HRP20090548T1 - Poboljšani postupak za pročišćavanje perindoprila - Google Patents
Poboljšani postupak za pročišćavanje perindoprila Download PDFInfo
- Publication number
- HRP20090548T1 HRP20090548T1 HR20090548T HRP20090548T HRP20090548T1 HR P20090548 T1 HRP20090548 T1 HR P20090548T1 HR 20090548 T HR20090548 T HR 20090548T HR P20090548 T HRP20090548 T HR P20090548T HR P20090548 T1 HRP20090548 T1 HR P20090548T1
- Authority
- HR
- Croatia
- Prior art keywords
- perindopril
- dicyclohexylamine
- salt
- compound
- formula
- Prior art date
Links
- 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 abstract 26
- 229960002582 perindopril Drugs 0.000 title claims abstract 25
- 238000000034 method Methods 0.000 title claims 8
- 238000000746 purification Methods 0.000 title claims 4
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 8
- 238000002955 isolation Methods 0.000 claims 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- 239000012445 acidic reagent Substances 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 125000004971 nitroalkyl group Chemical group 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 238000001757 thermogravimetry curve Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Dicikloheksilamin sol spoja formule I, odnosno perindoprila, koja ima uzorak difrakcije X-zraka na prahu sa slijedećim karakterističnim signalima (2θ): 8.462, 10.624, 18.693, 9.424, 17.272, 14.177, 19.499, 20.765, 21.409 i 14.540. Patent sadrži još 13 patentnih zahtjeva.
Claims (14)
1. Dicikloheksilamin sol spoja formule I, odnosno perindoprila, koja ima uzorak difrakcije X-zraka na prahu sa slijedećim karakterističnim signalima (2θ): 8.462, 10.624, 18.693, 9.424, 17.272, 14.177, 19.499, 20.765, 21.409 i 14.540.
[image]
2. Dicikloheksilamin sol perindoprila prema zahtjevu 1, koja ima difraktogram X-zraka, ili u biti isti difraktogram X-zraka, kao što je prikazano na slici 1.
3. Dicikloheksilamin sol perindoprila prema zahtjevu 1, koja ima DSC termogram kao što je prikazano na slici 2.
4. Dicikloheksilamin sol perindoprila prema zahtjevu 1, koja ima TGA termogram kao što je prikazano na slici 3.
5. Postupak pročišćavanja spoja formule I, odnosno perindoprila
[image]
koji obuhvaća stupnjeve
i. tretiranje perindoprila s dicikloheksilaminom u prisustvu otapala da bi se dobila sol perindoprila s dicikloheksilaminom;
ii. izoliranje spomenute dicikloheksilamin soli spoja formule I;
iii. tretiranje dicikloheksilamin soli spoja formule I opcijski u prisustvu organskog otapala da bi se dobila sol s terc-butil aminom.
6. Postupak pročišćavanja spoja formule I, odnosno perindoprila
[image]
koji obuhvaća stupnjeve:
i. tretiranje perindoprila s dicikloheksilaminom u prisustvu otapala da bi se dobila sol perindoprila s dicikloheksilaminom;
ii. izoliranje spomenute dicikloheksilamin soli spoja formule I;
iii. tretiranje dicikloheksilamin soli spoja formule I opcijski u prisustvu organskog otapala da bi se dobila sol s terc butil aminom;
iv. izoliranje spoja formule I s nepoznatim nečistoćama;
v. pretvaranje u dicikloheksilamin sol spoja formule I visoke čistoće.
7. Postupak pročišćavanja perindoprila prema zahtjevu 5 ili 6, gdje je u stupnju (i) spomenuto otapalo acetonitril.
8. Postupak pročišćavanja peridoprila prema zahtjevu 5 ili 6, gdje je u stupnju (iii) spomenuto otapalo izabran iz grupe koju čine ketoni, alkoholi, nitrili, nitroalkani, acetali, eteri, aromatični ugljikvodici, klorirana otapala ili njihova smjesa.
9. Postupak pročišćavanja perindoprila prema zahtjevima 5 ili 6, gdje je u stupnju (iii) spomenuto otapalo izabran iz grupe koju čine aceton, etanol, acetonitril, nitrometan, 2,2-dimetoksi propan, diizopropil eter, toluen, diklorometan ili njihova smjesa.
10. Postupak pročišćavanja spoja formule I, odnosno perindoprila
[image]
koji obuhvaća stupnjeve:
i. tretiranje perindoprila u otapalu s dicikloheksilaminom da bi se dobio spoj formule I u obliku soli s dicikloheksilaminom;
ii. izoliranje spomenute dicikloheksilamin soli perindoprila:
iii. tretiranje perindoprila u obliku soli s dicikloheksilaminom s kiselim reagensom da bi se dobila slobodna baza perindopila; i
iv. izoliranje perindoprila u obliku slobodne baze.
11. Postupak pročišćavanja perindoprila prema zahtjevu 10, gdje je u stupnju (i) spomenuto otapalo acetonitril.
12. Postupak pročišćavanja perindoprila prema zahtjevu 10, gdje je u stupnju (iii) spomenuti kiseli reagens klorovodonična kiselina.
