CH643548A5 - Derives de 1,3-benzoxazine-2,4-dione, leur preparation et medicaments les contenant. - Google Patents
Derives de 1,3-benzoxazine-2,4-dione, leur preparation et medicaments les contenant. Download PDFInfo
- Publication number
- CH643548A5 CH643548A5 CH773579A CH773579A CH643548A5 CH 643548 A5 CH643548 A5 CH 643548A5 CH 773579 A CH773579 A CH 773579A CH 773579 A CH773579 A CH 773579A CH 643548 A5 CH643548 A5 CH 643548A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzoxazine
- dione
- formula
- chloro
- derivatives
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title claims description 5
- OAYRYNVEFFWSHK-UHFFFAOYSA-N carsalam Chemical class C1=CC=C2OC(=O)NC(=O)C2=C1 OAYRYNVEFFWSHK-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000460 chlorine Substances 0.000 claims description 16
- GBNWQQUVAPTWKO-UHFFFAOYSA-N 6-chloro-3-methyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Cl)C=C2C(=O)N(C)C(=O)OC2=C1 GBNWQQUVAPTWKO-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkyl radical Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- HKZCOWRJCWNNFP-UHFFFAOYSA-N 6-chloro-3-(furan-2-ylmethyl)-1,3-benzoxazine-2,4-dione Chemical compound O=C1C2=CC(Cl)=CC=C2OC(=O)N1CC1=CC=CO1 HKZCOWRJCWNNFP-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 claims description 2
- FNXRPOPDYIZQHW-UHFFFAOYSA-N 6-chloro-3-(2-phenoxyphenyl)-1,3-benzoxazine-2,4-dione Chemical compound O=C1C2=CC(Cl)=CC=C2OC(=O)N1C1=CC=CC=C1OC1=CC=CC=C1 FNXRPOPDYIZQHW-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JNZZLCUTRFPQPJ-UHFFFAOYSA-N 6-bromo-3-methyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Br)C=C2C(=O)N(C)C(=O)OC2=C1 JNZZLCUTRFPQPJ-UHFFFAOYSA-N 0.000 description 2
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 2
- 229920003084 Avicel® PH-102 Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229940080018 acetylcholine injection Drugs 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- IEJOONSLOGAXNO-UHFFFAOYSA-N 5-bromo-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1O IEJOONSLOGAXNO-UHFFFAOYSA-N 0.000 description 1
- GOMXAFKCHRQJPQ-UHFFFAOYSA-N 6-chloro-3-(2-thiophen-2-yloxyphenyl)-1,3-benzoxazine-2,4-dione Chemical compound ClC=1C=CC2=C(C(N(C(O2)=O)C2=C(C=CC=C2)OC=2SC=CC=2)=O)C=1 GOMXAFKCHRQJPQ-UHFFFAOYSA-N 0.000 description 1
- RUSRJCQXSADYBI-UHFFFAOYSA-N 6-chloro-3-ethyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Cl)C=C2C(=O)N(CC)C(=O)OC2=C1 RUSRJCQXSADYBI-UHFFFAOYSA-N 0.000 description 1
- OAJNFZRAWNMFEC-UHFFFAOYSA-N 6-chloro-3-propyl-1,3-benzoxazine-2,4-dione Chemical compound C1=C(Cl)C=C2C(=O)N(CCC)C(=O)OC2=C1 OAJNFZRAWNMFEC-UHFFFAOYSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241001539019 Monolene Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 229920003110 Primojel Polymers 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- ZEHGKSPCAMLJDC-UHFFFAOYSA-M acetylcholine bromide Chemical compound [Br-].CC(=O)OCC[N+](C)(C)C ZEHGKSPCAMLJDC-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229950005514 glycyclamide Drugs 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7824674A FR2434158A1 (fr) | 1978-08-25 | 1978-08-25 | Nouveaux derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643548A5 true CH643548A5 (fr) | 1984-06-15 |
Family
ID=9212085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH773579A CH643548A5 (fr) | 1978-08-25 | 1979-08-24 | Derives de 1,3-benzoxazine-2,4-dione, leur preparation et medicaments les contenant. |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5533484A (de) |
| AR (1) | AR222494A1 (de) |
| AT (1) | AT373591B (de) |
| BE (1) | BE878395A (de) |
| BG (1) | BG30929A3 (de) |
| CA (1) | CA1128511A (de) |
| CH (1) | CH643548A5 (de) |
| CS (1) | CS208131B2 (de) |
| DD (1) | DD145534A5 (de) |
| DE (1) | DE2934166A1 (de) |
| EG (1) | EG14355A (de) |
| ES (1) | ES481856A1 (de) |
| FI (1) | FI68818C (de) |
| FR (1) | FR2434158A1 (de) |
| GB (1) | GB2031410B (de) |
| GR (1) | GR69619B (de) |
| HU (1) | HU182916B (de) |
| IL (1) | IL58096A (de) |
| NL (1) | NL7906408A (de) |
| PL (1) | PL116771B1 (de) |
