JPS5896036A - 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
JPS5896036A
JPS5896036A JP57190681A JP19068182A JPS5896036A JP S5896036 A JPS5896036 A JP S5896036A JP 57190681 A JP57190681 A JP 57190681A JP 19068182 A JP19068182 A JP 19068182A JP S5896036 A JPS5896036 A JP S5896036A
Authority
JP
Japan
Prior art keywords
formula
manufacture
compounds
naphthalene derivative
novel 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.)
Granted
Application number
JP57190681A
Other languages
English (en)
Other versions
JPS605580B2 (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

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  • 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)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

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の製法に
関するものである。
ある釉のナフタレン誘導体は有用な抗炎症性を有し、種
々のリウ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
ナフタレン誘導体のひとつに式（１）を有するナゾロキ
セン（Ｎａｐｒｏｘｅｎ）がア７）。ｊ（７）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１．２
７１．１３２号、同第１．２７４．２７１号同第１．２
７４．２７２号、同第１．２７４．２７３号、同第１．
２９１．３８６号、同第１．２１１．１３４号、同第１
．２９７．３０６号、同第１．２７６．２６１号、同第
１．２１６．８８２号、同第１．２８９．０４１号、同
第１．３２１．３４７号、および同第１．２９６．４９
３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〔ＪｅＭｅｄ−Ｃｈｅｍ＊　、１３゜
２０３、（１９７０）　、Ｊ＠Ｐｈａｍ＠Ｅｘｐ−Ｔｈ
ｅｒａ。
１７９、　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。
り 本発明によって、他のナス２レン誘導体が良好な抗炎症
性を有するばかシでなく、冑腸内の刺激に基いて体重に
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（…）（式中、Ｒ１け水素原子ま
たはメチル基であり、点線は追加の結合を表わすかまた
は点線が達する二つの炭素原子の各々に結合した水素原
子を表わす）を有する化合物である。
Ｒ１がメチル基である式（Ｉｔ）の化合物は投与量を多
くすると発情性作用を示す傾向があるが、Ｒ１が水素で
ある式ｉ）の化合物はこの作用を示す傾向が小さくなる
。
式（ＩＩ）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（ＩＩ）の薬効成分を２０〜１０００■、さ
らに一般的には１００〜６００　ｍｙ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ｌ″ｉ１日２〜４回に、７０ｋＣ！の体重の人間の１
日投与量が通常３００〜３０００■、さらに好オしくに
５００〜２０００■たとえば６００〜１６００■に力る
ようにすることができる。
式（ＩＩ） （式中、Ｒ１は水素原子寸たはメチル基であり、点線は
追加の結合を表わすかまたは点線が達する二つの炭素原
子の各々に結合した水素原子を表わす）を有する化合物
を還元して式（ＩＩ）（式中、Ｒ１および点線Ｆｉ！ｉ
＋述の意味を表わす）を有する化合物とする。
カルボニル基である式（１）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ＮａＢＨ４、ＬｉＡｌ
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。
接触水素添加はオレフィン系二重結合を還元することが
あるので、このような二重結合を有する化合物を製造す
るときには好ましくない。
実施例１ ４−（６’−メトキシ−２′−ナフチル）−ペンタン−
２−オル メタノール１００ｒｎｌ中の４−（６’−メトキシ−２
′−ナフチル）−ペンタン−２−オ＞　２　ｔ　ノ溶液
を水中で冷却し、これに水素化ホウ累ナトリウム１ｔ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１００ｄずつで３回抽出する。水洗したエー
テル抽出物を無水Ｎａｇ　ｓｏ４　　で乾燥し、蒸発す
ると、透明な無色油状物１．３ｔを得る。
ＩＲ：３４００ｔＭ−”ＯＨの吸収帯、ＣＯの吸収帯は
消失 代理人　弁理士　　秋　沢　政　光 他１名

Claims (1)

    【特許請求の範囲】
  1. （１）式（ＩＩＩ） （式中、Ｒ１は水素原子またはメチル基であり、点線は
    追加の結合を表わすかまたは点線が達する二つの炭素原
    子の各々に結合した水素原子を表わす） を有する化合物を還元することを特徴とする式（） （式中、Ｒ１は前述の意味を有する） を有する化合物の製法。
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 true JPS5896036A (ja) 1983-06-07
JPS605580B2 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
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
JPS605580B2 (ja) 1985-02-12
MY8100197A (en) 1981-12-31
CH613932A5 (ja) 1979-10-31
CH603543A5 (ja) 1978-08-31

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