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
- Publication number
- 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
- Authority
- HR
- Croatia
- Prior art keywords
- azepine
- carboxamide
- dibenz
- carbon atoms
- dihydro
- Prior art date
Links
- 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
-
- 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
Landscapes
- 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)
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 (pt) |
| EP (1) | EP1789395B8 (pt) |
| JP (1) | JP2008506676A (pt) |
| CN (1) | CN100582095C (pt) |
| AR (1) | AR050170A1 (pt) |
| AT (1) | ATE420864T1 (pt) |
| AU (1) | AU2005261497A1 (pt) |
| BR (1) | BRPI0513383A (pt) |
| CA (1) | CA2574002C (pt) |
| DE (1) | DE602005012405D1 (pt) |
| DK (1) | DK1789395T3 (pt) |
| ES (1) | ES2320155T3 (pt) |
| GB (1) | GB2416167A (pt) |
| HR (1) | HRP20090212T1 (pt) |
| MX (1) | MX2007000575A (pt) |
| PL (1) | PL1789395T3 (pt) |
| PT (1) | PT103308B (pt) |
| RU (1) | RU2382772C2 (pt) |
| SI (1) | SI1789395T1 (pt) |
| WO (1) | WO2006005951A1 (pt) |
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 |
| WO2010113179A2 (en) * | 2009-04-02 | 2010-10-07 | Glenmark Generics Limited | A process for the purification of eslicarbazepine acetate |
| RU2012106827A (ru) | 2009-07-27 | 2013-09-10 | БИАЛ-ПОРТЕЛА энд КА., С.А. | Применение производных 5н-дибенз/в, f/азепин-5-карбоксамида для лечения фибромиалгии |
| 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 |
| WO2012120356A2 (en) | 2011-03-08 | 2012-09-13 | Jubilant Life Sciences Limited | Process for the preparation of (s)-(+)-or (r)-(-)-10 hydroxy dihydrodibenz[b,f]azepines by enantioselective reduction of 10, 11-dihydro-10-oxo-5h-dibenz[b,f]azepines and polymorphs thereof |
| 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 |
| WO2014049550A1 (en) | 2012-09-26 | 2014-04-03 | Ranbaxy Laboratories Limited | Process for the preparation of oxcarbazepine and its use as intermediate in the preparation of eslicarbazepine acetate |
| 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
-
2005
- 2005-07-13 SI SI200530622T patent/SI1789395T1/sl unknown
- 2005-07-13 DE DE602005012405T patent/DE602005012405D1/de active Active
- 2005-07-13 PT PT103308A patent/PT103308B/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 US US11/572,077 patent/US7999100B2/en active Active
- 2005-07-13 JP JP2007520888A patent/JP2008506676A/ja active Pending
- 2005-07-13 EP EP05759707A patent/EP1789395B8/en active Active
- 2005-07-13 WO PCT/GB2005/002744 patent/WO2006005951A1/en active Application Filing
- 2005-07-13 ES ES05759707T patent/ES2320155T3/es active Active
- 2005-07-13 MX MX2007000575A patent/MX2007000575A/es active IP Right Grant
- 2005-07-13 CA CA2574002A patent/CA2574002C/en active Active
- 2005-07-13 DK DK05759707T patent/DK1789395T3/da active
- 2005-07-13 PL PL05759707T patent/PL1789395T3/pl unknown
- 2005-07-13 AU AU2005261497A patent/AU2005261497A1/en not_active Abandoned
- 2005-07-13 BR BRPI0513383-1A patent/BRPI0513383A/pt not_active IP Right Cessation
- 2005-07-13 RU RU2007105228/04A patent/RU2382772C2/ru not_active IP Right Cessation
- 2005-07-13 CN CN200580030684A patent/CN100582095C/zh not_active Expired - Fee Related
-
2009
- 2009-04-08 HR HR20090212T patent/HRP20090212T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE602005012405D1 (de) | 2009-03-05 |
| GB2416167A (en) | 2006-01-18 |
| DK1789395T3 (da) | 2009-04-20 |
| CA2574002C (en) | 2014-02-04 |
| GB0415664D0 (en) | 2004-08-18 |
| PT103308B (pt) | 2008-06-11 |
| RU2007105228A (ru) | 2008-08-20 |
| EP1789395B8 (en) | 2009-08-12 |
| SI1789395T1 (sl) | 2009-06-30 |
| EP1789395A1 (en) | 2007-05-30 |
| CN101023061A (zh) | 2007-08-22 |
| WO2006005951A1 (en) | 2006-01-19 |
| JP2008506676A (ja) | 2008-03-06 |
| AU2005261497A1 (en) | 2006-01-19 |
| RU2382772C2 (ru) | 2010-02-27 |
| ATE420864T1 (de) | 2009-01-15 |
| PL1789395T3 (pl) | 2009-06-30 |
| CN100582095C (zh) | 2010-01-20 |
| BRPI0513383A (pt) | 2008-05-06 |
| AR050170A1 (es) | 2006-10-04 |
| US20080293934A1 (en) | 2008-11-27 |
| MX2007000575A (es) | 2007-03-30 |
| ES2320155T3 (es) | 2009-05-19 |
| PT103308A (pt) | 2007-01-31 |
| US7999100B2 (en) | 2011-08-16 |
| EP1789395B1 (en) | 2009-01-14 |
| CA2574002A1 (en) | 2006-01-19 |
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