 12 C atoms, O-alkenyl containing 2 to 12 C atoms, O-aryl containing 5 to 20 C atoms, ester of 2 to 12 C atoms, carboxylic ester of 1 to 12 C atoms, alkyl of 1 to 12 C atoms, alkenyl of 2 to 12 C atoms, cycloalkyl of 3 to 12 atoms C, cycloalkenyl containing 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, or heteroaryl that does not contain a nitrogen atom containing 4 to 20 C atoms.

In an alternative embodiment of option (b) of a compound of formula (1) and/or a compound of formula (2) and/or a compound of formula (3) and/or a compound of formula (3a), at least one organic residue W2a has a common formula (4b), (5b), (6b), (7b), (8b) or (9b), preferably the general formula (5b), (7b) or (9b):

where, optionally, at least one of the residues Q ¹ and Q ² , preferably each of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one, preferably from 1 to 9, more preferably , 1 to 7, more preferably 1 to 5, more preferably 1 to 4, more preferably 2 to 3 organic residues W1b with the general formula (4b), (5b), (6b), (7b) , (8b) or (9b), preferably with the general formula (5b), (7b) or (9b),

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, preferably oxygen, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, preferably (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged , preferably quaternary, nitrogen atom, where the specified at least one neutral nitrogen atom, which can be protonated, is not an amino residue (-NH ₂ ), and where the specified at least one positively charged nitrogen atom is not a protonated amino - residue (-NH ₃ ⁺ ) and is not a guanylate residue.

In a preferred embodiment In an alternative embodiment of option (b) a compound of formula (1) and/or a compound of formula (2) and/or a compound of formula (3) and/or a compound of formula (3a), an organic moiety X ^b , respectively , independently of the others, is a residue of formula (20a), (20b), (21), (22a), (22b), (23a), (23b) or (24), preferably a residue of formula (20a), ( 20b), (21) or (24), preferably a residue of formula (20a), (20b) or (21):

where each of the residues R ^(IVa) , R ^(IVb) , R ^(X) , R ^(XI) , R ^(XII) , R ^(XIII) , and R ^(XIV) , preferably each of the residues R(iva) and r (ivb), respectively, independently of the others, are hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched containing from 1 to 8 C atoms, and

where each of the residues R ^(Va) , R ^(Vb) , R ^(VIb) , R ^(VII) , R ^(VIII) , R ^(XV) , and R ^(XVII) is preferably each of R ^(IVa) , R ^{(Vb )} , R ^(VIb) ,R ^(XV) , R ^(XVI) , R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and

where the remainder of formula (22a) and the remainder of formula (23a):

represents a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a double bond, and

where the remainder of formula (22b) and the remainder of formula (23b):

represent a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a single bond.

In one preferred embodiment of a compound of formula (100), a compound of formula (101), and/or a compound of formula (103), the organic moiety X, respectively, independently of the others, is a moiety of formula (20a), (20b), ( 21), (22a), (22b), (23a), (23b) or (24), preferably a residue of formula (20a), (20b) or (21):

where each of the residues R ^(IVa) , R ^(Va) , R ^(IVb) , R ^(Vb) , R ^(VIb) , R ^(VII) , R ^(VIII) , R ^(IX) , R ^(X) , R ^(XI) , R ^(XII) , R ^(XIII) , and R ^(XIV) , respectively, independently of the others, are hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and

where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represents an aryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 up to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and

where the remainder of formula (22a) and the remainder of formula (23a):

represents a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a double bond, and

where the remainder of formula (22b) and the remainder of formula (23b):

represents a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a single bond.

In one preferred embodiment of a compound of formula (1), a compound of formula (2), and/or a compound of formula (3), the organic moiety X ^b and/or X ^c , respectively, independently of the others, is a moiety of formula (20a) , (20b), (21), (22a), (22b), (23a), (23b) or (24):

where each of the residues R ^(IVa) , R ^(Va) , R ^(IVb) , R ^(Vb) , R ^(VIb) , R ^(VII) , R ^(VIII) , R ^(IX) , R ^(X) , R ^(XI) , R ^(XII) , R ^(XIII) , and R ^(XIV) , respectively, independently of the others, are hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and

where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represents an aryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 up to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and

where the remainder of formula (22a) and the remainder of formula (23a):

represents a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a double bond, and

where the remainder of formula (22b) and the remainder of formula (23b):

represents a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a single bond.

More preferably, each residue of formula (23a) is selected from the group consisting of residues of formulas (25a), (25b) and (25c):

where R ^(XI) may respectively represent an aryl residue containing from 5 to 20 C atoms, for example, phenyl or benzyl, an alkyl residue, which may be linear or branched, containing from 1 to 20 C atoms, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl or tert-butyl, an alkenyl radical, which may be linear or branched, containing from 2 to 20 C atoms, a hydroxyalkyl radical, which may be linear or branched, containing from 1 to 20 C atoms, e.g. hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl or 1-hydroxy-1-methylethyl, or an ethyl residue which may be linear or branched containing from 2 to 20 C atoms, e.g. methoxymethyl, methoxyethyl, methoxypropyl , ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl, propoxyethyl or propoxypropyl.

In a more preferred embodiment, each residue of formula (22a) is selected from the group consisting of residues of formula (26):

where the residues R ^(XIIa) - R ^(XIIe) , respectively, independently of the others, may be hydrogen, an aryl residue containing from 5 to 20 C atoms, for example, phenyl or benzyl, an alkyl residue, which may be linear or branched, containing from 1 to 20 C atoms, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl or tert-butyl, an alkenyl radical, which may be linear or branched, containing from 2 to 20 C atoms, a hydroxyalkyl radical, which may be linear or branched, containing from 1 to 20 C atoms, for example, hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl or 1-hydroxy-1-methyl-ethyl, or an ether residue, which may be linear or branched, containing from 2 to 20 C atoms, for example methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl, propoxyethyl or propoxypropyl. In a preferred embodiment, the residues R ^(XIIa) - R ^(XIIe) , respectively, independently of the others, are hydrogen, methyl, ethyl, prop-1-yl, but-1-yl, pent-1-yl, hex-1-yl , hept-1- or oct-1-yl.

In a more preferred embodiment, the residue of formula (21b) is 1-methylpyrrolidin-1-yl-1-yl, 1-methylpiperazin-1-yl-1-yl, or 4-methylmorpholin-4-yl-4-yl.

In a more preferred embodiment of a compound of formula (100), a compound of formula (101), and/or a compound of formula (103), the organic moiety X, respectively, independently of the others, is a moiety of formula (20c), (20d), (21) or (24), preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be linear or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, preferably hydrogen, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) ), respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, preferably an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, or an alkyl residue that May be linear or branched, containing 1 to 8 C atoms.

In a more preferred embodiment, in a compound of formula (100), a compound of formula (101), and/or a compound of formula (103), the residues R ^(IVa) , R ^(Va) , R ^(IVb) , R ^(Vb) , R ^{(VIb )} , R ^(VII) , R ^(VIII) , R ^(IX) , R ^(X) , R ^(XI) , R ^(XII) , R ^(XIII) , R ^(XIV) , R ^(XV) , R ^{(XVI )} and R ^(XVII) are independently selected from hydrogen and alkyl groups with the general formula -(CH ₂ ) _n -CH ₃ , where n is an integer from 0 to 19, preferably from 1 to 17.

In a more preferred embodiment, in a compound of formula (1) and/or a compound of formula (2) and/or a compound of formula (3) and/or a compound of formula (3a) and/or a compound of formula (100) and/ or a compound of formula (101), and/or a compound of formula (102) residues R ^(IVa) , R ^(Va) , R ^(IVb) , R ^(Vb) , R ^(VIb) , R ^(VII) , R ^(VIII) , R ^(IX) , R ^(X) , R ^(XI) , R ^(XII) , R ^(XIII) and R ^(XIV) are independently selected from the group consisting of hydrogen, methyl, ethyl, prop-1- yl, prop-2-yl, but-1-yl, but-2-yl, 2-methylprop-1-yl, 2-methylprop-2-yl, pent-1-yl, pent-2-yl, pent- 3-yl, 2-methylbut-1-yl, 2-methylbut-2-yl, 2-methylbut-3-yl, 2-methylbut-4-yl, 2,2-dimethylprop-1-yl, hex-1- yl, hex-2-yl, hex-3-yl, hept-1-yl, oct-1-yl, 2-methylpent-1-yl, 2-methylpent-2-yl, 2-methylpent-3-yl, 2-methylpent-4-yl, 2-methylpent-5-yl, 3-methylpent-1-yl, 3-methylpent-2-yl, 3-methylpent-3-yl, 2,2-dimethylbut-1-yl, 2,2-dimethylbut-3-yl, 2,2-dimethylbut-4-yl, 2,3-dimethylbut-1-yl, 2,3-dimethylbu t-2-yl, phenyl and benzyl.

In a particularly preferred embodiment of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), formula (2), formula (3) and/or formula (3a) and also 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100), formula (101) and/or formula (102) for use in accordance with the present invention, residues R ^(XV) , R ^{( XVI)} and R ^(XVII) ) corresponding to formula (24),

independently selected from methyl, ethyl, prop-1-yl, prop-2-yl, but-1-yl, but-2-yl, 2-methylprop-1-yl, 2-methylprop-2-yl, pent -1-yl, pent-2-yl, pent-3-yl, 2-methylbut-1-yl, 2-methylbut-2-yl, 2-methylbut-3-yl, 2-methylbut-4-yl, 2 ,2-dimethylprop-1-yl, hex-1-yl, hex-2-yl, hex-3-yl, hept-1-yl, oct-1-yl, 2-methylpent-1-yl, 2-methylpent -2-yl, 2-methylpent-3-yl, 2-methylpent-4-yl, 2-methylpent-5-yl, 3-methylpent-1-yl, 3-methylpent-2-yl, 3-methylpent-3 -yl, 2,2-dimethylbut-1-yl, 2,2-dimethylbut-3-yl, 2,2-dimethylbut-4-yl, 2,3-dimethylbut-1-yl and 2,3-dimethylbut-2 -yl, phenyl and benzyl.

In a more preferred embodiment of a compound of formula (100), a compound of formula (101), and/or a compound of formula (103), the residues R ^(IVa) , R ^(Va) , R ^(IVb) , R ^(Vb) , R ^(VIb) , R ^(VII) , R ^(VIII) , R ^(IX) , R ^(X) , R ^(XI) , R ^(XII) , R ^(XIII) , R ^(XIV) , R ^(XV) , R ^(XVI) and R ^(XVII) ) is independently selected from hydrogen or a residue of formula (10):

where, respectively, r represents an integer from 1 to 20, preferably from 1 to 8, more preferably from 1 to 4.

In a more preferred embodiment of the 1,7-diaryl-1,6-hepta-diene-3,5-dione derivative of formula (100) and/or formula (101) and/or formula (102), the organic organic residue W2 and /or W1, respectively, independently of the others, represent an organic residue with the general formula (30a), (30b), (30c), (30d), (30e), (30f), (30g), (30h), (30i ), (30k), (30m), (30n), (30p), (31a), (31b), (32), (33), (34), (35), (36), (37a) or (37b), preferably an organic residue with the general formula (30a), (30b), (30c), (30d), (30e), (30f), (30g), (30h), (30i), (30k), (30m), (30n), (30p), (31a), (31b), (32), (33), (34), (35) or (36), preferably an organic residue with the general formula (37a):

where Y ^- represents an anion, which, respectively, independently of the others, represents fluoride, chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms. In a preferred embodiment, the carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms is independently formate, acetate, n-propionate, lactate, oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate, or citrate.

In a more preferred embodiment of the 1,7-diaryl-1,6-hepta-diene-3,5-dione derivative of the present invention of formula (1) and/or formula (2) and/or formula (3) and/ or formula (3a), the organic residue W1a, respectively, independently of the others, represents an organic residue with the general formula (31a), (31b), (32), (34), (37a) or (37b), preferably an organic residue with a general formula (31a), (31b), (32) or (34), preferably an organic residue with the general formula (37a):

where Y ^- represents an anion, which, respectively, independently of the others, represents fluoride, chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms. In a preferred embodiment, the carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms is, Regardless of others, formate, acetate, n-propionate, lactate, oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate or citrate.

In a more preferred embodiment of the 1,7-diaryl-1,6-hepta-diene-3,5-dione derivative of the present invention of formula (1) and/or formula (2) and/or formula (3), and /or formula (3a) organic residue W2a, and/or W1b, and/or W1c, respectively, independently of others, represent an organic residue with the general formula (31a), (31b), (32), (34), (35 ), (37a) or (37b), preferably an organic residue with the general formula (31a), (31b), (32), (34) or (35), preferably an organic residue with the general formula (37a):

where Y ^- represents an anion, which, respectively, independently of the others, represents fluoride, chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms. In a preferred embodiment, the carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms is, and independently, formate, acetate, n-propionate, lactate, oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate or citrate.

In a more preferred embodiment of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) for use in accordance with the present invention, said compound is at least one compound of formula (40)-( 67), preferably at least one compound of formula (40)-(63), (66) or (67), preferably a compound of formula (64):

In a more preferred embodiment of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) for use in accordance with the present invention, said compound is at least one compound of formula (40)-( 67) and (110)-(229).

In a more preferred embodiment of the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1), said compound is at least one compound of formula (40)-(65), preferably , at least one compound of formula (40)-(62), preferably at least one compound of formula (40)-(58), (60), (61), (62) or (63), preferably at least one compound of formula (64):

In a more preferred embodiment, the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (2) or the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (102) for use in accordance with the present invention, said compound is at least one compound of formula (68), (69a) or (69b):

In a more preferred embodiment, the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (3) or the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (101) for use in accordance with the present invention, said compound is at least one compound of formula (70):

In the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) according to the present invention, as well as in a derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione of formula (100), and/or formula (101), and/or formula (102), and/or formula ( 3a) for use in accordance with the present invention, said ketone residues, carboxylic acid residues, carboxylic acid amide residues, cycloalkyl residues, cycloalkenyl residues, alkyl residues and alkenyl residues may be linear or branched, preferably linear, and may also be unsubstituted or may contain as substituents at least one residue which is a halogen, preferably chlorine, bromine, iodine or fluorine, nitro, hydroxy, alkyloxy, preferably methoxy, ethoxy, n-propyloxy, iso-propyloxy, n-butyloxy or n-pentyloxy , or alkanoyloxy, preferably formyloxy, acetoxy or n-propanoyloxy.

In a more preferred embodiment or alkyl radicals, respectively, independently of the others, are selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-pentyl, 3 -methylbutyl, 2,2-dimethylpropyl, n-hexyl, n-heptyl and n-octyl.

In a more preferred embodiment, said alkyl moieties may be selected from non-cyclic polyol moieties with the general formula -CH ₂ (CH(OH)) _g CH ₂ OH, where G is an integer from 1 to 10, preferably from 1 to 4. B more preferably, the non-cyclic polyol residues are selected from the group consisting of arabityl, ribityl, xylityl, erythrityl, threityl, lactityl, mannityl and sorbityl, more preferably D-ribityl and D-arabityl.

In a more preferred embodiment, said cycloalkyl moieties and cycloalkenyl moieties may contain oxygen atoms as ring atoms and may be unsubstituted or may be substituted with at least a moiety selected from hydroxyl, alkyloxy, preferably methoxy, ethoxy, n-propyloxy, iso-propyloxy, n-butyloxy or n-pentyloxy, oyl or alkanoyloxy, preferably formyloxy, acetoxy or n-propanoyloxy.

In a more preferred embodiment, said cycloalkyl moieties and cycloalkenyl moieties which contain oxygen atoms as ring atoms, respectively, are independently selected from the group consisting of tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl and dioxanyl.

In a more preferred embodiment, said aryl moieties respectively contain a maximum of 4, more preferably a maximum of 3, more preferably a maximum of 2, fused rings. In an even more preferred embodiment, each of the aryl residues contain 1 ring.

Preferably, said aryl radicals are, respectively, independently selected from the group consisting of phenyl, benzyl, naphthyl, anthracenyl, phenanthrenyl and pyrenyl.

In a preferred embodiment, said alkenyl residues, respectively, independently of the others, contain from 2 to 17 C atoms, more preferably from 2 to 13 C atoms, more preferably from 2 to 9 C atoms, more preferably from 2 to 5 C atoms. In a more preferred embodiment, said alkenyl radicals are, respectively, independently selected from the group consisting of ethenyl, n-propenyl and n-butenyl.

In a more preferred embodiment, said aldehydes, respectively, independently of the others, contain from 1 to 17 C atoms, more preferably from 1 to 13 C atoms, more preferably from 1 to 9 C atoms, more preferably from 1 to 5 C atoms. In a more preferred embodiment, said aldehydes are, respectively, independently selected from the group consisting of methanal-1-yl (formyl), ethanal-1-yl (2-oxoethyl), n-propanal-1-yl (3 -oxopropyl) and n-butanal-1-yl (4-oxobutyl).

In a more preferred embodiment, said ketones, respectively, independently of the others, contain from 2 to 17 C atoms, more preferably from 3 to 14 C atoms, more preferably from 3 to 9 C atoms. In a more preferred embodiment, said ketones, respectively are independently selected from the group consisting of dimethyl ketyl, methyl ethyl ketyl, ethyl methyl ketyl, diethyl ketyl, methyl propyl ketyl, ethyl propyl ketyl, propyl methyl ketyl, propyl ethyl ketyl and di-propyl ketyl, which may be linear or branched.

In a more preferred embodiment, said aldehyde residues and/or ketone residues may be monosaccharide residues, preferably pentose or ketose residues.

In a preferred embodiment, suitable monosaccharide residues, respectively, independently of others, contain from 3 to 7 carbon atoms, preferably from 5 to 6 carbon atoms, and contain a carbonyl group, preferably an aldehyde group or a keto group, as well as at least hydroxyl group, and may be open or cyclic, preferably as furanose or pyranose.

In a preferred embodiment, suitable monosaccharide residues are derived from monosaccharide residues, respectively, independently selected from the group consisting of D-glyceraldehyde, L-glyceraldehyde, D-erythrose, L-erythrose, D-threose, L- threoses, D-riboses, L-riboses, D-arabinoses, L-arabinoses, D-xyloses, L-xyloses, D-lyxoses, L-lyxoses, D-alloses, L-alloses, D-altroses, L-altroses, D-glucose, L-glucose, D-mannose, L-mannose, D-gulose, L-gulose, D-idose, L-idose, D-galactose, L-galactose, D-talose, L-talose, dihydroxyacetone, D-erythrulose, L-erythrulose, D-ribulose, L-ribulose, D-xylulose, L-xylulose, D-psicose, L-psicose, D-fructose, L-fructose, D-sorbose, L-sorbose, D- tagatose and L-tagatose. More preferably, suitable monosaccharides are selected from the group consisting of D-ribose, L-ribose, D-arabinose, L-arabinose, D-xylose, L-xylose, D-lyxose, L-lyxose, D-allose, L -allose, D-altrose, L-altrose, D-glucose, L-glucose, D-mannose, L-mannose, D-gulose, L-gulose, D-idose, L-idose, D-galactose, L-galactose , D-talose, L-talose, D-ribulose, L-ribulose, D-xylulose, L-xylulose, D-psicose, L-psicose, D-fructose, L-fructose, D-sorbose, L-sorbose, D -tagatose and L-tagatose.

In a more preferred embodiment, said carboxylic acid esters, respectively, independently of the others, contain from 1 to 17 C atoms, more preferably from 1 to 15 C atoms, more preferably from 1 to 12 C atoms, with preferably the C atom of the carboxylate group is linked to one of the residues Q ¹ - Q ^4a . In a more preferred embodiment, said carboxylic acid esters are, respectively, independently selected from the group consisting of ethyl ester, n-propyl ether, iso-propyl ether, n-butyl ether, sec-butyl ether, t-butyl ether and benzyl ether. More preferably, said carboxylic acid esters are selected from the group consisting of methoxycarboyl, 2-methoxy-2-oxo-eth-1-yl, 3-methoxy-3-oxo-prop-1-yl, 4-methoxy- 4-oxo-but-1-yl, ethoxycarboyl, 2-ethoxy-2-oxo-eth-1-yl, 3-ethoxy-3-oxo-prop-1-yl, 4-ethoxy-4-oxo-but- 1-yl, propoxycarboyl, 2-hydroxy-2-propoxy-eth-1-yl, 3-oxo-3-propoxy-prop-1-yl, 4-oxo-4-propoxy-but-1-yl, isopropoxycarbonyl, 2-isopropoxy-2-oxo-eth-1-yl, 3-isopropoxy-3-oxo-prop-1-yl, 4-isopropoxy-4-oxo-but-1-yl, butoxycarbonyl, 2-butoxy-2- oxo-eth-1-yl, 3-butoxy-3-oxo-prop-1-yl, 4-butoxy-4-oxo-but-1-yl, isobutoxycarbonyl, 2-isobutoxy-2-oxo-et-1- yl, 3-isobutoxy-3-oxo-prop-1-yl, 4-isobutoxy-4-oxo-but-1-yl, tert-butoxycarbonyl, 2-tert-butoxy-2-oxo-eth-1-yl, 3-tert-butoxy-3-oxo-prop-1-yl, 4-tert-butoxy-4-oxo-but-1-yl, phenoxycarbonyl, 2-hydroxy-2-phenoxy-eth-1-yl, 3- oxo-3-phenoxy-prop-1-yl, 4-oxo-4-phenoxy-but-1-yl, benzyloxycarbonyl, 2-be nzyloxy-2-oxo-eth-1-yl, 3-benzyloxy-3-oxo-prop-1-yl and 4-benzyloxy-4-oxo-but-1-yl.

In a more preferred embodiment, said amides of carboxylic acids, respectively, independently of the others, contain from 1 to 17 C atoms, more preferably from 1 to 15 C atoms, more preferably from 1 to 12 C atoms, and preferably the C atom of the carboxamide group , respectively, is associated with one of the residues Q ¹ - Q ^4a .

Said amides of carboxylic acids are preferably not carbamides.

In a more preferred embodiment, said carboxylic acid amides are, respectively, independently selected from the group consisting of carbamoyl, 2-amino-2-oxo-eth-1-yl, 3-amino-3-oxo-prop-1 -yl, 4-amino-4-oxo-but-1-yl, methylcarbamoyl, 2-(methylamino)-2-oxo-eth-1-yl, 3-(methylamino)-3-oxo-prop-1-yl , 4-(methylamino)-4-oxo-but-1-yl, dimethylcarbamoyl, 2-(dimethylamino)-2-oxo-eth-1-yl, 3-(dimethylamino)-3-oxo-prop-1-yl , 4-(dimethylamino)-4-oxo-but-1-yl, ethylcarbamoyl, 2-(ethylamino)-2-oxo-eth-1-yl, 3-(ethylamino)-3-oxo-prop-1-yl , 4-(ethylamino)-4-oxo-but-1-yl, ethyl(methyl)carbamoyl, 2-[ethyl(methyl)amino]-2-oxo-eth-1-yl, 3-[ethyl(methyl) amino]-3-oxo-prop-1-yl, 4-[ethyl(methyl)amino]-4-oxo-but-1-yl, dimethylcarbamoyl, 2-(dimethylamino)-2-oxo-eth-1-yl , 3-(dimethylamino)-3-oxo-prop-1-yl, 4-(dimethylamino)-4-oxo-but-1-yl, dipropylcarbamoyl, 2-(dipropylamino)-2-oxo-eth-1-yl , 3-(dipropylamino)-3-oxo-prop-1-yl, 4-(dipropylamino)-4-oxo-but-1-yl, diisopropy lcarbamoyl, 2-(diisopropylamino)-2-oxo-eth-1-yl, 3-(diisopropylamino)-3-oxo-prop-1-yl, 4-(diisopropylamino)-4-oxo-but-1-yl, dibutylcarbamoyl, 2-(dibutylamino)-2-oxo-eth-1-yl, 3-(dibutylamino)-3-oxo-propyl, 4-(dibutylamino)-4-oxo-but-1-yl, di-tert- butylcarbamoyl, 2-(di-tert-butylamino)-2-oxo-et-1-yl, 3-(di-tert-butylamino)-3-oxo-propyl and 4-(di-tert-butylamino)-4- oxo-but-1-yl.

