WO2011004980A3 - 트리사이클릭 유도체의 제조방법 - Google Patents

트리사이클릭 유도체의 제조방법 Download PDF

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WO2011004980A3
WO2011004980A3 PCT/KR2010/004212 KR2010004212W WO2011004980A3 WO 2011004980 A3 WO2011004980 A3 WO 2011004980A3 KR 2010004212 W KR2010004212 W KR 2010004212W WO 2011004980 A3 WO2011004980 A3 WO 2011004980A3
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tricyclic derivatives
present
compounds
preparing
conducting
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PCT/KR2010/004212
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English (en)
French (fr)
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WO2011004980A2 (ko
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김명화
예인해
최종희
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제일약품주식회사
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Priority to CN2010800376861A priority Critical patent/CN102548958A/zh
Priority to US13/381,036 priority patent/US8742160B2/en
Priority to EP10797254.9A priority patent/EP2452931B1/en
Priority to ES10797254.9T priority patent/ES2633838T3/es
Priority to JP2012517404A priority patent/JP5457555B2/ja
Publication of WO2011004980A2 publication Critical patent/WO2011004980A2/ko
Publication of WO2011004980A3 publication Critical patent/WO2011004980A3/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • 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
    • C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/34—Benzoheptalenes; Hydrogenated benzoheptalenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

본 발명은 트리사이클릭 유도체의 제조방법에 관한 것으로, 더욱 구체적으로는 2-플루오로이소프탈릭에시드 화합물을 에스테르화 반응시키고, 치환반응시켜 히드록시기를 도입한 후, 피페리딜기를 도입하고 다시 환원반응시켜 히드록시기를 도입시킨 후에 가수분해시켜 이루어지는 수율 및 순도가 높은 신규한 트리사이클릭 유도체의 중간체의 제조방법 및 상기 중간체를 이용한 트리사이클릭 유도체의 제조방법에 관한 것이다. 본 발명에 따른 제조방법에 의하면, 관 크로마토그래피법으로 정제하였던 종래의 방법 대신 재결정법으로 정제함으로써 종래의 방법보다 생산성 및 경제성이 높고 순도 및 수율이 높은 트리사이클릭 유도체 및 이의 중간체를 제조할 수 있을 뿐만 아니라, 높은 화재의 위험 때문에 산업적으로 이용하기 힘든 리튬보로하이드라이드를 사용하는 종래의 방법 대신 화재 위험이 적은 소듐보로하이드라이드 또는 리튬알루미늄하이드를 사용하므로 공업적인 대량생산에 유용하게 사용할 수 있다.
PCT/KR2010/004212 2009-07-08 2010-06-29 트리사이클릭 유도체의 제조방법 WO2011004980A2 (ko)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN2010800376861A CN102548958A (zh) 2009-07-08 2010-06-29 制备三环衍生物的方法
US13/381,036 US8742160B2 (en) 2009-07-08 2010-06-29 Method for preparing tricyclic derivatives
EP10797254.9A EP2452931B1 (en) 2009-07-08 2010-06-29 Method for preparing tricyclic derivatives
ES10797254.9T ES2633838T3 (es) 2009-07-08 2010-06-29 Método para preparar derivados tricíclicos
JP2012517404A JP5457555B2 (ja) 2009-07-08 2010-06-29 トリサイクリック誘導体の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2009-0061983 2009-07-08
KR1020090061983A KR101077609B1 (ko) 2009-07-08 2009-07-08 트리사이클릭 유도체의 제조방법

Publications (2)

Publication Number Publication Date
WO2011004980A2 WO2011004980A2 (ko) 2011-01-13
WO2011004980A3 true WO2011004980A3 (ko) 2011-04-14

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ID=43429644

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PCT/KR2010/004212 WO2011004980A2 (ko) 2009-07-08 2010-06-29 트리사이클릭 유도체의 제조방법

Country Status (7)

Country Link
US (1) US8742160B2 (ko)
EP (1) EP2452931B1 (ko)
JP (1) JP5457555B2 (ko)
KR (1) KR101077609B1 (ko)
CN (2) CN103772193B (ko)
ES (1) ES2633838T3 (ko)
WO (1) WO2011004980A2 (ko)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2470499T3 (pl) 2009-08-26 2019-11-29 Alberta Health Services Nowe pochodne kolchicyny, sposoby i ich zastosowania
CN104649943B (zh) * 2015-01-28 2016-10-05 中国科学院上海高等研究院 秋水仙碱衍生物及其制备方法和应用
KR101881870B1 (ko) 2017-11-09 2018-07-25 (주) 태광 김양식용 부구
KR20190113315A (ko) 2018-03-28 2019-10-08 유옥수 다공과 살빼기형 양식용 코팅 부자
KR20190113312A (ko) 2018-03-28 2019-10-08 유옥수 다공과 살빼기형 양식용 코팅 부자
KR20190126485A (ko) 2018-05-02 2019-11-12 주영테크 주식회사 발포성형 부표의 코팅을 위한 양식용 부표와 그 제조방법
KR102230914B1 (ko) 2020-08-13 2021-03-24 정용현 발포성형 부구를 코팅한 친환경 부구와 그 제조방법
CN112047890A (zh) * 2020-10-20 2020-12-08 连云港杰瑞药业有限公司 一种奥拉帕尼制备方法

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WO2002100824A1 (en) * 2001-05-28 2002-12-19 Chemtech Research Incorporation A novel alkaloid derivative and a pharmaceutical composition containing the same
WO2004113281A1 (en) * 2003-06-25 2004-12-29 Je Il Pharmaceutical Co., Ltd. Tricyclic derivatives or pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them

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JP2000086583A (ja) * 1998-09-17 2000-03-28 Asahi Glass Co Ltd 含フッ素ベンジル誘導体の製造方法
ITMI20040164A1 (it) * 2004-02-03 2004-05-03 Indena Spa Derivati di n.deacetiltiocolchicina loro uso e formulazioni farmaceutiche che li contengono

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002100824A1 (en) * 2001-05-28 2002-12-19 Chemtech Research Incorporation A novel alkaloid derivative and a pharmaceutical composition containing the same
WO2004113281A1 (en) * 2003-06-25 2004-12-29 Je Il Pharmaceutical Co., Ltd. Tricyclic derivatives or pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them

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MARZI, E. ET AL.: "Fluoro-or trifluoromethyl-substituted benzyl and phenethyl alcohols: Substrates for metal-mediated site-selective functionalization", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, pages 2508 - 2517, XP008150117 *

Also Published As

Publication number Publication date
CN103772193A (zh) 2014-05-07
CN102548958A (zh) 2012-07-04
US20120101296A1 (en) 2012-04-26
KR101077609B1 (ko) 2011-10-27
EP2452931B1 (en) 2017-05-17
US8742160B2 (en) 2014-06-03
WO2011004980A2 (ko) 2011-01-13
KR20110004528A (ko) 2011-01-14
EP2452931A2 (en) 2012-05-16
CN103772193B (zh) 2015-11-18
JP5457555B2 (ja) 2014-04-02
ES2633838T3 (es) 2017-09-25
EP2452931A4 (en) 2013-12-25
JP2012531407A (ja) 2012-12-10

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