JPS5890526A - 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

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Publication number
JPS5890526A
JPS5890526A JP57190679A JP19067982A JPS5890526A JP S5890526 A JPS5890526 A JP S5890526A JP 57190679 A JP57190679 A JP 57190679A JP 19067982 A JP19067982 A JP 19067982A JP S5890526 A JPS5890526 A JP S5890526A
Authority
JP
Japan
Prior art keywords
formula
compound
manufacture
methyl group
naphthalene derivative
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
JP57190679A
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English (en)
Other versions
JPS6033818B2 (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
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Filing date
Publication date
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Publication of JPS5890526A publication Critical patent/JPS5890526A/ja
Publication of JPS6033818B2 publication Critical patent/JPS6033818B2/ja
Expired legal-status Critical Current

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    • 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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  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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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】 本発明社医薬としての効果を有するナフタレン誘導体の
製法に関するものである。
ある種のす７タレン誘導体は有用な抗炎症性を有し、＊
ｈｏリク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糟に効果があるす７タレン誘導体
のひとつに次式（１）％式％３ 号、同第り鵞ｉｌｌ、３８６号、同第１，２１１，１３
４号、岡ｊｌＬ！１１７，３０６号、同第１．２７（２
８１号、同第Ｌ＝１へ８８２号、同第１４８亀０４１号
同ＫＬ＠　雪Ｌｍ４７１ｔ＆！びｆｉ［Ｌ２１４！、４
９３号の各明細書に記載されている。この種Ｏ化合物の
薬層学的効果も文献［Ｊ＠Ｍ・ｄ・Ｃｈ＠ｍｓ、■。
２０　ｍ　（１ｆＪ　７０　）　、Ｊ＠Ｐｈａｍ＠Ｅｘ
ｐｓＴｈ＠ｒａ。
１７９、　１１４　（１９７１）、）Ｋ記載されている
Ｏ 残念ながら式（１）の化合物は治療用投与ｊｊｋ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、他のナフタレン誘導体が良好な抗炎症
性を有するばかヤでなく、胃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（１）（式中８１　　は水素原子
あるいはメチル基を表わす）である。
Ｒ１がメチル基である式（１）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（鳳）の化合物はこの作用を示す傾向が小さくなる
。従ってこの好適な化合物は下記の化合物である＠ ４−（６’−メトキシ−２′−ナフチル）ブタン−２−
オン 前述の化合物およびそのａ炭素原子にメチル置換基を有
する化合物はネｙニジのカラゲニン抗炎症性゛試験で１
００１１Ｆ／１９／日の投与量で試験したとき顕著な抗
炎症性を示したが、３倍も高い投与量で胃に刺激を与え
なかった０ 式（１）０化合物は４人間に対する経口投与に適した抗
炎性および（また＃ｉ）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、カプセ羨剤、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（１）の薬効成分を２０−１０００＋ｖ、
さらに一般的には１００〜５ｏｏｑｔｔ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
＃ｉ１［〜４■に、７０＆Ｆの体重の人間の１日投与量
が通常ｓｏｏ〜３０００”ｆｓさらに好ましく社ｉｏｏ
〜意ｅｅｅｑたとえＦ！６００〜１８００４になるよう
にすることができる。
本発明によれば下記よりなる前記（ＩＩ）の新しい化合
物の製法が得られる。
（ＩＬ）式（！［） （式中％Ｒ１は水素またはメチル基を表わす）を有する
化合物を還元して式（１）の化合物とすることができる
。
（＃式（Ｉｌ） （式中ｓ　Ｒ１は水素またはメチル基を表わし、Ｂａ　
は塩素、臭素またはヨウ素または同様な置換可能な基會
表わす） を有する化合物をアセチルアセトンから誘導されよアニ
オンと反応させて式（厘）の化合物とすることができる
。
方法（ａ） 還元は活性炭に支持したパラジウムのような膚移金属触
媒Ｏ存在下の水素添加によって実施することができる・
反応は任意Ｏあまル極端でない手頃な温度で実施するこ
とができるが、常温が好ましい０通常反応は常圧または
常圧よ）少し高い圧力Ｏ水嵩を使用し、酢酸エチルまた
はエタノール＠０有機の不活性溶媒中で実施される。
方法（ロ） アセチルアセシンのアニオンの生成は式（Ｖ）の化合物
０導入前に１あるいは反応中に起すことができる０反応
は一般に酢酸エチ＾のような中性溶媒中で実施される。
あｔシ極端でない温度であれば使用できるが、一般に室
温またはそれ以上の温度えとえば２Ｇ−１２・０℃が好
適である・この反応は完結するまでに畏い期間を要する
ことがある。もし式アセチルアセトンＯアニオンをその
場８　　て発生させるときには、少なくとも１当量の非
親核性塩基たとえば水素化ナトリウム、炭酸ナトリウム
、炭酸カリウム等を存在させなけれはならない。
参考例１ ６−メドキシー２−ナンドアルデヒド３０Ｆをアセトン
５０〇−中で１０％の水酸化ナトリウム水溶液１０１１
ｄと３時間かきまぜる。漬液を酸性にし、エーテルで抽
出する。エーテル溶液をＭｇＳＯ４で乾燥し、減圧下で
薫香すると固体３０Ｆを得る。
この不純物をシリカダルのコラムで溶離剤にベンゼンを
使用して精製すると、融点１２（）”Ｃの４−（６′−
メトキシ−２′−す７チル）−３−ブテン−２−オン１
５Ｆを得る。
実施例１ ４−（６’−メトキシ−２′−す７チル）ブタ／−２−
オン 酢酸エチル５ＯＯ−中の４−（６’−メトキシ−２′−
ナフチル）−３−！テンー２−オ／３２ｆを炭素に支持
した１０％〜元３ｔとともに、水素の吸収がなくなるま
で室温で常圧の水素と振盪すると、融点７＆５℃の４−
（６−メドキシー２−す７チル）−ブタン−２−オンを
２２５を得る。
実施例２ ４−（４’−メトキシ−２′−ナフチル）−ブタン−オ
ン エタノール１２５−中の６−メドキシー２−デμモメチ
ルナフタレンα１モル、アセチルアセＦンα１モルおよ
び炭酸カリウムａ１モルの良合物を１６時間還流加熱す
る。エタノールを減圧下で蒸発し残留物を水とエーテル
との１：ｌの混液４００−と振盪し、エーテル層をＭｇ
５Ｏａで乾燥し、真空蒸発すると、透明油状物を得、こ
れを１Ｎ４Ｈすると、４−（６−メドキシー２−ナフチ
ル）−ブタン−２−オンの固体を得る。
潰ＡＬＪ　薬理学的データ 通常のアレ７、トイジー試験（Ａｌｉｅｎ−Ｄｏ量畠ｙ
Ｔ＠ｓｔ　）　を使用し、本発明の化合物０発惰性を試
験した結果を第１表に示す。ネズミの足のカラｒエン標
準試験法（５ｔａｎｄａｒｄ　Ｒａｔ　Ｐａｗ　Ｃａｒ
ｒａｇｅ＠ｎ−１ｎ　Ｔ＠ｓｔ　）を使用し、本発明の
化合物の抗炎症性を試験した結果も第１表に示す。
これらの結果は過度の発情性が期待されないような投与
量で本発明の化合物は高水準の鎮静作用を有することを
示している。またａ−炭素原子に分枝鎖がないことは、
化合物の抗炎症性に大して影畳を与えないで、発情性を
著しく低下させるものと思われる。
また本発明の式（１） を有する化合物（式中Ｒ，Ｆｉ水素またＦ１皿、を表わ
す）は３００ｓｖ／＆９／日を経口投与して３日後のネ
ズンの胃に過度の刺激を与えないが、式（りの化合物を
同一投与量で経口投与した場合には１５日後に、激しい
胃の刺激が認められる。

