JP2010535743A - オルメサルタンメドキソミルの調製のための方法 - Google Patents
オルメサルタンメドキソミルの調製のための方法 Download PDFInfo
- Publication number
- JP2010535743A JP2010535743A JP2010519469A JP2010519469A JP2010535743A JP 2010535743 A JP2010535743 A JP 2010535743A JP 2010519469 A JP2010519469 A JP 2010519469A JP 2010519469 A JP2010519469 A JP 2010519469A JP 2010535743 A JP2010535743 A JP 2010535743A
- Authority
- JP
- Japan
- Prior art keywords
- olmesartan medoxomil
- base
- trityl
- organic solvent
- process according
- 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.)
- Pending
Links
- 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 66
- 238000000034 method Methods 0.000 title claims abstract description 63
- 239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 title claims abstract description 56
- 229960001199 olmesartan medoxomil Drugs 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 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 claims abstract description 71
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 24
- 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 claims description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 11
- QCLFSYYUWPUWQR-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one Chemical compound CC=1OC(=O)OC=1CCl QCLFSYYUWPUWQR-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 4
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 3
- AMEKVNNTFGYYTQ-UHFFFAOYSA-N ethyl 2-propyl-1h-imidazole-5-carboxylate Chemical compound CCCC1=NC=C(C(=O)OCC)N1 AMEKVNNTFGYYTQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 abstract description 5
- 239000002585 base Substances 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- 238000005580 one pot reaction Methods 0.000 description 18
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 2-hydroxypropan-2-yl Chemical group 0.000 description 8
- 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 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000005804 alkylation reaction Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000002955 isolation Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HXXOPVULXOEHTK-UHFFFAOYSA-N 4-methyl-1,3-dioxol-2-one Chemical compound CC1=COC(=O)O1 HXXOPVULXOEHTK-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006642 detritylation reaction Methods 0.000 description 2
- RYYGFMDEVYVZGY-UHFFFAOYSA-N ethyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate Chemical compound CCCC1=NC(C(C)(C)O)=C(C(=O)OCC)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 RYYGFMDEVYVZGY-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 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 2
- ALWQOCCSPUVEKX-UHFFFAOYSA-N 2-trityltetrazole Chemical compound N1=CN=NN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ALWQOCCSPUVEKX-UHFFFAOYSA-N 0.000 description 1
- QYIOFABFKUOIBV-UHFFFAOYSA-N 4,5-dimethyl-1,3-dioxol-2-one Chemical class CC=1OC(=O)OC=1C QYIOFABFKUOIBV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07114004A EP2036904A1 (en) | 2007-08-08 | 2007-08-08 | A process for the preparation of olmesartan medoxomil |
| EP07114000A EP2022790A1 (en) | 2007-08-08 | 2007-08-08 | A process for the preparation or purification of olmesartan medoxomil |
| PCT/EP2008/060400 WO2009019304A1 (en) | 2007-08-08 | 2008-08-07 | A process for the preparation of olmesartan medoxomil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2010535743A true JP2010535743A (ja) | 2010-11-25 |
Family
ID=39789494
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010519469A Pending JP2010535743A (ja) | 2007-08-08 | 2008-08-07 | オルメサルタンメドキソミルの調製のための方法 |
| JP2010519468A Expired - Fee Related JP5685082B2 (ja) | 2007-08-08 | 2008-08-07 | オルメサルタンメドキソミルの調製または精製の方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010519468A Expired - Fee Related JP5685082B2 (ja) | 2007-08-08 | 2008-08-07 | オルメサルタンメドキソミルの調製または精製の方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20110224271A1 (enExample) |
| EP (2) | EP2176253B1 (enExample) |
| JP (2) | JP2010535743A (enExample) |
| CN (2) | CN101778842B (enExample) |
| AT (1) | ATE528305T1 (enExample) |
| BR (2) | BRPI0815111A2 (enExample) |
| CA (2) | CA2707365A1 (enExample) |
| SI (1) | SI2176253T1 (enExample) |
| WO (2) | WO2009019304A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010535742A (ja) * | 2007-08-08 | 2010-11-25 | レツク・フアーマシユーテイカルズ・デー・デー | オルメサルタンメドキソミルの調製または精製の方法 |
| JP2014524887A (ja) * | 2011-05-19 | 2014-09-25 | ハンミ ファイン ケミカル カンパニー，リミテッド | アジルサルタンの改善された製造方法 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101630885B1 (ko) | 2008-06-09 | 2016-06-15 | 다이이찌 산쿄 가부시키가이샤 | 1-비페닐메틸이미다졸 화합물의 제조 방법 |
| CA2760031C (en) * | 2009-04-28 | 2015-03-10 | Daiichi Sankyo Company, Limited | Acetone solvate crystals of trityl olmesartan medoxomil |
| 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 |
| CA2769704A1 (en) * | 2009-07-31 | 2011-02-03 | 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 |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007017135A2 (en) * | 2005-07-29 | 2007-02-15 | Krka | Process for the preparation of olmesartan medoxomil |
| WO2008043996A2 (en) * | 2006-10-09 | 2008-04-17 | Cipla Limited | Process for preparing trityl olmesartan medoxomil and olmesartan medoxomil |
| JP2010535742A (ja) * | 2007-08-08 | 2010-11-25 | レツク・フアーマシユーテイカルズ・デー・デー | オルメサルタンメドキソミルの調製または精製の方法 |
Family Cites Families (13)
| 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 |
| ATE199548T1 (de) * | 1992-06-02 | 2001-03-15 | Sankyo Co | 4-carboxyimidazolderivate als angiotensin-ii- antagonisten und ihre therapeutische verwendung |
| 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. |
| CN1993355A (zh) * | 2004-09-02 | 2007-07-04 | 特瓦制药工业有限公司 | 奥美沙坦酯的纯化方法 |
| JP4437141B2 (ja) * | 2004-09-02 | 2010-03-24 | テバ ファーマシューティカル インダストリーズ リミティド | オルメサルタンメドキソミルの精製法 |
| 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 |
| 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 |
| CA2654218C (en) * | 2006-04-07 | 2014-07-22 | Lek Pharmaceuticals D.D. | Process for the preparation of pure irbesartan |
| US8048904B2 (en) | 2006-06-19 | 2011-11-01 | Matrix Laboratories Ltd. | Process for the preparation of olmesartan medoxomil |
-
2008
- 2008-08-07 CA CA2707365A patent/CA2707365A1/en not_active Abandoned
- 2008-08-07 JP JP2010519469A patent/JP2010535743A/ja active Pending
- 2008-08-07 SI SI200830507T patent/SI2176253T1/sl unknown
- 2008-08-07 AT AT08786993T patent/ATE528305T1/de not_active IP Right Cessation
- 2008-08-07 CN CN200880102267.4A patent/CN101778842B/zh not_active Expired - Fee Related
- 2008-08-07 WO PCT/EP2008/060400 patent/WO2009019304A1/en not_active Ceased
- 2008-08-07 CA CA2707334A patent/CA2707334C/en not_active Expired - Fee Related
- 2008-08-07 BR BRPI0815111-3A2A patent/BRPI0815111A2/pt not_active Application Discontinuation
- 2008-08-07 US US12/672,264 patent/US20110224271A1/en not_active Abandoned
- 2008-08-07 EP EP08786993A patent/EP2176253B1/en not_active Not-in-force
- 2008-08-07 US US12/672,267 patent/US8592474B2/en active Active
- 2008-08-07 JP JP2010519468A patent/JP5685082B2/ja not_active Expired - Fee Related
- 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 EP EP08786996.2A patent/EP2173741B1/en not_active Not-in-force
- 2008-08-07 CN CN200880102268A patent/CN101778843A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007017135A2 (en) * | 2005-07-29 | 2007-02-15 | Krka | Process for the preparation of olmesartan medoxomil |
| WO2008043996A2 (en) * | 2006-10-09 | 2008-04-17 | Cipla Limited | Process for preparing trityl olmesartan medoxomil and olmesartan medoxomil |
| JP2010535742A (ja) * | 2007-08-08 | 2010-11-25 | レツク・フアーマシユーテイカルズ・デー・デー | オルメサルタンメドキソミルの調製または精製の方法 |
Non-Patent Citations (1)
| Title |
|---|
| JPN6013018821; ＹＡＮＡＧＩＳＡＷＡ，Ｈ． ｅｔ ａｌ: Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．３９, 1996, ｐ．３２３-３３８ * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010535742A (ja) * | 2007-08-08 | 2010-11-25 | レツク・フアーマシユーテイカルズ・デー・デー | オルメサルタンメドキソミルの調製または精製の方法 |
| JP2014524887A (ja) * | 2011-05-19 | 2014-09-25 | ハンミ ファイン ケミカル カンパニー，リミテッド | アジルサルタンの改善された製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110224271A1 (en) | 2011-09-15 |
| WO2009019303A3 (en) | 2009-04-02 |
| WO2009019303A2 (en) | 2009-02-12 |
| EP2176253A2 (en) | 2010-04-21 |
| CA2707334A1 (en) | 2009-02-12 |
| US8592474B2 (en) | 2013-11-26 |
| JP5685082B2 (ja) | 2015-03-18 |
| CA2707365A1 (en) | 2009-02-12 |
| JP2010535742A (ja) | 2010-11-25 |
| BRPI0815111A2 (pt) | 2015-01-27 |
| US20110263666A1 (en) | 2011-10-27 |
| CN101778842B (zh) | 2014-10-29 |
| CN101778843A (zh) | 2010-07-14 |
| CA2707334C (en) | 2015-11-24 |
| EP2173741A1 (en) | 2010-04-14 |
| EP2173741B1 (en) | 2013-10-02 |
| ATE528305T1 (de) | 2011-10-15 |
| CN101778842A (zh) | 2010-07-14 |
| EP2176253B1 (en) | 2011-10-12 |
| WO2009019304A1 (en) | 2009-02-12 |
| BRPI0815134A2 (pt) | 2015-02-03 |
| SI2176253T1 (sl) | 2012-02-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010535743A (ja) | オルメサルタンメドキソミルの調製のための方法 | |
| TWI439457B (zh) | （ｓ）－２－胺基－３－（４－（２－胺基－６－（（ｒ）－１－（４－氯－２－（３－甲基－１ｈ－吡唑－１－基）苯基）－２，２，２－三氟乙氧）－嘧啶－４－基）苯基）丙酸乙酯之固體形式與其使用方法 | |
| JP2010018638A (ja) | 相間移動触媒を用いるｎ−置換複素環式誘導体の製造法 | |
| CN1050187A (zh) | 新的喹啉化合物及其制备方法 | |
| US9663490B2 (en) | Process for making reverse transcriptase inhibitors | |
| EP2036904A1 (en) | A process for the preparation of olmesartan medoxomil | |
| CA2619955A1 (en) | Process for preparing valsartan | |
| JP2012523444A (ja) | 内皮受容体アンタゴニスト（ボセンタン）を調製するための方法 | |
| WO2014012880A1 (en) | Process for the preparation of intermediates for the synthesis of dabigatran etexilate, and crystalline forms of said intermediates | |
| US7943780B2 (en) | Process for the preparation of candesartan cilexetil | |
| US8212051B2 (en) | Process for the preparation of pure irbesartan | |
| JP2010254692A (ja) | パリペリドンの精製方法 | |
| US6673939B2 (en) | Process for the preparation of 1,2,4-triazolin-5-one derivatives | |
| JP2007112800A (ja) | アンジオテンシンｉｉ拮抗化合物の製造方法 | |
| ES2264641B1 (es) | Procedimiento para la obtencion de derivados de bencimidazol y sus intermedios. | |
| JP2012232980A (ja) | 新規製造方法 | |
| EP2022790A1 (en) | A process for the preparation or purification of olmesartan medoxomil | |
| KR20100110438A (ko) | 올메살탄의 신규한 에스테르 화합물, 이의 중간체, 이의 제조방법 및 이를 포함하는 조성물 | |
| WO2008041957A1 (en) | Method for producing pure crystalline form of 2-n-butyl-3-((2-(1h-tetrazole-5-yl) (1,1'-biphenyl)-4-methyl)-1,3-diazapspiro (4,4') non -1- en-4-one | |
| KR20080070745A (ko) | 유기 화합물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110802 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20130206 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20130311 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130423 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20131105 |