MXPA00004634A - 2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors - Google Patents

Abstract

The invention relates to 2-phenyl substituted imidazotriazinones with short, unbranched alkyl radicals in position 9 in accordance with general formula (I). Said 2-phenyl substituted imidazotriazinones are produced from the corresponding 2-phenyl imdazotriazinones by chlorosulphonation and subsequent reaction with the amines. These compounds inhibit cGMP-metabolising phosphodiesterases and are suitable for use as the active agents in medicaments for treating cardiovascular and cerebrovascular diseases and/or diseases of the urogenital system, especially for treating erectile dysfunction.

Description

IM DAZOTRIAZINONAS 2-PHENYL SUBSTITUTED AS INHIBITORS • OF PHOSPHODYESTERASE DESCRIPTION OF THE INVENTION The present invention relates to 2-phenyl substituted imidazotriazinones, to the process for their preparation and to their use as medicaments, in particular as inhibitors of phosphodiesterases that metabolize cGMP. In the published specification DE 28 11 780 i idazotriazines are described as bronchodilators with spasmolytic activity and inhibitory activity against phosphodiesterases that metabolize cyclic adenosine monophosphate (cAMP-PDE, nomenclature according to Beavo: PDE-III and PDE-IV). No inhibitory action against phosphodiesterases that metabolize cyclic guanosine monophosphate (cGMP-PDE, nomenclature according to Beavo and Reifsnyder (Trends in P armacol.Sci. 11, 150-155, 1990) PDE-I, PBE- is described. TI and PDE-IV). No compound containing a sulfonamide group is claimed in the aryl radical in the 2-position. In addition, iraidazotriazokines are described in documents FR 22 13 058, CH 59 46 71, DE 22 55 172, DE 23 64 076 and EP 000 9384 , which do not have any substituent in position 2 and are also described REF .: 120082 as bronchodilators that have inhibitory action of cAMP-PDE. WO 94/28902 describes pyrazolopyrimidinones which are suitable for the treatment of impotence. The compounds according to the invention are potent inhibitors of one or more phosphodiesterases that metabolize guanosine 3 ', 5'-cyclic monophosphate (cGMP-PDE). According to the nomenclature of Beavo and Reifsnyder (Trends in Pharmacol. Sci. 11, 150-155, 1990), these are the phosphodiesterase isoenzymes PDE-I, PDE-II and PDE-V. An increase in the concentration of cGMP can produce a healing effect, antiplatelet, antithrombotic, antiproliferative, antivasoespastic, vasodilator, natriuretic and diuretic. It may influence the short-term or long-term modulation of vascular and cardiac inotropy, heart rhythm and the transmission of cardiac excitation (JC Stoclet, T. Keravis, N. Komas and C. Kugnier, Exp. Opin. Invest. Drugs (1995), 4 (11), 1081-1110). The present invention, therefore, provides the 2-phenyl-substituted i idazotriazinones of the general formula (I) in which R 1 represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, R represents chain alkyl linear that has up to 4 carbon atoms, RJ and R4 are the same or different and each represent hydrogen or _ represent Or straight or branched chain alkenyl or alkoxy having on each up to 8 carbon atoms, or represent a straight or branched chain alkyl chain having up to 10 carbon atoms. carbon atoms, which is optionally interrupted by an oxygen atom and which is optionally mono- or polysubstituted with identical or different substituents selected from the group consisting of trifluoromethyl, trifluoromethoxy, hydroxy, halogen, carboxyl, benzyloxycarbonyl, straight or branched chain alkoxycarbonyl having up to 6 carbon atoms and / or with radicals of the formulas - S03H, - (A) a-NR7R8, -0-CO- NR7'R8 ', -S (0) b -R9, - P (0) (OR10) (OR11), where a and b are the same or different and each represents a number of 0 or 1, 15 A represents a radical CO or S02, R7, R7 ', R8 and R8' are the same or different and each represents hydrogen, or represent cycloalkyl with 3 to 8 carbon atoms, aryl with 6 to 10 carbon atoms, an optionally benzo-condensed, partially unsaturated or saturated heterocycle of 5 to 6 elements, with up to 3 heteroatoms of the group consisting of S, N and O, wherein the Ring systems mentioned above are optionally mono- or polysubstituted by substituents The same or different from the group consisting of straight or branched hydroxy, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, halogen, alkoxy or alkoxycarbonyl having in each case up to 6. carbon atoms or with a group of the formula - (S02) C-NR12R13, in which c represents a number of 0 6 1, R12 and R13 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 5 carbon atoms, or R7, R7 ', R8 and R8' each represents straight or branched chain alkoxy having up to 6 carbon atoms, or represents the alkyl of straight or branched chain having up to 8 carbon atoms which is optionally mono- or polysubstituted with substituents same or different from the group consisting of hydroxy, halogen, aryl having 6 to 10 carbon atoms, alkoxy or straight or branched chain alkoxycarbonyl having in each case up to 6 carbon atoms or with a group of the formula - (CO) d-NR 14 R 15, wherein R 14 and R 15 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, and 20 d represents a number of 0 or 1, or R7 and R8 and / or R7 'and R8' together with the nitrogen atom form a saturated heterocycle of 5 to 7 elements, which can optionally be Containing an additional heteroatom of the group consisting of S or O or a radical of the formula -NR16, wherein R16 represents hydrogen, aryl having 6 to 10 carbon atoms, benzyl, an aromatic or saturated heterocycle of 5 to 7 elements having up to 3 heteroatoms of the group consisting of S, N and 0, which is optionally substituted with methyl, or represents a straight or branched chain alkyl having up to 6 carbon atoms, which is optionally substituted with hydroxyl, R9 represents aryl having 6 to 10 carbon atoms. carbon, or represents straight or branched chain alkyl having up to 4 carbon atoms, R 10 and R 11 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, and / or the above-mentioned alkyl chain under R3 / R4 is optionally substituted with cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or with an optionally benzocondensate, optionally unsaturated, saturated or unsaturated heterocycle, of 5 to 7 elements, which may contain up to 4 heteroatoms of the group consisting of S, N and O or a radial of the formula -NR17, in which 10 R 17 represents hydrogen, hydroxyl, formyl, trifluoromethyl, acyl or straight or branched chain alkoxy having in each case up to 4 carbon atoms , or straight or branched chain alkyl, Having up to 6 carbon atoms, which is optionally mono- or polysubstituted with the same or different substituents selected from the group consisting of hydroxyl and straight-chain alkoxy or Branched having up to 6 carbon atoms, and wherein the aryl and the heterocycle are optionally mono- or polysubstituted, with the same or different substituents, selected from the group consisting of nitro, halogen, -S03H, alkyl or straight or branched chain alkoxy each having up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy and / or with a radical of the formula -S02NR18R19, in wherein R18 and R19 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 6 carbon atoms, and / or R3 or R4 represents a group of the formula -NR20R21, wherein R20 and R21 they have the aforementioned meaning of R18 and R19 and are the same or different from these, and / or R3 or R4 represent adamantyl, or represent the radicals of the formula or represents cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or represents an optionally benzocondensate, partially unsaturated, saturated or unsaturated heterocycle of 5 to 7 elements, which may contain up to 4 heteroatoms of the group consisting of of S, N and O, or a radical of the formula -NR22, wherein R 22 has the aforementioned meaning ofR, 16 and is the same or different from this, or represents straight or branched chain carboxyl, formyl or acyl having up to 5 carbon atoms, and wherein the cycloalkyl, aryl and / or heterocycle are optionally mono- or polysubstituted with substituents identical or different with the group consisting of halogen, triazolyl, trifluoromethyl, trifluoromethoxy, carboxyl, acyl or straight or branched chain alkoxycarbonyl each having up to 6 carbon atoms, nitro and / or with groups of the formula S03H, - OR23, (S02) CNR24R25, -P (0) (OR26) (OR27), in which e represents a number of 0 or 1, R represents a radical of the formula represents cycloalkyl having 3 to 7 carbon atoms, or represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, which is optionally substituted with cycloalkyl having 3 to 7 carbon atoms, benzyloxy, tetrahydropyranyl, tetrahydrofuranyl, straight chain or branched alkoxy or alkoxycarbonyl each having up to 6 carbon, carboxyl, benzyloxycarbonyl or phenyl atoms, which in turn may be mono- or polysubstituted, by the same or different substituents, selected from the group consisting of straight or branched chain having up to 4 carbon, hydroxyl and halogen atoms, and / or alkyl is optionally substituted with radicals of formulas -CO-NR8R29 or -C0-R3r, wherein R28 and R29 are the same or different and represent each hydrogen or straight or branched chain alkyl with up to 8 carbon atoms, or R and R together with the nitrogen atom form a saturated heterocycle of 5-7 elements which optionally can contain an additional heteroatom of the group consisting of S and O, and R30 represents phenyl or adamantyl, R24 and R25 have the above-mentioned meaning of R18 and R19 and are the same or different from these, R26 and R27 have the aforementioned meaning of R10 and R11 and are the same or different from these and / or cycloalkyl, aryl and / or heterocycle are optionally substituted with straight chain alkyl or branched having up to 6 carbon atoms, which are optionally substituted with hydroxyl, carboxyl, with a heterocycle of 5 to 7 elements having up to 3 heteroatoms of the group consisting of S, N and 0, or with the groups of the formula S0 £ -R31, P (0) (OR32) (OR33) or -NR34R35, where R31 represents hydrogen or has the same meaning as quoted above of R "and is the same or different from this, R3Z and R33 have the meaning above cited from R 10 and R11 and are the same or different from these, R34 and R35 are the same or different and represent hydrogen or straight or branched chain alkyl having up to 6 carbon atoms, which is optionally substituted with hydroxyl or straight or branched chain alkoxy which has up to 4 carbon atoms, or R34 and R35 together with the nitrogen atom form a saturated heterocycle of 5 to 6 elements which may contain an additional heteroatom of the group consisting of S and O, or a radial of the formula -NR36, wherein R36 represents hydrogen, hydroxyl, straight or branched chain alkoxycarbonyl having up to 7 carbon atoms or straight or branched chain alkyl having up to 5 carbon atoms, which is optionally substituted with hydroxyl, R and R together with the nitrogen atom form an optionally unsaturated or saturated or partially unsaturated benzocondensate heterocycle of 5 to 7 elements, which may optionally contain up to 3 heteroatoms of the group consisting of S, N and O, or a radical of the formula -NRj7, wherein R 37 represents straight-chain hydrogen, hydroxyl, formyl, trifluoromethyl, acyl, alkoxy or alkoxycarbonyl or Branched, in each case with up to 4 carbon atoms, or represents straight or branched chain alkyl having up to 6 carbon atoms, which is optionally mono- or is polysubstituted with substituents which are the same or different from the group consisting of straight-chain or branched hydroxyl, trifluoromethyl, carboxyl, alkoxy or alkoxycarbonyl in each case with up to 6. carbon atoms, or with groups of the formula - (D) f_NR38R39, -CO- (CH) g-0-CO-R, 40, -CO- (CH2) h-OR41 or -P (O) - ( OR42) (OR43), where g and h are the same or different and each represents a number of 1, 2, 3, or 4, and f represents a number of 0 or 1, D represents a group of the formula -CO or - S02, R 38 and R39 are the same or different and each one have the aforementioned meaning of R7 and RB, R40 represents straight or branched chain alkyl having up to 6 carbon atoms, R1 represents straight or branched chain alkyl having up to 6 carbon atoms, R * and R43 they are the same or different and each one represents hydrogen or chain alkyl linear or branched that has up to 4 carbon atoms, R 37 represents a radical of the formula - (COK-E, in which 25 i represents a number of 0 or 1, E represents cycloalkyl having 3 to 7 carbon atoms or benzyl, represents aryl having 6 to 10 carbon atoms to an aromatic heterocycle of 5 to 6 elements having up to 4 heteroatoms from the group consisting of S, N and 0, wherein the aforementioned ring systems are optionally mono- or polysubstituted with the same or different constituents, selected from the group consisting of of nitro, halogen, -S03H, straight or branched chain alkoxy having up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy, or with a radical of the formula -S02-NR4R45, wherein R44 and R45 have the above meaning cited from R18 and R19 and are the same or different from these, - or E represents the radicals of the formulas H and the heterocycle quoted under R3 and R4, which is formed together with the nitrogen atom, is optionally mono- or polysubstituted, with the same or different substituents, selected from the group consisting of straight chain hydroxyl, formyl, carboxyl, acyl or alkoxycarbonyl or branched it has in each case to 6 carbon atoms, nitro and groups of the formulas -P (0) (0R ">) (OR, 4" 7,) Wherein R46 and R47 have the above meaning of R10 and R11 and are the same or different from these, R48 represents hydroxyl or straight or branched chain alkoxy having up to 4 carbon atoms, j represents 0 or 1, and R49 and R50 are the same or different and have the above-indicated meaning of R 4 and R 15, and / or the heterocycle mentioned under R 3 and R 4, which is formed together with the atom of nitrogen, which is optionally substituted with straight or branched chain alkyl having up to 6 carbon atoms, which is optionally mono- or polysubstituted with the same or different substituents selected from the group consisting of hydroxyl, halogen, carboxyl, cycloalkyl or cycloalkoxy each having 3 to 8 carbon atoms, Or straight chain or branched alkoxycarbonyl in each case up to 6 carbon atoms, or with a radical of the formulas - S03H, -NR51R52 or P (O) OR53OR54, in which R51 and R53 are the same or different and each one represents hydrogen, phenyl, carboxyl, benzyl or straight or branched chain alkyl or alkoxy each having up to 6 carbon atoms, R53 and R54 are the same or different and have the aforementioned meaning of R10 and R11, and / or the alkyl is optionally substituted with aryl having 6 to 10 carbon atoms, which in turn may be mono- or polysubstituted, with the same or different substituents, from the group consisting of halogen, hydroxyl, chain alkoxy Linear or branched having up to 6 carbon atoms, or with a group of the formula -NR51'R52 ', in which R51' and R52 'have the aforementioned meaning above of R51 and R53 and are the same or different from these, and / or the heterocycle mentioned under R3 and R4, which is formed together with the nitrogen atom, is optionally substituted with aryl having 6 to 10 carbon atoms or with a saturated, partially unsaturated or unsaturated heterocycle of 5 to 7 elements having up to 3 heteroatoms from the group consisting of S, N and O, Optionally also linked by a nitrogen function, wherein the ring systems in turn may be substituted with hydroxyl or with straight or branched chain alkyl or alkoxy, each having up to 6 carbon atoms, or R3 and R4 together with the nitrogen atom form radicals of the formulas R5 and R6 are the same or different and each represents hydrogen, straight or branched chain alkyl, having up to 6 carbon atoms, hydroxyl or straight or branched chain alkoxy having up to 6 carbon atoms, and their salts, hydrates, N-oxides and isomeric forms, The compounds according to the invention can exist in stereoisomeric forms, which are related either as image and image to the mirror (enantiomers), or which are not related as image and image to the mirror (diastereomers). The invention relates both to the enantiomers or diastereomers and to their corresponding mixtures. The racemic forms can be separated equally as the diastereomers in known manner in the stereoisomerically pure components. The substances according to the invention can also be present as salts. In the context of the invention, physiologically acceptable salts are preferred. The physiologically acceptable salts can be salts of the compounds according to the invention with inorganic or organic acids. Salts with inorganic acids, such as hydrochloric acid, hydrobromic acid, phosphoric acid or sulfuric acid or salts with carboxylic or sulphonic acids, such as acetic acid, maleic acid, fumaric acid, are preferred. , malic acid, citric acid, tartaric acid, lactic acid, benzoic acid or methanesulfonic acid, ethanesulfonic acid, phenylsulfonic acid, toluenesulfonic acid or naphthalenedisulfonic acid. The physiologically acceptable salts can also be metal or ammonium salts of the compounds according to the invention. Particularly preferred, for example, are sodium, potassium, magnesium or calcium salts, as well as ammonium salts derived from ammonia or organic amines, such as, for example, ethylamine, di- or triethylamine, di- or triethanolamine, dicyclohexylamine, dimethylaminoethanol, arginine. , lysine, ethylenediamine or 2-phenylethylamine. A heterocycle, optionally benzocondensate, generally represented in the context of the invention is a saturated, partially unsaturated or unsaturated heterocycle of 5 to 7 elements which can contain up to 4 heteroatoms of the group consisting of S, N and O. For example, azepine, diazepine, indolyl, isoquinolyl, quinolyl, benzo [b] thiophene, benzo [b] furanyl, pyridyl, thienyl, tetrahydrofuranyl, tetrahydropyranyl, furyl, pyrrolyl, thiazolyl, triazolyl, tetrazolyl, isoxazolyl, imidazolyl, morpholinyl, thiomorpholinyl, pyrrolidinyl, piperazinyl, N-methylpiperazinyl or piperidinyl. Quinolyl, furyl, pyridyl, thienyl, piperidinyl, pyrrolidinyl, piperazinyl, azepine, diazepine, thiazolyl, triazolyl, tetrazolyl, tetrahydrofuranyl, tetrahydropyranyl, morpholinyl and thiomorpholinyl are preferred. A straight or branched chain acyl radical having 1 to 6 carbon atoms, represented in the context of the invention, for example, acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, butylcarbonyl, isobutylcarbonyl, pentylcarbonyl and hexylcarbonyl. A straight or branched chain acyl radical having 1 to 4 carbon atoms is preferred. Acetyl and ethylcarbonyl are particularly preferred. A straight or branched chain alkoxy radical having 1 to 6 or 1 to 4 carbon atoms represented in the context of the invention methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, n-pentoxy and n-hexoxy. A straight or branched chain alkoxy radical with 1 to 6, 1 to 4 or 1 to 3 carbon atoms is preferred. A straight or branched chain alkoxy radical having 1 to 3 carbon atoms is particularly preferred. A straight or branched chain alkoxycarbonyl radical having 1 to 6 carbon atoms represented in the context of the invention, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonyl. A straight or branched chain alkoxycarbonyl radical having 1 to 4 carbon atoms is preferred. A straight or branched chain alkoxycarbonyl radical with 1 to 3 carbon atoms is particularly preferred. A straight or branched chain alkyl radical having 4, 6, or 10 carbon atoms represented in the context of the invention, for example, methyl, ethyl, n-propyl, isopropyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl. Preferred are straight or branched chain alkyl radicals having 1 to 3, 1 to 4 or 1 to 8 carbon atoms. Alkyl radicals of 1 to 4 or 1 to 3 carbon atoms are particularly preferred. Linear alkyl having up to 4 carbon atoms represented in the context of the invention, for example, methyl, ethyl, n-propyl and n-butyl. Aryl (Cd-Cio), represents, generally, an aromatic radical of 6 to 10 carbon atoms. The aryl, phenyl and naphthyl radicals are preferred.

Cycloalkyl having 3 to 8 or 3 to 7 carbon atoms represented in the context of the invention, for example, cyclopropyl, cyclopentyl, cyclobutyl, cyclohexyl, cycloheptyl or cyclooctyl. Preferred are: cyclopropyl, cyclopentyl and cyclohexyl. The cycloalkyloxy having 3 to 8 carbon atoms represented in the context of the invention cyclopropyloxy, cyclopentyloxy, cyclobutyloxy, cyclohexyloxy, cycloheptyloxy or cyclooctyloxy. Preferred are: cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. The halogen represented in the context of the invention, in general, fluorine, chlorine, bromine and iodine. Fluorine, chlorine and bromine are preferred. Fluorine and chlorine are particularly preferred. A saturated heterocycle of 5 to 6 elements or 7 elements, which may contain an additional heteroatom of the group consisting of S, N and O, represented in the context of the invention and depending on the aforementioned substituents, for example, morpholinyl, piperidinyl , piperazinyl, tetrahydropyranyl or tetrahydrofuranyl. Morpholinyl, tetrahydropyranyl, piperidinyl and piperazinyl are preferred.

