HRP20100420T1 - Postupak za pripravu nebivolola - Google Patents
Postupak za pripravu nebivolola Download PDFInfo
- Publication number
- HRP20100420T1 HRP20100420T1 HR20100420T HRP20100420T HRP20100420T1 HR P20100420 T1 HRP20100420 T1 HR P20100420T1 HR 20100420 T HR20100420 T HR 20100420T HR P20100420 T HRP20100420 T HR P20100420T HR P20100420 T1 HRP20100420 T1 HR P20100420T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- diastereomer
- image
- mixture
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 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 1
- 229960000619 nebivolol Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 84
- 239000000203 mixture Substances 0.000 claims abstract 56
- 238000006243 chemical reaction Methods 0.000 claims abstract 27
- -1 vinyl Grignard reagent Chemical class 0.000 claims abstract 9
- MEYRABVEYCFHHB-UHFFFAOYSA-N 2-bromo-4-fluorophenol Chemical compound OC1=CC=C(F)C=C1Br MEYRABVEYCFHHB-UHFFFAOYSA-N 0.000 claims abstract 7
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 6
- YSGPYVWACGYQDJ-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde Chemical compound CC1(C)OCC(C=O)O1 YSGPYVWACGYQDJ-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000007818 Grignard reagent Substances 0.000 claims abstract 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract 5
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims abstract 5
- 229920002554 vinyl polymer Polymers 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000000376 reactant Substances 0.000 claims abstract 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052796 boron Inorganic materials 0.000 claims abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 10
- 239000003054 catalyst Substances 0.000 claims 6
- 229910052763 palladium Inorganic materials 0.000 claims 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- CJIWSSICZXCQSS-UHFFFAOYSA-N (2-bromo-4-fluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C=C1Br CJIWSSICZXCQSS-UHFFFAOYSA-N 0.000 claims 3
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 claims 1
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06124837 | 2006-11-27 | ||
| PCT/EP2007/010185 WO2008064827A2 (en) | 2006-11-27 | 2007-11-23 | Process for preparing nebivolol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100420T1 true HRP20100420T1 (hr) | 2010-09-30 |
Family
ID=39149443
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100420T HRP20100420T1 (hr) | 2006-11-27 | 2010-07-29 | Postupak za pripravu nebivolola |
| HRP20130774TT HRP20130774T1 (hr) | 2006-11-27 | 2013-08-16 | Nebivolol formijat |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20130774TT HRP20130774T1 (hr) | 2006-11-27 | 2013-08-16 | Nebivolol formijat |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7999124B2 (ja) |
| EP (2) | EP2099790B1 (ja) |
| JP (2) | JP5259612B2 (ja) |
| CN (2) | CN101553485B (ja) |
| AT (1) | ATE473224T1 (ja) |
| AU (1) | AU2007324896B2 (ja) |
| BR (1) | BRPI0719281B8 (ja) |
| CA (2) | CA2667919C (ja) |
| DE (1) | DE602007007666D1 (ja) |
| ES (2) | ES2346371T3 (ja) |
| HR (2) | HRP20100420T1 (ja) |
| IL (2) | IL198555A (ja) |
| PL (2) | PL2228374T3 (ja) |
| PT (1) | PT2228374E (ja) |
| SI (2) | SI2228374T1 (ja) |
| WO (1) | WO2008064827A2 (ja) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE533752T1 (de) | 2008-09-08 | 2011-12-15 | Cadila Pharmaceuticals Ltd | Verbesserter herstellungsprozess für nebivolol- hydrocholorid |
| IT1392067B1 (it) * | 2008-10-31 | 2012-02-09 | Zach System Spa | Processo di preparazione di nebivololo |
| IT1395354B1 (it) * | 2009-07-23 | 2012-09-14 | Zach System Spa | Processo di preparazione di nebivololo |
| DE102010005953A1 (de) * | 2010-01-27 | 2011-07-28 | Corden PharmaChem GmbH, 68305 | Verfahren zur Herstellung von Nebivolol |
| IT1397962B1 (it) | 2010-02-11 | 2013-02-04 | Menarini Int Operations Lu Sa | Processo per la preparazione del nebivololo. |
| WO2011132140A2 (en) * | 2010-04-20 | 2011-10-27 | Cadila Pharmaceuticals Limited | Process for the conversion of (2r)-6-fluoro-2-[(2s)-oxiran-2-yl]-3,4-dihydro-2h-chromene to (2r)-6-fluoro-2-[(2r)-oxiran-2-yl]-3,4-dihydro-2h-chromene |
