HRP960232A2 - A process for the optical purification of compounds - Google Patents
A process for the optical purification of compounds Download PDFInfo
- Publication number
- HRP960232A2 HRP960232A2 HRPCT/SE95/00817A HRP960232A HRP960232A2 HR P960232 A2 HRP960232 A2 HR P960232A2 HR P960232 A HRP960232 A HR P960232A HR P960232 A2 HRP960232 A2 HR P960232A2
- Authority
- HR
- Croatia
- Prior art keywords
- benzimidazole
- methyl
- enantiomer
- methoxy
- compound
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000000746 purification Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 title claims description 54
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims description 10
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical group COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims description 9
- PSIREIZGKQBEEO-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n-methyl-n-(2-methylpropyl)aniline Chemical group CC(C)CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 PSIREIZGKQBEEO-UHFFFAOYSA-N 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- JWMQOWBYKLZSPY-UHFFFAOYSA-N 9-(1h-benzimidazol-2-ylsulfinyl)-4-methoxy-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridine Chemical group N=1C2=CC=CC=C2NC=1S(=O)C1CCCCC2=C1N=CC=C2OC JWMQOWBYKLZSPY-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 21
- BHVRHDLXKLRTEY-UHFFFAOYSA-N 2-sulfinyl-1,3-dihydrobenzimidazole Chemical class C1=CC=C2NC(=S=O)NC2=C1 BHVRHDLXKLRTEY-UHFFFAOYSA-N 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical class N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 28
- 239000000706 filtrate Substances 0.000 description 20
- 229960000381 omeprazole Drugs 0.000 description 16
- 150000003462 sulfoxides Chemical class 0.000 description 16
- 239000006188 syrup Substances 0.000 description 16
- 235000020357 syrup Nutrition 0.000 description 16
- -1 ( 2 -(N - isobutyl - N - methylamino) benzyl) sulfinyl Chemical group 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000011914 asymmetric synthesis Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229960003174 lansoprazole Drugs 0.000 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 5
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229950007395 leminoprazole Drugs 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000027119 gastric acid secretion Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- PWWDEIMGEBPTJL-UHFFFAOYSA-N 1-(pyridin-2-ylmethylsulfinyl)benzimidazole Chemical compound C1=NC2=CC=CC=C2N1S(=O)CC1=CC=CC=N1 PWWDEIMGEBPTJL-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XURCIPRUUASYLR-UHFFFAOYSA-N Omeprazole sulfide Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=NC=C(C)C(OC)=C1C XURCIPRUUASYLR-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- YSAVZVORKRDODB-PHDIDXHHSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-PHDIDXHHSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9500817 | 1995-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP960232A2 true HRP960232A2 (en) | 1998-02-28 |
Family
ID=20397468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRPCT/SE95/00817A HRP960232A2 (en) | 1995-07-03 | 1996-05-21 | A process for the optical purification of compounds |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US5929244A (fr) |
| EP (2) | EP1498416A1 (fr) |
| JP (1) | JP4195507B2 (fr) |
| KR (1) | KR100451078B1 (fr) |
| CN (1) | CN1098261C (fr) |
| AT (1) | ATE418549T1 (fr) |
| AU (1) | AU698638B2 (fr) |
| BR (1) | BR9609450A (fr) |
| CA (1) | CA2226184C (fr) |
| CZ (1) | CZ295430B6 (fr) |
| DE (1) | DE69637788D1 (fr) |
| DK (1) | DK0836601T3 (fr) |
| DZ (1) | DZ2057A1 (fr) |
| EE (1) | EE03444B1 (fr) |
| ES (1) | ES2318850T3 (fr) |
| HK (1) | HK1010193A1 (fr) |
| HR (1) | HRP960232A2 (fr) |
| HU (1) | HUP9901717A3 (fr) |
| IL (1) | IL122811A (fr) |
| IS (1) | IS2666B (fr) |
| MA (1) | MA23921A1 (fr) |
| MY (1) | MY114018A (fr) |
| NO (1) | NO313008B1 (fr) |
| NZ (1) | NZ311842A (fr) |
| PL (1) | PL186702B1 (fr) |
| PT (1) | PT836601E (fr) |
| RS (1) | RS49826B (fr) |
| RU (1) | RU2144031C1 (fr) |
| SA (1) | SA96170103B1 (fr) |
| SI (1) | SI0836601T1 (fr) |
| SK (1) | SK284780B6 (fr) |
| TN (1) | TNSN96090A1 (fr) |
| TR (1) | TR199701754T1 (fr) |
| TW (1) | TW444010B (fr) |
| UA (1) | UA49838C2 (fr) |
| WO (1) | WO1997002261A1 (fr) |
| ZA (1) | ZA965205B (fr) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP960232A2 (en) * | 1995-07-03 | 1998-02-28 | Astra Ab | A process for the optical purification of compounds |
| US6699885B2 (en) * | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of using same |
| US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US6645988B2 (en) | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| EP0983263A1 (fr) * | 1997-05-30 | 2000-03-08 | Dr. Reddy's Research Foundation | Nouveaux benzimidazoles utilises comme agents antiulcereux, leur procede de preparation et compositions pharmaceutiques les contenant |
| JP2002501897A (ja) * | 1998-01-30 | 2002-01-22 | セプラコール， インク． | Ｒ−ランソプラゾール組成物及び方法 |
| SE9900274D0 (sv) | 1999-01-28 | 1999-01-28 | Astra Ab | New compound |
| TWI289557B (en) | 1999-06-17 | 2007-11-11 | Takeda Chemical Industries Ltd | A crystal of a hydrate of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
| DE60020967T2 (de) | 1999-06-30 | 2006-05-04 | Takeda Pharmaceutical Co. Ltd. | Kristalle von lansoprazole |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US6262085B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6369087B1 (en) | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| DE60131649T2 (de) | 2000-05-15 | 2008-10-30 | Takeda Pharmaceutical Co. Ltd. | Verfahren zur herstellung eines kristalls |
| CA2417311C (fr) | 2000-08-04 | 2012-07-10 | Takeda Chemical Industries, Ltd. | Sels cristallins de metal alcalin et de lansoprazole et methode de production et utilisation connexes |
| KR20100002278A (ko) | 2000-12-01 | 2010-01-06 | 다케다 야쿠힌 고교 가부시키가이샤 | (ｒ)- 또는 (ｓ)-란소프라졸의 결정 |
| KR100433735B1 (ko) * | 2001-06-27 | 2004-06-04 | 주식회사 씨트리 | 결정형 ⅰ을 갖는 란소프라졸의 제조방법 |
| SE0104295D0 (sv) * | 2001-12-18 | 2001-12-18 | Astrazeneca Ab | New process |
| US20040006111A1 (en) * | 2002-01-25 | 2004-01-08 | Kenneth Widder | Transmucosal delivery of proton pump inhibitors |
| MY148805A (en) | 2002-10-16 | 2013-05-31 | Takeda Pharmaceutical | Controlled release preparation |
| US8697094B2 (en) | 2002-10-16 | 2014-04-15 | Takeda Pharmaceutical Company Limited | Stable solid preparations |
| DE10254167A1 (de) | 2002-11-20 | 2004-06-09 | Icon Genetics Ag | Verfahren zur Kontrolle von zellulären Prozessen in Pflanzen |
| MXPA05005762A (es) | 2002-12-06 | 2005-08-16 | Altana Pharma Ag | Procedimiento para preparar compuestos activos opticamente puros. |
| PL375695A1 (en) | 2002-12-06 | 2005-12-12 | Altana Pharma Ag | Process for preparing (s)-pantoprazole |
| US20040248942A1 (en) * | 2003-02-20 | 2004-12-09 | Bonnie Hepburn | Novel formulation, omeprazole antacid complex-immediate release for rapid and sustained suppression of gastric acid |
| CA2517714A1 (fr) * | 2003-02-28 | 2004-09-10 | Ranbaxy Laboratories Limited | Polymorphes de s-omeprazole |
| US20050031700A1 (en) * | 2003-07-18 | 2005-02-10 | Sanatarus, Inc. | Pharmaceutical formulation and method for treating acid-caused gastrointestinal disorders |
| US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US7005732B2 (en) * | 2003-10-21 | 2006-02-28 | Honeywell International Inc. | Methods and systems for providing MEMS devices with a top cap and upper sense plate |
| FR2863609A1 (fr) * | 2003-12-15 | 2005-06-17 | Isochem Sa | Procede d'enrichissement enantiomerique d'un melange d'enantiomeres d'alpha-aminoacides |
| SE0400410D0 (sv) * | 2004-02-20 | 2004-02-20 | Astrazeneca Ab | New compounds |
| US8906940B2 (en) * | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8815916B2 (en) * | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| EP1768668A2 (fr) | 2004-06-16 | 2007-04-04 | Tap Pharmaceutical Products, Inc. | Forme posologique a doses ppi multiples |
| EP1801110A1 (fr) | 2005-12-22 | 2007-06-27 | KRKA, tovarna zdravil, d.d., Novo mesto | Sel d'arginine d'ésoméprazole |
| US7553857B2 (en) | 2005-12-23 | 2009-06-30 | Lek Pharmaceuticals D.D. | S-omeprazole magnesium |
| US7786309B2 (en) * | 2006-06-09 | 2010-08-31 | Apotex Pharmachem Inc. | Process for the preparation of esomeprazole and salts thereof |
| FR2909380B1 (fr) * | 2006-12-04 | 2009-02-20 | Sidem Pharma Sa Sa | Conglomerats de sels de potassium de tenatoprazole |
| EP1947099A1 (fr) | 2007-01-18 | 2008-07-23 | LEK Pharmaceuticals D.D. | Procédé pour l'élimination de solvant des sels d'oméprazole |
| CN101323609B (zh) * | 2007-06-15 | 2013-05-01 | 成都福瑞生物工程有限公司 | 不对称氧化硫醚成亚砜合成对映体含量高的苯并咪唑衍生物的方法 |
| KR101432866B1 (ko) * | 2007-06-15 | 2014-08-26 | 엠큐어 파마슈티컬즈 리미티드 | 생활성 화합물의 설폭사이드화 방법 |
| FR2920428B1 (fr) * | 2007-08-29 | 2012-06-15 | Univ Rouen | Procede de dedoublement de sels de l'omeprazole |
| PE20091680A1 (es) | 2008-03-10 | 2009-11-16 | Takeda Pharmaceutical | Cristal de compuestos de bencimidazol |
| WO2010058409A2 (fr) | 2008-11-18 | 2010-05-27 | Hetero Research Foundation | Purification optique d'esoméprazole |
| KR101001646B1 (ko) * | 2008-12-12 | 2010-12-17 | 한미약품 주식회사 | (ｒ)-(+)-란소프라졸의 제조방법 및 이에 사용되는 중간체 |
| WO2011004387A2 (fr) | 2009-06-18 | 2011-01-13 | Matrix Laboratories Ltd | Procédé de préparation de formes polymorphes du dexlansoprazole |
| US8748619B2 (en) | 2009-11-12 | 2014-06-10 | Hetero Research Foundation | Process for the resolution of omeprazole |
| AU2011210328A1 (en) | 2010-01-29 | 2012-08-16 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline forms of dexlansoprazole |
| US10071996B2 (en) | 2014-07-30 | 2018-09-11 | Aetas Pharma Co., Ltd. | Optical isomer of 1,4-benzothiazepine-1-oxide derivative, and pharmaceutical composition prepared using same |
| EP3064495B1 (fr) | 2015-03-06 | 2016-12-14 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Procédé amélioré pour la préparation de l'esomeprazole optiquement pure |
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| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| JPS6150978A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| AU4640985A (en) * | 1984-08-31 | 1986-03-06 | Nippon Chemiphar Co. Ltd. | Benzimidazole derivatives |
| FI90544C (fi) * | 1986-11-13 | 1994-02-25 | Eisai Co Ltd | Menetelmä lääkeaineina käyttökelpoisten 2-pyridin-2-yyli-metyylitio- ja sulfinyyli-1H-bensimidatsolijohdannaisten valmistamiseksi |
| ES2057338T3 (es) * | 1989-11-29 | 1994-10-16 | Toa Eiyo Ltd | Derivados de cicloheptenopiridina, procedimiento para su preparacion y agentes antiulcerosos que los contienen. |
| DE4035455A1 (de) * | 1990-11-08 | 1992-05-14 | Byk Gulden Lomberg Chem Fab | Enantiomerentrennung |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| IS4232A (is) * | 1993-12-06 | 1995-06-07 | Astra Aktiebolag | Súbstitúerað bensimidasól, aðferðir við framleiðslu þess og lyfjafræðileg notkun |
| HRP960232A2 (en) * | 1995-07-03 | 1998-02-28 | Astra Ab | A process for the optical purification of compounds |
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