CA2406963A1 - Oxidation process for preparing the intermediate 6.alpha.,9.alpha.-difluoro-11.beta.,17.alpha.-dihydroxy-16.alpha.-methyl-androst-1,4-dien-3-one 17.beta.-carboxylic acid - Google Patents
Oxidation process for preparing the intermediate 6.alpha.,9.alpha.-difluoro-11.beta.,17.alpha.-dihydroxy-16.alpha.-methyl-androst-1,4-dien-3-one 17.beta.-carboxylic acid Download PDFInfo
- Publication number
- CA2406963A1 CA2406963A1 CA002406963A CA2406963A CA2406963A1 CA 2406963 A1 CA2406963 A1 CA 2406963A1 CA 002406963 A CA002406963 A CA 002406963A CA 2406963 A CA2406963 A CA 2406963A CA 2406963 A1 CA2406963 A1 CA 2406963A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- water
- process according
- alpha
- 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.)
- Abandoned
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 23
- 230000003647 oxidation Effects 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 34
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 15
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical group OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 239000007800 oxidant agent Substances 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- 239000012296 anti-solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229960003469 flumetasone Drugs 0.000 description 7
- WXURHACBFYSXBI-GQKYHHCASA-N flumethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 5
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229960000289 fluticasone propionate Drugs 0.000 description 3
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 3
- -1 hydroxy acid androstane derivative compound Chemical class 0.000 description 3
- 150000001261 hydroxy acids Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0017988.7 | 2000-07-21 | ||
| GBGB0017988.7A GB0017988D0 (en) | 2000-07-21 | 2000-07-21 | Novel process |
| PCT/GB2001/003289 WO2002008243A1 (en) | 2000-07-21 | 2001-07-20 | Oxidation process for preparing the intermediate 6.alpha.,9.alpha.-difluoro-11.beta.,17.alpha.-dihydroxy-16.alpha.-methyl-androst-1,4-dien-3-one 17.beta.-carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2406963A1 true CA2406963A1 (en) | 2002-01-31 |
Family
ID=9896132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002406963A Abandoned CA2406963A1 (en) | 2000-07-21 | 2001-07-20 | Oxidation process for preparing the intermediate 6.alpha.,9.alpha.-difluoro-11.beta.,17.alpha.-dihydroxy-16.alpha.-methyl-androst-1,4-dien-3-one 17.beta.-carboxylic acid |
Country Status (26)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| CZ2003353A3 (cs) | 2000-08-05 | 2003-05-14 | Glaxo Group Limited | Estery steroidních thiokyselin |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| ES2314052T3 (es) | 2001-04-30 | 2009-03-16 | Glaxo Group Limited | Derivados de ester de 17beta-carbotioato de androstano con un grupo ester ciclico en la posicion 17alfa. |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| IL150654A (en) | 2002-07-09 | 2006-12-10 | Ori Lerman | Method for acid isolation 6α, 9α - difluoro - ß, 17α11 - dihydroxy - 16α - methylfargana - 3 - oxo - 1, 4 - diene - 17ß - carboxylate |
| EP1466920A1 (en) * | 2003-04-04 | 2004-10-13 | Alpharma APS | Process for the preparation of steroidal 17 beta-carbothioates |
| US20070270584A1 (en) * | 2003-04-04 | 2007-11-22 | Trond Loevli | Process for the Preparation of Steroidal Carbothioic Acid Derivatives and Intermediates |
| EP1526139A1 (en) * | 2003-10-24 | 2005-04-27 | S.N.I.F.F. Italia S.P.A. | A process for preparing highly pure androstane 17-beta-carboxylic acids and androstane 17-beta-carbothioic acid fluoromethyl esters |
| GB0612027D0 (en) | 2006-06-16 | 2006-07-26 | Glaxo Group Ltd | Novel process |
| NO331891B1 (no) * | 2007-03-20 | 2012-04-30 | Clavis Pharma Asa | Kjemiske forbindelser, et farmasoytisk preparat inneholdende slike forbindelser, samt anvendelse derav for behandling av kreft, inflammasjon og KOLS |
| PT105139B (pt) * | 2010-06-01 | 2013-01-29 | Hovione Farmaciencia S A | Método para a monofluorometilação de substratos orgânicos para preparação de compostos orgânicos biologicamente activos |
| JP2013536835A (ja) | 2010-09-01 | 2013-09-26 | カディラ・ヘルスケア・リミテッド | プロピオン酸／フロ酸フルチカゾンを調製するための方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636010A (en) * | 1968-12-23 | 1972-01-18 | Ciba Geigy Corp | Esters of steroid-17-carboxylic acids |
| NL187577C (nl) * | 1978-04-05 | 1991-11-18 | Sibla Srl | 3-acetoxy-9beta,11beta-epoxy-pregna-1,3,5-trienen, werkwijze voor de bereiding daarvan en werkwijze voor de bereiding van 6alfa-halogeen-pregna-1,4-dieen-3-onen. |
| US4188385A (en) * | 1978-04-05 | 1980-02-12 | Syntex (U.S.A.) Inc. | Thioetianic acid derivatives |
| US4263289A (en) * | 1978-04-05 | 1981-04-21 | Syntex (U.S.A.) Inc. | Thio etianic acid derivatives |
| US4198336A (en) * | 1978-04-05 | 1980-04-15 | Syntex (U.S.A.) Inc. | Chemical process for preparing androsta-4-ene 17α-carboxylic acids |
| GB2088877B (en) * | 1980-02-15 | 1984-07-04 | Glaxo Group Ltd | Androstane 17 carbothioates |
| US5646136A (en) * | 1994-01-04 | 1997-07-08 | Duke University | Methods of inhibiting angiogenesis and tumor growth, and treating ophthalmologic conditions with angiostatic and therapeutic steroids |
| EP0876392B1 (en) * | 1995-12-29 | 2000-07-05 | Glaxo Group Limited | Lactone derivatives of 17.beta.-carboxy, carbothio and amide androstane derivatives |
| US20020133032A1 (en) * | 2000-02-25 | 2002-09-19 | Jufang Barkalow | Method for the preparation of fluticasone and related 17beta-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods |
| EP1268214B1 (en) * | 2000-04-04 | 2006-06-07 | Celanese International Corporation | Ink receptive coating compositions containing poly(vinyl alcohol) grafted with amine functional groups |
| US6777400B2 (en) * | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
-
2000
- 2000-07-21 GB GBGB0017988.7A patent/GB0017988D0/en not_active Ceased
-
2001
- 2001-07-20 HU HU0301108A patent/HUP0301108A3/hu unknown
- 2001-07-20 SI SI200130851T patent/SI1301526T1/sl unknown
- 2001-07-20 IL IL15234801A patent/IL152348A0/xx active IP Right Grant
- 2001-07-20 EP EP01949791A patent/EP1301526B1/en not_active Expired - Lifetime
- 2001-07-20 MX MXPA02010967A patent/MXPA02010967A/es active IP Right Grant
- 2001-07-20 KR KR1020027014367A patent/KR100787293B1/ko not_active Expired - Fee Related
- 2001-07-20 CN CNB018114407A patent/CN1315864C/zh not_active Expired - Fee Related
- 2001-07-20 JP JP2002514148A patent/JP2004504403A/ja active Pending
- 2001-07-20 DE DE60134472T patent/DE60134472D1/de not_active Expired - Lifetime
- 2001-07-20 PL PL359462A patent/PL206652B1/pl not_active IP Right Cessation
- 2001-07-20 CZ CZ20023472A patent/CZ302592B6/cs not_active IP Right Cessation
- 2001-07-20 AU AU7090601A patent/AU7090601A/xx active Pending
- 2001-07-20 AT AT01949791T patent/ATE398628T1/de active
- 2001-07-20 BR BR0110430-6A patent/BR0110430A/pt not_active Application Discontinuation
- 2001-07-20 PT PT01949791T patent/PT1301526E/pt unknown
- 2001-07-20 CA CA002406963A patent/CA2406963A1/en not_active Abandoned
- 2001-07-20 NZ NZ522083A patent/NZ522083A/en not_active IP Right Cessation
- 2001-07-20 WO PCT/GB2001/003289 patent/WO2002008243A1/en not_active Ceased
- 2001-07-20 US US10/333,537 patent/US20040043974A1/en not_active Abandoned
- 2001-07-20 DK DK01949791T patent/DK1301526T3/da active
- 2001-07-20 HK HK03106680.9A patent/HK1056179B/en not_active IP Right Cessation
- 2001-07-20 AU AU2001270906A patent/AU2001270906B2/en not_active Ceased
- 2001-07-20 ES ES01949791T patent/ES2307628T3/es not_active Expired - Lifetime
-
2002
- 2002-10-17 ZA ZA200208372A patent/ZA200208372B/en unknown
- 2002-10-17 IL IL152348A patent/IL152348A/en not_active IP Right Cessation
- 2002-10-21 NO NO20025054A patent/NO324836B1/no not_active IP Right Cessation
-
2008
- 2008-09-03 CY CY20081100942T patent/CY1108553T1/el unknown
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