CA2707334C - A process for the preparation or purification of olmesartan medoxomil - Google Patents
A process for the preparation or purification of olmesartan medoxomil Download PDFInfo
- Publication number
- CA2707334C CA2707334C CA2707334A CA2707334A CA2707334C CA 2707334 C CA2707334 C CA 2707334C CA 2707334 A CA2707334 A CA 2707334A CA 2707334 A CA2707334 A CA 2707334A CA 2707334 C CA2707334 C CA 2707334C
- Authority
- CA
- Canada
- Prior art keywords
- olmesartan medoxomil
- hydrohalide salt
- acid
- process according
- olmesartan
- 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
- 239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 title claims abstract description 172
- 229960001199 olmesartan medoxomil Drugs 0.000 title claims abstract description 172
- UQGKUQLKSCSZGY-UHFFFAOYSA-N Olmesartan medoxomil Chemical compound C=1C=C(C=2C(=CC=CC=2)C2=NNN=N2)C=CC=1CN1C(CCC)=NC(C(C)(C)O)=C1C(=O)OCC=1OC(=O)OC=1C UQGKUQLKSCSZGY-UHFFFAOYSA-N 0.000 title claims abstract description 133
- 238000000034 method Methods 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000000746 purification Methods 0.000 title abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 7
- 206010020772 Hypertension Diseases 0.000 claims abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 34
- 239000003960 organic solvent Substances 0.000 claims description 32
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 238000002329 infrared spectrum Methods 0.000 claims description 17
- 238000002441 X-ray diffraction Methods 0.000 claims description 12
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000012296 anti-solvent Substances 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 230000015556 catabolic process Effects 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 29
- 239000002244 precipitate Substances 0.000 description 18
- IJOPLMOXIPGJIJ-UHFFFAOYSA-N (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate Chemical compound C=1C=C(C=2C(=CC=CC=2)C=2N(N=NN=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1CN1C(CCC)=NC(C(C)(C)O)=C1C(=O)OCC=1OC(=O)OC=1C IJOPLMOXIPGJIJ-UHFFFAOYSA-N 0.000 description 17
- 239000002585 base Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- -1 by Yanagisawa et al Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 238000006642 detritylation reaction Methods 0.000 description 3
- KZBJJAFGNMRRHN-UHFFFAOYSA-N ethyl 5-(2-hydroxypropan-2-yl)-2-propyl-1h-imidazole-4-carboxylate Chemical compound CCCC1=NC(C(=O)OCC)=C(C(C)(C)O)N1 KZBJJAFGNMRRHN-UHFFFAOYSA-N 0.000 description 3
- VTRAEEWXHOVJFV-UHFFFAOYSA-N olmesartan Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 VTRAEEWXHOVJFV-UHFFFAOYSA-N 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000005480 Olmesartan Substances 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical group [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229960005117 olmesartan Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- ZTFVTXDWDFIQEU-UHFFFAOYSA-N 5-[2-[4-(bromomethyl)phenyl]phenyl]-1-trityltetrazole Chemical compound C1=CC(CBr)=CC=C1C1=CC=CC=C1C1=NN=NN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZTFVTXDWDFIQEU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102000008873 Angiotensin II receptor Human genes 0.000 description 1
- 108050000824 Angiotensin II receptor Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 229910002483 Cu Ka Inorganic materials 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000004102 olmesartan derivatives Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07114000A EP2022790A1 (en) | 2007-08-08 | 2007-08-08 | A process for the preparation or purification of olmesartan medoxomil |
| EP07114004.0 | 2007-08-08 | ||
| EP07114004A EP2036904A1 (en) | 2007-08-08 | 2007-08-08 | A process for the preparation of olmesartan medoxomil |
| EP07114000.8 | 2007-08-08 | ||
| PCT/EP2008/060396 WO2009019303A2 (en) | 2007-08-08 | 2008-08-07 | A process for the preparation or purification of olmesartan medoxomil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2707334A1 CA2707334A1 (en) | 2009-02-12 |
| CA2707334C true CA2707334C (en) | 2015-11-24 |
Family
ID=39789494
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2707365A Abandoned CA2707365A1 (en) | 2007-08-08 | 2008-08-07 | A process for the preparation of olmesartan medoxomil |
| CA2707334A Expired - Fee Related CA2707334C (en) | 2007-08-08 | 2008-08-07 | A process for the preparation or purification of olmesartan medoxomil |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2707365A Abandoned CA2707365A1 (en) | 2007-08-08 | 2008-08-07 | A process for the preparation of olmesartan medoxomil |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8592474B2 (OSRAM) |
| EP (2) | EP2176253B1 (OSRAM) |
| JP (2) | JP5685082B2 (OSRAM) |
| CN (2) | CN101778842B (OSRAM) |
| AT (1) | ATE528305T1 (OSRAM) |
| BR (2) | BRPI0815111A2 (OSRAM) |
| CA (2) | CA2707365A1 (OSRAM) |
| SI (1) | SI2176253T1 (OSRAM) |
| WO (2) | WO2009019304A1 (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2176253B1 (en) * | 2007-08-08 | 2011-10-12 | LEK Pharmaceuticals d.d. | A process for the preparation or purification of olmesartan medoxomil or olmesartan medoxomil hydrohalide salt |
| HUE025230T2 (en) | 2008-06-09 | 2016-02-29 | Daiichi Sankyo Co Ltd | Process for the preparation of 1-biphenylmethylimidazole compound |
| ES2753874T3 (es) | 2009-04-28 | 2020-04-14 | Daiichi Sankyo Co Ltd | Cristales de solvato novedosos |
| ES2527686T3 (es) | 2009-04-28 | 2015-01-28 | Daiichi Sankyo Company, Limited | Procedimiento de producción de olmesartán medoxomil |
| WO2011007368A2 (en) * | 2009-07-14 | 2011-01-20 | Cadila Healthcare Limited | An improved process for preparation of olmesartan |
| US20120184751A1 (en) * | 2009-07-31 | 2012-07-19 | Ranbaxy Laboratories Limited | Polymorphic form of olmesartan medoxomil |
| WO2011021224A2 (en) * | 2009-08-19 | 2011-02-24 | Msn Laboratories Limited | Process for (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl4-(1-hydroxy-1-methylethyl)-2-propyl-1-[4-[2-tetrazol-5-yl)phenyl]phenyl]methylimidazole-5-carboxylate |
| CZ2010785A3 (cs) * | 2010-10-29 | 2012-05-16 | Zentiva, K.S. | Zpusob výroby olmesartanu medoxomilu |
| KR101275092B1 (ko) * | 2011-05-19 | 2013-06-17 | 한미정밀화학주식회사 | 아질사르탄의 개선된 제조방법 |
| CN102351849B (zh) * | 2011-10-26 | 2013-10-02 | 齐鲁天和惠世制药有限公司 | 一种奥美沙坦酯的制备方法 |
| CN103304550B (zh) * | 2012-03-16 | 2016-01-27 | 湖南欧亚生物有限公司 | 一种奥美沙坦酯的制备方法 |
| CN103319461A (zh) * | 2013-07-02 | 2013-09-25 | 临海天宇药业有限公司 | 奥美沙坦酯中间体的制备方法以及奥美沙坦酯的合成方法 |
| CN103435602A (zh) * | 2013-07-31 | 2013-12-11 | 山东省医学科学院药物研究所 | 一种奥美沙坦酯的制备方法 |
| CN104262332A (zh) * | 2014-09-16 | 2015-01-07 | 上海信谊百路达药业有限公司 | 一种奥美沙坦酯的制备方法 |
| CN104447715B (zh) * | 2014-11-28 | 2017-06-20 | 山东新华制药股份有限公司 | 奥美沙坦酯的制备方法 |
| CN104817546B (zh) * | 2015-05-20 | 2020-02-07 | 浙江华海药业股份有限公司 | 一种奥美沙坦酯母液回收的方法 |
| CN107311990B (zh) * | 2017-07-25 | 2021-09-03 | 浙江华海致诚药业有限公司 | 一种奥美沙坦酯的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5616599A (en) * | 1991-02-21 | 1997-04-01 | Sankyo Company, Limited | Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use |
| ES2155827T3 (es) * | 1992-06-02 | 2001-06-01 | Sankyo Co | 4-carboxiimidazoles como antagonistas de la angiotensina ii y su uso terapeutico. |
| JP2001226372A (ja) * | 1999-12-06 | 2001-08-21 | Sumika Fine Chemicals Co Ltd | ロサルタンの結晶性または結晶化された酸付加塩およびロサルタンの精製方法 |
