PL122586B1 - Process for manufacturing novel derivatives of anthraquinone - Google Patents

Description

The subject of the invention is a method for producing new anthraquinone derivatives having pharmacological properties. In the patent description: Great Britain No. 1,157,506 discloses one compound of the anthraquinone type, namely 1,4-bis(-aminoethylamino/anthraquinone), used as an intermediate for photographic dye disintegrators. M.S. Simon, J.A.C.S. 85, 1974 (1963); G. Kalopissis et al., C. A., 62, 11947f (1965); M. Ichikawa et al. C. A. 61, 1977f (1964) and C. W. Greenhalgh et al. J. Ohem.Soc. 1284 (1968) disclosed similar compounds, but found that they only act as intermediates in the preparation of dyes or have no useful properties at all. No publication discloses the pharmacological properties of this type of compounds. The method according to the invention produces new anthraquinone derivatives of the general formula 1 and their tautomeric varieties and pharmacologically permitted acid addition salts, in which formula 1 A-B means a group such as CH=CH or CH2-CH2, Q means a divalent group such as a group of the formula -/CH3/n-, formula 2, formula 3, formula 4, formula 5, formula 6, formula 7 , formula 8 and formula 9, in which formulas n denotes an integer numerical value from 2 to 4 inclusive, Ri and R2 each separately denote a hydrogen atom, an alkyl group with 1-4 carbon atoms, a monohydroxyalkyl group with 2-4 carbon atoms, in which there should be no hydroxyl group at the carbon atom in the a position in relation to the nitrogen atom, a dihydroxyalkyl group with 3-6 carbon atoms, in which the carbon atom in the a position in the ratio the nitrogen atom should not contain a hydroxyl group, a formal group, an alkanoyl group with 2-4 carbon atoms, a trifluoroacetyl group or a group with the formula -/CH2/n-CN, -/CH2/n-0-R or formula 10 , in which formulas n denotes an integer value from 2 to 4 inclusive, R denotes an alkyl group with 1-4 carbon atoms, and R3 and R4 each separately denotes a hydrogen atom, an alkyl group with 1-4 4 carbon atoms or a monohydrocayalkyl group with 2-4 carbon atoms, in which there cannot be a hydroxyl group at the carbon atom in position a in relation to the nitrogen atom, Ri and R2 including the nitrogen atom associated with them and R3 and R4 together with the nitrogen atom associated with them nitrogen atom is a morpholino, thiomorpholino, piperazine, 4-methylyl-1-piperazine group or a group of formula 11, in which m is a total numerical value from 2 to 6 inclusive, where the ratio of the total number of atoms carbon to the sum of the total number of oxygen atoms and the total number of nitrogen atoms in the side chains in positions 1 and 4 122 586122 586 cannot exceed 4, R5 is a hydrogen atom, a hydroxyl group, a halogen or an alkanyloxy group with 1-6 carbon atoms , Re is a hydrogen atom or a hydroxyl group, R7 is a hydrogen atom, a hydroxyl group, a halogen, an alkanoyloxy group with 1-6 carbon atoms or a group of formula 12, in which R8 and R9 each separately represent a methyl, ethyl or . /?- hydroxyethyl, and if Q is -/CH2/n-, then: a) Ri, R2, R5, Re and R7 cannot simultaneously represent a hydrogen atom, b) if R5, R6 and R7 are hydrogen, R1/R2 cannot be H/monohydroxyalkyl and in case n is 2, then R1/R2 may be -/CH^-O-ZCng/g-H/CHa, H/C2H5 or C2H5/CIH5 and in the case where n is 3, R1/R2 must not be CH3/CH3 or -/CH2/5-, c) in the case where R5 and R7 represent a hydroxyl group and n is 2, then Ri/R2 cannot be CH3/CH3, C4H9/C4H9 or -/CH2/5-, and in case n is 3, then RjyR2 cannot be H/H, CH3/CH3, C3H7/C3H7 or -/CH2/2-0-/Ce2/2- and in the case where n is 4, then Ri/R2 must not be C2H5/C2H5, C4H9/C4H9 or -/CH2/4- d) in the case when R5 represents a hydroxyl group, then one of the substituents with the symbols Re and R7 must represent a hydrogen atom, and in the case where R5 represents a hydrogen atom, then each of the substituents with the symbols Re and R7 must represent a hydrogen atom and e) only one of the substituents with the symbols Ri and R2 may constitute an alkanoyl group. The compounds covered by the above general formula 1, in which A-iB is CH2JCH2, are generally stable and are known as leuko forms of the corresponding anthraquinones. These leuko forms are known to exist in corresponding tautomeric forms and all these forms are equivalent for the purposes of the present invention. The leuko forms, here leucobases, and their tautomers can be represented by general formulas 13 and 14 (scheme attached to the drawing). The invention therefore concerns a method for preparing new compounds represented by the general formulas 1, 13 and 14. The method according to the invention consists in the fact that the compound of the general formula 15 in which R5, R5 and R7 as well as A-B have the meanings given above, and hal means a chlorine, bromine or iodine atom reacts with a compound of the formula H2N-Q-N <^R , in which Ri, R2 and Q have the meanings given above with the limitation that in the case where one of the substituents with the symbols R5 and R7 denotes a halogen or alkanoyloxy group, then the second one has the same meaning and R6 represents a hydrogen atom or when R5 = R7 = halogen or an alkanoyloxy group, these groups are converted into a hydroxyl group and, if desired, converted A—B when it is CH2^CH2, in CH—OH, and then the obtained compound is contacted under conditions favoring salt formation with a reagent forming a pharmacologically acceptable salt. Thus, the invention concerns also the preparation of acid addition salts of new compounds covered by formulas 1, 13 and 14. The new compounds are obtained in the form of crystals with a reddish-brown to blue-black color, with a characteristic melting point and absorption spectrum, which can be purified by leaching using lower alkanols because the free bases are mostly insoluble in water and some of them are insoluble in most organic solvents. Organic bases of formulas 1, 13 and 14 are prepared according to the process of the invention, non-toxic addition salts are formed with various pharmacologically acceptable organic and mercury salt-forming reagents. Thus, acid addition salts are prepared by mixing the organic free base with 1, 2 or up to 8 equivalents of the acid, co preferably in an inert solvent medium, are obtained using acids such as sulfuric acid, phosphoric acid, hydrochloric acid, hydrobromic acid, sulfamic acid, citric acid, lactic acid, malic acid, succinic acid, tartaric acid, acetic acid, benzoic acid, gluconic acid, ascorbic acid, etc. Preferred acids are salt and acetic acid. For the purposes of the present invention, the free bases are equivalent to their non-toxic acid addition salts. Acid addition salts of organic bases obtained by the method of the invention are generally crystalline bodies, characterized by relatively good solubility in water, methanol and ethanol, but are relatively insoluble in organic non-polar solvents, such as ethyl ether , benzene, toluene, etc. It should be understood that all these salts can be converted by known methods back into the corresponding free-form compounds covered by the formulas 1, 13 and 14 and that all these salts as well as the free-form compounds are equivalent within the meaning of the present invention. In a preferred process according to the invention, compounds of the general formula 16 and their pharmacologically acceptable acid addition salts are prepared, in which formula 16 A-B and Q have the meanings given above. Rj denotes a hydrogen atom, an alkyl group with 1-4 carbon atoms or a monohydroxyalkyl group with 2-4 carbon atoms, in which there should be no hydroxyl group at the carbon atom in position a 55 in relation to the nitrogen atom, R2 denotes a monohydroxyalkyl group with 2-4 carbon atoms, in which there should be no pa hydroxyl group at the carbon atom in position a in relation to the nitrogen atom, a dihydroxyalkyl group with 3-6 carbon atoms, in which there should be no hydroxyl group at the carbon atom in position a in relation to the nitrogen atom there should be no hydroxyl group or a group of the formula 10, in which n, R3 1 R4 W have the meaning given above, with the ratio of the total number of carbon atoms to the sum of the total number of oxygen atoms and the total number of nitrogen atoms in the side chains in positions 1 and 4 must not exceed 4. In another preferred method of the invention, compounds of the general formula 17 and their pharmacologically acceptable acid addition salts are prepared, in which then of formula 17 R stands for a hydrogen atom or an alkyl group with 1-4 carbon atoms, and A-B, n and Q have the meanings given above, with the ratio of the total number of carbon atoms to the sum of the total number of oxygen altoms and the total the number of nitrogen atoms in the side chains in positions 1 and 4 must not exceed 4. In a further preferred method of the invention, compounds of the general formula 18 and their pharmacologically acceptable acid addition salts are prepared, in which the formula 18 n, Rj, R2 and A-B have the meanings given above for the first preferred process of the invention. In a further preferred process of the invention, compounds of the general formula 19 and their pharmacologically acceptable acid addition salts are prepared, in which formula 19 Ri represents a hydrogen atom or - CH2CH2OH. Preferred salts include hydrochloride and acetate. The reaction is preferably carried out by heating the reactants at a temperature of about 40°-110°C for about 2-10 hours in an inert solvent such as water or a lower alkali such as methanol. , ethanol, propanol, isoprtfpanol, any of the isomeric butanols and the like, or in an amide medium such as formamide, dimethylformamide and the like, or in a solvent medium such as N,N,N',N'-tetramethylethylene diamine, or in their mixtures. The above-mentioned temperatures, time periods and types of solvents and their combinations are in most cases sufficient to carry out the process according to the invention. Sometimes it may be desirable to use other solvents and reaction parameters and to select such additional solvents. and reaction parameters are within the knowledge of the researcher, and these data should be considered equivalent to those given above in the sense of the present invention. In most cases, the desired compound is obtained in solid form, crystallizing, either spontaneously or after seeding, with the solvent constituting the reaction medium, after cooling. It can be isolated by filtration or decantation. In other cases, the reaction mixture can be concentrated, e.g. at elevated temperature, under reduced pressure, and after cooling, the obtained compound crystallizes and can be isolated. by filtration or decantation as described above. In some cases it may be necessary to evaporate the solvent to dryness to isolate the compound obtained, or, alternatively, to mix or dilute the reaction mixture with another miscible solution. ¬ with an admixture such as water, followed by isolation of the product by, for example, filtration or extraction. The choice of method depends on the knowledge of the researcher and all these methods should be considered equivalent in the sense of the present invention. The obtained compound after isolation can be purified by, for example, crystallization, thin-layer or column chromatography, or, preferably, by leaching with a lower alcohol. . Other methods may also be used, such as maceration or kneading in a solvent, e.g. an organic solvent such as ethanol, and all of these purification methods are to be considered equivalent for the purposes of the present invention. It is known that in the case of preparing the desired compound in the leuko form, the starting three-ring compound should also be used in the leuko form, and it should be protected, especially under elevated temperature conditions, such as temperatures above room temperature, against the influence of oxidizing agents, such as oxygen. Therefore, when it is desired to obtain a given compound in the leuko form, the process is usually carried out effectively in an atmosphere excluding the presence of air. Thus, the reaction can be carried out in an atmosphere such as nitrogen or argon, and this care should also be taken when purifying the compound, especially when it is necessary to use an elevated temperature. In this case, when it is desired to obtain an aromatic and an aromatic starting compound has been used, such care is generally not necessary. It is also known that, if necessary, a given compound in the leuko form can be easily converted into the compound in the aromatic form by various methods. One of them is oxidation with air, another one is oxidation with e.g. hot nitrobenzene, chloranil, hydrogen peroxide or sodium perborate. All these methods, as well as other methods of converting the leuko form into the aromatic form, should be considered equivalent for the purposes of the present invention. Therapeutic agents containing as active substances the compounds produced by the method of the invention inhibit the growth of a transplantable murine tumor and also cause regression or amelioration of leukemia and similar cancers in mammals when administered in amounts ranging from about 5 mg to about 200 mg/kg body weight per day. The preferred dosage for optimal results is in the range from about 5 mg to about 50 mg/kg body weight per day, which corresponds to administering the active compound to a person weighing about 70 kg over a 24-hour period with a total dose of about 350 mg to about 3.5 g. This dosage regimen can be adjusted so that to obtain optimal treatment results. For example, the drug can be administered in several divided doses, or the dose of Motan can be proportionally reduced in accordance with the current treatment requirements. The unquestionable practical advantage is the ability to administer the active compound in any convenient manner, such as by oral, intravenous, intramuscular or subcutaneous routes. The active ingredients may be administered orally, for example in combination with an inert diluent or an absorbable edible carrier, or in the form of in hard or soft coated gelatin capsules, or compressed into tablets, or directly with food in the diet. Active compounds intended for oral administration can be combined with excipients and used in the form of swallowable tablets, buccal tablets, earrings, capsules, elixirs, suspensions, syrups, wafers, etc. Such products and preparations should contain at least 0.1% of the active compound. Of course, the percentage of the active compound in the products and preparations may vary and is preferably from about 2 to approximately 60P/a by weight of the unit dose. The amount of active ingredient in such therapeutically useful compositions is such as to permit appropriate dosing. Preferred compositions and preparations are formulated so that an oral unit dose contains from about 5 to 200 mg of active compound. Tablets, earrings, pills, capsules, etc. may also contain the following excipients: binders, such as gum tragacanth , gum arabic, corn starch or gelatin, excipients such as calcium monohydrate phosphate, disintegrating agents such as corn starch, potato starch, alginic acid and the like, lubricants such as magnesium stearate, sweetening agents such as such as sucrose, lactose or saccharin and flavors such as mint, stewed or cherry. In this case, when the unit dose is a capsule, it may contain, in addition to the ingredients mentioned above, a liquid carrier. Various other substances may also be present as agents for coating or otherwise altering the physical form of the dosage unit, for example tablets, pills or capsules may be coated with shellac, sugar or both. The syrup or elixir may contain the active compound, sucrose as a sweetener, methyl or propyl parabanate as a preservative, and a color and flavor such as cherry or orange. Of course, any material used to prepare each unit dose should be stable. essentially pharmaceutically pure substances. non-toxic in the amount used. Moreover, the active compound can be incorporated into long-acting preparations or agents. The active compounds can also be administered parenterally or intraperitoneally. A solution of the active compound, as the free base or pharmacologically acceptable sori, can be prepared in water, suitably mixed with a surface-active substance such as hydroxypropyl cesium. Suspensions may also be prepared in glycerol, liquid polyethylene glycol, mixtures thereof and oils. Under normal conditions of storage and use, these preparations contain preservatives to prevent the growth of microorganisms. Pharmaceutical forms suitable for use in injection, these are sterile aqueous solutions or suspensions and sterile powders intended for the preparation of a sterile solution or suspension for injection immediately before administration. In all these cases, the agent must be sterile and sufficiently liquid that the syringe can be easily filled and emptied. It must be stable under the conditions of manufacture and storage and must be protected against changes caused by microorganisms such as bacteria and fungi. The carrier may be a solvent or dispersion medium containing, for example, water, ethanol, polyhydric alcohol such as glycerol, propylene glycol or liquid polyethylene glycol, etc., suitable mixtures thereof, and vegetable oils. Suitable fluidity may be maintained, for example by the use of a coating agent such as lecithin, by maintaining the required particle size in the case of a suspension, and also by the use of surface-active substances. Protection against the action of microorganisms can be provided by various antibacterial and antifungal agents, such as parabanates, chlorobutanol, phenol, sorbic acid, thiomorsal, etc. In many cases, it is beneficial to introduce isotonic agents, such as sugars. or sodium chloride. Prolonged absorption of injectables can be achieved by the inclusion of absorption delaying agents such as aluminum monostearate and gelatin. Sterile injectable solutions are prepared by introducing the active ingredient in the desired amount into a suitable solvent containing, if this is necessary, the various ingredients listed above, and then sterilization by filtration. Generally, suspensions are prepared by introducing the active ingredient sterilized in one way or another into a sterile vehicle containing the basic dispersion medium and the necessary other ingredients from those enumerated above. In the case of sterile powders for the preparation of sterile injectable solutions, the preferred methods of preparation are: vacuum drying and freeze-drying. Using these methods, the active ingredient is obtained from a previously sterilized solution, along with the additional desired ingredient, in the form of powder.! In this specification, the term "pharmacologically acceptable vehicle" includes any and all solvents, dispersing media, coating agents, antiphobacterial and antifungal agents, theotonic agents, and absorption delaying agents, etc. The use of these vehicles and the like 45 60 55 60122 586 9 if the factors involved in the use of pharmaceutical active substances are known. Except in those cases where the substrates or sensors are usually incompatible with the active ingredient, their use in therapeutic agents is envisaged. Additional active ingredients may also be included. It is particularly advantageous to prepare parenteral formulations in unit dosage form to facilitate administration and standardize dosing. A unit dosage as used herein refers to a physically separate unit adapted for unit dosing. mammalian individuals for the purpose of their treatment, each individual containing, together with the necessary pharmaceutical carrier, the active substance in a predetermined amount calculated to produce the desired therapeutic effect. The specification of a new unit dose of agents is dictated by and directly depends on: a) the unique properties of the active substance and the specific therapeutic effect achieved, and b) the limitations inherent in the method of incorporating the active substance into the treatment of living people who are in a state of disease, with excessive important physical health, as described in detail herein. The active ingredients of the medicinal compositions may represent compounds of the general formula I and their tautomeric variants and pharmacologically acceptable acid addition salts, wherein the formula I A-B denotes a moiety such as CH=CH or CH2—CH2, Q denotes a divalent moiety such as the group of formula -/CH2/n-, formula 2, formula 3, formula 4, formula 5, formula 6, formula 7, formula 8 and formula 9, wherein then the formulas n denote an integer numerical value from 2 to 4 inclusive, Ri and R2 each separately denote a hydrogen atom, an alkyl group with 1-4 carbon atoms, a monohydroxyalkyl group with 2-4 carbon atoms, in which at the carbon atom in there should be no hydroxyl group at position a in relation to the nitrogen atom, a dihydroxyalkyl group with 3-6 carbon atoms, in which there should be no hydroxyl group at the carbon atom in position a in relation to the nitrogen atom, a Formyl group, an alkanoyl group with 2-4 carbon atoms, a trifluoroacetyl group or a moiety with the formula -/CH2/n-CN, -/H2/n-O-R or -formula 10, in which formulas n is an integer value from 2 to 4 inclusive, R represents an alkyl group having 1-4 carbon atoms, and R3 and R4 each separately represent a hydrogen atom, an alkyl group having 1-4 carbon atoms, or a monohydroxyalkyl group having 2-4 carbon atoms carbon, in which there cannot be a hydroxyl group at the carbon atom in position a in relation to the nitrogen atom, Rj and R2 together with the nitrogen atom associated with them and R3 and R4 together with the nitrogen atom associated with them constitute the moTpholine, thiomorpholino group , pperazine, 4-methyl-l-piperazine or a moiety of formula 11, in which n is an integer from 2 to 6 inclusive, wherein the ratio of the total number of carbon atoms to the sum of the total number of oxygen atoms and the total number of atoms nitrogen in the side chains in positions 1 and 4 must not exceed 4, R5 represents a hydrogen atom, a hydroxyl group, Re 5 represents a hydrogen atom or a hydroxyl group, R7 represents a hydrogen atom, a hydroxyl group or a group of formula 12, in which Rg and R9 each separately represent a methyl, ethyl or ?-hydroxyethyl group, however, if R5 represents a hydroxyl group, then one of the substituents with the symbols Ra and R7 must represent a hydrogen atom, and if R5 represents connects a hydrogen atom, then each of the substituents with the symbols Re and R7 must represent a hydrogen atom. Preferred active ingredients of medicinal products include compounds of the general formula 16 and their pharmacologically acceptable acid addition salts, in which the formula 16 A-B, Q , Rj and R2 have the meanings given above. Preferred salts are hydrochloride and acetate. More preferred active pharmaceutical ingredients include compounds of the general formula 17 and their pharmacologically acceptable acid addition salts, in which formula 18 A-B, Q and n have the meanings given above. , and R is a hydrogen atom or an alkyl group with 1-4 carbon atoms. Preferred salts are hydrochloride and acetate. The second, more preferred group of active ingredients of medicinal products includes compounds of the general formula 18 and their acid addition salts, in which formula 18 n, Ri and A-B have the meanings given above. . Preferred salts are hydrochloride and acetate. The most preferred active ingredients of medicinal products are compounds of the general formula 20, in which Rj and R2 each separately represent a hydrogen atom or the -GH2CH2°H group and their hydrochlorides and acetates. Regression and alleviation of cancer are achieved. eg, by oral or injectable administration. For example, a single oral or intravenous dose may be administered, or the dosage may be repeated daily. Daily dosing for about 5 or 10 days is often sufficient. It is often also possible to skip one daily dose, or one dose every other day or less frequently. As will be seen from this dosing regimen, the amount of principal active ingredient administered is an amount effective to cause regression or amelioration of leukemia or related diseases without excessive harmful effects. side effects of a cytotoxic nature in the host whose body is the site of the tumor. This amount is referred to herein as the effective amount. In this specification, cancer means malignant blood diseases such as leukemia; as well as other malignant diseases caused by solid or non-solid tumors, such as sarcomas, lung cancers and mammary gland tumors. Regression and alleviation is understood as stopping or delaying the growth of the tumor or other symptoms - 1 $ 20 » 36 35 40 45 50 55 40122586 11 12 of the disease compared to the course of the untreated disease. A method of inducing regression and/or alleviation of neoplastic diseases in mammals consists in administering to the mammals orally or parenterally an effective amount of a compound of general formula 1 , its tauiomeric forms and pharmacologically acceptable acid addition salts, wherein the formula 1 A-B denotes a group such as CH=CH or CH2-CH2, Q denotes a divalent moiety such as a group of the formula -/CH2/n - formula 2, formula 3, formula 4, formula 5, formula 6, formula 7, formula 8 and formula 9, in which formulas n means an integer numerical value from 2 to 4 inclusive, Ri and R2 each separately represent a hydrogen atom , an alkyl group with 1-4 carbon atoms, a monohydroxyalkyl group with 2-4 carbon atoms, in which there should be no hydroxyl group at the carbon atom in position a in relation to the nitrogen atom, a dihydroxyalkyl group with 3-6 atoms carbon, in which the carbon atom in position a in relation to the nitrogen atom should not contain a hydroxyl group, a formyl group, an alkanol group with 2-4 carbon atoms, a trifluoroacetyl group or a group with the formula WCH2/n-^CN, -/CH2/n-O-R or formula 10, in which formulas n is an integer from 2 to 4 inclusive, R is an alkyl group with 1 to 4 carbon atoms, and R3 and R4 each separately represent a hydrogen atom, an alkyl group with 1-4 carbon atoms or a monohydroxyalkyl group with 2-4 carbon atoms, in which no hydroxyl group, Ri and R2, including a nitrogen atom bonded thereto, and R3 and R4 combined with a nitrogen atom bonded thereto constitute a morpholino, thiomortolyho, piperazino, 4-methyl-1-piperazino group or a moiety of the formula 11, where n is an integer numerical from 2 to 6 inclusive, where the ratio of the total number of carbon atoms to the sum of the total number of oxygen atoms and the total number of nitrogen atoms in the side chains in the Li 4 position cannot exceed 4, R5 is a hydrogen atom or a hydroxyl group, Re is a hydrogen atom or a hydroxyl group, R7 is a hydrogen atom, a hydroxyl group or a moiety of formula 12, wherein Rg and R9 each individually represent a methyl, ethyl or ?-hydroxyl group, and in the case where R5 is a hydroxyl group, then one of the substituents with the symbols R5 and R7 must represent a hydrogen atom, and in the case where R5 represents a hydrogen atom, then each of the substituents with the symbols Rfl and R7 must represent a hydrogen atom. In the preferred case, inducing regression and /or alleviating cancerous diseases in mammals consists in administering to said mammals orally or parenterally an effective amount of a compound of general formula 16 and pharmacologically acceptable addition salts thereof, wherein formula 16 A-B, Q, Rj and R2 have the meanings given above. Preferred salts are the hydrochloride and acetate salts. In an even more preferred case of inducing regression and/or amelioration of cancerous diseases in mammals, the mammal is administered orally or parenterally an effective amount of a compound of general formula 21 and its pharmacologically acceptable quaternary and addition salts, in which formula 21 A-B and Q have the meanings given above, and R denotes a hydrogen atom or an alkyl group with 1-4 carbon atoms. Preferred salts are hydrochloride and acetate. In the second more preferred case of inducing regression and/or amelioration of neoplastic diseases in mammals, the mammal is administered orally or parenterally an effective amount of a compound of general formula 18 and its pharmacologically acceptable acid salts. additions, in which formula 18 n, R1, R2 and A-B have the meanings given above. Preferred salts are hydrochloride and acetate. Most preferably, for inducing regression and/or amelioration of neoplastic diseases in mammals, the mammal is administered orally or parenterally an effective amount of the compound of formula 20 and its pharmacologically acceptable acid addition salts, in which formula Ri and R2 each separately represent a hydrogen atom or a -CH2CH2OH group. Preferred salts are hydrochloride and acetate. The new compounds of this invention are useful as chelating, complexing and sequestering agents. The complexes formed with polyvalent metal ions are particularly stable and generally soluble in a variety of organic solvents. Of course, these properties make them useful in many applications where metal ion contamination is a problem. For example, they are useful as stabilizers of various organic systems, such as saturated and unsaturated lubricating oils and hydrocarbons, fatty acids and waxes, in which metal ion contamination accelerates oxidative deterioration and color development. .They are further useful in the analysis of multivalent metal ions, which can be complexed or extracted using