NL8001545A - Isoindoline derivaat, werkwijze voor zijn bereiding en therapeutische preparaten welke deze stof bevatten. - Google Patents

Isoindoline derivaat, werkwijze voor zijn bereiding en therapeutische preparaten welke deze stof bevatten. Download PDF

Info

Publication number: NL8001545A
Authority: NL; Netherlands
Prior art keywords: methyl; isoindoline; tert; chloro; animals
Prior art date: 1979-03-15

Application number

NL8001545A

Other languages

English (en)

Dutch (nl)

Original Assignee

Farmatis Spa

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.)

1979-03-15

Filing date

1980-03-14

Publication date

1980-09-17

1980-03-14 Application filed by Farmatis Spa filed Critical Farmatis Spa

1980-09-17 Publication of NL8001545A publication Critical patent/NL8001545A/nl

Links

238000000034 method Methods 0.000 title claims description 12
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 8
230000001225 therapeutic effect Effects 0.000 title description 4
239000000126 substance Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 21
230000001882 diuretic effect Effects 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
239000002934 diuretic Substances 0.000 claims description 10
230000000894 saliuretic effect Effects 0.000 claims description 8
150000007530 organic bases Chemical class 0.000 claims description 7
QHCAOYAJCBJOLE-UHFFFAOYSA-N 1-methyl-1,3-dihydroisoindol-2-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(C)N(N)CC2=C1 QHCAOYAJCBJOLE-UHFFFAOYSA-N 0.000 claims description 5
230000003276 anti-hypertensive effect Effects 0.000 claims description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
239000003495 polar organic solvent Substances 0.000 claims description 4
BHUKYXOYJMLRAK-UHFFFAOYSA-N 4-chloro-n-(1-methyl-1,3-dihydroisoindol-2-yl)-3-sulfamoylbenzamide Chemical compound C1C2=CC=CC=C2C(C)N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 BHUKYXOYJMLRAK-UHFFFAOYSA-N 0.000 claims description 3
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
238000003756 stirring Methods 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
239000000654 additive Substances 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
241001465754 Metazoa Species 0.000 description 32
NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 description 21
241000700159 Rattus Species 0.000 description 20
229960004569 indapamide Drugs 0.000 description 20
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 19
229910052700 potassium Inorganic materials 0.000 description 19
239000011591 potassium Substances 0.000 description 19
239000000243 solution Substances 0.000 description 15
239000000047 product Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
239000011734 sodium Substances 0.000 description 12
210000002700 urine Anatomy 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
230000037396 body weight Effects 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000003304 gavage Methods 0.000 description 9
230000036772 blood pressure Effects 0.000 description 7
239000000203 mixture Substances 0.000 description 7
229920000084 Gum arabic Polymers 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241000978776 Senegalia senegal Species 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000205 acacia gum Substances 0.000 description 6
235000010489 acacia gum Nutrition 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
210000000936 intestine Anatomy 0.000 description 5
210000002784 stomach Anatomy 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
RRCYYLHJWRYWEI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOO RRCYYLHJWRYWEI-UHFFFAOYSA-N 0.000 description 4
241000700157 Rattus norvegicus Species 0.000 description 4
230000002503 metabolic effect Effects 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
230000004872 arterial blood pressure Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
230000029142 excretion Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
210000004400 mucous membrane Anatomy 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 2
JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 2
208000004880 Polyuria Diseases 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
-1 amino compound Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000035619 diuresis Effects 0.000 description 2
229940030606 diuretics Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 1
NOVIRODZMIZUPA-UHFFFAOYSA-N 2,3-dihydro-1h-isoindole;hydrochloride Chemical compound Cl.C1=CC=C2CNCC2=C1 NOVIRODZMIZUPA-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
241000772991 Aira Species 0.000 description 1
108010082126 Alanine transaminase Proteins 0.000 description 1
108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
208000037157 Azotemia Diseases 0.000 description 1
235000007575 Calluna vulgaris Nutrition 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
206010020565 Hyperaemia Diseases 0.000 description 1
208000029422 Hypernatremia Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
241001024304 Mino Species 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
229910006074 SO2NH2 Inorganic materials 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
231100000460 acute oral toxicity Toxicity 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
208000037849 arterial hypertension Diseases 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
238000009530 blood pressure measurement Methods 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
238000004737 colorimetric analysis Methods 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
208000002173 dizziness Diseases 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
208000036796 hyperbilirubinemia Diseases 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000001452 natriuretic effect Effects 0.000 description 1
230000008693 nausea Effects 0.000 description 1
230000009826 neoplastic cell growth Effects 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
238000001050 pharmacotherapy Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000028327 secretion Effects 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
231100000456 subacute toxicity Toxicity 0.000 description 1
231100000064 subacute toxicity study Toxicity 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000003867 tiredness Effects 0.000 description 1
208000016255 tiredness Diseases 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
230000001228 trophic effect Effects 0.000 description 1
230000036269 ulceration Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

NL8001545A 1979-03-15 1980-03-14 Isoindoline derivaat, werkwijze voor zijn bereiding en therapeutische preparaten welke deze stof bevatten. NL8001545A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT20991/79A IT1113879B (it)	1979-03-15	1979-03-15	Derivato isoindolinico,processo per la sua preparazione e composizioni terapeutiche che lo comprendono come principio attivo
IT2099179		1979-03-15

Publications (1)

Publication Number	Publication Date
NL8001545A true NL8001545A (nl)	1980-09-17

Family

ID=11175061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8001545A NL8001545A (nl)	1979-03-15	1980-03-14	Isoindoline derivaat, werkwijze voor zijn bereiding en therapeutische preparaten welke deze stof bevatten.

Country Status (17)

Country	Link
US (1)	US4338331A (el)
JP (1)	JPS55127369A (el)
AT (1)	AT374179B (el)
AU (1)	AU533082B2 (el)
BE (1)	BE882239A (el)
CA (1)	CA1117130A (el)
CS (1)	CS210641B2 (el)
DE (1)	DE3009932C2 (el)
ES (1)	ES8102554A1 (el)
FR (1)	FR2451365A1 (el)
GB (1)	GB2047241B (el)
GR (1)	GR66632B (el)
IT (1)	IT1113879B (el)
NL (1)	NL8001545A (el)
SE (1)	SE8002001L (el)
YU (1)	YU70080A (el)
ZA (1)	ZA801426B (el)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2654726B1 (fr) *	1989-11-23	1992-02-14	Rhone Poulenc Sante	Nouveaux derives de l'isoindolone et leur preparation.
RU2191572C1 (ru) *	2001-09-26	2002-10-27	Нестерук Владимир Викторович	Диуретическое и гипотензивное средство в виде таблетки

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL129208C (el) *	1965-07-14
GB1193289A (en) *	1965-07-14	1970-05-28	Science Union & Cie	New Isoindolino-Sulphonylurea Derivatives and Process for Preparing them
FR1557903A (el) *	1968-01-09	1969-02-21
GB1203691A (en) *	1968-03-06	1970-09-03	Science Union & Cie	New disubstituted n-amino indoline derivatives and process for preparing them
CH603581A5 (el) *	1974-03-29	1978-08-31	Siegfried Ag
US4178293A (en) *	1978-04-14	1979-12-11	Zoecon Corporation	Isoindolinyl derivatives

1979
- 1979-03-15 IT IT20991/79A patent/IT1113879B/it active
1980
- 1980-03-11 ZA ZA00801426A patent/ZA801426B/xx unknown
- 1980-03-12 GB GB8008368A patent/GB2047241B/en not_active Expired
- 1980-03-12 FR FR8005504A patent/FR2451365A1/fr active Granted
- 1980-03-13 AT AT0139780A patent/AT374179B/de not_active IP Right Cessation
- 1980-03-13 CS CS801738A patent/CS210641B2/cs unknown
- 1980-03-13 AU AU56407/80A patent/AU533082B2/en not_active Expired - Fee Related
- 1980-03-13 GR GR61432A patent/GR66632B/el unknown
- 1980-03-14 BE BE0/199808A patent/BE882239A/fr not_active IP Right Cessation
- 1980-03-14 ES ES489539A patent/ES8102554A1/es not_active Expired
- 1980-03-14 YU YU00700/80A patent/YU70080A/xx unknown
- 1980-03-14 CA CA000347681A patent/CA1117130A/en not_active Expired
- 1980-03-14 NL NL8001545A patent/NL8001545A/nl not_active Application Discontinuation
- 1980-03-14 DE DE3009932A patent/DE3009932C2/de not_active Expired
- 1980-03-14 SE SE8002001A patent/SE8002001L/xx not_active Application Discontinuation
- 1980-03-14 JP JP3171380A patent/JPS55127369A/ja active Pending
1981
- 1981-01-09 US US06/223,798 patent/US4338331A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IT7920991A0 (it)	1979-03-15
IT1113879B (it)	1986-01-27
ES489539A0 (es)	1981-02-16
GB2047241B (en)	1983-01-26
AT374179B (de)	1984-03-26
CS210641B2 (en)	1982-01-29
AU533082B2 (en)	1983-10-27
US4338331A (en)	1982-07-06
YU70080A (en)	1983-01-21
ATA139780A (de)	1983-08-15
CA1117130A (en)	1982-01-26
GB2047241A (en)	1980-11-26
FR2451365A1 (fr)	1980-10-10
ES8102554A1 (es)	1981-02-16
AU5640780A (en)	1980-09-18
SE8002001L (sv)	1980-09-16
FR2451365B1 (el)	1983-03-11
ZA801426B (en)	1980-12-31
BE882239A (fr)	1980-07-01
GR66632B (el)	1981-04-03
JPS55127369A (en)	1980-10-02
DE3009932C2 (de)	1983-04-07
DE3009932A1 (de)	1980-09-25

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