| CN102311417B (zh) * | 2010-06-29 | 2013-09-18 | 成都弘达药业有限公司 | 一种苯并二氢吡喃类化合物的制备方法 |
| CN102311418B (zh) * | 2010-06-29 | 2013-12-25 | 成都康弘药业集团股份有限公司 | 一种苯并二氢吡喃类化合物的制备方法 |
| CN102344431B (zh) * | 2010-08-05 | 2014-03-26 | 成都康弘药业集团股份有限公司 | 一种制备奈必洛尔盐酸盐的方法 |
| IT1402974B1 (it) | 2010-11-30 | 2013-09-27 | Menarini Int Operations Lu Sa | Processo per la preparazione del nebivololo. |
| CN102180855B (zh) * | 2011-03-01 | 2015-11-25 | 浙江华海药业股份有限公司 | 一种奈必洛尔中间体的提纯方法 |
| ITRM20110418A1 (it) * | 2011-08-02 | 2013-02-03 | Menarini Int Operations Lu Sa | Processo per la preparazione di epossidi quali intermedi per la sintesi del nebivololo. |
| EP2907810A1 (en) | 2014-02-14 | 2015-08-19 | Corden Pharma International GmbH | A new method for producing nebivolol hydrochloride of high purity |
| 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 |
| 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 |
| GB201506691D0 (en) | 2015-04-20 | 2015-06-03 | Greif Int Holding Bv | Closure caps |
| KR20230068441A (ko) * | 2015-05-19 | 2023-05-17 | 저장 아우선 파마슈티칼 씨오., 엘티디. | 네비볼롤 합성방법 및 그의 중간 화합물 |
| JP6921913B2 (ja) * | 2015-05-19 | 2021-08-18 | チョーチアン オウスン ファーマシューティカル カンパニー リミテッド | ネビボロールの合成方法及びその中間化合物 |
| MX2022006087A (es) * | 2019-11-19 | 2022-08-11 | Lupin Ltd | Proceso de preparación de compuestos de cromano. |
| JP7302870B2 (ja) | 2019-12-24 | 2023-07-04 | 株式会社サンセイアールアンドディ | 遊技機 |
Family Cites Families (9)
| 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 |
| CA1337432C (en) * | 1988-03-23 | 1995-10-24 | Raymond M. Xhonneux | Method of lowering the blood pressure |
| US8225408B2 (en) * | 1997-11-06 | 2012-07-17 | Finjan, Inc. | Method and system for adaptive rule-based content scanners |
| 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 |
| EP1741712B1 (en) * | 2004-07-30 | 2011-06-15 | Torrent Pharmaceuticals Ltd | amorphous form of nebivolol hydrochloride and its preparation |
| DE602004026789D1 (de) | 2004-08-11 | 2010-06-02 | Hetero Drugs Ltd | Neues verfahren zur herstellung von nebivololzwischenprodukten |
| CN1279035C (zh) | 2004-08-30 | 2006-10-11 | 中国科学院理化技术研究所 | 光学对映体6－氟－3，4－二氢－2h－1－苯骈吡喃－2－羧酸及6－氟－3，4－二氢－2h－1－苯骈吡喃－2－羧酸酯的合成方法 |
| AP2764A (en) * | 2005-01-31 | 2013-09-30 | Mylan Lab Inc | Hydroxylated nebivolol metabolites |
| US7560575B2 (en) * | 2005-12-28 | 2009-07-14 | Acino Pharma Ag | Process for preparation of racemic Nebivolol |
-
2007
- 2007-11-23 ES ES07846785T patent/ES2346371T3/es active Active
- 2007-11-23 PL PL10162649T patent/PL2228374T3/pl unknown
- 2007-11-23 WO PCT/EP2007/010185 patent/WO2008064827A2/en active Application Filing
- 2007-11-23 EP EP07846785A patent/EP2099790B1/en active Active
- 2007-11-23 DE DE602007007666T patent/DE602007007666D1/de active Active
- 2007-11-23 PT PT101626497T patent/PT2228374E/pt unknown
- 2007-11-23 AT AT07846785T patent/ATE473224T1/de not_active IP Right Cessation
- 2007-11-23 CA CA2667919A patent/CA2667919C/en active Active
- 2007-11-23 BR BRPI0719281A patent/BRPI0719281B8/pt active IP Right Grant
- 2007-11-23 CN CN2007800441591A patent/CN101553485B/zh active Active
- 2007-11-23 AU AU2007324896A patent/AU2007324896B2/en active Active
- 2007-11-23 JP JP2009537552A patent/JP5259612B2/ja active Active
- 2007-11-23 EP EP10162649.7A patent/EP2228374B1/en active Active
- 2007-11-23 CA CA2835833A patent/CA2835833C/en active Active
- 2007-11-23 SI SI200731290T patent/SI2228374T1/sl unknown
- 2007-11-23 CN CN201210566913.0A patent/CN103087028B/zh active Active
- 2007-11-23 ES ES10162649T patent/ES2426399T3/es active Active
- 2007-11-23 US US12/515,375 patent/US7999124B2/en not_active Expired - Fee Related
- 2007-11-23 SI SI200730293T patent/SI2099790T1/sl unknown
- 2007-11-23 PL PL07846785T patent/PL2099790T3/pl unknown
-
2009
- 2009-05-04 IL IL198555A patent/IL198555A/en active IP Right Grant
-
2010
- 2010-07-29 HR HR20100420T patent/HRP20100420T1/hr unknown
-
2011
- 2011-04-29 US US13/097,453 patent/US8258323B2/en active Active
-
2012
- 2012-11-01 IL IL222787A patent/IL222787A/en active IP Right Grant
-
2013
- 2013-03-04 JP JP2013041640A patent/JP5735025B2/ja active Active
- 2013-08-16 HR HRP20130774TT patent/HRP20130774T1/hr unknown
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