JP2018506503A5 - - Google Patents
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- JP2018506503A5 JP2018506503A5 JP2017502582A JP2017502582A JP2018506503A5 JP 2018506503 A5 JP2018506503 A5 JP 2018506503A5 JP 2017502582 A JP2017502582 A JP 2017502582A JP 2017502582 A JP2017502582 A JP 2017502582A JP 2018506503 A5 JP2018506503 A5 JP 2018506503A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- acid
- salt
- stereoisomer
- 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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- 238000000034 method Methods 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 25
- 239000000203 mixture Substances 0.000 claims 20
- 239000002904 solvent Substances 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 3
- 229960002510 mandelic acid Drugs 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 claims 1
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims 1
- CMIBUZBMZCBCAT-HOTGVXAUSA-N (2s,3s)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@H](C(O)=O)[C@@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HOTGVXAUSA-N 0.000 claims 1
- MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 claims 1
- YONLFQNRGZXBBF-UHFFFAOYSA-N 2,3-dibenzoyloxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)OC(C(O)=O)C(C(=O)O)OC(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-UHFFFAOYSA-N 0.000 claims 1
- -1 3,5-difluoro-4-methanesulfonylamino-phenyl Chemical group 0.000 claims 1
- VHHASABNDZHVDW-UHFFFAOYSA-N 3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound C(CC)C1=NC(=CC=C1C=CC(=O)N)C(F)(F)F VHHASABNDZHVDW-UHFFFAOYSA-N 0.000 claims 1
- CNCIJHJOEHBPBF-UHFFFAOYSA-N 3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enoic acid Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1C=CC(O)=O CNCIJHJOEHBPBF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 101100348848 Mus musculus Notch4 gene Proteins 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UKGJZDSUJSPAJL-GFCCVEGCSA-N n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1C=CC(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-GFCCVEGCSA-N 0.000 claims 1
- FORFBJNKDYMFQR-RXMQYKEDSA-N n-[4-[(1r)-1-aminoethyl]-2,6-difluorophenyl]methanesulfonamide Chemical group C[C@@H](N)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 FORFBJNKDYMFQR-RXMQYKEDSA-N 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020150024334A KR20160101554A (ko) | 2015-02-17 | 2015-02-17 | N-[4-(1-아미노에틸)-페닐]-메탄술폰아미드 유도체의 카이랄 분할 방법 |
| KR10-2015-0024334 | 2015-02-17 | ||
| EP15174617 | 2015-06-30 | ||
| EP15174617.9 | 2015-06-30 | ||
| PCT/KR2016/001474 WO2016133317A1 (ko) | 2015-02-17 | 2016-02-15 | Ｎ-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018506503A JP2018506503A (ja) | 2018-03-08 |
| JP2018506503A5 true JP2018506503A5 (enExample) | 2019-01-31 |
| JP6687596B2 JP6687596B2 (ja) | 2020-04-22 |
Family
ID=56692658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017502582A Active JP6687596B2 (ja) | 2015-02-17 | 2016-02-15 | Ｎ−［４−（１−アミノエチル）−フェニル］−スルホンアミド誘導体のキラル分割方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10479763B2 (enExample) |
| EP (1) | EP3162793B1 (enExample) |
| JP (1) | JP6687596B2 (enExample) |
| KR (1) | KR101791119B1 (enExample) |
| CN (1) | CN106660949B (enExample) |
| BR (1) | BR112017001516B1 (enExample) |
| TW (1) | TWI687396B (enExample) |
| WO (1) | WO2016133317A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102565407B1 (ko) * | 2016-01-04 | 2023-08-10 | (주)아모레퍼시픽 | 극성 비양자성 용매를 이용한 n-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 |
