CN100503596C - 纯化6-甲氧基奥美拉唑的方法 - Google Patents
纯化6-甲氧基奥美拉唑的方法 Download PDFInfo
- Publication number
- CN100503596C CN100503596C CNB028084594A CN02808459A CN100503596C CN 100503596 C CN100503596 C CN 100503596C CN B028084594 A CNB028084594 A CN B028084594A CN 02808459 A CN02808459 A CN 02808459A CN 100503596 C CN100503596 C CN 100503596C
- Authority
- CN
- China
- Prior art keywords
- methoxyl group
- methyl
- sulfinyl
- benzoglyoxaline
- pyridyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 229960000381 omeprazole Drugs 0.000 title abstract description 41
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 210000004211 gastric acid Anatomy 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 238000002288 cocrystallisation Methods 0.000 description 3
- 239000006186 oral dosage form Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 238000001237 Raman spectrum Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/839,449 | 2001-04-20 | ||
| US09/839,449 US6608091B2 (en) | 2001-04-20 | 2001-04-20 | Process for purifying 6-methoxy omeprazole |
| US09/839,395 US6673936B2 (en) | 2001-04-20 | 2001-04-20 | Process for purifying 6-methoxy omeprazole |
| US09/839,395 | 2001-04-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1503791A CN1503791A (zh) | 2004-06-09 |
| CN100503596C true CN100503596C (zh) | 2009-06-24 |
Family
ID=27126104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB028084594A Expired - Fee Related CN100503596C (zh) | 2001-04-20 | 2002-04-17 | 纯化6-甲氧基奥美拉唑的方法 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1379518A2 (no) |
| JP (1) | JP2004528331A (no) |
| KR (1) | KR20030088506A (no) |
| CN (1) | CN100503596C (no) |
| CA (1) | CA2443605A1 (no) |
| HU (1) | HUP0304004A2 (no) |
| NO (1) | NO20034679D0 (no) |
| WO (1) | WO2002085312A2 (no) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001013919A1 (en) * | 1999-08-26 | 2001-03-01 | Applied Analytical Industries, Inc. | Ft-raman spectroscopic measurement of omeprazole isomer ratio in a composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5768886A (en) * | 1985-05-24 | 1986-11-27 | G.D. Searle & Co. | 2-((1-h-benzimidazol-2-ylsulfinyl)methyl)benzenamines |
-
2002
- 2002-04-17 WO PCT/US2002/015254 patent/WO2002085312A2/en not_active Application Discontinuation
- 2002-04-17 KR KR10-2003-7013544A patent/KR20030088506A/ko not_active Application Discontinuation
- 2002-04-17 EP EP02736828A patent/EP1379518A2/en not_active Withdrawn
- 2002-04-17 CA CA002443605A patent/CA2443605A1/en not_active Abandoned
- 2002-04-17 HU HU0304004A patent/HUP0304004A2/hu unknown
- 2002-04-17 CN CNB028084594A patent/CN100503596C/zh not_active Expired - Fee Related
- 2002-04-17 JP JP2002582888A patent/JP2004528331A/ja active Pending
-
2003
- 2003-10-20 NO NO20034679A patent/NO20034679D0/no not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001013919A1 (en) * | 1999-08-26 | 2001-03-01 | Applied Analytical Industries, Inc. | Ft-raman spectroscopic measurement of omeprazole isomer ratio in a composition |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030088506A (ko) | 2003-11-19 |
| CA2443605A1 (en) | 2002-10-31 |
| HUP0304004A2 (hu) | 2004-04-28 |
| EP1379518A2 (en) | 2004-01-14 |
| WO2002085312A3 (en) | 2003-04-03 |
| CN1503791A (zh) | 2004-06-09 |
| NO20034679L (no) | 2003-10-20 |
| JP2004528331A (ja) | 2004-09-16 |
| NO20034679D0 (no) | 2003-10-20 |
| WO2002085312A2 (en) | 2002-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20090624 Termination date: 20100417 |