HRP20151208T1 - Novi polimorfni oblici perindopril (l)-arginina i postupak za njihovo pripravljanje - Google Patents
Novi polimorfni oblici perindopril (l)-arginina i postupak za njihovo pripravljanje Download PDFInfo
- Publication number
- HRP20151208T1 HRP20151208T1 HRP20151208TT HRP20151208T HRP20151208T1 HR P20151208 T1 HRP20151208 T1 HR P20151208T1 HR P20151208T T HRP20151208T T HR P20151208TT HR P20151208 T HRP20151208 T HR P20151208T HR P20151208 T1 HRP20151208 T1 HR P20151208T1
- Authority
- HR
- Croatia
- Prior art keywords
- perindopril
- arginine
- polymorphic form
- solvent
- preparing
- Prior art date
Links
- 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 claims 21
- 238000000034 method Methods 0.000 title claims 9
- 239000002904 solvent Substances 0.000 claims 9
- 238000002955 isolation Methods 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 5
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 239000012296 anti-solvent Substances 0.000 claims 4
- 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 claims 4
- 229960002582 perindopril Drugs 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 229930064664 L-arginine Natural products 0.000 claims 2
- 235000014852 L-arginine Nutrition 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 238000004090 dissolution Methods 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- 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
- A61P9/12—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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (13)
1. Polimorfni oblik γ perindopril (L)-arginina naznačen obrascem rendgenske difrakcije praha s vršnim vrijednostima od 4.21, 7.87, 13.19, 14.12, 17.60, 20.15 6 0.2 stupnjeva 2-theta.
2. Polimorfni oblik γ prema zahtjevu 1, koji ima stupanj kristalnosti ispod 60%.
3. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 koji uključuje sljedeće korake:
a) otapanje slobodne kiseline perindopril u vodi,
b) dodavanje L-arginina,
c) odstranjivanje otapala i
d) izoliranje polimorfnog oblika γ perindopril (L)-arginina,
4. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 koji uključuje sljedeće korake:
a) otapanje perindopril L- arginina u nekom otapalu,
b) dodavanje antisolventa,
c) izoliranje polimorfnog oblika γ perindopril (L)-arginina
5. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 koji uključuje sljedeće korake:
a) suspendiranje slobodne kiseline perindopril i L-arginina u nekom otapalu
b) zagrijavanje reakcijske mase do temperature refluksa,
c) dodavanje antisolventa i
d) izoliranje polimorfnog oblika γ perindopril (L)-arginina.
6. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 koji uključuje sljedeće korake:
a) otapanje slobodne kiseline perindopril i (L)-arginina u vodi,
b) dodavanje prvog otapala
c) hlađenje reakcijske smjese,
d) dodavanje drugog otapala i
e) izoliranje polimorfnog oblika γ perindopril (L)-arginina.
7. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 koji uključuje sljedeće korake:
a) otapanje slobodne kiseline perindopril u mješavini otapala,
b) dodavanje otopine (L)-arginina u vodi i
c) izoliranje polimorfnog oblika γ perindopril (L)-arginina.
8. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 koji uključuje sljedeće korake:
a) suspendiranje perindopril (L)-arginina u nekom otapalu,
b) miješanje suspenzije iz koraka (a) na temperaturi između 20 do 115° C i
c) izoliranje polimorfnog oblika γ perindopril (L)-arginina.
9. Postupak prema zahtjevu 8, naznačen time da je otapalo odabrano među ugljikovodicima kao što su toluen, pentan, n-heptan, cikloheksan, n-heksan, ili nitrita kao što su acetonitril ili njihove mješavine.
10. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 koji uključuje sljedeće korake:
a) suspendiranje perindopril (L)-arginina u nekom otapalu,
b) azeotropna destilacija suspenzije iz koraka (a) na temperaturi od oko 80-110°C
c) dodavanje antisolventa i
d) izoliranje polimorfnog oblika γ perindopril (L)-arginina.
