SK10592003A3 - Protiplesňové triazolové činidlá rozpustné vo vode - Google Patents

Protiplesňové triazolové činidlá rozpustné vo vode Download PDF

Info

Publication number: SK10592003A3
Authority: SK; Slovakia
Prior art keywords: group; coch; substituent; same; acceptable salt
Prior art date: 2001-02-22

Application number

SK1059-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Makoto Mori

Yoshiko Kagoshima

Takuya Uchida

Toshiyuki Konosu

Takahiro Shibayama

Original Assignee

Sankyo Company Limited

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.)

2001-02-22

Filing date

2002-02-20

Publication date

2004-05-04

2002-02-20 Application filed by Sankyo Company Limited filed Critical Sankyo Company Limited

2004-05-04 Publication of SK10592003A3 publication Critical patent/SK10592003A3/sk

Links

150000003852 triazoles Chemical class 0.000 title description 3
230000000855 fungicidal effect Effects 0.000 title 1
239000000417 fungicide Substances 0.000 title 1
-1 triazole compound Chemical class 0.000 claims abstract description 439
150000001875 compounds Chemical class 0.000 claims abstract description 324
125000001424 substituent group Chemical group 0.000 claims abstract description 134
150000003839 salts Chemical class 0.000 claims abstract description 106
125000003118 aryl group Chemical group 0.000 claims abstract description 24
230000000843 anti-fungal effect Effects 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 134
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 78
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 54
125000005843 halogen group Chemical group 0.000 claims description 46
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 33
125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000001072 heteroaryl group Chemical group 0.000 claims description 24
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 14
125000001624 naphthyl group Chemical group 0.000 claims description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
125000002950 monocyclic group Chemical group 0.000 claims description 12
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 10
125000002619 bicyclic group Chemical group 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000001425 triazolyl group Chemical group 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000004957 naphthylene group Chemical group 0.000 claims description 4
125000000962 organic group Chemical group 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
241000287531 Psittacidae Species 0.000 claims 1
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 252
239000000203 mixture Substances 0.000 description 193
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 180
238000000034 method Methods 0.000 description 166
239000000243 solution Substances 0.000 description 162
239000002904 solvent Substances 0.000 description 152
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239000011541 reaction mixture Substances 0.000 description 114
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 107
238000006243 chemical reaction Methods 0.000 description 103
230000002829 reductive effect Effects 0.000 description 101
125000000446 sulfanediyl group Chemical group *S* 0.000 description 100
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 98
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
239000003480 eluent Substances 0.000 description 92
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 89
238000002329 infrared spectrum Methods 0.000 description 86
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 80
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 80
125000005336 allyloxy group Chemical group 0.000 description 79
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
238000010898 silica gel chromatography Methods 0.000 description 76
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 69
125000006239 protecting group Chemical group 0.000 description 67
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 66
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 55
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 48
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 44
239000010779 crude oil Substances 0.000 description 43
229910052739 hydrogen Inorganic materials 0.000 description 40
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 40
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
239000012044 organic layer Substances 0.000 description 36
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239000011780 sodium chloride Substances 0.000 description 34
239000012043 crude product Substances 0.000 description 32
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 31
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 30
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 30
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 28
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
238000003756 stirring Methods 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 25
239000002585 base Substances 0.000 description 25
238000007796 conventional method Methods 0.000 description 25
239000007858 starting material Substances 0.000 description 25
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 23
238000000605 extraction Methods 0.000 description 23
229910000030 sodium bicarbonate Inorganic materials 0.000 description 23
235000017557 sodium bicarbonate Nutrition 0.000 description 23
239000012312 sodium hydride Substances 0.000 description 23
229910000104 sodium hydride Inorganic materials 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 22
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
239000002253 acid Substances 0.000 description 21
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 21
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230000000052 comparative effect Effects 0.000 description 20
150000008282 halocarbons Chemical class 0.000 description 20
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
239000004215 Carbon black (E152) Substances 0.000 description 17
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 17
239000006185 dispersion Substances 0.000 description 17
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MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 15
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 15
235000019270 ammonium chloride Nutrition 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 15
238000004440 column chromatography Methods 0.000 description 15
229940125782 compound 2 Drugs 0.000 description 15
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 15
230000002441 reversible effect Effects 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
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238000001816 cooling Methods 0.000 description 13
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QBLCHHSGJTUNSJ-UHFFFAOYSA-N n-bis(prop-2-enoxy)phosphanyl-n-propan-2-ylpropan-2-amine Chemical compound C=CCOP(N(C(C)C)C(C)C)OCC=C QBLCHHSGJTUNSJ-UHFFFAOYSA-N 0.000 description 13
150000003536 tetrazoles Chemical class 0.000 description 13
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 12
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LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
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ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
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239000011734 sodium Substances 0.000 description 8
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125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 4
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
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229910052794 bromium Inorganic materials 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
229940125810 compound 20 Drugs 0.000 description 4
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ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
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150000004820 halides Chemical class 0.000 description 4
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WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
KPOORJWULWXLPB-UHFFFAOYSA-N 1-(cyclononen-1-yl)-3-diazocyclononene Chemical compound [N-]=[N+]=C1CCCCCCC(C=2CCCCCCCC=2)=C1 KPOORJWULWXLPB-UHFFFAOYSA-N 0.000 description 3
AGBWDHTZUCGTAI-UHFFFAOYSA-N 1-(cycloundecen-1-yl)-3-diazocycloundecene Chemical compound [N-]=[N+]=C1CCCCCCCCC(C=2CCCCCCCCCC=2)=C1 AGBWDHTZUCGTAI-UHFFFAOYSA-N 0.000 description 3
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 3
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GTOFKXZQQDSVFH-UHFFFAOYSA-N 2-benzylsuccinic acid Chemical compound OC(=O)CC(C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-UHFFFAOYSA-N 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
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YOZMWKCMXYWHLA-UHFFFAOYSA-N 6-(hydroxymethyl)-3h-2-benzofuran-1-one Chemical compound OCC1=CC=C2COC(=O)C2=C1 YOZMWKCMXYWHLA-UHFFFAOYSA-N 0.000 description 3
QSLQEQHQWZHUEW-UHFFFAOYSA-N 7-methyl-3h-2-benzofuran-1-one Chemical compound CC1=CC=CC2=C1C(=O)OC2 QSLQEQHQWZHUEW-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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206010017533 Fungal infection Diseases 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
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230000002411 adverse Effects 0.000 description 3
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125000004429 atom Chemical group 0.000 description 3
YTFJQDNGSQJFNA-UHFFFAOYSA-L benzyl phosphate Chemical compound [O-]P([O-])(=O)OCC1=CC=CC=C1 YTFJQDNGSQJFNA-UHFFFAOYSA-L 0.000 description 3
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
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229940125846 compound 25 Drugs 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
AKMLXRWHUXQISP-UHFFFAOYSA-L disodium;benzyl phosphate Chemical compound [Na+].[Na+].[O-]P([O-])(=O)OCC1=CC=CC=C1 AKMLXRWHUXQISP-UHFFFAOYSA-L 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
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230000002452 interceptive effect Effects 0.000 description 3
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238000004519 manufacturing process Methods 0.000 description 3
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239000002773 nucleotide Substances 0.000 description 1
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125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
125000005475 oxolanyl group Chemical group 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
201000000317 pneumocystosis Diseases 0.000 description 1
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NOTVAPJNGZMVSD-UHFFFAOYSA-N potassium oxide Chemical class [K]O[K] NOTVAPJNGZMVSD-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
OPAHEYNNJWPQPX-RCDICMHDSA-N ravuconazole Chemical compound C=1SC([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=1C1=CC=C(C#N)C=C1 OPAHEYNNJWPQPX-RCDICMHDSA-N 0.000 description 1
229950004154 ravuconazole Drugs 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
229910001958 silver carbonate Inorganic materials 0.000 description 1
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical class [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
229910001488 sodium perchlorate Inorganic materials 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
206010052366 systemic mycosis Diseases 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005458 thianyl group Chemical group 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
150000003657 tungsten Chemical class 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
229960004740 voriconazole Drugs 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- A61P31/10—Antimycotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- 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
- C07D403/14—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 three or more hetero rings
- 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
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
- 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
- C07D405/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)

