UA72040C2 - A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile - Google Patents
A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile Download PDFInfo
- Publication number
- UA72040C2 UA72040C2 UA2002118916A UA2002118916A UA72040C2 UA 72040 C2 UA72040 C2 UA 72040C2 UA 2002118916 A UA2002118916 A UA 2002118916A UA 2002118916 A UA2002118916 A UA 2002118916A UA 72040 C2 UA72040 C2 UA 72040C2
- Authority
- UA
- Ukraine
- Prior art keywords
- synthesis
- alanine
- perindoprile
- carboxybutyl
- ethers
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000000034 method Methods 0.000 title abstract description 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- 229960003767 alanine Drugs 0.000 title 1
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 abstract 1
- 229960002582 perindopril Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- YERWBBMSDMSDKT-UHFFFAOYSA-N ethyl 2-oxopentanoate Chemical compound CCCC(=O)C(=O)OCC YERWBBMSDMSDKT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0004610A FR2807430B1 (fr) | 2000-04-11 | 2000-04-11 | Nouveau procede de synthese des esters de la n-[(s)-1- carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
| PCT/FR2001/001088 WO2001056972A1 (fr) | 2000-04-11 | 2001-04-10 | Nouveau procede de synthese des esters de la n-[(s)-1-carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA72040C2 true UA72040C2 (en) | 2005-01-17 |
Family
ID=8849107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002118916A UA72040C2 (en) | 2000-04-11 | 2001-10-04 | A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6774259B2 (ru) |
| EP (1) | EP1272454B1 (ru) |
| JP (1) | JP3872344B2 (ru) |
| KR (1) | KR100520700B1 (ru) |
| CN (1) | CN1176903C (ru) |
| AP (1) | AP1417A (ru) |
| AR (1) | AR027782A1 (ru) |
| AT (1) | ATE362913T1 (ru) |
| AU (2) | AU2001250467B2 (ru) |
| BG (1) | BG65833B1 (ru) |
| BR (1) | BR0109963A (ru) |
| CA (1) | CA2405466C (ru) |
| CY (1) | CY1106720T1 (ru) |
| CZ (1) | CZ302603B6 (ru) |
| DE (1) | DE60128554T2 (ru) |
| DK (1) | DK1272454T3 (ru) |
| EA (1) | EA004265B1 (ru) |
| EE (1) | EE05030B1 (ru) |
| ES (1) | ES2287114T3 (ru) |
| FR (1) | FR2807430B1 (ru) |
| GE (1) | GEP20063798B (ru) |
| HK (1) | HK1053300A1 (ru) |
| HR (1) | HRP20020887B1 (ru) |
| HU (1) | HU229189B1 (ru) |
| ME (1) | ME00442B (ru) |
| MX (1) | MXPA02009888A (ru) |
| NO (1) | NO327970B1 (ru) |
| NZ (1) | NZ521846A (ru) |
| OA (1) | OA12246A (ru) |
| PL (1) | PL346553A1 (ru) |
| PT (1) | PT1272454E (ru) |
| RS (1) | RS50240B (ru) |
| SK (1) | SK287067B6 (ru) |
| UA (1) | UA72040C2 (ru) |
| WO (1) | WO2001056972A1 (ru) |
| ZA (1) | ZA200207689B (ru) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2807037B1 (fr) * | 2000-03-31 | 2002-05-10 | Adir | NOUVEAU PROCEDE DE SYNTHESE DES ESTERS DE LA N-[(s)-1- CARBOXYBUTYL]-(S)-ALANINE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL |
| FR2827860B1 (fr) * | 2001-07-24 | 2004-12-10 | Servier Lab | Nouveau procede de synthese de derives de l'acide (2s, 3as, 7as)-1-[(s)-alanyl]-octahydro-1h-indole-2-carboxyline et application a la synthese du perindopril |
| SI1603558T1 (sl) | 2003-02-28 | 2008-12-31 | Servier S A Lab | Postopek za pripravo perindoprila in njegovih soli |
| SI1362845T1 (sl) * | 2003-09-01 | 2010-01-29 | Servier Lab | Nov postopek za pripravo estrov n((s)-1-karboksibutil)-(s)-alanina in uporaba za sintezo perindoprila |
