SK150797A3 - Antifungal composition - Google Patents
Antifungal composition Download PDFInfo
- Publication number
- SK150797A3 SK150797A3 SK1507-97A SK150797A SK150797A3 SK 150797 A3 SK150797 A3 SK 150797A3 SK 150797 A SK150797 A SK 150797A SK 150797 A3 SK150797 A3 SK 150797A3
- Authority
- SK
- Slovakia
- Prior art keywords
- azole
- composition
- preparation
- terbinafine
- fungicidal
- Prior art date
Links
- 239000012871 anti-fungal composition Substances 0.000 title 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 112
- 229960004884 fluconazole Drugs 0.000 claims abstract description 33
- 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 claims abstract description 33
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims abstract description 25
- 229960002722 terbinafine Drugs 0.000 claims abstract description 24
- 230000002538 fungal effect Effects 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 17
- 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 claims abstract description 15
- 229960004130 itraconazole Drugs 0.000 claims abstract description 15
- 239000003112 inhibitor Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 30
- 241000222122 Candida albicans Species 0.000 claims description 22
- 206010017533 Fungal infection Diseases 0.000 claims description 19
- 230000000855 fungicidal effect Effects 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 14
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 12
- 208000031888 Mycoses Diseases 0.000 claims description 12
- 208000024386 fungal infectious disease Diseases 0.000 claims description 8
- 229940095731 candida albicans Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000003211 malignant effect Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- 241001337994 Cryptococcus <scale insect> Species 0.000 claims description 2
- 230000002238 attenuated effect Effects 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- -1 1-cyclopropyl-1-methylethyl Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract description 4
- 229940123185 Squalene epoxidase inhibitor Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 206010022998 Irritability Diseases 0.000 description 8
- 241000222178 Candida tropicalis Species 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 4
- 244000197813 Camelina sativa Species 0.000 description 4
- 241000725303 Human immunodeficiency virus Species 0.000 description 4
- 241000235645 Pichia kudriavzevii Species 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 206010022000 influenza Diseases 0.000 description 4
- 229960004125 ketoconazole Drugs 0.000 description 4
- 206010050346 Oropharyngeal candidiasis Diseases 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 206010007134 Candida infections Diseases 0.000 description 2
- 201000007336 Cryptococcosis Diseases 0.000 description 2
- 241000221204 Cryptococcus neoformans Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 108010017796 epoxidase Proteins 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 description 1
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- MPIPASJGOJYODL-SFHVURJKSA-N (R)-isoconazole Chemical compound ClC1=CC(Cl)=CC=C1[C@@H](OCC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 MPIPASJGOJYODL-SFHVURJKSA-N 0.000 description 1
- OCQPZTCGZAFWSG-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-2-(1,2,4-triazol-1-ylmethyl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)COC1=CC=C(Cl)C=C1 OCQPZTCGZAFWSG-UHFFFAOYSA-N 0.000 description 1
- AFNXATANNDIXLG-SFHVURJKSA-N 1-[(2r)-2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CS[C@H](C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 AFNXATANNDIXLG-SFHVURJKSA-N 0.000 description 1
- ZCJYUTQZBAIHBS-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)benzyl]oxy}ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC(SC=2C=CC=CC=2)=CC=1)CN1C=NC=C1 ZCJYUTQZBAIHBS-UHFFFAOYSA-N 0.000 description 1
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 description 1
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
- 208000008818 Chronic Mucocutaneous Candidiasis Diseases 0.000 description 1
- WHPAGCJNPTUGGD-UHFFFAOYSA-N Croconazole Chemical compound ClC1=CC=CC(COC=2C(=CC=CC=2)C(=C)N2C=NC=C2)=C1 WHPAGCJNPTUGGD-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
