LU82728A1 - 6-(pyridinyl)-3(2h)pyridazinones,leur preparation et leur utilisation therapeutique - Google Patents

6-(pyridinyl)-3(2h)pyridazinones,leur preparation et leur utilisation therapeutique Download PDF

Info

Publication number: LU82728A1
Authority: LU; Luxembourg
Prior art keywords: pyridinyl; pyridazinone; dihydro; methyl; acid
Prior art date: 1979-08-30

Application number

LU82728A

Other languages

English (en)

French (fr)

Original Assignee

Sterling Drug Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-08-30

Filing date

1980-08-26

Publication date

1981-03-24

1980-08-26 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1981-03-24 Publication of LU82728A1 publication Critical patent/LU82728A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 9
FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 title 1
230000001225 therapeutic effect Effects 0.000 title 1
150000003839 salts Chemical class 0.000 claims description 44
-1 4-pyridinyl Chemical group 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 13
230000003177 cardiotonic effect Effects 0.000 claims description 10
LPRDIYKZZIDTPV-UHFFFAOYSA-N 3-pyridin-4-yl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(C=2C=CN=CC=2)=N1 LPRDIYKZZIDTPV-UHFFFAOYSA-N 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
230000000747 cardiac effect Effects 0.000 claims description 6
YWJGORHFDXGFTF-UHFFFAOYSA-N 2-methyl-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C1=CC=NC=C1 YWJGORHFDXGFTF-UHFFFAOYSA-N 0.000 claims description 5
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
FBOQGQULUAPQCC-UHFFFAOYSA-N 3-pyridin-4-yl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CN=CC=2)=N1 FBOQGQULUAPQCC-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
239000012458 free base Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
IRWZLWUYVNDDIX-UHFFFAOYSA-N 2-methyl-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical class C1CC(=O)N(C)N=C1C1=CC=NC=C1 IRWZLWUYVNDDIX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
UTISRGMYIPHHBR-UHFFFAOYSA-N 4-oxo-4-pyridin-4-ylbutanenitrile Chemical compound N#CCCC(=O)C1=CC=NC=C1 UTISRGMYIPHHBR-UHFFFAOYSA-N 0.000 description 5
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000004310 lactic acid Substances 0.000 description 5
235000014655 lactic acid Nutrition 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000496 cardiotonic agent Substances 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 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
238000006356 dehydrogenation reaction Methods 0.000 description 3
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000010247 heart contraction Effects 0.000 description 3
239000012493 hydrazine sulfate Substances 0.000 description 3
229910000377 hydrazine sulfate Inorganic materials 0.000 description 3
210000003540 papillary muscle Anatomy 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000008247 solid mixture Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000010998 test method Methods 0.000 description 3
IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
DDCLFSUBVBCSFN-UHFFFAOYSA-N 3-pyridin-2-yl-1h-pyridazin-6-one Chemical class N1C(=O)C=CC(C=2N=CC=CC=2)=N1 DDCLFSUBVBCSFN-UHFFFAOYSA-N 0.000 description 2
INOKSURCXXQEIB-UHFFFAOYSA-N 3-pyridin-3-yl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=NC=CC=2)=N1 INOKSURCXXQEIB-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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
125000005059 halophenyl group Chemical group 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 2
ONUGLWXPCMEGCK-UHFFFAOYSA-N hydrazine;methanesulfonic acid Chemical compound NN.CS(O)(=O)=O.CS(O)(=O)=O ONUGLWXPCMEGCK-UHFFFAOYSA-N 0.000 description 2
150000002429 hydrazines Chemical class 0.000 description 2
230000001077 hypotensive effect Effects 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
238000001819 mass spectrum Methods 0.000 description 2
HTAWQGONZIWLRC-UHFFFAOYSA-N methylhydrazine;dihydrochloride Chemical compound Cl.Cl.CNN HTAWQGONZIWLRC-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 2
210000005245 right atrium Anatomy 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
