JP2007533727A5 - - Google Patents
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- Publication number
- JP2007533727A5 JP2007533727A5 JP2007509005A JP2007509005A JP2007533727A5 JP 2007533727 A5 JP2007533727 A5 JP 2007533727A5 JP 2007509005 A JP2007509005 A JP 2007509005A JP 2007509005 A JP2007509005 A JP 2007509005A JP 2007533727 A5 JP2007533727 A5 JP 2007533727A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- temperature
- organic
- 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
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- 150000001875 compounds Chemical class 0.000 claims 22
- 238000000034 method Methods 0.000 claims 22
- 150000007530 organic bases Chemical class 0.000 claims 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- 150000007529 inorganic bases Chemical class 0.000 claims 9
- 239000003960 organic solvent Substances 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 238000006467 substitution reaction Methods 0.000 claims 7
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 239000000543 intermediate Substances 0.000 claims 6
- 150000002941 palladium compounds Chemical class 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000003944 tolyl group Chemical group 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 4
- 239000012429 reaction media Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 229960004295 valine Drugs 0.000 claims 4
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims 3
- 230000006181 N-acylation Effects 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000005580 one pot reaction Methods 0.000 claims 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 125000005270 trialkylamine group Chemical group 0.000 claims 3
- -1 trimethylsilyl (TMS) Chemical group 0.000 claims 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 claims 3
- 229960004699 valsartan Drugs 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 2
- 238000009739 binding Methods 0.000 claims 2
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003536 tetrazoles Chemical group 0.000 claims 2
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical group C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 238000010626 work up procedure Methods 0.000 claims 2
- XSCGSICSNALYDV-VWMHFEHESA-N (2s)-2-amino-3-methylbutanoic acid;4-methylbenzenesulfonic acid Chemical group CC(C)[C@H](N)C(O)=O.CC1=CC=C(S(O)(=O)=O)C=C1 XSCGSICSNALYDV-VWMHFEHESA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 claims 1
- 101150003085 Pdcl gene Proteins 0.000 claims 1
- GVRXWYFECKHTSJ-UHFFFAOYSA-N [2-(2h-tetrazol-5-yl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=NNN=N1 GVRXWYFECKHTSJ-UHFFFAOYSA-N 0.000 claims 1
- CCCUVHHPYBWVOW-UHFFFAOYSA-K [Na+].[Na+].[Na+].[O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1 Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1 CCCUVHHPYBWVOW-UHFFFAOYSA-K 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 0 CC(C)C(C(O)=O)NCc1ccc(*)cc1 Chemical compound CC(C)C(C(O)=O)NCc1ccc(*)cc1 0.000 description 2
- ACWBQPMHZXGDFX-UHFFFAOYSA-N CCCCC(N(Cc(cc1)ccc1-c1ccccc1-c1nnn[nH]1)C(C(C)C)C(O)=O)=O Chemical compound CCCCC(N(Cc(cc1)ccc1-c1ccccc1-c1nnn[nH]1)C(C(C)C)C(O)=O)=O ACWBQPMHZXGDFX-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200400949A ES2251292B1 (es) | 2004-04-20 | 2004-04-20 | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y de sus intermedios de sintesis. |
| PCT/IB2005/001100 WO2005102987A1 (en) | 2004-04-20 | 2005-04-18 | Process for the preparation of valsartan and precursors thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007533727A JP2007533727A (ja) | 2007-11-22 |
| JP2007533727A5 true JP2007533727A5 (enExample) | 2008-07-03 |
Family
ID=34966329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007509005A Pending JP2007533727A (ja) | 2004-04-20 | 2005-04-18 | バルサルタンおよびその前駆体の製造方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7728021B2 (enExample) |
| EP (1) | EP1747190B1 (enExample) |
| JP (1) | JP2007533727A (enExample) |
| KR (1) | KR20060135959A (enExample) |
| AT (1) | ATE401300T1 (enExample) |
| DE (1) | DE602005008224D1 (enExample) |
| ES (2) | ES2251292B1 (enExample) |
| PL (1) | PL1747190T3 (enExample) |
| PT (1) | PT1747190E (enExample) |
| SI (1) | SI1747190T1 (enExample) |
| TW (1) | TWI283576B (enExample) |
| WO (1) | WO2005102987A1 (enExample) |
| ZA (1) | ZA200608986B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200505879A (en) | 2003-04-21 | 2005-02-16 | Teva Pharma | Process for the preparation of valsartan |
