JPS605580B2 - 新ナフタレン誘導体の製法 - Google Patents

新ナフタレン誘導体の製法

Info

Publication number
JPS605580B2
JPS605580B2 JP57190681A JP19068182A JPS605580B2 JP S605580 B2 JPS605580 B2 JP S605580B2 JP 57190681 A JP57190681 A JP 57190681A JP 19068182 A JP19068182 A JP 19068182A JP S605580 B2 JPS605580 B2 JP S605580B2
Authority
JP
Japan
Prior art keywords
naphthalene derivatives
formula
manufacturing
compound
new naphthalene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
JP57190681A
Other languages
English (en)
Other versions
JPS5896036A (ja
Inventor
アンソニ−・ウイリアム・レイク
カ−ル・ジヨ−ン・ロ−ズ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Publication of JPS5896036A publication Critical patent/JPS5896036A/ja
Publication of JPS605580B2 publication Critical patent/JPS605580B2/ja
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal 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
    • C07C45/26—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydration of carbon-to-carbon triple bonds
    • 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
    • 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
    • C07C45/46—Friedel-Crafts reactions
    • 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
    • C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Rheumatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

【発明の詳細な説明】 本発明は製薬上活性を有するナフタレン誘導体を製造す
る方法に関するものである。
ある種のナフタレン誘導体は有用な抗炎症性を有し、種
々のりゥマチ性および関節炎性病状の治療に使用するの
に適していることが知られている。
臨床的に使用できることが知られている特に効果がある
ナフタレン譲導体のひとつに式（１）を有するナプロキ
セン（Ｎａｐｒｏｘｅｎ）がある。この化合物およびこ
れに関連するある種の化合物は英国特許第１２７１１３
２号、同第１２７４２７１号、同第１２７４２７２号、
同第１２７４２７３号、同第１２９１３８６号、同第１
２１１１３４号、同第１２９７３０６号、同第１２７６
２６１号、同第１２１６８８２号、同第１２８９０４１
号、同第１３２１３４７号、および同第１２９６４９３
号の各明細書に記載されている。この種の化合物の薬理
学的効果も文献〔Ｊ．Ｍｅｄ．Ｃｈｅｍ．、１３ ２０
３（１９７０）、Ｊ．Ｐｈａｍ．Ｅ×ｐ．ｍｅｒａ、１
７９ １１４、（１９７１）〕に記載されている。残念
ながら式（１）の化合物は治療用投与量をあまり大して
越えない投与量で、ある被験者の胃腸に激しい刺激を生
じることがある。本発明によって、他のナフタレン譲導
体が良好な抗炎症性を有するばかりでなく、胃腸内の刺
激に塞いて体重に対する薬効量の比率が改良されている
ことが分かった。
このような化合物は式（〇）を有する化合物である。
式（０）の化合物は人間に対する経口投与に適した抗炎
性および（または）鎮痛性組成物に入れることができる
。
この種の組成物は錠剤、カプセル剤、粉末等任意の形に
することができる。単位投与量を含有する形のときには
通常式（Ｄ）の薬効成分を２０〜１０００の９、さらに
一般的には１００〜６００の夕を含有する。このような
単位投与量を含有する形は１日１回以上、好ましくは１
日２〜４回に、７０ｋ９の体重の人間の１日投与量が通
常３００〜３０００の９、さらに好ましくは５００〜２
０００の２たとえば６００〜１６００ののこなるように
することができる。本発明によれば下記よりなる前記（
０）の新しい化合物の製法が得られる。式（ｍ） を有する化合物を還元して式（０） を有する化合物とする。
カルボニル基である式（ｍ）の化合物を還元して対応す
る第二アルコールにする反応は遷移金属触媒の存在下の
水素添加または水素化物たとえばＮａＢ日４、ＬｉＡＩ
Ｈ４等の使用のような通常行なわれている還元法を使用
して実施することができる。
実施例 １４一（６−メトキシ−２′−ナフチル）ーベ
ンタン−２ーオルメタノール１００凧【中の４一（６−
メトキシ−２ーナフチル）ーベンタン−２−オン２夕の
溶液を氷中で冷却し、これに水素化ホウ素ナトリウム１
夕を加え、溶液を１時間かきまぜてから、希塩酸で酸性
にし、エーテル１００の【ずつで３回抽出する。
水洗したエーテル抽出物を無水Ｎａ２Ｓ０４で乾燥し、
蒸発すると、透明な無色油状物１．３夕を得る。ＩＲ三
３４００肌‐１０日の吸収帯、ＣＯの吸収帯は消失。

Claims (1)

  1. 【特許請求の範囲】 １ 式（III） ▲数式、化学式、表等があります▼ を有する化合物を還元することを特徴とする式（II）▲
    数式、化学式、表等があります▼ を有する化合物を製造する方法。
JP57190681A 1973-09-11 1982-10-29 新ナフタレン誘導体の製法 Expired JPS605580B2 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB4255073A GB1474377A (en) 1973-09-11 1973-09-11 Naphthalene derivatives
GB42550 1973-09-11

Publications (2)

Publication Number Publication Date
JPS5896036A JPS5896036A (ja) 1983-06-07
JPS605580B2 true JPS605580B2 (ja) 1985-02-12

Family

ID=10424914

Family Applications (4)

Application Number Title Priority Date Filing Date
JP49103764A Expired JPS5920655B2 (ja) 1973-09-11 1974-09-09 新ナフタレン誘導体の製法
JP57190679A Expired JPS6033818B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法
JP57190680A Expired JPS5921850B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法
JP57190681A Expired JPS605580B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法

