BG62768B1 - Пиридазинонови производни и методи за получаването им - Google Patents
Пиридазинонови производни и методи за получаването им Download PDFInfo
- Publication number
- BG62768B1 BG62768B1 BG100684A BG10068496A BG62768B1 BG 62768 B1 BG62768 B1 BG 62768B1 BG 100684 A BG100684 A BG 100684A BG 10068496 A BG10068496 A BG 10068496A BG 62768 B1 BG62768 B1 BG 62768B1
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- BG
- Bulgaria
- Prior art keywords
- group
- substituted
- atom
- pyridyl
- carbon atoms
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 19
- -1 sulphonyl group Chemical group 0.000 claims abstract description 187
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 77
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 15
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 154
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000003277 amino group Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- RCVLQLLCIGNCNJ-UHFFFAOYSA-N N1=CC(=CC=C1)C(=O)NCCCCC1=CC=C(C=C1)C1=CC=CN=N1 Chemical compound N1=CC(=CC=C1)C(=O)NCCCCC1=CC=C(C=C1)C1=CC=CN=N1 RCVLQLLCIGNCNJ-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 description 68
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 55
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000013078 crystal Substances 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 14
- 239000005457 ice water Substances 0.000 description 14
- 230000000704 physical effect Effects 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 230000036772 blood pressure Effects 0.000 description 11
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 201000008383 nephritis Diseases 0.000 description 7
- 230000002861 ventricular Effects 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241001631457 Cannula Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 206010040070 Septic Shock Diseases 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 229960003512 nicotinic acid Drugs 0.000 description 5
- 235000001968 nicotinic acid Nutrition 0.000 description 5
- 239000011664 nicotinic acid Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 230000035488 systolic blood pressure Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- WZICYOARYXPFCD-UHFFFAOYSA-N 1h-pyridazin-6-one;hydrobromide Chemical compound Br.O=C1C=CC=NN1 WZICYOARYXPFCD-UHFFFAOYSA-N 0.000 description 4
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- RBNITPVPQPJIPE-UHFFFAOYSA-N C1CC(=NN=C1)C2=CC3=C(CC(C3)CNS(=O)(=O)C4=CC=C(C=C4)Cl)C=C2 Chemical compound C1CC(=NN=C1)C2=CC3=C(CC(C3)CNS(=O)(=O)C4=CC=C(C=C4)Cl)C=C2 RBNITPVPQPJIPE-UHFFFAOYSA-N 0.000 description 4
- 206010014824 Endotoxic shock Diseases 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000005544 phthalimido group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000033764 rhythmic process Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 4
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VHCSBTPOPKFYIU-UHFFFAOYSA-N 2-chloroethanesulfonyl chloride Chemical compound ClCCS(Cl)(=O)=O VHCSBTPOPKFYIU-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- ZHWPTBJQTJMPJA-UHFFFAOYSA-N n-(4-phenylbutyl)acetamide Chemical compound CC(=O)NCCCCC1=CC=CC=C1 ZHWPTBJQTJMPJA-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- NYLYQIYULMIBEX-UHFFFAOYSA-N 3-[4-(4-aminobutoxy)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(OCCCCN)=CC=C1C1=NNC(=O)CC1 NYLYQIYULMIBEX-UHFFFAOYSA-N 0.000 description 2
- LVCNCVDHHGUFDG-UHFFFAOYSA-N 3-[4-(4-aminobutyl)phenyl]-1h-pyridazin-6-one Chemical compound C1=CC(CCCCN)=CC=C1C1=NNC(=O)C=C1 LVCNCVDHHGUFDG-UHFFFAOYSA-N 0.000 description 2
- JYNXPPLBHZEBBN-UHFFFAOYSA-N 3-[4-(4-aminobutyl)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(CCCCN)=CC=C1C1=NNC(=O)CC1 JYNXPPLBHZEBBN-UHFFFAOYSA-N 0.000 description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Optical Couplings Of Light Guides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16062095 | 1995-06-27 | ||
| JP1985996 | 1996-02-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG100684A BG100684A (bg) | 1997-03-31 |
| BG62768B1 true BG62768B1 (bg) | 2000-07-31 |
Family
ID=26356726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG100684A BG62768B1 (bg) | 1995-06-27 | 1996-06-27 | Пиридазинонови производни и методи за получаването им |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5698554A (de) |
| EP (1) | EP0751132B1 (de) |
| KR (1) | KR970061873A (de) |
| CN (1) | CN1144802A (de) |
| AR (1) | AR002602A1 (de) |
| AT (1) | ATE195937T1 (de) |
| AU (1) | AU694955B2 (de) |
| BG (1) | BG62768B1 (de) |
| CA (1) | CA2179939A1 (de) |
| DE (1) | DE69610036T2 (de) |
| DK (1) | DK0751132T3 (de) |
| ES (1) | ES2151110T3 (de) |
| GR (1) | GR3034910T3 (de) |
| HU (1) | HUP9601766A3 (de) |
| IL (1) | IL118631A (de) |
| MY (1) | MY132263A (de) |
| NO (1) | NO311084B1 (de) |
| PT (1) | PT751132E (de) |
| RU (1) | RU2131419C1 (de) |
| SG (1) | SG46741A1 (de) |
| TW (1) | TW432052B (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2235911C (en) * | 1997-05-27 | 2003-07-29 | Schneider (Usa) Inc. | Stent and stent-graft for treating branched vessels |
| DOP2000000070A (es) * | 1999-09-28 | 2002-02-28 | Bayer Healthcare Llc | Piridinas y piridacinas sustituidas con actividad de inhibición de angiogénesis |
| KR20030061051A (ko) * | 2002-01-07 | 2003-07-18 | 대한민국 (경상대학교 총장) | 신규한 아렌(혹은 알케인)술폰일피리다진온 유도체, 이의제조방법 및 유기반응에서의 용도 |
| AR050552A1 (es) * | 2004-09-02 | 2006-11-01 | Osi Pharm Inc | Mercaptoamidas como inhibidores de histona desacetilasa |
| UA91602C2 (ru) * | 2006-03-17 | 2010-08-10 | Сумитомо Кемикал Компани, Лимитед | Пиридазиноновое производное, его применение в качестве гербицида и промежуточное соединение |
| HRP20130044T1 (hr) | 2006-07-25 | 2013-02-28 | Cephalon, Inc. | Derivati piridizinona |
| EP2220073B1 (de) * | 2007-11-15 | 2014-09-03 | MSD Italia S.r.l. | Pyridazinonderivate als parp-inhibitoren |
| EP2547203A4 (de) | 2010-03-19 | 2013-12-25 | Purdue Research Foundation | Ccr5-modulatoren zur hiv-behandlung |
| CN103201279A (zh) | 2010-11-05 | 2013-07-10 | 赛诺米克斯公司 | 作为trpm8的调节剂有用的化合物 |
| EP2723718A1 (de) | 2011-06-24 | 2014-04-30 | Amgen Inc. | Trpm8-antagonisten und ihre verwendung bei behandlungen |
| JP2014527511A (ja) | 2011-06-24 | 2014-10-16 | アムジエン・インコーポレーテツド | Ｔｒｐｍ８拮抗剤及び治療におけるそれらの使用 |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| CN108473484B (zh) | 2015-10-01 | 2021-06-29 | 弗门尼舍公司 | 可用作trpm8调节剂的化合物 |
| PT3442972T (pt) | 2016-04-15 | 2020-05-29 | Abbvie Inc | Inibidores de bromodomínio |
| US11192900B2 (en) * | 2018-10-30 | 2021-12-07 | Nuvation Bio Inc. | Substituted 1,6-dihydropyridinones and 1,2-dihydroisoquinolinones as bet inhibitors |
| WO2020097258A1 (en) | 2018-11-06 | 2020-05-14 | Edgewise Therapeutics, Inc. | Pyridazinone compounds and uses thereof |
| ES2958954T3 (es) | 2018-11-06 | 2024-02-16 | Edgewise Therapeutics Inc | Compuestos de piridazinona y usos de los mismos |
| EP3877052B1 (de) | 2018-11-06 | 2023-08-16 | Edgewise Therapeutics, Inc. | Pyridazinonverbindungen und ihre verwendungen |
| KR102677015B1 (ko) | 2019-07-02 | 2024-06-19 | 누베이션 바이오 인크. | Bet 억제제로서의 헤테로시클릭 화합물 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6053022B2 (ja) | 1977-04-07 | 1985-11-22 | ウェルファイド株式会社 | ピリダジノン誘導体 |
| GB8323553D0 (en) * | 1983-09-02 | 1983-10-05 | Smith Kline French Lab | Pharmaceutical compositions |
| JPS6193169A (ja) * | 1984-10-12 | 1986-05-12 | Sankyo Co Ltd | ピリダジノン誘導体及びその製法 |
| DE3508692A1 (de) | 1985-03-12 | 1986-09-18 | Dr. Karl Thomae Gmbh, 7950 Biberach | 3-(4-(2-benzolsulfonylamino-aethyl)-benzoyl)propionsaeure, diese verbindung enthaltende arzneimittel und verfahren zu ihrer herstellung |
| EP0194548A3 (de) * | 1985-03-12 | 1988-08-17 | Dr. Karl Thomae GmbH | Neue Sulfonylaminoäthylverbindungen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| KR860007219A (ko) * | 1985-03-12 | 1986-10-08 | 베쩰, 좀머 | 설포닐아미노에틸 화합물의 제조방법 |
| DE3623944A1 (de) * | 1986-07-16 | 1988-02-11 | Thomae Gmbh Dr K | Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| JPS63145272A (ja) * | 1986-12-09 | 1988-06-17 | Morishita Seiyaku Kk | ４，５−ジヒドロ−６−（４−置換フエニル）−３（２ｈ）−ピリダジノン誘導体 |
| SU1486061A3 (ru) * | 1987-03-26 | 1989-06-07 | Mitsubishi Chem Ind | Способ получения производных пиридазинона или их солей |
| DE3728491A1 (de) * | 1987-08-26 | 1989-03-09 | Heumann Pharma Gmbh & Co | Dihydropyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE4134467A1 (de) * | 1991-10-18 | 1993-04-22 | Thomae Gmbh Dr K | Heterobiarylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DK0589037T3 (da) | 1991-03-01 | 1996-09-16 | Zeria Pharm Co Ltd | Indanderivat og thromboxanantagonist indeholdende samme |
| JP2616584B2 (ja) * | 1992-07-02 | 1997-06-04 | 田辺製薬株式会社 | ピリダジノン誘導体及びその製法 |
| CA2099743A1 (en) * | 1992-07-02 | 1994-01-03 | Akihiko Ishida | Pyridazinone derivatives and processes for preparing the same |
| CA2139088A1 (en) * | 1993-12-28 | 1995-06-29 | Akihiko Ishida | Indane derivatives, processes for preparing the same and synthetic intermediate of the same |
| CA2138812A1 (en) * | 1993-12-28 | 1995-06-29 | Akihiko Ishida | Indane derivative and processes for preparing the same |
| JP2757353B2 (ja) * | 1993-12-28 | 1998-05-25 | 田辺製薬株式会社 | インダン誘導体、その製法及びその合成中間体 |
-
1996
- 1996-06-01 IL IL11863196A patent/IL118631A/en not_active IP Right Cessation
- 1996-06-21 NO NO19962643A patent/NO311084B1/no unknown
- 1996-06-26 SG SG1996010164A patent/SG46741A1/en unknown
- 1996-06-26 RU RU96112778/04A patent/RU2131419C1/ru not_active IP Right Cessation
- 1996-06-26 TW TW085107678A patent/TW432052B/zh not_active IP Right Cessation
- 1996-06-26 HU HU9601766A patent/HUP9601766A3/hu unknown
- 1996-06-26 AR AR10332096A patent/AR002602A1/es unknown
- 1996-06-26 MY MYPI96002583A patent/MY132263A/en unknown
- 1996-06-26 CA CA002179939A patent/CA2179939A1/en not_active Abandoned
- 1996-06-27 CN CN96106873A patent/CN1144802A/zh active Pending
- 1996-06-27 DE DE69610036T patent/DE69610036T2/de not_active Expired - Fee Related
- 1996-06-27 ES ES96110412T patent/ES2151110T3/es not_active Expired - Lifetime
- 1996-06-27 AU AU56221/96A patent/AU694955B2/en not_active Ceased
- 1996-06-27 PT PT96110412T patent/PT751132E/pt unknown
- 1996-06-27 US US08/671,485 patent/US5698554A/en not_active Expired - Fee Related
- 1996-06-27 DK DK96110412T patent/DK0751132T3/da active
- 1996-06-27 KR KR1019960024718A patent/KR970061873A/ko not_active Ceased
- 1996-06-27 EP EP96110412A patent/EP0751132B1/de not_active Expired - Lifetime
- 1996-06-27 AT AT96110412T patent/ATE195937T1/de not_active IP Right Cessation
- 1996-06-27 BG BG100684A patent/BG62768B1/bg unknown
-
1997
- 1997-08-25 US US08/917,113 patent/US5808065A/en not_active Expired - Fee Related
-
2000
- 2000-11-24 GR GR20000402616T patent/GR3034910T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR3034910T3 (en) | 2001-02-28 |
| SG46741A1 (en) | 1998-02-20 |
| EP0751132A1 (de) | 1997-01-02 |
| ES2151110T3 (es) | 2000-12-16 |
| AU5622196A (en) | 1997-01-09 |
| DK0751132T3 (da) | 2000-11-13 |
| CA2179939A1 (en) | 1996-12-28 |
| AR002602A1 (es) | 1998-03-25 |
| NO311084B1 (no) | 2001-10-08 |
| HUP9601766A3 (en) | 1998-04-28 |
| DE69610036T2 (de) | 2001-04-12 |
| PT751132E (pt) | 2000-12-29 |
| EP0751132B1 (de) | 2000-08-30 |
| CN1144802A (zh) | 1997-03-12 |
| US5808065A (en) | 1998-09-15 |
| HU9601766D0 (en) | 1996-08-28 |
| US5698554A (en) | 1997-12-16 |
| KR970061873A (ko) | 1997-09-12 |
| NO962643D0 (no) | 1996-06-21 |
| TW432052B (en) | 2001-05-01 |
| ATE195937T1 (de) | 2000-09-15 |
| IL118631A (en) | 2002-05-23 |
| DE69610036D1 (de) | 2000-10-05 |
| MY132263A (en) | 2007-09-28 |
| HUP9601766A2 (en) | 1997-02-28 |
| IL118631A0 (en) | 1996-10-16 |
| NO962643L (no) | 1996-12-30 |
| RU2131419C1 (ru) | 1999-06-10 |
| BG100684A (bg) | 1997-03-31 |
| AU694955B2 (en) | 1998-08-06 |
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