FI56383C - Foerfarande foer framstaellning av nya pao hjaertverksamheten verkande 2-amino-5,6-dihydro-8,9-dialkoxi-pyrazolo(5,1-a)isokinolin-derivat - Google Patents
Foerfarande foer framstaellning av nya pao hjaertverksamheten verkande 2-amino-5,6-dihydro-8,9-dialkoxi-pyrazolo(5,1-a)isokinolin-derivat Download PDFInfo
- Publication number
- FI56383C FI56383C FI772711A FI772711A FI56383C FI 56383 C FI56383 C FI 56383C FI 772711 A FI772711 A FI 772711A FI 772711 A FI772711 A FI 772711A FI 56383 C FI56383 C FI 56383C
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- FI
- Finland
- Prior art keywords
- group
- formula
- compound
- dihydro
- phenacetyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 235000016709 nutrition Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- -1 alcohol alkali metal hydroxide Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000000747 cardiac effect Effects 0.000 claims description 4
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010008631 Cholera Diseases 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000004872 arterial blood pressure Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000002861 ventricular Effects 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000004217 heart function Effects 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 230000036284 oxygen consumption Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QPOFIDVRLWJICD-UHFFFAOYSA-N 3,3-diphenyl-n-(1-phenylpropan-2-yl)propan-1-amine;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 QPOFIDVRLWJICD-UHFFFAOYSA-N 0.000 description 2
- SQCICHPABTVAFF-UHFFFAOYSA-N 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-2-methyl-5-phenyl-3H-1,2,4-oxadiazole Chemical compound COC=1C=C2CCN=C(C2=CC=1OC)C1N(OC(=N1)C1=CC=CC=C1)C SQCICHPABTVAFF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 230000002107 myocardial effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- FMQQYJCCZKFNAH-UHFFFAOYSA-N 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-2-methyl-5-propyl-3H-1,2,4-oxadiazole Chemical compound COC=1C=C2CCN=C(C2=CC=1OC)C1N(OC(=N1)CCC)C FMQQYJCCZKFNAH-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- STCQKKWVPZJEBN-UHFFFAOYSA-N 8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinolin-2-amine Chemical compound NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 STCQKKWVPZJEBN-UHFFFAOYSA-N 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 102100027045 High affinity choline transporter 1 Human genes 0.000 description 1
- 101000693882 Homo sapiens High affinity choline transporter 1 Proteins 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- RWRNWINLPRLICF-UHFFFAOYSA-N N-benzyl-8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinolin-2-amine Chemical compound C(C1=CC=CC=C1)NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 RWRNWINLPRLICF-UHFFFAOYSA-N 0.000 description 1
- BVTDQRBFYGYOHV-UHFFFAOYSA-N O.O.Cl.NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 Chemical compound O.O.Cl.NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 BVTDQRBFYGYOHV-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000008557 oxygen metabolism Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000004088 pulmonary circulation Effects 0.000 description 1
- 230000036593 pulmonary vascular resistance Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001248 | 1972-06-30 | ||
| HUCI1248A HU167240B (OSRAM) | 1972-06-30 | 1972-06-30 | |
| FI205473 | 1973-06-27 | ||
| FI2054/73A FI55199C (fi) | 1972-06-30 | 1973-06-27 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-amino-5 6-dihydro-8 9-dialkoxiimidazo(5 1-a)isokinolinderivat |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772711A7 FI772711A7 (OSRAM) | 1977-09-14 |
| FI56383B FI56383B (fi) | 1979-09-28 |
| FI56383C true FI56383C (fi) | 1980-01-10 |
Family
ID=26156559
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772711A FI56383C (fi) | 1972-06-30 | 1977-09-14 | Foerfarande foer framstaellning av nya pao hjaertverksamheten verkande 2-amino-5,6-dihydro-8,9-dialkoxi-pyrazolo(5,1-a)isokinolin-derivat |
| FI772709A FI56381C (fi) | 1972-06-30 | 1977-09-14 | Foerfarande foer framstaellning av 2-amino-5,6-dihydro-8,9-dialkoxipyrazolo(5,1-a)isokinolinderivat och deras salter |
| FI772710A FI56382C (fi) | 1972-06-30 | 1977-09-14 | Foerfarande foer framstaellning av 3-amino-5,6-dihydro-8,9-dialkoxi-imidazo(5,1-a)isokinolinderivat och deras salter |
| FI772708A FI56380C (fi) | 1972-06-30 | 1977-09-14 | Foerfarande foer framstaellning av 3-amino-5,6-dihydro-8,9-dialkoxi-imidazo(5,1-a)isokinolinderivat |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772709A FI56381C (fi) | 1972-06-30 | 1977-09-14 | Foerfarande foer framstaellning av 2-amino-5,6-dihydro-8,9-dialkoxipyrazolo(5,1-a)isokinolinderivat och deras salter |
| FI772710A FI56382C (fi) | 1972-06-30 | 1977-09-14 | Foerfarande foer framstaellning av 3-amino-5,6-dihydro-8,9-dialkoxi-imidazo(5,1-a)isokinolinderivat och deras salter |
| FI772708A FI56380C (fi) | 1972-06-30 | 1977-09-14 | Foerfarande foer framstaellning av 3-amino-5,6-dihydro-8,9-dialkoxi-imidazo(5,1-a)isokinolinderivat |
Country Status (1)
| Country | Link |
|---|---|
| FI (4) | FI56383C (OSRAM) |
-
1977
- 1977-09-14 FI FI772711A patent/FI56383C/fi not_active IP Right Cessation
- 1977-09-14 FI FI772709A patent/FI56381C/fi not_active IP Right Cessation
- 1977-09-14 FI FI772710A patent/FI56382C/fi not_active IP Right Cessation
- 1977-09-14 FI FI772708A patent/FI56380C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI56382B (fi) | 1979-09-28 |
| FI772709A7 (OSRAM) | 1977-09-14 |
| FI56380B (fi) | 1979-09-28 |
| FI56381C (fi) | 1980-01-10 |
| FI56382C (fi) | 1980-01-10 |
| FI56383B (fi) | 1979-09-28 |
| FI56380C (fi) | 1980-01-10 |
| FI772711A7 (OSRAM) | 1977-09-14 |
| FI772708A7 (OSRAM) | 1977-09-14 |
| FI772710A7 (OSRAM) | 1977-09-14 |
| FI56381B (fi) | 1979-09-28 |
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| Date | Code | Title | Description |
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| MM | Patent lapsed |
Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK |