HRP20120168T1 - Postupak i međuprodukti kod dobivanja derivata n-(1-benzhidrilazetidin-3-il)-n-fenilmetilsulfonamida - Google Patents
Postupak i međuprodukti kod dobivanja derivata n-(1-benzhidrilazetidin-3-il)-n-fenilmetilsulfonamida Download PDFInfo
- Publication number
- HRP20120168T1 HRP20120168T1 HR20120168T HRP20120168T HRP20120168T1 HR P20120168 T1 HRP20120168 T1 HR P20120168T1 HR 20120168 T HR20120168 T HR 20120168T HR P20120168 T HRP20120168 T HR P20120168T HR P20120168 T1 HRP20120168 T1 HR P20120168T1
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- unbranched
- carbon atoms
- branched alkyl
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- 238000000034 method Methods 0.000 title claims abstract 13
- 239000000543 intermediate Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract 17
- 229910052794 bromium Inorganic materials 0.000 claims abstract 16
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims abstract 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract 14
- 150000002367 halogens Chemical class 0.000 claims abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 14
- 229910052740 iodine Inorganic materials 0.000 claims abstract 14
- 230000015572 biosynthetic process Effects 0.000 claims abstract 13
- 238000003786 synthesis reaction Methods 0.000 claims abstract 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 7
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 239000003960 organic solvent Substances 0.000 claims abstract 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract 3
- 239000011707 mineral Substances 0.000 claims abstract 3
- 150000007530 organic bases Chemical class 0.000 claims abstract 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims abstract 2
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 claims abstract 2
- 229940124530 sulfonamide Drugs 0.000 claims abstract 2
- 150000003456 sulfonamides Chemical class 0.000 claims abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 2
- -1 trifluoromethoxy radicals Chemical class 0.000 claims 12
- 239000000460 chlorine Substances 0.000 claims 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical group [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 5
- 239000002585 base Substances 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- 238000001308 synthesis method Methods 0.000 claims 5
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims 4
- 235000019798 tripotassium phosphate Nutrition 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- XJEIUGUQDIKUSM-UHFFFAOYSA-N bis(4-chlorophenyl)methanamine Chemical compound C=1C=C(Cl)C=CC=1C(N)C1=CC=C(Cl)C=C1 XJEIUGUQDIKUSM-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000012071 phase Substances 0.000 claims 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 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 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- 235000010755 mineral Nutrition 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 150000003254 radicals Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 235000009518 sodium iodide Nutrition 0.000 claims 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims 1
- BUWXUSLQPDDDSD-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-yloxy)butane Chemical compound CCC(C)(C)OC(C)(C)CC BUWXUSLQPDDDSD-UHFFFAOYSA-N 0.000 claims 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical group OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- PGDDYDAGRXBVAI-UHFFFAOYSA-N FC1=CC(F)=CC(CN(C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(=O)=O)=C1 Chemical compound FC1=CC(F)=CC(CN(C2CN(C2)C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)S(=O)=O)=C1 PGDDYDAGRXBVAI-UHFFFAOYSA-N 0.000 claims 1
- USIVBZYEQWGVKT-UHFFFAOYSA-N FC1=CC(F)=CC(CNS(=O)=O)=C1 Chemical compound FC1=CC(F)=CC(CNS(=O)=O)=C1 USIVBZYEQWGVKT-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 238000007171 acid catalysis Methods 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 229910052792 caesium Inorganic materials 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003983 crown ethers Chemical group 0.000 claims 1
- 230000006198 deformylation Effects 0.000 claims 1
- 238000006344 deformylation reaction Methods 0.000 claims 1
- 229940117389 dichlorobenzene Drugs 0.000 claims 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- BKVTZJMXNVXSLR-UHFFFAOYSA-N n-[bis(4-chlorophenyl)methyl]formamide Chemical compound C1=CC(Cl)=CC=C1C(NC=O)C1=CC=C(Cl)C=C1 BKVTZJMXNVXSLR-UHFFFAOYSA-N 0.000 claims 1
- DMDPGPKXQDIQQG-UHFFFAOYSA-N pentaglyme Chemical compound COCCOCCOCCOCCOCCOC DMDPGPKXQDIQQG-UHFFFAOYSA-N 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
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- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0410845A FR2876689B1 (fr) | 2004-10-14 | 2004-10-14 | Nouveau procede et intermediaires de preparation de derives de n-(1-benzhydryl-azetidin-3-yl)-n-phenyl-methylsulfonamide |
