CA1154763A - In 5-position substituted 5,10-dihydro-11h- dibenzo[b,e][1,4] diazepine-11-ones, processes for their preparation, and pharmaceutical compositions containing these compounds - Google Patents
In 5-position substituted 5,10-dihydro-11h- dibenzo[b,e][1,4] diazepine-11-ones, processes for their preparation, and pharmaceutical compositions containing these compoundsInfo
- Publication number
- CA1154763A CA1154763A CA000382372A CA382372A CA1154763A CA 1154763 A CA1154763 A CA 1154763A CA 000382372 A CA000382372 A CA 000382372A CA 382372 A CA382372 A CA 382372A CA 1154763 A CA1154763 A CA 1154763A
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- dibenzo
- compound
- group
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims description 30
- 230000008569 process Effects 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title description 10
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- KVVFXAAMMFTLGN-UHFFFAOYSA-N 5,11-dihydrobenzo[b][1,4]benzodiazepin-6-one Chemical class O=C1NC2=CC=CC=C2NC2=CC=CC=C12 KVVFXAAMMFTLGN-UHFFFAOYSA-N 0.000 title 1
- -1 pyrrolidino, piperidino, 2-methyl-piperidino, 2-ethyl-piperidino, 2,6-dimethylpiperidino Chemical group 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 229910052801 chlorine Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 20
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
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- 239000000126 substance Substances 0.000 claims description 7
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- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 4
- LEGYNZZRECSDDJ-UHFFFAOYSA-N 11-(3-chloropropanoyl)-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2N(C(=O)CCCl)C2=CC=CC=C21 LEGYNZZRECSDDJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- QPHUWSLVGFCPLN-UHFFFAOYSA-N 11-(3-chloropropanoyl)-5-methylbenzo[b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CC=C2N(C(=O)CCCl)C2=CC=CC=C21 QPHUWSLVGFCPLN-UHFFFAOYSA-N 0.000 claims 1
- JGZLXFZEFXOFNM-UHFFFAOYSA-N 11-(3-piperidin-1-ylpropanoyl)-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound C12=CC=CC=C2NC(=O)C2=CC=CC=C2N1C(=O)CCN1CCCCC1 JGZLXFZEFXOFNM-UHFFFAOYSA-N 0.000 claims 1
- AMMHEQDHXGTZNN-UHFFFAOYSA-N 5-methyl-11-(3-pyrrolidin-1-ylpropanoyl)benzo[b][1,4]benzodiazepin-6-one Chemical compound C12=CC=CC=C2C(=O)N(C)C2=CC=CC=C2N1C(=O)CCN1CCCC1 AMMHEQDHXGTZNN-UHFFFAOYSA-N 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 14
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- 241001465754 Metazoa Species 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
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- 239000003995 emulsifying agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Photoreceptors In Electrophotography (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3028001.4 | 1980-07-24 | ||
| DE19803028001 DE3028001A1 (de) | 1980-07-24 | 1980-07-24 | Neue, in 5-stellung substituierte 5,10-dihydro-11h-dibenzo (b,e)(1,4) diazepin-11-one, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1154763A true CA1154763A (en) | 1983-10-04 |
Family
ID=6107969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000382372A Expired CA1154763A (en) | 1980-07-24 | 1981-07-23 | In 5-position substituted 5,10-dihydro-11h- dibenzo[b,e][1,4] diazepine-11-ones, processes for their preparation, and pharmaceutical compositions containing these compounds |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4377576A (en, 2012) |
| EP (1) | EP0044989B1 (en, 2012) |
| JP (1) | JPS5756470A (en, 2012) |
| AT (1) | ATE3548T1 (en, 2012) |
| AU (1) | AU543677B2 (en, 2012) |
| CA (1) | CA1154763A (en, 2012) |
| DD (1) | DD202023A5 (en, 2012) |
| DE (2) | DE3028001A1 (en, 2012) |
| DK (1) | DK326481A (en, 2012) |
| ES (1) | ES8301224A1 (en, 2012) |
| FI (1) | FI67697C (en, 2012) |
| GB (1) | GB2081264B (en, 2012) |
| GR (1) | GR75281B (en, 2012) |
| HU (1) | HU187340B (en, 2012) |
| IL (1) | IL63381A0 (en, 2012) |
| NO (1) | NO812529L (en, 2012) |
| NZ (1) | NZ197809A (en, 2012) |
| PH (1) | PH16815A (en, 2012) |
| PT (1) | PT73402B (en, 2012) |
| YU (1) | YU182581A (en, 2012) |
| ZA (1) | ZA815043B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3204158A1 (de) * | 1982-02-06 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | "substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel" |
| DE3204157A1 (de) * | 1982-02-06 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| DE3204403A1 (de) | 1982-02-09 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| IT1212743B (it) * | 1983-05-17 | 1989-11-30 | Dompe Farmaceutici Spa | Sali quaternari di derivati di benzo[ 1,4 ]diazepinonici,pirido [1,4]benzodiazepinonici,prido [1,5]benzodiazepinonici e loro atti vita' farmacologica |
| IT1212742B (it) * | 1983-05-17 | 1989-11-30 | Dompe Farmaceutici Spa | Derivati dibenzo [1,4]diazepinonici pirido [1,4] benzodiazepinonici,pirido [1,5] benzodiazepinonici e loro attivita' farmacologica |
| DD236731B3 (de) * | 1983-10-19 | 1992-12-10 | Dresden Arzneimittel | Verfahren zur herstellung von neuen in 5-stellung substituierten 5,10-dihydro-11h-dibenzo|b,e¨|1,4¨diazepin-11-onen |
| DE3409237A1 (de) * | 1984-03-14 | 1985-09-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3531682A1 (de) * | 1985-09-05 | 1987-03-12 | Thomae Gmbh Dr K | (+)-6-chlor-5,10-dihydro-5-((1-methyl-4- piperidinyl)acetyl)-11h-dibenzo(b,e)(1,4) diazepin-11-on, seine isolierung und verwendung als arzneimittel |
| DE3643666A1 (de) * | 1986-12-20 | 1988-06-30 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DD293582A5 (de) * | 1989-07-31 | 1991-09-05 | Arzneimittelwerk Dresden,De | Neue 5-(omega-aminoacyl)-5,10-dihydro-11h-dibenzo/b,e//1,4/-diazepin-11-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US6277592B1 (en) | 1996-07-31 | 2001-08-21 | Purina Mills, Inc. | Porcine leptin protein, nucleic acid sequences coding therefor and uses thereof |
| US6297027B1 (en) | 1996-07-31 | 2001-10-02 | Purina Mills, Inc. | Bovine leptin protein, nucleic acid sequences coding therefor and uses thereof |
| WO2007056388A2 (en) * | 2005-11-07 | 2007-05-18 | The General Hospital Corporation | Compositions and methods for modulating poly (adp-ribose) polymerase activity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI49509C (fi) * | 1968-08-20 | 1975-07-10 | Thomae Gmbh Dr K | Menetelmä farmakologisesti vaikuttavien 5-asemaan substituoitujen 5,10 -dihydro-11H-dibentso/b,e//1,4/deatsepiini-11-onien ja niiden suolojen valmistamiseksi. |
| DE1931487C3 (de) * | 1969-06-20 | 1975-12-18 | Dr. Karl Thomae Gmbh, 7950 Biberach | In 5-Stellung substituierte 5,10-Dihydro-11H-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11 -one und Verfahren zu ihrer Herstellung |
| DE1795176C3 (de) * | 1968-08-20 | 1974-10-24 | Dr. Karl Thomae Gmbh, 7950 Biberach | hT-substituierte 5-Aminoacetyl-5,10-dihydro-l lH-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11one und Verfahren zu ihrer Herstellung |
-
1980
- 1980-07-24 DE DE19803028001 patent/DE3028001A1/de not_active Withdrawn
-
1981
- 1981-07-11 AT AT81105421T patent/ATE3548T1/de not_active IP Right Cessation
- 1981-07-11 EP EP81105421A patent/EP0044989B1/de not_active Expired
- 1981-07-11 DE DE8181105421T patent/DE3160360D1/de not_active Expired
- 1981-07-13 US US06/282,501 patent/US4377576A/en not_active Expired - Fee Related
- 1981-07-17 DD DD81231897A patent/DD202023A5/de unknown
- 1981-07-20 PT PT73402A patent/PT73402B/pt unknown
- 1981-07-20 GR GR65563A patent/GR75281B/el unknown
- 1981-07-20 JP JP56113421A patent/JPS5756470A/ja active Pending
- 1981-07-22 DK DK326481A patent/DK326481A/da not_active Application Discontinuation
- 1981-07-22 IL IL63381A patent/IL63381A0/xx unknown
- 1981-07-22 YU YU01825/81A patent/YU182581A/xx unknown
- 1981-07-23 NZ NZ197809A patent/NZ197809A/xx unknown
- 1981-07-23 AU AU73370/81A patent/AU543677B2/en not_active Expired - Fee Related
- 1981-07-23 ZA ZA815043A patent/ZA815043B/xx unknown
- 1981-07-23 CA CA000382372A patent/CA1154763A/en not_active Expired
- 1981-07-23 PH PH25957A patent/PH16815A/en unknown
- 1981-07-23 NO NO812529A patent/NO812529L/no unknown
- 1981-07-23 HU HU812160A patent/HU187340B/hu unknown
- 1981-07-23 FI FI812321A patent/FI67697C/fi not_active IP Right Cessation
- 1981-07-23 ES ES504206A patent/ES8301224A1/es not_active Expired
- 1981-07-23 GB GB8122782A patent/GB2081264B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2081264B (en) | 1984-01-25 |
| NO812529L (no) | 1982-01-25 |
| PH16815A (en) | 1984-03-06 |
| GB2081264A (en) | 1982-02-17 |
| FI67697B (fi) | 1985-01-31 |
| EP0044989B1 (de) | 1983-05-25 |
| PT73402B (de) | 1983-06-15 |
| ES504206A0 (es) | 1982-11-16 |
| DE3160360D1 (en) | 1983-07-07 |
| JPS5756470A (en) | 1982-04-05 |
| PT73402A (de) | 1981-08-01 |
| EP0044989A1 (de) | 1982-02-03 |
| AU543677B2 (en) | 1985-04-26 |
| ES8301224A1 (es) | 1982-11-16 |
| US4377576A (en) | 1983-03-22 |
| IL63381A0 (en) | 1981-10-30 |
| AU7337081A (en) | 1982-01-28 |
| HU187340B (en) | 1985-12-28 |
| NZ197809A (en) | 1983-06-14 |
| FI67697C (fi) | 1985-05-10 |
| YU182581A (en) | 1984-02-29 |
| DK326481A (da) | 1982-01-25 |
| ATE3548T1 (de) | 1983-06-15 |
| ZA815043B (en) | 1983-03-30 |
| FI812321L (fi) | 1982-01-25 |
| DD202023A5 (de) | 1983-08-24 |
| DE3028001A1 (de) | 1982-02-18 |
| GR75281B (en, 2012) | 1984-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |