SK286156B6 - Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát - Google Patents
Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát Download PDFInfo
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- SK286156B6 SK286156B6 SK1681-2000A SK16812000A SK286156B6 SK 286156 B6 SK286156 B6 SK 286156B6 SK 16812000 A SK16812000 A SK 16812000A SK 286156 B6 SK286156 B6 SK 286156B6
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- 238000000034 method Methods 0.000 title claims abstract description 52
- 239000003814 drug Substances 0.000 title claims abstract description 11
- 230000008569 process Effects 0.000 title claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 150000003851 azoles Chemical class 0.000 title abstract description 3
- -1 1,2,3,4-tetrahydro-naphthalenyl Chemical group 0.000 claims abstract description 156
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims abstract description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 116
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000002883 imidazolyl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 13
- 150000007980 azole derivatives Chemical class 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 206010017533 Fungal infection Diseases 0.000 claims description 10
- 208000031888 Mycoses Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 15
- 150000002431 hydrogen Chemical group 0.000 abstract description 7
- 125000000815 N-oxide group Chemical group 0.000 abstract description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 92
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- 150000003254 radicals Chemical class 0.000 description 33
- 239000002904 solvent Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 229940121375 antifungal agent Drugs 0.000 description 27
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- 239000003429 antifungal agent Substances 0.000 description 25
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- 239000003480 eluent Substances 0.000 description 13
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- 229940097362 cyclodextrins Drugs 0.000 description 11
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- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 108010037444 diisopropylglutathione ester Proteins 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 241000233866 Fungi Species 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
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- 230000002538 fungal effect Effects 0.000 description 7
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
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- 229920003169 water-soluble polymer Polymers 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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Classifications
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- 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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 (en) | 1998-05-14 | 1998-05-14 | Water soluble azoles as broad-spectrum antifungals |
| PCT/EP1999/003242 WO1999058529A1 (en) | 1998-05-14 | 1999-05-06 | Water soluble azoles as broad-spectrum antifungals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK16812000A3 SK16812000A3 (sk) | 2001-08-06 |
| SK286156B6 true SK286156B6 (sk) | 2008-04-07 |
Family
ID=8233724
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1681-2000A SK286156B6 (sk) | 1998-05-14 | 1999-05-06 | Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát |
| SK1682-2000A SK285763B6 (sk) | 1998-05-14 | 1999-05-06 | Azol, spôsob jeho prípravy a medziprodukt na jehoprípravu, jeho použitie a farmaceutický prostriedok s jeho obsahom |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1682-2000A SK285763B6 (sk) | 1998-05-14 | 1999-05-06 | Azol, spôsob jeho prípravy a medziprodukt na jehoprípravu, jeho použitie a farmaceutický prostriedok s jeho obsahom |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6384030B1 (cs) |
| EP (3) | EP0957101A1 (cs) |
| JP (2) | JP2002514646A (cs) |
| KR (2) | KR100575147B1 (cs) |
| CN (2) | CN1137118C (cs) |
| AR (2) | AR016482A1 (cs) |
| AT (2) | ATE221884T1 (cs) |
| AU (2) | AU751135B2 (cs) |
| BG (2) | BG64388B1 (cs) |
| BR (2) | BR9910448A (cs) |
| CA (2) | CA2331187C (cs) |
| CO (1) | CO5021227A1 (cs) |
| CZ (2) | CZ298702B6 (cs) |
| DE (2) | DE69907171T2 (cs) |
| DK (1) | DK1077976T3 (cs) |
| EE (2) | EE04346B1 (cs) |
| ES (2) | ES2198915T3 (cs) |
| HR (2) | HRP20000741B1 (cs) |
| HU (2) | HUP0102031A3 (cs) |
| IL (2) | IL139647A0 (cs) |
| MY (2) | MY122147A (cs) |
| NO (2) | NO319760B1 (cs) |
| NZ (2) | NZ507965A (cs) |
| PL (2) | PL194085B1 (cs) |
| PT (1) | PT1077976E (cs) |
| SI (1) | SI1077976T1 (cs) |
| SK (2) | SK286156B6 (cs) |
| TR (2) | TR200003323T2 (cs) |
| TW (2) | TW572899B (cs) |
| WO (2) | WO1999058529A1 (cs) |
| ZA (2) | ZA200007173B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0957101A1 (en) * | 1998-05-14 | 1999-11-17 | Janssen Pharmaceutica N.V. | Water soluble azoles as broad-spectrum antifungals |
| JP2004501867A (ja) * | 2000-03-07 | 2004-01-22 | ランバクシー ラボラトリーズ リミテッド | 真菌感染症に対する治療薬としてのアゾール化合物 |
| EP1413301A1 (fr) * | 2002-10-24 | 2004-04-28 | Bayer CropScience SA | Médicaments antifongiques à base de dérivés d'arylamidine |
| 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 |
| MX342850B (es) * | 2010-05-19 | 2016-10-14 | Sandoz Ag | Proceso para la preparacion de triazolonas quirales. |
| 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 |
| PT3003038T (pt) * | 2013-06-07 | 2019-11-19 | Scripps Research Inst | Derivados 2h-1,2,3-triazólicos como inibidores de fibrose |
| AU2015356795B2 (en) | 2014-12-05 | 2020-01-16 | Pulmocide Limited | Antimycotic compound |
| KR102548066B1 (ko) * | 2014-12-10 | 2023-06-26 | 더 스크립스 리서치 인스티튜트 | 섬유증의 소분자 억제제 |
| AU2016263669B2 (en) * | 2015-05-21 | 2020-04-30 | Pulmocide Limited | Antifungal 4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4- difluorophenyl)tetrahydrofuran-3-yl) methoxy)-3-methylphenyl)piperazin-1-yl)-N- (2-hydroxycyclohexyl) benzamide, or a pharmaceutically acceptable salt thereof |
| 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 |
| EP3669191A4 (en) | 2017-08-20 | 2021-04-14 | University of Connecticut | NITROGEN-TYPE COMPOUND ANALOGUES AND THEIR METHODS OF USE |
| US12435067B2 (en) | 2019-08-09 | 2025-10-07 | University Of Connecticut | Truncated itraconazole 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 |
| AU665988B2 (en) * | 1992-03-18 | 1996-01-25 | Janssen Pharmaceutica N.V. | Itraconazole and saperconazole stereoisomers |
| JP2834889B2 (ja) * | 1993-12-21 | 1998-12-14 | シェーリング コーポレイション | テトラヒドロフラン抗真菌剤 |
| SG48386A1 (en) * | 1994-01-24 | 1998-04-17 | Janssen Pharmaceutica Nv | Watersoluble azole antifungals |
| 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 |
| ES2203707T3 (es) * | 1995-06-19 | 2004-04-16 | Schering Corporation | Antifungicos de tetrahidrofurano. |
| EP0958289B1 (en) * | 1997-02-11 | 2004-06-30 | Janssen Pharmaceutica N.V. | Amino acid ester containing azole antifungals |
| EP0957101A1 (en) * | 1998-05-14 | 1999-11-17 | Janssen Pharmaceutica N.V. | Water soluble azoles as broad-spectrum antifungals |
-
1998
- 1998-05-14 EP EP98201588A patent/EP0957101A1/en not_active Withdrawn
-
1999
- 1999-05-06 EP EP99926304A patent/EP1077976B1/en not_active Expired - Lifetime
- 1999-05-06 CN CNB998059560A patent/CN1137118C/zh not_active Expired - Fee Related
- 1999-05-06 US US09/700,251 patent/US6384030B1/en not_active Expired - Lifetime
- 1999-05-06 EE EEP200000651A patent/EE04346B1/xx not_active IP Right Cessation