| PT (1) | PT70107A (de) |
| RO (1) | RO78156A (de) |
| SE (1) | SE446865B (de) |
| SU (1) | SU797576A3 (de) |
| YU (1) | YU40849B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8263657B2 (en) | 2000-12-18 | 2012-09-11 | Institute Of Medicinal Molecular Design, Inc. | Inhibitors against the production and release of inflammatory cytokines |
| CA2488363C (en) * | 2002-06-06 | 2011-01-04 | Institute Of Medicinal Molecular Design, Inc. | O-substituted hydroxyaryl derivatives |
| TW200402291A (en) | 2002-06-06 | 2004-02-16 | Inst Med Molecular Design Inc | Antiallergic |
| CN108658887B (zh) * | 2018-06-20 | 2022-04-05 | 中南大学 | 苯并[d][1,3]噁嗪-2,4(1H)-二酮衍生物及其合成方法和用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476559A (en) * | 1946-10-01 | 1949-07-19 | Gen Aniline & Film Corp | Oxazine diones |
| DE1153375B (de) * | 1960-05-25 | 1963-08-29 | Thomae Gmbh Dr K | Verfahren zur Herstellung von Benzoxazin-(1, 3)-dionen-(2, 4) |
| GB1069367A (en) * | 1964-10-01 | 1967-05-17 | Aspro Nicholas Ltd | Improvements in or relating to the production of 1:3-benzoxazine-2:4-dione |
| CH459211A (de) * | 1965-01-25 | 1968-07-15 | Robapharm Ag | Verfahren zur Herstellung von neuen basischen Derivaten des Dihydro-1,3-benzoxazin-2,4-dions |
-
1978
- 1978-08-25 FR FR7824674A patent/FR2434158A1/fr active Granted
-
1979
- 1979-06-06 ES ES481856A patent/ES481856A1/es not_active Expired
- 1979-08-21 DD DD79215096A patent/DD145534A5/de not_active IP Right Cessation
- 1979-08-22 GB GB7929266A patent/GB2031410B/en not_active Expired
- 1979-08-22 CA CA334,287A patent/CA1128511A/fr not_active Expired
- 1979-08-22 PL PL1979217893A patent/PL116771B1/pl unknown
- 1979-08-22 GR GR52886A patent/GR69619B/el unknown
- 1979-08-22 RO RO7998518A patent/RO78156A/ro unknown
- 1979-08-22 BG BG044725A patent/BG30929A3/xx unknown
- 1979-08-22 HU HU79PO694A patent/HU182916B/hu not_active IP Right Cessation
- 1979-08-23 SU SU792804596A patent/SU797576A3/ru active
- 1979-08-23 BE BE0/196852A patent/BE878395A/fr not_active IP Right Cessation
- 1979-08-23 FI FI792632A patent/FI68818C/fi not_active IP Right Cessation
- 1979-08-23 AR AR277829A patent/AR222494A1/es active
- 1979-08-23 AT AT0568379A patent/AT373591B/de not_active IP Right Cessation
- 1979-08-23 PT PT70107A patent/PT70107A/pt unknown
- 1979-08-23 IL IL58096A patent/IL58096A/xx not_active IP Right Cessation
- 1979-08-23 JP JP10764779A patent/JPS5533484A/ja active Pending
- 1979-08-23 YU YU2073/79A patent/YU40849B/xx unknown
- 1979-08-23 DE DE19792934166 patent/DE2934166A1/de not_active Ceased
- 1979-08-24 NL NL7906408A patent/NL7906408A/nl not_active Application Discontinuation
- 1979-08-24 CH CH773579A patent/CH643548A5/fr not_active IP Right Cessation
- 1979-08-24 SE SE7907067A patent/SE446865B/sv not_active IP Right Cessation
- 1979-08-24 CS CS795769A patent/CS208131B2/cs unknown
- 1979-08-27 EG EG520/79A patent/EG14355A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| IL58096A0 (en) | 1979-12-30 |
| FI68818C (fi) | 1985-11-11 |
| PT70107A (fr) | 1979-09-01 |
| AT373591B (de) | 1984-02-10 |
| PL116771B1 (en) | 1981-06-30 |
| DE2934166A1 (de) | 1980-02-28 |
| ES481856A1 (es) | 1980-02-16 |
| RO78156A (ro) | 1982-02-01 |
| GR69619B (de) | 1982-07-06 |
| GB2031410A (en) | 1980-04-23 |
| PL217893A1 (de) | 1980-04-21 |
| SE7907067L (sv) | 1980-02-26 |
| YU207379A (en) | 1983-02-28 |
| SE446865B (sv) | 1986-10-13 |
| CS208131B2 (en) | 1981-08-31 |
| JPS5533484A (en) | 1980-03-08 |
| HU182916B (en) | 1984-03-28 |
| CA1128511A (fr) | 1982-07-27 |
| FI68818B (fi) | 1985-07-31 |
| NL7906408A (nl) | 1980-02-27 |
| BE878395A (fr) | 1980-02-25 |
| FR2434158A1 (fr) | 1980-03-21 |
| SU797576A3 (ru) | 1981-01-15 |
| YU40849B (en) | 1986-06-30 |
| AR222494A1 (es) | 1981-05-29 |
| EG14355A (en) | 1983-12-31 |
| ATA568379A (de) | 1983-06-15 |
| FR2434158B1 (de) | 1985-05-03 |
| IL58096A (en) | 1982-12-31 |
| DD145534A5 (de) | 1980-12-17 |
| BG30929A3 (en) | 1981-09-15 |
| FI792632A (fi) | 1980-02-26 |
| GB2031410B (en) | 1982-12-01 |
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