13. Upotreba dicikloheksil amin soli perindoprila za pročišćavanje perindoprila prema bilo kojem od zahtjeva 5 do 12.
14. Upotreba terc-butil amin soli perindoprila za pročišćavanje perindoprila prema bilo kojem zahtjevu 5 do 12.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN275MU2005 | 2005-03-14 | ||
| PCT/IN2005/000189 WO2006097941A1 (en) | 2005-03-14 | 2005-06-09 | An improved process for the purification of perindopril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090548T1 true HRP20090548T1 (hr) | 2009-11-30 |
Family
ID=35840279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090548T HRP20090548T1 (hr) | 2005-03-14 | 2009-10-14 | Poboljšani postupak za pročišćavanje perindoprila |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7728151B2 (hr) |
| EP (1) | EP1861367B1 (hr) |
| AU (1) | AU2005329237B2 (hr) |
| CA (1) | CA2601647C (hr) |
| CY (1) | CY1109432T1 (hr) |
| DE (1) | DE602005015492D1 (hr) |
| DK (1) | DK1861367T3 (hr) |
| EA (1) | EA012420B1 (hr) |
| ES (1) | ES2329923T3 (hr) |
| HR (1) | HRP20090548T1 (hr) |
| NO (1) | NO20075237L (hr) |
| NZ (1) | NZ561684A (hr) |
| PL (1) | PL1861367T3 (hr) |
| PT (1) | PT1861367E (hr) |
| RS (1) | RS51147B (hr) |
| SI (1) | SI1861367T1 (hr) |
| WO (1) | WO2006097941A1 (hr) |
| ZA (1) | ZA200708802B (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090099370A1 (en) * | 2005-08-12 | 2009-04-16 | Sandoz Ag | Crystalline Form of Perindopril Erbumine |
| SI22543A (sl) * | 2007-06-27 | 2008-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove soli perindoprila |
| GB0910692D0 (en) | 2009-06-20 | 2009-08-05 | Teva Pharma | Compound |
| EP3658549B1 (en) * | 2017-07-24 | 2021-05-05 | Interquim, S.A. | Process for preparing and purifying the lfa-1 antagonist lifitegrast |
Family Cites Families (4)
| 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 |
| FR2838648B1 (fr) * | 2002-04-18 | 2004-05-21 | Servier Lab | Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent |
| US7521566B2 (en) * | 2003-02-28 | 2009-04-21 | Les Laboratoires Servier | Process for preparation of perindopril and salts thereof |
| US7445296B1 (en) * | 2006-07-24 | 2008-11-04 | Chosen Co., Ltd. | Bicycle hub having enhanced strength |
-
2005
- 2005-06-09 NZ NZ561684A patent/NZ561684A/en not_active IP Right Cessation
- 2005-06-09 ZA ZA200708802A patent/ZA200708802B/xx unknown
- 2005-06-09 WO PCT/IN2005/000189 patent/WO2006097941A1/en active Application Filing
- 2005-06-09 DE DE602005015492T patent/DE602005015492D1/de active Active
- 2005-06-09 EA EA200701862A patent/EA012420B1/ru not_active IP Right Cessation
- 2005-06-09 EP EP05799448A patent/EP1861367B1/en active Active
- 2005-06-09 RS RSP-2009/0430A patent/RS51147B/sr unknown
- 2005-06-09 ES ES05799448T patent/ES2329923T3/es active Active
- 2005-06-09 AU AU2005329237A patent/AU2005329237B2/en not_active Ceased
- 2005-06-09 PT PT05799448T patent/PT1861367E/pt unknown
- 2005-06-09 PL PL05799448T patent/PL1861367T3/pl unknown
- 2005-06-09 US US11/886,382 patent/US7728151B2/en not_active Expired - Fee Related
- 2005-06-09 DK DK05799448T patent/DK1861367T3/da active
- 2005-06-09 SI SI200530795T patent/SI1861367T1/sl unknown
- 2005-06-09 CA CA2601647A patent/CA2601647C/en not_active Expired - Fee Related
-
2007
- 2007-10-12 NO NO20075237A patent/NO20075237L/no unknown
-
2009
- 2009-09-24 CY CY20091100999T patent/CY1109432T1/el unknown
- 2009-10-14 HR HR20090548T patent/HRP20090548T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI1861367T1 (sl) | 2009-12-31 |
| DE602005015492D1 (de) | 2009-08-27 |
| CA2601647A1 (en) | 2006-09-21 |
| ES2329923T3 (es) | 2009-12-02 |
| DK1861367T3 (da) | 2009-11-02 |
| NZ561684A (en) | 2009-10-30 |
| US7728151B2 (en) | 2010-06-01 |
| EA200701862A1 (ru) | 2008-02-28 |
| PL1861367T3 (pl) | 2009-12-31 |
| ZA200708802B (en) | 2009-01-28 |
| AU2005329237B2 (en) | 2011-09-01 |
| EP1861367B1 (en) | 2009-07-15 |
| EP1861367A1 (en) | 2007-12-05 |
| WO2006097941A1 (en) | 2006-09-21 |
| PT1861367E (pt) | 2009-10-08 |
| NO20075237L (no) | 2007-10-12 |
| US20080139823A1 (en) | 2008-06-12 |
| AU2005329237A1 (en) | 2006-09-21 |
| CA2601647C (en) | 2013-07-30 |
| RS51147B (sr) | 2010-10-31 |
| CY1109432T1 (el) | 2014-08-13 |
| EA012420B1 (ru) | 2009-10-30 |
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