An aromatic heterocycle of 5 to 6 elements having up to 3 or 4 heteroatoms from the group consisting of S, N and O, represented in the context of the invention, for example, pyridyl, pyrimidyl, pyridazinyl, thienyl, furyl, pyrrolyl, thiazolyl , oxazolyl or imidazolyl. Pyridyl, pyrimidyl, pyridazinyl, furyl and thiazolyl are preferred. An unsaturated, partially unsaturated or saturated heterocycle of 5 to 6 elements, may contain up to 3 or 4 heteroatoms of the group consisting of S, N and O, represented in the context of the invention, for example, pyridyl, pyrimidyl, pyridazinyl, thienyl, furyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, piperidinyl, piperazinyl or morpholinyl. Preferred are pyridyl, pyrimidyl, piperazinyl, pyridazinyl, morpholinyl, furyl and thiazolyl. The compounds according to the invention, in particular the salts, can also be present as hydrates. In the context of the invention, hydrates are understood as those compounds that contain water in their crystals. Such compounds may contain one or more, usually 1 to 5, equivalents of water. The hydrates can be prepared, for example, by crystallizing the corresponding compound in water or in the form of an aqueous solvent. Preferred are compounds according to the invention of the general formula (I) in which R 1 represents straight or branched chain alkyl having up to 3 carbon atoms, R 2 represents straight chain alkyl having up to 3 carbon atoms, R 3 and R4 are the same or different and each represents hydrogen or represents alkenyl or straight or branched chain alkoxy having in each up to 6 carbon atoms, or _ represents a straight or branched chain alkyl chain having up to 8 carbon atoms , which is optionally interrupted by an oxygen atom and which is optionally mono- or polysubstituted with identical or different substituents selected from the group consisting of hydroxyl, fluoro, chloro, carboxyl, benzyloxycarbonyl, straight-chain or branched alkoxycarbonyl having up to 5 atoms of carbon and / or radicals of the formulas -S03H, - (A) to -NR R8, -0-CO- NR 'Rc -S (O) -R- -P (O) (OR 1? 0?, ) (OR where a and b are the same or different and each one represents a number of 0 6 1, A represents a radical CO or S02, R7, R7 ', R8 and R8' are the same or different and each represents hydrogen, or cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, Phenyl, piperidinyl and pyridyl, wherein the aforementioned ring systems are optionally mono- or tri-substituted by substituents same or different from the group consisting of hydroxyl, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, fluorine, chlorine, alkoxy or chain alkoxycarbonyl linear or branched which in each case has up to 4 carbon atoms, or with a group of the formula - (S02) C-NR12R13, in which c represents a number of 0 or 1, R12 and R13 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, or R7, R7 ', R8 and R8' each represents straight or branched chain alkoxy having up to 3 carbon atoms, or represents the straight or branched chain alkyl having up to 7 carbon atoms Carbon that is optionally mono- or polysubstituted with substituents which are the same as or different from the group consisting of hydroxyl, fluoro, chloro, phenyl, alkoxy or straight-chain alkoxycarbonyl - or Branched having in each case up to 4 carbon atoms, or with a group of the formula - (CO) d-NR 14 R 15, wherein R 14 and R 15 are the same or different and each represents hydrogen or straight or branched chain alkyl that has up to 3 carbon atoms, d represents a number of 0 or 1, 10 or R7 and R8 and / or R7 'and R8' together with the nitrogen atom form a pyrrolidinyl, morpholinyl, piperidinyl or a triazolyl ring or radicals of the formulas Wherein R 16 represents hydrogen, phenyl, benzyl, morpholinyl, pyrrolinyl, piperidinyl, piperazinyl or N-methylpiperazinyl, or represents a straight or branched chain alkyl having up to 5 carbon atoms, which is optionally substituted with hydroxyl, R " represents straight or branched chain alkyl of up to 3 carbon atoms, Ra and R11 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, and / or the alkyl chain above cited under R 3 / R 4 is optionally substituted with cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, pyridyl, quinolyl, pyrrolidinyl, pyrimidyl, morpholinyl, furyl, piperidinyl, tetrahydrofuranyl or with radicals of the formula, wherein R17 represents hydrogen, hydroxyl, formyl, trifluoromethyl, acyl or straight or branched chain alkoxy having in each case up to 3 carbon atoms, or represents linear or branched chain alkyl, having up to 4 carbon atoms, which is optionally mono- or tri-substituted with the same substituents or Different selected from the group consisting of hydroxyl and straight or branched chain alkoxy having up to 4 carbon atoms, and wherein the phenyl and the heterocycle are Optionally mono- or trisubstituted, with the same or different substituents, selected from the group consisting of nitro, fluoro, chloro, -S03H, alkyl or straight or branched chain alkoxy having Each case up to 4 carbon atoms, hydroxyl, and / or with a radical of the formula - S02NR18R19, in which R18 and R19 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, and / or R3 or R4 represents a group of the formula wherein R20 and R21 have the above-mentioned meaning of R18 and R19 and are the same or different these, and / or R3 or R4 represent adamantyl, or represent the radicals of the formula or represents cyclopentyl, cyclohexyl, cycloheptyl, phenyl, morpholinyl, oxazolyl, thiazolyl, quinolyl, isoxazolyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl or represents radicals of the formulas in which R22 has the aforementioned meaning of R 1 6 and is the same or different from this, or represents straight or branched chain carboxyl, formyl or acyl having up to 3 carbon atoms, and wherein the cycloalkyl, the phenyl and / or the heterocycles are optionally mono- or trisubstituted, with substituents identical or different, selected from the group consisting of fluoro, chloro, triazolyl, trifluoromethyl, trifluoromethoxy, carboxyl, acyl or straight or branched chain alkoxycarbonyl each having up to 5 carbon atoms, nitro and / or with groups of the formulas S03H, -OR23, (S02) .NR24R25, -P (0) (OR26) (OR2!, In which e represents a number 0 or 1,, 23 represents a radical of the formula represents cyclopropyl, cyclopentyl, cyclobutyl, cyclohexyl or cycloheptyl, represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, which may be optionally substituted by cyclopropyl, cyclopentyl, cyclohexyl, benzyloxy, tetrahydropyranyl, straight or branched chain tetrahydrofuranyl, alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, benzyloxycarbonyl or phenyl, which in turn may be mono- or polysubstituted, with the same or different substituents selected from the group consisting of alkoxy straight or branched chain having up to 3 carbon atoms, hydroxyl, fluorine or chlorine, and / or wherein the alkyl is, optionally substituted with radicals of the formulas -CO- NR28R29 or -CO-R30, wherein R 28 and R are the same or different and each represent hydrogen or straight or branched chain alkyl having up to 5 carbon atoms, or R28 and R29 together with the nitrogen atom form a morpholinyl, pyrrolidinyl or piperidinyl ring, and R30 represents phenyl or adamantyl, R 24 and R25 have the meaning cited above of R18 and R19 and are the same or different from these, R1 and R27 have the aforementioned meaning of R10 and R11 and are the same or different from these and / or cycloalkyl, phenyl and / or the heterocycles are optionally substituted with straight or branched chain alkyl having up to 4 carbon atoms, which is optionally substituted with hydroxyl, carboxyl, pyridyl, pyrimidyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, triazolyl or with groups of the formulas -S02-R, -P (O) (OR, 3J2.) (0R, 333J) and NR34R35, in where R has the above-mentioned meaning of R 'is the same or different from this, R 32 and R33 have the aforementioned meaning of R 10 and R 11 and are the same or different from these, R 34 and R "are the same and each represent hydrogen or straight or branched chain alkyl having up to 5 carbon atoms, which is optionally substituted by hydroxy or straight or branched chain alkoxy having up to 3 carbon atoms, or R 34 and R 35 together with the nitrogen atom form a morpholinyl, triazolyl or thiomorpholinyl ring or a radical of formula wherein R36 represents hydrogen, hydroxyl, straight or branched chain alkoxycarbonyl with up to 5 carbon atoms or straight or branched chain alkyl having up to 4 carbon atoms, which is optionally substituted with hydroxyl, or R3 and R4 together with the Nitrogen atom forms a morpholinyl, thiomorpholinyl, pyrrolidinyl, piperidinyl ring or a radical of the formula wherein R represents hydrogen, hydroxyl, formyl, trifluoromethyl, acyl, alkoxy or straight or branched chain alkoxycarbonyl, each having up to 4 carbon atoms, or represents straight or branched chain alkyl having up to 5 carbon atoms , which is optionally mono- or trisubstituted, with the same or different substituents selected from the group consisting of hydroxyl, trifluoromethyl, carboxyl, alkoxy or straight or branched chain alkoxycarbonyl each having up to 4 carbon atoms, or with groups of the formula - (D) £ _NR38R39, -C0- (CH2) g-0-CO-R 4"0 -CO- (CH2) h-OR 41 P (O) (OR4 ') (OR, 43. where g and h are the same or different and represent a number 1, 2, or 3, and f represents a number 0 or 1, D represents a group of the formula -CO or -10 S02, R38 and R39 are the same or different and have the same meaning of R7 and R8 cited above, R40 represents straight chain alkyl or Branched having up to 4 carbon atoms, R41 represents straight or branched chain alkyl having up to 4 carbon atoms, R42 and R43 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 3 carbon atoms. carbon atoms, , 37 represents a radical of the formula - (CO) j.-E, in which i is a number 0 or 1, E represents cyclopentyl, cyclohexyl, cycloheptyl, benzyl, phenyl, pyridyl, pyrimidyl or furyl, wherein the systems of the aforementioned ring are optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of nitro, fluoro, chloro, -S03H, straight or branched chain alkoxy having up to 4 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy with a radical of the formula -S02-NR44R45, wherein R44 and R45 have the above-mentioned meaning of R18 and R19 and are the same or different from these, or E represents radicals of the formulas - ?? -CH, and the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally mono- or trisubstituted, with the same or different substituents, optionally also geminally, selected from the group consists of hydroxyl, formyl, carboxyl, acyl or straight-chain or branched alkoxycarbonyl in each case with up to 5 carbon atoms, nitro and groups of the formulas -P (O) (OR46) (OR47), where R46 and R47 have the meaning above of R10 and R11 and are the same or different from these, R represents hydroxy or straight or branched chain alkoxy having up to 3 carbon atoms, j is a number 0 or 1, and R49 and R50 are the same or different and have the above-indicated meaning of R14 and R15, and / or the heterocycles formed together with the Nitrogen atom, mentioned under R 3 and R 4, are optionally substituted with straight or branched chain alkyl having up to 5 carbon atoms, which are optionally mono- or polysubstituted with the same or different substituents selected from the group consisting of hydroxyl, fluoro, chloro, carboxyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, alkoxy or straight or branched chain alkoxycarbonyl each having up to 4 carbon atoms or with a radical of the formula -S03H, -NR51R52 or -P (O) or R53OR5, in which R51 and R52 are the same or different and each represents hydrogen, phenyl, carboxyl, benzyl or straight or branched chain alkyl or alkoxy in each case with up to 4 carbon atoms, R53 and R54 are the same or different and have the above-mentioned meaning of R10 and R11, and / or alkyl is optionally substituted with phenyl, which in turn may be mono- or trisubstituted, with the same or different substituents, selected from the group consisting of fluorine, chlorine, hydroxyl, chain alkoxy linear or branched having up to 4 carbon atoms, or with a group of the formula -NR51'R52 ', wherein R, 51' and R have the aforementioned meaning above of R51_ and R52 and are the same or different from these, and / or the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally substituted with Phenyl, pyridyl, piperidinyl, pyrrolidinyl or tetrazolyl, optionally also linked by a function, wherein the ring systems in turn can be substituted with hydroxyl or with straight or branched chain alkyl or alkoxy, each having up to 5 carbon atoms. carbon atoms, R3 and R4 together with the nitrogen atom form radicals of the formulas R5 and R6 are the same or different and represent hydrogen, hydroxyl or straight or branched chain alkoxy and each with up to 4 carbon atoms, and their salts, N-oxides, hydrates and isomeric forms. Particularly preferred are the compounds according to the invention of the general formula (I), in which R 1 represents straight or branched chain alkyl having up to 3 carbon atoms, R 2 represents straight chain alkyl having up to 3 carbon atoms , R3 and R4 are the same or different and each represents hydrogen or represents alkenyl or straight or branched chain alkoxy each having up to 4 carbon atoms, or represents a straight or branched chain alkyl chain having up to 6 atoms carbon, which is optionally interrupted with an oxygen atom and which is optionally mono- or trisubstituted, with the same or different substituents, selected from the group consisting of hydroxyl, fluoro, chloro, carboxyl, straight or branched chain alkoxycarbonyl having up to 4 carbon atoms and / or radicals of the formulas -S03H, - (A) to -NR7R8, -0-CO-NR7'Re • S (O) bR ' where a and b are the same or different and each represent a number 0 or 1, A represents a radical CO or S02, R7, R7 ', Rs and R8' are the same or different and each represent hydrogen, or Represent cyclopentyl, cyclohexyl , cycloheptyl, phenyl, piperidinyl and pyridyl, wherein the aforementioned ring systems are optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of hydroxy, nitro, carboxyl, fluoro, chloro, alkoxy or alkoxycarbonyl of straight or branched chain having in each case up to 3 carbon atoms, or with a group of the formula - (S02) c, -NR12R13, where c represents a number 0 or 1, 10 R12 and R13 are the same or different and they represent hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, R, R, R and R each represent methoxy, or represent straight or branched chain alkyl having up to 6 carbon atoms which are optionally mono- or disubstituted, with the same substituents or different, selected from the group consisting of hydroxyl, fluoro, chloro, phenyl, alkoxy or alkoxycarbonyl straight chain or branched in each case up to 3 carbon atoms, or with a group of the Formula - (CO) d-NR 14 R 15, in which R 14 and R 15 are the same or different and each represents hydrogen, methyl or ethyl, and d represents a number 0 or 1, R7 and R8 and / or R7 'and R8' together with the nitrogen atom form a morpholinyl, piperidinyl or triazolyl ring or radicals of the formulas Wherein R16 represents hydrogen, phenyl, benzyl, morpholinyl, pyrrolidinyl, piperidinyl, piperazinyl or N-methylpiperazinyl, or represents straight or branched chain alkyl having up to 3 carbon atoms, which is optionally substituted with hydroxyl, R9 represents methyl , R 10 and R are the same or different and each represents hydrogen, methyl or ethyl, and / or the alkyl chain mentioned under R 3 / R 4 is optionally substituted with Cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, morpholinyl, furyl, tetrahydrofuranyl or with radicals of the formulas fifteen wherein R17 represents hydrogen, hydroxyl, formyl, acetyl or alkoxy having up to 3 atoms carbon, or represents straight or branched chain alkyl, having up to 3 carbon atoms, which is optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of hydroxyl or straight or branched chain alkoxy which has up to 3 carbon atoms, and wherein the phenyl and the heterocycles are optionally mono- or tri-substituted, with the same or different substituents, selected from the group consisting of fluorine, chlorine, -S? 3H, alkyl or straight or branched chain alkoxy having in each case up to 3 carbon atoms, hydroxyl, and / or with a radical of the formula -S02-NR18R19, wherein R18 and R19 are the same or different and each represents hydrogen or straight or branched chain alkyl which has up to 3 carbon atoms, and / or R- R 4 represents a group of the formula -NR 20 R 21, wherein R 20 and R have the above-mentioned meaning of R 1 R 1 and are the same as these, and / or R 3 or R 4 r they represent adamantyl, or represent radicals of the formulas or represent cyclopentyl, cyclohexyl, cycloheptyl, phenyl, morpholinyl, oxazolyl, thiazolyl, quinolyl, isoxazolyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl, or represent radicals of the formulas wherein R2 has the aforementioned meaning of R16 and is the same or different from this, or represents formyl or acetyl, and wherein cycloalkyl, phenyl and / or heterocycles are optionally mono- or disubstituted, with the same or different substituents , selected from the group consisting of fluoro, chloro, triazolyl, carboxyl, acyl or straight or branched chain alkoxycarbonyl having in each case up to 4 carbon atoms, nitro and / or with groups of the formulas - S03H, -OR23, (S02) eNR24R25, -P (0) (OR26) (OR27), in which - _ e represents a number 0 or 1, 15 R33 represents a radical of the formula represent cyclopropyl, cyclopentyl, Cyclobutyl or cyclohexyl, represent hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, which is optionally substituted by cyclopropyl, cyclohexyl, benzyloxy, tetrahydropyranyl, alkoxy or straight or branched chain alkoxycarbonyl each having up to 3 carbon atoms. carbon atoms, benzyloxycarbonyl or phenyl, which in turn may be optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of methoxy, hydroxyl, fluorine or chlorine, and / or wherein the alkyl is optionally substituted with radicals of the formulas -CO- in which R28 and R29 are the same or different and each one represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, or R28 and R29 together with the nitrogen atom form a morpholinyl ring, Pyrrolidinyl or piperidinyl, and R 30 represents phenyl or adamantyl, R 24 and R ~ have the abovementioned meaning of R18 and R19 and are the same or Other than these, R26 and R27 have the above-mentioned meaning of R10 and R11 and are the same or different from these and / or cycloalkyl, phenyl and / or the heterocycles are optionally substituted with straight or branched chain alkyl with up to 3 carbon atoms. carbon, which is optionally substituted with hydroxyl, carboxyl, pyridyl, Pyrimidyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, triazolyl with groups of the formulas -SO2-R31, P (O) (OR32) (OR33) or -NR34R35, in which R31 represents methyl, R32 and R33 have the above-mentioned meaning of R10 R 11 are the same or different from these, R34 and R35 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, which is optionally substituted with hydroxyl or methoxy, or R34 and R together with the nitrogen atom form a morpholinyl, triazolyl or thiomorpholinyl ring or a radical of the formula wherein R36 represents hydrogen, hydroxy, straight or branched chain alkoxycarbonyl having up to 3 carbon atoms or straight or branched chain alkyl having up to 3 carbon atoms, which is optionally substituted with hydroxyl, R together with the nitrogen atom forms a morpholinyl, thiomorpholinyl, pyrrolidinyl, piperidinyl ring or a radical of the formula wherein R represents hydrogen, hydroxyl, formyl, acyl, alkoxy or straight or branched chain alkoxycarbonyl, each having up to 3 carbon atoms, or represents straight or branched chain alkyl having up to 4 carbon atoms, which is optionally mono- or Disubstituted, with the same or different substituents, selected from the group consisting of straight or branched chain alkoxy or alkoxycarbonyl each having up to 3 carbon atoms, or groups of the formulas (D) f_NR38R39, -C0- (CH2) g-0-CO-R 40, -CO- (CH2 • OR4 (O) (OR42); OR43) in which g and h are the same or different and represent a number 1 or 2, and f represents a number 0 or 1, D represents a group of the formula -CO or -so2, R38 and R39 are the same or different and have the above-mentioned meaning of R7 and R8, R represents straight chain branched alkyl having up to 3 carbon atoms, R 41 represents straight or branched chain alkyl having up to 3 carbon atoms, R 10 and R 43 are the same or different and represent hydrogen, methyl or ethyl, R 37 represents a radical of the formula - (COK-E, in which i is a number 0 or 1, E represents cyclopentyl, benzyl, phenyl, pyridyl, pyrimidyl or furyl, where the ring systems The aforesaid are optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of nitro, fluoro, chloro, -SO3H, alkoxy, Linear or branched chain having up to 3 carbon atoms, hydroxyl, or with a radical of the formula -SO; -NR44R45, wherein and Rq have the above-mentioned meaning of R18 and R19 and are the same or different from these, or E represents radicals of formulas 10 And the heterocycles formed together with the nitrogen atom, mentioned under R 3 and R 4, are optionally mono- or tri-substituted, with the same or different substituents, optionally also geminally, selected from the group consisting of hydroxyl, formyl, carboxyl, straight or branched chain alkoxycarbonyl having in each case up to 3 carbon atoms, or groups of the formulas 4 6, P (O)! OR ") (OR4 ') wherein R 4 6 and R have the above-mentioned meaning of R 10 R 11 are the same or different from these, R represents hydroxyl or methoxy, j is a number 0 or 1, and R 4 and R are the same or different and have the aforementioned meaning of R14 and R15, and / or the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally substituted with straight or branched chain alkyl which has up to 4 carbon atoms, which are optionally mono- or trisubstituted, with the same or different substituents, selected from the group consisting of hydroxyl, fluoro, chloro, carboxyl, cyclopropyl, cycloheptyl, alkoxy or straight or branched chain alkoxycarbonyl having in each case up to 3 carbon atoms or with a radical of the formulas -S03H, -NR51R53 or P (O) OR5 OR54, in which R51 and R52 are the same or different and each represents hydrogen, phenyl, carboxyl, benzyl or alkyl_ or alkoxy of straight or branched chain having in each case up to 3 carbon atoms, R53 and R54 are the same or different and have the aforementioned meaning of R10 and R11, and / or the alkyl is optionally substituted with phenyl, which at its may optionally be mono- or disubstituted, with the same or different substituents, selected from the group consisting of Fluorine, chlorine, hydroxyl, methoxy or with a group of the formula -NR51'R52 ', wherein, 51' and R- have the same meaning cited above of R51 and R52 and are identical or different from these, and / or the heterocycles formed together with the nitrogen atom, mentioned under R 3 and R 4, which are optionally substituted with phenyl, pyridyl, piperidinyl, pyrrolidinyl or tetrazolyl, are also suitable for joining by a function , wherein the ring systems in turn can be substituted with hydroxyl or with straight or branched chain alkyl or alkoxy, which in each case has up to 3 carbon atoms, R3 and R4 together with the nitrogen atom form radicals of the formulas R5 and R6 are the same or different and represent hydrogen, hydroxyl or represent straight or branched chain alkoxy having up to 3 carbon atoms, and their salts, N-oxides, hydrates and isomeric forms. Very particularly preferred are the compounds of the invention of general formula (I), in which R1 represents methyl or ethyl, R2 represents ethyl or propyl, RJ and R4 are the same or different and each represents a straight-chain alkyl chain or branched having up to 5 carbon atoms, which optionally is substituted up to twice with identical or different substituents, selected from the group consisting of hydroxyl or methoxy, or R4 together with the nitrogen atom form a piperidinyl, morpholinyl, thiomorpholinyl ring or a radical of the formula wherein Rjl represents hydrogen, formyl, acyl or straight or branched chain alkoxycarbonyl, which in each case has up to 3 carbon atoms, or represents straight or branched chain alkyl with up to 3 carbon atoms which optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of hydroxyl, carboxyl, alkoxy or straight-chain or branched alkoxycarbonyl having in each case up to 3 carbon atoms or with groups of the formulas - (D) f_R38R39 or -P (O ) (OR42) (OR43), where f represents a number 0 or 1, D represents a group of the formula -CO, R38 and R39 are the same or different and each represents hydrogen or methyl, R42 and R43 are the same or different and each one represents hydrogen, methyl or ethyl, R 37 represents cyclopentyl, and the heterocycles formed together with the nitrogen atom, mentioned under R 3 and R 4, are optionally mono- or disubstituted, with identical or different substituents, also optionally geminal, selected from the group consisting of straight chain or branched hydroxyl, formyl, carboxyl, acyl or alkoxycarbonyl. having in each case up to 3 carbon atoms or groups of the formulas - P (O) (OR46) (OR47) or - (CO)? NR49R50, in which R46 and R4 ^ are the same or different and each represents hydrogen, methyl or ethyl, j represents a number 0 or 1, and R49 and R50 are the same or different and represent hydrogen or methyl and / or the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally substituted with straight-chain alkyl or branched having up to 3 carbon atoms, which are optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of hydroxyl, carboxyl or with a radical of the formula P (0) 0R530R54, in which R53 and R54 are the same or different and each represents hydrogen, methyl or ethyl, and / or the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally substituted with piperidinyl or pyrrolidinyl attached by nitrogen, RE is hydrogen, and R6 is ethoxy or propoxy, and its salts, hydrates, N-oxides and isomeric forms. Also, very particularly preferred are those compounds according to the invention of general formula (I), in which R 5 represents hydrogen and the radicals Rd and -S02NR 3 R 4 are in a position for one or another phenyl ring. Particularly preferred compounds are those listed in Table A.

Table A: Additionally the invention provides a process for the preparation of the compounds of the general formula (I), according to the invention, characterized in that initially the compounds of the general formula (II) wherein R1 and R2 are as defined above and L represents straight or branched chain alkyl having up to 4 carbon atoms, are converted with compounds of the general formula (III) wherein R5 and R6 are each as defined above, in a two-step reaction, in the ethanol and phosphorus oxychloride / dichloroethane systems, in the compounds of the general formula (IV) (IV) wherein R1, R2, R5 and R6 are as defined above, which are reacted in an additional step with chlorosulfonic acid to give the compounds of the general formula (V) wherein R1, R2, R5 and R6 are each as defined above, which are finally reacted with amines of the general formula (VI) HN3R4 (VI) wherein R3 and R4 are each as defined above. in inert solvent The process according to the invention can be illustrated using the following scheme as an example: Ethanol Phosphorus oxychloride / dichloroethane The solvents that are suitable for the individual steps are the usual organic solvents that do not change under the reaction conditions. These preferably include ethers such as diethyl ether, dioxane, tetrahydrofuran, glycol dimethyl ether or hydrocarbons, such as benzene, toluene, xylene, hexane, cyclohexane or mineral oil fractions, or halogenated hydrocarbons, such as dichloromethane, trichloromethane, carbon tetrachloride, dichloroethane, trichlorethylene or chlorobenzene or ethyl acetate, dimethylformamide, hexamethylphosphoric triamide, acetonitrile, acetone, dimethoxyethane or pyridine. It is also possible to use mixtures of the solvents mentioned above. Particularly preferred for the first stage is ethanol and for the second stage dichloroethane. The reaction temperature can generally vary within a relatively greater range. In general, it can be carried out in the range from -20 ° C to 200 ° C, preferably from 0 ° C to 70 ° C. The steps of the process according to the invention are generally carried out under normal pressure.

However, it is also possible to perform them under high pressure or under reduced pressure (for example, in a range of between 0.5 and 5 bar). The reaction to give the compounds of the general formula (V) is carried out in a temperature range from 0 ° C to room temperature and at normal pressure. The reaction with the amines of the general formula (VI) is carried out in one of the chlorinated hydrocarbons mentioned above, preferably in dichloromethane.

The reaction temperature can generally vary within a relatively greater range. In general, it is carried out at temperatures in a range from -20 ° C to 200 ° C, preferably from 0 ° C to room temperature. The reaction is carried out usually at normal pressure. However, it is also possible to perform it under high pressure or under reduced pressure (for example, in a range from 0.5 to 5 bar). Some compounds of the general formula (II) are known, or are new and can be prepared by converting the compounds of the general formula (VII) R -CO-T (VII) wherein R 2 is as defined above and T represents halogen, preferably chlorine, initially by reacting it with compounds of the general formula (VIII) wherein R1 is as defined above in inert solvents, optionally in the presence of a base and trimethylsilyl chloride, in the compounds of the general formula (IX) wherein R1 and R2 are each as defined above, and finally reacted with the compound of the formula (X) wherein L is as defined above, in inert solvents, optionally in the presence of a base. The solvents for the individual steps are suitable customary organic solvents which do not undergo any modification under reaction conditions. These preferably include ethers such as diethyl ether, dioxane, tetrahydrofuran, glycol dimethyl ether or hydrocarbons, such as benzene, toluene, xylene, hexane, cyclohexane or mineral oil or halogenated hydrocarbon fractions, such as dichloromethane, trichloromethane, carbon tetrachloride, dichloroethylene, trichlorethylene or chlorobenzene. or ethyl acetate, dimethylformamide, hexamethylphosphoric triamide, acetonitrile, acetone, di ethoxyethane or pyridine. It is also possible to use mixtures of the solvents mentioned above. Particularly preferred for the first stage is dichloromethane and for the second stage a mixture of tetrahydrofuran and pyridine. Suitable bases are generally alkali metal hydrides or alkoxides, such as, for example, sodium hydride or potassium tert-butylate or cyclic amines, such as, for example, piperidine, pyridine, dimethylaminopyridine or alkylamines of 1 to 4 carbon atoms, such as example, triethylamine. Triethylamine, pyridine and / or dimethylaminopyridine are preferred. The base e ^ usually uses in an amount from 1 to 4 moles, preferably from 1.2 to 3 moles, in each case based on 1 mole of the compound of the formula (X).

The reaction temperature can vary generally in a relatively larger range. In general, the reaction is carried out in a range from -20 ° C to 200 ° C, preferably from 0 ° C to 100 ° C. The compounds of the general formulas (VII), (VIII), (IX) and (X) are known per se, or are prepared by customary methods. The compounds of the general formula (III) can be prepared by reaction of the compounds of the general formula (XI) wherein R5 and R6 are each as mentioned above with ammonium chloride in toluene and in the presence of trimethylaluminum in hexane in a temperature range from -20 ° C to room temperature, preferably at 0 ° C and normal pressure, and the resulting amine is optionally reacted in situ with hydrazine hydrate.

The compounds of the general formula (XI) are known per se or can be prepared by customary methods. Some of the compounds of the general formula (IV) are partially known or new and can be prepared by known methods [see David R. Marshall, Chemistry and Industry, 2 May 1983, 331-335]. The compounds of the general formula (V) are new per se, but can be prepared from the compounds of the general formula (IV) according to Publication of Organi um, VEB Deutscher Verlag der issenschaften, Berlin 1974, pages 338-339. The compounds according to the invention of the general formula (I) show a spectrum of pharmacologically valuable and unpredictable activity. These inhibit one or more phosphodiesterases that metabolize cGMP (PDE I, PDE II and PDE V). This produces an increase in cGMP. The differentiated expression of the phosphodiesterases in different cells, tissues and organs, as well as the differentiated subcellular localization of these enzymes make it possible, in combination with the selective inhibitors according to the invention, to selectively target the different processes regulated by cGMP.

In addition, the compounds according to the invention reinforce the activity of substances such as EDRF (endothelium-derived relaxant factor), ANP (atrial natriuretic peptide), nitrovasodilators and all other substances that are otherwise different from those of other substances. inhibitors of phosphodiesterases, which increase the concentration of cGMP. Therefore, they can be used in medicines for the treatment of cardiovascular diseases such as for the treatment of hypertension, neuronal hypertension, stable and unstable angina, peripheral and cardial vascular diseases, arrhythmias, for the treatment of thromboembolic diseases and ischemias such as myocardial infarction, cerebral apoplexy, transient and ischemic attacks, angina pectoris, circulation disorders peripheral, impediment of restenosis after thrombolytic therapy, percutaneous transluminal angioplasty (PTA), percutaneous transluminal coronary angioplasty (PTCA) and deviation (bypass). In addition, they may also be important for cerebrovascular diseases. The relaxing action on the smooth muscles makes it suitable for the treatment of diseases of the urogenital system, such as prostatic hypertrophy, incontinence, and in particular for the treatment of erectile dysfunction and female sexual dysfunction.

Phosphodiesterases (PDE) activity The cGMP-stimulated PDE II, the 'PDE III inhibited by cGMP and the specific PDE IV cAMP were isolated from pig or cow myocardium. PDE I stimulated by Ca2 + -calmodulin was isolated from pig aorta, from pig brain or preferably from cow aorta. The PDE V specifies GMPc. it was obtained from the small intestine of the pig, from the pig aorta, from human platelets and preferably from the cow aorta. Purification was performed by anion exchange chromatography on MonoQ® Pharmacia, essentially following the method of M. Hoey and Miles D. Houslay, Biochemical Pharmacology, Vol. 40_, 193-202 (1990) and C. Lugman et al. Biochemical Pharmacology Vol. 35 1743-1751 (1986). The determination of the enzymatic activity is carried out in a 100 ml assay preparation in tris / HCl buffer pH 7.5 containing 5 mM MgCl 2, 0.1 mg / ml of bovine albumin serum and either 800 Bq of [3 H] cAMP or of. [3H] cGMP. The final concentration of the corresponding nucleotides is 10 6 mol / 1 The reaction is initiated by the addition of the enzyme, and the enzymatic quantity is dimensioned such that, during the 30 minute incubation time, approximately 50% of the substrate reacts . To test the cGMP-stimulated PDE II, [3H] cAMP is used as a substrate and 10"6 mol / 1 unlabeled cGMP is added to the mixture.To assay the Ca2 + -dependent PDE I -calmodulin, it is added to the mixture reaction reaction 1 mM CaCl 2 and 0.1 mM calmodulin The reaction is stopped by the addition of 100 ml of acetonitrile, containing 1 mM cAMP and 1 mM AMP, 100 ml are separated from the reaction mixture by HPLC, and the product is quantitatively determined. of "in line" excision with a continuous flow scintillation counter The concentration of the substance at which the reaction rate decreases by 50% is measured. Phosphodiesterase [3H] cAMP-SPA enzime essay "and the" Phosphodiesterase [3H] cGMP-SPA enzime essay "from the company Amersham Life Science The test was carried out according to the manufacturer's test protocol. PDE II was used the [JH] cAMP-SPA trial where it was added to the 10 ~ 6 M cGMP reaction mixture for activation of the enzyme. For measurement of PDE I, 107 M calmodulin and 1 mM CaCl 2 were added to the reaction mixture. PDE V was measured with the [3 H] cGMP-SPA assay.