| EP1838681A2 (en) * | 2004-12-22 | 2007-10-03 | Enantia, S.L. | Intermediate compounds for the preparation of an angiotensin ii receptor and process for the preparation of valsartan |
| ES2259909B1 (es) * | 2005-02-28 | 2007-06-16 | Inke, S.A. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y de su intermedio de sintesis. |
| EP1812411A2 (en) * | 2005-07-05 | 2007-08-01 | Teva Pharmaceutical Industries Ltd. | Process for preparing valsartan |
| ES2288376B1 (es) * | 2005-10-20 | 2008-11-01 | Inke, S.A. | Procedimiento para la obtencion de intermedios utiles en la obtencion de un compuesto farmaceuticamente activo. |
| ITMI20051989A1 (it) * | 2005-10-20 | 2007-04-21 | Dipharma Spa | Procedimerntyo per la preparazione di composti antagonisti di angiotensina ii |
| WO2007071750A1 (en) * | 2005-12-22 | 2007-06-28 | Enantia, S.L. | Intermediates and processes for the preparation of valsartan |
| ES2300175B1 (es) * | 2006-02-14 | 2009-06-08 | Inke, S.A. | Procedimiento para la obtencion de intermedios utiles en la obtencion de un compuesto farmaceuticamente activo. |
| WO2008007391A2 (en) * | 2006-07-10 | 2008-01-17 | Manne Satyanarayana Reddy | An improved process for the preparation of valsartan |
| ATE412640T1 (de) * | 2007-06-07 | 2008-11-15 | Inke Sa | Verfahren zur gewinnung eines zur gewinnung von valsartan nützlichen valsartan-salzes |
| US8492577B2 (en) | 2008-04-07 | 2013-07-23 | Hetero Research Foundation | Process for preparation of valsartan intermediate |
| KR101012135B1 (ko) * | 2008-12-18 | 2011-02-07 | 주식회사 대희화학 | 발사르탄 메틸 에스테르의 제조방법 |
| CN102702118B (zh) * | 2012-06-11 | 2014-04-16 | 吉林三善恩科技开发有限公司 | 一种缬沙坦有机药物共晶及其制备方法 |
| CN103804313B (zh) * | 2014-01-27 | 2015-12-09 | 云南现代民族药工程技术研究中心 | 一种简洁的低成本高效率制备缬沙坦的方法 |
| US9687475B1 (en) | 2016-03-24 | 2017-06-27 | Ezra Pharma Llc | Extended release pharmaceutical formulations with controlled impurity levels |
| US9675585B1 (en) | 2016-03-24 | 2017-06-13 | Ezra Pharma | Extended release pharmaceutical formulations |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL97219A (en) * | 1990-02-19 | 1995-12-08 | Ciba Geigy Ag | Biphenyl substituted aliphatic amino compounds process for their preparation and pharmaceutical compositions containing them |
| DE4319041A1 (de) * | 1992-10-23 | 1994-04-28 | Bayer Ag | Trisubstituierte Biphenyle |
| DE4319040A1 (de) | 1992-10-23 | 1994-04-28 | Bayer Ag | Alkoxymethylsubstituierte Pyridonbiphenyle |
| DE4313747A1 (de) * | 1993-04-27 | 1994-11-03 | Bayer Ag | Verfahren zur Herstellung von substituierten Biphenyltetrazolen |
| DE4320432A1 (de) * | 1993-06-21 | 1994-12-22 | Bayer Ag | Substituierte Mono- und Bipyridylmethylderivate |
| DE4407488A1 (de) | 1994-03-07 | 1995-09-14 | Bayer Ag | Verwendung von Biphenyl- und Pyridylmethylpyridonen |
| DK0782996T3 (da) | 1994-09-20 | 1999-09-20 | Wakunaga Seiyaku Kk | Fremgangsmåde til fremstilling af N-biphenylmethylthiadiazolinderivat eller salt deraf og mellemprodukt til fremstilling af |
| US6207665B1 (en) * | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
| IL156811A0 (en) * | 2001-01-19 | 2004-02-08 | Pharmacopeia Inc | Bisaryl derivatives and pharmaceutical compositions containing the same |
| GB0121033D0 (en) * | 2001-08-30 | 2001-10-24 | Novartis Ag | Organic compounds |
-
2004
- 2004-04-20 ES ES200400949A patent/ES2251292B1/es not_active Expired - Fee Related
-
2005
- 2005-04-18 ZA ZA200608986A patent/ZA200608986B/en unknown
- 2005-04-18 TW TW094112179A patent/TWI283576B/zh not_active IP Right Cessation
- 2005-04-18 DE DE602005008224T patent/DE602005008224D1/de not_active Expired - Fee Related
- 2005-04-18 ES ES05733764T patent/ES2309741T3/es not_active Expired - Lifetime
- 2005-04-18 KR KR1020067024308A patent/KR20060135959A/ko not_active Ceased
- 2005-04-18 PL PL05733764T patent/PL1747190T3/pl unknown
- 2005-04-18 WO PCT/IB2005/001100 patent/WO2005102987A1/en not_active Ceased
- 2005-04-18 EP EP05733764A patent/EP1747190B1/en not_active Expired - Lifetime
- 2005-04-18 AT AT05733764T patent/ATE401300T1/de not_active IP Right Cessation
- 2005-04-18 JP JP2007509005A patent/JP2007533727A/ja active Pending
- 2005-04-18 SI SI200530408T patent/SI1747190T1/sl unknown
- 2005-04-18 PT PT05733764T patent/PT1747190E/pt unknown
- 2005-04-18 US US11/568,054 patent/US7728021B2/en not_active Expired - Fee Related
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