LU83512A1 - Procede de preparation d'oxazolidine-2,4-diones substituees en position 5 - Google Patents

Procede de preparation d'oxazolidine-2,4-diones substituees en position 5 Download PDF

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Publication number
LU83512A1
LU83512A1 LU83512A LU83512A LU83512A1 LU 83512 A1 LU83512 A1 LU 83512A1 LU 83512 A LU83512 A LU 83512A LU 83512 A LU83512 A LU 83512A LU 83512 A1 LU83512 A1 LU 83512A1
Authority
LU
Luxembourg
Prior art keywords
formula
chloro
compound
oxazolidine
dione
Prior art date
Application number
LU83512A
Other languages
English (en)
French (fr)
Inventor
Rodney C Schnur
Original Assignee
Pfizer
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 Pfizer filed Critical Pfizer
Publication of LU83512A1 publication Critical patent/LU83512A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • 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
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
    • 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
    • C07C45/008—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with tri- or tetrahalomethyl compounds
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C07D239/62—Barbituric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • C07D263/44—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • C07D263/46—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
LU83512A 1980-07-28 1981-07-27 Procede de preparation d'oxazolidine-2,4-diones substituees en position 5 LU83512A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US17320680A 1980-07-28 1980-07-28
US17320680 1980-07-28
US22220281 1981-01-02
US06/222,202 US4367234A (en) 1980-07-28 1981-01-02 Hypoglycemic 5-substituted oxazolidine-2,4-diones

Publications (1)

Publication Number Publication Date
LU83512A1 true LU83512A1 (fr) 1982-02-17

Family

ID=26868872

Family Applications (1)

Application Number Title Priority Date Filing Date
LU83512A LU83512A1 (fr) 1980-07-28 1981-07-27 Procede de preparation d'oxazolidine-2,4-diones substituees en position 5

Country Status (27)

