KR880002354B1 - 1,2-디하이드로-6-(저급알킬)-2-옥소-5-(피리디닐)니코티노니트릴류 및 니코틴아미드류의 제조방법 - Google Patents
1,2-디하이드로-6-(저급알킬)-2-옥소-5-(피리디닐)니코티노니트릴류 및 니코틴아미드류의 제조방법 Download PDFInfo
- Publication number
- KR880002354B1 KR880002354B1 KR1019830002192A KR830002192A KR880002354B1 KR 880002354 B1 KR880002354 B1 KR 880002354B1 KR 1019830002192 A KR1019830002192 A KR 1019830002192A KR 830002192 A KR830002192 A KR 830002192A KR 880002354 B1 KR880002354 B1 KR 880002354B1
- Authority
- KR
- South Korea
- Prior art keywords
- pyridinyl
- dihydro
- oxo
- methyl
- ethoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000004076 pyridyl group Chemical group 0.000 title description 4
- 235000005152 nicotinamide Nutrition 0.000 title description 3
- 150000005480 nicotinamides Chemical class 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 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 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims 2
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- -1 alkyl ketone Chemical class 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- IATKKGJZTHMRBF-UHFFFAOYSA-N 4-ethoxy-3-pyridin-4-ylbut-3-en-2-one Chemical compound CCOC=C(C(C)=O)C1=CC=NC=C1 IATKKGJZTHMRBF-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical group CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 8
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- ILRVKOYYFFNXDB-UHFFFAOYSA-N 1-pyridin-4-ylpropan-2-one Chemical compound CC(=O)CC1=CC=NC=C1 ILRVKOYYFFNXDB-UHFFFAOYSA-N 0.000 description 5
- HELYUXSLDDBUOQ-UHFFFAOYSA-N 2-oxo-3h-pyridine-3-carbonitrile Chemical compound O=C1N=CC=CC1C#N HELYUXSLDDBUOQ-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OJVKUKRZKKCYGI-UHFFFAOYSA-N 1-ethoxy-2-pyridin-4-ylhex-1-en-3-one Chemical compound C(CC)C(=O)C(=COCC)C1=CC=NC=C1 OJVKUKRZKKCYGI-UHFFFAOYSA-N 0.000 description 3
- HFXSLWPMSHEBFJ-UHFFFAOYSA-N 6-methyl-2-oxo-5-pyridin-3-yl-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=NC=CC=2)=C1C HFXSLWPMSHEBFJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KVBRNDROCOGHBU-UHFFFAOYSA-N 1-(2-methylpyridin-4-yl)propan-2-one Chemical compound CC(=O)CC1=CC=NC(C)=C1 KVBRNDROCOGHBU-UHFFFAOYSA-N 0.000 description 2
- DXAZRERQWGCIIB-UHFFFAOYSA-N 1-ethoxy-2-pyridin-4-ylpent-1-en-3-one Chemical compound CCOC=C(C(=O)CC)C1=CC=NC=C1 DXAZRERQWGCIIB-UHFFFAOYSA-N 0.000 description 2
- FBLVQXITSLUNLI-UHFFFAOYSA-N 1-pyridin-4-ylbutan-2-one Chemical compound CCC(=O)CC1=CC=NC=C1 FBLVQXITSLUNLI-UHFFFAOYSA-N 0.000 description 2
- DHCDIKLTFIGPCG-UHFFFAOYSA-N 3-(2,6-dimethylpyridin-4-yl)-4-ethoxybut-3-en-2-one Chemical compound CC(=O)C(=COCC)C1=CC(=NC(=C1)C)C DHCDIKLTFIGPCG-UHFFFAOYSA-N 0.000 description 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
- IOQQRBBQOMTPLF-UHFFFAOYSA-N 4-ethoxy-3-(2-ethylpyridin-4-yl)but-3-en-2-one Chemical compound CC(=O)C(=COCC)C1=CC(=NC=C1)CC IOQQRBBQOMTPLF-UHFFFAOYSA-N 0.000 description 2
- DUQJDCPBNCISPL-UHFFFAOYSA-N 4-ethoxy-3-(2-methylpyridin-4-yl)but-3-en-2-one Chemical compound CC(=O)C(=COCC)C1=CC(=NC=C1)C DUQJDCPBNCISPL-UHFFFAOYSA-N 0.000 description 2
- SLTYHJNNPGXHGM-UHFFFAOYSA-N 4-ethoxy-3-pyridin-3-ylbut-3-en-2-one Chemical compound CC(=O)C(=COCC)C=1C=NC=CC=1 SLTYHJNNPGXHGM-UHFFFAOYSA-N 0.000 description 2
- QAWDFXARIVUYCT-UHFFFAOYSA-N 4-methoxy-3-pyridin-4-ylbut-3-en-2-one Chemical compound COC=C(C(C)=O)C1=CC=NC=C1 QAWDFXARIVUYCT-UHFFFAOYSA-N 0.000 description 2
- ZCYOBGJUGWBFDI-UHFFFAOYSA-N 4-propoxy-3-pyridin-4-ylbut-3-en-2-one Chemical compound CC(=O)C(=COCCC)C1=CC=NC=C1 ZCYOBGJUGWBFDI-UHFFFAOYSA-N 0.000 description 2
- RWYYNPUQZIPKQN-UHFFFAOYSA-N 6-ethyl-2-oxo-5-pyridin-4-yl-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1CC RWYYNPUQZIPKQN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LCEJYTZYBXTSIX-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)propan-2-one Chemical compound CC(=O)CC1=CC(C)=NC(C)=C1 LCEJYTZYBXTSIX-UHFFFAOYSA-N 0.000 description 1
- RWNXXQFJBALKAX-UHFFFAOYSA-N 1-(dipropoxymethoxy)propane Chemical compound CCCOC(OCCC)OCCC RWNXXQFJBALKAX-UHFFFAOYSA-N 0.000 description 1
- WPDJRDYNRNXPBX-UHFFFAOYSA-N 1-pyridin-3-ylpropan-2-one Chemical compound CC(=O)CC1=CC=CN=C1 WPDJRDYNRNXPBX-UHFFFAOYSA-N 0.000 description 1
- HHKKDDOOJGFETF-UHFFFAOYSA-N 1-pyridin-4-ylpentan-2-one Chemical compound CCCC(=O)CC1=CC=NC=C1 HHKKDDOOJGFETF-UHFFFAOYSA-N 0.000 description 1
- JEWSSFGYFZDUGZ-UHFFFAOYSA-N 2,6-bis(2,6-dimethylpyridin-4-yl)-1,7-diethoxyhepta-1,6-dien-4-one Chemical compound C(C)OC=C(C1=CC(=NC(=C1)C)C)CC(=O)CC(=COCC)C1=CC(=NC(=C1)C)C JEWSSFGYFZDUGZ-UHFFFAOYSA-N 0.000 description 1
- KALBBNASERLKTK-UHFFFAOYSA-N 2-oxo-6-propyl-5-pyridin-4-yl-1h-pyridine-3-carbonitrile Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1CCC KALBBNASERLKTK-UHFFFAOYSA-N 0.000 description 1
- QJBRLLHXVORJEF-UHFFFAOYSA-N 2-pyridin-2-ylpyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1C1=CC=CC=N1 QJBRLLHXVORJEF-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- RQNVIBQEMYYZJE-UHFFFAOYSA-N 6-methyl-2-oxo-5-pyridin-3-yl-1h-pyridine-3-carboxamide Chemical compound N1C(=O)C(C(N)=O)=CC(C=2C=NC=CC=2)=C1C RQNVIBQEMYYZJE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002371 cardiac agent Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- QZNPXKRALPFXPR-UHFFFAOYSA-N n-pyridin-2-ylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC1=CC=CC=N1 QZNPXKRALPFXPR-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000008188 pellet 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US381062 | 1982-05-24 | ||
| US06/381,162 US4417054A (en) | 1982-05-24 | 1982-05-24 | 2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones |
| US381.162 | 1982-05-24 | ||
| US06/381,062 US4413127A (en) | 1982-05-24 | 1982-05-24 | Preparation of 1,2-dihydro-6-(lower alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles |
| US381.062 | 1982-05-24 | ||
| US381162 | 1982-05-24 | ||
| US06/471,961 US4469871A (en) | 1982-05-24 | 1983-03-03 | Process for preparing 2-(lower-alkoxy)-1-(pyridinyl) ethenyl lower-alkyl ketones |
| US471961 | 1983-03-03 | ||
| US471.961 | 1983-03-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850001191A KR850001191A (ko) | 1985-03-16 |
| KR880002354B1 true KR880002354B1 (ko) | 1988-10-29 |
Family
ID=27409519
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830002192A Expired KR880002354B1 (ko) | 1982-05-24 | 1983-05-18 | 1,2-디하이드로-6-(저급알킬)-2-옥소-5-(피리디닐)니코티노니트릴류 및 니코틴아미드류의 제조방법 |
| KR1019880012161D Expired KR890001543B1 (ko) | 1982-05-24 | 1983-05-18 | 2-(저급알콕시)-1-(피리디닐)에테닐 저급알킬케톤 및 그 제조방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880012161D Expired KR890001543B1 (ko) | 1982-05-24 | 1983-05-18 | 2-(저급알콕시)-1-(피리디닐)에테닐 저급알킬케톤 및 그 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0095152B1 (https=) |
| KR (2) | KR880002354B1 (https=) |
| AU (1) | AU559149B2 (https=) |
| DE (1) | DE3367091D1 (https=) |
| DK (1) | DK157488C (https=) |
| ES (2) | ES522506A0 (https=) |
| FI (1) | FI80021C (https=) |
| GR (1) | GR78573B (https=) |
| HK (1) | HK79591A (https=) |
| IE (1) | IE55135B1 (https=) |
| IL (1) | IL68671A (https=) |
| NO (1) | NO163008C (https=) |
| NZ (1) | NZ204175A (https=) |
| PT (1) | PT76710B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4976774A (en) * | 1984-07-20 | 1990-12-11 | The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations | 1-(4'-pyridyl)-4-pyridone, its derivatives and herbicidal use thereof |
| CN111377858B (zh) * | 2018-12-30 | 2023-04-07 | 鲁南制药集团股份有限公司 | 一种米力农的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2824121A (en) * | 1954-11-04 | 1958-02-18 | Kay Fries Chemicals Inc | Process for preparation of oxy alkylidene compounds |
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
| DE2909287A1 (de) * | 1979-03-09 | 1980-09-18 | Bayer Ag | 3-substituierte pyridin-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| US4223149A (en) * | 1979-07-26 | 1980-09-16 | Sterling Drug Inc. | Process for producing 3-cyano-5-(pyridinyl)-2(1H)-pyridinones |
| US4313951A (en) * | 1979-11-26 | 1982-02-02 | Sterling Drug Inc. | 3-Substituted-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones, their cardiotonic use and intermediates therefor |
| US4310670A (en) * | 1980-02-26 | 1982-01-12 | Sterling Drug Inc. | Low-temperature, aqueous conversion of 4-picoline derivative to 5-cyano-[3,4'-bipyridin]-6(1H)-one |
| US4276293A (en) * | 1980-03-28 | 1981-06-30 | Sterling Drug Inc. | Compositions and their preparation |
| US4347363A (en) * | 1981-09-17 | 1982-08-31 | Sterling Drug Inc. | Process for preparing 1,2-dihydro-6-methyl-2-oxo-5-(pyridinyl)nicotinonitriles |
-
1983
- 1983-05-09 NO NO831638A patent/NO163008C/no not_active IP Right Cessation
- 1983-05-09 NZ NZ204175A patent/NZ204175A/xx unknown
- 1983-05-10 AU AU14423/83A patent/AU559149B2/en not_active Expired
- 1983-05-12 IL IL68671A patent/IL68671A/xx not_active IP Right Cessation
- 1983-05-17 IE IE1155/83A patent/IE55135B1/en not_active IP Right Cessation
- 1983-05-17 PT PT76710A patent/PT76710B/pt unknown
- 1983-05-17 FI FI831730A patent/FI80021C/fi not_active IP Right Cessation
- 1983-05-18 KR KR1019830002192A patent/KR880002354B1/ko not_active Expired
- 1983-05-18 ES ES522506A patent/ES522506A0/es active Granted
- 1983-05-18 KR KR1019880012161D patent/KR890001543B1/ko not_active Expired
- 1983-05-18 GR GR71382A patent/GR78573B/el unknown
- 1983-05-19 DE DE8383104984T patent/DE3367091D1/de not_active Expired
- 1983-05-19 EP EP83104984A patent/EP0095152B1/en not_active Expired
- 1983-05-19 DK DK224283A patent/DK157488C/da not_active IP Right Cessation
-
1984
- 1984-09-17 ES ES535990A patent/ES535990A0/es active Granted
-
1991
- 1991-10-10 HK HK795/91A patent/HK79591A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI80021C (fi) | 1990-04-10 |
| DK157488C (da) | 1990-06-11 |
| DK224283A (da) | 1983-11-25 |
| DK224283D0 (da) | 1983-05-19 |
| IL68671A0 (en) | 1983-09-30 |
| ES8601132A1 (es) | 1985-10-16 |
| AU559149B2 (en) | 1987-02-26 |
| DK157488B (da) | 1990-01-15 |
| EP0095152B1 (en) | 1986-10-22 |
| FI831730L (fi) | 1983-11-25 |
| KR850001191A (ko) | 1985-03-16 |
| NO163008B (no) | 1989-12-11 |
| HK79591A (en) | 1991-10-18 |
| ES8506693A1 (es) | 1985-08-01 |
| ES522506A0 (es) | 1985-08-01 |
| FI831730A0 (fi) | 1983-05-17 |
| NO163008C (no) | 1990-03-21 |
| AU1442383A (en) | 1983-12-01 |
| EP0095152A1 (en) | 1983-11-30 |
| FI80021B (fi) | 1989-12-29 |
| PT76710B (en) | 1985-12-27 |
| NO831638L (no) | 1983-11-25 |
| PT76710A (en) | 1983-06-01 |
| IE55135B1 (en) | 1990-06-06 |
| GR78573B (https=) | 1984-09-27 |
| IE831155L (en) | 1983-11-24 |
| ES535990A0 (es) | 1985-10-16 |
| DE3367091D1 (en) | 1986-11-27 |
| KR890001543B1 (ko) | 1989-05-08 |
| NZ204175A (en) | 1985-12-13 |
| IL68671A (en) | 1986-07-31 |
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