SU468418A3 - Способ получени 1-окси-2-пиридонов - Google Patents
Способ получени 1-окси-2-пиридоновInfo
- Publication number
- SU468418A3 SU468418A3 SU1896821A SU1896821A SU468418A3 SU 468418 A3 SU468418 A3 SU 468418A3 SU 1896821 A SU1896821 A SU 1896821A SU 1896821 A SU1896821 A SU 1896821A SU 468418 A3 SU468418 A3 SU 468418A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- pyridone
- hydroxy
- calculated
- yield
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical compound ON1C=CC=CC1=O SNUSZUYTMHKCPM-UHFFFAOYSA-N 0.000 title description 4
- -1 alkyl radical Chemical class 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 23
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 18
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000003927 aminopyridines Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 4
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 4
- 229950011175 aminopicoline Drugs 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002443 hydroxylamines Chemical class 0.000 description 3
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- GPKRKAFTZYODFF-UHFFFAOYSA-N 6-cyclohexyl-4-methylpyran-2-one Chemical compound O1C(=O)C=C(C)C=C1C1CCCCC1 GPKRKAFTZYODFF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QVWDCUMRWIBGJX-UHFFFAOYSA-N 1-hydroxy-4,6-dimethylpyridin-2-one Chemical compound CC=1C=C(C)N(O)C(=O)C=1 QVWDCUMRWIBGJX-UHFFFAOYSA-N 0.000 description 1
- DJOBTQHCXITUIN-UHFFFAOYSA-N 1-hydroxy-4-methyl-6-(2-phenylethenyl)pyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1C=CC1=CC=CC=C1 DJOBTQHCXITUIN-UHFFFAOYSA-N 0.000 description 1
- IEFRQNQEFHXQTF-UHFFFAOYSA-N 1-hydroxy-6-methylpyridin-2-one Chemical compound CC1=CC=CC(=O)N1O IEFRQNQEFHXQTF-UHFFFAOYSA-N 0.000 description 1
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- ZCBIDXBHQZNWFH-UHFFFAOYSA-N 3-(2-methylphenyl)-1h-pyridin-2-one Chemical compound CC1=CC=CC=C1C1=CC=CNC1=O ZCBIDXBHQZNWFH-UHFFFAOYSA-N 0.000 description 1
- FUEVOYOYVFWMIX-UHFFFAOYSA-N 3-benzhydryl-1h-pyridin-2-one Chemical compound O=C1NC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 FUEVOYOYVFWMIX-UHFFFAOYSA-N 0.000 description 1
- BJIDTOIFFSTUPG-UHFFFAOYSA-N 3-bromo-1-hydroxy-4,6-dimethylpyridin-2-one Chemical compound CC=1C=C(C)N(O)C(=O)C=1Br BJIDTOIFFSTUPG-UHFFFAOYSA-N 0.000 description 1
- AKKBLPYPBJKKBL-UHFFFAOYSA-N 3-methyl-6-(4-methylphenyl)-1H-pyridin-2-one Chemical compound CC=1C(NC(=CC=1)C1=CC=C(C=C1)C)=O AKKBLPYPBJKKBL-UHFFFAOYSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- AKUPLRLUIHAYFW-UHFFFAOYSA-N 4-ethyl-1-hydroxy-3,5,6-trimethylpyridin-2-one Chemical compound CCC=1C(C)=C(C)N(O)C(=O)C=1C AKUPLRLUIHAYFW-UHFFFAOYSA-N 0.000 description 1
- SJWHILBZPGQBJE-UHFFFAOYSA-N 4-ethylpyridin-2-amine Chemical compound CCC1=CC=NC(N)=C1 SJWHILBZPGQBJE-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- QZYNSXFRLAJMRK-UHFFFAOYSA-N 4-methyl-6-(phenylsulfanylmethyl)pyran-2-one Chemical compound O1C(=O)C=C(C)C=C1CSC1=CC=CC=C1 QZYNSXFRLAJMRK-UHFFFAOYSA-N 0.000 description 1
- QLBLKIZIBXMYKG-UHFFFAOYSA-N 4-methyl-6-[(3-nitrophenoxy)methyl]pyran-2-one Chemical compound O1C(=O)C=C(C)C=C1COC1=CC=CC([N+]([O-])=O)=C1 QLBLKIZIBXMYKG-UHFFFAOYSA-N 0.000 description 1
- YNIFVUNQJJTUFJ-UHFFFAOYSA-N 4-methyl-6-phenyl-5-prop-2-ynylpyran-2-one Chemical compound CC1=CC(=O)OC(C=2C=CC=CC=2)=C1CC#C YNIFVUNQJJTUFJ-UHFFFAOYSA-N 0.000 description 1
- METVSRFIOHSNJX-UHFFFAOYSA-N 5-(chloromethyl)-4,6,11-trioxa-1-aza-5-silabicyclo[3.3.3]undecane Chemical compound O1CCN2CCO[Si]1(CCl)OCC2 METVSRFIOHSNJX-UHFFFAOYSA-N 0.000 description 1
- FCJSXLNHYNZJRN-UHFFFAOYSA-N 5-benzyl-4,6-dimethylpyran-2-one Chemical compound CC1=CC(=O)OC(C)=C1CC1=CC=CC=C1 FCJSXLNHYNZJRN-UHFFFAOYSA-N 0.000 description 1
- IVLKWTYOECKEIO-UHFFFAOYSA-N 5-ethyl-1-hydroxy-4-methyl-6-(4-methylphenyl)pyridin-2-one Chemical compound CC1=CC(=O)N(O)C(C=2C=CC(C)=CC=2)=C1CC IVLKWTYOECKEIO-UHFFFAOYSA-N 0.000 description 1
- XCOABSHZBJENLV-UHFFFAOYSA-N 5-ethyl-4-methyl-6-(4-methylphenyl)pyran-2-one Chemical compound CC1=CC(=O)OC(C=2C=CC(C)=CC=2)=C1CC XCOABSHZBJENLV-UHFFFAOYSA-N 0.000 description 1
- NQWAAYIRALCSMU-UHFFFAOYSA-N 6-[2-(furan-2-yl)ethenyl]-1-hydroxy-4-methylpyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1C=CC1=CC=CO1 NQWAAYIRALCSMU-UHFFFAOYSA-N 0.000 description 1
- WFYCCNGMMNQOLT-UHFFFAOYSA-N 6-benzyl-4-methylpyran-2-one Chemical compound O1C(=O)C=C(C)C=C1CC1=CC=CC=C1 WFYCCNGMMNQOLT-UHFFFAOYSA-N 0.000 description 1
- ZZUKZMLPCBPVED-UHFFFAOYSA-N 6-cyclohexyl-3-methyl-1H-pyridin-2-one Chemical compound CC=1C(NC(=CC1)C1CCCCC1)=O ZZUKZMLPCBPVED-UHFFFAOYSA-N 0.000 description 1
- BHJSVHSYLOKRJP-UHFFFAOYSA-N 6-heptyl-1-hydroxy-4-methylpyridin-2-one Chemical compound CCCCCCCC1=CC(C)=CC(=O)N1O BHJSVHSYLOKRJP-UHFFFAOYSA-N 0.000 description 1
- NROFPJRBKHILJM-UHFFFAOYSA-N 6-methylpyran-2-one Chemical compound CC1=CC=CC(=O)O1 NROFPJRBKHILJM-UHFFFAOYSA-N 0.000 description 1
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
- UENBBJXGCWILBM-UHFFFAOYSA-N 6-methylpyridin-3-amine Chemical compound CC1=CC=C(N)C=N1 UENBBJXGCWILBM-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- 108010037781 Silimin Proteins 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical compound ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CXGFWBPQQXZELI-UHFFFAOYSA-N n-ethylpyridin-2-amine Chemical compound CCNC1=CC=CC=N1 CXGFWBPQQXZELI-UHFFFAOYSA-N 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 101150032584 oxy-4 gene Proteins 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722214608 DE2214608C3 (de) | 1972-03-25 | Verfahren zur Herstellung von J-Hydroxy-2-pyridonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU468418A3 true SU468418A3 (ru) | 1975-04-25 |
Family
ID=5840130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1896821A SU468418A3 (ru) | 1972-03-25 | 1973-03-23 | Способ получени 1-окси-2-пиридонов |
Country Status (27)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4178242A (en) * | 1975-11-11 | 1979-12-11 | Anic S.P.A. | Method for the purification of sewage waters which contain organic compounds of an anionic character |
| JPS5323145A (en) * | 1976-07-20 | 1978-03-03 | Kurita Water Ind Ltd | Method of dehydrating sludge |