11. Postupak prema zahtjevu 10, naznačen time da je to otapalo toulen.
12. Postupak prema zahtjevu 10, naznačen time da je antisolvent acetonitril.
13. Postupak pripravljanja polimorfnog oblika γ perindopril (L)-arginina prema zahtjevu 1 izlaganjem amorfnog oblika perindopril (L)-arginina relativnoj vlažnosti od oko 90% kroz nekoliko sati.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1535CH2008 | 2008-06-24 | ||
| PCT/IN2009/000357 WO2009157018A2 (en) | 2008-06-24 | 2009-06-22 | Novel polymorphic forms of perindopril (l)-arginine and process for the preparation thereof |
| EP09769810.4A EP2318365B1 (en) | 2008-06-24 | 2009-06-22 | Novel polymorphic forms of perindopril (l)-arginine and process for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20151208T1 true HRP20151208T1 (hr) | 2015-12-18 |
Family
ID=41203736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20151208TT HRP20151208T1 (hr) | 2008-06-24 | 2015-11-11 | Novi polimorfni oblici perindopril (l)-arginina i postupak za njihovo pripravljanje |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US8686161B2 (hr) |
| EP (2) | EP2682388B1 (hr) |
| AU (1) | AU2009263737B2 (hr) |
| CA (2) | CA2919564A1 (hr) |
| CY (1) | CY1116930T1 (hr) |
| DK (1) | DK2318365T3 (hr) |
| ES (1) | ES2552653T3 (hr) |
| HR (1) | HRP20151208T1 (hr) |
| HU (1) | HUE025982T2 (hr) |
| PL (1) | PL2318365T3 (hr) |
| PT (1) | PT2318365E (hr) |
| SI (1) | SI2318365T1 (hr) |
| WO (1) | WO2009157018A2 (hr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| FR2985511B1 (fr) | 2012-01-05 | 2014-01-03 | Servier Lab | Forme cristalline delta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2985512B1 (fr) * | 2012-01-05 | 2014-06-20 | Servier Lab | Procede de preparation du sel de l-arginine du perindopril |
| CN103172696B (zh) * | 2012-12-19 | 2014-12-17 | 宁波美诺华药业股份有限公司 | 一种γ晶型的培哚普利精氨酸盐的制备方法 |
| WO2016178591A2 (en) | 2015-05-05 | 2016-11-10 | Gene Predit, Sa | Genetic markers and treatment of male obesity |
| FR3050380B1 (fr) | 2016-04-20 | 2020-07-10 | Les Laboratoires Servier | Composition pharmaceutique comprenant un betabloquant, un inhibiteur de l'enzyme de conversion et un antihypertenseur ou un ains. |
| CN109725022A (zh) * | 2018-12-27 | 2019-05-07 | 湖南科技大学 | 一种结合水含量的快速测量方法 |
| EP3842035A1 (en) | 2019-12-23 | 2021-06-30 | KRKA, d.d., Novo mesto | Composition for the preparation of perindopril arginine granules, a method for their preparation and pharmaceutical composition comprising the granules |
| 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 |
| SI26268A (sl) * | 2021-11-18 | 2023-05-31 | Zupet Rok | Postopek za pripravo hidratirane oblike perindopril l-arginina |
| 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 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4616031A (en) * | 1979-12-07 | 1986-10-07 | Adir | Perhydroindole-2-carboxylic acids as antihypertensives |
| US4616030A (en) * | 1979-12-07 | 1986-10-07 | Adir | Perhydroindole-2-carboxylic acids as antihypertensives |
| US4508729A (en) | 1979-12-07 | 1985-04-02 | Adir | Substituted iminodiacids, their preparation and pharmaceutical compositions containing them |
| US5162362A (en) * | 1980-08-30 | 1992-11-10 | Hoechst Aktiengesellschaft | Octahydroindole-2-carboxylic acids |
| DE3226768A1 (de) * | 1981-11-05 | 1983-05-26 | Hoechst Ag, 6230 Frankfurt | Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung |
| FR2620709B1 (fr) | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| GB9101443D0 (en) | 1991-01-23 | 1991-03-06 | Plessey Telecomm | Coin mechanisms |
| FR2811318B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811319B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2838648B1 (fr) | 2002-04-18 | 2004-05-21 | Servier Lab | Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent |
| SI1603558T1 (sl) * | 2003-02-28 | 2008-12-31 | Servier S A Lab | Postopek za pripravo perindoprila in njegovih soli |
| ATE310012T1 (de) * | 2003-08-29 | 2005-12-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutisch annehmbaren salzen |
| ATE386745T1 (de) * | 2003-12-10 | 2008-03-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutisch annehmbaren salzen |
| US7615571B2 (en) * | 2004-05-31 | 2009-11-10 | Ipca Laboratories Ltd. | Process for manufacture of pure (2S, 3aS, 7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl) butyl]amino]-1-oxopropyl] octahydro-1H-indole-2-carboxylic acid and its tert. butyl amine salt |
| JP2008545006A (ja) * | 2005-07-05 | 2008-12-11 | シプラ・リミテッド | Ａｃｅ阻害剤の合成方法 |
| 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 |
| 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 |
| 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 |
| EP2906536B1 (en) * | 2012-10-10 | 2018-03-14 | Piramal Enterprises Limited | An improved process for preparation of perindopril intermediate |
-
2009
- 2009-06-22 AU AU2009263737A patent/AU2009263737B2/en active Active
- 2009-06-22 CA CA2919564A patent/CA2919564A1/en not_active Abandoned
- 2009-06-22 ES ES09769810.4T patent/ES2552653T3/es active Active
- 2009-06-22 CA CA2729604A patent/CA2729604C/en not_active Expired - Fee Related
- 2009-06-22 EP EP13003519.9A patent/EP2682388B1/en not_active Revoked
- 2009-06-22 SI SI200931310T patent/SI2318365T1/sl unknown
- 2009-06-22 US US13/001,180 patent/US8686161B2/en not_active Expired - Fee Related
- 2009-06-22 HU HUE09769810A patent/HUE025982T2/en unknown
- 2009-06-22 WO PCT/IN2009/000357 patent/WO2009157018A2/en active Application Filing
- 2009-06-22 EP EP09769810.4A patent/EP2318365B1/en not_active Revoked
- 2009-06-22 PL PL09769810T patent/PL2318365T3/pl unknown
- 2009-06-22 PT PT97698104T patent/PT2318365E/pt unknown
- 2009-06-22 DK DK09769810.4T patent/DK2318365T3/en active
-
2014
- 2014-01-23 US US14/161,967 patent/US20140135504A1/en not_active Abandoned
-
2015
- 2015-07-29 US US14/812,053 patent/US9725412B2/en active Active
- 2015-11-10 CY CY20151101010T patent/CY1116930T1/el unknown
- 2015-11-11 HR HRP20151208TT patent/HRP20151208T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8686161B2 (en) | 2014-04-01 |
| WO2009157018A2 (en) | 2009-12-30 |
| CA2729604C (en) | 2017-12-05 |
| CA2919564A1 (en) | 2009-12-30 |
| CY1116930T1 (el) | 2017-04-05 |
| US20110301357A1 (en) | 2011-12-08 |
| AU2009263737A1 (en) | 2009-12-30 |
| EP2682388A1 (en) | 2014-01-08 |
| SI2318365T1 (sl) | 2016-01-29 |
| PT2318365E (pt) | 2015-11-25 |
| WO2009157018A3 (en) | 2010-07-29 |
| EP2318365B1 (en) | 2015-08-12 |
| EP2318365A2 (en) | 2011-05-11 |
| CA2729604A1 (en) | 2009-12-30 |
| US9725412B2 (en) | 2017-08-08 |
| WO2009157018A9 (en) | 2010-06-10 |
| DK2318365T3 (en) | 2015-11-23 |
| PL2318365T3 (pl) | 2016-02-29 |
| ES2552653T3 (es) | 2015-12-01 |
| HUE025982T2 (en) | 2016-05-30 |
| AU2009263737B2 (en) | 2013-10-24 |
| US20150336890A1 (en) | 2015-11-26 |
| US20140135504A1 (en) | 2014-05-15 |
| EP2682388B1 (en) | 2018-01-10 |
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