NO980055L - Antisoppmiddel, forbindelse derfor og fremgangsmåte for fremstilling derav - Google Patents
Antisoppmiddel, forbindelse derfor og fremgangsmåte for fremstilling derav Download PDFInfo
- Publication number
- NO980055L NO980055L NO980055A NO980055A NO980055L NO 980055 L NO980055 L NO 980055L NO 980055 A NO980055 A NO 980055A NO 980055 A NO980055 A NO 980055A NO 980055 L NO980055 L NO 980055L
- Authority
- NO
- Norway
- Prior art keywords
- dichlorophenyl
- compound
- preparation
- ylidene
- dithiolan
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 title description 48
- 229940121375 antifungal agent Drugs 0.000 title description 9
- 239000003429 antifungal agent Substances 0.000 title description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 8
- 208000024386 fungal infectious disease Diseases 0.000 claims abstract description 8
- -1 R-(-)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolyl Chemical group 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000002334 glycols Chemical class 0.000 claims description 3
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 2
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 230000000843 anti-fungal effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- ZPGCVVBPGQJSPX-UHFFFAOYSA-N 2-imidazol-1-ylacetonitrile Chemical compound N#CCN1C=CN=C1 ZPGCVVBPGQJSPX-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000002538 fungal effect Effects 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- HZAZETJSOZQUJL-MRVPVSSYSA-N (1s)-1-(2,4-dichlorophenyl)ethane-1,2-diol Chemical compound OC[C@@H](O)C1=CC=C(Cl)C=C1Cl HZAZETJSOZQUJL-MRVPVSSYSA-N 0.000 description 2
- OMNYXCUDBQKCMU-UHFFFAOYSA-N 2,4-dichloro-1-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C(Cl)=C1 OMNYXCUDBQKCMU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000223238 Trichophyton Species 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000003113 dilution method Methods 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FAZJMFBMWUBHCS-MRVPVSSYSA-N (1s)-2-bromo-1-(2,4-dichlorophenyl)ethanol Chemical compound BrC[C@@H](O)C1=CC=C(Cl)C=C1Cl FAZJMFBMWUBHCS-MRVPVSSYSA-N 0.000 description 1
- NAUVKTAUGPDORY-LSLKUGRBSA-N (2r)-2-[1-(2,4-dichlorophenyl)cyclohexa-2,4-dien-1-yl]oxirane Chemical compound ClC1=CC(Cl)=CC=C1C1([C@H]2OC2)C=CC=CC1 NAUVKTAUGPDORY-LSLKUGRBSA-N 0.000 description 1
- VMKAFJQFKBASMU-KRWDZBQOSA-N (3as)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole Chemical compound C([C@H]12)CCN1B(C)OC2(C=1C=CC=CC=1)C1=CC=CC=C1 VMKAFJQFKBASMU-KRWDZBQOSA-N 0.000 description 1
- DASJDMQCPIDJIF-UHFFFAOYSA-N 2-bromo-1-(2,4-dichlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C(Cl)=C1 DASJDMQCPIDJIF-UHFFFAOYSA-N 0.000 description 1
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 108010023063 Bacto-peptone Proteins 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 229960003942 amphotericin b Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
- 229960004022 clotrimazole Drugs 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229930188428 trichomycin Natural products 0.000 description 1
- 235000019263 trisodium citrate Nutrition 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- 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
- A61P31/10—Antimycotics
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19617495 | 1995-07-08 | ||
| PCT/JP1996/001872 WO1997002821A2 (fr) | 1995-07-08 | 1996-07-05 | Agent antifongique, son compose, son procede de production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO980055D0 NO980055D0 (no) | 1998-01-06 |
| NO980055L true NO980055L (no) | 1998-03-06 |
Family
ID=16353435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO980055A NO980055L (no) | 1995-07-08 | 1998-01-06 | Antisoppmiddel, forbindelse derfor og fremgangsmåte for fremstilling derav |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5900488A (fr) |
| EP (1) | EP0839035B1 (fr) |
| KR (1) | KR100386491B1 (fr) |
| CN (1) | CN1091596C (fr) |
| AT (1) | AT407832B (fr) |
| CA (1) | CA2226214C (fr) |
| CH (1) | CH692045A5 (fr) |
| DE (1) | DE19681478B4 (fr) |
| DK (1) | DK176599B1 (fr) |
| ES (1) | ES2137888B1 (fr) |
| FI (1) | FI119357B (fr) |
| GB (1) | GB2317615B (fr) |
| HK (1) | HK1009751A1 (fr) |
| IL (1) | IL122618A (fr) |
| IN (1) | IN185384B (fr) |
| LU (1) | LU90190B1 (fr) |
| NO (1) | NO980055L (fr) |
| NZ (1) | NZ311796A (fr) |
| SE (1) | SE9800016L (fr) |
| TW (1) | TW450969B (fr) |
| WO (1) | WO1997002821A2 (fr) |
| ZA (1) | ZA965745B (fr) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6127397A (en) * | 1996-12-10 | 2000-10-03 | Nihon Nohyaku Co., Ltd. | Optically active (R)-(E)-(4-substituted-phenyl-1,3-dithiolan-2-ylidene)-1-imidazolylaceto nitrile derivative, antifungal composition comprising the same, and method for producing the same |
| JPWO2003105903A1 (ja) * | 2002-06-18 | 2005-10-13 | ポーラ化成工業株式会社 | 抗真菌医薬組成物 |
| CA2489854A1 (fr) * | 2002-06-18 | 2003-12-24 | Pola Chemical Industries Inc. | Composition medicinale fongicide |
| EP2005959B1 (fr) * | 2006-03-08 | 2015-01-21 | Nihon Nohyaku Co., Ltd. | Composition pharmaceutique pour l'usage externe |
| US8268876B2 (en) * | 2006-03-08 | 2012-09-18 | Nihon Nohyaku Co., Ltd. | Pharmaceutical composition for external use |
| MX2008011435A (es) | 2006-03-08 | 2009-02-03 | Nihon Nohyaku Co Ltd | Composicion farmaceutica para uso externo. |
| KR101184834B1 (ko) | 2007-08-27 | 2012-09-20 | 니혼노야쿠가부시키가이샤 | 진균성 피부염용제 |
| US20100204293A1 (en) | 2007-09-05 | 2010-08-12 | Pola Pharma Inc. | Pharmaceutical composition |
| CN101808639B (zh) | 2007-09-05 | 2012-12-05 | 宝丽制药股份有限公司 | 抗真菌医药组合物 |
| US20100173965A1 (en) | 2007-09-05 | 2010-07-08 | Pola Pharma Inc. | Antifungal composition |
| US8193232B2 (en) * | 2009-02-13 | 2012-06-05 | Topica Pharmaceuticals, Inc. | Anti-fungal formulation |
| EP2416758B8 (fr) | 2009-04-09 | 2017-10-18 | Pola Pharma Inc. | Composition pharmaceutique antimycotique |
| CN102387785B (zh) | 2009-04-09 | 2017-08-25 | 宝丽制药股份有限公司 | 抗真菌药物组合物 |
| KR101754697B1 (ko) | 2009-08-25 | 2017-07-06 | 가부시키가이샤 폴라 파마 | 항진균성 약제학적 조성물 |
| JP5832451B2 (ja) | 2010-06-11 | 2015-12-16 | 株式会社ポーラファルマ | 抗真菌医薬組成物 |
| CN103012385B (zh) * | 2012-02-17 | 2015-07-08 | 山东威智医药工业有限公司 | 卢立康唑的晶型及其制备方法 |
| WO2014041846A1 (fr) * | 2012-09-14 | 2014-03-20 | Pola Pharma Inc. | Utilisation de l'énergie libre de surface pour l'évaluation différentielle d'un cristal, cristal évalué en utilisant l'énergie libre de surface à titre d'indice, et composition pharmaceutique contenant ledit cristal |
| JP5460797B1 (ja) | 2012-09-14 | 2014-04-02 | 株式会社ポーラファルマ | アミド誘導体及び安定性指標としてのその使用 |
| EP2895479A1 (fr) * | 2012-09-14 | 2015-07-22 | Pola Pharma Inc. | Cristal ayant des habitus cristallins et composition pharmaceutique obtenue par traitement du cristal |
| WO2014042231A1 (fr) * | 2012-09-14 | 2014-03-20 | Pola Pharma Inc. | Cristal et préparation pharmaceutique le contenant |
| JP6254597B2 (ja) * | 2013-01-28 | 2017-12-27 | 株式会社ポーラファルマ | カンジダ等の病原微生物による疾患用の医薬組成物 |
| EP2948145A1 (fr) * | 2013-01-28 | 2015-12-02 | Pola Pharma Inc. | Composition pharmaceutique destinées à des maladies provoquées par des microorganismes pathogènes tels qu'aspergillus |
| JP5589110B1 (ja) | 2013-03-08 | 2014-09-10 | 株式会社ポーラファルマ | 晶癖を有する結晶及び該結晶を有効成分として含有する医薬組成物 |
| JP5680161B1 (ja) | 2013-09-06 | 2015-03-04 | 株式会社ポーラファルマ | 晶癖を有する結晶及び該結晶を有効成分として含有する医薬組成物 |
| JP5587488B1 (ja) | 2013-12-12 | 2014-09-10 | 株式会社ポーラファルマ | ルリコナゾールを含有する製剤の評価方法及び指標物質 |
| WO2015162271A1 (fr) * | 2014-04-25 | 2015-10-29 | Syngenta Participations Ag | Dérivés imidazoliques microbicides |
| WO2016092478A1 (fr) | 2014-12-12 | 2016-06-16 | Glenmark Pharmaceuticals Limited | Procédé de préparation de luliconazole |
| WO2017108972A1 (fr) | 2015-12-21 | 2017-06-29 | Laboratorios Lesvi, S.L. | Composés de r-(-)-(e)-[4-(2,4-dichlorophényl)-1,3-dithiolan-2-ylidène]-1-imidazolylacétonitrile-ha (luliconazole-ha) à titre d'antifongiques |
| CN106008166B (zh) * | 2016-05-17 | 2018-09-25 | 上海福乐医药科技有限公司 | 一种手性2-氯-1-(2,4-二氯苯基)乙醇的工业化生产方法 |
| EP3558304A2 (fr) | 2016-12-23 | 2019-10-30 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Inhibiteurs de l'élément 1 de la sous-famille b de la famille 7 du cytochrome p450 (cyp7b1) destinés à être utilisés dans le traitement de maladies |
| TR201714882A2 (tr) | 2017-10-03 | 2019-04-22 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Luli̇konazolün topi̇kal farmasöti̇k kompozi̇syonlari |
| US10898470B1 (en) | 2019-08-13 | 2021-01-26 | Sato Pharmaceutical Co., Ltd. | Pharmaceutical composition containing antifungal agent as active ingredient |
| WO2023131969A1 (fr) * | 2022-01-09 | 2023-07-13 | Kimia Biosciences Limited | Procédé amélioré pour la préparation de luliconazole |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0218736B1 (fr) * | 1985-10-10 | 1993-04-07 | Nihon Nohyaku Co., Ltd. | Dérivé de cétène-S,S-acétal, procédé pour sa préparation et méthode pour guérir la mycose utilisant ce dérivé |
| ATE87920T1 (de) * | 1985-10-09 | 1993-04-15 | Nihon Nohyaku Co Ltd | Keten-s,s,-acetalderivate, verfahren zu ihrer herstellung und methode zur heilung von mykose unter verwendung dieser derivate. |
| JP3030780B2 (ja) * | 1988-12-29 | 2000-04-10 | 日本農薬株式会社 | 光学活性なケテンジチオアセタール誘導体及びその製造方法 |
| JPH0386337A (ja) * | 1989-08-28 | 1991-04-11 | Maeda Seisakusho:Kk | エクスパンディングチャックを用いた多重巻締め機および多重巻締め方法 |
| CN1038247C (zh) * | 1990-05-16 | 1998-05-06 | 云南省建筑材料科学研究设计院 | 一种新型磷石膏胶结料 |
| JP3038519B2 (ja) * | 1992-01-28 | 2000-05-08 | 日本農薬株式会社 | 創傷治癒促進剤 |
-
1996
- 1996-07-05 EP EP96922243A patent/EP0839035B1/fr not_active Expired - Lifetime
- 1996-07-05 IN IN1499DE1996 patent/IN185384B/en unknown
- 1996-07-05 ZA ZA965745A patent/ZA965745B/xx unknown
- 1996-07-05 US US08/981,420 patent/US5900488A/en not_active Expired - Lifetime
- 1996-07-05 IL IL12261896A patent/IL122618A/en not_active IP Right Cessation
- 1996-07-05 ES ES009750013A patent/ES2137888B1/es not_active Expired - Fee Related
- 1996-07-05 DE DE19681478T patent/DE19681478B4/de not_active Expired - Lifetime
- 1996-07-05 WO PCT/JP1996/001872 patent/WO1997002821A2/fr active IP Right Grant
- 1996-07-05 CN CN96196659A patent/CN1091596C/zh not_active Expired - Lifetime
- 1996-07-05 AT AT0906196A patent/AT407832B/de not_active IP Right Cessation
- 1996-07-05 CA CA002226214A patent/CA2226214C/fr not_active Expired - Lifetime
- 1996-07-05 GB GB9726766A patent/GB2317615B/en not_active Expired - Lifetime
- 1996-07-05 NZ NZ311796A patent/NZ311796A/xx not_active IP Right Cessation
- 1996-07-05 KR KR10-1998-0700071A patent/KR100386491B1/ko not_active IP Right Cessation
- 1996-07-05 CH CH00023/98A patent/CH692045A5/de not_active IP Right Cessation
- 1996-07-06 TW TW085108169A patent/TW450969B/zh not_active IP Right Cessation
-
1997
- 1997-12-31 LU LU90190A patent/LU90190B1/de active
-
1998
- 1998-01-06 NO NO980055A patent/NO980055L/no not_active Application Discontinuation
- 1998-01-07 FI FI980023A patent/FI119357B/fi not_active IP Right Cessation
- 1998-01-07 DK DK199800013A patent/DK176599B1/da not_active IP Right Cessation
- 1998-01-07 SE SE9800016A patent/SE9800016L/xx not_active Application Discontinuation
- 1998-09-18 HK HK98110741A patent/HK1009751A1/xx not_active IP Right Cessation
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