| JPS54144759A (en) * | 1978-04-29 | 1979-11-12 | Tobata Tekko Kk | Method of decoloring waste water containing dyestuffs |
| GB8325496D0 (en) * | 1983-09-23 | 1983-10-26 | Hider R C | Pharmaceutical compositions |
| US4912118A (en) * | 1983-09-23 | 1990-03-27 | National Research Development Corporation | Pharmaceutical compositions |
| USRE34313E (en) * | 1983-09-23 | 1993-07-13 | National Research Development Corporation | Pharmaceutical compositions |
| US5817825A (en) * | 1994-11-02 | 1998-10-06 | Hoechst Aktiengesellschaft | Process for the preparation of 1-hydroxy-2-pyridones |
| WO2004078727A1 (ja) * | 2003-02-05 | 2004-09-16 | Nippon Soda Co., Ltd. | 新規６－フルオロアルキル－２（１ｈ）－ピリジノン、６－フルオロアルキルピリジン化合物及びその製造方法 |
| US11753379B2 (en) * | 2018-05-30 | 2023-09-12 | Clariant International Ltd | Process for forming 2-hydroxypyridine-1-oxide or derivatives thereof |
| EP4122918A1 (en) * | 2021-07-19 | 2023-01-25 | Clariant International Ltd | Process for the preparation of n-hydroxypyridone compounds |
| WO2024104987A2 (en) * | 2022-11-16 | 2024-05-23 | Clariant International Ltd | Process for the crystallization or precipitation of piroctone |
| WO2024115319A1 (en) * | 2022-11-28 | 2024-06-06 | Clariant International Ltd | Process for the preparation of n-hydroxypyridone compounds |
-
1973
- 1973-03-11 EG EG86/73A patent/EG10850A/xx active
- 1973-03-12 CA CA166,905A patent/CA979449A/en not_active Expired
- 1973-03-20 NL NLAANVRAGE7303870,A patent/NL175177C/xx not_active IP Right Cessation
- 1973-03-20 ES ES412847A patent/ES412847A1/es not_active Expired
- 1973-03-21 BG BG025589A patent/BG22814A3/xx unknown
- 1973-03-21 BG BG023052A patent/BG22817A3/xx unknown
- 1973-03-21 GB GB1358773A patent/GB1416397A/en not_active Expired
- 1973-03-22 YU YU784/73A patent/YU35583B/xx unknown
- 1973-03-22 FI FI896/73A patent/FI55331C/fi active
- 1973-03-22 PH PH14455*UA patent/PH9480A/en unknown
- 1973-03-22 KR KR7300464A patent/KR780000095B1/ko not_active Expired
- 1973-03-22 CH CH420473A patent/CH579050A5/xx not_active IP Right Cessation
- 1973-03-23 HU HUHO1556A patent/HU166579B/hu unknown
- 1973-03-23 AT AT262473A patent/AT327190B/de not_active IP Right Cessation
- 1973-03-23 NO NO1205/73A patent/NO139861C/no unknown
- 1973-03-23 RO RO7300074280A patent/RO62622A/ro unknown
- 1973-03-23 ZA ZA732042A patent/ZA732042B/xx unknown
- 1973-03-23 DD DD169759A patent/DD105612A5/xx unknown
- 1973-03-23 SE SE7304111A patent/SE383151B/xx unknown
- 1973-03-23 SU SU1896821A patent/SU468418A3/ru active
- 1973-03-23 JP JP48032786A patent/JPS5233B2/ja not_active Expired
- 1973-03-23 DK DK162073A patent/DK139966C/da not_active IP Right Cessation
- 1973-03-23 AR AR247210A patent/AR219038A1/es active
- 1973-03-24 PL PL1973161446A patent/PL91738B1/pl unknown
- 1973-03-26 BE BE129278A patent/BE797346A/xx not_active IP Right Cessation
- 1973-03-26 FR FR7310713A patent/FR2177963B1/fr not_active Expired
- 1973-03-26 CS CS7300002187A patent/CS183686B2/cs unknown
-
1978
- 1978-12-30 MY MY114/78A patent/MY7800114A/xx unknown
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