CO6491043A2 - Proceso para la síntesis de ácido (2s, 3ar, 7as)-octahidro-1h- indol carboxílico como intermediario para trandolapril - Google Patents
Proceso para la síntesis de ácido (2s, 3ar, 7as)-octahidro-1h- indol carboxílico como intermediario para trandolaprilInfo
- Publication number
- CO6491043A2 CO6491043A2 CO12005568A CO12005568A CO6491043A2 CO 6491043 A2 CO6491043 A2 CO 6491043A2 CO 12005568 A CO12005568 A CO 12005568A CO 12005568 A CO12005568 A CO 12005568A CO 6491043 A2 CO6491043 A2 CO 6491043A2
- Authority
- CO
- Colombia
- Prior art keywords
- trandolapril
- compound
- octahidro
- indol
- intermediary
- Prior art date
Links
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 title abstract 4
- 229960002051 trandolapril Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- CQYBNXGHMBNGCG-CSMHCCOUSA-N (2s,3ar,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2N[C@H](C(=O)O)C[C@H]21 CQYBNXGHMBNGCG-CSMHCCOUSA-N 0.000 abstract 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 239000005541 ACE inhibitor Substances 0.000 abstract 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 abstract 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 abstract 1
- 229940127291 Calcium channel antagonist Drugs 0.000 abstract 1
- 206010019280 Heart failures Diseases 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 abstract 1
- 230000036772 blood pressure Effects 0.000 abstract 1
- 239000000480 calcium channel blocker Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 229940030606 diuretics Drugs 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- -1 methanesulfonate ester Chemical class 0.000 abstract 1
- 229940126701 oral medication Drugs 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- AHYHTSYNOHNUSH-HXFGRODQSA-N trandolaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 AHYHTSYNOHNUSH-HXFGRODQSA-N 0.000 abstract 1
- 229960002651 trandolaprilat Drugs 0.000 abstract 1
- 229960001722 verapamil Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22603009P | 2009-07-16 | 2009-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO6491043A2 true CO6491043A2 (es) | 2012-07-31 |
Family
ID=42585097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO12005568A CO6491043A2 (es) | 2009-07-16 | 2012-01-16 | Proceso para la síntesis de ácido (2s, 3ar, 7as)-octahidro-1h- indol carboxílico como intermediario para trandolapril |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8288565B2 (https=) |
| EP (1) | EP2454235A1 (https=) |
| JP (1) | JP2012533563A (https=) |
| CN (1) | CN102498098A (https=) |
| AU (1) | AU2010273259B2 (https=) |
| CA (1) | CA2768239A1 (https=) |
| CO (1) | CO6491043A2 (https=) |
| IN (1) | IN2012DN00453A (https=) |
| RU (1) | RU2012103753A (https=) |
| WO (1) | WO2011009021A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111620788B (zh) * | 2020-04-20 | 2022-09-30 | 广东莱佛士制药技术有限公司 | 一种制备(2s,3s)-3-氨基-二环[2.2.2]辛烷-2-甲酸酯的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US487932A (en) | 1892-12-13 | George b | ||
| US4350704A (en) | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
| CA1341296C (en) * | 1981-12-29 | 2001-09-25 | Hansjorg Urbach | 2-azabicycloalkane-3-carboxylic acid derivatives, processes for their preparation, agents containing these compounds and their use |
| US4490386A (en) | 1982-09-23 | 1984-12-25 | Warner-Lambert Company | Phosphate salts of 1-[2-[(1-alkoxycarbonyl-3-aralkyl)-amino]-1-oxoalkyl]octahydro-1H-indole-2-carboxylic acids, preparation of, and medical compositions thereof |
| US4556655A (en) | 1984-09-24 | 1985-12-03 | Schering Corporation | Antihypertensive compounds having both diuretic and angiotensin converting enzyme inhibitory activity |
| FR2605630B1 (fr) | 1986-10-22 | 1989-06-30 | Roussel Uclaf | Procede de preparation de derives de l'octahydroindole et intermediaires de preparation |
| DE19900205A1 (de) | 1999-01-07 | 2000-07-13 | Basf Ag | Verfahren zur Herstellung von (2S,4R,9S)-Octahydro-1H-indol-2-carbonsäure und Zwischenprodukte dafür |
| WO2004065368A1 (ja) | 2003-01-21 | 2004-08-05 | Ohara Chemical Industries, Ltd. | トランドラプリル合成中間体の製造方法 |
| EP1354874B1 (fr) * | 2003-04-15 | 2004-11-24 | Les Laboratoires Servier | Nouveau procédé de synthèse de l'acide (2s, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application a la synthèse du perindopril |
| SI21507A (sl) | 2003-05-16 | 2004-12-31 | LEK farmacevtska dru�ba d.d. | Postopek za pripravo spojin z ace inhibitornim delovanjem |
| EP1687271A1 (en) * | 2003-11-25 | 2006-08-09 | Texcontor Etablissement | A method for the preparation of (2s, 3ar, 7as)-octahydro-1h-indole-2-carboxylic acid as key intermediate in the preparation of trandolapril by reacting a cyclohexyl aziridine with a dialkyl malonate |
| US20070135513A1 (en) | 2003-11-28 | 2007-06-14 | Mirko Pogutter | Method for producing {n-[1-(s)-carbalkoxy-3-phenylpropyl]-s-alanyl-2s, 3ar, 7as-octahydroindole-2-carboxylic acid} compounds |
| WO2006014916A2 (en) | 2004-07-26 | 2006-02-09 | Dr. Reddy's Laboratories Ltd. | Preparation of trandolapril |
| AU2005327440A1 (en) | 2005-02-14 | 2006-08-17 | Lupin Limited | Improved process for preparation of highly pure trandolapril |
| ATE386718T1 (de) | 2005-05-06 | 2008-03-15 | Sochinaz Sa | Verfahren zur herstellung von (2s, 3ar, 7as)- octahydroindole-2-carbonsäure und umwandlung zum trandolapril |
| US7973173B2 (en) | 2005-07-05 | 2011-07-05 | Cipla Limited | Process for the synthesis of an ACE inhibitor |
| US8536198B2 (en) | 2007-07-24 | 2013-09-17 | Bristol-Myers Squibb Company | Piperidine derivatives as modulators of chemokine receptor activity |
| CN101423490B (zh) * | 2008-06-16 | 2012-07-18 | 重庆南松医药科技股份有限公司 | 群多普利关键中间体（2S,3aR,7as）-八氢－1H－吲哚－2－羧酸的合成方法 |
-
2010
- 2010-07-16 AU AU2010273259A patent/AU2010273259B2/en not_active Ceased
- 2010-07-16 US US12/837,686 patent/US8288565B2/en not_active Expired - Fee Related
- 2010-07-16 EP EP10737165A patent/EP2454235A1/en not_active Withdrawn
- 2010-07-16 JP JP2012520807A patent/JP2012533563A/ja active Pending
- 2010-07-16 RU RU2012103753/04A patent/RU2012103753A/ru not_active Application Discontinuation
- 2010-07-16 CN CN2010800413803A patent/CN102498098A/zh active Pending
- 2010-07-16 IN IN453DEN2012 patent/IN2012DN00453A/en unknown
- 2010-07-16 CA CA2768239A patent/CA2768239A1/en not_active Abandoned
- 2010-07-16 WO PCT/US2010/042219 patent/WO2011009021A1/en not_active Ceased
-
2012
- 2012-01-16 CO CO12005568A patent/CO6491043A2/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| AU2010273259B2 (en) | 2013-03-07 |
| IN2012DN00453A (https=) | 2015-05-15 |
| CN102498098A (zh) | 2012-06-13 |
| EP2454235A1 (en) | 2012-05-23 |
| CA2768239A1 (en) | 2011-01-20 |
| WO2011009021A1 (en) | 2011-01-20 |
| RU2012103753A (ru) | 2013-08-27 |
| AU2010273259A1 (en) | 2012-02-09 |
| US20110065930A1 (en) | 2011-03-17 |
| JP2012533563A (ja) | 2012-12-27 |
| US8288565B2 (en) | 2012-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Application granted |