UA74571C2 - Compounds of pyridazinylphenyl hydrazone being used in congestive heart failure - Google Patents
Compounds of pyridazinylphenyl hydrazone being used in congestive heart failure Download PDFInfo
- Publication number
- UA74571C2 UA74571C2 UA2002108100A UA2002108100A UA74571C2 UA 74571 C2 UA74571 C2 UA 74571C2 UA 2002108100 A UA2002108100 A UA 2002108100A UA 2002108100 A UA2002108100 A UA 2002108100A UA 74571 C2 UA74571 C2 UA 74571C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methyl
- hydrogen
- alkyl
- hydroxy
- pyridazin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- -1 pyridazinylphenyl hydrazone Chemical class 0.000 title claims abstract description 27
- 206010007559 Cardiac failure congestive Diseases 0.000 title claims abstract description 6
- 206010019280 Heart failures Diseases 0.000 title claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000004442 acylamino group Chemical group 0.000 claims abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910002514 Co–Co Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 13
- 229910052791 calcium Inorganic materials 0.000 abstract description 13
- 239000011575 calcium Substances 0.000 abstract description 13
- 210000004165 myocardium Anatomy 0.000 abstract description 8
- 230000035945 sensitivity Effects 0.000 abstract description 8
- 102000002585 Contractile Proteins Human genes 0.000 abstract description 7
- 108010068426 Contractile Proteins Proteins 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 238000005481 NMR spectroscopy Methods 0.000 description 46
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 39
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000007429 general method Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000835 fiber Substances 0.000 description 8
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 210000005240 left ventricle Anatomy 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002429 hydrazines Chemical class 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000010412 perfusion Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HDJKGUBFDGUPFK-UHFFFAOYSA-N 3-(4-hydrazinylphenyl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(NN)C=C1 HDJKGUBFDGUPFK-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 210000003540 papillary muscle Anatomy 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000002604 ultrasonography Methods 0.000 description 3
- AQKWZDZQPZSATN-UHFFFAOYSA-N 3-(3-hydrazinylphenyl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=CC(NN)=C1 AQKWZDZQPZSATN-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- MWDICCJVJOMHSI-UHFFFAOYSA-N 2,4-dihydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC(O)=C([N+]([O-])=O)C=C1C=O MWDICCJVJOMHSI-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- SNHLRYZWIWHWFX-UHFFFAOYSA-N 3-(3-aminophenyl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=CC(N)=C1 SNHLRYZWIWHWFX-UHFFFAOYSA-N 0.000 description 1
- NWUOGOISBQCNKQ-UHFFFAOYSA-N 3-(4-aminophenyl)-4-methyl-1h-pyridazin-6-one Chemical compound CC1=CC(=O)NN=C1C1=CC=C(N)C=C1 NWUOGOISBQCNKQ-UHFFFAOYSA-N 0.000 description 1
- FVTHDBGLGNPRCR-UHFFFAOYSA-N 3-(4-hydrazinylphenyl)-4-methyl-1h-pyridazin-6-one Chemical compound CC1=CC(=O)NN=C1C1=CC=C(NN)C=C1 FVTHDBGLGNPRCR-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- PHCNQUJHXJQLQR-UHFFFAOYSA-N 4-hydroxy-3-methoxy-2-nitrobenzaldehyde Chemical compound COC1=C(O)C=CC(C=O)=C1[N+]([O-])=O PHCNQUJHXJQLQR-UHFFFAOYSA-N 0.000 description 1
- MDVFJPDMXLCQFR-UHFFFAOYSA-N 6-(4-aminophenyl)-2,5-dimethylpyridazin-3-one Chemical compound CC1=CC(=O)N(C)N=C1C1=CC=C(N)C=C1 MDVFJPDMXLCQFR-UHFFFAOYSA-N 0.000 description 1
- PAPOUVTXLICLIG-UHFFFAOYSA-N 6-(4-aminophenyl)-2-methylpyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C1=CC=C(N)C=C1 PAPOUVTXLICLIG-UHFFFAOYSA-N 0.000 description 1
- ARHJNGMCJNVJSD-UHFFFAOYSA-N 6-(4-hydrazinylphenyl)-2,5-dimethylpyridazin-3-one Chemical compound CC1=CC(=O)N(C)N=C1C1=CC=C(NN)C=C1 ARHJNGMCJNVJSD-UHFFFAOYSA-N 0.000 description 1
- VBBCUFVTWROALH-UHFFFAOYSA-N 6-(4-hydrazinylphenyl)-2-methylpyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C1=CC=C(NN)C=C1 VBBCUFVTWROALH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000004420 Creatine Kinase Human genes 0.000 description 1
- 108010042126 Creatine kinase Proteins 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010044467 Isoenzymes Proteins 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 108010010677 Phosphodiesterase I Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001964 calcium overload Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000005246 left atrium Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 102000005681 phospholamban Human genes 0.000 description 1
- 108010059929 phospholamban Proteins 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003492 pulmonary vein Anatomy 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 208000013220 shortness of breath Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 1
- 229950001870 spizofurone Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20000577A FI20000577A0 (fi) | 2000-03-13 | 2000-03-13 | Pyridatsinyylifenyylihydratsoneja |
| PCT/FI2001/000241 WO2001068611A1 (en) | 2000-03-13 | 2001-03-12 | Pyridazinyl phenyl hydrazones useful against congestive heart failure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA74571C2 true UA74571C2 (en) | 2006-01-16 |
Family
ID=8557913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002108100A UA74571C2 (en) | 2000-03-13 | 2001-12-03 | Compounds of pyridazinylphenyl hydrazone being used in congestive heart failure |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6699868B2 (es) |
| EP (1) | EP1265871B1 (es) |
| JP (1) | JP2003527375A (es) |
| KR (1) | KR20030001379A (es) |
| CN (1) | CN1191241C (es) |
| AR (1) | AR027644A1 (es) |
| AT (1) | ATE317388T1 (es) |
| AU (2) | AU4657701A (es) |
| BG (1) | BG65859B1 (es) |
| BR (1) | BR0109136A (es) |
| CA (1) | CA2403188A1 (es) |
| CZ (1) | CZ20022997A3 (es) |
| DE (1) | DE60117131T2 (es) |
| DK (1) | DK1265871T3 (es) |
| EA (1) | EA005574B1 (es) |
| EE (1) | EE200200520A (es) |
| ES (1) | ES2256222T3 (es) |
| FI (1) | FI20000577A0 (es) |
| HK (1) | HK1052008A1 (es) |
| HR (1) | HRP20020816A2 (es) |
| HU (1) | HUP0300177A3 (es) |
| IL (2) | IL151492A0 (es) |
| MX (1) | MXPA02008997A (es) |
| NO (1) | NO324172B1 (es) |
| NZ (1) | NZ521162A (es) |
| PL (1) | PL357107A1 (es) |
| RS (1) | RS50439B (es) |
| SI (1) | SI1265871T1 (es) |
| SK (1) | SK287163B6 (es) |
| UA (1) | UA74571C2 (es) |
| WO (1) | WO2001068611A1 (es) |
| ZA (1) | ZA200206917B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0015228D0 (en) * | 2000-06-21 | 2000-08-16 | Portela & Ca Sa | Substituted nitrated catechols, their use in the treatment of some central and peripheral nervous system disorders |
| JP4561698B2 (ja) * | 2002-02-19 | 2010-10-13 | 小野薬品工業株式会社 | 縮合ピリダジン誘導体化合物およびその化合物を有効成分として含有する薬剤 |
| EP1612204A4 (en) * | 2003-03-31 | 2007-04-11 | Daiichi Seiyaku Co | HYDRAZONE DERIVATIVE |
| GB0503962D0 (en) | 2005-02-25 | 2005-04-06 | Kudos Pharm Ltd | Compounds |
| WO2008013838A2 (en) | 2006-07-25 | 2008-01-31 | Cephalon, Inc. | Pyridizinone derivatives |
| US20100286150A1 (en) | 2007-01-17 | 2010-11-11 | Fia Westerholm | Levosimendan for use in treating chronic valvular disease |
| EP2762465B1 (en) * | 2011-09-27 | 2018-01-10 | Zeon Corporation | Intermediate for manufacture of polymerizable compound and process for manufacture thereof |
| ES2684776T3 (es) * | 2013-01-18 | 2018-10-04 | Bristol-Myers Squibb Company | Ftalazinonas e isoquinolinonas como inhibidores de ROCK |
| JPWO2019235569A1 (ja) * | 2018-06-08 | 2021-07-08 | 日産化学株式会社 | キナーゼ阻害剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3531658A1 (de) | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Heterocyclisch substituierte indole, zwischenprodukte, verfahren zu ihrer herstellung und arzneimittel |
| GB8903130D0 (en) * | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
| US5185332A (en) * | 1989-02-11 | 1993-02-09 | Orion-Yhtyma Oy | Thiadiazines and pharmaceutical compositions thereof as well as method of use |
| FI973804A (fi) * | 1997-09-26 | 1999-03-27 | Orion Yhtymae Oy | Levosimendaanin oraalisia koostumuksia |
-
2000
- 2000-03-13 FI FI20000577A patent/FI20000577A0/fi unknown
-
2001
- 2001-03-12 BR BR0109136-0A patent/BR0109136A/pt not_active IP Right Cessation
