JP2009527509A5 - - Google Patents
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- Publication number
- JP2009527509A5 JP2009527509A5 JP2008555597A JP2008555597A JP2009527509A5 JP 2009527509 A5 JP2009527509 A5 JP 2009527509A5 JP 2008555597 A JP2008555597 A JP 2008555597A JP 2008555597 A JP2008555597 A JP 2008555597A JP 2009527509 A5 JP2009527509 A5 JP 2009527509A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetrazol
- biphenyl
- imidazole
- chloro
- 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.)
- Granted
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 48
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims description 37
- -1 1,3-dihydro-3-oxo-iso Benzofuran-1-yl Chemical group 0.000 claims description 35
- 235000010290 biphenyl Nutrition 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 22
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- 230000011987 methylation Effects 0.000 claims description 10
- 238000007069 methylation reaction Methods 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 7
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 7
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- KLWYPRNPRNPORS-UHFFFAOYSA-N ethyl 1h-imidazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=CN1 KLWYPRNPRNPORS-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 102000005862 Angiotensin II Human genes 0.000 claims 1
- 101800000733 Angiotensin-2 Proteins 0.000 claims 1
- 239000002083 C09CA01 - Losartan Substances 0.000 claims 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims 1
- 229950006323 angiotensin ii Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 229940127088 antihypertensive drug Drugs 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229960000519 losartan potassium Drugs 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000000243 solution Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 0 *C(c1c2cccc1)OC2=O Chemical compound *C(c1c2cccc1)OC2=O 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 1
- GWFALVUXAGYMHR-UHFFFAOYSA-N 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one Chemical compound CC=1OC(=O)OC=1CBr GWFALVUXAGYMHR-UHFFFAOYSA-N 0.000 description 1
- DVTFHPFIWRQJLP-UHFFFAOYSA-N CC(OCCl)OC(C)(C)C Chemical compound CC(OCCl)OC(C)(C)C DVTFHPFIWRQJLP-UHFFFAOYSA-N 0.000 description 1
- OPTCHSMAUQAOEX-UHFFFAOYSA-N CCC(O1)=C(C)OC1=O Chemical compound CCC(O1)=C(C)OC1=O OPTCHSMAUQAOEX-UHFFFAOYSA-N 0.000 description 1
- UXABWSFGZWKARE-UHFFFAOYSA-N CCCCC(C(Cc(cc1)ccc1-c(cccc1)c1-c1nnn[nH]1)CC1)=NC(Cl)=C1C(O)=O Chemical compound CCCCC(C(Cc(cc1)ccc1-c(cccc1)c1-c1nnn[nH]1)CC1)=NC(Cl)=C1C(O)=O UXABWSFGZWKARE-UHFFFAOYSA-N 0.000 description 1
- RTFGZMKXMSDULM-UHFFFAOYSA-N chloromethyl ethyl carbonate Chemical compound CCOC(=O)OCCl RTFGZMKXMSDULM-UHFFFAOYSA-N 0.000 description 1
- JHYNXXBAHWPABC-UHFFFAOYSA-N chloromethyl propan-2-yl carbonate Chemical compound CC(C)OC(=O)OCCl JHYNXXBAHWPABC-UHFFFAOYSA-N 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006100239910A CN101024643A (zh) | 2006-02-20 | 2006-02-20 | 咪唑－5－羧酸类衍生物、制备方法及其应用 |
