JP2012513966A5 - - Google Patents
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- Publication number
- JP2012513966A5 JP2012513966A5 JP2011542822A JP2011542822A JP2012513966A5 JP 2012513966 A5 JP2012513966 A5 JP 2012513966A5 JP 2011542822 A JP2011542822 A JP 2011542822A JP 2011542822 A JP2011542822 A JP 2011542822A JP 2012513966 A5 JP2012513966 A5 JP 2012513966A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- compound
- phenol
- chiral
- dimethylamino
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 31
- 238000000034 method Methods 0.000 claims 23
- COJRWHSKVYUZHQ-ZCFIWIBFSA-N 3-[(1r)-1-hydroxyethyl]phenol Chemical compound C[C@@H](O)C1=CC=CC(O)=C1 COJRWHSKVYUZHQ-ZCFIWIBFSA-N 0.000 claims 9
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 238000002360 preparation method Methods 0.000 claims 8
- 229960004136 rivastigmine Drugs 0.000 claims 8
- GQZXRLWUYONVCP-QMMMGPOBSA-N 3-[(1s)-1-(dimethylamino)ethyl]phenol Chemical compound CN(C)[C@@H](C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-QMMMGPOBSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 238000006276 transfer reaction Methods 0.000 claims 6
- 230000001476 alcoholic effect Effects 0.000 claims 5
- 238000010531 catalytic reduction reaction Methods 0.000 claims 5
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 claims 4
- VPLSOSGETUGSOD-GRHHLOCNSA-N CN([C@@H](C)C=1C=C(C=CC1)O)C.CN([C@@H](C)C=1C=C(C=CC1)O)C Chemical compound CN([C@@H](C)C=1C=C(C=CC1)O)C.CN([C@@H](C)C=1C=C(C=CC1)O)C VPLSOSGETUGSOD-GRHHLOCNSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 150000004820 halides Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- -1 tetrafluoroborate Chemical compound 0.000 claims 4
- 229910052723 transition metal Inorganic materials 0.000 claims 4
- 150000003624 transition metals Chemical class 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000001414 amino alcohols Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 238000012377 drug delivery Methods 0.000 claims 2
- 239000012458 free base Substances 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
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- CLPXHEDITUKVCC-UHFFFAOYSA-K 1-methyl-4-propan-2-ylbenzene;trichlororuthenium Chemical class Cl[Ru](Cl)Cl.CC(C)C1=CC=C(C)C=C1 CLPXHEDITUKVCC-UHFFFAOYSA-K 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- ZUOFYVXFZNJPND-ZETCQYMHSA-N C[C@@H](C1=CC=CC(=C1)CS(=O)(=O)O)O Chemical compound C[C@@H](C1=CC=CC(=C1)CS(=O)(=O)O)O ZUOFYVXFZNJPND-ZETCQYMHSA-N 0.000 claims 1
- ZUOFYVXFZNJPND-SSDOTTSWSA-N C[C@H](C1=CC=CC(=C1)CS(=O)(=O)O)O Chemical compound C[C@H](C1=CC=CC(=C1)CS(=O)(=O)O)O ZUOFYVXFZNJPND-SSDOTTSWSA-N 0.000 claims 1
- NPYAZCQPWJLMFH-SSDOTTSWSA-N C[C@H](CS(=O)(=O)O)C1=CC(=CC=C1)O Chemical compound C[C@H](CS(=O)(=O)O)C1=CC(=CC=C1)O NPYAZCQPWJLMFH-SSDOTTSWSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- KORBNZMNKRINHE-SSDOTTSWSA-N [(1r)-1-(3-hydroxyphenyl)ethyl] methanesulfonate Chemical compound CS(=O)(=O)O[C@H](C)C1=CC=CC(O)=C1 KORBNZMNKRINHE-SSDOTTSWSA-N 0.000 claims 1
- CZCQMRZQDWWULM-SECBINFHSA-N [3-[(1r)-1-(dimethylamino)ethyl]phenyl] methanesulfonate Chemical compound CN(C)[C@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 CZCQMRZQDWWULM-SECBINFHSA-N 0.000 claims 1
- WAPZHQZXWPVDMP-MRVPVSSYSA-N [3-[(1r)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate Chemical compound CS(=O)(=O)O[C@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 WAPZHQZXWPVDMP-MRVPVSSYSA-N 0.000 claims 1
- CZCQMRZQDWWULM-VIFPVBQESA-N [3-[(1s)-1-(dimethylamino)ethyl]phenyl] methanesulfonate Chemical compound CN(C)[C@@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 CZCQMRZQDWWULM-VIFPVBQESA-N 0.000 claims 1
- WAPZHQZXWPVDMP-QMMMGPOBSA-N [3-[(1s)-1-methylsulfonyloxyethyl]phenyl] methanesulfonate Chemical compound CS(=O)(=O)O[C@@H](C)C1=CC=CC(OS(C)(=O)=O)=C1 WAPZHQZXWPVDMP-QMMMGPOBSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UOPFIWYXBIHPIP-NHCUHLMSSA-N n-[(1r,2r)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@H](C=1C=CC=CC=1)[C@H](N)C1=CC=CC=C1 UOPFIWYXBIHPIP-NHCUHLMSSA-N 0.000 claims 1
- KMJTTWREVXZPTK-UHFFFAOYSA-M n-ethyl-n-methylcarbamate Chemical compound CCN(C)C([O-])=O KMJTTWREVXZPTK-UHFFFAOYSA-M 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0823554.1 | 2008-12-24 | ||
| GBGB0823554.1A GB0823554D0 (en) | 2008-12-24 | 2008-12-24 | Process for the preparation of optically active compounds using transfer hydrogenation |
| PCT/EP2009/067821 WO2010072798A1 (en) | 2008-12-24 | 2009-12-23 | Process for the preparation of optically active compounds using transfer hydrogenation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012513966A JP2012513966A (ja) | 2012-06-21 |
| JP2012513966A5 true JP2012513966A5 (enExample) | 2013-02-21 |
Family
ID=40344210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542822A Pending JP2012513966A (ja) | 2008-12-24 | 2009-12-23 | 水素移動反応を使用する光学活性化合物の調製の方法 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8415508B2 (enExample) |
| EP (1) | EP2382172A1 (enExample) |
| JP (1) | JP2012513966A (enExample) |
| KR (1) | KR20110098964A (enExample) |
| CN (1) | CN102264672A (enExample) |
| AR (1) | AR075496A1 (enExample) |
| AU (1) | AU2009331493B2 (enExample) |
| BR (1) | BRPI0923394A2 (enExample) |
| CA (1) | CA2748349A1 (enExample) |
| CL (1) | CL2011001563A1 (enExample) |
| CO (1) | CO6382153A2 (enExample) |
| EC (1) | ECSP11011221A (enExample) |
| GB (1) | GB0823554D0 (enExample) |
| IL (1) | IL213520A0 (enExample) |
| MA (1) | MA32983B1 (enExample) |
| MX (1) | MX2011006918A (enExample) |
| MY (1) | MY151103A (enExample) |
| NZ (1) | NZ593493A (enExample) |
| SG (1) | SG172052A1 (enExample) |
| TN (1) | TN2011000290A1 (enExample) |
| TW (1) | TW201035028A (enExample) |
| WO (1) | WO2010072798A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193600B (zh) * | 2012-01-07 | 2016-04-06 | 浙江九洲药物科技有限公司 | 卡巴拉汀中间体的制备方法 |
| CN105246873A (zh) * | 2013-06-14 | 2016-01-13 | 日产化学工业株式会社 | 光学活性醇化合物的制造方法 |
| CN103980270A (zh) * | 2014-05-19 | 2014-08-13 | 埃斯特维华义制药有限公司 | 一种（r）-3-奎宁醇的制备方法 |
| CN108752322A (zh) * | 2018-09-12 | 2018-11-06 | 广州新民培林医药科技有限公司 | 一种新型Tepotinib衍生物和制备方法及其在抗肿瘤药物中的应用 |
| CN109809967B (zh) * | 2019-03-04 | 2022-03-18 | 陕西师范大学 | 一种合成手性醇的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU201906B (en) * | 1987-03-04 | 1991-01-28 | Sandoz Ag | Process for producing phenyl-carbamate derivative and acid additional salts and pharmaceutical compositions containing them |
| US4996235A (en) * | 1987-11-25 | 1991-02-26 | Eli Lilly And Company | 3,4-diphenylbutanamines |
| JPH0899940A (ja) * | 1994-09-30 | 1996-04-16 | Kanegafuchi Chem Ind Co Ltd | 光学活性な１−（３，４−ジメトキシフェニル）−２−アミノプロパンの製造法 |
| GB9706321D0 (en) | 1997-03-26 | 1997-05-14 | Zeneca Ltd | Catalytic hydrogenation |
| JP3938651B2 (ja) * | 2000-04-13 | 2007-06-27 | セントラル硝子株式会社 | 光学活性α−メチル−ビス−３、５−（トリフルオロメチル）ベンジルアミンの製造方法 |
| EP1346972A4 (en) | 2000-12-25 | 2005-06-01 | Ajinomoto Kk | PROCESS FOR PREPARING OPTICALLY ACTIVE HALOHYDRIN COMPOUND |
| CN100439307C (zh) * | 2003-07-08 | 2008-12-03 | 荷兰联合利华有限公司 | 化妆活性物质的制备方法 |
| GB0329284D0 (en) | 2003-12-18 | 2004-01-21 | Avecia Ltd | Process |
| KR101085804B1 (ko) | 2004-03-29 | 2011-11-22 | 간토 가가꾸 가부시키가이샤 | 광학 활성 알코올의 제법 |
| US6939981B1 (en) * | 2004-06-25 | 2005-09-06 | Eastman Chemical Company | Ruthenium complexes of phosphine-aminophosphine ligands |
| RU2393148C2 (ru) * | 2004-11-08 | 2010-06-27 | Эмкюр Фармасьютикалз Лимитед | Способ получения (s)-3-[(1-диметиламино)этил]-фенил-n-этил-n-метил-карбамата |
| WO2006137167A1 (ja) | 2005-06-20 | 2006-12-28 | Kanto Kagaku Kabushiki Kaisha | スルホナート触媒及びそれを利用したアルコール化合物の製法 |
| TWI389709B (zh) | 2005-12-01 | 2013-03-21 | Novartis Ag | 經皮治療系統 |
| WO2007147897A1 (de) | 2006-06-23 | 2007-12-27 | Basf Se | Verfahren zur herstellung von optisch aktiven 2-halogen-1-phenylethanol-derivaten und folgeprodukten davon |
| CA2760386A1 (en) | 2008-05-01 | 2009-11-05 | Kanata Chemical Technologies Inc. | Cationic transition-metal arene catalysts |
-
2008
- 2008-12-24 GB GBGB0823554.1A patent/GB0823554D0/en not_active Ceased
-
2009
- 2009-12-17 US US12/653,748 patent/US8415508B2/en not_active Expired - Fee Related
- 2009-12-22 AR ARP090105061A patent/AR075496A1/es not_active Application Discontinuation
- 2009-12-23 BR BRPI0923394A patent/BRPI0923394A2/pt not_active IP Right Cessation
- 2009-12-23 AU AU2009331493A patent/AU2009331493B2/en not_active Ceased
- 2009-12-23 SG SG2011042108A patent/SG172052A1/en unknown
- 2009-12-23 CN CN2009801523437A patent/CN102264672A/zh active Pending
- 2009-12-23 MA MA34036A patent/MA32983B1/fr unknown
- 2009-12-23 JP JP2011542822A patent/JP2012513966A/ja active Pending
- 2009-12-23 CA CA2748349A patent/CA2748349A1/en not_active Abandoned
- 2009-12-23 MY MYPI20112891 patent/MY151103A/en unknown
- 2009-12-23 KR KR1020117017258A patent/KR20110098964A/ko not_active Ceased
- 2009-12-23 EP EP09799106A patent/EP2382172A1/en not_active Withdrawn
- 2009-12-23 NZ NZ593493A patent/NZ593493A/xx not_active IP Right Cessation
- 2009-12-23 TW TW098144595A patent/TW201035028A/zh unknown
- 2009-12-23 WO PCT/EP2009/067821 patent/WO2010072798A1/en not_active Ceased
- 2009-12-23 MX MX2011006918A patent/MX2011006918A/es not_active Application Discontinuation
-
2011
- 2011-06-09 TN TN2011000290A patent/TN2011000290A1/fr unknown
- 2011-06-13 IL IL213520A patent/IL213520A0/en unknown
- 2011-06-23 CL CL2011001563A patent/CL2011001563A1/es unknown
- 2011-06-29 CO CO11081447A patent/CO6382153A2/es active IP Right Grant
- 2011-07-22 EC EC2011011221A patent/ECSP11011221A/es unknown
-
2012
- 2012-12-05 US US13/705,884 patent/US8637713B2/en not_active Expired - Fee Related
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