JP2008506676A5 - - Google Patents
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- JP2008506676A5 JP2008506676A5 JP2007520888A JP2007520888A JP2008506676A5 JP 2008506676 A5 JP2008506676 A5 JP 2008506676A5 JP 2007520888 A JP2007520888 A JP 2007520888A JP 2007520888 A JP2007520888 A JP 2007520888A JP 2008506676 A5 JP2008506676 A5 JP 2008506676A5
- Authority
- JP
- Japan
- Prior art keywords
- term
- carbon atoms
- dibenz
- azepine
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000004432 carbon atoms Chemical group C* 0.000 claims 12
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1H-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 7
- 239000012038 nucleophile Substances 0.000 claims 7
- 239000004215 Carbon black (E152) Substances 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 150000002430 hydrocarbons Chemical class 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000002723 alicyclic group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- USVVENVKYJZFMW-UHFFFAOYSA-L N-carboxylatoiminocarbamate Chemical class [O-]C(=O)N=NC([O-])=O USVVENVKYJZFMW-UHFFFAOYSA-L 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 3
- 239000011630 iodine Substances 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 150000003003 phosphines Chemical class 0.000 claims 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N Diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 238000005886 esterification reaction Methods 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
- 150000002431 hydrogen Chemical class 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- QSMUFXXTSUEZJA-UHFFFAOYSA-N 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid Chemical compound O=C1N(CC=2C=CC=CC=2)C(C(=O)O)C(C(O)=O)N1CC1=CC=CC=C1 QSMUFXXTSUEZJA-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 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
- 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
- KCXYZMFPZHYUFO-UHFFFAOYSA-N N-methyl-N-phosphanylmethanamine Chemical compound CN(C)P KCXYZMFPZHYUFO-UHFFFAOYSA-N 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N Tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 claims 1
- NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (NE)-N-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-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
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical group 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
Claims (20)
- 光学的に純粋な、又は光学的に濃縮された、(R)-(−)-10,11-ジヒドロ-10-ヒドロキシ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(II)を、実質的に不活性な溶媒中で、三置換ホスフィンと二置換アゾジカルボキシレートの存在下、カルボン酸求核試薬と反応させることを含む、光学的に純粋な、又は光学的に濃縮された、(R)-(−)-10,11-ジヒドロ-10-ヒドロキシ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(II)をキラル反転、及びエステル化する方法。
- 光学的に純粋な、又は光学的に濃縮された、(S)-(＋)-10,11-ジヒドロ-10-ヒドロキシ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(II)を、実質的に不活性な溶媒中で、三置換ホスフィンと二置換アゾジカルボキシレートの存在下、カルボン酸求核試薬と反応させることを含む、光学的に純粋な、又は光学的に濃縮された、(S)-(＋)-10,11-ジヒドロ-10-ヒドロキシ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(II)をキラル反転、及びエステル化する方法。
- 該カルボン酸求核試薬が、アリール基、又はハロゲンによって任意に置換されている、炭素原子１〜１８個を含む直鎖、又は分鎖脂肪族カルボン酸である（用語「ハロゲン」は、フッ素、塩素、臭素、又はヨウ素を意味する。）、請求項１、又は２記載の方法。
- 該カルボン酸求核試薬が酢酸である、請求項１、２、又は３記載の方法。
- 該カルボン酸求核試薬が、炭素原子４〜７個を含む環状酸である、請求項１、又は２記載の方法。
- 該カルボン酸求核試薬が、アルコキシ、ハロゲン、又はニトロ基によって任意に置換されている安息香酸である、請求項１、又は２記載の方法。
- 該カルボン酸求核試薬が、少なくとも１個の窒素原子を含む複素環式芳香族酸である、請求項１、又は２記載の方法。
- 該三置換ホスフィンが、トリ-n-プロピルホスフィン、トリ-n-ブチルホスフィン、トリフェニルホスフィン、トリ-o-トリルホスフィン、ジフェニル(2-ピリジル)ホスフィン、(4-ジメチルアミノ)ジフェニルホスフィン、及びトリス(ジメチルアミノ)ホスフィンから選択される、請求項１又は２記載の方法。
- 該二置換アゾジカルボキシレートが、ジメチルアゾジカルボキシレート、ジエチルアゾジカルボキシレート、ジイソプロピルアゾジカルボキシレート、ジ-tert-ブチルアゾジカルボキシレート、及び1,1'-(アゾジカルボニル)ジピペリジンから選択される、請求項１又は２記載の方法。
- 該実質上不活性な溶媒が、ジクロロメタン、クロロホルム、四塩化炭素、テトラヒドロフラン、ジエチルエーテル、ジメチルホルムアミド、ジオキサン、及びトルエンから選択される、請求項１、又は２記載の方法。
- 一般式(VIII)の化合物の製造方法であって、
- 該用語「アルキル」が、炭素原子１〜８個を含む直鎖、又は分鎖炭化水素を意味する、請求項１１記載の方法。
- 該用語「アルキル」が、炭素原子１〜４個を含む直鎖、又は分鎖炭化水素を意味する、請求項１１記載の方法。
- 該用語「シクロアルキル」が、炭素原子５個、又は６個を有する脂環式飽和基を意味する、請求項１１、１２、又は１３記載の方法。
- 一般式(IX)の化合物の製造方法であって、
- 該用語「アルキル」が、炭素原子１〜８個を含む直鎖、又は分鎖炭化水素を意味する、請求項１５記載の方法。
- 該用語「アルキル」が、炭素原子１〜４個を含む直鎖、又は分鎖炭化水素を意味する、請求項１５記載の方法。
- 該用語「シクロアルキル」が、炭素原子５個、又は６個を有する脂環式飽和基を意味する、請求項１５、１６、又は１７記載の方法。
- 光学的に純粋な、又は光学的に濃縮された、(R)-(−)-10,11-ジヒドロ-10-ヒドロキシ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(II)を、請求項１記載の方法によって反応させることを含む、(S)-(−)-10-アセトキシ-10,11-ジヒドロ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(V)の製造方法。
- 光学的に純粋な、又は光学的に濃縮された、(S)-(＋)-10,11-ジヒドロ-10-ヒドロキシ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(I)を、請求項２記載の方法によって反応させることを含む、(R)-(＋)-10-アセトキシ-10,11-ジヒドロ-5H-ジベンズ/b,f/アゼピン-5-カルボキサミド(VI)の製造方法。
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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2008506676A JP2008506676A (ja) | 2008-03-06 |
| JP2008506676A5 true JP2008506676A5 (ja) | 2008-07-24 |
Family
ID=32893499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007520888A Pending JP2008506676A (ja) | 2004-07-13 | 2005-07-13 | （Ｓ）−（＋）−、及び（Ｒ）−（−）−１０，１１−ジヒドロ−１０−ヒドロキシ−５Ｈ−ジベンズ／ｂ，ｆ／アゼピン−５−カルボキサミド、及びその光学的濃縮混合物をキラル反転する方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7999100B2 (ja) |
| EP (1) | EP1789395B8 (ja) |
| JP (1) | JP2008506676A (ja) |
| CN (1) | CN100582095C (ja) |
| AR (1) | AR050170A1 (ja) |
| AT (1) | ATE420864T1 (ja) |
| AU (1) | AU2005261497A1 (ja) |
| BR (1) | BRPI0513383A (ja) |
| CA (1) | CA2574002C (ja) |
| DE (1) | DE602005012405D1 (ja) |
| DK (1) | DK1789395T3 (ja) |
| ES (1) | ES2320155T3 (ja) |
| GB (1) | GB2416167A (ja) |
| HR (1) | HRP20090212T1 (ja) |
| MX (1) | MX2007000575A (ja) |
| PL (1) | PL1789395T3 (ja) |
| PT (1) | PT103308B (ja) |
| RU (1) | RU2382772C2 (ja) |
| SI (1) | SI1789395T1 (ja) |
| WO (1) | WO2006005951A1 (ja) |
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 |
| CA2769181C (en) | 2009-07-27 | 2017-11-28 | 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 |
| US20150232426A1 (en) | 2012-09-26 | 2015-08-20 | 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 AU AU2005261497A patent/AU2005261497A1/en not_active Abandoned
- 2005-07-13 JP JP2007520888A patent/JP2008506676A/ja active Pending
- 2005-07-13 CA CA2574002A patent/CA2574002C/en active Active
- 2005-07-13 SI SI200530622T patent/SI1789395T1/sl unknown
- 2005-07-13 MX MX2007000575A patent/MX2007000575A/es active IP Right Grant
- 2005-07-13 PL PL05759707T patent/PL1789395T3/pl unknown
- 2005-07-13 WO PCT/GB2005/002744 patent/WO2006005951A1/en active Application Filing
- 2005-07-13 DE DE602005012405T patent/DE602005012405D1/de 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 ES ES05759707T patent/ES2320155T3/es active Active
- 2005-07-13 AT AT05759707T patent/ATE420864T1/de active
- 2005-07-13 DK DK05759707T patent/DK1789395T3/da active
- 2005-07-13 CN CN200580030684A patent/CN100582095C/zh not_active Expired - Fee Related
- 2005-07-13 AR ARP050102910A patent/AR050170A1/es unknown
- 2005-07-13 PT PT103308A patent/PT103308B/pt not_active IP Right Cessation
- 2005-07-13 BR BRPI0513383-1A patent/BRPI0513383A/pt not_active IP Right Cessation
- 2005-07-13 US US11/572,077 patent/US7999100B2/en active Active
-
2009
- 2009-04-08 HR HR20090212T patent/HRP20090212T1/hr unknown
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