TETRAHYDROCARBAZOLES, A PROCESS FOR THE PREPARATION OF THOSE COMPOUNDS, AND THE USE THEREOF

Abstract: There are described tetrahydrocarbazoles of formula (1) or (2). The compounds are suitable as antimicrobial active ingredients.

Description: Tetrahydrocarbazoles, a process for the preparation of those compounds, and the use thereof The present invention relates to novel tetrahydrocarbazoles, to a process for the preparation of those compounds and to the use thereof as antimicrobial active ingredients. The tetrahydrocarbazoles according to the invention correspond to formula wherein Ri is hydrogen; C Czoalkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycIoalkynyl; phenyl or phenyl-C,-C 5 alkyl each unsubstituted or substituted by C C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C r C 7 alkylcarbonyl, C r C 7 alkoxycarbonyl, C 3 -C 12 cycloalkylcarbonyl, C 3 -C 12 -cycloalkoxy- carbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C.,-C 20 alkyl- amino or by nitro, R 2 is hydrogen; hydroxy; C,-C 20 alkyl; C 3 -C 12 cycloalkyl; C^Caohydroxyalkyl; C C 20 - hydroxyalkoxy; C C^aminoalkyl; N-C Csomonoalkylamino-C^Czoalkyl; N-C 1 -C 20 - monoalkylaminohydroxy-CrC^alkoxy; N.N-CrCzodialkylamino-C^C^alkyl; N,N- C Czodialkylaminohydroxy-CrC^alkoxy; carboxy; carboxy-C r C 20 alkyl ester; C,-C 2 o- haloalkyl; C r C 20 haIoalkoxy; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 - cycloalkynyl; Cr joalkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl; R 3 and R 4 are each independently of the other hydrogen; or C,-C 20 alkyl; or R 3 and R 4 together denote a C 2 -C 20 alkylene radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 -alkynylene radical; or a C 3 -C 20 alkylene radical interrupted by -N(R 6 )-, it being possible for such bivalent radicals to be further substituted by one or more ^-C^al y!, C 3 -C 12 -cycloalkyl, C 2 -C 20 alkenyl, C 4 - C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, CrCy-alkoxycarbonyl, or phenyl or phenyl-CrCgalkyl each unsubstituted or substituted by Chalk !, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C^C^-alkoxycarbonyl, C 3 - C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di- C C^alkylamino or by nitro; or R 3 and R 4 together denote a bicyclo[x.y.z.]C 4 -C 20 alkylene; or bicyclo[x.y.z.]C 4 -C 20 alkylene interrupted by -N(R 6 )-, wherein x, y and z are each independently of the others from 0 to 10; R 5 is hydrogen; hydroxy; C r C 20 alkyl; C^Cuoalkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloaIkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C r C 5 alkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 -cyclo- Ikoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, tri- luoroethyl, pentafluoroethyl, amino, N,N-mono- or di-C^C^alkylamino or by nitro; R 6 is hydrogen; ^-C^alky!; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 7 alkoxycarbonyl; phenyl or phenyl-C^Csalkyl each unsubstituted or substituted by C^Csalkyl, C 3 -C 12 cycloalkyl, C^Csalkoxy, C 3 -C 12 -cyclolkoxy, halogen, carboxy, C,-C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C r C 20 alkylamino or by nitro; Q is -SO 2 -; -O-; or -(CO)-; X is -CH-; or -N-; m is from 1 to 3; and t is 0 or 1. CrCzoAlkyl denotes straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooc- tyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl. C 3 -C 12 Cycloalkyl is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclodocecyl and especially cyclohexyl. Within the scope of the meanings given, alkenyl includes inter alia allyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4-enyl. CrC 20 Alkoxy denotes straight-chain or branched radicals, such as methoxy, ethoxy, propoxy, butoxy or pentyloxy, hexyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecy- loxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy or eicosyloxy. Halogen is fluorine, chlorine, bromine or iodine. Preference is given to the use of compounds of formula (1) or (2) wherein R, is hydrogen; C,-C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-CrCsalkyl each unsubstituted or substituted by C C 5 alkyl, C 3 -C 12 cycloalkyl, C^Csalkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C r C 7 alkylcarbonyl, C r C 7 alkoxycarbonyl, C 3 -C 12 cycloalkylcarbonyl, C 3 -C 12 -cycloalkoxy- arbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-CrCzoalkylmino or by nitro, R 2 is hydrogen; hydroxy; CrCzoalkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 - C 20 alkynyl; C 4 -Cι 2 cycloalkynyl; C r C 20 alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl; R 3 and R 4 are each independently of the other hydrogen; or C^C^alkyl; or R 3 and R 4 denote a C 2 -C 20 alkylene radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 alkynylene radical; or a C 3 - C 20 alkylene radical interrupted by -N(R 6 )- , it being possible for such bivalent radicals to be further substituted by one or more C C 20 alkyl, C 3 -C 12 cycloalkyl, C 2 -C 20 -alkenyl, C 4 - C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, C T ^alkoxycarbonyl, or phenyl or phenyl-CrCgalkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 -cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, Cr^alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-CrC^alkylamino or by nitro; R 5 is hydrogen; hydroxy; C.,-C 20 alkyl; C,-C 20 alkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by ^-Csalkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 - cycloalkoxy, halogen, carboxy, C r C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-CrC 20 alkylamino or by nitro; R 6 is hydrogen; C r C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; C C 7 alkoxycarbonyl; phenyl or phenyl-CrCsalkyl each unsubstituted or substituted by Chalky!, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 -cycloalkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-CrC^alkylamino or by nitro; Q is -SO 2 -; -O-; or -(CO)-; X is -CH-; or -N-; m is from 1 to 3; and t is O or l. In formula (1) R, is preferably hydrogen; C C 20 alkyl; phenyl or phenyl-C r C s alkyl, and is especially hydrogen; or CrCsalkyl. Preference is given also to compounds of formula (1) wherein R 2 is hydrogen; C,-C 20 alkyl; C r C 20 alkoxy; or halogen and is especially hydrogen; C r C 5 alkyl; C^Csalkoxy; or halogen. Very special preference is given to compounds of formula wherein R, is hydrogen; C r C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C^Csalkyl each unsubstituted or substituted by C C 5 alkyl, C 3 -C 12 cycloalkyl, CrCsalkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C,- C 7 alkylcarbonyl, C^C^Ikoxycarbonyl, C 3 -C 12 cycloalkylcarbonyl, C 3 -C 12 -cycloalkoxy- arbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C^Czoalkylmino or by nitro, R 2 is hydrogen; hydroxy; C r C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 - C 20 alkynyl; C 4 -C 12 cycloalkynyl; C^Czoalkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C r C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl; R 5 is hydrogen; hydroxy; C r C 20 alkyl; C^Czoalkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C r C 5 alkyl each unsubstituted or substituted by C r C 5 alkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 - cycloalkoxy, halogen, carboxy, C^C^Ikoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C,-C 20 alkylamino or by nitro; R 6 is hydrogen; C^Czoalkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; C r C 7 alkoxycarbonyl; phenyl or phenyl-C Csalkyl each unsubstituted or substituted by C^Csalkyl, C 3 -C 12 cycloalkyl, C C 5 alkoxy, C 3 -C 12 -cycloalkoxy, halogen, carboxy, C r C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C^C^alkylamino or by nitro; Q is -SO 2 -; -O-; or -(CO)-; T, is C 2 -C 20 alkylene; C 2 -C 20 alkenylene; C 4 -C 20 alkynylene; or C 3 -C 20 alkylene interrupted by R 3 I 3 -N- ; X is -CH-; or -N-; s is from 1 to 4; and t is O or 1. Preference is given to compounds of formula (3) or (4) wherein , is a -(CH 2 ) 2 . 12 - radical and R 6 is hydrogen; or C C 5 alkyl, and especially to compounds of formula (3) or (4) wherein T, is a -(CH 2 ) 3 -, -(CH 2 ) 4 -, -(CH 2 ) 5 -, or -(CH 2 ) 10 - radical; and R 6 is hydrogen; or C C 5 alkyl. R 5 in formula (1) is preferably hydrogen; C C 20 alkyl; phenyl or phenyl-C,-C 5 alkyl; and more especially hydrogen; C r C 5 alkyl; or phenyl. More especially preferred compounds according to the invention correspond to formula wherein R 6 ' and R 6 " are each independently of the other hydrogen; C r C 20 alkyl; C,-C 7 alkoxy-carbonyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C^Csalkyl, C,- C 7 alkoxycarbonyl, N,N-mono- or di-C Cajalkylamino or by nitro; \ I , is -CH- ; -(CH 2 ) 7 - or -N— ; and R,, R 2 , R 5 , R 6 and X are as defined for formula (3). In formulae (5) and (6) preferably R 6 ', R 6 " and R 6 are each independently of the others hydrogen; C,-C 20 alkyl; C C 7 - alkoxycarbonyl; phenyl; or phenyl-CrCsalkyl. Special preference is given to compounds of formula (5) and (6) wherein R 6 ' and R 6 " and R 6 are each independently of the others hydrogen; C r C 5 alkyl; C r C 7 - alkoxycarbonyl; phenyl or benzyl. Further preferred compounds according to the invention correspond to formula wherein R T is hydrogen; or Chalky!; R 2 is hydrogen; Chalky!; CI or Br; R 5 is hydrogen; d-Csalkyl; or phenyl R 6 ' and R 6 " are each independently of the other hydrogen, C^Csalk l; or C^C^Ikoxy- carbonyl; R 6 is hydrogen; C C 5 alkyl; C C 7 alkylcarbonyl; or phenyl-C r C 5 alkyl; l I T, is -CH- ; or — N— ; and X is -CH-. Compounds according to the invention are listed in Tables 1 a and b below by way of example: -34 35 The preparation of the tetrahydrocarbazoles according to the invention is carried out according to widely known methods in a 3-component reaction, as described in the publication by W. Noland et al., J. Heterocycl. Chem., 1993, 30, 81-91. For that purpose, mixtures of a (substituted) indole, ketone or aldehyde and a dienophile are reacted in a suitable solvent, e.g. 1-butanol, toluene, DMF, DMSO or Tetralin, using acid catalysts, e.g. hydrochloric acid, trifluoroacetic acid, toluenesulfonic acid, etc.. The ketone or aldehyde component can also serve as solvent. The mixture is heated for several hours at a temperature of from 50°C to 140°C. The resulting tetrahydrocarbazoles are filtered off and washed, or precipitated from the solvent with cold n-hexane and filtered off. Some of the substances are also obtained by concentrating the reaction mixture by evaporation. The course of the reaction can be represented schematically as follows: (2) The tetrahydrocarbazoles obtained in that manner are generally obtained in the form of race- mates and are mainly in the cis stereochemical form. Some compounds also form trans stereochemical isomers. The invention relates also to the process for the preparation of those compounds. The tetrahydrocarbazoles according to the invention exhibit pronounced antimicrobial activity, especially against pathogenic gram-positive and gram-negative bacteria and against bacteria of the skin flora, and also against yeasts and moulds. They are accordingly especially suitable for disinfection, deodorisation, and for the general and antimicrobial treatment of the skin and mucosa, and integumentary appendages (hair), especially for the disinfection of hands and wounds. The compounds are accordingly suitable as antimicrobial active ingredients and as preservatives in personal care preparations, such as shampoos, bath additives, hair care products, liquid and solid soaps (based on synthetic surfactants and salts of saturated and/or unsaturated fatty acids), lotions and creams, deodorants, other aqueous or alcoholic solutions, e.g. cleansing solutions for the skin, moist wipes, oils or powders. The invention accordingly relates also to a personal care preparation comprising at least one compound of formula (1) or (2) and cosmetically tolerable carriers or adjuvants. The personal care preparation according to the invention contains from 0.01 to 15 % by weight, preferably from 0.1 to10 % by weight, based on the total weight of the composition, of a compound of formula (1) or (2) and cosmetically tolerable adjuvants. Depending upon the form of the personal care preparation, it comprises, in addition to the compound of formula (1) or (2), further constituents, such as sequestering agents, colourings, perfume oils, thickening or solidifying agents (consistency regulators), emollients, UV- absorbers, skin protective agents, antioxidants, additives that improve the mechanical properties, such as dicarboxylic acids and/or aluminium, zinc, calcium or magnesium salts of Cι -C 22 fatty acids and, optionally, preservatives. The personal care preparation according to the invention may be in the form of a water-in-oil or oil-in-water emulsion, an alcoholic or alcohol-containing formulation, a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, a gel, a solid stick or an aerosol formulation. As a water-in-oil or oil-in-water emulsion the cosmetically tolerable adjuvant contains preferably from 5 to 50 % of an oil phase, from 5 to 20 % of an emulsifier and from 30 to 90 % water. The oil phase may comprise any oil suitable for cosmetic formulations, for example one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol. Preferred mono- or poly-ols are ethanol, isopropanol, propylene glycol, hexylene glycol, glyc- erol and sorbitol. Cosmetic formulations according to the invention are used in various fields. There come into consideration, for example, especially the following preparations: skin-care preparations, e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, synthetic detergents or washing pastes, bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts; skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils; cosmetic personal care preparations, e.g. facial make-up in the form of day creams or powder creams, face powder (loose or compressed), rouge or cream make-up, eyecare preparations, e.g. eyeshadow