AU776254B2 - Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders - Google Patents
Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders Download PDFInfo
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- AU776254B2 AU776254B2 AU12262/01A AU1226201A AU776254B2 AU 776254 B2 AU776254 B2 AU 776254B2 AU 12262/01 A AU12262/01 A AU 12262/01A AU 1226201 A AU1226201 A AU 1226201A AU 776254 B2 AU776254 B2 AU 776254B2
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- 208000003556 Dry Eye Syndromes Diseases 0.000 title claims description 46
- 206010013774 Dry eye Diseases 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 21
- 150000002442 hydroxyeicosatetraenoic acids Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 95
- 238000011282 treatment Methods 0.000 claims description 60
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 51
- 101150065749 Churc1 gene Proteins 0.000 claims description 51
- 102100038239 Protein Churchill Human genes 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 43
- 150000002148 esters Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000002091 cationic group Chemical group 0.000 claims description 15
- 150000001768 cations Chemical class 0.000 claims description 15
- 238000009736 wetting Methods 0.000 claims description 15
- -1 2,3,4,5 -tetrazol- 1 -yl Chemical group 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 150000007970 thio esters Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 208000024891 symptom Diseases 0.000 claims description 7
- 238000001356 surgical procedure Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 101150039033 Eci2 gene Proteins 0.000 claims 1
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- 229910020813 Sn-C Inorganic materials 0.000 claims 1
- 229910018732 Sn—C Inorganic materials 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 52
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 25
- 150000001299 aldehydes Chemical class 0.000 description 24
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
- 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 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 108010063954 Mucins Proteins 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 13
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 13
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000009833 condensation Methods 0.000 description 12
- 230000005494 condensation Effects 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 208000035475 disorder Diseases 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 description 9
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- 150000002367 halogens Chemical class 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000013459 approach Methods 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- LQZCYXCHWNQBKX-UHFFFAOYSA-N 1-dimethoxyphosphorylheptan-2-one Chemical compound CCCCCC(=O)CP(=O)(OC)OC LQZCYXCHWNQBKX-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 150000003904 phospholipids Chemical class 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 description 6
- 101000799461 Homo sapiens Thrombopoietin Proteins 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 102100034195 Thrombopoietin Human genes 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 238000013375 chromatographic separation Methods 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 6
- 229940051875 mucins Drugs 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000607 artificial tear Substances 0.000 description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 description 5
- 210000000981 epithelium Anatomy 0.000 description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
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- 239000003795 chemical substances by application Substances 0.000 description 4
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- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 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 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
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- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
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- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/04—Artificial tears; Irrigation solutions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16437199P | 1999-11-09 | 1999-11-09 | |
| US16438699P | 1999-11-09 | 1999-11-09 | |
| US16436999P | 1999-11-09 | 1999-11-09 | |
| US60/164386 | 1999-11-09 | ||
| US60/164369 | 1999-11-09 | ||
| US60/164371 | 1999-11-09 | ||
| PCT/US2000/029243 WO2001034551A1 (en) | 1999-11-09 | 2000-10-23 | Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1226201A AU1226201A (en) | 2001-06-06 |
| AU776254B2 true AU776254B2 (en) | 2004-09-02 |
Family
ID=27389011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU12262/01A Ceased AU776254B2 (en) | 1999-11-09 | 2000-10-23 | Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1228029B1 (https=) |
| JP (1) | JP4663193B2 (https=) |
| KR (1) | KR100781354B1 (https=) |
| CN (1) | CN1390191A (https=) |
| AR (1) | AR029769A1 (https=) |
| AT (2) | ATE271534T1 (https=) |
| AU (1) | AU776254B2 (https=) |
| BR (1) | BR0015424A (https=) |
| CA (1) | CA2386627C (https=) |
| DE (2) | DE60017810T2 (https=) |
| DK (1) | DK1228029T3 (https=) |
| ES (2) | ES2233921T3 (https=) |
| HK (1) | HK1045983B (https=) |
| MX (1) | MXPA02004704A (https=) |
| PL (1) | PL202040B1 (https=) |
| PT (2) | PT1418167E (https=) |
| TW (1) | TWI281395B (https=) |
| WO (1) | WO2001034551A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030109508A1 (en) * | 2001-10-11 | 2003-06-12 | Alcon, Inc. | Methods for treating dry eye |
| US8710252B2 (en) * | 2006-04-19 | 2014-04-29 | Cecil Pace-Asciak | Hepodxilin analog enantiomers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4906467A (en) | 1988-03-24 | 1990-03-06 | New York Medical College | Novel, long-duration treatment for glaucoma |
| US5696166A (en) * | 1995-10-31 | 1997-12-09 | Yanni; John M. | Compositions containing hydroxyeicosatetraenoic acid derivatives and methods of use in treating dry eye disorders |
-
2000
- 2000-10-23 PT PT04003004T patent/PT1418167E/pt unknown
- 2000-10-23 ES ES04003004T patent/ES2233921T3/es not_active Expired - Lifetime
- 2000-10-23 DE DE60017810T patent/DE60017810T2/de not_active Expired - Lifetime
- 2000-10-23 DK DK00973791T patent/DK1228029T3/da active
- 2000-10-23 WO PCT/US2000/029243 patent/WO2001034551A1/en not_active Ceased
- 2000-10-23 HK HK02107320.4A patent/HK1045983B/en not_active IP Right Cessation
- 2000-10-23 PL PL356105A patent/PL202040B1/pl unknown
- 2000-10-23 AU AU12262/01A patent/AU776254B2/en not_active Ceased
- 2000-10-23 MX MXPA02004704A patent/MXPA02004704A/es active IP Right Grant
- 2000-10-23 JP JP2001536502A patent/JP4663193B2/ja not_active Expired - Fee Related
- 2000-10-23 ES ES00973791T patent/ES2220559T3/es not_active Expired - Lifetime
- 2000-10-23 AT AT00973791T patent/ATE271534T1/de active
- 2000-10-23 DE DE60012358T patent/DE60012358T2/de not_active Expired - Lifetime
- 2000-10-23 CN CN00815492A patent/CN1390191A/zh active Pending
- 2000-10-23 CA CA002386627A patent/CA2386627C/en not_active Expired - Fee Related
- 2000-10-23 EP EP00973791A patent/EP1228029B1/en not_active Expired - Lifetime
- 2000-10-23 PT PT00973791T patent/PT1228029E/pt unknown
- 2000-10-23 KR KR1020027004596A patent/KR100781354B1/ko not_active Expired - Fee Related
- 2000-10-23 BR BR0015424-5A patent/BR0015424A/pt not_active Application Discontinuation
- 2000-10-23 AT AT04003004T patent/ATE287866T1/de active
- 2000-11-07 TW TW089123506A patent/TWI281395B/zh not_active IP Right Cessation
- 2000-11-08 AR ARP000105868A patent/AR029769A1/es not_active Application Discontinuation
Non-Patent Citations (3)
| Title |
|---|
| J. BIOCHEM, 314, 1996, PP 911-916 * |
| J. CHROMATOGRAPHY 416, 1987, PP 219-235 * |
| J. LIPID RESEARCH, 25, 1984, PP 1090-1095 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60017810D1 (de) | 2005-03-03 |
| CN1390191A (zh) | 2003-01-08 |
| ES2220559T3 (es) | 2004-12-16 |
| DE60012358D1 (de) | 2004-08-26 |
| PL356105A1 (en) | 2004-06-14 |
| BR0015424A (pt) | 2002-07-16 |
| PT1418167E (pt) | 2005-05-31 |
| AU1226201A (en) | 2001-06-06 |
| ATE287866T1 (de) | 2005-02-15 |
| ATE271534T1 (de) | 2004-08-15 |
| HK1045983A1 (en) | 2002-12-20 |
| PT1228029E (pt) | 2004-10-29 |
| KR100781354B1 (ko) | 2007-11-30 |
| TWI281395B (en) | 2007-05-21 |
| DE60017810T2 (de) | 2005-08-25 |
| MXPA02004704A (es) | 2004-09-10 |
| ES2233921T3 (es) | 2005-06-16 |
| KR20020040849A (ko) | 2002-05-30 |
| JP4663193B2 (ja) | 2011-03-30 |
| CA2386627A1 (en) | 2001-05-17 |
| CA2386627C (en) | 2008-12-23 |
| PL202040B1 (pl) | 2009-05-29 |
| DE60012358T2 (de) | 2005-02-17 |
| AR029769A1 (es) | 2003-07-16 |
| DK1228029T3 (da) | 2004-10-25 |
| JP2003528042A (ja) | 2003-09-24 |
| HK1045983B (en) | 2004-12-24 |
| WO2001034551A1 (en) | 2001-05-17 |
| HK1063623A1 (en) | 2005-01-07 |
| EP1228029B1 (en) | 2004-07-21 |
| EP1228029A1 (en) | 2002-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC | Change of applicant's name (sec. 104) |
Owner name: ALCON, INC. Free format text: FORMER NAME: ALCON UNIVERSAL LTD. |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |