HRP921145A2 - Tri-substituted tetrahydrofuran antifungals - Google Patents
Tri-substituted tetrahydrofuran antifungals Download PDFInfo
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- HRP921145A2 HRP921145A2 HR921145A HRP921145A HRP921145A2 HR P921145 A2 HRP921145 A2 HR P921145A2 HR 921145 A HR921145 A HR 921145A HR P921145 A HRP921145 A HR P921145A HR P921145 A2 HRP921145 A2 HR P921145A2
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- Prior art keywords
- compound
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- formula
- triazol
- phenyl
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- 229940121375 antifungal agent Drugs 0.000 title claims abstract description 22
- -1 Tri-substituted tetrahydrofuran Chemical class 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 238000000034 method Methods 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 8
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 6
- 208000031888 Mycoses Diseases 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 241000124008 Mammalia Species 0.000 claims abstract 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 17
- 229920000858 Cyclodextrin Polymers 0.000 claims description 9
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical group CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 8
- 239000003429 antifungal agent Substances 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
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- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 2
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- 230000000843 anti-fungal effect Effects 0.000 abstract description 26
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- HUADITLKOCMHSB-AVQIMAJZSA-N 2-butan-2-yl-4-[4-[4-[4-[[(2s,4r)-2-(2,4-difluorophenyl)-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(C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3O[C@@](CN4N=CN=C4)(OC3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 HUADITLKOCMHSB-AVQIMAJZSA-N 0.000 description 7
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
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- OFVLGDICTFRJMM-WESIUVDSSA-N tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 description 1
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- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78535791A | 1991-10-30 | 1991-10-30 | |
| US90726292A | 1992-07-01 | 1992-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP921145A2 true HRP921145A2 (en) | 1994-08-31 |
Family
ID=27120397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR921145A HRP921145A2 (en) | 1991-10-30 | 1992-10-29 | Tri-substituted tetrahydrofuran antifungals |
Country Status (22)
| Country | Link |
|---|---|
| EP (2) | EP0610377B1 (fi) |
| JP (1) | JP3210017B2 (fi) |
| CN (1) | CN1037267C (fi) |
| AT (1) | ATE198888T1 (fi) |
| AU (1) | AU665218B2 (fi) |
| CA (1) | CA2122270C (fi) |
| CZ (1) | CZ102794A3 (fi) |
| DE (1) | DE69231661T2 (fi) |
| ES (1) | ES2153364T3 (fi) |
| FI (1) | FI941986A (fi) |
| HR (1) | HRP921145A2 (fi) |
| HU (1) | HUT70742A (fi) |
| IL (1) | IL103558A0 (fi) |
| MX (1) | MX9206222A (fi) |
| MY (1) | MY109529A (fi) |
| NO (1) | NO941589L (fi) |
| NZ (1) | NZ244910A (fi) |
| SG (1) | SG42920A1 (fi) |
| SI (1) | SI9200285A (fi) |
| SK (1) | SK48894A3 (fi) |
| WO (1) | WO1993009114A1 (fi) |
| YU (1) | YU94792A (fi) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5403937A (en) * | 1993-04-30 | 1995-04-04 | Schering Corporation | Process for preparing intermediates for the synthesis of antifungal agents |
| US5349099A (en) * | 1993-12-13 | 1994-09-20 | Schering Corporation | Process for preparing intermediates for the synthesis of antifungal agents |
| US5703079A (en) * | 1993-12-21 | 1997-12-30 | Schering Corporation | Tetrahydrofuran antifungals |
| US5693626A (en) * | 1993-12-21 | 1997-12-02 | Schering Corporation | Tetrahydrofuran antifungals |
| US5714490A (en) * | 1993-12-21 | 1998-02-03 | Schering Corporation | Tetrahydrofuran antifungals |
| US5661151A (en) * | 1993-12-21 | 1997-08-26 | Schering Corporation | Tetrahydrofuran antifungals |
| DK0736030T3 (da) * | 1993-12-21 | 2001-10-29 | Schering Corp | Fungicide tetrahydrofuraner |
| US5703236A (en) * | 1993-12-21 | 1997-12-30 | Schering Corporation | Tetrahydrofuran antifungals |
| US5710154A (en) * | 1993-12-21 | 1998-01-20 | Schering Corporation | Tetrahydrofuran antifungals |
| PL181947B1 (en) * | 1994-01-24 | 2001-10-31 | Janssen Pharmaceutica Nv | Water-soluble azole-type antimycotic agents |
| ES2158944T3 (es) * | 1994-04-19 | 2001-09-16 | Kanegafuchi Chemical Ind | Procedimiento para producir un 2-aril-3-aciloxi-1,2-propanodiol opticamente activo. |
| US5442093A (en) * | 1994-05-09 | 1995-08-15 | Schering Corporation | Process for preparing intermediates for the synthesis of antifungal agents |
| US5486625A (en) * | 1994-07-08 | 1996-01-23 | Schering Corporation | Process for the preparation of chiral intermediates useful for the synthesis of antifungal agents |
| EP0725146A4 (en) * | 1994-07-18 | 1998-12-23 | Daicel Chem | METHOD FOR PRODUCING OPTICALLY ACTIVE TRIAZOLE COMPOUNDS AND METHOD FOR RAZEMIZING OPTICALLY ACTIVE TRIAZOLE COMPOUNDS |
| US5616777A (en) * | 1995-04-19 | 1997-04-01 | Schering Corporation | Chiral hydrazine derivatives |
| US5625064A (en) * | 1995-04-19 | 1997-04-29 | Schering Corporation | Process for the preparation of triazolones |
| WO1996038443A1 (en) * | 1995-06-02 | 1996-12-05 | Schering Corporation | Tetrahydrofuran antifungals |
| AU6257396A (en) * | 1995-06-19 | 1997-01-15 | Schering Corporation | Tetrahydrofuran antifungals |
| US5698557A (en) * | 1995-06-19 | 1997-12-16 | Schering Corporation | Hydroxy-substituted antifungals |
| US5834472A (en) * | 1996-05-24 | 1998-11-10 | Schering Corporation | Antifungal composition with enhanced bioavailability |
| US5846971A (en) * | 1996-06-28 | 1998-12-08 | Schering Corporation | Oral antifungal composition |
| TW593312B (en) | 1997-07-11 | 2004-06-21 | Janssen Pharmaceutica Nv | 2,4,4-trisubstituted-1,3-dioxolane antifungals |
| WO1999018097A1 (en) * | 1997-10-07 | 1999-04-15 | Schering Corporation | Crystalline antifungal polymorph |
| CN1628119A (zh) * | 2002-04-12 | 2005-06-15 | 兰贝克赛实验室有限公司 | 作为抗真菌剂的2,2,4－三取代的四氢呋喃衍生物 |
| BR112012029228A2 (pt) | 2010-05-19 | 2021-08-03 | Sandoz Ag | processo para a preparação de um sal de cloreto de hidrogênio, sal de cloreto de hidrogênio, sal de cloreto de hidrogênio cristalino, uso de um sal e uso do processo |
| US9040539B2 (en) | 2010-05-19 | 2015-05-26 | Sandoz Ag | Process for the preparation of chiral triazolones |
| RU2588570C2 (ru) | 2010-05-19 | 2016-07-10 | Сандоз Аг | Способ получения хиральных гидразидов |
| RU2580318C2 (ru) | 2010-05-19 | 2016-04-10 | Сандоз Аг | Получение промежуточных продуктов для синтеза позаконазола |
| CN103635465A (zh) | 2011-06-16 | 2014-03-12 | 桑多斯股份公司 | 制备手性化合物的方法 |
| TN2015000519A1 (en) * | 2013-06-07 | 2017-04-06 | The California Institute For Biomedical Res | Small molecule inhibitors of fibrosis |
| CN106397417A (zh) * | 2016-08-30 | 2017-02-15 | 甘肃皓天化学科技有限公司 | 用于制备泊沙康唑的中间体的制备方法 |
Family Cites Families (13)
| 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 |
| 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 |
| DE3346123A1 (de) | 1983-12-21 | 1985-06-27 | Janssen Pharmaceutica, N.V., Beerse | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung |
| US4727064A (en) | 1984-04-25 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Pharmaceutical preparations containing cyclodextrin derivatives |
| DK354185A (da) * | 1984-08-31 | 1986-03-01 | Hoffmann La Roche | 1,3-dioxolanderivater |
