KR101791119B1 - N-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 - Google Patents

N-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 Download PDF

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KR101791119B1
KR101791119B1 KR1020177000413A KR20177000413A KR101791119B1 KR 101791119 B1 KR101791119 B1 KR 101791119B1 KR 1020177000413 A KR1020177000413 A KR 1020177000413A KR 20177000413 A KR20177000413 A KR 20177000413A KR 101791119 B1 KR101791119 B1 KR 101791119B1
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South Korea
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group
compound
acid
salt
equivalents
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KR1020177000413A
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Korean (ko)
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KR20170042548A (ko
Inventor
우병영
이기화
신광현
박미영
정경미
최준호
최계영
조원경
박영호
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(주)아모레퍼시픽
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/04—Monocyclic monocarboxylic acids
    • C07C63/06—Benzoic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
KR1020177000413A 2015-02-17 2016-02-15 N-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 Expired - Fee Related KR101791119B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
KR1020150024334 2015-02-17
KR1020150024334A KR20160101554A (ko) 2015-02-17 2015-02-17 N-[4-(1-아미노에틸)-페닐]-메탄술폰아미드 유도체의 카이랄 분할 방법
EP15174617.9 2015-06-30
EP15174617 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 (2)

Publication Number Publication Date
KR20170042548A KR20170042548A (ko) 2017-04-19
KR101791119B1 true KR101791119B1 (ko) 2017-11-20

Family

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Family Applications (1)

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KR1020177000413A Expired - Fee Related KR101791119B1 (ko) 2015-02-17 2016-02-15 N-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법

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)

* Cited by examiner, † Cited by third party
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
EP4107148A4 (en) 2020-02-16 2024-05-15 Ayala Pharmaceuticals Inc. PROCESS FOR PREPARING CHIRAL BENZODIAZEPINONE DERIVATIVES

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007129188A1 (en) * 2006-05-10 2007-11-15 Pfizer Japan Inc. Cyclopropanecarboxamide compound

Family Cites Families (15)

* Cited by examiner, † Cited by third party
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
JP2009536657A (ja) * 2006-05-10 2009-10-15 レノビス， インコーポレイテッド イオンチャンネルリガンドとしてのアミド誘導体およびそれを用いる医薬組成物および方法
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
EP1882687A1 (en) * 2006-07-27 2008-01-30 Amorepacific Corporation Heterocyclic compounds useful as vanilloid receptor antagonists and pharmaceutical compositions containing the same
JP5254228B2 (ja) * 2006-07-27 2013-08-07 株式會社アモーレパシフィック バニロイド受容体アンタゴニストとしての、新規化合物、その異性体またはその薬学的に許容される塩；並びにそれを含む医薬組成物
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
US8461334B2 (en) 2008-11-07 2013-06-11 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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007129188A1 (en) * 2006-05-10 2007-11-15 Pfizer Japan Inc. Cyclopropanecarboxamide compound

Also Published As

Publication number Publication date
CN106660949A (zh) 2017-05-10
TW201636319A (zh) 2016-10-16
US20170342027A1 (en) 2017-11-30
BR112017001516B1 (pt) 2023-10-31
CN106660949B (zh) 2020-11-13
EP3162793A4 (en) 2018-01-03
KR20170042548A (ko) 2017-04-19
TWI687396B (zh) 2020-03-11
EP3162793B1 (en) 2019-04-10
JP6687596B2 (ja) 2020-04-22
EP3162793A1 (en) 2017-05-03
BR112017001516A2 (pt) 2018-01-30
WO2016133317A1 (ko) 2016-08-25
JP2018506503A (ja) 2018-03-08
US10479763B2 (en) 2019-11-19

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