CS195744B2 - Method of producing new derivatives of imidazole - Google Patents
Method of producing new derivatives of imidazole Download PDFInfo
- Publication number
- CS195744B2 CS195744B2 CS767763A CS776376A CS195744B2 CS 195744 B2 CS195744 B2 CS 195744B2 CS 767763 A CS767763 A CS 767763A CS 776376 A CS776376 A CS 776376A CS 195744 B2 CS195744 B2 CS 195744B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carbon atoms
- alkyl
- group
- imidazole
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000002460 imidazoles Chemical class 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- -1 5-chloro-2-thienyl Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 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 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 235000006408 oxalic acid Nutrition 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 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 7
- 230000000855 fungicidal effect Effects 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LYBPCSNKKPXYMD-UHFFFAOYSA-N 1-[2-chloro-2-(5-chlorothiophen-2-yl)ethyl]imidazole Chemical compound ClC=1SC(=CC1)C(CN1C=NC=C1)Cl LYBPCSNKKPXYMD-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- CZRYPOFWTPUSJP-UHFFFAOYSA-N 3-chloro-2-(1h-imidazol-2-yl)-5-nitropyridine Chemical class ClC1=CC([N+](=O)[O-])=CN=C1C1=NC=CN1 CZRYPOFWTPUSJP-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 201000007336 Cryptococcosis Diseases 0.000 description 1
- 241000221204 Cryptococcus neoformans 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
- 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
- 241000699670 Mus sp. Species 0.000 description 1
- 150000007945 N-acyl ureas Chemical group 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 241000222126 [Candida] glabrata Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 150000005303 alkyl halide derivatives Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 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
- 239000011230 binding agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002506 iron compounds Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- LPSGLVVLTUUMIZ-UHFFFAOYSA-N pyridin-2-yl thiohypochlorite Chemical compound ClSC1=CC=CC=N1 LPSGLVVLTUUMIZ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 238000011200 topical administration 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49797/75A GB1511390A (en) | 1975-12-04 | 1975-12-04 | Imidazolylalkyl sulphide antifungal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195744B2 true CS195744B2 (en) | 1980-02-29 |
Family
ID=10453567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS767763A CS195744B2 (en) | 1975-12-04 | 1976-11-30 | Method of producing new derivatives of imidazole |
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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS195744B2 (en) | Method of producing new derivatives of imidazole | |
| US4358458A (en) | Tertiary imidazolyl alcohols and method for the treatment of generalized and local infections caused by fungi and yeasts | |
| IL33918A (en) | Substituted n-benzylimidazoles,their production and pharmaceutical compositions containing them | |
| US4062966A (en) | 1-Aryl-2-(1-imidazolyl) alkyl ethers and thioethers | |
| JPS6345672B2 (en, 2012) | ||
| US4518712A (en) | Piperazine derivative and analgesic composition containing the same | |
| IE56055B1 (en) | Triazole antifungal agents | |
| HU201015B (en) | Process for producing pyridine derivatives | |
| EP0097014A2 (en) | Triazole antifungal agents | |
| US4678789A (en) | Triazole antifungal agents | |
| CS272226B2 (en) | Method of new lensofuran-2 ylimidazol derivatives production | |
| US4282230A (en) | Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them | |
| DE2360550A1 (de) | Indenylaethyltetrazole, -sulfonsaeuren und -phosphorsaeuren | |
| US4705855A (en) | 1-[2-(2,4-dichlorophenyl)-2-(4-substituted piperazine)ethyl]-1H-imidazoles having antimycotic and antibacterial activities, pharmaceutical compositions containing them | |
| JPS6025990A (ja) | トリアゾ−ル系ジオキソラン誘導体 | |
| US4159380A (en) | Imidazolylethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols | |
| SK281688B6 (sk) | Regioselektívny spôsob prípravy derivátov 1-(1,2,4-triazol-1-yl)-propan-2-olu | |
| EP0276793B1 (en) | 3-aryl-5-alkylthio-4h-1,2,4-triazoles | |
| US11739082B2 (en) | Thiophene compounds, process for synthesis and use thereof | |
| JPH0625145B2 (ja) | １−〔（２−フルオロフェニル）（４−フルオロフェニル）フェニルメチル〕−１ｈ−イミダゾール | |
| KR800001314B1 (ko) | 이미다졸 유도체의 제법 | |
| NZ232724A (en) | Heterocyclic substituted pyrazole amide derivatives and pharmaceutical compositions | |
| US3928348A (en) | N-methyl-imidazole derivatives and their production | |
| JPH01258671A (ja) | ５−（１ｈ−イミダゾール−１−イル）−３（２ｈ）−ピリダジノン誘導体 | |
| DK161517B (da) | 1,1-diperfluoralkyl-2-(1h-1,2,4-triazol-1-yl)ethanol-forbindelser og farmaceutisk acceptable salte deraf samt farmaceutiske praeparater indeholdende disse forbindelser |