In principle, the inhibition of one or more phosphodiesterases of this type produces an increase in the concentration of cGMP. In this way, the compounds are interesting for all therapies in which an increase in the concentration of cGMP is considered as curative. The analysis of the cardiovascular actions was carried out in SH rats and in dogs. The substances were administered intravenously or orally.

The analysis of the stimulating action of the erection was performed using awake rabbits [Naganuma H. Egashira T. Fuji J. Clinical and Experimental Pharmacology and Physiology 20, 177-183 (1993)]. The substances were administered intravenously, orally or parenterally. The new active compounds, as well as their physiologically acceptable salts (for example, hydrochlorides, maleates or lactates) can be incorporated in accordance with a known form in the usual pharmaceutical formulations such as tablets, dragees, pills, granules, aerosols, syrups, emulsions, suspensions and solutions, using inert, non-toxic, pharmaceutically acceptable excipients or solvents. In this case, the therapeutically active compound must be present in each case a concentration of approximately 0.5 to 90% by weight of the total mixture, ie, in sufficient quantities to achieve the indicated dosage range. The formulations are prepared for example by spreading the active compounds using solvents and / or excipients, optionally using emulsifiers and / or dispersants, it being possible to use, for example, in case water is used as a diluent, optionally organic solvents as auxiliary solvents. The administration is carried out in a customary manner, preferably orally, transdermally or parenterally, for example, perlingually, buccally, intravenously, nasally, rectally or by inhalation. For human use, in the case of oral administration, it is convenient to practice administering dosages ranging from 0.001 to 50 mg / kg, preferably 0.01 mg / kg-20 mg / kg. In the case of parenteral administration, as for example, through the nasal mucosa, buccally or by inhalation, it is convenient to practice the use of dosages from 0.001 mg / kg - 0.5 mg / kg. However, it may be necessary to optionally vary the amounts mentioned, depending on the body weight or type of route of administration, the individual response to the drug, the type of formulation and the time or interval in which the administration is performed. In this way, in some cases smaller quantities than those mentioned above are sufficient, while in other cases the upper limit mentioned must be exceeded. In the case of the administration of larger quantities, it may be advisable to distribute these in several individual doses throughout the day. The compounds according to the invention are also suitable for use in veterinary medicine. For uses in veterinary medicine, the compounds or their non-toxic salts can be administered in the appropriate formulation in accordance with general veterinary practice. The veterinarian can establish the type of use and dosage according to the type of animal to be treated.

Starting Materials Example IA 2-butyrylaminopropionic acid 22.27 g (250 mmoles) of D, L-alanine and 55.66 g (550 mmoles) of triethylamine were dissolved in 250 ml of dichloromethane and the solution was cooled to 0 ° C. 59.75 g (550 mmoles) were added dropwise. trimethylsilyl chloride and the solution was stirred for 1 hour at room temperature and for one hour at 40 ° C. After cooling to -10 ° C, 26.64 g (250 mmol) of butyryl chloride was added dropwise and the resulting mixture was stirred for 2 hours at -10 ° C and for one hour at room temperature. Upon cooling with ice, 125 ml of water was added dropwise and the reaction mixture was stirred for 15 minutes at room temperature. The aqueous phase was evaporated to dryness, the residue was triturated with acetone and the mother liquor was filtered off with suction. The solvent was removed and the residue chromatographed. The resulting product was dissolved in 3N aqueous sodium hydroxide and the resulting solution was evaporated to dryness. The residue is suspended in concentrated HCl, and evaporated again to dryness. The residue was stirred with acetone, the precipitated solid was separated by filtration with suction and the solvent was removed under reduced pressure. 28.2 g (71%) of a viscous oil are obtained, which after a certain time crystallizes. 200 M H NMR (DMSO-d6): 0.84, t, 3H; 1.22, d, 3H; 1.50, sext., 2H; 2.07, t, 2H; 4.20, quint., 1H; 8.09, d, 1H.

Example 2A 2-Butyrylaminobutyric acid .78 g of 2-aminobutyric acid (250 mmoles) and 55.66 g (550 mmoles) of triethylamine were dissolved in 250 ml of dichloromethane and the solution was cooled to 0 ° C. 59.75 g (550 mmol) of tri-ethylsilyl chloride were added dropwise, and the solution was stirred for 1 hour at room temperature and for 1 hour at 40 ° C. After cooling to -10 ° C, 26.64 g (250 mmol) of butyryl chloride were added dropwise, and the resulting mixture was stirred for 2 hours at -10 ° C and for one hour at room temperature. Upon cooling with ice, 125 ml of water was added dropwise and the reaction mixture was stirred at room temperature for 15 minutes. The organic phase was mixed with aqueous sodium hydroxide and the organic solvent was removed under reduced pressure. After acidification, the precipitated solid is stirred once with water and twice with petroleum ether and dried under reduced pressure at 45 ° C. 29.1 g (67%) of a colorless solid are obtained. RMN-1 !! 200 MHz (DMS0-d6): 0.88, 2t, 6H; 1.51, quad, 2H, 1.65, m, 2H, 2.09, t, 2H, 4.10, m, 1H; 8.01, d, 1H; 12.25, s,, 1H.

Example 3A 2-Ethoxybenzonitrile g (210 mmol) of 2-hydroxybenzonitrile were hydrated overnight with 87 g of potassium carbonate and 34.3 g (314.8 mol) of ethyl bromide in 500 ml of acetone. The solid was filtered, the solvent was removed under reduced pressure and the residue was distilled under reduced pressure. 30.0 g (97%) of a colorless liquid are obtained. RMN-1 !! 200 MHz (DMS0-d6): 1.48, t, 3H; 4.15, quad., 2H; 6.99, dt, 2H; 7.51, dt, 2H.

Example 4 A 2-e Hydrochloride "toxibenzamidine" 21.4 g (400 mmol) of ammonium chloride were suspended in 375 ml of toluene and the suspension was cooled to 0 ° C. 200 ml of a 2M solution of trimethylaluminum in hexane was added dropwise and the mixture was stirred at room temperature until the evolution of gas ceased. After the addition of 29.44 g (200 mmol) of 2-ethoxybenzonitrile, the reaction mixture was stirred overnight at 80 ° C (bath). The cooled reaction mixture was added, by cooling with ice, to a suspension of 100 g of silica gel and 950 ml of chloroform, and the mixture was stirred for 30 minutes at room temperature. The mixture was filtered with suction and the filter residue was washed with the same amount of methanol. The mother liquor was concentrated, the residue obtained was stirred with a mixture of dichloromethane and methanol (9: 1), the solid was filtered with suction and the mother liquor was concentrated. 30.4 g (76%) of a colorless solid are obtained. RMN-1 !! 200 MHz (DMSO-d6): 1.36 t, 3H; 4.12, quad., 2H; 7.10, t, 1H; 7.21, d, 1H; 7.52, m, 2H; 9.30, s, broad, 4H.

Example 5A 2-Propoxybenzonitrile 75 g (630 ml) of 2-hydroxybenzonitrile were heated to reflux overnight with 174 g (1.26 mol) of potassium carbonate and 232.2 g (1.89 mmol) of ethyl bromide in 1 l of acetone. The solid was filtered, the solvent was removed under reduced pressure and the residue was distilled under reduced pressure. Peb: 89 ° C (0.7 mbar) Yield: 95.1 g (93.7%) Eg 6A 2-propoxybenzamidine hydrochloride 21.41 g (400 mmol) of ammonium chloride were suspended in 400 ml of toluene and cooled to 0-5 ° C. 200 ml of a 2 M solution of triethylaluminum in hexane was added dropwise and the mixture was stirred at room temperature until the evolution of gas ceased. After the addition of 32.2 g (200 mmol) of 2-propoxybenzonitrile, the reaction mixture was stirred overnight at 80 ° C (bath). The cooled reaction mixture was added, by cooling with ice, to a suspension of 300 g of silica gel and 2.85 1 of ice-cooled chloroform, and stirred for 30 minutes. The mixture was filtered with suction and the filter residue was washed with the same amount of methanol. The solvent was distilled under reduced pressure, the residue was stirred with 500 ml of a mixture of dichloromethane and methanol (9: 1), the solid was filtered and the mother liquor was concentrated. The residue was stirred with petroleum ether and filtered with suction. 22.3 g (52%) of the product were obtained. NMR - ^ - H (200 MHz, CD30D): 1.05 (3H), 1.85 (sext., 2H); 4.1 (A, 2H); 7.0 - 7.2 (, 2H); 7.5-7.65 (m, 2H).

Example 7A 2-Ethoxy-4-methoxybenzonitrile Reflux 30.0 g (201 mmoles) of 2-hydroxy-4-methoxybenzonitrile with 83.4 g of potassium carbonate (603 mmole) and 32.88 g (301 mmole) of bromine for 18 hours in 550 ml of acetone. After filtration, the solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel (cyclohexane: ethyl acetate = 10: 1): 35.9 g of an oil. Rf = 0.37 (cyclohexane: ethyl acetate = 3: 1) 200 MHz-NMR-NMR (CDCl3): 1.48, t, 3H; 3.85, s, 3H; 4.12 quadr., 2H; 6.46, m, 2H; 7.48, d, 1H.

Example 8A 2-Ethoxy-4-methoxybenzamidine hydrochloride 6.98 g (130 mmol) of ammonium chloride were suspended in 150 ml of toluene, and the suspension was cooled to 0 ° C. 70 ml of a 2M solution of trimethylaluminum in hexane was added dropwise and the mixture was stirred at room temperature until the evolution of gas ceased. After the addition of 11.56 g (65 mmol) of 2-ethoxy-4-methoxy-benzonitrile, the reaction mixture was stirred overnight at 80 ° C (bath). The cooled reaction mixture was added, cooled with ice, to a suspension of 100 g of silica gel and 950 ml of dichloromethane, and the mixture was stirred for 30 minutes at room temperature. The mixture was filtered with suction and the filter residue was washed with the same amount of methanol. The mother liquor was concentrated, the obtained residue was stirred with a mixture of dichloromethane and methanol (9: 1), the solid was filtered with suction and the mother liquor evaporated. The residue was stirred with petroleum ether and filtered. 7.95 g (50%) of a solid were obtained. 200 MHz-NMR-XH (DMSO-d6): 1.36 t, 3H; 3.84, s, 3H; 4.15, quad., 2H; 6.71, m, 2H; 7.53, d, 1H, 8.91, s, broad, 3H.

Example 9A 2- (2-Ethoxyphenyl) -5,7-dimethyl-3yr-imidazo [5, 1-f] [1, 2, 4] triazin-4-one Initially, 24.4 g (0.816 mol) of γ-acetyl-D, L-alanine were charged in 200 ml of absolute tetrahydrofuran and 45 ml of absolute pyridine and 0.5 g of 4-dimethylaminopyridine were added. The mixture was heated to reflux, and 51.85 g (0.372 mol) of oxalyl ester chloride was added dropwise. The mixture was heated for a further 90 minutes at reflux, cooled, poured into ice water, extracted three times with ethyl acetate. The organic phase was dried over sodium sulfate, concentrated and suspended in 62.5 ml of methanol. 9 g of sodium bicarbonate was added, and the mixture was stirred for 2.5 hours under reflux and filtered. To a solution of 38.26 g (190.65 mmol) of 2-ethoxy-4-methoxybenzamidine hydrochloride in 250 ml of methanol was added dropwise, cooling with ice, 9.54 g (190.65 mmol) of hydrazine hydrate, and the resulting suspension was stirred another 30 minutes at room temperature. To this reaction mixture was added the methanolic solution described above, and stirred 4 hours at 70 ° C bath temperature. After filtration, the mixture was concentrated, the residue was partitioned between dichloromethane and water, the organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was suspended in 250 ml of 1,2-dichloroethane, 32.1 ml (348 mmol) of phosphorus oxychloride was added dropwise and the mixture was heated under reflux for two hours. The mixture was cooled, concentrated, suspended in a little methylene chloride and mixed with diethyl ether and the solid filtered with suction. After chromatography on silica gel (methylene chloride / methanol 95: 5), the solution was concentrated and the crystalline residue was stirred with diethyl ether. Yield: 8.1 g (14.9% of theoretical) NMR-1! 200 MHz (CDC1¿): 1.58, t, 3H; 2.62, s, 3H; 2.68 s, 3H;, 4".25, quadr., 2H; 7.04, d, 1H; 7.12, t, 1H; 7.5, dt, 1H; 8.19, dd, 1H; 10.02, s, 1H.

Example 10A 2- (2-Ethoxy-f-enyl) -5-methyl-7-propyl-3H-imidazo [5, 1-f] [1, 2, 4] triazin-4-one 7.16 g (45 mmol) of 2-butyrylamino-propionic acid are dissolved with 10.67 g of pyridine in 45 ml of THF and then a spatula tip of DMAP is added, heated to reflux. 12.29 g (90 mmol) of oxalic acid ethyl ester chloride was added dropwise, and the reaction mixture was refluxed for 3 hours. The mixture was poured into ice water and extracted three times with ethyl acetate and the organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. The residue was suspended in 15 ml of ethanol and heated to reflux with 2.15 g of sodium bicarbonate for 2.5 hours. The cooled solution was filtered. To a solution of 9.03 g (45 mmol) of 2-ethoxybenzamidine hydrochloride in 45 ml of ethanol was added dropwise, cooled with ice, 2.25 g (45 mmol) of hydrazine hydrate and the resulting suspension was stirred for another 10 minutes. at room temperature. To this reaction mixture was added the above-described ethanolic solution and the mixture was stirred for 4 hours at a bath temperature of 70 ° C. After filtration, the mixture was concentrated, the residue was partitioned between dichloromethane and water, the organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. This residue was dissolved in 60 ml of 1,2-dichloroethane and, after 7.5 ml of phosphorus oxychloride was added, it was heated to reflux for 2 hours. The mixture was diluted with dichloromethane and neutralized by the addition of a solution of sodium bicarbonate and solid sodium bicarbonate. The organic phase was dried and the solvent was removed under reduced pressure. Chromatography was used with ethyl acetate and crystallization gave 4.00 g (28%) of a colorless solid, Rf = 0.42 (dichloromethane / methanol = 95: 5) RMN-1! 200 MHz (CDC13): 1.02, t, 3H; 1.56, t, 3H; 1.89, sext., 2H; 2.67, s, 3H; 3.00, t, 2H; 4.26 quadr., 2H; 7.05, m, 2H; 7.50, dt, 1H; 8.17, dd, 1H; 10.00, s, 1H.

Example HA 2- (2-propoxy-f-enyl) -5-methyl-7-propyl-3-yl-imidazo [5, 1-f] [1,2, 4] triazin-4-one 7.16 g (45 mmol) of 2-butyrylaminopropionic acid and 10.67 g of pyridine were dissolved in 45 ml of tetrahydrofuran and, after the addition of the tip of a dimethylaminopyridine spatula, it was heated to reflux. 12.29 g (90 mmol) of oxalic acid ethyl chloride were slowly added dropwise and the reaction mixture was heated to reflux for 3 hours. The mixture was poured into ice water, extracted three times with ethyl acetate, and the organic phase was dried over sodium sulfate and concentrated using a rotary evaporator. The residue was suspended in 15 ml of ethanol and 2.15 g of sodium bicarbonate was heated at reflux for 2.5 hours. The cooled solution was filtered. To a solution of 9.66 g (45 mmol) of 2-propoxybenzamidine hydrochloride in 45 ml of ethanol, 2.25 g (45 mmol) of hydrazine hydrate was added dropwise, cooled with ice, and the resulting suspension was stirred. 10 minutes at room temperature. To this reaction mixture, the above-described ethanolic solution was added and stirred for 4 hours at a bath temperature of 70 ° C. After filtration, the mixture was concentrated, the residue was partitioned between dichloromethane and water, the organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. This residue was dissolved in 60 ml of 1,2-dichloroethane and then 7.5 ml of phosphorus oxychloride was added, and the mixture was refluxed for 2 hours. The mixture was diluted with dichloromethane and by the addition of a solution of sodium bicarbonate and solid sodium bicarbonate was neutralized. The organic phase was dried and the solvent was removed under reduced pressure. Crystallization of ethyl acetate gives 2.85 g (19.18) of a yellow solid, the chromatographic purification of the mother liquor gives an additional 1.25 g (8.4%) of the product Rf = 0.45 (dichloroethane / methanol = 95: 5) NMR- 1!! 200 MHz (CDC13): 1.03, t, 3H; 1.15, t, 3H; 1.92, m, 4H; 2.67, s, 3H; 3.01, t, 2H; 4.17, t, 2H; 7.09, m, 2H; 7.50, dt, 1H; 8.17, dd, 1H; 10.02, s, 1H.

Example 12A 2- (2-ethoxy-4-methoxyphenyl) -5-methyl-7-propyl-3H-imidazo [5, l-_f] [1,2, 4] triazin-4-one .50 g (34.8 mmol) of 2-butyrylaminopropionic acid were dissolved with 8.19 g of pyridine in 35 ml of tetrahydrofuran and, after the addition of a spatula tip of dimethylaminopyridine, it was heated to reflux. 9.43 g (69 mmol) of oxalic acid ethyl chloride was added dropwise and the reaction mixture was refluxed for 3 hours. the mixture was poured into ice water and the organic phase was extracted three times with ethyl acetate, and dried over sodium sulfate and concentrated using a rotary evaporator. The residue was suspended in 11 ml of methanol and heated to reflux with 1.65 g of sodium bicarbonate for 2.5 hours. The cooled solution was filtered. To a solution of 7.95 g (34.5 mmol) of 2-ethoxy-4-methoxybenzamidine hydrochloride in 35 ml of ethanol was added dropwise, cooled with ice, 1.73 g (34.5 mmol) of hydrazine hydrate and the resulting suspension was stirred another 30 minutes at room temperature. To this reaction mixture was added the above-described methanolic solution, and the mixture was stirred 4 hours at a bath temperature at 70 ° C. After filtration, the mixture was concentrated, the residue was partitioned between dichloromethane and water, the organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. This residue was dissolved in 46 ml of 1,2-dichloroethane and after the addition of 5.74 ml of phosphorus oxychloride, it was heated to reflux for 2 hours. The mixture was diluted with dichloromethane and neutralized by the addition of a solution of sodium bicarbonate and solid sodium bicarbonate. The organic phase was dried and the solvent was removed under reduced pressure. Chromatography (dichloromethane-methanol = 50: 1) gives 0.31 g (2.5% t) of a solid.

Rf = * 0.46 (dichloromethane methanol = 20: 1) NMR-1! 200 MHz (CDCl 3): 1.03, t, 3H; 1.58, t, 3H; 1.88, m, 2H; 2.62, s, 3H; 2.98, t, 2H; 3.89, s, 3H; 4.25, quad., 2H; 6.54, d, 1H; 6.67, dd, 1H; 8.14, d, 1H; 9.54, s, 1H.

Example 13A 2- (2-ethoxy-phenyl) -5-ethyl-7-propyl-3ff-imidazo [5, lf] [1,2,4] triazin-4-one 29.06 g (167.8 mmol) of 2-butyrylaminopropionic acid and 39.76 g of pyridine were dissolved in 170 ml of tetrahydrofuran and after addition of a spatula tip of dimethylaminopyridine, it was heated to reflux. 45.81 g was slowly added dropwise (335.5 mmol) of oxalic acid ethyl chloride and the reaction mixture was heated to reflux for 3 hours. The mixture was poured into ice water, and extracted three times with ethyl acetate, and the organic phase was dried over sodium sulfate and concentrated using a rotary evaporator. The residue was suspended in 15 ml of methanol and half of the solution was heated to reflux with 7.69 g of sodium bicarbonate for 2.5 hours. The cooled solution was filtered. To a solution of 16.83 g (83.9 mmol) of 2-ethoxybenzamidine hydrochloride in 85 ml of ethanol, 4.20 g (83.9 mmol) of hydrazine hydrate was added dropwise, cooled with ice, and the resulting suspension was stirred further. minutes at room temperature. To this reaction mixture was added the methanolic solution described above, and stirred 4 hours at a bath temperature of 70 ° C. After filtration, the mixture was concentrated, the residue was partitioned between dichloromethane and water, the organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. This residue was dissolved in 112 ml of 1,2-dichloroethane and after the addition of 14 ml of phosphorus oxychloride it was heated to reflux for 2 hours. The mixture was diluted with dichloromethane and neutralized by the addition of a solution of sodium bicarbonate and solid sodium bicarbonate. The organic phase was dried and the solvent was removed under reduced pressure. Chromatography (dichloromethane / methanol = 50: 1) gives 3.69 g (12.4%) of a colorless solid. Rf = 0.46 (dichloromethane methanol = 20: 1) NMR-1! 200 MHz (CDC13): 1.32, t, 3H; 1.57, t, 3H; 1.94, m, 8H; 3.03, quad., 2H; 3.64, quint. , 1 HOUR; 4.27, quadr., 2H; 7.06, d, 1H; 7.12, t, 1H; 7.50, dt, 1H; 8.16, dd, 1H; 9.91, s, 1H.

Example 14A 4-Ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1-f] [1, 2,4] triazin-2-yl) -benzenesulfonyl acid chloride 7.25 g (25.5 mmol) of 2- (2-ethoxyphenyl) -5,7-dimethyl-3i? -imidazo] [5, lf] [1,2,4] -triazin-4-one was initially charged and added, cooled with ice, 26.74 g (0.23 mol) of chlorosulfonic acid. The mixture was stirred overnight at room temperature and poured into ice water, and the crystals were filtered with suction and dried in the desiccator under vacuum.

Yield: 9.5 g (97% of theory) NMR-1! 200 MHz (d6-DMSO): 1.32, t, 3H; 2.63, s, 3H; 2.73, s, 3H; 4.13, c, 2H; 7.15, d, 1H; 7.77, m, 2H; 12 »5 s / 1H.

Example 15A 4-Ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) - Chloride benzenesulfonic 2.00 g (6.4 mmol) of 2- (2-ethoxy-phenyl) -5-methyl-7-propyl-3i-imidazo [5, 1] [1,2,4] -triazin-4-one was added slowly to 3.83 ml of chlorosulfonic acid at 0 ° C. The reaction mixture was stirred at room temperature overnight, and poured into ice water and extracted with dichloromethane. 2.40 g (91%) of a colorless foam is obtained.

RMN-1 !! 200 MHz (CDC1): 1.03, t, 3H; 1.61, t, 2H; 1.92, sext., 2H; 2.67, s, 3H; 3.10, t, 2H; 4.42, quad., 2H; 7.27, t, 1H; 8.20, dd, 1H; 8.67, d, 1H; 10.18, s, 1H.

Example 16A 4-Propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl) - Chloride benzenesulfonic 2.80 g (8.6 mmol) of 2- (2-propoxy-phenyl) -5-methyl-7-propyl-3i-imidazo [5, 1-f] [1, 2, 4] -triazin-4one was slowly added. to 5.13 ml of chlorosulfonic acid at 0 ° C. The reaction mixture was stirred at room temperature overnight, and poured into ice water and extracted with dichloromethane. 3.50 g (96%) of a colorless foam was obtained. Rf = 0.49 (dichloromethane / methanol = 95: 5) RMN-1! 200 MHz (CDC13) • * 1.03, 2t, 6H; 1.95, m, 4H; 2.81, s, 3H; 3.22, t, 2H; 4.11, t, 2H; 7.09, m, 1H; 8.06, dd, 1H; 8.21 m, 1H; 12.0, s, 1H.

Example 17A Chloride of 4-ethoxy-2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1, 2, 4] triazin-2-yl acid ) benzenesulfonic 0.31 g (0.9 mmol) of 2- (2-ethoxy-4-methoxy phenyl) -5-methyl-7-propyl-3i? -imidazo [5,1-f] [1, 2, 4] - was added slowly. triazin-4-one at 0.54 ml of chlorosulfonic acid at 0 ° C. The reaction mixture was stirred at room temperature overnight and then poured into ice water and extracted with dichloromethane. 0.355 g (89%) of a colorless foam was obtained. Rf = 0.50 (dichloromethane / methane = 20: 1) 200 MHz-NMR-NMR (CDC1): 1.05, t, 3H; 1.66 t, 3H; 1.95, m, 2H; 2.61, s, 3H; 3.11 t, 2H; 4.15 s, 3H; 4.40 quadr., 2H; 6.65 s, 1H; 8.72, s, 1H; 9.75, s, 1H.

Example 18A 4-Ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydroxy-idazo [5, 1-f] [1,2,4] triazin-2-yl) -benzenesulfonic acid chloride 1.70 g (5.21 mmol) of 2- (2-ethoxy-phenyl) -5-ethyl-7-propyl-3H-imidazo [5, 1-f] [1, 2, 4] triazin-4-one was slowly added. to 3.12 ml of chlorosulfonic acid at 0 ° C. The reaction mixture was stirred at room temperature overnight and poured into ice water and extracted with dichloromethane. 2.10 g (94%) of a colorless foam was obtained. RMN-1 !! 400 MHz (CDCl 3): 1.03, t, 3H; 1.35, t, 3H; 1.62, t, 3H; 1.92, sext., 2H; 3.07, quad., 2H; 3. 12, t, 2H; 4.42, quad., 2H; 7.38, d, 1H; 19, dd, 1H; 8.70, d, 1H; 10.08, s, broad, 2H.

Example 19A (4-piperidinylmethyl) -phosphonate diethyl 2.11 g (528 mmol) of 60% sodium hydroxide were initially charged in 50 ml of absolute tetrahydrofuran and 15.7 g (52.8 mmol) of methandifosphonate diethyl was added dropwise. The mixture was stirred other minutes at room temperature and 10.1 g (52.8 mmol) of 1-benzyl-4-piperidone was added dropwise. The mixture was stirred for one hour at room temperature and heated at reflux for one hour, concentrated, mixed with water and extracted three times with dichloromethane, and the organic phase was dried over sodium sulfate and concentrated. The residue was hydrogenated in 50 ml of ethanol over 1.7 g of 10% palladium-active carbon at room temperature and 3 bars. The catalyst was filtered with suction and the filtrate was concentrated. Yield: 12.5 g (100% of theory). 400 MHz-NMR (CDC13): 1.13, m, 2H; 1.32, t, 6H; 1.69, dd, 2H; 1.74 - 1.95 m, 4H; 2.62, dt, 2H; 3.05, m, 2H; 4.1, m, 4H.

Example 20A 5-Methyl-4-furoxancarbaldehyde 40 g (571 mmol) of crotonaldehyde are dissolved in 80 ml of acetic acid and mixed by adding dropwise at 0 ° C with a solution of 137 g (1.99 mol) of sodium nitrite in 300 ml of water. The mixture was stirred for 2 hours at room temperature, diluted with 800 ml of water and extracted 3 times with dichloromethane. The organic phase was then dried, and 13.8 g (18.9%) of 5-methyl-4-furoxancarbaldehyde was chromatographed (cyclohexane / ethyl acetate). 200 MHz-NMR-XH (CDC13): 2.39, s, 3H; 10.10, s, 1H.

Example 21A 5-Methyl-4-furoxancarbonyl chloride 13.5 g (105 mmol) of 5-methyl-4-furoxancarbaldehyde are dissolved in 200 ml of acetone and mixed by adding dropwise at 0 ° C with a solution of 16.86 g (168 mmol) of chromium trioxide in 120 ml. of 2.2 M sulfuric acid. The mixture was stirred for 2 hours at 10-15 ° C and then at room temperature overnight. 100 ml of isopropanol was added dropwise under cooling with ice and after 30 minutes, the solvent was removed under reduced pressure. The aqueous phase was extracted 3 times with ether, the organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was dissolved in a 1 M sodium hydroxide solution and the solution extracted 3 times with ether. The aqueous phase was acidified and extracted 3 times with ether. The organic phase was dried and the solvent was removed under reduced pressure. The residue was stirred with petroleum ether and filtered with suction. 6.92 g of the residue was heated to reflux with 10 ml of thionyl chloride in 20 ml of dichloromethane for 6 hours. The mixture was diluted with toluene, filtered and concentrated using a rotary evaporator. The residue was in turn suspended in dichloromethane, mixed with 10 ml of thionyl chloride and heated to reflux for 48 hours. The solvent was removed under reduced pressure and the residue was distilled under reduced pressure. 2.00 g (25%) of colorless crystals were obtained. 200 MHz-NMR (CDC13): 2.41, s.

Example 22A 1- (5-methyl-4-furoxancarbonyl) -4-tert-butyl-oxycarbonyl-piperazine 2.75 g (14.7 mmol) of Boc-piperazine were dissolved with 1.49 g of triethylamine in 20 ml of dichloromethane and mixed in portions at 0 ° C with 2.00 g. (12.3 mmol) of 5-methyl-4-furoxancarbonyl chloride.

The mixture was stirred for 30 minutes at 0 ° C and for 2 hours at room temperature, diluted with dichloromethane and washed with water. The solvent was removed under reduced pressure and the residue was purified by chromatography (cyclohexane / ethyl acetate). 3.33 g (87%) of 1- (5-methyl-4-furoxancarbonyl) -4-tert-butyl-oxycarbonyl-piperazine were obtained. RMN-1 !! 200 MHz (CDC13): 1.50, s, 9H; 2.30, s, 3H; 3.55,, 4H; 3.78, m, 2H; 3.87,, 2H.

Example 23A 1- (5-Methyl-4-furoxancarbonyl) -piperazine trifluoroacetate 3.12 g (10 mmol) of l- (5-methyl-4-furoxancarbonyl) -4-tert-butyl-oxycarbonyl-piperazine were dissolved in 20 ml of dichloromethane and mixed at 0 ° C with 2 ml of trifluoroacetic acid. The mixture was warmed to room temperature and stirred for 72 hours. After the addition of 10 ml of ether, the precipitate was filtered off with suction and dried. 2.47 g (83%) of 1- (5-methyl-4-furoxancarbonyl) -piperazine were obtained. 200 MHz-NMR (DMSO-d6): 2.18, s, 3H; 3.18, m, 2H; 3.25, m, 2H; 3.83, m, 2H; 3.90, m, 2H; 8.89, s, broad, 2H.

Preparation examples EXAMPLE 1 2- [2-Ethoxy-5- (4-methyl-piperazin-1-sulfonyl) -phenyl] -5,7-dimethyl-3J-imidazo [5, 1] [1, 2, 4] triazine 4-one 0.1 g (0.26 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo- [5,1-f] [1, 2, 4] triazine chloride was dissolved. 2-yl) -benzenesulfonyl in 10 ml of dichloromethane and cooled to 0 ° C. After the addition of the tip of a DMAP spatula, 80 g (0.784 mmol) of N-methylpiperazine was added and the reaction mixture was stirred at room temperature overnight.

The mixture was diluted with dichloromethane, the organic phase was washed with a solution of ammonium chloride and dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (dichloromethane / methanol 9: 1). Yield: 40 mg (34.5% of theory) Mass spectrum: 447 (M + H); 284; 256; 224.

Example 2 2- [2-Ethoxy-5- (4-hydroxyethylpiperazin-1-sulfonyl) -phenyl] -5,7-dimethyl-3J [beta] -imidazo [5, 1] - [1, 2,4] triazin-4 -one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, lf] [1,2,4] chloride triazin-2-yl) -benzenesulfonyl and 100 mg (0.784 mmol) of 4-hydroxypiperazine gave 45 mg (36.1% of theory) of 2- [2-ethoxy-5- (4-hydroxyethyl-piperazine-1-sulfonyl) - phenyl] -5,7-dimethyl-3H-imidazo [5, lf] - [1,2,4] triazin-4-one. Mass spectrum: 477 (M + H); 284; 256; 239 Example 3 2- [2-Ethoxy-5- (4-hydroxypiperidin-1-sulfonyl) -phenyl] -5,7-dimethyl-3-yl-imidazo [5, 1] - [1, 2, 4] triazin-4 -one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, lf] [1,2,4] triazin-2-yl) -benzenesulfonyl chloride and 80 mg (0.784 mmol) of 4-hydroxypiperidine afforded 35 mg (29.8% of theory) of 2- [2-ethoxy-5- (4-hydroxy-piperidin-1-sulphonyl) -phenyl] -5,7 -dimethyl-3i? -i? aidazo [5, lf] - [1,2,4] triazin-4-one. 200 MHz-NMR (CDC13): 1.61, t, 3H; 1.69, m, 2H; 1.94, m, 2H; 2.67, s, 3H; 2.70, s, 3H; 3.02, ", 2H, 3.30, m, 2H, 3.84, m, 1H, 4.37, c, 2H, 7.18, d, 1H, 7.90, dd, 1H, 8.52, d, 1H, 9.73, s, 1H.

Example 4 2- [2-ethoxy-5- (4-hydroxymethylpiperidine-1-sulfonyl) -phenyl] -5,7-dimethyl-32α-imidazo [5, 1] [1,2,4] triazine-4 ona By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, lf] [l, 2,4] chloride] triazin-2-yl) -benzenesulfonyl and 90 mg (0.784 mmol) of 4-hydroxymethylpiperidine, 22 mg (18% of theory) of 2- [2-ethoxy-5- (4-hydroxy-methyl-piperidine-1-sulfonyl) were obtained. ) -phenyl] -5,7-dimethyl-3i? -imidazo [5, 1-f] [1, 2, 4] triazin-4-one. RMN-1 !! 200 MHz (CDC1,): 1.38, dt, 2H; 1.62, t, 3H; 1.82, dd, 2H; 2.35, dt, 2H; 2.78, s, 3H; 2.84, s, 3H; 3.5, d, 2H; 3.87, d, 2H; 4.39, c, 2H; 7.21, d, 1H; 7.95, dd, 1H; 8.51, d, 1H; 10.03, sa, 1H.

Example 5 2- [2-ethoxy-5- (3-hydroxypyrrolidin-1-sulfonyl) -phenyl] -5,7-dimethyl-3H-imidazo [5, 1-f] [1,2,4] triazin-4-one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1,2,4] chloride triazin-2-yl) -benzenesulfonyl and 70 mg (0.784 mmol) of 3-hydroxypyrrolidine yielded 13 mg (11.1% of theory) of 2- [2-ethoxy-5- (3-hydroxy-pyrrolidin-Isulfonyl) - phenyl] -5,7-dimethyl-3H-imidazo [5, 1-f] [1, 2, 4] triazin-4-one. Mass spectrum: 434 (M + H) Example 6 4-Ethoxy-N-ethyl-N- (2-hydroxyethyl) -3- (5,7-dimethyl-4-oxo-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl) benzenesulfonamide By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, lf] [1,2,4] triazin-2-yl) -benzenesulfonyl chloride and 70 mg (0.784 mmol) of 2- (ethylamino) -ethanol yielded 23 mg (20.1% of theory) of 4-ethoxy-N-ethyl-N- (2-hydroxyethyl) -3- (5,7-dimethyl) -4-oxo-3,4-dihydroimidazo [5, lf] [1,2,4] triazin-2-yl) -benzenesulfonamide-. NMR --- H 200 MHz (CDC13): 1.2, t, 3H; 1.6, t, 3H; 2.17, sa, 1H; 2.69, s, 3H; 2.75, s, 3H; 3.33, 4H; 3.8, t, 2H; 4.36, c, 2H; 7.18, d, 1H; 7.99, dd, 1H; 8.6 d, 1H; 9.84, sa, 1H.

Use 7 N, N-diethyl-4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl benzenesulfonamide By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1,2,4] chloride triazin-2-yl) -benzenesulfonyl and 60 mg (0.784 mmol) of diethylamine, 21 mg (18.6% of theory) of N, N-diethyl-4-ethoxy-3- (5,7-dimethyl-4-) were obtained oxo-3, 4-dihydro-imidazo [5, 1-f] [1, 2,] triazin-2-yl) benzenesulfonamide. 200 MHz-NMR (CDC13) * 1.18, t, 6H; 1.61, t, 3H; 2.68, s, 3H; 2.72, s, 3H; 3.29, c, 4H; 4.35, c, 2H; 7.15, d, 1H; 7.95, dd, 1H; 8.58, d, 1H; 9.8, sa, 1H.

EXAMPLE 8 2- [2-Ethoxy-5- (4- (2-pyrimidinyl) -piperazin-1-sulfonyl) -phenyl] -5,7-dimethyl-3J? -imidazo [5, lf] [1,2, 4] triazin-4-one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1,2,4] chloride triazin-2-yl) -benzenesulfonyl and 130 mg (0.784 mmol) of 1- (2-pyrimidinyl) -piperazine, 38 mg (28.2% of theory) of 2- [2-ethoxy-5- (4- ( 2-pyrimidinyl) -piperazin-1-sulfonyl) -phenyl] -5,7-dimethyl-3i? -imidazo [5, 1-f] [1, 2, 4] triazin-4-one. 200 MHz-NMR-NMR (CDC13): 1.6, t, 3H; 2.68, s, 3H; 2.72, s, 3H; 3.12, t, 4H; 3.96, t, 4H; 4.34, c, 2H; 6.5, t, 1H; 7.18, d, 1H; 7.9, dd, 1H; 8.28, d, 2H; 8.51, d, 1H; 9.7, sa, 1H.

Example 9 2- [2-Ethoxy-5- (morpholin-4-sulfonyl) -phenyl] -5,7-dimethyl-3'T-imidazo [5, 1-f] [1,2,4] triazin-4-one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1,2,4] chloride triazin-2-yl) -benzenesulfonyl and 70 mg (0.784 mmol) of morpholine, 28 mg (24.2% of theory) of 2- [2-ethoxy-5- (morpholin-4-sulfonyl) -phenyl] -5 were obtained , 7-dimethyl-3i? -imidazo [5, 1-f] [1, 2, 4] triazin-4-one.

RMN-1 !! 200 MHz (CDC1): 1.53, t, 3H; 2.69, s, 3H; 2.72, s, 3H; 3.06, t, 4H; 3.77, t, 4H; 4.39, quad., 2H; 7.2 d, 1H; 7.91, dd, 1H; 8.51, d, 1H; 9.78, sa, 1H.

Example 10 2- [2-ethoxy-5- (1,4-dioxa-6-azaspiro [4.4] nonan-6-sulfonyl) -phenyl] -5,7-dimethyl-3i? -imidazo [5, 1-f ] [1, 2, 4] triazin-4-one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, lf] [l, 2,4] chloride] triazin-2-yl) -benzenesulfonyl and 100 mg (0.784 mmol) of 1, 4-dioxa-6-azaspiro [4.4] nonane, 45 mg (35.3% of theory) of 2- [2-ethoxy-5- (1,4-dioxa-6-azaspiro [4.4] nonan-6-sulfonyl) -phenyl] -5,7-dimethyl-3J-imidazo [5, lf] [1,2,4] triazin-4-one.

NMR--? 200 MHz (CDC13): 1.58, t, 3H; 2.02, t, 2H; 2.61, s, 3H; 2.65, s, 3H; 3.32, s, 2H; 3.41, t, 2H; 3.88, m, 4H; 4.34, quad., 2H; 7.17, d, 1H; 7.92, dd, 1H; 8.51, d, 1H; 9.92, sa, 1H.

Example 11 N, N-bis- (2-methoxyethyl) -4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazin-2-yl) benzenesulfonamide By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1, 2, 4] chloride triazin-2-yl) -benzenesulfonyl and 100 mg (0.784 mmol) of bis- (2-methoxyethyl) -amine, 37 mg (27.5% of theory) of N, N-bis- (2-methoxy-ethyl) were obtained -4-ethoxy-3- (5, 7-dimethyl-1,4-oxo-3,4-dihydro-imidazo [5, 1] [1, 2,4] triazin-2-yl) -benzenesulfonamide.

NMR --- H 200 MHz (CDC1): 1.58, t, 3H; 2.61 s, 3H; 2.46, s, 3H; 3.3 s, 6H; 3.46, t, 4H; 3.56, t, 4H; 4.32, c, 2H; 7.12, d, 1H; 7.95, dd, 1H; 8.51, d, 1H; 9.9, sa, 1 HOUR.

Example 12 N- (3-isoxazolyl) -4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazin-2- il) benzenesulfonamide By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1, 2, 4] chloride triazin-2-yl) -benzenesulfonyl and 70 mg (0.784 mmol) of 3-aminoisoxazole, there was obtained 20 mg (17.2% of theory) of N- (3-isoxazolyl) -4-ethoxy-3- (5, 7- dimethyl-4-oxo-3,4-dihydroimidazo [5, lf] [l, 2,4] triazin-2-yl) benzenesulfonamide.

RMN-1 !! 200 MHz (CDCl 3) * 1.6, t, 3H; 2.73, s, 3H; 2.81, s, 3H; 4.35, - c, 2H; 6.6, d, 1H; 7.14, d, 1H; 8.05, dd, 1H; 8.27, d, 1H; 8.63, d, 1H; 9.61, sa, 1H.

EXAMPLE 13 2- [2-Ethoxy-5- (2-t-butoxycarbonylaminomethyl-morpholin-4-sulfonyl) -phenyl] -5,7-dimethyl-3-imidazo [5,1-f] [1, 2, 4] triazin -4-one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1,2,4] chloride triazin-2-yl) -benzenesulfonyl and 170 mg (0.784 mmol) of 2-t-butoxycarbonylaminomethylmorpholine, 64 mg (42.2% of theory) of 2- [2-ethoxy-5- (2-t-butoxycarbonylaminomethyl) morpholine-4 were obtained -sulfonyl) -phenyl] -5,7-dimethyl-3iT-imidazo [5, lf] [1,2,4] triazin-4-one. Mass spectrum: 563 (M + H) EXAMPLE 14 2- [2-Ethoxy-5- (4-phenylpiperazin-1-sulfonyl) -phenyl] -5,7-dimethyl-3J? -imidazo [5, lf] [ 1, 2, 4] triazin-4-one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1,2,4] chloride triazin-2-yl) -benzenesulfonyl and 130 mg (0.784 mmol) of 1-phenylpiperazine afforded 38 mg (28.3% of theory) of 2- [2-ethoxy-5- (4-phenylpiperazine-1-sulfonyl) phenyl) ] -5,7-dimethyl-3l-imidazo [5, lf] [1,2,4] triazin-4-one. NMR-H 200 MHz (CDC13): 1.62, t, 3H, 2.27, s, 3H; 2.77, s, 3H; 3.25, m, 8H; 4.38, c, 2H; 6.92, m, 2H; 7.02, d, 1H; 7.18-7.37, m, 3H; 7.94, dd, 1H; 8.55, m, 1H; 9.79, sa, 1H.

Example 15 2- [2-ethoxy-5- (3-hydroxy-3-methoxymethylpyrrolidin-1-sulfonyl) -phenyl] -5,7-dimethyl-3J [beta] -imidazo [5, 1-f] [1, 2, ] triazin-4-one By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3- (5,7-dimethyl-4-oxo-3,4-dihydroimidazo [5, 1]] [1, 2, 4] chloride triazin-2-yl) -benzenesulfonyl and 100 mg (0.784 mmol) of 3-hydroxy-3-methoxymethylpyrrolidine yielded 30 mg (23.5% of theory) of 2- [2-ethoxy-5- (3-hydroxy-3 -methoxymethylpyrrolidin-1-sulfonyl) -phenyl] -5,7-dimethyl-3i? -imidazo [5, lf] [1, 2, 4] triazin-4-one. Mass spectrum: 478 (M + H) Example 16 2- [2-Ethoxy-5- (4-methyl-piperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3J-imidazo [5, lf] [1,2,4] triazin-4-one 1.23 g (3 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, 1-f] chloride [1, 2, 4] were dissolved. ] triazin-2-yl) -benzenesulfonyl in 40 ml of dichloromethane and cooled to 0 ° C. After the addition of a DMAP spatula tip, 0.90 g (9.00 mmol) of N-methylpiperazine was added and the reaction mixture was stirred overnight at room temperature. The mixture was diluted with dichloromethane, the organic phase was washed twice with water, dried over sodium sulfate and the solvent was removed under reduced pressure. Crystallization from ether gives 1.25 g (88%) of a colorless solid. 200 MHz-NMR-NMR (CDC13): 1.01, t, 3H; 1.59, t, 3H; 1.88, sext., 2H; 2.29, s, 3H; 2.51, m, 4H; 2.63, s, 3H; 3.00, t, 2H; 3.08, m, 4H; 4.33, quad., 2H; 7.17, d, 1H; 7.88, dd, 1H; 8.44, d, 1H; 9.75, s, 1H.

Example 17 2- [2-Ethoxy-5- (4-methyl-piperazin-1-sulfonyl) phenyl] -5-methyl-7-propyl-3J [beta] -imidazo [5, 1-f] [1, 2] lactate , 4] triazin-4-one 100 mg (0.211 mmol) of 2- [2-ethoxy-5- (4-methyl-piperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3i-imidazo was suspended [5, lf] [1, 2, 4] triazin-4-one in 5 ml of ether and mixed with 20 mg of an 85% solution of lactic acid in water. The mixture was stirred for 10 minutes at room temperature and evaporated to dryness. The residue was triturated with ether and filtered with suction. 110 mg (92%) of 2- [2-ethoxy-5- (4-methyl-piperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3H-imidazo [5, lf] lactate was obtained. ] [1,2,4] triazin-4-one. 200 MHz-NMR-1H (DMSO-d6): 0.92, t, 3H; 1.22, d, 3H; 1.31, t, 3H; 1.74, m, 1H; 2.15, s, 3H; 2.38,, 4H; 2.81, t, 2H; 2.91,, 4H; 4.05, quadr., 1H; 4.21, quad., 2H; 7.40, d, 1H; 7.85, m, 2H; 11.71, s, broad, 1H. Example 18 2- [2-Ethoxy-5- (4-methyl-piperazin-1-sulphonyl) phenyl] -5-methyl-7-propyl-3i-r-imidazo [5, 1-f] [] hydrochloride 1, 2,] triazin-4-one 100 mg (0.211 mmol) of 2- [2-ethoxy-5- (4-methylpiperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3-yl-imidazo [5, 1] [1] was suspended. 2,4] Triazin-4-one in 5 ml of diethyl ether was mixed with 0.23 ml of a 1M solution of HCl in ether and stirred for 15 minutes at room temperature. The solvent is removed under reduced pressure. "107 mg (97%) of 2- [2-ethoxy-5- (4-methyl-piperazin-1-sulfonyl) -phenyl] -5-methyl-7- hydrochloride were obtained. propyl-3ff-imidazo [5, 1-f] [1, 2, 4] triazin-4-one NMR-XH 200 MHz (DMS0-d6): 0.93, t, 3H, 1.35, t, 3H, 1.75, sext., 2H, 2.72, s, 3H, 2.86, m, 4H, 3.15, m, 2H, 3.45, m, 2H, 3.81, m, 2H, 4.25, quad, 2H, 7.45, d, 1H, 7.95, m, 2H; 11.39, s, 1H; 11.90, s, 1H.

Example 19 2- [2-Ethoxy-5- (4-ethyl-piperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3H-imidazo [5, 1] [1,2,4] triazine -4-one 470 mg (1.14 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3 chloride was dissolved., 4-dihydro-imidazo [5, 1-f] [1, 2, 4] triazin-2-yl) -benzenesulfonyl in 20 ml of dichloromethane and cooled to 0 ° C. 390 mg (3.42 mmol) of N-ethylpiperazine was added, and the reaction mixture was stirred overnight at room temperature. It was diluted with dichloromethane, the organic phase was washed twice with water, dried over sodium sulfate and the solvent was removed under reduced pressure. Crystallization from ether gives 370 g (66%) of a colorless solid. NMR ^ H 400 MHz (CDC13): 1.01, t, 3H; 1.59, t, 3H; 1.88, sext., 2H; 2.42, quadr., 2H; 2.56,, 4H; 2.63, s, 3H; 3.00, t, 2H; 3.10, m, 4H; 4.33, quad., 2H; 7.17, d, 1H; 7.88, dd, 1H; 8.44, d, 1H; 9.75, s, 1H.

EXAMPLE 20 2- [2-Ethoxy-5- (4-ethyl-piperazin-1-sulfonyl) phenyl] -5-methyl-7-propyl-3ff-imidazo [5, 1-f] [1, 2, 4] triazin-4-one 0.35 g (0.712 mmol) of 2- [2-ethoxy-5- (4-ethylpiperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3H-imidazo [5, 11] [1] was suspended. 2,4] triazin-4-one in 8 ml of ether and dichloromethane was added until a homogeneous solution was obtained. 0.8 ml of a 1 M solution of HCl in ether was added, and the mixture was stirred for 20 minutes at room temperature and filtered with suction. 372 mg (99%) of 2- [2-ethoxy-5- (4-ethylpiperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3H-imidazo hydrochloride [5, lf] [ 1,2,4] triazin-4-one. 200 MHz-NMR-XH (DMSO-d6): 0.96, t, 3H; 1.22, t, 3H; 1.36, t, 3H; 1.82, sext., 2H; 2.61, s, 3H; 2.88, m, 2H; 3.08,, 6H; 3.50, m, 2H; 3.70, m, 2H; 4.25, quad., 2H; 7.48, d, 1H; 7.95, m, 2H; 11.42, s, 1H; 12.45, s, 1H.

Example 21 2- [2-Ethoxy-5- (4-methyl-1-amino-piperazin-1-sulfonyl) -phenyl] -5-methyl-1-7-propyl-3-yl-imidazo [5, 1] [1, 2] , 4] triazin-4-one By the same method starting with 0.04 g (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2] chloride , 4] triazin-2-yl) -benzenesulfonyl and 0.03 g (0.29 mmol) of l-amino-4-methylpiperazine, 40 mg (83%) of 2- [2-ethoxy-5- (4-methyl-) l-aminopiperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3-p-imidazo [5, 1] [1,2,4] triazin-4-one. Rf = 0.99 (dichloromethane / methanol = 19: 1) 200 MHz-NMR (CDC13): 1.02, t, 3H; 1.59, t, 3H; 1.90, sext., 2H; 2.22, s, 3H; 2.40, m, 4H; 2.62, s, 3H; 2.71, m, 4H; 3.00, m, 2H; 4.32, quad., 2H; 7.14, d, 1H; 8.05, dd, 1H; 8.60, d, 1H.

EXAMPLE 22 2- [2-Ethoxy-5- (4-hydroxyethyl-1-amino-piperazin-1-sulfonyl) phenyl] -5-methyl-7-propyl-3ι-imidazo [5, 1-f] [1, 2, 4] triazin-4-one By the same method, starting with 0.04 g (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride. 2, 4] triazin-2-yl) -benzenesulfonyl and 0.04 g (0.29 mmol) of l-amino-4-hydroxyethylpiperazine, 46 mg (91%) of 2- [2-ethoxy-5- (4-hydroxyethyl -l-aminopiperazin-l-sulfonyl) -phenyl] -5-methyl-7-propyl-3J? -imidazo [5, lf] [l, 2,4] triazin-4-one. Rf = 0.08 (dichloromethane / methanol = 19: 1) NMR--? 200 MHz (CDC13): 1.02, t, 3H; 1.59, t, 3H; 1.90, sext., 2H; 2.49, m, 6H; 2.62, s, 3H; 2.71, m, 4H; 3.00, t, 2H; 3.55, t, 2H; 4.31, quad., 2H; 7.14, d, 1H; 8.05, dd, 1H; 8.60, d, 1H.

Example 23 N, N-Bishydroxyethylaminoethyl-4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2- il) benzenesulfonamide By the same method, starting with 0.04 g (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride. 2, 4] triazin-2-yl) -benzenesulfonyl and 0.043 g (0.29 mmol) of N, N-bishydroxyethylamino-ethylamine, 46 mg (91%) of N, N-bishydroxyethylaminoethyl-4-ethoxy-3- ( 5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazin-2-yl) benzenesulfonamide. 200 MHz-NMR (CDC13): 1.02, t, 3H; 1.53, t, 3H; 1.70, m, 2H; 1.86, sext., 2H; 2.9, m, 9H; 2.95, t, 2H; 3.09, t, 2H; 3.65, t, 4H; 4.28, quad., 2H; 7.14, d, 1H; 7.95, dd, 1H; -8.35, d, 1H.

Example 24 2- [2-ethoxy-5- (4-dimethoxyphosphorylmethyl-piperazin-1-sulfonyl) phenyl] -5-methyl-7-propyl-3H-imidazo [5, 1-f] [1, 2, 4 ] triazin-4-one By the same method, starting with 0.4 g (0.97 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3, 4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) -benzenesulfonyl, 390 mg of triethylamine and 0.86 g (2.99 mmol) of 4-dimethoxyphosphorylmethyl-piperazine trifluoroacetate, 321 mg (53%) of 2- [2-ethoxy-5 - (4-dimethoxyphosphorylmethyl-piperazin-1-sulfonyl) phenyl] -5-methyl-7-propyl-3-imidazo [5, lf] [1,2,4] triazin-4-one.

Rf = 0.4 (dichloromethane / methanol = 20: 1) NMR-1! 200 MHz (CDC13): 1.02, t, 3H; 1.60, t, 3H; 1.88, sext., 2H; 2.62, s, 3H; 2.75, m, 4H; 3.02, t, 2H; 3.11, m, 4H; 3.70, s, 3H; 3.75, s, 3H; 4.35, quad., 2H; 5.30, s, 2H; 7.18, d, 1H; 7.88, dd, 1H; 8.45, d, 1H; 9.71, s, 1H.

Example 25 2- [2-ethoxy-5- (4-diethoxyphosphorylmethyl-piperidin-1-sulfonyl) phenyl] -5-methyl-7-propyl-3J [beta] -imidazo [5, 1-f] [1, 2, 4 ] triazin-4-one By the same method, starting with 0.4 g (0.97 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3, 4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) -benzenesulfonyl and 0.86 g (3.7 mmol) of 4-diethoxyphosphorylmethyl-piperidine, 366 mg were obtained (49%) of 2- [2-ethoxy-5- (4-diethoxyphosphorylmethyl-piperidin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3-yl-imidazo [5, 1-f] [1, 2,4] triazin-4-one Rf = 0.4 (dichloromethane / methanol = 20: 1) RMN-1! 200 MHz (DMS0-d6): 0.92, t, 3H; 1.20, t, 6H; 1.35, t, 3H; 1.75, m, 7H; 2.25, m, 2H; 2.82, t, 2H; 3.61, d, 2H; 3.95, quin., 4H; 4.21, quad., 2H; 7.38, d, 1H; 7.87, m, 2H; 11.70, s, 1H.

EXAMPLE 26 2- [2-Ethoxy-5- (4-hydroxy-piperidin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3-yl-imidazo [5, lf] [1,2,4] triazin -4-one By the same method, starting with 531 mg (1.29 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 393 mg (3.88 mmol) of 4-hydroxypiperidine, 400 mg (64%) of 2- [2-ethoxy-5- (4-hydroxy-piperidin-1) were obtained -sulfonyl) -phenyl] -5-methyl-7-propyl-3-J-imidazo [5, lf] [1,2,4] triazin-4-one. RMN-1 !! 200 MHz (DMS0-d5): 0.941, t, 3H; 1.32, t, 3H; 1.45, m, 2H; 1.71, m, 4H; 2.48, s, 3H; 2.82", m, 4H, 3.11, m, 2H, 3.55, m, 1H, 4.20, quad, 2H, 4.72, d, 1H, 7.39, d, 1H, 7.87, m, 2H, 11.70, s, 1H.

Example 27 2-. { 2-Ethoxy-5- [4- (2-hydroxy-ethyl) -piperazin-1-sulfonyl] phenyl} -5-methyl-7-propy1-3 H-imidazo [5,1-f] [1, 2, 4] triazin-4-one By the same method, starting with 411 mg (1 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 391 mg (3 mmol) of 4-hydroxyethylpiperazine gave 380 mg (75%) of 2- [2-ethoxy-5- [4- (2-hydroxyethyl) ethyl) -piperazin-1-sulfonyl] phenyl} -5-methyl-7-propyI-3J? -imidazo [5,1-f] [1, 2, 4] triazin-4-one. Rf = 0.198 (dichloromethane / methanol = 95: 5) NMR-1! 200 MHz (CDC13) * 1.02, t, 3H; 1.61, t, 3H; 1.87, sext., 3H; 2.60, m, 7H; 3.00, t, 2H; 3.10,, 4H; 3.60, t, 2H; 4.36, quad., 2H; 7.18, d, 1H; 7.89, dd, 1H; 8.47, d, 1H; 9.71, s, 1H.

Example 28 2- Hydrochloride. { 2-Ethoxy-5- [4- (2-hydroxy-ethyl) piperazin-1-sulfonyl] -phenyl} -5-methy1-7-propyl-3H-imidazo [5, l-f] [1,2,4] triazin-4-one 200 mg (0.39 mmol) of 2- was suspended. { 2-ethoxy-5- [4- (2-hydroxy-ethyl) -piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propyl-3i? -imidazo [5, lf] [1, 2,] triazin-4-one in ether was mixed with 2 ml of a 1 M solution of HCl in ether and stirred for 20 minutes at room temperature. After removing the solvent, 209 mg (100%) of 2- hydrochloride were obtained. { 2-ethoxy-5- [4- (2-hydroxy-ethyl) -piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propyl-3i-imidazo [5, 1-f] [1,2,4] triazin-4-one. RMN-1 !! 200 MHz (DMSO-d6): 0.96, t, 3H; 1.35, t, 3H; 1.70, sext., 2H; 2.59, s, 3H; 2.85, t, 2H; 2.99, t, 2H; 3.18, m, 4H; 3.59, d, 2H; 3.75, m, 4H; 4.25, quad., 2H; 7.49, d, 1H; 7.95, m, 2H; 10.62, s, 1H; 12.31, s, 1H.

Example 29 2-. { 2-ethoxy-5- [4- (3-hydroxy-propyl) -piperazin-1-sulphonyl] -phenyl} -5-methyl-7-propyl-3J? -imidazo [5,1-f] [1, 2, 4] triazin-4-one By the same method, starting with 150 mg (0.37 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3, 4-dihydro-imidazo [5, lf] [1, 2,4] triazin-2-yl) -benzenesulfonyl and 158 mg (1.09 mmol) of 4- (3-hydroxypropyl) -piperazine gave 167 mg (83%) of 2-. { 2-ethoxy-5- [4- (3-hydroxy-propyl) -piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propyl-3i? -imidazo [5, 1-f] [1, 2, 4] triazin-4-one. Rf = 0.52 (dichloromethane / methanol = 10: 1) 200 MHz-NMR (CDC13): 1.02, t, 3H; 1.61, t, 3H; 1.70, m, 5; 2.62, m, 8H; 3.00, t, 2H; 3.10, m, 4H; 3.72, t, 2H; 4.36, quad., 2H; 7.18, d, 1H; 7.89, dd, 1H; 8.47, d, 1H; 9.71, s, 1H.

EXAMPLE 30 N-Allyl-4-ethoxy-N- (2-hydroxy-ethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2,4] triazin-2-yl) benzenesulfonamide By the same method, starting with 420 mg (1.02 mmol) (1 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3, 4-dihydro-imidazo chloride [5, lf ] [1, 2, 4] triazin-2-yl) -benzenesulfonyl and 300 mg (3 mmol) of allylhydroxyethylamine, 400 mg (82%) of N-allyl-4-ethoxy-N- (2-hydroxy) were obtained. ethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imi-azo [5, lf] [1,2,4] triazin-2-yl) -benzenesulfonamide. Rf = 0.345 (dichloromethane / methanol = 95: 5) NMR-1! 200 VHz (CDC13): 1.02, t, 3H; 1.61, t, 3H; 1.90,, 2H, 2.22, s, broad, 1H; 2.62, s, 3H; 2.99, t, 2H; 3.31, t, 2H; 3.78, t, 2H; 3.92, d, 2H; 4.37, quadr., 2H; 5.23, m, 2H; 5.71, m, 1H; 7.15, d, 1H; 7.98, dd, 1H; 8.56, d, 1H; 9.66, s, 1H.

EXAMPLE 31 N-Ethyl-4-ethoxy-N- (2-hydroxy-ethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) benzenesulfonamide By the same method, starting with 411 mg (1.0 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3, -dihydroimidazo [5, lf] [1,2,4 Triazin-2-yl) -benzenesulfonyl and 267 mg (3 mmol) of ethylhydroxyethylamine gave 325 mg (70%) of N-ethyl-4-ethoxy-N- (2-hydroxy-ethyl) -3- ( -methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl) benzenesulfonamide. Rf = 0.29 (dichloromethane / methanol = 95: 5) NMR-1! 200 MHz (CDC13): 1.02, t, 3H; 1.20, t, 3H; 1.61, t, 3H; 1.88, sext., 2H; 2.30, s, broad, 1H; 2.62, s, 3H; 2.99, t, 2H; 3.32, m, 4H; 3.78, t, 2H; 3.80,, 2H; 4.37, quadr., 2H; 7.15, d, 1H; 7.98, dd, 1H; 8.56, d, 1H; 9.70, s, 1H.

EXAMPLE 32 N, N-Diethyl-4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazin-2- __ _ _ il) benzenesulfonamide By the same method, starting with 400 mg (0.97 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) -benzenesulfinyl and 210 mg (2.92 mmol) of diethylamine gave 398 mg (89%) of N, N-diethyl-4-ethoxy-3- (5-methyl-4-). oxo-7-propyl-3,4-dihydro-imidazo [5, 1-f] [1, 2, 4] triazin-2-yl) benzenesulfonamide.

Rf = 0.49 (dichloromethane / methanol = 20: 1) NMR--? 200 MHz (CDC13): 1.02, t, 3H; 1.20, t, 6H; 1.49, t, 1.61, t, 3H; 1.88, sext., 2H; 2.30, s, broad, 1H; 2.62, s, 3H; 2.99, t, 2H; 3.32,, 4H; 3.78, t, 2H; 3.80, m, 2H; 4.37, quadr., 2H; 7.15, d, 1H; 7.98, dd, 1H; 8.56, d, 1H; 9.70, s, 1H.

Example 33 N- (2-methoxyethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2, 4] triazin-2-yl) 4-ethoxy-beneenosulfonamide Using the same method, starting with 1.23 g (3 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl chloride. ) -benzenesulfonyl and 680 mg (9 mmol) of 2-methoxyethylamine, 900 mg (67%) of N- (2-methoxy-ethyl) -3- (5-methyl-4-oxo-7-propyl-3 was obtained , 4-dihydro-imidazo [5, 1-f] [1,2,4] triazin-2-yl) 4-ethoxy-benzenesulfonamide.

Rf = 0.25 (dichloroethane / methanol = 95: 5) 1 H 400 MHz NMR (CDC13): 1.01, t, 3H; 1.58, t, 3H; 1.88, sext-, 2H; __ 2.62, s, 3H; 3.01, t, 2H; 3.18, quad., 2H; 3.30, s, 3H; 3.45, t, 2H; 4.32, quad., 2H; 5.12, t, 1H; 7.13, "d, 1H; 7.97, dd, 1H; 8.53, d, 1H; 9.82, s, 1H.

Example 34 N- (2-N, N-dimethylethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazine- 2-yl) -4-ethoxy-benzenesulfonamide By the same method, starting with 210 mg (0.49 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3, -dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl chloride) -benzenesulfonyl and 130 mg (9 mmol) of 2-N, N-dimethylethylamine, 150 mg (59%) of N- (2-N, N-dimethylethyl) -3- (5-methyl-4-oxo-) were obtained. 7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2-, 4] triazin-2-yl) -4-ethoxy-benzenesulfonamide. 200 MHz-NMR-XH (CDC13): 1.01, t, 3H; 1.62, m, 4H; 1.88, sext., 2H; 2.11, s, 6H; 2.39, t, 2H; 2.63, s, 3H; 3.01, m, 3H; 4.38, quadr., 2H; 7.13, d, 1H; 7.97, dd, 1H; 8.53, d, 1H; 9.82, s, 1H.

Example 35 N- [3- (1-morpholino) propyl] -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazin -2-yl) -4-ethoxy-benzenesulfonamide Using the same method, starting with 1.23 g (3 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-pro-yl-3,4-dihydroimidazo [5, lf] [1,2,4] triazin-2-yl chloride) -benzenesulfonyl and 1.3 g (9 mmol) of 3- (1-morpholino) -propylamine gave 1.38 g (88%) of N- [3- (l-morpholino) propyl] -3- (5-methyl-4) -oxo-7-propyl-3, 4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl) -4-ethoxy-benzenesulfonamide. Rf = 0.23 (dichloromethane / methanol = 95: 5) NMR-1! 200 MHz (CDC13): 1.01, t, 3H; 1.58, t, 3H; 1.72, m, 2H; 1.88, sext., 2H; 2.46,, 6H; 2.62, s, 3H; 3.01, t, 2H; 3.15, t, 2H; 3.71, t, 4H; 4.32, quadr., 2H; 7.13, d, 1H; 7.97, dd, 1H; 8.53, d, 1H; 9.79, s, 1H.

Example 36 N- [3- [1- (4-methyl) piperazino] propyl} -3- (5-Methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, 1-f] [1,2,4] triazin-2-yl) -4-ethoxy-benzenesulfonamide Using the same method, starting with 0.04 g (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl chloride ) -benzenesulfonyl and 0.05 g (0.29 mmol) of 3- [l- (4-methyl) piperazino] -propylamine, 0.04 g (77%) of N- (3- [1- (4-methyl) piperazino] were obtained] propyl.}. -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl) -4-ethoxy- benzenesulfonamide, Rf = 0.11 (dichloromethane / methanol = 95: 5) 200 MHz-NMR-NMR (CDC13): 1.01, t, 3H, 1.55, t, 3H, 1.68, m, 2H, 1.88 , sext., 2H, 2.27, s, 3H, 2.45, m, 8H, 2.62, s, 3H, 2.98, m, 3H, 3.10, t, 2H, 3.46, s, 1H; 4.30, quadr., 2H, 7.13, d, 1H, 7.97, dd, 1H, 8.53, d, 1H.

Example 37 2-. { 2-Ethoxy-5- [4- (2-methoxy-ethyl) -piperazin-1-sulfonyl] -phenyl} -5-m.ethyl-7-propyl-3.ff-imidazo [5, l-f] [1, 2, 4] triazin-4-one By the same method, starting with 40 mg (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 40 mg (0.29 mmol) of 4-methoxyethylpiperazine, 50 mg (99%) of 2- were obtained. { 2-Ethoxy-5- [4- (2-methoxy-ethyl) -piperazin-1-sulfonyl] -phenyl} 5-methyl-7-propyl-3H-imidazo [5, 1-f] [1,2,4] triazin-4-one. Rf = 0.27 (dichloromethane / methanol = 95: 5) 200 MHz-NMR (CDC13): 1.02, t, 3H; 1.61, t, 3H; 1.87, sext., 3H; 2.60, m, 9H; 2.97, t, 2H; 3.10, m, 4H; 3.60, s, 3H; 3.46, t, 2H; 4.36, quadr., 2H; 7.18, d, 1H; 7.89, dd, 1H; 8.47, d, 1H; 9.71, s, 1H.

Example 38 2-. { 2-ethoxy-5- [4- (2-N, N-dimethyl-ethyl) -piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propyl-3l-imidazo [5,1-f] [1, 2, 4] triazin-4-one By the same method, starting with 40 mg (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3, 4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) -benzenesulfonyl and 50 mg (0.29 mmol) of 4- (2-N, N-dimethyl) -ethylpiperazine, 50 mg (99%) of 2- were obtained. { 2-Ethoxy-5- [4- (2-N, N-dimethyl-ethyl) -piperazin-1-sulphonyl] -phenyl} -5-methyl-7-propyl-3 f -imidazo [5,1-f] [1, 2, 4] triazin-4-one. Rf = 0.11 (dichloromethane / methanol = 95: 5) 200 MHz-NMR (CDC13): 1.02, t, 3H; 1.61, t, 3H; 1.87, sext., 3H; 2.20, s, 6H; 2.42, m, 4H; 2.58, m, 4H; 2.63, s, 3H; 2.99, m, 3H; 3.10, m, 4H; 4.36, quadr., 2H; 7.18, d, 1H; 7.89, dd, 1H; 8.47, d, 1H; 9.71, s, 1H.

Use 39 2- [2-ethoxy-5- [4- (3-N, N-dimethyl-propyl) -piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propyl-3i? -imidazo [5, 1-f] [1, 2, 4] triazin-4-one By the same method, starting with 100 mg (0.243 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 130 mg (0.73 mmol) of 4- (3-N, N-dimethyl) -propylpiperazine afforded 72 mg (54%) of 2-. { 2-Ethoxy-5- [4- (3-N, N-dimethylpropyl) -piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propyl-3J? -imidazo [5,1-f] [1, 2,] triazin-4-one. Rf = 0.08 (dichloromethane / methanol = 95: 5) NMR-1! 200 MHz (CDC13) * 1.02, t, 3H; 1.61, t, 3H; 1.87, sext., 3H; 2.20, s, 6H; 2.25, m, 2H; 2.38, t, 2H; 2.52, m, 4H; 2.63, s, 3H; 2.99, m, 6H; 4.33, quadr., 2H; 7.18, d, 1H; 7.89, dd, 1H; 8.47, d, 1H; 9.71, s, 1H.

EXAMPLE 40 2- [2-ethoxy-5- (4-dioxolane-piperidin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3i-imidazo [5, lf] [1,2,4 ] triazin-4-one By the same method, starting with 100 mg (0.243 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) ~ benzenesulfonyl and 100 mg (0.73 mmol) of 4-dioxolanepiperidine, 111 mg (88%) of 2- [2-ethoxy-5- (4-dioxolane-piperidin-1) were obtained -sulfonyl) -phenyl] -5-methyl-7-propyl-3i? -imidazo [5, lf] [l, 2,4] triazin-4-one. 200 MHz-NMR-NMR (CDC13): 1.02, t, 3H; 1.61, t, 3H; 1.80, m, 6H; 2.63, s, 3H; 2.99, t, 2H; 3.20, m, 4H; 3.90, s, 4H; 4.33, quadr., 2H; 7.18, d, 1H; 7.89, dd, 1H; 8.47, d, 1H; 9.71, s, 1H.

Example 41 2- [2-Ethoxy-5- (4- (5-methyl-4-furoxancarbonyl) -piperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3i-imidazo [5.1 -f] [1, 2, 4] triazin-4-one 410 mg (1.0 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2,] triazine chloride was dissolved. 2-yl) -benzenesulfonyl in ml of dichloromethane and cooled to 0 ° C. 590 mg (2.00 mmol) of 1- (5-methyl-4-furoxancarbonyl) piperazine trifluoroacetate and 400 mg of triethylamine were added and the reaction mixture was stirred at room temperature overnight. It was diluted with dichloromethane, the organic phase was washed with a solution of ammonium chloride, 1 M hydrochloric acid and water, and dried over sodium sulfate and the solvent was removed under reduced pressure. Crystallization from ether gives 48 mg (74%) of a colorless solid. 200 MHz-NMR-XH (CDC13): 1.01, t, 3H; 1.59, t, 3H; 1.88, sext., 2H; 2.25, s, 3H; 2.63, s, 3H; 3.00, t, 2H; 3.20, m, 4H; 3.90, m, 2H; 4.02, m, 2H; 4.33, quadr., 2H; 7.19, d, 1H; 7.89, dd, 1H; 8.48, d, 1H; 9.57, s, 1H.

E ng 42 2-. { 2-Ethoxy-5- [4-acetyl-piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propy1-3 H-imidazo [5, l-f] [1,2,4] triazin-4-one By the same method, starting with 40 mg (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 40 mg (0.29 mmol) of N-acetylpiperazine gave 9 mg (18%) of 2-. { 2-ethoxy-5- [4-acetyl-piperazin-1-sulfonyl] -phenyl} -5-methyl-7-propyl-3IT-imidazo [5, 1-f] [1,2,4] triazin-4-one. Rf = 0.34 (dichloromethane / methanol = 95: 5) RM ^ H 200 MHz (CDCl 3): 1.02, t, 3H; 1.61, t, 3H; 1.87, sext., 3H; 2.05, s, 3H; 2.63, s, 3H; 3.00, m, 6H; 3.59,, 2H; 3.72, m, 2H; 4.33, quadr., 2H; 7.18, d, 1H; 7.89, dd, 1H; 8.47, d, 1H; 9.71, s, 1H.

EXAMPLE 43 2- [2-Ethoxy-5- [4-formyl-piperazin-1-sulfonyl] -phenyl) -5-methyl-7-propyl-3J-imidazo [5, 1] [1,2,4] triazin-4-one By the same method, starting with 40 mg (0.097 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 30 mg (0.29 mmol) of N-formylpiperazine afforded 35 mg (73%) of 2- (2-ethoxy-5- [4-formyl-piperazine-1 -sulfonyl] -phenyl.}. -5-methyl-7-propyl-3i? -imidazo [5, lf] [1,2,4] triazin-4-one R = 0.29 (dichloromethane / methanol = 95: 5 ) NMR-1 !! 200 MHz (CDC13): 1.02, t, 3H, 1.61, t, 3H, 1.87, sext., 3H, 2.05, s, 3H, 2.63, s , 3H, 3.00, m, 6H, 3.50, m, 2H, 3.69, m, 2H, 4.33, quadr, 2H, 7.18, d, 1H, 7.89, dd, 1H; 8.00, s, 1H, 8.47, d, 1H, 9.71, s, 1H.

Example 44 2- [2-Ethoxy-5- (3-butylsidnonimine) -1-sulfonyl) -phenyl] -5-ethyl-7-propy1-3 H-imidazo [5, lf] [1,2,4] triazin -4-one 110 mg (0.6 mmol) of 3-butylsidnominine hydrochloride was dissolved in 2.5 ml of pyridine and cooled to 0 ° C. 210 mg (0.5 mmol) of 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, 1-f] chloride [1, 2, 4] was added. triazin-2-yl) -benzenesulfonyl and the reaction mixture was stirred for 2 hours at 0 ° C overnight at room temperature. The mixture was diluted with dichloromethane, the organic phase was washed with water, and dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography (dichloromethane / ethanol) yielded 16 mg (6%) of 2- [2-ethoxy-5- (3-butylsidnonimin) -1-sulphonyl) -phenyl] -5-methyl-7-propyl-3í- imidazo [5, lf] [1,2,4] triazin-4-one. Rf = 0.41 (dichloromethane / methanol = 95: 5) 200 MHz-NMR-NMR (CDCl3): 1.01, 2t, 6H; 1.47, sext., 2H; 1.55, t, 3H; 1.88, m, 2H; 2.04, quin., 2H; 2.62, s, 3H; 2.98, t, 2H; 4.29, quad., 2H; 4.41, t, 2H; 7.08, d, 1H; 7.56, s, 1H; 7.98, dd, 1H; 8.58, d, 1H; 9.79, s, broad, 1H.

Example 45 5-methyl-2- [5- (4-methyl-piperazin-1-sulfonyl) -2-propoxy-phenyl] -7-propyl-3H-imidazo [5, lf] [1,2,4] triazin -4-one 0.85 g (2 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazin chloride were dissolved. -2-yl) -benzenesulfonyl in 20 ml of dichloromethane and cooled to 0 ° C. After the addition of the tip of a DMAP spatula, 0.60 g (6.00 mmol) of N-methylpiperazine was added and the reaction mixture was stirred overnight at room temperature. The mixture was diluted with dichloromethane, the organic phase was washed with a solution of ammonium chloride, dried over sodium sulfate and the solvent was removed under reduced pressure. Crystallization from ether gave 0.80 g (77%) of a colorless solid. Rf = 0.233 (dichloromethane / methanol = 95: 5) NMR-: H 200 MHz (CDC13): 1.01, t, 3H; 1.15, t, 3H; 1.87, sext., 2H; 1.99, sext., 2H; 2.30, s, 3H; 2.52, m, 4H; 2.62, s, 3H; 2.99, t, 2H; 3.10, m, 4H; 4.21, t, 2H; 7.17, d, 1H; 7.87, dd, 1H; 8.48, d, 1H; 9.70, s, 1H.

Example 46 5-Methyl-2- [5- (4-methyl-piperazin-1-sulfonyl) -2-propoxy-phenyl] -7-propyl-3H-imidazo hydrochloride [5, 1-f] [1, 2, 4 ] triazin-4-one 22 mg (0.045 mmol) of 5-methyl-2- [5- (4-methylpiperazin-1-sulfonyl) -2-propoxy-phenyl] -7-propyl-3iJ-imidazo [5, 1] [1] was dissolved. 2,4] triazin-4-one in 2 ml of ether and 1 ml of dichloromethane and was mixed with 0.1 ml of a 1M solution of HCl in ether. The precipitate was filtered with suction after 20 minutes and dried. 200 MHz-NMR-NMR (CDC13) * 0.95, t, 3H; 1.75, m, 2H; 2.56, s, 3H; 2.75, m, 4H; 2.97, t, 2H; 3.15, m, 2H; 3.44, m, 2H; 3.81, m, 2H; 4.15, t, 2H; 7.47, d, 1H; 7.95, m, 2H; 11.12, s, 1H; 12.22, s, 1H.

EXAMPLE 47 2- [5- (4-Hydroxypiperidine-1-sulfonyl) -2-propoxy-phenyl] -5-methyl-7-propyl-3-yl-imidazo [5, lf] [1,2,4] triazin-4 -one By the same method, starting with 850 mg (2 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [l, 2, 4] triazin-2-yl) -benzenesulfonyl and 610 mg (6 mmol) of 4-hydroxypiperidine, 736 mg (75%) of 2- [5- (4-hydroxypiperidine-1-sulfonyl) -2-propoxy were obtained -pheny11 -5-methyl-7-propyl-3-f-imidazo [5, lf] [1,2, 4] triazin-4-one. Rf = 0.07 (dichloromethane / methanol = 95: 5) RMN ^ H 200 MHz "CCDC1"): 1.01, t, 3H, 1.16, t, 3H; 1.80, m, 9H; 2.65, s, 3H; 3.00, m, 4H; 3.32, m, 2H; 3.85, m, 1H; 4.22, t, 2H; 7.17, d, 1H; 7.89, dd, 1H; 8.50, d, 1H; 11.70, s, 1H.

EXAMPLE 48 2- [5- (4-hydroxymethylpiperidine-1-sulfonyl) -2-propoxy-phenyl] -5-methyl-7-propyl-3-yl-imidazo [5, 1] [l, 2,4] triazine-4 -one By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1, 2, 4] triazin-2-yl) -benzenesulfonyl and 35 mg (0.3 mmol) of 4-hydroxymethylpiperidine, 41 mg (82%) of 2- [5- (4-hydroxymethylpiperidine-1-sulfonyl) -2-propoxyphenyl] were obtained] -5-methy1-7-propyl-3iT-imidazo [5, lf] [1,2,4] triazin-4-one. Rf = 0.52 (dichloromethane / methanol = 9: 1) NMR-1! 200 MHz (CDC1): 1.001, t, 3H; 1.16, t, 3H; 1.60, m, 4H; 1.82, m, 5H; 2.31, t, 2H; 2.62, s, 3H; 2.98, t, 2H; 3.48, d, 2H; 3.85, d, 2H; 4.21, t, 2H; 7.17, d, 1H; 7.88, dd, 1H; 8.45, d, 1H; 9.71, s, 1H.

Example 49 2-. { 5- [4- (2-hydroxyethyl) -piperazin-1-sulfonyl] -2- propoxy phenyl} -5-methyl-7-propyl-3H-imidazo [5,1- f] [1, 2, 4] triazin-4-one By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7- propyl-3,4-dihydroimidazo [5, lf] [1, 2, 4] triazin-2-yl) -benzenesulfonyl and 39 mg (0.3 mmol) of 4-hydroxyethylpiperazine, 50 mg (96%) of 2- were obtained. { 5- [4- (2-hydroxyethyl) -piperazin-1-sulphonyl] -2propoxy- • phenyl} -5-methyl-7-propyl-3i? -imidazo [5, 1-f] [1, 2, 4] triazin-4-one. Rf = 0.43 (dichloromethane / methanol = 9: 1) 200 MHz-NMR (CDC13): 1.01, t, 3H; 1.15, t, 3H; 1.88, m, 2H; 2.00, m, 2H; 2.62, m, 9H; 3.00, t, 2H; 3.07, m, 4H; 3.58, t, 2H; 4.23, t, 2H; 7.19, d, 1H; 7.88, dd, 1H; 8.43, d, 1H; 9.85, s, 1H.

For example 50 N- (1, l-dioxotetrahydro-l6-thiophen-3-yl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf ] [1,2,4] triazin-2-yl) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1,2, 4] triazin-2-yl) -benzenesulfonyl and 41 mg (0.3 mmol) of 2-aminosulfolane, 8 mg (14%) of N- (1, 1-dioxotetrahydro-l6-thiophene-3-amide was obtained. il) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] triazin-2-yl) -4-propoxy-benzenesulfonamide . Rf = 0.49 (dichloromethane / methanol = 9: 1) NMR-1! 200 MHz (CDC13): 1.01, t, 3H; 1.15, t, 3H; 1.85,, 2H; 1.99, m, 2H; 2.30,, 1H; 2.50, m, 1H; 2.62, s, 3H; 2.95, m, 4H; 3.21,, 1H; 4.20, m, 3H; 5.98, s, 1H; 7.18, d, 1H; 8.51, d, 1H; 9.71, s, 1H.

Example 51 N- (2-Dimethylaminoethyl) -N-methyl-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, 1] [1, 2, 4] triazin -2-il) 4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-midazo [5, lf] [1, 2, 4] triazin-2-yl) -benzenesulfonyl and 31 mg (0.3 mmol) of 1,1,4-trimethyldiaminoethane, 39 mg (79%) of N- (2-dimethylaminoethyl) -N-methyl-3 were obtained - (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] triazin-2-yl) -4-propoxy-benzenesulfonamide.

Rf = 0.28 (dichloromethane / methanol = 9: 1) 200 MHz-NMR (CDC13): 1.01, t, 3H; 1.15, t, 3H; 1.88, m, 2H; 2.01, m, 2H; 2.25, s, 6H; 2.50, t, 2H; 2.62, s, 3H; 2.82, s, 3H; 3.01, t, 2H; 3.18, t, 2H; 4.21, t, 2H; 7.16, d, 1H; 7.91, dd, 1H; 8.50, d, 1H; 9.70, s, 1H.

Example 52 3- (5-Methyl-4-oxo-7-propyl-3,4-dihydroimidazo- [5, 1-f] [1, 2, 4] triazin-2-yl) -N- (3-morpholine) -4-ylpropyl) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [l, 2,4] triazin-2-yl) chloride - Benzenesulfonyl and 43 mg (0.3 mmol) of l- (3-aminopropyl) -morpholine gave 52 mg (97%) of 3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazole). - [5, 1-f] [1,2,4] triazin-2-yl) -N- (3-morpholin-4-yl-propyl) -4-propoxy-benzenesulfonamide. Rf = 0.33 (dichloromethane / methanol = 9: 1) 200 MHz-NMR (CDC13): 1.01, t, 3H; 1.15, t, 3H; 1.71, m, 2H; 1.93, m, 4H; 2.43, m, 6H; 2.62, s, 3H; 2.98, t, 2H; 3.12, t, 2H; 3.70,, 4H; 4.21, t, 2H; 7.15, d, 1H; 7.96, dd, 1H; 8.55, d, 1H; 9.85, s, 1H.

Example 53 N, N-bis- (2-hydroxyethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1, 2, 4] triazin -2-yl) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3, -dihydroimidazo [5, 1] [l, 2,4] triazin-2-yl) -benzenesulfonyl chloride and 32 mg (0.3 mmol) of bishydroxyethylamine gave 34 mg (69%) of N, N-bis- (2-hydroxyethyl) -3- (5-methyl-4-oxo-7-propyl-3, 4- dihydro-imidazo- [5, lf] [l, 2,4] triazin-2-yl) -4-propoxy-benzenesulfonamide. Rf = 0.36 (dichloromethane / methanol = 9: 1) 200 MHz-NMR (CDC13): 1.01, t, 3H; 1,15, t, 3H; 1.85, m, 2H; 1.97, m, 2H; 2.60, s, 3H; 2.98 ^ t, 2H; 3.33, t, 4H; 3.87, t, 4H; 4.20, t, 2H; , 7.15, d, 1H; 7.92, dd, 1H; 8.49, d, 1H; 9.85, s, 1H.

Example 54 N- (3-hydroxybenzyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, 1] [1, 2, 4] triazin-2-yl -4-Propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3, -dihydroimidazo [5, lf] [1,2,4 chloride ] triazin-2-yl) -benzenesulfonyl 'and 37 mg (0.3 mmol) of 31-hydroxybenzylamine? 4 mg (8%) of N- (3-hydroxybenzyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1, 2, 4] triazin-2-yl) -4-propoxy-benzenesulfonamide. Rf = 0.43 (dichloromethane / methanol = 9: 1) 200 MHz-NMR (CDCl3): 1.01, t, 3H; 1.13, t, 3H; 1.83, m, 2H; 1.96, m, 2H; 2.59, s, 3H; 2.96, t, 2H; 4.16,, 4H; 5.05, t, 1H; 6.52, s, 1H; 6.70, m, 2H; 7.06, m, 2H; 7.93, dd, 1H; 8.41, d, 1H; 9.77, s, 1H.

Example 55 N-Ethyl-N- (2-hydroxyethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] triazin -2-yl) -4-propoxy-15-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1,2,4] triazin-2-yl chloride) -benzenesulfonyl and 27 mg (0.3 mmol) of ethylhydroxyethylamine, 18 mg (38%) of N-ethyl-N- (2-hydroxyethyl) -3- (5-methyl-4-oxo-7-propyl) were obtained. 3, 4-dihydro-imidazo- [5, lf] [1,2,4] triazin-2-yl) -4-propoxy-benzenesulfonamido. Rf = 0.48 (dichloromethane / methanol = 9: 1) NMR-1! 200 MHz (CDC1) * 1.01, t, 3H; 1.15, 2t, 6H; 1.75, s, 2H; 1.85, m, 2H; 1.98, m, 2H; 2.40, s, 1H; 2.62, s, 3H; 2.99, t, 2H; 3.32,, 4H; 3.90, quadr., 2H; 4.21, quadr., 2H; 7.15, d, 1H; 7.95, dd, 1H; 8.55, d, 1H; 9.73, s, 1H.

Example 56 N- (3-ethoxypropyl-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, 1] 1, 2, 4] triazin-2-yl) - 4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1,2] chloride. 4] triazin-2-yl) -benzenesulfonyl and 31 mg (0.3 mmol) of 3-ethoxypropylamine gave 47 mg (96%) of N- (3-ethoxypropyl-3- (5-methyl-4-oxo-7) -propyl-3, 4-dihydro-imidazo- [5, lf] [1, 2, 4] triazin-2-yl) -4-propoxy-benzenesulfanamide, Rf = 0.60 (dichloromethane / methanol = 9: 1) 200 MHz-NMR (CDC13): 1.01, t, 3H, 1.15, m, 6H, 1.89,, 7H, 2.62, s, 3H, 3.00, t, 2H, 3, 12, quadr., 2H, 3.46,, 4H, 4.20, t, 2H, 5.52, m, 1H, 7.15, d, 1H, 7.98, dd, 1H, 8.55, d, 1H; 9.85, s, 1H.

Example 57 2- [5- (4-hydroxypiperidine-1-sulfonyl) -2-propoxy-phenyl] -5-methyl-7-propyl-3i [beta] -imidazo- [5, 1] [1,2,4] triazine -4-one By the same method, starting with 212 mg (0.5 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1,2, 4] triazin-2-yl) -benzenesulfonyl and 152 mg (1.5 mmol) of 4-hydroxypiperidine gave 125 mg (50%) of 2- [5- (4-hydroxy-iperidin-1-sulfonyl) -2-propoxy] phenyl] -5-methyl-7-propyl-3β-imidazo- [5, lf] [1,2,4] triazin-4-one. Rf = 0.07 (dichloromethane / methanol = 19: 1) 200 MHz-NMR-NMR (CDC13): 1.05, t, 3H; 1,18, t, 3H; 1.98,, 8H; 2.71, s, 3H; 3.10, m, 2H; 3.28,, 4H; 3.88,, 1H; 4.28, t, 2H; 7.21, d, 1H; 7.97, dd, 1H; 8.45, d, 1H; 10.45, s, 1H.

Example 58 3- (5-Methyl-4-oxo-7-propyl-3,4-dihydroimidazo- [5,1-f] [1,2,4] triazin-2-yl) -4-propoxy-N- pyridin-4-yl-benzenesulfonamide By the same method, starting with 85 mg (0.2 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1, 2, 4] triazin-2-yl) -benzenesulfonyl and 56 mg (0.6 mmol) of 4-aminopyridine after refluxing for 18 hours in 1 ml of THF gave 24 mg (25%) of 3- (5-methyl) -4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2, 4] triazin-2-yl) -4-propoxy-N-pyridin-4-yl-benzenesulfonamide. Rf = 0.13 (dichloromethane / methanol = 9: 1) 200 MHz-NMR-NMR (CDC13 + CD30D): 1.01, t, 3H; 1.09, t, 3H; 1.90,, 4H; 2.60, s, 3H; 2.99, t, 2H; 4.16, t, 2H; 7.05, d, 2H; d, 2H; 8.05, dd, 1H; 8.41, d, 1H; 7.15, d, 1H; 7.88, d 2H; 8.05, dd, 1H; 8.41, d, 1H.

Example 59 N, N-diethyl-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] triazin-2-yl) - 4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3, 4-dihydroimidazo [5, lf] [1,2,4 ] triazin-2-yl) -benzenesulfonyl and 22 mg (0.6 mmol) of diethylamine, 42 mg (92%) of N, N-diethyl-3- (5-methyl-4-oxo-7-propyl-3 were obtained , -dihydro-imidazo- [5, lf] [1,2,4] triazin-2-yl) -4-propoxy-benzenesulfonamide. Rf = 0.64 (dichloromethane / methanol NMR-XH 200 MHz (CDC13): 1.01, t, 3H, 1.18, 2t, 9H, 1.92, 2 sext., 4H, 2.62, s, 3H, 3.00, t, 2H, 3.29, quad, 4H, 4.21, t, 2H, 7.13, d, 7.93, dd, 1H, 8.51, d, 1H, 9.85, s, 1H.

EXAMPLE 60 1- [3- (5-Methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, 1] [1,2,4] triazin-2-yl) -4- acid propoxy-benzenesulfonyl] -piperidine-4-carboxylic acid By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3, -dihydroimidazo [5, lf] [1,2,4 chloride ] triazin-2-yl) -benzenesulfonyl and 14 mg (0.6 mmol) of piperidinecarboxylic acid in 1 ml of a mixture of THF and water (1: 1) with 26.5 mg of sodium carbonate, 21 mg (41%) was obtained of 1- [3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1, 2,] triazin-2-yl) -4-propoxy-benzenesulfonyl] -piperidine-4-carboxylic acid.

Rf = 0.28 (dichloromethane / methanol = 9: 1) NMR-1! 200 MHz (CDC13): 0.90, t, 3H, 1.04, t, 3H; 1.80, m 4H; 2.21, m, 2H; 2.51, s, 3H; 2.85,, 2H, 3.56, m, 6H; 4.10, t, 2H; 7.12, d, 1H; 7.71, dd, 1H; 8.10, d, 1H; 10.72, s, broad, 1H.

Example 61 5-methyl-2- [5- (morpholin-4-sulf onyl) -2-propy-phenyl] -7-propyl-3i? -imidazo- [5,1-f] [1,2, 4] triazin-4-one By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1, 2, 4] triazin-2-yl) -benzenesulfonyl and 26 mg (0.3 mmol) of morpholine, 34 mg (71%) of 5-methyl-2- [5- (morpholin-4-sulfonyl) -2-propoxy-phenyl was obtained ] -7-propyl-3ff-imidazo- [5, 1-f] [1, 2, 4] triazin-4-one. Rf = 0.64 (dichloromethane / methanol = 9: 1) NMR-1! 200 MHz (CDC13): 1.01, t, 3H; 1,16, t, 3H; 1.89, sext., 2H; 2.00, sext., 2H; 2.63, s, 3H; 3.02, m, 4H; 4.25, t, 2H; 7.19, d, 1H; 7.89, dd, 1H; 8.48, d, 1H; 9.78, s, 1H.

Example 62 N- (2-hydroxyethyl) -N-ethyl-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] triazin -2-il) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2, 4] triazin-2-yl) -benzenesulfonyl and 23 mg (0.63 mmol) of methylhydroxyethylamine gave 25 mg (54%) of N- (2-hydroxyethyl) -N-methyl-3- (5-methyl- 4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf) [1, 2,] triazin-2-yl-) 4-propoxy-benzenesulfonamide.

Rf = 0.53 (dichloromethane / methanol = 9: 1) 200 MHz-NMR-NMR (CDC13): 1.01, t, 3H; 1.15, t, 3H; 1.82, m, 2H, 1.99, sext., 2H; 2.40, s, broad, 1H; 2.62, s, 3H; 2.89, s, 3H; 2.99, t, 2H; 3.21, t, 2H; 3.80. s, broad, 2H; 4.21, t, 2H; 7.16, d, 1H; 7.92, dd, 1H; 8.50, d, 1H; 9.79, s, 1H.

Example 63 N- (2-hydroxyethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- (5, lf) [l, 2,4] triazin-2-yl ) -4-propexy-N-propyl-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propexy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl chloride ) -benzenesulfonyl and 31 mg (0.6 mmol) of propylhydroxyethylamine, gave 20 mg (40%) of N- (2-hydroxyethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro) -imidazo- [5, lf] [1,2,4] triazin-2-yl) -4-propoxy-N-propyl-benzenesulfonamide. Rf = 0.52 (dichloromethane / methanol = 9: 1) NMR-1! 200 MHz (CDC13): 0.90, t, 3H, 1.01, t, 3H; 1.15, t, 3H; 1.52, m, 2H; 1.88, m, 2H; 2.00, m, 2H; 2.40, s, 1H; 2.63, s, 3H; 3.01, t, 2H; 3.22, m, 4H; 3.80, quad., 2H; 4.21, t, 2H; 7.15, d, 2H; 7.95, dd, 1H; 8.55, d, 1H; 9.75, z, 1H.

EXAMPLE 64 N- [2- (3,4-Dimethoxy-phenyl) ethyl] -N-methyl-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf ] [1,2,4] triazin-2-yl) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1,2, 4] triazin-2-yl) -benzenesulfonyl and 59 mg (0.3 mmol) of N-methyl-3,4-dimethoxyphenylethylamine gave 45 mg (73%) of N- [2- (3,4-dimethoxy-phenyl) ) ethyl] -N-methy1-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [l, 2,4] triazin-2-iI) ~ 4-benzenesulfonamide. Rf = 0.35 (dichloromethane / methanol = 19: 1) NMR-1! 200 MHz (CDC13): 0.90, t, 3H; 1.07, t, 3H; 1.92, m, 2H; 2.55, s, 3H; 2.73, s, 3H; 2.78, m, 2H; 2.89, t, 2H; 3.23, t, 2H, 3.80, s, 6H; 4.15, t, 2H; 6.65, m, 3H; 7.05, d, 1H; 7.75, dd, 1H; 8.41, d, 1H; 9, 67, s, 1H.

Example 65 N-Allyl-N- (2-hydroxyethyl) -3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [l, 2,4] triazin -2-il) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 31 mg (0.3 mmol) of allylhydroxyethylamine gave 34 mg (70%) of N-allyl-N- (2-hydroxyethyl) -3- (5-methyl- 4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1, 2, 4] triazin-2-yl) -4-propoxybenzenesulfonamide. Rf = 0.52 (dichloromethane / methanol = 9: 1) 200 MHz-NMR (CDC13) * 1.01, t, 3H; 1.15, t, 3H; 1.85, m, 2H; 1.99, m, 2H; 2.38, s, broad, 1H; 2.63, s, 3H; 3.00, t, 2H; 3.32, t, 2H; 3.86, t, 2H; 3.90, d, 2H; 4.25 t, 2H; 5.21, m, 2H; 5.71, m, 1H; 7.15 d, 1H, 7.95, dd, 1H; 8.55, d, 1H; 9.77, s, 1H.

EXAMPLE 66 N-Allyl-N-cyclopentyl-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, 1] [l, 2,4] triazin-2-yl ) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) ~ benzenesulfonyl and 78 mg (0.3 mmol) of allylcyclopentylamine gave 33 mg (64%) of N-allyl-N-cyclopentyl-3- (5-methyl-4-oxo- 7-propyl-3,4-dihydro-imidazo- [5, lf] [1, 2, 4] triazin-2-yl) - -propoxy-benzenesulfonamide Rf = 0.43 (dichloromethane / methanol = 19: 1) NMR ^ H 200 MHz (CDClj): 1.01, t, 3H; 1.15, t, 3H; 1.53, m, 9H; 2.00, m, 4H; 2.63, s, 3H; 3.00, t, 2H; 3.80, m, 2H; 4.21, t, 2H; 5.20, m, 2H; 5.88, m, 1H; 7.12, d, 1H; 7.95, dd, 1H; 8.55, d, 1H; 9.75, s, 1H.

Example 67 N-Allyl-N-ethyl-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] triazin-2-yl ) -4-propoxy-benzenesulfonamide By the same method, starting with 42 mg (0.1 mmol) of 4-propoxy-3- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2, 4] triazin-2-yl) -benzenesulfonyl and 26 mg (0.3 mmol) of allylethylamine, 30 mg (64%) of N-allyl-N-ethyl-3- (5-methyl-4-oxo- 7-propyl-3,4-dhydro-imidazo [5, lf] [1, 2, 4] triazin-2-yl) -4-propoxy-benzenesulfonamide. Rf = 0.44 (dichloromethane / methanol = 19: 1) 200 MHz-NMR (CDC13): 1.01, t, 3H; 1.15, t, 6H; 1.89, m, 2H; 2.01, m, 2H; 2.63, s, 3H; 3.00, t, 2H; 3.27, quadr., 2H, 3.87, d, 2H; 4.23, t, 2H; 5.20, m, 2H; .72, m, 1H; 7.15, d, 1H; 7.95, dd, 1H; 8.55, d, 1H; 9.89, s, 1H.

EXAMPLE 68 2 [2-Ethoxy-4-methoxy-5- (4-methylpiperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3-imidazo- [5,1-f] [1, 2, 4] triazin-4-one mg (0.045 mmol) of 4-ethoxy chloride 2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, 11] [1, 2, 4] triazin-2-yl] -benzenesulfonyl in 0.5 ml of dichloromethane and the tip of a spatula of dimethylaminopyridine and 14 mg (0.136 mmol) of N-methylpiperazine was mixed and the reaction mixture was stirred at room temperature overnight After purification on silica gel, 12.8 mg (55%) of 2- [2-ethoxy-4-methoxy-5-imidazo- [5, 1-f] [1, 2, 4] triazine was obtained. 4-one Rf = 0.22 (dichloromethane / methanol = 20: 1) NMR-1 !! 200 MHz (CDC1): 0.94, t, 3H, 1.55, t, 3H, 1.80,, 2H, 2 24, s, 3H, 2.42, t, 4H, 2.55, s, 3H, 2.92, t, 2H, 3.19, t, 4H, 3.91, s, 3H, 4.25 , quadr., 2H; 6; 48, s, 1H; 8.57, s, 1H; 9.54, s, 1H.

Example 69 2-. { 2-Ethoxy-5- [4- (2-hydroxyethyl) -piperazin-1-sulfonyl] -4-methoxy-phenyl} -5-methyl-7-propyl-3i? -imidazo- [5,1-f] [1, 2, 4] triazin-4-one By the same method, starting with 20 mg (0.045 mmol) of 4-ethoxy-2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo) chloride [5, lf] [1,2,4] triazin-2-yl) -benzenesulfonyl and 18 mg (0.14 mmol) of 4-hydroxyethylpiperazine afforded 11 mg (46%) of 2-. { 2-Ethoxy-5- [4- (2-hydroxyethyl) -piperazin-1-sulfonyl] -4-ethoxyphenyl) -5-methyl-7-propyl-3-yl-imidazo [5, 1-f] [1, 2, 4) triazin-4-one. Rf-0.34 (dichloromethane / methanol = 15: 1) 200 MHz-NMR (CDC13): 0.94, t, 3H; 1.55, t, 3H; 1.80, m, 3H; 2.52, m, 9H; 2.92, t, 2H; 3.20, t, 4H; 3.44. t, 2H; 3.92, s, 3H; 4.25, quadr., 2H; 6.49, s, 1H; 8.56, s, 1H; 9.55, s, 1H.

EXAMPLE 70 4-Ethoxy-N-ethyl-N- (2-hydroxyethyl) -2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [ 1, 2, 4] triazin-2-yl) benzenesulfonamide By the same method, starting with 20 mg (0.045 mmol) of 4-ethoxy-2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo) chloride [5, lf ] [1, 2,4] triazin-2-yl) -benzenesulfonyl and 12 mg (0.14 mmol) of ethylhydroxyethylamine gave 8 mg (34%) of 4-ethoxy-N-ethyl-N- (2-hydroxyethyl) -2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] -benzenesulfonamide Rf = 0.45 (dichloromethane / methanol = 15: 1) 200 MHz-NMR (CDC13): 1.02, t, 3H, 1.18, t, 3H, 1.61, t, 2H, 1.88, m, 2H, 2.39, s, broad, 1H, 2.65, s, 3H, 3.00, t, 2H, 3.38, quadr., 2H, 3.45, t, 2H, 3.78, m, 2H, 4.01, s , 3H; 4.20, quadr., 2H; 6.58, s, 1H; 8.67, s, 1H; 9.61, 6, 1H.

EXAMPLE 71 4-Ethoxy-N- (4-ethoxyphenyl) -2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2 , 4] triazin-2-yl) -benzenesulfonamide By the same method, starting with 20 mg (0.045 mmol) of 4-ethoxy-2-methoxy-5- (5-methyl-4-oxo-7-propyl-3, 4-dihydro-imidazo chloride (5, lf ] [l, 2,4] triazin-2-yl) -benzenesulfonyl and 19 mg (0.14 mmol) -of 4-ethoxyaniline gave 7 mg (34%) of 4-ethoxy-N- (4-ethoxyphenyl) - 2-methoxy-5- (5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [l, 2,4] triazin-2-yl) -benzenesulfonamide. 0.36 (dichloromethane / methanol = 20: 1) 200 MHz-NMR-NMR (CDC13): 1.02, t, 3H, 1.33, t, 3H, 1.59, t, 3H, 1.86, sext., 2H, 2.62, s, 3H, 3.02, t, 2H, 3.92, quad, 2H, 4.11, s, 3H, 4.31, quad, 2H, 6.58, s, 1H, 6.72, d, 2H, 6.88, s, broad, 1H, 6.99, d, 2H, 8.50, s, 1H, 9.59, s, 1H.

Example 72 4-Ethoxy-N-ethyl-N- (2-hydroxy-ethyl) -3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2,4] triazin-2-yl) benzenesulfonamide 0.64 mg (1.5 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazine chloride was dissolved. 2-yl) -benzenesulfonyl in 20 ml of dichloromethane and cooled to 0 ° C. After adding the tip of a dimethylaminopyridine spatula, 0.40 mg (4.50 mmol) of 2- (ethylamino) -ethanol was added, and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane, the organic phase was washed with water and dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography (dichloromethane / methanol = 95: 5) gave 0.454 g (63%) of a colorless solid.

RMN-1 !! 200 MHz (CDCl 3): 1.02, t, 3H; 1.20, t, 3H; 1.35, t, 3H; 1.61, t, 3H; 1.88, sext., 2H; 2.25, s, broad, 1H; 3.01,, 4H; 3.32 m, 4H; 3.70, m, 2H; 3.80, m, 2H; 4.37, quadr., 2H; 7.15, d, 1H; 7.98, dd, 1H; 8.56, d, 1H; 9.70, s, 1H.

EXAMPLE 73 N- (2-methoxyethyl) -3- (5-ethyl-4-oxo-7-propyl-3,4-daharyl-imidazo- [5, lf] [1,2,4] triazin-2-yl -4-ethoxybenzenesulfonamide By the same method, starting with 40 mg (0.094 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydroimidazo [5, lf] [1,2, 4] triazin-2-yl) -benzenesulfonyl and 21 mg (0.282 mmol) of 2-methoxyethylamine gave 15 mg (34%) of N- (2-methoxyethyl) -3- (5-ethyl-4-oxo- 7-propyl-3,4-dihydroimidazo [5, lf] [1,2, 4] triazin-2-yl) -4-ethoxybenzenesulfonamide. Rf = 0.2 (ethyl acetate / cyclohexane = 2: 1) NMR-1! 200 MHz (CDC13): 0.97, t, 3H; 1.25, t, 3H; 1.53, t, 3H; 1.82, sext., 2H; 2.97, m, 4H; 3.11, m, 2H, 3.22, s, 3H; 3.39, t, 2H; 4.37, cuart., 2H; 5.00, t, 1H; 7.17, d, 1H; 7.97, dd, 1H, 8.53, d, 1H; 9.82, s, 1H.

Example 74 N, N-bis- (2-methoxyethyl) -3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1, 2, 4] triazine- 2-yl) -4-toxibenzenesulfonamide By the same method, starting with 40 mg (0.094 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl chloride ) -benzenesulfonyl and 38 mg (0.28 mmol) of bis-methoxyethylamine gave 17 mg (34%) of N, N-bi-2- (2-methoxyethyl) -3- (5-ethyl-4-oxo-7-propyl) 3, 4-dihydro-imidazo- [5, lf] [1,2,4] -triazin-2-yl) -4-ethoxyhencenesulfonamide. Rf = 0.34 (ethyl acetate / cyclohexane = 2: 1) 200 MHz-NMR (CDC13): 0.97, t. 3H; 1.27, t, 3H; 1.53, t, 3H; 1.80, sext., 2H; 2.95, m, 4H; 3.22, s, 6H; 3.39, m, 4H; 3.49, m, 4H; 4.27, quadr., 2H; 7.17, d, 1H; 7.97, dd, 1H; 8.53, d, 1H; 9.82, s, 3H.

Example 75 2- [5- (4-hydroxypiperidine-l-sulfonal) -2-ethoxy-enyl] -5-ethyl-7-propyl-3H-imidazo- [5, 1-y] [1, 2, 4] -triazin-4-one By the same method, starting with 640 mg (1.5 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride. 2,4] triazin-2-yl) -benzenesulfonyl and 460 mg (4.5 mmol) of 4-hydroxypiperidine, 495 mg (66%) of 2- [5- (4-hydroxypiperidine-1-sulfonyl) -2- were obtained ethoxyphenyl) -5-ethyl-7-propyl-3i? -imidazo [5, lf] [1,2,4] triazin-4-one. Rf = 0.37 (dichloromethane / methanol = 19: 1) RMN - ^ - H 200 MHz (CDC13)): 1.02, t, 3H; 1.32, t, 3H; 1.60, t, 3H; 1.80, m, 7H; 2.97, m, 6H; 3.30, m, 2H; 3.82,, 1H; 4.34. quadr., 2H; 7.17, d, 1H; 7.90, dd, 1H; 8.45, d, 1H; 9.75, s, 1H.

Example 76 2- [5- (4-hydroxymethylpiperidine-1-sulfonyl) -2-ethoxy-phenyl] -5-ethyl-7-propyl-3H-imidazo- [5, lf] [1,2,4] -triazin -4-one By the same method, starting with 40 mg (0.094 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 33 mg (0.28 mmol) of 4-hydroxymethylpiperidine afforded 23 mg (48%) of 2- [5- (4-hydroxymethylpiperidine-1-sulfonyl) -2- ethoxyphenyl] -5-ethyl-7-propyl-3ff-imidazo- [5, lf] [1,2,4] triazin-4-one. Rf = 0.33 (dichloromethane / methanol = 10: 1) 200 MHz-NMR (CDC13): 1.01, t, 3H; 1.33, t, 3H; 1.60, t, 3H; 1.80, m, 8H; 2.41, m, 2H; 3.00, m, 4H; 9.56, m, 4H; 4.95, quad. 2H; 7.17, d, 1H; 7.88, dd, 1H; 8.45, d, 1H; 9.71, s, 1H.

Example 77 2-. { 2-Ethoxy-5- [4- (2-hydroxyethyl) -piperazin-1-sulfonyl] -phenyl) -5-ethyl-7-propyl-3i-imidazo- [5, lf] [1,2,4] triazin-4-one By the same method, starting with 40 mg (0.094 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [l, 2,4] triazin-2-yl) -benzenesulfonyl and 37 mg (0.28 mmol) of 4-hydroxyethylpiperazine afforded 35 mg (71%) of 2- (2-ethoxy-5- [4- (2-hydroxyethyl) -piperazin-1-sulfonyl] -phenyl.} - 5-ethyl-7-propyl-3i-imidazo- [5, lf] [l 2,4] triazin-4-one Rf = 0.65 (dichloromethane / methanol = 10: 1) EXAMPLE 78 2- [2-Ethoxy-5- (4-methyl-piperazin-1-sulfonyl) -phenyl] -5-ethyl-7-propyl-3H-imidazo- [5, 1] [1,2,4] triazine- 4-one By the same method, starting with 640 mg (1.50 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1] chloride, 2,4] triazin-2-yl) -benzenesulfonyl and 450 mg (4.5 mmol) of 4-hydroxyethylpiperazine, 495 mg (66%) of 2- [2-ethoxy-5- (4-methylpiperazine-1-sulfonyl) were obtained ) -phenyl] -5-ethyl-7-propyl-3'T-imidazo- [5, lf] [1,2,4] triazin-4-one. Rf = 0.65 (dichloromethane / methanol = 19: 1) NMR-1! 200 MHz (CDC13): 1.01, t, 3H; 1.35, t, 3H; 1.61, t, 3H; 1.89, sext., 2H; 2.31, s, 3H; 2.53, m, 4H; 3.05, m, 8H; 4.35, quadr., 2H; 7.17, d, 1H; 7.89, dd, 1H; 8.48, d, 1H; 9.65, s, 1H.

Example 79 2- [2-Ethoxy-5- (4-methylpiperazin-1-sulfonyl) -phenyl] -5-ethyl-7-propy1-3H-imidazo [5,1-f] [1, 2, 4] hydrochloride ] triazin-4-one 300 mg (0.61 mmol) of 2- (2-ethoxy-5- (4-methylpiperazin-1-sulfonyl) -phenyl] -5-ethyl-7-propyl-3H-imidazo [5, 1] [1] was dissolved. 2,4] triazin-4-one in a mixture of ether and dichloromethane and mixed with 2 ml of a 1M solution of HCl in ether.After 20 minutes, the precipitated solid was filtered off with suction and dried. 200 MHz (DMSO-d6): 0.95, t, 3H, 1.32, 2t, 6H, 1.80, sext, 2H, 2.76, m, 4H, 3.01, m, 4H, 3.15 , m, 2H, 3.44,, 2H, 3.81, m, 2H, 4.25, quadr., 2H, 7.49, d, 1H, 7.95, m, 2H, 11.25, s, 1H; 12.30, s, 1H.

Example 80 3- (5-ethyl-4-oxo-7-propyl-3,4-dihydroimidazo [5,1-f] [1, 2, 4] triaz'in-2-yl) -N- (3- morpholin-4-yl-propyl; -4-ethoxybenzenesulfonamide By the same method, starting with 640 mg (1.5 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo [5, lf] [1,2,4] triazin-2-yl chloride ) -benzenesulfonyl and 650 mg (4.5 mmol) of I-. { 3-aminopropyl) -morpholine, 476 mg (59%) of 3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo- [5, 1- f] [1,2 , 4] triazin-2-yl) -N- (3-morpholin-4-yl-propyl) -4-ethoxybenzenesulfonamide. i Rf = 0.18 (dichloromethane / methanol = 19: 1) NMR-1! 200 MHz (CDC13) * 1.01, t, 3H: 1.32, t, 3H; 1.60, t, 3H; 1.70, m, 3H; 1.89, sext., 2H; 2.43, m, 7H; 3.01, m, 4H; 3.15, t, 2H; 3.70, m, 4H; 4.35, quad., 2H; 7.15, d, 1H; 7.95, dd, 1H; 8.55, d, 1H; 9.82, s, 1H.

Example 81 10 N- (2-hydroxyethyl) -3- (5-ethyl-4-oxo-7-propyI-3,4-dihydro-imidazo- [5, lf] [1, 2, 4] eriazin-2 -yl) -4-ethoxy-N-propyl-benzenesulfonamide By the same method, starting with 640 mg (1.5 mmol) of 4-ethoxy-3- (5-ethyl-4-oxo-7- propyl-3,4-dihydro-imdazo [5, lf] [1] chloride. , 2,4] triazin-2-yl) -benzenesulfonyl and 464 mg (4.5 mmol) of propylhydroxyethylamine, 600 mg (81%) of N- (2-hydroxyethyl) -3- (5-ethyl-4- oxo-7-propyl-3,4-dihydro-imidazo- [5, lf] [1,2,4] triazin-2-yl) -4-ethoxy-N-propyl-benzenesulfonamide. Rf = 0.73 (dichloromethane / methanol = 10: 1) NMR-1! 200 MHz (CDC13): 0.91, t, 3H; 1.01, t, 3H; 1.32, t, 3H; 1.62, m, 5H; 1.88, m, 2H; 2.32, s, 1H; 3.01, m, 4H; 3.22, m, 4H; 3.80, m, 2H; 4.35, t, 2H; 7.15, d, 2H; 7.95, dd, 1H; 8.55, d, 1H; 9.75, s, 1H.

The sulfonamides listed in Tables 1, 2, 3, 4 and 6 below were prepared by an automated parallel synthesis from 4-ethoxy-3- (5-methyl-4-oxo-7-propyl-3 chloride, 4-dihydro-imidazo [5, 1] [1, 2,4] triazin-2-yl) -benzenesulfonyl and the corresponding amine using one of the following three standard procedures. The sulfonamides listed in Table 5 were prepared by the same methods by an automated parallel synthesis from the 4-ethoxy-3- (5-ethyl-4-oxo-7-propyl-3,4-dihydro-imidazo chloride. 5, 1-f] [1, 2, 4] triazin-2-yl) benzenesulfonyl and the corresponding amine. The purity of the final products was determined by HPLC, and is characterized by LC-MS. The content of the desired compound according to HPLC-MS is given in percent in the tables in the column "HPLC". The standard procedure A was used for the amines with acidic functionalities, the standard B procedure was used for the amines with neutral functionalities, the standard procedure C was used for the amines with additional basic functionalities. In the structural formulas of the following Tables 1, 2, 3, 4, 5 and 6 occasionally hydrogen atoms were not represented. The nitrogen atoms with a free valence are therefore understood as radicals -NH-. Standard procedure A: Reaction of amines with acidic functionalities. Initially, 0.005 mmol of amine is charged, 0. 042 mmol of sulfonyl chloride and 0.10 mmol of Na 2 CO 3, and 0.5 ml of a THF / H 20 mixture are added by hand pipetting. After 24 hours at room temperature, it was mixed with 0.5 ml of a 1M H2SO4 solution and filtered through a two-phase cartridge (500 mg Extrelut (upper phase) and 500 mg of SiO2, mobile phase of ethyl acetate) After concentrating the filtrate under reduced pressure, the product is obtained. Standard procedure B: Reaction of animals with neutral functionalities.

Initially 0.125 mmol of amine is charged and 0.03 mmol of sulfonyl chloride is pipped from the synthesizer as a solution in 1,2-dichloroethane. After 24 hours, the mixture was mixed with 0.5 ml of a 1M H2SO4 solution and filtered through a two-phase cartridge (500 mg Extrelut (Upper phase) and 500 mg Si02, mobile phase: linden acetate ). The filtrate was concentrated under reduced pressure. Standard procedure C: Reaction of amines with basic functionalities. Initially 0.05 mmol of amine is charged and 0.038 mmol of sulfonyl chloride is pipped from the synthesizer as a solution in 1,2-dichloroethane and 0.05 mmol of triethylamine. After 24 hours, the mixture is initially mixed with 3 ml of a saturated NaHCO 3 solution and the reaction mixture is filtered through the two-phase cartridge. The product was obtained after concentrating the filtrate under reduced pressure. All reactions are monitored by thin layer chromatography. If the reaction was not completed after 24 hours at room temperature, the mixture is heated for another 12 hours at 60 ° C and then the experiment is finished.

Example 336 Trihydrate 2- [2-ethoxy-5- (4-ethylpiperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3H-imidazo- [5, 1-f] [1, 2, 4] hydrochloride ] triazin-4-one If the free base of Example 19 was crystallized from a mixture of an organic solvent and dilute aqueous hydrochloric acid, a trihydrate hydrochloride was thus obtained. p.f. : 218 ° C Water content: 9.4% (K. Fischer) Chloride content: 6.1% Example 337 2- [2-Ethoxy-5- (4-ethyl-piperazin-1-sulfonyl) -phenyl] -5-hydrochloride -methyl-7-propyl-3H-imidazo- [5, 1-f] [1, 2, 4] triazin-4-one 0.35 g (0.712 mmol) of 2- [2-ethoxy-5- (4-ethyl-piperazin-1-sulfonyl) -phenyl] -5-methyl-7-propyl-3H-imidazo [5, lf) was suspended. 1, 2,] triazin-4-one in 8 ml of ether and dichloromethane was added until a homogeneous solution formed. 24 ml of a 1M solution of HCl in ether was added and the mixture was stirred for 20 minutes at room temperature and filtered with suction. 372 mg (99%) of 2- [2-ethoxy-5- (4-ethylpiperazin-l-sulfonyl) -phenyl] -5-methyl-7-propyl-3H-imidazo- [5, lf] dihydrochloride were obtained. [1,2,4] triazin-4-one.

NMR --- H 200 MHz (DMSO-d6): 0.96, t, 3H; 1.22, t, 3H; 1.36, t, 3H; ?, 82, sext., 2H; 2.61, s, 3H; 2.88, m, 2H; 3.08,, 6H; 3.50, m, 2H; 3.70, m, 2H; 4.25, quadr., 2H; 7.48, d, 1H; 7.95, m, 2H; 11.42, s, 1H; 12.45, s, 1H. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects or products to which it refers. Having described the invention as above, property is claimed as contained in the following:

Claims (11)

1. 2-phenyl-substituted imidazotriazinones of the general formula (I) wherein R1 represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, R2 represents straight chain alkyl having up to 4 carbon atoms, R- and R4 are the same or different and each represent hydrogen or represent alkenyl or straight or branched chain alkoxy having on each up to 8 carbon atoms, or representing a straight or branched chain alkyl chain having up to 10 carbon atoms, which is optionally interrupted by an oxygen atom and which is optionally mono- or polysubstituted with identical or different substituents selected from the group consisting of trifluoromethyl, trifluoromethoxy, hydroxy, halogen, carboxyl, benzyloxycarbonyl, straight or branched chain alkoxycarbonyl having up to 6 carbon atoms and / or radicals of the formulas - 10 S03H, - (A) a-NR7R8, -0-CO-NR7'R8 ', -S (0) b -R9, - P (O) (OR10) (OR11), where a and b are the same or different and each represents a number of 0 or 1, A represents a radical CO or S02, R7, R7 ', R8 and R8' are the same or different and each represents hydrogen, or they represent cycloalkyl with 3 to 8 carbon atoms, aryl with 6 to 10 carbon atoms, a heterocycle optionally 10 benzocondensate, partially unsaturated or saturated of 5 to 6 elements, with up to 3 heteroatoms of the group consisting of S, N and O, wherein the aforementioned ring systems are optionally 15 mono- or polysubstituted by substituents identical or different from the group consisting. of straight chain hydroxy, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, halogen, alkoxy or alkoxycarbonyl or Branched having in each case up to 6 carbon atoms or coa a group of the formula - (S0) C-NR12R13, in which c represents a number of 0 or 1, R12 and R13 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 5 carbon atoms, OR 'R7', R8 and R8 'each represents straight or branched chain alkoxy having up to 6 carbon atoms, or represents straight chain alkyl or Branched having up to 8 carbon atoms which is optionally mono- or polysubstituted with substituents same or different from the group consisting of hydroxy, halogen, aryl having 6 to 10 15 carbon atoms, alkoxy or straight or branched chain alkoxycarbonyl having in each case up to 6 carbon atoms or with a group of the formula - (CO) d-NR 14 R 15, in which R 14 and R 15 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, and 25 d represents a number of 0 or 1, R7 and R8 and / or R7 'and R8' together with the nitrogen atom form a heterocycle saturated from 5 to 7 elements, which optionally may contain an additional heteroatom of the group consisting of S 0 or a radical of the formula -NR 16, wherein R 16 represents hydrogen, aryl having 6 10 to 10 carbon atoms, benzyl, an aromatic or saturated heterocycle of 5 to 7 elements having up to 3 heteroatoms of the group consisting of S, N and 0, which is optionally substituted with methyl, or 15 represents a straight or branched chain alkyl having up to 6 carbon atoms, which is optionally substituted with hydroxyl, R9 represents aryl having 6 to 10 carbon atoms. 20 carbon, or represents straight or branched chain alkyl having up to 4 carbon atoms, R10 and R11 are the same or different and each 25 represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, and / or the above-mentioned alkyl chain under R3 / R4 is optionally substituted with cycloalkyl having 3 to 8 carbon atoms, aryl having 6 a 10 carbon atoms or with an optionally benzo-condensed, optionally unsaturated, saturated or 10 unsaturated, from 5 to 7 elements, which may contain up to 4 heteroatoms of the group consisting of S, N and O or a radial of the formula -NR17, in which 15 R17 represents hydrogen, hydroxyl, formyl, trifluoromethyl, acyl or straight or branched chain alkoxy having in each case up to 4 carbon atoms, or straight or branched chain alkyl, 20 having up to 6 carbon atoms, which is optionally mono- or polysubstituted with the same or different substituents selected from the group consisting of hydroxyl and straight or branched chain alkoxy having up to 6 carbon atoms, and wherein the aryl and the heterocycle they are optionally mono- or polysubstituted, with the same or different substituents, selected from the group consisting of nitro, halogen, -S03H, alkyl or straight or branched chain alkoxy each having up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy and / or with a radical of the formula -S02NR18R19, wherein R18 and R19 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 6 carbon atoms, and / or R3 or R4 represents a group of the formula -NR20R21, wherein R20 and R21 have the above-mentioned meaning of R18 and R19 and are the same or different from these, and / or R3 or R4 represent adamantyl, or represent so the radicals of the formula or represents cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or represents an optionally benzocondensate, partially unsaturated, saturated or unsaturated heterocycle of 5 to 7 elements, which may contain up to 4 heteroatoms of the group consisting of of S, N and O, or a radical of the formula -NR22, wherein R22 has the above-mentioned meaning of R16 and is the same or different from this, or represents carboxyl, formyl or acyl straight or branched chain having up to 5 carbon atoms, and wherein the cycloalkyl, aryl and / or heterocycle are optionally mono- or polysubstituted with the same or different substituents with the group consisting of straight chain halogen, triazolyl, trifluoromethyl, trifluoromethoxy, carboxyl, acyl or alkoxycarbonyl or which has in each case up to 6 carbon atoms, nitro and / or with groups of the formula - S03H, -OR23, (S02) CNR24R25, -P (O) (OR26) (OR27), in which e represents a num 0 or 1, R23 represents a radical of the formula represents cycloalkyl having 3 to 7 carbon atoms, or represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, which is optionally substituted with cycloalkyl having 3 to 7 carbon atoms, benzyloxy, tetrahydropyranyl, tetrahydrofuranyl, straight chain or branched alkoxy or alkoxycarbonyl each having up to 6 carbon, carboxyl, benzyloxycarbonyl or phenyl atoms, which in turn may be mono- or polysubstituted, by the same or different substituents, selected from the group consisting of straight or branched chain having up to 4 carbon, hydroxyl and halogen atoms, and / or alkyl is optionally substituted with radicals of formulas -CO-NR28R29 or -CO-R30 / in which R 28 and R are the same or different and each represents hydrogen or straight or branched chain alkyl with up to 8 carbon atoms, or R28 and R29 together with the nitrogen atom form a saturated heterocycle or from 5 to 7 elements which optionally may contain an additional heteroatom of the group consisting of S and O, and R30 represents phenyl or adamantyl, R24 and R25 have the above-mentioned meaning of R18 and R19 and are the same or different from these, R26 and R27 have the meaning cited above of R10 and R11 and are the same or different? these and / or the cycloalkyl, aryl and / or heterocycle are optionally substituted with straight or branched chain alkyl having up to 6 carbon atoms, which are optionally substituted with hydroxyl, carboxyl, with a 5- to 7-membered heterocycle having up to 3 heteroatoms of the group consisting of S, N and O, or with the groups of the formula -S02-R31, P (O) (OR32) (OR33) or -NR34R35, in which R31 represents hydrogen or has the same meaning as cited above of R9 and is the same or other than this, R32 and R33 have the above-mentioned meaning of R10 and R11 and are the same or different from these, R3 and R35 are the same or different and represent hydrogen or straight or branched chain alkyl having up to 6 carbon atoms, which it is optionally substituted with hydroxy or straight or branched chain alkoxy having up to 4 carbon atoms, or Rj4 and R35 together with the nitrogen atom form a saturated heterocycle of 5 to 6 elements which may contain an additional heteroatom of the group consisting of S and 0, or a radial of the formula -NR36, wherein R 36 represents hydrogen, hydroxyl, straight or branched chain alkoxycarbonyl having up to 7 carbon atoms or straight or branched chain alkyl having up to 5 carbon atoms , what it is optionally substituted with hydroxyl, R3 and R4 together with the nitrogen atom form an optionally benzocondensate unsaturated or saturated or partially heterocycle 10 unsaturated from 5 to 7 elements, which may optionally contain up to 3 heteroatoms from the group consisting of S, N and O, or a radical of the formula -NR37, wherein R 37 represents hydrogen, hydroxyl, formyl, trifluoromethyl, Acyl, alkoxy or straight or branched chain alkoxycarbonyl, each having "up to 4 carbon atoms," or represents straight or branched chain alkyl having up to 6 carbon atoms, which is optionally mono- or polysubstituted with the same substituents or different from the group that consists of 25 hydroxyl, trifluoromethyl, carboxyl, alkoxy or straight chain or branched alkoxycarbonyl each with up to 6 carbon atoms, or with groups of the formula (D) f_NRjaR- -C0- (CH; -0-C0-R 4" 0 -CO- (CH2) h-OR41 or -P (0) - (OR42) (OR43), where h are the same or different and each represents a number of 1, 2, 3, or 4, f represents a number of 0 or 1, D represents a group of the formula -CO or -S02, R38 and R39 are the same or different and each have the above-mentioned meaning of R7 and R8, R40 represents straight or branched chain alkyl having up to 6 carbon atoms, R41 represents straight or branched chain alkyl having up to 6 carbon atoms. carbon, R42 and R43 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, R "represents a radical of the formula - (CO)? - E, in which i represents a number of 0 or 1, E represents cycloalkyl having 3 to 7 carbon atoms or benzyl, represents aryl having 6 to 10 carbon atoms or an aromatic heterocycle of 5 to 6 elements having up to 4 heteroatoms of the group consisting of S, N and 0, wherein the aforementioned ring systems are optionally mono- or polysubstituted with the same or different constituents, selected from the group consisting of nitro, halogen, -SO3H, straight-chain alkoxy or branched having up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy, or with a radical of the formula -S02-NR44R45, wherein R44 and R45 have the above-mentioned meaning of R18 and R19 and are the same or different from these, E represents the radicals of the formulas and the heterocycle mentioned under R3 and R4, which is formed together with the nitrogen atom, is optionally mono- or polysubstituted, with the same or different substituents, selected 10 of the group consisting of straight chain or branched hydroxyl, formyl, carboxyl, acyl or alkoxycarbonyl having in each case up to 6 carbon atoms, nitro and groups of the formulas -P (O) (OR46) (OR47), where R46 and R47 have the above meaning of R10 and R11 and are the same or different from these, R48 represents straight or branched chain alkoxy hydroxy having up to 4 carbon atoms, j represents 0 or 1, and R 49 and R are the same or different and have the above-mentioned meaning of R14 and R15, and / or the heterocycle mentioned under R3 and R4, which 10 is formed together with the nitrogen atom, which is optionally substituted with straight or branched chain alkyl having up to 6 carbon atoms, which is optionally mono- or 15 polysubstituted with the same or different substituents selected from the group consisting of hydroxyl, halogen, carboxyl, cycloalkyl or cycloalkoxy having in each case 3 to 8 carbon atoms, 20 alkoxy or straight chain or branched alkoxycarbonyl in each case up to 6 carbon atoms, or with a radical of the formulas - S03H, -NR51R52 or P (0) OR53OR54, in which R51 and R53 are the same or different and each they represent hydrogen, phenyl, carboxyl, benzyl or straight or branched chain alkyl or alkoxy each having up to 6 carbon atoms, R53 and R54 are the same or different and have the aforementioned meaning of R10 and R11, and / or the alkyl is optionally 10 substituted with aryl having 6 to 10 carbon atoms, which in turn may be mono- or polysubstituted, with the same or different substituents, of the group consisting of halogen, hydroxyl, chain alkoxy Linear or branched having up to 6 carbon atoms, or with a group of the formula -NR51'R52 ', in which R51' and R52 'have the aforementioned meaning 20 above of R51 and R53 and are the same or different from these, and / or the heterocycle mentioned under R3 and R4, which is formed together with the nitrogen atom, is optionally substituted 25 with aryl having 6 to 10 carbon atoms or with a saturated, partially unsaturated or unsaturated heterocycle of 5 to 7 elements having up to 3 heteroatoms from the group consisting of S, N and 0, optionally also linked by a nitrogen function , wherein the ring systems in turn may be substituted with hydroxyl or with straight or branched chain alkyl or alkoxy, each having up to 6 carbon atoms, R3 and R4 together with the nitrogen atom form radicals of the formulas R5 and R6 are the same or different and each represents hydrogen, straight or branched chain alkyl having up to 6 carbon atoms, hydroxyl or straight or branched chain alkoxy having up to 6 carbon atoms, and their salts, hydrates, N -oxides and isomeric forms

