FI62300C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-ryl-2-(1-imidazolyl)-etylsulfidderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-ryl-2-(1-imidazolyl)-etylsulfidderivat Download PDFInfo
- Publication number
- FI62300C FI62300C FI763471A FI763471A FI62300C FI 62300 C FI62300 C FI 62300C FI 763471 A FI763471 A FI 763471A FI 763471 A FI763471 A FI 763471A FI 62300 C FI62300 C FI 62300C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- halogen
- group
- ethyl
- ether
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000004458 analytical method Methods 0.000 title description 4
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- -1 melate Chemical compound 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 5
- 229960002509 miconazole Drugs 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229960001270 d- tartaric acid Drugs 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 150000003891 oxalate salts Chemical class 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 241000845082 Panama Species 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 235000003891 ferrous sulphate Nutrition 0.000 description 2
- 239000011790 ferrous sulphate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- YZJSKNMPZQWOMW-UHFFFAOYSA-N 3-chloro-1h-pyridine-2-thione Chemical compound ClC1=CC=CNC1=S YZJSKNMPZQWOMW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 241000228405 Blastomyces dermatitidis Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 241001480036 Epidermophyton floccosum Species 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000233866 Fungi Species 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 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
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 241000222126 [Candida] glabrata Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 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
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical class CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 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
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product 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
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- 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
- C07D233/66—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 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
- C07D233/84—Sulfur atoms
-
- 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
- C07D233/66—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 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49797/75A GB1511390A (en) | 1975-12-04 | 1975-12-04 | Imidazolylalkyl sulphide antifungal agents |
| GB4979775 | 1975-12-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI763471A7 FI763471A7 (en, 2012) | 1977-06-05 |
| FI62300B FI62300B (fi) | 1982-08-31 |
| FI62300C true FI62300C (fi) | 1982-12-10 |
Family
ID=10453567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI763471A FI62300C (fi) | 1975-12-04 | 1976-12-02 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-ryl-2-(1-imidazolyl)-etylsulfidderivat |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4107314A (en, 2012) |
| JP (1) | JPS5277062A (en, 2012) |
| AR (1) | AR223634A1 (en, 2012) |
| AT (1) | AT354435B (en, 2012) |
| AU (1) | AU504085B2 (en, 2012) |
| BE (1) | BE849012A (en, 2012) |
| BG (1) | BG28261A3 (en, 2012) |
| CA (1) | CA1056380A (en, 2012) |
| CH (1) | CH599163A5 (en, 2012) |
| CS (1) | CS195744B2 (en, 2012) |
| DD (1) | DD127186A5 (en, 2012) |
| DE (1) | DE2654665C3 (en, 2012) |
| DK (1) | DK545076A (en, 2012) |
| EG (1) | EG12483A (en, 2012) |
| ES (1) | ES453867A1 (en, 2012) |
| FI (1) | FI62300C (en, 2012) |
| FR (1) | FR2333506A1 (en, 2012) |
| GB (1) | GB1511390A (en, 2012) |
| GR (1) | GR61774B (en, 2012) |
| HU (1) | HU177882B (en, 2012) |
| IE (1) | IE44105B1 (en, 2012) |
| IL (1) | IL50869A (en, 2012) |
| LU (1) | LU76326A1 (en, 2012) |
| NL (1) | NL165463C (en, 2012) |
| NO (1) | NO145791C (en, 2012) |
| NZ (1) | NZ182565A (en, 2012) |
| PH (1) | PH14175A (en, 2012) |
| PL (1) | PL104366B1 (en, 2012) |
| PT (1) | PT65904B (en, 2012) |
| RO (1) | RO72349A (en, 2012) |
| SE (1) | SE423544C (en, 2012) |
| SU (1) | SU635871A3 (en, 2012) |
| YU (1) | YU40157B (en, 2012) |
