HRP20141023T1 - Novi postupak sinteze ivabradina i njegovih adicijskih soli sa farmaceutski prihvatljivom kiselinom - Google Patents
Novi postupak sinteze ivabradina i njegovih adicijskih soli sa farmaceutski prihvatljivom kiselinom Download PDFInfo
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- HRP20141023T1 HRP20141023T1 HRP20141023AT HRP20141023T HRP20141023T1 HR P20141023 T1 HRP20141023 T1 HR P20141023T1 HR P20141023A T HRP20141023A T HR P20141023AT HR P20141023 T HRP20141023 T HR P20141023T HR P20141023 T1 HRP20141023 T1 HR P20141023T1
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- Prior art keywords
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- optionally substituted
- heteroaromatic
- aromatic
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Classifications
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
- B01J2235/05—Nuclear magnetic resonance [NMR]
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (14)
1. Postupak za sintezu ivabradina formule (I):
[image]
naznačen time, da je spoj formule (V):
[image]
podvrgnut reakciji redukcijske aminacije sa aminom formule (VI):
[image]
u prisutnosti katalizatora na bazi željeza formule (VII):
[image]
pri čemu R1, R2, R3 i R4 neovisno predstavljaju:
• atom vodika, ili
• skupinu - SiR5R6R7, pri čemu R5, R6 i R7 neovisno predstavljaju po izboru supstituiranu, ravnu ili razgrananu (C1-C6)alkilnu skupinu ili po izboru supstituiranu aromatičnu ili heteroaromatičnu skupinu, ili
• po izboru supstituiranu aromatičnu ili heteroaromatičnu skupinu, ili
• po izboru supstituiranu, ravnu ili razgrananu (C1-C6) alkilnu skupinu, ili
• skupinu koja privlači elektrone, ili
• amino skupinu koja je alifatska, aromatska, heteroaromatska ili nosi skupinu koja privlači elektrone ili
• alifatsku, aromatsku ili heteroaromatsku eter skupinu,
ili parovi R1 i R2, ili R2 i R3, ili R3 i R4 tvore, zajedno s atomom ugljika koji ih nosi, 3- do 7-eročlani karbocikl ili heterocikl,
X predstavlja:
• atom kisika, ili
• -NH skupinu, ili atom dušika koji je supstituiran s alifatskom, aromatskom, heteroaromatskom ili skupinom koja privlači elektrone ili
• -PH skupinu, ili fosforni atom koji je supstituiran s jednom ili više alifatskih, aromatskih ili skupina koje privlače elektrone, ili
• atom sumpora,
L1, L2 i L3 neovisno predstavljaju karbonil, nitril, izonitril, heteroaromat, fosfin, fosfit, fosfonit, fosforamidit, fosfonit, fosfolan, fosfolen, alifatski amin, aromatski amin, heteroaromatski amin, skupinu koja privlači elektrone i nosi amin, alifatski eter, aromatski eter, heteroaromatski eter, sulfon, sulfoksid ili sulfoksimin skupinu ili N-heterocikličnu karbensku skupinu koja ima jednu od sljedeće dvije formule:
[image]
pri čemu Y i Z neovisno predstavljaju atom sumpora ili atom kisika ili skupinu NR8 i R8 predstavlja po izboru supstituiranu alkil skupinu ili po izboru supstituiranu aromatsku ili heteroaromatsku skupinu,
K predstavlja atom ugljika ili atom dušika,
R9 i R10 neovisno predstavljaju atom vodika, po izboru supstituiranu alkilnu skupinu, po izboru supstituiranu aromatičnu ili heteroaromatičnu skupinu, atom halogena, alifatsku, aromatsku ili heteroaromatsku etersku skupinu, alifatsku, aromatsku ili heteroaromatsku amino skupinu, ili par R9 i R10 tvori zajedno s atomima koji ih nose, 3- do 7-člani karbocikl ili heterocikl, ili
[image]
pri čemu R11 i R12 neovisno predstavljaju po izboru supstituiranu alkilnu skupinu ili po izboru supstituiranu aromatsku ili heteroaromatsku skupinu, a n je 1 ili 2, u prisutnosti ili bez trimetilamin N-oksida, pod tlakom dihidrogena od 1 do 20 bara, u organskom otapalu ili smjesi organskih otapala, pri temperaturi od 25 do 100°C.
2. Postupak sinteze u skladu s patentnim zahtjevom 1, naznačen time, da katalizator na bazi željeza ima sljedeću opću formulu:
[image]
pri čemu R2 i R3 svaki predstavlja atom vodika ili pak zajedno s atomom ugljika koji ih nosi, tvori 3 do 7-člani karbocikl ili heterocikl, a R1 i R4 neovisno predstavljaju:
• bilo skupinu -SiR5R6R7, pri čemu R5, R6 i R7 neovisno predstavljaju po izboru supstituiranu, ravnu ili razgrananu (C1-C6)alkil skupinu ili po izboru supstituiranu arilnu skupinu,
• ili po izboru supstituiranu aromatsku ili heteroaromatsku skupinu,
• ili po izboru supstituiranu, ravnu ili razgrananu (C1-C6)alkil skupinu.
