DK169817B1 - Analogifremgangsmåde til fremstilling af benzo(5,6)cyclohepta(1,2-b)pyridiner - Google Patents
Analogifremgangsmåde til fremstilling af benzo(5,6)cyclohepta(1,2-b)pyridiner Download PDFInfo
- Publication number
- DK169817B1 DK169817B1 DK263481A DK263481A DK169817B1 DK 169817 B1 DK169817 B1 DK 169817B1 DK 263481 A DK263481 A DK 263481A DK 263481 A DK263481 A DK 263481A DK 169817 B1 DK169817 B1 DK 169817B1
- Authority
- DK
- Denmark
- Prior art keywords
- compound
- formula
- cyclohepta
- benzo
- reacted
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- VVJQGUSMDLABEG-UHFFFAOYSA-N 11h-benzo[1,2]cyclohepta[3,4-b]pyridine Chemical class C1=CC2=CC=CN=C2CC2=CC=CC=C21 VVJQGUSMDLABEG-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 229910052736 halogen Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 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 4
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 abstract description 4
- 230000001624 sedative effect Effects 0.000 abstract description 3
- 229940125715 antihistaminic agent Drugs 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- -1 N-Carboethoxy-4-piperidylidene-6,11-dihydro-5H-benzo [5,6] cyclohepta [1,2-b] pyridine Chemical compound 0.000 description 18
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- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 3
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- ACGXYICMMNRYMS-UHFFFAOYSA-N 1-methylsulfonyl-5-piperidin-4-ylidene-6,11-dihydro-2h-benzo[1,2]cyclohepta[6,7-b]pyridine Chemical compound CS(=O)(=O)N1CC=CC2=C1CC1=CC=CC=C1CC2=C1CCNCC1 ACGXYICMMNRYMS-UHFFFAOYSA-N 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 1
- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 1
- TYDPEPRGSQPCKB-UHFFFAOYSA-N 10-(1-methylpiperidin-2-ylidene)-5h-benzo[1,2]cyclohepta[3,4-b]thiophen-4-one Chemical compound CN1CCCCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 TYDPEPRGSQPCKB-UHFFFAOYSA-N 0.000 description 1
- VEHMROQZMLRPSA-UHFFFAOYSA-N 11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[3,4-b]pyridine Chemical compound C1CNCCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 VEHMROQZMLRPSA-UHFFFAOYSA-N 0.000 description 1
- HCLXLZGAYCTHQJ-UHFFFAOYSA-N 1h-cyclohepta[b]pyridine Chemical compound C1=CC=CC=C2NC=CC=C21 HCLXLZGAYCTHQJ-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- SYHCARCAUJVIDU-UHFFFAOYSA-N 9-ethylidene-4-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene Chemical compound C(C)=C1CC2=C(CC3=NC=CC=C31)C=CC=C2 SYHCARCAUJVIDU-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- 206010030113 Oedema Diseases 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- 208000036284 Rhinitis seasonal Diseases 0.000 description 1
- 240000001890 Ribes hudsonianum Species 0.000 description 1
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 1
- 235000001466 Ribes nigrum Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- 230000002567 autonomic effect Effects 0.000 description 1
- SEBMTIQKRHYNIT-UHFFFAOYSA-N azatadine Chemical compound C1CN(C)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 SEBMTIQKRHYNIT-UHFFFAOYSA-N 0.000 description 1
- 229960000383 azatadine Drugs 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 208000024376 chronic urticaria Diseases 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
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- MTDZGBSATVLDRM-UHFFFAOYSA-N ethyl 2-(4-oxo-5h-benzo[1,2]cyclohepta[3,4-b]thiophen-10-ylidene)piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 MTDZGBSATVLDRM-UHFFFAOYSA-N 0.000 description 1
- YVMQUVFVYIFGLY-UHFFFAOYSA-N ethyl 4-(5,6-dihydrobenzo[1,2]cyclohepta[3,4-b]pyridin-11-ylidene)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 YVMQUVFVYIFGLY-UHFFFAOYSA-N 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- AGNOKNMESONMLJ-UHFFFAOYSA-N methyl 4-(5,6-dihydrobenzo[1,2]cyclohepta[3,4-b]pyridin-11-ylidene)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 AGNOKNMESONMLJ-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
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- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (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)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Plant Substances (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06160795 US4282233B1 (en) | 1980-06-19 | 1980-06-19 | Antihistaminic 11-(4-piperidylidene)-5h-benzoÄ5,6Ü-cyclohepta-Ä1,2Ü-pyridines |
| US16079580 | 1980-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK263481A DK263481A (da) | 1981-12-20 |
| DK169817B1 true DK169817B1 (da) | 1995-03-06 |
Family
ID=22578489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK263481A DK169817B1 (da) | 1980-06-19 | 1981-06-16 | Analogifremgangsmåde til fremstilling af benzo(5,6)cyclohepta(1,2-b)pyridiner |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4282233B1 (es) |
| EP (1) | EP0042544B1 (es) |
| JP (1) | JPS5735586A (es) |
| KR (1) | KR850000744B1 (es) |
| AT (1) | ATE9695T1 (es) |
| AU (1) | AU543054B2 (es) |
| CA (1) | CA1160230A (es) |
| CY (1) | CY1405A (es) |
| DE (1) | DE3166441D1 (es) |
| DK (1) | DK169817B1 (es) |
| ES (1) | ES8300779A1 (es) |
| FI (1) | FI70213C (es) |
| HK (1) | HK94387A (es) |
| HU (1) | HU186774B (es) |
| IE (1) | IE51303B1 (es) |
| IL (1) | IL63122A (es) |
| KE (1) | KE3758A (es) |
| LU (1) | LU88359I2 (es) |
| MY (1) | MY8700761A (es) |
| NL (1) | NL930094I2 (es) |
| NZ (1) | NZ197435A (es) |
| PH (1) | PH19252A (es) |
| PT (1) | PT73200B (es) |
| SG (1) | SG70587G (es) |
| ZA (1) | ZA814062B (es) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419565A (en) * | 1963-04-24 | 1968-12-31 | Schering Corp | Aza-dibenzocycloheptenes |
| NL132137C (es) * | 1963-04-24 | |||
| US3264342A (en) * | 1963-05-24 | 1966-08-02 | Geigy Chem Corp | Derivatives of 5h-dibenzo[a, d] cycloheptene |
| US3491103A (en) * | 1963-12-19 | 1970-01-20 | Sandoz Ag | Certain 4h-benzo(4,5)cyclohepta-(1,2-b) thiophenes |
| US3464983A (en) * | 1964-02-04 | 1969-09-02 | Sandoz Ag | 4h-benzo(4,5)cyclohepta(1,2-b)thiophenes |
| US3435073A (en) * | 1966-04-19 | 1969-03-25 | Colgate Palmolive Co | 5-(n-benzyl-n-lower alkylaminoalkylene)-5h-dibenzo(a,d)cycloheptenes |
| US3513201A (en) * | 1966-10-25 | 1970-05-19 | Merck & Co Inc | Process for preparing 5-(3-alkylaminopropyl)-5h-dibenzo(a,d)cycloheptenes |
| US3917669A (en) * | 1966-11-08 | 1975-11-04 | Hoffmann La Roche | Intermediates for tricyclic amines |
| ES356805A1 (es) * | 1967-08-03 | 1970-05-01 | Hoffmann La Roche | Procedimiento para la preparacion de compuestos tricicli- cos. |
| US3952017A (en) * | 1968-05-03 | 1976-04-20 | Hoffmann-La Roche Inc. | Tricyclic compounds |
| CH531000A (de) * | 1970-03-11 | 1972-11-30 | Sandoz Ag | Verfahren zur Herstellung neuer Benzocycloheptathiophene |
| GB1329733A (en) * | 1970-12-02 | 1973-09-12 | Science Union & Cie | Derivatives of isonipecotic acid and a process for their prepa- ration |
-
1980
- 1980-06-19 US US06160795 patent/US4282233B1/en not_active Expired - Lifetime
-
1981
- 1981-06-11 AT AT81104480T patent/ATE9695T1/de active
- 1981-06-11 DE DE8181104480T patent/DE3166441D1/de not_active Expired
- 1981-06-11 EP EP81104480A patent/EP0042544B1/en not_active Expired
- 1981-06-11 CY CY140581A patent/CY1405A/xx unknown
- 1981-06-16 NZ NZ197435A patent/NZ197435A/en unknown
- 1981-06-16 FI FI811878A patent/FI70213C/sv not_active IP Right Cessation
- 1981-06-16 PT PT73200A patent/PT73200B/pt unknown
- 1981-06-16 CA CA000379879A patent/CA1160230A/en not_active Expired
- 1981-06-16 IE IE1328/81A patent/IE51303B1/en active Protection Beyond IP Right Term
- 1981-06-16 ES ES503085A patent/ES8300779A1/es not_active Expired
- 1981-06-16 AU AU71862/81A patent/AU543054B2/en not_active Expired
- 1981-06-16 DK DK263481A patent/DK169817B1/da not_active IP Right Cessation
- 1981-06-16 ZA ZA814062A patent/ZA814062B/xx unknown
- 1981-06-17 PH PH25770A patent/PH19252A/en unknown
- 1981-06-17 JP JP9369181A patent/JPS5735586A/ja active Granted
- 1981-06-17 KR KR1019810002204A patent/KR850000744B1/ko active
- 1981-06-18 IL IL63122A patent/IL63122A/xx unknown
- 1981-06-18 HU HU811795A patent/HU186774B/hu unknown
-
1987
- 1987-08-24 KE KE3758A patent/KE3758A/xx unknown
- 1987-08-27 SG SG705/87A patent/SG70587G/en unknown
- 1987-12-10 HK HK943/87A patent/HK94387A/xx not_active IP Right Cessation
- 1987-12-30 MY MY761/87A patent/MY8700761A/xx unknown
-
1993
- 1993-06-24 NL NL930094C patent/NL930094I2/nl unknown
- 1993-07-01 LU LU88359C patent/LU88359I2/fr unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| CTFF | Application for supplementary protection certificate (spc) filed |
Free format text: CA 1995 00009, 950704 |
|
| CTFG | Supplementary protection certificate (spc) issued |
Free format text: CA 1995 00009, 950704, EXPIRES: 20021201 |
|
| PUP | Patent expired |