ES2532854T3 - Proceso para la preparación de esomeprazol magnésico dihidrato - Google Patents
Proceso para la preparación de esomeprazol magnésico dihidrato Download PDFInfo
- Publication number
- ES2532854T3 ES2532854T3 ES09178721.8T ES09178721T ES2532854T3 ES 2532854 T3 ES2532854 T3 ES 2532854T3 ES 09178721 T ES09178721 T ES 09178721T ES 2532854 T3 ES2532854 T3 ES 2532854T3
- Authority
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- Prior art keywords
- methoxy
- magnesium
- dimethyl
- preparation
- pyridinyl
- Prior art date
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- -1 magnesium esomeprazole dihydrate Chemical class 0.000 title abstract description 6
- 229960004770 esomeprazole Drugs 0.000 title description 5
- 239000011777 magnesium Substances 0.000 title description 5
- 229910052749 magnesium Inorganic materials 0.000 title description 5
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 21
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- ZQLYTERQDSWLIN-VRMKZKMYSA-N magnesium;6-methoxy-2-[(s)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole;dihydrate Chemical compound O.O.[Mg].C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C ZQLYTERQDSWLIN-VRMKZKMYSA-N 0.000 abstract 1
- DCUGZOBNIZLALZ-UHFFFAOYSA-N magnesium;dihydrate Chemical compound O.O.[Mg] DCUGZOBNIZLALZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 4
- 229940091250 magnesium supplement Drugs 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical class C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 description 2
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 2
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PSEPRWKZZJWRCB-UHFFFAOYSA-N (4-methoxy-3,5-dimethylpyridin-2-yl)methanol Chemical compound COC1=C(C)C=NC(CO)=C1C PSEPRWKZZJWRCB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- LCJDHJOUOJSJGS-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridin-1-ium;chloride Chemical compound Cl.COC1=C(C)C=NC(CCl)=C1C LCJDHJOUOJSJGS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KOFBRZWVWJCLGM-UHFFFAOYSA-N 5-methoxy-1,3-dihydrobenzimidazole-2-thione Chemical compound COC1=CC=C2NC(S)=NC2=C1 KOFBRZWVWJCLGM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un proceso para preparar la Forma A del (S)-5-metoxi-2-[[(4-metoxi-3,5-dimetil-2-piridinil)-metil]sulfinil]-1Hbenzimidazol magnésico dihidrato que comprende cristalizar o recristalizar el (S)-5-metoxi-2-[[(4-metoxi-3,5-dimetil-2- piridinil)metil]-1H-benzimidazol magnésico dihidrato bruto en presencia de acetato de etilo y en el que el producto de la cristalización o de la recristalización se filtra y se lava con acetato de etilo.
Description
E09178721
13-03-2015
por oxidación asimétrica y, finalmente, puede ser convertido en esomeprazol magnésico dihidrato.
En otra realización, la Forma II del 5-metoxi-2[[(4-metoxi-3,5-dimetil-2-piridinil)-metil]tio]-1H-benzimidazol que se forma como un intermedio se oxida con un agente oxidante tal como hidroperóxido de cumeno y un complejo quiral 5 de titanio, en ausencia de una base. La oxidación puede llevarse a cabo en un disolvente orgánico tal como tolueno
o diclorometano, más preferiblemente tolueno a una temperatura por debajo de 25 °C y puede convertirse en la sal de potasio correspondiente por tratamiento con una fuente de potasio, tal como hidróxido de potasio metanólico, metóxido de potasio metanólico, hidróxido de potasio etanólico, más preferiblemente hidróxido de potasio metanólico, a una temperatura por debajo de 40 °C durante una duración de menos de 5 horas, más preferiblemente
10 menos de 3 horas. El proceso es reproducible industrialmente.
En otra realización, la Forma A del esomeprazol magnésico dihidrato A se prepara de una manera sistemática por conversión de la sal de esomeprazol, por ejemplo, la sal de potasio, en la correspondientes sal de magnesio en una Forma A polimórfica por tratamiento con una fuente de magnesio, tal como cloruro de magnesio hexahidrato, sulfato 15 de magnesio, más preferiblemente cloruro de magnesio hexahidrato, en ausencia de cualquier base orgánica en un disolvente orgánico tal como metanol, alcohol desnaturalizado, alcohol isopropílico, dimetilformamida, más preferiblemente metanol y alcohol desnaturalizado. La solución se filtra, se destila y la precipitación se inicializa mediante la adición de un anti-disolvente tal como una mezcla de agua y acetato de etilo. El producto se filtra y se lava con acetato de etilo durante el aislamiento después del aislamiento del producto bruto o se agita durante un
20 periodo de tiempo suficiente para facilitar la formación de la Forma A después del aislamiento del producto bruto seguido de secado a vacío para dar la Forma A de una manera extremadamente reproducible en el laboratorio y en una aplicación a gran escala. El tiempo necesario para la agitación puede variar de 15 minutos a 3 horas, preferiblemente de 15 minutos a 1 hora, más preferiblemente de 15 minutos a 30 minutos.
25 El producto así aislado se seca a temperatura elevada, por ejemplo, a una temperatura por debajo de 75 °C, en vacío para obtener la forma polimórfica deseada de esomeprazol magnésico dihidrato, es decir, la Forma A.
El esomeprazol también puede prepararse a partir de la Forma I del 5-metoxi-2-[[(4-metoxi-3,5-dimetil-2-piridinil)metil]tio]-1H-benzimidazol utilizando las condiciones anteriores, pero los rendimientos son más bajos con una pureza
30 enantiomérica baja ya que se forman más impurezas sulfona debido a su mayor solubilidad en disolvente, que le hace que sea más reactivo.
En otra realización, el proceso para la preparación de la Forma II 5-metoxi-2-[[(4-metoxi-3,5-dimetil-2-piridinil)metil]tio]-1H-benzimidazol comprende el tratamiento del clorhidrato de 2-hidroximetil-3,5-dimetil-4-metoxipiridina con 35 cloruro de tionilo en un disolvente orgánico adecuado, tal como cloruro de metileno, cloroformo, cloruro de etileno, etc., preferiblemente cloruro de metileno, a una temperatura que varía de 10 a 25 °C. La masa de reacción que contiene clorhidrato de 2-clorometil-3,5-dimetil-4-metoxi piridina se hace reaccionar adicionalmente con 2-mercapto5-metoxi benzimidazol en presencia de un catalizador como bromuro de tetrabutilamonio en condiciones básicas. Después de completarse la reacción, la capa orgánica se separa, se extrae con cloruro de metileno, la capa
40 orgánica se lava con agua, se concentra y se extrae en acetato de etilo. Se añade más acetato de etilo, se calienta a 50 a 60 °C y se enfría. El sólido resultante se filtra y se lava con acetato de etilo frío. El sólido obtenido se seca a 30 a 35 °C para obtener la Forma II de 5-metoxi-2-[[(4-metoxi-3,5-dimetil-2-piridinil)-metil]tio]-1H-benzimidazol.
Las formas polimórficas I y II del compuesto intermedio 5-metoxi-2-[[(4-metoxi-3,5-dimetil-2-piridinil)-metil]tio]-1H
45 benzimidazol se caracterizan por difractograma de rayos X y se pueden distinguir por sus patrones de difracción de polvo de rayos X característico que indican ángulos de difracción (es decir, grados 2θ) e intensidades relativas (es decir, % I/Io) proporcionados en la siguiente Tabla II.
El XRPD se midió en un difractómetro de polvo de rayos X Rigaku Miniflex 50
Tabla II
- Forma I
- Forma II
- Grados 2θ
- % I/Io Grados 2θ % I/Io
- 9,110
- 45 8,100 32
- 9,720
- 6 9,110 40
- 11,920
- 11 9,750 7
- 12,430
- 59 10,150 7
- 14,200
- 22 11,980 37
- 15,490
- 9 12,430 55
- 16,220
- 20 13,700 17
- 16,510
- 13 14,210 21
- 16,580
- 14 14,990 12
7
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| INMU03482007 | 2007-02-21 | ||
| IN348MU2007 | 2007-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2532854T3 true ES2532854T3 (es) | 2015-04-01 |
Family
ID=39575692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09178721.8T Active ES2532854T3 (es) | 2007-02-21 | 2008-02-21 | Proceso para la preparación de esomeprazol magnésico dihidrato |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8394963B2 (es) |
| EP (3) | EP2125783A2 (es) |
| JP (1) | JP2010519284A (es) |
| KR (2) | KR101522219B1 (es) |
| AU (1) | AU2008217603C1 (es) |
| CA (2) | CA2678702A1 (es) |
| ES (1) | ES2532854T3 (es) |
| NZ (1) | NZ579136A (es) |
| WO (1) | WO2008102145A2 (es) |
| ZA (2) | ZA200905878B (es) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010519284A (ja) | 2007-02-21 | 2010-06-03 | シプラ・リミテッド | エソメプラゾールマグネシウム二水和物の調製方法 |
