CS240992B2 - Production method of triazle derivatives - Google Patents
Production method of triazle derivatives Download PDFInfo
- Publication number
- CS240992B2 CS240992B2 CS84575A CS57584A CS240992B2 CS 240992 B2 CS240992 B2 CS 240992B2 CS 84575 A CS84575 A CS 84575A CS 57584 A CS57584 A CS 57584A CS 240992 B2 CS240992 B2 CS 240992B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- compounds
- triazole
- compound
- mixture
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
- -1 chloro, bromo, iodo, methanesulphonyloxy Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 abstract description 6
- 150000003852 triazoles Chemical class 0.000 abstract description 3
- 239000003429 antifungal agent Substances 0.000 abstract 2
- 230000002514 anti-leishmanial effect Effects 0.000 abstract 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000000843 anti-fungal effect Effects 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000222122 Candida albicans Species 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 206010017533 Fungal infection Diseases 0.000 description 5
- 208000031888 Mycoses Diseases 0.000 description 5
- 229940095731 candida albicans Drugs 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 2
- 241001225321 Aspergillus fumigatus Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 201000007336 Cryptococcosis Diseases 0.000 description 2
- 241000221204 Cryptococcus neoformans Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000222727 Leishmania donovani Species 0.000 description 2
- 241000222732 Leishmania major Species 0.000 description 2
- 241001480037 Microsporum Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000223238 Trichophyton Species 0.000 description 2
- 206010047505 Visceral leishmaniasis Diseases 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940091771 aspergillus fumigatus Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000010413 gardening Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XTGYEAXBNRVNQU-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-iodopropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)I XTGYEAXBNRVNQU-UHFFFAOYSA-N 0.000 description 1
- XVMIKRZPDSXBTP-UHFFFAOYSA-N 1,3-dibromobutan-2-one Chemical compound CC(Br)C(=O)CBr XVMIKRZPDSXBTP-UHFFFAOYSA-N 0.000 description 1
- LDWNLMPWSLBXSW-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)-3,3,4,4,5,5,5-heptafluoropentan-2-ol Chemical compound ClCC(O)(CCl)C(F)(F)C(F)(F)C(F)(F)F LDWNLMPWSLBXSW-UHFFFAOYSA-N 0.000 description 1
- HEEACTTWORLLPM-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)ethanol Chemical compound OCCC1=CNC=N1 HEEACTTWORLLPM-UHFFFAOYSA-N 0.000 description 1
- MYDBIEFADJLRGI-UHFFFAOYSA-N 4,4,5,5,6,6,6-heptafluoro-2-(1,2,4-triazol-1-yl)-3-(1,2,4-triazol-1-ylmethyl)hexan-3-ol Chemical compound C1=NC=NN1CC(O)(C(F)(F)C(F)(F)C(F)(F)F)C(C)N1C=NC=N1 MYDBIEFADJLRGI-UHFFFAOYSA-N 0.000 description 1
- RAPQQGKTEAINIZ-UHFFFAOYSA-N 4,4,5,5,6,6,7,7,7-nonafluoro-2-(1,2,4-triazol-1-yl)-3-(1,2,4-triazol-1-ylmethyl)heptan-3-ol Chemical compound C1=NC=NN1CC(O)(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(C)N1C=NC=N1 RAPQQGKTEAINIZ-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000688200 Cingulata Species 0.000 description 1
- 241000223203 Coccidioides Species 0.000 description 1
- 241000223205 Coccidioides immitis Species 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- 241001480036 Epidermophyton floccosum Species 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000228402 Histoplasma Species 0.000 description 1
- 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 1
- 206010061217 Infestation Diseases 0.000 description 1
- 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 1
- 208000004554 Leishmaniasis Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010065764 Mucosal infection Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000007027 Oral Candidiasis Diseases 0.000 description 1
- 241001537205 Paracoccidioides Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000222126 [Candida] glabrata Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012871 anti-fungal composition Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 201000000626 mucocutaneous leishmaniasis Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dentistry (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838302500A GB8302500D0 (en) | 1983-01-29 | 1983-01-29 | Antifungal agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS57584A2 CS57584A2 (en) | 1985-06-13 |
| CS240992B2 true CS240992B2 (en) | 1986-03-13 |
Family
ID=10537168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS84575A CS240992B2 (en) | 1983-01-29 | 1984-01-25 | Production method of triazle derivatives |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4560697A (en, 2012) |
| EP (1) | EP0115416B1 (en, 2012) |
| JP (1) | JPS59181266A (en, 2012) |
| KR (1) | KR870001006B1 (en, 2012) |
| AT (1) | ATE35411T1 (en, 2012) |
| AU (1) | AU543535B2 (en, 2012) |
| CA (1) | CA1244038A (en, 2012) |
| CS (1) | CS240992B2 (en, 2012) |
| DD (1) | DD216928A5 (en, 2012) |
| DE (1) | DE3472403D1 (en, 2012) |
| DK (1) | DK157929C (en, 2012) |
| ES (1) | ES529252A0 (en, 2012) |
| FI (1) | FI75812C (en, 2012) |
| GB (1) | GB8302500D0 (en, 2012) |
| GR (1) | GR81669B (en, 2012) |
| HU (1) | HU193278B (en, 2012) |
| IE (1) | IE56611B1 (en, 2012) |
| IL (1) | IL70797A (en, 2012) |
| NO (1) | NO840336L (en, 2012) |
| NZ (1) | NZ206969A (en, 2012) |
| PH (1) | PH19572A (en, 2012) |
| PL (1) | PL245930A1 (en, 2012) |
| PT (1) | PT78016B (en, 2012) |
| YU (1) | YU13484A (en, 2012) |
| ZA (1) | ZA84633B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2660673A (en) * | 1945-09-15 | 1953-11-24 | Gen Electric | Magnetic induction accelerator |
| GB8414519D0 (en) * | 1984-06-07 | 1984-07-11 | Pfizer Ltd | Triazole antifungal agents |
| EP0181529B1 (de) * | 1984-11-02 | 1991-03-27 | Bayer Ag | Optisch aktives 2-(4-Chlorphenoxymethyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol, ein Verfahren zu dessen Herstellung und dessen Verwendung als Antimykotikum |
| DE3630129A1 (de) * | 1986-09-04 | 1988-03-17 | Bayer Ag | Mercapto-substituierte hydroxyethyl-(triazol-1-yl)-derivate |
| US5611210A (en) * | 1993-03-05 | 1997-03-18 | Ikon Corporation | Fluoroiodocarbon blends as CFC and halon replacements |
| CA2106032C (en) * | 1993-09-13 | 1995-11-07 | Gamini Weeratunga | Methods for the manufacture of fluconazole and forms thereof, intermediates useful in the manufacture thereof, and combinations comprising fluconazole |
| US6270689B1 (en) | 1998-03-26 | 2001-08-07 | Ikon Corporation | Blend compositions of trifluoroiodomethane, tetrafluoroethane and difluoroethane |
| JP6397483B2 (ja) * | 2013-04-12 | 2018-09-26 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 新規トリアゾール誘導体 |
| WO2014167009A1 (en) * | 2013-04-12 | 2014-10-16 | Bayer Cropscience Ag | Novel triazole derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2918894A1 (de) * | 1979-05-10 | 1980-11-20 | Bayer Ag | Fluorierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2938534A1 (de) * | 1979-09-24 | 1981-04-23 | Bayer Ag, 5090 Leverkusen | Acylierte triazolyl-(gamma)-fluorpinakolyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| DE3033592A1 (de) * | 1980-09-06 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Fluorierte 1-azolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE3262386D1 (en) * | 1981-06-06 | 1985-03-28 | Pfizer Ltd | Antifungal agents, processes for their preparation, and pharmaceutical compositions containing them |
-
1983
- 1983-01-29 GB GB838302500A patent/GB8302500D0/en active Pending
-
1984
- 1984-01-16 US US06/571,218 patent/US4560697A/en not_active Expired - Lifetime
- 1984-01-24 DE DE8484300401T patent/DE3472403D1/de not_active Expired
- 1984-01-24 EP EP84300401A patent/EP0115416B1/en not_active Expired
- 1984-01-24 AT AT84300401T patent/ATE35411T1/de not_active IP Right Cessation
- 1984-01-25 CS CS84575A patent/CS240992B2/cs unknown
- 1984-01-26 KR KR1019840000346A patent/KR870001006B1/ko not_active Expired
- 1984-01-26 YU YU00134/84A patent/YU13484A/xx unknown
- 1984-01-26 IE IE176/84A patent/IE56611B1/en not_active IP Right Cessation
- 1984-01-26 GR GR73632A patent/GR81669B/el unknown
- 1984-01-27 NZ NZ206969A patent/NZ206969A/en unknown
- 1984-01-27 CA CA000446219A patent/CA1244038A/en not_active Expired
- 1984-01-27 HU HU84376A patent/HU193278B/hu unknown
- 1984-01-27 DK DK038484A patent/DK157929C/da not_active IP Right Cessation
- 1984-01-27 AU AU23857/84A patent/AU543535B2/en not_active Ceased
- 1984-01-27 FI FI840353A patent/FI75812C/fi not_active IP Right Cessation
- 1984-01-27 DD DD84259681A patent/DD216928A5/de not_active IP Right Cessation
- 1984-01-27 NO NO840336A patent/NO840336L/no unknown
- 1984-01-27 IL IL70797A patent/IL70797A/xx not_active IP Right Cessation
- 1984-01-27 PL PL24593084A patent/PL245930A1/xx unknown
- 1984-01-27 PT PT78016A patent/PT78016B/pt not_active IP Right Cessation
- 1984-01-27 ZA ZA84633A patent/ZA84633B/xx unknown
- 1984-01-27 ES ES529252A patent/ES529252A0/es active Granted
- 1984-01-30 PH PH30172A patent/PH19572A/en unknown
- 1984-01-30 JP JP59015001A patent/JPS59181266A/ja active Granted
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