SE8008252L - 5- (PYRIDINYL) -2 (1H) -PYRIDINONES, USED AS CARDIOTONIC AGENTS AND THEIR PREPARATION - Google Patents

5- (PYRIDINYL) -2 (1H) -PYRIDINONES, USED AS CARDIOTONIC AGENTS AND THEIR PREPARATION

Info

Publication number
SE8008252L
SE8008252L SE8008252A SE8008252A SE8008252L SE 8008252 L SE8008252 L SE 8008252L SE 8008252 A SE8008252 A SE 8008252A SE 8008252 A SE8008252 A SE 8008252A SE 8008252 L SE8008252 L SE 8008252L
Authority
SE
Sweden
Prior art keywords
alkyl
compounds
amino
pyridinyl
pyridinones
Prior art date
Application number
SE8008252A
Other languages
Swedish (sv)
Other versions
SE442398B (en
Inventor
George Yohe Lesher
Richard Everett Philion
Donald Frederick Page
Chester Joseph Opalka Jr
Original Assignee
Sterling Drug Inc
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
Priority claimed from US06/135,100 external-priority patent/US4297360A/en
Priority claimed from US06/198,461 external-priority patent/US4313951A/en
Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of SE8008252L publication Critical patent/SE8008252L/en
Publication of SE442398B publication Critical patent/SE442398B/en

Links

Classifications

    • 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
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • 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
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1-R1-3-[unsubstituted, amino, cyano, carbamyl, halo, lower- alkylamino, di-(lower-alkyl)amino, lower-acylamino carboxy or lower- carbalkoxy]-6-(lower-alkyl)-5- (optionally lower-allyl substituted pyridinyl)-2(1H)-pyridinones or pharmaceutically- acceptable acid-addition or cationic salts thereof are useful as cardiotonic agents, where R1 is hydrogen, lower-alkyl or lower- hydroxyalkyl. 1-R1-3-amino-6-(lower- alkyl)-5-(pyridinyl)-2(1H)-pyridinones are prepared by hydrolyzing the corresponding 3-cyano compounds to produce the corresponding 3-carbamyl compounds and reacting the latter with a reagent capable of converting carbamyl to amino. The 1-R1-3-cyano-6- (lower-alkyl)-5-(pyridinyl)-2(1H)- pyridinones are prepared by reacting (pyridinylmethyl) lower-alkyl ketones with dimethylformamide di-(lower- alkyl)acetal to produce 1-(pyridinyl)-2- (dimethylamino)ethenyl lower-alkyl ketones and reacting said ketones with N-R1-O-cyanoacetamide to produce the 1-R1-3-cyano-6-(lower-alkyl)-5- (pyridinyl)-2(1H)-pyridinones. Also shown are the conversions: of the 3- cyano compounds to the 3-H and 3- carboxy compounds; of the 3-H compounds to the 3-halo compounds; of the 3-halo compounds to the 3-[mono- (lower-alkyl)-or di-(lower-alkyl)- amino]compounds; of the 3-amino compounds to the 3-lower-acylamino or 3-[mono-(lower-alkyl)- or di-(lower- alkyl) amino] compounds, and of the 3-carboxy compounds to the 3- carbethoxy compounds.
SE8008252A 1979-11-26 1980-11-25 5- (PYRIDINYL) -2 (1H) -PYRIDINONES, PROCEDURE FOR PREPARING THESE, AND A CARDIOTONIC COMPOSITION SE442398B (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US9750479A 1979-11-26 1979-11-26
US06/135,100 US4297360A (en) 1980-03-28 1980-03-28 5-(Pyridinyl)pyridine-2,3-diamines, preparation thereof and their cardiotonic use
US06/198,461 US4313951A (en) 1979-11-26 1980-10-20 3-Substituted-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones, their cardiotonic use and intermediates therefor
US06/204,726 US4312875A (en) 1980-03-28 1980-11-06 5-(Pyridinyl)-6-(lower-alkyl)-2(1H)-pyridinones, 1,2-dihydro-2-oxo-5-(pyridinyl)-6-(lower-alkyl)nicotinic acids and lower-alkyl esters thereof, and cardiotonic use thereof

Publications (2)

Publication Number Publication Date
SE8008252L true SE8008252L (en) 1981-05-27
SE442398B SE442398B (en) 1985-12-23

Family

ID=27492921

Family Applications (1)

Application Number Title Priority Date Filing Date
SE8008252A SE442398B (en) 1979-11-26 1980-11-25 5- (PYRIDINYL) -2 (1H) -PYRIDINONES, PROCEDURE FOR PREPARING THESE, AND A CARDIOTONIC COMPOSITION

Country Status (20)

