SI22752B - Optično čiste soli piridinilmetil sulfinil-1H-benzimidazolovih spojin - Google Patents
Optično čiste soli piridinilmetil sulfinil-1H-benzimidazolovih spojin Download PDFInfo
- Publication number
- SI22752B SI22752B SI9420085A SI9420085A SI22752B SI 22752 B SI22752 B SI 22752B SI 9420085 A SI9420085 A SI 9420085A SI 9420085 A SI9420085 A SI 9420085A SI 22752 B SI22752 B SI 22752B
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- Slovenia
- Prior art keywords
- salt
- preparation
- treatment
- omeprazole
- enantiomer
- Prior art date
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- 150000003839 salts Chemical class 0.000 title abstract 2
- 125000006513 pyridinyl methyl group Chemical class 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract 8
- 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 claims abstract 6
- 238000000034 method Methods 0.000 claims abstract 6
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 229960000381 omeprazole Drugs 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 159000000000 sodium salts Chemical class 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 125000005042 acyloxymethyl group Chemical group 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 2
- 208000000689 peptic esophagitis Diseases 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims 1
- 206010019375 Helicobacter infections Diseases 0.000 claims 1
- 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 1
- 206010057969 Reflux gastritis Diseases 0.000 claims 1
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 206010046274 Upper gastrointestinal haemorrhage Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000000718 duodenal ulcer Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 210000004211 gastric acid Anatomy 0.000 claims 1
- 230000027119 gastric acid secretion Effects 0.000 claims 1
- 201000005917 gastric ulcer Diseases 0.000 claims 1
- 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 claims 1
- 201000000052 gastrinoma Diseases 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 230000036269 ulceration Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
Classifications
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- 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
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Medicinal Preparation (AREA)
Abstract
Opisane so nove optično čiste spojine, ki so Na+, Mg2+, Li+, K+, Ca2+ in N+(R)4 soli (+)-5-metoksi-2-(((4-metoksi-3,5-dimetil-2-piridinil)metil)sulfinil)-1H- benzimidazola in (-)-5-metoksi-2-(((4-metoksi-3,5-dimetil-2-piridinil)metil) sulfinil)-1H-benzimidazola, v katerih je R alkil z 1-4 ogljikovimi atomi, postopek njihove priprave in njihova uporaba v izdelavi farmacevtskih pripravkov. Podani so tudi novi intermediati v pripravi spojin izuma.
Claims (16)
1 EP 1020460 BI Patentni zahtevki 1. Natrijeva sol (-)-5-metoksi-2-[[(4-metoksi-3,5-dimetil-2-piridinil)metil]sulfinil]-lH-benzimidazola (Na-sol (-)-enantiomera omeprazola) z optično čistoto oz. enantiomemim prebitkom (e.e.) >99,8 %.
2. Na-sol, kot je definirano v zahtevku 1, v kristalinični obliki.
3. Postopek za pripravo Na-soli, kot je definirano v zahtevku 1, označen s tem, da diastereomemo zmes estra s formulo III:
(III) kjer acil pomeni kiralno acilno skupino, ki ima bodisi R- ali S-konfiguracijo, ločimo, da dobimo ločene diastereomere, nato diastereomer, ki obsega aciloksimetilni derivat (-)-enantiomera omeprazola, raztopimo v alkalni raztopini, v kateri se aciloksimetilna skupina odstrani s hidrolizo, tako da nastane (-)-enantiomer omeprazola, ki ga po izbiri pretvorimo v natrijevo sol.
4. Postopek po zahtevku 3, označen s tem, daje kiralna acilna skupina mandeloil.
5. Postopek po zahtevku 3, označen s tem, da diastereomere ločimo s kromatografijo ali frakcijsko kristalizacijo. 2
6. Postopek po zahtevku 3, označen s tem, da solvolizo izvedemo v alkalni raztopini, ki sestoji iz baze v protičnem topilu, kot so alkoholi ali voda, ali baze v aprotičnem topilu, kot je dimetilsulfoksid ali dimetilformamid.
