KR970061841A - 나부메톤의 제조방법 - Google Patents

나부메톤의 제조방법 Download PDF

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Publication number
KR970061841A
KR970061841A KR1019970002833A KR19970002833A KR970061841A KR 970061841 A KR970061841 A KR 970061841A KR 1019970002833 A KR1019970002833 A KR 1019970002833A KR 19970002833 A KR19970002833 A KR 19970002833A KR 970061841 A KR970061841 A KR 970061841A
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Prior art keywords
methoxy
naphthyl
represented
structural formula
bromo
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KR1019970002833A
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KR100199335B1 (ko
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빈첸쪼 카나타
아밀카레 베르토니
스테파노 비안키
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빈첸쪼 카나타
알파 케미칼스 이탈리아나 에스. 피. 에이.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Recrystallisation Techniques (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Professional, Industrial, Or Sporting Protective Garments (AREA)

Abstract

본 발명은 나부메톤(nabumetone)으로 알려지고 있는 4-(6-메톡시-2-나프틸)부탄-2-온〔4-(6-methoxy-2-naphthy)butan-2-one〕의 새로운 제조방법에 관한 것인바, 이는 2-아세틸-5-브로모-6-메톡시나프탈렌과 알킬 아세테이트를알칼리성 알콜레이트 존재하에 반응시켜 4-(5-브로모-6-메톡시-2-나프틸)-4-하이드록시부트-3-엔-2-온〔5-bromo-6-methoxy-2-naphthy)-4-hydroxybut-3-en-2-one〕을 얻고 이를 극성 용매와 염기 존재하에 접촉 수소화 반응으로 항염제로 유용한 나부메톤을 제조하는 것이다.

Description

나부메톤의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (2)

  1. 아래 제조공정으로 이루어진 것을 특징으로 하는 항염제로서 나부메톤으로 알려진 구조식(Ⅰ)로 표시되는 4-(6-메톡시-2-나프틸)부탄-2-온의 제조방법 :
    (Ⅰ)
    가) 구조식(Ⅱ)로 표시되는 1몰 당량의 2-아세틸-5-브로모-6-메톡시나프탈렌과
    (Ⅱ)
    용매로서도 작용하는 구조식(Ⅲ)으로 표시되는 알킬 아세티이트를
    (Ⅲ)
    (여기서,R은 탄소 원자 1~6까지의 알킬기 임)단독 또는 톨루엔, 아세토니트릴, 또는 N,N-디메틸포름아마이드와 같은 기타 용매와 혼합하여, 1~3몰 당량의 알칼리성 알콜레이트 존재하에 10~90℃의 온도에서 0.5~6시간동안 반응시켜, 유기산 또는 무기산 수용액으로 pH를 3~5로 조정하여 산성화시킨 후, 구조식(Ⅳ)로 표시되는 4-(5-브로모-6-메톡시-2-나프틸)-4-하이드록시부트-3-엔-2-온을 제조하는 공정.
    (Ⅳ)
    나) 1몰 당량의 구조식(Ⅳ)로 표시되는 4-(5-브로모-6-메톡시-2-나프틸)-4-하이드록시부트-3-엔-2-온과 수소를 극성 용매 또는 극성 용매나 비극성 용매의 혼합물 중에 0.005~0.05몰 당량의 수소화용 촉매와 0.30~0.99몰 당량의 염기 존재하에, 1~10기압의 압력 및 상온~90℃의 온도에서 2~24시간 동안 접촉 수소화시키는 공정, 다) 수소화된 혼합물을 여과하고 진공하에서 농축시키는 공정, 라) 탄소 원자 1~6까지의 알콜류로 결정화하거나 또는 극성 용매나 이들과 물과의 혼합물중에 나트륨 비설파이트로 비설파이트 착화물을 형성하게 하고, 생성된 결정성 비설파이트 착화물을 알칼리 금속의 하이드록사이드, 카르보네이트 또는 비카르보네이트 수용액으로 처리하여 얻은 다)공정에서의 기름상 물질을 정제하여 구조식(Ⅰ)로 표시되는 4-(6-메톡시-2-나프틸)부탄-2-온을 제조하는 공정.
  2. 제1항에 있어서, 알칼리성 알콜레이트는 탄소 원자 1~4를 포함하는 알콜의 나트륨 또는 칼륨 알콜레이트이고, 수소화 촉매는 5% 또는 10%의 Pd/c이며, 염기의 양은 0.90~0.98몰 당량으로써, 나트륨 또는 칼륨 카르보네이트, 아세티이트 중에서 선택하며, 수소화에 사용되는 용매는 탄소 원자 1~6까지의 알콜류 또는 이들과 물과의 혼합물 또는 이들과 비극성 용매와의 혼합물 중에서 선택하는 것을 특징으로 하는 구조식(Ⅰ)의 4-(6-메톡시-2-나프틸)부탄-2-온의 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019970002833A 1996-02-21 1997-01-30 나부메톤의 제조방법 KR100199335B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ITB096A000078 1996-02-21
ITBO96A000078 1996-02-21
IT96BO000078A IT1285567B1 (it) 1996-02-21 1996-02-21 Nuovo processo per la sintesi del nabumetone

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KR970061841A true KR970061841A (ko) 1997-09-12
KR100199335B1 KR100199335B1 (ko) 1999-06-15

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US (2) US5750793A (ko)
EP (1) EP0792860B1 (ko)
JP (1) JP2824051B2 (ko)
KR (1) KR100199335B1 (ko)
AT (1) ATE205465T1 (ko)
CA (1) CA2194414C (ko)
DE (1) DE69706580T2 (ko)
IT (1) IT1285567B1 (ko)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1291284B1 (it) * 1997-04-30 1999-01-07 Secifarma Spa Processo per la preparazione del 4-(6'-metossi-2'-naftil)butan-2-one (nabumetone).
FR2775284B1 (fr) * 1998-02-20 2000-04-21 Rhodia Chimie Sa Procede de preparation de composes cetoniques aromatiques
TWI262791B (en) 1999-10-27 2006-10-01 Nobex Corp 6-methoxy-2-naphthylacetic acid prodrugs
US6436990B1 (en) 1999-10-27 2002-08-20 Nobex Corporation 6-methoxy-2-naphthylacetic acid prodrugs
US6552078B2 (en) 1999-10-27 2003-04-22 Nobex Corp 6-methoxy-2-naphthylacetic acid prodrugs
ES2446647T3 (es) 2009-11-05 2014-03-10 Glaxosmithkline Llc Inhibidor de bromodominio de benzodiazepina

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2544562A (en) * 1947-07-18 1951-03-06 Stanolind Oil & Gas Co Process for recovering aldehydes and ketones
US4061779A (en) * 1973-09-11 1977-12-06 Beecham Group Limited Naphthalene derivatives having anti-inflammatory activity
DE2860631D1 (en) 1978-01-07 1981-05-07 Beecham Group Plc Process for the preparation of 4-(6-methoxy-2-naphthyl)butan-2-one and 2-acetyl-3-(6-methoxy-2-naphthyl) propenoic acid esters
US4221741A (en) 1978-01-27 1980-09-09 Beecham Group Limited Preparation of 4(6'-methoxy-2'-naphthyl)butan-2-one
GB8603766D0 (en) 1986-02-15 1986-03-19 Beecham Group Plc Process
IT1238008B (it) 1990-02-08 1993-06-21 Alfa Wassermann Spa Procedimento per la debromurazione di 2-sostituiti-5-bromo- 6-metossinaftaleni
US5344992A (en) * 1990-04-26 1994-09-06 Ciba-Geigy Corporation Process for the preparation of linear 1,3-diketones
DE4404059A1 (de) * 1994-02-09 1995-08-10 Huels Chemische Werke Ag Verfahren zur Herstellung von 1-Cyclopropylalkan-1,3-dionen

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EP0792860A1 (en) 1997-09-03
US5750793A (en) 1998-05-12
CA2194414C (en) 2001-12-25
KR100199335B1 (ko) 1999-06-15
EP0792860B1 (en) 2001-09-12
USRE37813E1 (en) 2002-08-06
DE69706580D1 (de) 2001-10-18
CA2194414A1 (en) 1997-08-21
DE69706580T2 (de) 2002-07-11
ITBO960078A1 (it) 1997-08-21
JPH09323952A (ja) 1997-12-16
IT1285567B1 (it) 1998-06-18
ITBO960078A0 (it) 1996-02-21
ATE205465T1 (de) 2001-09-15
JP2824051B2 (ja) 1998-11-11

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