RU2001108499A - Pyrazolopyrimidinones for the treatment of impotence - Google Patents

Claims (9)

1. Pyrazolopyrimidinones represented by the following formula 1

where R ₁ represents hydrogen, a (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₃ ) fluoroalkyl group or a (C ₃ -C ₆ ) cycloalkyl group; R ₂ represents hydrogen, a substituted or unsubstituted (C ₂ -C ₆ ) alkyl group, a (C ₁ -C ₃ ) fluoroalkyl group or a (C ₃ -C ₆ ) cycloalkyl group; R ₃ represents a substituted or unsubstituted (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) fluoroalkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a (C ₃ -C ₆ ) alkenyl group, or A (C ₃ -C ₆ ) alkynyl group; R ₄ represents a substituted or unsubstituted, linear or branched (C ₁ - ₁₀₎ alkyl group, a substituted or unsubstituted (C ₁ -C ₉₎ alkenyl group, a substituted or unsubstituted (C ₃ -C ₆₎ cycloalkyl group, a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocycle selected from the group consisting of pyridine, isoxazole, thiazole, pyrimidine, indane, benzthiazole, pyrazole, thiadiazole, oxazole, piperidine, morpholine, imidazole, pyrrolidine, thienyl Foot, triazole, pyrrole and furyl cycle, and their pharmaceutically acceptable salts. 2. Pyrazolopyrimidinones and their pharmaceutically acceptable salts according to claim 1, where R ₁ represents a (C ₁ -C ₃ ) -alkyl group. 3. Pyrazolopyrimidinones and their pharmaceutically acceptable salts according to claim 1, where R ₂ represents a substituted or unsubstituted (C ₂ -C ₆ ) -alkyl group. 4. Pyrazolopyrimidinones and their pharmaceutically acceptable salts according to claim 1, where R ₃ represents a substituted or unsubstituted (C ₂ -C ₆ ) -alkyl group. 5. Pyrazolopyrimidinones and their pharmaceutically acceptable salts according to claim 1, where R ₄ represents a substituted or unsubstituted (C ₁ -C ₆ ) -alkyl group, a substituted or unsubstituted (C ₃ -C ₆ ) -cycloalkyl group, substituted or unsubstituted benzene a ring or residue of substituted or unsubstituted pyridine; or a residue of substituted or unsubstituted pyrrole. 6. Pyrazolopyrimidinones and their pharmaceutically acceptable salts according to claims 1, 2, 3, 4 or 5, in which when R ₂ , R ₃ and R ₄ are substituted, the substituent is a halogen, substituted or unsubstituted benzene ring, substituted or an unsubstituted heterocycle selected from the group consisting of pyridine, pyrrolidine, piperidine, pyrrole residues, or a substituted or unsubstituted (C ₃ -C ₆ ) cycloalkyl group. 7. Pyrazolopyrimidinones and their pharmaceutically acceptable salts according to claim 1, wherein the compound of formula 1 is selected from the group consisting of: 1) 5- [2-ethoxy-5- (isopropylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 1 ); 2) 5- [2-ethoxy-5- (benzylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 2 ); 3) 5- [2-propyloxy-5- (isopropylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 3 ); 4) 5- [2-ethoxy-5- (isopropylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 5 ); 5) 5- [2-ethoxy-5- (propylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 7 ); 6) 5- [2-ethoxy-5- (propylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 8 ); 7) 5- [2-ethoxy-5- (butylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 9 ); 8) 5- [2-ethoxy-5- (butylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 10 ); 9) 5- [2-ethoxy-5- (cyclopropylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 13 ); 10) 5- [2-ethoxy-5- (cyclopropylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 14 ); 11) 5- [2-ethoxy-5- (cyclohexylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 19 ); 12) 5- [2-ethoxy-5- (benzylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 22 ); 13) 5- [2-propyloxy-5- (benzylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 23 ); 14) 5- [2-ethoxy-5- (benzylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of Example 24 ); 15) 5- [2-ethoxy-5- (4-fluorophenylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 26); 16) 5- [2-ethoxy-5- (4-tert-butylphenylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of example 28); 17) 5- [2-ethoxy-5- (4-tert-butylphenylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of example 29); 18) 5- [2-ethoxy-5- (4-isopropylphenylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound of example 31); 19) 5- [2-ethoxy-5- (4-fluorophenylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 33); 20) 5- [2-ethoxy-5- (4-pyridylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 34); 21) 5- [2-propyloxy-5- (4-pyridylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 35); 22) 5- [2-ethoxy-5- (4-pyridylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 36); 23) 5- [2-ethoxy-5- (4-pyridylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 37); 24) 5- [2-ethoxy-5- (3-pyridylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 38); 25) 5- [2-propyloxy-5- (3-pyridylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 39); 26) 5- [2-ethoxy-5- (3-pyridylamidosulfonyl) phenyl] -1-ethyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 40); 27) 5- [2-ethoxy-5- (3-pyridylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 41); 28) 5- [2-propyloxy-5- (4-pyridylmethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one ( the compound of example 44); 29) 5- [2-ethoxy-5- (4-pyridylmethylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 46); 30) 5- [2-ethoxy-5- (3-pyridylmethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one ( the compound of example 47); 31) 5- [2-ethoxy-5- (3-pyridylmethylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 48); 32) 5- [2-propyloxy-5- (3-pyridylmethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 49); 33) 5- [2-ethoxy-5- (2-pyridylmethylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 51); 34) 5- [2-propyloxy-5- (2-pyridylmethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7-one (compound Example 52); 35) 5- [2-propyloxy-5- (1-methyl-3-pyrrolidinylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of Example 53); 36) 5- [2-ethoxy-5- (1-methyl-3-pyrrolidinylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of example 54); 37) 5- [2-propyloxy-5- (1-methyl-2-pyrrolidinylmethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of example 56); 38) 5- [2-ethoxy-5- (1-methyl-2-pyrrolidinylmethylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of Example 58); 39) 5- [2-propyloxy-5- (1-methyl-3-pyrrolidinylmethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of Example 60); 40) 5- [2-ethoxy-5- (1-methyl-3-pyrrolidinylmethylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of Example 62); 41) 5- [2-propyloxy-5- (1-ethyl-3-pyrrolidinylmethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of Example 64); 42) 5- [2-ethoxy-5- (1-ethyl-3-pyrrolidinylmethylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of Example 66); 43) 5- [2-propyloxy-5- (1-methyl-2-pyrrolidinyl ethylamidosulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of example 68) and 44) 5- [2-ethoxy-5- (1-methyl-2-pyrrolidinyl ethylamidosulfonyl) phenyl] -1-methyl-3-isobutyl-1,6-dihydro-7H-pyrazolo (4,3-d) pyrimidin-7 -one (compound of example 70). 8. The method of obtaining pyrazolopyrimidinone according to claim 1, comprising the stages 1) reacting a chlorosulfonated compound of formula (2) and a primary amine (3) at a suitable temperature and in a suitable solvent to form sulfonamide (4) (step 1); 2) the interaction of the carboxylic acid (4) obtained in stage 1, and pyrazolamine (5) with the formation of amide (6) in a known manner to obtain an amide from a carboxylic acid and an amine (stage 2) and 3) cyclization of the amide (6) obtained in stage 2, with the formation of the target compound of formula 1, known cyclization reaction used to obtain pyrimidinone (stage 3).

where R ₁ , R ₂ , R ₃ and R ₄ have the meanings indicated in the definition of formula 1. 9. Pharmaceutical compositions for the treatment of impotence, containing as an active ingredient pyrazolopyrimidinones and / or their pharmaceutically acceptable salts according to claim 1.