In a more preferred embodiment, said heteroaryl moiety, which does not contain a nitrogen atom and contains 4 from 20 to C, is selected from the group consisting of furanyl and benzofuranyl.

In a more preferred embodiment, said ether moieties, respectively, independently of the others, contain from 2 to 17 C atoms, more preferably from 2 to 13 C atoms, more preferably from 2 to 9 C atoms. residues are, for example, selected from the group consisting of methoxymethyl, methoxyethyl, methoxy-n-propyl, ethoxymethyl, n-propoxymethyl, 2-ethoxyethoxymethyl, 2-(2-ethoxyethoxy)ethyl, iso-propoxymethyl, tert-butyloxymethyl, dioxa- 3,6-heptyl and benzyloxymethyl. In a more preferred embodiment, said ether moieties may be single ether moieties, oligoether moieties, polyester moieties, or mixtures thereof.

In accordance with the present invention, the term "halogen", respectively, independently, should be understood as meaning fluorine, chlorine, bromine or iodine. In accordance with the present invention, the term "halide", respectively, independently, should be understood as identifying fluoride, chloride, bromide or iodide.

Unless otherwise indicated, chiral centers may be in the R or S configuration. The present invention covers both optically pure volumes and stereoisomeric mixtures, such as enantiomeric mixtures and diastereomeric mixtures, in any ratio.

The present invention preferably also provides mesomers and/or tautomers of a compound of formula (1) and/or a compound of formula (2) and/or a compound of formula (3) and/or a compound of formula (100) and/or a compound of formula (101), and/or compounds of formula (102), as well as pure compounds and mixtures of isomers, in any ratio.

By way of example, the compound of formula (1) may be in keno form (1a) or enol form (1b):

A variant of the method for obtaining a derivative of 1,7-diaryl-1,6-heptadione-3,6-dione of the formula (1) includes the following steps:

(A) carrying out the reaction of a substituted aryl ketone of formula (80) with a substituted acetylacetone of formula (81) in the presence of a solvent, preferably ethyl acetate, dimethyl sulfoxide (DMSO), dimethyl formate (DMF) or mixtures thereof, in the presence of a dehydrogenating agent, preferably tributyl borate, B ₂ O ₃ or mixtures thereof, and a primary or and/or secondary amine, preferably n-butylamine, morpholine, piperidine, or mixtures thereof, to give a compound of formula (82):

where Q ¹ represents a substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

where the residue Q ¹ contains as substituents at least one organic residue W1a having the general formula (5a), (6a), (7a), (8a) or (9a):

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, and where the residues R ^{(I )} and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted,

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently of the others, represents a residue of formula (20e), (21) or (24), preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents a protecting group PG, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and

where the residues R1, R2, R3 and R4, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms , aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms,

(B) carrying out the reaction of a compound of formula (82) with a substituted aryl ketone of formula (83) in the presence of a solvent, preferably ethyl acetate, dimethyl sulfoxide (DMSO, DMSO), dimethyl formate (DMF) or mixtures thereof, in the presence of a dehydrogenating agent, preferably tributyl borate, B ₂ O ₃ or mixtures thereof, and a primary and/or secondary amine, preferably n-butylamine, morpholine, piperidine or mixtures thereof, resulting in a 1,7-diaryl-1,6-heptadione-3,6-dione derivative of formula (1a ):

where Q ² represents a substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

where the residue Q ² optionally contains at least one organic residue W1a having the general formula (5a), (6a), (7a), (8a) or (8a), and

where the residue R5 represents hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether, containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms,

(C) optionally, removing any PG protecting groups present.

Alternatively, the 1,7-diaryl-1,6-heptadione-3,6-dione derivative of formula (1) according to the present invention can be prepared by:

(A1) reacting curcumin with a compound of the general formula X ^a -(C(D)(E)) _h -OH in the presence of diethyl azodicarboxylate (DEAD) and triphenylphosphine (PPh ₃ ) and a solvent, preferably ethyl acetate, dimethyl sulfoxide (DMSO, DMSO), dimethyl formate (DMF) or mixtures thereof, or

(A2) reacting curcumin with a compound of the general formula X ^a -(C(D)(E)) _h -Z in the presence of K ₂ CO ₃ and KI and a solvent, preferably ethyl acetate, dimethyl sulfoxide (DMSO, DMSO), dimethyl formate (DMF) or mixtures thereof,

where h is an integer from 1 to 20, preferably from 2 to 8, where the residue Z, independently of the others, represents Cl, Br, I, tosylate (OTs) or mesylate (OMs), and where X ^a , respectively, independently from others, represents a residue of formula (20e), (21) or (24), preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents a protecting group PG, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 atoms C, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing 1 to 8 C atoms, and

(B) removing the PG protecting groups present.

An additional variant of the method for obtaining a derivative of 1,7-diaryl-1,6-heptadione-3,6-dione of the formula (1) includes the steps:

(A) reacting a substituted or unsubstituted aryl ketone of formula (80a) with a substituted acetylacetone of formula (81a) in the presence of a solvent, preferably ethyl acetate, dimethyl sulfoxide (DMSO, DMSO), dimethyl formate (DMF) or mixtures thereof, in the presence of a dehydrogenating agent, preferably tributyl borate, B ₂ O ₃ or mixtures thereof, and a primary and/or secondary amine, preferably n-butylamine, morpholine, piperidine or mixtures thereof, to give a compound of formula (82a),

where R3 is an organic residue W2a having the general formula (4b), (5b), (6b), (7b), (8b) or (9b):

where Q ¹ represents a substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

where the residue Q ¹ optionally contains as substituents at least one organic residue W1b having the general formula (4b), (5b), (6b), (7b), (8b) or (9b), and

where h is an integer from 1 to 20, preferably from 2 to 8, where k is an integer from 0 to 10, preferably from 1 to 8, preferably from 2 to 6, where I is an integer from 0 to 10 , preferably from 1 to 8, preferably from 2 to 6, and where m, n and p, respectively, independently of the others, represent an integer from 1 to 6, preferably from 2 to 4, and

where A, respectively, independently of the others, represents oxygen or sulfur,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR(l) or GC(=G)-R(II), where G, respectively, independently of the others, represents oxygen or sulfur, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted,

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^b , respectively, independently of the others, represents the residue of the formula (20e), (21) or (24), preferably the residue formula (20c), (20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents a protecting group PG, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 atoms C, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing 1 to 8 C atoms, and

where the residues R1, R2 and R4, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl , containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms,

(B) reacting a compound of formula (82a) with a substituted aryl ketone of formula (83a) in the presence of a solvent, preferably ethyl acetate, dimethyl sulfoxide (DMSO, DMSO), dimethyl formate (DMF) or mixtures thereof, in the presence of a dehydrogenating agent, preferably tributyl borate, B ₂ O ₃ or mixtures thereof, and a primary and/or secondary amine, preferably n-butylamine, morpholine, piperidine or mixtures thereof, to obtain a 1,7-diaryl-1,6-heptadione-3,6-dione derivative of formula (1a):

where Q ² represents a substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

where the residue Q ² optionally contains as substituents at least one organic residue W1a having the General formula (4b), (5b), (6b), (7b), (8b) or (9b), and

where the residue R5 represents hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether, containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms,

(C) optionally, removing the PG protecting groups present.

One method for preparing the 1,7-diaryl-1,6-heptadione-3,6-dione derivative of formula (2) includes the following:

(A) carrying out the reaction of the compound of formula (1) with a metal salt M(L ¹ )(L ² )

to obtain a 1,7-diaryl-1,6-heptadione-3,6-dione derivative of formula (2):

where L ¹ and L ² , respectively, independently of the others, represent water, halide, cyanide, thiocyanate, phosphate, hydrogen phosphate or carboxylation with a carboxylic acid containing from 1 to 10 carbon atoms, preferably formate, acetate, n-propionate, lactate, oxalate , fumarate, maleate, tartrate, succinylate, benzoate, salicylate or citrate, and where the residues Q ¹ and Q ² , respectively, independently, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and where

(a) at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1a having the general formula (5a), (6a), (7a), (8a) or (9a):

where h is an integer from 1 to 20, where k is an integer from 0 to 10, where I is an integer from 0 to 10, and where m, n and p, respectively, independently of others, represent an integer from 1 to 6, and

where A, respectively, independently of the others, represents oxygen or sulfur,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted,

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently of the others, represents a residue of formula (20e), (21) or (24), preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represent a protecting group PG, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 atoms C, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing 1 to 8 C atoms, and

where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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 where

(b) R3 is an organic residue W2a having the general formula (4b), (5b), (6b), (7b), (8b) or (9b):

and

where, optionally, at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1b having the general formula (4b), (5b), (6b), (7b ), (8b) or (9b),

where h is an integer from 1 to 20, where k is an integer from 0 to 10, where I is an integer from 0 to 10, and where m, n and p, respectively, independently of others, represent an integer from 1 to 6, and

where A, respectively, independently of the others, represents oxygen or sulfur,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted,

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^b , respectively, independently of the others, represents the residue of the formula (20e), (21) or (24), preferably the residue formula (20c), (20d) or (21), more preferably the remainder of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents a protecting group PG, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 atoms C, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^(XVI) and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing 1 to 8 C atoms, and

where the residues R1, R2, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing from 2 to 12 C atoms, or a glycol containing from 2 to 12 C atoms.

One method for preparing the 1,7-diaryl-1,6-heptadione-3,6-dione derivative of formula (3) includes the following steps:

(A) carrying out the reaction of the compound of formula (2):

with a compound of formula (1e):

to obtain a 1,7-diaryl-1,6-heptadione-3,6-dione derivative of formula (3):

where L ¹ and L ² , respectively, independently of the others, represent water, fluorine, chloride, bromide, iodide, phosphate, hydrogen phosphate, dihydrogen phosphate, sulfate, hydrogen sulfate, tosylate, mesylate, or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms and/or mixtures thereof,

where M ^z+ is a metal cation, where z is the formal oxidation state of said metal M, and where z is an integer from 1 to 7, preferably from 2 to 5, and

where the residues Q ¹ and Q ² , respectively, independently of the others, represent 1 substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and

where the residues Q ^1a and Q ^2a , respectively, independently of the others, represent 1 substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue,

and where

(a) at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1a, where the specified at least one organic residue W1a has the general formula (5a), ( 6a), (7a), (8a) or (9a):

where h is an integer from 1 to 20, where k is an integer from 0 to 10, where I is an integer from 0 to 10, and where m, n and p, respectively, independently of others, represent an integer from 1 to 6, and

where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively , independently of the others, represents oxygen or sulfur, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl, or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^a , respectively, independently of the others, represents the residue of formula (20c), (20d), (21) or (24), more preferably, the residue of formula (20c), (20d) or (21), more preferably, the residue formulas (24):

where each of the residues R ^(VII) , R ^(VIII) t R ^(IX) , respectively, independently of the others, represent hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched containing from 1 to 8 C atoms, or an ether residue which may be linear or branched containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^{(XVI )} and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and

where at least one of the residues Q ^1a and Q ^2a , respectively, independently of the others, contains as substituents at least one organic residue W1c, where the specified at least one organic residue W1c has the general formula (5c), (6c) , (7s), (8s) or (9s):

where h is an integer from 1 to 20, where k is an integer from 0 to 10, where I is an integer from 0 to 10, and where m, n and p, respectively, independently of others, represent an integer from 1 to 6, and

where A, respectively, independently of the others, represents oxygen or sulfur,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted,

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^c , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^c , respectively, independently, represents a residue of the formula (20c), (20d), (21) or (24) , more preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched containing from 1 to 8 C atoms, or an ether residue which may be linear or branched containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^{(XVI )} and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms,

where the residues R1, R1 ^a , R2, R2 ^a , R3, R3 ^a , R4, R4a, R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, 5 cycloalkyl, containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms, or where

(b) R3 or R3 ^a , respectively, independently of the others, is an organic residue W2a, wherein said single organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b):

and

where, optionally, at least one of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, has as substituents at least 20 one organic residue W1b having the general formula (4b), (5b) , (6b), (7b), (8b) or (9b),

where h is an integer from 1 to 20, where k is an integer from 0 to 10, where I is an integer from 0 to 10, and where m, n and p, respectively, independently of others, represent an integer from 1 to 6, and 25 where A, respectively, independently of the others, represents oxygen or sulfur,

preferably oxygen,

where D and E, respectively, independently of the others, represent hydrogen, halogen, GR ^(I) or GC(=G)-R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted,

where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom,

where X ^b , respectively, independently of the others, 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, preferably quaternary, atom nitrogen, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and preferably X ^b , respectively, independently, represents the residue of the formula (20c), (20d), (21) or (24) , more preferably a residue of formula (20c), (20d) or (21), more preferably a residue of formula (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue which may be linear or branched containing from 1 to 8 C atoms, or an ether residue which may be linear or branched containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^{(XVI )} t R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue that can be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, t

where the residues R1, R1 ^a , R2, R2 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 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.

When using different amino protecting groups of PG in the synthesis, an orthogonal protecting group strategy can be used, where different amino functional groups of the molecule can be directionally released one by one to participate in the reaction.

Suitable methods for removing PG amino protecting groups are known in the prior art. An example is benzyloxycarbonyl (Cbz), which can be removed by treatment with Lewis acids such as ZnBr2 in acetic acid. Di-tert-butyloxycarbonyl (boc) can be removed, for example, by acid hydrolysis. Allyloxycarbonyl (alloc) can, for example, be cleaved off by the action of tetrakis(triphenylphosphine)palladium(0) and a nucleophile.

The active or passive introduction, adhesion and spread of pathogens in the host organism is called infection. Sources of infectious particles are found everywhere. Accordingly, for example, the human body is colonized by a large number of microorganisms, which are usually under the control of a normal metabolism and an intact immune system. However, when the immune system is weakened, for example, a strong proliferation of pathogenic microorganisms can occur and, depending on the type of pathogen, various symptoms of the disease can appear. Medicine has special tools designed to treat many diseases caused by pathogenic microorganisms, for example, antibiotics against bacteria or antimycotic drugs against fungi or antiviral drugs against viruses. However, with the use of these agents, there has been an increase in the number of resistant (resistant) pathogens, which sometimes also have multidrug resistance. With the emergence of these resistant and multi-resistant pathogens, the treatment of infectious diseases is becoming increasingly difficult. The clinical consequences of resistance (resistance) are treatment failures, especially in immunosuppressed patients.

Single-celled or multicellular microorganisms can cause infectious diseases. The use of at least one pathogen-specific drug, for example, an antibiotic, antimycotic agent or antiviral therapeutic agent, can reduce the number of pathogens and/or lead to inactivation of the pathogen. The use of a pathogen-specific agent may be systemic and/or topical (local).

When applied systemically, the pathogen-specific agent is carried into the circulatory and lymphatic systems of the body being treated and thus distributed throughout the body. With the systemic use of a pathogen-specific drug, degradation of the drug and / or side effects may occur, for example, as a result of biochemical transformation (metabolism) of the drug.

When a pathogen-specific agent is applied topically, the agent is applied where it is to exert its therapeutic effect, for example, on an infected part of the skin, and healthy skin is not affected. This largely avoids systemic side effects.

Superficial infections of the skin or soft tissue need not be treated systemically with a pathogen-specific agent, as the agent can be applied directly to infected areas of the skin.

Known pathogen-specific agents exhibit side effects and interactions, some of which can be severe, both systemically and topically. In addition, in the case of topical application, incorrect medication intake (compliance) of the patient, in particular with the use of antibiotics, can lead to the emergence of resistance.

An alternative here is photodynamic inactivation of microorganisms, since resistance to photodynamic inactivation is unknown. Regardless of the type of microorganisms to be controlled and the infectious diseases associated with them, the number of pathogenic microorganisms is reduced and/or pathogenic microorganisms are destroyed. As an example, mixtures of different microorganisms, such as fungi and bacteria, or different strains of bacteria, can be controlled.

The object of the present invention is achieved by providing a method for inactivating microorganisms, which preferably include viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, algae, bloodborne parasites, or combinations thereof, wherein the method comprises the following steps:

(A) contacting microorganisms with at least one photosensitizer, said sensitizer being at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (101) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5- dione of formula (1), and/or at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione of formula (2), and/or at least one derivative of 1,7-diaryl- 1,6-heptadiene-3,5-dione of formula (3) or a pharmaceutically acceptable salt and/or ester and/or complex of said compound, and

(B) irradiating said microorganisms and at least one photosensitizer with electromagnetic radiation at a suitable wavelength and energy density.

In a preferred embodiment, the method in accordance with the present invention is carried out to inactivate microorganisms for (as part of) photodynamic therapy of the patient and / or photodynamic disinfection (cleaning, decontamination) of at least one surface of the product and / or at least one surface of the site.

In one of the preferred embodiments of the method according to the present invention, the irradiation of these microorganisms and at least one photosensitizer with electromagnetic radiation at a suitable wavelength and energy density is carried out in the presence of at least one oxygen donor compound, preferably a peroxide, and/or at least one oxygen-containing gas, preferably oxygen.

Said at least one oxygen donor compound and/or said at least one oxygen-containing gas can preferably be applied before or during step (B) of the process according to the present invention.

By adding additional oxygen in the form of at least one oxygen-containing compound and/or at least one oxygen-containing gas before or during irradiation of microorganisms and at least one photosensitizer with electromagnetic radiation at a suitable wavelength and energy density, the formation yield is increased. reactive oxygen species (ROS, ROS), preferably oxygen radicals and/or singlet oxygen.

In a preferred embodiment, the photosensitizer is at least one compound of formula (100), at least one compound of formula (101), at least one compound of formula (102), at least one compound of formula (1), at least one a compound of formula (2), at least one compound of formula (3), or a combination thereof, or a pharmaceutically acceptable salt and/or ester, and/or a complex of said compound.

More preferably, the photosensitizer is a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or a 1,7-diaryl-1,6-heptadiene derivative -3,5-dione according to the present invention of formula (2), and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (3), and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (3a), or a pharmaceutically acceptable salt and/or ester and/or complex of said compound.

The object of the present invention is also achieved by using at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (100) and/or at least one 1,7-diaryl-1 derivative ,6-heptadiene-3,5-dione of formula (101) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (102) or a pharmaceutically acceptable salt, and /or an ester, and/or a complex of said compound, as a photosensitizer for inactivating microorganisms, which preferably include viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, algae, blood-borne parasites, or combinations thereof.

More preferably, the 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1), and/or the 1,7-diaryl-1,6-heptadiene-3 derivative, 5-dione according to the present invention of formula (2) and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (3) and/or a derivative of 1, 7-diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (3a) or a pharmaceutically acceptable salt and/or ester and/or complex of said compound is used as a photosensitizer to inactivate microorganisms that preferably include viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, algae, bloodborne parasites, or combinations thereof.

1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use according to the present invention of formula (100) and/or formula (101) and/or formula (102) and/or derivative 1 ,7-diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1), and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (2), and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative in accordance with the present invention of formula (3), and/or a 1,7-diaryl-1 derivative, The 6-heptadiene-3,5-dione according to the present invention of formula (3a) has a high yield of singlet oxygen after irradiation with electromagnetic radiation at a suitable wavelength and energy density.

In the method according to the invention and/or the application according to the invention, the electromagnetic radiation is preferably in the visible, ultraviolet and/or infrared spectral range. More preferably, the wavelength of electromagnetic radiation is in the range from 280 to 1000 nm, more preferably from 380 to 1000 nm.

More preferably, the energy density of electromagnetic radiation is in the range from 1 μW/cm ² to 1 kW/cm ² , more preferably from 1 mW/cm ² to 100 W/cm ² , more preferably from 2 mW/cm ² to 50 W /cm ² , more preferably 6 mW/cm ² to 30 W/cm ² , more preferably 7 mW/cm ² to 25 W/cm ² .

The duration of exposure may vary depending on the type of organism and/or the severity of the infection. Preferably, the exposure time is in the range of 1 µs to 1 hour, more preferably 1 ms to 1000 s.

As an example, the irradiation procedure can be carried out as described in one of the documents: WO 96/29943 A1, EP 0437183 B1 or WO 2013/172977 A1.

Preferably, the irradiation device also includes devices for releasing at least one oxygen-containing compound, preferably a peroxide, and/or at least one oxygen-containing gas, preferably oxygen.

Preferably, the electromagnetic radiation is produced by a radiation source selected from the group consisting of artificial radiation sources such as UV lamps, IR lamps, fluorescent lamps, light emitting diodes, lasers, or chemical light.

Furthermore, the inventors surprisingly found that a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use according to the present invention of formula (100) and/or formula (101) and/or formula (102), and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1), and/or a 1,7-diaryl-1,6- heptadiene-3,5-dione according to the present invention of formula (2), and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (3), and/ or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (3a) and/or corresponding pharmaceutically acceptable salts and/or esters and/or complexes of said compound, preferably show high affinity for microorganisms.

By affinity, said at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101), and/ or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and /or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes effectively bind to microorganisms and form sufficient local singlet oxygen to inactivate microorganisms, preferably their destruction.

In a preferred photosensitizer application, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100,) and/or formula (101), and /or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are bound by microorganisms. After irradiation with electromagnetic radiation at a suitable wavelength and energy density, inactivation of microorganisms occurs, preferably their destruction by the action of the resulting reactive oxygen species (AFE, ROS), preferably oxygen radicals and/or singlet oxygen.

In a preferred embodiment, the binding of at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes with microorganisms results in staining or positioning of the microorganisms. This allows you to monitor the process of inactivation or decolonization of microorganisms.

In the context of the present invention, the term "decolonization" should be understood as meaning the removal, preferably the complete removal of microorganisms.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used in the inactivation of unicellular or multicellular microorganisms, which are preferably selected from the group consisting of viruses , archaea, bacteria, spores of bacteria, fungi such as filamentous fungi and yeasts, spores of bacteria, protozoa, algae and blood-borne parasites.

In a preferred embodiment, body surfaces, e.g. coda or mucous membranes, of a human or animals, preferably mammals can be treated. In this preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100), and/or formula (101), and/or formula (102), and/or at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5- a dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters, and /or complexes, preferably in a pharmaceutical preparation, are used to disinfect and/or decolonize the surface of the skin or soft tissues, and in the preferred embodiment, the integrity of the skin is maintained.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used in a pharmaceutical preparation for topical and/or topical, preferably nasal, oral, anal, vaginal or skin application (application).

The term "topical application" should also be understood to mean application to or into the ear, preferably the outer ear. The outer ear consists of the ear cartilage, pinna, earlobe, external auditory or ear canal, and the outer portion of the tympanic membrane.

The term "topical application" should also be understood to mean application to or in the nose and/or paranasal sinuses, such as, for example, the maxillary sinus, frontal sinus and/or sphenoid sinus.

The term "topical application" should also be understood to mean application to the surface of the eye, preferably the outer, apical side of the corneal epithelial layer and/or the outer surface of the ocular apparatus, preferably the lacrimal ducts, conjunctiva and/or eyelids.

The term "topical application" should also be understood as meaning application to the outer, apical side of the epithelium of hollow organs, for example, the esophagus, gastrointestinal tract, gallbladder, bile ducts, larynx, respiratory tract, bronchi, ovaries, uterus, vagina, urethra, bladder or urethra.

The term "topical application" should also be understood to mean application to or in teeth, for example, in a root canal and/or in a root cavity and/or in a tooth fissure, or in gingival pockets and/or at bone fenestration.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used for the preparation of a pharmaceutical preparation for the prevention and/or treatment of infectious, preferably viral, bacterial and/or mycotic skin disease, preferably selected from the group consisting of staphylococcal scalded skin syndrome, impetigo, skin abscesses, furuncles, carbuncles, phlegmon, cellulitis, acute lymphadenitis, pilionidal disease, pyoderma, purulent dermatitis, septic dermatitis, purulent dermatitis, erythrasma, erysipelas, custom new acne or fungal infections.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used for the preparation of a pharmaceutical preparation for wound healing, for example in the case of healing disorders after surgical interventions.

In a preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula ( 102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, or a pharmaceutical preparation containing at least one 1,7-diaryl-1 derivative, 6-heptadiene-3,5-dione for use according to the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl derivative -1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their corresponding pharmaceutically acceptable salts and/or esters and/or complexes, using used to disinfect and/or reduce bacteria in infected wounds.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formulas (3) and/or formulas (3a) and/or their corresponding pharmaceutically acceptable salts and/or esters and/or complexes are used for the preparation of a pharmaceutical preparation for the prevention and/or treatment of infectious, preferably viral, bacterial and / or fungal diseases, diseases of the ear, upper respiratory tract, oral cavity, throat, larynx, lower respiratory tract and / or esophagus.

The predominance of pathogenic microorganisms is, for example, the main cause of infection in the oral cavity. This raises the problem that microorganisms are organized synergistically into extremely complex biofilms. These biofilms, such as plaque or tartar, are composed of many complex layers and contain proteins, carbohydrates, phosphates and microorganisms. Tartar occurs, in particular, when the surface of the tooth is not freed from deposits during natural or artificial cleaning. Accordingly, this situation makes it difficult to access the microorganisms bound in the biofilm.

Conventional therapeutic agents such as antibiotics and mouth rinses or mechanical dentifrice can only be used to a limited extent because either they cannot directly affect bacteria, e.g. oral cavity, or their use in general is not justified due to negative side effects.

For example, in the United States, 20 million root canal procedures are performed each year, with over 2 million endodontic revision procedures that could have been avoided by improved root canal disinfection.

In a preferred embodiment, the method in accordance with the present invention, the use in accordance with the present invention is suitable for the effective destruction of microorganisms in the root canal system of the human tooth, including the root canal and dental tubules.

In one preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/ or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and /or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used as a photosensitizer in the photodynamic inactivation of microorganisms in the oral cavity.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used for the preparation of a pharmaceutical preparation for the treatment and/or prevention of an infectious, preferably viral, bacterial and/or mycotic lesions of the tooth tissue, preferably plaque, caries or pulpitis, and/or infectious, preferably viral, bacterial and/or mycotic periodontal lesions, preferably gingivitis, periodontitis, pulpitis or peri-implantitis.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, or a pharmaceutical preparation containing at least one derivative of 1,7-diaryl-1, 6-heptadiene-3,5-dione for use according to the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl derivative -1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their corresponding pharmaceutically acceptable salts and/or esters and/or comp Lexas are used to clean teeth, dentures and/or braces.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, or a pharmaceutical preparation containing at least one derivative of 1,7-diaryl- 1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one derivative 1,7 -diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a), and/ or their respective pharmaceutically acceptable salts and/or esters, and/or complexes are used in nasal decolonization of microorganisms.

As an example, methicillin-resistant strains of Staphylococcus aureus (MRSA) persist in oral and nasal colonization and are also highly resistant to external conditions. Accordingly, nasal decolonization, ie removal of microorganisms, also reduces colonization elsewhere in the body.

In addition, the present invention relates to a pharmaceutical composition containing at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100), and/or formula ( 101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes and one or more physiologically acceptable excipients.

In a preferred embodiment, the pharmaceutical composition contains at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, and one or more physiologically acceptable excipients.

In a preferred embodiment, the pharmaceutical composition is prepared by at least one compound of formula (100) and/or formula (101) and/or formula (102) and/or formula (1) and/or formula (2) and/or formula (3), and/or formula (3a) or their respective pharmaceutically acceptable salts and/or esters and/or complexes with one or more physiologically acceptable excipients and giving it a form suitable for administration.

A suitable administration form for the pharmaceutical composition according to the present invention is preferably selected from the group consisting of ointments, creams, gels, lotions, stir mixtures, solutions, for example in the form of drops or sprays, powders, microcapsules and pastes.

The pharmaceutical composition according to the present invention may be administered topically or topically, preferably nasally, orally, anally, vaginally or dermally.

Examples of physiologically acceptable excipients are liquid or solid excipients and bulking agents commonly used in the pharmaceutical industry, solvents, emulsifiers, lubricants, taste correctors, coloring agents and/or buffering agents.

In a preferred embodiment, the physiologically acceptable excipient is polyvinylpyrrolidone (PVP, PVP), cyclodextrin, polyethylene glycol (PEG, PEG) or mixtures thereof.

In a more preferred embodiment, the pharmaceutically acceptable composition contains liposomes.

In a more preferred embodiment, the pharmaceutically acceptable composition contains an effective amount of at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula ( 101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/or formula (3), and/or formula (3a), and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, where the effective amount is, respectively, from 0.01 μg up to 1000 μg per gram of composition, preferably from 0.1 μg to 500 μg per gram of composition, respectively.

In one of the preferred embodiments of the invention, the pharmaceutical composition contains at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100), and/or formula ( 101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, and at least one additional pharmaceutically active ingredient.

In a preferred embodiment, said at least one additional pharmaceutically active ingredient is selected from the group consisting of antibiotics, antimycotics, antivirals, antihistamines, sympathomimetics, antihemorrhagic drugs, emollients and skin protectants, analgesics, disinfectants, immunoenzymes and immunoglobulins, antiparasitic substances, insecticides, repellents and corticosteroids.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, or a pharmaceutical preparation containing at least one derivative of 1,7-diaryl- 1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one derivative 1,7 -diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a), and/ or their respective pharmaceutically acceptable salts and/or esters, and/or co The complexes are self-applied by the consumer, optionally followed by exposure to a suitable radiation source that generates electromagnetic radiation at a suitable wavelength and energy density.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, or a preparation containing at least one 1,7-diaryl-1 derivative ,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100), and/or formula (101), and/or formula (102), and/or at least one derivative of 1,7- diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, using t in the inactivation of microorganisms in biological fluids, preferably in medical blood products.

Suitable equipment for irradiating biological fluids is known to those skilled in the art and is described, for example, in WO 99/43790 A1, US 2009/0010806 A1 or WO 2010/141564 A2.

Examples of suitable biological fluids are blood and blood products, including frozen fresh plasma, erythrocyte concentrate, platelet concentrate, granulocyte concentrate, platelet rich plasma, stem cell preparations, concentrates of selected coagulation factors, human albumin, immunoglobulins, fibrin glue, antithrombin, protein C, protein S, fibrinolytics, or combinations thereof.

In one preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/ or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and /or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used for photodynamic disinfection of all types of surfaces. Photodynamic disinfection (cleaning, disinfection) of the surface leads to photodynamic inactivation of microorganisms on the treated surface.

Examples of suitable surfaces are plastic, metal, glass, textile, wood, stone, or combinations thereof.

More preferably, said 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (3) and/or formula (3a) or a pharmaceutically acceptable salt , and/or an ester and/or a complex of said compound is used in photodynamic disinfection, surface cleaning and/or coating (coating), preferably medical products, electronic devices, hygiene products, food packaging, foodstuffs, furniture, construction materials or areas.

More preferably, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/ or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and /or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are applied to and/or injected into the surface, optionally, then irradiated with a suitable source radiation that produces electromagnetic radiation at a suitable wavelength and energy density. In a preferred embodiment, said at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes provide "self-disinfection" of the surface during irradiation.

Accordingly, irradiation can be carried out immediately after surface treatment with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) , and/or formula (102), and/or at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1), and/or formula (2), and/or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, preferably after application (use) of at least one derivative of 1,7- diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one derivative 1 ,7-diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a), and/or their respective pharmaceutical products salts and/or esters and/or complexes are not available on the surface and/or the introduction of at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of the formula ( 100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of the present invention of formula (1 ), and/or formula (2), and/or formula (3), and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes into the surface and/or into later point in time.

More preferably, articles that have a limited shelf life due to temperature conditions are treated, such as articles made from thermoplastics or articles that are exposed to disinfectants.

Products that have a limited shelf life due to temperature conditions cannot be sufficiently sterilized, for example, due to the fact that at higher temperatures they lose their shape or become brittle.

In addition, incorrect and/or excessive use of disinfectants can lead to an increase in resistance as a result of the selection of more resistant microorganisms, if, for example, the concentration of the substance and the exposure time, and therefore the pathogenic reduction effect, are too low.

In a more preferred embodiment, the method according to the present invention is used to prevent bacterial infection, for example, before implantation or after successful decolonization, for example, to prevent new colonization by pathogens, such as, for example, periodontal pathogens.

To prevent infection by microorganisms, the method of the present invention can also be used to decolonize surfaces.

As an example, contact of immunosuppressed patients with contaminated devices often results in the development of an infection, since immunosuppressed patients are generally susceptible to infections, for example, even at low bacterial counts. In particular, the surfaces of medical devices, preferably medical supplies or dental supplies, more preferably medical supplies for invasive use, such as catheters, hollow probes, tubes or needles, must be disinfected before they are introduced into the human body.

Accordingly, in a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101), and /or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used to inactivate microorganisms on the surfaces of medical devices, preferably medical devices for invasive use such as, for example, contact lenses, surgical instruments, dental burs, dental mirrors, curettes, dental files, catheters, hollow probes, tubes or needles.

In a preferred embodiment, the medical devices are selected from wound dressings, dressings, surgical instruments, catheters, hollow probes, tubes or needles.

More preferably, the term "medical devices" should also be understood to include dental bridges, impression trays, occlusal splints, or artificial dental products such as dentures, crowns or implants.

Preferably, surface treatment of all types of articles with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101), and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and /or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes and/or coating and/or immobilization of at least one derivative 1.7 -diaryl-1,6-heptadiene-3,5-dione used in accordance with the present invention, formula (100) and/or formula (101) and/or formula (102), and/or at least one derivative 1,7-diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) , and/or their respective pharmaceutically acceptable salts, and/or sl esters and/or complexes on the surface of medical devices and subsequent irradiation with electromagnetic radiation at a suitable wavelength and energy density, reduces, preferably prevents, colonization of treated surfaces by microorganisms.

In a preferred embodiment, the surface treatment is carried out by atomization, brushing, injection (injection), spraying, dipping, or combinations thereof.

Irradiation can be carried out immediately after surface treatment with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101), and /or formula (102), and/or at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione according to the present invention of formula (1), and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, preferably after application of at least one 1,7-diaryl-1,6 derivative -heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one derivative of 1,7-diaryl- 1,6-heptadiene-3,5-dione according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or corresponding pharmacologically acceptable salt, and/or ester, and/or a complex of said compound on the surface and/or introducing at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100), and /or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1), and/or formula (2) and/or formula (3) and/or formula (3a) and/or the corresponding pharmacologically acceptable salt and/or ester and/or complex of said compound into the surface simultaneously with and /or at a later point in time, before or during the application of the processed product, for example, a medical device.

In a more preferred embodiment, the use of at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula ( 102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the invention of formula (1) and/or formula (2) and/or formula (3) , and/or formula (3a) and/or the corresponding pharmacologically acceptable salt and/or ester and/or complex of said compound in wound dressings and/or dressings, e.g. cotton gauze, during or after application of the wound dressing, and /or a dressing that contains at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101), and /or formula (102), and/or at least one derivative of 1,7-diaryl-1,6-heptadien-3,5-dione in accordance with the present invention of formula (1), and/yl and formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, electromagnetic irradiation can be carried out at a suitable length wave and energy density, after which there is a decrease in the number of microorganisms in the area of the wound or treated parts of the skin, preferably inactivation.

In a more preferred embodiment, in addition to at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101), and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, the wound dressing and/or dressing contains further components, preferably adsorbents, e.g. alginate calcium or foamed polyurethane or other pharmaceutically acceptable substances.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used to inactivate microorganisms on food packaging surfaces.

Examples of suitable food packaging include containers made from glass, metal, plastic, paper, cardboard, or combinations thereof.

Prior to dusting with food or drink, suitable containers may, for example, be treated with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100), and/ or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are then irradiated with a suitable radiation source which produces electromagnetic radiation at a suitable wavelength and energy density. A suitable food or drink can then be placed in the sanitized container and the container sealed.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used to inactivate microorganisms on food surfaces.

Curcumin is an approved food supplement with an E100 number. Accordingly, modified curcumins, for example, a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula ( 102), and/or a 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3), and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are preferably also acceptable nutritional supplements.

Examples of suitable foods are foods such as meat, fish, eggs, seeds, grains, nuts, berries, spices, fruits or vegetables that may come into contact with pathogenic bacterial species such as Salmonella, Clostridium, Escherichia coli - or Camphylobacter. The advantage is that the hatching eggs can also be disinfected.

The term "gastrointestinal infection" is used to describe a group of diseases that are primarily characterized by symptoms in the upper gastrointestinal tract, such as vomiting, diarrhea, and abdominal pain. Gastrointestinal infections are caused by viruses, bacteria, or parasites. Infection with pathogens usually occurs through contaminated water and/or contaminated food.

The best known sources of gastrointestinal infections are, for example, Salmonella, Campylobacter or Escherichia coli, such as, for example, enterohemorrhagic Escherichia coli (HEC). Diarrhea and vomiting due to food poisoning are mainly caused by staphylococci.

Most often, pathogens of gastrointestinal infections, such as salmonella, for example, enter the human digestive tract through food. The authors of the present invention have found that the use of the method in accordance with the present invention can effectively remove microorganisms from the surface of food products.

Salmonella, for example, is a bacterium that is found throughout the world. Salmonella disease is a typical food infection that causes diarrhea. Pathogens multiply in the gastrointestinal tract of humans and animals. Salmonella can multiply rapidly on unrefrigerated foods. Under certain conditions, bacteria enter the food due to poor hygiene in the kitchen, such as through dirty cutting boards and/or knives.

Examples of foods that often carry Salmonella are raw, ie. undercooked eggs and egg products such as mayonnaise, creams or salads based on eggs or raw dough. Other examples of foods that often carry salmonella are ice cream, raw meats such as raw minced meat or tartare, raw sausages such as smoked sausage or salami. Vegetable foods can also be colonized by Salmonella.

Campylobacter is a worldwide bacteria that causes infectious diarrhea. Campylobacter species live primarily in the gastrointestinal tract of animals, which usually do not get sick themselves. Campylobacter is the most common bacterial cause of diarrhea in Germany.

The main source of infection for Campylobacter is the consumption of foods that are contaminated with the bacteria. Often it is transmitted through poultry meat. Campylobacter cannot reproduce in food, but Camplobacter can survive for some time in the environment. Again, poor hygiene in the kitchen can lead to infection, for example through cutting boards and/or knives that are not properly cleaned after raw meat is cooked.

Examples of foods that are often contaminated with campylobacter are undercooked poultry and poultry products, unpasteurized milk or unpasteurized dairy products, minced meat that has not been thoroughly cooked or fresh raw sausages such as smoked sausage, and contaminated drinking water such as , from the well system.

Enterohemorrhagic Escherichia coli (EHEC) is present in the intestines of ruminants such as cattle, sheep, goats or deer. The bacteria are excreted in the faeces of infected animals. Because E. coli EHEC has a relatively low sensitivity, it can survive in the environment for several weeks. They retain infectivity and even a small amount of pathogens is sufficient to transmit infection. The skin of cattle and other ruminants may be contaminated with traces of faeces. If you touch and stroke animals, bacteria can get on your hand, and from there - into your mouth. Even playing in meadows where ruminants were kept can lead to infection in children.

The application of the method according to the invention allows photodynamic disinfection of the shoe surface, for example the sole.

In addition, the inventors have found that the method according to the present invention is also suitable for photodynamic disinfection of animal surfaces such as hide, leather, fur, fibers or wool.

As an example, due to poor hand hygiene, HEC bacteria can persist on touched products and spread from there.

The transition to humans can also occur with the help of foods that are eaten raw or insufficiently heated. Examples of foodstuffs that are often contaminated with EHEC are unpasteurized milk and unpasteurized dairy products, raw or undercooked meat products such as ground beef (eg hamburgers) and scattered raw sausages such as tea sausages. Vegetable foods are also often contaminated with EHEC, such as vegetables that are contaminated with pathogens from fertilization or contaminated water, unpasteurized fruit juices that are made from contaminated fruits, seeds that are used to grow sprouts, and all foods that are contaminated with pathogens. from contaminated food can be carried directly or indirectly by dirty hands or cooking utensils.

For example, Clostridium difficile is a bacterium that is found throughout the world. In healthy people, Clostridium difficile is a harmless intestinal bacterium. If competing normal gut microbiota are suppressed by antibiotics, Clostridium difficile can multiply and produce toxins that, under some circumstances, can lead to life-threatening diarrhea such as antibiotic-dependent colitis, particularly if antibiotic-induced diarrhea is already present.

Clostridium difficile is one of the most common hospital pathogens (nosocomial pathogens). In addition, Clostridium difficile can form resistant permanent forms, so-called spores, with which, under certain circumstances, bacteria can survive for many years outside the gastrointestinal tract. Accordingly, they can also be transmitted through objects and surfaces, such as toilets, doorknobs, handles and/or handrails, to which pathogens adhere.

The problems described above can be avoided by the method of the present invention, since the use of the method of the present invention effectively removes disease causing pathogens from infected surfaces.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used to inactivate microorganisms in an area such as a clean room or operating room. Once introduced into the area, for example by misting, spraying, squirting, or evaporating, the area can be irradiated with a suitable radiation source that generates electromagnetic radiation at a suitable wavelength and energy density, after which the microorganisms present are inactivated.

In a more preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are used to inactivate microorganisms in a liquid or liquid preparation. Examples of suitable liquids or liquid preparations are emulsion paints, coolants, cooling lubricants, lubricants, brake fluids, paints, adhesives or oils. In a preferred embodiment, the liquid formulation is an aqueous formulation.

Preferably, the liquid is water.

Accordingly, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102 ), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula ( 3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes can be used for the treatment of water in the beverage and food, pharmaceutical, chemical and cosmetic industries, and the electrical industry. In addition, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula ( 102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes can be used for the treatment of drinking water and rainwater, for the treatment of waste water or for the treatment of water for applications in air conditioning technology.

In a preferred embodiment, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102 ), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the invention of formula (1) and/or formula (2) and/or formula (3), and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, liquids or liquid preparations can then be irradiated with a suitable radiation source that generates electromagnetic radiation at a suitable wavelength and energy density. In a preferred embodiment, at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) , and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3 ), and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes provide self-disinfection of the liquid or liquid preparation during irradiation.

In a further preferred embodiment of at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula ( 102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1) and/or formula (2) and/or formula (3), and/ or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, said 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use according to the present formula (100) and/or formula (101) and/or formula (102) and/or said 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1 ), and/or formulas (2), and/or formulas (3), and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes can be fixed on a solid support and, accordingly, can be used as part of solid matrix.

In a particularly preferred embodiment, at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102 ) fixed on a solid support and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the invention of formula (1) and/or formula (2) and/or of formula (3) and/or formula (3a) fixed on a solid support and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes are introduced into the fluid to be treated, preferably water or blood.

In a particularly preferred embodiment, the support is a polymer which bears at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula ( 101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes which are covalently attached. This composition containing a support of at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/ or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes exhibits antimicrobial activity immediately upon exposure to electromagnetic radiation at a suitable wavelength and energy density.

Further, the present invention relates to coated or coated articles which contain or are coated with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100), and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) , and/or formula (2), and/or formula (3), and/or formula (3a), and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes. In a preferred embodiment, the product contains at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione in accordance with the present invention of formula (1) and/or formula (2) and/or formula ( 3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes and/or coated with them.

In a preferred embodiment, the surface of the coated article is provided with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101), and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) , and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes.

More preferably, the surface of the coated article is provided with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and /or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes.

The coated article can then be irradiated with a suitable radiation source that generates electromagnetic radiation at a suitable wavelength and energy density. In a preferred embodiment, said 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102), and/ or said 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes provide "self-disinfection" of the surface of the coated article during disinfection.

Accordingly, irradiation can be carried out immediately after treatment of an article coated with at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100), and/or formula (101 ), and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the invention of formula (1) and/or formula (2), and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, preferably after application of said at least one 1,7-diaryl- 1,6-heptadiene-3,5-dione for use according to the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl derivative -1,6-heptadiene-3,5-dione according to the invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts , and/ or esters, and/or complexes on the surface of the coated article and/or the introduction of at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1), and/or formula ( 2) and/or formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes on the surface of the coated article, and/or at a later time time, preferably before or during application of the coated article.

Examples of suitable products are medical products, food packaging, hygiene products (hygiene products), textiles, pens, handrails, contact lenses, building materials, banknotes, coins, game chips, cards, sports equipment, textiles, tableware, cutlery or electronic devices.

Other suitable products are devices or installations of water transmission lines and/or containers containing water, in which, for example, during the operation of the installation or unit, condensate is formed.

Examples of suitable products are seals, membranes, screens, filters, containers and/or pipes for hot water plants, hot water distributors, heat exchangers, air conditioners, humidifiers, refrigerators, cooling units, refrigerators, beverage dispensers, washing machines or dryers. devices.

For example, small numbers of microorganisms, despite filtering the outside air, can penetrate into the air conditioner and exist there for a short time. The metabolic products of these microorganisms can cause musty and moldy smells.

Further, for the air conditioner to work, it is necessary to remove moisture from the air and retain it. Most of the condensate is removed and, for example, passes through the condensate circuit. However, residual moisture remains on the surface of the air conditioning evaporator, in particular in a passenger car, where the air conditioning is switched off only when the engine is turned off, after which it is impossible to ensure temperature equalization.

Microorganisms that enter the evaporator from the air, such as fungal and/or bacterial spores, find themselves in an ideal warm, humid climate and can multiply uncontrollably.

Some molds, for example, pose a health risk, so air conditioning units should be regularly disinfected and the organisms present therein removed by the method of the present invention.

When replacing an air conditioner filter, such as a dust and/or pollen filter, the filter housing and the surrounding air conditioner ducts can be cleaned using the method of the present invention. Cleaning the evaporator of an air conditioning unit using the present invention also removes odors from the air of the air conditioning unit.

For example, legionella bacteria are bacteria that cause various symptoms in humans, such as flu-like symptoms or severe lung infections. Legionella bacteria preferably multiply at a temperature of from 25°C to 45°C. In particular, in artificial plumbing systems, such as water pipes in buildings, pathogens find good conditions to thrive due to the temperatures prevailing there. In addition, Legionella bacteria can thrive in deposits and pipeline linings. In this case, the method according to the present invention can be used, for example in combination with a scale and/or lining removal method.

Legionella bacteria (Legionella) are transmitted by sprayed water, fog. Droplets containing pathogens can be airborne and inhaled. Examples of possible sources of infection are hot water supplies such as showers, humidifiers or faucets, as well as cooling towers, air conditioners or other units that spray water into water droplets such as misters, fog fountains, water features, etc. Water transfer is also possible in swimming pools via waterfalls, slides, hot tubs and/or fountains. Legionella infestation can be prevented by applying the method of the present invention to the surfaces of contaminated articles.

The method according to the invention can, for example, be applied to equipment or installations of water supply lines and/or water tanks, for example, equipment or installations that are used in fish farming.

Epidemic diseases of fish are an example of a huge economic threat to all intensively operating fisheries, where farmed fish are kept in a confined space. To combat fish diseases, for example, antibiotics and/or chemical additives are added. Examples of chemical additives used are calcium hydroxide, hydrogen peroxide, peracetic acid preparations, copper sulfate, chloramines, sodium carbonate, sodium chloride or formaldehyde.

To reduce the use of the above antibiotics and/or chemical additives, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101 ), and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1), and/or formula ( 2) and/or formulas (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes can be used for photodynamic disinfection of fishery equipment or installations, e.g. fish ponds, pools, pumps, filters, pipes, nets, hooks or substrates. Similarly, fish and/or fish eggs can be subjected to photodynamic decontamination.

Similarly, terrariums, aquariums, sand, gravel and/or green plants can be subjected to photodynamic disinfection of dor and/or during their use.

Examples of suitable electronic equipment include hot plates, remote controls, headphones, speakerphones, headsets, mobile phones, or controls such as buttons, switches, touch screens, or keys.

Examples of suitable building materials include concrete, glass, sand, gravel, wall cladding, plaster, screed, and the like.

Examples of suitable wall claddings include wood panels, boards, solid wood panels, medium density fibreboard, plywood boards, multiplex boards, fiber reinforced concrete boards, gypsum boards, gypsum boards, and plastic, foam or cellulose wallpapers.

By way of example, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and/or formula (3) and/or formula (3a) and/or, respectively, its pharmaceutically acceptable salt and/or ester and/or complex can be used to remove mold.

Preferably, the moldy surface is treated with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) , and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1), and/or formula (2), and/or of formula (3) and/or formula (3a) and/or their respective pharmaceutically acceptable salt and/or ester and/or complexes, and then irradiated with a suitable radiation source which produces electromagnetic radiation at a suitable wavelength and energy density , after which there is a reduction in the amount, preferably inactivation, of mold on the treated surfaces.

In a more preferred embodiment, particles coated with at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1) and/or formula (2) and/or formula (3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes, for example inorganic or organic particles, form a coated article.

In a more preferred embodiment, the particles include at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention of formula (100), and/or formula (101), and/ or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2), and /or formula (3) and/or formula (3a) and/or, respectively, their pharmaceutically acceptable salts and/or esters and/or complexes, which are covalently linked to the said particles.

In said preferred embodiment of the use according to the present invention or the method according to the present invention, irradiation of microorganisms and at least one derivative of 1,7-diaryl-1,6-heptadiene-3,5-dione for use in accordance with the present invention formula (100) and/or formula (101) and/or formula (102) and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present the invention of formula (1) and/or formula (2) and/or formula (3) and/or formula (3a) and/or, respectively, their pharmaceutically acceptable salts and/or esters and/or complexes electromagnetic radiation at a suitable wavelength and energy density is carried out in the presence of at least one oxygen donor compound, preferably a peroxide, and/or at least one oxygen-containing gas, preferably oxygen.

The at least one oxygen donor compound and/or the at least one oxygen-containing gas can preferably be applied (applied) before or during exposure to electromagnetic radiation at a suitable wavelength and energy density.

By additionally providing oxygen in the form of at least one oxygen-containing compound and/or at least one oxygen-containing gas before or during irradiation of said microorganisms and at least one photosensitizer with electromagnetic radiation at a suitable wavelength and energy density, the yield of reactive oxygen species is increased. (AFE, ROS), preferably oxygen radicals and/or singlet oxygen.

According to the present invention, at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the present invention of formula (1) and/or formula (2) and/or formula ( 3) and/or formulas (3a) and/or their respective pharmaceutically acceptable salts and/or esters and/or complexes can be used as a medicinal agent.

Said pharmacologically acceptable complexes are preferably inclusion complexes of said at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative for use in accordance with the present invention of formula (100) and/or formula (101 ), and/or formula (102), and/or at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative of formula (1), and/or formula (2), and/ or formula (3) and/or formula (3a), preferably at least one 1,7-diaryl-1,6-heptadiene-3,5-dione derivative according to the invention of formula (1) and/or formula (2 ), and/or formula (3), and/or formula (3a), with polyvinylpyrrolidone (PVP, PVP), cyclodextrins or mixtures thereof.

A suitable method for the preparation of inclusion complexes of the corresponding 1,7-diaryl-1,6-heptadiene-3,5-dione derivatives is described, for example, in:

S. Winter, N. Tortik, A. Kubin, B. Krammer, K. Plaetzer, Back to the roots: photodynamic inactivation of bacteria based on water-soluble curcumin bound to polyvinylpyrrolidone as a photosensitizer, Photochem. photobiol. Sci., 2013.12, 1795-1802. DOI: 10.1039/C3PP50095K.

The present invention is illustrated by the following non-limiting drawings and examples.

Figure 1 shows photodynamic inactivation (PDI) of E. coli by SACUR-0 hydrochloride compared to controls (no light, no photosensitizer). Figure 2 shows photodynamic inactivation (PDI) of E. coli by

SACUR-01a hydrochloride versus controls (no light, no photosensitizer). Figure 3 shows photodynamic inactivation (PDI) of E. coli with SACUR-01b hydrochloride compared to controls (no light, no photosensitizer). Figure 4 shows photodynamic inactivation (PDI) of E. coli with SACUR-01c hydrochloride compared to controls (no light, no photosensitizer). Figure 5 shows photodynamic inactivation (PDI) of E. coli with SACUR-01e hydrochloride compared to controls (no light, no photosensitizer). Figure 6 shows photodynamic inactivation (PDI) of E. coli with SACUR-02 hydrochloride compared to controls (no light, no photosensitizer). Figures 7a and 7b show photodynamic inactivation (PDI) of E. coli by SACUR-03 hydrochloride compared to controls (no light, no photosensitizer). Figure 8 shows photodynamic inactivation (PDI) of E. coli with SACUR-04 hydrochloride compared to controls (no light, no photosensitizer). Figure 9 shows photodynamic inactivation (PDI) of E. coli with SACUR-05 hydrochloride compared to controls (no light, no photosensitizer). Figure 10 shows photodynamic inactivation (PDI) of E. coli with SACUR-08 hydrochloride compared to controls (no light, no photosensitizer). Figure 11 shows photodynamic inactivation (PDI) of E. coli with SACUR-09b hydrochloride compared to controls (no light, no photosensitizer). Figure 12 shows photodynamic inactivation (PDI) of E. coli with SACUR-10a chloride compared to controls (no light, no photosensitizer). Figure 13 shows photodynamic inactivation (PDI) of E. coli with SACUR-10b hydrochloride compared to controls (no light, no photosensitizer). Figure 14 shows photodynamic inactivation (PDI) of E. coli with SACUR-10c chloride compared to controls (no light, no photosensitizer). Figure 15 shows photodynamic inactivation (PDI) of E. coli with SACUR-11b hydrochloride compared to controls (no light, no photosensitizer). Figure 16 shows photodynamic inactivation (PDI) of E. coli with SACUR-12a hydrochloride compared to controls (no light, no photosensitizer). Figure 17 shows photodynamic inactivation (PDI) of E. coli with SACUR-13b hydrochloride compared to controls (no light, no photosensitizer). Figure 18 shows photodynamic inactivation (PDI) of E. coli by Zn-SACUR-1a hydrochloride against E. coli compared to controls (no light, no photosensitizer). Figure 19 shows photodynamic inactivation (PDI) of E. coli with RO-SACUR-1a hydrochloride compared to controls (no light, no photosensitizer). Figure 20 shows photodynamic inactivation (PDI) of E. coli by SACUR-14b

hydrochloride compared to controls (no light, no photosensitizer). Figure 21 shows the results of a phototoxicity assay using SACUR-01a against E. coli, ATCC 25922 (left) and against S. aureus, ATCC 25923 (right). Figure 22 shows the results of a phototoxicity assay using SACUR-03 against E. coli, ATCC 25922 (left) and against S. aureus, ATCC 25923 (right). Figure 23 shows the results of a phototoxicity assay using SACUR-07 against E. coli, ATCC 25922 (left) and against S. aureus, ATCC 25923 (right). Figure 24 shows the results of a phototoxicity assay using SACUR-01a BF2 against S. aureus, ATCC 25923. Figure 25 shows the results of a phototoxicity assay using SACUR-09a against S. aureus, ATCC 25923. against S. aureus ATCC 25923. Figure 27 shows the results of a phototoxicity test using SACUR-11C against S. aureus, ATCC 25923. Figure 28 shows the results of a phototoxicity test using SACUR-12b against S. aureus, ATCC 25923. Figure 29 shows the results of the analysis Figure 30 shows the results of a phototoxicity assay using SACUR-13a against S. aureus, ATCC 25923. Figure 31 shows the results of a phototoxicity assay using SACUR-14a against S. aureus, ATCC 25923. Figure 32 shows the results of a phototoxicity assay using SACUR-15a against S aureus, ATCC 25923. Figure 33 shows the results of a phototoxicity assay using SACUR-15b against S. aureus, ATCC 25923.

Example 1) Preparation of various derivatives of 1,7-diaryl-1,6-heptadiene-3,5-dione.

General synthesis scheme

All chemicals were purchased from traditional suppliers (TCI, ABCR, Acros, Merck and Fluka) and used without further purification. The solvents were distilled before use and, if necessary, dried in the usual way. Dry DMF was purchased from Fluka (Taufkirchen, Germany).

Thin layer chromatography was performed on thin film aluminum foils coated with silica gel 60 F254 (Merck, Darmstadt, Germany). Preparative thin layer chromatography was performed on commercially available glass plates coated with silica gel 60 (20 cm×20 cm, Carl Roth GmbH & Co. kg, Karlsruhe, Germany). Compounds were detected using ultraviolet light (=254 nm, 333 nm) and some were identified with the naked eye or stained with ninhydrin. Chromatography was performed using silica gel (0.060–0.200) from Acros (Waltham, USA).

NMR spectra were recorded on a Bruker Avance 300 spectrometer (300 MHz [ ¹ H-NMR], 75 MHz [ ¹³ C-NMR]) (Bruker Corporation, Bellerica, USA).

All chemical shifts are given in δ [ppm] relative to an external standard (tert-methylsilane, TMS). Coupling constants are respectively given in Hz; signal characteristics: s = singlet, d = doublet, t = triplet, m = multiplet, dd = doublet of doublets, br = wide. The relative number of atoms was determined by integration. The final identification of the signals in the carbon spectra was carried out by the DEPT method (pulse angle: 135°). Error limits: 0.01 ppm for 1H-NMR, 0.1 ppm for 13C-NMR and 0.1 Hz for coupling constants. The solvent used is that specified for each spectrum.

IR spectra were recorded on a Biorad Excalibur FTS 3000 spectrometer (Bio-Rad Laboratories GmbH, Munich, Germany).

ER-MS was measured on a ThermoQuest Finnigan TSQ 7000 spectrometer, all HRMS were determined on a ThermoQuest Finnigan MAT 95 spectrometer (respectively, Thermo Fisher Scientific Inc, Waltham, USA); argon was used as an ionizing gas for bombardment by accelerated atoms.

SMP-20 (Bűchi Labortechnik GmbH, Эссен, Германия) с использованием стеклянного капилляра.Melting points were determined using a special instrument

SMP-20 (Bűchi Labortechnik GmbH, Essen, Germany) using a glass capillary.

All UV/VIS spectra were recorded using a Varian Cary 50 Bio UV/VIS spectrometer; fluorescence spectra were recorded using a Varian Cary Eclipse spectrometer.

Solvents for a special class of spectroscopic purity of absorption and emission measurements were purchased from Acros or Baker, or Uvasol from Merck. Milli porous water (18 MΩ, Milli QPIus) was used for all measurements.

1. Synthesis of aldehyde components

The reagents and alkylating reagents listed in Table 1 were purchased from commercial sources.

The corresponding alkyl bromides or alkyl tosylates were used as alkylating agents.

General scheme 2: Synthesis of additional aldehyde components: Conditions: (a) K ₂ CO ₃ , KI, DMF or DMSO, T=60-80°C

1.1 Substituted vanillins

1.1.1 General procedure:

10 mmol of the corresponding reagent was placed under nitrogen atmosphere in 20 ml of dimethylformamide:

(I) 4-hydroxybenzaldehyde (1.22 g, 10 mmol)

(II) vanillin (1.52 g, 10 mmol)

(III) benzyloxyvanillin (2.28 g, 10 mmol)

(IV) 6-hydroxy-2-naphthaldehyde (1.72 g, 10 mmol)

(V) 4-hydroxy-3-methoxy-acetophenone (1.66 g, 10 mmol)

The corresponding alkylating reagent (12-15 mmol, 1.2-1.5 equiv.) in DMF (10 ml) and K ₂ CO ₃ (2.76 g, 20 mmol) were added successively. The mixture was stirred under nitrogen for 24 hours at 80°C. After cooling to room temperature, the reaction mixture was diluted with 60 ml of ethyl acetate and the organic phase was stirred three times, each time with 40 ml of saturated aqueous sodium chloride solution, and once with 50 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator.

Silica gel column chromatography was performed to purify the product.

E-1: 4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Reagent: 4-hydroxybenzaldehyde.

2-(tert-Butoxycarbonylamino)ethyl bromide (3.34 g, 15 mmol) was used as an alkylating agent.

Yield: 76% theoretical, 2.5 g pale yellow solid

Molecular weight = 265.30 g/mol; Empirical formula = C ₁₄ H ₁₉ NO ₄

¹ H-NMR (300 MHz, CDCl ₃ ), δ=9.87 (s, 1H), 7.82 (d, J=8.8 Hz, 2H), 6.98 (d, J=8.7 Hz, 2H), 5.05 (s, 1H ), 4.09 (t, J=5.2 Hz, 2H), 3.55 (dd, J=10.4, 5.1 Hz, 2H), 1.44 (s, 9H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 288.1 (17%, MNa ⁺ ), 265.1 (1%, MH ⁺ ), 210.1 (100%, MH ⁺ -C ₄ H ₉ ) , 166.1 (19%, MH ⁺ -boc).

E-3: 3-methoxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Reagent: vanillin (4-hydroxy-3-methoxybenzaldehyde).

2-(tert-Butoxycarbonylamino)ethyl bromide (3.34 g, 15 mmol) was used as an alkylating agent.

Yield: 79% theoretical, 2.54 g pale yellow solid

Molecular weight = 295.34 g/mol; Empirical formula = C ₁₅ H ₂₁ NO ₅

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.85 (s, 1H), 7.43 (d, J=1.8 Hz, 1H), 7.42 (m, 1H), 6.98 (d, J=8.0 Hz, 1Н), 5.10 (s, 1Н), 4.15 (t, J=5.1 Hz, 2Н), 3.92 (s, 3Н), 3.60 (dd, J=10.6, 5.3 Hz, 2Н), 1.44 (s, 9H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 318.1 (13%, MNa ⁺ ), 296.1 (100%, MH ⁺ ), 240.1 (45%, MH ⁺ -C ₄ H ₉ ), 196.1 (9%, MH ⁺ -boc).

E-15: 3-methoxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)acetophenone

Obtaining in accordance with A.1).

Reagent: 4-hydroxy-3-methoxyacetophenone (acetovanilone).

2-(tert-Butoxycarbonylamino)ethyl bromide (3.34 g, 15 mmol) was used as an alkylating agent.

Yield: 77% theoretical, 2.75 g pale yellow solid

Molecular weight = 309.36 g/mol; Empirical formula = C ₁₆ H ₂₃ NO ₅

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=7.51 (d, J=1.9 Hz, 1H), 7.49 (s, 1H), 6.94 (d, J=7.9 Hz, 1H), 5.19 (s, 1Н), 4.12 (t, J=5.1 Hz, 2Н), 3.89 (s, 3Н), 3.58 (q, 5.3 Hz, 2Н), 2.52 (s, 3Н), 1.43 (s, 9Н). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 332.1 (29%, MNa ⁺ ), 309.1 (2%, MH ⁺ ), 254.1 (33%, MH ⁺ -C ₄ H ₉ ), 210.1 (100%, MN ⁺ -boc).

E-14: 6-(2-N-tert-butyloxycarbonyl-aminoethoxy)naphthalene-2-carbaldehyde

Reagent: 6-hydroxy-2-naphthaldehyde.

2-(tert-Butoxycarbonylamino)ethyl bromide (3.34 g, 15 mmol) was used as an alkylating agent.

Yield: 71% theoretical, 2.30 g pale yellow solid

Molecular weight = 315.37 g/mol; Empirical formula = C ₁₈ H ₂₁ NO ₄

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=10.09 (s, 1H), 8.25 (s, 1H), 7.94-7.85 (m, 2H), 7.79 (d, J=8.5 Hz, 1H), 7.23 (dd, J=8.9, 2.5 Hz, 1H), 7.17 (d, J=2.3 Hz, 1H), 5.05 (s, 1H), 4.18 (t, J=5.1 Hz, 2H), 3.62 (dd, J =10.5, 5.3 Hz, 2H), 1.46 (s, 9H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 338.2 (11%, MNa ⁺ ), 316.2 (12%, MH ⁺ ), 260.1 (100%, MH ⁺ -C ₄ H ₉ ), 216.1 (14%, MH ⁺ -boc).

E-7: 3-benzyloxy-4-(2-N-tert-butyloxycarbonyl-aminopropyloxy)benzaldehyde

Reagent: benzyloxyvanillin (4-benzyloxy-3-methoxybenzaldehyde).

2-(tert-Butoxycarbonylamino)propyl bromide (3.34 g, 15 mmol) was used as an alkylating agent.

Yield: 82% theoretical, 2.64 g pale yellow solid

Molecular weight = 385.45 g/mol; Empirical formula = C ₂₂ H ₂₇ NO ₅

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.74 (s, 1H), 7.44-7.16 (m, 7H), 6.91 (dd, J=8.1, 1.4 Hz, 1H), 5.47 (s, 1H ), 5.21 (m, 2Н), 4.08 (td, J=5.6, 2.2 Hz, 2Н), 3.33 (d, J=5.2 Hz, 2Н), 2.03-1.92 (m, 2Н), 1.36 (s, 9Н) . MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 408.2 (37%, MNa ⁺ ), 386.1 (2%, MH ⁺ ), 330.1 (63%, MH ⁺ -C ₄ H ₉ ), 286.1 (100%, MH ⁺ -boc).

E-6: 3-methoxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxyethoxy)benzaldehyde

Reagent: vanillin (4-hydroxy-3-methoxybenzaldehyde).

2-[2-(tert-butoxycarbonylamino)ethoxy]ethyl-4-methyl benzenesulfonate (4.26 g, 12 mmol) was used as an alkylating agent.

Yield: 72% theoretical; 2.78 g pale yellow solid

Molecular weight = 339.39 g/mol; Empirical formula = C ₁₇ H ₂₅ NO ₆

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.76 (s, 1H), 7.42-7.26 (m, 2H), 6.92 (d, J=8.1 Hz, 1H), 5.08 (s, 1H), 4.21-4.12 (m, 2H), 3.86-3.78 (m, 2H), 3.84 (s, 3H), 3.54 (dd, J=7.4, 2.6 Hz, 2H), 3.26 (m, 2H), 1.35 (s, 9H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 356.9 (100%, MNH ₄ ⁺ ), 339.9 (41%, MH ⁺ ), 239.9 (6%, MH ⁺ -boc).

1.1.2 General procedure:

15 mmol of the corresponding reagent was placed under nitrogen atmosphere in 10 ml of dimethylformamide:

(VI) 4-hydroxy-3-methyl-benzaldehyde (2.04 g, 15 mmol)

(VII) 4-hydroxy-2-methoxy-benzaldehyde (2.28 g, 15 mmol)

The appropriate alkylating agent (12-15 mmol, 1.2-1.5 equiv.) in DMF (20 ml) and K ₂ CO ₃ (4.14 g, 30 mmol) was added successively. The mixture was stirred under nitrogen for 24 hours at 80°C. After cooling to room temperature, the reaction mixture was diluted with 120 ml of ethyl acetate and the organic phase was stirred three times, each time with 40 ml of a saturated aqueous sodium chloride solution, and once with 40 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. Silica gel column chromatography was performed to purify the product.

E-2: 3-methyl-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Reagent: 4-hydroxy-3-methylbenzaldehyde.

2-(tert-Butoxycarbonylamino)ethyl bromide (5.02 g, 22.5 mmol) was used as an alkylating agent.

Yield: 73% theoretical, 3.44 g yellowish solid

Molecular weight = 279.34 g/mol; Empirical formula = C ₁₅ H ₂₁ NO ₄

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.85 (s, 1H), 7.75-7.66 (m, 2H), 6.90 (d, J=8.9 Hz, 1H), 4.95 (s, 1H), 4.11 (t, J=5.2 Hz, 2H), 3.59 (m, 2H), 2.27 (s, 3H), 1.45 (s, 9H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 302.1 (11%, MNa ⁺ ), 280.1 (9%, MH ⁺ ), 224.1 (100%, MH ⁺ -C ₄ H ₉ ), 180.1 (4%, MN ⁺ -boc).

E-4: 2-methoxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Reagent: 4-hydroxy-2-methoxy-benzaldehyde.

2-(tert-Butoxycarbonylamino)ethyl bromide (5.02 g, 22.5 mmol) was used as an alkylating agent.

Yield: 71% theoretical, 3.94 g pale yellow solid

Molecular weight = 295.34 g/mol; Empirical formula = C ₁₅ H ₂₁ NO ₅

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=10.25 (d, J=1.2 Hz, 1H), 7.76 (dd, J=8.6, 1.5 Hz, 1H), 6.58-6.46 (m, 1H), 6.44 (s, 1Н), 5.06 (s, 1Н), 4.07 (t, J=5.0 Hz, 2Н), 3.87 (s, 3Н), 3.53 (m, 2Н), 1.43 (s, 9Н). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH+10 mmol NH ₄ OAc): 318.1 (8%, MNa ⁺ ), 296.1 (100%, MH ⁺ ), 240.1 (87%, MH ⁺ -C ₄ H ₉ ), 196.1 (3%, MN ⁺ -boc).

E-5: 3-methoxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)-5-iodo-benzaldehyde

5-iodovanillin (4.17 g, 15 mmol) was placed under nitrogen in 10 ml of dimethylformamide.

The alkylating agent was 2-(tert-butoxycarbonylamino)ethyl bromide (5.02 g, 22.5 mmol) dissolved in 20 ml of dimethylformamide. The alkylating agent and K ₂ CO ₃ (4.14 g, 30 mmol) were added successively. The mixture was stirred under nitrogen for 24 hours at 80°C. After cooling to room temperature, the Reaction mixture was diluted with 120 ml of ethyl acetate and the organic phase was stirred three times, each time with 40 ml of saturated aqueous sodium chloride solution, and once with 40 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. Silica gel column chromatography was performed to purify the product.

Yield: 66% theoretical, 3.07 g yellow solid

Molecular weight = 421.23 g/mol; Empirical formula = C ₁₅ H ₂₀ INO ₅

¹ H-NMR: (300 MHz, CDCl ₂ ), δ=9.82 (s, 1H), 7.84 (d, J=1.7 Hz, 1H), 7.39 (d, J=1.8 Hz, 1H), 5.40 (s, 1Н), 4.17 (t, J=4.9 Hz, 2H), 3.91 (s, 3Н), 3.52 (dd, J=10.3, 5.3 Hz, 2H), 1.45 (s, 9Н). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 444.1 (6%, MNa ⁺ ), 422.1 (3%, MH ⁺ ), 366.0 (63%, MH ⁺ -C ₄ H ₉ ), 322.0 (100%, MN ⁺ -bos).