7. Postopek po zahtevku 3, označen s tem, da natrijevo sol dobimo z obdelavo (-)-enantiomera omeprazola z bazo, ki obsega natrij, v nevodni raztopini.
8. Farmacevtski pripravek, ki vsebuje Na-sol, kot je definirano v zahtevku 1, skupaj s farmacevtsko sprejemljivim nosilcem.
9. Na-sol, kot je definirano v zahtevku 1, za uporabo pri terapiji.
10. Uporaba Na-soli, kot je definirano v zahtevku 1, za pripravo farmacevtske formulacije za zdravljenje bolezni, povezanih z želodčno kislino, z inhibicijo izločanja želodčne kisline.
11. Uporaba Na-soli, kot je definirano v zahtevku 1, za pripravo farmacevtske formulacije za zdravljenje gastrointestinalnih vnetnih bolezni.
12. Uporaba Na-soli, kot je definirano v zahtevku 1, za pripravo farmacevtske formulacije za zdravljenje gastričnega ulkusa, duodenalnega ulkusa, refluksnega ezofagitisa ali gastritisa.
13. Uporaba Na-soli, kot je definirano v zahtevku 1, za pripravo farmacevtske formulacije za zdravljenje refluksnega ezofagitisa.
14. Uporaba po zahtevku 10, kjer je pacient na NSAID-terapiji, ima gastrinom ali ima akutno krvavitev zgornjega gastrointestinalnega trakta. 3
15. Uporaba po zahtevku 10, kjer je zdravilo za zdravljenje pacienta v stanju intenzivne nege ali ga je treba uporabiti pred- in pooperativno za preprečenje kislinske aspiracije in stresne ulceracije.
16. Uporaba po zahtevku 10, kjer zdravilo uporabimo pri zdravljenju infekcije s Helicobacter.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE19939301830A SE9301830D0 (sv) | 1993-05-28 | 1993-05-28 | New compounds |
| PCT/SE1994/000509 WO1994027988A1 (en) | 1993-05-28 | 1994-05-27 | Optically pure salts of pyridinylmethyl sulfinyl-ih-benzimidazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI22752A SI22752A (sl) | 2009-10-31 |
| SI22752B true SI22752B (sl) | 2010-01-29 |
Family
ID=20390088
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9420002A SI9420002B (sl) | 1993-05-28 | 1994-05-27 | Optično čiste soli piridinilmetil sulfinil-1H-benzimidazolovih spojin |
| SI9420085A SI22752B (sl) | 1993-05-28 | 1994-05-27 | Optično čiste soli piridinilmetil sulfinil-1H-benzimidazolovih spojin |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9420002A SI9420002B (sl) | 1993-05-28 | 1994-05-27 | Optično čiste soli piridinilmetil sulfinil-1H-benzimidazolovih spojin |
Country Status (42)
| Country | Link |
|---|---|
| US (5) | US5693818A (sl) |
| EP (3) | EP0652872B1 (sl) |
| JP (3) | JP3549111B2 (sl) |
| KR (1) | KR100337274B1 (sl) |
| CN (2) | CN1055469C (sl) |
| AT (1) | ATE197452T1 (sl) |
| CA (2) | CA2139653C (sl) |
| CL (1) | CL2009000805A1 (sl) |
| CY (1) | CY2224B1 (sl) |
| CZ (1) | CZ287876B6 (sl) |
| DE (4) | DE69426254T2 (sl) |
| DK (3) | DK0652872T3 (sl) |
| DZ (1) | DZ1785A1 (sl) |
| EE (1) | EE03157B1 (sl) |
| ES (3) | ES2326404T3 (sl) |
| FI (2) | FI117755B (sl) |
| GR (2) | GR970300012T1 (sl) |
| HR (1) | HRP940307B1 (sl) |
| HU (1) | HU226824B1 (sl) |
| IL (1) | IL109684A (sl) |
| IS (1) | IS1854B (sl) |
| LT (1) | LT3287B (sl) |
| LU (1) | LU91870I2 (sl) |
| LV (1) | LV11034B (sl) |
| MA (1) | MA23210A1 (sl) |
| MY (1) | MY121192A (sl) |
| NO (2) | NO307378B1 (sl) |
