IE910456A1 - Aniline derivatives of Ó-styryl carbinols as antifungal¹agents - Google Patents

Aniline derivatives of Ó-styryl carbinols as antifungal¹agents

Info

Publication number: IE910456A1
Authority: IE; Ireland
Prior art keywords: compound; effective amount; mammal; fungal; pharmaceutically acceptable
Prior art date: 1990-02-13

Application number

IE045691A

Other languages

English (en)

Original Assignee

Du Pont

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-02-13

Filing date

1991-02-12

Publication date

1991-08-14

1991-02-12 Application filed by Du Pont filed Critical Du Pont

1991-08-14 Publication of IE910456A1 publication Critical patent/IE910456A1/en

Links

125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 91
238000000034 method Methods 0.000 claims abstract description 36
229940121375 antifungal agent Drugs 0.000 claims abstract description 25
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
230000000843 anti-fungal effect Effects 0.000 claims description 34
241000124008 Mammalia Species 0.000 claims description 30
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 24
208000031888 Mycoses Diseases 0.000 claims description 19
239000003937 drug carrier Substances 0.000 claims description 18
206010017533 Fungal infection Diseases 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 8
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
230000002538 fungal effect Effects 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims description 2
101100028482 Caenorhabditis elegans pal-1 gene Proteins 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
239000003429 antifungal agent Substances 0.000 abstract description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
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125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
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QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 description 3
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125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
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208000015181 infectious disease Diseases 0.000 description 3
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239000008101 lactose Substances 0.000 description 3
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125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
GVCFFVPEOLCYNN-UHFFFAOYSA-N 5-amino-2-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C(C(O)=O)=C1 GVCFFVPEOLCYNN-UHFFFAOYSA-N 0.000 description 2
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BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
241001529936 Murinae Species 0.000 description 1
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 description 1
KPPOWLDNLJLNFJ-UHFFFAOYSA-N N-[3-chloro-4-[1-[2-(2,4-difluorophenyl)oxiran-2-yl]ethenyl]phenyl]acetamide Chemical compound ClC1=CC(NC(=O)C)=CC=C1C(=C)C1(C=2C(=CC(F)=CC=2)F)OC1 KPPOWLDNLJLNFJ-UHFFFAOYSA-N 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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241001045770 Trichophyton mentagrophytes Species 0.000 description 1
AKBMWVRQIVUMPJ-UHFFFAOYSA-N [2-chloro-5-(dimethylamino)phenyl]-[2-(2,4-difluorophenyl)oxiran-2-yl]methanone Chemical compound CN(C)C1=CC=C(Cl)C(C(=O)C2(OC2)C=2C(=CC(F)=CC=2)F)=C1 AKBMWVRQIVUMPJ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000004808 allyl alcohols Chemical class 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
230000003064 anti-oxidating effect Effects 0.000 description 1
239000002543 antimycotic Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
150000007980 azole derivatives Chemical class 0.000 description 1
235000012216 bentonite Nutrition 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
238000002815 broth microdilution Methods 0.000 description 1
ZEXFAVZTIZXHFA-UHFFFAOYSA-N but-2-en-2-ol Chemical compound CC=C(C)O ZEXFAVZTIZXHFA-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
201000003984 candidiasis Diseases 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
238000004040 coloring Methods 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
SGFKGWBZTJDCEU-UHFFFAOYSA-L dipotassium;n,n-dimethylformamide;carbonate Chemical compound [K+].[K+].[O-]C([O-])=O.CN(C)C=O SGFKGWBZTJDCEU-UHFFFAOYSA-L 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000011049 filling Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002311 glutaric acids Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
230000036039 immunity Effects 0.000 description 1
238000005462 in vivo assay Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
LBNPBOFVHYOPIB-UHFFFAOYSA-N methyl 5-amino-2-chlorobenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1Cl LBNPBOFVHYOPIB-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960002509 miconazole Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000004200 microcrystalline wax Substances 0.000 description 1
235000019808 microcrystalline wax Nutrition 0.000 description 1
NASOEJJALHDLAO-UHFFFAOYSA-N n-(3-chloro-4-formylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C=O)C(Cl)=C1 NASOEJJALHDLAO-UHFFFAOYSA-N 0.000 description 1
STXGZOCRSMGIRB-UHFFFAOYSA-N n-[3-chloro-4-[2-(2,4-difluorophenyl)-1-hydroxyprop-2-enyl]phenyl]acetamide Chemical compound ClC1=CC(NC(=O)C)=CC=C1C(O)C(=C)C1=CC=C(F)C=C1F STXGZOCRSMGIRB-UHFFFAOYSA-N 0.000 description 1
QIZYCVIUFKUNQK-UHFFFAOYSA-N n-[3-chloro-4-[3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)but-1-en-2-yl]phenyl]acetamide Chemical compound ClC1=CC(NC(=O)C)=CC=C1C(=C)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=CN=C1 QIZYCVIUFKUNQK-UHFFFAOYSA-N 0.000 description 1
229940064438 nizoral Drugs 0.000 description 1
229960000988 nystatin Drugs 0.000 description 1
VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 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/CC/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)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 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
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
235000019629 palatability Nutrition 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000002810 primary assay Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 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
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 0.000 description 1

Classifications

- 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
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IE045691A 1990-02-13 1991-02-12 Aniline derivatives of Ó-styryl carbinols as antifungal¹agents IE910456A1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US48881390A	1990-02-13	1990-02-13

Publications (1)

Publication Number	Publication Date
IE910456A1 true IE910456A1 (en)	1991-08-14

Family

ID=23941225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE045691A IE910456A1 (en)	1990-02-13	1991-02-12	Aniline derivatives of Ó-styryl carbinols as antifungal¹agents

Country Status (5)

Country	Link
AU (1)	AU7184891A (fr)
IE (1)	IE910456A1 (fr)
IL (1)	IL97201A0 (fr)
NZ (1)	NZ237088A (fr)
WO (1)	WO1991012000A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4311944A1 (de) *	1993-04-10	1994-10-13	Degussa	Umhüllte Natriumpercarbonatpartikel, Verfahren zu deren Herstellung und sie enthaltende Wasch-, Reinigungs- und Bleichmittelzusammensetzungen
US5786375A (en) *	1993-09-16	1998-07-28	Bayer Aktiengesellschaft	Hydroxyethyl-azolyl derivatives
WO2019162228A1 (fr)	2018-02-21	2019-08-29	Bayer Aktiengesellschaft	Dérivés de 1-(imidazol-1-yl à substitution en position 5)but-3-ène et leur utilisation en tant que fongicides
EP3421460A1 (fr)	2018-03-15	2019-01-02	Bayer Aktiengesellschaft	Fongicides de 2-[(4-alkylphenoxy)-pyridinyl]-1-(1,2,4-triazol-1-yl)alkan-2-ol

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE45765B1 (en) *	1976-08-19	1982-11-17	Ici Ltd	Triazoles and imidazoles useful as plant fungicides and growth regulating agents
EP0097425B1 (fr) *	1982-06-14	1987-04-08	Imperial Chemical Industries Plc	Triazolyléthanols possédant une activité fongicide ou régulatrice de croissance des plantes
US4980367A (en) *	1987-12-17	1990-12-25	E. I. Du Pont De Nemours And Company	Antifungal carbinols

1991
- 1991-01-17 WO PCT/US1991/000193 patent/WO1991012000A1/fr not_active Ceased
- 1991-01-17 AU AU71848/91A patent/AU7184891A/en not_active Abandoned
- 1991-02-11 IL IL97201A patent/IL97201A0/xx unknown
- 1991-02-12 IE IE045691A patent/IE910456A1/en unknown
- 1991-02-12 NZ NZ237088A patent/NZ237088A/en unknown

Also Published As

Publication number	Publication date
AU7184891A (en)	1991-09-03
WO1991012000A1 (fr)	1991-08-22
IL97201A0 (en)	1992-05-25
NZ237088A (en)	1993-12-23

Publication	Publication Date	Title
FI82933B (fi)	1991-01-31	Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara 1-aryl-1-fluoralkyl-2-(1h-1,2,4-triazol-1 -yl) etanoler.
US4505919A (en)	1985-03-19	Antifungal S-arylmethyl- and S-heterocyclylmethyl ethers of 2-aryl-3-mercapto-1-(1H-1,2,4-triazol-1-yl) propan-2-ols
HU195647B (en)	1988-06-28	Fungicide composition containing triazol derivatives and process for producing the active agents
EP0115400B1 (fr)	1986-03-26	Agents antifongiques triazoliques
US4483863A (en)	1984-11-20	Triazole antifungal agents
US4678789A (en)	1987-07-07	Triazole antifungal agents
IE910456A1 (en)	1991-08-14	Aniline derivatives of Ó-styryl carbinols as antifungal¹agents
JPH0436153B2 (fr)	1992-06-15
EP0126581B1 (fr)	1987-06-03	Dérivés triazoliques anti-fongiques
US6376526B1 (en)	2002-04-23	Triazole antifungal agents
AU713049B2 (en)	1999-11-25	Azole compounds endowed with antimycotic activity for human and veterinary use
JPS6346070B2 (fr)	1988-09-13
JPS6346075B2 (fr)	1988-09-13
EP0140154B1 (fr)	1989-02-22	1,2,4-Triazolylpropanols, leur préparation et usage
EP0679647A1 (fr)	1995-11-02	Nouveau composé triazol fungicide, sa préparation et son utilisation
JPS635390B2 (fr)	1988-02-03
JPS638938B2 (fr)	1988-02-25
AP875A (en)	2000-09-27	Azole compounds with antimycotic activity for human and veterinary use.
EP1347758A1 (fr)	2003-10-01	Composes azoliques utilises comme antifongiques
JPS59104369A (ja)	1984-06-16	トリアゾ−ル系抗真菌薬
NZ205940A (en)	1986-09-10	Thioketal substituted n-alkyl-imidazole derivatives and pharmaceutical compositions