NO852677L - Fremgangsmaate for fremstilling av 1,6-naftyridin-2(ih)-oner for bruk som kardiotoniske midler. - Google Patents
Fremgangsmaate for fremstilling av 1,6-naftyridin-2(ih)-oner for bruk som kardiotoniske midler.Info
- Publication number
- NO852677L NO852677L NO852677A NO852677A NO852677L NO 852677 L NO852677 L NO 852677L NO 852677 A NO852677 A NO 852677A NO 852677 A NO852677 A NO 852677A NO 852677 L NO852677 L NO 852677L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- methyl
- formula
- phenyl
- prepared
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 25
- 239000000496 cardiotonic agent Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 103
- 150000003839 salts Chemical class 0.000 claims description 44
- -1 methoxy, ethoxy, hydroxy, amino, acetylamino, methanesulfonylamino, bromine Chemical group 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000002091 cationic group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000011737 fluorine Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 7
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 claims description 7
- LYPDYBMJPMTISK-UHFFFAOYSA-N 5-benzoyl-6-[2-(dimethylamino)ethenyl]-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C(=O)C=2C=CC=CC=2)=C1C=CN(C)C LYPDYBMJPMTISK-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- NLFVQLRHUHFOTM-UHFFFAOYSA-N CCOBrOC Chemical compound CCOBrOC NLFVQLRHUHFOTM-UHFFFAOYSA-N 0.000 claims description 5
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- LINHHQVEXUQKHI-UHFFFAOYSA-N 5-benzoyl-6-methyl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C(=O)C=2C=CC=CC=2)=C1C LINHHQVEXUQKHI-UHFFFAOYSA-N 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004799 bromophenyl group Chemical group 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- 239000000203 mixture Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 22
- 230000000875 corresponding effect Effects 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- 230000003177 cardiotonic effect Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 7
- 239000005695 Ammonium acetate Substances 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 235000019257 ammonium acetate Nutrition 0.000 description 7
- 229940043376 ammonium acetate Drugs 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000012265 solid product Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 210000003540 papillary muscle Anatomy 0.000 description 6
- APKKZTGSYROVPP-UHFFFAOYSA-N 5-phenyl-1h-1,6-naphthyridin-2-one Chemical compound N1=CC=C2NC(=O)C=CC2=C1C1=CC=CC=C1 APKKZTGSYROVPP-UHFFFAOYSA-N 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 5
- 230000008602 contraction Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- YUDVUOLTNNJZBT-UHFFFAOYSA-N chembl356805 Chemical compound C1=CC(O)=CC=C1C1=NC=CC2=C1C=CC(=O)N2 YUDVUOLTNNJZBT-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 3
- GZFHUOGWZQEZON-UHFFFAOYSA-N 3-amino-1-(4-methoxyphenyl)but-2-en-1-one Chemical compound COC1=CC=C(C(=O)C=C(C)N)C=C1 GZFHUOGWZQEZON-UHFFFAOYSA-N 0.000 description 3
- HRHPQDLRRMZGNI-UHFFFAOYSA-N 3-amino-1-(4-nitrophenyl)but-2-en-1-one Chemical compound CC(N)=CC(=O)C1=CC=C([N+]([O-])=O)C=C1 HRHPQDLRRMZGNI-UHFFFAOYSA-N 0.000 description 3
- RAJGKUAURONBLG-UHFFFAOYSA-N 4-(2-oxo-1h-1,6-naphthyridin-5-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=NC=CC2=C1C=CC(=O)N2 RAJGKUAURONBLG-UHFFFAOYSA-N 0.000 description 3
- FUCOQVXISRTDAC-UHFFFAOYSA-N 4-(2-oxo-1h-1,6-naphthyridin-5-yl)benzonitrile Chemical compound N1=CC=C2NC(=O)C=CC2=C1C1=CC=C(C#N)C=C1 FUCOQVXISRTDAC-UHFFFAOYSA-N 0.000 description 3
