KR920702342A - 벤조산 유도체의 신규 제조방법 - Google Patents

벤조산 유도체의 신규 제조방법

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Publication number
KR920702342A
KR920702342A KR1019910701646A KR910701646A KR920702342A KR 920702342 A KR920702342 A KR 920702342A KR 1019910701646 A KR1019910701646 A KR 1019910701646A KR 910701646 A KR910701646 A KR 910701646A KR 920702342 A KR920702342 A KR 920702342A
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KR
South Korea
Prior art keywords
lower alkyl
formula
benzoic acid
compound
iii
Prior art date
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KR1019910701646A
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English (en)
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KR960014911B1 (ko
Inventor
요시노리 하마다
이사무 야마다
마사아끼 우에나까
데루오 사까따
Original Assignee
요시또시 가즈오
시오노기세이야꾸 가부시끼가이샤
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Publication of KR920702342A publication Critical patent/KR920702342A/ko
Application granted granted Critical
Publication of KR960014911B1 publication Critical patent/KR960014911B1/ko

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Paper (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

내용 없음

Description

벤조산 유도체의 신규 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명의 제조방법에 따라 합성된 목적 화합물인 4-〔(5,6,7,8-테트라히드로-5,5,8,8-테트라메틸-2-나프틸)카르바모일〕벤조산의 IR 스펙트럼을 나타내는 도해이다.이 IR 스펙트럼은 Nujol을 사용하여 수득한 것이다. 제2도는 종래 기술 방법에 따라 합성된 4-〔(5,6,7,8-테트라히드로-5,5,8,8-테트라메틸-2-나프틸)카르바모일〕벤조산의 IR 스펙트럼을 나타내는 도해이다. 이 IR 스펙트럼은 Nujol을 사용하여 수득한 것이다. 제3도는 본 발명의 제조방법에 따라 합성된 목적 화합물의 열분해를 나타내는 도해이다. 본 화합물은 193℃에서 용융한다.

Claims (4)

  1. (a) 하기일반식(I)의 아실 아닐린 유도체 및 1,4-부틸 디할라이드 유도체(Ⅱ)를 프리에델-크라프트 반응시켜 하기 일반식(Ⅲ)의 비시클릭 아미드 화합물을 수득하고,
    〔식중, R1은 저급 알킬 또는 아릴이고, R2는 독립적으로 수소 또는 저급알킬이다〕
    〔식중, R3,R4,R5및 R6는 각각 독립적으로 저급알킬이고, R|7은 독립적으로 수소 또는 저급알킬이며, X는 할로겐이다〕
    〔식중,R1,R2,R3,R4,R5,R6및 R7은 각각 상기와 같다〕
    (b) (a)공정에서 수득된 화합물(Ⅲ)을 모노에스테르 테레프탈 할라이드와 반응시켜 하기 일반식(Ⅳ)의 화합물을 형성하며,
    〔식중,R2,R3,R4,R5,R6R7은 각각 상기와 같고, R8은 저급알킬이며, R9은 독립적으로 수소 또는 저급알킬이다 〕
    (c) (b)공정에서 수득된 화합물(Ⅳ)를 탈에스테르화 반응시켜 하기 알반식(Ⅴ)의 화합물을 수득함을 특징으로 하는 하기 일반식(Ⅴ)의 벤조산 유도체의 제조방법.
    〔식중,R2,R3,R4,R5,R6R7및 R9는 각각 상기와 같다〕
  2. 하기 일반식(Ⅲ)의 비시클릭 아미드.
    〔식중, R1,R2,R3,R4,R5,R6및 R7은 각각 상기와 같다〕
  3. X-선 회절각 및 강고 비율이 하기 표와 같은 4-〔(5,6,7,8-테트라히드로-5,5,8,8-테트라메틸-2-나프틸)카르바모일〕벤조산의 결정형태.
  4. 하기 식(Ⅴ)의 화합물을 메탄올형 용매로 재결정하는 공정을 포함하는 것을 특징으로 하는 제3항에 청구한 결정상 4-〔(5,6,7,8-테트라히드로-5,5,8,8-테트라메틸-2-나프틸)카르바모일〕벤조산의 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910701646A 1990-03-20 1991-03-15 벤조산 유도체의 신규 제조방법 KR960014911B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP7143390 1990-03-20
JP90-71433 1990-03-20
PCT/JP1991/000350 WO1991014673A1 (en) 1990-03-20 1991-03-15 Novel process for producing benzoic acid derivative

Publications (2)

Publication Number Publication Date
KR920702342A true KR920702342A (ko) 1992-09-03
KR960014911B1 KR960014911B1 (ko) 1996-10-21

Family

ID=13460393

Family Applications (1)