Claims (2)

    【特許請求の範囲】
  1. （１）　　式（厘） （式中、Ｒ１ｉｉ水素原子またはメチル基を表わす）を
    有する化合物を還元し、次いで式（１）（式中、Ｒ１＃
    ｉ前述の意味を表わす）゛を有する実質的に純粋な化合
    物を分離することを特徴とする式（１）０化合物の製法
    。
  2. （２）一般式ＣＷ） ｃ式中ｓ　”１　は水素原子ま九はメチル基を表わし、
    ”ｌ　　は置換可能な基（例えば、塩素、臭素。 を九は田つ素原子）を表わす〕 れ１アニオンと反応させ、次いで式（厘）しｒス （式中、Ｒ１は前述ｅｉｔ昧を表わす）を有する実質的
    に純粋な化合物を分離することを特徴とする式（１）の
    化合物の製法。
JP57190679A 1973-09-11 1982-10-29 新ナフタレン誘導体の製法 Expired JPS6033818B2 (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
JPS5890526A true JPS5890526A (ja) 1983-05-30
JPS6033818B2 JPS6033818B2 (ja) 1985-08-05

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
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
JP57190679A Expired JPS6033818B2 (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
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

Country Status (15)

Country Link
JP (4) JPS5920655B2 (ja)
BE (1) BE819794A (ja)
CH (8) CH603524A5 (ja)
CY (2) CY1082A (ja)
DE (2) DE2463219C2 (ja)
DK (1) DK156642C (ja)
FR (1) FR2242972B1 (ja)
GB (1) GB1474377A (ja)
HK (2) HK56180A (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)

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IE40001B1 (en) 1979-02-14
CH603525A5 (ja) 1978-08-15
ZA745441B (en) 1975-08-27
MY8100198A (en) 1981-12-31
CH603524A5 (ja) 1978-08-15
SE7907064L (sv) 1979-08-23
BE819794A (fr) 1975-03-11
DK156642B (da) 1989-09-18
DE2442305A1 (de) 1975-03-13
FR2242972A1 (ja) 1975-04-04
AU7313674A (en) 1976-03-11
MY8100197A (en) 1981-12-31
DK477674A (ja) 1975-05-12
SE7411261L (ja) 1975-03-12
JPS605580B2 (ja) 1985-02-12
IE40001L (en) 1975-03-11
CH599090A5 (ja) 1978-05-12
JPS5920655B2 (ja) 1984-05-15
KE3082A (en) 1980-10-03
JPS5053359A (ja) 1975-05-12
CY1083A (en) 1980-12-27
CH603523A5 (ja) 1978-08-15
SE7907064A0 (sv) 1979-08-23
HK56280A (en) 1980-10-10
CY1082A (en) 1980-12-27
CH603527A5 (ja) 1978-08-15
DE2463219C2 (ja) 1988-02-04
NL175812B (nl) 1984-08-01
JPS5896036A (ja) 1983-06-07
NL7412060A (nl) 1975-03-13
KE3081A (en) 1980-10-03
JPS5921850B2 (ja) 1984-05-22
GB1474377A (en) 1977-05-25
JPS6033818B2 (ja) 1985-08-05
CH613932A5 (ja) 1979-10-31
CH603543A5 (ja) 1978-08-31
JPS58113142A (ja) 1983-07-05
CH603526A5 (ja) 1978-08-15
NL175812C (nl) 1985-01-02
DK156642C (da) 1990-01-29
SE420598B (sv) 1981-10-19
DE2442305C2 (de) 1986-04-03
HK56180A (en) 1980-10-10
FR2242972B1 (ja) 1978-07-21

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