new compounds and as metal carriers. These compounds can also be used in applications typically found in sequestration. In addition, leucobases of the general formula 13 are useful as intermediates in the preparation of fully synthesized derivatives of the general formula 1, in which A- and B stands for CH=CH. The new compounds produced according to the method of the invention also have the property of inhibiting the growth of transplantable murine tumors, as this was determined on the basis of the following standard tests. Lymphocytic leukemia test P 388. The animals used are DBA/2 mice, all of one sex, weighing a minimum of 17 g, with differences in weight of all mice not exceeding 3 g. In the test groups there are: 5 or 6 10 15 20 25 30 35 40 45 50 55122 566 13 animals. The tumor is transplanted by intraperitoneal injection of 0.1 ml of diluted ascitic fluid containing 108 P 388 lymphocytic leukemia cells. The test compound is administered intraperitoneally on the first, fifth and ninth day of tumor inoculation, in various doses. Animals are weighed and the number of survivors is recorded in a uniform manner for 30 days. The median survival time and the ratio of survival time of treated animals (T) to control animals (C) are calculated. The positive control compound is 5-fluorouracil, administered* by injection in an amount of 60 mg/kg. The results of this test using representative compounds prepared according to the invention are given in Tables 1-1a. The effectiveness criterion is T/C X 100 ^ 125 %. Table 1 P 388 Lymphocytic Leukemia Test Compound Dose (mg/kg) Median Survival Time (days) T/C 5-Fluorouracil 1,4-Di[<2-dimethyl^minoe(tyl)-amiijnO']-5,8-di-hydroxyanJtrachanone - Control 5-Fluorouracil Leuco-1,4-di(2-morpholinoethylainine)-5, 8-dihydroxy- anthraquinone Control 5-Fluorouracil 100 50 25.0 12 6 3 1.5 0 60 1 *4.5 24.5 19.0 17.5 16.0 14.5 13.0 10.0 19, 0 50 25 12 6 3 0 60 100 50 25 0 60 25.0 20.5 23.0 21.0 19.5 9.0 19.5 13.0 12.0 11.0 12.0 9.5 19 ,5 245 246 190 175 160 1145 130 190 278 228 2S& 233 2117 217 137 )126 116 126 205 l,4-di(2-morpholinoethy,lóamino)-5,8-dihydroxyanthraquinone Control 5-Fluoroura cyl £00 100 60 14.0 12.0 9.5 19.5 147 126 205 Leuto-yl,4-Di[i(2-diethioaminoethylojamino]-5.8 - Dihydroxyldrocisyanltraichinone Control 5-Fluorouracil aoo 100 50 25 12 0 60 17.0 17 .0 15.0 13.0 12.0 9.5 19.5 179 179 158 137 126 205 1-Diethylaminoethyl-amino]-5,8-dihydroxy- anthraquinone Control 5-Fluorouracil 200 100 50 25 12 0 60 20.0 18.0 15.0 16.0 12.0 9.5 19.5 210 189 158 168 126 205122 586 15 16 cont. table 1 1 1 Leuco-1,4-di [ [2 - droxyanthraquinone Control 5-Fluorouracil 1,4-Di [ [2- (1-pyrrolidinyl)ethyl ] amino ]-5,8-dihydroxy- anthraquinone [ Control 5- Fluorouracil 1,4-Di[(3-dimethylaminopropyl)-amino]-5,8-d'dihydroxyanthraquinone Control 5-Fluorouracil Leuco-1,4-di[(2-aminotyl)amino]-5,8 -dihydroxyanthraquinone Control 5-Fluorouracil Leuko-l,4-di(3-aminopropylamino)-i5,8-dihydroxy- anthraquinone Control ¦- 5-Fluorouracil Leuco-l,4-di[2-(2-methylaminoethylamino)ethylamino ]- -5,8-dihydroxyanthraquinone 5-Fluorouracil Leu control! co-'l,4-di[2-dimethylaminopropylamino]-5,8-dWu- hydroxyanthraquinone Control 5-Fluorouracil 1,4-di[2^(2-hydrooxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone dihydrochloride Control 5-Fluorouracil and 1 2 1 200 100 50 25 0 60 100 50 25 12 0 1 60 50 25 12 0 60 100 50 25 12 0 60 200 100 50 25 12 0 60 200 100 50 25 12.5 6.2 0 60 ,200 100 50 25 12.5 0 60 12.5 6.2 3.1 1.5 0.78 0.39 0.19 0.09 0.04 0 60 | 1 3 1 23.0 19.0 16.0 15.0 11.0 | 20.0 24.0 23.0 1211.0 18.0 11.0 120.0 15.5 15.5 15.0 tl2.0 19.5 19.0 . 23.0 19.0 18.0 12.0 119.5 18.0 18.0 16.0 18.0 16.0 12.0 19.5 2.0 26.0 28.0 21.0 16, 0 15.0 11.0 17.0 18.0 15.0 14.0 13.0 11.0 9.0 18.5 13.0 20.0 22.0 29.0 29.0 27.0 2 (5.0 21.0 20.0 10.0 20.0 1 1 4 1 209 1173 145 136 182 218 209 1191 164 182 12.9 12.9 ' 126 160. 158 1 192 158 ^150 162 150 15 0 133 150 133 162 1 18.0 236.0 255.0 191.0 145.0 136 170 | 200 167 156 144 122 206 1 130 200 220 290 200 270 250 1210 1200 200 117 122 586 cjcL array 1 £ 1 1 Lemko-1, 4-Di[2-1(1-piperazylethylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-Dihydrochloride-5,8-dihydroxyanthraquinone Control 5-Fluorouracil Leuko-1 ,4-di[2-(2-hydroxy€tylamino)ephthylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil Lfeuko-1,4-di(4-aminobutylamino)-5,8-dihydroxyanthraquinone Control 5- Fluorouracil Leukcr-rM-di[2-(methylamino)ethylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil Leuko-1,4-di[2-i(2-isopropylamino)eitylamino]-5,8-di - hydroxyanthraquinone Control 5-Fluorouracil 1,4-Di[2H(2-aminoethylamino)-ethylamino]-5,8-d,dihydroxyanthraquinone Control 5-Fluorouracil | 2 | 3 200 100 50 25 12.5 0 60 25 12.5 6.2 3.1 1.5 0.78 0.39 0.19 0.09 0.04 0 60 25 12.5 6.2 3.1 1.5 0.78 0.39 0.19 0.09 0.04 0 60 400 300 200 ilOO 0 60 50 25, 12.5 6.2 3.1 1.5 0 60 . 100 50 25 12.5 0 60 200 100 50 25 0 60 1 7.0 21.0 16.0 1 15.0 14.0 9.0 18.5 9.0 16.0 20.0 22.0 22 .5 18.5 19.5 18.5 18.0 17.0 10.5 18.0 12.0 23.5 23.0 26.0 30.0 28.0 22.0 21.5 21.5 18.5 10.5 18.0 20.0 18.0 17.0 14.0 10.5 17.5 | 6.0 19.0 19.0 21.0 15.0 13.0 11.0 18.5 ' | 8.0 19.0 17.0 15.0 11.0 20.5 17.0 16.0 14.0 13.0 10.5 4 17.0 | 4 78 12133 178 (11617 156 206 '86 152 H90 210 '2l! 4 H'716 136 17:6 171 ' 171; ¦1II4I 224 2119 248 286 267 209 1205 (205 176 171 1 90 1711 ' 116(2 ' 1331 162 55 '173 173 11191 136) 118 1168 73 17l3l 155 136 186 162 152 11133 124 162122 586 19 20 continued table 1 1 1 Leuco-1,4-[2-[di(^-hydrooxyethyl)amino] eitylamino]-15, 8-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-di[2-(2-hydroxy-1-propylamino)ethylamino]-1,4-dihydroxyanthraquinone dihydrochloride Control 5-Fluorouracil 1,4-di[2-[ tetrahydrochloride i(2-no]ethylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-di[2-<3-hydroxy-1-proipylamino)ethylamino]-5,8-dihydroxyanthraquinone dihydrochloride Control 5-Fluorouracil Leuco-1,4-di[2-i(3-hydroxy-1-propylamino)ethylamino] - -5,8-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-di[2-[di(ytf-hydroixyethyl)ami dihydrochloride - no]-ethylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil | 2 | 3 200 100 50 25 12.5 6.2 0 40 25 12.5 6.2 3.1 1.56 0.78 0, 39 0 40 200 100 50 25 12.5 6.2 3.1 0 40 25 12.5 6.25 3.1 1.56 0.78 0 40 200 100 50 25 12.5 6.25 3.1 1 .56 0.78 0 40 200 100 50 25 12.5 6.2 3.1 1.56 0.78 0 60 19.0 17.0 16.0 15.0 13.5 12.0 10.0 18 ,0 12.0 24.0 2i3.0 22.0 19.0 19.0 17.5 10.0 18.0 9.5 20.0 18.5 19.5 15.0 14.0 13.0 10.0 18.0 8.5 30.0 26.0 25.0 22.0 " 21.5 11.0 (18.0 14.0 38.0 34.0 22.0 19.5 16.5 18.5 19.5 18.0 11.0 17.0 | 30.0 22.0 20.5 21.5 18.5 18.5 19.0 16.0 14.5 9.0 20.5 4 1 190 1170 160 150 135 120 180 | 120 240 230 220 190 190 175 180 1 95 200 185 195 150 140 130 180 | 77 273 236 227 200 195 164 1 127 345 309 200 177 150 168 177 164 155 | 333 244 228 239 206 206 211 178 161 228 |122 586 cjd. table 1 1 1 Leuco-1,4-di[3-<2-hydro,xyethylamino)-l-propylamino]- -5,8-dihydroxyanthraquinone Control 5-Fluorouraeyl Leuco-l,4-d:wu[2-hydroc ;sy-l-proipylamino)ethylamino]-l,4-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-di[3-(2-hydroxyethylamino)-l-propylamino]-5,8-dihydroxyanthraquinone dihydrochloride Control 5-Fluorouracil 1,4-Di[2-1(l-aziridino)ethylamino]-5,8-dihydroixyan-1 traquinone Control 5-Fluorouracil Tetrahydrochloride 1,4-di[2-,(2-methylaminoe1;ylamino)ethylamino] -5,8-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-di(2-aminoethylamino)-5,8-dihydroxyanthraquinone dihydrochloride Control 5-Fluorouracil I 2 200 100 50 25 12.5 6.25 3.12 0 40 200 100 50 25 12.5 1 6.25 0 40 100 50 25 12.5 1 6.25 3.12 1.56 0.78 0 40 100 50 25 12.5 6.25 3.12 1.56 0 .78 60 | 100 50 25 12.5 6.25 1.12 1.56 0 40 | 12.5 6.2 3.1 1.56 0.78 0.39 0.19 0 60 1 S 33.5 27.5 25.0 18.5 19.0 18.0 15.0 111.0 | 17.5 9.0 26.5 24.0 20.5 2il.5 20.0 11.0 17.5 12.5 32.0 26.5 22.5 19.0 19.0 16.0 15, 0 11.0 17.5 and 28.5 21.5 2<0.0 20.5 18.5 19.5 17.0 14.0 20.5 22.0 22.0 19.5 17.0 16 ,0 13.5 13.0 10.0 16.0 | 8.0 15.5 30.0 20.0 24.5 25.5 23.0 11.0 20.5 / 4 1 305 250 227 168 173 164 136 159 82 241 218 186 195 182 159 114 291 241 205 173 173 145 136 159 | 285 215 200 205 185 195# 170* 140 205 1 220 220 195 170 160 135 130 160 73 141 273 182 223 232 209 186 |27 122 586 Table 3 Leukemia test lymphatic L 1210 28 Compound 1,4HDwu<2-dimethylaminoethylamino)- aTitraquinone Control 5-Fluorouracil Dose (mg/kg) Days 1—9 50 25 12 0 20 Median survival time (days) 12.0 (11.0 9.4 8.9 17.6 T/C X 100 f/*) 135 124 106 ¦ — 188 1 Unpigmented melanoma test B 16. The animals used are C 57 BC/6 mice, all of the same sex, weighing a minimum of 17 g, with differences in the weight of all mice not exceeding 3 g. Test groups usually include 10 animals each. 1 g of B 16 unpigmented melanoma tumor tissue is homogenized in 10 ml of cold balanced salt solution, and then a 0.5 ml portion of the homogenate is implanted intraperitoneally in each of the tested mice. The compounds tested are administered intraperitoneally on the first day and next within 9 days (relative to tumor inoculation) in different doses. The animals are weighed and the number of animals surviving for 60 days is recorded in a uniform manner. The median survival time and the ratio of survival time of treated animals (T) to control animals (C) are calculated. The positive control compound is 5-fluoro-uracil, administered by injection at 20 mg/kg. The results of this test using representative compounds prepared according to the invention are given in Table 4 below. The performance criterion is 30 T/C -*di[(2-dimethylaminoethyl)a'mmo]-5,8-di- hydroxyanthraquinone Control 5-Fluorouracil 1,4hDi[(2-dimethylaminoethyl)-amino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil Leuiko -d'4-di[i(2-diylaminoethyl)amino] ^5,8-di-hydroxyanthraquinone Control 5-Fluorouracil 1,4-Di[<2-diethylaminoethyl)amino]-5,8-di - hydroxByaintrachinone Control 5-Fluorouracil 1 Dose (mg/kg) 2 25 12 6 3 0 20 25 12 6 