JP2005503354A5 - - Google Patents
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- Publication number
- JP2005503354A5 JP2005503354A5 JP2003500077A JP2003500077A JP2005503354A5 JP 2005503354 A5 JP2005503354 A5 JP 2005503354A5 JP 2003500077 A JP2003500077 A JP 2003500077A JP 2003500077 A JP2003500077 A JP 2003500077A JP 2005503354 A5 JP2005503354 A5 JP 2005503354A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- give
- group
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- VXIKDBJPBRMXBP-UHFFFAOYSA-N 3H-pyrrole Chemical compound C1C=CN=C1 VXIKDBJPBRMXBP-UHFFFAOYSA-N 0.000 claims 1
- OCZOIRGKMNHALH-UHFFFAOYSA-N O1NBCC1.O1NBCC1 Chemical compound O1NBCC1.O1NBCC1 OCZOIRGKMNHALH-UHFFFAOYSA-N 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- PUPAWTXNPAJCHR-UHFFFAOYSA-N oxazaborole Chemical compound O1C=CB=N1 PUPAWTXNPAJCHR-UHFFFAOYSA-N 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- -1 Phosphonate ester Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DICZUTMNXOMHQD-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one Chemical compound C1CCC2OC(=O)CC21 DICZUTMNXOMHQD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0112699.4A GB0112699D0 (en) | 2001-05-24 | 2001-05-24 | Process for the preparation of prostglandins and analogues thereof |
| PCT/GB2002/002462 WO2002096898A2 (en) | 2001-05-24 | 2002-05-24 | Process for the preparation of prostaglandins and analogues thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009278234A Division JP2010053149A (ja) | 2001-05-24 | 2009-12-08 | プロスタグランジン及びそれらの類縁体の製法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005503354A JP2005503354A (ja) | 2005-02-03 |
| JP2005503354A5 true JP2005503354A5 (enExample) | 2006-01-05 |
| JP4475943B2 JP4475943B2 (ja) | 2010-06-09 |
Family
ID=9915243
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003500077A Expired - Fee Related JP4475943B2 (ja) | 2001-05-24 | 2002-05-24 | プロスタグランジン及びそれらの類縁体の製法 |
| JP2009278234A Pending JP2010053149A (ja) | 2001-05-24 | 2009-12-08 | プロスタグランジン及びそれらの類縁体の製法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009278234A Pending JP2010053149A (ja) | 2001-05-24 | 2009-12-08 | プロスタグランジン及びそれらの類縁体の製法 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US20040249172A1 (enExample) |
| EP (2) | EP2311820A1 (enExample) |
| JP (2) | JP4475943B2 (enExample) |
| CN (2) | CN1301986C (enExample) |
| AU (1) | AU2002321396B2 (enExample) |
| BR (1) | BR0209984A (enExample) |
| CA (1) | CA2448088A1 (enExample) |
| GB (1) | GB0112699D0 (enExample) |
| HU (1) | HUP0400047A3 (enExample) |
| IL (1) | IL159030A0 (enExample) |
| NO (1) | NO329883B1 (enExample) |
| NZ (1) | NZ529634A (enExample) |
| SK (1) | SK14362003A3 (enExample) |
| WO (1) | WO2002096898A2 (enExample) |
| ZA (1) | ZA200308916B (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0112699D0 (en) * | 2001-05-24 | 2001-07-18 | Resolution Chemicals Ltd | Process for the preparation of prostglandins and analogues thereof |
| US7321057B2 (en) * | 2004-08-02 | 2008-01-22 | R-Tech Ueno, Ltd. | Method for manufacturing prostaglandin analogue |
| PL212658B1 (pl) * | 2005-04-18 | 2012-11-30 | Inst Farmaceutyczny | Sposób otrzymywania pochodnych 13,14-dihydro-PGF<sub>2</sub><sub>α</sub> |
| US20090287003A1 (en) * | 2005-09-29 | 2009-11-19 | Jiang Xing Chen | Process for the production of intermediates for making prostaglandin derivatives such as latanaprost, travaprost, and bimatoprost |
| US7511168B2 (en) | 2006-01-18 | 2009-03-31 | Shih-Yi Wei | Processes and intermediates for the preparations of prostaglandins |
