GB1299100A - Substituted pyridines and dihydropyridines - Google Patents
Substituted pyridines and dihydropyridinesInfo
- Publication number
- GB1299100A GB1299100A GB53254/70A GB5325470A GB1299100A GB 1299100 A GB1299100 A GB 1299100A GB 53254/70 A GB53254/70 A GB 53254/70A GB 5325470 A GB5325470 A GB 5325470A GB 1299100 A GB1299100 A GB 1299100A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- pyridone
- nitro
- methyl
- ethyl
- 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
- 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 title abstract 2
- 150000003222 pyridines Chemical class 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 15
- 150000001875 compounds Chemical class 0.000 abstract 13
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 alkanoylaminoalkyl Chemical group 0.000 abstract 4
- 230000007062 hydrolysis Effects 0.000 abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract 4
- 238000006396 nitration reaction Methods 0.000 abstract 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- MXEMPHBMPPUUBF-UHFFFAOYSA-N 4-ethyl-3-nitropyridin-2-amine Chemical compound CCC1=CC=NC(N)=C1[N+]([O-])=O MXEMPHBMPPUUBF-UHFFFAOYSA-N 0.000 abstract 2
- YVYDGIGILRUPED-UHFFFAOYSA-N 6-methyl-3-nitro-1h-pyridin-2-one Chemical compound CC1=CC=C([N+]([O-])=O)C(=O)N1 YVYDGIGILRUPED-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- CTMPEAVYTANNAJ-UHFFFAOYSA-N 1-acetyl-6-methyl-5-nitropyridin-2-one Chemical compound C(C)(=O)N1C(C=CC(=C1C)[N+](=O)[O-])=O CTMPEAVYTANNAJ-UHFFFAOYSA-N 0.000 abstract 1
- IMFZHDHQZJGAIV-UHFFFAOYSA-N 1-amino-4-tert-butyl-3-nitropyridin-2-one Chemical compound CC(C)(C)C1=C(C(=O)N(N)C=C1)[N+]([O-])=O IMFZHDHQZJGAIV-UHFFFAOYSA-N 0.000 abstract 1
- FNVVTPGMSLODRS-UHFFFAOYSA-N 2-(3-nitro-2-oxo-1h-pyridin-4-yl)acetic acid Chemical compound OC(=O)CC=1C=CNC(=O)C=1[N+]([O-])=O FNVVTPGMSLODRS-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- JQMSTSHOZJFYKE-UHFFFAOYSA-N 2-chloro-3-fluoro-4-methylpyridine Chemical compound CC1=CC=NC(Cl)=C1F JQMSTSHOZJFYKE-UHFFFAOYSA-N 0.000 abstract 1
- DIFCQOVMVHCCHY-UHFFFAOYSA-N 2-chloro-6-methyl-3-(trifluoromethyl)pyridine Chemical compound CC1=CC=C(C(F)(F)F)C(Cl)=N1 DIFCQOVMVHCCHY-UHFFFAOYSA-N 0.000 abstract 1
- IQTGEIJGILYRDG-UHFFFAOYSA-N 3-acetyl-6-methyl-1h-pyridin-2-one Chemical compound CC(=O)C1=CC=C(C)NC1=O IQTGEIJGILYRDG-UHFFFAOYSA-N 0.000 abstract 1
- NIRIZSPCLDUQST-UHFFFAOYSA-N 3-amino-6-ethyl-5-nitro-1H-pyridin-2-one Chemical compound NC=1C(NC(=C(C1)[N+](=O)[O-])CC)=O NIRIZSPCLDUQST-UHFFFAOYSA-N 0.000 abstract 1
- WESUTBLFFZUEKN-UHFFFAOYSA-N 3-fluoro-4-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=[N+]([O-])C=C1F WESUTBLFFZUEKN-UHFFFAOYSA-N 0.000 abstract 1
- NGFBYLSPYWFXKL-UHFFFAOYSA-N 3-fluoro-4-methyl-1h-pyridin-2-one Chemical compound CC=1C=CNC(=O)C=1F NGFBYLSPYWFXKL-UHFFFAOYSA-N 0.000 abstract 1
- WZMOEPZZTTWDIA-UHFFFAOYSA-N 3-fluoro-4-methylpyridine Chemical compound CC1=CC=NC=C1F WZMOEPZZTTWDIA-UHFFFAOYSA-N 0.000 abstract 1
- DNWVOLPALFUHJN-UHFFFAOYSA-N 4-ethyl-3-nitro-1H-pyridin-2-one Chemical compound C(C)C1=C(C(NC=C1)=O)[N+](=O)[O-] DNWVOLPALFUHJN-UHFFFAOYSA-N 0.000 abstract 1
- REYDGDSWWAWBMT-UHFFFAOYSA-N 4-ethyl-5-fluoro-3-nitro-1H-pyridin-2-one Chemical compound C(C)C1=C(C(NC=C1F)=O)[N+](=O)[O-] REYDGDSWWAWBMT-UHFFFAOYSA-N 0.000 abstract 1
- YDXBSDCGUMCGOM-UHFFFAOYSA-N 4-ethyl-5-methylsulfanyl-3-nitro-1H-pyridin-2-one Chemical compound CSC=1C(=C(C(NC1)=O)[N+](=O)[O-])CC YDXBSDCGUMCGOM-UHFFFAOYSA-N 0.000 abstract 1
- UZVCWWHTIBGVGT-UHFFFAOYSA-N 4-ethyl-5-methylsulfonyl-3-nitro-1H-pyridin-2-one Chemical compound CS(=O)(=O)C=1C(=C(C(NC1)=O)[N+](=O)[O-])CC UZVCWWHTIBGVGT-UHFFFAOYSA-N 0.000 abstract 1
- SJWHILBZPGQBJE-UHFFFAOYSA-N 4-ethylpyridin-2-amine Chemical compound CCC1=CC=NC(N)=C1 SJWHILBZPGQBJE-UHFFFAOYSA-N 0.000 abstract 1
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 abstract 1
- OSRNBDZKFYFPPF-UHFFFAOYSA-N 4-methyl-5-nitro-6-oxo-1H-pyridine-3-carboxamide Chemical compound C(N)(=O)C=1C(=C(C(NC1)=O)[N+](=O)[O-])C OSRNBDZKFYFPPF-UHFFFAOYSA-N 0.000 abstract 1
- XPIHMRDMLRKYAM-UHFFFAOYSA-N 4-tert-butyl-1-methyl-3-nitropyridin-2-one Chemical compound C(C)(C)(C)C1=C(C(N(C=C1)C)=O)[N+](=O)[O-] XPIHMRDMLRKYAM-UHFFFAOYSA-N 0.000 abstract 1
- CMFQXPIZAKBRCG-UHFFFAOYSA-N 4-tert-butyl-1-oxidopyridin-1-ium Chemical compound CC(C)(C)C1=CC=[N+]([O-])C=C1 CMFQXPIZAKBRCG-UHFFFAOYSA-N 0.000 abstract 1
- HMDIDYRYZVRRBU-UHFFFAOYSA-N 4-tert-butyl-1h-pyridin-2-one Chemical compound CC(C)(C)C1=CC=NC(O)=C1 HMDIDYRYZVRRBU-UHFFFAOYSA-N 0.000 abstract 1
- BGJBOTZTJWICOV-UHFFFAOYSA-N 4-tert-butyl-3-nitro-1-phenylpyridin-2-one Chemical compound C(C)(C)(C)C1=C(C(N(C=C1)C1=CC=CC=C1)=O)[N+](=O)[O-] BGJBOTZTJWICOV-UHFFFAOYSA-N 0.000 abstract 1
- JSSVDCNRLCNIHC-UHFFFAOYSA-N 4-tert-butyl-5-nitro-6-oxo-1H-pyridine-3-carbonitrile Chemical compound C(C)(C)(C)C1=C(C(NC=C1C#N)=O)[N+](=O)[O-] JSSVDCNRLCNIHC-UHFFFAOYSA-N 0.000 abstract 1
- UTMFPWMQFRRHQH-UHFFFAOYSA-N 5-bromo-4-ethyl-3-nitro-1H-pyridin-2-one Chemical compound BrC=1C(=C(C(NC1)=O)[N+](=O)[O-])CC UTMFPWMQFRRHQH-UHFFFAOYSA-N 0.000 abstract 1
- GYHKKSMDDYZWBC-UHFFFAOYSA-N 5-chloro-4-methyl-3-nitro-1H-pyridin-2-one Chemical compound ClC=1C(=C(C(NC1)=O)[N+](=O)[O-])C GYHKKSMDDYZWBC-UHFFFAOYSA-N 0.000 abstract 1
- FLEYFJUCNSBCTM-UHFFFAOYSA-N 5-ethyl-2-methoxy-3-nitropyridine Chemical compound [N+](=O)([O-])C=1C(=NC=C(C1)CC)OC FLEYFJUCNSBCTM-UHFFFAOYSA-N 0.000 abstract 1
- MQKFQTZHFTWBCK-UHFFFAOYSA-N 5-ethyl-3-nitro-1-(oxan-2-yl)pyridin-2-one Chemical compound C(C)C=1C=C(C(N(C1)C1OCCCC1)=O)[N+](=O)[O-] MQKFQTZHFTWBCK-UHFFFAOYSA-N 0.000 abstract 1
- DILDWFPWXWLUEA-UHFFFAOYSA-N 5-ethyl-3-nitro-1H-pyridin-2-one Chemical compound [N+](=O)([O-])C=1C(NC=C(C1)CC)=O DILDWFPWXWLUEA-UHFFFAOYSA-N 0.000 abstract 1
- QXHPVZZFGCGDEC-UHFFFAOYSA-N 5-ethyl-3-nitro-6-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=NC(=C(C=C1[N+](=O)[O-])CC)C(F)(F)F QXHPVZZFGCGDEC-UHFFFAOYSA-N 0.000 abstract 1
- FMZYJTOWDXLLLS-UHFFFAOYSA-N 6-benzylsulfanyl-3-nitro-1H-pyridin-2-one Chemical compound [O-][N+](=O)C1=CC=C(NC1=O)SCC1=CC=CC=C1 FMZYJTOWDXLLLS-UHFFFAOYSA-N 0.000 abstract 1
- FIMGYEKEYXUTGD-UHFFFAOYSA-N 6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(O)=N1 FIMGYEKEYXUTGD-UHFFFAOYSA-N 0.000 abstract 1
