NO862723L - Fremgangsmaate ved fremstilling av hydropyridazinforbindelser. - Google Patents
Fremgangsmaate ved fremstilling av hydropyridazinforbindelser.Info
- Publication number
- NO862723L NO862723L NO862723A NO862723A NO862723L NO 862723 L NO862723 L NO 862723L NO 862723 A NO862723 A NO 862723A NO 862723 A NO862723 A NO 862723A NO 862723 L NO862723 L NO 862723L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen
- compound
- compounds
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 111
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 26
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- -1 alkyl bromoacetate Chemical compound 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- STZWBTLEBZNTIX-UHFFFAOYSA-N 3-[3-(6-oxo-1h-pyridazin-3-yl)phenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=C(C=CC=2)C2=NNC(=O)C=C2)=N1 STZWBTLEBZNTIX-UHFFFAOYSA-N 0.000 claims description 4
- MTPSKWYBRGLEBS-UHFFFAOYSA-N 3-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CC(=CC=2)C2=NNC(=O)C=C2)=N1 MTPSKWYBRGLEBS-UHFFFAOYSA-N 0.000 claims description 4
- BBWGKXPPKBMTTC-UHFFFAOYSA-N 3-[4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CC(=CC=2)C=2CCC(=O)NN=2)=N1 BBWGKXPPKBMTTC-UHFFFAOYSA-N 0.000 claims description 4
- YRRYDWCZPXJWOS-UHFFFAOYSA-N 4-methyl-3-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(C=2C(CC(=O)NN=2)C)C=C1 YRRYDWCZPXJWOS-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BDURSHFORVMXBD-UHFFFAOYSA-N 3-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(C2=NNC(=O)C=C2)C=C1 BDURSHFORVMXBD-UHFFFAOYSA-N 0.000 claims description 3
- ZYGTVVRIYKTLCI-UHFFFAOYSA-N 4-methyl-3-[4-(4-methyl-6-oxo-1h-pyridazin-3-yl)phenyl]-1h-pyridazin-6-one Chemical compound CC1=CC(=O)NN=C1C1=CC=C(C=2C(=CC(=O)NN=2)C)C=C1 ZYGTVVRIYKTLCI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- BKRIDRJBGVFWRN-UHFFFAOYSA-N 3-[4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CC(=CC=2)C2=NNC(=O)C=C2)=N1 BKRIDRJBGVFWRN-UHFFFAOYSA-N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229940124549 vasodilator Drugs 0.000 abstract description 4
- 239000003071 vasodilator agent Substances 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 230000000297 inotrophic effect Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 43
- 239000000203 mixture Substances 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 229960000583 acetic acid Drugs 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000010992 reflux Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 8
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 5
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229940095074 cyclic amp Drugs 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 230000001057 ionotropic effect Effects 0.000 description 5
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 230000002861 ventricular Effects 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 206010019280 Heart failures Diseases 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 3
- 102000000584 Calmodulin Human genes 0.000 description 3
- 108010041952 Calmodulin Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 3
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 2
- RJJQKFVSENWLLE-UHFFFAOYSA-N 1-(4-propanoylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C(=O)CC)C=C1 RJJQKFVSENWLLE-UHFFFAOYSA-N 0.000 description 2
- ZNBVIYMIVFKTIW-UHFFFAOYSA-N 1-(4-propylphenyl)ethanone Chemical compound CCCC1=CC=C(C(C)=O)C=C1 ZNBVIYMIVFKTIW-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- BNLGPCDIXZTQCF-UHFFFAOYSA-N 3-(4-propanoylphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(C(=O)CC)=CC=C1C1=NNC(=O)C=C1 BNLGPCDIXZTQCF-UHFFFAOYSA-N 0.000 description 2
- JDOKMTFQTLPOJN-UHFFFAOYSA-N 3-(4-propylphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(CCC)=CC=C1C1=NNC(=O)C=C1 JDOKMTFQTLPOJN-UHFFFAOYSA-N 0.000 description 2
- SMRHLUPFZBNLAK-UHFFFAOYSA-N 3-(dimethylamino)-1-[4-[3-(dimethylamino)-2-methylpropanoyl]phenyl]-2-methylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CN(C)CC(C)C(=O)C1=CC=C(C(=O)C(C)CN(C)C)C=C1 SMRHLUPFZBNLAK-UHFFFAOYSA-N 0.000 description 2
- NNJRXHFVSRKPMR-UHFFFAOYSA-N 3-[4-[3-(dimethylamino)-2-methylpropanoyl]phenyl]-1h-pyridazin-6-one;hydrochloride Chemical compound Cl.C1=CC(C(=O)C(CN(C)C)C)=CC=C1C1=NNC(=O)C=C1 NNJRXHFVSRKPMR-UHFFFAOYSA-N 0.000 description 2
- ZFVOVZIUPMOJED-UHFFFAOYSA-N 3-methyl-4-oxo-4-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]butanenitrile Chemical compound C1=CC(C(=O)C(CC#N)C)=CC=C1C1=NNC(=O)C=C1 ZFVOVZIUPMOJED-UHFFFAOYSA-N 0.000 description 2
- GZQXEVCGHYDTKD-UHFFFAOYSA-N 4-[4-(3-carboxy-2-methylpropanoyl)phenyl]-3-methyl-4-oxobutanoic acid Chemical compound OC(=O)CC(C)C(=O)C1=CC=C(C(=O)C(C)CC(O)=O)C=C1 GZQXEVCGHYDTKD-UHFFFAOYSA-N 0.000 description 2
- ICEAMAAUNDBLBI-UHFFFAOYSA-N 4-[4-(3-cyano-2-methylpropanoyl)phenyl]-3-methyl-4-oxobutanenitrile Chemical compound N#CCC(C)C(=O)C1=CC=C(C(=O)C(C)CC#N)C=C1 ICEAMAAUNDBLBI-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- 229920002271 DEAE-Sepharose Polymers 0.000 description 2
- WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 description 2
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 2
- 229960002105 amrinone Drugs 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- 239000000168 bronchodilator agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229960000648 digitoxin Drugs 0.000 description 2
- WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 2
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- 230000002588 toxic effect Effects 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858517051A GB8517051D0 (en) | 1985-07-05 | 1985-07-05 | Chemical compounds |
| GB868606853A GB8606853D0 (en) | 1986-03-20 | 1986-03-20 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO862723D0 NO862723D0 (no) | 1986-07-04 |
| NO862723L true NO862723L (no) | 1987-01-06 |
Family
ID=26289481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO862723A NO862723L (no) | 1985-07-05 | 1986-07-04 | Fremgangsmaate ved fremstilling av hydropyridazinforbindelser. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4904664A (xx) |
| EP (1) | EP0208517B1 (xx) |
| JP (1) | JPS6212765A (xx) |
| CN (1) | CN86105663A (xx) |
| AT (1) | ATE56440T1 (xx) |
| AU (1) | AU580677B2 (xx) |
| DE (1) | DE3674094D1 (xx) |
| DK (1) | DK316986A (xx) |
| ES (1) | ES2000209A6 (xx) |
| FI (1) | FI862840A (xx) |
| GR (1) | GR861719B (xx) |
| HU (1) | HUT41393A (xx) |
| IL (1) | IL79280A (xx) |
| NO (1) | NO862723L (xx) |
| NZ (1) | NZ216741A (xx) |
| PT (1) | PT82876B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4962110A (en) * | 1985-03-12 | 1990-10-09 | Smith Kline & French Laboratories Limited | Pyridazinone derivatives |
| US4970210A (en) * | 1987-07-17 | 1990-11-13 | Abbott Laboratories | Triazinone lipoxygenase compounds |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088762A (en) * | 1971-02-22 | 1978-05-09 | Bdh Pharmaceuticals Limited | 6-(P-PIPERAZINO)-PHENYL-4,5-DIHYDRO-3(2H)pyridazinones |
| US3975388A (en) * | 1971-02-22 | 1976-08-17 | Bdh Pharmaceuticals Limited | Pyridazinones |
| BE790106A (fr) * | 1971-10-14 | 1973-04-13 | Basf Ag | Dihydropyridazones, leur preparation et leurs utilisations therapeutiques |
| EP0059688B1 (de) * | 1981-03-04 | 1985-05-15 | Ciba-Geigy Ag | Pyridazinone, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen und deren Verwendung |
