NO331507B1 - Metode for fremstilling av metyl 2-difenylmetylsulfinylacetat. - Google Patents
Metode for fremstilling av metyl 2-difenylmetylsulfinylacetat. Download PDFInfo
- Publication number
- NO331507B1 NO331507B1 NO20053602A NO20053602A NO331507B1 NO 331507 B1 NO331507 B1 NO 331507B1 NO 20053602 A NO20053602 A NO 20053602A NO 20053602 A NO20053602 A NO 20053602A NO 331507 B1 NO331507 B1 NO 331507B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- acid
- reaction
- acetate
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- KJPGMBAVZUTLAA-UHFFFAOYSA-N o-methyl 3,3-diphenylpropanethioate Chemical compound C=1C=CC=CC=1C(CC(=S)OC)C1=CC=CC=C1 KJPGMBAVZUTLAA-UHFFFAOYSA-N 0.000 claims abstract description 16
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 15
- 150000007522 mineralic acids Chemical class 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 230000035484 reaction time Effects 0.000 claims description 13
- 150000008065 acid anhydrides Chemical class 0.000 claims description 11
- 239000000010 aprotic solvent Substances 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 238000002955 isolation Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- -1 benzhydrol carboxylate Chemical class 0.000 claims description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 6
- 229940011051 isopropyl acetate Drugs 0.000 claims description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 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 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229960001165 modafinil Drugs 0.000 claims description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 2
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940045872 sodium percarbonate Drugs 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 8
- 230000003647 oxidation Effects 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000012429 reaction media Substances 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- QBKMWJRMLACRJD-UHFFFAOYSA-N benzhydryl acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C1=CC=CC=C1 QBKMWJRMLACRJD-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- PYHXGXCGESYPCW-UHFFFAOYSA-N diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000012958 reprocessing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BIASHYVHAQBNGV-UHFFFAOYSA-N 3,3-diphenylpropanethioic s-acid Chemical compound C=1C=CC=CC=1C(CC(=S)O)C1=CC=CC=C1 BIASHYVHAQBNGV-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- JFMZFATUMFWKEA-UHFFFAOYSA-N methyl 2-benzhydrylsulfinylacetate Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)OC)C1=CC=CC=C1 JFMZFATUMFWKEA-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- VDIVXMYEGUTCEL-UHFFFAOYSA-N o-methyl 2,2-diphenylethanethioate Chemical compound C=1C=CC=CC=1C(C(=S)OC)C1=CC=CC=C1 VDIVXMYEGUTCEL-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20030290082 EP1437345A1 (en) | 2003-01-13 | 2003-01-13 | Novel method for preparing methyl 2-diphenylmethylsulfinylacetate |
| PCT/IB2004/000002 WO2004063149A1 (en) | 2003-01-13 | 2004-01-08 | Method for preparing methyl 2-diphenylmethylsulfinylacetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20053602L NO20053602L (no) | 2005-07-22 |
| NO331507B1 true NO331507B1 (no) | 2012-01-16 |
Family
ID=32479973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20053602A NO331507B1 (no) | 2003-01-13 | 2005-07-22 | Metode for fremstilling av metyl 2-difenylmetylsulfinylacetat. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7211684B2 (enExample) |
| EP (2) | EP1437345A1 (enExample) |
| JP (1) | JP4690304B2 (enExample) |
| KR (1) | KR101062281B1 (enExample) |
| CN (1) | CN100516035C (enExample) |
| AR (1) | AR042842A1 (enExample) |
| AU (1) | AU2004203975B2 (enExample) |
| BR (1) | BRPI0406489A (enExample) |
| CA (1) | CA2512084C (enExample) |
| EA (1) | EA010381B1 (enExample) |
| IL (1) | IL169517A (enExample) |
| IS (1) | IS7958A (enExample) |
| MX (1) | MXPA05007419A (enExample) |
| NO (1) | NO331507B1 (enExample) |
| NZ (1) | NZ541089A (enExample) |
| PL (1) | PL212412B1 (enExample) |
| TW (1) | TWI323250B (enExample) |
| UA (1) | UA80598C2 (enExample) |
| WO (1) | WO2004063149A1 (enExample) |
| ZA (1) | ZA200505381B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1437345A1 (en) | 2003-01-13 | 2004-07-14 | Organisation de Synthese Mondiale Orsymonde | Novel method for preparing methyl 2-diphenylmethylsulfinylacetate |
| EP1516869A1 (en) | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| US7368591B2 (en) | 2003-09-19 | 2008-05-06 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| CN100393699C (zh) * | 2005-03-10 | 2008-06-11 | 浙江工业大学 | 2-（二苯基甲基亚硫酰基）乙酰胺的合成方法 |
| EP1702915A1 (en) | 2005-03-14 | 2006-09-20 | Cephalon France | Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation |
| WO2007103221A2 (en) * | 2006-03-01 | 2007-09-13 | Teva Pharmaceutical Industries Ltd. | An improved process for the preparation of armodafinil |
| CN104059004A (zh) * | 2014-06-25 | 2014-09-24 | 江苏斯威森生物医药工程研究中心有限公司 | 一种2-[(4,4’-二卤-二苯基甲基)巯基]乙酸酯的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE198165C (enExample) | ||||
| GB1520812A (en) * | 1975-10-02 | 1978-08-09 | Lafon Labor | Benzhydrylsulphinyl derivatives |
| GB1584462A (en) * | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
| DE2812542A1 (de) | 1978-03-22 | 1979-10-04 | Thomae Gmbh Dr K | Neue schwefelhaltige fluorenyl-und phenanthryl-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| FR2528038B2 (fr) * | 1982-06-04 | 1985-08-09 | Lafon Labor | Derives de benzhydrylsulfinylacetamide et leur utilisation en therapeutique |
| FR2528041A1 (fr) * | 1982-06-04 | 1983-12-09 | Lafon Labor | Acides halogenobenzhydrylsulfinylacetohydroxamiques, procede de preparation et utilisation en therapeutique |
| US4964893A (en) * | 1986-04-17 | 1990-10-23 | Monsanto Company | Benzhydryl compounds as herbicide antidotes |
| JP3233806B2 (ja) * | 1995-01-23 | 2001-12-04 | ユーシービージャパン株式会社 | スルフェニル酢酸誘導体の製造法 |
| US5571825A (en) * | 1995-03-31 | 1996-11-05 | Warner-Lambert Company | Method of selectively inhibiting prostaglandin G/H synthase-2 |
| EP1437345A1 (en) | 2003-01-13 | 2004-07-14 | Organisation de Synthese Mondiale Orsymonde | Novel method for preparing methyl 2-diphenylmethylsulfinylacetate |
-
2003
- 2003-01-13 EP EP20030290082 patent/EP1437345A1/en not_active Withdrawn
-
2004
- 2004-01-05 TW TW093100155A patent/TWI323250B/zh not_active IP Right Cessation
- 2004-01-08 EP EP04700742A patent/EP1583739A1/en not_active Withdrawn
- 2004-01-08 EA EA200501125A patent/EA010381B1/ru not_active IP Right Cessation
- 2004-01-08 BR BR0406489-5A patent/BRPI0406489A/pt not_active IP Right Cessation
- 2004-01-08 AU AU2004203975A patent/AU2004203975B2/en not_active Ceased
- 2004-01-08 MX MXPA05007419A patent/MXPA05007419A/es active IP Right Grant
- 2004-01-08 KR KR1020057012882A patent/KR101062281B1/ko not_active Expired - Fee Related
- 2004-01-08 JP JP2006500269A patent/JP4690304B2/ja not_active Expired - Fee Related
- 2004-01-08 PL PL377822A patent/PL212412B1/pl unknown
- 2004-01-08 NZ NZ541089A patent/NZ541089A/en not_active IP Right Cessation
- 2004-01-08 WO PCT/IB2004/000002 patent/WO2004063149A1/en not_active Ceased
- 2004-01-08 US US10/541,527 patent/US7211684B2/en not_active Expired - Fee Related
- 2004-01-08 CN CNB2004800021479A patent/CN100516035C/zh not_active Expired - Fee Related
- 2004-01-08 CA CA2512084A patent/CA2512084C/en not_active Expired - Fee Related
- 2004-01-12 AR ARP040100073A patent/AR042842A1/es not_active Application Discontinuation
- 2004-08-01 UA UAA200508009A patent/UA80598C2/uk unknown
-
2005
- 2005-07-04 IL IL169517A patent/IL169517A/en not_active IP Right Cessation
- 2005-07-04 ZA ZA200505381A patent/ZA200505381B/xx unknown
- 2005-07-22 NO NO20053602A patent/NO331507B1/no not_active IP Right Cessation
- 2005-07-26 IS IS7958A patent/IS7958A/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200505381B (enExample) | 2006-04-26 |
| CA2512084A1 (en) | 2004-07-29 |
| CA2512084C (en) | 2012-03-20 |
| IL169517A (en) | 2012-06-28 |
| JP4690304B2 (ja) | 2011-06-01 |
| KR20050091085A (ko) | 2005-09-14 |
| EP1583739A1 (en) | 2005-10-12 |
| US20060235237A1 (en) | 2006-10-19 |
| NZ541089A (en) | 2008-05-30 |
| PL377822A1 (pl) | 2006-02-20 |
| AU2004203975A1 (en) | 2004-07-29 |
| MXPA05007419A (es) | 2005-09-12 |
| CN100516035C (zh) | 2009-07-22 |
| CN1735591A (zh) | 2006-02-15 |
| AU2004203975B2 (en) | 2010-07-01 |
| EP1437345A1 (en) | 2004-07-14 |
| BRPI0406489A (pt) | 2005-12-06 |
| AR042842A1 (es) | 2005-07-06 |
| NO20053602L (no) | 2005-07-22 |
| PL212412B1 (pl) | 2012-09-28 |
| JP2006516560A (ja) | 2006-07-06 |
| US7211684B2 (en) | 2007-05-01 |
| IS7958A (is) | 2005-07-26 |
| WO2004063149A1 (en) | 2004-07-29 |
| TWI323250B (en) | 2010-04-11 |
| UA80598C2 (en) | 2007-10-10 |
| TW200420530A (en) | 2004-10-16 |
| EA200501125A1 (ru) | 2005-12-29 |
| KR101062281B1 (ko) | 2011-09-06 |
| EA010381B1 (ru) | 2008-08-29 |
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