DD150001A5 - Verfahren zur herstellung einer pyranon-verbindung - Google Patents
Verfahren zur herstellung einer pyranon-verbindung Download PDFInfo
- Publication number
- DD150001A5 DD150001A5 DD80220216A DD22021680A DD150001A5 DD 150001 A5 DD150001 A5 DD 150001A5 DD 80220216 A DD80220216 A DD 80220216A DD 22021680 A DD22021680 A DD 22021680A DD 150001 A5 DD150001 A5 DD 150001A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydrogen
- halogen
- compound
- coor
- alkyl
- Prior art date
Links
- -1 PYRANONE COMPOUND Chemical class 0.000 title claims abstract description 57
- VOLMSPGWNYJHQQ-UHFFFAOYSA-N Pyranone Natural products CC1=C(O)C(=O)C(O)CO1 VOLMSPGWNYJHQQ-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 239000001257 hydrogen Substances 0.000 claims abstract description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 59
- 150000002367 halogens Chemical class 0.000 claims abstract description 59
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 abstract description 5
- 208000026935 allergic disease Diseases 0.000 abstract description 5
- 230000009610 hypersensitivity Effects 0.000 abstract description 5
- 208000006673 asthma Diseases 0.000 abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- 101100354192 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) exp5 gene Proteins 0.000 abstract 4
- 101100505001 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) glpO gene Proteins 0.000 abstract 3
- 101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 2
- 102100032837 Exportin-6 Human genes 0.000 abstract 1
- 101710147891 Exportin-6 Proteins 0.000 abstract 1
- 101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
- 101100439974 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) clpE gene Proteins 0.000 abstract 1
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
- 101150109310 msrAB1 gene Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 161
- 239000000243 solution Substances 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- 235000019441 ethanol Nutrition 0.000 description 54
- 239000000047 product Substances 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 239000007787 solid Substances 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 239000012265 solid product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000012258 stirred mixture Substances 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000004494 ethyl ester group Chemical class 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical class O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical compound CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 3
- XJCMXUBEABHMOI-UHFFFAOYSA-N 3-bromo-4-oxo-6-phenylpyran-2-carboxylic acid Chemical compound O=C1C(Br)=C(C(=O)O)OC(C=2C=CC=CC=2)=C1 XJCMXUBEABHMOI-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- JAPJOXVGMCJAQO-UHFFFAOYSA-N ethyl 6-(4-methoxyphenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=C(OC)C=C1 JAPJOXVGMCJAQO-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- FZZFPTPSFVJXGD-UHFFFAOYSA-N 2,4,6-trioxohexanoic acid Chemical compound OC(=O)C(=O)CC(=O)CC=O FZZFPTPSFVJXGD-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- PEYODCCEJQCEBL-UHFFFAOYSA-N 2-methyl-6-phenylpyran-4-one Chemical compound O1C(C)=CC(=O)C=C1C1=CC=CC=C1 PEYODCCEJQCEBL-UHFFFAOYSA-N 0.000 description 2
