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
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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
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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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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/58Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation 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
    • C07C29/136Preparation 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
    • C07C29/143Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation 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
    • C07C29/136Preparation 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
    • C07C29/143Preparation 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
    • C07C29/145Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36Preparation 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
    • C07C29/38Preparation 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
    • C07C29/40Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/26Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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    • C07C45/46Friedel-Crafts reactions
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/62Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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
    • C07C45/68Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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
    • C07C45/68Preparation 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
    • C07C45/72Preparation 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
    • C07C45/74Preparation 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
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
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  • 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
JP57190679A Expired JPS6033818B2 (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 (2)

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

Family Applications After (1)

Application Number Title Priority Date Filing Date
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) CY1083A (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)

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
DE69120491T2 (de) * 1990-09-18 1996-11-14 Fujitsu Ltd Cursorverschiebungssteuerungsgerät für eine Rechneranzeige
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

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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

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

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