CA2485428A1 - A process for the preparation of modafinil - Google Patents
A process for the preparation of modafinil Download PDFInfo
- Publication number
- CA2485428A1 CA2485428A1 CA002485428A CA2485428A CA2485428A1 CA 2485428 A1 CA2485428 A1 CA 2485428A1 CA 002485428 A CA002485428 A CA 002485428A CA 2485428 A CA2485428 A CA 2485428A CA 2485428 A1 CA2485428 A1 CA 2485428A1
- Authority
- CA
- Canada
- Prior art keywords
- diphenylmethyl
- sulfinyl
- sodium
- acetate
- acetic acid
- 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
- 238000000034 method Methods 0.000 title claims abstract description 22
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229960001165 modafinil Drugs 0.000 title description 10
- TVJWZSWDEPQVDV-UHFFFAOYSA-M sodium;2-benzhydrylsulfanylacetate Chemical compound [Na+].C=1C=CC=CC=1C(SCC(=O)[O-])C1=CC=CC=C1 TVJWZSWDEPQVDV-UHFFFAOYSA-M 0.000 claims abstract description 8
- 230000003647 oxidation Effects 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
- QARQPIWTMBRJFX-UHFFFAOYSA-N modafinil acid Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)O)C1=CC=CC=C1 QARQPIWTMBRJFX-UHFFFAOYSA-N 0.000 claims description 13
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 8
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 8
- MAINYRWJUGRISM-UHFFFAOYSA-M sodium;2-benzhydrylsulfinylacetate Chemical compound [Na+].C=1C=CC=CC=1C(S(=O)CC(=O)[O-])C1=CC=CC=C1 MAINYRWJUGRISM-UHFFFAOYSA-M 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 abstract description 2
- 150000003462 sulfoxides Chemical class 0.000 abstract description 2
- 238000001212 derivatisation Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- HCRQRIFRHGPWBH-UHFFFAOYSA-N 2-benzhydrylsulfanylacetamide Chemical compound C=1C=CC=CC=1C(SCC(=O)N)C1=CC=CC=C1 HCRQRIFRHGPWBH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- -1 hydrochloric Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003368 psychostimulant agent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- HTHFEDOFDBZPRX-UHFFFAOYSA-N 2-benzhydrylsulfanylacetic acid Chemical compound C=1C=CC=CC=1C(SCC(=O)O)C1=CC=CC=C1 HTHFEDOFDBZPRX-UHFFFAOYSA-N 0.000 description 1
- SRCCYSUDRUXYQJ-UHFFFAOYSA-N 2-benzhydrylsulfanylacetyl chloride Chemical compound C=1C=CC=CC=1C(SCC(=O)Cl)C1=CC=CC=C1 SRCCYSUDRUXYQJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- USHWCUHXXAVVLF-UHFFFAOYSA-N ethyl 2-benzhydrylsulfanylacetate Chemical compound C=1C=CC=CC=1C(SCC(=O)OCC)C1=CC=CC=C1 USHWCUHXXAVVLF-UHFFFAOYSA-N 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Optical Modulation, Optical Deflection, Nonlinear Optics, Optical Demodulation, Optical Logic Elements (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2002A000991 | 2002-05-10 | ||
| IT2002MI000991A ITMI20020991A1 (it) | 2002-05-10 | 2002-05-10 | Procedimento per la sintesi del modafinil |
| PCT/EP2003/004229 WO2003095423A1 (en) | 2002-05-10 | 2003-04-23 | A process for the preparation of modafinil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2485428A1 true CA2485428A1 (en) | 2003-11-20 |
Family
ID=11449867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002485428A Abandoned CA2485428A1 (en) | 2002-05-10 | 2003-04-23 | A process for the preparation of modafinil |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7057068B2 (enExample) |
| EP (1) | EP1503983B1 (enExample) |
| JP (1) | JP4351626B2 (enExample) |
| KR (1) | KR20040108789A (enExample) |
| AT (1) | ATE364593T1 (enExample) |
| AU (1) | AU2003227668A1 (enExample) |
| CA (1) | CA2485428A1 (enExample) |
| DE (1) | DE60314410T2 (enExample) |
| DK (1) | DK1503983T3 (enExample) |
| EA (1) | EA007327B1 (enExample) |
| ES (1) | ES2286429T3 (enExample) |
| IL (1) | IL165121A0 (enExample) |
| IT (1) | ITMI20020991A1 (enExample) |
| MX (1) | MXPA04011141A (enExample) |
| PL (1) | PL371679A1 (enExample) |
| PT (1) | PT1503983E (enExample) |
| WO (1) | WO2003095423A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE20122504U1 (de) | 2000-07-27 | 2005-12-29 | Teva Pharmaceutical Industries Ltd. | Kristallines und reines Modafinil |
| ITMI20051971A1 (it) * | 2005-10-18 | 2007-04-19 | Dipharma Spa | Procedimento per la preparazione di - modafinil |
| KR20070119037A (ko) * | 2006-02-21 | 2007-12-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | 아르모다피닐의 신규한 결정질 형태 및 이것의 제조 방법 |
| EP1954652A2 (en) * | 2006-03-01 | 2008-08-13 | Teva Pharmaceutical Industries Ltd | An improved process for the preparation of armodafinil |
| WO2008008879A2 (en) * | 2006-07-12 | 2008-01-17 | Elan Corporation, Plc | Nanoparticulate formulations of modafinil |
| US7960586B2 (en) * | 2007-08-16 | 2011-06-14 | Teva Pharmaceutical Industries Ltd. | Purification of armodafinil |
| EP1911739A3 (en) | 2007-11-05 | 2008-09-17 | Dipharma Francis S.r.l. | Crystalline form of (S)-2-phenylethylammonium (R)-diphenyl-methanesulphinyl-acetate |
| US9616068B2 (en) | 2014-10-27 | 2017-04-11 | Pohela LLC | Animal training using cognitive enhancement |
| CN114044730B (zh) * | 2021-11-26 | 2024-04-23 | 台州学院 | 一种亚砜类化合物的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE221261C (enExample) * | ||||
| DE2546319C2 (de) * | 1975-10-16 | 1986-02-27 | Dr. Karl Thomae Gmbh, 7950 Biberach | Cyclohexylphenyl-Derivate, Verfahren zu deren Herstellung und diese enthaltende Mittel |
| GB1584462A (en) * | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
| FR2593809B1 (fr) * | 1986-01-31 | 1988-07-22 | Lafon Labor | Benzhydrylsulfinylacetamide, procede de preparation et utilisation en therapeutique |
| US4964893A (en) * | 1986-04-17 | 1990-10-23 | Monsanto Company | Benzhydryl compounds as herbicide antidotes |
| DE20122504U1 (de) | 2000-07-27 | 2005-12-29 | Teva Pharmaceutical Industries Ltd. | Kristallines und reines Modafinil |
-
2002
- 2002-05-10 IT IT2002MI000991A patent/ITMI20020991A1/it unknown
-
2003
- 2003-04-23 EP EP03725083A patent/EP1503983B1/en not_active Expired - Lifetime
- 2003-04-23 MX MXPA04011141A patent/MXPA04011141A/es active IP Right Grant
- 2003-04-23 US US10/513,881 patent/US7057068B2/en not_active Expired - Fee Related
- 2003-04-23 WO PCT/EP2003/004229 patent/WO2003095423A1/en not_active Ceased
- 2003-04-23 AU AU2003227668A patent/AU2003227668A1/en not_active Abandoned
- 2003-04-23 DK DK03725083T patent/DK1503983T3/da active
- 2003-04-23 ES ES03725083T patent/ES2286429T3/es not_active Expired - Lifetime
- 2003-04-23 PT PT03725083T patent/PT1503983E/pt unknown
- 2003-04-23 PL PL03371679A patent/PL371679A1/xx not_active IP Right Cessation
- 2003-04-23 KR KR10-2004-7018040A patent/KR20040108789A/ko not_active Withdrawn
- 2003-04-23 JP JP2004503444A patent/JP4351626B2/ja not_active Expired - Fee Related
- 2003-04-23 DE DE60314410T patent/DE60314410T2/de not_active Expired - Lifetime
- 2003-04-23 CA CA002485428A patent/CA2485428A1/en not_active Abandoned
- 2003-04-23 AT AT03725083T patent/ATE364593T1/de not_active IP Right Cessation
- 2003-04-23 EA EA200401235A patent/EA007327B1/ru not_active IP Right Cessation
-
2004
- 2004-11-09 IL IL16512104A patent/IL165121A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005525420A (ja) | 2005-08-25 |
| JP4351626B2 (ja) | 2009-10-28 |
| EA200401235A1 (ru) | 2005-06-30 |
| KR20040108789A (ko) | 2004-12-24 |
| EP1503983A1 (en) | 2005-02-09 |
| EA007327B1 (ru) | 2006-08-25 |
| IL165121A0 (en) | 2005-12-18 |
| PT1503983E (pt) | 2007-07-31 |
| DE60314410D1 (de) | 2007-07-26 |
| ITMI20020991A0 (it) | 2002-05-10 |
| DK1503983T3 (da) | 2007-09-10 |
| PL371679A1 (en) | 2005-06-27 |
| ES2286429T3 (es) | 2007-12-01 |
| ITMI20020991A1 (it) | 2003-11-10 |
| DE60314410T2 (de) | 2008-02-14 |
| ATE364593T1 (de) | 2007-07-15 |
| AU2003227668A1 (en) | 2003-11-11 |
| MXPA04011141A (es) | 2005-07-01 |
| WO2003095423A1 (en) | 2003-11-20 |
| US20050154063A1 (en) | 2005-07-14 |
| EP1503983B1 (en) | 2007-06-13 |
| US7057068B2 (en) | 2006-06-06 |
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