SE448096B - Substituerade pyrrolo/2,1-b/kinazoliner och pyrido/2,1-b/kinazoliner och forfarande for deras framstellning - Google Patents
Substituerade pyrrolo/2,1-b/kinazoliner och pyrido/2,1-b/kinazoliner och forfarande for deras framstellningInfo
- Publication number
- SE448096B SE448096B SE8204034A SE8204034A SE448096B SE 448096 B SE448096 B SE 448096B SE 8204034 A SE8204034 A SE 8204034A SE 8204034 A SE8204034 A SE 8204034A SE 448096 B SE448096 B SE 448096B
- Authority
- SE
- Sweden
- Prior art keywords
- tetrahydro
- benzylidene
- formula
- compound
- pyrrolo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 78
- -1 methylenedioxy group Chemical group 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000002244 precipitate Substances 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 230000007935 neutral effect Effects 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 150000004702 methyl esters Chemical class 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- SRKXVESHUPPYMO-UHFFFAOYSA-N quinazoline-7-carboxylic acid Chemical compound C1=NC=NC2=CC(C(=O)O)=CC=C21 SRKXVESHUPPYMO-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- 238000001914 filtration Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 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 5
- 241000700159 Rattus Species 0.000 description 5
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- 229910052801 chlorine Inorganic materials 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
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- OKXPYKHKJCATPX-UHFFFAOYSA-N quinazoline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=NC=C21 OKXPYKHKJCATPX-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 235000015424 sodium Nutrition 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- RMZDXTBIBYDFHR-UHFFFAOYSA-N 2h-quinazoline-3-carboxylic acid Chemical compound C1=CC=CC2=CN(C(=O)O)CN=C21 RMZDXTBIBYDFHR-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16K—VALVES; TAPS; COCKS; ACTUATING-FLOATS; DEVICES FOR VENTING OR AERATING
- F16K1/00—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces
- F16K1/16—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members
- F16K1/18—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members with pivoted discs or flaps
- F16K1/22—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members with pivoted discs or flaps with axis of rotation crossing the valve member, e.g. butterfly valves
- F16K1/226—Shaping or arrangements of the sealing
- F16K1/2263—Shaping or arrangements of the sealing the sealing being arranged on the valve seat
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16K—VALVES; TAPS; COCKS; ACTUATING-FLOATS; DEVICES FOR VENTING OR AERATING
- F16K1/00—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces
- F16K1/16—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members
- F16K1/18—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members with pivoted discs or flaps
- F16K1/22—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members with pivoted discs or flaps with axis of rotation crossing the valve member, e.g. butterfly valves
- F16K1/226—Shaping or arrangements of the sealing
- F16K1/2268—Sealing means for the axis of rotation
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8120126 | 1981-06-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8204034D0 SE8204034D0 (sv) | 1982-06-29 |
| SE8204034L SE8204034L (sv) | 1982-12-31 |
| SE448096B true SE448096B (sv) | 1987-01-19 |
Family
ID=10522894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8204034A SE448096B (sv) | 1981-06-30 | 1982-06-29 | Substituerade pyrrolo/2,1-b/kinazoliner och pyrido/2,1-b/kinazoliner och forfarande for deras framstellning |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4428952A (de) |
| JP (1) | JPS588082A (de) |
| AT (2) | AT377586B (de) |
| AU (1) | AU552065B2 (de) |
| BE (1) | BE893694A (de) |
| CA (1) | CA1183135A (de) |
| CH (1) | CH657618A5 (de) |
| DE (1) | DE3224213A1 (de) |
| DK (1) | DK292782A (de) |
| FI (1) | FI73997C (de) |
| FR (1) | FR2508457B1 (de) |
| GB (1) | GB2103207B (de) |
| IL (1) | IL66146A (de) |
| IT (1) | IT1159069B (de) |
| NL (1) | NL8202602A (de) |
| SE (1) | SE448096B (de) |
| SU (1) | SU1279530A1 (de) |
| ZA (1) | ZA824502B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU553266B2 (en) * | 1982-02-04 | 1986-07-10 | Farmitalia Carlo Erba S.P.A. | Substituted 1,3,4-thiadiazolo(3,2-a) pyrimidines |
| ES8406476A1 (es) * | 1982-04-29 | 1984-07-01 | Erba Farmitalia | Procedimiento para preparar derivados cicloalifaticos condensados de pirido(1,2-a)pirimidinas sustituidas. |
| IL69274A (en) * | 1982-08-05 | 1986-08-31 | Erba Farmitalia | (substituted amino)derivatives of 3-benzylidene-pyrrolo(2,1-b)quinazolin-9-ones and 6-benzylidene-pyrido(2,1-b)quinazolin-11-ones,their preparation and pharmaceutical compositions containing them |
| JPH06509576A (ja) * | 1991-07-29 | 1994-10-27 | ワーナー−ランバート・コンパニー | アセチルコリンエステラーゼ阻害剤としてのキナゾリン誘導体 |
| JP2003535865A (ja) * | 2000-06-07 | 2003-12-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | カスパーゼインヒビターおよびその使用 |
| BR112020001698A2 (pt) * | 2017-08-03 | 2020-07-21 | Galectin Sciences, Llc | compostos para prevenção e tratamento de distúrbios médicos e usos dos mesmos |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992221A (en) * | 1958-07-03 | 1961-07-11 | Petersen Siegfried | Polymethylene-oxoquinazolines and their production |
| US3271396A (en) | 1964-08-17 | 1966-09-06 | Squibb & Sons Inc | Pyrido-quinazoline derivatives |
| DE1670416A1 (de) | 1966-12-30 | 1971-02-11 | Chem Fab Von Heyden Gmbh Muenc | Verfahren zur Herstellung von aminosubstituierten Chinazolinonderivaten |
| HU174693B (hu) | 1976-02-12 | 1980-03-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija kondensirovannykh proizvodnykh pirimidina |
| DE2739020A1 (de) | 1977-08-26 | 1979-03-01 | Schering Ag | Pyrido eckige klammer auf 2,1-b eckige klammer zu -chinazolinon-derivate, ihre herstellung und verwendung |
| US4310526A (en) | 1979-05-08 | 1982-01-12 | Farmitalia Carlo Erba S.P.A. | Substituted 6,7-methylene pyrido[1,2-a]pyrimidines useful as anti-allergic and anti-ulcer agents |
| HU183173B (en) * | 1980-06-24 | 1984-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 6-hydrazono-pyrido-aracket-2,1-b-bracket closed-quinazolin-11-ones |
-
1978
- 1978-10-30 AT AT0775378A patent/AT377586B/de not_active IP Right Cessation
-
1982
- 1982-06-10 US US06/387,181 patent/US4428952A/en not_active Expired - Fee Related
- 1982-06-16 AU AU84922/82A patent/AU552065B2/en not_active Ceased
- 1982-06-18 CH CH3785/82A patent/CH657618A5/de not_active IP Right Cessation
- 1982-06-23 IT IT22005/82A patent/IT1159069B/it active
- 1982-06-24 ZA ZA824502A patent/ZA824502B/xx unknown
- 1982-06-25 AT AT0247582A patent/AT381092B/de not_active IP Right Cessation
- 1982-06-28 IL IL66146A patent/IL66146A/xx unknown
- 1982-06-28 GB GB08218609A patent/GB2103207B/en not_active Expired
- 1982-06-28 NL NL8202602A patent/NL8202602A/nl not_active Application Discontinuation
- 1982-06-29 SE SE8204034A patent/SE448096B/sv not_active IP Right Cessation
- 1982-06-29 JP JP57110921A patent/JPS588082A/ja active Pending
- 1982-06-29 SU SU823459054A patent/SU1279530A1/ru active
- 1982-06-29 DK DK292782A patent/DK292782A/da not_active Application Discontinuation
- 1982-06-29 CA CA000406308A patent/CA1183135A/en not_active Expired
- 1982-06-29 DE DE19823224213 patent/DE3224213A1/de not_active Withdrawn
- 1982-06-29 BE BE0/208486A patent/BE893694A/fr not_active IP Right Cessation
- 1982-06-30 FI FI822329A patent/FI73997C/fi not_active IP Right Cessation
- 1982-06-30 FR FR8211493A patent/FR2508457B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT377586B (de) | 1985-04-10 |
| AU552065B2 (en) | 1986-05-22 |
| SU1279530A3 (ru) | 1986-12-23 |
| IL66146A (en) | 1985-12-31 |
| CH657618A5 (de) | 1986-09-15 |
| FI822329A0 (fi) | 1982-06-30 |
| JPS588082A (ja) | 1983-01-18 |
| SE8204034D0 (sv) | 1982-06-29 |
| ATA775378A (de) | 1984-08-15 |
| ZA824502B (en) | 1983-04-27 |
| NL8202602A (nl) | 1983-01-17 |
| IT8222005A0 (it) | 1982-06-23 |
| FR2508457A1 (fr) | 1982-12-31 |
| DE3224213A1 (de) | 1983-01-27 |
| AU8492282A (en) | 1983-01-06 |
| CA1183135A (en) | 1985-02-26 |
| DK292782A (da) | 1982-12-31 |
| BE893694A (fr) | 1982-12-29 |
| FR2508457B1 (fr) | 1985-08-30 |
| SU1279530A1 (ru) | 1986-12-23 |
| AT381092B (de) | 1986-08-25 |
| GB2103207A (en) | 1983-02-16 |
| FI73997B (fi) | 1987-08-31 |
| FI73997C (fi) | 1987-12-10 |
| IT1159069B (it) | 1987-02-25 |
| SE8204034L (sv) | 1982-12-31 |
| IL66146A0 (en) | 1982-09-30 |
| GB2103207B (en) | 1985-01-09 |
| US4428952A (en) | 1984-01-31 |
| ATA247582A (de) | 1986-01-15 |
| FI822329L (fi) | 1982-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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