SE437514B - N-/3-dimetylamino-2-(4-pyridinyl)-2-propenyliden/-n-metylmetaniminiumsalt, sett att framstella detta och kardioton komposition for okning av hjertkontraktiliteten - Google Patents
N-/3-dimetylamino-2-(4-pyridinyl)-2-propenyliden/-n-metylmetaniminiumsalt, sett att framstella detta och kardioton komposition for okning av hjertkontraktilitetenInfo
- Publication number
- SE437514B SE437514B SE8101205A SE8101205A SE437514B SE 437514 B SE437514 B SE 437514B SE 8101205 A SE8101205 A SE 8101205A SE 8101205 A SE8101205 A SE 8101205A SE 437514 B SE437514 B SE 437514B
- Authority
- SE
- Sweden
- Prior art keywords
- pyridinyl
- salt
- dimethylamino
- propenylidene
- acid addition
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 48
- 239000000203 mixture Substances 0.000 title claims description 17
- -1 4-PYRIDINYL Chemical class 0.000 title description 7
- 210000002216 heart Anatomy 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 33
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000012458 free base Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- 230000003177 cardiotonic effect Effects 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000000747 cardiac effect Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 230000001746 atrial effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000022244 formylation Effects 0.000 description 3
- 238000006170 formylation reaction Methods 0.000 description 3
- 210000003540 papillary muscle Anatomy 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MKNJJNFVIWDHEM-UHFFFAOYSA-N 1-pyridin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=NC=C1 MKNJJNFVIWDHEM-UHFFFAOYSA-N 0.000 description 1
- UAOTWASOGSHQAI-UHFFFAOYSA-N 2-methoxy-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC=C1C1=CC=NC=C1 UAOTWASOGSHQAI-UHFFFAOYSA-N 0.000 description 1
- NTHQYHTZRJMPFI-UHFFFAOYSA-N 2-oxo-5-pyridin-2-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=CC=N1 NTHQYHTZRJMPFI-UHFFFAOYSA-N 0.000 description 1
- PNAHPHGJXNKLNF-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylprop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC=C1 PNAHPHGJXNKLNF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- MPAYEWNVIPXRDP-UHFFFAOYSA-N ethanimine Chemical class CC=N MPAYEWNVIPXRDP-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- OWVFJYJLBSWYII-UHFFFAOYSA-N n,n-dimethyl-2-pyridin-4-ylethenamine Chemical compound CN(C)C=CC1=CC=NC=C1 OWVFJYJLBSWYII-UHFFFAOYSA-N 0.000 description 1
- NYVSDPNXBIEFPW-UHFFFAOYSA-N n-methylmethanimine Chemical class CN=C NYVSDPNXBIEFPW-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/124,808 US4264609A (en) | 1980-02-26 | 1980-02-26 | N-[3-Dimethylamino-2-(4-pyridinyl)-2-propenylidene]-N-methylmethaniminium chloride hydrochloride, its use in preparing 5-(cyano or carbamyl)-[3,4'-bipyridin]-6(1H)-one and its use as a cardiotonic |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8101205L SE8101205L (sv) | 1981-08-27 |
| SE437514B true SE437514B (sv) | 1985-03-04 |
Family
ID=22416880
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8101205A SE437514B (sv) | 1980-02-26 | 1981-02-24 | N-/3-dimetylamino-2-(4-pyridinyl)-2-propenyliden/-n-metylmetaniminiumsalt, sett att framstella detta och kardioton komposition for okning av hjertkontraktiliteten |
