MD4415C1 - Procedeu de preparare a formei cristaline delta a sării perindopril-L-arginină - Google Patents
Procedeu de preparare a formei cristaline delta a sării perindopril-L-argininăInfo
- Publication number
- MD4415C1 MD4415C1 MDA20120129A MD20120129A MD4415C1 MD 4415 C1 MD4415 C1 MD 4415C1 MD A20120129 A MDA20120129 A MD A20120129A MD 20120129 A MD20120129 A MD 20120129A MD 4415 C1 MD4415 C1 MD 4415C1
- Authority
- MD
- Moldova
- Prior art keywords
- perindopril
- arginine salt
- preparation
- crystalline form
- arginine
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- RYCSJJXKEWBUTI-YDYAIEMNSA-N perindopril arginine Chemical compound OC(=O)[C@@H](N)CCCNC(N)=N.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 RYCSJJXKEWBUTI-YDYAIEMNSA-N 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 abstract 1
- 229930064664 L-arginine Natural products 0.000 abstract 1
- 235000014852 L-arginine Nutrition 0.000 abstract 1
- 150000008535 L-arginines Chemical class 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 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
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 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
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (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)
Abstract
Prezenta invenţie se referă la un procedeu de preparare a sării de L-arginină a perindoprilului cu formula (I):ce cuprinde reacţia dintre perindopril şi L-arginină într-un amestec de solvenţi selectat dintr-un:amestec binar de acetonitril şi dimetilsulfoxid,amestec binar de acetat de etil şi dimetilsulfoxid,amestec ternar de acetonitril, dimetilsulfoxid şi toluen,la o temperatură cuprinsă între 10 şi 100°C,urmată de izolarea prin filtrare a sării de L-arginină obţinută în acest mod.Procedeul descris permite de a obţine sare de L-arginină a perindoprilului cu un randament bun şi de o puritate excelentă, totodată izolarea sării din amestecul de reacţie are loc foarte uşor.
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 (3)
| Publication Number | Publication Date |
|---|---|
| MD20120129A2 MD20120129A2 (ro) | 2013-07-31 |
| MD4415B1 MD4415B1 (ro) | 2016-04-30 |
| MD4415C1 true MD4415C1 (ro) | 2016-11-30 |
Family
ID=47427278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20120129A MD4415C1 (ro) | 2012-01-05 | 2012-12-28 | Procedeu de preparare a formei cristaline delta a sării perindopril-L-arginină |
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 |
| EP3692520A4 (en) | 2017-10-06 | 2021-07-28 | Rad, Steve | AUGMENTED REALITY SYSTEM AND KIT |
| US10430658B2 (en) | 2017-10-06 | 2019-10-01 | Steve Rad | Augmented reality system and kit |
| 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 |
| CN114149357A (zh) * | 2021-12-29 | 2022-03-08 | 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 |
| CN114894940A (zh) * | 2022-06-02 | 2022-08-12 | 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 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0049658A1 (fr) * | 1980-10-02 | 1982-04-14 | Adir | Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant |
| EP1279665A2 (en) * | 2001-07-24 | 2003-01-29 | Adir | A process for the preparation of perindopril, its analogous compounds and salts thereof using 2,5-dioxo-oxazolidine intermediate compounds |
| EP1354873A1 (fr) * | 2002-04-18 | 2003-10-22 | Les Laboratoires Servier | Sel de périndopril et les compositions pharmaceutiques qui le contiennent |
| WO2007099216A2 (fr) * | 2006-02-28 | 2007-09-07 | Les Laboratoires Servier | FORME CRISTALLINE β DU SEL D'ARGININE DU PERINDOPRIL, SON PROCEDE DE PREPARATION, ET LES COMPOSITIONS PHARMACEUTIQUES QUI LA CONTIENNENT |
| EP1989182A1 (fr) * | 2006-02-28 | 2008-11-12 | Les Laboratoires Servier | Forme cristalline du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| WO2009157018A2 (en) * | 2008-06-24 | 2009-12-30 | Matrix Laboratories Ltd | Novel polymorphic forms of perindopril (l)-arginine and process for the 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| US7451943B2 (en) | 2003-09-18 | 2008-11-18 | Research Laboratories Of Australia Pty Ltd. | Marking liquid method of preparation and product produced thereby |
| US7291745B2 (en) * | 2005-03-21 | 2007-11-06 | Glenmark Pharmaceuticals Limited | Process for the preparation of perindopril |
| EP1864973A1 (en) * | 2006-06-09 | 2007-12-12 | Sochinaz SA | Process for the preparation of perindopril and salts 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 |
-
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 AU AU2012268816A patent/AU2012268816B2/en active Active
- 2012-12-20 PE PE2012002463A patent/PE20131098A1/es not_active Application Discontinuation
- 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 UY UY0001034553A patent/UY34553A/es unknown
- 2012-12-27 MY MYPI2012701295A patent/MY160902A/en unknown
- 2012-12-27 TW TW101150662A patent/TWI449693B/zh active
- 2012-12-28 MD MDA20120129A patent/MD4415C1/ro active IP Right Grant
- 2012-12-28 EA EA201201667A patent/EA022573B1/ru unknown
-
2013
- 2013-01-02 SA SA113340172A patent/SA113340172B1/ar unknown
- 2013-01-02 AP AP2013006655A patent/AP2013006655A0/xx unknown
- 2013-01-02 MA MA35525A patent/MA35001B1/fr unknown
- 2013-01-03 US US13/733,353 patent/US8865915B2/en active Active
- 2013-01-03 CA CA 2801089 patent/CA2801089C/fr active Active
- 2013-01-03 CL CL2013000022A patent/CL2013000022A1/es unknown
- 2013-01-03 AR ARP130100016A patent/AR089632A1/es not_active Application Discontinuation
- 2013-01-03 UA UAA201300118A patent/UA111333C2/uk unknown
- 2013-01-04 PL PL13150305.4T patent/PL2612851T3/pl unknown
- 2013-01-04 EP EP13150305.4A patent/EP2612851B1/fr active Active
- 2013-01-04 CU CUP2013000003A patent/CU24293B1/xx unknown
- 2013-01-04 DK DK13150305.4T patent/DK2612851T3/en active
- 2013-01-04 CN CN201310001282.2A patent/CN103193863B/zh active Active
- 2013-01-04 JP JP2013000108A patent/JP5722924B2/ja active Active
- 2013-01-04 EC ECSP13012366 patent/ECSP13012366A/es unknown
- 2013-01-04 HU HUE13150305A patent/HUE030042T2/en unknown
- 2013-01-04 ES ES13150305.4T patent/ES2595236T3/es active Active
- 2013-01-04 ME MEP-2016-171A patent/ME02493B/me unknown
- 2013-01-04 PT PT131503054T patent/PT2612851T/pt unknown
- 2013-01-04 SI SI201330308A patent/SI2612851T1/sl unknown
- 2013-01-04 LT LTEP13150305.4T patent/LT2612851T/lt unknown
- 2013-01-04 GT GT201300002A patent/GT201300002A/es unknown
- 2013-01-04 BR BR102013000256-9A patent/BR102013000256B1/pt active IP Right Grant
- 2013-01-04 GE GEAP201312951A patent/GEP20146183B/en unknown
- 2013-01-04 KR KR1020130001012A patent/KR101502946B1/ko active IP Right Grant
- 2013-01-04 WO PCT/FR2013/050017 patent/WO2013102740A1/fr active Application Filing
- 2013-01-04 RS RS20160720A patent/RS55096B1/sr unknown
- 2013-01-07 MX MX2013000009A patent/MX2013000009A/es active IP Right Grant
-
2016
- 2016-09-06 HR HRP20161145TT patent/HRP20161145T1/hr unknown
- 2016-10-05 CY CY20161100993T patent/CY1118079T1/el unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0049658A1 (fr) * | 1980-10-02 | 1982-04-14 | Adir | Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant |
| EP1279665A2 (en) * | 2001-07-24 | 2003-01-29 | Adir | A process for the preparation of perindopril, its analogous compounds and salts thereof using 2,5-dioxo-oxazolidine intermediate compounds |
| EP1354873A1 (fr) * | 2002-04-18 | 2003-10-22 | Les Laboratoires Servier | Sel de périndopril et les compositions pharmaceutiques qui le contiennent |
| WO2007099216A2 (fr) * | 2006-02-28 | 2007-09-07 | Les Laboratoires Servier | FORME CRISTALLINE β DU SEL D'ARGININE DU PERINDOPRIL, SON PROCEDE DE PREPARATION, ET LES COMPOSITIONS PHARMACEUTIQUES QUI LA CONTIENNENT |
| EP1989182A1 (fr) * | 2006-02-28 | 2008-11-12 | Les Laboratoires Servier | Forme cristalline du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| WO2009157018A2 (en) * | 2008-06-24 | 2009-12-30 | Matrix Laboratories Ltd | Novel polymorphic forms of perindopril (l)-arginine and process for the 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 |
Non-Patent Citations (1)
| Title |
|---|
| Vania Andre and M.Teresa Duarte. Novel Challenges in Crystall Engineering: Polymorphs and New Crystall Forms of Active Pharmaceutical Ingredients, in Current Trends in Crystallography, pag. 69-94. Edited by Annamalai Chandrasekaran, Publisher Intech, ISBN 978-953-307-754-3. Published online 16, December, 2011. Regăsit în Internet la 2014.11.27, url: http://cdn.intechopen.com/pdfs-wm/25134.pdf vezi pag. 82-86. * |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued |