DK1723156T3 - Process for Preparation of Pyridine Derivatives - Google Patents
Process for Preparation of Pyridine Derivatives Download PDFInfo
- Publication number
- DK1723156T3 DK1723156T3 DK04804186.7T DK04804186T DK1723156T3 DK 1723156 T3 DK1723156 T3 DK 1723156T3 DK 04804186 T DK04804186 T DK 04804186T DK 1723156 T3 DK1723156 T3 DK 1723156T3
- Authority
- DK
- Denmark
- Prior art keywords
- propyl
- substituted
- alkyl
- amino
- aryl
- Prior art date
Links
- 150000003222 pyridines Chemical class 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 229910052740 iodine Inorganic materials 0.000 claims description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000000543 intermediate Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 claims 1
- DHJDPIHFALRNER-UHFFFAOYSA-N 4-amino-1,1,1-trifluorobut-3-en-2-one Chemical compound NC=CC(=O)C(F)(F)F DHJDPIHFALRNER-UHFFFAOYSA-N 0.000 claims 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- -1 6-substituted pyridine Chemical class 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- XPYGGHVSFMUHLH-UUSULHAXSA-N falecalcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(O)(C(F)(F)F)C(F)(F)F)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C XPYGGHVSFMUHLH-UUSULHAXSA-N 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical compound CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 8
- IKHLLNMSMFVTLP-UHFFFAOYSA-N 4-(trifluoromethyl)-1h-pyridin-2-one Chemical compound OC1=CC(C(F)(F)F)=CC=N1 IKHLLNMSMFVTLP-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- WCWACXRUGJZEMU-UHFFFAOYSA-N 2-[hydroxy(methoxy)phosphinothioyl]acetonitrile Chemical compound COP(=S)(O)CC#N WCWACXRUGJZEMU-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- UVIJMESDQMPSLI-UHFFFAOYSA-N 1,1-diethoxy-2-(trifluoromethyl)pent-1-ene Chemical compound FC(F)(F)C(=C(OCC)OCC)CCC UVIJMESDQMPSLI-UHFFFAOYSA-N 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000003905 agrochemical Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- CERDCNUMTCLHAP-UHFFFAOYSA-N 2-ethoxy-4-(trifluoromethyl)pyridine Chemical compound CCOC1=CC(C(F)(F)F)=CC=N1 CERDCNUMTCLHAP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002900 organolithium compounds Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- VTNDOJMFRURHFW-UHFFFAOYSA-N 4-ethoxy-1,1,1-trifluorobut-3-en-2-one 4-(trifluoromethyl)-1H-pyridin-2-one Chemical compound OC1=NC=CC(=C1)C(F)(F)F.C(C)OC=CC(C(F)(F)F)=O VTNDOJMFRURHFW-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- SAFQZYRQIXIKDC-UHFFFAOYSA-N cyanomethylphosphonic acid Chemical compound OP(O)(=O)CC#N SAFQZYRQIXIKDC-UHFFFAOYSA-N 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical class [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- DHJDPIHFALRNER-OWOJBTEDSA-N (e)-4-amino-1,1,1-trifluorobut-3-en-2-one Chemical compound N\C=C\C(=O)C(F)(F)F DHJDPIHFALRNER-OWOJBTEDSA-N 0.000 description 1
- GRCBQYDZUYASQL-UHFFFAOYSA-N 1,1-diethoxy-3-(trifluoromethyl)pent-1-ene Chemical compound FC(C(C=C(OCC)OCC)CC)(F)F GRCBQYDZUYASQL-UHFFFAOYSA-N 0.000 description 1
- AHZDTXAEITWOEF-UHFFFAOYSA-N 5,5-diethoxy-2-methylsulfanyl-3-(trifluoromethyl)pent-2-enenitrile Chemical compound CCOC(OCC)CC(=C(SC)C#N)C(F)(F)F AHZDTXAEITWOEF-UHFFFAOYSA-N 0.000 description 1
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000003482 Pinner synthesis reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- 238000006198 methoxylation reaction Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 150000007944 thiolates Chemical group 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- 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
-
- 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
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53161403P | 2003-12-23 | 2003-12-23 | |
| EP03029730 | 2003-12-23 | ||
| PCT/EP2004/014590 WO2005063780A1 (en) | 2003-12-23 | 2004-12-22 | Process for the preparation of pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK1723156T3 true DK1723156T3 (en) | 2015-04-27 |
Family
ID=34923925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK04804186.7T DK1723156T3 (en) | 2003-12-23 | 2004-12-22 | Process for Preparation of Pyridine Derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7687632B2 (enExample) |
| EP (1) | EP1723156B1 (enExample) |
| JP (3) | JP5160092B2 (enExample) |
| KR (1) | KR101164694B1 (enExample) |
| CN (1) | CN1898255B (enExample) |
| AR (1) | AR046775A1 (enExample) |
| AU (1) | AU2004309054B2 (enExample) |
| BR (1) | BRPI0418047B8 (enExample) |
| CA (1) | CA2550693C (enExample) |
| DK (1) | DK1723156T3 (enExample) |
| ES (1) | ES2528716T3 (enExample) |
| IL (1) | IL176472A (enExample) |
| IN (2) | IN2012DN02545A (enExample) |
| PL (1) | PL1723156T3 (enExample) |
| WO (1) | WO2005063780A1 (enExample) |
| ZA (1) | ZA200605471B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101648906B (zh) * | 2004-04-08 | 2012-07-11 | 美国陶氏益农公司 | 杀虫用n-取代亚磺酰亚胺 |
| US7488828B2 (en) * | 2004-06-25 | 2009-02-10 | Dow Agrosciences Llc | Process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone |
| TW201309635A (zh) | 2006-02-10 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（６-鹵烷基吡啶-３-基）烷基磺醯亞胺（二） |
| TWI381811B (zh) * | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | 用以防治可抵抗一般殺蟲劑之昆蟲的方法 |
| TWI387585B (zh) * | 2006-09-01 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（雜芳基）烷基烴基硫亞胺 |
| US7863303B2 (en) * | 2006-09-01 | 2011-01-04 | Dow Agrosciences Llc | Insecticidal N-substituted (2-substituted-1,3-thiazol)alkyl sulfoximines |
| TWI395736B (zh) * | 2006-11-08 | 2013-05-11 | Dow Agrosciences Llc | 作為殺蟲劑之雜芳基（取代的）烷基ｎ-取代的磺醯亞胺（二） |
| US7709648B2 (en) * | 2007-02-09 | 2010-05-04 | Dow Agrosciences Llc | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
| AR066366A1 (es) * | 2007-05-01 | 2009-08-12 | Dow Agrosciences Llc | Mezclas sinergicas plaguicidas |
| US20090023782A1 (en) * | 2007-07-20 | 2009-01-22 | Dow Agrosciences Llc | Increasing plant vigor |
| KR20100127255A (ko) * | 2008-03-03 | 2010-12-03 | 다우 아그로사이언시즈 엘엘씨 | 살충제 |
| CN102875548A (zh) * | 2011-07-14 | 2013-01-16 | 中国科学院大连化学物理研究所 | 一类基于肟的通过[2+2+2]环加成合成吡啶衍生物的方法 |
| EP2607343A1 (en) | 2011-12-22 | 2013-06-26 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones and of alkenones |
| CN117624038A (zh) * | 2016-12-01 | 2024-03-01 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性杂环衍生物 |
| US12077505B2 (en) | 2018-12-27 | 2024-09-03 | Corteva Agriscience Llc | Preparation of sulfonamide herbicide process intermediates |
| CN113227052B (zh) * | 2018-12-27 | 2025-05-06 | 科迪华农业科技有限责任公司 | 磺酰胺除草剂方法中间体的制备 |
| CN115286568B (zh) * | 2022-08-24 | 2023-12-12 | 常州沃腾化工科技有限公司 | 一种2-羟基-4-三氟甲基吡啶的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE611728A (fr) * | 1960-07-12 | 1962-06-19 | American Cyanamid Co | Perfectionnements aux compositions contenant des antibiotiques à base de tétracycline |
| US3993656A (en) | 1974-11-19 | 1976-11-23 | Merck & Co., Inc. | 1,8-Naphthyridine compounds |
| JPS5221196A (en) * | 1975-08-12 | 1977-02-17 | Fujio Hashimoto | Device for removing red tide |
| JPS5384990A (en) * | 1976-12-29 | 1978-07-26 | Yamanouchi Pharmaceut Co Ltd | Novel nitrogen-containing heterocyclic compound and its preparation |
| JPS53121764A (en) * | 1977-03-31 | 1978-10-24 | Yamanouchi Pharmaceut Co Ltd | Heterocyclic compounds and process for their preparation |
| JPS53127490A (en) * | 1977-04-13 | 1978-11-07 | Yamanouchi Pharmaceut Co Ltd | Novel nitrogen-containing heterocyclic compound |