Country Link
US (1) US4367234A (OSRAM)
KR (3) KR850000381B1 (OSRAM)
AR (3) AR228061A1 (OSRAM)
AT (1) AT376424B (OSRAM)
AU (1) AU526905B2 (OSRAM)
CA (1) CA1155855A (OSRAM)
CH (1) CH653025A5 (OSRAM)
DD (1) DD202149A5 (OSRAM)
DE (1) DE3129309A1 (OSRAM)
DK (1) DK151882C (OSRAM)
ES (3) ES504322A0 (OSRAM)
FI (1) FI77457C (OSRAM)
FR (1) FR2487348B1 (OSRAM)
GB (3) GB2083810B (OSRAM)
GR (1) GR74590B (OSRAM)
HU (1) HU185682B (OSRAM)
IE (1) IE51427B1 (OSRAM)
IL (1) IL63422A (OSRAM)
IT (1) IT1138110B (OSRAM)
LU (1) LU83512A1 (OSRAM)
NL (1) NL8103536A (OSRAM)
NO (1) NO812558L (OSRAM)
NZ (1) NZ197853A (OSRAM)
PH (1) PH17421A (OSRAM)
PT (1) PT73437B (OSRAM)
SE (1) SE460849B (OSRAM)
YU (3) YU185281A (OSRAM)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4689336A (en) * 1981-01-02 1987-08-25 Pfizer Inc. Hypoglycemic 5-substituted oxazolidine 2,4-diones
GR78120B (OSRAM) * 1982-03-01 1984-09-26 Pfizer
US4430337A (en) 1982-06-23 1984-02-07 Pfizer Inc. Alicyclic substituted oxazolidine-2,4-diones having hypoglycemic activity
JPS59186916A (ja) * 1983-04-06 1984-10-23 Aiji Noda 膵石症治療剤
US5130379A (en) * 1988-03-08 1992-07-14 Pfizer Inc. Hypoglycemic thiazolidinedione derivatives
US4946942A (en) * 1988-03-11 1990-08-07 Bioresearch, Inc. Urethane-protected amino acid-N-carboxyanhydrides
US5442124A (en) * 1989-06-30 1995-08-15 Firmenich Sa Process for the preparation of novel aromatic compounds
WO1991007107A1 (en) * 1989-11-13 1991-05-30 Pfizer Inc. Oxazolidinedione hypoglycemic agents
US5036079A (en) * 1989-12-07 1991-07-30 Pfizer Inc. Hypoglycemic thiazolidinedione derivatives
KR100215627B1 (ko) * 1990-06-07 1999-08-16 레슬리 제인 에드워즈 치료용 헤테로사이클 화합물
GB9017218D0 (en) * 1990-08-06 1990-09-19 Beecham Group Plc Novel compounds
US5334604A (en) * 1990-08-23 1994-08-02 Pfizer Inc. Hypoglycemic hydroxyurea derivatives
TW222626B (OSRAM) 1991-07-22 1994-04-21 Pfizer
US5498621A (en) * 1992-05-01 1996-03-12 Pfizer Inc. Oxazolidinedione hypoglycemic agents
US5401761A (en) * 1993-12-09 1995-03-28 Pfizer, Inc. Thiazolidinedione hypoglycemic agents
US5925656A (en) * 1995-04-10 1999-07-20 Dr. Reddy's Research Foundation Compounds having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
GB9604242D0 (en) 1996-02-28 1996-05-01 Glaxo Wellcome Inc Chemical compounds
US5889025A (en) * 1996-05-06 1999-03-30 Reddy's Research Foundation Antidiabetic compounds having hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
US5919782A (en) * 1996-05-06 1999-07-06 Dr. Reddy's Research Foundation Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
US5801173A (en) * 1996-05-06 1998-09-01 Dr. Reddy's Research Foundation Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
ZA973848B (en) * 1996-05-06 1997-12-02 Reddy Research Foundation Novel heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them.
US6372750B2 (en) * 1996-07-01 2002-04-16 Dr. Reddy's Research Foundation Heterocyclic compounds, process for their preparation and pharmaceutical compounds containing them and their use in the treatment of diabetes and related diseases
USRE39266E1 (en) * 1996-07-01 2006-09-05 Dr. Reddy's Laboratories, Limited Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
US6114526A (en) * 1996-07-01 2000-09-05 Dr. Reddy's Research Foundation Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
BR9711098B1 (pt) 1996-07-01 2011-10-04 compostos heterocìclicos, processo para sua preparação e composições farmacêuticas contendo os mesmos e seu uso no tratamento de diabetes e doenças relacionadas.
ID27787A (id) * 1998-08-21 2001-04-26 Viro Pharma Inc Senyawa, komposisi dan metode untuk pengobatan atau pencegahan infeksi yang disebabkan oleh virus dan penyakit-penyakit yang berkaitan
WO2000018745A1 (en) * 1998-09-30 2000-04-06 Roche Diagnostics Gmbh Oxazolidine derivatives for the treatment and prevention of metabolic bone disorders
CA2377246A1 (en) 1999-06-18 2000-12-28 Ranjit C. Desai Arylthiazolidinedione and aryloxazolidinedione derivatives
CA2376919C (en) 1999-06-18 2008-11-04 Merck & Co., Inc. Arylthiazolidinedione and aryloxazolidinedione derivatives
TW200901959A (en) 2007-03-09 2009-01-16 Indigene Pharmaceuticals Inc Combination of metformin R-(+) lipoate and antihyperlipidemic agents for the treatment of diabetic hyperglycemia and diabetic complications
JP5417860B2 (ja) * 2008-08-26 2014-02-19 住友化学株式会社 α−ヒドロキシエステル類の製造方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE729852C (de) * 1939-07-06 1943-01-04 Carl Nachtigall Verfahren zur Herstellung von 2, 4-Dioxooxazolidinen
US2338220A (en) * 1942-01-31 1944-01-04 Mallinckrodt Chemical Works Process of making oxazolidinediones
US2721197A (en) * 1953-01-05 1955-10-18 Bristol Lab Inc Bicyclic lactams
US2961377A (en) * 1957-08-05 1960-11-22 Us Vitamin Pharm Corp Oral anti-diabetic compositions and methods
FR1284516A (fr) * 1957-11-20 1962-02-16 France Etat Produits utilisables notamment comme agents susceptibles d'agir sur la croissance des plantes et leur procédé de fabrication
GB1227428A (OSRAM) * 1968-04-08 1971-04-07
US3699229A (en) * 1970-12-18 1972-10-17 Abbott Lab 2-oxo-5-phenyl-4-oxazolidinone as an anti-depressant agent
AT322266B (de) * 1972-11-06 1975-05-12 Rath Karl Friedrich Vorrichtung zum einsetzen von pflanzen
FR2207706B1 (OSRAM) * 1972-11-24 1975-11-28 Orsymonde
DE2813873A1 (de) * 1978-03-31 1979-10-11 Basf Ag Verfahren zur herstellung von oxazolidin-2,4-dionen
US4200642A (en) * 1978-08-21 1980-04-29 Pfizer Inc. Spiro-oxazolidindiones

Also Published As

Publication number Publication date
NO812558L (no) 1982-01-29
FI77457C (fi) 1989-03-10
SE460849B (sv) 1989-11-27
ES514665A0 (es) 1983-05-01
YU88283A (en) 1983-12-31
GB2128987B (en) 1984-09-26
ES514666A0 (es) 1983-05-01
ES8306367A1 (es) 1983-05-16
DK334681A (da) 1982-03-05
IL63422A0 (en) 1981-10-30
DK151882C (da) 1988-06-06
KR830006247A (ko) 1983-09-20
KR850000382B1 (ko) 1985-03-23
KR850003290A (ko) 1985-06-13
HU185682B (en) 1985-03-28
GB2132609A (en) 1984-07-11
GB8317145D0 (en) 1983-07-27
NL8103536A (nl) 1982-02-16
IT1138110B (it) 1986-09-17
IE51427B1 (en) 1986-12-24
KR850000387B1 (ko) 1985-03-25
NZ197853A (en) 1986-09-10
PT73437A (en) 1981-08-01
GB2132609B (en) 1985-01-03
AU526905B2 (en) 1983-02-03
KR850000381B1 (ko) 1985-03-23
CA1155855A (en) 1983-10-25
PH17421A (en) 1984-08-08
AR230834A1 (es) 1984-07-31
GB2083810B (en) 1984-03-14
PT73437B (en) 1983-09-01
GB2083810A (en) 1982-03-31
YU185281A (en) 1983-12-31
ATA328681A (de) 1984-04-15
DK151882B (da) 1988-01-11
FR2487348A1 (fr) 1982-01-29
AR231721A1 (es) 1985-02-28
IT8123175A0 (it) 1981-07-27
KR850003291A (ko) 1985-06-13
AR228061A1 (es) 1983-01-14
ES8306132A1 (es) 1983-05-01
DE3129309A1 (de) 1982-03-18
GB2128987A (en) 1984-05-10
SE8104542L (sv) 1982-01-29
CH653025A5 (fr) 1985-12-13
YU88183A (en) 1983-12-31
IE811695L (en) 1982-01-28
AT376424B (de) 1984-11-26
FI77457B (fi) 1988-11-30
US4367234A (en) 1983-01-04
GR74590B (OSRAM) 1984-06-29
GB8317144D0 (en) 1983-07-27
DE3129309C2 (OSRAM) 1987-06-19
FR2487348B1 (fr) 1986-05-02
FI812340L (fi) 1982-01-29
IL63422A (en) 1984-11-30
DD202149A5 (de) 1983-08-31
ES8306133A1 (es) 1983-05-01
ES504322A0 (es) 1983-05-16

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