| US8492551B2 (en) * | 2007-06-07 | 2013-07-23 | Aurobindo Pharma. Ltd. | Process for preparing an optically active proton pump inhibitor |
| EP2195309A4 (en) * | 2007-10-08 | 2013-04-24 | Hetero Drugs Ltd | SALT POLYMORPHS OF THE ESOMEPRAZOLE |
| EP2147918A1 (en) | 2008-07-21 | 2010-01-27 | LEK Pharmaceuticals D.D. | Process for the preparation of S-omeprazole magnesium in a stable form |
| WO2010097583A1 (en) | 2009-02-24 | 2010-09-02 | Cipla Limited | Esomeprazole potassium polymorph and its preparation |
| WO2010150276A2 (en) * | 2009-06-02 | 2010-12-29 | Sun Pharmaceutical Industries Limited | Process for preparing sulphoxide compounds |
| WO2011012957A1 (en) * | 2009-07-29 | 2011-02-03 | Orchid Chemicals & Pharmaceuticals Ltd | An improved process for the preparation of esomeprazole magnesium dihydrate |
| FR2959509B1 (fr) | 2010-05-03 | 2012-07-13 | Prod Chim Auxiliaires Et De Synthese | Phase precurseur et son utilisation pour preparer le sel de magnesium tetrahydrate d'un enantiomere d'omeprazole |
| CN104844577A (zh) * | 2011-07-31 | 2015-08-19 | 连云港润众制药有限公司 | 埃索美拉唑镁的晶型 |
| US8962851B2 (en) * | 2011-12-27 | 2015-02-24 | Cadila Healthcare Limited | One-pot process for the preparation of benzimidazole derivatives |
| CN102633776B (zh) * | 2012-03-28 | 2014-06-18 | 中山市仁合药业有限公司 | 一种埃索美拉唑及其钠盐的制备方法 |
| CN103224489B (zh) * | 2013-05-20 | 2015-03-04 | 青岛正大海尔制药有限公司 | 一种提高埃索美拉唑生产收率和速率的方法 |
| CN104250243B (zh) * | 2013-06-27 | 2016-12-28 | 四川国为制药有限公司 | 一种埃索美拉唑镁二水合物a晶型的制备方法 |
| CN103694223B (zh) * | 2013-07-03 | 2016-08-10 | 乐普药业股份有限公司 | 一种一锅法制备埃索美拉唑镁的方法 |
| FR3018812A1 (fr) | 2014-03-21 | 2015-09-25 | Minakem | Nouvelle phase intermediaire de la forme a du sel de magnesium dihydrate d'un enantiomere de l'omeprazole |
| CN104356113A (zh) * | 2014-10-31 | 2015-02-18 | 广东东阳光药业有限公司 | 制备埃索美拉唑镁二水合物的方法 |
| CN104557864A (zh) * | 2015-01-08 | 2015-04-29 | 浙江长典医药有限公司 | 艾司奥美拉唑新化合物实体及其制备方法与药物组合制剂 |
| FR3062129B1 (fr) * | 2017-01-23 | 2019-04-05 | Minakem | Procede d'obtention du sel de magnesium dihydrate de l'esomeprazole |
| CN114209697A (zh) * | 2021-12-14 | 2022-03-22 | 重庆大学附属三峡医院 | 一种质子泵抑制剂、制备方法及应用 |
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| US20030212274A1 (en) * | 2000-05-15 | 2003-11-13 | Bakthavathsalan Vijayaraghavan | Novel amorphous form of omeprazole salts |
| WO2003054171A1 (en) * | 2001-12-06 | 2003-07-03 | The Regents Of The University Of California | Method for differentiating islet precursor cells into beta cells |
| TR200401671T1 (tr) | 2002-01-23 | 2005-04-21 | Ulkar Ki̇mya Sanayi̇i̇ Ve Ti̇caret A.Ş. | Piridin benzimidazol sülfinil bileşiklerinin sentesi sırasında oluşan sulfon analoglarının elimine edilmesi yöntemi |
| US7169793B2 (en) | 2002-06-27 | 2007-01-30 | Dr. Reddy's Laboratories Limited | Process for preparation of optically pure or optically enriched sulfoxide compounds, including amorphous esomeprazole and salts thereof |
| EP1546131A1 (en) * | 2002-08-30 | 2005-06-29 | Dr. Reddy's Laboratories Ltd. | Amorphous hydrates of esomeprazole magnesium and process for the preparation thereof |
| EA200500673A1 (ru) | 2002-10-22 | 2005-12-29 | Рэнбакси Лабораториз Лимитед | Аморфная форма соли эзомепразола, способ ее получения и фармацевтическая композиция на её основе |
