JP2015507023A5 - - Google Patents
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- Publication number
- JP2015507023A5 JP2015507023A5 JP2014557883A JP2014557883A JP2015507023A5 JP 2015507023 A5 JP2015507023 A5 JP 2015507023A5 JP 2014557883 A JP2014557883 A JP 2014557883A JP 2014557883 A JP2014557883 A JP 2014557883A JP 2015507023 A5 JP2015507023 A5 JP 2015507023A5
- Authority
- JP
- Japan
- Prior art keywords
- metal catalyst
- formula
- isotopologue
- chiral
- ligand
- 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.)
- Granted
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- 239000003054 catalyst Substances 0.000 claims 43
- 239000003446 ligand Substances 0.000 claims 37
- 239000002184 metal Substances 0.000 claims 37
- 229910052751 metal Inorganic materials 0.000 claims 37
- 238000000034 method Methods 0.000 claims 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 16
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 14
- 239000002904 solvent Substances 0.000 claims 14
- 239000010948 rhodium Substances 0.000 claims 13
- 239000003153 chemical reaction reagent Substances 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 12
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 9
- 229910000085 borane Inorganic materials 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 7
- 235000019253 formic acid Nutrition 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 6
- 150000002081 enamines Chemical class 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- -1 hydrates Chemical class 0.000 claims 6
- 150000004677 hydrates Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 238000005984 hydrogenation reaction Methods 0.000 claims 5
- AJNZWRKTWQLAJK-VGWMRTNUSA-N (2s,5s)-1-[2-[(2s,5s)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane Chemical compound C[C@H]1CC[C@H](C)P1C1=CC=CC=C1P1[C@@H](C)CC[C@@H]1C AJNZWRKTWQLAJK-VGWMRTNUSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 4
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims 4
- 229910052703 rhodium Inorganic materials 0.000 claims 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 4
- IRCDUOCGSIGEAI-AAVRWANBSA-N (2r,5r)-1-[2-[(2r,5r)-2,5-dimethylphospholan-1-yl]ethyl]-2,5-dimethylphospholane Chemical compound C[C@@H]1CC[C@@H](C)P1CCP1[C@H](C)CC[C@H]1C IRCDUOCGSIGEAI-AAVRWANBSA-N 0.000 claims 3
- GTIXSUJKFAATAE-UHFFFAOYSA-N (r)-c3-tunephos Chemical compound C=12C(C(=CC=C3)P(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3OCCCOC2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 GTIXSUJKFAATAE-UHFFFAOYSA-N 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 3
- ZYPSDHCBNMCWCZ-JQDLGSOUSA-N [(1r)-1-[2-bis[4-(trifluoromethyl)phenyl]phosphanylcyclopentyl]ethyl]-ditert-butylphosphane;cyclopentane;iron Chemical compound [Fe].[CH]1[CH][CH][CH][CH]1.CC(C)(C)P(C(C)(C)C)[C@H](C)[C]1[CH][CH][CH][C]1P(C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 ZYPSDHCBNMCWCZ-JQDLGSOUSA-N 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 3
- FWXAUDSWDBGCMN-ZEQRLZLVSA-N chiraphos Chemical compound C=1C=CC=CC=1P([C@@H](C)[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-ZEQRLZLVSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 150000007517 lewis acids Chemical class 0.000 claims 3
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 claims 3
- GYZZZILPVUYAFJ-UHFFFAOYSA-N phanephos Chemical compound C1CC(C(=C2)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C2CCC2=CC=C1C=C2P(C=1C=CC=CC=1)C1=CC=CC=C1 GYZZZILPVUYAFJ-UHFFFAOYSA-N 0.000 claims 3
- 229910000077 silane Inorganic materials 0.000 claims 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 2
- HYMSONXJNGZZBM-ODQAEMFESA-L [1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane;dichlororuthenium;(1r,2r)-1,2-diphenylethane-1,2-diamine Chemical compound Cl[Ru]Cl.C1([C@@H](N)[C@H](N)C=2C=CC=CC=2)=CC=CC=C1.CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 HYMSONXJNGZZBM-ODQAEMFESA-L 0.000 claims 2
- DQDVNUGYAGPIFX-UHFFFAOYSA-N acetic acid;[4-[5-bis(3,5-dimethylphenyl)phosphanyl-1,3-benzodioxol-4-yl]-1,3-benzodioxol-5-yl]-bis(3,5-dimethylphenyl)phosphane;ruthenium Chemical compound [Ru].CC(O)=O.CC(O)=O.CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C(=C3OCOC3=CC=2)C=2C(=CC=C3OCOC3=2)P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 DQDVNUGYAGPIFX-UHFFFAOYSA-N 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229910052707 ruthenium Inorganic materials 0.000 claims 2
- AJNZWRKTWQLAJK-KLHDSHLOSA-N (2r,5r)-1-[2-[(2r,5r)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane Chemical compound C[C@@H]1CC[C@@H](C)P1C1=CC=CC=C1P1[C@H](C)CC[C@H]1C AJNZWRKTWQLAJK-KLHDSHLOSA-N 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- XYUIGBMTIMBDDQ-UHFFFAOYSA-N borane N-ethyl-N-propan-2-ylaniline Chemical group B.CCN(C(C)C)C1=CC=CC=C1 XYUIGBMTIMBDDQ-UHFFFAOYSA-N 0.000 claims 1
- KHYAFFAGZNCWPT-UHFFFAOYSA-N boron;n,n-diethylaniline Chemical group [B].CCN(CC)C1=CC=CC=C1 KHYAFFAGZNCWPT-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 238000006459 hydrosilylation reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims 1
- PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 0 CC(*)(C(*)C1)C=CC1(C)C(N)=** Chemical compound CC(*)(C(*)C1)C=CC1(C)C(N)=** 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261601480P | 2012-02-21 | 2012-02-21 | |
| US61/601,480 | 2012-02-21 | ||
| US201261648521P | 2012-05-17 | 2012-05-17 | |
| US61/648,521 | 2012-05-17 | ||
| PCT/US2013/027010 WO2013126495A2 (en) | 2012-02-21 | 2013-02-21 | Asymmetric synthetic processes for the preparation of aminosulfone compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015507023A JP2015507023A (ja) | 2015-03-05 |
| JP2015507023A5 true JP2015507023A5 (enExample) | 2016-04-07 |
| JP6147769B2 JP6147769B2 (ja) | 2017-06-14 |
Family
ID=47755082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014557883A Active JP6147769B2 (ja) | 2012-02-21 | 2013-02-21 | アミノスルホン化合物の調製のための不斉合成方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9126906B2 (enExample) |
| EP (1) | EP2817289B1 (enExample) |
| JP (1) | JP6147769B2 (enExample) |
| ES (1) | ES2613850T3 (enExample) |
| WO (1) | WO2013126495A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR090100A1 (es) | 2012-02-21 | 2014-10-22 | Celgene Corp | Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
| US8981117B2 (en) | 2012-09-14 | 2015-03-17 | Celgene Corporation | Processes for the preparation of isoindole compounds and isotopologues thereof |
| EP2949645A1 (en) | 2014-05-28 | 2015-12-02 | LEK Pharmaceuticals d.d. | Processes for the preparation of ß-aminosulfone compounds |
| CN105622380B (zh) * | 2014-10-29 | 2020-06-30 | 南京安源生物医药科技有限公司 | 一种阿普斯特的制备方法及其中间体 |
| CN104447443B (zh) * | 2014-12-05 | 2016-07-27 | 新发药业有限公司 | 一种阿普斯特及其中间体的制备方法 |
| CN104761474B (zh) * | 2015-03-11 | 2016-11-30 | 中山奕安泰医药科技有限公司 | 一种阿普斯特手性胺中间体的合成方法 |
| EP3280701B1 (en) | 2015-04-09 | 2019-10-16 | Zentiva K.S. | A method of chiral resolution of the key intermediate of the synthesis of apremilast and its use for the preparation of pure apremilast |
| CN104803897A (zh) * | 2015-04-23 | 2015-07-29 | 中山奕安泰医药科技有限公司 | 一种阿普斯特中间体的合成工艺 |
| WO2016189486A1 (en) * | 2015-05-26 | 2016-12-01 | Lupin Limited | An improved process for preparation of apremilast and novel polymorphs thereof |
| CZ2015383A3 (cs) | 2015-06-05 | 2016-12-14 | Zentiva, K.S. | Způsob přípravy klíčového intermediátu apremilastu, využívající enzymatické štěpení racemických aminů |
| EP3106457A1 (en) | 2015-06-15 | 2016-12-21 | LEK Pharmaceuticals d.d. | A novel synthetic pathway towards apremilast |
| EP3144393A1 (en) | 2015-09-18 | 2017-03-22 | LEK Pharmaceuticals d.d. | A synthetic pathway towards apremilast |
| WO2017059040A1 (en) | 2015-09-29 | 2017-04-06 | Pliva Hrvatska D.O.O. | Processes for the preparation of apremilast and intermediates thereof |
| CN105218428A (zh) * | 2015-10-20 | 2016-01-06 | 南京美嘉宁逸医药研究开发有限公司 | 一种高手性纯度的阿普斯特的制备方法 |
| CN105461602B (zh) * | 2015-11-27 | 2018-01-02 | 东华大学 | 手性S或R‑3‑乙氧基‑4‑甲氧基‑α‑[(甲磺酰基)甲基]苯甲醇的制备方法 |
| CN105330586B (zh) * | 2015-11-27 | 2017-12-22 | 东华大学 | 一种阿普斯特的制备方法 |
| US10774041B2 (en) | 2016-04-15 | 2020-09-15 | Davuluri Ramamohan Rao | Process for the preparation of apremilast |
| IT201600083132A1 (it) * | 2016-08-05 | 2018-02-05 | Dipharma Francis Srl | Procedimento per la preparazione di un inibitore della fosfodiesterasi 4 |
| EP3606908B1 (en) | 2017-04-04 | 2020-06-17 | Quimica Sintetica, S.A. | Resolution of racemic beta-aminosulfone compounds |
| EP3421455B1 (en) * | 2017-06-29 | 2019-03-27 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of chiral 3-amino-piperidins, useful intermediates for the preparation of tofacitinib |
| CN112645854B (zh) * | 2020-12-23 | 2023-04-07 | 中山奕安泰医药科技有限公司 | 阿普斯特类中间体的精制方法 |
| CN115894310A (zh) * | 2021-08-13 | 2023-04-04 | 江苏正大清江制药有限公司 | 阿普斯特手性胺中间体新的制备方法 |
| CN115850129B (zh) * | 2023-02-28 | 2023-05-16 | 凯莱英生命科学技术(天津)有限公司 | （s）-1-(3-乙氧基-4-甲氧基苯基)-2-（甲磺酰基）乙胺的制备方法 |
| CN118834155B (zh) * | 2024-06-21 | 2025-08-12 | 江苏知原药业股份有限公司 | 阿普米司特的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR205978A1 (es) * | 1972-11-15 | 1976-06-23 | Sarl | Una bandeja de embalaje apilable |
| US5250731A (en) * | 1992-03-17 | 1993-10-05 | E. I. Du Pont De Nemours And Company | Preparation of optically active hydrazines and amines |
| EA001207B1 (ru) | 1996-03-22 | 2000-12-25 | Дюпон Фармасьютикалз Компани | Способ получения r-альфа-пропил-пиперониламина и его аналогов, промежуточные продукты, используемые в этом способе |
| WO1997047633A1 (en) * | 1996-06-14 | 1997-12-18 | The Penn State Research Foundation | Asymmetric synthesis catalyzed by transition metal complexes with cyclic chiral phosphine ligands |
| US6121184A (en) * | 1997-07-29 | 2000-09-19 | E. I. Du Pont De Nemours And Company | Supported bis(phosphorus) ligands |
| DE19741399A1 (de) * | 1997-09-19 | 1999-03-25 | Bayer Ag | Tetrahydrochinoline |
| WO1999015481A1 (en) * | 1997-09-24 | 1999-04-01 | Darwin Discovery Limited | Asymmetric hydrogenation |
| CN102076634A (zh) | 2008-06-27 | 2011-05-25 | 默克弗罗斯特加拿大有限公司 | 手性胺的合成 |
| HRP20130356T1 (en) * | 2008-09-10 | 2013-05-31 | Celgene Corporation | Processes for the preparation of aminosulfone compounds |
| AU2010246749B8 (en) | 2009-05-14 | 2014-03-20 | Ganzhou Hemay Pharmaceutical Co., Ltd | Thiophene derivatives |
| US20110040091A1 (en) * | 2009-08-13 | 2011-02-17 | Stephan Bachmann | Process for the preparation of (r)-2-phenyl propionic acid derivatives |
| AR090100A1 (es) * | 2012-02-21 | 2014-10-22 | Celgene Corp | Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
| US8981117B2 (en) * | 2012-09-14 | 2015-03-17 | Celgene Corporation | Processes for the preparation of isoindole compounds and isotopologues thereof |
-
2013
- 2013-02-20 US US13/772,242 patent/US9126906B2/en active Active
- 2013-02-21 JP JP2014557883A patent/JP6147769B2/ja active Active
- 2013-02-21 EP EP13706907.6A patent/EP2817289B1/en active Active
- 2013-02-21 ES ES13706907.6T patent/ES2613850T3/es active Active
- 2013-02-21 WO PCT/US2013/027010 patent/WO2013126495A2/en not_active Ceased
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