JPS58185553A - Alpha-protected oxyimino-beta-keto-gamma-halogenobutyric acid - Google Patents

Alpha-protected oxyimino-beta-keto-gamma-halogenobutyric acid

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Publication number
JPS58185553A
JPS58185553A JP58012560A JP1256083A JPS58185553A JP S58185553 A JPS58185553 A JP S58185553A JP 58012560 A JP58012560 A JP 58012560A JP 1256083 A JP1256083 A JP 1256083A JP S58185553 A JPS58185553 A JP S58185553A
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JP
Japan
Prior art keywords
formula
group
protected
compound
alpha
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
JP58012560A
Other languages
Japanese (ja)
Other versions
JPS6155905B2 (en
Inventor
Michihiko Ochiai
落合　道彦
Akira Morimoto
明 森本
Yoshihiro Matsushita
義弘 松下
Nobuchika Aki
修躬 安芸
Taiichi Okada
泰一 岡田
Kenji Kawakita
川喜多　健二
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries Ltd
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 Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of JPS58185553A publication Critical patent/JPS58185553A/en
Publication of JPS6155905B2 publication Critical patent/JPS6155905B2/ja
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/34—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

NEW MATERIAL:A compound of formula I [X is halogen: Y and Z incorporate to form a group, =NR<5> (R<5> is protected hydroxyl)], its salt or ester. EXAMPLE:Ethyl alpha-ethoxyimino-2-aminothiazol-4-ylacetate hydrobromide. USE:A synthetic intermediate of antibacterials. PREPARATION:The customary halogenation of a compound of formula II such as a beta-ketobutyric acid bearing a protected oxyimino group in the alpha-position gives the compound of formula I . In the compound of formula I , methyl, phenyl or acetyl is cited as a protecting group for the hydroxyl and methyl, tolyl or benzyl for the carboxyl. The protected oxyimino group has syn- and anti-forms theoretically.

Description

【発明の詳細な説明】 本発明は、式 （式中、Ｘｌ−４ハロケンｆ、Ｙ　トＪ）ｉ−ＮＲ５（
Ｒ５は保護された水酸基）で表わされる基を示す。〕で
表わされる化合物、その基壇たはエステル、及びその製
造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a compound having the formula (wherein,
R5 represents a group represented by a protected hydroxyl group. ], its base or ester, and its production method.

本発明の化合物〔罵〕、その権またはエステルは、式 ％式％ １武中、Ｂ１２は低級アルコキシ基ｔたは保護されでい
てもよいアミノ基を示す。〕で表わされる化合物と反応
させ、要すれば保護基を除去することにより、式 〔一式中、′Ｒ１３は水酸基または保護されていてもよ
いアミノ基を、他は前記と同、ｆ表。〕で表わされる化
合物を製進する丸めの有用な合成中間体であって、得ら
れる化合物ＣＸＩＶ）は、たとえば式〔式中、Ｒ３は水
素またはメトキン１＆を、Ｒ４は水素または求核性化合
物残基を示す。〕で表わされる化合物と反応させ、要す
れば保護基を除去して、広くダラム嚇性繭、鴎性−に対
し高い抗菌力をボす式 〔式中の記号は前記と同意義。〕で表わされる化合物な
どを＃造するのに有用である。The compound of the present invention, its right or ester, has the formula % Formula % 1 where B12 represents a lower alkoxy group or an optionally protected amino group. By reacting with a compound represented by the formula [In the formula, R13 is a hydroxyl group or an optionally protected amino group, the others are the same as above, Table f. ], the resulting compound CXIV) is a useful synthetic intermediate for the preparation of compounds of the formula Indicates the group. [Symbols in the formula have the same meanings as above. It is useful for producing compounds represented by the following.

化合物〔１〕において、ＸとＹは一緒になって武−ＮＲ
５で表わされる基を示し、Ｒ５は保−された水酸Ｊ＆を
示す。このような水酸基の保護基としては本発１４ｉＩ
ＩＫおける各反応を阻害しない限りいかなるものでもよ
く通常メチμ、エチルのような低級アルキル基、フェニ
ル、チエ二μのようなアリール基、アセチル、ベンゾイ
ルのようなアｙ）ｖ基が用いられる。化合物〔罵〕中、
ＸＦｉ樵素、臭素。In compound [1], X and Y together form -NR
5, and R5 represents a preserved hydroxyl J&. As a protecting group for such a hydroxyl group, the present invention 14iI
Any group may be used as long as it does not inhibit each reaction in IK, and usually lower alkyl groups such as methyμ and ethyl, aryl groups such as phenyl and thiene, and y)v groups such as acetyl and benzoyl are used. During the compound [expletive]
XFi woodcutter, bromine.

ヨウ素、フッ章などのハロゲンを示す。ｔｉ、力〜ボキ
Ｖル基は保−されていてもよい。このような保−基とし
ては、酸性条件、アルカリ性条件。Indicates halogens such as iodine and fluoride. The ti, and the groups may be retained. Such holding groups include acidic conditions and alkaline conditions.

遁元条件等の緩和な条件で除去しうるものなら何でもよ
く、たとえば一般にペプチド合成においてカルボキシル
基の保−基として用いられるものから選択され、たとえ
ばメチル、エチル、プロピル。Any group may be used as long as it can be removed under mild conditions such as release conditions, and is selected from those generally used as carboxyl group holding groups in peptide synthesis, such as methyl, ethyl, and propyl.

イソプロピル、ブチル、第２ブチμ、イソグチル。Isopropyl, butyl, sec-butyl, isobutyl.

第３グチルなどのアルキル基、β−メチμスルホニルエ
チル、トリクロルエチル、ジフェニルメチルなどの直涙
アルキル基、フェニル、トリルナトのアリー／ｌ’基、
　ｌ）−第３ブチ〜フエニル、ｐ−ニトロフエニｌＬ／
ナトのＷｔ俟アリール基、ベンジル。Alkyl groups such as tertiary glutyl, direct alkyl groups such as β-methyμsulfonyl ethyl, trichloroethyl, diphenylmethyl, ary/l' groups of phenyl, tolylunato,
l)-tertiary buty-phenyl, p-nitrophenyl/
Nat's Wt aryl group, benzyl.

フェネチル、トルベンジルなどの７フルキＡ’基。7-fulky A' group such as phenethyl and tolbendyl.

ｐ−メトキンベンジル、ｐ−ニトロベンジ／Ｌ／ナトの
置換アフ々キル晟などが用いられる。この化合物〔虐〕
は保＾され九オキシイミノ基に関して坤纜的に５ｙｎ−
およびａｎｔｉ−の絢異性体が存在し、両者とも同様に
有用な合成中間体として用いられる。p-methquinbenzyl, p-nitrobenzyl/L/nato substituted afkyl, etc. are used. This compound
is preserved and is strictly 5yn- with respect to the 9oximino group.
and anti-isomers exist, both of which are equally useful synthetic intermediates.

化合物〔−Ｍ〕は、対応するα位に保護されたオキシイ
ミノ基を有するβ−ケト酪＃ｌＩＡを常法に便ってハロ
ゲン化することによって得られる。Compound [-M] can be obtained by halogenating β-ketobutyric #lIA having a corresponding oximino group protected at the α-position using a conventional method.

５ｆｉ！施例１ α−エトキンイミノ−β−ケト酪酸エチルエステル１８
．７ｆをクロロホルム１００ｓ／に溶解し、水冷下に臭
素１５．９ｆをクロロホルム２０ｓ／に溶解した故を徐
々に滴トする。３０分間攪拌したのち、寥温にもどして
さらに１．５時間攪拌する。反応混合物を水洗し、廣酸
水素ナトリウム水浴液にて沈降したのち、さらに水洗し
硫酸マグネシウムで乾燥する。溶媒留去後エタノ−７’
２５０ｓｒを加え、チオ尿意１５．２ｆを加えて２時間
還流する。5fi! Example 1 α-ethquinimino-β-ketobutyric acid ethyl ester 18
．． 7f was dissolved in 100s/chloroform, and a solution of 15.9f bromine dissolved in 20s/chloroform was gradually added dropwise while cooling with water. After stirring for 30 minutes, the mixture was returned to the original temperature and stirred for an additional 1.5 hours. The reaction mixture was washed with water, precipitated in a sodium hydrogen hydroxide bath, further washed with water, and dried over magnesium sulfate. After solvent distillation, ethanol-7'
Add 250sr, add 15.2f of thiourine, and reflux for 2 hours.

冷却し九のち溶媒を減圧留去し、残留物に水２５０ｄを
加えると固体が析出する。これを′ｆ３取し、水洗した
のち乾燥するとα−エトキンイミノ−２−アミノチアゾ
−〜−４−イｆｉ７＃酸エチルエステμ臭化水嵩酸樵１
７．９ｆが得られる。収率５５襲。After cooling, the solvent was distilled off under reduced pressure and 250 d of water was added to the residue to precipitate a solid. This was taken out, washed with water, and then dried.
7.9f is obtained. Yield: 55%.

元素分析値　Ｃ，Ｉｉ、４Ｎ３０３ＳＢｒ針算値：　Ｃ
，３３，３４；　Ｈ４，３５＋　Ｎ　１２．９＆ｗＳ値
：　ｃ　３２．５２＋　ＩＩ　３．９８；　ｘ　１２．
９２本品の核磁気共鳴スペクトル（１００ＭＨｚ、ｄ６
−１）Ｍ２Ｏ中）は１．３０および１．３２ｐｐｍＫ２
橋類のエチル基メチル水素の三重線、４．２８および４
、３７　ｐｐｍ＋に２櫨艙のエチル基メチレン水嵩の四
重纏、７．６３ｐｐｍにチアゾール５位水素の単線、９
、１２　ｐｐｒｎにアミノ基水素の巾広い単線共鳴線を
ボす。Elemental analysis value C, Ii, 4N303SBr needle value: C
, 33, 34; H4, 35+ N 12.9&wS value: c 32.52+ II 3.98; x 12.
92 Nuclear magnetic resonance spectrum of this product (100MHz, d6
-1) in M2O) is 1.30 and 1.32 ppm K2
Bridges ethyl group methyl hydrogen triplet, 4.28 and 4
, a quadruple coat of ethyl group methylene water volume of 2 h at 37 ppm+, a single line of hydrogen at the 5-position of thiazole at 7.63 ppm, 9
, 12 pprn shows a wide single resonance line of amino group hydrogen.

東施例２ （１）α−メトキシイミノ−ρ−ケト醋酸エチル２７．
３１をクロロホルム１２０ｄに溶かし、これに氷〜ト臭
素２５．３ｆをクロロホルム３０ｍＫ浴かした猷を３０
分間で滴丁する。その後室温で１時間ｒＪｌ井し反応さ
せる。反応物を希＊＊水嵩ナトリウム水溶猷、水で洗浄
した後有機層を乾燥する。浴剤を留去して粗製のα−メ
トキメイミノ−β−ケト−γ−１０ム醋酸エチルを油状
物として得る。East Example 2 (1) Ethyl α-methoxyimino-ρ-keto acetate 27.
31 was dissolved in 120 d of chloroform, and 25.3 f of ice to bromine was bathed in 30 mK of chloroform.
Drop in minutes. Thereafter, the mixture was allowed to react at room temperature for 1 hour. The reaction product was washed with dilute sodium chloride solution and water, and the organic layer was dried. The bath agent is distilled off to obtain crude ethyl acetate as an oil.

（２）氷晶全量をエタノ−Ａ／２５０ｍＫ浴かし、これ
にチオ尿素２４９を加えてａｖｆ間加熱加熱還流る。(2) The entire amount of ice crystals is placed in an ethanol-A/250 mK bath, thiourea 249 is added thereto, and the mixture is heated to reflux during avf.

冷後析出物を１取しエタノールで洗浄する。得られ九結
晶状物賞を酢酸エチルコテトラヒドロフラン（１：１）
混合物３００ｍ／に懸濁し１０％炭酸水素ナトリウム水
溶液を２００ｓ／加えてよくふシｆ＃４′機鳩を分取す
る。乾燥後溶剤を留去して得られた結晶をエーテルで洗
浄しα−メトキシイミノ−α−（２−アミノチアゾール
−４−イＡ／）ｇｌｉｌｌエチルを得る。１６．８６Ｆ
、融点１１２〜１１３℃。After cooling, take one precipitate and wash with ethanol. The nine crystals obtained were ethylcotetrahydrofuran acetate (1:1)
Suspend the mixture in 300 m/ml, add 10% aqueous sodium bicarbonate solution for 200 s/ml, and separate the F#4' pigeons. After drying, the solvent was distilled off and the resulting crystals were washed with ether to obtain α-methoxyimino-α-(2-aminothiazol-4-yA/)grill ethyl. 16.86F
, melting point 112-113°C.

元素分析値　Ｃ８Ｈよ、Ｎ３０３Ｓ ＊ｔＪ：値：　Ｃ４１，９１ｉ　Ｈ４，８４寮Ｉ８値：
　ｃ　４１，２０；　Ｈ４，７０核磁気共鳴スペクト／
Ｌ／（６０ＭＨｚ、ＣＤＣｌ３中）は４、０４　ｐｐｍ
にメトキシ水素の単線、７．４４ｐｐｍにチアゾール１
１５位水素の単線共鳴線を示す。Elemental analysis value C8H, N303S *tJ: value: C41,91i H4,84 dormitory I8 value:
c 41,20; H4,70 nuclear magnetic resonance spectrum/
L/(60MHz, in CDCl3) is 4.04 ppm
single line of methoxy hydrogen, thiazole 1 at 7.44 ppm
A single resonance line of hydrogen at position 15 is shown.

Claims (1)

【特許請求の範囲】 （１１式 Ｃ式中、Ｘはハロゲン原子を、Ｙと２は一緒になって式
−ＮＪ？５（１？５　は保護された水酸基を示す）で表
わされる基を示す〕で表わされる化合物、その墳または
エステ〜。 （２ン式 し式中、Ｙと２は一緒になって武＝ＮＲ５（Ｒ５は体層
された水酸基を示す）で表わされる基を示す〕で表わさ
れる化合物、その墳またはエステＡ／′にハロゲン化す
ることを特徴とする式 １式中、ＸＦｉハロゲン原子を、Ｙ、ＺＶ１前記と同ｔ
ＩＩＩＩを示す〕で表わされる化合物、その塩を九はエ
ステルの製造法。[Claims] (In formula 11C, X represents a halogen atom, and Y and 2 together represent a group represented by the formula -NJ?5 (1?5 represents a protected hydroxyl group) ] Compounds, their mounds or esthetics ~ (In the formula, Y and 2 together represent a group represented by MU = NR5 (R5 represents a layered hydroxyl group)) In the formula 1, the XFi halogen atom is replaced by Y, ZV1, the same t as above.
9 is a method for producing an ester of a compound represented by III] and its salt.
JP58012560A 1975-06-09 1983-01-27 Alpha-protected oxyimino-beta-keto-gamma-halogenobutyric acid Granted JPS58185553A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB24611/75 1975-06-09
GB24611/75A GB1536281A (en) 1975-06-09 1975-06-09 Cephem compounds

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
JP56087403A Division JPS5858353B2 (en) 1975-06-09 1981-06-05 Cefem or penam compound and its production method

Publications (2)

Publication Number Publication Date
JPS58185553A true JPS58185553A (en) 1983-10-29
JPS6155905B2 JPS6155905B2 (en) 1986-11-29

Family

ID=10214399

Family Applications (5)

Application Number Title Priority Date Filing Date
JP51067524A Expired JPS5822039B2 (en) 1975-06-09 1976-06-08 Thiazole compound and its manufacturing method
JP56087403A Expired JPS5858353B2 (en) 1975-06-09 1981-06-05 Cefem or penam compound and its production method
JP58012560A Granted JPS58185553A (en) 1975-06-09 1983-01-27 Alpha-protected oxyimino-beta-keto-gamma-halogenobutyric acid
JP58178160A Pending JPS5989686A (en) 1975-06-09 1983-09-28 Cephem or penam compound
JP60232072A Granted JPS61143388A (en) 1975-06-09 1985-10-16 Cephem compound

Family Applications Before (2)

Application Number Title Priority Date Filing Date
JP51067524A Expired JPS5822039B2 (en) 1975-06-09 1976-06-08 Thiazole compound and its manufacturing method
JP56087403A Expired JPS5858353B2 (en) 1975-06-09 1981-06-05 Cefem or penam compound and its production method

Family Applications After (2)

Application Number Title Priority Date Filing Date
JP58178160A Pending JPS5989686A (en) 1975-06-09 1983-09-28 Cephem or penam compound
JP60232072A Granted JPS61143388A (en) 1975-06-09 1985-10-16 Cephem compound

Country Status (7)

Country Link
JP (5) JPS5822039B2 (en)
AT (2) AT344894B (en)
GB (1) GB1536281A (en)
HK (1) HK2282A (en)
HU (1) HU172304B (en)
MY (1) MY8200219A (en)
SE (1) SE444809B (en)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1536281A (en) * 1975-06-09 1978-12-20 Takeda Chemical Industries Ltd Cephem compounds
DK154939C (en) * 1974-12-19 1989-06-12 Takeda Chemical Industries Ltd METHOD OF ANALOGUE FOR THE PREPARATION OF THIAZOLYLACETAMIDO-CEPHEM COMPOUNDS OR PHARMACEUTICAL ACCEPTABLE SALTS OR ESTERS THEREOF
FR2346014A1 (en) * 1976-01-23 1977-10-28 Roussel Uclaf Amino-thiazolyl-hydroxyimino-acetamido-cephalosporanic acids - with antibacterial activity
SE440655B (en) * 1976-01-23 1985-08-12 Roussel Uclaf SET TO MAKE NEW OXIME DERIVATIVES OF 7-AMINO-THIAZOLYL-ACETAMIDO-CEPHALOSPORANIC ACID
GB1576625A (en) * 1976-04-12 1980-10-08 Fujisawa Pharmaceutical Co Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof
FI771866A (en) * 1976-06-28 1977-12-29 Fujisawa Pharmaceutical Co
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JPS51149296A (en) 1976-12-22
SE444809B (en) 1986-05-12
ATA967775A (en) 1977-12-15
GB1536281A (en) 1978-12-20
JPS5756485A (en) 1982-04-05
JPS5822039B2 (en) 1983-05-06
AT347587B (en) 1979-01-10
MY8200219A (en) 1982-12-31
HU172304B (en) 1978-07-28
SE7713233L (en) 1977-11-23
JPS5989686A (en) 1984-05-23
JPS61143388A (en) 1986-07-01
JPH0346474B2 (en) 1991-07-16
ATA517177A (en) 1978-05-15
AT344894B (en) 1978-08-10
HK2282A (en) 1982-01-22
JPS6155905B2 (en) 1986-11-29
JPS5858353B2 (en) 1983-12-24

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