| KR102599958B1 (ko) | 2016-09-28 | 2023-11-09 | (주)아모레퍼시픽 | (r)-n-[4-(1-아미노-에틸)-2,6-다이플루오로-페닐]-메테인설폰아마이드의 제조방법 |
| KR102587339B1 (ko) * | 2016-12-22 | 2023-10-12 | (주)아모레퍼시픽 | N-[4-(1-아미노-에틸)-2,6-다이플루오로-페닐]-메테인설폰아마이드의 거울상 이성질체들의 라세미화 방법 |
| CN109608368B (zh) * | 2018-10-24 | 2021-03-09 | 常州市阳光药业有限公司 | N-[4-(1-氨基乙基)-2,6-二氟苯基]甲磺酰胺的合成及拆分方法 |
| KR20200053746A (ko) * | 2018-11-09 | 2020-05-19 | (주)아모레퍼시픽 | 졸-겔 조성물 |
| CN115103836A (zh) * | 2020-02-16 | 2022-09-23 | 艾雅拉制药公司 | 制备手性苯并二氮杂卓酮衍生物的方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60152425A (ja) * | 1984-01-20 | 1985-08-10 | Oyo Seikagaku Kenkyusho:Kk | ラセミ体の新規な光学分割法 |
| US4968837A (en) | 1989-07-28 | 1990-11-06 | Ethyl Corporation | Resolution of racemic mixtures |
| ATE125254T1 (de) * | 1989-09-19 | 1995-08-15 | Hoechst Roussel Pharma | Verfahren zur racematspaltung von 5-alkoxy- substituierten (+/-)-1,3- dimethyloxindolylethylaminen. |
| US6265615B1 (en) | 1998-07-01 | 2001-07-24 | The Regents Of The University Of California | Chiral recognition polymer and its use to separate enantiomers |
| DE19956786A1 (de) * | 1999-11-25 | 2001-05-31 | Basf Ag | Verfahren zur Herstellung optisch aktiver Amine |
| US7301023B2 (en) * | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| BRPI0608436A2 (pt) * | 2005-03-17 | 2009-12-29 | Pfizer | derivados de n-(n-sulfonilaminometil) ciclopropanocarboxamida utilizáveis para o tratamento de dor |
| US20120041225A1 (en) * | 2006-02-03 | 2012-02-16 | Vaidya Niteen A | Kit for automated resolving agent selection and method thereof |
| WO2007129188A1 (en) * | 2006-05-10 | 2007-11-15 | Pfizer Japan Inc. | Cyclopropanecarboxamide compound |
| WO2007133637A2 (en) | 2006-05-10 | 2007-11-22 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
| EP1862454A1 (en) * | 2006-06-02 | 2007-12-05 | Amorepacific Corporation | Novel compounds, isomer thereof or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and a pharmaceutical composition containing the same |
| PL2054411T3 (pl) | 2006-07-27 | 2015-02-27 | Amorepacific Corp | Nowe związki, ich izomery lub ich farmaceutycznie dopuszczalne sole jako antagoniści receptora waniloidowego oraz zawierające je kompozycje farmaceutyczne |
| EP1882687A1 (en) * | 2006-07-27 | 2008-01-30 | Amorepacific Corporation | Heterocyclic compounds useful as vanilloid receptor antagonists and pharmaceutical compositions containing the same |
| JP2011201778A (ja) * | 2008-07-23 | 2011-10-13 | Mochida Pharmaceut Co Ltd | ｐ−置換アリールアセトアミドを有するヘテロシクリデン誘導体 |
| EP2356121A1 (en) | 2008-11-07 | 2011-08-17 | Cipla Limited | Process for resolving zopiclone |
| KR20160101554A (ko) | 2015-02-17 | 2016-08-25 | (주)아모레퍼시픽 | N-[4-(1-아미노에틸)-페닐]-메탄술폰아미드 유도체의 카이랄 분할 방법 |
-
2016
- 2016-02-15 CN CN201680002149.0A patent/CN106660949B/zh active Active
- 2016-02-15 WO PCT/KR2016/001474 patent/WO2016133317A1/ko not_active Ceased
- 2016-02-15 JP JP2017502582A patent/JP6687596B2/ja active Active
- 2016-02-15 EP EP16752647.4A patent/EP3162793B1/en active Active
- 2016-02-15 US US15/325,349 patent/US10479763B2/en active Active
- 2016-02-15 KR KR1020177000413A patent/KR101791119B1/ko not_active Expired - Fee Related
- 2016-02-15 BR BR112017001516-1A patent/BR112017001516B1/pt not_active IP Right Cessation
- 2016-02-16 TW TW105104399A patent/TWI687396B/zh active
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