| US20040242642A1 (en) | 2002-11-18 | 2004-12-02 | Dr. Reddy's Laboratories Limited | Crystalline esomeprazole compounds and process for the preparation thereof |
| SE0302382D0 (sv) | 2003-09-04 | 2003-09-04 | Astrazeneca Ab | New salts II |
| EP1740571B1 (en) * | 2004-04-28 | 2009-07-29 | Hetero Drugs Limited | A process for preparing pyridinylmethyl-1h- benzimidazole compounds in enantiomerically enriched form or as single enantiomers |
| US20050267157A1 (en) * | 2004-05-28 | 2005-12-01 | David White | Magnesium-S-omeprazole |
| DE602004025386D1 (de) | 2004-05-28 | 2010-03-18 | Hetero Drugs Ltd | Neue stereoselektive synthese von benzimidazolsulfoxiden |
| PL1802584T3 (pl) * | 2004-10-11 | 2010-03-31 | Ranbaxy Laboratories Ltd | Sposób wytwarzania podstawionych sulfotlenków |
| WO2006096709A2 (en) | 2005-03-08 | 2006-09-14 | Dr. Reddy's Laboratories Ltd. | Process for preparing amorphous salts |
| DE102005061720B3 (de) * | 2005-12-22 | 2006-10-19 | Ratiopharm Gmbh | Enantioselektive Herstellung von Benzimidazolderivaten und ihren Salzen |
| WO2008018091A1 (en) * | 2006-08-08 | 2008-02-14 | Jubilant Organosys Limited | Process for producing sulphoxide compounds |
| JP2010519284A (ja) | 2007-02-21 | 2010-06-03 | シプラ・リミテッド | エソメプラゾールマグネシウム二水和物の調製方法 |
-
2008
- 2008-02-21 JP JP2009550757A patent/JP2010519284A/ja active Pending
- 2008-02-21 US US12/527,967 patent/US8394963B2/en not_active Expired - Fee Related
- 2008-02-21 NZ NZ579136A patent/NZ579136A/en not_active IP Right Cessation
- 2008-02-21 AU AU2008217603A patent/AU2008217603C1/en not_active Ceased
- 2008-02-21 CA CA002678702A patent/CA2678702A1/en not_active Abandoned
- 2008-02-21 EP EP08709485A patent/EP2125783A2/en not_active Withdrawn
- 2008-02-21 ES ES09178721.8T patent/ES2532854T3/es active Active
- 2008-02-21 KR KR1020097019506A patent/KR101522219B1/ko not_active Expired - Fee Related
- 2008-02-21 WO PCT/GB2008/000602 patent/WO2008102145A2/en not_active Ceased
- 2008-02-21 EP EP14190724.6A patent/EP2842953A1/en not_active Withdrawn
- 2008-02-21 KR KR1020147033405A patent/KR101522865B1/ko not_active Expired - Fee Related
- 2008-02-21 EP EP09178721.8A patent/EP2186807B1/en not_active Not-in-force
- 2008-02-21 CA CA2889878A patent/CA2889878A1/en not_active Abandoned
-
2009
- 2009-08-25 ZA ZA2009/05878A patent/ZA200905878B/en unknown
-
2010
- 2010-04-06 ZA ZA2010/02379A patent/ZA201002379B/en unknown
-
2013
- 2013-02-05 US US13/759,468 patent/US20130150587A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2125783A2 (en) | 2009-12-02 |
| AU2008217603B2 (en) | 2013-02-07 |
| EP2186807A1 (en) | 2010-05-19 |
| KR20140146226A (ko) | 2014-12-24 |
| EP2186807B1 (en) | 2015-01-07 |
| CA2678702A1 (en) | 2008-08-28 |
| WO2008102145A3 (en) | 2008-11-13 |
| JP2010519284A (ja) | 2010-06-03 |
| NZ579136A (en) | 2012-05-25 |
| KR101522219B1 (ko) | 2015-05-21 |
| ZA201002379B (en) | 2010-11-24 |
| AU2008217603C1 (en) | 2013-08-15 |
| US20100113526A1 (en) | 2010-05-06 |
| US20130150587A1 (en) | 2013-06-13 |
| CA2889878A1 (en) | 2008-08-28 |
| ZA200905878B (en) | 2011-02-23 |
| WO2008102145A2 (en) | 2008-08-28 |
| AU2008217603A1 (en) | 2008-08-28 |
| EP2842953A1 (en) | 2015-03-04 |
| KR101522865B1 (ko) | 2015-05-26 |
| KR20100014468A (ko) | 2010-02-10 |
| US8394963B2 (en) | 2013-03-12 |
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