preparations, mascara, eyeliner, eyecreams or eye-fix creams; lip-care preparations, e.g. lipsticks, lip gloss, lip contour pencils, nail-care preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle removers; intimate hygiene preparations, e.g. intimate washing lotions or intimate sprays; foot-care preparations, e.g. foot baths, foot powders, foot creams or foot balsams, special deodorants and antiperspirants or callus-removing preparations; light-protective preparations, such as sun milks, lotions, creams, oils, sun-blocks or tropicals, pre-tanning preparations or after-sun preparations; skin-tanning preparations, e.g. self-tanning creams; depigmenting preparations, e.g. preparations for bleaching the skin or skin-lightening preparations; insect repellents, e.g. insect-repellent oils, lotions, sprays or sticks; deodorants, such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons; antiperspirants, e.g. antiperspirant sticks, creams or roll-ons; preparations for cleansing and caring for blemished skin, e.g. synthetic detergents (solid or liquid), peeling or scrub preparations or peeling masks; hair-removal preparations in chemical form (depilation), e.g. hair-removing powders, liquid hair-removing preparations, cream- or paste-form hair-removing preparations, hair- removing preparations in gel form or aerosol foams; shaving preparations, e.g. shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, preshave preparations for dry shaving, aftershaves or aftershave lotions; fragrance preparations, e.g. fragrances (eau de Cologne, eau de toilette, eau de perfume, perfume de toilette, perfume), perfume oils or perfume creams; dental care, denture-care and mouth-care preparations, e.g. toothpastes, gel toothpastes, tooth powders, mouthwash concentrates, anti-plaque mouthwashes, denture cleaners or denture fixatives; cosmetic hair-treatment preparations, e.g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e.g. pre-treatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair- setting preparations, hair foams, hairsprays, bleaching preparations, e.g. hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colourants, preparations containing self-oxidising dyes, or natural hair colourants, such as henna or camomile. An antimicrobial soap has, for example, the following composition: 0.01 to 5 % by weight of a compound of formula (1) or (2), 0.3 to 1 % by weight titanium dioxide, 1 to 10 % by weight stearic acid, ad 100 % soap base, e.g. a sodium salt of tallow fatty acid or coconut fatty acid, or glycerol. A shampoo has, for example, the following composition: 0.01 to 5 % by weight of a compound of formula (1) or (2), 12.0 % by weight sodium laureth-2-sulfate, 4.0 % by weight cocamidopropylbetaine, 3.0 % by weight NaCl and water ad 100 %. A deodorant has, for example, the following composition: 0.01 to 5 % by weight of a compound of formula (1) or (2), 60 % by weight ethanol, 0.3 % by weight perfume oil, and water ad 100 %. The invention relates also to an oral composition comprising 0.01 to 15 % by weight, based on the total weight of the composition, of a compound of formula (1) or (2), and orally tolerable adjuvants. Example of an oral composition: 10 % by weight sorbitol, 10 % by weight glycerol, 15 % by weight ethanol, 15 % by weight propylene glycol, 0.5 % by weight sodium lauryl sulfate, 0.25 % by weight sodium methylcocyl taurate, 0.25 % by weight polyoxypropylene/polyoxyethylene block copolymer, 0.10 % by weight peppermint flavouring, 0.1 to 0.5 % by weight of a compound of formula (1) or (2) and 48.6 % by weight water. The oral composition according to the invention may be, for example, in the form of a gel, a paste, a cream or an aqueous preparation (mouthwash). The oral composition according to the invention may also comprise compounds that release fluoride ions which are effective against the formation of caries, for example inorganic fluoride salts, e.g. sodium, potassium, ammonium or calcium fluoride or organic fluoride salts, e.g. amine fluorides, which are known under the trade name Olafluor. The tetrahydrocarbazoles of formula (1) or (2) used according to the invention are also suitable for treating, especially preserving, textile fibre materials. Such materials are undyed and dyed or printed fibre materials, e.g. of silk, wool, polyamide or polyurethanes, and especially cellulosic fibre materials of all kinds. Such fibre materials are, for example, natural cellulose fibres, such as cotton, linen, jute and hemp, as well as cellulose and regenerated cellulose. Preferred suitable textile fibre materials are made of cotton. The tetrahydrocarbazoles according to the invention are suitable also for treating, especially imparting antimicrobial properties to or preserving, plastics, e.g. polyethylene, polypropylene, polyurethane, polyester, polyamide, polycarbonate, latex, etc.. Fields of use therefore are, for example, floor coverings, plastics coatings, plastics container and packaging materials; kitchen and bathroom utensils (e.g. brushes, shower curtains, sponges, bathmats), latex, filter materials (air and water filters), plastics articles used in the field of medicine, e.g. dressing materials, syringes, catheters, etc., so-called "medical devices", gloves and mattresses. Paper, for example papers used for hygiene purposes, may also be provided with antimicrobial properties using the tetrahydrocarbazoles according to the invention. It is also possible for nonwovens, e.g. nappies/diapers, sanitary towels, panty liners, and cloths for hygiene and household uses, to be provided with antimicrobial properties in accordance with the invention. The tetrahydrocarbazoles of formula (1) or (2) are also used in washing and cleaning formulations, e.g. in liquid or powder washing agents or softeners. The tetrahydrocarbazoles of formula (1) or (2) can be used especially in household and general-purpose cleaners for cleaning and disinfecting hard surfaces. A cleaning preparation has, for example, the following composition: 0.01 to 5 % of a compound of formula (1) or (2), 3.0 % octyl alcohol 4EO, 1.3 % fatty alcohol C 8 -C 10 polyglucoside, 3.0 % isopropanol, ad 100 % water. In addition to preserving cosmetic and household products, the preservation of technical products, the provision of technical products with antimicrobial properties and use as a bio- cide in technical processes are also possible, for example in paper treatment, especially in paper treatment liquors, print thickeners of starch or of cellulose derivatives, surface coatings and paints. The tetrahydrocarbazoles of formula (1 ) or (2) according to the invention are suitable also for the antimicrobial treatment of wood and for the antimicrobial treatment of leather, the preservation of leather and the provision of leather with antimicrobial properties. The compounds according to the invention are also suitable for the protection of cosmetic products and household products from microbial damage. The tetrahydrocarbazoles according to the invention are suitable also as medicaments for the treatment of bacterial infections for oral, intravenous, subcutaneous or parenteral administration of the active ingredient. The invention accordingly relates also to a medicament comprising a compound of formula (1) or (2) and therapeutically tolerable adjuvants, for the treatment of bacterial infections. The following Examples illustrate the invention. General procedure for the preparation of the tetrahydrocarbazoles according to the invention: The appropriate (substituted) indole (compound (I)) (1 mmol) is dissolved with (substituted) maleimide (compound (IV) (1.2 mmol) and an aldehyde/ketone (compound (II) (2 mmol) in 1- butanol (1 ml). There is then added to the mixture aqueous hydrochloric acid (2N; 50 μl; 0.1 mmol) or, in the case of piperidones, concentrated hydrochloric acid (32 %; 220 μl; 1.1 mmol). The mixture is then heated at 95°C for 3 hours. After cooling to 25°C, the resulting tetrahydrocarbazole (compound (1)) is precipitated with n- hexane (3 ml). After filtration, the filtrate is cooled to 5°C in order to obtain further crystals. The combined crystals are washed with n-hexane/ethyl acetate and dried in vacuo. All the compounds, that is to say the compounds of formulae (9) to (181), are characterised by LC-MS (for yields, see Table 1). Some of the compounds are analysed by NMR spectros- copy. The compounds are obtained in the form of mixtures of isomers (racemates or exo/endo isomers). Preparation Examples: Example 1 : 10-Bromo-3a.3b,4.5.6.7,8.8a,13.13b-decahvdro-1H-cvclohepta[clpyrrolo- [3,4-alcarbazole-1 ,3(2H)-dione (compound of formula (32)) Yield: 72 % LC-MS: [M+H] + = 386 ( 79 Br) NMR data: For reasons of clarity, the numbering used is not in accordance with lUPAC. Example 2: 2.6-Dimethyl-3b.4.5.6.7,7a.12,12b-octahvdrobenzo[clpyrrolo[3,4 alcarbazole- 1 ,3(2H.3aH)-dione (compound of formula (117)) Yield: 79 % LC-MS: [M+H] + = 322 NMR data: For reasons of clarity, the numbering used is not in accordance with lUPAC. Example 3: 9-Bromo-6-methyl-3b,4,5.6.7.7a.12,12b-octahydrobenzo[c1pyrrolo- [3.4-alcarbazole-1 ,3(2H,3aH)-dione (compound of formula (70)) Yield: 71 % LC-MS: [M+Hf = 386 ( 79 Br) Example 3: g-Bromo-e-methyl-SbAδ, 6.7,7a, 12.12b-octahvdrobenzofc1pyrrolo- [3,4-a1carbazole-1 ,3(2H,3aH)-dione (compound of formula (70)) Yield: 71 % LC-MS: [M+H] + = 386 ( 79 Br) NMR data: For reasons of clarity, the numbering used is not in accordance with lUPAC. 3 V H - 5 = 4.1 HZ The remaining compounds listed in Table 1 can be prepared in analogous manner. 4. Microbiological test results Nutrient: Casein/soybean flour peptone bouillon for the preparation of pre-cultures of the test bacteria and yeast. Mycological slant agar for the pre-culture of moulds Examples of test organisms: Staphylococcus hominis DMS 20328 Staphylococcus epidermidis Escherichia coli NCTC 8196 ATCC 12228 Corynebacterium xerosis ATCC 373 P.ovale ATCC 14521 Enterococcus hirae ATCC 10541 Actinomyces viscosus DSM 43329 Micrococcus luteus ATCC 9341 Porphyromonas gingivalis DSM 20709 Candida albicans ATCC 10259 Selenomonas artemidis ATCC 43528 Staphylococcus aureus (methicillin- Streptococcus mutans ATCC 25175 resistant) NCTC 11940 Streptococcus sobrinus DSM 20742 Staphylococcus aureus (methicillin- Epidermophyton floccosum resistant) NCTC 12493 DSM 10709 Staphylococcus aureus (penicillin- Tr. mentagrophytes ATCC 9533 resistant) NCTC 10443 Trichophyton rubrum DSM 4167 Staphylococcus aureus (rifampicin- resisTrichoderma longibrachiatum tant) NCTC 10703 DSM 768 Propionibacterium acnes ATCC 25746 Aspergillus niger ATCC 6175 Procedure: The test substances are pre-dissolved in dimethyl sulfoxide (DMSO) and tested in a dilution series of 1 :2. Bacteria and yeast are cultured overnight in CASO bouillon, the mould is cultured overnight on mycological slant agar, and washed off with 10 ml of 0.85 % sodium chloride solution (+ 0.1% TritonX-100). All the test organisms are adjusted to an organism count of 1 - 5 x 10 6 CFU/ml using 0.85 % sodium chloride solution. The test substances are pre-pipetted into microtitre plates in an amount of 8 μl per well. Pre-diluted organism suspensions are diluted 1 :100 in CASO bouillon (bacteria and yeast) or Sabouraud 2% glucose bouillon (mould) and are added in an amount of 192 μl per well to the test substances. The test batches are incubated for 48 hours at 37°C (bacteria and yeast) or for 5 days at 28°C (mould). After incubation, the growth is evaluated by reference to the turbidity of the test batches (optical density) at 620 nm in a microplate reader. The minimum inhibitory concentration (MIC value) is the concentration of substance at which (compared with the growth of the control) an appreciable inhibition of growth (< 20 % growth) of the test organisms is ascertained. One microtitre plate is used for each test organism and substance concentration. All the substances are tested in duplicate. The results are compiled in Table 2: Table 2: Minimum inhibitory concentrations (MIC) in ppm of the compounds synthesised against Staphylococcus hominis DMS 20328 and Escherichia coli

Claims: What is claimed is: 1. A compound of formula wherein R ! is hydrogen; C r C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C Csalkyl each unsubstituted or substituted by C,-C 5 alkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C,- C 7 alkylcarbonyl, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkylcarbonyl, C 3 -C 12 - cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C,- C 20 alkylamino or by nitro, R 2 is hydrogen; hydroxy; C^Czoalkyl; C 3 -C 12 cycloalkyl; C 1 -C 20 hydroxyalkyl; C r C 2 ohydroxy- alkoxy; C r C 20 aminoalkyl; N-C Czomonoalkylamino-C Czoalkyl; N-C r C 20 monoalkyl- aminohydroxy-C^C^alkoxy; N.N-CrCajdialkylamino-CrCzoalkyl; N. -CrCzodialkyl- aminohydroxy-C Czoalkoxy; carboxy; carboxy-C^C^alkyl ester; C^C^haloalkyl; CrC 2 o- haloalkoxy; C 2 -C 20 alkenyl; C 4 -C 12 cycloaIkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycIoalkynyl; C^Czo- alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C^C^Ikylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl; R 3 and R 4 are each independently of the other hydrogen; or CrCzoalkyl; or R 3 and R 4 together denote a C 2 -C 20 alkylene radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 -alkynylene radical; or a C 3 -C 20 alkylene radical interrupted by -N(R 6 )-, it being possible for such bivalent radicals to be further substituted by one or more CrC^alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 20 alkenyl, C 4 -C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, C C 7 -alkoxycarbonyl, or phenyl or phenyl-CrCgalkyl each unsubstituted or substituted by 0,-Csalkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 -alkoxycarbonyl, C 3 - C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di- C C^alkylamino or by nitro; or R 3 and R 4 together denote a bicyclo[x.y.z.]C 4 -C 20 alkylene; or bicyclo[x.y.z.]C 4 -C 20 alkylene interrupted by -N(R 