CH627648A5 - Nouveaux derives de 20,21-dinoreburnamenine, procede de preparation et compositions pharmaceutiques. - Google Patents
Nouveaux derives de 20,21-dinoreburnamenine, procede de preparation et compositions pharmaceutiques. Download PDFInfo
- Publication number
- CH627648A5 CH627648A5 CH193078A CH193078A CH627648A5 CH 627648 A5 CH627648 A5 CH 627648A5 CH 193078 A CH193078 A CH 193078A CH 193078 A CH193078 A CH 193078A CH 627648 A5 CH627648 A5 CH 627648A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- isomer
- dihydro
- hydrogen atom
- compounds
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 11
- 239000011707 mineral Substances 0.000 claims description 11
- 150000007522 mineralic acids Chemical class 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 235000005985 organic acids Nutrition 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- KOIGYXJOGRVNIS-HAIWGOBWSA-N dihydrodinoreburnameninol Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@H]4CC(O)N5C2=C1 KOIGYXJOGRVNIS-HAIWGOBWSA-N 0.000 claims description 3
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- JUJWROOIHBZHMG-QYKNYGDISA-N 2-deuteriopyridine Chemical compound [2H]C1=CC=CC=N1 JUJWROOIHBZHMG-QYKNYGDISA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000002490 cerebral effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- -1 for example Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 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 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7705067A FR2381048A1 (fr) | 1977-02-22 | 1977-02-22 | Nouveaux derives de 20,21-dinoreburnamenine, un procede pour leur preparation et leur application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627648A5 true CH627648A5 (fr) | 1982-01-29 |
Family
ID=9187054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH193078A CH627648A5 (fr) | 1977-02-22 | 1978-02-22 | Nouveaux derives de 20,21-dinoreburnamenine, procede de preparation et compositions pharmaceutiques. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4291038A (en, 2012) |
| JP (1) | JPS6031833B2 (en, 2012) |
| AT (1) | AT357274B (en, 2012) |
| BE (1) | BE864173A (en, 2012) |
| CA (1) | CA1095520A (en, 2012) |
| CH (1) | CH627648A5 (en, 2012) |
| DE (1) | DE2807643A1 (en, 2012) |
| DK (1) | DK151805C (en, 2012) |
| ES (2) | ES467185A1 (en, 2012) |
| FR (1) | FR2381048A1 (en, 2012) |
| GB (1) | GB1596207A (en, 2012) |
| HU (1) | HU176707B (en, 2012) |
| IE (1) | IE46466B1 (en, 2012) |
| IL (1) | IL54069A (en, 2012) |
| LU (1) | LU79099A1 (en, 2012) |
| MX (1) | MX5256E (en, 2012) |
| NL (1) | NL187397C (en, 2012) |
| PT (1) | PT67686B (en, 2012) |
| SE (1) | SE436356B (en, 2012) |
| ZA (1) | ZA781020B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2433528A2 (fr) * | 1978-08-16 | 1980-03-14 | Roussel Uclaf | Nouveaux derives de 20,21-dinoreburnamenine, un procede pour leur preparation et leur application comme medicaments |
| JPS55100383A (en) * | 1979-01-25 | 1980-07-31 | Sumitomo Chem Co Ltd | Preparation of novel nitrogen-containing polycyclic compound |
| FR2514357A1 (fr) * | 1981-10-08 | 1983-04-15 | Roussel Uclaf | Nouveaux derives de 20,21-dinoreburnamenine eventuellement substitues sur le cycle e, procede de preparation et application comme medicaments |
| HU187139B (en) * | 1982-06-30 | 1985-11-28 | Richter Gedeon Vegyeszet | Process for preparing new eburnan derivatives |
| FR2623501B1 (fr) * | 1987-11-19 | 1990-03-16 | Roussel Uclaf | Nouveaux derives substitues de 20,21-dinoreburnamenine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| FR2623503B1 (en, 2012) * | 1987-11-19 | 1991-04-05 | Roussel Uclaf | |
| FR2731154B1 (fr) * | 1995-03-03 | 1997-05-09 | Roussel Uclaf | Compositions pharmaceutiques comprenant des derives de dinoreburnamenine |
| FR2865650B1 (fr) * | 2004-01-30 | 2008-06-13 | Biocortech | Utilisation du 14,15 dihydro 20,21-dinoreburnamenin14-ol pour traiter et/ou prevenir les depressions majeures et les desordres du cycle veille-sommeil |
| FR2865649A1 (fr) * | 2004-01-30 | 2005-08-05 | Biocortech | Utilisation du 14,15-dihydro 20,21-dinoreburnamenin14-ol pour traiter et/ou prevenir les depressions majeures |
| FR2869034B1 (fr) | 2004-04-14 | 2008-04-04 | Biocortech Soc Par Actions Sim | Derive du 14,15-dihydro 20,21-dinoreburnamenin 14-ol et leur utilisation pour le traitement des depressions |
| FR2926077A1 (fr) | 2008-01-04 | 2009-07-10 | Servier Lab | Nouveaux derives d'1h-indol-1-yl uree, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1586697A (en, 2012) * | 1967-08-23 | 1970-02-27 | ||
| US3542796A (en) * | 1969-07-07 | 1970-11-24 | Miles Lab | Certain hexahydro-1,12-trimethylene-indolo(2,3-a)quinolizines |
| FR2081587B1 (en, 2012) * | 1970-03-26 | 1973-04-06 | Anvar | |
| FR2168853B1 (en, 2012) * | 1972-01-24 | 1975-04-25 | Centre Etd Ind Pharma | |
| HU166766B (en, 2012) * | 1972-12-08 | 1975-05-28 | ||
| JPS5147720A (en, 2012) * | 1974-10-22 | 1976-04-23 | Komatsu Mfg Co Ltd |
-
1977
- 1977-02-22 FR FR7705067A patent/FR2381048A1/fr active Granted
-
1978
- 1978-01-31 SE SE7801153A patent/SE436356B/sv not_active IP Right Cessation
- 1978-02-17 IL IL54069A patent/IL54069A/xx unknown
- 1978-02-20 AT AT121178A patent/AT357274B/de active
- 1978-02-20 NL NLAANVRAGE7801887,A patent/NL187397C/xx not_active IP Right Cessation
- 1978-02-21 ES ES467185A patent/ES467185A1/es not_active Expired
- 1978-02-21 LU LU79099A patent/LU79099A1/xx unknown
- 1978-02-21 HU HU78RO965A patent/HU176707B/hu not_active IP Right Cessation
- 1978-02-21 DK DK075878A patent/DK151805C/da not_active IP Right Cessation
- 1978-02-21 IE IE377/78A patent/IE46466B1/en not_active IP Right Cessation
- 1978-02-21 BE BE185355A patent/BE864173A/xx not_active IP Right Cessation
- 1978-02-21 GB GB6874/78A patent/GB1596207A/en not_active Expired
- 1978-02-21 ZA ZA00781020A patent/ZA781020B/xx unknown
- 1978-02-21 CA CA297,373A patent/CA1095520A/fr not_active Expired
- 1978-02-21 MX MX786873U patent/MX5256E/es unknown
- 1978-02-21 PT PT67686A patent/PT67686B/pt unknown
- 1978-02-22 DE DE19782807643 patent/DE2807643A1/de active Granted
- 1978-02-22 CH CH193078A patent/CH627648A5/fr not_active IP Right Cessation
- 1978-02-22 JP JP53018636A patent/JPS6031833B2/ja not_active Expired
-
1979
- 1979-01-15 ES ES476866A patent/ES476866A1/es not_active Expired
-
1980
- 1980-04-07 US US06/137,913 patent/US4291038A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK75878A (da) | 1978-08-23 |
| IL54069A (en) | 1982-01-31 |
| NL7801887A (nl) | 1978-08-24 |
| LU79099A1 (fr) | 1978-09-28 |
| BE864173A (fr) | 1978-08-21 |
| DK151805C (da) | 1988-06-13 |
| DE2807643C2 (en, 2012) | 1992-04-09 |
| FR2381048B1 (en, 2012) | 1980-12-19 |
| MX5256E (es) | 1983-05-23 |
| GB1596207A (en) | 1981-08-19 |
| JPS6031833B2 (ja) | 1985-07-24 |
| AT357274B (de) | 1980-06-25 |
| ES476866A1 (es) | 1980-03-01 |
| SE7801153L (sv) | 1978-08-23 |
| ZA781020B (en) | 1979-03-28 |
| IE780377L (en) | 1978-08-22 |
| JPS53103500A (en) | 1978-09-08 |
| IE46466B1 (en) | 1983-06-15 |
| PT67686A (fr) | 1979-05-16 |
| HU176707B (en) | 1981-04-28 |
| ATA121178A (de) | 1979-11-15 |
| NL187397B (nl) | 1991-04-16 |
| CA1095520A (fr) | 1981-02-10 |
| FR2381048A1 (fr) | 1978-09-15 |
| ES467185A1 (es) | 1979-06-16 |
| AU3346978A (en) | 1979-08-30 |
| PT67686B (fr) | 1980-03-04 |
| DE2807643A1 (de) | 1978-08-24 |
| NL187397C (nl) | 1991-09-16 |
| US4291038A (en) | 1981-09-22 |
| DK151805B (da) | 1988-01-04 |
| IL54069A0 (en) | 1978-04-30 |
| SE436356B (sv) | 1984-12-03 |
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