3 0 20 50 0 20 50 0 20 Median survival time (days) 3 25.0 23.0 21.5 21, 0 16.5 25.0 24.5 28.5 27.0 25.5 18.0 26.0 23.0 16.5 25.0 20.5 16.5 , 25.0 | T/C table 4 1 1 I^uco-1,4Hdi[[2i(1-pyrrolidinyl)-ethyl]amino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-Di[[2-(l - pyrrolidinyl)ethyl]amino ] -5,8-dihydroxy- anthraquinone Control 5-Fluorouracil 1,4-iDi[((3-dimethylaminoipropyl)-amino] -5,8-dihydroxy- cysyantraquinone Control 5-Fluorouracil Leuko-1,4 -di[(2-aminoethyl)amino]-5,8-dihydroxy- anthraquinone Control 5-Fluorouracil Lreuko-l,4-di(3-afminopropylamino)-5,8^dihydroxy- anthraquinone Control 5-Fluorouracil / Leuko-l ,f-di[2-(2-methylamino€tylamino]-5,8-dihydroxyanthraquinone Control " 5-Fluorouracil Leuco-l,4-di[2-(l-piperazinyl)-ethylamino]-5,8- dihydroxyanthraquinone and * Control 5-Fluorouracil l,4-d,wu[2-i(2-arninoethylamino)-ethylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil l,4-di[ 2-dimethylaminopropylamino]-5,8-di-hydroxyanthraquinone Control 5-FluoTOuracil 1,4-di[2-(2-hydroxyethylamino]-5,8-dihydroxyanthraquinone dihydrochloride 1 2 1 50 25 12 0 20 25 12 6 0 20 25 0 20 12 0 20 50 25 12 6 0 20 50 25 12.5 6.2 0 20 50 25 12.5 6 3 0 20.0 50 25 12 6 0 20 100 50 25 12.5 6 0 20 12 6 3 1.5 0.7 0.3 | 1 3 23.0 22.0 21.0 16.0 26.5 24.5 22.0 22.0 16.0 26.5 20.0 16.0 26.5 32.0 16.0 26.5 31.5 27.0 23.5 22.5 (16.0 26.5 12.5 35.0 39.5 28.5 17.0 30.0 34.5 30.5 26.0 22.0 20 .5 17.0 30 24.0 22.5 22.0 20.0 16.0 27.0 21.0 28.5 24.5 20.5 19.5 17.0 30.0 11.0 " 15 ,0 28.5 34.0 34.0 34 1 4 1 144 137 131 — 166 153 137 137 — 166 125 — 166 . 200 — 166 . 197 169 147 141 — 166 73 206 232 168 — 176 203 179 153 129 121 — 176 150 141 138 125 — 169 124 168 144 121 115 — 176 73 100 190 227 227 227 1122 586 31 32 continued table 4 1 l 1 2 Control 5-Fluorouracil Leukx)-l,4-d wu[2H(2-isopropylamino )-ethylamino]-5,8-di-hydroxyanthraquinone Control 5-Fluorouracil 1,4-di[2-!( methylamino)ethylamino]- -5,8-dihydroxyanthraquinone dihydrochloride Control 5-Fluorouracil Leuico-1,4-di( 4-aminobU!tylamino)-5,8-dihydroxy- anthraquinone Control 5-Fluorouracil L8uko-1,4-di[2-(2-hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil Leu:co- 1,4-Di[2-{methylamino)ethylamino]-5,8-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-Di(2-dimethylaminoethylamino)-anthraquinone Control 5-Fluorouracil 1,4-Di(2-morpholmoethylamino) )-anthraquinone Control 5-Fluorouracil Deuco-l,4-di(2-aminoethylamino)-anthraquinone Control 5-Fluorouracil l,4-DwiU{2-aminoethylamino)-ainthraquinone 1 1 ° | 60 50 25 12 6 0 1 20 12.5 6.2 3.1 1.5 0.78 0.39 0.19 0 60 100 50 25 12 0 20 6 3 1.5 0.75 0.37 0 20 12 6 3 1.5 0.7 0 20 50 25 12 0 20 400 200 0 20 100 50 25 12 6 0 20 | 12 6 3 1 1 3 1 15.0 | 23.0 6.5 31.0 30.0 25.0 16.5 | 16.5 11.5 26.5 49.0 33.0 35.0 25.0 29.5 19.5 25.0 2:1.0 20.0 18.5 16.0 17.0 30.0 9.5 20.5 30.0 28.5 22.0 16.0 27.5 28.0 32.5 31.0 36.0 27.5 16.0 27.5 23.0 19.5 13, 5 16.5 1 25.5 24.0 20.0 18.0 26.0 | 25.0 35.5 33.0 27.5 22.0 17.5 26.0 1 31.0 30.5 29.0 1 4 | 153 39 188 182 151 1 10° 59 136 251 169 179 128 151 128 | 124 118 109 94 176 | 59 128 187 178 137 172 j 175 203 194 225 172 172 139 118 84 155 133 1 111 144 143 1 203 187 157 126 149 182 179 171 |122 586 33 34 c.d. table 4 1 1 Control 5-Fluorouracil 1,4-Di(2-methylaminoethylamino)-anthraquinone Control 5-Fluorouracil 1,4,5-Tri[(2-aminoethyl)amino]-8-hydroxiyantraquinone Control 5-Fluorouracil 1,4 -Di[(2-diume,tylaminoethyl)-amino]-5,6-dihydroxyanthraquinone Control 5-Fluorouracil 1,4-Di(3-aminopropylamino)-5,8-dihydroxyanthraquinone Control 5-Fluorouracil 2 1, 5 0.7 0 20 12 6 3 1.5 0.7 0 20 6 0 20 50 25 12 6 0 20 12 6 0 20 3 23.5 22.0 17.0 26.0 33.0 37.5 36 ,0 28.5 24.5 17.5 26.0 26.0 16.0 26.5 23 24 23 22.5 16.0 26.5 24.0 30.0 16.0 26.5 4 1 138 129 153 187 214 206 163 140 149 163 166 153 160 153 150 166 150 187 166 Ridgway osteosarcoma test. The animals used are AKD2F1/J mice, all of the same sex, weight zace minimum 17 g, with differences in weight of all mice do not exceed 3 g. Test groups usually contain 8 animals. The tumor is implanted subcutaneously using a trocar, administering 5 2-mm fragments per mouse. Test compounds are administered intraperitoneally daily for 4 days, with a total number of injections of 6, starting on day 15, relative to tumor inoculation. in different doses. The animals are weighed and the number of survivors recorded uniformly for 90 days. Tumor regressions are recorded in all animals examined. The results of this test using a representative compound of the invention are given in Table 5 below, as the percentage of animals showing tumor regression. Table 5 Ridigway Osteosarcoma Test Compound 1 Placebo Dose (mg/kg) 2 - 1 day before pregnancy. treatment Number of mice in group 3 8 Tumor (mm) 2 4 64 7 days after the end of treatment Ratio of the number of mice that did not develop cancer to the number of mice that survived 5 0/5 Tumor (mm ) 2 6 1189 P/» tumor growth inhibition 7% of mice showing 50n/o inhibition. cancer growth 8 0 63 days after completion of treatment Median survival time. (days) 9 44.5 T/C i(%) 10 |122 586 35 36 cont. table 5 1 1 l,4-di[<2-di-methyl|»minoethyl)-amino]-5,8-di- hydroxyanthrachi- Inone Methotrexate Vincristine 2 100 50 25 12 6 25 12 6 0.5 1.0 0.5 | 3 7 8 8 7 7 8 8 8 8 6 7 .4 77 68 82 84 83 51 52 54 42 99 94 5 2/5 2/6 0/8 0/3 0/6 1/6 0/5 0/4 4/4 6/6 4/7 6 52 268 653 470 960 546 916 758 0 0 77 7 96 78 41 61 19 54 23 m 100 100 93 8 28 25 0 0 0 12 0 0 100 100 57 9 48 92.5 78 37 57.5 52.5 49 46 68 &5 83 10 108 208 175 83 129 | 118 110 103 | 153 191 186 | The invention is explained by the following examples. Example I. Method for preparing leuco-1,4-di[(2-dimethylaminoe1;yl)amino]-5j8-dihydrolxyanthradlinone. Reaction mixture containing 10.58 g of N,N-dimethylethylene diamine, 60 ml of N 'N,N',N'-tetramethylethylene diamine and 10.96 g of leuco-1,4,5,8-tetrahydroxyanthraquinone are flushed with nitrogen and heated in an oil bath for 2 hours in a nitrogen atmosphere. at a temperature of 49-51°C. The mixture is then left under nitrogen to cool, and then the precipitate is isolated and washed with ethanol, obtaining 14.78 g of the desired compound in the form of a dark red solid. At a temperature of 224°C the product sinters and up to a temperature of 300°C the product does not melt. Example II. Method for producing 1,4-di[i(2-dimethylaminoethyl)amino]-5,8-dihydroxyanthraquinone. 12.00 g of leuco-1,4-di[(2-dimethylaminoethyl) amino]-5,8-dihydroxyanthraquinone in 100 ml of nitrobenzene are heated under reflux for 15 minutes and then filtered hot. The obtained filtrate is heated. until boiling, then left to cool, the precipitate is isolated and washed with ethanol, obtaining 8.44 g of the desired compound in the form of blue-black crystals, melting point 236-238°C. Example III. Method for preparing leuco-1,4-di(2-morpholinoethylamino)-5,8-dihydroxyanthraquinone. Solution of 15.62 g of N-(2-aminoethyl)morpholine in 40 ml of N,N,N'N'-tetramethylenediamine deaired by bubbling nitrogen through it for 15 minutes, then 10.97 g of leuco-(1,4,5-8-tetrahydroxyanthraquinone) are slowly added with stirring. The obtained suspension is processed in method as described above in Example 1, obtaining 18.07 g of the desired compound in the form of an olive-colored solid, melting point 223-227° C. Example 4. Method for preparing l4-di- (2-,morpholinoethylamino)- 5,8-dihydroxyanthraquinone in 100 ml of nitrobenzene is oxidized as described above in Example II, obtaining 10.30 g of the desired compound in the form of black rods, melting point 241-243°C. Example V. Method of preparing leuco-1,4-di[(2-diethylaminoethyl)amino] -5,8-dihydroxyanthraquinone. The process is carried out as described above in Example 3, with the difference that instead of N-(2-aminoethyl)morpholine, 13.95 g of N,N- - diethylethylenediamine, obtaining 13.97 g of the desired compound in the form of a red-brown solid, melting point 182-185°C. Example VI. Process for preparing 1,4-di[(2-diethylaminoethyl)amino]-5,8-dihydroxyanthraquinone. 10.90 g of leuco-1,4-di[(2-diethylaminoethyl)amino]-5,8-dihydroxyanthraquinone are oxidized as described in Example II above, obtaining 6.35 g of the desired compound in the form of blue-black needles, melting point 202-204°C. Example VII. Method for producing leuco-1,4-di[2-< 1-pyrrolidinyl)ethylamino]-5,8-dihydroxyanthraquinone. The process is carried out as described above in Example 3, with the difference that instead of N -(2-aminoethyl)morpholine, 12.05 g of N-2-pyrrolidinoethylamine and also 80 ml of N,N,N',N'-tetramethylethylene diamine are used to obtain 13.24 g of the desired compound in the form of a solid of ¬ red-brown, melting point 180-185°C. Example 8. Method of preparing 1,4-di-[2-traquinone. 8.61 g of leulco-1,4^di[[<2-(! 