NO319760B1 - Vannloselige azoler som bredspektrede antifungale midler, deres fremstilling og anvendelse samt farmasoytiske sammensetninger omfattende dem - Google Patents
Vannloselige azoler som bredspektrede antifungale midler, deres fremstilling og anvendelse samt farmasoytiske sammensetninger omfattende dem Download PDFInfo
- Publication number
- NO319760B1 NO319760B1 NO20005713A NO20005713A NO319760B1 NO 319760 B1 NO319760 B1 NO 319760B1 NO 20005713 A NO20005713 A NO 20005713A NO 20005713 A NO20005713 A NO 20005713A NO 319760 B1 NO319760 B1 NO 319760B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- triazol
- amino
- piperazinyl
- formula
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 229940121375 antifungal agent Drugs 0.000 title description 29
- 239000003429 antifungal agent Substances 0.000 title description 27
- 150000003851 azoles Chemical class 0.000 title description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 170
- 150000001875 compounds Chemical class 0.000 claims description 161
- -1 hydroxy, mercapto Chemical class 0.000 claims description 145
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 86
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000001475 halogen functional group Chemical group 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 206010017533 Fungal infection Diseases 0.000 claims description 10
- 208000031888 Mycoses Diseases 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
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- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005002 aryl methyl group Chemical group 0.000 claims description 4
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- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
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- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
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- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- WMZZTYIRJLUTIN-UHFFFAOYSA-N n-(1,4-dioxaspiro[4.5]decan-8-ylamino)formamide Chemical compound C1CC(NNC=O)CCC21OCCO2 WMZZTYIRJLUTIN-UHFFFAOYSA-N 0.000 description 1
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- WWJFFVUVFNBJTN-UHFFFAOYSA-N neopolyoxin C Natural products C=1C=C(O)C=NC=1C(O)C(C)C(N)C(=O)NC(C(O)=O)C(C(C1O)O)OC1N1C=CC(=O)NC1=O WWJFFVUVFNBJTN-UHFFFAOYSA-N 0.000 description 1
- WWJFFVUVFNBJTN-VHDFTHOZSA-N nikkomycin Z Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@H]2O)O)[C@H](NC(=O)[C@@H](N)[C@H](C)[C@H](O)C=2N=CC(O)=CC=2)C(O)=O)C=CC(=O)NC1=O WWJFFVUVFNBJTN-VHDFTHOZSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 108010058641 papulacandins Proteins 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000001814 pectin Chemical class 0.000 description 1
- 229920001277 pectin Chemical class 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NTGBUUXKGAZMSE-UHFFFAOYSA-N phenyl n-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]carbamate Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(NC(=O)OC=3C=CC=CC=3)=CC=2)CC1 NTGBUUXKGAZMSE-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 230000002265 prevention Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- JADFCQKRKICRKI-UHFFFAOYSA-N quinoline;sulfane Chemical compound S.N1=CC=CC2=CC=CC=C21 JADFCQKRKICRKI-UHFFFAOYSA-N 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- JTDQWSANBKDIGJ-UHFFFAOYSA-N tert-butyl n-benzyl-n-[3-(methylamino)butan-2-yl]carbamate Chemical compound CNC(C)C(C)N(C(=O)OC(C)(C)C)CC1=CC=CC=C1 JTDQWSANBKDIGJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000004879 turbidimetry Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- 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
-
- 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
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98201588A EP0957101A1 (de) | 1998-05-14 | 1998-05-14 | Wasserlösliche Azole als Breitspektrum-antifungus |
| PCT/EP1999/003243 WO1999058530A1 (en) | 1998-05-14 | 1999-05-06 | Water soluble azoles as broad-spectrum antifungals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20005713D0 NO20005713D0 (no) | 2000-11-13 |
| NO20005713L NO20005713L (no) | 2001-01-11 |
| NO319760B1 true NO319760B1 (no) | 2005-09-12 |
Family
ID=8233724
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20005712A NO319851B1 (no) | 1998-05-14 | 2000-11-13 | Vannloselige azoler som bredspektrede antifungale midler |
| NO20005713A NO319760B1 (no) | 1998-05-14 | 2000-11-13 | Vannloselige azoler som bredspektrede antifungale midler, deres fremstilling og anvendelse samt farmasoytiske sammensetninger omfattende dem |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20005712A NO319851B1 (no) | 1998-05-14 | 2000-11-13 | Vannloselige azoler som bredspektrede antifungale midler |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US6384030B1 (de) |
| EP (3) | EP0957101A1 (de) |
| JP (2) | JP2002514646A (de) |
| KR (2) | KR100593395B1 (de) |
| CN (2) | CN1137118C (de) |
| AR (2) | AR016482A1 (de) |
| AT (2) | ATE238296T1 (de) |
| AU (2) | AU751135B2 (de) |
| BG (2) | BG64388B1 (de) |
| BR (2) | BR9911057A (de) |
| CA (2) | CA2331187C (de) |
| CO (1) | CO5021227A1 (de) |
| CZ (2) | CZ298702B6 (de) |
| DE (2) | DE69902461T2 (de) |
| DK (1) | DK1077976T3 (de) |
| EE (2) | EE04311B1 (de) |
| ES (2) | ES2198915T3 (de) |
| HK (2) | HK1033312A1 (de) |
| HR (2) | HRP20000741B1 (de) |
| HU (2) | HUP0103536A3 (de) |
| IL (2) | IL139649A (de) |
| MY (2) | MY122147A (de) |
| NO (2) | NO319851B1 (de) |
| NZ (2) | NZ507965A (de) |
| PL (2) | PL194085B1 (de) |
| PT (1) | PT1077976E (de) |
| SI (1) | SI1077976T1 (de) |
| SK (2) | SK286156B6 (de) |
| TR (2) | TR200003323T2 (de) |
| TW (2) | TWI259835B (de) |
| WO (2) | WO1999058530A1 (de) |
| ZA (2) | ZA200007173B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0957101A1 (de) * | 1998-05-14 | 1999-11-17 | Janssen Pharmaceutica N.V. | Wasserlösliche Azole als Breitspektrum-antifungus |
| AU3402301A (en) * | 2000-03-07 | 2001-09-17 | Ranbaxy Laboratories Limited | Azole compounds as therapeutic agents for fungal infections |
| EP1413301A1 (de) * | 2002-10-24 | 2004-04-28 | Bayer CropScience SA | Antimykotische Medikamente auf der Basis von Arylamidinderivaten |
| ITMI20032020A1 (it) * | 2003-10-17 | 2005-04-18 | Italfarmaco Spa | Nuovi agenti antifungini azolici con diminuita interazione con i citocromi metabolici |
| AR052342A1 (es) * | 2004-12-21 | 2007-03-14 | Janssen Pharmaceutica Nv | Derivados sustituidos de triazolona,tetrazolona e imidazolona con actividad selectiva antagonista de alfa2c-adenoreceptores |
| WO2011144653A1 (en) * | 2010-05-19 | 2011-11-24 | Sandoz Ag | Process for the preparation of chiral triazolones |
| US11028078B2 (en) * | 2011-09-07 | 2021-06-08 | The Johns Hopkins University | Itraconazole analogs and use thereof |
| US9346791B2 (en) | 2011-09-07 | 2016-05-24 | The Johns Hopkins University | Itraconazole analogs and use thereof |
| US9663499B2 (en) * | 2013-06-07 | 2017-05-30 | The California Institute For Biomedical Research | Small molecule inhibitors of fibrosis |
| WO2016087878A1 (en) | 2014-12-05 | 2016-06-09 | Pulmocide Limited | Antimycotic compound |
| WO2016094570A1 (en) * | 2014-12-10 | 2016-06-16 | The California Institute For Biomedical Research | Small molecule inhibitors of fibrosis |
| DK3298006T3 (da) | 2015-05-21 | 2020-03-30 | Pulmocide Ltd | Antifungal 4-(4-(4-(((3r,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorphenyl)tetrahydrofuran-3-yl)methoxy)-3-methylphenyl)piperazin-1-yl)-n-(2-hydroxycyclohexyl)benzamid eller et farmaceutisk acceptabelt salt deraf |
| CN105237392B (zh) * | 2015-11-24 | 2017-12-12 | 辽宁渤大化工有限公司 | 芳烷基水杨酸及其衍生物的制备方法 |
| AU2018321287A1 (en) | 2017-08-20 | 2020-04-02 | University Of Connecticut | Azole analogues and methods of use thereof |
| CN111138421A (zh) * | 2019-12-26 | 2020-05-12 | 上海英诺富成生物科技有限公司 | 抗真菌水溶性化合物及其制备方法与应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| PL172358B1 (en) * | 1992-03-18 | 1997-09-30 | Janssen Pharmaceutica Nv | Stereoisomeric form of itraconazole or saperconazole and method of obtaining same |
| AU681753B2 (en) * | 1993-12-21 | 1997-09-04 | Merck Sharp & Dohme Corp. | Tetrahydrofuran antifungals |
| NZ278882A (en) * | 1994-01-24 | 1997-06-24 | Janssen Pharmaceutica Nv | Piperazine-containing azole antifungal compounds |
| FI98688C (fi) * | 1994-07-20 | 1997-07-25 | Nokia Telecommunications Oy | Menetelmä lyhytsanomalähetyksen käynnistämiseksi solukkoradiojärjestelmässä, solukkoradiojärjestelmä sekä solukkoradiojärjestelmän tilaajarekisteri |
| ATE240319T1 (de) * | 1995-06-02 | 2003-05-15 | Schering Corp | Antifungale tetrahydrofurane |
| WO1997000255A1 (en) * | 1995-06-19 | 1997-01-03 | Schering Corporation | Tetrahydrofuran antifungals |
| DE69824834T2 (de) | 1997-02-11 | 2005-07-21 | Janssen Pharmaceutica N.V. | Azole enthaltende antifungale aminosäure-ester |
| EP0957101A1 (de) * | 1998-05-14 | 1999-11-17 | Janssen Pharmaceutica N.V. | Wasserlösliche Azole als Breitspektrum-antifungus |
-
1998
- 1998-05-14 EP EP98201588A patent/EP0957101A1/de not_active Withdrawn
-
1999
- 1999-05-06 WO PCT/EP1999/003243 patent/WO1999058530A1/en active IP Right Grant
- 1999-05-06 PT PT99926304T patent/PT1077976E/pt unknown
- 1999-05-06 IL IL13964999A patent/IL139649A/en not_active IP Right Cessation
- 1999-05-06 EP EP99924942A patent/EP1077975B1/de not_active Expired - Lifetime
- 1999-05-06 JP JP2000548334A patent/JP2002514646A/ja active Pending
- 1999-05-06 SK SK1681-2000A patent/SK286156B6/sk not_active IP Right Cessation
- 1999-05-06 AU AU41417/99A patent/AU751135B2/en not_active Ceased
- 1999-05-06 EP EP99926304A patent/EP1077976B1/de not_active Expired - Lifetime
- 1999-05-06 ES ES99924942T patent/ES2198915T3/es not_active Expired - Lifetime
- 1999-05-06 DE DE69902461T patent/DE69902461T2/de not_active Expired - Lifetime
- 1999-05-06 PL PL99344047A patent/PL194085B1/pl unknown
- 1999-05-06 IL IL13964799A patent/IL139647A0/xx not_active IP Right Cessation
- 1999-05-06 TR TR2000/03323T patent/TR200003323T2/xx unknown
- 1999-05-06 WO PCT/EP1999/003242 patent/WO1999058529A1/en active IP Right Grant
- 1999-05-06 AT AT99924942T patent/ATE238296T1/de not_active IP Right Cessation
- 1999-05-06 CZ CZ20004109A patent/CZ298702B6/cs not_active IP Right Cessation
- 1999-05-06 CZ CZ20004108A patent/CZ299481B6/cs not_active IP Right Cessation
- 1999-05-06 JP JP2000548333A patent/JP2002514645A/ja active Pending
- 1999-05-06 NZ NZ507965A patent/NZ507965A/en not_active IP Right Cessation
- 1999-05-06 NZ NZ507966A patent/NZ507966A/xx not_active IP Right Cessation
- 1999-05-06 BR BR9911057-1A patent/BR9911057A/pt not_active Application Discontinuation
- 1999-05-06 CA CA002331187A patent/CA2331187C/en not_active Expired - Fee Related
- 1999-05-06 EE EEP200000657A patent/EE04311B1/xx not_active IP Right Cessation
- 1999-05-06 PL PL99344037A patent/PL194086B1/pl unknown
- 1999-05-06 DK DK99926304T patent/DK1077976T3/da active
- 1999-05-06 CA CA002331141A patent/CA2331141C/en not_active Expired - Fee Related
- 1999-05-06 ES ES99926304T patent/ES2182531T3/es not_active Expired - Lifetime
- 1999-05-06 AU AU43615/99A patent/AU758876B2/en not_active Ceased
- 1999-05-06 AT AT99926304T patent/ATE221884T1/de active
- 1999-05-06 CN CNB998059560A patent/CN1137118C/zh not_active Expired - Fee Related
- 1999-05-06 CN CNB998060690A patent/CN1135229C/zh not_active Expired - Fee Related
- 1999-05-06 KR KR1020007009640A patent/KR100593395B1/ko active IP Right Grant
- 1999-05-06 SK SK1682-2000A patent/SK285763B6/sk not_active IP Right Cessation
- 1999-05-06 US US09/700,251 patent/US6384030B1/en not_active Expired - Lifetime
- 1999-05-06 SI SI9930131T patent/SI1077976T1/xx unknown
- 1999-05-06 HU HU0103536A patent/HUP0103536A3/hu unknown
- 1999-05-06 BR BR9910448-2A patent/BR9910448A/pt not_active Application Discontinuation
- 1999-05-06 DE DE69907171T patent/DE69907171T2/de not_active Expired - Lifetime
- 1999-05-06 US US09/700,166 patent/US6448244B1/en not_active Expired - Lifetime
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- 1999-05-06 TR TR2000/03322T patent/TR200003322T2/xx unknown
- 1999-05-10 TW TW088107505A patent/TWI259835B/zh not_active IP Right Cessation
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- 1999-05-13 AR ARP990102276A patent/AR016482A1/es active IP Right Grant
- 1999-05-13 AR ARP990102270A patent/AR016480A1/es active IP Right Grant
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2000
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2001
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