6 )- , wherein x, y and z are each independently of the others from 0 to 10; R 5 is hydrogen; hydroxy; C r C 20 alkyl; C 1 -C 20 alkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -Cz 0 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C Csalkyl each unsubstituted or substituted by C C 5 alkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C^C^Ikoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-CrCzoalkylamino or by nitro; R 6 is hydrogen; C^Czoalkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 7 alkoxycarbonyl; phenyl or phenyl-C r C 5 alkyl each unsubstituted or substituted by 0,-Csalkyl, C 3 -C 12 cycloalkyl, CpCsalkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C C 20 alkylamino or by nitro; Q is -SO 2 -; -O-; or -(CO)-; X is -CH-; or -N-; m is from 1 to 3; and t is O or l. 2. A compound of formula (1) or (2) according to claim 1, wherein R, is hydrogen; C^Czoalkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-CrCsalkyl each unsubstituted or substituted by C C 5 aIkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C C 7 alkylcarbonyl, C r C 7 alkoxycarbonyl, C 3 -C 12 cycloalkylcarbonyl, C 3 -C 12 - cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N.N-mono- or di-C,- C 20 alkylamino or by nitro, R 2 is hydrogen; hydroxy; C r C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 - C 20 alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 20 alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl; R 3 and R 4 are each independently of the other hydrogen; or C r C 20 alkyl; or R 3 and R 4 denote a C 2 -C 20 alkylene radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 alkynylene radical; or a C 3 - C 20 alkylene radical interrupted by -N(R 6 )- , it being possible for such bivalent radicals to be further substituted by one or more C r C 20 alkyl, C 3 -C 12 cycloalkyl, C 2 -C 20 -alkenyl, C 4 - C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, C r C 7 alkoxycarbonyl, or phenyl or phenyl-C,-C 5 alkyl each unsubstituted or substituted by CrCsal yl, C 3 -C 12 -cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C 1 -C 20 alkylamino or by nitro; R 5 is hydrogen; hydroxy; C,-C 20 alkyl; C r C 20 alkoxy; C 3 -C 12 cycloalkyl; C-rCzoalkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C r C 5 alkyl each unsubstituted or substituted by C r C 5 alkyl, C 3 -C 12 cycloalkyl, C r C 5 alkoxy, C 3 -C 12 cyclo- alkoxy, halogen, carboxy, C^C^Ikoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C r C 20 alkylamino or by nitro; R 6 is hydrogen; CrCzoalkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloaIkynyl; C r C 7 alkoxycarbonyl; phenyl or phenyl-C^Csalkyl each unsubstituted or substituted by Chalky!, C 3 -C 12 cycloalkyl, C C 5 alkoxy, C 3 -C 12 cyclo- alkoxy, halogen, carboxy, C^C^Ikoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C^Czoalkylamino or by nitro; Q is -SO 2 -; -O-; or -(CO)-; X is -CH-; or -N-; m is from 1 to 3; and t is 0 or 1. 3. A compound according to claim 1 or claim 2, wherein R, is hydrogen; C C 20 alkyl; phenyl or phenyl-C r C 5 alkyl. 4. A compound according to any one of claims 1 to 3, wherein R, is hydrogen; or C r C 5 alkyl. 5. A compound according to any one of claims 1 to 4, wherein R 2 is hydrogen; CrCzoalkyl; C r C 20 alkoxy; or halogen. 6. A compound according to any one of claims 1 to 5, wherein R 2 is hydrogen; C C 5 alkyl; C r C 5 alkoxy; or halogen. 7. A compound according to any one of claims 1 to 6 that corresponds to formula wherein R 1 is hydrogen; C r C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C,-C 5 alkyl each unsubstituted or substituted by CrCsalkyl, C 3 -C 12 cycloalkyl, C C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C,- C 7 alkylcarbonyl, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkylcarbonyl, C 3 -C 12 - cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C^ C 20 alkylamino or by nitro, R 2 is hydrogen; hydroxy; CrCzoalkyl; C 3 -C 12 cycioalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 - C 20 alkynyl; C 4 -C 12 cycloalkynyl; C,-C 20 alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl; R 5 is hydrogen; hydroxy; CrCzoalkyl; C Czoalkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C r C 5 alkyl each unsubstituted or substituted by C r C s alkyl, C 3 -C 12 cycloalkyl, CpCsalkoxy, C 3 -C 12 cyclo- alkoxy, halogen, carboxy, C r C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-CrC-zoalkylamino or by nitro; R 6 is hydrogen; C r C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycIoalkenyl; C 3 -C 20 - alkynyl; C 4 -C 12 cycloalkynyl; C C 7 alkoxycarbonyl; phenyl or phenyl-CpCsalkyl each unsubstituted or substituted by CrCsalkyl, C 3 -C 12 cycloalkyl, C Csalkoxy, C 3 -C 12 cyclo- alkoxy, halogen, carboxy, C C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-CrCzoalkylamino or by nitro; Q is -SO 2 -; -O-; or -(CO)-; T, is C 2 -C 20 alkylene; C 2 -C 20 alkenylene; C 4 -C 20 alkynylene; or C 3 -C 20 alkylene interrupted by I 3 -N- ; X is -CH-; or -N-; s is from 1 to 4; and t is 0 or 1. 8. A compound according to claim 7, wherein T, is a -(CH 2 ) 2-1 z- radical and Re is hydrogen; or C|-C 3 alkyl. 9. A compound according to claim 8, wherein T, is a -(CH 2 ) 3 -, -(CH 2 ) 4 -, -(CH 2 ) 5 -, or -(CH 2 ) 10 - radical; and R 6 is hydrogen; or Chalky!. 10. A compound according to any one of claims 1 to 9, wherein R 5 is hydrogen; C,-C 2 oalkyl; phenyl or phenyl-C,-C 5 alkyl. 11. A compound according to any one of claims 1 to 10, wherein R 5 is hydrogen; CrCsalkyl; or phenyl. 12. A compound according to any one of claims 1 to 11 of formula wherein R 6 ' and R 6 " are each independently of the other hydrogen; C 1 -C 20 alkyl; CrCyalkoxy-carbonyl; phenyl or phenyl-C|-C 5 alkyi each unsubstituted or substituted by C C 5 alkyl, C r C 7 alkoxycarbonyl, N,N-mono- or di-C r C 20 alkylamino or by nitro; T, is -CH- ; -(CH 2 )r or -N— ; and Rι, R 2> s, Re and X are as defined in claim 6. 13. A compound according to claim 12, wherein R 6 ', R 6 " and R 6 are each independently of the others hydrogen; C r C 20 alkyl; C f Cr- alkoxycarbonyl; phenyl; or phenyl-CrCsalkyl. 14. A compound according to claim 13, wherein R 6 ', R 6 " and R 6 are each independently of the others hydrogen; C^Csalkyl; C^C alkoxycarbonyl; phenyl or benzyl. 15. A compound according to any one of claims 1 to 14 that corresponds to formula wherein R, is hydrogen; or C r C 5 alkyl; R 2 is hydrogen; Cι-C 4 alkyl; CI or Br; R 5 is hydrogen; Cι-C 3 alkyl; or phenyl R 6 ' and R 6 " are each independently of the other hydrogen; C^Csalkyl; or C,-C 7 alkoxy- carbonyl; R 6 is hydrogen, C Csalkyi; C r C 7 alkylcarbonyl; or phenyl-C Csalkyl; \ I T, is -CH- ; or — N— ; and X is -CH-. 16. A process for the preparation of a compound of formula (1) or (2) according to claim 1, wherein an indole compound (I), a keto or aldehyde compound of formula (II) and a dienophile of formula (IV) or (V), respectively, are reacted in a suitable solvent using an acid catalyst at a temperature of from 50°C to 140°C to form a compound of formula (1) or (2), respectively, in accordance with the following scheme: (2) 17. Use of a compound of formula (1) or (2) according to claim 1 in the antimicrobial treatment, deodorisation and disinfection of the skin, mucosa and hair. 18. Use according to claim 17, wherein the compound of formula (1) or (2) is used for disinfection and deodorisation. 19. Use of a compound of formula (1) or (2) according to claim 1 in the treatment of textile fibre materials. 20. Use according to claim 19, wherein the compound of formula (1) or (2) is used for preservation. 21. Use of a compound of formula (1) or (2) according to claim 1 in washing and cleaning formulations. 22. Use of a compound of formula (1) or (2) according to claim 1 in imparting antimicrobial properties to and preserving plastics, paper, nonwovens, wood or leather. 23. Use of a compound of formula (1) or (2) according to claim 1 in imparting antimicrobial properties to and preserving technical products, especially print thickeners of starch or of cellulose derivatives, surface coatings and paints. 24. Use of a compound of formula (1) or (2) according to claim 1 as a biocide in technical processes, especially in paper treatment. 25. A personal care preparation comprising from 0.01 to 15 % by weight, based on the total weight of the composition, of a compound of formula (1) or (2) according to claim 1 and cosmetically tolerable adjuvants. 26. An oral composition comprising from 0.01 to 15 % by weight, based on the total weight of the composition, of a compound of formula (1) or (2) according to claim 1 and orally tolerable adjuvants. 27. A medicament comprising a compound of formula (1) or (2) according to claim 1 and therapeutically tolerable adjuvants, for the treatment of bacterial infections.

Inventors: HAAP WOLFGANG, HOELZL WERNER, MEHLIN ANDREAS, OCHS DIETMAR, PETZOLD KARIN, HAAP, WOLFGANG, HOELZL, WERNER, MEHLIN, ANDREAS, OCHS, DIETMAR, PETZOLD, KARIN
Applicants: CIBA SC HOLDING AG, HAAP WOLFGANG, HOELZL WERNER, MEHLIN ANDREAS, OCHS DIETMAR, PETZOLD KARIN, CIBA SPECIALTY CHEMICALS HOLDING INC., HAAP, WOLFGANG, HOELZL, WERNER, MEHLIN, ANDREAS, OCHS, DIETMAR, PETZOLD, KARIN
Application year: 2001
Main classification: C07D487
IPC codes: A61K8, A61L2, A61Q11, A61Q15, A61Q17, C07D471, C07D487, C11D3, D21H21, D21H25