SK1059-2003A 2001-02-22 2002-02-20 Protiplesňové triazolové činidlá rozpustné vo vode SK10592003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2001046890		2001-02-22
PCT/JP2002/001500 WO2002066465A1 (en)	2001-02-22	2002-02-20	Water-soluble triazole fungicide

Publications (1)

Publication Number	Publication Date
SK10592003A3 true SK10592003A3 (sk)	2004-05-04

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SK1059-2003A SK10592003A3 (sk)	2001-02-22	2002-02-20	Protiplesňové triazolové činidlá rozpustné vo vode

Country Status (22)

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US (1)	US7230023B2 (de)
EP (1)	EP1362856B1 (de)
KR (1)	KR100851800B1 (de)
CN (2)	CN100349569C (de)
AT (1)	ATE407932T1 (de)
AU (1)	AU2002234892C9 (de)
BR (1)	BR0207534A (de)
CA (1)	CA2439001C (de)
CZ (1)	CZ20032218A3 (de)
DE (1)	DE60228821D1 (de)
ES (1)	ES2314028T3 (de)
HU (1)	HUP0303249A3 (de)
IL (1)	IL157440A0 (de)
MX (1)	MXPA03007588A (de)
NO (1)	NO326520B1 (de)
NZ (1)	NZ527693A (de)
PL (1)	PL363523A1 (de)
PT (1)	PT1362856E (de)
RU (1)	RU2276670C2 (de)
SK (1)	SK10592003A3 (de)
WO (1)	WO2002066465A1 (de)
ZA (1)	ZA200306547B (de)

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2002
- 2002-02-02 HU HU0303249A patent/HUP0303249A3/hu unknown
- 2002-02-20 DE DE60228821T patent/DE60228821D1/de not_active Expired - Lifetime
- 2002-02-20 CN CNB2005100916023A patent/CN100349569C/zh not_active Expired - Fee Related
- 2002-02-20 CZ CZ20032218A patent/CZ20032218A3/cs unknown
- 2002-02-20 EP EP02701569A patent/EP1362856B1/de not_active Expired - Lifetime
- 2002-02-20 BR BR0207534-2A patent/BR0207534A/pt not_active IP Right Cessation
- 2002-02-20 WO PCT/JP2002/001500 patent/WO2002066465A1/ja not_active Ceased
- 2002-02-20 PT PT02701569T patent/PT1362856E/pt unknown
- 2002-02-20 RU RU2003125879/04A patent/RU2276670C2/ru not_active IP Right Cessation
- 2002-02-20 AT AT02701569T patent/ATE407932T1/de not_active IP Right Cessation
- 2002-02-20 CN CNB028084713A patent/CN100430390C/zh not_active Expired - Fee Related
- 2002-02-20 ES ES02701569T patent/ES2314028T3/es not_active Expired - Lifetime
- 2002-02-20 KR KR1020037011103A patent/KR100851800B1/ko not_active Expired - Fee Related
- 2002-02-20 AU AU2002234892A patent/AU2002234892C9/en not_active Ceased
- 2002-02-20 SK SK1059-2003A patent/SK10592003A3/sk unknown
- 2002-02-20 PL PL02363523A patent/PL363523A1/xx not_active IP Right Cessation
- 2002-02-20 IL IL15744002A patent/IL157440A0/xx unknown
- 2002-02-20 CA CA2439001A patent/CA2439001C/en not_active Expired - Fee Related
- 2002-02-20 NZ NZ527693A patent/NZ527693A/en unknown
- 2002-02-20 MX MXPA03007588A patent/MXPA03007588A/es active IP Right Grant
2003
- 2003-08-20 US US10/647,023 patent/US7230023B2/en not_active Expired - Fee Related
- 2003-08-21 NO NO20033723A patent/NO326520B1/no not_active IP Right Cessation
- 2003-08-21 ZA ZA200306547A patent/ZA200306547B/en unknown

Also Published As

Publication number	Publication date
IL157440A0 (en)	2004-03-28
HUP0303249A3 (en)	2007-03-28
US20040198790A1 (en)	2004-10-07
CN1503795A (zh)	2004-06-09
EP1362856B1 (de)	2008-09-10
CA2439001A1 (en)	2002-08-29
CN100430390C (zh)	2008-11-05
MXPA03007588A (es)	2003-12-04
CN1720913A (zh)	2006-01-18
EP1362856A1 (de)	2003-11-19
HUP0303249A2 (hu)	2004-01-28
CN100349569C (zh)	2007-11-21
NO20033723L (no)	2003-10-21
KR20030080030A (ko)	2003-10-10
RU2003125879A (ru)	2005-03-20
ES2314028T3 (es)	2009-03-16
PT1362856E (pt)	2008-12-16
RU2276670C2 (ru)	2006-05-20
NO20033723D0 (no)	2003-08-21
KR100851800B1 (ko)	2008-08-13
CZ20032218A3 (cs)	2004-03-17
WO2002066465A1 (en)	2002-08-29
PL363523A1 (en)	2004-11-29
EP1362856A4 (de)	2004-11-24
AU2002234892C1 (en)	2005-06-02
ZA200306547B (en)	2004-09-01
AU2002234892A1 (en)	2003-02-27
NO326520B1 (no)	2008-12-22
BR0207534A (pt)	2004-07-20
NZ527693A (en)	2004-10-29
AU2002234892B2 (en)	2005-01-06
US7230023B2 (en)	2007-06-12
ATE407932T1 (de)	2008-09-15
AU2002234892C9 (en)	2006-01-05
HK1058037A1 (en)	2004-04-30
CA2439001C (en)	2010-05-04
DE60228821D1 (de)	2008-10-23

Legal Events

Date	Code	Title	Description
2011-04-05	FB9A	Suspension of patent application procedure

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