ME02493B - Postupak za pripravu L-argininske soli perindoprila - Google Patents
Postupak za pripravu L-argininske soli perindoprilaInfo
- Publication number
- ME02493B ME02493B MEP-2016-171A MEP2016171A ME02493B ME 02493 B ME02493 B ME 02493B ME P2016171 A MEP2016171 A ME P2016171A ME 02493 B ME02493 B ME 02493B
- Authority
- ME
- Montenegro
- Prior art keywords
- perindopril
- arginine salt
- preparation
- arginine
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 7
- 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 title claims 6
- 229960002582 perindopril Drugs 0.000 title claims 6
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 title 1
- 238000000034 method Methods 0.000 claims 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 6
- 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 claims 6
- AUVAVXHAOCLQBF-UHFFFAOYSA-N 2-[(1-ethoxy-1-oxopentan-2-yl)azaniumyl]propanoate Chemical compound OC(=O)C(C)NC(CCC)C(=O)OCC AUVAVXHAOCLQBF-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 3
- 229930064664 L-arginine Natural products 0.000 claims 3
- 235000014852 L-arginine Nutrition 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 230000003213 activating effect Effects 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 claims 1
- CQYBNXGHMBNGCG-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCCC2NC(C(=O)O)CC21 CQYBNXGHMBNGCG-UHFFFAOYSA-N 0.000 claims 1
- 150000008535 L-arginines Chemical class 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- YHNUDLCUIKMNSN-UHFFFAOYSA-N bis(1,2,4-triazol-1-yl)methanone Chemical compound C1=NC=NN1C(=O)N1C=NC=N1 YHNUDLCUIKMNSN-UHFFFAOYSA-N 0.000 claims 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010612 desalination reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical compound CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 (6)
1. Postupak za pripravu perindopril L-argininske soli formule (I):naznačen time, da se sastoji od reakcije između perindoprila i L-arginina u sustavu otapala koji je odabran od:binarne mješavine acetonitrila i dimetil sulfoksida,binarne mješavine etil acetata i dimetil sulfoksida,trodjelne mješavine acetonitrila, dimetil sulfoksida i toluena,pri temperaturi od 10 do 100°C,nakon čega slijedi izolazija putem filtracije tako dobivene L-argininske soli.
2. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 1, naznačen time, da je perindopril dobiven reakcijom N-[1-(S)-etoksikarbonil-butil]-(S)-alanina formule (II): sa sredstvom za aktiviranje formule X2C=O pri čemu X predstavlja odlazeću skupinu, u organskom otapalu ili sustavu organskih otapala, pri temperaturi od -20 do 80°C, uz reakciju tako dobivenog intermedijernog spoja formule (III): sa (2S, 3aS, 7aS)-2-karboksiperhidroindolom pri temperaturi od 0 do 80°C, a potom tako dobiveni perindopril reagira s L-argininom iz postupka prema patentnom zahtjevu 1.
3. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 2, naznačen time, da je sredstvo za aktiviranje N,N’-karbonildiimidazol, fosgen, trifosgen, (1,1’-karbonildi(1,2,4-triazol) ili di(N-sukcinimidil) karbonat.
4. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 3, naznačen time, da je sredstvo za aktivaciju N,N’-karbonildiimidazol, a količina N,N’-karbonildiimidazola je između 0.8 i 1.2 mola, uključeno, po molu od N-[1-(S)-etoksikarbonil-butil]-(S)-alanina.
5. Postupak za pripravu perindopril L-argininske soli prema bilo kojem od patentnih zahtjeva 2 do 4, naznačen time, da je količina (2S, 3aS, 7aS)-2-karboksiperhidroindola između 0.8 i 1.2 mola, uključujući, po molu od N-[1-(S)-etoksikarbonil-butil]-(S)-alanina.
6. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 1, naznačen time, da je perindopril dobiven desalinizacijom perindopril terc-butilamina djelovanjem kiseline, a potom tako dobiveni perindopril reagira L-argininom prema postupku iz patentnog zahtjeva 1.
Applications Claiming Priority (2)
| 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 |
| EP13150305.4A EP2612851B1 (fr) | 2012-01-05 | 2013-01-04 | Procédé de préparation du sel de l-arginine du périndopril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02493B true ME02493B (me) | 2017-02-20 |
Family
ID=47427278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-171A ME02493B (me) | 2012-01-05 | 2013-01-04 | Postupak za pripravu L-argininske soli perindoprila |
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 |
| CN111344775A (zh) | 2017-10-06 | 2020-06-26 | S·拉德 | 增强现实系统和套件 |
| 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 |
| 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 |
| EP2472333A1 (en) | 2003-09-18 | 2012-07-04 | Xeikon IP BV | Method of preparation of a liquid electrostatographic toner and liquid electrostatographic toner |
| 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 |
| US8686161B2 (en) * | 2008-06-24 | 2014-04-01 | Mylan Laboratories Limited | 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 |
-
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 CR CR20120654A patent/CR20120654A/es unknown
- 2012-12-19 SG SG2012093589A patent/SG192337A1/en unknown
- 2012-12-19 JO JOP/2012/0384A patent/JO3196B1/ar 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
- 2012-12-20 AU AU2012268816A patent/AU2012268816B2/en active Active
- 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 EA EA201201667A patent/EA022573B1/ru unknown
- 2012-12-28 MD MDA20120129A patent/MD4415C1/ro active IP Right Grant
-
2013
- 2013-01-02 AP AP2013006655A patent/AP2013006655A0/xx unknown
- 2013-01-02 MA MA35525A patent/MA35001B1/fr unknown
- 2013-01-02 SA SA113340172A patent/SA113340172B1/ar unknown
- 2013-01-03 CA CA 2801089 patent/CA2801089C/fr active Active
- 2013-01-03 US US13/733,353 patent/US8865915B2/en active Active
- 2013-01-03 AR ARP130100016A patent/AR089632A1/es not_active Application Discontinuation
- 2013-01-03 CL CL2013000022A patent/CL2013000022A1/es unknown
- 2013-01-03 UA UAA201300118A patent/UA111333C2/uk unknown
- 2013-01-04 PL PL13150305.4T patent/PL2612851T3/pl unknown
- 2013-01-04 HU HUE13150305A patent/HUE030042T2/en unknown
- 2013-01-04 JP JP2013000108A patent/JP5722924B2/ja active Active
- 2013-01-04 CN CN201310001282.2A patent/CN103193863B/zh active Active
- 2013-01-04 WO PCT/FR2013/050017 patent/WO2013102740A1/fr not_active Ceased
- 2013-01-04 BR BR102013000256-9A patent/BR102013000256B1/pt active IP Right Grant
- 2013-01-04 DK DK13150305.4T patent/DK2612851T3/en active
- 2013-01-04 ES ES13150305.4T patent/ES2595236T3/es active Active
- 2013-01-04 LT LTEP13150305.4T patent/LT2612851T/lt unknown
- 2013-01-04 EC ECSP13012366 patent/ECSP13012366A/es unknown
- 2013-01-04 PT PT131503054T patent/PT2612851T/pt unknown
- 2013-01-04 GE GEAP201312951A patent/GEP20146183B/en unknown
- 2013-01-04 EP EP13150305.4A patent/EP2612851B1/fr active Active
- 2013-01-04 GT GT201300002A patent/GT201300002A/es unknown
- 2013-01-04 KR KR1020130001012A patent/KR101502946B1/ko active Active
- 2013-01-04 RS RS20160720A patent/RS55096B1/sr unknown
- 2013-01-04 SI SI201330308A patent/SI2612851T1/sl unknown
- 2013-01-04 CU CUP2013000003A patent/CU24293B1/xx unknown
- 2013-01-04 ME MEP-2016-171A patent/ME02493B/me 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
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