| US8546114B2 (en) | 2006-01-18 | 2013-10-01 | Chirogate International Inc. | Processes for the preparation of optically active cyclopentenones and cyclopentenones prepared therefrom |
| EP2735566A1 (en) * | 2006-02-07 | 2014-05-28 | R-Tech Ueno, Ltd. | Method for preparing prostaglandin derivative |
| JP2008037782A (ja) * | 2006-08-04 | 2008-02-21 | Daiichi Fine Chemical Co Ltd | プロスタグランジン誘導体の製造方法 |
| US7642370B2 (en) * | 2006-08-07 | 2010-01-05 | Daiichi Fine Chemical Co., Ltd. | Method for preparing prostaglandin derivative |
| US20090233830A1 (en) * | 2008-03-14 | 2009-09-17 | Penny Sue Dirr | Automatic detergent dishwashing composition |
| EP2135860A1 (en) | 2008-06-20 | 2009-12-23 | Sandoz AG | Improved process for the production of bimatoprost |
| EP2143712A1 (en) | 2008-07-10 | 2010-01-13 | Sandoz AG | Improved Process for the Production of Prostaglandins and Prostaglandin Analogs |
| IT1392492B1 (it) * | 2008-12-24 | 2012-03-09 | Ind Chimica Srl | Processo per la purificazione del latanoprost, analogo sintetico della prostaglandina pgf2alfa. |
| KR101045935B1 (ko) * | 2009-03-11 | 2011-07-01 | 연성정밀화학(주) | 프로스타글란딘 유도체의 제조방법 |
| US8519178B2 (en) * | 2009-06-22 | 2013-08-27 | Johnson Matthey Public Limited Company | Method for the purification of prostaglandins |
| CA2777290C (en) * | 2009-10-16 | 2016-06-28 | Cayman Chemical Company, Incorporated | Process for the preparation of f-series prostaglandins |
| WO2011055377A1 (en) * | 2009-11-05 | 2011-05-12 | Biocon Limited | A novel process for the preparation of prostaglandins and intermediates thereof |
| WO2011095990A2 (en) | 2010-02-03 | 2011-08-11 | Fdc Limited | Process for the purification of prostaglandins and analogues thereof |
| EP2495235B1 (en) | 2011-03-04 | 2015-08-05 | Newchem S.p.A. | Process for the synthesis of prostaglandins and intermediates thereof |
| HU231203B1 (hu) * | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
| TWI435752B (zh) * | 2012-08-15 | 2014-05-01 | Everlight Chem Ind Corp | 使用製備型高效液相層析儀純化含氟之前列腺素之方法 |
| US9115109B2 (en) | 2013-08-15 | 2015-08-25 | Chirogate International Inc. | Processes and intermediates for the preparations of isomer free prostaglandins |
| HU231214B1 (hu) | 2014-03-13 | 2021-11-29 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás nagytisztaságú prosztaglandinok előállítására |
| CN104513186B (zh) * | 2015-01-13 | 2016-10-05 | 宁波第二激素厂 | 一种光学纯的右旋氯前列醇钠的制备方法 |
| HU231175B1 (hu) * | 2015-12-04 | 2021-06-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Tetszőleges, előre meghatározott minőségű Latanoprostene bunod előállítása gravitációs kromatográfiával |
| EP3950672A4 (en) * | 2019-03-27 | 2023-01-11 | Kyowa Pharma Chemical Co., Ltd. | PROCESS FOR PRODUCTION OF PROSTAGLANDIN |
| CN112608294B (zh) * | 2020-12-16 | 2021-10-26 | 西安国康瑞金制药有限公司 | 一种拉坦前列腺素的制备方法 |
| WO2022138586A1 (ja) * | 2020-12-23 | 2022-06-30 | 協和ファーマケミカル株式会社 | 幾何異性体の分離方法 |
| CN115991691B (zh) * | 2023-03-23 | 2023-05-16 | 西南交通大学 | 一种拉坦前列素中间体的制备方法及其用途 |
| WO2025149165A1 (en) | 2024-01-12 | 2025-07-17 | Intervet International B.V. | A PROCESS FOR PURIFICATION OF INTERMEDIATES OF PROSTAGLANDIN F2Αα COMPOUNDS AND ITS USE IN THE PREPARATION OF PROSTAGLANDIN F2α COMPOUNDS |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3549688A (en) * | 1967-02-16 | 1970-12-22 | Gen Electric | Process for the preparation of carboxylic acid esters |
| US3778450A (en) | 1971-03-23 | 1973-12-11 | Upjohn Co | Certain bicyclic lactones |
| CA971957A (en) | 1971-12-13 | 1975-07-29 | Upjohn Company (The) | PROCESS FOR PREPARING PROSTAGLANDIN E'S FROM PROSTAGLANDIN F.alpha.'S |
| US4100355A (en) | 1972-09-15 | 1978-07-11 | The Upjohn Company | 8β,12α-PGE2 -type compounds |
| US3864387A (en) | 1973-05-21 | 1975-02-04 | Upjohn Co | 5-Oxa phenyl-and phenoxy-substituted prostaglandin F{HD 1{301 {0 {B analogs |
| US3931279A (en) | 1973-05-21 | 1976-01-06 | The Upjohn Company | 5-Oxa prostaglandin F2.sub.α analogs |
| GB1484591A (en) * | 1974-04-11 | 1977-09-01 | Ono Pharmaceutical Co | Prostaglandin compositions |
| US4036832A (en) | 1974-07-03 | 1977-07-19 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandins |
| DE2434133C2 (de) | 1974-07-12 | 1987-03-19 | Schering AG, 1000 Berlin und 4709 Bergkamen | 15,15-Äthylendioxy-Prostansäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2517773A1 (de) * | 1975-04-18 | 1976-10-28 | Schering Ag | Neue 11-oxo-prostaglandin-derivate und verfahren zu ihrer herstellung |
| US4158667A (en) * | 1976-02-04 | 1979-06-19 | The Upjohn Company | 6-Keto PGF analogs |
| EP0059307A1 (de) | 1981-02-26 | 1982-09-08 | Grünenthal GmbH | Verfahren zur Herstellung von 2-Oxabicyclo(3.3.0)octanderivaten und danach erhältliche Produkte |
| US4599353A (en) | 1982-05-03 | 1986-07-08 | The Trustees Of Columbia University In The City Of New York | Use of eicosanoids and their derivatives for treatment of ocular hypertension and glaucoma |
| JPS6137752A (ja) * | 1984-07-30 | 1986-02-22 | Kuraray Co Ltd | 高度不飽和長鎖脂肪酸またはそのエステルの分離精製法 |
| US4680415A (en) * | 1985-06-24 | 1987-07-14 | Hoffmann-La Roche Inc. | Intermediates for 7-fluoro dihydro PGI compounds |
| US4943635A (en) | 1987-08-27 | 1990-07-24 | President & Fellows Of Harvard College | Enantioselective reduction of ketones |
| EP0394263B1 (en) | 1987-09-04 | 1994-03-16 | The Upjohn Company | Process for production of prostaglandin intermediates |
| US5321128A (en) * | 1988-09-06 | 1994-06-14 | Kabi Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
| ATE420857T1 (de) | 1988-09-06 | 2009-01-15 | Pfizer Health Ab | Prostaglandin-derivate zur behandlung von glaukom und ocularer hypertension |
| JP2855450B2 (ja) | 1989-09-11 | 1999-02-10 | 小野薬品工業株式会社 | プロスタグランジン誘導体の中間体の製造方法 |
| SE9002596D0 (sv) | 1990-08-08 | 1990-08-08 | Pharmacia Ab | A method for synthesis of prostaglandin derivatives |
| EP0472338A3 (en) * | 1990-08-21 | 1993-05-19 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Method of manufacturing prostaglandin intermediate |
| JPH085873B2 (ja) | 1990-08-21 | 1996-01-24 | 株式会社上野製薬応用研究所 | プロスタグランジン中間体の製法 |
| HU212570B (en) | 1991-06-24 | 1996-08-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 13,14-dihydro-15(r)-17-phenyl-18,19,20-trinor-pgf2alfa-isopropylester |
| US5223537A (en) * | 1991-07-23 | 1993-06-29 | Kabi Pharmacia Ab | Method and composition for treatment of gastric and duodenal disorders |
| US5688819A (en) | 1992-09-21 | 1997-11-18 | Allergan | Cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| JP3207203B2 (ja) | 1992-09-30 | 2001-09-10 | 株式会社上野製薬応用研究所 | α，β−不飽和ケトンの製造法 |
| DE4323331A1 (de) | 1993-07-08 | 1995-01-12 | Schering Ag | Neue bicyclische Lactone |
| US6184250B1 (en) * | 1993-08-03 | 2001-02-06 | Alcon Laboratories, Inc. | Use of cloprostenol and fluprostenol analogues to treat glaucoma and ocular hypertension |
| US5510383A (en) | 1993-08-03 | 1996-04-23 | Alcon Laboratories, Inc. | Use of cloprostenol, fluprostenol and their salts and esters to treat glaucoma and ocular hypertension |
| NL194919C (nl) * | 1993-09-07 | 2003-07-04 | Tno | Werkwijze voor het oxideren van koolhydraten. |
| US5545665A (en) | 1993-12-28 | 1996-08-13 | Allergan | Cyclopentane(ene) heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents |
| US5698733A (en) | 1994-09-30 | 1997-12-16 | Alcon Laboratories, Inc. | Use of 9-deoxy prostaglandin derivatives to treat glaucoma |
| HU223345B1 (hu) | 1995-12-20 | 2004-08-30 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Eljárás alfa, béta-telítetlen ketonok sztereoszelektív redukciójára |
| ATE202557T1 (de) * | 1996-11-12 | 2001-07-15 | Alcon Lab Inc | 15-fluoro-prostaglandine als augendrucksenkende mittel |
| SE9702681D0 (sv) | 1997-07-10 | 1997-07-10 | Pharmacia & Upjohn Ab | Method and composition for treatment of impotence |
| SE9702706D0 (sv) | 1997-07-11 | 1997-07-11 | Pharmacia & Upjohn Ab | Prostaglandin derivatives devoid of side-effects for the treatment of glaucoma |
| WO1999012899A1 (en) | 1997-09-09 | 1999-03-18 | The Procter & Gamble Company | A process for making prostaglandin f analogs |
| WO2000020386A1 (en) | 1998-10-05 | 2000-04-13 | Alcon Laboratories, Inc. | Stannane synthesis of prostanoids |
| SE9900025D0 (sv) | 1999-01-08 | 1999-01-08 | Synphora Ab | Method and composition for treatment of female sexual dysfunction |
| WO2000040246A1 (en) | 1999-01-08 | 2000-07-13 | University Of Massachusetts | Detection of human immunodeficiency virus |
| JP3501025B2 (ja) | 1999-07-15 | 2004-02-23 | 松下電器産業株式会社 | 電気調理器 |
| IL134241A (en) | 2000-01-27 | 2006-06-11 | Finetech Pharmaceutical Ltd | Process for the preparation of latanoprost |
| AU2001233286B2 (en) | 2000-02-01 | 2006-04-06 | Cayman Chemical Company, Incorporated | Internal 1,15-lactones of fluprostenol and related prostaglandin F2alpha analogs and their use in the treatment of glaucoma and intraocular hypertension |
| WO2001067816A1 (en) | 2000-03-07 | 2001-09-13 | Daimlerchrysler Ag | Skin effect heating system for a structural member |
| WO2001087816A1 (en) * | 2000-05-15 | 2001-11-22 | Pharmacia & Upjohn Company | Process and intermediates to prepare latanoprost |
| GB0112699D0 (en) | 2001-05-24 | 2001-07-18 | Resolution Chemicals Ltd | Process for the preparation of prostglandins and analogues thereof |
| KR100581647B1 (ko) * | 2001-07-17 | 2006-05-22 | 파마시아 앤드 업존 캄파니 엘엘씨 | 라타노프로스트 제조를 위한 방법 및 중간체 |
-
2001
- 2001-05-24 GB GBGB0112699.4A patent/GB0112699D0/en not_active Ceased
-
2002
- 2002-05-24 HU HU0400047A patent/HUP0400047A3/hu unknown
- 2002-05-24 CN CNB028146344A patent/CN1301986C/zh not_active Expired - Fee Related
- 2002-05-24 SK SK1436-2003A patent/SK14362003A3/sk not_active Application Discontinuation
- 2002-05-24 IL IL15903002A patent/IL159030A0/xx unknown
- 2002-05-24 US US10/478,513 patent/US20040249172A1/en not_active Abandoned
- 2002-05-24 NZ NZ529634A patent/NZ529634A/en not_active IP Right Cessation
- 2002-05-24 CN CNA2006100636760A patent/CN101003503A/zh active Pending
- 2002-05-24 JP JP2003500077A patent/JP4475943B2/ja not_active Expired - Fee Related
- 2002-05-24 BR BR0209984-5A patent/BR0209984A/pt not_active IP Right Cessation
- 2002-05-24 CA CA002448088A patent/CA2448088A1/en not_active Abandoned
- 2002-05-24 EP EP10186205A patent/EP2311820A1/en not_active Withdrawn
- 2002-05-24 WO PCT/GB2002/002462 patent/WO2002096898A2/en not_active Ceased
- 2002-05-24 EP EP02755096A patent/EP1389198A2/en not_active Withdrawn
- 2002-05-24 AU AU2002321396A patent/AU2002321396B2/en not_active Ceased
-
2003
- 2003-11-14 ZA ZA200308916A patent/ZA200308916B/xx unknown
- 2003-11-20 NO NO20035162A patent/NO329883B1/no not_active IP Right Cessation
-
2005
- 2005-07-27 US US11/189,986 patent/US7268239B2/en not_active Expired - Fee Related
- 2005-07-27 US US11/189,985 patent/US7498458B2/en not_active Expired - Fee Related
-
2009
- 2009-12-08 JP JP2009278234A patent/JP2010053149A/ja active Pending
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