CS225850B2 - Process for preparing new r,r-n-(2-phenyl-2-hydroxyethyl)-1-methyl-3-phenylpropylamines - Google Patents
Process for preparing new r,r-n-(2-phenyl-2-hydroxyethyl)-1-methyl-3-phenylpropylamines Download PDFInfo
- Publication number
- CS225850B2 CS225850B2 CS794629A CS462979A CS225850B2 CS 225850 B2 CS225850 B2 CS 225850B2 CS 794629 A CS794629 A CS 794629A CS 462979 A CS462979 A CS 462979A CS 225850 B2 CS225850 B2 CS 225850B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- hydrogen
- compounds
- phenyl
- hydroxyethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 5
- 229910052731 fluorine Chemical group 0.000 claims abstract description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004041 inotropic agent Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 37
- -1 hydroxy, fluoro, aminocarbonyl Chemical group 0.000 description 31
- 239000000203 mixture Substances 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
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- 230000002829 reductive effect Effects 0.000 description 27
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 26
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- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
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- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 11
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
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- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- FPECOSYBIOUTMG-CQSZACIVSA-N (2r)-4-(4-phenylmethoxyphenyl)butan-2-amine Chemical compound C1=CC(CC[C@H](N)C)=CC=C1OCC1=CC=CC=C1 FPECOSYBIOUTMG-CQSZACIVSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 3
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- 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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- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 3
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
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- CQQSQBRPAJSTFB-UHFFFAOYSA-N 4-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CBr)C=C1 CQQSQBRPAJSTFB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (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 |
|---|---|
| CS225850B2 true CS225850B2 (en) | 1984-02-13 |
Family
ID=25445784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS794629A CS225850B2 (en) | 1978-07-03 | 1979-07-02 | Process for preparing new r,r-n-(2-phenyl-2-hydroxyethyl)-1-methyl-3-phenylpropylamines |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0007205A1 (es) |
| JP (1) | JPS559098A (es) |
| AR (2) | AR221884A1 (es) |
| AT (1) | ATA463779A (es) |
| AU (1) | AU4849079A (es) |
| BE (1) | BE877391A (es) |
| BG (4) | BG31491A3 (es) |
| CA (1) | CA1145766A (es) |
| CS (1) | CS225850B2 (es) |
| DD (1) | DD145265A5 (es) |
| DK (1) | DK269079A (es) |
| ES (4) | ES482154A1 (es) |
| FI (1) | FI792079A7 (es) |
| FR (1) | FR2430408A1 (es) |
| GB (1) | GB2029407A (es) |
| GR (1) | GR72939B (es) |
| IL (1) | IL57673A0 (es) |
| LU (1) | LU81455A1 (es) |
| NZ (1) | NZ190860A (es) |
| PH (1) | PH15040A (es) |
| PL (3) | PL117514B1 (es) |
| PT (1) | PT69841A (es) |
| RO (1) | RO77729A (es) |
| SU (1) | SU936804A3 (es) |
| ZA (1) | ZA793298B (es) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2965655D1 (en) * | 1978-06-28 | 1983-07-21 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
| IL57671A (en) * | 1978-07-03 | 1982-11-30 | Lilly Co Eli | Phenethanolamines,process for their preparation and pharmaceutical and animal feed compositions containing the same |
| 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 (en) * | 1993-10-20 | 1995-04-27 | Tokyo Tanabe Company Limited | Novel arylethanolamino(aryl)propanol compound |
| WO2002020821A2 (en) * | 2000-09-08 | 2002-03-14 | 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 (es) * | 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 DK DK269079A patent/DK269079A/da unknown
- 1979-06-26 IL IL57673A patent/IL57673A0/xx 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 AU AU48490/79A patent/AU4849079A/en not_active Abandoned
- 1979-06-28 SU SU792784252A patent/SU936804A3/ru active
- 1979-06-28 PT PT69841A patent/PT69841A/pt not_active IP Right Cessation
- 1979-06-29 FR FR7916991A patent/FR2430408A1/fr not_active Withdrawn
- 1979-07-02 BG BG045313A patent/BG31491A3/xx unknown
- 1979-07-02 RO RO7998010A patent/RO77729A/ro unknown
- 1979-07-02 BG BG044170A patent/BG31376A3/xx unknown
- 1979-07-02 BG BG045314A patent/BG31492A3/xx unknown
- 1979-07-02 LU LU81455A patent/LU81455A1/xx unknown
- 1979-07-02 BE BE1/9442A patent/BE877391A/fr unknown
- 1979-07-02 CS CS794629A patent/CS225850B2/cs unknown
- 1979-07-02 FI FI792079A patent/FI792079A7/fi not_active Application Discontinuation
- 1979-07-02 GR GR59489A patent/GR72939B/el unknown
- 1979-07-02 GB GB7922951A patent/GB2029407A/en not_active Withdrawn
- 1979-07-02 BG BG045315A patent/BG31493A3/xx unknown
- 1979-07-02 JP JP8489279A patent/JPS559098A/ja active Pending
- 1979-07-02 EP EP79301280A patent/EP0007205A1/en not_active Withdrawn
- 1979-07-03 PL PL1979216812A patent/PL117514B1/pl unknown
- 1979-07-03 ZA ZA793298A patent/ZA793298B/xx unknown
- 1979-07-03 DD DD79214068A patent/DD145265A5/de unknown
- 1979-07-03 PL PL1979227655A patent/PL118515B1/pl unknown
- 1979-07-03 AR AR277164A patent/AR221884A1/es active
- 1979-07-03 ES ES482154A patent/ES482154A1/es not_active Expired
- 1979-07-03 AT AT0463779A patent/ATA463779A/de not_active Application Discontinuation
- 1979-07-03 PL PL1979227656A patent/PL118755B1/pl unknown
-
1980
- 1980-04-01 ES ES490211A patent/ES8105263A1/es not_active Expired
- 1980-04-01 ES ES490213A patent/ES490213A0/es active Granted
- 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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