| JPS55104266A (en) * | 1979-02-02 | 1980-08-09 | Yamanouchi Pharmaceut Co Ltd | Novel pyridone derivative |
| JPS6210087A (ja) * | 1985-07-03 | 1987-01-19 | Shionogi & Co Ltd | ４，７−ジヒドロチエノ〔２，３−ｂ〕ピリジン誘導体，その製造法および循環器系疾患治療剤 |
| JPS6413065A (en) * | 1987-07-06 | 1989-01-17 | Mitsubishi Chem Ind | Peptide derivative of beta-chloro-l-(z)- dehydroglutamic acid |
| DK177191D0 (da) * | 1991-10-23 | 1991-10-23 | Novo Nordisk As | Heterocyclic compounds and their preparation and use |
| US5391745A (en) * | 1992-07-23 | 1995-02-21 | Sloan-Kettering Institute For Cancer Research | Methods of preparation of camptothecin analogs |
| CN1159297C (zh) | 1996-09-24 | 2004-07-28 | 道农业科学公司 | N-([1,2,4]三唑并吖嗪基)苯磺酰胺和吡啶磺酰胺化合物和它们作为除草剂的用途 |
| DE69919707T2 (de) * | 1998-06-19 | 2005-09-01 | Chiron Corp., Emeryville | Glycogen synthase kinase 3 inhibitoren |
| EP1301483A1 (de) * | 2000-07-18 | 2003-04-16 | Basf Aktiengesellschaft | 1-aryl-4-halogenalkyl-2-(1h)-pyridone und ihre verwendung als herbizide |
| US6399781B1 (en) | 2000-10-10 | 2002-06-04 | Boehringer Ingelheim Chemicals, Inc. | Process for making 3-amino-2-chloro-4-methylpyridine |
| US7488828B2 (en) * | 2004-06-25 | 2009-02-10 | Dow Agrosciences Llc | Process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone |
-
2004
- 2004-12-11 ZA ZA200605471A patent/ZA200605471B/en unknown
- 2004-12-22 US US10/584,354 patent/US7687632B2/en not_active Expired - Lifetime
- 2004-12-22 BR BRPI0418047A patent/BRPI0418047B8/pt not_active IP Right Cessation
- 2004-12-22 PL PL04804186T patent/PL1723156T3/pl unknown
- 2004-12-22 KR KR1020067012653A patent/KR101164694B1/ko not_active Expired - Lifetime
- 2004-12-22 IN IN2545DEN2012 patent/IN2012DN02545A/en unknown
- 2004-12-22 ES ES04804186.7T patent/ES2528716T3/es not_active Expired - Lifetime
- 2004-12-22 CA CA2550693A patent/CA2550693C/en not_active Expired - Lifetime
- 2004-12-22 EP EP04804186.7A patent/EP1723156B1/en not_active Expired - Lifetime
- 2004-12-22 JP JP2006546051A patent/JP5160092B2/ja not_active Expired - Lifetime
- 2004-12-22 AU AU2004309054A patent/AU2004309054B2/en not_active Expired
- 2004-12-22 CN CN2004800388844A patent/CN1898255B/zh not_active Expired - Lifetime
- 2004-12-22 AR ARP040104854A patent/AR046775A1/es active IP Right Grant
- 2004-12-22 IN IN2546DEN2012 patent/IN2012DN02546A/en unknown
- 2004-12-22 WO PCT/EP2004/014590 patent/WO2005063780A1/en not_active Ceased
- 2004-12-22 DK DK04804186.7T patent/DK1723156T3/en active
-
2006
- 2006-06-21 IL IL176472A patent/IL176472A/en active IP Right Grant
-
2012
- 2012-06-21 JP JP2012139429A patent/JP2012214487A/ja active Pending
- 2012-10-16 JP JP2012229144A patent/JP2013047245A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL176472A (en) | 2010-11-30 |
| CN1898255B (zh) | 2010-06-09 |
| IN2012DN02546A (enExample) | 2015-08-28 |
| PL1723156T3 (pl) | 2015-07-31 |
| KR101164694B1 (ko) | 2012-07-11 |
| BRPI0418047B8 (pt) | 2022-06-28 |
| EP1723156B1 (en) | 2015-01-21 |
| IL176472A0 (en) | 2006-10-05 |
| BRPI0418047B1 (pt) | 2013-12-31 |
| AR046775A1 (es) | 2005-12-21 |
| JP2013047245A (ja) | 2013-03-07 |
| IN2012DN02545A (enExample) | 2015-07-17 |
| JP2012214487A (ja) | 2012-11-08 |
| CN1898255A (zh) | 2007-01-17 |
| US20070249837A1 (en) | 2007-10-25 |
| KR20060128896A (ko) | 2006-12-14 |
| CA2550693C (en) | 2013-07-30 |
| AU2004309054B2 (en) | 2010-07-08 |
| BRPI0418047A (pt) | 2007-04-17 |
| JP2007519625A (ja) | 2007-07-19 |
| US7687632B2 (en) | 2010-03-30 |
| ES2528716T3 (es) | 2015-02-12 |
| JP5160092B2 (ja) | 2013-03-13 |
| EP1723156A1 (en) | 2006-11-22 |
| WO2005063780A1 (en) | 2005-07-14 |
| CA2550693A1 (en) | 2005-07-14 |
| AU2004309054A1 (en) | 2005-07-14 |
| ZA200605471B (en) | 2007-11-28 |
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