| DE60300806T2 (de) * | 2003-09-30 | 2006-03-23 | Les Laboratoires Servier | Verfahren zur Herstellung von N-((S)-1-(Ethoxycarbonyl)butyl)-(S)-alanin und Verwendung in der Synthese von Perindopril |
| EP1400531B1 (fr) * | 2003-09-30 | 2006-01-04 | Les Laboratoires Servier | Procédé de synthèse de la N-[(S)-1-carbéthoxybutyl]-(S)-alanine et application à la synthèse du perindopril |
| PL1729739T3 (pl) * | 2004-03-29 | 2017-04-28 | Les Laboratoires Servier | Sposób wytwarzania stałej kompozycji farmaceutycznej |
| SI21800A (sl) | 2004-05-14 | 2005-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek sinteze perindoprila |
| EP1792896A1 (en) | 2005-12-01 | 2007-06-06 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the preparation of perindopril and salts thereof |
| FI126564B (fi) | 2011-02-28 | 2017-02-15 | Andritz Oy | Menetelmä ja laitteisto meesan polttamiseksi |
| CN107098949B (zh) * | 2017-04-20 | 2021-03-16 | 上药东英（江苏）药业有限公司 | 一种制备培哚普利叔丁胺盐的绿色合成新工艺 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2503155A2 (fr) * | 1980-10-02 | 1982-10-08 | Science Union & Cie | Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| US4344949A (en) * | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| US4296110A (en) * | 1980-10-28 | 1981-10-20 | E. I. Du Pont De Nemours And Company | Antihypertensive I-substituted cyclic lactam-2-carboxylic acids |
| US4503043A (en) * | 1981-12-07 | 1985-03-05 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acids |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| FR2620699B1 (fr) * | 1987-09-17 | 1990-06-01 | Adir | Procede de synthese d'alpha amino acides n alkyles et de leurs esters. application a la synthese de carboxyalkyl dipeptides |
| FR2620700B1 (fr) * | 1987-09-17 | 1990-06-01 | Adir | Procede de synthese d'alpha amino acides n alkyles et leurs esters. application a la synthese de carboxyalkyl dipeptides |
-
2000
- 2000-04-11 FR FR0004610A patent/FR2807430B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-20 PL PL01346553A patent/PL346553A1/xx not_active Application Discontinuation
- 2001-03-30 HU HU0101337A patent/HU229189B1/hu not_active IP Right Cessation
- 2001-04-09 AR ARP010101670A patent/AR027782A1/es not_active Application Discontinuation
- 2001-04-10 RS YU76702A patent/RS50240B/sr unknown
- 2001-04-10 OA OA1200200313A patent/OA12246A/en unknown
- 2001-04-10 ES ES01923776T patent/ES2287114T3/es not_active Expired - Lifetime
- 2001-04-10 ME MEP-2008-671A patent/ME00442B/me unknown
- 2001-04-10 AU AU2001250467A patent/AU2001250467B2/en not_active Ceased
- 2001-04-10 JP JP2001556822A patent/JP3872344B2/ja not_active Expired - Fee Related
- 2001-04-10 MX MXPA02009888A patent/MXPA02009888A/es active IP Right Grant
- 2001-04-10 AU AU5046701A patent/AU5046701A/xx active Pending
- 2001-04-10 CA CA002405466A patent/CA2405466C/fr not_active Expired - Fee Related
- 2001-04-10 EP EP01923776A patent/EP1272454B1/fr not_active Expired - Lifetime
- 2001-04-10 CZ CZ20023323A patent/CZ302603B6/cs not_active IP Right Cessation
- 2001-04-10 US US10/257,239 patent/US6774259B2/en not_active Expired - Lifetime
- 2001-04-10 BR BR0109963-9A patent/BR0109963A/pt not_active Application Discontinuation