| ZA (1) | ZA766280B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001654B1 (de) * | 1977-10-13 | 1981-07-22 | Siegfried Aktiengesellschaft | Imidazolyläthyl-oxyalkoxy-Derivate und ihre Thio-Analoge, pharmazeutische Zubereitungen mit diesen Stoffen und Verfahren zu ihrer Herstellung |
| DE2756269A1 (de) * | 1977-12-16 | 1979-06-21 | Bayer Ag | Azolylalkyl-pyridinyl-aether, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| US4343805A (en) * | 1978-12-16 | 1982-08-10 | John Wyeth & Brother Limited | Heterocyclic compounds |
| US4272545A (en) * | 1979-02-02 | 1981-06-09 | Syntex (U.S.A.) Inc. | Derivatives of thienyl- and furyl-substituted N-butyl and N-phenyl imidazoles |
| US4307105A (en) | 1979-07-05 | 1981-12-22 | E. R. Squibb & Sons, Inc. | Imidazolylethoxymethyl derivatives of thiazole |
| US4248881A (en) * | 1979-12-20 | 1981-02-03 | E. R. Squibb & Sons, Inc. | Imidazolylethoxymethyl derivatives of pyrazole |
| CA1155853A (en) * | 1980-06-06 | 1983-10-25 | Joseph A. Martin | Imidazole derivatives and preparation thereof |
| US4458079A (en) * | 1980-08-08 | 1984-07-03 | Bristol-Myers Company | Sulfur-containing imidazoles |
| IN158970B (en, 2012) * | 1981-06-09 | 1987-02-28 | Ici Plc | |
| GB8308601D0 (en) * | 1983-03-29 | 1983-05-05 | Ici Plc | Heterocyclic compounds |
| GB2161160B (en) * | 1984-07-06 | 1989-05-24 | Fisons Plc | Heterocyclic sulphinyl compounds |
| US4661602A (en) * | 1985-03-29 | 1987-04-28 | G. D. Searle & Co. | Substituted alkyl imidazole derivatives |
| US4628104A (en) * | 1985-04-08 | 1986-12-09 | G. D. Searle & Co. | Imidazole ketone derivatives |
| US4761483A (en) * | 1985-06-26 | 1988-08-02 | G. D. Searle & Co. | Chloro-substituted ketone imidazole derivatives |
| AT389874B (de) * | 1988-04-29 | 1990-02-12 | Agrolinz Agrarchemikalien | Neue pyridyl-thio-ethylazole, verfahren zu deren herstellung und diese enthaltende fungizide mittel |
| US6545163B1 (en) * | 1995-10-02 | 2003-04-08 | Napp Technologies | Process to prepare 1-aryl-2-(1-imidazolyl) alkyl ethers and thioethers |
| DE10130706A1 (de) * | 2001-06-26 | 2003-01-02 | Bayer Ag | Thiazine und Thiazole als Materialschutzmittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| GB1475271A (en) * | 1975-04-30 | 1977-06-01 | Pfizer Ltd | 1-aryl-2-1-imidazolyl-alkyl ethers and thioethers and their use as antifungal agents |
-
1975
- 1975-12-04 GB GB49797/75A patent/GB1511390A/en not_active Expired
-
1976
- 1976-01-22 AR AR265558A patent/AR223634A1/es active
- 1976-10-21 ZA ZA766280A patent/ZA766280B/xx unknown
- 1976-11-08 NZ NZ182565A patent/NZ182565A/xx unknown
- 1976-11-09 IL IL50869A patent/IL50869A/xx unknown
- 1976-11-15 PH PH19125A patent/PH14175A/en unknown
- 1976-11-16 AU AU19688/76A patent/AU504085B2/en not_active Expired
- 1976-11-18 YU YU2816/76A patent/YU40157B/xx unknown
- 1976-11-21 EG EG722/76A patent/EG12483A/xx active
- 1976-11-22 JP JP51140604A patent/JPS5277062A/ja active Granted
- 1976-11-22 CA CA266,272A patent/CA1056380A/en not_active Expired
- 1976-11-26 US US05/745,305 patent/US4107314A/en not_active Expired - Lifetime
- 1976-11-30 CS CS767763A patent/CS195744B2/cs unknown
- 1976-11-30 RO RO7688592A patent/RO72349A/ro unknown
- 1976-11-30 PT PT65904A patent/PT65904B/pt unknown
- 1976-12-01 AT AT889476A patent/AT354435B/de not_active IP Right Cessation
- 1976-12-02 ES ES453867A patent/ES453867A1/es not_active Expired
- 1976-12-02 HU HU76PI554A patent/HU177882B/hu unknown
- 1976-12-02 FI FI763471A patent/FI62300C/fi not_active IP Right Cessation
- 1976-12-02 SU SU762426153A patent/SU635871A3/ru active
- 1976-12-02 DE DE2654665A patent/DE2654665C3/de not_active Expired
- 1976-12-02 GR GR52301A patent/GR61774B/el unknown
- 1976-12-02 NL NL7613425.A patent/NL165463C/xx not_active IP Right Cessation
- 1976-12-02 BE BE172928A patent/BE849012A/xx not_active IP Right Cessation
- 1976-12-03 FR FR7636611A patent/FR2333506A1/fr active Granted
- 1976-12-03 PL PL1976194143A patent/PL104366B1/pl unknown
- 1976-12-03 SE SE7613615A patent/SE423544C/xx unknown
- 1976-12-03 IE IE2655/76A patent/IE44105B1/en unknown
- 1976-12-03 BG BG034825A patent/BG28261A3/xx unknown
- 1976-12-03 NO NO764134A patent/NO145791C/no unknown
- 1976-12-03 CH CH1526776A patent/CH599163A5/xx not_active IP Right Cessation
- 1976-12-03 DK DK545076A patent/DK545076A/da not_active Application Discontinuation
- 1976-12-03 DD DD196105A patent/DD127186A5/xx unknown
- 1976-12-03 LU LU76326A patent/LU76326A1/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: PFIZER CORPORATION |