| NZ (1) | NZ266915A (sl) |
| PL (1) | PL178994B1 (sl) |
| PT (3) | PT652872E (sl) |
| RU (1) | RU2137766C1 (sl) |
| SA (2) | SA94140756B1 (sl) |
| SE (1) | SE9301830D0 (sl) |
| SG (1) | SG49283A1 (sl) |
| SI (2) | SI9420002B (sl) |
| SK (1) | SK282524B6 (sl) |
| TN (1) | TNSN94058A1 (sl) |
| TW (1) | TW389761B (sl) |
| UA (1) | UA60289C2 (sl) |
| WO (1) | WO1994027988A1 (sl) |
| YU (1) | YU49065B (sl) |
| ZA (1) | ZA943557B (sl) |
Families Citing this family (214)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5877192A (en) * | 1993-05-28 | 1999-03-02 | Astra Aktiebolag | Method for the treatment of gastric acid-related diseases and production of medication using (-) enantiomer of omeprazole |
| US6875872B1 (en) | 1993-05-28 | 2005-04-05 | Astrazeneca | Compounds |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| PT1078628E (pt) | 1994-07-08 | 2009-01-27 | Astrazeneca Ab | Forma de dosagem em comprimidos com unidades múltiplas |
| SE504459C2 (sv) * | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
| SE9500422D0 (sv) * | 1995-02-06 | 1995-02-06 | Astra Ab | New oral pharmaceutical dosage forms |
| SE9500478D0 (sv) * | 1995-02-09 | 1995-02-09 | Astra Ab | New pharmaceutical formulation and process |
| HRP960232A2 (en) * | 1995-07-03 | 1998-02-28 | Astra Ab | A process for the optical purification of compounds |
| US6489346B1 (en) * | 1996-01-04 | 2002-12-03 | The 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 |
| US6645988B2 (en) | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US6699885B2 (en) * | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of using same |
| SE9600070D0 (sv) | 1996-01-08 | 1996-01-08 | Astra Ab | New oral pharmaceutical dosage forms |
| SE508669C2 (sv) * | 1996-04-26 | 1998-10-26 | Astra Ab | Nytt förfarande |
| SE510666C2 (sv) * | 1996-12-20 | 1999-06-14 | Astra Ab | Nya Kristallmodifikationer |
| SE9702000D0 (sv) * | 1997-05-28 | 1997-05-28 | Astra Ab | New pharmaceutical formulation |
| US6747155B2 (en) | 1997-05-30 | 2004-06-08 | Astrazeneca Ab | Process |
| SE510650C2 (sv) * | 1997-05-30 | 1999-06-14 | Astra Ab | Ny förening |
| SE510643C2 (sv) * | 1997-06-27 | 1999-06-14 | Astra Ab | Termodynamiskt stabil omeprazol natrium form B |
| US6096340A (en) * | 1997-11-14 | 2000-08-01 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| US6174548B1 (en) | 1998-08-28 | 2001-01-16 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| DK1037607T3 (da) * | 1997-12-08 | 2004-06-21 | Altana Pharma Ag | Hidtil ukendt suppositoriumsform, der omfatter en syrelabil aktiv forbindelse |
| SE9704870D0 (sv) | 1997-12-22 | 1997-12-22 | Astra Ab | New pharmaceutical formulation I |
| SE9704869D0 (sv) * | 1997-12-22 | 1997-12-22 | Astra Ab | New pharmaceutical formulaton II |
| EP1004305B1 (en) * | 1998-04-20 | 2011-09-28 | Eisai R&D Management Co., Ltd. | Stabilized compositions containing benzimidazole-type compounds |
| BR9912937A (pt) | 1998-08-10 | 2001-05-08 | Partnership Of Michael E Garst | Pró-drogas de inibidores de bomba de prótons |
| US6733778B1 (en) * | 1999-08-27 | 2004-05-11 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| SE9803772D0 (sv) | 1998-11-05 | 1998-11-05 | Astra Ab | Pharmaceutical formulation |