1-pyrrolidinyl)ethyl]amino]-5,8-dihydroxyanthraquinone is oxidized as described in Example 2. The reaction mixture obtained is evaporated to dryness and the residue is crystallized from toluene. , obtaining 5.12 g of the desired compound in the form of blue-black crystals, melting point 193-196°C. Example 9. Method for preparing leuco-1,4-di[2-(methylamino ethylamino]-5,8-dihydroxy-anthraquinone. The process is carried out as described above in Example 7, with the difference that instead of N-2-pyrrolidinoethylamine, 8.90 g of N-methylethylene diamine are used, obtaining 13 .73 g of the given compound in the form of a dark green solid, melting point 157-160°C. Example - droxyanthraquinone. Nitrogen is bubbled through 80 ml of dimethylaminopropylamine for 15 minutes, then 10.97 g of leubo-1,4,5,8-tetrahydroanthraquinone are added slowly and with stirring. The obtained mixture is heated in a nitrogen atmosphere at a temperature of 50-52°C for 2 hours and then left to cool. Then the precipitate is isolated and washed with cold ethanol, obtaining 5.59 g of dark, orange-red crystals, melting point 115-118°C. Example XI. Method for producing 1,4-di[(3-dimethylamiopropyl)amino]-5,8-dihydroxyanthraquinone. Suspension of 6.00 g of leukoJl,4-di[(3Hdimethylaminopropyl)amino]-5,8dihydrocByanTachinone in 60 ml of N,N,N^N'-tetramethylethylene diamine is heated for 12 hours in a steam bath under a reflux condenser, while air is passed through the suspension. The obtained solution is cooled, leading to the separation of a precipitate, which is isolated and washed twice with heptane and once with petroleum ether. The obtained precipitate is crystallized by extraction with 350 ml of hot heptane, filtration of the obtained extract and concentration of the filtrate to 300 ml. After crystallization and washing with petroleum ether, 3.72 g of the desired compound are obtained in the form of black needles. , melting point 154-157°C. Example XII. Method for preparing leuco-1,4-di(2-aminoethylamino)-5,8-dihydroxyanthraquinone. Reaction mixture consisting of 10.97 g of leuco-1,4,5,8-tetrahydroxyanthraquinone in 80 ml of deaerated N,N,N^N'-tetramethylethylene diamine containing 7.22 g of ethylene diamine was heated with stirring at 48-50° C. under nitrogen for 1 hour. The resulting mixture is allowed to stand while maintaining a slow flow of nitrogen, leading to the formation of a precipitate, which is isolated and washed with ethyl acetate, acetonitrile and petroleum ether, obtaining 13.8 g of the desired compound in the form of a red-black solid. . The product does not melt up to a temperature of 350°C. JR.: 6.34; 820 nm. Example XIII. Method for producing leuco-19-1,4-di(3-aminopropylamino)-5,8-dihydroxyanthraquinone. Suspension 10.97 g of leuco-1,4,5,8-tetraquinone in deaerated solution 8.90 g 5 1,3-Diaminopropane in 80 ml of N,N,N',N'-tetramethylethylene diamine is stirred and heated at 49°C under nitrogen for 1 hour and then left to cool. The precipitate obtained is isolated and washed with cold ethanol, obtaining 14.21 g of the desired compound in the form of a black solid. The product does not melt up to a temperature of 350°C. JR: 6.44; 8.22 nm. Example XIV. Method for producing leuco-1,4-di[2-<2-hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone. Suspension of 12.5 g of 2-i(2-aminoethylamino)ethanol in 40 ml of NyNjIl^N^tetramethylethylene diamine stirred and deaerated by bubbling nitrogen for 15 minutes. 10.97 g of leuco-1,4,5,8-tetrahydroxyanthraquinone are then added gradually and with stirring to this suspension, and then the suspension is stirred and heated under nitrogen in an oil bath at a temperature of 50-52°C. within 5 hours. Then the mixture is left to cool under nitrogen for 12 hours, after which the precipitate is isolated by decantation, macerated in ethanol, isolated again and washed with ethanol, obtaining 15.06 g of the desired compound in the form of a green solid. -gray, melting point 129-131°C. Example 15. Method for producing leuco-1,4-39-di[2-[di(^-hydroxyethyl)amino]1ethylamino]-5,8-dihydroxyanthraquinone. Solution 17.8 g of N,LN-di<2-hydroxyethyl)ethyl- diamine in 100 ml of methanol is cooled in a bath of ice, mixed and deaerated by bubbling nitrogen for 15 minutes. Then 10.97 g of leu|co-ll,4,5,8-tetrahydroxyantrachlinone are gradually added with stirring and the mixture is then cooled. The obtained suspension is heated and stirred in a nitrogen atmosphere in an oil bath at a temperature of 50-52° C. for 1 hour, and then the resulting mixture is left to cool under nitrogen overnight. Then the precipitate is isolated and washed with ethanol, obtaining 14.8 g of the desired compound in the form of a red-brown solid, melting point 165-168°C. Example XVI. Method for producing 1,4-di[2-(methylamino)ethylamino]-5,8-dihydroxyanthraquinone dihydrochloride. 55 To a suspension of 11.60 g (0.03 nibs) of leukol-1,4-di[2^(methylamino)ethylamino]-5,8^dihydroxyanthraquinone in 200 ml of 2Hmethoxymethanol, 15 ml are gradually added with stirring 8 N ethanolic hydrogen chloride solution. The mixture is cooled and stirred in an ice bath, while gradually adding 7.50 g (0.0305 mol) of chloranil powder. The resulting mixture is stirred overnight at room temperature, then diluted with 600 ml of ether and the precipitate is isolated and washed. tetrahydrofurane 39 122 586 40 14.16 g of the compound is obtained, which is crystallized by dissolving it in 130 ml of water and adding 650 ml of acetone, obtaining 13.15 g of the given compound in the form of a solid of blue and black. This product does not melt up to 350°C. JR: 6.20; 6.39; 8.26, 12.13 nm. Example XVII. Method for preparing 1,4-di[2-(2-aminoethylamino)ethylamino]-5,8- xyanthraquinone. As described above in Example 3, from a mixture of 10.97 g of leuco-1,4,5,8- tetrahydroxy-anthraquinone, 80 ml of N,N,N',N'-esteromethylethylene diamine and 21.84 g (0.24 mol) of diethylene triamine, a thick, congealed mass is obtained which cannot be mixed effectively, so that reaction time is extended to 24 hours. The resulting mixture is allowed to cool, then the supernatant is decanted and discarded. The solution of the solidified mass in 100 ml of methanol is filtered and then left to oxidize with air for 4 days in a flask only partially covered. During this time, a gelatinous mass is released, which solidifies by mixing the mixture with 200 ml of acetonitrile and then standing for 1 hour. The obtained precipitate is isolated and washed, first with acetonitrile and then with ether, to obtain 10.86 g of the desired compound in the form of a blue-black powder. This product does not melt up to 350°C. JR: 6.21; 6.42; 8.31 nm. Example 18. Method for preparing leuko*-1,4-di(4-aminobutylamine)-5,8-dihydroxyanthraquinone. The process is carried out as described in Example 3 above, with the difference that 45 is used as the primary amine. ml of 1,4-di-amdnobutane, obtaining 12.20 g of the desired compound in the form of a dull gray-green solid. This product does not melt up to 350°C. JR: 6.31; 8.12; 12.02 nm. Example XIX. Process for producing leuco-1,4-di[2-dimethylaminopropylamino]-5,8-dihydroxyanthraquinone. 12.26 g of 2Mdimethylamidnopropylamine are reacted with 10.97 g of leuco-(1,4,5,8-terohydrotosymtraquinone in 100 ml of ethanol for 1 hour, as described in Example I above, to obtain 7, 2<9 g of the desired compound in the form of red-brown crystals. This product darkens at 255°C, does not melt up to 350°C. JR: 6.31; 8.11, 12.02 nm. Example XX. Method for preparing leuco-1,4-di[2-(2-methylaminoethylamino)ethylamino]-5,8-dihydroxyanthrammonium. To a solution of 14.10 g of 1-methyldiethylenetriamine in 50 ml of ethanol and 40 ml of N,N,N',N'-tetramethylethylene diamine, 10.97 g of leuco-1,4,5,8-tetrahydroxyanthraquinone are added as described in Example I. The resulting mixture is heated at 50° C and stirred in a nitrogen atmosphere for 1 hour, then cooled in an ice bath, then the precipitate was isolated and washed with cold ethanol, obtaining 7.23 g of the desired compound in the form of green-black crystals with a melting point 108^1il! l°C. Example XXI. Process for producing leuco-1,4-di[2-(l-piperazinyl)ethylamino]-5,8-dihydroxyanthraquinone. 15.50 g of N-<2-aminoethyl)piperazine are processed as described above in Example XX, obtaining 3.92 g of the product in the form of a black powder which does not melt at a temperature of 350°C and remains rejected. However, a precipitate is separated from the mother liquors and ethanol washings during standing in an uncapped flask and partial evaporation within two weeks, which is isolated and washed with ethanol, obtaining 6-19 g of the desired compound in the form of a solid. black solid, melting point 200-203°C. Example XXII. Method for producing 1,4-di(2-aminoethylamino)-5,8-dihydroxyanthraquinone dihydrochloride. 28.25 g of the compound prepared as above in Example XII was oxidized with chloranil as described in Example XVI, obtaining 29.66 g of the crude product in the form of a blue-black solid. , which is then subjected to extraction by mixing with 800 ml of water for 14 hours. The solid parts of the mixture are removed by centrifugation, and the supernatant is freeze-dried, obtaining 16.38 g of the desired compound in the form of a blue-black solid that does not melt at a temperature of 350°C. Example XXIII. Method for preparing 1,4-di[2-(2-hydrocrylamino)ethylamino]-5,8-dihydroxyanthraquinone dihydrochloride. 17.86 g of the compound prepared as described in Example 14 above is oxidized with chloranil in the same manner as described in Example 16, but omitting recrystallization, to obtain 21.34 g of the desired compound in the form of a solid. blue-black in color, melting point 203-205°C. Example XXIV. Method for producing 1,4-di[2-i(2-methylammoethylamano)ethylamino]-5,8-dihydroxyanthraquinone tetrahydrochloride. 11.70 g of the compound prepared by; as described above in Example XX is oxidized using chloranil in the manner described above in Example XVI, obtaining 18.03 g of the desired compound in the form of blue-black crystals, melting point 190-203°C. Example XXV. Method for preparing 1,4-*-di[2(2-hydroxyethylamino)ethylamino]-5,8-dihydroxyantraiquinone. The process is carried out in the same way as described in Example XIV, with the difference that the solvent is 100 ml of ethanol. The mother liquor remaining after the isolation of leuco-compound-41 122 5S6 42 ku is left for two weeks in an uncorked flask, during which time the oxidized product is isolated, washed with ethanol, and then recrystallized from ethanol to obtain the desired compound. in the form of blue-black crystals, melting point 175-177°C. Example XXVI. Method for preparing leuco-1-dihydroxyamine-1-propylamino]-5,8-dihydroxyanthraquinone. The process is carried out in the same way as described in Example 15, with the difference that solution 14 is used. 18 g of 2v(3-aminopropylamino)ethanol in 100 ml of ethanol. The obtained solution is filtered and the filtrate is diluted with 300 ml of ether, leading to the precipitation of a sticky mass. The supernatant is then decanted and the sticky mass is crystallized by shaking it with 100 ml of tetrahydrofuran. After washing with ethanol, 12.96 g of the desired compound are obtained in the form of a green-black solid, melting point 101-1040C. Example XXVII. Method for preparing 1,4-di[3-<2-hydroxyethylamine]-1-propylamino]-5,8-dihydroxyanthraquinone dihydrochloride. 9.95 g of leuco-1,4-di[3H(12-hydroxyethylamino)propylamino]-5,8-dihydroxyanthraquinone are oxidized with chloranil in the manner described above in Example 16, obtaining 11 .70 g of the desired compound in the form of a blue solid that does not melt up to a temperature of 350°C. Example XXVIII. Method for producing leuco-1,4-di[2H(3-hydroxy-1-propylamine©)ethyla! mino]-5,8-dihydroxyanthraquinone. The process is carried out as described in Example 15, using 14.18 g of N-i(3-hydroxypropyl)ethylene diamine in 100 ml of ethanol, obtaining 14.63 given compound in the form of red-brown crystals with a melting point of 58-60°C. m ' Example XXIX. Method for producing 1,4-dWu[2-(3-hydroxy-1-propylamino)ethylaphliino]-i5,8-dihydroxyanthraquinone dihydrochloride. 10.77 g of the compound prepared as described above in Example XXVIII is oxidized using chloramil as described above in Example XVI, obtaining 11.64 g of the desired compound in the form of a dark blue solid with a melting point ' property 210-216°C. Example XXX. Method for preparing leuco-1,4-di[2-(2-hydroxy-1-propyfloaimino)ethylamino]-5,8-dihydrolxyanthraquinone. The process is carried out as described above in Example 15, using 14.18 g of 1-(2-aminoethylamino)-2-propanol in 100 ml of ethanol, obtaining 17.61 g of the desired compound in the form of green-black crystals, melting point 50-60°C. Example XXXI . Method for the preparation of 1,4-di[2-(2-hydroxy-1-propylaminolethylamino]-5,8-dihydroxyanthraquinone dihydrochloride. Filtered solution 14.44 g of leuko^l,4-di[2-(2- 20 35 40 50 55 60 S-hydroxy-1-proipylamino)ethylamino]-11,4-dihydroxyanthraquinone in 215 ml of 2-methoxyethanol is oxidized with 7.65 g of chloranil as described above in the example XVI, obtaining 16.75 g of the desired compound in the form of a purple solid, melting point 177-185°C. Example XXXII. Method for preparing leuco-1,4-di[2 - [! 2- (2 -hydroxyethylamino)ethylamino]ethylamino]-58-dihydroxyaritraquinone. The process is carried out as described in Example ml of methanol, obtaining a solution that is filtered, then diluted with 300 ml of ether, causing a sticky mass to form which hardens on standing overnight. This hardening is completed by thorough maceration in a solvent. Then the precipitate is isolated and washed with ether. obtaining 16.82 g of the desired compound in the form of a green-black solid. This product maintains its granular structure when stored at -25°C, but becomes a compact mass when stored at 25°C. Melting point 75-85°C. Example XXXIII. Method for preparing 1,4-di[2-[2-(2-hydroxyethylamlino)ethylamino]ethylamino]-5,8-dihydr;0:xyanthraquinone tetrahydrochloride. ¦» 12.10 g of the compound prepared as described above in Example XXXII are oxidized using chloranil in the manner described above in Example 16, with the difference that the obtained precipitate is additionally washed 3 times with methanol, obtaining 12, 46 g of the desired compound in the form of a dark-colored solid. blue.- Melting point 190°^205°C.JR: 6.21; 6.33; 8.33 frames.Example XXXIV. Method of producing two-; 1,4k1wu[2-(2,3-dihydroxypropylamino)ethylamino]-5,8-dihydroxyanthraquinone hydrochloride. The process is carried out as described in Example XV, using a solution of 16.10 g of 3-<2 -aminoethylamino)-1,2-propanediol (A. R. Surrey, C. M. Suter and J. S. Buck, J; Am. Chem. Soc., 74, 4102 (1952)) in 100 ml of methanol, obtaining a sticky mass that separates from solvent by cooling in an ice bath and then decanting. The sticky mass is washed 4 times, stirring it for 1 1/2 hours at 25°C with 100 ml portions of methanol, cooling in an ice bath and decanting. The sticky mass is then dissolved in 280 ml of 2-methoxyethanol, the obtained solution is filtered and oxidized with 10.01 g of chloranil in the manner described above in Example 16. The obtained product is additionally washed with ethanol to obtain 15.25 g of the desired compound in the form of a blue-black solid, melting point 191-1-3°C. Example XXXV. Method for preparing leu-122 586 43 44 co-1,4-di[2-(1-aziridino)ethylamino]-5,;8-dihydroxyanthraquinone. The process is carried out as described above in Example 15, using 10.33 g of N-{2-aminoethyl)azaridine in 80 ml of N,N,N',N'-tetramethylethylenedimethylene, obtaining the product in the form of a hard gum. The next day, the supernatant is discarded, 100 ml of ether is added and the gummy mass is periodically macerated in it for the next day, during which it hardens even more. This hardening was completed during maceration by washing the precipitate three times with ether, obtaining 17.66 g of the desired compound in the form of a granular blue-black powder. Melting point 120°^192 (C. JR: 6.37; 6.89; 8.20; 12.03 nm. Example XXXVI. Method for the preparation of 1,4-di[2-[2n/ll-imoyl)tetrahydrochloride (liino/ethylaminojethylamino]-5,8-hydroxyanthraquinone The process is carried out as described above in Example , which is filtered and diluted with 900 ml of ether. During this, a sticky mass is precipitated. The supernatant is decanted and the sticky mass is dissolved in 175 ml of 2-methoxyethanol and oxidized with 5.29 g of chloranil as described in the example above XVI, obtaining 17.7 g of the desired compound in the form of a dark blue solid. Melting point: 265°C. Example XXXVII. Method for preparing 1,4-di[2-[di/1^-hydroxyethyl/amino-dihydrochloride [ethylamino]-5,8-dihydroxyanthraquinone 10.77 g of the compound prepared as above in Example 15 were oxidized with chloranil as described in Example 16 to give 11.64 g of the desired compound in form of a solid, dark blue in color, melting point 216°C. Example XXXVIII. Process for the preparation of 1,4-dwii(2-,mo(rpholineethylamino)anthraquinone 9.60 g of quinizarine, 46.90 g of N-(2-aminoethyl/morpholino) and 56 ml of water are processed as follows: , as described in Example 1 above, to obtain 9.92 g of the desired compound in the form of a blue-black solid, melting point 158-159*0. Example XXXIX. Process for the preparation of 1,4-diyl 2nd diethylaiminoethylaminoZ-anthraquinone A mixture of 42 amines, 17.43 g of N,N-diethylethylene diamine and 12.0.1 g of quinizarin is stirred and heated under reflux for 15 hours. The obtained solution is evaporated to dryness, and then the residue is dissolved. in chloroform and the obtained solution is filtered through a layer of 300 g of aluminum oxide. The blue filtrate is chromatographed on silica gel in a column covered with a NylonR layer, using a 6:1 mixture of chloroform and methanol for development. The main band blue color is cut out and then eluted with a 6:2:1 mixture of chloroform, methanol and triethylamine. The obtained eluate is evaporated and the residue is crystallized from hexane and then washed with petroleum ether, obtaining 1.43 g of the desired compound in the form of blue-black plates, melting point 109°C. .Example XL. Process for the preparation of leuco-1,4-di(2-aminoethylamino)-anthraquinone 125 ml of ethylene diamine are deaerated by passing nitrogen for 15 minutes. Then 12.0 g of leucoquinizarin are added and the mixture obtained is heated with stirring and under nitrogen at 50° C. for 1 hour, after which the mixture is allowed to cool. The obtained precipitate is isolated and washed successively with ethyl acetate, acetonitrile and petroleum ether, obtaining 8.07 g of the desired compound in the form of green-gold crystals, melting point 162-165°C (with decomposition) at a temperature increase rate of 9°/minute.' Example ¬, heated at 50°C, air is passed through for 1 hour. The obtained mixture is diluted with 87.5 ml of acetonitrile, then left to cool, and then the obtained precipitate is isolated and washed with acetonitrile, obtaining 5, 43 g of the desired compound in the form of a dark blue solid, melting point 170-171°IC 35 Example and 25 g of deaerated Nnmethylethylene diamine are heated at 50° C. with stirring, in a nitrogen atmosphere, for 1 hour. Air is then passed through the mixture for 40 minutes, continuing to heat at 50°C. The resulting mixture is evaporated to dryness and then evaporated twice with 45-25 ml of ethanol. The obtained residue is crystallized from a mixture of ethanol and ether at a temperature of -70°C, obtaining 2.32 g of the crude product in the form of a solid, which is crystallized twice from carbon tetrachloride, obtaining 1.92 g of the desired compound. in the form of dark blue crystals, melting point 131-32°C. Example XLIII. Method for preparing 1,4-di/2-pyridineethylamino/anthraquinone 65 A mixture of 4.07 g of quinizarine, 21.74 g of N-/2-aminoethyl/ipiperidine and 26 ml of water is stirred under reflux for 2 hours, then set aside overnight. The separated gummy precipitate is isolated and washed with water by centrifugation, obtaining 1.99 g of a blue-black precipitate, which is dissolved in 15 ml of chloroform and chromatographed using the short method on a wet column. containing 100 g of aluminum oxide, using chloroform for elution. E-5 eluate in a total volume of 180 ml is collected in eight separate fractions, starting from the moment when the eluate turns blue until the black band approaches the bottom of the column. Fractions 1-6 combines and evaporates to obtain 1.42 g of blue-black crystals, which are crystallized from ethanol to obtain 1.35 g of the desired compound in the form of blue-black needles, melting point 140- 141°C. This compound, after drying under reduced pressure at 78°C, has a melting point of 156-157°C. Example XLIV. Method for preparing leuco-1,4-di/2-dimethylaminoethylamino/anthrachithion f A solution of 26.44 g of NjN-dimethylethylene diamine in 75 ml of N,N,N',N'-tetramethylethylene diamine is deaerated with by passing nitrogen through the holes for 15 minutes, then 12.11 g of leucoquinizarin are added and the obtained mixture is stirred under nitrogen and heated to a temperature of 48-50°C for 21 hours. The obtained mixture is cooled overnight. in an atmosphere of nitrogen, and then the obtained precipitate is isolated by filtration and washed three times by mixing in the form of a slurry with acetonitrile and twice with petroleum ether, obtaining 12.52 g of the desired compound in the form of dark green crystals, melting point 150-157°C, and when using a microscope with a heated stage 153-154°C. Patent claim: A method of preparing new anthraquinone derivatives of the general formula I and their tautomeric variants and pharmacologically acceptable acid addition salts, in which A-B denotes a group such as CH=CH or CH2--CH2, Q denotes a divalent moiety , such as the group of the formula -ffi^n - the group of the formulas 2-9, where n is an integer from 2 to 4 inclusive; Ri and R2 each separately represent a hydrogen atom, an alkyl group with 1-4 carbon atoms, and a monohydroxy-4g alkyl group with 2-4 carbon atoms, in which there should be no hydroxy group at the carbon atom in position a in relation to the nitrogen atom. a dihydroxyalkyl group with 3-6 carbon atoms, in which there should be no hydroxyl group at the carbon atom in the 5Q position in relation to the nitrogen atom, a formyl group, an alkanoyl group with 2-4 carbon atoms, a trifluoroacetyl group or a moiety with the formula —/CH2/n-HCN, —/CHjj/n^O—R or formula 10, in which n is an integer from 2 to 4 inclusive, R is an alkyl group with 1-4 carbon atoms, and R3 and R4 each individually represent a hydrogen atom, an alkyl group with 1-4 carbon atoms or a monohydroxyalkyl group with 2-4 carbon atoms, in which there should be no hydroxyl group at the carbon atom in position a in relation to the nitrogen atom. , Rt and R2 together with the nitrogen atom attached to them and R3 and R4 together with the nitrogen atom attached to them constitute a morpholide, thiomorpholino, piperazine, 4-methyl-1-piperazine group or a moiety of formula 11, in which m means an integer numerical value from 2 to 6 inclusive, where the ratio of the total number of carbon atoms to the sum of the total number of oxygen atoms and the total number of nitrogen atoms in the side chains in positions 1 and 4 cannot exceed 4, R5 means a hydrogen atom, a hydroxyl group, a halogen or an alkanoyloxy group with 1-6 carbon atoms, Re means a hydrogen atom or a hydroxyl group, R7 means a hydrogen atom, a hydroxyl group, a halogen, an alkanoyloxy group with 1-6 carbon atoms or a moiety with formula 12, in which R8 and R9 each individually represent a methyl, ethyl or 1-hydroxyethyl group, with the limitation that when Q is -/OH3/n-, then R1, R2, R5, R6 and R7 are not mxyga can also be hydrogen, and when R5, Re and R7 are hydrogen, R1/R2 cannot be H/monohydroxyalkyl, and when n is 2, then Ri/R2 cannot be -/CH:/2^0- /CH2/2, H/GHs, H/C2H5 or C2H5//C2H5, and when n is 3, Ri/R2 cannot be CH3/CH3 or -/CHa/s- and when R5 and R7 are hydroxyl and n is 2, then Ri/R2 cannot be CH3/CH3, C4H9/C4H9 or -ICK2/5-, and when n is 3, then Ri/R2 cannot be H7IH, CH3/CH3, CJH7/C3H7 or -^/CH2/2—O—/UH.^2— and when n is 4, then Ri^R2 cannot be C2H5/C2H5 C4H9/C4H9 or —/CH^— and when R5 is a hydroxyl group , then one of the substituents with the symbols Re and R7 must represent a hydrogen atom, when R5 represents a hydrogen atom, then each of the substituents with the symbols Re and R7 must represent a hydrogen atom, and only one of the substituents Ri and R2 may constitute a group alkanoyl, characterized in that the compound of formula 15, in which R5, Re and R7 and A—B have the meanings given above, and hal is a chlorine, bromine or iodine atom, reacts /Ri with the compound of the formula H^N—Q -^N< R in which Hi, R2 and Q have the meanings given above, with the limitation that if one of the substituents with the symbols R5 and R7 is halogen or an alkanoyloxy group, then the other one has the same meaning, and Re is hydrogen and optionally the product in which the moiety A-B is CH2-CH2 is oxidized to the product in which the moiety A-B is CHi= =GH; then the obtained compound is contacted under conditions favoring salt formation with a reagent that forms a pharmacologically acceptable salt! 15 20 25 30 35 40 45 50122 586 R5 O NH-Q—N. \ R7 O NH—Q—N.R2 -Ri FORMULA 1 CH3 I -CH —CH2— FORMULA 2 CH3 I - CH2— CH — WZClR 3 CH3CH3 I I —CH-CH— FORMULA U 92H5 -CH—CH2- WZdR 5 C2H5 - CH2- CH — FORMULA 6 CH3 AND CH -CH2-CH2- FORMULA 7 CH3 AND ¦CH2 CH — CH2 ^- WZdR 8 CH3 AND CH2-CH2-CH- WZdR 9122 586 -Rq — (CH2)n-N; FORMULA 10 -N (CH,) 2'm FORMULA 11 — NH^l^CI-^-N O N—Q-N.-Rl r7 o n—q-n; -R, tautomeric form R2 FORMULA U SCHEME 1122 586 R( R5 O hal R7 O hal FORMULA 15 OH O NH-O-N FORMULA 16 \ R- OH O NH-Q-N-(CH2)n-OH ho O NH-( CH2)n-N /*!A R yB R OH O NH-Q-N-(CH2) -OH FORMULA 17 \ R- HO O NH-(CH2)n-N FORMULA 18 A ^Ro HO O NHCH2CH2NCH2CH2OH HO O NHCH2CH2NCH2CH2OH Ri FORMULA 19 OH O NHOUCH ^N' I Tl 1 l Z - / Ri ¦R2 ,Ri oh o nhch2ch2n; MODEL 20 ^R 2122 58 CH2CH2OH CH2CH2OH MODEL 21 PL PL PL PL PL PL PL PL PL

Claims (1)

1. Patent claim A method for preparing new anthraquinone derivatives of the general formula 1 and their tautomeric variants and pharmacologically acceptable acid addition salts, in which A-B denotes a group such as CH=CH or CH2--CH2, Q denotes a group divalent, such as the group of the formula -ffi^n - the group of the formulas 2-9, in which n is an integer numerical value from 2 to 4 inclusive; Ri and R2 each separately represent a hydrogen atom, an alkyl group with 1-4 carbon atoms, and a monohydroxy-4g alkyl group with 2-4 carbon atoms, in which there should be no hydroxy group at the carbon atom in position a in relation to the nitrogen atom. a dihydroxyalkyl group with 3-6 carbon atoms, in which there should be no hydroxyl group at the carbon atom in the 5Q position in relation to the nitrogen atom, a formyl group, an alkanoyl group with 2-4 carbon atoms, a trifluoroacetyl group or a moiety with the formula —/CH2/n-HCN, —/CHjj/n^O—R or formula 10, in which n is an integer from 2 to 4 inclusive, R is an alkyl group with 1-4 carbon atoms, and R3 and R4 each individually represent a hydrogen atom, an alkyl group with 1-4 carbon atoms or a monohydroxyalkyl group with 2-4 carbon atoms, in which there should be no hydroxyl group at the carbon atom in position a in relation to the nitrogen atom. , Rt and R2 together with the nitrogen atom attached to them and R3 and R4 together with the nitrogen atom attached to them constitute a morpholide, thiomorpholino, piperazine, 4-methyl-1-piperazine group or a moiety of formula 11, in which m means an integer numerical value from 2 to 6 inclusive, where the ratio of the total number of carbon atoms to the sum of the total number of oxygen atoms and the total number of nitrogen atoms in the side chains in positions 1 and 4 cannot exceed 4, R5 means a hydrogen atom, a hydroxyl group, a halogen or an alkanoyloxy group with 1-6 carbon atoms, Re means a hydrogen atom or a hydroxyl group, R7 means a hydrogen atom, a hydroxyl group, a halogen, an alkanoyloxy group with 1-6 carbon atoms or a moiety with formula 12, in which R8 and R9 each individually represent a methyl, ethyl or 1-hydroxyethyl group, with the limitation that when Q is -/OH3/n-, then R1, R2, R5, R6 and R7 are not mxyga can also be hydrogen, and when R5, Re and R7 are hydrogen, R1/R2 cannot be H/monohydroxyalkyl, and when n is 2, then Ri/R2 cannot be -/CH:/2^0- /CH2/2, H/GHs, H/C2H5 or C2H5//C2H5, and when n is 3, Ri/R2 cannot be CH3/CH3 or -/CHa/s- and when R5 and R7 are hydroxyl and n is 2, then Ri/R2 cannot be CH3/CH3, C4H9/C4H9 or -ICK2/5-, and when n is 3, then Ri/R2 cannot be H7IH, CH3/CH3, CJH7/C3H7 or -^/CH2/2—O—/UH.^2— and when n is 4, then Ri^R2 cannot be C2H5/C2H5 C4H9/C4H9 or —/CH^— and when R5 is a hydroxyl group , then one of the substituents with the symbols Re and R7 must represent a hydrogen atom, when R5 represents a hydrogen atom, then each of the substituents with the symbols Re and R7 must represent a hydrogen atom, and only one of the substituents Ri and R2 may constitute a group alkanoyl, characterized in that the compound of formula 15, in which R5, Re and R7 and A—B have the meanings given above, and hal is a chlorine, bromine or iodine atom, reacts /Ri with the compound of the formula H^N—Q -^N< R in which Hi, R2 and Q have the meanings given above, with the limitation that if one of the substituents with the symbols R5 and R7 is halogen or an alkanoyloxy group, then the other one has the same meaning, and Re is hydrogen and optionally the product in which the moiety A-B is CH2-CH2 is oxidized to the product in which the moiety A-B is CHi= =GH; then the obtained compound is contacted under conditions favoring salt formation with a reagent that forms a pharmacologically acceptable salt! 15 20 25 30 35 40 45 50122 586 R5 O NH-Q—N. \ R7 O NH—Q—N. R2 -Ri FORMULA 1 CH3 I -CH —CH2— FORMULA 2 CH3 I - CH2— CH — WZClR 3 CH3CH3 I I —CH-CH— FORMULA U 92H5 -CH—CH2- WZdR 5 C2H5 - CH2- CH — FORMULA 6 CH3 I CH -CH2-CH2- FORMULA 7 CH3 I ¦CH2 CH — CH2 ^- WZdR 8 CH3 I CH2-CH2-CH- WZdR 9122 586 -Rq — (CH2)n-N; FORMULA 10 -N (CH,) 2'm FORMULA 11 — NH^l^CI-^-N R5 O N -Q-N. -Rl r7 o n—q-n; -R, tautomeric form •R2 FORMULA U SCHEME 1122 586 R( R5 O hal R7 O hal FORMULA 15 OH O NH-O-N FORMULA 16 \ R- OH O NH-Q-N-(CH2)n-OH ho O NH- (CH2)n-N /*! A R yB R OH O NH-Q-N-(CH2) -OH FORMULA 17 \ R- HO O NH-(CH2)n-N FORMULA 18 A ^Ro HO O NHCH2CH2NCH2CH2OH HO O NHCH2CH2NCH2CH2OH Ri FORMULA 19 OH O NHOUCH^N' I Tl 1 l Z - / Ri ¦R2 ,Ri oh o nhch2ch2n; MODEL 20 ^R 2122 58 CH2CH2OH CH2CH2OH MODEL 21 PL PL PL PL PL PL PL PL PL