FI90766B - Förfarande för framställning av farmaceutiskt aktiva 4-(2,6,6-trimetyl-cyklohex-1-enyl)-but-3-en-1-ynylsubstituerade föreningar - Google Patents

Förfarande för framställning av farmaceutiskt aktiva 4-(2,6,6-trimetyl-cyklohex-1-enyl)-but-3-en-1-ynylsubstituerade föreningar Download PDF

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FI90766B
FI90766B FI875681A FI875681A FI90766B FI 90766 B FI90766 B FI 90766B FI 875681 A FI875681 A FI 875681A FI 875681 A FI875681 A FI 875681A FI 90766 B FI90766 B FI 90766B
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enyl
formula
compound
ynyl
trimethylcyclohex
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FI875681A
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Finnish (fi)
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FI90766C (sv
FI875681A0 (sv
FI875681A (sv
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Roshantha A S Chandraratna
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Allergan Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
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    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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    • C07D213/48—Aldehydo radicals
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
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    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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Claims (8)

1. Förfarande för framställning av en farmaceutiskt ak-tiv 4-(2,6,6-trimetylcyklohex-l-enyl)-but-3-en-1-ynyl-substituerad förening med formeln (I) A-B Jy i väri A är pyridyl, furyl eller tienyl; och B är -COOH eller ett farmaceutiskt acceptabelt sait därav eller en lägrealkylester därav, -CHO, dilägrealkoximetyl, l-hydroxi-lägrealkyl eller lägrealkylkarbonyloximetyl, kännetecknat av att en förening med följande formel II om-sättes med en förening med följande formel III i närvaro av Pd(PQ3)4 (Q är fenyl) eller ett liknande kömpi ex s**- ZnCl X-A-B II III i vilken formel III A har ovan angiven betydelse, X är halogen, företrädesvis jod, och B är en skyddad karboxylsyra, alkohol eller aldehyd, för erhällande av en förening med formeln I, och möjligen överförs en erhällen förening med formeln I tili en annan förening med formeln I.
2. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I väri A är pyridyl.
3. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I väri B är -COOH eller en lägrealkylester, -CHO eller -CH2OH eller ett farmaceutiskt acceptabelt sait därav.
4. Förfarande enligt patentkravet 3, kännetecknat av att man framställer etylestern av 6-[4-(2,6,6-trimetylcyklohex- 1-enyl)-but-3-en-l-ynyl]nikotinsyra eller 6-[4-(2,6,6-trime-tylcsyklohex-1-enyl)-but-3-en-l-ynyl]nikotinsyra eller ett farmaceutiskt acceptabelt sait därav.
5. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I väri A är furyl.
6. Förfarande enligt patentkravet 5, kännetecknat av att man framställer etylestern av 5-[4-(2,6,6-trimetylcyklohex- 1-enyl)-but-3-en-l-ynyl]furankarboxylsyra eller 5-[4-(2,6,6-t rimetylcyklohex-1-enyl)-but- 3 -en-1-yny1]furankarboxylsyra.
7. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I väri A är tienyl.
8. Förfarande enligt patentkravet 1, kännetecknat av att man framställer etylestern av 5-[4-(2,6,6-trimetylcyklohex- l-enyl) -but-3-en-l-ynyl]tiofen-2-karboxylsyra eller 5-[4-(2,6,6-trimetylcyklohex-l-enyl)-but-3-en-l-ynyl]tiofen-2-karboxylsyra.
FI875681A 1986-12-24 1987-12-22 Förfarande för framställning av farmaceutiskt aktiva 4-(2,6,6-trimetyl-cyklohex-1-enyl)-but-3-en-1-ynylsubstituerade föreningar FI90766C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94674986A 1986-12-24 1986-12-24
US94674986 1986-12-24

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FI875681A0 FI875681A0 (sv) 1987-12-22
FI875681A FI875681A (sv) 1988-06-25
FI90766B true FI90766B (sv) 1993-12-15
FI90766C FI90766C (sv) 1994-03-25

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FI875681A FI90766C (sv) 1986-12-24 1987-12-22 Förfarande för framställning av farmaceutiskt aktiva 4-(2,6,6-trimetyl-cyklohex-1-enyl)-but-3-en-1-ynylsubstituerade föreningar

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EP (1) EP0272921B1 (sv)
JP (1) JP2693957B2 (sv)
KR (1) KR960000074B1 (sv)
CN (1) CN1024006C (sv)
AT (1) ATE62899T1 (sv)
AU (1) AU599444B2 (sv)
CA (1) CA1326853C (sv)
DE (1) DE3769618D1 (sv)
DK (1) DK167011B1 (sv)
EG (1) EG19587A (sv)
ES (1) ES2036591T3 (sv)
FI (1) FI90766C (sv)
GR (1) GR3002101T3 (sv)
HU (1) HU198295B (sv)
IE (1) IE61902B1 (sv)
IL (1) IL84878A (sv)
MY (1) MY103040A (sv)
NO (1) NO175205C (sv)
NZ (1) NZ222968A (sv)
PH (1) PH23861A (sv)
PT (1) PT86442B (sv)
ZA (1) ZA879595B (sv)

Families Citing this family (55)

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US5272156A (en) * 1989-09-19 1993-12-21 Allergan, Inc. Acetylenes disubstituted with a heteroaromatic group and a 2-substituted 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity
US5399561A (en) * 1989-09-19 1995-03-21 Allergan, Inc. Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-oxochromanyl, 2-oxothiochromanyl or 2-oxo-1,2,3,4-tetrahydro-quinolinyl group having retinoid-like biological activity
US5264456A (en) * 1989-12-29 1993-11-23 Allergan, Inc. Acetylenes disubstituted with a furyl group and a substituted phenyl group having retinoid like activity
US5134159A (en) * 1991-03-26 1992-07-28 Allergan, Inc. 7-chromanyl esters of phenols and benzoic acids having retinoid-like activity
JP3499553B2 (ja) * 1992-02-11 2004-02-23 アラーガン、インコーポレイテッド レチノイド様生物学的活性を有するヘテロアリール置換フェニルエテニル化合物
US5324840A (en) 1992-06-11 1994-06-28 Allergan, Inc. Method of treatment with compounds having retinoid-like activity and reduced skin toxicity and lacking teratogenic effects
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US6172115B1 (en) 1993-02-11 2001-01-09 Allergan Sales, Inc. Method for preventing onset of restenosis after angioplasty employing an RXR-specific retinoid
US5475022A (en) * 1993-10-18 1995-12-12 Allergan, Inc. Phenyl or heteroaryl and tetrahydronaphthyl substituted diene compounds having retinoid like biological activity
US5470999A (en) * 1993-12-30 1995-11-28 Allergan, Inc. Cyclohexene and bicyclic aromatic substituted ethyne compounds having retinoid-like biological activity
US5451605A (en) * 1993-12-30 1995-09-19 Allergan, Inc. 1,2-epoxycyclohexanyl and bicyclic aromatic substituted ethyne compounds having retinoid-like biological activity
US5426118A (en) * 1993-12-30 1995-06-20 Allergan, Inc. [4-(1,2-epoxycyclohexanyl)but-3-en-1-ynyl]aromatic and heteroaromatic acids and derivatives having retinoid-like biological activity
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US5556996A (en) * 1994-12-29 1996-09-17 Allergan Oxiranyls disubstituted with a phenyl group and a substituted chromanyl or tetrahydroquinolinyl group having retinoid like activity
US5514825A (en) * 1994-12-29 1996-05-07 Allergan, Inc. Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
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PT86442A (en) 1988-01-01
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DK682087D0 (da) 1987-12-22
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DK682087A (da) 1988-06-25
CN1024006C (zh) 1994-03-16
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AU599444B2 (en) 1990-07-19
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NO175205B (sv) 1994-06-06
EP0272921A1 (en) 1988-06-29
HU198295B (en) 1989-09-28
KR960000074B1 (ko) 1996-01-03
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ATE62899T1 (de) 1991-05-15
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ZA879595B (en) 1989-09-27
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