- KPFVRGJJYZUOHH-UHFFFAOYSA-N 6-methyl-3-(trifluoromethyl)-1h-pyridin-2-one Chemical compound CC1=CC=C(C(F)(F)F)C(=O)N1 KPFVRGJJYZUOHH-UHFFFAOYSA-N 0.000 abstract 1
- BGOBNUJEUMXROZ-UHFFFAOYSA-N CC=1C=C(C(NC1)=O)[N+](=O)[O-].C(C)(C)(C)C1=CC(NC=C1[N+](=O)[O-])=O Chemical compound CC=1C=C(C(NC1)=O)[N+](=O)[O-].C(C)(C)(C)C1=CC(NC=C1[N+](=O)[O-])=O BGOBNUJEUMXROZ-UHFFFAOYSA-N 0.000 abstract 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000005887 phenylation reaction Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 abstract 1
- 229940071536 silver acetate Drugs 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000101 thioether group Chemical group 0.000 abstract 1
Classifications
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- 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
- C07D213/61—Halogen atoms or nitro 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- 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
-
- 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
- C07D213/60—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US87605969A | 1969-11-12 | 1969-11-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1299100A true GB1299100A (en) | 1972-12-06 |
Family
ID=25366913
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB53254/70A Expired GB1299100A (en) | 1969-11-12 | 1970-11-09 | Substituted pyridines and dihydropyridines |
Country Status (14)
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3721676A (en) * | 1969-11-12 | 1973-03-20 | Merck & Co Inc | Certain 3-amino-2(1h)pyridones |
GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
US4578459A (en) * | 1973-05-03 | 1986-03-25 | Smithkline & French Laboratories Limited | Heterocyclic alkylaminoheterocycles |
US4260744A (en) * | 1973-05-03 | 1981-04-07 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds |
US4035374A (en) * | 1973-05-03 | 1977-07-12 | Smith Kline & French Laboratories Limited | Imidazolyl alkylaminopyridone and pyridinethione compounds |
US4467087A (en) * | 1973-05-03 | 1984-08-21 | Smith Kline & French Laboratories Limited | 1,2,4-Triazines |
DE3106460A1 (de) * | 1980-03-03 | 1982-01-28 | Sandoz-Patent-GmbH, 7850 Lörrach | 2(1h)-pyridinon-derivate, ihre herstellung und sie enthaltende pharmazeutische zubereitungen |
US4371537A (en) * | 1981-08-13 | 1983-02-01 | The Dow Chemical Company | Sulfur-substituted phenoxypyridines having antiviral activity |
US4412077A (en) * | 1982-03-15 | 1983-10-25 | Sterling Drug Inc. | Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinone |
US4524149A (en) * | 1982-03-15 | 1985-06-18 | Sterling Drug Inc. | 5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use |
US4451469A (en) * | 1982-12-16 | 1984-05-29 | Sterling Drug Inc. | Selected 6-alkyl-and 4,6-dialkyl-2(1H)-pyridinones as cardiotonics |
US4681873A (en) * | 1985-07-29 | 1987-07-21 | Warner-Lambert Company | 4-amino-3-halo-2-pyridinone nucleoside and nucleotide compounds |
US5164506A (en) * | 1988-12-14 | 1992-11-17 | Bayer Aktiengesellschaft | Substituted 2-pyridones and pyrid-2-thiones compounds |
US5032602A (en) * | 1988-12-14 | 1991-07-16 | Bayer Aktiengesellschaft | Inhibiting HMG-CoA reductase with novel substituted 2-pyridones and pyrid-2-thiones |
US5308854A (en) * | 1990-06-18 | 1994-05-03 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
GB9016578D0 (en) * | 1990-07-27 | 1990-09-12 | Ici Plc | Fungicides |
PL218749B1 (pl) * | 2002-02-14 | 2015-01-30 | Pharmacia Corp | Pochodna pirydynonu oraz jej zastosowanie do wytwarzania leku |
KR100901931B1 (ko) | 2002-02-14 | 2009-06-10 | 파마시아 코포레이션 | P38 map 키나제의 조절제로서의 치환된 피리디논 |
AU2007202607B2 (en) * | 2002-02-14 | 2008-12-18 | Pharmacia Corporation | Substituted Pyridinones as Modulators of p38 MAP Kinase |
CL2004002050A1 (es) * | 2003-08-13 | 2005-06-03 | Pharmacia Corp Sa Organizada B | Compuestos derivados de piridinonas sustituidas; su uso en el tratamiento de afecciones causadas o exacerbadas por actividad p38 map kinasa y/o tnf no regulada, tales como inflamaciones, tumores, sida y otros. |
US10696635B2 (en) * | 2016-04-18 | 2020-06-30 | The Scripps Research Institute | Versatile ligand for palladium-catalyzed meta-C—H functionalizations of aromatic substrates |
CN116120225B (zh) * | 2023-01-06 | 2024-09-06 | 利尔化学股份有限公司 | 一种除去三氯吡氧乙酸乙酯中吡啶酮杂质的方法及其应用 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE596728C (de) * | 1932-10-26 | 1934-05-09 | Chem Fab Von Heyden Akt Ges | Verfahren zur Darstellung von 2-Oxy-5-aminopyridin bzw. dessen Kernsubstitutionsprodukten |
DE626687C (de) * | 1934-07-05 | 1936-09-01 | Chem Fab Von Heyden Akt Ges | Verfahren zur Darstellung von Alkoxyaminopyridinen |
NL6816241A (enrdf_load_stackoverflow) * | 1967-12-01 | 1969-06-03 |
-
0
- BE BE758759D patent/BE758759A/xx unknown
-
1969
- 1969-11-12 US US876059A patent/US3654291A/en not_active Expired - Lifetime
-
1970
- 1970-10-28 NL NL7015826A patent/NL7015826A/xx not_active Application Discontinuation
- 1970-11-02 IL IL35568A patent/IL35568A/xx unknown
- 1970-11-05 CA CA097,512A patent/CA968803A/en not_active Expired
- 1970-11-09 GB GB53254/70A patent/GB1299100A/en not_active Expired
- 1970-11-10 FR FR707040455A patent/FR2073341B1/fr not_active Expired
- 1970-11-10 ES ES385397A patent/ES385397A1/es not_active Expired
- 1970-11-10 CH CH1670070A patent/CH549569A/xx not_active IP Right Cessation
- 1970-11-11 DE DE19702055513 patent/DE2055513A1/de active Pending
- 1970-11-11 SE SE7015220A patent/SE386439B/xx unknown
- 1970-11-11 ZA ZA707636A patent/ZA707636B/xx unknown
- 1970-11-11 NO NO4295/70A patent/NO133669C/no unknown
- 1970-11-12 JP JP45099159A patent/JPS4815950B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
DE2055513A1 (de) | 1971-05-19 |
NO133669C (enrdf_load_stackoverflow) | 1976-06-09 |
IL35568A0 (en) | 1971-01-28 |
US3654291A (en) | 1972-04-04 |
SE386439B (sv) | 1976-08-09 |
CH549569A (de) | 1974-05-31 |
FR2073341A1 (enrdf_load_stackoverflow) | 1971-10-01 |
NO133669B (enrdf_load_stackoverflow) | 1976-03-01 |
JPS4815950B1 (enrdf_load_stackoverflow) | 1973-05-18 |
BE758759A (fr) | 1971-05-10 |
IL35568A (en) | 1974-09-10 |
FR2073341B1 (enrdf_load_stackoverflow) | 1973-08-10 |
ES385397A1 (es) | 1973-11-01 |
CA968803A (en) | 1975-06-03 |
ZA707636B (en) | 1972-06-28 |
NL7015826A (enrdf_load_stackoverflow) | 1971-05-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |