DE2715355A1 - Trans-hexahydro-pyrido-indole, verfahren zu ihrer herstellung sowie sie enthaltende arzneimittel - Google Patents
Trans-hexahydro-pyrido-indole, verfahren zu ihrer herstellung sowie sie enthaltende arzneimittelInfo
- Publication number
- DE2715355A1 DE2715355A1 DE19772715355 DE2715355A DE2715355A1 DE 2715355 A1 DE2715355 A1 DE 2715355A1 DE 19772715355 DE19772715355 DE 19772715355 DE 2715355 A DE2715355 A DE 2715355A DE 2715355 A1 DE2715355 A1 DE 2715355A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- cycloalkyl
- compounds
- pyrido
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229940126601 medicinal product Drugs 0.000 title description 3
- CCFNZJZCYYFGHV-KWQFWETISA-N (3aS,9bS)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline Chemical compound C1CC2=NC=CC=C2[C@@H]2[C@@H]1CCN2 CCFNZJZCYYFGHV-KWQFWETISA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 86
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
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- 239000000969 carrier Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004480 active ingredient Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
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- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
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- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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- 231100001015 blood dyscrasias Toxicity 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 230000036471 bradycardia Effects 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- 229940125904 compound 1 Drugs 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- 235000019634 flavors Nutrition 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
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- 239000012458 free base Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 208000018706 hematopoietic system disease Diseases 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 201000003102 mental depression Diseases 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67511276A | 1976-04-08 | 1976-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2715355A1 true DE2715355A1 (de) | 1977-10-20 |
Family
ID=24709111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772715355 Withdrawn DE2715355A1 (de) | 1976-04-08 | 1977-04-06 | Trans-hexahydro-pyrido-indole, verfahren zu ihrer herstellung sowie sie enthaltende arzneimittel |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4141980A (OSRAM) |
| JP (1) | JPS52125197A (OSRAM) |
| AR (1) | AR218246A1 (OSRAM) |
| AT (1) | AT360533B (OSRAM) |
| AU (1) | AU516432B2 (OSRAM) |
| BE (1) | BE853422A (OSRAM) |
| CA (1) | CA1071210A (OSRAM) |
| CH (1) | CH633795A5 (OSRAM) |
| DD (1) | DD132015A5 (OSRAM) |
| DE (1) | DE2715355A1 (OSRAM) |
| DK (1) | DK154877A (OSRAM) |
| ES (1) | ES457665A1 (OSRAM) |
| FI (1) | FI62304C (OSRAM) |
| FR (1) | FR2347365A1 (OSRAM) |
| GB (1) | GB1572057A (OSRAM) |
| GR (1) | GR63666B (OSRAM) |
| HU (1) | HU176956B (OSRAM) |
| IE (1) | IE45189B1 (OSRAM) |
| IL (1) | IL51840A (OSRAM) |
| LU (1) | LU77091A1 (OSRAM) |
| NL (1) | NL7703898A (OSRAM) |
| NO (1) | NO771242L (OSRAM) |
| NZ (1) | NZ183824A (OSRAM) |
| PH (1) | PH13152A (OSRAM) |
| PT (1) | PT66407B (OSRAM) |
| SE (1) | SE7702301L (OSRAM) |
| SU (1) | SU719503A3 (OSRAM) |
| ZA (1) | ZA772166B (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7702300L (sv) * | 1976-04-15 | 1977-10-16 | Endo Lab | Reduktionsforlopp |
| US4224329A (en) * | 1979-01-23 | 1980-09-23 | Pfizer Inc. | 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles |
| US4252812A (en) * | 1977-05-23 | 1981-02-24 | Pfizer Inc. | 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles |
| US4267331A (en) * | 1979-01-23 | 1981-05-12 | Pfizer Inc. | Process for the production of 2-substituted pyrido[4,3-b]-indoles |
| US4432978A (en) * | 1979-07-30 | 1984-02-21 | Pfizer Inc. | Hexahydro-trans-pyridoindole |
| US4352807A (en) * | 1979-07-30 | 1982-10-05 | Pfizer Inc. | Hexahydro-trans-pyridoindole neuroleptic agents |
| US4337250A (en) * | 1979-07-30 | 1982-06-29 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4431649A (en) * | 1979-07-30 | 1984-02-14 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4252811A (en) * | 1979-07-30 | 1981-02-24 | Pfizer Inc. | Hexahydro-trans-pyridoindole neuroleptic agents |