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 1
KOOCPRQXWCJHNW-UHFFFAOYSA-N 2-(2-hydroxyethyl)-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CCO)N=C1C1=CC=NC=C1 KOOCPRQXWCJHNW-UHFFFAOYSA-N 0.000 description 1
MIFCHHIMUJKAEI-UHFFFAOYSA-N 2-(2-hydroxyethyl)-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CCO)N=C1C1=CC=NC=C1 MIFCHHIMUJKAEI-UHFFFAOYSA-N 0.000 description 1
WYWBURABCIWPBH-UHFFFAOYSA-N 2-(2-hydroxypropyl)-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CC(O)C)N=C1C1=CC=NC=C1 WYWBURABCIWPBH-UHFFFAOYSA-N 0.000 description 1
MSJLJOBINJMLPA-UHFFFAOYSA-N 2-(2-hydroxypropyl)-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CC(O)C)N=C1C1=CC=NC=C1 MSJLJOBINJMLPA-UHFFFAOYSA-N 0.000 description 1
WSTBGHOXXJYEHT-UHFFFAOYSA-N 2-(2-methylpropyl)-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CC(C)C)N=C1C1=CC=NC=C1 WSTBGHOXXJYEHT-UHFFFAOYSA-N 0.000 description 1
MZOBUXRIAFXDEP-UHFFFAOYSA-N 2-(2-methylpropyl)-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CC(C)C)N=C1C1=CC=NC=C1 MZOBUXRIAFXDEP-UHFFFAOYSA-N 0.000 description 1
ACDMWJLHEOKSAJ-UHFFFAOYSA-N 2-(3-hydroxypropyl)-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CCCO)N=C1C1=CC=NC=C1 ACDMWJLHEOKSAJ-UHFFFAOYSA-N 0.000 description 1
BHCBOPYPAJDMJL-UHFFFAOYSA-N 2-(3-hydroxypropyl)-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CCCO)N=C1C1=CC=NC=C1 BHCBOPYPAJDMJL-UHFFFAOYSA-N 0.000 description 1
JQGSUFYBABFXPW-UHFFFAOYSA-N 2-(4-hydroxybutyl)-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CCCCO)N=C1C1=CC=NC=C1 JQGSUFYBABFXPW-UHFFFAOYSA-N 0.000 description 1
PZBHMJQTZBQVNM-UHFFFAOYSA-N 2-(4-hydroxybutyl)-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CCCCO)N=C1C1=CC=NC=C1 PZBHMJQTZBQVNM-UHFFFAOYSA-N 0.000 description 1
XQVQIBFPZHYXTC-UHFFFAOYSA-N 2-ethyl-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CC)N=C1C1=CC=NC=C1 XQVQIBFPZHYXTC-UHFFFAOYSA-N 0.000 description 1
RDBIYYHHRLWXJB-UHFFFAOYSA-N 2-hexyl-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CCCCCC)N=C1C1=CC=NC=C1 RDBIYYHHRLWXJB-UHFFFAOYSA-N 0.000 description 1
YKLFPKNCJCUCSG-UHFFFAOYSA-N 2-hexyl-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CCCCCC)N=C1C1=CC=NC=C1 YKLFPKNCJCUCSG-UHFFFAOYSA-N 0.000 description 1
LFIKHFDBARUUPN-UHFFFAOYSA-N 2-methyl-6-(2-methylpyridin-3-yl)pyridazin-3-one Chemical compound CC1=NC=CC=C1C1=NN(C)C(=O)C=C1 LFIKHFDBARUUPN-UHFFFAOYSA-N 0.000 description 1
RSAJRAAFBGTDKP-UHFFFAOYSA-N 2-methyl-6-(5-methylpyridin-3-yl)-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(C)N=C1C1=CN=CC(C)=C1 RSAJRAAFBGTDKP-UHFFFAOYSA-N 0.000 description 1
PJJIWKUZDWXSAU-UHFFFAOYSA-N 2-methyl-6-(5-methylpyridin-3-yl)pyridazin-3-one Chemical compound CC1=CN=CC(C2=NN(C)C(=O)C=C2)=C1 PJJIWKUZDWXSAU-UHFFFAOYSA-N 0.000 description 1
SHEYTAJXEIGSIO-UHFFFAOYSA-N 2-methyl-6-pyridin-3-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(C)N=C1C1=CC=CN=C1 SHEYTAJXEIGSIO-UHFFFAOYSA-N 0.000 description 1
XKNIUVQBSHGDJM-UHFFFAOYSA-N 2-methyl-6-pyridin-3-ylpyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C1=CC=CN=C1 XKNIUVQBSHGDJM-UHFFFAOYSA-N 0.000 description 1
UUVWBIZOMLVGJT-UHFFFAOYSA-N 2-propan-2-yl-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(C(C)C)N=C1C1=CC=NC=C1 UUVWBIZOMLVGJT-UHFFFAOYSA-N 0.000 description 1
PGSCRFOXTNJWEB-UHFFFAOYSA-N 2-propan-2-yl-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(C(C)C)N=C1C1=CC=NC=C1 PGSCRFOXTNJWEB-UHFFFAOYSA-N 0.000 description 1
VPXIHRAAMJQAEA-UHFFFAOYSA-N 2-propyl-6-pyridin-4-yl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CCC)N=C1C1=CC=NC=C1 VPXIHRAAMJQAEA-UHFFFAOYSA-N 0.000 description 1
RPUYCTDFHXPWHJ-UHFFFAOYSA-N 2-propyl-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=CC(=O)N(CCC)N=C1C1=CC=NC=C1 RPUYCTDFHXPWHJ-UHFFFAOYSA-N 0.000 description 1
QSZSECGVFAOGHT-UHFFFAOYSA-N 3-(2-methylpyridin-3-yl)-1h-pyridazin-6-one Chemical compound CC1=NC=CC=C1C1=CC=C(O)N=N1 QSZSECGVFAOGHT-UHFFFAOYSA-N 0.000 description 1
WQIZIWHVMZHADV-UHFFFAOYSA-N 3-(2-methylpyridin-3-yl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1=NC=CC=C1C1=NNC(=O)CC1 WQIZIWHVMZHADV-UHFFFAOYSA-N 0.000 description 1
AYJCYJJVFFRRAF-UHFFFAOYSA-N 3-(3-ethylpyridin-4-yl)-1h-pyridazin-6-one Chemical compound CCC1=CN=CC=C1C1=NNC(=O)C=C1 AYJCYJJVFFRRAF-UHFFFAOYSA-N 0.000 description 1
