NZ575780A - Process for preparing trityl olmesartan medoxomil and olmesartan medoxomil - Google Patents
Process for preparing trityl olmesartan medoxomil and olmesartan medoxomilInfo
- Publication number
- NZ575780A NZ575780A NZ575780A NZ57578007A NZ575780A NZ 575780 A NZ575780 A NZ 575780A NZ 575780 A NZ575780 A NZ 575780A NZ 57578007 A NZ57578007 A NZ 57578007A NZ 575780 A NZ575780 A NZ 575780A
- Authority
- NZ
- New Zealand
- Prior art keywords
- process according
- acid
- olmesartan medoxomil
- formula
- alkali metal
- Prior art date
Links
- 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 title claims abstract description 44
- 239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 title claims description 39
- 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 description 39
- 229960001199 olmesartan medoxomil Drugs 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 71
- -1 trityl biphenyl bromide Chemical compound 0.000 claims abstract description 27
- 239000002585 base Substances 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 12
- 150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 12
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 11
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 59
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229940113088 dimethylacetamide Drugs 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 150000007522 mineralic acids Chemical class 0.000 claims description 12
- 238000010511 deprotection reaction Methods 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000002027 dichloromethane extract Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 150000003460 sulfonic acids Chemical class 0.000 claims 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 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 238000002955 isolation Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229940050176 methyl chloride Drugs 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 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 4
- 239000005480 Olmesartan Substances 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 229960005117 olmesartan Drugs 0.000 description 4
- 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 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000006642 detritylation reaction Methods 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- GWUMKPSVXXQYKZ-UHFFFAOYSA-N 2-(2-propyl-1H-imidazol-5-yl)propan-2-ol Chemical compound OC(C)(C)C=1N=C(NC1)CCC GWUMKPSVXXQYKZ-UHFFFAOYSA-N 0.000 description 1
- XUZAELSNXSKADN-UHFFFAOYSA-N 5-(2-hydroxypropan-2-yl)-3-[[4-phenyl-3-(2H-tetrazol-5-yl)phenyl]methyl]-2-propylimidazole-4-carboxylic acid Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC(C=C1C2=NNN=N2)=CC=C1C1=CC=CC=C1 XUZAELSNXSKADN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-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
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 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 1
- TZQDBKJBKJIHPR-UHFFFAOYSA-N ethyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(1-trityltetrazol-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=2N(N=NN=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 TZQDBKJBKJIHPR-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- KEXCCKULFIYUHC-UHFFFAOYSA-M lithium;5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate Chemical compound [Li+].CCCC1=NC(C(C)(C)O)=C(C([O-])=O)N1CC1=CC=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=C1 KEXCCKULFIYUHC-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1663MU2006 | 2006-10-09 | ||
| PCT/GB2007/003821 WO2008043996A2 (en) | 2006-10-09 | 2007-10-09 | Process for preparing trityl olmesartan medoxomil and olmesartan medoxomil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ575780A true NZ575780A (en) | 2011-09-30 |
Family
ID=39149309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ575780A NZ575780A (en) | 2006-10-09 | 2007-10-09 | Process for preparing trityl olmesartan medoxomil and olmesartan medoxomil |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8076492B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2074116A2 (cg-RX-API-DMAC10.html) |
| JP (1) | JP5269798B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR101458369B1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU2007306171B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2663981C (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ575780A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2008043996A2 (cg-RX-API-DMAC10.html) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101458369B1 (ko) | 2006-10-09 | 2014-11-05 | 씨아이피엘에이 엘티디. | 트리틸 올메사탄 메독소밀 및 올메사탄 메독소밀의 제조방법 |
| ATE528305T1 (de) | 2007-08-08 | 2011-10-15 | Lek Pharmaceuticals | Verfahren zur herstellung oder reinigung von olmesartan-medoxomil oder von olmesartan- medoxomil-hydrohalid-salz |
| EP2036904A1 (en) * | 2007-08-08 | 2009-03-18 | LEK Pharmaceuticals D.D. | A process for the preparation of olmesartan medoxomil |
| EP2298763B1 (en) | 2008-06-09 | 2015-03-25 | Daiichi Sankyo Company, Limited | Method for producing 1-biphenylmethylimidazole compound |
| MY150973A (en) | 2008-12-17 | 2014-03-31 | Daiichi Sankyo Co Ltd | Method for producing diamine derivative |
| WO2010104078A1 (ja) | 2009-03-10 | 2010-09-16 | 第一三共株式会社 | ジアミン誘導体の製造方法 |
| US8859600B2 (en) * | 2009-04-28 | 2014-10-14 | Daiichi Sankyo Company, Limited | Acetone solvate crystals of trityl olmesartan medoxomil |
| CA2759163C (en) | 2009-04-28 | 2015-02-17 | Daiichi Sankyo Company, Limited | Method for producing olmesartan medoxomil |
| JP2012527446A (ja) * | 2009-05-20 | 2012-11-08 | ランバクシー ラボラトリーズ リミテッド | オルメサルタン・メドキソミルの調製方法 |
| WO2011007368A2 (en) | 2009-07-14 | 2011-01-20 | Cadila Healthcare Limited | An improved process for preparation of olmesartan |
| 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 |
| KR101257272B1 (ko) * | 2010-01-15 | 2013-04-23 | 종근당바이오 주식회사 | 탈보호화 반응을 이용한 고혈압 치료용 비페닐테트라졸 화합물의 제조방법 |
| KR101628758B1 (ko) * | 2010-03-31 | 2016-06-09 | 주식회사 씨티씨바이오 | 올메사탄 실렉세틸의 제조 방법 |
| WO2012001694A1 (en) * | 2010-06-28 | 2012-01-05 | Hetero Research Foundation | Process for olmesartan medoxomil |
| AR083523A1 (es) | 2010-10-29 | 2013-03-06 | Interquim Sa | Procedimiento de obtencion del olmesartan medoxomilo |
| CZ303188B6 (cs) * | 2010-10-29 | 2012-05-16 | Zentiva, K.S. | Zpusob výroby olmesartanu medoxomilu |
| KR101696851B1 (ko) * | 2010-12-21 | 2017-01-17 | 대봉엘에스 주식회사 | 올메사탄 메독소밀의 유연물질의 제조방법 |
| MX2014001298A (es) | 2011-08-05 | 2014-09-01 | Lupin Ltd | Procedimiento para la preparacion de olmesartan medoxomilo. |
| 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 |
| JP5925899B2 (ja) * | 2012-08-31 | 2016-05-25 | 株式会社エーピーアイ コーポレーション | ビアリール化合物の製造方法 |
| IN2015DN02241A (cg-RX-API-DMAC10.html) * | 2012-09-26 | 2015-08-21 | Api Corp | |
| KR101526249B1 (ko) * | 2013-11-14 | 2015-06-10 | 동방에프티엘(주) | 올메사탄 메독소밀 유도체의 개선된 제조방법 |
| CN104592213A (zh) * | 2014-12-15 | 2015-05-06 | 山东新华制药股份有限公司 | 奥美沙坦酯中间体的制备方法 |
Family Cites Families (5)
| 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 |
| US5310929A (en) * | 1992-08-06 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Prodrugs of imidazole carboxylic acids as angiotensin II receptor antagonists |
| CN1271068C (zh) | 2003-03-25 | 2006-08-23 | 上海医药工业研究院 | 一种奥美沙坦酯的制备方法 |
| CA2616466A1 (en) * | 2005-07-29 | 2007-02-15 | Krka | Process for the preparation of olmesartan medoxomil |
| KR101458369B1 (ko) | 2006-10-09 | 2014-11-05 | 씨아이피엘에이 엘티디. | 트리틸 올메사탄 메독소밀 및 올메사탄 메독소밀의 제조방법 |
-
2007
- 2007-10-09 KR KR1020097009497A patent/KR101458369B1/ko not_active Expired - Fee Related
- 2007-10-09 WO PCT/GB2007/003821 patent/WO2008043996A2/en not_active Ceased
- 2007-10-09 NZ NZ575780A patent/NZ575780A/en not_active IP Right Cessation
- 2007-10-09 AU AU2007306171A patent/AU2007306171B2/en not_active Ceased
- 2007-10-09 US US12/444,502 patent/US8076492B2/en not_active Expired - Fee Related
- 2007-10-09 EP EP07824075A patent/EP2074116A2/en not_active Withdrawn
- 2007-10-09 JP JP2009531902A patent/JP5269798B2/ja not_active Expired - Fee Related
- 2007-10-09 CA CA2663981A patent/CA2663981C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2663981C (en) | 2014-05-27 |
| EP2074116A2 (en) | 2009-07-01 |
| US8076492B2 (en) | 2011-12-13 |
| CA2663981A1 (en) | 2008-04-17 |
| KR20090080516A (ko) | 2009-07-24 |
| AU2007306171A1 (en) | 2008-04-17 |
| KR101458369B1 (ko) | 2014-11-05 |
| AU2007306171B2 (en) | 2013-02-21 |
| JP5269798B2 (ja) | 2013-08-21 |
| WO2008043996A2 (en) | 2008-04-17 |
| US20100160643A1 (en) | 2010-06-24 |
| WO2008043996A3 (en) | 2008-10-02 |
| JP2010505926A (ja) | 2010-02-25 |
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