| US4431646A (en) * | 1979-07-30 | 1984-02-14 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4427679A (en) | 1981-01-16 | 1984-01-24 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US5319087A (en) * | 1987-04-16 | 1994-06-07 | Eli Lilly And Company | Piperidine opioid antagonists |
| US4992450A (en) * | 1987-04-16 | 1991-02-12 | Eli Lilly And Company | Piperidine opioid antagonists |
| US4891379A (en) * | 1987-04-16 | 1990-01-02 | Kabushiki Kaisha Kobe Seikosho | Piperidine opioid antagonists |
| US5270328A (en) * | 1991-03-29 | 1993-12-14 | Eli Lilly And Company | Peripherally selective piperidine opioid antagonists |
| US5159081A (en) * | 1991-03-29 | 1992-10-27 | Eli Lilly And Company | Intermediates of peripherally selective n-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists |
| US5250542A (en) * | 1991-03-29 | 1993-10-05 | Eli Lilly And Company | Peripherally selective piperidine carboxylate opioid antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH303833A (de) * | 1951-04-30 | 1954-12-15 | Bayer Ag | Verfahren zur Herstellung von Derivaten des Tetrahydro-y-carbolins. |
| JPS50126699A (OSRAM) * | 1974-03-20 | 1975-10-04 |
-
1977
- 1977-03-02 SE SE7702301A patent/SE7702301L/xx not_active Application Discontinuation
- 1977-04-06 GR GR53175A patent/GR63666B/el unknown
- 1977-04-06 PH PH19641A patent/PH13152A/en unknown
- 1977-04-06 ES ES457665A patent/ES457665A1/es not_active Expired
- 1977-04-06 NO NO771242A patent/NO771242L/no unknown
- 1977-04-06 AU AU24012/77A patent/AU516432B2/en not_active Expired
- 1977-04-06 FI FI771088A patent/FI62304C/fi not_active IP Right Cessation
- 1977-04-06 DE DE19772715355 patent/DE2715355A1/de not_active Withdrawn
- 1977-04-06 IE IE724/77A patent/IE45189B1/en unknown
- 1977-04-06 DK DK154877A patent/DK154877A/da not_active IP Right Cessation
- 1977-04-06 PT PT66407A patent/PT66407B/pt unknown
- 1977-04-06 SU SU772468108A patent/SU719503A3/ru active
- 1977-04-06 AT AT242377A patent/AT360533B/de not_active IP Right Cessation
- 1977-04-06 CA CA275,677A patent/CA1071210A/en not_active Expired
- 1977-04-06 AR AR267148A patent/AR218246A1/es active
- 1977-04-07 FR FR7710596A patent/FR2347365A1/fr active Granted
- 1977-04-07 CH CH446877A patent/CH633795A5/de not_active IP Right Cessation
- 1977-04-07 DD DD7700198299A patent/DD132015A5/xx unknown
- 1977-04-07 ZA ZA00772166A patent/ZA772166B/xx unknown
- 1977-04-07 NL NL7703898A patent/NL7703898A/xx not_active Application Discontinuation
- 1977-04-07 NZ NZ183824A patent/NZ183824A/xx unknown
- 1977-04-07 IL IL51840A patent/IL51840A/xx unknown
- 1977-04-08 JP JP3962477A patent/JPS52125197A/ja active Pending
- 1977-04-08 BE BE176568A patent/BE853422A/xx unknown
- 1977-04-08 HU HU77EO342A patent/HU176956B/hu unknown
- 1977-04-08 LU LU77091A patent/LU77091A1/xx unknown
- 1977-04-12 GB GB15071/77A patent/GB1572057A/en not_active Expired
- 1977-12-13 US US05/860,212 patent/US4141980A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK154877A (da) | 1977-10-09 |
| JPS52125197A (en) | 1977-10-20 |
| AU2401277A (en) | 1978-10-12 |
| AU516432B2 (en) | 1981-06-04 |
| NZ183824A (en) | 1980-10-24 |
| ES457665A1 (es) | 1978-07-16 |
| IE45189L (en) | 1977-10-08 |
| ZA772166B (en) | 1978-05-30 |
| IE45189B1 (en) | 1982-07-14 |
| DD132015A5 (de) | 1978-08-16 |
| FR2347365B1 (OSRAM) | 1979-03-02 |
| FR2347365A1 (fr) | 1977-11-04 |
| GB1572057A (en) | 1980-07-23 |
| AT360533B (de) | 1981-01-12 |
| NO771242L (no) | 1977-10-11 |
| BE853422A (fr) | 1977-10-10 |
| IL51840A (en) | 1980-10-26 |
| FI62304B (fi) | 1982-08-31 |
| ATA242377A (de) | 1980-06-15 |
| GR63666B (en) | 1979-11-28 |
| FI771088A7 (OSRAM) | 1977-10-09 |
| IL51840A0 (en) | 1977-06-30 |
| FI62304C (fi) | 1982-12-10 |
| SE7702301L (sv) | 1977-10-09 |
| SU719503A3 (ru) | 1980-02-29 |
| PT66407B (en) | 1978-09-13 |
| US4141980A (en) | 1979-02-27 |
| AR218246A1 (es) | 1980-05-30 |
| PH13152A (en) | 1979-12-18 |
| HU176956B (hu) | 1981-06-28 |
| CH633795A5 (de) | 1982-12-31 |
| NL7703898A (nl) | 1977-10-11 |
| LU77091A1 (OSRAM) | 1977-12-01 |
| PT66407A (en) | 1977-05-01 |
| CA1071210A (en) | 1980-02-05 |
Similar Documents
| Publication | Publication Date | Title |
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