CH651833A5 - Pyrido(1,4)benzodiazepines phenyl-substituees methanones correspondantes et medicaments les contenant. - Google Patents
Pyrido(1,4)benzodiazepines phenyl-substituees methanones correspondantes et medicaments les contenant. Download PDFInfo
- Publication number
- CH651833A5 CH651833A5 CH2288/82A CH228882A CH651833A5 CH 651833 A5 CH651833 A5 CH 651833A5 CH 2288/82 A CH2288/82 A CH 2288/82A CH 228882 A CH228882 A CH 228882A CH 651833 A5 CH651833 A5 CH 651833A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrido
- phenyl
- amino
- benzodiazepine
- propanamine
- Prior art date
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- 229940049706 benzodiazepine Drugs 0.000 title claims description 29
- 239000003814 drug Substances 0.000 title claims 5
- 150000001557 benzodiazepines Chemical class 0.000 title description 3
- -1 N, N-dimethyl-6-phenyl-1H-pyrido- [2,3-b] - [1,4] -benzodiazepine- 11-ethanamine Chemical compound 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 87
- 229910052757 nitrogen Inorganic materials 0.000 claims description 86
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 59
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 52
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 14
- WUFWBVLAMURTLR-UHFFFAOYSA-N 6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine Chemical compound N=1C2=CC=CN=C2NC2=CC=CC=C2C=1C1=CC=CC=C1 WUFWBVLAMURTLR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 9
- RYCQVMPEIVZMII-UHFFFAOYSA-N 11h-pyrido[2,3-b][1,4]benzodiazepine Chemical compound C1=NC2=CC=CN=C2NC2=CC=CC=C21 RYCQVMPEIVZMII-UHFFFAOYSA-N 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 claims description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000020401 Depressive disease Diseases 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- ALNYFJCONXXPNA-UHFFFAOYSA-N [2-[(3-aminopyridin-2-yl)amino]phenyl]-(4-fluorophenyl)methanone Chemical compound NC1=CC=CN=C1NC1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 ALNYFJCONXXPNA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 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 description 4
- MHKLFRMMDOUFTE-UHFFFAOYSA-N [2-[(3-aminopyridin-2-yl)amino]phenyl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound NC1=CC=CN=C1NC1=CC=CC=C1C(=O)C1=CC=CC(C(F)(F)F)=C1 MHKLFRMMDOUFTE-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- ZKZOPKIJENNGNH-UHFFFAOYSA-N 6-(4-chlorophenyl)-11H-pyrido[2,3-b][1,4]benzodiazepine Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC=CN=C2NC2=CC=CC=C12 ZKZOPKIJENNGNH-UHFFFAOYSA-N 0.000 claims description 2
- WPIWBUGGJBCRMB-UHFFFAOYSA-N 6-(4-fluorophenyl)-11H-pyrido[2,3-b][1,4]benzodiazepine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC=CN=C2NC2=CC=CC=C12 WPIWBUGGJBCRMB-UHFFFAOYSA-N 0.000 claims description 2
- KUORZWTVGDBHBR-UHFFFAOYSA-N 6-(4-methylphenyl)-11H-pyrido[2,3-b][1,4]benzodiazepine Chemical compound C1=CC(C)=CC=C1C1=NC2=CC=CN=C2NC2=CC=CC=C12 KUORZWTVGDBHBR-UHFFFAOYSA-N 0.000 claims description 2
- OCWGEIWZCDZNQX-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-6,11-dihydro-5h-pyrido[2,3-b][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2NC2=NC=CC=C2NC1C1=CC=CC=C1Cl OCWGEIWZCDZNQX-UHFFFAOYSA-N 0.000 claims description 2
- OJNKGLCGQGJFRJ-UHFFFAOYSA-N [2-[(3-aminopyridin-2-yl)amino]phenyl]-(3-chlorophenyl)methanone Chemical compound NC1=CC=CN=C1NC1=CC=CC=C1C(=O)C1=CC=CC(Cl)=C1 OJNKGLCGQGJFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- CGZOELPTETZMTJ-UHFFFAOYSA-N 3-[6-(4-methoxyphenyl)pyrido[2,3-b][1,4]benzodiazepin-11-yl]-n,n-dimethylpropan-1-amine Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=CN=C2N(CCCN(C)C)C2=CC=CC=C12 CGZOELPTETZMTJ-UHFFFAOYSA-N 0.000 claims 1
- GQCRQJCSOBMDBQ-UHFFFAOYSA-N 6-(4-methoxyphenyl)-11H-pyrido[2,3-b][1,4]benzodiazepine Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=CN=C2NC2=CC=CC=C12 GQCRQJCSOBMDBQ-UHFFFAOYSA-N 0.000 claims 1
- BZIZLNVGYWUQCE-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-11-methylpyrido[2,3-b][1,4]benzodiazepine Chemical compound N=1C2=CC=CN=C2N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl BZIZLNVGYWUQCE-UHFFFAOYSA-N 0.000 claims 1
- NCVDGWAAFROCBX-UHFFFAOYSA-N [2-[(3-aminopyridin-2-yl)amino]-4-chlorophenyl]-phenylmethanone Chemical compound NC1=CC=CN=C1NC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 NCVDGWAAFROCBX-UHFFFAOYSA-N 0.000 claims 1
- DTSZGOYWJREPIZ-UHFFFAOYSA-N [2-[(3-aminopyridin-2-yl)amino]-5-chlorophenyl]-(2-chlorophenyl)methanone Chemical compound NC1=CC=CN=C1NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl DTSZGOYWJREPIZ-UHFFFAOYSA-N 0.000 claims 1
- MVGZNJBYLCBMQG-UHFFFAOYSA-N [2-[(3-aminopyridin-2-yl)amino]phenyl]-(3-fluorophenyl)methanone Chemical compound NC1=CC=CN=C1NC1=CC=CC=C1C(=O)C1=CC=CC(F)=C1 MVGZNJBYLCBMQG-UHFFFAOYSA-N 0.000 claims 1
- JKOYHSGPAKBGAG-UHFFFAOYSA-N [2-[(3-aminopyridin-2-yl)amino]phenyl]-phenylmethanone Chemical compound NC1=CC=CN=C1NC1=CC=CC=C1C(=O)C1=CC=CC=C1 JKOYHSGPAKBGAG-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- RQVMHYTXWPYJBW-UHFFFAOYSA-N n,n-diethyl-3-(6-phenylpyrido[2,3-b][1,4]benzodiazepin-11-yl)propan-1-amine Chemical compound N=1C2=CC=CN=C2N(CCCN(CC)CC)C2=CC=CC=C2C=1C1=CC=CC=C1 RQVMHYTXWPYJBW-UHFFFAOYSA-N 0.000 claims 1
- SSKCKXFBESPLGT-UHFFFAOYSA-N n,n-dimethyl-2-(6-phenylpyrido[2,3-b][1,4]benzodiazepin-11-yl)ethanamine Chemical compound N=1C2=CC=CN=C2N(CCN(C)C)C2=CC=CC=C2C=1C1=CC=CC=C1 SSKCKXFBESPLGT-UHFFFAOYSA-N 0.000 claims 1
- OIVGIIWPZYHINE-UHFFFAOYSA-N n,n-dimethyl-3-(6-phenyl-5,6-dihydropyrido[2,3-b][1,4]benzodiazepin-11-yl)propan-1-amine Chemical compound N1C2=CC=CN=C2N(CCCN(C)C)C2=CC=CC=C2C1C1=CC=CC=C1 OIVGIIWPZYHINE-UHFFFAOYSA-N 0.000 claims 1
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- CJHKJXZMFZKGHI-UHFFFAOYSA-N 1h-pyrido[2,3-i][1,2]benzodiazepine Chemical class N1N=CC=CC2=CC=C(N=CC=C3)C3=C12 CJHKJXZMFZKGHI-UHFFFAOYSA-N 0.000 description 12
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- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical group Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
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- XMQMWATVTGDHKZ-UHFFFAOYSA-N n,n-dimethyl-3-[6-phenyl-9-(trifluoromethyl)pyrido[2,3-b][1,4]benzodiazepin-11-yl]propan-1-amine Chemical compound N=1C2=CC=CN=C2N(CCCN(C)C)C2=CC(C(F)(F)F)=CC=C2C=1C1=CC=CC=C1 XMQMWATVTGDHKZ-UHFFFAOYSA-N 0.000 description 1
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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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
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30508081A | 1981-09-24 | 1981-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH651833A5 true CH651833A5 (fr) | 1985-10-15 |
Family
ID=23179241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2288/82A CH651833A5 (fr) | 1981-09-24 | 1982-04-15 | Pyrido(1,4)benzodiazepines phenyl-substituees methanones correspondantes et medicaments les contenant. |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS5865290A (es) |
| KR (1) | KR890000764B1 (es) |
| BE (1) | BE891666A (es) |
| CA (1) | CA1199324A (es) |
| CH (1) | CH651833A5 (es) |
| DE (1) | DE3150522A1 (es) |
| DK (3) | DK186282A (es) |
| EG (1) | EG15904A (es) |
| ES (6) | ES8303348A1 (es) |
| FI (1) | FI71935C (es) |
| FR (1) | FR2515183B1 (es) |
| GR (1) | GR78473B (es) |
| HU (2) | HU189426B (es) |
| IE (1) | IE52493B1 (es) |
| IL (1) | IL64284A (es) |
| IN (1) | IN156080B (es) |
| IT (1) | IT1146728B (es) |
| LU (1) | LU83865A1 (es) |
| NL (1) | NL8200549A (es) |
| NO (1) | NO157700C (es) |
| NZ (1) | NZ198999A (es) |
| PH (2) | PH17847A (es) |
| PL (6) | PL143597B1 (es) |
| PT (1) | PT74286B (es) |
| SE (2) | SE448629B (es) |
| YU (1) | YU46128B (es) |
| ZA (1) | ZA817866B (es) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3825549A (en) * | 1972-10-24 | 1974-07-23 | Squibb & Sons Inc | Certain dihydropyrido(2,1-b)(1,3)benzodi-azepines and benzodiazocines |
| DE2424811C3 (de) * | 1974-05-22 | 1981-08-20 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| SE422799B (sv) * | 1975-05-28 | 1982-03-29 | Merck & Co Inc | Analogiforfarande for framstellning av 1,3-dihydroimidazo (4,5-b)pyridin-2-oner |
-
1981
- 1981-11-05 SE SE8106573A patent/SE448629B/sv not_active IP Right Cessation
- 1981-11-12 NO NO813839A patent/NO157700C/no unknown
- 1981-11-12 ZA ZA817866A patent/ZA817866B/xx unknown
- 1981-11-13 IN IN1261/CAL/81A patent/IN156080B/en unknown
- 1981-11-13 IL IL64284A patent/IL64284A/xx unknown
- 1981-11-17 GR GR66553A patent/GR78473B/el unknown
- 1981-11-18 PH PH26507A patent/PH17847A/en unknown
- 1981-11-25 IE IE2769/81A patent/IE52493B1/en unknown
- 1981-12-09 IT IT68605/81A patent/IT1146728B/it active
- 1981-12-10 FI FI813976A patent/FI71935C/fi not_active IP Right Cessation
- 1981-12-15 ES ES507971A patent/ES8303348A1/es not_active Expired
- 1981-12-15 HU HU843212A patent/HU189426B/hu not_active IP Right Cessation
- 1981-12-15 HU HU813777A patent/HU187393B/hu not_active IP Right Cessation
- 1981-12-21 DE DE19813150522 patent/DE3150522A1/de not_active Withdrawn
- 1981-12-23 PL PL1981253539A patent/PL143597B1/pl unknown
- 1981-12-23 PL PL1981241410A patent/PL137068B1/pl unknown
- 1981-12-23 PL PL1981253538A patent/PL143596B1/pl unknown
- 1981-12-23 PL PL1981253540A patent/PL143322B1/pl unknown
- 1981-12-23 PL PL1981234426A patent/PL138859B1/pl unknown
- 1981-12-23 PL PL1981241409A patent/PL139381B1/pl unknown
- 1981-12-23 FR FR8124111A patent/FR2515183B1/fr not_active Expired
- 1981-12-30 BE BE0/206969A patent/BE891666A/fr not_active IP Right Cessation
-
1982
- 1982-01-05 LU LU83865A patent/LU83865A1/fr unknown
- 1982-01-12 EG EG11/82A patent/EG15904A/xx active
- 1982-01-14 JP JP57004813A patent/JPS5865290A/ja active Pending
- 1982-01-15 PT PT74286A patent/PT74286B/pt unknown
- 1982-01-18 CA CA000394367A patent/CA1199324A/en not_active Expired
- 1982-02-02 KR KR8200420A patent/KR890000764B1/ko not_active Expired
- 1982-02-12 NL NL8200549A patent/NL8200549A/nl not_active Application Discontinuation
- 1982-02-18 NZ NZ198999A patent/NZ198999A/en unknown
- 1982-03-23 YU YU62582A patent/YU46128B/sh unknown
- 1982-04-15 CH CH2288/82A patent/CH651833A5/fr not_active IP Right Cessation
- 1982-04-26 DK DK186282A patent/DK186282A/da not_active Application Discontinuation
- 1982-09-29 ES ES516052A patent/ES516052A0/es active Granted
- 1982-09-29 ES ES516051A patent/ES8308563A1/es not_active Expired
-
1983
- 1983-10-19 ES ES526562A patent/ES526562A0/es active Granted
- 1983-10-19 ES ES526563A patent/ES8604531A1/es not_active Expired
-
1984
- 1984-08-17 PH PH31120A patent/PH20536A/en unknown
-
1985
- 1985-05-21 ES ES543328A patent/ES8607726A1/es not_active Expired
-
1986
- 1986-02-17 SE SE8600688A patent/SE455305B/sv not_active IP Right Cessation
-
1987
- 1987-08-03 DK DK403387A patent/DK403387A/da not_active Application Discontinuation
- 1987-08-03 DK DK403487A patent/DK403487D0/da not_active Application Discontinuation
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| Date | Code | Title | Description |
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| PK | Correction | ||
| PL | Patent ceased | ||
| PL | Patent ceased |