| UA72748C2 (en) * | 1998-11-10 | 2005-04-15 | Astrazeneca Ab | A novel crystalline form of omeprazole |
| IL142629A0 (en) | 1998-11-18 | 2002-03-10 | Astra Ab | Improved chemical process and pharmaceutical formulation |
| SE9900274D0 (sv) * | 1999-01-28 | 1999-01-28 | Astra Ab | New compound |
| US6852739B1 (en) * | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
| TWI243672B (en) | 1999-06-01 | 2005-11-21 | Astrazeneca Ab | New use of compounds as antibacterial agents |
| EP1191948A2 (en) * | 1999-06-11 | 2002-04-03 | Neorx Corporation | High dose radionuclide complexes for bone marrow suppression |
| US7094885B2 (en) * | 1999-07-11 | 2006-08-22 | Neorx Corporation | Skeletal-targeted radiation to treat bone-associated pathologies |
| ATE306483T1 (de) * | 1999-08-26 | 2005-10-15 | Aaipharma Inc | Alkoxy-substituierte benzimidazolverbindungen , diese enthaltende arzneimittel und ihre verwendung |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| EP1595879A3 (en) * | 1999-08-26 | 2010-01-27 | aaiPharma Inc. | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| 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 |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| 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 |
| AU2878801A (en) * | 1999-10-01 | 2001-05-10 | Natco Pharma Limited | An improved pharmaceutical composition and a process for its preparation |
| DE60036014T2 (de) * | 1999-10-20 | 2008-04-30 | Eisai R&D Management Co., Ltd. | Methode zur stabilisierung von benzimidazol-verbindungen |
| SE9903831D0 (sv) | 1999-10-22 | 1999-10-22 | Astra Ab | Formulation of substituted benzimidazoles |
| AU5424500A (en) | 2000-02-24 | 2001-09-03 | Kopran Res Lab Ltd | Orally administrable acid stable anti-ulcer benzimidazole derivatives |
| SE0000774D0 (sv) | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| CA2409258A1 (en) * | 2000-05-15 | 2001-11-22 | Ranbaxy Laboratories Limited | Novel amorphous form of omeprazole salts |
| US6306435B1 (en) * | 2000-06-26 | 2001-10-23 | Yung Shin Pharmaceutical Industrial Co. Ltd. | Oral pharmaceutical preparation embedded in an oily matrix and methods of making the same |
| CA2386716C (en) * | 2002-05-17 | 2012-07-24 | Bernard Charles Sherman | Magnesium salt of s-omeprazole |
| AU2003204233B8 (en) * | 2000-08-04 | 2008-06-26 | Bernard Charles Sherman | Magnesium salt of S-omeprazole |
| ATE342263T1 (de) | 2000-08-04 | 2006-11-15 | Takeda Pharmaceutical | Salze von benzimidazol-derivaten und deren verwendung |
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| EP3239146A4 (en) | 2014-12-26 | 2018-05-30 | The University of Tokyo | Method for producing proton pump inhibitor compound having optical activity |
| ES2615637T3 (es) | 2015-03-06 | 2017-06-07 | F.I.S.- Fabbrica Italiana Sintetici S.P.A. | Procedimiento mejorado para la purificación óptica del esomeprazol |
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| OU02 | Decision according to article 73(2) ipa 1992, publication of decision on partial fulfilment of the invention and change of patent claims |
Effective date: 20091118 |