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Country Status (14)

Country Link
US (1) US5214202A (ko)
EP (1) EP0478787B1 (ko)
JP (2) JP3001632B2 (ko)
KR (1) KR960014911B1 (ko)
AT (1) ATE115946T1 (ko)
AU (1) AU628732B2 (ko)
DE (1) DE69106098T2 (ko)
DK (1) DK0478787T3 (ko)
ES (1) ES2069285T3 (ko)
FI (1) FI915445A0 (ko)
GR (1) GR3015138T3 (ko)
HU (2) HU210300B (ko)
NO (1) NO300206B1 (ko)
WO (1) WO1991014673A1 (ko)

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US5675033A (en) 1995-06-06 1997-10-07 Allergan 2,4-pentadienoic acid derivatives having retinoid-like biological activity
US5917082A (en) 1995-06-06 1999-06-29 Allergan Sales, Inc. 2,4-pentadienoic acid derivatives having retinoid-like biological activity
US6218128B1 (en) 1997-09-12 2001-04-17 Allergan Sales, Inc. Methods of identifying compounds having nuclear receptor negative hormone and/or antagonist activities
US5776699A (en) * 1995-09-01 1998-07-07 Allergan, Inc. Method of identifying negative hormone and/or antagonist activities
US5958954A (en) 1995-09-01 1999-09-28 Allergan Sales, Inc. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
US6008204A (en) 1995-09-01 1999-12-28 Allergan Sales, Inc. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
US5952345A (en) 1995-09-01 1999-09-14 Allergan Sales, Inc. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
US5675024A (en) 1995-11-22 1997-10-07 Allergan Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4,-tetrahydroquinoline carboxylic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity
US5763635A (en) 1996-06-21 1998-06-09 Allergan Tetrahydronaphthalene derivatives substituted in the 8 position with alkyhidene groups having retinoid and/or retinoid antagonist-like biological activity
US5741896A (en) 1996-06-21 1998-04-21 Allergan O- or S- substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US5773594A (en) 1996-06-21 1998-06-30 Allergan Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US6555690B2 (en) 1996-06-21 2003-04-29 Allergan, Inc. Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US5728846A (en) 1996-12-12 1998-03-17 Allergan Benzo 1,2-g!-chrom-3-ene and benzo 1,2-g!-thiochrom-3-ene derivatives
US6037488A (en) 1997-04-19 2000-03-14 Allergan Sales, Inc. Trisubstituted phenyl derivatives having retinoid agonist, antagonist or inverse agonist type biological activity
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DE60143166D1 (de) 2000-09-01 2010-11-11 Toko Pharmaceutical Ind Co Ltd Verfahren zur herstellung von kristallen von benzoesäure-derivaten
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CN101200435B (zh) * 2006-12-12 2011-12-07 江苏恒瑞医药股份有限公司 他米巴罗汀ⅱ型结晶的制备方法
WO2008120711A1 (ja) 2007-03-30 2008-10-09 Tmrc Co., Ltd. タミバロテンカプセル剤
WO2009114966A1 (zh) * 2008-03-19 2009-09-24 江苏恒瑞医药股份有限公司 他米巴罗汀ii型结晶的制备方法
CN101665449B (zh) * 2009-09-24 2012-12-12 山东大学 他米巴罗汀的水溶性前药及其制备方法与应用
CN102633673A (zh) * 2012-03-30 2012-08-15 上海共价化学科技有限公司 他米巴罗汀的合成方法

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NO914519L (no) 1992-01-07
HU208417B (en) 1993-10-28
KR960014911B1 (ko) 1996-10-21
HUT61272A (en) 1992-12-28
EP0478787A1 (en) 1992-04-08
HU913801D0 (en) 1992-07-28
NO300206B1 (no) 1997-04-28
HUT61270A (en) 1992-12-28
ES2069285T3 (es) 1995-05-01
DE69106098D1 (de) 1995-02-02
US5214202A (en) 1993-05-25
GR3015138T3 (en) 1995-05-31
HU9202856D0 (en) 1992-11-30
EP0478787B1 (en) 1994-12-21
JP2000034262A (ja) 2000-02-02
FI915445A0 (fi) 1991-11-18
JP3076569B2 (ja) 2000-08-14
ATE115946T1 (de) 1995-01-15
NO914519D0 (no) 1991-11-19
EP0478787A4 (en) 1992-07-01
DK0478787T3 (da) 1995-02-20
HU210300B (en) 1995-03-28
DE69106098T2 (de) 1995-05-24
WO1991014673A1 (en) 1991-10-03
JP3001632B2 (ja) 2000-01-24
AU628732B2 (en) 1992-09-17
AU7482691A (en) 1991-10-21

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