Family Applications Before (3)

Application Number Title Priority Date Filing Date
JP49103764A Expired JPS5920655B2 (ja) 1973-09-11 1974-09-09 新ナフタレン誘導体の製法
JP57190679A Expired JPS6033818B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法
JP57190680A Expired JPS5921850B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法

Country Status (15)

Country Link
JP (4) JPS5920655B2 (ja)
BE (1) BE819794A (ja)
CH (8) CH599090A5 (ja)
CY (2) CY1083A (ja)
DE (2) DE2463219C2 (ja)
DK (1) DK156642C (ja)
FR (1) FR2242972B1 (ja)
GB (1) GB1474377A (ja)
HK (2) HK56280A (ja)
IE (1) IE40001B1 (ja)
KE (2) KE3081A (ja)
MY (2) MY8100198A (ja)
NL (1) NL175812C (ja)
SE (2) SE420598B (ja)
ZA (1) ZA745441B (ja)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL52006A0 (en) * 1976-05-13 1977-07-31 Beecham Group Ltd Novel nephthalene derivatives their preparation and pharmaceutical compositions containing them
GB2014993B (en) * 1977-11-03 1982-05-12 Beecham Group Ltd Chemical compounds
EP0003074B1 (en) * 1978-01-07 1981-04-15 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
CA1142965A (en) * 1979-06-08 1983-03-15 Alexander C. Goudie Substituted decalins, their preparation and use
GB8416638D0 (en) * 1984-06-29 1984-08-01 Beecham Group Plc Topical treatment and composition
GB8607119D0 (en) * 1986-03-21 1986-04-30 Beecham Group Plc Process
EP0477098B1 (en) * 1990-09-18 1996-06-26 Fujitsu Limited Cursor displacement control device for a computer display
GB9108128D0 (en) * 1991-04-15 1991-06-05 Zambeletti Spa L Novel formulation
GB9201857D0 (en) 1992-01-29 1992-03-18 Smithkline Beecham Plc Novel compound
GB9222849D0 (en) * 1992-10-31 1992-12-16 Smithkline Beecham Plc Novel use of pharmaceutical compositions
WO1997032837A1 (fr) * 1996-03-06 1997-09-12 Sumitomo Pharmaceuticals Co., Ltd. Derives estrogenes non steroidiens
US5861538A (en) * 1997-08-04 1999-01-19 Albemarle Corporation Production of alkoxynaphthyl-substituted ketones from naphthaldehydes
CN1675154A (zh) * 2002-06-07 2005-09-28 科蒂科股份有限公司 抑制巨噬细胞移动抑制因子(mif)的细胞因子或生物活性的萘衍生物
EP2123621A1 (de) 2008-05-20 2009-11-25 Bayer Schering Pharma Aktiengesellschaft Neue {F-18}-markierte L-Glutaminsäure- und L-Glutaminderivate (I), ihre Verwendung sowie Verfahren zu ihrer Herstellung
EP2123619A1 (de) 2008-05-20 2009-11-25 Bayer Schering Pharma AG Neue [F-18]-Markierte L-Glutaminsäure-und L-Glutaminderivate (II), ihre Verwendung sowie Verfahren zu ihrer Herstellung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO125971B (ja) * 1969-05-22 1972-12-04 Syntex Corp
BR6915468D0 (pt) * 1969-10-09 1973-03-13 Syntex Corp Processo para a preparacao de d 2-(6-substituido-2-naftil)-propanal

Also Published As

Publication number Publication date
CY1082A (en) 1980-12-27
JPS5896036A (ja) 1983-06-07
CH603525A5 (ja) 1978-08-15
FR2242972A1 (ja) 1975-04-04
CH603526A5 (ja) 1978-08-15
JPS5921850B2 (ja) 1984-05-22
CH599090A5 (ja) 1978-05-12
JPS5890526A (ja) 1983-05-30
KE3082A (en) 1980-10-03
IE40001B1 (en) 1979-02-14
NL175812B (nl) 1984-08-01
JPS6033818B2 (ja) 1985-08-05
NL7412060A (nl) 1975-03-13
SE7907064L (sv) 1979-08-23
CH603524A5 (ja) 1978-08-15
CH603523A5 (ja) 1978-08-15
FR2242972B1 (ja) 1978-07-21
SE420598B (sv) 1981-10-19
JPS5920655B2 (ja) 1984-05-15
DE2442305C2 (de) 1986-04-03
CH603527A5 (ja) 1978-08-15
DK156642B (da) 1989-09-18
MY8100198A (en) 1981-12-31
SE7411261L (ja) 1975-03-12
HK56280A (en) 1980-10-10
JPS5053359A (ja) 1975-05-12
AU7313674A (en) 1976-03-11
HK56180A (en) 1980-10-10
DK156642C (da) 1990-01-29
DE2442305A1 (de) 1975-03-13
KE3081A (en) 1980-10-03
IE40001L (en) 1975-03-11
DK477674A (ja) 1975-05-12
BE819794A (fr) 1975-03-11
GB1474377A (en) 1977-05-25
ZA745441B (en) 1975-08-27
SE7907064A0 (sv) 1979-08-23
DE2463219C2 (ja) 1988-02-04
CY1083A (en) 1980-12-27
NL175812C (nl) 1985-01-02
JPS58113142A (ja) 1983-07-05
MY8100197A (en) 1981-12-31
CH613932A5 (ja) 1979-10-31
CH603543A5 (ja) 1978-08-31

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