CN106660949B - N-[4-(1-氨基乙基)-苯基]-磺酰胺衍生物的手性拆分方法 - Google Patents

N-[4-(1-氨基乙基)-苯基]-磺酰胺衍生物的手性拆分方法 Download PDF

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Publication number
CN106660949B
CN106660949B CN201680002149.0A CN201680002149A CN106660949B CN 106660949 B CN106660949 B CN 106660949B CN 201680002149 A CN201680002149 A CN 201680002149A CN 106660949 B CN106660949 B CN 106660949B
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acid
compound
mixture
stereoisomers
chiral
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Chinese (zh)
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CN106660949A (zh
Inventor
禹柄英
李玘和
申光炫
朴美渶
郑京美
崔俊镐
崔季英
赵原庆
朴永镐
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Amorepacific Corp
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Amorepacific Corp
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    • 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
    • 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
    • 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
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • 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)
CN201680002149.0A 2015-02-17 2016-02-15 N-[4-(1-氨基乙基)-苯基]-磺酰胺衍生物的手性拆分方法 Active CN106660949B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
KR10-2015-0024334 2015-02-17
KR1020150024334A KR20160101554A (ko) 2015-02-17 2015-02-17 N-[4-(1-아미노에틸)-페닐]-메탄술폰아미드 유도체의 카이랄 분할 방법
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 (2)

Publication Number Publication Date
CN106660949A CN106660949A (zh) 2017-05-10
CN106660949B true CN106660949B (zh) 2020-11-13

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Country Status (8)

Country Link
US (1) US10479763B2 (cg-RX-API-DMAC7.html)
EP (1) EP3162793B1 (cg-RX-API-DMAC7.html)
JP (1) JP6687596B2 (cg-RX-API-DMAC7.html)
KR (1) KR101791119B1 (cg-RX-API-DMAC7.html)
CN (1) CN106660949B (cg-RX-API-DMAC7.html)
BR (1) BR112017001516B1 (cg-RX-API-DMAC7.html)
TW (1) TWI687396B (cg-RX-API-DMAC7.html)
WO (1) WO2016133317A1 (cg-RX-API-DMAC7.html)

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
WO2021163676A1 (en) * 2020-02-16 2021-08-19 Ayala Pharmaceuticals Inc. Methods of preparing chiral benzodiazepinone derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN101160285A (zh) * 2005-03-17 2008-04-09 辉瑞大药厂 适用于治疗疼痛的n-(n-磺酰氨基甲基)环丙烷甲酰胺衍生物

Family Cites Families (14)

* 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
DE69020989T2 (de) 1989-09-19 1996-02-08 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
US20120041225A1 (en) * 2006-02-03 2012-02-16 Vaidya Niteen A Kit for automated resolving agent selection and method thereof
US20120088746A1 (en) 2006-05-10 2012-04-12 Pfizer Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
WO2007129188A1 (en) * 2006-05-10 2007-11-15 Pfizer Japan Inc. Cyclopropanecarboxamide compound
EP1882687A1 (en) * 2006-07-27 2008-01-30 Amorepacific Corporation Heterocyclic compounds useful as vanilloid receptor antagonists and pharmaceutical compositions 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
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
JP2012508219A (ja) 2008-11-07 2012-04-05 シプラ・リミテッド ゾピクロンを分割するための方法
KR20160101554A (ko) 2015-02-17 2016-08-25 (주)아모레퍼시픽 N-[4-(1-아미노에틸)-페닐]-메탄술폰아미드 유도체의 카이랄 분할 방법

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101160285A (zh) * 2005-03-17 2008-04-09 辉瑞大药厂 适用于治疗疼痛的n-(n-磺酰氨基甲基)环丙烷甲酰胺衍生物
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

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chain-branched 1,3-dibenzylthioureas as vanilloid receptor 1 antagonists;Chong Hyun Ryu等;《Bioorganic & Medicinal Chemistry Letters》;20041231;第14卷;1751-1755 *
Oral and topical pharmacokinetic studies of a novel TRPV1 antagonist,PAC-14028 in rats and minipigs using liquid chromatography/tandem mass spectrometric method;Yang-Hui Park等;《Journal of Pharmaceutical and Biomedical Analysis》;20121117;第61卷;8-14 *

Also Published As

Publication number Publication date
EP3162793A4 (en) 2018-01-03
TW201636319A (zh) 2016-10-16
EP3162793A1 (en) 2017-05-03
CN106660949A (zh) 2017-05-10
EP3162793B1 (en) 2019-04-10
JP6687596B2 (ja) 2020-04-22
US10479763B2 (en) 2019-11-19
US20170342027A1 (en) 2017-11-30
JP2018506503A (ja) 2018-03-08
TWI687396B (zh) 2020-03-11
BR112017001516B1 (pt) 2023-10-31
WO2016133317A1 (ko) 2016-08-25
BR112017001516A2 (pt) 2018-01-30
KR20170042548A (ko) 2017-04-19
KR101791119B1 (ko) 2017-11-20

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