1.2 Polysubstituted aldehydes

The corresponding reagent was placed under nitrogen atmosphere in 10 ml of dimethylformamide:

(VIII) 3,4-dihydroxybenzaldehyde (3.45 g, 25 mmol)

(IX) 3,4,5-trihydroxybenzaldehyde (2.31 g, 15 mmol)

The alkylating agent was 2-(tert-butoxycarbonylamino)ethyl bromide (11.2 g, 50 mmol, 2 equiv.) dissolved in 30 ml of dimethylformamide. The alkylating agent was added successively. To ₂ CO ₃ (13.8 g, 100 mmol) was added. The mixture was stirred under nitrogen for 16 hours at 80°C. A second portion of the alkylating reagent (50 mmol, 2 eq.) in 20 ml of dimethylformamide was added and the mixture was stirred for another 24 h at 80°C. After cooling to room temperature, the reaction mixture was diluted with 250 ml of ethyl acetate and the organic phase was stirred three times, each time with 150 ml of a saturated aqueous sodium chloride solution, and once with 100 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. Silica gel column chromatography was carried out to purify the product (Reagent: first petroleum ether: ethyl acetate = 3:1, then petroleum ether: ethyl acetate = 3:2).

E-11: 3,4-bis-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Reagent: 3,4-dihydroxybenzaldehyde

Yield: 8.1 g pale yellow glassy substance, 69% theoretical

Molecular weight = 424.50 g/mol; Empirical formula = C ₂₁ H ₃₂ N ₂ O ₇

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.83 (s, 1H), 7.52-7.37 (m, 2H), 6.99 (d, J=8.2 Hz, 1H), 5.20 (s, 2H), 4.17-4.06 (m, 4H), 3.56 (m, 4H), 1.44 (s, 9H), 1.43 (s, 9H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 447.2 (100%, MNa ⁺ ), 425.2 (70%, MH ⁺ ), 369.2 (49%, MH ⁺ -C ₄ H ₉ ) , 269.1 (78%, MH ⁺ -boc).

E-12: 3,4,5-tris-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Reagent: 3,4,5-trihydroxybenzaldehyde

Yield: 6.22 g pale yellow glassy substance, 61% theoretical

Molecular weight = 583.68 g/mol; Empirical formula = C ₂₈ H ₄₅ N ₃ O ₁₀

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.82 (s, 1H), 7.11 (s, 2H), 5.71 (s, 1H), 5.21 (s, 2H), 4.12 (t, J=4.6 Hz, 6H), 3.62-3.51 (m, 4H), 3.42 (d, J=4.9 Hz, 2H), 1.44 (d, J=8.7 Hz, 27H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 606.3 (47%, MNa ⁺ ), 584.3 (100%, MH ⁺ ), 528.3 (4%, MH ⁺ -C ₄ H ₉ ), 484.3 (23%, MN ⁺ -boc).

1.3 Mixed substituted benzaldehydes

Stage 1:

3,4-dihydroxybenzaldehyde (3.45 g, 25 mmol) was placed under nitrogen in 20 ml of dimethylformamide. 2-(tert-Butoxycarbonylamino)ethyl bromide (6.72 g, 30 mmol) in 30 ml dimethylformamide was added successively and K ₂ CO ₃ (4.6 g, 33 mmol) was added. The mixture was stirred under nitrogen for 24 hours at 80°C. After cooling to room temperature, the reaction mixture was diluted with 150 ml of ethyl acetate and the organic phase was stirred three times, each time with 100 ml of a saturated aqueous sodium chloride solution, and once with 100 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. The products were purified by silica gel column chromatography.

E-8: 3-hydroxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Yield: 1.48 g pale yellow glassy substance, 17% theoretical Molecular weight = 281.31 g/mol; Empirical formula = C ₁₄ H ₁₉ NO ₅

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.78 (s, 1H), 7.42 (d, J=1.9 Hz, 1H), 7.36 (dd, J=8.2, 1.9 Hz, 1H), 7.14 ( s, 1Н), 6.89 (d, J=8.2 Hz, 1Н), 5.53 (s, 1Н), 4.13 (t, J=4.9 Hz, 2Н), 3.58 (dd, J=10.6, 5.2 Hz, 2Н), 1.42 (s, 9H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 304.1 (19%, MNa ⁺ ), 282.1 (2%, MH ⁺ ), 226.1 (100%, MH ⁺ -C ₄ H ₉ ), 182.1 (42%, MH ⁺ -boc).

E-8a: 4-hydroxy-3-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Yield: 2.60 g pale yellow glassy substance, 37% theoretical

Molecular weight = 281.31 g/mol; - Empirical formula = C ₁₄ H ₁₉ NO ₅

E-11: 3,4-bis-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Yield: 1.38 g pale yellow glassy substance, 13% theoretical

Molecular weight = 424.50 g/mol; Empirical formula = C ₂₁ H ₃₂ N ₂ O ₇

¹ H-NMR and MS as described above.

Stage 2:

1.41 g (5 mmol) of 3-hydroxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde (E-8) was placed under nitrogen in 10 ml of dimethylformamide. An alkylating reagent, namely triethylene glycol monotosylate or 1-bromooctanol, and K ₂ CO ₃ (2.07 g, 15 mmol) were added successively, each dissolving in 10 ml of dimethylformamide. The mixture was stirred under nitrogen for 24 hours at 80°C. After cooling to room temperature, the reaction mixture was diluted with 80 ml of ethyl acetate and the organic phase was stirred three times, each time with 50 ml of a saturated aqueous sodium chloride solution, and once with 50 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. Silica gel column chromatography was performed to purify the product.

E-10: 3-(2-(2-(2-hydroxy-ethoxy)ethoxy)ethoxy)-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

Triethylene glycol monotosylate (3.04 g, 10 mmol) was used as a reagent for alkylation. Column chromatography with ethyl ether EE/EtOH = 3:1

Yield: 1.53 g pale yellow glassy substance, 74% theoretical

Molecular weight = 413.47 g/mol; Empirical formula = C ₂₀ H ₃₁ NO ₈

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.83 (s, 1H), 7.48-7.38 (m, 2H), 6.96 (d, J=8.1 Hz, 1H), 4.24 (dd, J=5.3 , 3.4 Hz, 2Н), 4.12 (t, J=4.8 Hz, 2Н), 3.92 (dd, J=5.3, 3.4 Hz, 2Н), 3.74 (t, J=4.6 Hz, 6Н), 3.66-3.61 (m , 2Н), 3.58 (t, J=4.7 Hz, 2Н), 1.43 (s, 9Н). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 436.2 (35%, MNa ⁺ ), 414.2 (33%, MH ⁺ ), 370.2 (5%, MH ⁺ -C ₄ H ₉ ), 314.2 (100%, MH ⁺ -boc).

E-9: 3-octyloxy-4-(2-N-tert-butyloxycarbonyl-aminoethoxy)benzaldehyde

1-Bromooctanol (1.93 g, 10 mmol) was used as an alkylation agent. Column chromatography with petroleum ether: ethyl acetate = 3:1

Yield: 1.53 g pale yellow glassy substance, 78% theoretical

Molecular weight = 393.53 g/mol; Empirical formula = C ₂₂ H ₃₅ NO ₅

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=9.81 (s, 1H), 7.43-7.32 (m, 2H), 6.96 (d, J=8.4 Hz, 1H), 4.11 (t, J=5.3 Hz, 2H), 4.02 (t, J=6.7 Hz, 2H), 3.55 (dd, J=10.2, 5.0 Hz, 2H), 1.91-1.76 (m, 2H), 1.47-1.39 (m, 2H), 1.42 (s, 9Н), 1.36-1.16 (m, 8Н), 0.90-0.80 (m, 3Н). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 416.2 (51%, MNa ⁺ ), 396.2 (4%, MH ⁺ ), 338.2 (7%, MH ⁺ -C ₄ H ₉ ), 294.2 (100%, MN ⁺ -boc).

1.4 Substituted naphthaldehyde

E-13: 4-(2-N-tert-butyloxycarbonyl-aminoethoxy)naphthalene-1-carbaldehyde

4-Hydroxynaphth-1-aldehyde (1.74 g, 10 mmol) was placed under nitrogen in 10 ml of dimethylformamide. 2-(tert-Butoxycarbonylamino)ethyl bromide (4.4 g, 20 mmol) in 10 ml of dimethylformamide, potassium iodide (10 mmol, 1.66 g) and Cs ₂ CO ₃ (6.5 g, 20 mmol) were added successively. The mixture was stirred under nitrogen for 24 hours at 80°C. After cooling to room temperature, the reaction mixture was diluted with 80 ml of ethyl acetate and the organic phase was shaken three times, each time with 50 ml of a saturated aqueous sodium chloride solution, and once with 100 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. The crude product was washed with a mixture of ethyl ether/petroleum ether 1:19 to remove excess reagent. The orange solid was then extracted with 1:2 ethyl ether/petroleum ether (3x, 100 ml each time) and the precipitate filtered off. The solution was evaporated on a rotary evaporator, and the residue was dissolved in 250 ml of diethyl ether. The organic phase was shaken twice, each time with 50 ml of 3 M NaOH, and once with 100 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. For further purification of the product was carried out column chromatography on silica gel. Yield: 2.08 g pale yellow solid, 47% theoretical

Molecular weight = 315.37 g/mol; Empirical formula = C ₁₈ H ₂₁ NO ₄

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=10.19 (s, 1H), 9.30 (d, J=8.5 Hz, 1H), 8.33 (d, J=8.4 Hz, 1H), 7.94-7.86 ( m, 1Н), 7.76-7.64 (m, 1Н), 7.62-7.51 (m, 1Н), 6.94-6.82 (m, 1Н), 5.07 (s, 1Н), 4.29 (dd, J=6.9, 3.2 Hz, 2H), 3.73 (m, 2Н), 1.46 (s, 9Н). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 338.2 (16%, MNa ⁺ ), 316.2 (19%, MH ⁺ ), 260.1 (100%, MH ⁺ -C ₄ H ₉ ), 216.1 (4%, MN ⁺ -boc).

2. Synthesis of substituted curcumins

The corresponding curcumins were synthesized using the preliminary steps described above as curcumins protected with tert-butyloxycarbonyl (boc). Thereafter, the "boc" protecting group was removed.

2.1 Synthesis of symmetrically substituted curcumins

General scheme 3: Synthesis of various symmetrically substituted curcumins: Conditions: (a) acetylacetone, B ₂ O ₃ , B(OBu) ₃ , n-butylamine, ethyl acetate, 80°C, 6 h, then hydrolysis using HOAc 40% for nights, CT; (b) acetylacetone, B ₂ O ₃ , B(OBu) ₃ , n-butylamine, DMF, 80° C., 6 h, then overnight hydrolysis with HOAc 40%, RT; (c) 3,5-heptanedione, B ₂ O ₃ , B(OBu) ₃ , n-butylamine, DMF, 80° C., 6 h, then overnight hydrolysis with HOAc 40%, RT; (d) DCM, TFA, RT, 5 h; then Amberlite IRA-958 ion exchange resin, water.

2.1.1 General procedure:

Acetylacetone (0.1 g, 1 mmol) and boron oxide B ₂ O ₃ (0.07 g, 1 mmol) were dissolved in ethyl acetate (2 ml) and stirred for 30 minutes at 50°C. Substituted benzaldehyde (20 mmol) in ethyl acetate (3 ml) together with tributylborate (0.7 g, 3 mmol) were added sequentially and the mixture was stirred for another half hour. Then n-butylamine (0.1 ml in 1 ml ethyl ether) was added dropwise over 5 minutes. After stirring for another five hours at 50° C., the reaction mixture was left to stand overnight. The solution was evaporated on a rotary evaporator and the residue was quickly dried under high vacuum. 10 ml of ethyl acetate per 1 g of crude product was added and the crude product was dissolved. For subsequent hydrolysis of the boron complex, a double volume of 50% acetic acid (20 ml per 1 g of crude product) was added. After stirring for 24 hours at room temperature, protected from light, the solvent mixture was removed under reduced pressure. The residue was extracted three times with ethyl ether (3 x 20 ml) and the insoluble salt was filtered off. The combined organic phases were washed with water (30 ml), dried with MgSO ₄ and finally the solvent was removed under reduced pressure. Purification was carried out by column chromatography on silica gel using a combination of acetone/petroleum ether. The resulting purified curcumin fraction was then dissolved in the minimum possible amount of ethyl acetate. Dropwise addition of this solution to an excess of petroleum ether precipitated the product as a fine yellow-orange powder.

1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione (tretramethoxycurcumin)

Amount of appropriate aldehyde used: 334 mg = 2 mmol

Silica gel column chromatography using acetone/petroleum ether = 2:5 → 1:2

Yield: 289 mg, 73% theoretical, orange viscous solid or orange yellow powder. Molecular weight = 396.44 g/mol; Empirical formula \u003d C ₂₃ H ₂₄ O ₆

C-1: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-phenoxy)-ethyl1-carbamic acid tert-butyl ester

Quantity of the respective aldehyde E-1 used: 530 mg = 2 mmol

Silica gel column chromatography using acetone/petroleum ether = 1:3 → 2:3

Yield: 363 mg, 67% theoretical, yellow solid or yellow powder

Molecular weight = 594.71 g/mol; Empirical formula = C ₃₃ H ₄₂ N ₂ O ₈

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=7.61 (d, J=15.8 Hz, 2H), 7.50 (d, J=8.8 Hz, 4H), 6.89 (d, J=8.7 Hz, 4H) , 6.50 (d, J=15.8 Hz, 2H), 5.02 (s, 2H), 4.05 (t, J=5.1 Hz, 4H), 3.60-3.48 (m, 4H), 1.45 (s, 18H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAC): 595.3 (100%, MH ⁺ ), 539.2 (18%, MH ⁺ -C ₄ H ₉ ).

C-5: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methyl-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-2- methyl-phenoxy)-ethyl]-carbamic acid tert-butyl ester

Quantity of the corresponding E-2 aldehyde used: 559 mg = 2 mmol

Silica gel column chromatography using acetone/petroleum ether = 1:3 → 2:3

Yield: 442 mg, 59% theoretical, orange-yellow solid or orange-yellow powder. Molecular weight = 622.77 g/mol; Empirical formula = C ₃₅ H ₄₆ N ₂ O ₈

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=7.59 (d, J=15.8 Hz, 2H), 7.36 (d, J=10.8 Hz, 4H), 6.80 (d, J=8.3 Hz, 2H) , 6.49 (d, J=15.8 Hz, 2Н), 4.94 (s, 2Н), 4.06 (t, J=5.0 Hz, 4Н), 3.58 (m, 4Н), 2.25 (s, 6Н), 1.46 (s, 18H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 623.3 (100%, MH ⁺ ), 567.3 (21%, MH ⁺ -C ₄ H ₉ ).

C-3: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-2-octyloxy-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-3- octyloxyphenoxy)-ethyl]-carbamic acid tert-butyl ester

Amount of appropriate E-4 aldehyde used: 591 mg = 2 mmol Silica gel column chromatography using acetone/petroleum ether = 1:3 → 2:3

Yield: 393 mg, 58% theoretical, orange viscous solid or orange yellow powder. Molecular weight = 654.76 g/mol; Empirical formula = C ₃₅ H ₄₆ N ₂ O ₁₀

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=7.89 (d, J=16.0 Hz, 2H), 7.47 (d, J=8.5 Hz, 2H), 6.62 (d, J=16.0 Hz, 2H) , 6.52-6.39 (m, 4H), 4.99 (s, 2H), 4.06 (t, J=5.1 Hz, 4H), 3.88 (s, 6H), 3.55 (m, 4H), 1.45 (s, 18H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 655.3 (100%, MH ⁺ ).

C-4: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methoxy-5-iodophenyl]-3,5-dioxo-hepta-1,6-dienyl}- 2-octyloxy-6-iodophenoxy)-ethyl1-carbamic acid tert-butyl ester

Amount of appropriate E-5 aldehyde used: 842 mg = 2 mmol Silica gel column chromatography using acetone/petroleum ether = 1:4 → 1:2

Yield: 580 mg, 64% theoretical, orange viscous solid or orange yellow powder. Molecular weight = 906.56 g/mol; Empirical formula = C ₃₅ H ₄₄ I ₂ N ₂ O ₁₀

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=7.57 (d, J=1.5 Hz, 2H), 7.50 (d, J=15.8 Hz, 2H), 7.02 (d, J=1.5 Hz, 2H) , 6.51 (d, J=15.8 Hz, 2H), 5.47 (s, 2H), 4.11 (t, J=4.7 Hz, 4H), 3.90 (s, 6H), 3.52 (m, 4H), 1.46 (s, 18H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 929.1 (100%, MNa ⁺ ), 907.1 (100%, MH ⁺ ), 807.1 (42%, MH ⁺ -boc).

C-2: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methoxy-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-2- methoxyphenoxy)-ethyl]-carbamic acid tert-butyl ester

Quantity of the corresponding E-15 aldehyde used: 590 mg = 2 mmol

Silica gel column chromatography using acetone/petroleum ether = 1:3 → 2:3

Yield: 354 mg, 54% theoretical, orange viscous solid or orange yellow powder. Molecular weight = 654.76 g/mol, Empirical formula = C ₃₅ H ₄₆ N ₂ O ₁₀

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=7.58 (d, J=15.7 Hz, 2H), 7.14-6.99 (m, 4H), 6.87 (d, J=8.3 Hz, 2H), 6.48 ( d, J=15.8 Hz, 2H), 5.16 (s, 2H), 4.09 (t, J=4.9 Hz, 4H), 3.90 (s, 6H), 3.56 (m, 4H), 1.44 (s, 18H). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 655.3 (100%, MH ⁺ ), 555.3 (26%, MH ⁺ -boc).

C-6: (2-{2-[4-(7-{4-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-3-methoxy-phenyl}-3,5-dioxo-hepta- 1,6-dienyl)-2-methoxy-phenoxy1-ethoxy}-ethyl)-carbamic acid tert-butyl ester

Amount of appropriate E-7 aldehyde used: 679 mg = 2 mmol Yield: 349 mg, 47% of theory, orange viscous solid or orange powder

Silica gel column chromatography using acetone/petroleum ether = 1:2 → 1:1

Molecular weight = 742.87 g/mol; Empirical formula = C ₃₉ H ₅₄ N ₂ O ₁₂

¹ H-NMR: (300 MHz, CDCl ₃ ), δ=7.59 (d, J=15.8 Hz, 2H), 7.18 - 7.03 (m, 4H), 6.90 (d, J=8.3 Hz, 2H), 6.49 ( d, J=15.8 Hz, 2H), 5.07 (s, 2H), 4.24-4.15 (m, 4H), 3.91 (s, 6H), 3.88-3.83 (m, 4H), 3.61 (t, J=5.1 Hz , 4H), 3.33 (m, 4Н), 1.43 (s, 18Н). MS: (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 671.3 (51%, MNa ⁺ ), 655.3 (86%, MH ⁺ ), 555.3 (100%, MH ⁺ -boc).

C-7: {2-[4-{7-[3,4-bis-(2-tert-butoxycarbonylamino-ethoxy)-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-2- (2-tert-butoxycarbonylamino-ethoxy)-phenoxy]-ethyl}-carbamic acid tert-butyl ester

Quantity of the corresponding E-11 aldehyde used: 850 mg = 2 mmol

Yield: 374 mg, 41% theoretical, orange very viscous solid or orange-red powder

Silica gel column chromatography using acetone/petroleum ether = 1:3 → 1:2

Molecular weight = 913.08 g/mol; Empirical formula = C ₄₇ H ₆₈ N ₄ O ₁₄

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.57 (d, J=15.8 Hz, 2H), 7.19-7.12 (m, 4H), 6.98-6.86 (m, 2H), 6.50 (d, J= 15.8 Hz, 2H), 5.28 (s, 4H), 4.10 (t, J=4.4 Hz, 8H), 3.55 (m, 8H), 1.46 (s, 18H), 1.45 (s, 18H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 913.5 (100%, MH ⁺ ), 457.3 (7%, (M + 2H ⁺ ) ²⁺ ):

C-8: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-benzyloxy-phenyl1-3,5-dioxo-hepta-1,6-dienyl}-2-benzyloxy -phenoxy)-ethyl]-carbamic acid tert-butyl ester

Quantity of the corresponding E-7 aldehyde used: 738 mg = 2 mmol

Yield: 518 mg, 62% theoretical, orange solid or orange powder

Silica gel column chromatography using acetone/petroleum ether = 1:3 → 2:3

Molecular weight = 835.02 g/mol; Empirical formula = C ₄₉ H ₅₈ N ₂ O ₁₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.55 (d, J=15.8 Hz, 2H), 7.45-7.31 (m, 10H), 7.14-7.04 (m, 4H), 6.86 (d, J= 8.3 Hz, 2H), 6.46 (d, J=15.8 Hz, 2H), 5.39 (s, 2H), 5.22 (s, 4H), 4.14 (t, J=5.9 Hz, 4H), 3.39 (m, 4H) , 2.09–2.00 (m, 4Н), 1.41 (s, 18Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 857.4 (100%, MNa ⁺ ), 835.4 (76%, MH ⁺ ), 735.4 (53%, MH ⁺ -boc).

C-9: {2-[4-{7-[3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-phenyl1-3,5-dioxo-hepta-1,6-dienyl}-2 ,6-bis-(2-tert-butoxycarbonylamino-ethoxy)-phenoxy1-ethyl}-carbamic acid tert-butyl ester

The amount of the corresponding E-11 aldehyde used: 1166 mg = 2 mmol

Yield: 554 mg, 45% theoretical, orange very viscous solid or orange-red powder. Silica gel column chromatography using a combination of acetone/petroleum ether = 1:4 → 1:2. Molecular weight = 1231.46 g/mol; Empirical formula = C ₆₁ H ₉₄ N ₆ O ₂₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.52 (d, J=15.1 Hz, 2H), 6.79 (s, 4H), 6.51 (d, J=15.1 Hz, 2H), 5.75 (s, 2H ), 5.25 (s, 3Н), 4.10 (m, 12Н), 3.57 (m, 8Н), 3.41 (m, 4Н), 1.47 (s, 18Н), 1.47 (s, 36Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 1253.6 (100%, MNa ⁺ ), 1231.6 (49%, MH ⁺ ), 1131.3 (51%, MH ⁺ -boc).

C-10: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-octyloxy-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-2- octyloxyphenoxy)-ethyl]-carbamic acid tert-butyl ester

Quantity of the corresponding E-10 aldehyde used: 787 mg = 2 mmol

Silica gel column chromatography using acetone/petroleum ether = 1:4 → 1:2

Yield: 400 mg, 47% theoretical, orange viscous solid or orange yellow powder. Molecular weight = 851.14 g/mol; Empirical formula = C ₄₉ H ₇₄ N ₂ O ₁₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.58 (d, J=15.7 Hz, 2H), 7.15-7.05 (m, 4H), 6.89 (d, J=8.2 Hz, 2H), 6.48 (d , J=15.8 Hz, 2Н), 5.17 (s, 2Н), 4.09 (t, J=5.0 Hz, 4Н), 4.03 (t, J=6.7 Hz, 4Н), 3.54 (m, 4Н), 1.91-1.80 (m, 4H), 1.41 (s, 18H), 1.51–1.26 (m, 20H), 0.89 (t, 4.5 Hz, 6H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 873.5 (100%, MNa ⁺ ), 851.4 (13%, MH ⁺ ), 751.5 (38%, MH ⁺ -boc).

2.1.2 General procedure:

The reaction was carried out under a nitrogen atmosphere protected from light. As beta-diketone used:

(X) acetylacetone (0.1 g, 1 mmol)

(XI) 3-methyl-2,4-pentanedione (0.12 g, 1 mmol)

(XII) 3,5-heptanedione (0.13 g, 0.137 ml, 1 mmol) or

(XIII) 2-acetylcyclohexanone (0.14 g, 1 mmol).

The corresponding beta-diketone and boron oxide B ₂ O ₃ (0.05 g, 0.7 mmol) were dissolved in dry DMF (2 ml) and stirred for 30 minutes at 70°C. The corresponding substituted aldehyde (2 mmol) together with tributylborate (0.46 g, 2 mmol) was dissolved in dry DMF (5 mL). This solution was added to the composition and stirred for another half hour at 85°C. Then, n-butylamine (0.1 ml in 1 ml of dimethylformamide) was added dropwise, the composition was added and stirred at 70°C for 4 h. ).

