AU3402301A - Azole compounds as therapeutic agents for fungal infections - Google Patents
Azole compounds as therapeutic agents for fungal infections Download PDFInfo
- Publication number
- AU3402301A AU3402301A AU34023/01A AU3402301A AU3402301A AU 3402301 A AU3402301 A AU 3402301A AU 34023/01 A AU34023/01 A AU 34023/01A AU 3402301 A AU3402301 A AU 3402301A AU 3402301 A AU3402301 A AU 3402301A
- Authority
- AU
- Australia
- Prior art keywords
- hydroxy
- group
- amino
- compound
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 208000031888 Mycoses Diseases 0.000 title claims description 23
- 206010017533 Fungal infection Diseases 0.000 title claims description 22
- 239000003814 drug Substances 0.000 title description 10
- 150000003851 azoles Chemical class 0.000 title description 7
- 229940124597 therapeutic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 307
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 196
- 229910052736 halogen Inorganic materials 0.000 claims description 150
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 150
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 141
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 140
- 150000002367 halogens Chemical class 0.000 claims description 137
- 125000003545 alkoxy group Chemical group 0.000 claims description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims description 131
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 125
- 125000001424 substituent group Chemical group 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 108
- -1 nitro, amino Chemical group 0.000 claims description 96
- 239000001257 hydrogen Substances 0.000 claims description 91
- 125000005843 halogen group Chemical group 0.000 claims description 80
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 61
- 150000002431 hydrogen Chemical group 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 39
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 36
- 125000004193 piperazinyl group Chemical group 0.000 claims description 35
- 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 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 29
- 125000002541 furyl group Chemical group 0.000 claims description 29
- 125000002883 imidazolyl group Chemical group 0.000 claims description 29
- 125000002971 oxazolyl group Chemical group 0.000 claims description 29
- 125000001544 thienyl group Chemical group 0.000 claims description 29
- 125000001425 triazolyl group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 24
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 24
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 22
- 125000004423 acyloxy group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 18
- 239000012312 sodium hydride Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 claims description 17
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 15
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 15
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000001439 semicarbazido group Chemical group [H]N([H])C(=O)N([H])N([H])* 0.000 claims description 14
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000002207 metabolite Substances 0.000 claims description 13
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 11
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 10
- 150000002924 oxiranes Chemical class 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 claims description 6
- UUMQGSBAGXRQJR-UHFFFAOYSA-N 5-methyl-1,2,4-triazol-3-one Chemical compound CC1=NC(=O)N=N1 UUMQGSBAGXRQJR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- QDXQWKIKBKUTRB-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)propan-1-one Chemical compound CC(Cl)C(=O)C1=CC=C(F)C=C1F QDXQWKIKBKUTRB-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 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 claims description 4
- SXAPWZGSXWDLTL-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-[4-[3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]oxyphenyl]piperazin-1-yl]urea Chemical compound C1=NC=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(C)OC(C=C1)=CC=C1N(CC1)CCN1NC(=O)NC1=CC=C(Cl)C=C1 SXAPWZGSXWDLTL-UHFFFAOYSA-N 0.000 claims description 4
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 4
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 238000006722 reduction reaction Methods 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- NCAOZZDODSUBRB-UHFFFAOYSA-N 1-(4-hydroxy-1-piperazin-1-ylcyclohexa-2,4-dien-1-yl)ethanone Chemical compound C1CNCCN1C1(C(=O)C)CC=C(O)C=C1 NCAOZZDODSUBRB-UHFFFAOYSA-N 0.000 claims description 3
- UIXQTZYZQHYHRL-UHFFFAOYSA-N 1-[[2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole Chemical compound FC1=CC(F)=CC=C1C1(CN2N=CN=C2)OC1 UIXQTZYZQHYHRL-UHFFFAOYSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 claims description 3
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 3
- DGWHDIYEULVUTH-UHFFFAOYSA-N 1-(1,2,4-triazol-1-yl)propan-2-ol Chemical compound CC(O)CN1C=NC=N1 DGWHDIYEULVUTH-UHFFFAOYSA-N 0.000 claims description 2
- RICSLPAUQXJPJI-UHFFFAOYSA-N 2-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-4-[4-[4-(3,4-difluorophenyl)piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound N1=CN(C=2C=CC(=CC=2)N2CCN(CC2)C=2C=C(F)C(F)=CC=2)C(=O)N1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RICSLPAUQXJPJI-UHFFFAOYSA-N 0.000 claims description 2
- JEQDSBVHLKBEIZ-UHFFFAOYSA-N 2-chloropropanoyl chloride Chemical compound CC(Cl)C(Cl)=O JEQDSBVHLKBEIZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 2
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 150000003349 semicarbazides Chemical class 0.000 claims description 2
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims 5
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 230000000875 corresponding effect Effects 0.000 claims 2
- 101100079846 Homo sapiens NEU1 gene Proteins 0.000 claims 1
- 102100028760 Sialidase-1 Human genes 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
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- 239000007787 solid Substances 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 239000012044 organic layer Substances 0.000 description 19
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
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- 239000002904 solvent Substances 0.000 description 14
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- 235000011152 sodium sulphate Nutrition 0.000 description 13
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
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- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 7
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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
-
- 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
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN198/DEL/2000 | 2000-03-07 | ||
| IN198DE2000 IN191188B (de) | 2000-03-07 | 2000-03-07 | |
| US09575578 | 2000-05-22 | ||
| US09/575,578 US6670363B1 (en) | 2000-03-07 | 2000-05-22 | Azole compounds as therapeutic agents for fungal infections |
| PCT/IB2001/000300 WO2001066551A2 (en) | 2000-03-07 | 2001-03-01 | Azole compounds as therapeutic agents for fungal infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU3402301A true AU3402301A (en) | 2001-09-17 |
Family
ID=26324879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU34023/01A Abandoned AU3402301A (en) | 2000-03-07 | 2001-03-01 | Azole compounds as therapeutic agents for fungal infections |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1278755A2 (de) |
| JP (1) | JP2004501867A (de) |
| AU (1) | AU3402301A (de) |
| CA (1) | CA2402345A1 (de) |
| NZ (1) | NZ521241A (de) |
| PL (1) | PL365072A1 (de) |
| RU (1) | RU2002126272A (de) |
| WO (1) | WO2001066551A2 (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002044160A1 (en) * | 2000-11-30 | 2002-06-06 | Senju Pharmaceutical Co., Ltd. | Pancreatitis remedies and medicines for prevention and therapy of reflux esophagitis |
| BR0116570A (pt) | 2000-12-26 | 2005-04-12 | Ranbaxy Lab Ltd | Compostos de azol e seu uso como agentes antifúngicos |
| KR100891887B1 (ko) | 2001-01-29 | 2009-04-03 | 시오노기세이야쿠가부시키가이샤 | 5-메틸-1-페닐-2-(1ｈ)-피리돈을 활성 성분으로서 함유하는의약 제제 |
| HUP0303249A3 (en) | 2001-02-22 | 2007-03-28 | Sankyo Co | Water-soluble triazole fungicide compounds and pharmaceutical compositions containing them |
| IN192526B (de) * | 2001-09-25 | 2004-04-24 | Ranbaxy Lab | |
| AU2002328176A1 (en) * | 2002-08-26 | 2004-03-11 | Ranbaxy Laboratories Limited | Azole derivatives as antifungal agents |
| EP1413301A1 (de) * | 2002-10-24 | 2004-04-28 | Bayer CropScience SA | Antimykotische Medikamente auf der Basis von Arylamidinderivaten |
| WO2007020888A1 (ja) | 2005-08-12 | 2007-02-22 | Takeda Pharmaceutical Company Limited | 脳・神経細胞保護剤および睡眠障害治療薬 |
| WO2012158844A1 (en) | 2011-05-17 | 2012-11-22 | Shionogi & Co., Ltd. | Heterocyclic compounds |
| BR112013033239A2 (pt) | 2011-06-22 | 2016-09-06 | Vyome Biosciences | pró-farmácos de conjugado baseado em atifungicos e antibacterianos |
| CN102617494B (zh) * | 2012-03-15 | 2014-10-29 | 南京工业大学 | 一种含有烯醚结构的三唑类化合物及其制备方法和用途 |
| MX2015016675A (es) | 2013-06-04 | 2016-07-15 | Vyome Biosciences Pvt Ltd | Particulas recubiertas y composiciones que comprenden las mismas. |
| ES2784307T3 (es) | 2014-01-29 | 2020-09-24 | Vyome Therapeutics Ltd | Besifloxacina para el tratamiento del acné resistente |
| CA2937365C (en) | 2016-03-29 | 2018-09-18 | F. Hoffmann-La Roche Ag | Granulate formulation of 5-methyl-1-phenyl-2-(1h)-pyridone and method of making the same |
| WO2018060070A1 (en) | 2016-09-29 | 2018-04-05 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW218017B (de) * | 1992-04-28 | 1993-12-21 | Takeda Pharm Industry Co Ltd | |
| CA2134417A1 (en) * | 1993-12-22 | 1995-06-23 | Katsumi Itoh | Optically active azole derivatives, their production and use |
| US5639754A (en) * | 1994-07-12 | 1997-06-17 | Janssen Pharmaceutica N.V. | Urea and thiourea derivatives of azolones |
| EP0957101A1 (de) * | 1998-05-14 | 1999-11-17 | Janssen Pharmaceutica N.V. | Wasserlösliche Azole als Breitspektrum-antifungus |
-
2001
- 2001-03-01 PL PL01365072A patent/PL365072A1/xx not_active Application Discontinuation
- 2001-03-01 WO PCT/IB2001/000300 patent/WO2001066551A2/en not_active Ceased
- 2001-03-01 RU RU2002126272/04A patent/RU2002126272A/ru not_active Application Discontinuation
- 2001-03-01 NZ NZ521241A patent/NZ521241A/en unknown
- 2001-03-01 AU AU34023/01A patent/AU3402301A/en not_active Abandoned
- 2001-03-01 JP JP2001565367A patent/JP2004501867A/ja active Pending
- 2001-03-01 CA CA002402345A patent/CA2402345A1/en not_active Abandoned
- 2001-03-01 EP EP01906061A patent/EP1278755A2/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| RU2002126272A (ru) | 2004-08-10 |
| EP1278755A2 (de) | 2003-01-29 |
| PL365072A1 (en) | 2004-12-27 |
| WO2001066551A8 (en) | 2003-06-26 |
| JP2004501867A (ja) | 2004-01-22 |
| WO2001066551A2 (en) | 2001-09-13 |
| NZ521241A (en) | 2004-02-27 |
| CA2402345A1 (en) | 2001-09-13 |
| WO2001066551A3 (en) | 2002-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK6 | Application lapsed section 142(2)(f)/reg. 8.3(3) - pct applic. not entering national phase |