- LHXVKSVFYVKRMC-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-oxopyran-2-carboxylic acid Chemical compound O1C=CC(=O)C(C=2C=CC(Cl)=CC=2)=C1C(=O)O LHXVKSVFYVKRMC-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- RSMYYOYTUZKGLT-UHFFFAOYSA-N 5-benzoylpyran-2-one Chemical compound C1=CC(=O)OC=C1C(=O)C1=CC=CC=C1 RSMYYOYTUZKGLT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 238000003512 Claisen condensation reaction Methods 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- UHGFEVJWBJWZLU-UHFFFAOYSA-N ethyl 2,4,6-trioxo-6-phenylhexanoate Chemical compound CCOC(=O)C(=O)CC(=O)CC(=O)C1=CC=CC=C1 UHGFEVJWBJWZLU-UHFFFAOYSA-N 0.000 description 2
- XLXLBEYJBCRVLF-UHFFFAOYSA-N ethyl 5,6-dibromo-6-(4-methoxyphenyl)-2,4-dioxohexanoate Chemical compound CCOC(=O)C(=O)CC(=O)C(Br)C(Br)C1=CC=C(OC)C=C1 XLXLBEYJBCRVLF-UHFFFAOYSA-N 0.000 description 2
- GIJGVIXGGPQSFH-UHFFFAOYSA-N ethyl 6-(2-nitrophenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=CC=C1[N+]([O-])=O GIJGVIXGGPQSFH-UHFFFAOYSA-N 0.000 description 2
- NERKQWKNYPWTSI-UHFFFAOYSA-N ethyl 6-(3-nitrophenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=CC([N+]([O-])=O)=C1 NERKQWKNYPWTSI-UHFFFAOYSA-N 0.000 description 2
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- PWRSHSYTZHHGQD-UHFFFAOYSA-N ethyl 5-bromo-6-(4-chlorophenyl)-2,4-dioxohex-5-enoate Chemical compound CCOC(=O)C(=O)CC(=O)C(Br)=CC1=CC=C(Cl)C=C1 PWRSHSYTZHHGQD-UHFFFAOYSA-N 0.000 description 1
- GFTIUCDVJVWJBK-UHFFFAOYSA-N ethyl 5-hydroxy-6-(4-methoxyphenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C(O)=C1C1=CC=C(OC)C=C1 GFTIUCDVJVWJBK-UHFFFAOYSA-N 0.000 description 1
- DBBRLYJMABEPOM-UHFFFAOYSA-N ethyl 5-methyl-2,4,6-trioxo-6-phenylhexanoate Chemical compound CCOC(=O)C(=O)CC(=O)C(C)C(=O)C1=CC=CC=C1 DBBRLYJMABEPOM-UHFFFAOYSA-N 0.000 description 1
- QZMUHQLCTIXRBQ-UHFFFAOYSA-N ethyl 6-(2-chlorophenyl)-2,4-dioxohex-5-enoate Chemical compound CCOC(=O)C(=O)CC(=O)C=CC1=CC=CC=C1Cl QZMUHQLCTIXRBQ-UHFFFAOYSA-N 0.000 description 1
- VAJQGPSJLRRXOJ-UHFFFAOYSA-N ethyl 6-(2-chlorophenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=CC=C1Cl VAJQGPSJLRRXOJ-UHFFFAOYSA-N 0.000 description 1
- AUNIQVTXEVLATP-UHFFFAOYSA-N ethyl 6-(2-hydroxyphenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=CC=C1O AUNIQVTXEVLATP-UHFFFAOYSA-N 0.000 description 1
- UICLZCSFIXCUPM-UHFFFAOYSA-N ethyl 6-(3-acetamidophenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=CC(NC(C)=O)=C1 UICLZCSFIXCUPM-UHFFFAOYSA-N 0.000 description 1
- WRZHJJYTAGVSBY-UHFFFAOYSA-N ethyl 6-(4-chlorophenyl)-2,4,6-trioxohexanoate Chemical compound CCOC(=O)C(=O)CC(=O)CC(=O)C1=CC=C(Cl)C=C1 WRZHJJYTAGVSBY-UHFFFAOYSA-N 0.000 description 1
- YXKBBYDCEWCPBY-UHFFFAOYSA-N ethyl 6-(4-methylphenyl)-2,4,6-trioxohexanoate Chemical compound CCOC(=O)C(=O)CC(=O)CC(=O)C1=CC=C(C)C=C1 YXKBBYDCEWCPBY-UHFFFAOYSA-N 0.000 description 1
- JXGKTRVXWZALGQ-UHFFFAOYSA-N ethyl 6-(4-methylsulfanylphenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=C(SC)C=C1 JXGKTRVXWZALGQ-UHFFFAOYSA-N 0.000 description 1