10 ml of ethyl acetate was added per 1 g of crude product and the crude product was dissolved. For subsequent hydrolysis of the boron complexes, a double volume of 50% acetic acid was added (20 ml per 1 g of crude product). After stirring for 24 hours at room temperature, protected from light, the solvent mixture was removed under reduced pressure (maximum water bath temperature 50°C). The residue was extracted three times with ethyl ether (3 x 50 ml) and the insoluble salt was filtered off. The combined organic phases were washed with water (50 ml), dried with MgSO ₄ and finally the solvent was removed under reduced pressure. Purification was carried out by column chromatography on silica gel using a combination of acetone/petroleum ether. The pure curcumin fraction was then dissolved in as little ethyl acetate as possible. Adding this solution dropwise to an excess of petroleum ether precipitated the product as a yellow-orange powder.

C-26: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-hydroxy-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-2- hydroxyphenoxy)-ethyl]-carbamic acid tert-butyl ester

Beta-diketone: acetylacetone

Quantity of appropriate E-10 aldehyde used: 560 mg = 2 mmol

Silica gel column chromatography using acetone/petroleum ether = 1:2 → 2:3

Yield: 28% theoretical, orange viscous solid (180 mg). Molecular weight = 626.71 g/mol; Empirical formula = C ₃₃ H ₄₂ N ₂ O ₁₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.57 (d, J=15.8 Hz, 2H), 7.34 (m, H), 7.19-7.08 (m, 2H), 6.85 (d, J=8.4 Hz , 2Н), 6.64 (d, J=15.8 Hz, 2Н), 5.17 (s, 2Н), 4.07 (t, J=5.0 Hz, 4Н), 3.58-3.44 (m, 4Н), 1.43 (s, 18Н) . MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 627.2 (100%, MH ⁺ ), 527.2 (37%, MH ⁺ -boc).

C-18: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-naphthyl]-3,5-dioxo-hepta-1,6-dienyl}-naphthoxy)-ethyl]- carbamic acid tert-butyl ester

Beta-diketone: acetylacetone

Quantity of the corresponding E-13 aldehyde used: 630 mg = 2 mmol

Silica gel column chromatography using acetone/petroleum ether = 2:7 → 1:2

Yield: 62% theoretical, orange viscous solid (430 mg).

Molecular weight = 694.83 g/mol; Empirical formula = C ₄₁ H ₄₆ N ₂ O ₈

¹ H-NMR (300 MHz, CDCl ₃ ), δ=8.48 (d, J=15.5 Hz, 2H), 8.33 (d, J=8.1 Hz, 2H), 8.25 (d, J=8.0 Hz, 2H), 7.80 (d, J=8.1 Hz, 2H), 7.63 (t, J=6.9 Hz, 2H), 7.55 (t, J=6.8 Hz, 2H), 6.86 (d, J=8.2 Hz, 2H), 6.68 ( d, J=15.5 Hz, 2H), 5.04 (s, 2H), 4.26 (t, J=5.0 Hz, 4H), 3.72 (q, J=5.0 Hz, 5H), 1.47 (s, 18H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 717.3 (100%, MNa ⁺ ), 695.3 (56%, MH ⁺ ), 639.3 (73%, MH ⁺ -C ₄ H ₉ ) .

C-19: [2-(6-{7-[6-(2-tert-butoxycarbonylamino-ethoxy)-naphthyl]-3,5-dioxo-hepta-1,6-dienyl}-naphthoxy)-ethyl]- carbamic acid tert-butyl ester

Beta-diketone: acetylacetone

The amount of the corresponding E-19 aldehyde used: 1.26 g=4 mmol

Yield: 820 mg, 59% theoretical, reddish viscous solid or orange powder.

Molecular weight = 694.83 g/mol; Empirical formula = C ₄₁ H ₄₆ N ₂ O ₈

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.85 (d, J=15.8 Hz, 2H), 7.79-7.63 (m, 8H), 7.20-7.08 (m, 4H), 6.71 (d, J= 15.8 Hz, 2Н), 5.06 (s, 2Н), 4.15 (t, J=5.0 Hz, 4Н), 3.61 (m, 4Н), 1.46 (s, 18Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 717.3 (58%, MNa ⁺ ), 695.3 (100%, MH ⁺ ), 639.3 (97%, MH ⁺ -C ₄ H ₉ ) .

C-13: tert-butyl-N-[2-[4-[(E)-3-[(3E)-3-[[4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-phenyl ]methylene]-2-oxo-cyclohexyl]-3-oxo-prop-1-enyl]-2-methoxyphenoxy]ethyl]carbamate

Beta-diketone: 2-acetylcyclohexanone

Amount of appropriate aldehyde used: 580 mg = 2 mmol

Flash chromatography on silica gel using acetone/petroleum ether = 2:5 → 1:2

The fractions containing the product were rotary evaporated and the crude product was recrystallized from a mixture of acetone/petroleum ether 1:3. After slow cooling to RT, it was first slowly cooled overnight in the refrigerator, then cooled for 3 hours in the freezer. The solid was extracted several times with a small amount of 1:3 acetone/petroleum ether and finally washed with petroleum ether. The product was air dried. Then a small crystalline fraction was obtained by crystallization of the initial liquid.

Yield: 68% theoretical, orange opaque crystalline needles (472 mg).

Molecular weight = 694.83 g/mol; Empirical formula = C ₃₈ H ₅₀ N ₂ O ₁₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.76-7.62 (m, 2H), 7.17 (dd, J=8.3, 1.5 Hz, 1H), 7.09 (d, J=1.7 Hz, 1H), 7.06 -6.85 (m, 5H), 5.22-5.08 (m, 2H), 4.11 (t, J=4.5 Hz, 4H), 3.92 (s, 3H), 3.89 (s, 3H), 3.57 (m, 4H), 2.83-2.73 (m, 2H), 2.71-2.64 (m, 2H), 1.86-1.77 (m, 2H), 1.45 (s, 18H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAC): 717.4 (24%, MNa ⁺ ), 695.4 (100%, MH ⁺ ), 595.3 (30%, MH ⁺ -boc).

C-9: {2-[4-{7-[3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-phenyl]-3,5-dioxo-hepta-1,6-dienyl}- 2,6-bis-(2-tert-butoxycarbonylamino-ethoxy)-phenoxy]-ethyl}-carbamic acid tert-butyl ester

Beta-diketone: acetylacetone

The amount of the corresponding E-12 aldehyde used: 1160 mg = 2 mmol

Yield: 66% theoretical, orange viscous solid or orange-red powder (810 mg).

Column chromatography on silica gel using a combination of acetone/petroleum ether = 1:4 → 2:3.

Molecular weight = 1231.46 g/mol; Empirical formula = C ₆₁ H ₉₄ N ₆ O ₂ 0

¹ H-NMR and MS as described above.

C-11: tert-butyl-N-[2-[4-[(1E,6E)-7-[4-[2-(tert-butoxycarbonylamino)ethoxy]-3-[2-[2-(2- hydroxyethoxy)ethoxy]ethoxy]phenyl]-3,5-dioxo-hepta-1,6-dienyl1-2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]phenoxy]ethyl]carbamate

Beta-diketone: acetylacetone

Quantity of the respective E-10 aldehyde used: 830 mg = 2 mmol

Yield: 37% theoretical, orange very viscous solid (330 mg) Silica gel column chromatography, acetone/petroleum ether = 1:2 → 1:1; teacher TLC, acetone/petroleum ether (PE)=1:1. Molecular weight = 891.03 g/mol; Empirical formula = C ₄₅ H ₆₆ N ₂ O ₁₆

¹ H-NMR (600 MHz, CDCl ₃ ), δ=7.58 (d, J=15.7 Hz, 2H), 7.20-7.06 (m, 4H), 6.88 (d, J=8.1 Hz, 2H), 6.48 (d , J=15.8 Hz, 2Н), 5.91 (s, 2Н), 4.25-4.17 (m, 4Н), 4.12-4.04 (m, 4Н), 3.93-3.86 (m, 4Н), 3.83-3.46 (m, 20Н ), 1.44 (s, 18H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 891.7 (92%, MH ⁺ ), 446.3 (100%, (M+2H ⁺ ) ²⁺ ).

C-23: tert-butyl-N-[2-[4-[(1E,6E)-7-[4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-phenyl]-2,6- dimethyl-3,5-dioxo-hepta-1,6-dienyl]-2-methoxyphenoxy]ethyl]carbamate

Beta-diketone: 3,5-heptanedione.

Quantity of the respective acetophenone E-3 used: 608 mg = 2 mmol

Yield: 72% theoretical, orange solid (490 mg).

Column chromatography on silica gel, acetone/petroleum ether = 2:5 → 1:2; teacher TLC, acetone/petroleum ether = 1:2. Molecular weight = 682.82 g/mol; Empirical formula = C ₃₇ H ₅₀ N ₂ O ₁₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.55 (s, 2H), 7.07-6.88 (m, 6H), 6.31 (s, 1H), 5.16 (s, 2H), 4.12 (t, J= 5.0 Hz, 4H), 3.89 (s, 6H), 3.57 (q, J=5.1 Hz, 4H), 2.18 (s, 6H), 1.45 (s, 18H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 705.2 (MNa ⁺ , 67%), 683.4 (MH ⁺ , 100%), 627.3 (MH ⁺ - C ₄ H ₉ , 4%) , 583.3 (MH ⁺ -boc, 63%), 527.2 (MH ⁺ - boc -C ₄ H ₉ , 27%).

C-24: tert-butyl-N-[2-[4-[(1E,6E)-7-[4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxyphenyl]-1,2, 6-trimethyl-3,5-dioxo-octa-1,6-dienyl]-2-methoxyphenoxy]ethyl]carbamate

Beta-diketone: 3,5-heptanedione

Quantity of the respective acetophenone E-15 used: 608 mg = 2 mmol

Yield: 19% theoretical, orange very viscous solid (137 mg)

Column chromatography on silica gel, acetone/petroleum ether = 2:5 → 1:2; teacher TLC, acetone/petroleum ether = 1:2. Molecular weight = 710.87 g/mol; Empirical formula = C ₃₉ H ₅₄ N ₂ O ₁₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.12-6.91 (m, 6H), 6.26 (s, 1H), 5.14 (s, 2H), 4.13 (t, J=5.3 Hz, 4H), 3.91 (s, 6H), 3.56 (q, J=5.2 Hz, 4H), 2.17 (s, 6H), 2.12 (s, 6H), 1.44 (s, 18H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 732.4 (MNa ⁺ , 88%), 710.4 (MH+, 100%), 654.4 (8%, MH ⁺ -C ₄ H ₉ ) , 610.4 (53%, MH ⁺ -boc).

C-12: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methoxy-phenyl]-3,5-dioxo-hepta-4-methyl-1,6-dienyl }-2-methoxy-phenoxy)-ethyl]-carbamic acid tert-butyl ester

Beta-diketone: 3-methyl-2,4-pentanedione

The amount of the corresponding E-3 aldehyde used: 2.94 g = 0.01 mol

Silica gel column chromatography using acetone/petroleum ether = 1:3 → 2:3

Yield: 59% theoretical, orange viscous solid or orange-yellow powder (403 mg).

Molecular weight = 682.82 g/mol; Empirical formula = C ₃₆ H ₄₈ N ₂ O ₁₀

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.74-7.56 (m, 2H), 7.20-6.82 (m, 7H), 6.70 (d, J=15.9 Hz, 1H), 5.13 (s, 2H) , 4.10 (dd, J=10.7, 5.3 Hz, 4Н), 3.92 (s, 3Н), 3.88 (s, 3Н), 3.56 (m, 4Н), 2.17 (m, 3Н), 1.44 (s, 9Н), 1.43 (s, 9H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 691.3 (43%, MNa ⁺ ), 669.3 (100%, MH ⁺ ), 569.3 (17%, MH ⁺ -boc).

2.2 Modification with guanidine

C-14: tert-butyl-(2,2'-(4,4'-((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy -4,1-phenylene))bis(oxy)bis(ethane-2,1-diyl))bis(azanediyl)bis((tert-butoxycarbonylamino)methane-1-yl-1-ylidene)dicarbamate

N,N'-di-boc-N''-triflylguanidine was prepared in a manner analogous to that described in Organic Syntheses, Coll. Vol. 10, p. 266 (2004); T. 78, p. 91 (2002).

Curcumin C-2 was precipitated in dichloromethane (DCM) at room temperature (RT) for 5 h with trifluoroacetic acid (TFA). The resulting trifluoroacetate salt was separated by centrifugation. Triethylamine (0.51 g, 0.66 ml, 5 mmol) was slowly added dropwise via syringe to N,N'-di-boc-N''-triflylguanidine (0.82 g, 2 mmol) in dichloromethane (10 ml) with and 2- 5°C. Curcumin C-2 trifluoroacetate (550 mg, 0.8 mmol) was added. After stirring for 5 h at room temperature, it was diluted with dichloromethane (30 ml) and the organic phase was washed with an aqueous solution of potassium hydrogen sulfate (3%, 20 ml) and water (20 ml). After drying with MgSO ₄ the solution was filtered and rotary evaporated. The crude material was purified by silica gel column chromatography using an acetone/petroleum ether (PE) combination (acetone/petroleum ether = 1:3 → 1:2). Yield: 47% theoretical, orange viscous solid or orange-yellow powder (437 mg).

Molecular weight = 930.08 g/mol; Empirical formula = C ₄₇ H ₆₆ N ₆ O ₁₄

¹ H-NMR (300 MHz, CDCl ₃ ), δ=11.47 (s, 2H), 8.79 (s, 2H), 7.59 (d, J=15.8 Hz, 2H), 7.16-7.05 (m, 4H), 7.01 (d, J=8.3 Hz, 2H), 6.50 (d, J=15.8 Hz, 2H), 4.20 (t, J=5.3 Hz, 4H), 3.92 (s, 6H), 3.89-3.81 (m, 4H) , 1.51 (s, 18Н), 1.49 (s, 18Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 939.6 (9%, MH ⁺ ), 470.4 (100%, (M+2H ⁺ ) ²⁺ ).

2.3 Synthesis of substituted curcumins using the Mitsunobu reaction

The synthesis was carried out in a manner similar to those described by Lepore, S.D. and He, Y.: ("Application of Sonication for the Coupling of Sterically Hindered Substrates in the Phenolic Mitsunobu Reaction"; J. Org. Chem. 68, 2003, pages 8261-8263).

General scheme 5: Synthesis of substituted curcumins via the Mitsunobu reaction using curcumin as starting material: Conditions: (a) 2-N-tert-butyloxycarbonyl-aminoethanol, DEAD, PPh ₃ , DMF or THF or DCM, 0°C → CT; (b) 2-(2-N-tert-butoxycarbonyl-aminoethoxy)ethanol, DEAD, PPh ₃ , DMF, or THF, or DCM, 0°C → RT; (c) 3-bromo-propan-1-ol, DEAD, PPh ₃ , THF or DCM, 0°C → RT;

2.3.1 General procedure:

Curcumin (0.36 g, 1 mmol) was taken along with triphenylphosphine (1.04 g, 4 mmol) and the corresponding boc-protected amino alcohol (1 mmol or 3 mmol) in dry THF (4 ml). Diethyl azodicarboxylate (DEAD) (0.7 g, 4 mmol, 40% in toluene) in dry THF (6 ml) was added dropwise over 20 minutes at approximately 2°C to 5°C, and then the mixture was stirred for 4 h at k.t. In the dark. The mixture was diluted with 40 ml of acetic acid in ethyl ether (EE) and the organic solution was shaken three times, each time with 20 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. The residue was purified by silica gel column chromatography using a combination of acetone/petroleum ether (Dry Load). For further purification, the product was dissolved in the minimum possible amount of ethyl ether and precipitated by adding 10 times the amount of petroleum ether.

[2-(4-{7-[4-hydroxy-3-methoxy-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-2-methoxy-phenoxy)-ethyl]-carbamic acid tert- butyl ether

Quantity of boc-substituted amino alcohol tert-butyl-N-(2-hydroxyethyl)carbamate used appropriately: 161 mg = 1 mmol.

Column chromatography on silica gel with a combination of acetone/petroleum ether (PE)=1:2;

Preparative thin layer chromatography with a combination of acetone/petroleum ether (PE)=2:3.

Yield: 41% theoretical, orange viscous solid or orange-yellow powder (210 mg).

Molecular weight = 511.58 g/mol; Empirical formula = C ₂₈ H ₃₃ NO ₈

C-2: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methoxy-phenyl]-3,5-dioxo-hepta-1,6-dienyl}-2- methoxyphenoxy)-ethyl]-carbamic acid tert-butyl ester

Quantity of boc-protected amino alcohol tert-butyl-N-(2-hydroxyethyl)carbamate used appropriately: 483 mg = 3 mmol.

Column chromatography on silica gel with a combination of acetone/petroleum ether (PE)=1:3 → 1:2.

Yield: 71% theoretical, orange viscous solid (465 mg).

Molecular weight = 654.76 g/mol; Empirical formula = C ₃₅ H ₄₆ N ₂ O ₁₀

¹ H-NMR and MS as described above.

C-6: (2-{2-[4-(7-{4-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-3-methoxy-phenyl}-3,5-dioxo-hepta- 1,6-dienyl)-2-methoxy-phenoxy]-ethoxy}-ethyl)-carbamic acid tert-butyl ester

The amount of the corresponding boc-substituted amino alcohol used 2-(2-N-tert-butoxycarbonyl-aminoethoxy)ethanol: 715 mg = 3 mmol.

Yield: 52% theoretical, orange viscous solid or orange powder (386 mg)

Silica gel column chromatography using acetone/petroleum ether = 1:2 → 2:3

Molecular weight = 742.87 g/mol; Empirical formula = C ₃₉ H ₅₄ N ₂ O ₁₂

¹ H-NMR and MS as described above.

C-25: (1E,6E)-1,7-bis[4-(3-bromopropoxy)-3-methoxy-phenyl]hepta-1,6-diene-3,5-dione

Curcumin (2.00 g, 5.4 mmol) together with triphenylphosphine (5.26 g, 20 mmol) and 3-bromo-propan-1-ol (2.25 g, 1.51 ml, 16.2 mmol) in dry THF (40 ml) and degassed at 0°C FROM. Diethyl azodicarboxylate (DEAD) (7 ml, 40% in toluene, 20 mmol) was added dropwise over 20 minutes and the mixture was stirred overnight in a melting ice bath in the dark, excluding moisture. The mixture was poured into three times the amount of diethyl ether. After precipitation, the supernatant solution was carefully decanted.

The residue was extracted twice, each time using 50 ml of diethyl ether. The combined organic solutions were shaken with 100 ml of water. The organic phase was separated, dried with MgSO ₄ and evaporated on a rotary evaporator. The residue was suspended in a mixture of acetone/petroleum ether 1:2 and the yellow-orange solution was filtered off from colorless crystals. The filter cake was washed several times with small portions of a cold solvent mixture and the filtrate was evaporated on a rotary evaporator. Pre-purification of the residue was carried out by plunge filtration on silica gel using a combination of acetone/petroleum ether 1:2. After removing the solvent mixture, the solid residue was suspended in ethanol in an ultrasonic bath (30 ml), centrifuged and the supernatant solution was decanted. This washing step was repeated three times in total, after which the product was air dried. Yield: 2.08 g orange powder, 63% theoretical. Molecular weight = 610.34 g/mol; Empirical formula = C ₂₇ H ₃₀ Br ₂ O ₆

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.61 (d, J=15.8 Hz, 2H), 7.16-7.04 (m, 4H), 6.92 (d, J=8.3 Hz, 2H), 6.50 (d , J=15.8 Hz, 2H), 4.20 (t, J=6.0 Hz, 4H), 3.91 (s, 6H), 3.64 (t, J=6.4 Hz, 4H), 2.39 (p, J=6.1 Hz, 4H ). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 609.1 (57%, MH ⁺ ), 611.0 (100%, MH ⁺ ).

Curcumins C-27 - C-30 were obtained from bis-(3-bromo-propoxy)curcumin C-25:

General scheme 6: Synthesis of symmetrically substituted curcumins from C-25: Conditions: (a) pyridine, DMF, 50°C, overnight; (b) trimethylamine in ethanol, DMF, 50° C. overnight; (c) trimethylphosphine in toluene, DMF, argon, 50° C. overnight; (d) triphenylphosphine, DMF, 50°C, overnight;

2.4 Curcumins with quaternary charges

Bis-(3-bromo-propoxy)curcumin (61 mg, 0.1 mmol) C-25 was placed in dry DMF (3 ml). Trimethylamine (2 ml, 5.6 M in ethanol, 11 mmol) or pyridine (790 mg, 0.8 ml, 10 mmol) in DMF (2 ml) was added dropwise through a septum using a syringe over 5 minutes and the mixture was stirred overnight in dark at 50°C, excluding moisture.

The mixture was poured into five times the amount of diethyl ether. The precipitate was allowed to settle and the solution was carefully decanted. The residue was washed several times with diethyl ether and then suspended in 15 ml of a mixture of chloroform/diethyl ether 1:1. The suspensions were allowed to settle completely, the supernatant solution was poured out and dried with a vacuum pump. The product was purified by HPLC.

Ion exchange chromatography

The column was loaded with Amberlite 954 resin and the ion exchange resin was conditioned with 0.1M HCl solution. After washing with water, it was reconditioned with a mixture of water/MeOH/MeCN 3:1:1. The TFA salt in a small amount of solvent mixture was then slowly poured onto the resin and rinsed with a small amount of solvent. After removing the solvent under reduced pressure, the remaining solution was freeze-dried.

C-28: 3,3'-(4,4'-((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1- phenylene)) bis(oxy)bis(N,N,N-trimethylpropane-1-aminium) chloride

Yield: 30 mg orange solid, 45% theoretical

Molecular weight: 568.76 + 2x 35.45 = 639.66 g/mol; Empirical formula: C ₃₃ H ₄₈ N ₂ O ₆ Cl ₂

¹ H-NMR and MS: see below (SA-CUR-10a).

C-27: 1,1'-(3,3'-(4,4'-((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2- methoxy-4,1-phenylene)) bis (oxy) bis (propane-3,1-diyl)) dipyridinite chloride

Yield: 36 mg orange solid, 78% of theory

Molecular weight: 608.74+2x 35.45=679.64 g/mol; Empirical formula: C ₃₇ H ₄₀ N ₂ O ₆ Cl ₂

¹ H-NMR and MS: see below (SA-CUR-10c).

2.5 Curcumin with phosphonium groups

Bis-(3-bromo-propoxy)curcumin C-25 (122 mg, 0.2 mmol) was placed in dry dichloromethane (DCM) (10 mL) and stirred under nitrogen atmosphere. Used phosphine in toluene (2 ml, 1 M, 2 mmol) was added dropwise over 5 minutes through the septum using a syringe. The mixture was stirred overnight in a Schlenk tube at 50° C., excluding moisture, in the dark and under a protective gas atmosphere. All volatile components were removed under reduced pressure, and the residue was suspended in 30 ml of diethyl ether using an ultrasonic bath. The precipitate was allowed to settle and the supernatant solution was carefully poured off. The residue was washed several times with diethyl ether. After precipitation of the precipitate, the supernatant solution was decanted and the residue was dried using a vacuum pump.

Ion exchange chromatography

Amberlite 954 resin was loaded into a short column and the ion exchange resin was conditioned with 0.1 M HCl solution. After washing with water, it was reconditioned with a mixture of water/MeOH/MeCN 3:1:1. The TFA salt in a small amount of solvent mixture was then slowly eluted through the resin and then rinsed with a small amount of solvent. After removing the solvent under reduced pressure, the remaining solution was freeze-dried. quantitative output.

C-29: 3,3'-(4,4'-(1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene ))bis(oxy)bis(trimethylpropane-1-phosphonium) chloride

Phosphine: trimethylphosphine

Yield: 58 mg orange solid, 21% theoretical

Molecular weight: 602.69 + 2x 35.45=673.59 g/mol; Empirical formula: C ₃₃ H ₄₈ P ₂ O ₆ Cl ₂

¹ H-NMR and MS: see SA-CUR-15a below.

C-30: 3,3'-(4,4'-((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1- phenylene)) bis(oxy)bis(triphenylpropane-1-phosphonium) chloride

Phosphine: triphenylphosphine

Yield: 107 mg orange solid, 56% theoretical

Molecular weight: 975.12 + 2x 35.45=1046.02 g/mol; Empirical formula: C ₆₃ H ₆₀ P ₂ O ₆ Cl ₂

¹ H-NMR and MS: see SA-CUR-15b below.

2.6 Synthesis of substituted curcumins by alkylation

General scheme 7: Synthesis of substituted curcumins by alkylation: Conditions: (a) 2-N-tert-butyloxycarbonyl-amino bromide, DBU, toluene, or DCM, or THF, 0°C → RT → 60°C; (b) DCM, TFA, RT, 5 h; then Amberlite IRA-958 ion exchange resin, water

Tertramethoxycurcumin (0.4 g, 1 mmol) or curcumin C-2 (0.6 g, 1 mmol) and 2-N-tert-butoxycarbonylaminoethyl bromide (0.34 g, 1.5 mmol) were placed in toluene (4 ml). 1.8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.15 g, 1 mmol) was added and the mixture was stirred for 15 h at room temperature. The solution was diluted with ethyl acetate (30 ml) and washed with sodium chloride solution (30 ml), potassium hydrogen sulfate solution (5%, 30 ml) and water (30 ml). After drying with MgSO ₄ it was evaporated on a rotary evaporator and the residue was purified by column chromatography on silica gel with a mixture of ethyl acetate/petroleum ether, and then by preparative thin layer chromatography.

C-15: 1,7-bis-(3,4-dimethoxyphenyl)-hepta-4-(2-tert-butoxycarbonylaminoethyl)-1,6-diene-3,5-dione

Silica gel column chromatography using acetone/petroleum ether = 1:1

Yield: 14% theoretical, orange solid or orange-yellow powder (76 mg)

Molecular weight = 539.63 g/mol; Empirical formula = C ₃₀ H ₃₇ NO ₈

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.72-7.53 (m, 2H), 7.22-7.04 (m, 4H), 6.86 (d, J=8.1 Hz, 2H), 6.54 (d, J= 15.7 Hz, 2Н), 5.11 (s, 1Н), 3.88–3.72 (m, 2Н), 3.93 (s, 12Н), 2.81–2.70 (m, 2Н), 1.43 (s, 9Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 562.3 (MNa ⁺ , 13%), 540.3 (MH ⁺ , 100%), 484.2 (2%, MH ⁺ -C ₄ H ₉ ) , 440.3 (61%, MN ⁺ -boc).

C-20: [2-(4-{7-[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methoxy-phenyl]-3,5-dioxo-hepta-4-(2-tert-butoxycarbonylamino- ethyl)-1,6-dienyl}-2-methoxy-phenoxy)-ethyl]-carbamic acid tert-butyl ester

Silica gel column chromatography using acetone/petroleum ether = 1:3 → 1:1

Yield: 12% theoretical, orange, orange-yellow powder (96 mg).

Molecular weight = 797.95 g/mol; Empirical formula = C ₄₂ H ₅₉ N ₃ O ₁₂

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.64 (d, J=15.7 Hz, 2H), 7.24-7.01 (m, 6H), 6.78 (d, J=15.8 Hz, 2H), 5.16 (s , 2Н), 4.12 (dd, J=10.6, 5.4 Hz, 4Н), 3.93 (s, 3Н), 3.90 (s, 3Н), 3.86-3.75 (m, 2Н), 3.54 (m, 4Н), 2.82- 2.71 (m, 2H), 1.45 (s, 9H), 1.44 (s, 9H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 820.4 (MNa ⁺ , 69%), 798.4 (MH ⁺ , 100%), 742.4 (6%, MH ⁺ -C ₄ H ₉ ) , 698.3 (36%, MN ⁺ -boc).

2.7 Synthesis of asymmetrically substituted curcumins

General procedure:

Stage 1:

As beta-diketones, acetylacetone (1.5 g, 15 mmol) or 3-methyl-2,4-pentanedione (3.42 g, 30 mmol) was used. The appropriate beta-diketone and boron oxide B ₂ O ₃ (1.5 g, 21 mmol) were suspended in ethyl acetate (20 ml) and stirred for 60 minutes at 70°C. Substituted benzaldehyde E-3 (1.02 g, 3.5 mmol) in ethyl acetate (5 ml) and tributylborate (1.68 g, 7 mmol) were added and the mixture was stirred for half an hour at 85°C. Then n-butylamine (0.5 ml in 3 ml ethyl acetate) was added dropwise over 10 minutes. After stirring for another hour at 80°C, it was cooled to 50°C and 100 ml of 50% acetic acid was added to hydrolyze the boron complex. After stirring overnight at room temperature, the solvent mixture was removed, protected from light, and the residue was extracted three times with ethyl ether (each time using 30 ml). The combined organic phases were washed twice with water (50 ml each pax), dried with MgSO ₄ and finally the solvent was removed under reduced pressure.

E-16: tert-butyl-2-(4-(3,5-dioxohex-1-enyl)-2-methoxyphenoxy)ethylcarbamate

Acetylacetone was used as the beta-diketone. Purification was carried out by column chromatography on silica gel using a combination of acetone/petroleum ether = 2:5 → 1:2. The corresponding symmetrically substituted curcumin has a lower solubility in EtOH than the indicated product.

Yield: 687 mg, 52% theoretical, yellow solid.

Molecular weight = 377.44 g/mol; Empirical formula = C ₂₀ H ₂₇ NO ₆

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.53 (d, J=15.8 Hz, 1H), 7.12-7.00 (m, 2H), 6.88 (d, J=8.3 Hz, 1H), 6.34 (d , J=15.8 Hz, 1H), 5.16 (s, 1H), 4.10 (t, J=5.1 Hz, 2H), 3.90 (s, 3H), 3.56 (d, J=5.3 Hz, 2H), 2.16 (s , 3Н), 1.44 (s, 9Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 777.4 (46%, 2MNa ⁺ ), 400.2 (38%, MNa ⁺ ), 378.2 (12%, MH ⁺ ), 322.1 (100% , MH ⁺ -C ₄ H ₉ ), 278.1 (47%, MH ⁺ - boc).

E-17: tert-butyl-2-(4-(3,5-dioxo-4-methyl-hex-1-enyl)-2-methoxyphenoxy)-ethylcarbamate

3-methyl-2,4-pentanedione was used as beta-diketone. Purification was carried out by column chromatography on silica gel using a combination of acetone/petroleum ether = 1:3 and preparative TLC using a combination of acetone/petroleum ether = 1:2.

Yield: 644 mg, 47% theoretical, yellow solid.

Molecular weight = 391.47 g/mol; Empirical formula = C ₂₁ H ₂₉ NO ₆

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.58 (dd, J=15.7, 6.5 Hz, 1H), 7.13 (d, J=8.3 Hz, 1H), 7.05 (dd, J=4.9, 1.8 Hz , 1Н), 6.89 (d, J=8.3 Hz, 1Н), 6.74 (dd, J=37.9, 15.7 Hz, 1Н), 5.11 (s, 1Н), 4.10 (t, J=5.1 Hz, 2Н), 3.91 (s, 3Н), 3.56 (m, 2Н), 2.25+2.18 (s, 3Н), 2.02 (s, 3Н), 1.44 (s, 10Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAC): 805.5 (24%, 2MNa ⁺ ), 414.3 (53%, MNa ⁺ ), 392.3 (19%, MH ⁺ ), 336.2 (100% , MH ⁺ -C ₄ H ₉ ), 292.2 (34%, MH ⁺ - boc).

Stage 2:

tert-Butyl-2-(4-(3,5-dioxohex-1-enyl)-2-methoxyphenoxy)ethylcarbamate (185 mg, 0.5 mmol) or tert-butyl-2-(4-(3,5-dioxo- 4-methyl-hex-1-enyl)-2-methoxyphenoxy)ethylcarbamate (191 mg, 0.5 mmol) and boron oxide B ₂ O ₃ (0.07 g, 1 mmol) were suspended in ethyl acetate (3 ml) and stirred for 60 minutes at 80°C. Substituted benzaldehyde (0.6 mmol) in ethyl acetate (3 ml) was added successively and tributylborate (0.24 g, 1 mmol) was added and the mixture was stirred for half an hour at 80°C. Then n-butylamine (0.1 ml in 1 ml ethyl ether) was added dropwise over 5 minutes. After stirring for another three hours at 80° C., the slightly cooled solution at a temperature of about 50° C. was poured into 40 ml of 50% acetic acid. After stirring overnight at room temperature, protected from light, the solvent mixture was removed under reduced pressure and the residue was extracted three times with ethyl ether (each time using 20 ml). The combined organic phases were washed twice with water (using 20 ml each time), dried with MgSO ₄ and finally the solvent was removed under reduced pressure. Purification was carried out using column chromatography on silica gel.

C-16: tert-butyl-2-(4-((1E,6E)-7-(3,4-dimethoxyphenyl)-3,5-dioxohepta-1,6-dienyl)-2-methoxyphenoxy)ethyl carbamate

The amount of the corresponding E-16 aldehyde used: 100 mg = 0.6 mmol

Column chromatography using acetone/petroleum ether = 1:2 → 2:3

Yield: 121 mg, 46% theoretical, orange viscous solid or orange-yellow powder.

Molecular weight = 525.60 g/mol; Empirical formula = C ₂₉ H ₃₅ NO ₈

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.60 (dd, J=15.7, 4.5 Hz, 2H), 7.15-7.06 (m, 4H), 6.89 (dd, J=8.3, 3.3 Hz, 2H) , 6.50 (d, J=15.8 Hz, 2Н), 5.13 (s, 1Н), 4.11 (t, J=5.0 Hz, 2Н), 3.94 (s, 3Н), 3.93 (s, 3Н), 3.92 (s, 3H), 3.62-3.52 (m, 2H), 1.45 (s, 9H).

MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 1073.5 (19%, 2M+Na ⁺ ), 526.2 (100%, MH ⁺ ), 470.2 (21%, MH ⁺ -C ₄ H ₉ ).

C-21: 2-(4-((1E,6E)-7-(3A-bis(2-(tert-butoxycarbonylamino)ethoxy)phenyl)-3,5-dioxohepta-1,6-dienyl)-2- methoxyphenoxy)ethylcarbamate

The amount of the corresponding E-16 aldehyde used: 255 mg = 0.6 mmol

Column chromatography using acetone/petroleum ether = 2:5 → 1:2

Yield: 172 mg, 44% theoretical, orange, very viscous solid.

Molecular weight = 783.92 g/mol; Empirical formula = C ₄₁ H ₅₇ N ₃ O ₁₂

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.57 (dd, J=15.7, 9.3 Hz, 2H), 7.17-7.05 (m, 4H), 6.90 (dd, J=8.2, 6.6 Hz, 2H) , 6.49 (d, J=15.7 Hz, 2Н), 5.27 (s, 2Н), 5.14 (s, 1Н), 4.10 (m, 6Н), 3.91 (s, 3Н), 3.55 (m, 6Н), 1.46 ( s, 9Н), 1.44 (s, 18Н). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 804.6 (73%, MNa ⁺ ), 784.4 (100%, MH ⁺ ), 684.3 (71%, MH ⁺ -boc).

C-17: tert-butyl-2-(4-((1E,6E)-7-(3A-dimethoxyphenyl)-3,5-dioxo-4-methyl-hepta-1,6-dienyl)-2-methoxyphenoxy )ethyl carbamate

The amount of the corresponding E-17 aldehyde used: 100 mg = 0.6 mmol

Column chromatography using acetone/petroleum ether = 1:2 → 2:3

Yield: 113 mg, 42% theoretical, orange, viscous solid

Molecular weight = 539.63 g/mol; Empirical formula = C ₃₀ H ₃₇ NO ₈

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.75-7.56 (m, 2H), 7.20-6.82 (m, 7H), 6.70 (d, J=15.9 Hz, 1H), 5.15 (s, 1H) , 4.15-4.06 (m, 2Н), 3.95 (s, 3Н), 3.91 (s, 3Н), 3.89 (s, 3Н), 3.57 (m, 2Н), 2.18 (s, 3Н), 1.44 (s, 9H ). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 562.2 (MNa ⁺ , 41%), 540.3 (MH ⁺ , 100%), 484.2 (MH ⁺ -C ₄ H ₉ , 46%) , 440.3 (MH ⁺ -boc, 3%).

C-22: 2-(4-((1E,6E)-7-(3,4-bis(2-(tert-butoxycarbonylamino)ethoxy)phenyl)-3,5-dioxo-4-methyl-hepta-1 ,6-dienyl)-2-methoxyphenoxy)ethylcarbamic acid

The amount of the corresponding E-17 aldehyde used: 255 mg = 0.6 mmol

Column chromatography using acetone/petroleum ether = 2:5 → 1:2

Yield: 160 mg, 40% theoretical, orange, very viscous solid. Molecular weight = 797.95 g/mol; Empirical formula = C ₄₂ H ₅₉ N ₃ O ₁₂

¹ H-NMR (300 MHz, CDCl ₃ ), δ=7.74-7.52 (m, 2H), 7.21-6.88 (m, 7H), 6.70 (d, J=15.9 Hz, 1H), 5.29 (s, 2H) , 5.16 (s, 1Н), 4.10 (t, J=4.8 Hz, 6Н), 3.90 (m, 3Н), 3.56 (m, 6Н), 2.17 (m, 3Н), 1.46 (s, 9Н), 1.45 ( s, 18H). MS (electrospray ionization, CH ₂ Cl ₂ /MeOH + 10 mmol NH ₄ OAc): 820.4 (100%, MNa ⁺ ), 798.3 (43%, MH ⁺ ), 698.4 (67%, MH ⁺ -boc).

3. Removal of the Boc protecting group from curcumins and ion exchange chromatography

The appropriate boc-protected curcumin (0.2 mmol, 120-160 mg) was dissolved in DCM (6 ml). 4 ml of a 10% solution of TFA in DCM (containing 6% TIS) was added dropwise slowly with stirring. After stirring for 5 h at rt. when protected from light, precipitated the product by adding diethyl ether (10 ml). The precipitate was removed by centrifugation, and then the supernatant was removed. The solid was suspended in diethyl ether (30 ml) and again removed by centrifugation. The supernatant was also removed. The washing step was repeated one more time and the product was air dried in the dark.

Ion exchange chromatography

The column was loaded with Amberlite 954 resin and the ion exchange resin was conditioned with 0.1M HCl. After washing with water to a very weak acid reaction, reconditioning was carried out if necessary using a mixture of water/MeOH/MeCN. The TFA salt was then slowly eluted through the resin in as little solvent mixture as possible and rinsed several times with a small amount of solvent. After removing the solvent under reduced pressure, the remaining solution was freeze-dried. quantitative output.

Eluent:

4. Curcumin complexes

4.a) The TFA salt of SA-CUR-01a (68 mg, 0.1 mmol) was placed in dry DCM (10 ml). Boron etherate trifluoride (20 μl, 0.12 mmol) was added dropwise and the mixture was stirred overnight. The solution was diluted with diethyl ether (20 ml), divided into two Blue Caps tubes and centrifuged. The clot was washed several times with diethyl ether and dried in air. Red powder (TFA salt), quantitative yield.

Ion exchange chromatography

Amberlite 954 resin was loaded into a short column and the ion exchange resin was conditioned using 0.1 M HCl. After washing with water until very slightly acidic, the TFA salt was washed with a minimum amount of water, eluted slowly through the resin, and rinsed several times with a small amount of solvent. The aqueous solution was lyophilized. quantitative output.

4.b) SA-CUR-01a chloride (108 mg, 0.2 mmol) and boron trioxide (0.05 mmol) were stirred overnight in aqueous HCl (1 M, 2 ml) at room temperature. The solvent was removed under a stream of nitrogen and the residue was dried. Red powder, quantitative yield.

4.c) SA-CUR-01a chloride (54 mg, 0.1 mmol) and zinc acetate dihydrate (0.05 mmol) were heated under reflux in a mixture of ethanol/acetic acid/water 3:2:1 (3 ml) for 2 days . The solvent was removed under a stream of nitrogen and the residue was dried. Orange powder, quantitative yield.

A summary of the compounds obtained is given in General Scheme 8.

Example 2) Phototoxicity Experiments

a) Obtaining growing cultures of bacterial strains

All of these experiments were performed under sterile conditions in a sterile box (Biosafe 4-130, Ehret, Emmendingen, Germany). After the addition of photoactive compounds, all work was carried out in complete darkness.

A cell sample of Staphylococcus aureus (ATCC number: 25923) or Escherichia coli (ATCC number: 25922) cells was taken from the cryo-frozen culture and grown under aerobic conditions at 37°C and 175 rpm overnight in an orbital shaker (MAXQ4000, Thermo Scientific, Dubuque, Iowa, USA). Growth was carried out in 20 ml Todd-Hewitt broth (Carl Roth, Karlsruhe, Germany) containing 0.3% yeast extract (AppliChem, Darmstadt, Germany).

Alternatively, Mueller-Hinton medium was used for growth:

Mueller-Hinton liquid medium (Merck KGaA, Darmstadt, Germany) 2.0 g/l meat extract, 17.5 g/l casein hydrolyzate, 1.5 g/l starch, pH: 7.4+0.2.

Muller-Hinton Agar (Merck KGaA, Darmstadt, Germany)

2.0 g/l meat extract, 17.5 g/l casein hydrolyzate, 1.5 g/l starch, 15 g/l agar, pH: 7.4+0.2.

b) Getting a culture in the exponential growth phase

Dilutions were then made (0, 5, 10, 25 and 20% v/v overnight culture) and their absorbances measured at 600 nm in triplicate in 100 μl (Infinite 200 M Pro, Tecan, Mennedorf, Switzerland). A calibration curve (Microsoft Excel) was used to calculate the volume required to obtain a 20 ml culture with an absorbance of 0.05 at 600 nm. The indicated calculated volume of overnight culture was added to 20 ml of Todd-Newit broth (composition indicated above) and grown for two hours at 37°C with constant stirring (175 rpm, MAXQ4000). These cultures were in the exponential growth phase; absorbance at 600 nm was between 0.3 and 0.45.

Subsequent incubation with photoactive substances, as well as irradiation with electromagnetic radiation and the determination of phototoxicity, were carried out by two different methods.

c.1) Incubation, irradiation and determination of phototoxicity

The 2 hour cultures were divided into 1800 µl aliquots. After centrifugation at 20°C, 830 g, 5 min (centrifuge 5417R, Eppendorf, Hamburg, Germany), the pellets were resuspended in phosphate buffer (Dulbecco's modified phosphate buffered saline, DPBS, Sigma-Aldrich) with either 10 or 50 μM solution of the appropriate photosensitizer, with a final volume of 1800 μl.

The resulting solutions were immediately grown in an orbital mixer (parameters see above) for 5 or 25 minutes.

For each photosensitizer, three controls were used simultaneously. The light-only control contained DPBS without photosensitizer. A photosensitizer-only control ("PS-only") was grown in the same manner as the PDI samples, but was not irradiated and kept strictly in the dark. The next control (double negative, "Co-/-") received neither light nor photosensitizer.

After incubation, duplicate samples (500 μl each) were transferred to a 24-well microtiter plate (Cellstar, Greiner Bio-on, Frickenhausen, Germany). The "PS only" and "Co -/-" samples were placed in their own microtiter plate, which was wrapped in aluminum foil to ensure complete opacity.

Growth was carried out with constant stirring (MTS4, IKA, Staufen, Germany, ~175 rpm) from below on an LED matrix with maximum uniformity of the illuminating surface. All of these controls were mixed equally. Technical data for the light source are given in Table 2; the total dose of light was 33.8 J/cm ² .

Determination of the number of colony forming units (CFU) was carried out in accordance with the method published by Miles and Misra (Miles, AA; Misra, SS, Irwin, JO (1938 Nov), "The estimation of the bactericidal power of the blood" The Journal of hygiene 38 (6): 732-49). In this regard, serial dilutions (1:10) of the respective bacterial suspension were obtained in DPBS. Then 5×10 µl of each bacterial dilution was dropped onto Todd-Hewitt plates (with broth containing 1.5% agar (agar-agar, Kobe I, Roth, Karlsruhe, Germany) and grown at 37°C for 24 h. Then the number of surviving colony forming units was determined All tests were performed four times.

c.2) Incubation, irradiation and determination of phototoxicity

In the second experiment, the used photosensitizers (PS) were dissolved in Millipore water and adjusted to various concentrations. 25 μl of bacterial suspension grown overnight (~10 ⁸ /ml) were grown with 25 μl of various concentrations of photosensitizer solution at room temperature for 10 seconds in the dark in a 96-well plate.

Then the suspension was irradiated for 5-20 minutes. For irradiation, a BlueV light source from Waldmann (Villingen-Schwenningen, Germany) was used, which emits light from 380 to 480 nm (maximum emission at about 420 nm). The applied energy density was 17.5 mW/cm ² .

Each experiment was followed by three controls to eliminate the side effect of irradiation/photosensitizer (PS) on bacterial survival: (i) no PS, light only (= light control), (ii) no light, PS only (= dark control), and (iii) no light, no PS (=baseline control). Determination of the number of colony forming units (CFU) per ml was also carried out in accordance with the method published by Miles, Misra and Irwin, described above in section c.1). All tests were performed four times.

d) Results of experiments on phototoxicity

The results of the phototoxicity experiments described above in section c.1) are shown in Figures 1-20. The photosensitizers were tested on the bacterial strain E. coli ATCC 25922. Figures 1-20 show the measured amounts of colony forming units (CFU).

The results of the phototoxicity experiments described in section c.2) are shown in Figures 21 to 33. The photosensitizers (PS) SACUR-01a, SACUR-03 and SACUR-07 were tested on S. aureus ATCC 25923 and E. coli ATCC bacterial strains. 25922 (Fig. 21-23). All other PSs were tested on S. aureus strain ATCC 25923 (FIGS. 24-33). On FIG. 21-33 show the log reduction after illumination relative to control.

On FIG. 21 shows the results of a phototoxicity experiment using SACUR-01a on E. coli strain ATCC 25922 (left) and on S. aureus strain ATCC 25923 (right). The exposure time for E. coli was 15 minutes; for S. aureus, 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (without light, without PS) was 3.6×10 ⁸ /ml for E. coli and 3.9×10 ⁸ /ml for S. aureus.

On FIG. 22 shows the results of a phototoxicity experiment using SACUR-03 on E. coli strain ATCC 25922 (left) and on S. aureus strain ATCC 25923 (right). The exposure time for E. coli was 15 minutes; for S. aureus, 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (without light, without PS) was 3.3×10 ⁸ /ml for E. coli and 4.3×10 ⁸ /ml for S. aureus.

On FIG. 23 shows the results of a phototoxicity experiment using SACUR-07 on E. coli strain ATCC 25922 (left) and on S. aureus strain ATCC 25923 (right). The exposure time for E. coli was 45 minutes; for S. aureus, 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (without light, without PS) was 2.6×10 ⁸ /ml for E. coli and 3.6×10 ⁸ /ml for S. aureus.

On FIG. 24 shows the results of a phototoxicity experiment using SACUR-01a BF2 on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~3.6 x 10 ⁸ bacteria per ml.

On FIG. 25 shows the results of a phototoxicity experiment using SACUR-09a on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~3.3×10 ⁸ bacteria per ml.

On FIG. 26 shows the results of a phototoxicity experiment using SACUR-11a on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~6.3×10 ⁸ bacteria per ml.

On FIG. 27 shows the results of a phototoxicity experiment using SACUR-11c on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~5.1 x 10 ⁸ bacteria per ml.

On FIG. 28 shows the results of a phototoxicity experiment using SACUR-12b on S. aureus strain ATCC 25923. The exposure time for S. aureus was 30 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~6.2 x 10 ⁸ bacteria per ml.

On FIG. 29 shows the results of a phototoxicity experiment using SACUR-13a on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~7.5 x 10 ⁸ bacteria per ml.

On FIG. 30 shows the results of a phototoxicity experiment using SACUR-13C on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~5.5 x 10 ⁸ bacteria per ml.

On FIG. 31 shows the results of a phototoxicity experiment using SACUR-14a on S. aureus strain ATCC 25923. The exposure time for S. aureus was 10 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~4.2×10 ⁸ bacteria per ml.

On FIG. 32 shows the results of a phototoxicity experiment using SACUR-15a on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~3.6 x 10 ⁸ bacteria per ml.

On FIG. 33 shows the results of a phototoxicity experiment using SACUR-15b on S. aureus strain ATCC 25923. The exposure time for S. aureus was 5 minutes. The mean baseline control (arithmetic mean with standard deviation) (no light, no PS) was ~6.3×10 ⁸ bacteria per ml.

As can be seen from FIG. 1-33, irradiation of the used microorganisms, Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli), with the described light dose of blue light (390-500 nm) in the absence of a photosensitizer (0 μM of the corresponding curcumin) did not affect the number of surviving microorganisms compared to unilluminated control.

Table 3 shows the effect of the test substances on E. coli strain ATCC 25922 with an applied light dose of 33.8 J/cm ² for a maximum emission at approximately 435 nm (60 minutes of illumination at an intensity of 9.4 mW/cm ² ). The value for the mean baseline control (arithmetic mean with standard deviation) (without light, without PS) was 3.6×10 ⁸ /ml. Log reduction after illumination is shown relative to baseline control. The corresponding upper value indicated by * refers to an incubation period of 5 minutes and correspondingly the lower value indicated by # refers to an incubation period of 25 minutes.

Table 4 shows the effect of the test substances on the E. coli strain ATCC 25922 for an applied light dose of 15.7 J/cm ² with a maximum emission at about 420 nm (15 min of illumination at an intensity of 17.5 mW/cm ² ). The value for the mean baseline control (arithmetic mean with standard deviation) (without light, without PS) was 3.6×10 ⁸ /ml for E. coli. Log reduction after illumination is shown relative to baseline control.

Table 5 shows the effect of the test substances on the strain S. aureus ATCC 25923. The exposure time was 5 minutes (radiation maximum at about 420 nm) for an applied intensity of 17.5 mW/cm ² , i.e. applied light energy (dosage) 5.3 J/cm ² . The value for the mean baseline control (arithmetic mean with standard deviation) (without light, without PS) was 3.9×10 ⁸ /ml. Log reduction after illumination is shown relative to baseline control.

As clearly seen from FIG. 1-33, after incubation of the microorganisms according to the concentrations of the respective photosensitizers used and subsequent irradiation with the above dosage of light, there is a reduction in CFU/ml and thus inactivation of E. coli and S. aureus.

Comparative Example 3

Subsequently, the stability and phototoxicity of the following compounds were tested.

The CRANAD-2 compound is a good fluorophore that has a fluorescence quantum yield comparable to rhodamine or Cy5 dyes.

Incubation of CRANAD-2 with bacterial strains S. aureus ATCC 25923 and E. coli ATCC 25922, as well as irradiation with electromagnetic radiation and determination of phototoxicity, was carried out as described in sections c.1) and c.2) above. Inactivation of the tested bacterial strains S. aureus ATCC 25923 and E. coli ATCC 25922 under illumination in the presence of CRANAD-2 was not detected by any of the methods.

Due to the presence of amine substituents directly on the aromatic ring, which can act as electron pair donors, photophysics shifts to a singlet process, and much less energy is available for triplet processes. Good energy transfer to the triplet level should be a prerequisite for a photodynamic effect, which, however, was not observed for the CRANAD-2 compound.

Incubation of compound (71) (SACUR-01d) with bacterial strains S. aureus ATCC 25923 and E. coli ATCC 25922, as well as irradiation with electromagnetic radiation and determination of phototoxicity, were carried out as described in sections c.1) and c.2) above. Any inactivation of the tested bacterial strains S. aureus ATCC 25923 and E. coli ATCC 25922 was not observed in any of the methods under illumination in the presence of compound (71) (SACUR-01d), because the decomposition of the compound in the measured solution meant that there were no reliable values are obtained. Compound (71) (SACUR-01d) showed low stability in aqueous solution, which was comparable to the natural base substance curcumin. Free OH groups contribute a lot to this photoinstability because they allow the compound to be easily converted to the quinoid mesomer and thus facilitate the elimination of one half of the molecule to form ferulic acids or substituted vanillins.

The molar extinction coefficient for compound (71) (SACUR-01d) at 420 nm in aqueous solutions A-C below varied between 8000 and 16000 M ^-1 cm ^-1 and thus was significantly less than the known value for curcumin (ε ₄₂₀ , H ₂ O=23800 M ^-1 cm ^-1 ) (see Arnaut LG, Formosinho SJ. J. Photochem. Photobiol. A: Chem. 75, 1993, pages 1-20). These results show that compound (71) does not have sufficient stability in aqueous solution to establish a photodynamic effect after irradiation. Aqueous solution A: distilled water.

Aqueous solution B: isotonic sodium chloride solution (0.9 wt.% NaCl). Aqueous solution C: PBS buffer, pH 7.4 (for composition see Sambrook, J.; Maniatis, T.; Russel, D.W.: Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Press; 3rd edition (2001) ).

Claims (215)

1. 1,7-diaryl-1,6-heptadiene-3,5-dione compound of formula (1)

, (one) where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, where the 1,7-diaryl-1,6-heptadiene-3,5-dione compound of formula (1) does not contain an OH group that is directly linked to the organic residue Q ¹ or Q ² , and where K is hydrogen or a cation, and where (a) at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1a, where said at least one organic residue W1a has the general formula (5a), (6a), (7a), (8a) or (9a):

where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, and p, respectively, independently represent an integer from 1 to 6 , and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, where X ^a , respectively, independently of the others, represents the remainder of the formula (20c), (20d) or (21):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be straight or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, and where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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 where (b) 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, preferably quaternary, nitrogen atom and/or at least one positively charged , preferably quaternary, a phosphorus atom, where said one organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b):

and where, optionally, at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1b having the general formula (4b), (5b), (6b), ( 7b), (8b) or (9b), where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, and p, respectively, independently represent an integer from 1 to 6 , and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, nitrogen atom or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and where the residues R1, R2, R4 and R5, respectively, independently of the others, are hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing 2 to 12 C atoms, or a glycol containing 2 to 12 C atoms. 2. Connection according to claim 1, where K is the cation M ^z+ of the metal M, where z is the formal oxidation state of said metal M and is an integer from 1 to 7, preferably from 2 to 5, and where the specified compound has the formula (2)

, (2) where L ¹ and L ² , respectively, independently of the others, represent water, halide, cyanide, thiocyanate, phosphate, hydrogen phosphate or carboxylate ion of a carboxylic acid containing from 1 to 10 carbon atoms, preferably formate, acetate, n-propionate, lactate , oxalate, fumarate, maleate, tartrate, succinylate, benzoate, salicylate or citrate. 3. 1,7-diaryl-1,6-heptadiene-3,5-dione compound of formula (3)

where M ^z+ is a metal cation, where z is the formal oxidation state of said metal M and is an integer from 1 to 7, preferably from 2 to 5, and where Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and where the residues Q ^1a and Q ^2a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue, and where (a) at least one of the residues Q ¹ and Q ² , respectively, independently of the others, has as substituents at least one organic residue W1a having the general formula (5a), (6a), (7a), (8a ) or (9a):

where at least one of the residues Q ^1a and Q ^2a , respectively, independently of the others, contains as substituents at least one organic residue W1c having the general formula (5c), (6c), (7c), (8c) or (9c):

where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, and p, respectively, independently represent an integer from 1 to 6 , and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, and where X ^a , respectively, independently of the others, represents the remainder of the formula (20c), (20d), (21) or (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^{(XVI )} and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and where X ^c , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, nitrogen atom or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and where the residues R1, R1 ^a , R2, R2 ^a , R3, R3 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl, containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms, or where (b) the residue R3 or R3 ^a , respectively, independently of the others, is an organic residue W2a, where said one organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b):

and where, optionally, at least one of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, contains as substituents at least one organic residue W1b having the general formula (4b), (5b) , (6b), (7b), (8b) or (9b), where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, p, and r, respectively, independently represent an integer from 1 up to 6, and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and where the residues R1, R1 ^a , R2, R2 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 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. 4. The compound according to claim 3, characterized in that the compound of formula (3) has the formula (3a)

, (3a) where M ^z+ is a metal cation, where z is the formal oxidation state of said metal M and is an integer from 1 to 7, preferably from 2 to 5, and where Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and where (a) at least one of the residues Q ¹ and Q ² , respectively, independently of the others, has as substituents at least one organic residue W1a having the general formula (5a), (6a), (7a), (8a ) or (9a):

where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, and p, respectively, independently represent an integer from 1 to 6 , and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, and where X ^a , respectively, independently of the others, represents the remainder of the formula (20c), (20d), (21) or (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^{(XVI )} and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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 where (b) the residue R3, respectively, independently of the others, is an organic residue W2a, where the specified one organic residue W2a has the General formula (4b), (5b), (6b), (7b), (8b) or (9b) :

and where, optionally, at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1b having the general formula (4b), (5b), (6b), (7b), (8b) or (9b), where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, p, and r, respectively, independently represent an integer from 1 up to 6, and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and where the residues R1, R2, R4 and R5, respectively, independently of the others, are hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing 2 to 12 C atoms, or a glycol containing 2 to 12 C atoms. 5. Connection according to any one of paragraphs. 2, 3 or 4, where M is selected from the group which consists of B, Al, Zn, Cu, Mg, Ca, Fe, Si, Ga, Sn, Rh, Co, Ti, Zr, V, Cr, Mo, Mn, Ru, Pd, Ir , Ni and their combinations. 6. The connection according to any one of paragraphs. fifteen, where the residues Q ¹ , Q ^1a , Q ³ and Q ^3a , respectively, independently of the others, represent an aromatic residue with the general formula (11a), (12a), (13a), (14a), (15a), (16a) , (17a), (18a) or (19a):

and where the residues Q ² , Q ^2a , Q ⁴ and Q ^4a , respectively, independently of others, represent an aromatic residue with the General formula (11b), (12b), (13b), (14b), (15b), (16b), (17b), (18b) or (19b):

and where, respectively, at least 1 residue R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^25a - R ^33a , R ^34a - R ^42a , R ^43a - R ^51a , R ^52a - R ^60a , R ^61a - R ^69a , R ^70a - R ^78a , R ^6b - R ^10b , R ^11b - R ^17b , R ^18b - R ^24b , R ^25b - R ^33b , R ^34b - R ^42b , R ^43b - R ^51b , R ^52b - R ^60b , R ^61b - R ^69b or R ^70b - R ^78b , respectively, independently of the others, represents an organic residue W1a, or an organic residue W1b, or an organic residue W1c, and where the residues are R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^25a - R ^33a , R ^34a - R ^42a , R ^43a - R ^51a , R ^52a - R ^60a , R ^61a - R ^69a , R ^70a - R ^78a , R ^6b - R ^10b , R ^11b - R ^17b , R ^18b - R ^24b , R ^25b - R ^33b , R ^34b - R ^42b , R ^43b - R ^51b , R ^52b - R ^60b , R ^61b - R ^69b or R ^70b - R ^78b which is not an organic residue W1a, or an organic residue W1b, or an organic residue W1c, respectively, independently of the others, are identical or different and represent hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate , aldehyde containing from 1 to 8 C atoms, ketone containing from 2 to 8 C atoms, O-alkyl containing from 1 to 12 C atoms, S-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, S-alkenyl containing from 2 to 12 C atoms, O-aryl containing from 5 to 20 C atoms, S-aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, a thioether containing from 2 to 12 C atoms, a carboxylic acid ester containing from 1 to 12 C atoms, carboxylic acid amide containing 1 to 12 C atoms, thioester containing 1 to 12 C atoms, alkyl containing 1 to 12 C atoms, alkenyl containing 2 to 12 C atoms, cycloalkyl containing 3 to 12 C atoms, cycloalkenyl containing 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, or heteroaryl which does not contain a nitrogen atom containing 4 to 20 C atoms. 7. Connection according to claim 6, where the residues Q ¹ , Q ^1a , Q ³ and Q ^3a , respectively, independently of others, represent an aromatic residue with the General formula (11a), (12a) or (13a) and where the residues Q ² , Q ^2a , Q ⁴ and Q ^4a , respectively, independently of the others, represent an aromatic residue with the general formula (11b), (12b) or (13b), and where, respectively, at least 1 residue R ^6a - R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^6b - R ^10b , R ^11b - R ^17b or R ^18b - R ^24b , respectively, regardless of the others , represents an organic residue W1a, or an organic residue W1b, or an organic residue W1c, where the residues R ^10a , R ^11a - R ^17a , R ^18a - R ^24a , R ^6b - R ^10b , R ^11b - R ^17b and R ^18b - R ^24b , which are not organic residue W1a, or organic residue W1b, or organic residue W1c, respectively, independently of the others, are identical or different and represent hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate, aldehyde containing from 1 to 8 C atoms, ketone containing from 2 to 8 C atoms, O-alkyl, containing from 1 to 12 C atoms, S-alkyl containing from 1 to 12 C atoms, O-alkenyl containing from 2 to 12 C atoms, S-alkenyl containing from 2 to 12 C atoms, O-aryl containing from 5 to 20 C atoms, S-aryl containing 5 to 20 C atoms, ester containing 2 to 12 C atoms, thioether containing 2 to 12 C atoms, carboxylic acid ester containing 1 to 12 C atoms, carboxylic acid amide of 1 to 12 C atoms, thioester of 1 to 12 C atoms, alkyl of 1 to 12 C atoms, alkenyl of 2 to 12 C atoms, chi cloalkyl containing 3 to 12 C atoms, cycloalkenyl containing 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, or heteroaryl which does not contain a nitrogen atom, containing 4 to 20 C atoms. 8. Connection according to any one of paragraphs. 1 - 7, where the organic residue X ^b and/or X ^c , respectively, independently of the others, represents a residue of formula (20a), (20b), (21), (22a), (22b), (23a), (24b) or (24 ):

where each of the residues R ^(IVa) , R ^(Va) , R ^(IVb) , R ^(Vb) , R ^(VIb) , R ^(VII) , R ^(VIII) , R ^(X) , R ^(XI) , R ^(XII) , R ^(XIII) , R ^(XIV) , R ^(XV) , R ^(XVI) , and R ^(XVII) , respectively, independently of the others, represent hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be straight or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, and where the remainder of formula (22a) and the remainder of formula (23a):

represent a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a double bond, and where the remainder of formula (22b) and the remainder of formula (23b):

represent a substituted or unsubstituted heterocyclic residue containing from 5 to 7 ring atoms, which include at least 1 carbon atom and at least 1 nitrogen atom, and optionally 1 or 2 oxygen atoms, where 1 nitrogen atom forms a single bond. 9. Connection according to any one of paragraphs. eighteen, where the organic residue W2a and/or W1b and/or W1c, respectively, independently of the others, represent an organic residue with the general formula (31a), (31b), (32), (34), (35), (37a) or (37b):

where Y ^- represents an anion, which, respectively, independently of the others, represents fluoride, chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms. 10. Connection according to any one of paragraphs. 19, where the organic residue W1a, respectively, independently of the others, represents an organic residue with the general formula (31a), (31b), (32) or (34):

and where Y ^- represents an anion, which, respectively, independently of the others, represents fluoride, chloride, bromide, iodide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms. 11. The connection according to any one of paragraphs. 1 - 10, where said compound is at least one compound of formula (40) - (63), (68), (69a), (69b) or (70):

. 12. Use of a 1,7-diaryl-1,6-heptadiene-3,5-dione compound of formula (1) and/or (3) or, respectively, its pharmacologically acceptable salt and/or ester as a photosensitizer in medical treatment for the inactivation of microorganisms, and the specified connection is at least one connection according to any one of paragraphs. 1-11, where formula (1) is

where the residues Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, where the compound of formula (1) does not contain an OH group, which is directly linked to the organic residue Q ¹ or Q ² , and where K is hydrogen or a cation, and where (a) at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1a, where said at least one organic residue W1a has the general formula (5a), (6a), (7a), (8a) or (9a):

where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, and p, respectively, independently represent an integer from 1 to 6 , and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, where X ^a , respectively, independently of the others, represents the remainder of the formula (20c), (20d) or (21):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl radical, which may be straight or branched, containing from 1 to 8 C atoms, or an ether radical, which may be linear or branched, containing from 1 to 8 C atoms, and where the residues R1, R2, R3, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl containing from 1 to 12 C atoms, alkylaryl containing from 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 where (b) 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, preferably quaternary, nitrogen atom and/or at least one positively charged , preferably quaternary, a phosphorus atom, where said one organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b):

and where, optionally, at least one of the residues Q ¹ and Q ² , respectively, independently of the others, contains as substituents at least one organic residue W1b having the general formula (4b), (5b), (6b), ( 7b), (8b) or (9b), where h is an integer from 1 to 20, where k is an integer from 0 to 10, where l is an integer from 0 to 10, and where m, n, and p, respectively, independently, represent an integer from 1 to 6 , and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, nitrogen atom or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and where the residues R1, R2, R4 and R5, respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms , an ether containing from 2 to 12 C atoms, or a glycol containing from 2 to 12 C atoms; and where formula (3) is:

where M ^z+ is a metal cation, where z is the formal oxidation state of said metal M and is an integer from 1 to 7, preferably from 2 to 5, and where Q ¹ and Q ² , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue, and where the residues Q ^1a and Q ^2a , respectively, independently of the others, represent one substituted or unsubstituted, monocyclic or polycyclic aromatic residue or one substituted or unsubstituted, monocyclic or polycyclic heteroaromatic residue, and where (a) at least one of the residues Q ¹ and Q ² , respectively, independently of the others, has as substituents at least one organic residue W1a having the general formula (5a), (6a), (7a), (8a ) or (9a):

where at least one of the residues Q ^1a and Q ^2a , respectively, independently of the others, contains as substituents at least one organic residue W1c having the general formula (5c), (6c), (7c), (8c) or (9c):

where h is an integer from 1 to 20, where k is an integer from 0 to 10, where l is an integer from 0 to 10, and where m, n, and p, respectively, independently, represent an integer from 1 to 6 , and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, and where X ^a , respectively, independently of the others, represents the remainder of the formula (20c), (20d), (21) or (24):

where each of the residues R ^(VII) , R ^(VIII) and R ^(IX) , respectively, independently of the others, represents hydrogen, an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing from 1 to 8 C atoms, and where each of the residues R ^(XV) , R ^{(XVI )} and R ^(XVII) , respectively, independently of the others, represent an aryl residue containing from 5 to 12 C atoms, an alkylaryl residue containing from 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing from 1 to 8 C atoms, or an ether residue which may be linear or branched, containing from 1 to 8 C atoms, and where X ^c , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, or (ii) contains at least one positively charged, preferably quaternary, nitrogen atom or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and where the residues R1, R1 ^a , R2, R2 ^a , R3, R3 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, cycloalkyl, containing from 1 to 12 C atoms, alkylaryl containing from 1 to 12 C atoms, aryl containing from 5 to 20 C atoms, ether containing from 2 to 12 C atoms, or glycol containing from 2 to 12 C atoms, or where (b) the residue R3 or R3 ^a , respectively, independently of the others, is an organic residue W2a, where said one organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b) or (9b):

and where, optionally, at least one of the residues Q ¹ , Q ^1a , Q ² and Q ^2a , respectively, independently of the others, contains as substituents at least one organic residue W1b having the general formula (4b), (5b) , (6b), (7b), (8b) or (9b), where h represents an integer from 1 to 20, where k represents an integer from 0 to 10, where l represents an integer from 0 to 10, and where m, n, p, and r, respectively, independently represent an integer from 1 up to 6, and where A, respectively, independently of the others, represents oxygen or sulfur, where D and E, respectively, independently of the others, represent hydrogen, halogen, G–R ^(I) or G–C(=G)–R ^(II) , where G, respectively, independently of the others, represents oxygen or sulfur, and where the residues R ^(I) and R ^(II) , respectively, independently of the others, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, and phenyl and benzyl may be unsubstituted or substituted , where aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group that does not contain a nitrogen atom, where X ^b , respectively, independently of the others, is an organic residue that (i) contains at least one neutral nitrogen atom that can be protonated, (ii) contains at least one positively charged, preferably quaternary, nitrogen atom, or (iii) contains at least one positively charged, preferably quaternary, phosphorus atom, and where the residues R1, R1 ^a , R2, R2 ^a , R4, R4 ^a , R5 and R5 ^a , respectively, independently of the others, represent hydrogen, halogen, alkyl containing from 1 to 12 C atoms, alkylaryl containing from 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. 13. The method of inactivation of microorganisms, including the following steps: (A) bringing the microorganisms into contact with at least one photosensitizer, said photosensitizer being at least one compound according to any one of paragraphs. 1-11, and (B) irradiating said microorganisms and at least one photosensitizer with electromagnetic radiation. 14. The method according to claim 13, where K in the compound is a cation M ^z+ of metal M, where z is the formal oxidation state of said metal M, and where z is an integer from 1 to 7, preferably from 2 to 3, and where said compound has the formula (102):

where L ¹ and L ² , respectively, independently of the others, represent water, fluoride, chloride, bromide, iodide, phosphate, hydrogen phosphate, dihydrogen phosphate, sulfate, hydrogen sulfate, tosylate, mesylate, or at least one carboxylation with a carboxylic acid containing from 1 to 15 carbon atoms and/or mixtures thereof. 15. The method according to claim 13 or 14, where the irradiation of said microorganisms and at least one photosensitizer with electromagnetic radiation is carried out in the presence of at least one oxygen donor compound, preferably a peroxide and/or at least one oxygen-containing gas, preferably oxygen. 16. The method according to claim 13 or 15, where the wavelength of electromagnetic radiation is in the range from 280 to 1000 nm, more preferably from 380 to 1000 nm. 17. The method according to claim 13 or 15, where the energy density of electromagnetic radiation is in the range from 1 μW/cm ² to 1 kW/cm ² , more preferably from 1 mW/cm ² to 100 W/cm ² , more preferably from 2 mW/cm ² to 50 W/cm ² , more preferably 6 mW/cm ² to 30 W/cm ² , more preferably 7 mW/cm ² to 25 W/cm ² . 18. The method according to any one of paragraphs. 13 - 17, where the specified at least photosensitizer is at least one compound according to any one of paragraphs. 4-11 and/or a pharmaceutically acceptable salt and/or ester thereof. 19. Non-medical use of the compounds according to any one of paragraphs. 1-11 and/or a pharmaceutically acceptable salt and/or ester thereof as a photosensitizer for inactivating microorganisms, which are preferably selected from the group consisting of viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, algae and bloodborne parasites. 20. Use according to claim 19 for cleaning the surface and / or coating of the product. 21. Use according to claim 19 or 20 for surface cleaning and / or coating of medical products, food packaging, textiles; building materials, electronic devices, furniture or hygiene products. 22. Use according to claim 19 or 20 for the disinfection of liquids. 23. Use according to claim 19 or 20 for food disinfection. 24. A coated product, characterized in that at least one compound according to any one of paragraphs is applied to the surface of the product. 1-11.

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