| ITMI20032338A1 (it) * | 2003-11-28 | 2005-05-29 | Dinamite Dipharma S P A In Forma A Bbreviata Diph | Composti feniltetrazolici. |
| CN1976926A (zh) | 2004-09-02 | 2007-06-06 | 特瓦制药工业有限公司 | 奥美沙坦酯的制备 |
| WO2006029057A1 (en) * | 2004-09-02 | 2006-03-16 | Teva Pharmaceutical Industries, Ltd. | Purification of olmesartan medoxomil |
| GB2419592A (en) * | 2004-10-26 | 2006-05-03 | Cipla Ltd | Process for the preparation of irbesartan hydrochloride |
| US20060281800A1 (en) | 2005-04-12 | 2006-12-14 | Glenmark Pharmaceuticals Limited | Polymorphic form of olmesartan and process for its preparation |
| US7943779B2 (en) * | 2005-07-29 | 2011-05-17 | Krka | Process for the preparation of olmesartan medoxomil |
| EP1816131A1 (en) | 2006-02-06 | 2007-08-08 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the preparation of olmesartan medoxomil |
| WO2007052301A2 (en) | 2005-08-31 | 2007-05-10 | Alembic Limited | Process for the preparation of irbesartan |
| EP1801111B1 (en) | 2005-12-20 | 2014-07-16 | LEK Pharmaceuticals d.d. | Novel polymorph forms of olmesartan medoxomil |
| US8212051B2 (en) * | 2006-04-07 | 2012-07-03 | Lek Pharmaceuticals, D.D. | Process for the preparation of pure irbesartan |
| WO2007148344A2 (en) | 2006-06-19 | 2007-12-27 | Matrix Laboratories Limited | Process for the preparation of olmesartan medoxomil |
| NZ575780A (en) | 2006-10-09 | 2011-09-30 | Cipla Ltd | Process for preparing trityl olmesartan medoxomil and olmesartan medoxomil |
| EP2176253B1 (en) * | 2007-08-08 | 2011-10-12 | LEK Pharmaceuticals d.d. | A process for the preparation or purification of olmesartan medoxomil or olmesartan medoxomil hydrohalide salt |
-
2008
- 2008-08-07 EP EP08786993A patent/EP2176253B1/en not_active Not-in-force
- 2008-08-07 BR BRPI0815111-3A2A patent/BRPI0815111A2/pt not_active Application Discontinuation
- 2008-08-07 US US12/672,267 patent/US8592474B2/en not_active Expired - Fee Related
- 2008-08-07 CN CN200880102267.4A patent/CN101778842B/zh not_active Expired - Fee Related
- 2008-08-07 JP JP2010519468A patent/JP5685082B2/ja not_active Expired - Fee Related
- 2008-08-07 EP EP08786996.2A patent/EP2173741B1/en not_active Not-in-force
- 2008-08-07 CA CA2707365A patent/CA2707365A1/en not_active Abandoned
- 2008-08-07 CN CN200880102268A patent/CN101778843A/zh active Pending
- 2008-08-07 JP JP2010519469A patent/JP2010535743A/ja active Pending
- 2008-08-07 AT AT08786993T patent/ATE528305T1/de not_active IP Right Cessation
- 2008-08-07 US US12/672,264 patent/US20110224271A1/en not_active Abandoned
- 2008-08-07 WO PCT/EP2008/060400 patent/WO2009019304A1/en not_active Ceased
- 2008-08-07 BR BRPI0815134-2A2A patent/BRPI0815134A2/pt not_active Application Discontinuation
- 2008-08-07 WO PCT/EP2008/060396 patent/WO2009019303A2/en not_active Ceased
- 2008-08-07 SI SI200830507T patent/SI2176253T1/sl unknown
- 2008-08-07 CA CA2707334A patent/CA2707334C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2176253A2 (en) | 2010-04-21 |
| EP2173741A1 (en) | 2010-04-14 |
| BRPI0815134A2 (pt) | 2015-02-03 |
| JP5685082B2 (ja) | 2015-03-18 |
| BRPI0815111A2 (pt) | 2015-01-27 |
| CN101778842A (zh) | 2010-07-14 |
| SI2176253T1 (sl) | 2012-02-29 |
| CA2707365A1 (en) | 2009-02-12 |
| US8592474B2 (en) | 2013-11-26 |
| CN101778843A (zh) | 2010-07-14 |
| JP2010535742A (ja) | 2010-11-25 |
| US20110224271A1 (en) | 2011-09-15 |
| ATE528305T1 (de) | 2011-10-15 |
| US20110263666A1 (en) | 2011-10-27 |
| EP2173741B1 (en) | 2013-10-02 |
| EP2176253B1 (en) | 2011-10-12 |
| JP2010535743A (ja) | 2010-11-25 |
| WO2009019304A1 (en) | 2009-02-12 |
| CA2707334A1 (en) | 2009-02-12 |
| WO2009019303A3 (en) | 2009-04-02 |
| CN101778842B (zh) | 2014-10-29 |
| WO2009019303A2 (en) | 2009-02-12 |
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