HRP20090212T1 - Postupak za kiralnu inverziju (s)-(+)- i (r)-(-)10,11-dihidro-10-hidroksi-5h-dibenz/b,f/azepin-5-karboksamida i njegovih optički obogaćenih smjesa - Google Patents
Postupak za kiralnu inverziju (s)-(+)- i (r)-(-)10,11-dihidro-10-hidroksi-5h-dibenz/b,f/azepin-5-karboksamida i njegovih optički obogaćenih smjesa Download PDFInfo
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- HRP20090212T1 HRP20090212T1 HR20090212T HRP20090212T HRP20090212T1 HR P20090212 T1 HRP20090212 T1 HR P20090212T1 HR 20090212 T HR20090212 T HR 20090212T HR P20090212 T HRP20090212 T HR P20090212T HR P20090212 T1 HRP20090212 T1 HR P20090212T1
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- Prior art keywords
- azepine
- carboxamide
- dibenz
- carbon atoms
- dihydro
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 33
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 title claims abstract 16
- 239000000203 mixture Substances 0.000 title 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 8
- 239000012038 nucleophile Substances 0.000 claims abstract 8
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- 238000005886 esterification reaction Methods 0.000 claims abstract 4
- 239000012442 inert solvent Substances 0.000 claims abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract 3
- 230000032050 esterification Effects 0.000 claims abstract 3
- 150000003003 phosphines Chemical class 0.000 claims abstract 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 238000013375 chromatographic separation Methods 0.000 claims 5
- 238000002425 crystallisation Methods 0.000 claims 5
- 230000008025 crystallization Effects 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- 125000002723 alicyclic group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005604 azodicarboxylate group Chemical group 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 239000011630 iodine Substances 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 1
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 claims 1
- SVABQOITNJTVNJ-UHFFFAOYSA-N diphenyl-2-pyridylphosphine Chemical compound C1=CC=CC=C1P(C=1N=CC=CC=1)C1=CC=CC=C1 SVABQOITNJTVNJ-UHFFFAOYSA-N 0.000 claims 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical group COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 claims 1
- OQJBFFCUFALWQL-UHFFFAOYSA-N n-(piperidine-1-carbonylimino)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)N=NC(=O)N1CCCCC1 OQJBFFCUFALWQL-UHFFFAOYSA-N 0.000 claims 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 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 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- -1 tri-substituted phosphine Chemical class 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 claims 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Postupak za kiralnu inverziju i esterifikaciju optički čistog ili optički obogaćenog (R)-(-)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (II), naznačen time da obuhvaća reagiranje optički čistog ili obogaćenog (R)-(-)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (II) sa nukleofilom karboksilne kiseline u prisutnosti trisupstituiranog fosfina i disupstituiranog azodikarboksilata u inertnom otapalu. Patent sadrži još 24 patentna zahtjeva.
Claims (25)
1. Postupak za kiralnu inverziju i esterifikaciju optički čistog ili optički obogaćenog (R)-(-)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (II), naznačen time da obuhvaća reagiranje optički čistog ili obogaćenog (R)-(-)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (II) sa nukleofilom karboksilne kiseline u prisutnosti trisupstituiranog fosfina i disupstituiranog azodikarboksilata u inertnom otapalu.
2. Postupak za kiralnu inverziju i esterifikaciju optički čistog ili optički obogaćenog (S)-(+)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (I) naznačen time da obuhvaća reagiranje optički čistog ili obogaćenog (S)-(+)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (I) sa nukleofilom karboksilne kiseline u prisutnosti trisupstituiranog fosfina i disupstituiranog azodikarboksilata u inertnom otapalu.
3. Postupak prema patentnom zahtjevu 1 ili 2 naznačen time da je nukleofil karboksilne kiseline alifatska karboksilna kiselina, linearna ili razgranata, koja sadrži jedan do osamnaest atoma ugljika, te može biti supstituirana aril grupom ili halogenom pri čemu izraz halogen znači fluor, klor, brom ili jod.
