SE447993B - PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE - Google Patents

PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE

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Publication number
SE447993B
SE447993B SE8401554A SE8401554A SE447993B SE 447993 B SE447993 B SE 447993B SE 8401554 A SE8401554 A SE 8401554A SE 8401554 A SE8401554 A SE 8401554A SE 447993 B SE447993 B SE 447993B
Authority
SE
Sweden
Prior art keywords
bis
benzamide
piperidylmethyl
trifluoroethoxy
procedure
Prior art date
Application number
SE8401554A
Other languages
Swedish (sv)
Other versions
SE8401554D0 (en
SE8401554L (en
Inventor
C M Leir
Original Assignee
Riker Laboratories 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
Application filed by Riker Laboratories Inc filed Critical Riker Laboratories Inc
Publication of SE8401554D0 publication Critical patent/SE8401554D0/en
Publication of SE8401554L publication Critical patent/SE8401554L/en
Publication of SE447993B publication Critical patent/SE447993B/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • 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
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • 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
    • C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

15 20 25 30 35 447 993 2 Förfarandet kan genomföras direkt fràn den mättade diamin-2-(aminometyl)piperidinen eller indirekt från 'den oreducerade diamin-2-(aminometyl)pyridinen. Sålunda kan 2-aminometylpiperidin omsättas med 2,5-bis(2,2,2- -trifluoretoxi)-a,a,a-trikloracetofenon eller kan föreningen 2-aminometylpyridin omsättas med trikloraceto- fenonen. I vardera fallet fortskrider reaktionen lätt utan yttre värmning i ett inert lösningsmedel, såsom toluen, bensen, isopropylalkohol, cyklohexan och lik- nande. Reaktionen fortskrider särskilt lätt och med höga utbyten när den oreducerade diaminen omsättes i en blandning av toluen och cyklohexan. The process can be carried out directly from the saturated diamine-2- (aminomethyl) piperidine or indirectly from the unreduced diamine-2- (aminomethyl) pyridine. Thus, 2-aminomethylpiperidine can be reacted with 2,5-bis (2,2,2--trifluoroethoxy) -α, α, α-trichloroacetophenone or the compound 2-aminomethylpyridine can be reacted with the trichloroacetophenone. In each case, the reaction proceeds easily without external heating in an inert solvent such as toluene, benzene, isopropyl alcohol, cyclohexane and the like. The reaction proceeds particularly easily and in high yields when the unreduced diamine is reacted in a mixture of toluene and cyclohexane.

Följande exempel illustrerar förfarandet enligt uppfinningen och är inte avsedda att begränsa uppfin- ningens omfång, sådant det beskrivs ovan.The following examples illustrate the process of the invention and are not intended to limit the scope of the invention, as described above.

EXEMPEL 1 Förfarandet genomfört i två reaktioner Till en lösning av 0,05 mol (21,0 g) 2,5-bis-(2,2,2- -trifluoretoxi)-a,d,d-trikloracetofenon i 60 ml toluen ' sättes droppvis en lösning av 0,055 mol (6,0 g) 2-amino- metylpyridin i 50 ml cyklohexan och 10 ml toluen. Reak- tionen är exoterm och en fällning bildas omedelbart.EXAMPLE 1 The procedure carried out in two reactions To a solution of 0.05 mol (21.0 g) of 2,5-bis- (2,2,2-trifluoroethoxy) -α, d, d-trichloroacetophenone in 60 ml of toluene A solution of 0.055 mol (6.0 g) of 2-aminomethylpyridine in 50 ml of cyclohexane and 10 ml of toluene is added dropwise. The reaction is exothermic and a precipitate forms immediately.