2. 2-phenyl-substituted imidazotriazinones of the general formula (I) according to claim 1, characterized in that R1 represents straight or branched chain alkyl having up to 3 carbon atoms, R2 represents straight chain alkyl having up to 3 atoms of carbon, R3 and R4 are the same or different and each represents hydrogen or represents alkenyl or straight or branched chain alkoxy having in each up to 6 carbon atoms, or represents a straight or branched chain alkyl chain having up to 8 carbon atoms. carbon atoms, which is optionally interrupted by an oxygen atom and which is optionally mono- or polysubstituted with identical or different substituents selected from the group consisting of hydroxyl, fluoro, chloro, carboxyl, benzyloxycarbonyl, straight or branched chain alkoxycarbonyl having up to 5 carbon atoms and / or radicals of the formulas -S03H, - (A) to -NR 7'nR8 °, -O-CO- NR7'R8 ' , -S (0) b-R9 / -P (O) (OR10) (OR11), 10 15 in which a and b are the same or different and each represents a number of 0 or 1, A represents a radical CO or S02, R7, R7 ', R8 and R8' are the same or different and each represents hydrogen, or cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, piperidinyl and pyridyl, wherein the aforementioned ring systems are optionally mono- or tri-substituted by substituents same or different from the group consisting of hydroxyl, nitro, trifluoromethyl, Straight or branched chain trifluoromethoxy, carboxyl, fluoro, chloro, alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms, or with a group of the formula - (S02) C-NR12R13, in which c represents a number of 0 or 1,. R12 and R13 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 20 carbon atoms, R, R, R and R each represents straight or branched chain alkoxy having up to 3 carbon atoms, or represents straight or branched chain alkyl having up to 7 carbon atoms which is optionally mono- or polysubstituted with like substituents or other than the group consisting of linear chain hydroxy, fluoro, chloro, phenyl, alkoxy or alkoxycarbonyl. branch that has in each case up to 4 carbon atoms, or with a group of Formula - (CO) d-NR 14 R 15, in which R 14 and R 15 are the same or different and each represents hydrogen or straight or branched chain alkyl having 15 to 3 carbon atoms, and d represents a number of 0 or 1, or R7 and R8 and / or R7 'and R8' together with the Nitrogen forms a pyrrolidinyl, morpholinyl, piperidinyl or a triazolyl ring or radicals of the formulas wherein R 1 6 represents hydrogen, phenyl, benzyl, morpholinyl, pyrrolinyl, piperidinyl, piperazinyl or N-methylpiperazinyl, or represents a straight-chain alkyl or Branched having up to 5 carbon atoms, which is optionally substituted with hydroxyl, R represents straight or branched chain alkyl of up to 3 carbon atoms, R10 and R11 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, and / or the alkyl chain above 20 cited under R 3 / R 4 is optionally substituted with cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, pyridyl, quinolyl, pyrrolidinyl, pyrimidyl, morpholinyl, furyl, piperidinyl, tetrahydrofuranyl or with radicals of the formula, wherein 1 7 10 R represents hydrogen, hydroxyl, formyl, trifluoromethyl, acyl or straight chain or branched alkoxy having in each case up to 3 carbon atoms, or represents straight chain alkyl or Branched, having up to 4 carbon atoms, which is optionally mono- or tri-substituted with the same or different substituents selected from the group consisting of hydroxyl and chain alkoxy Linear or branched having up to 4 carbon atoms, and wherein the phenyl and the heterocycle are optionally mono- or tri-substituted, with the same or different substituents, selected from the group consisting of nitro, fluoro, chloro, -S03H, alkyl or alkoxy straight or branched chain having in each case up to 4 carbon atoms, hydroxyl, and / or with a radical of the formula - S02NR18R19, in which R18 and R19 are the same or different and each represents hydrogen or straight chain alkyl or branched having up to 4 carbon atoms, and / or R3 or R4 represents a group of the formula -NR20R21, wherein R20 and R21 have the above-mentioned meaning of R18 and R19 and are the same or different from these, and / or R3 or R4 represent adamantyl, or represent the radicals of the formula or represents cyclopentyl, cyclohexyl, cycloheptyl, phenyl, morpholinyl, oxazolyl, thiazolyl, quinolyl, isoxazolyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl or represent radicals of the formulas wherein R22 has the above-mentioned meaning of R16 and is the same or different from this, or represents straight or branched chain carboxyl, formyl or acyl having up to 3 carbon atoms, and wherein cycloalkyl, phenyl and / or the heterocycles are optionally mono- or trisubstituted, with the same or different substituents selected from the group consisting of fluoro, chloro, triazolyl, trifluoromethyl, trifluoromethoxy, carboxyl, acyl or straight-chain or branched alkoxycarbonyl each having up to 5 carbon atoms , nitro and / or with groups of the formulas -S03H, -OR23, (S02) eNR24R25, -P (O) (OR2d) (OR27), in which e represents a number 0 or 1, R23 represents a radical of the formula represents cyclopropyl, cyclopentyl, cyclobutyl, cyclohexyl or cycloheptyl, represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, which may be optionally substituted with cyclopropyl, cyclopentyl, cyclohexyl, benzyloxy, tetrahydropyranyl, tetrahydrofuranyl, alkoxy or alkoxycarbonyl straight or branched chain having in each case up to 4 carbon atoms, benzyloxycarbonyl or phenyl, which in turn may be mono- or polysubstituted, with the same or different substituents, selected from the group consisting of straight or branched chain alkoxy having up to 3 carbon atoms, hydroxyl, fluorine or chlorine, and / or wherein the alkyl is optionally substituted with radicals of the formulas -CO-NR28R29 or -CO-R30, wherein R28 and R29 are the same or different and each represent hydrogen or straight or branched chain alkyl having up to 5 carbon atoms, or R28 and R29 together with the nitrogen atom form a morpholinyl, pyrrolidinyl or piperidinyl ring, and R30 represents phenyl or adamantyl, R25 have the aforementioned meaning of R18 and R19 and are the same as or different from these, R'26 and R have the aforementioned meaning of R 10 and R 11 and are the same or different from these and / or cycloalkyl, phenyl and / or the heterocycles are optionally substituted with straight or branched chain alkyl having up to 4 carbon atoms, which is optionally substituted with hydroxyl, carboxyl, pyridyl, pyrimidyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, triazolyl or with groups of 10 the formulas -S02-R 31 -P (0) (ORJ2) (OR, 3J3J,] NR34R35, in which R 31 has the above-mentioned meaning of R9 and is the same or different from this, 15 R32 and R33 have the above-mentioned meaning of R10 and R11 and are the same or different from these, R34 and R35 are the same or different and each represent hydrogen or chain alkyl Linear or branched having up to 5 carbon atoms, which is optionally substituted with hydroxyl or straight or branched chain alkoxy having up to 3 carbon atoms, or R34 and R35 together with the nitrogen atom form a morpholinyl, triazolyl or thiomorpholinyl or a radical of formula wherein R36 represents hydrogen, hydroxyl, straight or branched chain alkoxycarbonyl with up to 5 carbon atoms or straight or branched chain alkyl having up to 4 carbon atoms, which is optionally substituted with hydroxyl, or R3 and R4 together with the Nitrogen atom form a ring morpholinyl, thiomorpholinyl, pyrrolidinyl, piperidinyl or a radical of the formula wherein R 37 represents straight or branched chain hydrogen, hydroxyl, formyl, trifluoromethyl, acyl, alkoxy or alkoxycarbonyl, each having up to 4 carbon atoms, or represents straight or branched chain alkyl having up to 5 carbon atoms , which is optionally mono- or Trisubstituted, with the same or different substituents selected from the group consisting of straight chain or branched hydroxyl, trifluoromethyl, carboxyl, alkoxy or alkoxycarbonyl having in 15 each case up to 4 carbon atoms, or with groups of the formula - (D) f_NR38R39, -CO-; CH2) g-0-CO-R 440 -CO- (CH 2) h '-OR 41 PÍO) (OR4) (OR43) in which 20 g and h are the same or different and represent a number 1, 2, or 3, and f represents a number 0 or 1, D represents a group of the formula -CO or - 25 S02, R and R are the same or different and have the same meaning of R7 and R8 cited above, R 40 represents straight or branched chain alkyl having up to 4 carbon atoms, R 41 represents straight or branched chain alkyl having up to 4 atoms of carbon, R42 and R43 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, OR 37 represents a radical of the formula - (CO) iE, wherein i is a No. 0 or 1, E represents cyclopentyl, cyclohexyl, cycloheptyl, benzyl, phenyl, pyridyl, pyrimidyl or furyl, where the aforementioned ring systems are optionally mono- or disubstituted, with the same or different substituents, selected from the group c It consists of nitro, fluorine, chlorine, -SO3H, straight or branched chain alkoxy having up to 4 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy or with a radical of the formula -S02-NR 4R45, wherein and R 45 have the aforementioned meaning of R18 and R19 and are the same or different from 10 these, E represents radicals of the formulas fifteen And the heterocycles formed together with the nitrogen atom, mentioned under R 3 and R 4, are optionally mono- or trisubstituted, with the same or different substituents, optionally also geminally, selected from the group consisting of hydroxyl, formyl, carboxyl, acyl or alkoxycarbonyl of straight or branched chain in each case with up to 5 carbon atoms, nitro and groups of the formulas - PÍO) (OR46) (OR47), in which R 46 R have the above-mentioned meaning of R, 1i0U and R 11 and are equal Other than these, Rq represents straight or branched chain alkoxy hydroxy having up to 3 carbon atoms, j is a number 0 or 1, 20 and R 49 and R are the same and have the above-indicated meaning of R and R15, and / or the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally substituted with straight or branched chain alkyl having up to 5 carbon atoms, which are optionally mono- or polysubstituted with the same or different substituents selected of the group consisting of hydroxyl, fluorine, chlorine, carboxyl, cyclopropyl, cyclopentyl, cyclohexyl, Straight or branched chain cycloheptyl, alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms or with a radical of the formula -S03H, -NR51R52 or -P (O) or R53OR54, wherein R51 and R52 are the same or different and each represents hydrogen, phenyl, carboxyl, benzyl or alkyl or straight or branched chain alkoxy in each case with up to 4 carbon atoms, R53 and R54 are the same or different and have the aforementioned meaning of R10 and R11 , and / or the alkyl is optionally substituted with phenyl, which in turn may be mono- or 25 trisubstituted, with the same or different substituents, selected from the group consisting of fluorine, chlorine, hydroxyl, straight or branched chain alkoxy having up to 4 carbon atoms, or with a group of the formula -NR51'R52 ', in the that R51 'and R52' have the aforementioned meaning of R51 and R52 and are the same or different from these, and / or the heterocycles formed together with the Nitrogen atom, mentioned under R 3 and R 4, are optionally substituted with phenyl, pyridyl, piperidinyl, pyrrolidinyl or tetrazolyl, optionally also linked by a function, wherein the ring systems at their They can be substituted with hydroxyl or with straight or branched chain alkyl or alkoxy, each having up to 5 carbon atoms, or R3 and R4 together with the nitrogen atom form radicals of the formulas R5 and R6 are the same or different and represent hydrogen, hydroxyl or straight or branched chain alkoxy and each with up to 4 carbon atoms, and their salts, N-oxides, hydrates and isomeric forms.

3. 2-phenyl substituted imidazotriazinones of the general formula 1) according to claim 1, characterized in that R 1 represents straight or branched chain alkyl having up to 3 carbon atoms, R 2 represents straight chain alkyl having up to 3 carbon atoms, R3 and R4 are the same or different and each represents hydrogen or represents alkenyl or straight or branched chain alkoxy each having up to 4 carbon atoms, or represents a straight or branched chain alkyl chain having up to 6 carbon atoms carbon, which is optionally interrupted with an oxygen atom and which is optionally mono- or trisubstituted, with 10 identical or different substituents, selected from the group consisting of hydroxyl, fluoro, chloro, carboxyl, straight or branched chain alkoxycarbonyl having up to 4 carbon atoms and / or 15 radicals of the formulas -S03H, - (A) to -NR7R8, -O-CO-NR 'R6 • S (0) b -R, -PIO) (OR 1? 0 ?,) (OR1J-) where a and b are the same or different and each represent a number 0 or 1, A represents a radical CO or S02, R7, R7 ', R8 and R8' are the same or different and each represent hydrogen, or Represent cyclopentyl, cyclohexyl , Cycloheptyl, phenyl, piperidinyl and pyridyl, wherein the aforementioned ring systems are optionally mono- or disubstituted, with the same or different substituents, 15 selected from the group consisting of straight or branched chain hydroxy, nitro, carboxyl, fluoro, chloro, alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or with a group of the Formula - (S02) c, -NR12R13, wherein c represents a number 0 or 1, R12 and R13 are the same or different and represent hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, R, R, R and each represents methyxy, or represent straight or branched chain alkyl having up to 6 carbon atoms which are optionally mono- or 10 disubstituted, with the same or different substituents, selected from the group consisting of hydroxyl, fluoro, chloro, phenyl, alkoxy or alkoxycarbonyl of straight or branched chain in each case up to 3. 15 carbon atoms, or with a group of the formula - (CO) d-NR 14 R 15, in which R 4 and R 15 are the same or different and each represents hydrogen, methyl or ethyl, 20 and d represents a number 0 6 1, R7 and R8 and / or R7 'and R8' together with the nitrogen atom form a morpholinyl, piperidinyl or triazolyl ring or radicals of the formulas wherein - R 16 represents hydrogen, phenyl, benzyl, morpholinyl, pyrrolidinyl, piperidinyl, piperazinyl or N-methylpiperazinyl, or represent straight or branched chain alkyl having up to 3 carbon atoms, which is optionally substituted with hydroxyl, R 9 represents methyl , R10 and R11 are the same or different and each represents hydrogen, methyl or ethyl, and / or the alkyl chain mentioned under R3 / R4 is optionally substituted with cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, morpholinyl, furyl, tetrahydrofuranyl or with radicals of the formulas wherein R 17 represents hydrogen, hydroxyl, formyl, acetyl or alkoxy having up to 3 10 carbon atoms, or represents straight or branched chain alkyl, having up to 3 carbon atoms, which is optionally mono- or disubstituted, with equal substituents 15 or different, selected from the group consisting of hydroxyl or straight or branched chain alkoxy having up to 3 carbon atoms, and wherein the phenyl and the heterocycles are Optionally mono- or trisubstituted, with the same or different substituents, selected from the group consisting of fluorine, chlorine, -S03H, alkyl or straight or branched chain alkoxy each having up to 3 carbon atoms, hydroxyl, and / or with a radical of the formula -S02-NR18R19, wherein R18 and R19 are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, and / or RJ or R4 represents a group of the formula -NR20R21, wherein, 20 R have the above-mentioned meaning of R 18 R 19 and are the same or different from these, and / or R 3 or R 4 represent adamantyl, or represent radicals of the formulas or represent cyclopentyl, cyclohexyl, cycloheptyl, phenyl, morpholinyl, oxazolyl, thiazolyl, quinolyl, isoxazolyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl, or represent radicals of the formulas Wherein R22 has the aforementioned meaning of Rld and is the same or different from this, or represents formyl or acetyl, and where cycloalkyl, phenyl and / or heterocycles are optionally mono- or disubstituted, with the same substituents or different, selected from the group consisting of fluorine, chlorine, triazolyl, carboxyl, acyl or Straight or branched chain alkoxycarbonyl having in each case up to 4 carbon atoms, nitro and / or with groups of the formulas - S03H, -OR, 2 '3, 27, S02) eNR ^ R, - P (O) (OR 2¿ 6D,) (OR in which e represents a number 0 or 1, R33 represents a radical of the formula represent cyclopropyl, cyclopentyl, Cyclobutyl or cyclohexyl, represents hydrogen or straight or branched chain alkyl having up to 3 carbon atoms, which is optionally substituted by cyclopropyl, cyclohexyl, benzyloxy, Or tetrahydropyranyl, alkoxy or straight-chain or branched alkoxycarbonyl having in each case up to 3 carbon atoms, benzyloxycarbonyl or phenyl, which in turn may be optionally mono- or disubstituted, with 20 identical or different substituents, selected from the group consisting of methoxy, hydroxyl, fluorine or chlorine, and / or wherein the alkyl is optionally substituted with radicals of the formulas -C0- NR28R29 or -CO-R30, wherein R 28 and R are the same or different and each represents hydrogen or straight or branched chain alkyl having up to 4 carbon atoms, or R28 and R29 together with the nitrogen atom form a morpholinyl, pyrrolidinyl or piperidinyl ring, and R30 represents phenyl or adamantyl, R24 and R25 have the meaning cited above of R18 and R19 and are the same or different from these, R 26 and R 27 have the above-mentioned meaning of R 10 and R 11 and are the same or different from these and / or cycloalkyl, phenyl and / or the heterocycles are optionally substituted with straight or branched chain alkyl with up to 3 carbon atoms, which is optionally substituted with hydroxyl, carboxyl, pyridyl, pyrimidyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, triazolyl or with groups of the formulas -S02-R, P (O) (OR, 3J2-,) (OR, 3"3,) NR34R35, wherein R31 represents methyl, R 32 and R have the above-mentioned meaning of R10 and R11 and are the same or other than these, R 34 and R 35 are the same or different and each represents hydrogen or chain alkyl Linear or branched having up to 3 carbon atoms, which is optionally substituted with hydroxyl or methoxy, or R34 and R35 together with the nitrogen atom form a morpholinyl, triazolyl or 15 thiomorpholinyl or a radical of the formula wherein R 20 represents hydrogen, hydroxy, straight or branched chain alkoxycarbonyl having up to 3 carbon atoms or straight or branched chain alkyl having up to 3 carbon atoms, which is optionally substituted by hydroxyl, or R 3 and R 4 together with the nitrogen atom they form a morpholinyl, thiomorpholinyl, pyrrolidinyl, piperidinyl ring or a radical of the formula wherein R 37 represents straight or branched chain hydrogen, hydroxyl, formyl, acyl, alkoxy or alkoxycarbonyl, each having up to 3 carbon atoms, or represents straight or branched chain alkyl having up to 4 carbon atoms, which is optionally mono- or di-substituted, with the same or different substituents, selected from the group consisting of straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or with groups of the formulas (D) f_NR JoR -n J »-CO- (CH2) g-0-CO-R 4 * 0u, -CO- (CH2) h-OR 41 P (0) 10R 42, (OR43) where g and g are the same or different and represent a number 1 or 2, and f represents a number 0 or 1, D represents a group of the formula -CO or -S02, 10 R 38 and R39 are the same or different and have the above-mentioned meaning of R7 and R8, R40 represents straight-chain branched alkyl having up to 3 atoms 15 carbon, R 41 represents straight or branched chain alkyl having up to 3 carbon atoms, R42 and R43 are the same or different and 20 represent hydrogen, methyl or ethyl, R represents a radical of the formula - (CO) iE, wherein i is a number 0 or 1, E represents cyclopentyl, benzyl, phenyl, pyridyl, pyrimidyl or furyl, wherein the aforementioned ring systems are optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of nitro, fluoro, chloro, -S03H, alkoxy, Linear or branched chain having up to 3 carbon atoms, hydroxyl, or with a radical of the formula -S02- NR44R45, wherein R44 and R45 have the above-mentioned meaning of R18 and R19 and are the same or different from these , E represents radicals of formulas 20 and the heterocycles formed together with the nitrogen atom, cited under R3 and R4, are optionally mono- or trisubstituted, with the same or different substituents, optionally also geminally, selected from the group consisting of hydroxyl, formyl, carboxyl, acyl or alkoxycarbonyl linear or branched chain Having in each case up to 3 carbon atoms, or groups of the formulas P (O) (OR46) (OR47), Wherein R46 and R47 have the above-mentioned meaning of R10 and R11 and are the same or different from these, R49 represents hydroxyl or methoxy, j is a number 0 or 1, and, 49 and R are the same or different and have the above-indicated meaning of R, 14 and R15, and / or the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally substituted with straight or branched chain alkyl having up to 4 carbon atoms, which are optionally mono- or tri-substituted, with identical substituents or 10 different, selected from the group consisting of hydroxyl, fluorine, chlorine, carboxyl, cyclopropyl, cycloheptyl, alkoxy or straight or branched chain alkoxycarbonyl each having up to 3 carbon atoms. Or carbon with a radical of the formulas -S03H, -NR51R53 or P (0) OR53OR54, in which R 51 and R52 are the same or different and each represents hydrogen, phenyl, carboxyl, The benzyl or straight or branched chain alkyl or alkoxy having in each case up to 3 carbon atoms, R 53 and R54 are the same or different and have the abovementioned meaning of R 10. 25 and R11, and / or the alkyl is optionally substituted with phenyl, which in turn may be optionally mono- or disubstituted, with the same or different substituents, selected from the group consisting of fluorine, chlorine, hydroxyl, methoxy or with a group of the formula -NR51'R52 ', in which R51' and R52 'have the same meaning as 10 above of R51 and R52 and are the same or different from these, and / or the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, which are optionally substituted with phenyl, Pyridyl, piperidinyl, pyrrolidinyl or tetrazolyl, if they are also suitable for joining by a function, wherein the ring systems in turn may be substituted with hydroxyl or with alkyl or chain alkoxy 20 linear or branched, which in each case has up to 3 carbon atoms, or R3 and R4 together with the nitrogen atom form radicals of the formulas R and R are the same or different and represent hydrogen, hydroxyl or represent straight or branched chain alkoxy having up to 3 carbon atoms, and their salts, N-oxides, hydrates and isomeric forms. ~

4. 2-phenyl substituted imidazotriazinones of the general formula (I) according to claim 1, characterized in that R 1 represents methyl or ethyl, R 2 represents ethyl or propyl, R 3 and R 4 are the same or different and each represents a chain alkyl chain linear or branched having up to 5 carbon atoms, which optionally is substituted up to twice with identical or different substituents, selected from the group consisting of hydroxyl or methoxy, or R3 and R4 together with the nitrogen atom form a piperidinyl ring, morpholinyl, thiomorpholinyl or a radical of the formula wherein R 37 represents hydrogen, formyl, acyl or straight or branched chain alkoxycarbonyl, each having up to 3 carbon atoms, or represents straight or branched chain alkyl with up to 3 carbon atoms which optionally mono- or disubstituted , with the same or different substituents, selected from the group consisting of hydroxyl, carboxyl, alkoxy or straight or branched chain alkoxycarbonyl each having up to 3 carbon atoms or with groups of the formulas - (D) f_R38R39 or -P ( O) (OR42) (OR43), where f represents a number 0 or 1, D represents a group of the formula -CO, R38 and R39 are the same or different and each represents hydrogen or methyl, R42 and R43 are same or different and each one represents hydrogen, methyl or ethyl, 15 or R37 represents cyclopentyl, and the heterocycles formed together with the nitrogen atom, mentioned under R3 and R4, are optionally mono- or disubstituted, with 20 identical or different substituents, also optionally geminally, selected from the group consisting of straight chain or branched hydroxyl, formyl, carboxyl, acyl or alkoxycarbonyl having in each case up to 3 carbon atoms or groups of the formulas -P ( O) (OR46) (OR47) or - (CO i.NR ^ R50, where R46 and R47 are the same or different and each represents hydrogen, methyl or ethyl, j represents a number 0 or 1, and R49 and R50 they are the same or different and represent hydrogen or methyl 10 and / or the heterocycles formed together with the nitrogen atom, mentioned under R 3 and R 4, are optionally substituted with straight or branched chain alkyl having up to 3 carbon atoms, which are optionally mono- or 15 disubstituted, with the same or different substituents, selected from the group consisting of hydroxyl, carboxyl or with a radical of the formula P (O) OR53OR54, in which R53 and R54 are the same or different and each represents hydrogen, methyl or ethyl, and / or the heterocycles formed together with the nitrogen atom, mentioned under R 3 and R 4, are optionally substituted with piperidinyl or 25 pyrrolidinyl bonded by nitrogen, R is hydrogen, and R is ethoxy or propoxy, and their salts, hydrates, N-oxides isomeric forms.

5. Substituted 2-phenyl imidazotriazinones according to claims 1 or 4, characterized in that they have the following structures: Structure Structure Structure Structure

6. 2-phenyl substituted imidazotriazinones of the general formula (I) according to claim 1, characterized for the treatment of diseases.

7. A process for the preparation of 2-phenyl substituted imidazotriazinones according to claim 1, characterized in that first of all the compounds of the general formula (ID wherein R1 and R2 are as defined above and L represents straight or branched chain alkyl having up to 4 carbon atoms, are converted with compounds of the general formula (III) III wherein R5 and R6 are each as defined above, • - in a two-step reaction, in the ethanol and phosphorus oxychloride / dichloroethane systems, in the compounds of the general formula (IV) wherein R1, R2, R5 and R6 are as defined above, which are reacted in an additional step with chlorosulfonic acid to give the compounds of the general formula (V) wherein R1, R2, R5 and R6 are each as defined above, which are finally reacted with amines of the general formula (VI) HN3R4 (vi: wherein RJ and R4 are each as defined above, - - in an inert solvent.

8. A medicament containing at least one 2-phenyl substituted imidazotriazinone according to claim 1, and characterized for pharmaceutically acceptable formulation agents.

9. A medicament according to claim 8, characterized for the treatment of cardiovascular, cerebrovascular diseases and / or diseases of the urogenital tract.

10. A medicament according to claim 9, characterized for the treatment of erectile dysfunction.

11. The use of the 2-phenyl-substituted imidazotriazinone according to claim 1, characterized for preparing medicaments.