PL98624B1 - Sposob wytwarzania nowych pochodnych imidazolu - Google Patents
Sposob wytwarzania nowych pochodnych imidazolu Download PDFInfo
- Publication number
- PL98624B1 PL98624B1 PL1971187173A PL18717371A PL98624B1 PL 98624 B1 PL98624 B1 PL 98624B1 PL 1971187173 A PL1971187173 A PL 1971187173A PL 18717371 A PL18717371 A PL 18717371A PL 98624 B1 PL98624 B1 PL 98624B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- alkyl
- optionally substituted
- compounds
- group
- Prior art date
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkyl radicals Chemical class 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 14
- 208000015181 infectious disease Diseases 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 206010007134 Candida infections Diseases 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 201000003984 candidiasis Diseases 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000000243 solution 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
- 241001480043 Arthrodermataceae Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 3
- 208000007163 Dermatomycoses Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 208000007027 Oral Candidiasis Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000287411 Turdidae Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000037304 dermatophytes Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000223238 Trichophyton Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 201000003929 dermatomycosis Diseases 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 230000006103 sulfonylation Effects 0.000 description 2
- 238000005694 sulfonylation reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- 241000219321 Caryophyllaceae Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000223203 Coccidioides Species 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000002845 Dianthus plumarius Nutrition 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- 241000204888 Geobacter sp. Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000005428 Pistacia lentiscus Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000012287 Prolapse Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 206010067409 Trichophytosis Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000005486 naphthalic acid group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2041771A DE2041771C3 (de) | 1970-08-22 | 1970-08-22 | derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL98624B1 true PL98624B1 (pl) | 1978-05-31 |
Family
ID=5780483
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971187173A PL98624B1 (pl) | 1970-08-22 | 1971-08-21 | Sposob wytwarzania nowych pochodnych imidazolu |
| PL1971176733A PL96369B1 (pl) | 1970-08-22 | 1971-08-21 | Sposob wytwarzania nowych pochodnych imidazolu |
| PL1971176730A PL95241B1 (instruction) | 1970-08-22 | 1971-08-21 | |
| PL1971187174A PL99299B1 (pl) | 1970-08-22 | 1971-08-21 | Sposob wytwarzania nowych pochodnych imidazolu |
| PL1971150130A PL81801B1 (instruction) | 1970-08-22 | 1971-08-21 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971176733A PL96369B1 (pl) | 1970-08-22 | 1971-08-21 | Sposob wytwarzania nowych pochodnych imidazolu |
| PL1971176730A PL95241B1 (instruction) | 1970-08-22 | 1971-08-21 | |
| PL1971187174A PL99299B1 (pl) | 1970-08-22 | 1971-08-21 | Sposob wytwarzania nowych pochodnych imidazolu |
| PL1971150130A PL81801B1 (instruction) | 1970-08-22 | 1971-08-21 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US3796704A (instruction) |
| JP (3) | JPS5640716B1 (instruction) |
| AR (1) | AR193119A1 (instruction) |
| AT (3) | AT315836B (instruction) |
| AU (1) | AU462239B2 (instruction) |
| BE (1) | BE771584A (instruction) |
| BG (3) | BG19162A3 (instruction) |
| CA (1) | CA923898A (instruction) |
| CH (3) | CH568981A5 (instruction) |
| DD (1) | DD94821A5 (instruction) |
| DE (1) | DE2041771C3 (instruction) |
| EG (1) | EG10169A (instruction) |
| ES (2) | ES394421A1 (instruction) |
| FI (1) | FI55500C (instruction) |
| FR (1) | FR2103452B1 (instruction) |
| GB (1) | GB1354909A (instruction) |
| HU (1) | HU163071B (instruction) |
| IE (1) | IE35547B1 (instruction) |
| IL (1) | IL37537A (instruction) |
| LU (1) | LU63699A1 (instruction) |
| NL (1) | NL7111537A (instruction) |
| NO (3) | NO133402C (instruction) |
| PH (1) | PH10341A (instruction) |
| PL (5) | PL98624B1 (instruction) |
| RO (3) | RO64454A (instruction) |
| SE (3) | SE387342B (instruction) |
| SU (3) | SU451244A3 (instruction) |
| YU (1) | YU34679B (instruction) |
| ZA (1) | ZA715635B (instruction) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3892764A (en) * | 1970-08-22 | 1975-07-01 | Bayer Ag | Phenyl-imidazolyl-alkanyl derivatives, their production and use |
| DE2242454A1 (de) * | 1972-08-29 | 1974-03-07 | Bayer Ag | 1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US3928374A (en) * | 1973-06-22 | 1975-12-23 | Janssen Pharmaceutica Nv | Nitroimidazole derivatives |
| DE2348663A1 (de) * | 1973-09-27 | 1975-04-03 | Bayer Ag | Verfahren zur herstellung von neuen 1-aethyl-azolylderivaten |
| DE2350123C2 (de) * | 1973-10-05 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | 1-Propyl-imidazol-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| IL47885A (en) * | 1974-09-23 | 1979-01-31 | Syntex Inc | Imidazole derivatives,their preparation and antifungal and antibacterial compositions containing them |
| EG11928A (en) * | 1974-12-16 | 1979-03-31 | Hoechst Ag | Process for preparing of 1-alkyl-2-(phenoxy-methyl)-5-nitro-imidazoles |
| CA1065873A (en) * | 1975-01-27 | 1979-11-06 | Janssen Pharmaceutica Naamloze Vennootschap | Imidazole derivatives |
| US4085209A (en) * | 1975-02-05 | 1978-04-18 | Rohm And Haas Company | Preparation and safening effect of 1-substituted imidazole metal salt complexes |
| US4055652A (en) * | 1975-07-07 | 1977-10-25 | Syntex (U.S.A.) Inc. | 1-[β(R-thio)phenethyl]imidazoles and derivatives thereof |
| EG12284A (en) * | 1975-07-12 | 1978-09-30 | Hoechst Ag | Process for the preparation of 1-methyl-2-(phenyl 6 oxymethyl)-5-nitro-imidazoles |
| US4045568A (en) * | 1975-07-28 | 1977-08-30 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles |
| US4078071A (en) * | 1976-03-08 | 1978-03-07 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles |
| MX3866E (es) * | 1975-07-28 | 1981-08-26 | Syntex Inc | Metodo mejorado para preparar derivados de imidazoles n-alquil sustituidos |
| DE2604761A1 (de) * | 1976-02-07 | 1977-08-11 | Bayer Ag | Acylierte imidazolyl-o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US4172141A (en) * | 1976-03-17 | 1979-10-23 | Syntex (U.S.A.) Inc. | N-(naphthylethyl)imidazole derivatives |
| DE2635666A1 (de) * | 1976-08-07 | 1978-02-09 | Bayer Ag | 1-azolyl-4-hydroxy-butan-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und bakterizide |
| DE2635665A1 (de) * | 1976-08-07 | 1978-02-09 | Bayer Ag | Antimikrobielle mittel |
| US4123542A (en) * | 1977-01-19 | 1978-10-31 | Syntex (U.S.A.) Inc. | Derivatives of N-alkyl imidazoles |
| US4213991A (en) * | 1978-05-30 | 1980-07-22 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles and compositions and methods containing the same |
| US4215220A (en) * | 1978-09-11 | 1980-07-29 | Cilag-Chemie A.G. | 1-(2-Oxysubstituted-3-anilinopropyl)-imidazoles |
| US4439441A (en) * | 1979-01-11 | 1984-03-27 | Syntex (U.S.A.) Inc. | Contraceptive compositions and methods employing 1-substituted imidazole derivatives |
| US4430445A (en) | 1979-07-19 | 1984-02-07 | Asahi Kasei Kogyo Kabushiki Kaisha | Novel basic imidazolylmethylstyrene compound, its polymer, a process for the preparation thereof and a use as ion exchange resin |
| US4458079A (en) * | 1980-08-08 | 1984-07-03 | Bristol-Myers Company | Sulfur-containing imidazoles |
| DE3045055A1 (de) * | 1980-11-29 | 1982-07-01 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Heterocyclische verbindungen |
| DE3628545A1 (de) * | 1985-09-23 | 1987-04-23 | Hoechst Ag | Arylmethylazole und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| DE3644616A1 (de) * | 1986-12-29 | 1988-07-07 | Lentia Gmbh | Imidazolderivate, verfahren zur herstellung und deren verwendung |
| DE3707151A1 (de) * | 1987-03-06 | 1988-09-15 | Hoechst Ag | 1-(1-aryl-2-hydroxy-ethyl)-imidazole und deren salze, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| GB9127304D0 (en) * | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| GB9312893D0 (en) * | 1993-06-22 | 1993-08-04 | Boots Co Plc | Therapeutic agents |
| GB9409882D0 (en) * | 1994-05-18 | 1994-07-06 | Sandoz Ltd | Organic compounds |
Family Cites Families (1)
| 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 |
-
1970
- 1970-08-22 DE DE2041771A patent/DE2041771C3/de not_active Expired
-
1971
- 1971-08-11 EG EG358/71A patent/EG10169A/xx active
- 1971-08-11 LU LU63699D patent/LU63699A1/xx unknown
- 1971-08-16 US US00172201A patent/US3796704A/en not_active Expired - Lifetime
- 1971-08-17 BG BG019804A patent/BG19162A3/xx unknown
- 1971-08-17 BG BG019805A patent/BG19802A3/xx unknown
- 1971-08-17 CA CA120737A patent/CA923898A/en not_active Expired
- 1971-08-17 BG BG018370A patent/BG20589A3/xx unknown
- 1971-08-18 AU AU32467/71A patent/AU462239B2/en not_active Expired
- 1971-08-18 HU HUBA2631A patent/HU163071B/hu unknown
- 1971-08-19 RO RO7170519A patent/RO64454A/ro unknown
- 1971-08-19 RO RO7170518A patent/RO67637A/ro unknown
- 1971-08-19 IE IE1048/71A patent/IE35547B1/xx unknown
- 1971-08-19 SU SU1861747A patent/SU451244A3/ru active
- 1971-08-19 YU YU2137/71A patent/YU34679B/xx unknown
- 1971-08-19 RO RO7100067999A patent/RO64158A/ro unknown
- 1971-08-19 SU SU1693076A patent/SU415875A3/ru active
- 1971-08-20 GB GB3919671A patent/GB1354909A/en not_active Expired
- 1971-08-20 NO NO3118/71A patent/NO133402C/no unknown
- 1971-08-20 CH CH1228471A patent/CH568981A5/xx not_active IP Right Cessation
- 1971-08-20 CH CH251275A patent/CH580594A5/xx not_active IP Right Cessation
- 1971-08-20 CH CH251375A patent/CH567486A5/xx not_active IP Right Cessation
- 1971-08-20 IL IL37537A patent/IL37537A/xx unknown
- 1971-08-20 FR FR7130448A patent/FR2103452B1/fr not_active Expired
- 1971-08-20 AT AT1007072A patent/AT315836B/de not_active IP Right Cessation
- 1971-08-20 NL NL7111537A patent/NL7111537A/xx not_active Application Discontinuation
- 1971-08-20 PH PH12767A patent/PH10341A/en unknown
- 1971-08-20 AT AT730071A patent/AT310739B/de not_active IP Right Cessation
- 1971-08-20 FI FI2333/71A patent/FI55500C/fi active
- 1971-08-20 BE BE771584A patent/BE771584A/xx unknown
- 1971-08-20 AT AT1006972A patent/AT315835B/de not_active IP Right Cessation
- 1971-08-20 DD DD157236A patent/DD94821A5/xx unknown
- 1971-08-21 PL PL1971187173A patent/PL98624B1/pl unknown
- 1971-08-21 PL PL1971176733A patent/PL96369B1/pl unknown
- 1971-08-21 PL PL1971176730A patent/PL95241B1/pl unknown
- 1971-08-21 PL PL1971187174A patent/PL99299B1/pl unknown
- 1971-08-21 ES ES394421A patent/ES394421A1/es not_active Expired
- 1971-08-21 PL PL1971150130A patent/PL81801B1/pl unknown
- 1971-08-21 JP JP6337671A patent/JPS5640716B1/ja active Pending
- 1971-08-23 SE SE7110671A patent/SE387342B/xx unknown
- 1971-08-23 ZA ZA715635A patent/ZA715635B/xx unknown
- 1971-09-23 SE SE7404140A patent/SE387941B/xx unknown
-
1972
- 1972-06-07 ES ES72403583A patent/ES403583A1/es not_active Expired
- 1972-07-26 AR AR243281A patent/AR193119A1/es active
- 1972-12-22 SU SU1861748A patent/SU552025A3/ru active
-
1974
- 1974-03-27 SE SE7404139A patent/SE405115B/xx unknown
-
1975
- 1975-03-04 NO NO75750726A patent/NO135787C/no unknown
- 1975-03-04 NO NO750727A patent/NO135363C/no unknown
-
1981
- 1981-03-16 JP JP3667381A patent/JPS56156265A/ja active Pending
- 1981-03-16 JP JP3667481A patent/JPS56156266A/ja active Pending
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