- DGDURBVAMYFIQP-UHFFFAOYSA-N ethyl 6-(4-methylsulfonylphenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=C(S(C)(=O)=O)C=C1 DGDURBVAMYFIQP-UHFFFAOYSA-N 0.000 description 1
- GUDWRIQIHRQGKY-UHFFFAOYSA-N ethyl 6-(4-nitrophenyl)-4-oxopyran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C=C1C1=CC=C([N+]([O-])=O)C=C1 GUDWRIQIHRQGKY-UHFFFAOYSA-N 0.000 description 1
- LMBXFWLYIKNCSS-UHFFFAOYSA-N ethyl 6-naphthalen-1-yl-2,4,6-trioxohexanoate Chemical compound C1=CC=C2C(C(=O)CC(=O)CC(=O)C(=O)OCC)=CC=CC2=C1 LMBXFWLYIKNCSS-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 229940080428 lactose 200 mg Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- RMQKWNMRTURXEE-UHFFFAOYSA-N methyl 3-bromo-4-oxo-6-phenylpyran-2-carboxylate Chemical compound O=C1C(Br)=C(C(=O)OC)OC(C=2C=CC=CC=2)=C1 RMQKWNMRTURXEE-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7912062 | 1979-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD150001A5 true DD150001A5 (de) | 1981-08-12 |
Family
ID=10504371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80220216A DD150001A5 (de) | 1979-04-05 | 1980-04-03 | Verfahren zur herstellung einer pyranon-verbindung |
Country Status (32)
| Country | Link |
|---|---|
| US (3) | US4304728A (cs) |
| JP (1) | JPS55133375A (cs) |
| AR (4) | AR224149A1 (cs) |
| AT (1) | AT371456B (cs) |
| AU (1) | AU536369B2 (cs) |
| BE (1) | BE882643A (cs) |
| CA (1) | CA1142526A (cs) |
| CH (1) | CH645370A5 (cs) |
| CS (4) | CS222198B2 (cs) |
| DD (1) | DD150001A5 (cs) |
| DE (1) | DE3012584A1 (cs) |
| DK (1) | DK142080A (cs) |
| ES (1) | ES8104267A1 (cs) |
| FI (1) | FI801019A7 (cs) |
| FR (2) | FR2453169A1 (cs) |
| GB (2) | GB2047698B (cs) |
| GR (1) | GR67747B (cs) |
| HU (1) | HU182115B (cs) |
| IE (1) | IE49658B1 (cs) |
| IL (1) | IL59747A (cs) |
| IT (1) | IT1143085B (cs) |
| LU (1) | LU82335A1 (cs) |
| NL (1) | NL8002024A (cs) |
| NZ (1) | NZ193344A (cs) |
| PH (1) | PH16517A (cs) |
| PL (4) | PL123699B1 (cs) |
| PT (1) | PT71049A (cs) |
| RO (3) | RO84586B (cs) |
| SE (1) | SE8002514L (cs) |
| SU (1) | SU1083909A3 (cs) |
| YU (1) | YU91980A (cs) |
| ZA (1) | ZA801978B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4644071A (en) * | 1984-07-11 | 1987-02-17 | G. D. Searle & Co. | Aralkoxy and aryloxyalkoxy kojic acid derivatives |
| DK59688A (da) * | 1987-03-20 | 1988-09-21 | Hoffmann La Roche | Styrylketoner |
| DE69707860T2 (de) * | 1996-04-26 | 2002-04-11 | Daiichi Pharmaceutical Co., Ltd. | Verfahren zur herstellung von tetrahydroindolizinen |
| TW587079B (en) * | 1998-09-25 | 2004-05-11 | Almirall Prodesfarma Ag | 2-phenylpyran-4-one derivatives |
| PE20011333A1 (es) * | 2000-03-16 | 2002-01-16 | Almirall Prodesfarma Ag | Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2 |
| CA2412985A1 (en) * | 2000-06-16 | 2001-12-27 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| ES2213485B1 (es) * | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
| US8598086B2 (en) | 2009-06-08 | 2013-12-03 | Dow Agrosciences, Llc. | 3-halo-(arly)-4-iminotetrahydropicolinates and their use as herbicides |
| US8252938B2 (en) | 2009-06-08 | 2012-08-28 | Dow Agrosciences, Llc. | Process for the preparation of 6-(aryl)-4-aminopicolinates |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065290A (en) * | 1975-07-03 | 1977-12-27 | Eli Lilly And Company | Herbicidal β-phenyl-4-piperidinones |