| NZ223799A (en) * | 1987-03-25 | 1989-12-21 | Janssen Pharmaceutica Nv | Azolylmethyl-dioxolanylmethoxyphenyl-piperazinyl-phenyl-triazolones and antimicrobial compositions |
| US5006513A (en) | 1987-11-09 | 1991-04-09 | Miles Inc. | Antimycotic compositions of nikkomycin compounds and azole antimycotica |
| EP0386143A1 (en) | 1987-11-20 | 1990-09-12 | Schering Corporation | Tri- and tetra-substituted-oxetanes and tetrahydrofurans and intermediates thereof |
| US5002935A (en) | 1987-12-30 | 1991-03-26 | University Of Florida | Improvements in redox systems for brain-targeted drug delivery |
| CA1331757C (en) * | 1988-02-29 | 1994-08-30 | Janssen Pharmaceutica Naamloze Vennootschap | 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols |
| NZ233502A (en) * | 1989-06-09 | 1991-11-26 | Janssen Pharmaceutica Nv | 4-(1,2,4-triazole- or imidazole-phenyl-substituted) -1-(1,3-dioxolan-4-ylmethoxyphenyl) piperazine derivatives; preparatory processes: fungicidal and antiviral compositions |
| US5039676A (en) | 1990-05-11 | 1991-08-13 | Schering Corporation | Tri- and tetra-substituted-oxetanes and tetrahydrofurans and intermediates thereof |
| US20040220100A1 (en) | 2000-07-21 | 2004-11-04 | Essentia Biosystems, Inc. | Multi-component biological transport systems |
-
1992
- 1992-10-27 IL IL103558A patent/IL103558A0/xx unknown
- 1992-10-28 CZ CZ941027A patent/CZ102794A3/cs unknown
- 1992-10-28 SK SK488-94A patent/SK48894A3/sk unknown
- 1992-10-28 CA CA002122270A patent/CA2122270C/en not_active Expired - Lifetime
- 1992-10-28 DE DE69231661T patent/DE69231661T2/de not_active Expired - Lifetime
- 1992-10-28 MY MYPI92001943A patent/MY109529A/en unknown
- 1992-10-28 MX MX9206222A patent/MX9206222A/es unknown
- 1992-10-28 EP EP92923060A patent/EP0610377B1/en not_active Expired - Lifetime
- 1992-10-28 SG SG1996000735A patent/SG42920A1/en unknown
- 1992-10-28 HU HU9401256A patent/HUT70742A/hu unknown
- 1992-10-28 NZ NZ244910A patent/NZ244910A/en unknown
- 1992-10-28 ES ES92923060T patent/ES2153364T3/es not_active Expired - Lifetime
- 1992-10-28 AU AU29169/92A patent/AU665218B2/en not_active Ceased
- 1992-10-28 JP JP50846493A patent/JP3210017B2/ja not_active Expired - Fee Related
- 1992-10-28 AT AT92923060T patent/ATE198888T1/de active
- 1992-10-28 EP EP92118413A patent/EP0539938A1/en active Pending
- 1992-10-28 WO PCT/US1992/008981 patent/WO1993009114A1/en active IP Right Grant
- 1992-10-29 SI SI19929200285A patent/SI9200285A/sl unknown
- 1992-10-29 YU YU94792A patent/YU94792A/sh unknown
- 1992-10-29 CN CN92113399A patent/CN1037267C/zh not_active Expired - Fee Related
- 1992-10-29 HR HR921145A patent/HRP921145A2/hr not_active Application Discontinuation
-
1994
- 1994-04-29 NO NO941589A patent/NO941589L/no unknown
- 1994-04-29 FI FI941986A patent/FI941986A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP3210017B2 (ja) | 2001-09-17 |
| NO941589L (fi) | 1994-06-23 |
| CZ102794A3 (en) | 1995-03-15 |
| MY109529A (en) | 1997-02-28 |
| HU9401256D0 (en) | 1994-08-29 |
| EP0610377B1 (en) | 2001-01-24 |
| YU94792A (sh) | 1995-12-04 |
| FI941986A0 (fi) | 1994-04-29 |
| CN1037267C (zh) | 1998-02-04 |
| NZ244910A (en) | 1996-01-26 |
| SK48894A3 (en) | 1995-02-08 |
| EP0539938A1 (en) | 1993-05-05 |
| ES2153364T3 (es) | 2001-03-01 |
| WO1993009114A1 (en) | 1993-05-13 |
| SG42920A1 (en) | 1997-10-17 |
| NO941589D0 (fi) | 1994-04-29 |
| SI9200285A (en) | 1993-06-30 |
| DE69231661D1 (de) | 2001-03-01 |
| CA2122270A1 (en) | 1993-05-13 |
| HUT70742A (en) | 1995-10-30 |
| AU665218B2 (en) | 1995-12-21 |
| ATE198888T1 (de) | 2001-02-15 |
| DE69231661T2 (de) | 2001-08-02 |
| EP0610377A1 (en) | 1994-08-17 |
| IL103558A0 (en) | 1993-03-15 |
| AU2916992A (en) | 1993-06-07 |
| CN1073944A (zh) | 1993-07-07 |
| CA2122270C (en) | 2006-05-23 |
| MX9206222A (es) | 1993-04-01 |
| FI941986A (fi) | 1994-04-29 |
| JPH07500605A (ja) | 1995-01-19 |
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