ZA200109045B - Antifungal ethers. - Google Patents
Antifungal ethers. Download PDFInfo
- Publication number
- ZA200109045B ZA200109045B ZA200109045A ZA200109045A ZA200109045B ZA 200109045 B ZA200109045 B ZA 200109045B ZA 200109045 A ZA200109045 A ZA 200109045A ZA 200109045 A ZA200109045 A ZA 200109045A ZA 200109045 B ZA200109045 B ZA 200109045B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- 4alkyl
- compound
- compounds
- radical
- Prior art date
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- 229940121375 antifungal agent Drugs 0.000 title description 23
- 230000000843 anti-fungal effect Effects 0.000 title description 8
- 150000002170 ethers Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 95
- -1 hydroxy, mercapto Chemical class 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 206010017533 Fungal infection Diseases 0.000 claims description 12
- 208000031888 Mycoses Diseases 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000815 N-oxide group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000002950 monocyclic 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
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 2
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000850 2H-chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000007126 N-alkylation reaction Methods 0.000 claims description 2
- 238000010934 O-alkylation reaction Methods 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=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
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005879 dioxolanyl 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
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002265 phtalazinyl group Chemical group 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
- 125000003373 pyrazinyl group Chemical group 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
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl 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
- 125000003718 tetrahydrofuranyl group Chemical group 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
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001166 thiolanyl group Chemical group 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 238000000844 transformation Methods 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
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 2
- 241000237519 Bivalvia Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 235000020639 clam Nutrition 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 239000007962 solid dispersion Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 229920003169 water-soluble polymer Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000006104 solid solution Substances 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 229920000858 Cyclodextrin Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 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 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 150000004862 dioxolanes Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 150000003335 secondary amines Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 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 3
- 241000233866 Fungi Species 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000010195 Onychomycosis Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229940097362 cyclodextrins Drugs 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 229960004130 itraconazole Drugs 0.000 description 3
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
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- 230000003389 potentiating effect Effects 0.000 description 3
- 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 3
- 239000007787 solid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 201000005882 tinea unguium Diseases 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 201000007336 Cryptococcosis Diseases 0.000 description 2
- 241000221204 Cryptococcus neoformans Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 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 2
- 206010061598 Immunodeficiency Diseases 0.000 description 2
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- 230000000144 pharmacologic effect Effects 0.000 description 2
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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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
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|---|---|---|---|
| US13269999P | 1999-05-04 | 1999-05-04 |
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|---|---|
| ZA200109045B true ZA200109045B (en) | 2003-02-03 |
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| ZA200109045A ZA200109045B (en) | 1999-05-04 | 2001-11-01 | Antifungal ethers. |
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| US (1) | US6583136B1 (et) |
| EP (1) | EP1177192B1 (et) |
| JP (1) | JP4610744B2 (et) |
| KR (1) | KR20010094761A (et) |
| CN (1) | CN1349540A (et) |
| AT (1) | ATE234833T1 (et) |
| AU (1) | AU768491B2 (et) |
| BG (1) | BG105863A (et) |
| BR (1) | BR0010279A (et) |
| CA (1) | CA2372691C (et) |
| CZ (1) | CZ20013866A3 (et) |
| DE (1) | DE60001734T2 (et) |
| EA (1) | EA200101172A1 (et) |
| EE (1) | EE200100575A (et) |
| ES (1) | ES2194723T3 (et) |
| HR (1) | HRP20010763A2 (et) |
| HU (1) | HUP0200872A3 (et) |
| ID (1) | ID30409A (et) |
| IL (1) | IL146302A0 (et) |
| MX (1) | MXPA01011117A (et) |
| NO (1) | NO20015372L (et) |
| NZ (1) | NZ515118A (et) |
| PL (1) | PL351749A1 (et) |
| SK (1) | SK15772001A3 (et) |
| TR (1) | TR200103212T2 (et) |
| WO (1) | WO2000066580A2 (et) |
| ZA (1) | ZA200109045B (et) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2282463C1 (ru) * | 2005-11-07 | 2006-08-27 | Сергей Алексеевич Балехов | Способ изготовления дезинфицирующего средства |
| RU2727520C2 (ru) | 2014-11-21 | 2020-07-22 | Ф2Г Лимитед | Противогрибковые агенты |
| GB201609222D0 (en) | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459731A (en) | 1966-12-16 | 1969-08-05 | Corn Products Co | Cyclodextrin polyethers and their production |
| 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 |
| US4619931A (en) | 1983-02-28 | 1986-10-28 | Janssen Pharmaceutica, N.V. | [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles |
| CA1292472C (en) | 1985-12-03 | 1991-11-26 | Alfonsus Guilielmus Knaeps | Derivatives of ¬¬4-¬4-(4-phenyl-1-piperazinyl)- phenoxymethyl|-1,3-dioxolan-2-yl|methyl|-1h-imidazoles and 1h-1,2,4-triazoles |
| US4791111A (en) | 1985-12-23 | 1988-12-13 | Janssen Pharmaceutica, N.V. | [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles having anti-microbial properties |
| US5006513A (en) | 1987-11-09 | 1991-04-09 | Miles Inc. | Antimycotic compositions of nikkomycin compounds and azole antimycotica |
| CA1331757C (en) | 1988-02-29 | 1994-08-30 | Janssen Pharmaceutica Naamloze Vennootschap | 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols |
| CZ294823B6 (cs) | 1993-12-21 | 2005-03-16 | Schering Corporation | Fungicidní tetrahydrofurany |
| AR002751A1 (es) * | 1995-06-02 | 1998-04-29 | Schering Corp | Antifungicos de tetrahidrofurano, composiciones farmaceuticas que los contienen y el uso de los compuestos para preparar composiciones farmaceuticas utiles para el tratamiento de infecciones fungicas |
| WO1997000255A1 (en) | 1995-06-19 | 1997-01-03 | Schering Corporation | Tetrahydrofuran antifungals |
| EP0862463A1 (en) | 1995-11-23 | 1998-09-09 | Janssen Pharmaceutica N.V. | Solid mixtures of cyclodextrins prepared via melt-extrusion |
| JP4347911B2 (ja) * | 1997-02-11 | 2009-10-21 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | アミノ酸エステル含有アゾール抗真菌剤 |
| JPH10231296A (ja) * | 1997-02-19 | 1998-09-02 | Schering Plough Corp | テトラヒドロフラン抗真菌剤 |
| US5883097A (en) * | 1998-04-16 | 1999-03-16 | Schering Corporation | Soluble azole antifungal salt |
-
2000
- 2000-04-20 BR BR0010279-2A patent/BR0010279A/pt not_active Application Discontinuation
- 2000-04-20 TR TR2001/03212T patent/TR200103212T2/xx unknown
- 2000-04-20 SK SK1577-2001A patent/SK15772001A3/sk unknown
- 2000-04-20 JP JP2000615610A patent/JP4610744B2/ja not_active Expired - Fee Related
- 2000-04-20 AU AU45571/00A patent/AU768491B2/en not_active Ceased
- 2000-04-20 CZ CZ20013866A patent/CZ20013866A3/cs unknown
- 2000-04-20 PL PL00351749A patent/PL351749A1/xx not_active Application Discontinuation
- 2000-04-20 EE EEP200100575A patent/EE200100575A/et unknown
- 2000-04-20 ID IDW00200102392A patent/ID30409A/id unknown
- 2000-04-20 NZ NZ515118A patent/NZ515118A/xx unknown
- 2000-04-20 EA EA200101172A patent/EA200101172A1/ru unknown
- 2000-04-20 EP EP00927057A patent/EP1177192B1/en not_active Expired - Lifetime
- 2000-04-20 KR KR1020017010002A patent/KR20010094761A/ko not_active Application Discontinuation
- 2000-04-20 AT AT00927057T patent/ATE234833T1/de not_active IP Right Cessation
- 2000-04-20 CA CA002372691A patent/CA2372691C/en not_active Expired - Fee Related
- 2000-04-20 MX MXPA01011117A patent/MXPA01011117A/es not_active Application Discontinuation
- 2000-04-20 HU HU0200872A patent/HUP0200872A3/hu unknown
- 2000-04-20 DE DE60001734T patent/DE60001734T2/de not_active Expired - Lifetime
- 2000-04-20 ES ES00927057T patent/ES2194723T3/es not_active Expired - Lifetime
- 2000-04-20 WO PCT/EP2000/003740 patent/WO2000066580A2/en not_active Application Discontinuation
- 2000-04-20 US US09/980,560 patent/US6583136B1/en not_active Expired - Lifetime
- 2000-04-20 CN CN00807061A patent/CN1349540A/zh active Pending
- 2000-04-20 IL IL14630200A patent/IL146302A0/xx unknown
-
2001
- 2001-09-01 BG BG105863A patent/BG105863A/bg unknown
- 2001-10-19 HR HR20010763A patent/HRP20010763A2/hr not_active Application Discontinuation
- 2001-11-01 ZA ZA200109045A patent/ZA200109045B/en unknown
- 2001-11-02 NO NO20015372A patent/NO20015372L/no not_active Application Discontinuation
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