- LTVPUVNQNUTHCI-UHFFFAOYSA-N 5-(3-nitrophenyl)-1h-1,6-naphthyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=3C=CC(=O)NC=3C=CN=2)=C1 LTVPUVNQNUTHCI-UHFFFAOYSA-N 0.000 description 3
- KOMWSZKBNQXMPA-UHFFFAOYSA-N 5-(4-methoxybenzoyl)-6-methyl-1h-pyridin-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C)NC(=O)C=C1 KOMWSZKBNQXMPA-UHFFFAOYSA-N 0.000 description 3
- WEDRUZVVMHJSPZ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1h-1,6-naphthyridin-2-one Chemical compound C1=CC(OC)=CC=C1C1=NC=CC2=C1C=CC(=O)N2 WEDRUZVVMHJSPZ-UHFFFAOYSA-N 0.000 description 3
- ZRLZAHIVMCDYJI-UHFFFAOYSA-N 6-[2-(dimethylamino)ethenyl]-5-(4-methoxybenzoyl)-1h-pyridin-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=CN(C)C)NC(=O)C=C1 ZRLZAHIVMCDYJI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- 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 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 230000036772 blood pressure Effects 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
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 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
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- PIOGKVWSMAZIFA-UHFFFAOYSA-N 1-methyl-5-phenyl-1,6-naphthyridin-2-one Chemical compound C=12C=CC(=O)N(C)C2=CC=NC=1C1=CC=CC=C1 PIOGKVWSMAZIFA-UHFFFAOYSA-N 0.000 description 2
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 2
- NCKAHKIOHMPLBS-UHFFFAOYSA-N 3-amino-1-(4-chlorophenyl)but-2-en-1-one Chemical compound CC(N)=CC(=O)C1=CC=C(Cl)C=C1 NCKAHKIOHMPLBS-UHFFFAOYSA-N 0.000 description 2
- GHPWHAXKMNDINZ-UHFFFAOYSA-N 3-amino-1-phenylbut-2-en-1-one Chemical compound CC(N)=CC(=O)C1=CC=CC=C1 GHPWHAXKMNDINZ-UHFFFAOYSA-N 0.000 description 2
- VLGQQOJFPDTUIM-UHFFFAOYSA-N 4-(3-aminobut-2-enoyl)benzonitrile Chemical compound CC(N)=CC(=O)C1=CC=C(C#N)C=C1 VLGQQOJFPDTUIM-UHFFFAOYSA-N 0.000 description 2
- OSLAYKKXCYSJSF-UHFFFAOYSA-N 4-aminopent-3-en-2-one Chemical compound CC(N)=CC(C)=O OSLAYKKXCYSJSF-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- JOUKJSSZAZZANB-UHFFFAOYSA-N 5-(3-aminophenyl)-1h-1,6-naphthyridin-2-one;hydrate;dihydrochloride Chemical compound O.Cl.Cl.NC1=CC=CC(C=2C=3C=CC(=O)NC=3C=CN=2)=C1 JOUKJSSZAZZANB-UHFFFAOYSA-N 0.000 description 2
- VEJYVKGEEONCRU-UHFFFAOYSA-N 5-(3-hydroxyphenyl)-1h-1,6-naphthyridin-2-one Chemical compound OC1=CC=CC(C=2C=3C=CC(=O)NC=3C=CN=2)=C1 VEJYVKGEEONCRU-UHFFFAOYSA-N 0.000 description 2
- BHOFTHJUIDFRSC-UHFFFAOYSA-N 5-(4-aminophenyl)-1h-1,6-naphthyridin-2-one Chemical compound C1=CC(N)=CC=C1C1=NC=CC2=C1C=CC(=O)N2 BHOFTHJUIDFRSC-UHFFFAOYSA-N 0.000 description 2
- GNFCMXOCRJBWPE-UHFFFAOYSA-N 5-(4-bromobenzoyl)-6-[2-(dimethylamino)ethenyl]-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C(=O)C=2C=CC(Br)=CC=2)=C1C=CN(C)C GNFCMXOCRJBWPE-UHFFFAOYSA-N 0.000 description 2
- VVTAYQTXKGQXNN-UHFFFAOYSA-N 5-(4-bromobenzoyl)-6-methyl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C(=O)C=2C=CC(Br)=CC=2)=C1C VVTAYQTXKGQXNN-UHFFFAOYSA-N 0.000 description 2
- NKOZXQIGXMFWOL-UHFFFAOYSA-N 5-(4-bromophenyl)-1h-1,6-naphthyridin-2-one Chemical compound C1=CC(Br)=CC=C1C1=NC=CC2=C1C=CC(=O)N2 NKOZXQIGXMFWOL-UHFFFAOYSA-N 0.000 description 2
- AUILCJVWKPZDAX-UHFFFAOYSA-N 5-(4-chlorobenzoyl)-6-[2-(dimethylamino)ethenyl]-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1C=CN(C)C AUILCJVWKPZDAX-UHFFFAOYSA-N 0.000 description 2
- UXYFWTHOXNRVAJ-UHFFFAOYSA-N 5-(4-ethoxybenzoyl)-6-methyl-1h-pyridin-2-one Chemical compound C1=CC(OCC)=CC=C1C(=O)C1=C(C)NC(=O)C=C1 UXYFWTHOXNRVAJ-UHFFFAOYSA-N 0.000 description 2
- QSWPMVXMORPNQR-UHFFFAOYSA-N 5-(4-ethoxyphenyl)-1h-1,6-naphthyridin-2-one Chemical compound C1=CC(OCC)=CC=C1C1=NC=CC2=C1C=CC(=O)N2 QSWPMVXMORPNQR-UHFFFAOYSA-N 0.000 description 2
- FNJVPACKKSXDGC-UHFFFAOYSA-N 5-(4-ethylbenzoyl)-6-methyl-1h-pyridin-2-one Chemical compound C1=CC(CC)=CC=C1C(=O)C1=C(C)NC(=O)C=C1 FNJVPACKKSXDGC-UHFFFAOYSA-N 0.000 description 2
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- ZYRYXEYNFDAQCY-UHFFFAOYSA-N 5-acetyl-6-methyl-3,4-dihydro-1h-pyridin-2-one Chemical compound CC(=O)C1=C(C)NC(=O)CC1 ZYRYXEYNFDAQCY-UHFFFAOYSA-N 0.000 description 2
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- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor 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
- HFRIUTDHBGBINS-UHFFFAOYSA-N n-[3-(2-oxo-1h-1,6-naphthyridin-5-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=3C=CC(=O)NC=3C=CN=2)=C1 HFRIUTDHBGBINS-UHFFFAOYSA-N 0.000 description 1
- IASBXSVZWOMJLL-UHFFFAOYSA-N n-[3-(2-oxo-1h-1,6-naphthyridin-5-yl)phenyl]acetamide;hydrate Chemical compound O.CC(=O)NC1=CC=CC(C=2C=3C=CC(=O)NC=3C=CN=2)=C1 IASBXSVZWOMJLL-UHFFFAOYSA-N 0.000 description 1
- SONNNXKRBOHVBI-UHFFFAOYSA-N n-[3-(2-oxo-1h-1,6-naphthyridin-5-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C=3C=CC(=O)NC=3C=CN=2)=C1 SONNNXKRBOHVBI-UHFFFAOYSA-N 0.000 description 1
- LRYAEDAZTVMYBA-UHFFFAOYSA-N n-[3-(2-oxo-1h-1,6-naphthyridin-5-yl)phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NC1=CC=CC(C=2C=3C=CC(=O)NC=3C=CN=2)=C1 LRYAEDAZTVMYBA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- BYTCDABWEGFPLT-UHFFFAOYSA-L potassium;sodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[K+] BYTCDABWEGFPLT-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 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
- 238000001953 recrystallisation Methods 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007909 solid dosage form 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
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 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
- 229960001367 tartaric acid Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 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
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/630,810 US4560691A (en) | 1984-07-13 | 1984-07-13 | 5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use and preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852677L true NO852677L (no) | 1986-01-14 |
Family
ID=24528649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852677A NO852677L (no) | 1984-07-13 | 1985-07-03 | Fremgangsmaate for fremstilling av 1,6-naftyridin-2(ih)-oner for bruk som kardiotoniske midler. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4560691A (pt) |
| EP (1) | EP0168037B1 (pt) |
| JP (1) | JPS6140286A (pt) |
| KR (1) | KR870001089B1 (pt) |
| AR (1) | AR242388A1 (pt) |
| AT (1) | ATE50259T1 (pt) |
| AU (1) | AU584103B2 (pt) |
| DE (1) | DE3575926D1 (pt) |
| DK (1) | DK318985A (pt) |
| ES (1) | ES8706151A1 (pt) |
| FI (1) | FI852765L (pt) |
| GR (1) | GR851677B (pt) |
| IL (1) | IL75733A (pt) |
| MX (1) | MX161361A (pt) |
| NO (1) | NO852677L (pt) |
| NZ (1) | NZ212647A (pt) |
| PH (1) | PH21844A (pt) |
| PT (1) | PT80809B (pt) |
| ZA (1) | ZA855280B (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4532247A (en) * | 1983-08-08 | 1985-07-30 | Sterling Drug Inc. | 5-(Hydroxyalkyl or alkanoyloxymethyl)-1,6-naphthyridin-2(1H)-one and cardiotonic use thereof |
| US4567186A (en) * | 1985-01-14 | 1986-01-28 | Sterling Drug Inc. | 5-Heteryl-1,6-naphthyridin-2(1H)-ones, cardiotonic use thereof and intermediates therefor |
| NZ214837A (en) * | 1985-01-28 | 1988-10-28 | Sterling Drug Inc | 5-substituted 1,6 naphthyridin-2(1h)-ones |
| DE3840341A1 (de) * | 1988-11-30 | 1990-06-07 | Basf Ag | Verfahren zur herstellung von 1-nitroanthrachinon-2-carbonsaeure |
| US7235551B2 (en) * | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
| EP1333833B1 (en) * | 2000-10-23 | 2011-08-24 | GlaxoSmithKline LLC | Novel trisubstituted-8H-pyrido[2,3-d]pyrimidin-7-one compound for the treatment of CSBP/p38 kinase mediated diseases |
| BR0309053A (pt) * | 2002-04-19 | 2005-02-22 | Smithkline Beecham Corp | Compostos |
| MXPA05008612A (es) * | 2003-02-14 | 2005-12-05 | Smithkline Beecham Corp | Compuestos novedosos. |
| CN101495475A (zh) * | 2005-03-25 | 2009-07-29 | 葛兰素集团有限公司 | 制备吡啶并[2,3-d]嘧啶-7-酮和3,4-二氢嘧啶并[4,5-d]嘧啶-2(1H)-酮衍生物的方法 |
| JP2008535822A (ja) * | 2005-03-25 | 2008-09-04 | グラクソ グループ リミテッド | 新規化合物 |
| AR053346A1 (es) | 2005-03-25 | 2007-05-02 | Glaxo Group Ltd | Compuesto derivado de 8h -pirido (2,3-d) pirimidin -7 ona 2,4,8- trisustituida composicion farmaceutica y uso para preparar una composicion para tratamiento y profilxis de una enfermedad mediada por la quinasa csbp/ rk/p38 |
| TW200724142A (en) * | 2005-03-25 | 2007-07-01 | Glaxo Group Ltd | Novel compounds |
| CN105218388B (zh) * | 2015-10-26 | 2017-07-11 | 西北农林科技大学 | β‑羰基烯胺类化合物及作为制备植物病原菌抗菌剂的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4412077A (en) * | 1982-03-15 | 1983-10-25 | Sterling Drug Inc. | Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinone |
| US4415580A (en) * | 1982-08-02 | 1983-11-15 | Sterling Drug Inc. | Certain 2-(1H)-pyridinones cardiotonic compositions containing same and method of using same |
-
1984
- 1984-07-13 US US06/630,810 patent/US4560691A/en not_active Expired - Fee Related
-
1985
- 1985-07-03 NO NO852677A patent/NO852677L/no unknown
- 1985-07-04 NZ NZ212647A patent/NZ212647A/xx unknown
- 1985-07-05 IL IL75733A patent/IL75733A/xx unknown
- 1985-07-05 GR GR851677A patent/GR851677B/el unknown
- 1985-07-09 AT AT85108538T patent/ATE50259T1/de not_active IP Right Cessation
- 1985-07-09 EP EP85108538A patent/EP0168037B1/en not_active Expired - Lifetime
- 1985-07-09 MX MX8266A patent/MX161361A/es unknown
- 1985-07-09 DE DE8585108538T patent/DE3575926D1/de not_active Expired - Fee Related
- 1985-07-10 AU AU44747/85A patent/AU584103B2/en not_active Ceased
- 1985-07-10 JP JP15215885A patent/JPS6140286A/ja active Pending
- 1985-07-11 PH PH32510A patent/PH21844A/en unknown
- 1985-07-11 AR AR85300954A patent/AR242388A1/es active
- 1985-07-12 KR KR1019850004976A patent/KR870001089B1/ko not_active IP Right Cessation
- 1985-07-12 ZA ZA855280A patent/ZA855280B/xx unknown
- 1985-07-12 DK DK318985A patent/DK318985A/da unknown
- 1985-07-12 ES ES545139A patent/ES8706151A1/es not_active Expired
- 1985-07-12 PT PT80809A patent/PT80809B/pt unknown
- 1985-07-12 FI FI852765A patent/FI852765L/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA855280B (en) | 1986-02-26 |
| AU584103B2 (en) | 1989-05-18 |
| DK318985A (da) | 1986-01-14 |
| NZ212647A (en) | 1988-07-28 |
| IL75733A0 (en) | 1985-11-29 |
| PT80809B (en) | 1987-01-12 |
| DK318985D0 (da) | 1985-07-12 |
| FI852765A0 (fi) | 1985-07-12 |
| IL75733A (en) | 1988-07-31 |
| FI852765L (fi) | 1986-01-14 |
| AR242388A1 (es) | 1993-03-31 |
| KR860001109A (ko) | 1986-02-22 |
| KR870001089B1 (ko) | 1987-06-04 |
| MX161361A (es) | 1990-09-18 |
| ATE50259T1 (de) | 1990-02-15 |
| EP0168037A2 (en) | 1986-01-15 |
| JPS6140286A (ja) | 1986-02-26 |
| PH21844A (en) | 1988-03-17 |
| PT80809A (en) | 1985-08-01 |
| ES545139A0 (es) | 1987-06-01 |
| EP0168037A3 (en) | 1986-03-26 |
| DE3575926D1 (de) | 1990-03-15 |
| EP0168037B1 (en) | 1990-02-07 |
| AU4474785A (en) | 1986-01-16 |
| ES8706151A1 (es) | 1987-06-01 |
| US4560691A (en) | 1985-12-24 |
| GR851677B (pt) | 1985-11-26 |
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