CS63591A2 - Heterocyclic mixtures - Google Patents
Heterocyclic mixtures Download PDFInfo
- Publication number
- CS63591A2 CS63591A2 CS91635A CS63591A CS63591A2 CS 63591 A2 CS63591 A2 CS 63591A2 CS 91635 A CS91635 A CS 91635A CS 63591 A CS63591 A CS 63591A CS 63591 A2 CS63591 A2 CS 63591A2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- phenyl
- alkyl
- carbon atoms
- formula
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 75
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 141
- -1 cyano, nitro, amino Chemical group 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 238000002360 preparation method Methods 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 230000001225 therapeutic effect Effects 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 208000015181 infectious disease Diseases 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 208000030852 Parasitic disease Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 244000045947 parasite Species 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- WTKMRPAPVMPLJW-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[4-[3-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=CC(OC(F)(F)F)=C1 WTKMRPAPVMPLJW-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 230000000865 phosphorylative effect Effects 0.000 claims description 4
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- GOLASOHIFSTCAI-UHFFFAOYSA-N [3-chloro-2,6-dimethyl-5-[4-[4-(trifluoromethoxy)phenoxy]phenyl]pyridin-4-yl] acetate Chemical compound CC(=O)OC1=C(Cl)C(C)=NC(C)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 GOLASOHIFSTCAI-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- JZQPVOWNOXEYCY-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[4-[3-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=CC(OC(F)(F)F)=C1 JZQPVOWNOXEYCY-UHFFFAOYSA-N 0.000 claims description 2
- LPCLQACEIMYBGP-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[4-[3-(trifluoromethyl)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 LPCLQACEIMYBGP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000004340 hydroxynaphthoquinones Chemical group 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- CSFWPUWCSPOLJW-UHFFFAOYSA-N hydroxynaphthoquinone Natural products C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 claims 1
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical group [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 53
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000001228 spectrum Methods 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000000969 carrier Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 241000224016 Plasmodium Species 0.000 description 5
- 241000223960 Plasmodium falciparum Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 201000004792 malaria Diseases 0.000 description 5
- 229920000137 polyphosphoric acid Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 230000003071 parasitic effect Effects 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000000069 prophylactic effect Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 208000003495 Coccidiosis Diseases 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 206010023076 Isosporiasis Diseases 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000037396 body weight Effects 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
- 238000004821 distillation Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000010255 intramuscular injection Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- FYMCXGILCMIOKD-UHFFFAOYSA-N (4-bromophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Br)C=C1 FYMCXGILCMIOKD-UHFFFAOYSA-N 0.000 description 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 2
- HVPNNUYILUSWTF-UHFFFAOYSA-N 2,6-dimethyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound N1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C HVPNNUYILUSWTF-UHFFFAOYSA-N 0.000 description 2
- RUPBVSMEXWASLE-UHFFFAOYSA-N 2,6-dimethyl-3-octyl-1h-pyridin-4-one Chemical compound CCCCCCCCC1=C(C)NC(C)=CC1=O RUPBVSMEXWASLE-UHFFFAOYSA-N 0.000 description 2
- DQOHCGOAPUGGIZ-UHFFFAOYSA-N 2,6-dimethyl-5-octyl-4-oxo-1h-pyridine-3-carbonitrile Chemical compound CCCCCCCCC1=C(C)NC(C)=C(C#N)C1=O DQOHCGOAPUGGIZ-UHFFFAOYSA-N 0.000 description 2
- XABACRVKHMHDNI-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(Cl)=CC=2)=C1C XABACRVKHMHDNI-UHFFFAOYSA-N 0.000 description 2
- VSCDKTPCBYFQQA-UHFFFAOYSA-N 3-[4-(4-chlorophenoxy)phenyl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound N1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=C1C VSCDKTPCBYFQQA-UHFFFAOYSA-N 0.000 description 2
- FWKQRBYAFCNBHM-UHFFFAOYSA-N 3-[4-(4-chlorophenoxy)phenyl]-2,6-dimethylpyran-4-one Chemical compound O1C(C)=CC(=O)C(C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=C1C FWKQRBYAFCNBHM-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
- TVSBOLNHZCJJAX-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[4-[4-(trifluoromethyl)phenoxy]phenyl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 TVSBOLNHZCJJAX-UHFFFAOYSA-N 0.000 description 2
- DIUMPEJAASPKTP-UHFFFAOYSA-N 3-bromo-5-(4-chlorophenyl)-1,2,6-trimethylpyridin-4-one Chemical compound CN1C(C)=C(Br)C(=O)C(C=2C=CC(Cl)=CC=2)=C1C DIUMPEJAASPKTP-UHFFFAOYSA-N 0.000 description 2
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 229960000611 pyrimethamine Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229960004591 robenidine Drugs 0.000 description 1
- 210000004767 rumen Anatomy 0.000 description 1
- 229960001548 salinomycin Drugs 0.000 description 1
- 235000019378 salinomycin Nutrition 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FLXOLGAJDUGCKN-UHFFFAOYSA-N tert-butyltin(3+) methanolate Chemical compound C[O-].C(C)(C)(C)[Sn+3].C[O-].C[O-] FLXOLGAJDUGCKN-UHFFFAOYSA-N 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XZSXEDPHMIFYOS-UHFFFAOYSA-N undec-2-yne Chemical compound CCCCCCCCC#CC XZSXEDPHMIFYOS-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- 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
- C07D213/68—One oxygen atom attached in position 4
-
- 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
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB909005518A GB9005518D0 (en) | 1990-03-12 | 1990-03-12 | Heterocyclic compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
CS63591A2 true CS63591A2 (en) | 1991-12-17 |
Family
ID=10672464
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS91635A CS63591A2 (en) | 1990-03-12 | 1991-03-11 | Heterocyclic mixtures |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP0447164A1 (hu) |
JP (1) | JPH05504961A (hu) |
AP (1) | AP271A (hu) |
CA (1) | CA2078147A1 (hu) |
CS (1) | CS63591A2 (hu) |
FI (1) | FI924071A0 (hu) |
GB (1) | GB9005518D0 (hu) |
HU (1) | HUT68035A (hu) |
IE (1) | IE910790A1 (hu) |
IL (1) | IL97501A (hu) |
MY (1) | MY106873A (hu) |
NZ (1) | NZ237377A (hu) |
OA (1) | OA09684A (hu) |
PT (1) | PT97002A (hu) |
TW (1) | TW201734B (hu) |
WO (1) | WO1991013873A1 (hu) |
ZA (1) | ZA911791B (hu) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0453210A3 (en) * | 1990-04-19 | 1993-01-13 | Imperial Chemical Industries Plc | Pyridine derivatives |
FR2687674B1 (fr) * | 1992-02-07 | 1995-05-19 | Roussel Uclaf | Nouveaux derives de la pyridone, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant. |
DE69735049T2 (de) * | 1996-02-02 | 2006-07-20 | Kumiai Chemical Industry Co., Ltd. | Pyridin derivate und herbizide |
EP1858876A2 (en) | 2005-03-04 | 2007-11-28 | Glaxo Group Limited | Pyridinone derivatives against malaria |
EP1967515A1 (en) * | 2007-03-08 | 2008-09-10 | Glaxo Group Limited | Heterocyclic compounds |
EP1862459A1 (en) * | 2006-05-31 | 2007-12-05 | Glaxo Group Limited | Novel heterocyclic compounds |