- 2001-04-10 GE GEAP20016688A patent/GEP20063798B/en unknown
- 2001-04-10 EA EA200201049A patent/EA004265B1/ru not_active IP Right Cessation
- 2001-04-10 NZ NZ521846A patent/NZ521846A/en not_active IP Right Cessation
- 2001-04-10 AP APAP/P/2002/002639A patent/AP1417A/en active
- 2001-04-10 WO PCT/FR2001/001088 patent/WO2001056972A1/fr active IP Right Grant
- 2001-04-10 DK DK01923776T patent/DK1272454T3/da active
- 2001-04-10 DE DE60128554T patent/DE60128554T2/de not_active Expired - Lifetime
- 2001-04-10 CN CNB018079210A patent/CN1176903C/zh not_active Expired - Fee Related
- 2001-04-10 AT AT01923776T patent/ATE362913T1/de active
- 2001-04-10 KR KR10-2002-7013604A patent/KR100520700B1/ko not_active IP Right Cessation
- 2001-04-10 PT PT01923776T patent/PT1272454E/pt unknown
- 2001-04-10 SK SK1457-2002A patent/SK287067B6/sk not_active IP Right Cessation
- 2001-04-10 EE EEP200200586A patent/EE05030B1/xx not_active IP Right Cessation
- 2001-10-04 UA UA2002118916A patent/UA72040C2/uk unknown
-
2002
- 2002-09-25 ZA ZA200207689A patent/ZA200207689B/xx unknown
- 2002-10-04 NO NO20024811A patent/NO327970B1/no not_active IP Right Cessation
- 2002-11-04 BG BG107250A patent/BG65833B1/bg unknown
- 2002-11-11 HR HR20020887A patent/HRP20020887B1/xx not_active IP Right Cessation
-
2003
- 2003-08-01 HK HK03105540A patent/HK1053300A1/xx not_active IP Right Cessation
-
2007
- 2007-07-12 CY CY20071100924T patent/CY1106720T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA72040C2 (en) | A method for synthesis of n-[(s)-1-carboxybutyl]-(s)-alanine ethers and use thereof in the synthesis of perindoprile | |
| EP0127411B1 (en) | Method of preparing alpha-l-aspartyl-l-phenylalanine methyl ester and its hydrochloride | |
| CN102964269B (zh) | 碘普罗胺的新制备方法 | |
| HU228925B1 (en) | Method for producing l-phenylephrine hydrochloride | |
| JPH0196194A (ja) | グルタミン誘導体の製造方法 | |
| US6794537B1 (en) | Manufacturing processes for Se-methyl-L-selenocysteine | |
| Myers et al. | A one-step synthesis of pseudoephedrine glycinamide, a versatile precursor for the synthesis of α-amino acids | |
| UA73562C2 (ru) | Способ синтеза n-[(s)-1-карбоксибутил]-(s)-аланиновых эфиров и их применение в синтезе периндоприла | |
| KR20010033648A (ko) | β-할로게노-α-아미노카르복실산 및 페닐시스테인유도체와, 그의 중간체의 제조 방법 | |
| JP3762980B2 (ja) | アミノ基導入法及びアミノ酸の合成方法 | |
| US11453648B2 (en) | Method for producing orotic acid derivative | |
| JPS59225152A (ja) | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法 | |
| JP6716903B2 (ja) | ジペプチドの製造方法 | |
| Ariyoshi et al. | The synthesis of a sweet peptide, α-l-aspartyl-l-phenylalanine methyl ester, without the use of protecting groups | |
| JP3400105B2 (ja) | 光学活性スルホン酸誘導体およびその製法 | |
| JP4405675B2 (ja) | Ｎ−（１（ｓ）−エトキシカルボニル−３−フェニルプロピル）−ｌ−アラニル−ｌ−プロリンのマレイン酸塩の晶出方法 | |
| SU576937A3 (ru) | Способ получени моно- - оксиэтил-7-рутина | |
| WO2007143886A1 (fr) | Procédé amélioré de synthèse de l-théanine | |
| JPS60156658A (ja) | カルボン酸の製造法 | |
| JPH0940675A (ja) | 新規なイミダゾピロロキノリン化合物 | |
| CN104293844A (zh) | 一种特拉匹韦中间体的合成方法 | |
| KR950005766B1 (ko) | 4-히드록시 만델산의 제조방법 | |
| CA1331255C (en) | Method of producing -l-aspartyl-l-phenylalanine methyl ester hydrochloride | |
| Lautens et al. | Palladium-Catalyzed Synthesis of Alkenylated α, β-Unsaturated Lactams | |
| CN115353892A (zh) | 一种阴离子和两性离子复合表面活性剂的合成方法 |