| CN200610023991.0 | 2006-02-20 | ||
| PCT/CN2006/001914 WO2007095789A1 (en) | 2006-02-20 | 2006-07-31 | Imidazol-5-carboxylic acid derivatives, preparation methods and use therrof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009527509A JP2009527509A (ja) | 2009-07-30 |
| JP2009527509A5 true JP2009527509A5 (enExample) | 2009-09-24 |
| JP5250760B2 JP5250760B2 (ja) | 2013-07-31 |
Family
ID=38436915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008555597A Expired - Fee Related JP5250760B2 (ja) | 2006-02-20 | 2006-07-31 | イミダゾール−５−カルボン酸系誘導体、製造方法及びその応用 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | USRE44873E1 (enExample) |
| EP (1) | EP1988090B1 (enExample) |
| JP (1) | JP5250760B2 (enExample) |
| KR (1) | KR101179110B1 (enExample) |
| CN (2) | CN101024643A (enExample) |
| AU (1) | AU2006338796B2 (enExample) |
| CA (1) | CA2643005C (enExample) |
| DK (1) | DK1988090T3 (enExample) |
| ES (1) | ES2424154T3 (enExample) |
| PL (1) | PL1988090T3 (enExample) |
| PT (1) | PT1988090E (enExample) |
| WO (1) | WO2007095789A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101024643A (zh) | 2006-02-20 | 2007-08-29 | 上海艾力斯医药科技有限公司 | 咪唑－5－羧酸类衍生物、制备方法及其应用 |
| ATE525371T1 (de) * | 2006-12-06 | 2011-10-15 | Shanghai Allist Pharmaceutical Inc | Salze von imidazol-5-carbonsäure-derivaten, herstellungsverfahren und verwendung davon |
| CN101214242A (zh) * | 2007-01-05 | 2008-07-09 | 上海艾力斯医药科技有限公司 | 新的药用组合物 |
| CN101317842A (zh) * | 2007-06-07 | 2008-12-10 | 上海艾力斯医药科技有限公司 | 一种咪唑-5-羧酸衍生物的治疗用途 |
| CN101407511B (zh) | 2007-10-11 | 2013-01-09 | 上海艾力斯生物医药有限公司 | 一种结晶型的咪唑-5-羧酸衍生物 |
| US8207208B2 (en) * | 2008-05-15 | 2012-06-26 | Merck Sharp & Dohme Corp. | Angiotensin II receptor antagonists |
| CN101596189A (zh) * | 2008-06-05 | 2009-12-09 | 上海艾力斯生物医药有限公司 | 含有咪唑-5-羧酸类衍生物的药用组合物 |
| JP5575783B2 (ja) * | 2008-12-12 | 2014-08-20 | ファーマコステック カンパニー リミテッド | トリフェニルメタン保護基の除去方法 |
| KR101213467B1 (ko) * | 2010-04-30 | 2012-12-20 | 진양제약주식회사 | 로자탄 대사체 이엑스피-3174 이수화물의 신규한 제조 방법 |
| CN103012377A (zh) * | 2011-09-27 | 2013-04-03 | 江苏艾力斯生物医药有限公司 | 一种咪唑-5-羧酸酯的重结晶方法 |
| CN102558064B (zh) * | 2012-01-29 | 2014-04-16 | 安润医药科技（苏州）有限公司 | 抗高血压化合物及其制备方法和应用，以及其在药学上可接受的盐 |
| CN104610232B (zh) * | 2013-11-01 | 2019-09-20 | 深圳信立泰药业股份有限公司 | 阿利沙坦酯无定形及其制备方法及含所述无定形的药物组合物 |
| CN103965171A (zh) * | 2014-04-30 | 2014-08-06 | 上海艾力斯医药科技有限公司 | 一种阿利沙坦酯的制备方法 |
| CN106188012B (zh) * | 2014-06-20 | 2018-11-30 | 深圳信立泰药业股份有限公司 | 一种阿利沙坦酯结晶及其制备方法及含有该结晶的药物组合物 |
| CN105218527B (zh) * | 2015-10-10 | 2018-04-24 | 江苏宝众宝达药业有限公司 | 一种exp-3174的制备方法 |
| EP3406610B1 (en) | 2016-01-20 | 2025-03-05 | Shenzhen Salubris Pharmaceuticals Co., Ltd | Angiotensin ii receptor antagonist metabolite and nep inhibitor composite, and preparation method thereof |
| CN119371408B (zh) * | 2024-12-27 | 2025-04-22 | 安徽艾立德制药有限公司 | 一种无定形的阿利沙坦酯及其制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138069A (en) | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| CA1334092C (en) * | 1986-07-11 | 1995-01-24 | David John Carini | Angiotensin ii receptor blocking imidazoles |
| US5196444A (en) | 1990-04-27 | 1993-03-23 | Takeda Chemical Industries, Ltd. | 1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate and compositions and methods of pharmaceutical use thereof |
| US5616599A (en) * | 1991-02-21 | 1997-04-01 | Sankyo Company, Limited | Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use |
| AT398202B (de) * | 1991-10-04 | 1994-10-25 | Chem Pharm Forsch Gmbh | Neue imidazolderivate, verfahren zu ihrer herstellung und ihre verwendung |
| ATE199548T1 (de) * | 1992-06-02 | 2001-03-15 | Sankyo Co | 4-carboxyimidazolderivate als angiotensin-ii- antagonisten und ihre therapeutische verwendung |
| JPH083162A (ja) * | 1994-04-19 | 1996-01-09 | Tanabe Seiyaku Co Ltd | イミダゾピリジン誘導体及びその製法 |
| CZ297975B6 (cs) * | 1995-06-07 | 2007-05-09 | G. D. Searle & Co. | Farmaceutická kombinace antagonisty receptoru proangiotensin II a epoxymexrenonu pro lécení kardiovaskulárních poruch |
| US20060276523A1 (en) * | 2003-07-31 | 2006-12-07 | Nicoletta Almirante | Nitoroxy derivatives of losartan, valsatan, candesartan, telmisartan, eprosartan and olmesartan as angiotensin-II receptor blockers for the treatment of cardiovascular diseases |
| EP1668008A4 (en) * | 2003-08-28 | 2009-02-25 | Nitromed Inc | NITROSED AND NITROSYLATED DIETETIC COMPOUNDS, COMPOSITIONS AND APPLICATION METHODS |
| ES2334386T3 (es) | 2005-04-22 | 2010-03-09 | Daiichi Sankyo Company, Limited | Producto farmaceutico para la prevencion o el tratamiento de una enfermedad metabolica osea. |
| CN101024643A (zh) | 2006-02-20 | 2007-08-29 | 上海艾力斯医药科技有限公司 | 咪唑－5－羧酸类衍生物、制备方法及其应用 |
| ATE525371T1 (de) | 2006-12-06 | 2011-10-15 | Shanghai Allist Pharmaceutical Inc | Salze von imidazol-5-carbonsäure-derivaten, herstellungsverfahren und verwendung davon |
| CN101214242A (zh) | 2007-01-05 | 2008-07-09 | 上海艾力斯医药科技有限公司 | 新的药用组合物 |
| CN101317842A (zh) | 2007-06-07 | 2008-12-10 | 上海艾力斯医药科技有限公司 | 一种咪唑-5-羧酸衍生物的治疗用途 |
| CN101407511B (zh) | 2007-10-11 | 2013-01-09 | 上海艾力斯生物医药有限公司 | 一种结晶型的咪唑-5-羧酸衍生物 |
-
2006
- 2006-02-20 CN CNA2006100239910A patent/CN101024643A/zh active Pending
- 2006-07-31 ES ES06775249T patent/ES2424154T3/es active Active
- 2006-07-31 DK DK06775249.3T patent/DK1988090T3/da active
- 2006-07-31 AU AU2006338796A patent/AU2006338796B2/en not_active Ceased
- 2006-07-31 KR KR1020087022811A patent/KR101179110B1/ko not_active Expired - Fee Related
- 2006-07-31 EP EP06775249.3A patent/EP1988090B1/en not_active Not-in-force
- 2006-07-31 US US13/727,587 patent/USRE44873E1/en active Active
- 2006-07-31 CA CA2643005A patent/CA2643005C/en not_active Expired - Fee Related
- 2006-07-31 PT PT67752493T patent/PT1988090E/pt unknown
- 2006-07-31 US US11/576,094 patent/US7858651B2/en active Active
- 2006-07-31 CN CNB2006800003978A patent/CN100506818C/zh active Active
- 2006-07-31 PL PL06775249T patent/PL1988090T3/pl unknown
- 2006-07-31 WO PCT/CN2006/001914 patent/WO2007095789A1/zh not_active Ceased
- 2006-07-31 JP JP2008555597A patent/JP5250760B2/ja not_active Expired - Fee Related
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