- 1999-05-06 BR BR9910448-2A patent/BR9910448A/pt not_active Application Discontinuation
- 1999-05-06 DK DK99926304T patent/DK1077976T3/da active
- 1999-05-06 SK SK1681-2000A patent/SK286156B6/sk not_active IP Right Cessation
- 1999-05-06 PL PL99344047A patent/PL194085B1/pl unknown
- 1999-05-06 CA CA002331187A patent/CA2331187C/en not_active Expired - Fee Related
- 1999-05-06 DE DE69907171T patent/DE69907171T2/de not_active Expired - Lifetime
- 1999-05-06 HR HR20000741A patent/HRP20000741B1/xx not_active IP Right Cessation
- 1999-05-06 AT AT99926304T patent/ATE221884T1/de active
- 1999-05-06 EE EEP200000657A patent/EE04311B1/xx not_active IP Right Cessation
- 1999-05-06 US US09/700,166 patent/US6448244B1/en not_active Expired - Lifetime
- 1999-05-06 CZ CZ20004109A patent/CZ298702B6/cs not_active IP Right Cessation
- 1999-05-06 WO PCT/EP1999/003242 patent/WO1999058529A1/en not_active Ceased
- 1999-05-06 CN CNB998060690A patent/CN1135229C/zh not_active Expired - Fee Related
- 1999-05-06 HR HR20000740A patent/HRP20000740B1/xx not_active IP Right Cessation
- 1999-05-06 CZ CZ20004108A patent/CZ299481B6/cs not_active IP Right Cessation
- 1999-05-06 PT PT99926304T patent/PT1077976E/pt unknown
- 1999-05-06 HU HU0102031A patent/HUP0102031A3/hu unknown
- 1999-05-06 AT AT99924942T patent/ATE238296T1/de not_active IP Right Cessation
- 1999-05-06 PL PL99344037A patent/PL194086B1/pl unknown
- 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 TR TR2000/03323T patent/TR200003323T2/xx unknown
- 1999-05-06 ES ES99924942T patent/ES2198915T3/es not_active Expired - Lifetime
- 1999-05-06 KR KR1020007011624A patent/KR100575147B1/ko not_active Expired - Fee Related
- 1999-05-06 AU AU41417/99A patent/AU751135B2/en not_active Ceased
- 1999-05-06 IL IL13964799A patent/IL139647A0/xx not_active IP Right Cessation
- 1999-05-06 JP JP2000548334A patent/JP2002514646A/ja active Pending
- 1999-05-06 EP EP99924942A patent/EP1077975B1/en not_active Expired - Lifetime
- 1999-05-06 KR KR1020007009640A patent/KR100593395B1/ko not_active Expired - Fee Related
- 1999-05-06 DE DE69902461T patent/DE69902461T2/de not_active Expired - Lifetime
- 1999-05-06 WO PCT/EP1999/003243 patent/WO1999058530A1/en not_active Ceased
- 1999-05-06 IL IL13964999A patent/IL139649A/en not_active IP Right Cessation
- 1999-05-06 AU AU43615/99A patent/AU758876B2/en not_active Ceased
- 1999-05-06 ES ES99926304T patent/ES2182531T3/es not_active Expired - Lifetime
- 1999-05-06 CA CA002331141A patent/CA2331141C/en not_active Expired - Fee Related
- 1999-05-06 BR BR9911057-1A patent/BR9911057A/pt not_active Application Discontinuation
- 1999-05-06 SI SI9930131T patent/SI1077976T1/xx unknown
- 1999-05-06 JP JP2000548333A patent/JP2002514645A/ja active Pending
- 1999-05-06 HU HU0103536A patent/HUP0103536A3/hu unknown
- 1999-05-06 TR TR2000/03322T patent/TR200003322T2/xx unknown
- 1999-05-06 SK SK1682-2000A patent/SK285763B6/sk not_active IP Right Cessation
- 1999-05-10 TW TW088107504A patent/TW572899B/zh not_active IP Right Cessation
- 1999-05-10 TW TW088107505A patent/TWI259835B/zh not_active IP Right Cessation
- 1999-05-11 MY MYPI99001862A patent/MY122147A/en unknown
- 1999-05-11 MY MYPI99001861A patent/MY120248A/en unknown
- 1999-05-13 AR ARP990102276A patent/AR016482A1/es active IP Right Grant
- 1999-05-13 AR ARP990102270A patent/AR016480A1/es active IP Right Grant
- 1999-05-13 CO CO99029778A patent/CO5021227A1/es unknown
-
2000
- 2000-08-28 BG BG104717A patent/BG64388B1/bg unknown
- 2000-11-09 BG BG104933A patent/BG64954B1/bg unknown
- 2000-11-13 NO NO20005713A patent/NO319760B1/no not_active IP Right Cessation
- 2000-11-13 NO NO20005712A patent/NO319851B1/no not_active IP Right Cessation
- 2000-12-04 ZA ZA200007173A patent/ZA200007173B/en unknown
- 2000-12-13 ZA ZA200007459A patent/ZA200007459B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20090506 |