NRAQCHGPXPVMFO-UHFFFAOYSA-N 3-(3-ethylpyridin-4-yl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound CCC1=CN=CC=C1C1=NN=C(O)CC1 NRAQCHGPXPVMFO-UHFFFAOYSA-N 0.000 description 1
PWKDVSFTKHEPKK-UHFFFAOYSA-N 3-(5-methylpyridin-3-yl)-1h-pyridazin-6-one Chemical compound CC1=CN=CC(C2=NNC(=O)C=C2)=C1 PWKDVSFTKHEPKK-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
UVEJMKKLGJZUPD-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-4-oxobutanenitrile Chemical compound CC1=CC(C(=O)CCC#N)=CC(C)=N1 UVEJMKKLGJZUPD-UHFFFAOYSA-N 0.000 description 1
AJCBVBSUGQKYPJ-UHFFFAOYSA-N 4-(2-methylpyridin-3-yl)-4-oxobutanenitrile Chemical compound CC1=NC=CC=C1C(=O)CCC#N AJCBVBSUGQKYPJ-UHFFFAOYSA-N 0.000 description 1
HRNOJFSHSRNNLF-UHFFFAOYSA-N 4-(3-ethylpyridin-4-yl)-4-oxobutanenitrile Chemical compound CCC1=CN=CC=C1C(=O)CCC#N HRNOJFSHSRNNLF-UHFFFAOYSA-N 0.000 description 1
IFMWGQWYIXZVEQ-UHFFFAOYSA-N 4-(5-methylpyridin-3-yl)-4-oxobutanenitrile Chemical compound CC1=CN=CC(C(=O)CCC#N)=C1 IFMWGQWYIXZVEQ-UHFFFAOYSA-N 0.000 description 1
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
RKXWIKVGGKZDJY-UHFFFAOYSA-N 4-oxo-4-pyridin-3-ylbutanenitrile Chemical compound N#CCCC(=O)C1=CC=CN=C1 RKXWIKVGGKZDJY-UHFFFAOYSA-N 0.000 description 1
QHBYZGQLPMSIFR-UHFFFAOYSA-N 4-oxo-4-pyridin-4-ylbutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=NC=C1 QHBYZGQLPMSIFR-UHFFFAOYSA-N 0.000 description 1
PBBPBFYHOLKTFP-UHFFFAOYSA-N 5-pyridin-2-yl-1h-pyridazin-6-one Chemical compound O=C1NN=CC=C1C1=CC=CC=N1 PBBPBFYHOLKTFP-UHFFFAOYSA-N 0.000 description 1
AKBFPXJWJKEUJH-UHFFFAOYSA-N 6-(2,6-dimethylpyridin-4-yl)-2-methyl-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(C)N=C1C1=CC(C)=NC(C)=C1 AKBFPXJWJKEUJH-UHFFFAOYSA-N 0.000 description 1
CMSAIAYYZTWCIZ-UHFFFAOYSA-N 6-(3-ethylpyridin-4-yl)-2-methyl-4,5-dihydropyridazin-3-one Chemical compound CCC1=CN=CC=C1C1=NN(C)C(=O)CC1 CMSAIAYYZTWCIZ-UHFFFAOYSA-N 0.000 description 1
YNVVGOQUHLIIRK-UHFFFAOYSA-N 6-(3-ethylpyridin-4-yl)-2-methylpyridazin-3-one Chemical compound CCC1=CN=CC=C1C1=NN(C)C(=O)C=C1 YNVVGOQUHLIIRK-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
241000894006 Bacteria Species 0.000 description 1
JCDOMILRKCFCBQ-UHFFFAOYSA-N CC1=NC(=CC(=C1)N1N=CC=CC1=O)C Chemical compound CC1=NC(=CC(=C1)N1N=CC=CC1=O)C JCDOMILRKCFCBQ-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 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
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
239000005909 Kieselgur Substances 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
229910019142 PO4 Inorganic materials 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-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
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
239000004480 active ingredient Substances 0.000 description 1
239000004019 antithrombin Substances 0.000 description 1
239000002585 base Substances 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
230000015572 biosynthetic process Effects 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
238000009835 boiling Methods 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
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003995 emulsifying agent Substances 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
238000001914 filtration Methods 0.000 description 1
239000007789 gas 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
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 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
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
229910052697 platinum Inorganic materials 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
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 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
230000001954 sterilising effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 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
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 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
229940095064 tartrate Drugs 0.000 description 1
210000005239 tubule Anatomy 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)

LU82728A 1979-08-30 1980-08-26 6-(pyridinyl)-3(2h)pyridazinones,leur preparation et leur utilisation therapeutique LU82728A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US7106579A	1979-08-30	1979-08-30
US7106579		1979-08-30
US06/144,576 US4304777A (en)	1979-08-30	1980-04-28	6-(Pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics
US14457680		1980-04-28

Publications (1)

Publication Number	Publication Date
LU82728A1 true LU82728A1 (fr)	1981-03-24

Family

ID=26751794

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82728A LU82728A1 (fr)	1979-08-30	1980-08-26	6-(pyridinyl)-3(2h)pyridazinones,leur preparation et leur utilisation therapeutique

Country Status (19)

Country	Link
US (1)	US4304777A (it)
AR (1)	AR226704A1 (it)
AT (1)	ATA427680A (it)
AU (1)	AU532052B2 (it)
CA (1)	CA1155848A (it)
DE (1)	DE3032137A1 (it)
DK (1)	DK364880A (it)
ES (1)	ES8107215A1 (it)
FI (1)	FI802676A7 (it)
FR (1)	FR2464264A1 (it)
GB (1)	GB2057438B (it)
IL (1)	IL60918A (it)
IT (1)	IT1141012B (it)
LU (1)	LU82728A1 (it)
NL (1)	NL8004815A (it)
NO (1)	NO802507L (it)
NZ (1)	NZ194811A (it)
PT (1)	PT71736B (it)
SE (1)	SE8005946L (it)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL62679A0 (en) *	1980-04-28	1981-06-29	Sterling Drug Inc	4,5-dihydro-3(2h)-pyridazinone derivatives,their preparation and pharmaceutical compositions containing them
US4486431A (en) *	1981-01-14	1984-12-04	Sterling Drug Inc.	Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones
US4404203A (en)	1981-05-14	1983-09-13	Warner-Lambert Company	Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents
US4397854A (en)	1981-05-14	1983-08-09	Warner-Lambert Company	Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents
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
IE54598B1 (en) *	1981-11-12	1989-12-06	Ici Plc	Pharmaceutically-active pyridylvinylpyridazinones
US4591591A (en) *	1984-03-08	1986-05-27	Eli Lilly And Company	Pyridazinone derivatives as inotropic agents
US4647564A (en) *	1984-05-14	1987-03-03	Eli Lilly And Company	Inotropic agents
US4617302A (en) *	1984-10-15	1986-10-14	Eli Lilly And Company	Inotropic agents
US4631279A (en) *	1984-10-15	1986-12-23	Eli Lilly And Company	6-(pyridinylphenyl)dihydropyridazinones as inotropic agents
HU195645B (en) *	1985-10-30	1988-06-28	Gyogyszerkutato Intezet	Process for preparing novel 3(2h)-pyridazinone derivatives and pharmaceutical compositions comprising the same
DE3626865A1 (de) *	1986-08-08	1988-02-11	Boehringer Mannheim Gmbh	Neue pyridazinon-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
GB9015764D0 (en) *	1990-07-18	1990-09-05	Fujisawa Pharmaceutical Co	Pyrazolopyridine compound and processes for preparation thereof
CN1038249C (zh) *	1991-08-28	1998-05-06	罗姆和哈斯公司	含有二氢哒嗪酮及其相关化合物的杀菌组合物
AU2016341445B2 (en)	2015-10-23	2020-08-27	Array Biopharma, Inc.	2-aryl- and 2-heteroaryl-substituted 2-pyridazin-3(2H)-one compounds as inhibitors of FGFR tyrosine kinases
WO2020131627A1 (en)	2018-12-19	2020-06-25	Array Biopharma Inc.	Substituted pyrazolo[1,5-a]pyridine compounds as inhibitors of fgfr tyrosine kinases
EP3898615A1 (en)	2018-12-19	2021-10-27	Array Biopharma, Inc.	7-((3,5-dimethoxyphenyl)amino)quinoxaline derivatives as fgfr inhibitors for treating cancer

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3822260A (en) *	1970-10-09	1974-07-02	American Cyanamid Co	6-(cyanophenyl)-4,5-dihydro-3(2h)-pyridazinones
US3812256A (en) *	1971-06-08	1974-05-21	American Cyanamid Co	Novel method for lowering blood pressure in mammals
US3746712A (en) *	1971-06-08	1973-07-17	A Ross	6-(substituted-phenyl)-5-methyl-4,5-dihydro-3(2h)-pyridazinones
US4004009A (en) *	1975-07-31	1977-01-18	Sandoz, Inc.	Antihypertensive aryl pyrazolo[4,3-c]pyridazinones
US4072746A (en) *	1975-10-14	1978-02-07	Sterling Drug Inc.	3-Amino-5-(pyridinyl)-2(1H)-pyridinones
US4004012A (en) *	1975-10-14	1977-01-18	Sterling Drug Inc.	3-Cyano-5-(pyridinyl)-2(1H)-pyridinones

1980
- 1980-04-28 US US06/144,576 patent/US4304777A/en not_active Expired - Lifetime
- 1980-08-20 IT IT24230/80A patent/IT1141012B/it active
- 1980-08-21 FR FR8018304A patent/FR2464264A1/fr active Pending
- 1980-08-21 GB GB8027262A patent/GB2057438B/en not_active Expired
- 1980-08-22 NO NO802507A patent/NO802507L/no unknown
- 1980-08-22 AT AT0427680A patent/ATA427680A/de not_active Application Discontinuation
- 1980-08-25 PT PT71736A patent/PT71736B/pt unknown
- 1980-08-25 SE SE8005946A patent/SE8005946L/xx not_active Application Discontinuation
- 1980-08-25 FI FI802676A patent/FI802676A7/fi not_active Application Discontinuation
- 1980-08-26 DE DE19803032137 patent/DE3032137A1/de not_active Withdrawn
- 1980-08-26 IL IL60918A patent/IL60918A/xx unknown
- 1980-08-26 NL NL8004815A patent/NL8004815A/nl not_active Application Discontinuation
- 1980-08-26 AR AR282296A patent/AR226704A1/es active
- 1980-08-26 DK DK364880A patent/DK364880A/da not_active Application Discontinuation
- 1980-08-26 LU LU82728A patent/LU82728A1/fr unknown
- 1980-08-28 ES ES494559A patent/ES8107215A1/es not_active Expired
- 1980-08-29 NZ NZ194811A patent/NZ194811A/en unknown
- 1980-08-29 CA CA000359361A patent/CA1155848A/en not_active Expired
- 1980-09-01 AU AU61928/80A patent/AU532052B2/en not_active Ceased

Also Published As

Publication number	Publication date
ATA427680A (de)	1983-12-15
NL8004815A (nl)	1981-03-03
IT1141012B (it)	1986-10-01
FR2464264A1 (fr)	1981-03-06
IL60918A (en)	1983-11-30
US4304777A (en)	1981-12-08
AU532052B2 (en)	1983-09-15
NZ194811A (en)	1984-05-31
AU6192880A (en)	1981-03-05
FI802676A7 (fi)	1981-01-01
GB2057438A (en)	1981-04-01
PT71736B (en)	1981-06-15
PT71736A (en)	1980-09-01
ES494559A0 (es)	1981-08-16
ES8107215A1 (es)	1981-08-16
GB2057438B (en)	1983-09-07
SE8005946L (sv)	1981-03-02
IT8024230A0 (it)	1980-08-20
CA1155848A (en)	1983-10-25
DE3032137A1 (de)	1981-03-19
NO802507L (no)	1981-03-02
AR226704A1 (es)	1982-08-13
DK364880A (da)	1981-03-01
IL60918A0 (en)	1980-10-26

Publication	Publication Date	Title
LU82728A1 (fr)	1981-03-24	6-(pyridinyl)-3(2h)pyridazinones,leur preparation et leur utilisation therapeutique
CH619936A5 (it)	1980-10-31
FR2553767A1 (fr)	1985-04-26	1-pyridinyl-2-(dialkyl-amino) ethenyl alkyl cetones et leur procede de preparation
LU83259A1 (fr)	1981-10-29	Imidazopyridines,leur preparation et leur utilisation comme agents cardiotiniques
US4331671A (en)	1982-05-25	5-(Pyridinyl)-1H-benzimidazoles and 1-hydroxy-6-(pyridinyl)-1H-benzimidazoles and their cardiotonic use
LU83214A1 (fr)	1981-10-30	Derives de pyrazolopyridine,leur preparation et leur utilisation comme agents cardiotoniques
US4298609A (en)	1981-11-03	4,5-Dihydro-6-(4-pyridinyl)-3-pyridazinol and salts, their preparation and use as blood pressure lowering agents
EP0150205A1 (en)	1985-08-07	ad(pyridinyl)-2-pyrimidinyl bdureas useful as cardiotonics and preparation thereof
BE884859A (fr)	1981-02-23	6-(pyridinyl)-3 (2h)pyridazinones, leur preparation et leur utilisation therapeutique
US4304775A (en)	1981-12-08	3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof
US4305943A (en)	1981-12-15	4-Amino-6-(pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics
LU83032A1 (fr)	1981-07-23	3-acylamino-5(pyridinyl)-2(1h)-pyridinones,leur preparation et leur utilisation comme agents cardiotoniques
US4337253A (en)	1982-06-29	4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a cardiotonic
US4346221A (en)	1982-08-24	Preparation of 4-amino-6-(pyridinyl)-3(2H)-pyridazinones from 6-(pyridinyl)-3(2H)-pyridazinones
US4486431A (en)	1984-12-04	Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones
US4590194A (en)	1986-05-20	3-[methyl or dimethyl)amino]-6-(pyridinyl)pyridazines and their cardiotonic use
FR2496659A1 (fr)	1982-06-25	Derives de 1,2 dihydro-5(pyridinyl)nicotinamide, leur preparation et leur utilisation comme agents cardiotoniques et intermediaires
LU83396A1 (fr)	1982-01-20	Compositions cardiotoniques contenant des aminophenylpyridines,nouvelles aminophenylpyridines et leur preparation
US4354026A (en)	1982-10-12	3-Chloro-6-(pyridinyl)-pyridazines
LU83322A1 (fr)	1981-12-01	6-(pyridinyl)-3(2h)-pyridazinones 4-substitutees,leur preparation,leur utilisation comme agents cardiotoniques,et composes intermediaires.
LU83320A1 (fr)	1981-12-01	4,5-dihydro-6-(pyridinyl)-3(2h)-pyridazinones,leur preparation et leur utilisation comme agents cardiotoniques
BE886574A (fr)	1981-06-10	6-(pyridinyl)-pyridazines, leur preparation et leur utilisation therapeutique
LU83498A1 (fr)	1982-02-17	Pyridinyl-amino-phenols,leur preparation et leur utilisation comme agents cardiotoniques
FR2478098A1 (fr)	1981-09-18	Pyrazolopyridinones et pyridinylnicotinates, leur preparation et leur utilisation comme agents cardiotoniques
LU83770A1 (fr)	1982-06-30	Derives de (pyridinyl) benzene leur preparation et leur utilisation comme agents cardiotoniques