4. Postupak prema patentnim zahtjevima 1, 2 ili 3 naznačen time da je nukleofil karboksilne kiseline octena kiselina.
5. Postupak prema patentnim zahtjevima 1 ili 2 naznačen time da je nukleofil karboksilne kiseline prstenasta kiselina koja sadrži četiri do sedam atoma ugljika.
6. Postupak prema patentnim zahtjevima 1 ili 2 naznačen time da je nukleofil karboksilne kiseline benzojeva kiselina, koja može biti supstituirana sa alkoksi, halogen ili nitro skupinama.
7. Postupak prema patentnom zahtjevu 1 ili 2 naznačen time da je nukleofil karboksilne kiseline heteroaromatska kiselina koja sadrži barem jedan atom dušika.
8. Postupak prema bilo kojem od prethodnih patentnih zahtjeva naznačen time da je tri-supstituirani fosfin izabran iz tri-n-propilfosfina, tri-n-butilfosfina, trifenilfosfina, tri-o-tolilfosfina,difenil(2-piridil)fosfina,(4-dimetilamino)difenilfosfina i tris(dimetilamino)fosfina.
9. Postupak prema bilo kojem od prethodnih patentnih zahtjeva naznačen time da je disupstituirani azodikarboksilat izabran iz dimetilazodikarboksilata, dietilazodikarboksilata, diizopropilazodikarboksilata, di-tert-butilazodikarboksilata i 1,1'-(azodikarbonil)dipiperidina.
10. Postupak prema bilo kojem od prethodnih patentnih zahtjeva naznačen time da je inertno otapalo izabrano iz diklormetana, kloroforma, tetraklor ugljika, tetrahidrofurana, dietil etera, dimetilformamida, dioksana i toluena.
11. Postupak prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da se produkt reakcije kiralne inverzije i esterifikacije pročišćava kristalizacijom iz prikladnog otapala bez bilo kojeg koraka kromatografskog odjeljivanja.
12. Postupak za pripravu spoja općenite formule (VIII):
[image]
(VIII)
gdje je R1 vodik, alkil, halogenalkil, aralkil, cikloalkil, cikloalkilaril, aril ili piridil; izraz alkil znači linearni ili razgranati ugljikovodični lanac koji sadrži 1 – 18 atoma ugljika; izraz halogen znači fluor, klor, brom ili jod; izraz cikloalkil znači alicikličku zasićenu skupinu sa 3 do 6 atoma ugljika; te izraz aril znači nesupstituiranu fenil skupinu ili fenil supstituiran alkoksi, halogen ili nitro grupom, pri čemu spomenuti postupak sadrži reagiranje (R)-(-)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (II) postupkom prema patentnom zahtjevu 1, ili prema bilo kojem od zahtjeva 3 do 12, kad se oni pozivaju na patentni zahtjev 1.
13. Postupak prema patentnom zahtjevu 12, naznačen time da izraz alkil znači linearni ili razgranati ugljikovodični lanac koji sadrži 1 do 8 atoma ugljika.
14. Postupak prema patentnom zahtjevu 12, naznačen time da izraz alkil znači linearni ili razgranati ugljikovodični lanac koji sadrži 1 do 4 atoma ugljika.
15. Postupak prema patentnom zahtjevu 12, 13 ili 14, naznačen time da izraz cikloalkil znači alicikličku zasićenu skupinu sa 5 ili 6 atoma ugljika.
16. Postupak prema bilo kojem od patentnih zahtjeva 12 do 15, naznačen time da se spoj formule (VIII) pročišćava kristalizacijom iz prikladnog otapala bez bilo kojeg koraka kromatografskog odjeljivanja.
17. Postupak za pripravu spoja općenite formule (IX):
[image]
(IX)
gdje je R1 vodik, alkil, halogenalkil, aralkil, cikloalkil, cikloalkilaril, aril ili piridil; izraz alkil znači linearni ili razgranati ugljikovodični lanac koji sadrži 1 – 18 atoma ugljika; izraz halogen znači fluor, klor, brom ili jod; izraz cikloalkil znači alicikličku zasićenu skupinu sa 3 do 6 atoma ugljika; te izraz aril znači nesupstituiranu fenil skupinu ili fenil supstituiran alkoksi, halogen ili nitro grupom, pri čemu spomenuti postupak sadrži reagiranje (S)-(+)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (I) postupkom prema patentnom zahtjevu 2, ili prema bilo kojem od zahtjeva 3 do 12, kad se oni pozivaju na patentni zahtjev 2.
18. Postupak prema patentnom zahtjevu 17, naznačen time da izraz alkil znači linearni ili razgranati ugljikovodični lanac koji sadrži 1 do 8 atoma ugljika.
19. Postupak prema patentnom zahtjevu 17, naznačen time da izraz alkil znači linearni ili razgranati ugljikovodični lanac koji sadrži 1 do 4 atoma ugljika.
20. Postupak prema patentnom zahtjevu 17, 18 ili 19, naznačen time da izraz cikloalkil znači alicikličku zasićenu skupinu sa 5 ili 6 atoma ugljika.
21. Postupak prema bilo kojem od patentnih zahtjeva 17 do 20, naznačen time da se spoj formule (IX) pročišćava kristalizacijom iz prikladnog otapala bez bilo kojeg koraka kromatografskog odjeljivanja.
22. Postupak za pripravu (S)-(-)-10-acetoksi-10,11-dihidro-5H-dibenz/b,f/azepin-5-karboksamida (V) naznačen time da obuhvaća reagiranje optički čistog ili optički obogaćenog (R)-(-)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (II) postupkom prema patentnom zahtjevu 1, ili prema bilo kojem od zahtjeva 3 do 12, kad se oni pozivaju na patentni zahtjev 1.
23. Postupak prema patentnom zahtjevu 22, naznačen time da se spoj formule V pročišćava kristalizacijom iz prikladnog otapala bez bilo kojeg koraka kromatografskog odjeljivanja.
24. Postupak za pripravu (R)-(+)-10-acetoksi-10,11-hidro-5H-dibenz/b,f/azepin-5-karboksamida (VI) naznačen time da obuhvaća reagiranje optički čistog ili optički obogaćenog (S)-(+)-10,11-dihidro-10-hidroksi-5H-dibenz/b,f/azepin-5-karboksamida (I) postupkom prema patentnom zahtjevu 2, ili prema bilo kojem od zahtjeva 3 do 12, kad se oni pozivaju na patentni zahtjev 2.
25. Postupak prema patentnom zahtjevu 24, naznačen time da se spoj formule VI pročišćava kristalizacijom iz prikladnog otapala bez bilo kojeg koraka kromatografskog odjeljivanja.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0415664A GB2416167A (en) | 2004-07-13 | 2004-07-13 | Chiral inversion and esterification of (S)- and (R)-10-hydroxy-dibenzazepine carboxamides |
| PCT/GB2005/002744 WO2006005951A1 (en) | 2004-07-13 | 2005-07-13 | Method for chiral inversion of (s)-(+)- and (r)-(-)-10,11-dihydro-10-hydroxy-5h-dibenz/b,f/azepine-5-carboxamide and optically enriched mixtures thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090212T1 true HRP20090212T1 (hr) | 2009-09-30 |
Family
ID=32893499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090212T HRP20090212T1 (hr) | 2004-07-13 | 2009-04-08 | Postupak za kiralnu inverziju (s)-(+)- i (r)-(-)10,11-dihidro-10-hidroksi-5h-dibenz/b,f/azepin-5-karboksamida i njegovih optički obogaćenih smjesa |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7999100B2 (hr) |
| EP (1) | EP1789395B8 (hr) |
| JP (1) | JP2008506676A (hr) |
| CN (1) | CN100582095C (hr) |
| AR (1) | AR050170A1 (hr) |
| AT (1) | ATE420864T1 (hr) |
| AU (1) | AU2005261497A1 (hr) |
| BR (1) | BRPI0513383A (hr) |
| CA (1) | CA2574002C (hr) |
| DE (1) | DE602005012405D1 (hr) |
| DK (1) | DK1789395T3 (hr) |
| ES (1) | ES2320155T3 (hr) |
| GB (1) | GB2416167A (hr) |
| HR (1) | HRP20090212T1 (hr) |
| MX (1) | MX2007000575A (hr) |
| PL (1) | PL1789395T3 (hr) |
| PT (1) | PT103308B (hr) |
| RU (1) | RU2382772C2 (hr) |
| SI (1) | SI1789395T1 (hr) |
| WO (1) | WO2006005951A1 (hr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0515690D0 (en) | 2005-07-29 | 2005-09-07 | Portela & Ca Sa | Asymmetric catalytic reduction |
| GB2437078A (en) * | 2006-04-11 | 2007-10-17 | Portela & Ca Sa | 10-Acyloxy-5H-dibenzo[b,f]azepine-5-carboxamides & their asymmetric hydrogenation to the chiral 10,11-dihydro derivatives |
| GB0700773D0 (en) | 2007-01-15 | 2007-02-21 | Portela & Ca Sa | Drug therapies |
| US8372431B2 (en) | 2007-10-26 | 2013-02-12 | Bial-Portela & C.A., S.A. | Pharmaceutical composition comprising licarbazepine acetate |
| EP2414335A2 (en) * | 2009-04-02 | 2012-02-08 | Glenmark Generics Limited | A process for the purification of eslicarbazepine acetate |
| WO2011014084A1 (en) | 2009-07-27 | 2011-02-03 | Bial - Portela & Ca., S.A. | Use of 5h-dibenz / b, f/ azepine-5-carboxamide derivatives for treating fibromyalgia |
| WO2011045648A2 (en) * | 2009-10-12 | 2011-04-21 | Matrix Laboratories Limited | Process for preparing (s)-(-)-10-acetoxy-10,11-dihydro-5h-dibenz[b,f]azepine-5-carboxamide and its esters thereof |
| WO2011091131A2 (en) * | 2010-01-23 | 2011-07-28 | Dr. Reddy's Laboratories Ltd. | Eslicarbazepine acetate and its polymorphs |
| WO2011117885A1 (en) * | 2010-03-23 | 2011-09-29 | Intas Pharmaceuticals Limited | Process for preparation of enantiomers of licarbazepine |
| EP2683691B1 (en) | 2011-03-08 | 2018-06-06 | Jubilant Life Sciences Limited | PROCESS FOR THE PREPARATION OF (S)-(+)-10,11-DIHYDRO-10-HYDROXY-5H-DIBENZ[b,f]AZEPINE-5-CARBOXAMIDE AND ESTERS THEREOF BY ENANTIOSELECTIVE REDUCTION OF 10,11-DIHYDRO-10-OXO-5H-DIBENZ[b,f]AZEPINE-5-CARBOXAMIDE |
| WO2012156987A2 (en) * | 2011-05-19 | 2012-11-22 | Glenmark Generics Limited | A novel process for the preparation of eslicarbazepine |
| US20150065704A1 (en) | 2011-07-13 | 2015-03-05 | Ketan Hirpara | Process for the preparation and purification of eslicarbazepine acetate and intermediates thereof |
| IN2015DN02296A (hr) | 2012-09-26 | 2015-08-21 | Ranbaxy Lab Ltd | |
| EP3064490A1 (en) | 2015-03-06 | 2016-09-07 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of eslicarbazepine and eslicarbazepine acetate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT101732B (pt) * | 1995-06-30 | 1997-12-31 | Portela & Ca Sa | Novas di-hidrodibenzo<b,f>azepinas substituidas processo para a sua preparacao composicoes farmaceuticas que as contem e utilizacao dos novos compostos na preparacao de composicoes farmaceuticas empregues em doencas do sistema nervoso |
| GB0111566D0 (en) * | 2001-05-11 | 2001-07-04 | Portela & Ca Sa | Method for preparation of (s)-(+)-and (r)-(-)-10,11-dihydro-10-hydroxy-5h-dibenz/b,f/azephine-5-carboxamide |
-
2004
- 2004-07-13 GB GB0415664A patent/GB2416167A/en not_active Withdrawn
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2005
- 2005-07-13 BR BRPI0513383-1A patent/BRPI0513383A/pt not_active IP Right Cessation
- 2005-07-13 AR ARP050102910A patent/AR050170A1/es unknown
- 2005-07-13 AT AT05759707T patent/ATE420864T1/de active
- 2005-07-13 PT PT103308A patent/PT103308B/pt not_active IP Right Cessation
- 2005-07-13 ES ES05759707T patent/ES2320155T3/es active Active
- 2005-07-13 CA CA2574002A patent/CA2574002C/en active Active
- 2005-07-13 SI SI200530622T patent/SI1789395T1/sl unknown
- 2005-07-13 CN CN200580030684A patent/CN100582095C/zh not_active Expired - Fee Related
- 2005-07-13 US US11/572,077 patent/US7999100B2/en active Active
- 2005-07-13 EP EP05759707A patent/EP1789395B8/en active Active
- 2005-07-13 RU RU2007105228/04A patent/RU2382772C2/ru not_active IP Right Cessation
- 2005-07-13 WO PCT/GB2005/002744 patent/WO2006005951A1/en active Application Filing
- 2005-07-13 JP JP2007520888A patent/JP2008506676A/ja active Pending
- 2005-07-13 AU AU2005261497A patent/AU2005261497A1/en not_active Abandoned
- 2005-07-13 DK DK05759707T patent/DK1789395T3/da active
- 2005-07-13 MX MX2007000575A patent/MX2007000575A/es active IP Right Grant
- 2005-07-13 DE DE602005012405T patent/DE602005012405D1/de active Active
- 2005-07-13 PL PL05759707T patent/PL1789395T3/pl unknown
-
2009
- 2009-04-08 HR HR20090212T patent/HRP20090212T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT103308A (pt) | 2007-01-31 |
| GB0415664D0 (en) | 2004-08-18 |
| PL1789395T3 (pl) | 2009-06-30 |
| ATE420864T1 (de) | 2009-01-15 |
| CN100582095C (zh) | 2010-01-20 |
| GB2416167A (en) | 2006-01-18 |
| DK1789395T3 (da) | 2009-04-20 |
| BRPI0513383A (pt) | 2008-05-06 |
| CA2574002C (en) | 2014-02-04 |
| AU2005261497A1 (en) | 2006-01-19 |
| ES2320155T3 (es) | 2009-05-19 |
| EP1789395B1 (en) | 2009-01-14 |
| AR050170A1 (es) | 2006-10-04 |
| PT103308B (pt) | 2008-06-11 |
| RU2007105228A (ru) | 2008-08-20 |
| SI1789395T1 (sl) | 2009-06-30 |
| CN101023061A (zh) | 2007-08-22 |
| CA2574002A1 (en) | 2006-01-19 |
| WO2006005951A1 (en) | 2006-01-19 |
| US20080293934A1 (en) | 2008-11-27 |
| DE602005012405D1 (de) | 2009-03-05 |
| JP2008506676A (ja) | 2008-03-06 |
| EP1789395A1 (en) | 2007-05-30 |
| RU2382772C2 (ru) | 2010-02-27 |
| MX2007000575A (es) | 2007-03-30 |
| EP1789395B8 (en) | 2009-08-12 |
| US7999100B2 (en) | 2011-08-16 |
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