| SE8402727A SE452764B (sv) | 1980-02-26 | 1984-05-21 | Forfarande for framstellning av 5-(cyano eller karbamyl)-(3,4-bipyridin)-6(1h)-on |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8402727A SE452764B (sv) | 1980-02-26 | 1984-05-21 | Forfarande for framstellning av 5-(cyano eller karbamyl)-(3,4-bipyridin)-6(1h)-on |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4264609A (enExample) |
| JP (1) | JPS56128758A (enExample) |
| KR (2) | KR840002067B1 (enExample) |
| AR (1) | AR230630A1 (enExample) |
| AT (2) | AT380237B (enExample) |
| AU (1) | AU541644B2 (enExample) |
| BE (1) | BE887663A (enExample) |
| CA (1) | CA1128523A (enExample) |
| CH (1) | CH647509A5 (enExample) |
| DE (1) | DE3107306A1 (enExample) |
| DK (1) | DK171253B1 (enExample) |
| ES (1) | ES499776A1 (enExample) |
| FI (1) | FI76787C (enExample) |
| FR (1) | FR2476646A1 (enExample) |
| GB (1) | GB2070600B (enExample) |
| HK (1) | HK71789A (enExample) |
| IE (1) | IE51696B1 (enExample) |
| IL (1) | IL62161A (enExample) |
| IT (1) | IT1210992B (enExample) |
| LU (1) | LU83169A1 (enExample) |
| MX (1) | MX6908E (enExample) |
| NL (1) | NL192109C (enExample) |
| NO (1) | NO156689C (enExample) |
| NZ (1) | NZ196282A (enExample) |
| PH (2) | PH19904A (enExample) |
| PT (1) | PT72573B (enExample) |
| SE (2) | SE437514B (enExample) |
| ZA (1) | ZA811124B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE77817T1 (de) | 1985-04-30 | 1992-07-15 | Dresden Arzneimittel | 3-cyan-pyridine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4004012A (en) * | 1975-10-14 | 1977-01-18 | Sterling Drug Inc. | 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones |
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
-
1980
- 1980-02-26 US US06/124,808 patent/US4264609A/en not_active Expired - Lifetime
-
1981
- 1981-02-17 NZ NZ196282A patent/NZ196282A/xx unknown
- 1981-02-18 IL IL62161A patent/IL62161A/xx not_active IP Right Cessation
- 1981-02-20 ZA ZA00811124A patent/ZA811124B/xx unknown
- 1981-02-20 AU AU67487/81A patent/AU541644B2/en not_active Expired
- 1981-02-20 GB GB8105369A patent/GB2070600B/en not_active Expired
- 1981-02-24 PH PH25258A patent/PH19904A/en unknown
- 1981-02-24 IT IT8119952A patent/IT1210992B/it active
- 1981-02-24 CH CH1222/81A patent/CH647509A5/fr not_active IP Right Cessation
- 1981-02-24 FR FR8103609A patent/FR2476646A1/fr active Granted
- 1981-02-24 SE SE8101205A patent/SE437514B/sv not_active IP Right Cessation
- 1981-02-25 MX MX819321U patent/MX6908E/es unknown
- 1981-02-25 PT PT72573A patent/PT72573B/pt unknown
- 1981-02-25 DK DK083981A patent/DK171253B1/da not_active IP Right Cessation
- 1981-02-25 KR KR1019810000616A patent/KR840002067B1/ko not_active Expired
- 1981-02-25 NL NL8100922A patent/NL192109C/nl not_active IP Right Cessation
- 1981-02-25 BE BE1/10150A patent/BE887663A/fr not_active IP Right Cessation
- 1981-02-25 FI FI810582A patent/FI76787C/fi not_active IP Right Cessation
- 1981-02-25 ES ES499776A patent/ES499776A1/es not_active Expired
- 1981-02-25 AT AT0088581A patent/AT380237B/de not_active IP Right Cessation
- 1981-02-25 NO NO810639A patent/NO156689C/no unknown
- 1981-02-25 CA CA371,690A patent/CA1128523A/en not_active Expired
- 1981-02-25 IE IE397/81A patent/IE51696B1/en not_active IP Right Cessation
- 1981-02-26 AR AR284447A patent/AR230630A1/es active
- 1981-02-26 DE DE19813107306 patent/DE3107306A1/de active Granted
- 1981-02-26 JP JP2759981A patent/JPS56128758A/ja active Granted