Country Link
AT (1) AT379387B (en)
CH (1) CH649535A5 (en)
DE (1) DE3044568A1 (en)
DK (1) DK151799C (en)
ES (1) ES8301920A1 (en)
FI (1) FI76564C (en)
FR (2) FR2470124B1 (en)
GB (2) GB2065642B (en)
GR (1) GR71608B (en)
HK (2) HK31189A (en)
IE (1) IE50632B1 (en)
IL (2) IL61501A (en)
IT (1) IT1148740B (en)
LU (1) LU82957A1 (en)
MX (1) MX155904A (en)
NL (2) NL192202C (en)
NO (2) NO154345C (en)
NZ (1) NZ195564A (en)
PT (1) PT72106B (en)
SE (1) SE442398B (en)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4305948A (en) * 1980-12-22 1981-12-15 Sterling Drug Inc. N-Hydroxy-1,2-dihydro-2-oxo-5-(pyridinyl)-nicotinimidamide and their cardiotonic use
US4465686A (en) * 1981-09-08 1984-08-14 Sterling Drug Inc. 5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones, their cardiotonic use and preparation
FR2529891A1 (en) * 1982-07-12 1984-01-13 Nativelle Sa Ets PYRIDYL-3 ALCOXY-5 PYRAZOLE DERIVATIVES, PREPARATION METHOD AND THERAPEUTIC APPLICATION
IL69407A (en) * 1982-08-23 1987-10-20 Warner Lambert Co 2(1h)-pyridinones,their preparation and pharmaceutical compositions containing them
IL70169A0 (en) * 1982-11-18 1984-02-29 Sterling Drug Inc 2(1h)-pyridinones,their preparation and pharmaceutical compositions containing them
GB8414220D0 (en) * 1984-06-04 1984-07-11 Sterwin Ag Medicaments in unit dose form
DE69108733T2 (en) * 1990-08-21 1995-09-14 Upjohn Co BISPHOSPHONIC ACID DERIVATIVES AS AN ANTIARTHRITIC AGENT.
CZ403592A3 (en) * 1992-02-20 1993-12-15 Hoechst Ag Arylcarbonylaminoalkyldihydrooxopyridines, process of their preparation and their use
US7772188B2 (en) 2003-01-28 2010-08-10 Ironwood Pharmaceuticals, Inc. Methods and compositions for the treatment of gastrointestinal disorders
RU2423351C2 (en) * 2004-12-16 2011-07-10 Вертекс Фармасьютикалз Инкорпорейтед Pyrid-2-ones applicable as protein kinase inhibitors of tec family for treating inflammatory, proliferative and immunologically mediated diseases
EP1956906A4 (en) 2005-11-09 2009-12-30 Combinatorx Inc Methods, compositions, and kits for the treatment of medical conditions
US20100120694A1 (en) 2008-06-04 2010-05-13 Synergy Pharmaceuticals, Inc. Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders
CA3089569C (en) 2007-06-04 2023-12-05 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
EP2321341B1 (en) 2008-07-16 2017-02-22 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
CN108676076A (en) 2011-03-01 2018-10-19 辛纳吉制药公司 The method for preparing guanosine cyclic mono-phosphate agonist
CN104023725B (en) 2011-08-16 2019-04-26 卡迪欧拉有限公司 Controlled release preparation
US20150119399A1 (en) 2012-01-10 2015-04-30 President And Fellows Of Harvard College Beta-cell replication promoting compounds and methods of their use
JP6499591B2 (en) 2013-02-25 2019-04-10 シナジー ファーマシューティカルズ インコーポレイテッド Guanylate cyclase receptor agonists for use in colon lavage
EP2970384A1 (en) 2013-03-15 2016-01-20 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase and their uses
JP2016514670A (en) 2013-03-15 2016-05-23 シナジー ファーマシューティカルズ インコーポレイテッド Guanylate cyclase receptor agonists in combination with other drugs
RS65632B1 (en) 2013-06-05 2024-07-31 Bausch Health Ireland Ltd Ultra-pure agonists of guanylate cyclase c, method of making and using same
WO2015021358A2 (en) 2013-08-09 2015-02-12 Dominique Charmot Compounds and methods for inhibiting phosphate transport
US10493067B2 (en) 2014-12-22 2019-12-03 Cardiora Pty Ltd. Method of treating heart failure with preserved ejection fraction by administering milrinone
JP2022533251A (en) 2019-05-21 2022-07-21 アルデリックス， インコーポレイテッド Combinations to lower serum phosphate in patients

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4004012A (en) * 1975-10-14 1977-01-18 Sterling Drug Inc. 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones
US4072746A (en) * 1975-10-14 1978-02-07 Sterling Drug Inc. 3-Amino-5-(pyridinyl)-2(1H)-pyridinones

Also Published As

Publication number Publication date
LU82957A1 (en) 1981-06-04
FI76564C (en) 1988-11-10
MX155904A (en) 1988-05-23
HK31189A (en) 1989-04-21
NO803550L (en) 1981-05-27
ES507620A0 (en) 1982-11-16
AT379387B (en) 1985-12-27
NL192202B (en) 1996-11-01
FI803652L (en) 1981-05-27
IT8026218A0 (en) 1980-11-25
GR71608B (en) 1983-06-17
IT1148740B (en) 1986-12-03
IE802430L (en) 1981-05-26
GB2065642B (en) 1984-04-04
FR2470124A1 (en) 1981-05-29
IE50632B1 (en) 1986-05-28
GB2131421A (en) 1984-06-20
HK83090A (en) 1990-10-19
ATA578080A (en) 1985-05-15
NZ195564A (en) 1983-09-30
GB8315983D0 (en) 1983-07-13
SE442398B (en) 1985-12-23
DK151799B (en) 1988-01-04
NO156127C (en) 1987-07-29
DE3044568C2 (en) 1990-11-29
NL192202C (en) 1997-03-04
CH649535A5 (en) 1985-05-31
DK151799C (en) 1988-06-20
NO154345B (en) 1986-05-26
NL8006399A (en) 1981-06-16
NO854001L (en) 1981-05-27
IL61501A0 (en) 1981-05-20
PT72106A (en) 1980-12-01
DE3044568A1 (en) 1981-08-27
FI76564B (en) 1988-07-29
NO154345C (en) 1986-09-03
GB2065642A (en) 1981-07-01
NL970028I2 (en) 1998-03-02
FR2470124B1 (en) 1986-12-19
NO156127B (en) 1987-04-21
IL61501A (en) 1984-06-29
ES8301920A1 (en) 1982-11-16
DK501180A (en) 1981-05-27
PT72106B (en) 1981-09-29
FR2553767A1 (en) 1985-04-26
NL970028I1 (en) 1997-10-01
FR2553767B1 (en) 1987-01-16
IL69847A0 (en) 1983-12-30
GB2131421B (en) 1985-06-26

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