- 206010028080 Mucocutaneous candidiasis Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 229960003942 amphotericin b Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 229960002206 bifonazole Drugs 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 229960005074 butoconazole Drugs 0.000 description 1
- SWLMUYACZKCSHZ-UHFFFAOYSA-N butoconazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 SWLMUYACZKCSHZ-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960004022 clotrimazole Drugs 0.000 description 1
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960003913 econazole Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229960001274 fenticonazole Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229960004849 isoconazole Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940089474 lamisil Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229960002509 miconazole Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 229960003483 oxiconazole Drugs 0.000 description 1
- QRJJEGAJXVEBNE-MOHJPFBDSA-N oxiconazole Chemical compound ClC1=CC(Cl)=CC=C1CO\N=C(C=1C(=CC(Cl)=CC=1)Cl)\CN1C=NC=C1 QRJJEGAJXVEBNE-MOHJPFBDSA-N 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 150000003421 squalenes Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 229960002607 sulconazole Drugs 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960000580 terconazole Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9509631.9A GB9509631D0 (en) | 1995-05-12 | 1995-05-12 | Antifungal combination |
| PCT/EP1996/002022 WO1996035423A1 (en) | 1995-05-12 | 1996-05-10 | Antifungal composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK150797A3 true SK150797A3 (en) | 1998-05-06 |
Family
ID=10774361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1507-97A SK150797A3 (en) | 1995-05-12 | 1996-05-10 | Antifungal composition |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5985906A (hu) |
| EP (1) | EP0824350B1 (hu) |
| JP (1) | JPH11504931A (hu) |
| KR (1) | KR100443535B1 (hu) |
| CN (1) | CN1100539C (hu) |
| AT (1) | ATE246504T1 (hu) |
| AU (1) | AU712914B2 (hu) |
| CA (1) | CA2219651C (hu) |
| CY (1) | CY2496B1 (hu) |
| CZ (1) | CZ291144B6 (hu) |
| DE (1) | DE69629367T2 (hu) |
| DK (1) | DK0824350T3 (hu) |
| ES (1) | ES2205042T3 (hu) |
| FI (1) | FI120079B (hu) |
| GB (1) | GB9509631D0 (hu) |
| HK (1) | HK1016064A1 (hu) |
| HU (1) | HU224920B1 (hu) |
| IL (2) | IL118219A (hu) |
| MX (1) | MX9708699A (hu) |
| NO (1) | NO317030B1 (hu) |
| PL (1) | PL322749A1 (hu) |
| PT (1) | PT824350E (hu) |
| SK (1) | SK150797A3 (hu) |
| TW (1) | TW464492B (hu) |
| WO (1) | WO1996035423A1 (hu) |
| ZA (1) | ZA963754B (hu) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187757B1 (en) * | 1995-06-07 | 2001-02-13 | Ariad Pharmaceuticals, Inc. | Regulation of biological events using novel compounds |
| ES2219388T3 (es) * | 1999-08-24 | 2004-12-01 | Ariad Gene Therapeutics, Inc. | 28-epi-rapalogos. |
| US7067526B1 (en) | 1999-08-24 | 2006-06-27 | Ariad Gene Therapeutics, Inc. | 28-epirapalogs |
| GB0001315D0 (en) * | 2000-01-20 | 2000-03-08 | Novartis Ag | Organic compounds |
| GB0003932D0 (en) * | 2000-02-18 | 2000-04-12 | Novartis Ag | Pharmaceutical compositions |
| US6673373B2 (en) | 2001-02-01 | 2004-01-06 | Carlsbad Technology Inc. | Antifungal formulation and the methods for manufacturing and using the same |
| US7244703B2 (en) | 2001-06-22 | 2007-07-17 | Bentley Pharmaceuticals, Inc. | Pharmaceutical compositions and methods for peptide treatment |
| JP2006516548A (ja) | 2002-12-30 | 2006-07-06 | アンジオテック インターナショナル アクツィエン ゲゼルシャフト | 迅速ゲル化ポリマー組成物からの薬物送達法 |
| US7112561B2 (en) | 2003-12-08 | 2006-09-26 | Bentley Pharmaceuticals, Inc. | Pharmaceutical compositions and methods for insulin treatment |
| US7740875B2 (en) * | 2004-10-08 | 2010-06-22 | Mediquest Therapeutics, Inc. | Organo-gel formulations for therapeutic applications |
| US20060078580A1 (en) | 2004-10-08 | 2006-04-13 | Mediquest Therapeutics, Inc. | Organo-gel formulations for therapeutic applications |
| RU2396955C2 (ru) | 2005-04-07 | 2010-08-20 | Тояма Кемикал Ко., Лтд. | Фармацевтическая комбинация и способ применения противогрибкового средства в комбинации |