- 1981-02-26 LU LU83169A patent/LU83169A1/fr unknown
-
1982
- 1982-03-01 PH PH26927A patent/PH17145A/en unknown
-
1983
- 1983-08-26 AT AT0305683A patent/AT380236B/de not_active IP Right Cessation
-
1984
- 1984-05-21 SE SE8402727A patent/SE452764B/sv not_active IP Right Cessation
- 1984-08-22 KR KR1019840005058A patent/KR840002066B1/ko not_active Expired
-
1989
- 1989-09-07 HK HK717/89A patent/HK71789A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE43956B1 (en) | Pyridinyl-2n1h)-pyridinones and preparation | |
| NL8201999A (nl) | Gesubstitueerde 1,2-diaminocyclobuteen-3,4-dionen, werkwijze voor het bereiden daarvan; geneesmiddelen; werkwijze voor het behandelen van door bemiddeling van histamine h2-receptoren tot stand gekomen toestanden. | |
| US6624178B2 (en) | Compounds for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof | |
| US4563467A (en) | Derivatives of N-iminopyridinium betaines having anti-hypertensive and salidiuretic activity and their preparation | |
| US4298609A (en) | 4,5-Dihydro-6-(4-pyridinyl)-3-pyridazinol and salts, their preparation and use as blood pressure lowering agents | |
| US4271168A (en) | Selected 3-acylamino-5-[4(or 3)-pyridinyl]-2(1H)-pyridinones | |
| SE437514B (sv) | N-/3-dimetylamino-2-(4-pyridinyl)-2-propenyliden/-n-metylmetaniminiumsalt, sett att framstella detta och kardioton komposition for okning av hjertkontraktiliteten | |
| NO851113L (no) | ((pyridinyl)-2-pyrimidinyl)ureaforbindelser egnet som kardiotoniske midler og fremgangsmaate for deres fremstilling | |
| US4317827A (en) | 4-[4(or 3)-Acylaminophenyl]pyridines and their use as cardiotonics | |
| PT96315B (pt) | Processo para a preparacao de derivados de diamina e de composicoes farmaceuticas que os contem | |
| US4302462A (en) | 4(or 3)-(3,4-Dihydroxyphenyl)pyridines, their cardiotonic use and cardiotonic use of their methyl ethers | |
| US4225601A (en) | 3-Hydroxy or hydroxymethyl-5-(4-pyridinyl)2(1H)-pyridinones, useful as cardiotonic agents and their preparation | |
| US4304775A (en) | 3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof | |
| US4305943A (en) | 4-Amino-6-(pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics | |
| US4376775A (en) | N-[4-(4-Pyridinyl)phenyl]ureas and their cardiotonic use | |
| US4463008A (en) | 2-Alkoxy-5-(pyridinyl)pyridines and cardiotonic use thereof | |
| US4473571A (en) | 8-Substituted-2-(4-pyridinyl)-9H-purin-6-amines and their cardiotonic use | |
| US4346221A (en) | Preparation of 4-amino-6-(pyridinyl)-3(2H)-pyridazinones from 6-(pyridinyl)-3(2H)-pyridazinones | |
| US4363911A (en) | 1,2-Dihydro-6-[2-(dimethylamino)ethenyl]-2-oxo-5-(pyridinyl) nicotinonitriles | |
| US4362735A (en) | 3-[(3-Oxo-1-butenyl)amino]-5-(pyridinyl)-2(1H)-pyridinones and their cardiotonic use | |
| US4377585A (en) | Use of 4-[4(or 3)-aminophenyl]pyridines as cardiotonic agents | |
| US4304776A (en) | 4-Substituted-6-(pyridinyl)-3(2h)-pyridazinones and their use as intermediates and cardiotonics | |
| EP0074229A1 (en) | Triazole gastric anti-secretory agents | |
| US4361569A (en) | 3-(Hydroxy or hydroxymethyl)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone and cardiotonic use thereof | |
| US4354026A (en) | 3-Chloro-6-(pyridinyl)-pyridazines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 8101205-6 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8101205-6 Format of ref document f/p: F |