3. Postupak sinteze u skladu s patentnim zahtjevom 2, naznačen time, da je katalizator na bazi željeza odabran između:
[image]
4. Postupak sinteze u skladu s patentnim zahtjevom 1, naznačen time, da katalizator na bazi željeza ima sljedeću opću formulu:
[image]
pri čemu R2 i R3 predstavljaju atom vodika ili pak zajedno s atomom ugljika koji ih nosi, tvore 3 do 7-člani karbocikl ili heterocikl, a R1 i R4 neovisno predstavljaju:
• bilo skupinu -SiR5R6R7, pri čemu R5, R6 i R7 neovisno predstavljaju po izboru supstituiranu, ravnu ili razgrananu (C1-C6)alkilnu skupinu ili po izboru supstituiranu aromatsku ili heteroaromatsku skupinu,
• ili po izboru supstituiranu aromatsku ili heteroaromatsku skupinu,
• ili po izboru supstituiranu, ravnu ili razgrananu (C1-C6)alkil skupinu.
5. Postupak sinteze u skladu s patentnim zahtjevom 4, naznačen time, da je katalizator na bazi željeza je odabran između:
[image]
6. Postupak prema zahtjevu 1, naznačen time, da katalizator na bazi željeza ima sljedeću formulu:
[image]
7. Postupak prema zahtjevu 1, naznačen time, da katalizator na bazi željeza ima sljedeću formulu:
[image]
8. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time, da je količina katalizatora korištenog u reakciji redukcijske aminacije od 1 mol% do 10 mol% u odnosu na aldehid.
9. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time, da je količina N-oksida korištenog u reakciji redukcijske aminacije od 0 do 3 ekvivalenta u odnosu na katalizator.
10. Postupak sinteze u skladu s patentnim zahtjevom 9, naznačen time, da je količina trimetilamin N-oksida koji se koristi u reakciji redukcijske aminacije od 0,5 do 1,5 ekvivalenata u odnosu na katalizator.
11. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačen time, da je tlak dihidrogena u reakciji redukcijske aminacije od 1 do 10 bara.
12. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 11, naznačen time, da je otapalo u reakciji redukcijske aminacije alkohol.
13. Postupak sinteze u skladu s patentnim zahtjevom 12, naznačen time, da je otapalo u reakciji redukcijske aminacije etanol.
14. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 13, naznačen time, da je temperatura reakcije redukcijske aminacije od 50 do 100°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1103933A FR2984319B1 (fr) | 2011-12-20 | 2011-12-20 | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20141023T1 true HRP20141023T1 (hr) | 2014-12-05 |
Family
ID=47115640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20141023AT HRP20141023T1 (hr) | 2011-12-20 | 2014-10-23 | Novi postupak sinteze ivabradina i njegovih adicijskih soli sa farmaceutski prihvatljivom kiselinom |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US8513410B2 (hr) |
| EP (1) | EP2607353B1 (hr) |
| JP (1) | JP5670406B2 (hr) |
| KR (1) | KR101470879B1 (hr) |
| CN (1) | CN103172566B (hr) |
| AR (1) | AR088678A1 (hr) |
| AU (1) | AU2012244188B2 (hr) |
| BR (1) | BR102012028614A2 (hr) |
| CA (1) | CA2795741C (hr) |
| CL (1) | CL2012003136A1 (hr) |
| CY (1) | CY1115682T1 (hr) |
| DK (1) | DK2607353T3 (hr) |
| EA (1) | EA026510B1 (hr) |
| ES (1) | ES2525032T3 (hr) |
| FR (1) | FR2984319B1 (hr) |
| GE (1) | GEP20156350B (hr) |
| HR (1) | HRP20141023T1 (hr) |
| JO (1) | JO3031B1 (hr) |
| MA (1) | MA34276B1 (hr) |
| MD (1) | MD4336C1 (hr) |
| MX (1) | MX2012012938A (hr) |
| MY (1) | MY170662A (hr) |
| PE (1) | PE20131097A1 (hr) |
| PL (1) | PL2607353T3 (hr) |
| PT (1) | PT2607353E (hr) |
| RS (1) | RS53541B1 (hr) |
| SA (1) | SA112330994B1 (hr) |
| SG (1) | SG191471A1 (hr) |
| SI (1) | SI2607353T1 (hr) |
| TW (1) | TWI440627B (hr) |
| UA (1) | UA111329C2 (hr) |
| UY (1) | UY34423A (hr) |
| WO (1) | WO2013093220A1 (hr) |
| ZA (1) | ZA201208160B (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2988720B1 (fr) * | 2012-03-27 | 2014-03-14 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| CN105669554A (zh) * | 2016-02-22 | 2016-06-15 | 徐建立 | 一种盐酸伊伐布雷定杂质及其制备方法和应用 |
| FR3071833B1 (fr) * | 2017-09-29 | 2020-01-03 | Universite Paris-Sud | Nouveau procede de synthese d'amines tertiaires dissymetriques |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2681862B1 (fr) * | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
| US6225487B1 (en) * | 1998-04-17 | 2001-05-01 | Symyx Technologies, Inc. | Ancillary ligands and metal complexes, catalysts and compositions using same and methods of testing |
| US6521793B1 (en) * | 1998-10-08 | 2003-02-18 | Symyx Technologies, Inc. | Catalyst ligands, catalytic metal complexes and processes using same |
| FR2868777B1 (fr) * | 2004-04-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| EP1595888A1 (en) * | 2004-05-11 | 2005-11-16 | Degussa AG | Cycloolefin phosphine ligands and their use in catalysis |
| WO2008065681A2 (en) * | 2006-11-30 | 2008-06-05 | Cadila Healthcare Limited | Process for preparation of ivabradine hydrochloride |
| PT2471780E (pt) * | 2007-05-30 | 2015-02-24 | Ind Swift Lab Ltd | Sais oxalato de ivabradina cristalinos e seus polimorfos |
| US7857994B2 (en) | 2007-05-30 | 2010-12-28 | GE Lighting Solutions, LLC | Green emitting phosphors and blends thereof |
| FR2920773B1 (fr) * | 2007-09-11 | 2009-10-23 | Servier Lab | Derives de 1,2,4,5-tetrahydro-3h-benzazepines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2933975B1 (fr) * | 2008-07-17 | 2011-02-18 | Servier Lab | Nouveau procede de preparation de benzocyclobutenes fonctionnalises,et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| FR2935381B1 (fr) * | 2008-08-29 | 2010-12-17 | Servier Lab | Nouveau procede de resolution des enantiomerees du (3,4-dimethoxy-bicyclo°4.2.0!octa-1,3,5-trien-7-yl)nitrile et application a la synthese de l'ivabradine |
| FR2940287B1 (fr) * | 2008-12-24 | 2010-12-24 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| FR2941695B1 (fr) * | 2009-02-04 | 2011-02-18 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
-
2011
- 2011-12-20 FR FR1103933A patent/FR2984319B1/fr not_active Expired - Fee Related
-
2012
- 2012-10-23 JO JOP/2012/0320A patent/JO3031B1/ar active
- 2012-10-23 SG SG2012078705A patent/SG191471A1/en unknown
- 2012-10-24 CA CA2795741A patent/CA2795741C/fr not_active Expired - Fee Related
- 2012-10-24 AU AU2012244188A patent/AU2012244188B2/en not_active Ceased
- 2012-10-25 PE PE2012002077A patent/PE20131097A1/es active IP Right Grant
- 2012-10-30 UY UY0001034423A patent/UY34423A/es not_active Application Discontinuation
- 2012-10-30 ZA ZA2012/08160A patent/ZA201208160B/en unknown
- 2012-10-30 MY MYPI2012700844A patent/MY170662A/en unknown
- 2012-10-31 MD MDA20120094A patent/MD4336C1/ro not_active IP Right Cessation
- 2012-11-06 TW TW101141192A patent/TWI440627B/zh not_active IP Right Cessation
- 2012-11-07 MA MA35353A patent/MA34276B1/fr unknown
- 2012-11-07 AR ARP120104179A patent/AR088678A1/es unknown
- 2012-11-07 MX MX2012012938A patent/MX2012012938A/es active IP Right Grant
- 2012-11-08 UA UAA201212746A patent/UA111329C2/uk unknown
- 2012-11-08 KR KR1020120126314A patent/KR101470879B1/ko not_active Expired - Fee Related
- 2012-11-08 CL CL2012003136A patent/CL2012003136A1/es unknown
- 2012-11-08 GE GEAP201212889A patent/GEP20156350B/en unknown
- 2012-11-08 BR BR102012028614-9A patent/BR102012028614A2/pt not_active IP Right Cessation
- 2012-11-08 CN CN201210443036.8A patent/CN103172566B/zh not_active Expired - Fee Related
- 2012-11-09 RS RSP20140509 patent/RS53541B1/en unknown
- 2012-11-09 US US13/673,145 patent/US8513410B2/en not_active Expired - Fee Related
- 2012-11-09 PL PL12191902T patent/PL2607353T3/pl unknown
- 2012-11-09 SI SI201230089T patent/SI2607353T1/sl unknown
- 2012-11-09 EP EP12191902.1A patent/EP2607353B1/fr active Active
- 2012-11-09 WO PCT/FR2012/000451 patent/WO2013093220A1/fr active Application Filing
- 2012-11-09 EA EA201201385A patent/EA026510B1/ru not_active IP Right Cessation
- 2012-11-09 JP JP2012247143A patent/JP5670406B2/ja active Active
- 2012-11-09 DK DK12191902.1T patent/DK2607353T3/en active
- 2012-11-09 PT PT121919021T patent/PT2607353E/pt unknown
- 2012-11-09 ES ES12191902.1T patent/ES2525032T3/es active Active
- 2012-11-10 SA SA112330994A patent/SA112330994B1/ar unknown
-
2014
- 2014-10-14 CY CY20141100832T patent/CY1115682T1/el unknown
- 2014-10-23 HR HRP20141023AT patent/HRP20141023T1/hr unknown
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