| DK2070536T3 (da) | 2006-10-06 | 2012-04-10 | Toyama Chemical Co Ltd | Farmaceutisk sammensætning med et phenylamidin-derivat og fremgangsmåde til anvendelse af den farmaceutiske sammensætning i kombination med et antifungalt middel |
| WO2008073863A2 (en) * | 2006-12-08 | 2008-06-19 | Auspex Pharmaceuticals, Inc. | Preparation and utility of substituted allylamines |
| US8921642B2 (en) | 2008-01-11 | 2014-12-30 | Massachusetts Eye And Ear Infirmary | Conditional-stop dimerizable caspase transgenic animals |
| CN105283553B (zh) | 2013-06-11 | 2021-06-25 | 克隆技术实验室有限公司 | 蛋白质富集的微泡及其制备和使用方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144346A (en) * | 1977-01-31 | 1979-03-13 | Janssen Pharmaceutica N.V. | Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles |
| US4218458A (en) * | 1978-06-23 | 1980-08-19 | Janssen Pharmaceutica, N.V. | Heterocyclic derivatives of (4-aryloxy-methyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles |
| GB2099818A (en) * | 1981-06-06 | 1982-12-15 | Pfizer Ltd | Triazoles |
| US4782059A (en) * | 1986-09-29 | 1988-11-01 | Merck & Co., Inc. | Method of controlling mycotic infections and compositions therefor |
| JP2581707B2 (ja) * | 1987-10-02 | 1997-02-12 | 科研製薬株式会社 | 抗真菌剤組成物 |
| CA2016738A1 (en) * | 1989-06-08 | 1990-12-08 | Philippe Guerry | Substituted aminoalkylbenzene derivatives |
| JPH0338521A (ja) * | 1989-07-05 | 1991-02-19 | Maruho Kk | 抗真菌性組成物 |
| JPH0338522A (ja) * | 1989-07-05 | 1991-02-19 | Maruho Kk | 抗真菌性組成物 |
| CA2020888A1 (en) * | 1989-07-27 | 1991-01-28 | Philippe Guerry | Substituted aminoalkoxybenzene derivatives |
| US5214046A (en) * | 1989-07-27 | 1993-05-25 | Hoffmann-La Roche Inc. | Substituted aminoalkoxybenzene anti-fungicidal compositions and use |
| CA2044533A1 (en) * | 1990-06-29 | 1991-12-30 | Philippe Guerry | Substituted aminoalkylbiphenyl derivatives |
| US5696164A (en) * | 1994-12-22 | 1997-12-09 | Johnson & Johnson Consumer Products, Inc. | Antifungal treatment of nails |
| JP3038521U (ja) | 1996-12-05 | 1997-06-20 | 啓次 小峰 | 排泄物一時保持具用の水溶繊維製ステック状吸液材 |
| JP3038522U (ja) | 1996-12-05 | 1997-06-20 | 秀俊 筬 | カード型紙箱ポプリ |
-
1995
- 1995-05-12 GB GBGB9509631.9A patent/GB9509631D0/en active Pending
-
1996
- 1996-05-10 KR KR1019970708050A patent/KR100443535B1/ko not_active IP Right Cessation
- 1996-05-10 IL IL11821996A patent/IL118219A/xx not_active IP Right Cessation
- 1996-05-10 HU HU9801140A patent/HU224920B1/hu not_active IP Right Cessation
- 1996-05-10 DE DE69629367T patent/DE69629367T2/de not_active Expired - Lifetime
- 1996-05-10 CA CA002219651A patent/CA2219651C/en not_active Expired - Fee Related
- 1996-05-10 SK SK1507-97A patent/SK150797A3/sk unknown
- 1996-05-10 PL PL96322749A patent/PL322749A1/xx unknown
- 1996-05-10 ES ES96919769T patent/ES2205042T3/es not_active Expired - Lifetime
- 1996-05-10 TW TW085105532A patent/TW464492B/zh active
- 1996-05-10 DK DK96919769T patent/DK0824350T3/da active
- 1996-05-10 MX MX9708699A patent/MX9708699A/es not_active IP Right Cessation
- 1996-05-10 IL IL11821995A patent/IL118219A0/xx unknown
- 1996-05-10 PT PT96919769T patent/PT824350E/pt unknown
- 1996-05-10 CZ CZ19973547A patent/CZ291144B6/cs not_active IP Right Cessation
- 1996-05-10 JP JP8533792A patent/JPH11504931A/ja active Pending
- 1996-05-10 EP EP96919769A patent/EP0824350B1/en not_active Expired - Lifetime
- 1996-05-10 US US08/952,288 patent/US5985906A/en not_active Expired - Fee Related
- 1996-05-10 WO PCT/EP1996/002022 patent/WO1996035423A1/en not_active Application Discontinuation
- 1996-05-10 AU AU58183/96A patent/AU712914B2/en not_active Ceased
- 1996-05-10 AT AT96919769T patent/ATE246504T1/de not_active IP Right Cessation
- 1996-05-10 ZA ZA9603754A patent/ZA963754B/xx unknown
- 1996-05-10 CN CN96193853A patent/CN1100539C/zh not_active Expired - Fee Related
-
1997
- 1997-09-26 FI FI973812A patent/FI120079B/fi not_active IP Right Cessation
- 1997-11-07 NO NO19975134A patent/NO317030B1/no not_active IP Right Cessation
-
1998
- 1998-12-10 HK HK98113058A patent/HK1016064A1/xx not_active IP Right Cessation
-
2004
- 2004-12-27 CY CY0400091A patent/CY2496B1/xx unknown
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