- 2001-03-12 JP JP2001567705A patent/JP2003527375A/ja not_active Withdrawn
- 2001-03-12 US US10/221,348 patent/US6699868B2/en not_active Expired - Fee Related
- 2001-03-12 CZ CZ20022997A patent/CZ20022997A3/cs unknown
- 2001-03-12 AT AT01919489T patent/ATE317388T1/de not_active IP Right Cessation
- 2001-03-12 NZ NZ521162A patent/NZ521162A/en unknown
- 2001-03-12 RS YUP-685/02A patent/RS50439B/sr unknown
- 2001-03-12 IL IL15149201A patent/IL151492A0/xx active IP Right Grant
- 2001-03-12 WO PCT/FI2001/000241 patent/WO2001068611A1/en active IP Right Grant
- 2001-03-12 SK SK1288-2002A patent/SK287163B6/sk not_active IP Right Cessation
- 2001-03-12 SI SI200130518T patent/SI1265871T1/sl unknown
- 2001-03-12 EE EEP200200520A patent/EE200200520A/xx unknown
- 2001-03-12 MX MXPA02008997A patent/MXPA02008997A/es active IP Right Grant
- 2001-03-12 AR ARP010101149A patent/AR027644A1/es unknown
- 2001-03-12 AU AU4657701A patent/AU4657701A/xx active Pending
- 2001-03-12 KR KR1020027012066A patent/KR20030001379A/ko not_active Application Discontinuation
- 2001-03-12 EP EP01919489A patent/EP1265871B1/en not_active Expired - Lifetime
- 2001-03-12 PL PL01357107A patent/PL357107A1/xx not_active Application Discontinuation
- 2001-03-12 CA CA002403188A patent/CA2403188A1/en not_active Abandoned
- 2001-03-12 CN CNB018065309A patent/CN1191241C/zh not_active Expired - Fee Related
- 2001-03-12 HU HU0300177A patent/HUP0300177A3/hu unknown
- 2001-03-12 DE DE60117131T patent/DE60117131T2/de not_active Expired - Fee Related
- 2001-03-12 DK DK01919489T patent/DK1265871T3/da active
- 2001-03-12 EA EA200200973A patent/EA005574B1/ru not_active IP Right Cessation
- 2001-03-12 AU AU2001246577A patent/AU2001246577B2/en not_active Ceased
- 2001-03-12 ES ES01919489T patent/ES2256222T3/es not_active Expired - Lifetime
- 2001-12-03 UA UA2002108100A patent/UA74571C2/uk unknown
-
2002
- 2002-08-26 IL IL151492A patent/IL151492A/en not_active IP Right Cessation
- 2002-08-28 ZA ZA200206917A patent/ZA200206917B/en unknown
- 2002-09-05 NO NO20024247A patent/NO324172B1/no not_active IP Right Cessation
- 2002-10-08 BG BG107175A patent/BG65859B1/bg unknown
- 2002-10-11 HR HRP20020816 patent/HRP20020816A2/hr not_active Application Discontinuation
-
2003
- 2003-06-16 HK HK03104272A patent/HK1052008A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0208874B1 (en) | Prophylactic and therapeutic agent for circulatory disorders | |
| JP2703408B2 (ja) | １，４‐ベンゾチアゼピン誘導体 | |
| UA74571C2 (en) | Compounds of pyridazinylphenyl hydrazone being used in congestive heart failure | |
| Sircar et al. | Cardiotonic agents. 9. Synthesis and biological evaluation of a series of (E)-4, 5-dihydro-6-[2-[4-(1H-imidazol-1-yl) phenyl] ethenyl]-3 (2H)-pyridazinones: a novel class of compounds with positive inotropic, antithrombotic, and vasodilatory activities for the treatment of congestive heart failure | |
| JPS62108814A (ja) | 過酸化脂質生成抑制剤 | |
| US4025649A (en) | Acetic acid derivatives having pharmacological activity and compositions containing the same | |
| US5905078A (en) | Use of a pyridazinone derivative | |
| SU1672929A3 (ru) | Способ получени производных гидразина или их фармацевтически совместимых солей | |
| US4280998A (en) | 1,4-Dihydropyridazine-3-carboxylic acid derivatives, a process for their preparation and their use as antihypertensives | |
| US4002751A (en) | 5-Hydrazinopyridazin-3(2H)-ones | |
| USRE35801E (en) | Prophylactic and therapeutic composition for circulatory disorders and method of treatment | |
| CA2820135C (fr) | Derives de diarylpyridazinones, leur preparation et leur application en therapeutique humaine | |
| JP3553158B2 (ja) | ピリダジノインドール誘導体 | |
| JPH01168683A (ja) | 新規な置換ニトロジヒドロピリジン、その製造法、及びその使用 | |
| US4024259A (en) | 3-Anilino-2,4-diazabicyclo[3.2.1]octenes | |
| US3951991A (en) | 4-Aryl-6-amino-3,4-dihydropyrid-2-one-3,5-dicarboxylic acid ester | |
| JPH0222069B2 (es) | ||
| EP0802900A1 (en) | Antiarrhythmic (s)-enantiomers of methanesulfonamides | |
| JP2004532249A (ja) | 緑内障ｖｉの治療方法 | |
| JPH0210133B2 (es) | ||
| JPH03251588A (ja) | ケイ素置換アリルアミン誘導体 | |
| IE42948B1 (en) | Pharmaceutically acceptable salts of alkanoic acid derivatives and compositions containing the same |