| PCT/FR2005/002489 WO2006040464A1 (fr) | 2004-10-14 | 2005-10-10 | Procede et intermediaires de preparation de derives de n-(1-benzhydryl-azetidin-3-yl)-n-phenyl-methylsulfonamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120168T1 true HRP20120168T1 (hr) | 2012-03-31 |
Family
ID=34953744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20120168T HRP20120168T1 (hr) | 2004-10-14 | 2012-02-20 | Postupak i međuprodukti kod dobivanja derivata n-(1-benzhidrilazetidin-3-il)-n-fenilmetilsulfonamida |
Country Status (32)
| Country | Link |
|---|---|
| US (3) | US7429668B2 (ja) |
| EP (1) | EP1802571B1 (ja) |
| JP (1) | JP4971986B2 (ja) |
| KR (1) | KR20070063540A (ja) |
| CN (1) | CN101039903A (ja) |
| AR (1) | AR051389A1 (ja) |
| AT (1) | ATE534624T1 (ja) |
| AU (1) | AU2005293453A1 (ja) |
| BR (1) | BRPI0516526A (ja) |
| CA (1) | CA2581781A1 (ja) |
| CR (1) | CR9008A (ja) |
| CY (1) | CY1112390T1 (ja) |
| DK (1) | DK1802571T3 (ja) |
| EA (2) | EA012523B1 (ja) |
| ES (1) | ES2378181T3 (ja) |
| FR (1) | FR2876689B1 (ja) |
| HR (1) | HRP20120168T1 (ja) |
| IL (1) | IL182277A0 (ja) |
| MA (1) | MA29005B1 (ja) |
| ME (1) | ME01297B (ja) |
| MX (1) | MX2007004483A (ja) |
| NO (1) | NO20072431L (ja) |
| PL (1) | PL1802571T3 (ja) |
| PT (1) | PT1802571E (ja) |
| RS (1) | RS52132B (ja) |
| SG (2) | SG144921A1 (ja) |
| SI (1) | SI1802571T1 (ja) |
| TN (1) | TNSN07115A1 (ja) |
| TW (1) | TW200626542A (ja) |
| UY (1) | UY29165A1 (ja) |
| WO (1) | WO2006040464A1 (ja) |
| ZA (1) | ZA200703011B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2925050B1 (fr) * | 2007-12-14 | 2010-01-08 | Sanofi Aventis | Nouveau procede de preparation de derives d'azetidine |
| US20120130130A1 (en) * | 2009-06-29 | 2012-05-24 | Merz Pharma Gmbh & Co. Kgaa | Method of preparing neramexane |
| DK2448909T3 (da) * | 2009-06-29 | 2013-07-15 | Merz Pharma Gmbh & Co Kgaa | Fremgangsmåde til fremstilling af 1-amino-1,3,3,5,5-pentamethylcyclohexan |
| CN107089918B (zh) * | 2017-04-08 | 2020-06-16 | 迪嘉药业集团有限公司 | 一种盐酸二苯甲胺的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9714129D0 (en) * | 1997-07-04 | 1997-09-10 | Pfizer Ltd | Azetidines |
| US6566356B2 (en) * | 2000-03-03 | 2003-05-20 | Aventis Pharma S.A. | Pharmaceutical compositions containing 3-aminoazetidine derivatives, novel derivatives and their preparation |
| FR2805817B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives d'azetidine, les nouveaux derives d'azetidine et leur preparation |
| FR2814678B1 (fr) * | 2000-10-04 | 2002-12-20 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et de sibutramine, les compositions pharmaceutiques les contenant et leur utilisation pour la traitement de l'obesite |
-
2004
- 2004-10-14 FR FR0410845A patent/FR2876689B1/fr not_active Expired - Fee Related
-
2005
- 2005-10-10 ME MEP-2012-19A patent/ME01297B/me unknown
- 2005-10-10 BR BRPI0516526-1A patent/BRPI0516526A/pt not_active IP Right Cessation
- 2005-10-10 KR KR1020077008412A patent/KR20070063540A/ko not_active Application Discontinuation
- 2005-10-10 PT PT05809316T patent/PT1802571E/pt unknown
- 2005-10-10 SG SG200805168-2A patent/SG144921A1/en unknown
- 2005-10-10 AU AU2005293453A patent/AU2005293453A1/en not_active Withdrawn
- 2005-10-10 CA CA002581781A patent/CA2581781A1/fr not_active Abandoned
- 2005-10-10 PL PL05809316T patent/PL1802571T3/pl unknown
- 2005-10-10 JP JP2007536213A patent/JP4971986B2/ja not_active Expired - Fee Related
- 2005-10-10 SG SG200805167-4A patent/SG144920A1/en unknown
- 2005-10-10 CN CNA2005800350930A patent/CN101039903A/zh active Pending
- 2005-10-10 EA EA200700842A patent/EA012523B1/ru not_active IP Right Cessation
- 2005-10-10 EP EP05809316A patent/EP1802571B1/fr active Active
- 2005-10-10 ES ES05809316T patent/ES2378181T3/es active Active
- 2005-10-10 EA EA200801990A patent/EA200801990A1/ru unknown
- 2005-10-10 MX MX2007004483A patent/MX2007004483A/es active IP Right Grant
- 2005-10-10 DK DK05809316.2T patent/DK1802571T3/da active
- 2005-10-10 ZA ZA200703011A patent/ZA200703011B/xx unknown
- 2005-10-10 SI SI200531476T patent/SI1802571T1/sl unknown
- 2005-10-10 WO PCT/FR2005/002489 patent/WO2006040464A1/fr active Application Filing
- 2005-10-10 AT AT05809316T patent/ATE534624T1/de active
- 2005-10-10 RS RS20120060A patent/RS52132B/en unknown
- 2005-10-13 TW TW094135609A patent/TW200626542A/zh unknown
- 2005-10-13 AR ARP050104295A patent/AR051389A1/es unknown
- 2005-10-14 UY UY29165A patent/UY29165A1/es unknown
-
2007
- 2007-03-21 CR CR9008A patent/CR9008A/es not_active Application Discontinuation
- 2007-03-28 TN TNP2007000115A patent/TNSN07115A1/fr unknown
- 2007-03-28 US US11/692,462 patent/US7429668B2/en active Active
- 2007-03-28 IL IL182277A patent/IL182277A0/en unknown
- 2007-05-04 MA MA29868A patent/MA29005B1/fr unknown
- 2007-05-11 NO NO20072431A patent/NO20072431L/no not_active Application Discontinuation
-
2008
- 2008-08-20 US US12/194,644 patent/US7652154B2/en active Active
-
2009
- 2009-12-11 US US12/635,965 patent/US8071788B2/en active Active
-
2012
- 2012-02-20 HR HR20120168T patent/HRP20120168T1/hr unknown
- 2012-02-23 CY CY20121100184T patent/CY1112390T1/el unknown
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