| US4060533A (en) * | 1976-06-25 | 1977-11-29 | Sandoz, Inc. | Pyranone carboxamides |
-
1980
- 1980-03-27 US US06/134,385 patent/US4304728A/en not_active Expired - Lifetime
- 1980-03-31 ES ES490121A patent/ES8104267A1/es not_active Expired
- 1980-03-31 IL IL59747A patent/IL59747A/xx unknown
- 1980-04-01 PH PH23843A patent/PH16517A/en unknown
- 1980-04-01 AU AU57032/80A patent/AU536369B2/en not_active Expired - Fee Related
- 1980-04-01 SE SE8002514A patent/SE8002514L/xx not_active Application Discontinuation
- 1980-04-01 DK DK142080A patent/DK142080A/da not_active IP Right Cessation
- 1980-04-01 DE DE19803012584 patent/DE3012584A1/de not_active Withdrawn
- 1980-04-01 FI FI801019A patent/FI801019A7/fi not_active Application Discontinuation
- 1980-04-02 FR FR8007448A patent/FR2453169A1/fr active Granted
- 1980-04-02 NZ NZ193344A patent/NZ193344A/xx unknown
- 1980-04-02 ZA ZA00801978A patent/ZA801978B/xx unknown
- 1980-04-02 AT AT0181980A patent/AT371456B/de not_active IP Right Cessation
- 1980-04-02 PT PT71049A patent/PT71049A/pt unknown
- 1980-04-02 IE IE670/80A patent/IE49658B1/en unknown
- 1980-04-02 HU HU80786A patent/HU182115B/hu unknown
- 1980-04-02 CH CH258880A patent/CH645370A5/fr not_active IP Right Cessation
- 1980-04-02 GR GR61606A patent/GR67747B/el unknown
- 1980-04-03 GB GB8011362A patent/GB2047698B/en not_active Expired
- 1980-04-03 PL PL1980223228A patent/PL123699B1/pl unknown
- 1980-04-03 BE BE6/47125A patent/BE882643A/fr not_active IP Right Cessation
- 1980-04-03 CA CA000349146A patent/CA1142526A/en not_active Expired
- 1980-04-03 PL PL1980230342A patent/PL123812B1/pl unknown
- 1980-04-03 GB GB08312569A patent/GB2123813B/en not_active Expired
- 1980-04-03 PL PL1980230341A patent/PL123813B1/pl unknown
- 1980-04-03 YU YU00919/80A patent/YU91980A/xx unknown
- 1980-04-03 PL PL1980230343A patent/PL123811B1/pl unknown
- 1980-04-03 DD DD80220216A patent/DD150001A5/de unknown
- 1980-04-04 CS CS615781A patent/CS222198B2/cs unknown
- 1980-04-04 CS CS802360A patent/CS222186B2/cs unknown
- 1980-04-04 JP JP4454980A patent/JPS55133375A/ja active Pending
- 1980-04-04 LU LU82335A patent/LU82335A1/fr unknown
- 1980-04-04 CS CS816158A patent/CS222199B2/cs unknown
- 1980-04-04 NL NL8002024A patent/NL8002024A/nl not_active Application Discontinuation
- 1980-04-04 CS CS816156A patent/CS222197B2/cs unknown
- 1980-04-04 IT IT48347/80A patent/IT1143085B/it active
- 1980-04-05 RO RO108190A patent/RO84586B/ro unknown
- 1980-04-05 RO RO108192A patent/RO84583B/ro unknown
- 1980-04-05 RO RO80100748A patent/RO80248A/ro unknown
- 1980-04-07 AR AR280565A patent/AR224149A1/es active
-
1981
- 1981-03-10 SU SU813254246A patent/SU1083909A3/ru active
- 1981-09-07 AR AR286666A patent/AR224318A1/es active
- 1981-09-07 AR AR286667A patent/AR226126A1/es active
- 1981-09-07 AR AR286668A patent/AR226127A1/es active
- 1981-09-17 US US06/303,297 patent/US4448787A/en not_active Expired - Fee Related
- 1981-11-27 FR FR8122254A patent/FR2493147A1/fr active Granted
-
1983
- 1983-05-20 US US06/496,704 patent/US4471129A/en not_active Expired - Fee Related
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