AP104A - Triazole antifungal agents. - Google Patents

Triazole antifungal agents. Download PDF

Info

Publication number: AP104A
Authority: AP; ARIPO
Prior art keywords: het; formula; compound; alkyl; pyridinyl
Prior art date: 1988-08-13

Application number

APAP/P/1989/000135A

Other languages

English (en)

Other versions

AP8900135A0 (en

Inventor

Dickinson Roger Peter Dr

Richardson Kenneth Dr

Original Assignee

Pfizer

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.)

1988-08-13

Filing date

1989-08-10

Publication date

1990-11-02

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10642109&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AP104(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1989-08-10 Application filed by Pfizer filed Critical Pfizer

1989-10-31 Publication of AP8900135A0 publication Critical patent/AP8900135A0/xx

1990-11-02 Application granted granted Critical

1990-11-02 Publication of AP104A publication Critical patent/AP104A/en

Links

229940121375 antifungal agent Drugs 0.000 title claims abstract description 10
239000003429 antifungal agent Substances 0.000 title claims abstract description 7
150000003852 triazoles Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 129
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 102
238000000034 method Methods 0.000 claims description 77
239000000203 mixture Substances 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 37
229910052799 carbon Inorganic materials 0.000 claims description 35
230000008569 process Effects 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 32
-1 C.-C Chemical group 0.000 claims description 26
238000011282 treatment Methods 0.000 claims description 25
125000004076 pyridyl group Chemical group 0.000 claims description 22
125000005843 halogen group Chemical group 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000003373 pyrazinyl group Chemical group 0.000 claims description 17
125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 17
125000002098 pyridazinyl group Chemical group 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 12
150000002924 oxiranes Chemical class 0.000 claims description 11
125000004306 triazinyl group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
239000011734 sodium Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 7
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
150000001204 N-oxides Chemical class 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
159000000000 sodium salts Chemical class 0.000 claims description 4
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
239000012954 diazonium Substances 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
229940045803 cuprous chloride Drugs 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
230000022244 formylation Effects 0.000 claims description 2
238000006170 formylation reaction Methods 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 8
238000002360 preparation method Methods 0.000 claims 5
150000001412 amines Chemical class 0.000 claims 3
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
241000207742 Nicrophorus apo Species 0.000 claims 1
239000000463 material Substances 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
238000005979 thermal decomposition reaction Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
239000000243 solution Substances 0.000 description 113
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
239000000047 product Substances 0.000 description 39
238000001704 evaporation Methods 0.000 description 36
230000008020 evaporation Effects 0.000 description 36
238000004458 analytical method Methods 0.000 description 34
238000010828 elution Methods 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
238000003756 stirring Methods 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 19
239000000284 extract Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 15
239000007787 solid Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
239000003960 organic solvent Substances 0.000 description 11
239000000543 intermediate Substances 0.000 description 10
229940043279 diisopropylamine Drugs 0.000 description 9
239000007858 starting material Substances 0.000 description 9
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000012043 crude product Substances 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
238000011065 in-situ storage Methods 0.000 description 7
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 6
230000000843 anti-fungal effect Effects 0.000 description 6
JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 6
125000001589 carboacyl group Chemical group 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
206010017533 Fungal infection Diseases 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
208000031888 Mycoses Diseases 0.000 description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
241000222122 Candida albicans Species 0.000 description 4
241000282414 Homo sapiens Species 0.000 description 4
239000012267 brine Substances 0.000 description 4
229940095731 candida albicans Drugs 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000006260 foam Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
YQUHULOBTDYMAG-UHFFFAOYSA-N methyl 2,4-difluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C=C1F YQUHULOBTDYMAG-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 3
XGHABZPSYISTKF-UHFFFAOYSA-N 4-ethylpyridazine Chemical compound CCC1=CC=NN=C1 XGHABZPSYISTKF-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
241001225321 Aspergillus fumigatus Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
229940091771 aspergillus fumigatus Drugs 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000012535 impurity Substances 0.000 description 3
230000011987 methylation Effects 0.000 description 3
238000007069 methylation reaction Methods 0.000 description 3
125000002524 organometallic group Chemical group 0.000 description 3
238000012360 testing method Methods 0.000 description 3
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 3
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
241000282412 Homo Species 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
241001480037 Microsporum Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
241000223238 Trichophyton Species 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000006071 cream Substances 0.000 description 2
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239000012458 free base Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
VQEVKEKJZVEGPH-UHFFFAOYSA-N lithium;chloromethane Chemical compound [Li+].Cl[CH2-] VQEVKEKJZVEGPH-UHFFFAOYSA-N 0.000 description 2
LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 2
CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000002674 ointment Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
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BAQLNPIEFOYKNB-UHFFFAOYSA-N pyridine-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CC=N1 BAQLNPIEFOYKNB-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
MDUSUFIKBUMDTJ-UHFFFAOYSA-N sodium;1h-1,2,4-triazole Chemical compound [Na].C=1N=CNN=1 MDUSUFIKBUMDTJ-UHFFFAOYSA-N 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000002424 x-ray crystallography Methods 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
NUOYJPPISCCYDH-BYPYZUCNSA-N (2s)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carbonyl chloride Chemical compound FC(F)(F)C(=O)N1CCC[C@H]1C(Cl)=O NUOYJPPISCCYDH-BYPYZUCNSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- A—HUMAN NECESSITIES
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- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
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APAP/P/1989/000135A 1988-08-13 1989-08-10 Triazole antifungal agents. AP104A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888819308A GB8819308D0 (en)	1988-08-13	1988-08-13	Triazole antifungal agents

Publications (2)

Publication Number	Publication Date
AP8900135A0 AP8900135A0 (en)	1989-10-31
AP104A true AP104A (en)	1990-11-02

Family

ID=10642109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1989/000135A AP104A (en)	1988-08-13	1989-08-10	Triazole antifungal agents.

Country Status (38)

Country	Link
US (2)	US5116844A (es)
EP (1)	EP0357241B1 (es)
JP (2)	JPH0786100B2 (es)
KR (1)	KR930002729B1 (es)
CN (1)	CN1029231C (es)
AP (1)	AP104A (es)
AR (1)	AR246963A1 (es)
AU (1)	AU602638B2 (es)
BG (1)	BG60865B1 (es)
CA (1)	CA1341325C (es)
CY (1)	CY1968A (es)
CZ (1)	CZ284318B6 (es)
DD (1)	DD284010A5 (es)
DE (1)	DE68913105T2 (es)
DK (1)	DK172471B1 (es)
ES (1)	ES2062009T4 (es)
FI (1)	FI96859C (es)
GB (1)	GB8819308D0 (es)
HU (2)	HU205348B (es)
IE (1)	IE61412B1 (es)
IL (1)	IL91231A (es)
IN (1)	IN175438B (es)
IS (1)	IS1586B (es)
LV (1)	LV10714B (es)
MA (1)	MA21610A1 (es)
MX (1)	MX17169A (es)
MY (1)	MY105092A (es)
NO (1)	NO174101C (es)
NZ (1)	NZ230283A (es)
OA (1)	OA09126A (es)
PE (1)	PE1591A1 (es)
PL (2)	PL163756B1 (es)
PT (1)	PT91440B (es)
RO (1)	RO108453B1 (es)
RU (2)	RU1836366C (es)
SK (1)	SK280775B6 (es)
YU (1)	YU47093B (es)
ZA (1)	ZA896151B (es)

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RU2295958C1 (ru) *	2005-07-04	2007-03-27	Федеральное государственное унитарное предприятие "Центр по химии лекарственных средств" (ФГУП ЦХЛС-ВНИХФИ)	Фармацевтический состав для лечения грибковых заболеваний и способ его получения
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CN102796087B (zh) *	2012-09-04	2015-04-15	西南大学	香豆素三唑醇及其制备方法和用途
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1988
- 1988-08-13 GB GB888819308A patent/GB8819308D0/en active Pending
1989
- 1989-07-18 IN IN634DE1989 patent/IN175438B/en unknown
- 1989-07-24 AU AU38930/89A patent/AU602638B2/en not_active Expired
- 1989-07-31 PE PE1989157445A patent/PE1591A1/es unknown
- 1989-08-03 DE DE68913105T patent/DE68913105T2/de not_active Expired - Lifetime
- 1989-08-03 ES ES89307920T patent/ES2062009T4/es not_active Expired - Lifetime
- 1989-08-03 EP EP89307920A patent/EP0357241B1/en not_active Expired - Lifetime
- 1989-08-07 IL IL9123189A patent/IL91231A/en active Protection Beyond IP Right Term
- 1989-08-08 MA MA21863A patent/MA21610A1/fr unknown
- 1989-08-10 MY MYPI89001091A patent/MY105092A/en unknown
- 1989-08-10 SK SK4761-89A patent/SK280775B6/sk unknown
- 1989-08-10 AP APAP/P/1989/000135A patent/AP104A/en active
- 1989-08-10 IS IS3499A patent/IS1586B/is unknown
- 1989-08-10 CZ CS894761A patent/CZ284318B6/cs not_active IP Right Cessation
- 1989-08-11 OA OA59624A patent/OA09126A/xx unknown
- 1989-08-11 PT PT91440A patent/PT91440B/pt not_active IP Right Cessation
- 1989-08-11 ZA ZA896151A patent/ZA896151B/xx unknown
- 1989-08-11 YU YU158789A patent/YU47093B/sh unknown
- 1989-08-11 HU HU894151A patent/HU205348B/hu unknown
- 1989-08-11 NO NO893248A patent/NO174101C/no not_active IP Right Cessation
- 1989-08-11 JP JP1209513A patent/JPH0786100B2/ja not_active Expired - Lifetime
- 1989-08-11 PL PL89297228A patent/PL163756B1/pl unknown
- 1989-08-11 AR AR89314635A patent/AR246963A1/es active
- 1989-08-11 RU SU894614663A patent/RU1836366C/ru active
- 1989-08-11 DK DK198903945A patent/DK172471B1/da not_active IP Right Cessation
- 1989-08-11 BG BG89519A patent/BG60865B1/bg unknown
- 1989-08-11 IE IE258289A patent/IE61412B1/en not_active IP Right Cessation
- 1989-08-11 PL PL28102089A patent/PL162953B1/pl unknown
- 1989-08-11 FI FI893809A patent/FI96859C/fi active IP Right Grant
- 1989-08-11 NZ NZ230283A patent/NZ230283A/xx unknown
- 1989-08-11 US US07/392,686 patent/US5116844A/en not_active Expired - Lifetime
- 1989-08-11 MX MX1716989A patent/MX17169A/es unknown
- 1989-08-11 RO RO141245A patent/RO108453B1/ro unknown
- 1989-08-11 CA CA000608083A patent/CA1341325C/en not_active Expired - Lifetime
- 1989-08-12 KR KR1019890011503A patent/KR930002729B1/ko not_active Expired - Lifetime
- 1989-08-12 CN CN89106679A patent/CN1029231C/zh not_active Expired - Lifetime
- 1989-08-14 DD DD89331760A patent/DD284010A5/de not_active IP Right Cessation
1992
- 1992-03-05 RU SU925010979A patent/RU2095358C1/ru active
1993
- 1993-03-04 US US08/026,671 patent/US5364938A/en not_active Expired - Lifetime
- 1993-11-15 LV LVP-93-1223A patent/LV10714B/lv unknown
1994
- 1994-12-12 JP JP6307468A patent/JP2713394B2/ja not_active Expired - Lifetime
1995
- 1995-06-26 HU HU95P/P00436P patent/HU211511A9/hu unknown
1997
- 1997-09-05 CY CY196897A patent/CY1968A/xx unknown

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Also Published As

Publication number	Publication date
AU3893089A (en)	1990-03-22
KR930002729B1 (ko)	1993-04-09
SK476189A3 (en)	2000-07-11
FI893809L (fi)	1990-02-14
PT91440A (pt)	1990-03-08
CZ284318B6 (cs)	1998-10-14
IE61412B1 (en)	1994-11-02
NO174101C (no)	1994-03-16
MX17169A (es)	1993-08-01
NO893248D0 (no)	1989-08-11
PL163756B1 (pl)	1994-04-29
RU1836366C (ru)	1993-08-23
PL162953B1 (pl)	1994-01-31
DE68913105D1 (de)	1994-03-24
RO108453B1 (ro)	1994-05-31
RU2095358C1 (ru)	1997-11-10
IN175438B (es)	1995-06-17
DK394589D0 (da)	1989-08-11
HK1000320A1 (en)	1998-02-27
BG89519A (bg)	1993-12-24
HUT52089A (en)	1990-06-28
CZ476189A3 (cs)	1998-09-16
NO174101B (no)	1993-12-06
EP0357241B1 (en)	1994-02-16
IS1586B (is)	1996-03-01
CN1040795A (zh)	1990-03-28
HU205348B (en)	1992-04-28
DK172471B1 (da)	1998-09-07
HU211511A9 (en)	1995-11-28
IS3499A7 (is)	1990-02-14
AP8900135A0 (en)	1989-10-31
IL91231A0 (en)	1990-03-19
EP0357241A1 (en)	1990-03-07
CY1968A (en)	1997-09-05
FI96859B (fi)	1996-05-31
JPH07173154A (ja)	1995-07-11
PE1591A1 (es)	1991-03-16
ES2062009T3 (es)	1994-12-16
LV10714A (lv)	1995-06-20
OA09126A (fr)	1991-10-31
LV10714B (en)	1995-12-20
AR246963A1 (es)	1994-10-31
MY105092A (en)	1994-08-30
CN1029231C (zh)	1995-07-05
IE892582L (en)	1990-02-13
MA21610A1 (fr)	1990-04-01
AU602638B2 (en)	1990-10-18
JPH0786100B2 (ja)	1995-09-20
SK280775B6 (sk)	2000-07-11
JP2713394B2 (ja)	1998-02-16
DK394589A (da)	1990-02-14
NO893248L (no)	1990-02-14
FI96859C (fi)	1996-09-10
KR900003157A (ko)	1990-03-23
NZ230283A (en)	1991-02-26
ES2062009T4 (es)	2006-07-01
IL91231A (en)	1994-08-26
JPH02104583A (ja)	1990-04-17
BG60865B1 (bg)	1996-05-31
PT91440B (pt)	1995-05-04
CA1341325C (en)	2001-12-11
DD284010A5 (de)	1990-10-31
US5364938A (en)	1994-11-15
DE68913105T2 (de)	1994-05-26
YU47093B (sh)	1994-12-28
US5116844A (en)	1992-05-26
YU158789A (en)	1991-04-30
ZA896151B (en)	1991-03-27
GB8819308D0 (en)	1988-09-14
FI893809A0 (fi)	1989-08-11

Publication	Publication Date	Title
US5116844A (en)	1992-05-26	Triazole antifungal agents
US5567817A (en)	1996-10-22	Triazole antifungal agents
US5278175A (en)	1994-01-11	Triazole antifungal agents
EP0115400B1 (en)	1986-03-26	Triazole antifungal agents
US4737508A (en)	1988-04-12	1-aryl-1-(1H-azol-1-ylalkyl)-1,3-dihydroisobenzofurans, related derivatives and pharmaceutical compositions thereof useful as antifungals
US5206364A (en)	1993-04-27	Triazole antifungal agents
JPH10158167A (ja)	1998-06-16	トリアゾール誘導体を含有する医薬
JP2902345B2 (ja)	1999-06-07	トリアゾール抗真菌剤
US4877801A (en)	1989-10-31	1-Aryl-1-(1H-azol-1-ylalkyl)-1,3-dihydroisobenzofurans, related derivatives and pharmaceutical compositions thereof useful as antifungals
US4925857A (en)	1990-05-15	Pyridinyl-1H-pyrazole-1-alkanamides as antiarrhythmic agents
IL106262A (en)	1996-01-19	Intermediates to triazole antifungal agents
HK1000320B (en)	1998-02-27	Triazole antifungal agents
JP2887523B2 (ja)	1999-04-26	新規なトリアゾール誘導体およびその塩