HRP20150554T1 - Postupak za pripravu nebivolola - Google Patents
Postupak za pripravu nebivolola Download PDFInfo
- Publication number
- HRP20150554T1 HRP20150554T1 HRP20150554TT HRP20150554T HRP20150554T1 HR P20150554 T1 HRP20150554 T1 HR P20150554T1 HR P20150554T T HRP20150554T T HR P20150554TT HR P20150554 T HRP20150554 T HR P20150554T HR P20150554 T1 HRP20150554 T1 HR P20150554T1
- Authority
- HR
- Croatia
- Prior art keywords
- debenzylation
- process according
- catalyst
- nebivolol
- weight
- Prior art date
Links
- KOHIRBRYDXPAMZ-YHBROIRLSA-N (S,R,R,R)-nebivolol Chemical compound C1CC2=CC(F)=CC=C2O[C@H]1[C@H](O)CNC[C@@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 KOHIRBRYDXPAMZ-YHBROIRLSA-N 0.000 title claims 5
- 229960000619 nebivolol Drugs 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 10
- 239000003054 catalyst Substances 0.000 claims 6
- 238000006264 debenzylation reaction Methods 0.000 claims 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 235000019253 formic acid Nutrition 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 239000000758 substrate Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Claims (11)
1. Postupak debenzilacije tvari formule (II)
[image]
koji obuhvaća reagiranje navedene tvari s mravljom kiselinom u prisutnosti katalizatora na bazi paladija;
pri čemu se debenzilacija provodi u prisutnosti sec-butanola.
2. Postupak u skladu s patentnim zahtjevom 1 pri čemu je katalizator Pd/C.
3. Postupak u skladu s patentnim zahtjevom 2 pri čemu je katalizator mokri tip Pd/C.
4. Postupak u skladu s patentnim zahtjevom 2 pri čemu katalizator čini 5% od težine Pd/C.
5. Postupak u skladu s patentnim zahtjevom 1 pri čemu se katalizator koristi u količini od 2-10% prema težini u usporedbi sa supstratom.
6. Postupak u skladu s patentnim zahtjevom 1 pri čemu se debenzilacija provodi na temperaturi od oko 70°C.
7. Postupak u skladu s patentnim zahtjevom 1 pri čemu je molarni omjer mravlje kiseline/supstrata 3:1.
8. Postupak za sintezu nebivolola ili njegove dodatne soli koji obuhvaća debenzilaciju tvari formule II s mravljom kiselinom u prisutnosti katalizatora na bazi paladija u skladu s patentnim zahtjevom 1.
9. Postupak u skladu s jednim od prethodnih patentnih zahtjeva gdje je tvar formule (II) prisutna u obliku racemične smjese (±)[R*, S*, S*, S*].
10. Postupak za sintezu nebivolola ili njegove dodatne soli čistoće od najmanje 99,9 % prema težini, koji obuhvaća debenzilaciju u skladu s patentnim zahtjevom 1.
11. Postupak za sintezu nebivolola ili njegove dodatne soli koji sadrže manje od 0,1 % „de-F“ nebivolola prema težini, koji obuhvaća debenzilaciju u skladu s patentnim zahtjevom 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2008A001924A IT1392067B1 (it) | 2008-10-31 | 2008-10-31 | Processo di preparazione di nebivololo |
| EP09751854.2A EP2346845B1 (en) | 2008-10-31 | 2009-10-28 | Process for preparing nebivolol |
| PCT/EP2009/064230 WO2010049455A1 (en) | 2008-10-31 | 2009-10-28 | Process for preparing nebivolol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150554T1 true HRP20150554T1 (hr) | 2015-07-03 |
Family
ID=40849284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150554TT HRP20150554T1 (hr) | 2008-10-31 | 2015-05-25 | Postupak za pripravu nebivolola |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8927742B2 (hr) |
| EP (1) | EP2346845B1 (hr) |
| JP (1) | JP5560279B2 (hr) |
| CN (1) | CN102186835B (hr) |
| AU (1) | AU2009309680B2 (hr) |
| BR (1) | BRPI0921632B8 (hr) |
| CA (1) | CA2737340C (hr) |
| DK (1) | DK2346845T3 (hr) |
| ES (1) | ES2540092T3 (hr) |
| HR (1) | HRP20150554T1 (hr) |
| HU (1) | HUE025673T2 (hr) |
| IL (1) | IL211497A (hr) |
| IT (1) | IT1392067B1 (hr) |
| PL (1) | PL2346845T3 (hr) |
| PT (1) | PT2346845E (hr) |
| SI (1) | SI2346845T1 (hr) |
| WO (1) | WO2010049455A1 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2907809B1 (en) | 2014-02-14 | 2018-08-22 | Corden Pharma International GmbH | Base-free process for the preparation of ketone intermediates usable for manufacture of nebivolol |
| EP2907810A1 (en) * | 2014-02-14 | 2015-08-19 | Corden Pharma International GmbH | A new method for producing nebivolol hydrochloride of high purity |
| DE102014107132A1 (de) | 2014-05-20 | 2015-11-26 | Corden Pharma International Gmbh | Verfahren zur Herstellung von Epoxiden die in der Herstellung von Nebivolol und dessen Derivaten einsetzbar sind |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1337429C (en) * | 1983-12-05 | 1995-10-24 | Guy Rosalia Eugene Van Lommen | Derivatives of 2,2'-iminobisethanol |
| HU227236B1 (en) * | 2002-11-06 | 2010-12-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | New process for the production of racemic and the pure [2s[2r*[r[r*]]]]-and [2r[2s*[s[s*]]]]-enantiomers of nebivolol |
| RU2378272C2 (ru) * | 2004-07-30 | 2010-01-10 | Торрент Фармасьютикалз Лимитед | Небиволол и его фармацевтически приемлемые соли, способ их получения и фармацевтические композиции небиволола |
| ATE465157T1 (de) * | 2004-08-11 | 2010-05-15 | Hetero Drugs Ltd | Neues verfahren zur herstellung von nebivololzwischenprodukten |
| EP1803716B1 (en) * | 2005-12-28 | 2012-07-25 | Acino Pharma AG | A process for preparation of racemic nebivolol |
| PL2228374T3 (pl) * | 2006-11-27 | 2013-11-29 | Zach System Spa | Mrówczan nebiwololu |
-
2008
- 2008-10-31 IT ITMI2008A001924A patent/IT1392067B1/it active
-
2009
- 2009-10-28 ES ES09751854.2T patent/ES2540092T3/es active Active
- 2009-10-28 DK DK09751854.2T patent/DK2346845T3/en active
- 2009-10-28 AU AU2009309680A patent/AU2009309680B2/en active Active
- 2009-10-28 CN CN200980140649.0A patent/CN102186835B/zh active Active
- 2009-10-28 BR BRPI0921632A patent/BRPI0921632B8/pt active IP Right Grant
- 2009-10-28 JP JP2011533712A patent/JP5560279B2/ja active Active
- 2009-10-28 WO PCT/EP2009/064230 patent/WO2010049455A1/en active Application Filing
- 2009-10-28 PL PL09751854T patent/PL2346845T3/pl unknown
- 2009-10-28 CA CA2737340A patent/CA2737340C/en active Active
- 2009-10-28 SI SI200931205T patent/SI2346845T1/sl unknown
- 2009-10-28 EP EP09751854.2A patent/EP2346845B1/en active Active
- 2009-10-28 PT PT97518542T patent/PT2346845E/pt unknown
- 2009-10-28 HU HUE09751854A patent/HUE025673T2/en unknown
- 2009-10-28 US US13/126,800 patent/US8927742B2/en active Active
-
2011
- 2011-03-01 IL IL211497A patent/IL211497A/en active IP Right Grant
-
2015
- 2015-05-25 HR HRP20150554TT patent/HRP20150554T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0921632B8 (pt) | 2021-05-25 |
| US8927742B2 (en) | 2015-01-06 |
| PT2346845E (pt) | 2015-07-30 |
| ES2540092T3 (es) | 2015-07-08 |
| EP2346845B1 (en) | 2015-03-25 |
| IL211497A0 (en) | 2011-05-31 |
| DK2346845T3 (en) | 2015-06-08 |
| JP5560279B2 (ja) | 2014-07-23 |
| AU2009309680B2 (en) | 2015-08-06 |
| PL2346845T3 (pl) | 2015-08-31 |
| IL211497A (en) | 2014-12-31 |
| EP2346845A1 (en) | 2011-07-27 |
| ITMI20081924A1 (it) | 2010-05-01 |
| AU2009309680A1 (en) | 2010-05-06 |
| CA2737340A1 (en) | 2010-05-06 |
| BRPI0921632B1 (pt) | 2021-03-23 |
| SI2346845T1 (sl) | 2015-10-30 |
| CN102186835A (zh) | 2011-09-14 |
| CN102186835B (zh) | 2016-01-13 |
| BRPI0921632A2 (pt) | 2015-08-18 |
| CA2737340C (en) | 2016-09-06 |
| WO2010049455A1 (en) | 2010-05-06 |
| BRPI0921632A8 (pt) | 2017-07-11 |
| JP2012506894A (ja) | 2012-03-22 |
| HUE025673T2 (en) | 2016-04-28 |
| IT1392067B1 (it) | 2012-02-09 |
| US20110207948A1 (en) | 2011-08-25 |
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