DD145265A5 - Verfahren zur herstellung von phenethanolaminen - Google Patents
Verfahren zur herstellung von phenethanolaminen Download PDFInfo
- Publication number
- DD145265A5 DD145265A5 DD79214068A DD21406879A DD145265A5 DD 145265 A5 DD145265 A5 DD 145265A5 DD 79214068 A DD79214068 A DD 79214068A DD 21406879 A DD21406879 A DD 21406879A DD 145265 A5 DD145265 A5 DD 145265A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methyl
- hydroxyphenyl
- hydroxyethyl
- hydrogen
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 49
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- 239000000203 mixture Substances 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 29
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 229950006768 phenylethanolamine Drugs 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
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- 125000006239 protecting group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 7
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- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
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- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 2
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- 210000004731 jugular vein Anatomy 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- COIKKWFDURTDOU-SECBINFHSA-N methyl 4-[(3r)-3-aminobutyl]benzoate Chemical compound COC(=O)C1=CC=C(CC[C@@H](C)N)C=C1 COIKKWFDURTDOU-SECBINFHSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000037074 physically active Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- WJKYOQDIQYJXSD-UHFFFAOYSA-N propan-1-imine Chemical compound CCC=N WJKYOQDIQYJXSD-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-M trichloroacetate Chemical group [O-]C(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003600 vasopressic effect Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/04—Five-membered rings
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hospice & Palliative Care (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92166778A | 1978-07-03 | 1978-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD145265A5 true DD145265A5 (de) | 1980-12-03 |
Family
ID=25445784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79214068A DD145265A5 (de) | 1978-07-03 | 1979-07-03 | Verfahren zur herstellung von phenethanolaminen |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0007205A1 (cs) |
| JP (1) | JPS559098A (cs) |
| AR (2) | AR221884A1 (cs) |
| AT (1) | ATA463779A (cs) |
| AU (1) | AU4849079A (cs) |
| BE (1) | BE877391A (cs) |
| BG (4) | BG31492A3 (cs) |
| CA (1) | CA1145766A (cs) |
| CS (1) | CS225850B2 (cs) |
| DD (1) | DD145265A5 (cs) |
| DK (1) | DK269079A (cs) |
| ES (4) | ES482154A1 (cs) |
| FI (1) | FI792079A7 (cs) |
| FR (1) | FR2430408A1 (cs) |
| GB (1) | GB2029407A (cs) |
| GR (1) | GR72939B (cs) |
| IL (1) | IL57673A0 (cs) |
| LU (1) | LU81455A1 (cs) |
| NZ (1) | NZ190860A (cs) |
| PH (1) | PH15040A (cs) |
| PL (3) | PL118755B1 (cs) |
| PT (1) | PT69841A (cs) |
| RO (1) | RO77729A (cs) |
| SU (1) | SU936804A3 (cs) |
| ZA (1) | ZA793298B (cs) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006735B1 (en) * | 1978-06-28 | 1983-06-15 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
| DK268779A (da) * | 1978-07-03 | 1980-01-04 | Lilly Co Eli | Fremgangsmaade til fremstilling af phenethanolaminer |
| JPS57116300A (en) * | 1981-01-12 | 1982-07-20 | Fuji Photo Film Co Ltd | Noise elimination in radiation image recording reproduction |
| CA1219865A (en) * | 1982-05-14 | 1987-03-31 | Leo Alig | Aziridine phenethanolamine derivatives |
| CA1258454A (en) * | 1982-08-10 | 1989-08-15 | Leo Alig | Phenethanolamines |
| US4690951A (en) * | 1983-01-31 | 1987-09-01 | Eli Lilly And Company | Growth promotion |
| US5643967A (en) * | 1983-01-31 | 1997-07-01 | Eli Lilly And Company | Growth promotion |
| US4562206A (en) * | 1983-12-23 | 1985-12-31 | Key Pharmaceuticals, Inc. | Orally effective inotropic compounds |
| IT1204416B (it) * | 1986-06-27 | 1989-03-01 | Midy Spa | Medicamenti a base di analoghi di feniletanolammine per il trattamento di disturbi gastro-intestinali ed uterini |
| US5108363A (en) * | 1988-02-19 | 1992-04-28 | Gensia Pharmaceuticals, Inc. | Diagnosis, evaluation and treatment of coronary artery disease by exercise simulation using closed loop drug delivery of an exercise simulating agent beta agonist |
| US5135955A (en) * | 1988-04-25 | 1992-08-04 | Eli Lilly And Company | Propanamine derivatives |
| WO1995011223A1 (fr) * | 1993-10-20 | 1995-04-27 | Tokyo Tanabe Company Limited | Nouveau compose d'arylethanolamino(aryl)propanol |
| AU2001294378A1 (en) * | 2000-09-08 | 2002-03-22 | Dsm N.V. | Process for the preparation of enantiomerically enriched amines |
| WO2005036980A1 (en) * | 2003-10-07 | 2005-04-28 | Eli Lilly And Company | Liquid formulations of ractopamine |
| WO2007143336A2 (en) * | 2006-05-30 | 2007-12-13 | Stirling Products Limited | Use of ractopamine enantiomers |
| US20070282010A1 (en) | 2006-05-30 | 2007-12-06 | Bridge Pharma, Inc. | Methods of Accelerating Muscle Growth, Decreasing Fat Deposits and Improving Feed Efficiency in Livestock Animals |
| WO2009073051A1 (en) | 2007-12-03 | 2009-06-11 | Bridge Pharma, Inc. | Use of rr/sr-ractopamine |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE894396C (de) * | 1944-05-21 | 1953-10-26 | Troponwerke Dinklage & Co | Verfahren zur Herstellung von 1-(o-, m- oder p-Oxyphenyl)-1-oxy-2-aralkylamino-aethanen |
| DE1182245B (de) * | 1961-01-23 | 1964-11-26 | Philips Nv | Verfahren zur Herstellung eines uterospasmolytisch wirksamen linksdrehenden 1-(4'-Hy-droxyphenyl)-2-(1"-methyl-3"phenylpropylamino)-propanols |
| DE1543918A1 (de) * | 1966-01-28 | 1970-01-08 | Troponwerke Dinklage & Co | 1-[m-Hydroxyphenyl]-2-[1-methyl-3-phenylpropyl-(1)-amino]-aethanol-(1) und Verfahren zu dessen Herstellung |
| NL6610530A (cs) * | 1966-07-27 | 1968-01-29 | ||
| DE2044573A1 (en) * | 1970-09-09 | 1972-03-23 | Troponwerke Dinklage & Co, 5000 Köln-Mülheim | 1-(hydroxyphenyl)-2-(1-phenyl-2-methylpropyl or 4-methylpentyl - -(2)-amino)-ethanols and their salts - betasympathicomometic |
| DE2413102C3 (de) * | 1974-03-19 | 1980-09-11 | C.H. Boehringer Sohn, 6507 Ingelheim | Verfahren zur Herstellung von l-(3,5-Dihydroxyphenyl)-t-hydroxy-2- eckige Klammer auf 1-methyl-2-(4-hydroxyphenyl)- äthyl] -aminoäthan |
-
1979
- 1979-06-26 IL IL57673A patent/IL57673A0/xx unknown
- 1979-06-26 DK DK269079A patent/DK269079A/da unknown
- 1979-06-26 CA CA000330555A patent/CA1145766A/en not_active Expired
- 1979-06-27 NZ NZ190860A patent/NZ190860A/xx unknown
- 1979-06-27 PH PH22699A patent/PH15040A/en unknown
- 1979-06-28 PT PT69841A patent/PT69841A/pt not_active IP Right Cessation
- 1979-06-28 SU SU792784252A patent/SU936804A3/ru active
- 1979-06-28 AU AU48490/79A patent/AU4849079A/en not_active Abandoned
- 1979-06-29 FR FR7916991A patent/FR2430408A1/fr not_active Withdrawn
- 1979-07-02 RO RO7998010A patent/RO77729A/ro unknown
- 1979-07-02 GB GB7922951A patent/GB2029407A/en not_active Withdrawn
- 1979-07-02 BG BG045314A patent/BG31492A3/xx unknown
- 1979-07-02 BG BG045315A patent/BG31493A3/xx unknown
- 1979-07-02 LU LU81455A patent/LU81455A1/xx unknown
- 1979-07-02 BE BE1/9442A patent/BE877391A/fr unknown
- 1979-07-02 FI FI792079A patent/FI792079A7/fi not_active Application Discontinuation
- 1979-07-02 BG BG045313A patent/BG31491A3/xx unknown
- 1979-07-02 EP EP79301280A patent/EP0007205A1/en not_active Withdrawn
- 1979-07-02 CS CS794629A patent/CS225850B2/cs unknown
- 1979-07-02 GR GR59489A patent/GR72939B/el unknown
- 1979-07-02 JP JP8489279A patent/JPS559098A/ja active Pending
- 1979-07-02 BG BG044170A patent/BG31376A3/xx unknown
- 1979-07-03 ES ES482154A patent/ES482154A1/es not_active Expired
- 1979-07-03 DD DD79214068A patent/DD145265A5/de unknown
- 1979-07-03 AT AT0463779A patent/ATA463779A/de not_active Application Discontinuation
- 1979-07-03 PL PL1979227656A patent/PL118755B1/pl unknown
- 1979-07-03 ZA ZA793298A patent/ZA793298B/xx unknown
- 1979-07-03 AR AR277164A patent/AR221884A1/es active
- 1979-07-03 PL PL1979227655A patent/PL118515B1/pl unknown
- 1979-07-03 PL PL1979216812A patent/PL117514B1/pl unknown
-
1980
- 1980-04-01 ES ES490211A patent/ES8105263A1/es not_active Expired
- 1980-04-01 ES ES490213A patent/ES8105265A1/es not_active Expired
- 1980-04-01 ES ES490212A patent/ES8105264A1/es not_active Expired
-
1981
- 1981-01-21 AR AR284013A patent/AR225653A1/es active
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