DK2612851T3 - Fremgangsmåde til fremstilling af L-argininsaltet af perindopril - Google Patents
Fremgangsmåde til fremstilling af L-argininsaltet af perindopril Download PDFInfo
- Publication number
- DK2612851T3 DK2612851T3 DK13150305.4T DK13150305T DK2612851T3 DK 2612851 T3 DK2612851 T3 DK 2612851T3 DK 13150305 T DK13150305 T DK 13150305T DK 2612851 T3 DK2612851 T3 DK 2612851T3
- Authority
- DK
- Denmark
- Prior art keywords
- perindopril
- arginine
- arginine salt
- acetonitrile
- mixture
- Prior art date
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Classifications
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (5)
1. Fremgangsmåde til fremstilling af L-argininsaltet af perindopril med formlen C):
ved reaktion mellem perindopril og L-arginin i et opløsningsmiddelsystem valgt blandt: en binær blanding af acetonitril og dimethylsulfoxid, en binær blanding af ethylacetat og dimethylsulfoxid, en ternær blanding af acetonitril, dimethylsulfoxid og toluen, ved en temperatur på 10 til 100°C, efterfulgt af isolering af det således opnåede L-argininsalt ved filtrering.
2. Fremgangsmåde til fremstilling af L-argininsaltet af perindopril ifølge krav 1, hvor perindoprilet er opnået ved omsætning af N-[1-(S)-ethoxycarbonyl-butyl]-(S)-alanin med formlen (II):
med et aktiveringsmiddel med formlen X2C=0, hvor X betegner en fraspaltelig enhed, i et organisk opløsningsmiddel eller system af organiske opløsningsmidler, ved en temperatur på -20 til 80°C, efterfulgt af omsætning af det således opnåede mellemprodukt med formlen (III):
(Ill) med (2S, 3aS, 7aS)-2-carboxyperhydroindol, ved en temperatur på O til 80°C, og derefter omsætning af det således opnåede perindopril med L-arginin ved fremgangsmåden ifølge krav 1.
3. Fremgangsmåde til fremstilling af L-argininsalt af perindopril ifølge krav 2, hvor aktiveringsmidlet er Ν,Ν'-carbonyldiimidazol, phosgen, triphosgen, (1,1 '-car-bonyldi(1,2,4-triazol) eller di(N-succinimidyl)carbonat.
4. Fremgangsmåde til fremstilling af L-argininsalt af perindopril ifølge krav 3, hvor aktiveringsmidlet er Ν,Ν'-carbonyldiimidazol, og mængden af N,N'-carbonyl-diimidazol er på mellem 0,8 og 1,2 mol pr. mol N-[1-(S)-ethoxycarbonyl-butyl]-(S)-alanin. 5 Fremgangsmåde til fremstilling af L-argininsalt af perindopril ifølge et hvilket som helst af kravene 2-4, hvor mængden af (2S, 3aS, 7aS)-2-carboxyperhydro-indol er på mellem 0,8 og 1,2 mol pr. mol N-[1-(S)-ethoxycarbonyl-butyl]-(S)-ala-nin.
6. Fremgangsmåde til fremstilling af L-argininsalt af perindopril ifølge krav 1, hvor perindoprilet er opnået ved afsaltning af perindopril-tert-butylamin ved indvirkning af en syre, og det således opnåede perindopril derefter omsættes med L-arginin ved fremgangsmåden ifølge krav 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1200034A FR2985512B1 (fr) | 2012-01-05 | 2012-01-05 | Procede de preparation du sel de l-arginine du perindopril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2612851T3 true DK2612851T3 (da) | 2016-10-03 |
Family
ID=47427278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13150305.4T DK2612851T3 (da) | 2012-01-05 | 2013-01-04 | Fremgangsmåde til fremstilling af L-argininsaltet af perindopril |
Country Status (46)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016178591A2 (en) | 2015-05-05 | 2016-11-10 | Gene Predit, Sa | Genetic markers and treatment of male obesity |
| TWI544987B (zh) | 2015-10-27 | 2016-08-11 | 財團法人工業技術研究院 | 輕便型動力工具 |
| US10430658B2 (en) | 2017-10-06 | 2019-10-01 | Steve Rad | Augmented reality system and kit |
| WO2019071209A1 (en) | 2017-10-06 | 2019-04-11 | Rad Steve | SYSTEM AND KIT OF INCREASED REALITY |
| CN110283104B (zh) * | 2018-08-22 | 2022-06-14 | 南京济群医药科技股份有限公司 | 一种精氨酸培哚普利的制备方法 |
| CN112047999B (zh) * | 2020-09-18 | 2022-12-02 | 天津力生制药股份有限公司 | 一种γ晶型的精氨酸培哚普利盐的制备方法 |
| CN114149357B (zh) * | 2021-12-29 | 2024-06-25 | 江苏嘉逸医药有限公司 | 一种γ晶型培哚普利精氨酸盐的制备方法 |
| CN114894940B (zh) * | 2022-06-02 | 2024-09-06 | 江苏嘉逸医药有限公司 | 一种高效液相色谱法测定精氨酸培哚普利中杂质的方法 |
Family Cites Families (12)
| 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 |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| AR036187A1 (es) * | 2001-07-24 | 2004-08-18 | Adir | Un proceso para la preparacion de perindopril, compuestos analogos y sus sales, compuesto intermediario 2,5-dioxo-oxazolidina y proceso para preparar un intermediario |
| FR2838648B1 (fr) * | 2002-04-18 | 2004-05-21 | Servier Lab | Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent |
| CN100472337C (zh) | 2003-09-18 | 2009-03-25 | 澳大利亚研究实验室持股有限公司 | 提高液体静电印刷调色剂或液体喷墨油墨的物理性质和电性质的方法 |
| US7291745B2 (en) * | 2005-03-21 | 2007-11-06 | Glenmark Pharmaceuticals Limited | Process for the preparation of perindopril |
| FR2897865B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline beta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2897866B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline alpha du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| EP1864973A1 (en) * | 2006-06-09 | 2007-12-12 | Sochinaz SA | Process for the preparation of perindopril and salts thereof |
| AU2009263737B2 (en) * | 2008-06-24 | 2013-10-24 | Mylan Laboratories Ltd. | Novel polymorphic forms of Perindopril (L)-Arginine and process for the preparation thereof |
| AU2009212902A1 (en) | 2008-09-03 | 2010-03-18 | Apotex Pharmachem Inc. | Amorphous form of an L-arginine salt of perindopril and processes of preparation thereof |
| SI23001A (sl) * | 2009-03-20 | 2010-09-30 | Diagen@d@o@o | Nove soli perindoprila nov postopek za njihovo pripravo in njihova uporaba za zdravljenje kardiovaskularnih bolezni |
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2012
- 2012-01-05 FR FR1200034A patent/FR2985512B1/fr not_active Expired - Fee Related
- 2012-12-18 PH PH12012000392A patent/PH12012000392A1/en unknown
- 2012-12-19 JO JOP/2012/0384A patent/JO3196B1/ar active
- 2012-12-19 CR CR20120654A patent/CR20120654A/es unknown
- 2012-12-19 SG SG2012093589A patent/SG192337A1/en unknown
- 2012-12-20 PE PE2012002463A patent/PE20131098A1/es not_active Application Discontinuation
- 2012-12-20 AU AU2012268816A patent/AU2012268816B2/en active Active
- 2012-12-20 IL IL223753A patent/IL223753A/en active IP Right Grant
- 2012-12-25 TN TNP2012000620A patent/TN2012000620A1/fr unknown
- 2012-12-26 CO CO12232909A patent/CO6700138A1/es unknown
- 2012-12-27 NI NI201200195A patent/NI201200195A/es unknown
- 2012-12-27 MY MYPI2012701295A patent/MY160902A/en unknown
- 2012-12-27 TW TW101150662A patent/TWI449693B/zh active
- 2012-12-27 UY UY0001034553A patent/UY34553A/es unknown
- 2012-12-28 MD MDA20120129A patent/MD4415C1/ro active IP Right Grant
- 2012-12-28 EA EA201201667A patent/EA022573B1/ru unknown
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2013
- 2013-01-02 MA MA35525A patent/MA35001B1/fr unknown
- 2013-01-02 AP AP2013006655A patent/AP2013006655A0/xx unknown
- 2013-01-02 SA SA113340172A patent/SA113340172B1/ar unknown
- 2013-01-03 AR ARP130100016A patent/AR089632A1/es not_active Application Discontinuation
- 2013-01-03 CA CA 2801089 patent/CA2801089C/fr active Active
- 2013-01-03 UA UAA201300118A patent/UA111333C2/uk unknown
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- 2013-01-03 US US13/733,353 patent/US8865915B2/en active Active
- 2013-01-04 ES ES13150305.4T patent/ES2595236T3/es active Active
- 2013-01-04 CU CUP2013000003A patent/CU24293B1/xx unknown
- 2013-01-04 WO PCT/FR2013/050017 patent/WO2013102740A1/fr active Application Filing
- 2013-01-04 KR KR1020130001012A patent/KR101502946B1/ko active IP Right Grant
- 2013-01-04 EP EP13150305.4A patent/EP2612851B1/fr active Active
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- 2013-01-04 BR BR102013000256-9A patent/BR102013000256B1/pt active IP Right Grant
- 2013-01-04 LT LTEP13150305.4T patent/LT2612851T/lt unknown
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- 2013-01-04 RS RS20160720A patent/RS55096B1/sr unknown
- 2013-01-04 CN CN201310001282.2A patent/CN103193863B/zh active Active
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- 2013-01-04 EC ECSP13012366 patent/ECSP13012366A/es unknown
- 2013-01-04 SI SI201330308A patent/SI2612851T1/sl unknown
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2016
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