TW200817331A (en) * | 2006-05-31 | 2008-04-16 | Glaxo Group Ltd | Novel heterocyclic compounds |
ATE541841T1 (de) | 2007-11-15 | 2012-02-15 | Boehringer Ingelheim Int | Inhibitoren der replikation des human immunodeficiency virus |
EA201200631A1 (ru) | 2007-11-16 | 2012-11-30 | Джилид Сайенсиз, Инк. | Ингибиторы репликации вируса иммунодефицита человека |
PE20091071A1 (es) * | 2007-11-30 | 2009-08-23 | Glaxo Group Ltd | Forma cristalina de un compuesto antimalarico |
WO2010081904A1 (en) | 2009-01-19 | 2010-07-22 | Glaxo Group Limited | 4 ( 1h) -pyridinone derivatives and their use as antimalaria agents |
EP2246329A1 (en) | 2009-01-19 | 2010-11-03 | Glaxo Group Limited | 4(1H)-pyridinone derivatives and their use as antimalaria agents |
TW201039834A (en) | 2009-02-20 | 2010-11-16 | Glaxo Group Ltd | Novel heterocyclic compounds |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL124395C (hu) * | 1963-09-25 | |||
FR1451373A (fr) * | 1965-07-06 | 1966-01-07 | Nouveaux dérivés de la pyridine utilisables notamment comme parasiticides, et procédé pour leur préparation | |
JPS448514Y1 (hu) * | 1966-09-10 | 1969-04-04 | ||
GB1291571A (en) * | 1969-03-29 | 1972-10-04 | Fisons Pharmaceuticals Ltd | Aza chromone-2-carboxylic acids |
DE2162238C3 (de) * | 1971-12-15 | 1981-07-02 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-Methyl-3,5-dijod-4-hydroxy-6-chlorpyridin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel |
AT362613B (de) * | 1975-08-27 | 1981-06-10 | Lilly Co Eli | Herbizides mittel |
JPS6032631B2 (ja) * | 1976-01-17 | 1985-07-29 | 日清製粉株式会社 | r−ピリドン系化合物、その製造方法およびそれらの化合物からなる農業用薬剤 |
US4235619A (en) * | 1977-06-27 | 1980-11-25 | Eli Lilly And Company | Method of controlling aquatic weeds and algae |
JPS6059236B2 (ja) * | 1977-07-06 | 1985-12-24 | 日清製粉株式会社 | γ−ピロン誘導体、その製造方法およびそれらの化合物からなる農業用薬剤 |
GB8310140D0 (en) * | 1983-04-14 | 1983-05-18 | Wellcome Found | Antiprotozoal agents |
DE3889167T2 (de) * | 1987-08-18 | 1994-09-08 | Ihara Chemical Ind Co | Pyridinon-Derivate und diese enthaltende fungizide Zusammenstellungen für die Landwirtschaft und Gartenbau. |
-
1990
- 1990-03-12 GB GB909005518A patent/GB9005518D0/en active Pending
-
1991
- 1991-03-11 MY MYPI91000401A patent/MY106873A/en unknown
- 1991-03-11 PT PT97002A patent/PT97002A/pt not_active Application Discontinuation
- 1991-03-11 NZ NZ237377A patent/NZ237377A/en unknown
- 1991-03-11 EP EP91302031A patent/EP0447164A1/en not_active Withdrawn
- 1991-03-11 CS CS91635A patent/CS63591A2/cs unknown
- 1991-03-11 JP JP3505415A patent/JPH05504961A/ja active Pending
- 1991-03-11 IE IE079091A patent/IE910790A1/en unknown
- 1991-03-11 TW TW080101913A patent/TW201734B/zh active
- 1991-03-11 WO PCT/GB1991/000380 patent/WO1991013873A1/en active Application Filing
- 1991-03-11 IL IL9750191A patent/IL97501A/en not_active IP Right Cessation
- 1991-03-11 CA CA002078147A patent/CA2078147A1/en not_active Abandoned
- 1991-03-11 HU HU9202903A patent/HUT68035A/hu unknown
- 1991-03-11 ZA ZA911791A patent/ZA911791B/xx unknown
- 1991-03-12 AP APAP/P/1991/000243A patent/AP271A/en active
-
1992
- 1992-09-09 OA OA60270A patent/OA09684A/en unknown
- 1992-09-11 FI FI924071A patent/FI924071A0/fi not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
ZA911791B (en) | 1992-11-25 |
IL97501A0 (en) | 1992-06-21 |
FI924071A (fi) | 1992-09-11 |
AP9100243A0 (en) | 1991-04-30 |
PT97002A (pt) | 1991-11-29 |
OA09684A (en) | 1993-05-15 |
IE910790A1 (en) | 1991-09-25 |
GB9005518D0 (en) | 1990-05-09 |
HUT68035A (en) | 1995-05-29 |
NZ237377A (en) | 1993-10-26 |
CA2078147A1 (en) | 1991-09-13 |
AP271A (en) | 1993-06-24 |
MY106873A (en) | 1995-08-30 |
WO1991013873A1 (en) | 1991-09-19 |
IL97501A (en) | 1995-03-15 |
EP0447164A1 (en) | 1991-09-18 |
TW201734B (hu) | 1993-03-11 |
FI924071A0 (fi) | 1992-09-11 |
JPH05504961A (ja) | 1993-07-29 |
HU9202903D0 (en) | 1993-04-28 |
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