| US4353905A (en) * | 1981-09-17 | 1982-10-12 | Warner-Lambert Company | Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones |
| HU190412B (en) * | 1981-09-17 | 1986-09-29 | Warner-Lambert Co,Us | Process for producing substituted 4,5-dihiydro-6-bracket-substituted-bracket closed-phenyl-3-bracket-2h-bracket closed-pyridazinones and 6-bracket-substituted-bracket closed-phenyl-3-bracket-2h-bracket closed-pyridazinones |
| IT1171604B (it) * | 1981-10-22 | 1987-06-10 | Roussel Maestretti Spa | Derivati di acido 4-fenil-4-ossobuten-2-oico dotati di proprieta' farmacologiche e loro procedimento di preparazione |
| JPS58113180A (ja) * | 1981-12-28 | 1983-07-05 | Mitsui Toatsu Chem Inc | ピリダジノン誘導体 |
| JPS58162577A (ja) * | 1982-03-19 | 1983-09-27 | Sankyo Co Ltd | ６−フエニルピリダジノン化合物の製造法 |
| DE3212304A1 (de) * | 1982-04-02 | 1983-10-06 | Nattermann A & Cie | Imidazolylphenyl-tetrahydropyridazine, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| NZ208107A (en) * | 1983-05-11 | 1986-12-05 | Byk Gulden Lomberg Chem Fab | 6-aryl-3(2h)-pyridazinones and pharmaceutical compositions |
| US4599332A (en) * | 1983-12-07 | 1986-07-08 | Warner-Lambert Company | 4,5-dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]-ethenyl]-3(2H)-pyridazinones and related compounds |
| JPS60197672A (ja) * | 1984-03-16 | 1985-10-07 | Mitsubishi Chem Ind Ltd | ビリダジノン誘導体またはその塩類 |
| DE3425632A1 (de) * | 1984-07-12 | 1986-01-16 | Basf Ag, 6700 Ludwigshafen | (pyrrol-1-yl)-phenyl-dihydropyridazinone, ihre herstellung und verwendung |
| US4816454A (en) * | 1984-09-21 | 1989-03-28 | Cassella Aktiengesellschaft | 4,5-dihydro-3(2H)-pyridazinones and their pharmacological use |
| US4631279A (en) * | 1984-10-15 | 1986-12-23 | Eli Lilly And Company | 6-(pyridinylphenyl)dihydropyridazinones as inotropic agents |
-
1986
- 1986-06-30 IL IL79280A patent/IL79280A/xx unknown
- 1986-07-01 US US06/880,849 patent/US4904664A/en not_active Expired - Fee Related
- 1986-07-01 GR GR861719A patent/GR861719B/el unknown
- 1986-07-01 PT PT82876A patent/PT82876B/pt unknown
- 1986-07-02 AU AU59488/86A patent/AU580677B2/en not_active Ceased
- 1986-07-03 DK DK316986A patent/DK316986A/da not_active Application Discontinuation
- 1986-07-03 NZ NZ216741A patent/NZ216741A/xx unknown
- 1986-07-04 DE DE8686305187T patent/DE3674094D1/de not_active Expired - Lifetime
- 1986-07-04 HU HU862821A patent/HUT41393A/hu unknown
- 1986-07-04 NO NO862723A patent/NO862723L/no unknown
- 1986-07-04 EP EP86305187A patent/EP0208517B1/en not_active Expired - Lifetime
- 1986-07-04 AT AT86305187T patent/ATE56440T1/de not_active IP Right Cessation
- 1986-07-04 ES ES8600129A patent/ES2000209A6/es not_active Expired
- 1986-07-04 JP JP61158634A patent/JPS6212765A/ja active Granted
- 1986-07-04 FI FI862840A patent/FI862840A/fi not_active Application Discontinuation
- 1986-07-05 CN CN198686105663A patent/CN86105663A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT82876B (en) | 1988-11-03 |
| CN86105663A (zh) | 1987-01-21 |
| NO862723D0 (no) | 1986-07-04 |
| FI862840A (fi) | 1987-01-06 |
| PT82876A (en) | 1986-08-01 |
| EP0208517B1 (en) | 1990-09-12 |
| HUT41393A (en) | 1987-04-28 |
| FI862840A0 (fi) | 1986-07-04 |
| DE3674094D1 (de) | 1990-10-18 |
| EP0208517A2 (en) | 1987-01-14 |
| JPS6212765A (ja) | 1987-01-21 |
| IL79280A (en) | 1990-07-12 |
| AU5948886A (en) | 1987-01-08 |
| AU580677B2 (en) | 1989-01-27 |
| EP0208517A3 (en) | 1988-03-23 |
| NZ216741A (en) | 1988-10-28 |
| DK316986A (da) | 1987-01-06 |
| DK316986D0 (da) | 1986-07-03 |
| ATE56440T1 (de) | 1990-09-15 |
| US4904664A (en) | 1990-02-27 |
| GR861719B (en) | 1986-11-04 |
| ES2000209A6 (es) | 1988-01-16 |
| JPH0586951B2 (xx) | 1993-12-14 |
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