Ytterligare toluen och cyklohexan tillsättes för att ge en blandningskonsistens som medgör omröring och om- röringen fortsättes i 2 h vid ca 25°C. Fastämnet sepa- reras därefter genom filtrering, tvättas med en bland- ning av toluen och cyklohexan och torkas för att ge ett vitt fastämne. Produkten är 2,5-bis(2,2,2-trifluor- etoxi)-N-(2~pyridylmetyl)bensamid, smp 104-106°C, 17,8 g, 89 % utbyte.Additional toluene and cyclohexane are added to give a mixing consistency that allows stirring and stirring is continued for 2 hours at about 25 ° C. The solid is then separated by filtration, washed with a mixture of toluene and cyclohexane and dried to give a white solid. The product is 2,5-bis (2,2,2-trifluoroethoxy) -N- (2-pyridylmethyl) benzamide, mp 104-106 ° C, 17.8 g, 89% yield.

En blandning av 0,33 mol (134,7 g) 2,5-bis(2,2,2- -trifluoretoxi)-N-(2-pyridylmetyl)bensamid, 1,347 liter isättíksyra och 13,5 g 5 % platina på kol reduceras i en Parr-apparat vid ett tryck av 13,6 kp väte vid rums- temperatur. Reaktionen är fullständig på 6-7 h. Reak- tionsblandningen filtreras och katalysatorn tvättas med 10 15 20 447 993 3 isopropylalkohol. Lösningen och tvättvätskorna indunstas för att ge en återstod. Hexan tillsättes till återstoden 'och det resulterande vita fastämnet uppsamlas och om- kristalliseras ur en blandning av aceton och hexan. Ett 71 % utbyte av 2,5-bis(2,2,2-trifluoretoxi)-N-(2-piperir dylmetyl)bensamidacetat, smp 150-l52°C, erhålles. Genom koncentration av den återstående vätskan erhålles ytter- ligare 18% produkt som en andra produktomgàng med en smp av 148-150°C.A mixture of 0.33 mol (134.7 g) of 2,5-bis (2,2,2--trifluoroethoxy) -N- (2-pyridylmethyl) benzamide, 1.347 liters of glacial acetic acid and 13.5 g of 5% platinum on carbon is reduced in a Parr apparatus at a pressure of 13.6 kp hydrogen at room temperature. The reaction is complete in 6-7 hours. The reaction mixture is filtered and the catalyst is washed with isopropyl alcohol. The solution and the washing liquids are evaporated to give a residue. Hexane is added to the residue and the resulting white solid is collected and recrystallized from a mixture of acetone and hexane. A 71% yield of 2,5-bis (2,2,2-trifluoroethoxy) -N- (2-piperidylmethyl) benzamide acetate, mp 150-125 ° C, is obtained. By concentrating the remaining liquid, an additional 18% of product is obtained as a second product cycle with a melting point of 148-150 ° C.

EXEMPEL 2 Förfarandet genomfört i en enkelreaktion Till en lösning av 0,01 mol (4,l9 g) 2,5-bis- -(2,2,2-trifluoretoxi)-a,a,a-trikloracetofenon i 50 ml isopropylalkohol sättes 0,01 mol (1,2 g) 2-aminomety1- piperidin. Blandningen blir gradvis fast under en period av 30 min. Blandningen får sätta sig i ca 16 h, varefter 0,01 M ättiksyra och 5 ml isopropylalkohol tillsättes och lösningen värms för att upplösa allt fastämnet. vid kylning erhålles 3,0 g vitt fast ämne. Filtratet indunstas och återstoden omkristalliseras ur isopropyl- alkohol för att ge ytterligare produkt som ett vitt fast ämne. Produkten är 2,S-bis-(2,2,2-trifluoretoxi)- -N-(2-piperidylmetyl)bensamidacetat enligt dess infra- röd- och kärnmagnetíska resonansspektra.EXAMPLE 2 The procedure carried out in a single reaction To a solution of 0.01 mol (4.19 g) of 2,5-bis- - (2,2,2-trifluoroethoxy) -α, α, α-trichloroacetophenone in 50 ml of isopropyl alcohol is added 0.01 mol (1.2 g) of 2-aminomethylpiperidine. The mixture gradually solidifies over a period of 30 minutes. The mixture is allowed to settle for about 16 hours, after which 0.01 M acetic acid and 5 ml of isopropyl alcohol are added and the solution is heated to dissolve all the solid. on cooling, 3.0 g of white solid are obtained. The filtrate is evaporated and the residue is recrystallized from isopropyl alcohol to give additional product as a white solid. The product is 2,5-bis- (2,2,2-trifluoroethoxy) -N- (2-piperidylmethyl) benzamide acetate according to its infrared and nuclear magnetic resonance spectra.

Claims (1)

1. 447 993 PATENTKRAV Förfarande för framställning av 2,5-bis(2,2,2- -trifluoretoxi)-N-(2-piperidylmetyl)bensamid, k ä n - n e t e c k n a t av omsättning av 2,5-bis(2,2,2-tri- fluoretoxi)-a,a,aftrikloracetofenon alternativt med 2-(aminometyl)piperidin för att bilda den önskade pro- dukten i ett steg eller med 2-(aminometyl)pyridin, och därefter reducering för att bilda den önskade pro- dukten, eventuellt som den fria basen.A process for the preparation of 2,5-bis (2,2,2- -trifluoroethoxy) -N- (2-piperidylmethyl) benzamide, characterized by the reaction of 2,5-bis (2, 2,2-trifluoroethoxy) -α, a, aftrichloroacetophenone alternatively with 2- (aminomethyl) piperidine to form the desired product in one step or with 2- (aminomethyl) pyridine, and then reduction to form the desired the product, possibly as the free base.
SE8401554A 1979-03-19 1984-03-21 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE SE447993B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2133179A 1979-03-19 1979-03-19
US2133279A 1979-03-19 1979-03-19

Publications (3)

Publication Number Publication Date
SE8401554D0 SE8401554D0 (en) 1984-03-21
SE8401554L SE8401554L (en) 1984-03-21
SE447993B true SE447993B (en) 1987-01-12

Family

ID=26694559

Family Applications (5)

Application Number Title Priority Date Filing Date
SE8002003A SE447992B (en) 1979-03-19 1980-03-14 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE
SE8401555A SE463260B (en) 1979-03-19 1984-03-21 acetophenone
SE8401554A SE447993B (en) 1979-03-19 1984-03-21 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE
SE8901533A SE463419B (en) 1979-03-19 1989-04-27 acetophenone
SE8901532A SE463418B (en) 1979-03-19 1989-04-27 acetophenone

Family Applications Before (2)

Application Number Title Priority Date Filing Date
SE8002003A SE447992B (en) 1979-03-19 1980-03-14 PROCEDURE FOR PREPARING 2,5-BIS (2,2,2-TRIFLUORETOXY) -N- (2-PIPERIDYLMETHYL) BENZAMIDE
SE8401555A SE463260B (en) 1979-03-19 1984-03-21 acetophenone

Family Applications After (2)

Application Number Title Priority Date Filing Date
SE8901533A SE463419B (en) 1979-03-19 1989-04-27 acetophenone
SE8901532A SE463418B (en) 1979-03-19 1989-04-27 acetophenone

Country Status (14)

Country Link
JP (8) JPH01125342A (en)
CA (1) CA1137486A (en)
CH (1) CH643829A5 (en)
DE (1) DE3010195A1 (en)
DK (3) DK167062B1 (en)
ES (1) ES8104227A1 (en)
FR (7) FR2454438A1 (en)
GB (2) GB2045760B (en)
IE (1) IE49558B1 (en)
IL (1) IL59623A (en)
IT (1) IT1195262B (en)
NL (1) NL191486C (en)
PT (1) PT70967A (en)
SE (5) SE447992B (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2519975A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR PREPARING TRIFLUOROMETHOXY OR TRIFLUOROMETHYLTHIOPHENYLCETONES
FR2519980A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE SULFONYLATION OF HALOGENO OR TRIHALOGENOMETHYLBENZENES
FR2519974A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE ACYLATION OF HALOGENO OR TRIHALOGENOMETHYLBENZENES
FR2519979A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF TRIFLUOROMETHOXY OR TRIFLUOROMETHYLTHIOPHENYLSULFONES
FR2525588A1 (en) * 1982-04-22 1983-10-28 Rhone Poulenc Spec Chim PROCESS FOR PREPARING PHENYLCETONES FROM HALOGENO OR TRIHALOGENOMETHYLBENZENES AND ALIPHATIC OR AROMATIC TRIHALOGENOMETHYL COMPOUNDS
EP0175188A1 (en) * 1984-09-11 1986-03-26 Nihon Tokushu Noyaku Seizo K.K. Carbamoylimidazole derivatives
US4675448A (en) * 1985-02-13 1987-06-23 Ethyl Corporation Chlorination process
FR2579594B1 (en) * 1985-03-29 1987-06-05 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF TRIFLUOROETHOXY OR TRIFLUOROETHYLTHIOBENZENES
FR2579591B1 (en) * 1985-03-29 1988-10-14 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF PENTAFLUOROETHOXY AND PENTAFLUOROETHYLTHIOBENZENIQUE DERIVATIVES
NZ219913A (en) * 1986-04-25 1990-08-28 Riker Laboratories Inc Various flecainide derivatives and antibodies raised thereto
DE3786037T2 (en) * 1986-04-25 1993-11-25 Abbott Lab Tracer for use in immunological fluorescence polarization methods for the detection of flecainide.
DE3644798A1 (en) * 1986-12-31 1988-07-14 Hoechst Ag NEW NITROHALOALCOXYBENZOLS, METHOD FOR THEIR PRODUCTION AND THEIR USE
FR2640262B1 (en) * 1988-12-14 1991-05-31 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF TRIFLUOROETHOXYLATED ARYLIC KETONES
IL120715A (en) 1997-04-21 2000-07-16 Finetech Ltd Process for the preparation of (2,2,2,-trifluoroethoxy)benzoic acids
IL121288A (en) 1997-07-11 2000-10-31 Finetech Ltd Process and a novel intermediate for the preparation of flecainide
US6316627B1 (en) 1997-04-21 2001-11-13 Fine Tech Ltd. Process for the preparation of flecainide
US7196197B2 (en) 2003-09-17 2007-03-27 Apotex Pharmachem Inc. Process for the preparation of Flecainide, its pharmaceutically acceptable salts and important intermediates thereof
JP4894226B2 (en) * 2005-10-31 2012-03-14 Ｄｉｃ株式会社 Method for producing fluorine-containing liquid crystal compound having hydroquinone skeleton

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3539642A (en) * 1967-07-19 1970-11-10 Geigy Chem Corp 2-phenyl-2-(1-naphthyl)acetamides
US3772304A (en) * 1969-10-30 1973-11-13 Hoffmann La Roche 4-hydroxy-isoquinolines and processes for their preparation
US3719687A (en) * 1970-07-22 1973-03-06 Riker Laboratories Inc N-(2-dialkylaminoalkylene)amides of 1,1-dihydroperfluoroalkoxy-substituted aryl acids and salts thereof
US3655728A (en) 1970-07-22 1972-04-11 Riker Laboratories Inc N-(2 - dialkylaminoalkylene)-esters of fluoroalkoxy-substituted aryl carboxylic acid and salts thereof
US3967949A (en) * 1973-06-18 1976-07-06 Eli Lilly And Company Fluoroalkoxyphenyl-substituted nitrogen heterocycles as plant stunting agents
US4169108A (en) * 1973-08-16 1979-09-25 Sterling Drug Inc. 5(OR 6)-[(Substituted-amino)alkyl]-2,3-naphthalenediols
US4005209A (en) * 1974-04-01 1977-01-25 Riker Laboratories, Inc. Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides
US3900481A (en) * 1974-04-01 1975-08-19 Riker Laboratories Inc Derivatives of pyrrolidine and piperidine
US4013670A (en) * 1974-04-01 1977-03-22 Riker Laboratories, Inc. Derivatives of pyrrolidine and piperidine
IL49803A (en) * 1975-06-28 1979-11-30 Fisons Ltd Preparation of pyrogallol
DE2616478C2 (en) * 1976-04-14 1986-05-22 Brickl, Rolf, Dr., 7951 Warthausen Medicines, biocides and cosmetics containing fluoroacylresorcins
JPS6023656B2 (en) * 1976-09-02 1985-06-08 川研フアインケミカル株式会社 Method for producing alkoxy aromatic compounds
US4097481A (en) * 1976-11-08 1978-06-27 Riker Laboratories, Inc. Tertiary amide derivatives of pyrrolidine and piperidine
US4071524A (en) * 1976-11-08 1978-01-31 Riker Laboratories, Inc. Derivatives of urea

Also Published As

Publication number Publication date
DK79891D0 (en) 1991-04-30
JPH022869B2 (en) 1990-01-19
DK164857C (en) 1993-01-18
DK79891A (en) 1991-04-30
SE463418B (en) 1990-11-19
NL8001551A (en) 1980-09-23
IT8020746A0 (en) 1980-03-18
IL59623A (en) 1983-07-31
GB2045760A (en) 1980-11-05
FR2454438A1 (en) 1980-11-14
JPH01125344A (en) 1989-05-17
NL191486C (en) 1995-08-04
SE8901532D0 (en) 1989-04-27
FR2468590B1 (en) 1983-09-23
SE8401554D0 (en) 1984-03-21
CA1137486A (en) 1982-12-14
DK112180A (en) 1980-09-20
JPH0251906B2 (en) 1990-11-08
DK122290D0 (en) 1990-05-17
JPH0251907B2 (en) 1990-11-08
DE3010195A1 (en) 1980-10-02
FR2468591A1 (en) 1981-05-08
JPH0251908B2 (en) 1990-11-08
IE800549L (en) 1980-09-19
GB2097000A (en) 1982-10-27
CH643829A5 (en) 1984-06-29
FR2468591B1 (en) 1983-07-22
DE3010195C2 (en) 1990-10-25
FR2468569B1 (en) 1983-03-11
FR2454438B1 (en) 1982-07-23
SE8901532L (en) 1989-04-27
JPH0372212B2 (en) 1991-11-18
JPH01104044A (en) 1989-04-21
FR2468569A1 (en) 1981-05-08
SE8401555L (en) 1984-03-21
SE8901533D0 (en) 1989-04-27
SE463419B (en) 1990-11-19
SE8002003L (en) 1980-09-20
FR2468590A1 (en) 1981-05-08
IT1195262B (en) 1988-10-12
FR2468570B1 (en) 1983-03-11
FR2468570A1 (en) 1981-05-08
IL59623A0 (en) 1980-06-30
JPH01104043A (en) 1989-04-21
NL191486B (en) 1995-04-03
JPH01125342A (en) 1989-05-17
JPH022870B2 (en) 1990-01-19
FR2468571B1 (en) 1983-03-11
SE8401554L (en) 1984-03-21
DK122290A (en) 1990-05-17
DK164857B (en) 1992-08-31
JPH01125341A (en) 1989-05-17
GB2045760B (en) 1983-05-11
SE8901533L (en) 1989-04-27
JPH0339498B2 (en) 1991-06-14
JPH01125339A (en) 1989-05-17
FR2468576A1 (en) 1981-05-08
SE8401555D0 (en) 1984-03-21
JPH01125343A (en) 1989-05-17
ES489629A0 (en) 1981-04-01
SE447992B (en) 1987-01-12
GB2097000B (en) 1983-11-30
IE49558B1 (en) 1985-10-30
JPH01104045A (en) 1989-04-21
JPH0149695B2 (en) 1989-10-25
ES8104227A1 (en) 1981-04-01
SE463260B (en) 1990-10-29
FR2468571A1 (en) 1981-05-08
PT70967A (en) 1980-04-01
FR2468576B1 (en) 1983-01-21
DK167062B1 (en) 1993-08-23

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