SU965350A3 - Способ получени R,S-изомера производных фенэтаноламина или их солей - Google Patents
Способ получени R,S-изомера производных фенэтаноламина или их солей Download PDFInfo
- Publication number
- SU965350A3 SU965350A3 SU792786202A SU2786202A SU965350A3 SU 965350 A3 SU965350 A3 SU 965350A3 SU 792786202 A SU792786202 A SU 792786202A SU 2786202 A SU2786202 A SU 2786202A SU 965350 A3 SU965350 A3 SU 965350A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- isomer
- salts
- formula
- producing
- carbon atom
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/06—Preparation of carboxylic acid nitriles from N-formylated amino compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Description
работанном дл демонстрации такой мобилизации, соединение ввод т восьм крысам линии Charlos River, получающим нормальный рацион: кажда из крыс весит от 180 до 200 г. Непосредственно перед введением вещества у каждой из крыс берут кровь на анализ , котора служит дл контрол за каждым из восьми животных. Далее каж дому животному ввод т предлагаемое сое динение подкожно в дозе 10 мг/кг веса те ла .Затем у каждого животного берут кров на анализ с интервалами в 30,60, 90 и мин после введени дозы вещества , затем дл каждого образца крови определ ют уровень свободных жирных кислот в сыворотке. Результаты свидетельствуют о том, что предлагаемые соединени вызывают существенное увеличение уровн свобедных жирных кислот в сыворотке кро ви.. В тесте, разработанном дл провер ки эффектов понижени веса соединени ми в KatrecTBe модели выбраны желтые мыши, подверженные генетическому ожирению. Все животные имеют возраст 6,5 мес к началу исследовани .. Живот ные получают пуриновый лабораторный корм и воду без ограничени в течение всего времени исследовани . П ть тучных животных получают 10 мг/к R,S -Н-(2-фенил-2-гидроксиэтил)-1:-метил-3- (-гидроксифенил)пропиламй на подкожно дважды в день, а п ть животных получают плацебо. Исходный вес тела каждого животного опредеЛ ют на первый день исследований до iпервой инъекции. Полученные результаты свидетельствуют о том, что предлагаемые соединени вызывают существенное уменьшение веса тела у половозрелых тучных животных без понижени количества поглощаемой ими пищи. Формула изобретени Способ получени R S-изомера производных фенэтаноламина общей формулы i он к, fj- dH-dnQi HdHCHiCHgr ,X А где R - метил, аминокарбонил или метиламинокарбонил, С -асимметрический атом углерода, имекиций R абсолютную конфигурацию, С,,- асимметрический атом углерода, имеющий S абсолютную конфигурацию, или их солей,отличающийс тем, что окись стирола формулы подвергают взаимодействию с производным пропиламина формулы H2K- iH- ( где R и R имеют вышеуказанные значени , с последующим выделением целевого продукта в виде свободного соединени или в виде соли. Источники информации, прин тые во внимание при экспертизе 1.Патент СССР по за вке № 2673556/23-0, выданный инофирме Яманоути Фармасьютикал КО, Лтд, Япони , кл. С 07 С 91/16, 26.10.77 2.Патент Англии N° 10693 1, кл. С 2 С, опублик. 1966.
Claims (1)
- Формула’ изобретенияСпособ получения R^S-изомера производных фенэтаноламина общей формуJ лы |ОН ΚίI IСН-.СИ2^НСНСН2СН2 X I х х где R^ - метил, R^_- аминокарбонил или метиламинокарбонил, С*- асимметрический атом углерода, имеющий R 15 абсолютную конфигурацию, Схк- асимметрический атом углерода, имеющий S абсолютную конфигурацию, или их солей, отличающийся тем, что окись стирола формулы 11 /=\ У 4- £н2 м ♦ - . _ подвергают взаимодействию с производным пропиламина формулы ..30 I ’ ζζζχН2И - Си - tH2~ CH2-^y-R2 где R^ и R^_ имеют вышеуказанные значения, с последующим выделением целевого продукта в виде свободного соединения или в виде соли.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US92167078A | 1978-07-03 | 1978-07-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU965350A3 true SU965350A3 (ru) | 1982-10-07 |
Family
ID=25445792
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU792782302A SU849997A3 (ru) | 1978-07-03 | 1979-07-02 | Способ получени производныхфЕНэТАНОлАМиНА B СВОбОдНОМ ВидЕ,B ВидЕ СОли, РАцЕМАТА или ОпТичЕСКи- АКТиВНОгО АНТипОдА |
SU792786202A SU965350A3 (ru) | 1978-07-03 | 1979-07-02 | Способ получени R,S-изомера производных фенэтаноламина или их солей |
SU802955864A SU957761A3 (ru) | 1978-07-03 | 1980-08-13 | Способ получени оптически активных производных фенэтаноламина или их солей |
SU802957757A SU1007554A3 (ru) | 1978-07-03 | 1980-08-13 | Способ получени R,S-изомера производных фенэтаноламина или их солей |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU792782302A SU849997A3 (ru) | 1978-07-03 | 1979-07-02 | Способ получени производныхфЕНэТАНОлАМиНА B СВОбОдНОМ ВидЕ,B ВидЕ СОли, РАцЕМАТА или ОпТичЕСКи- АКТиВНОгО АНТипОдА |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU802955864A SU957761A3 (ru) | 1978-07-03 | 1980-08-13 | Способ получени оптически активных производных фенэтаноламина или их солей |
SU802957757A SU1007554A3 (ru) | 1978-07-03 | 1980-08-13 | Способ получени R,S-изомера производных фенэтаноламина или их солей |
Country Status (31)
Country | Link |
---|---|
EP (3) | EP0048037A1 (ru) |
JP (2) | JPS559097A (ru) |
KR (1) | KR880002310B1 (ru) |
AR (4) | AR225744A1 (ru) |
AT (2) | AT367025B (ru) |
AU (2) | AU523720B2 (ru) |
BE (2) | BE877393A (ru) |
BG (4) | BG31646A3 (ru) |
CA (2) | CA1142954A (ru) |
CH (2) | CH643529A5 (ru) |
CS (4) | CS208662B2 (ru) |
DD (2) | DD144761A5 (ru) |
DE (2) | DE2964604D1 (ru) |
DK (2) | DK160936C (ru) |
EG (1) | EG14238A (ru) |
ES (4) | ES482155A1 (ru) |
FI (2) | FI792082A (ru) |
FR (3) | FR2430410B1 (ru) |
GB (3) | GB2028799B (ru) |
GR (2) | GR72940B (ru) |
HU (2) | HU179172B (ru) |
IE (2) | IE48769B1 (ru) |
IL (2) | IL57671A (ru) |
LU (2) | LU81457A1 (ru) |
NZ (2) | NZ190861A (ru) |
PH (2) | PH14522A (ru) |
PL (4) | PL121297B1 (ru) |
PT (2) | PT69843A (ru) |
RO (4) | RO83052B (ru) |
SU (4) | SU849997A3 (ru) |
ZA (2) | ZA793297B (ru) |
Families Citing this family (36)
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 |
EP0028105B1 (en) * | 1979-10-25 | 1983-01-19 | Beecham Group Plc | Secondary amines, their preparation and use in pharmaceutical compositions |
EP0029320B1 (en) * | 1979-11-15 | 1985-07-10 | Beecham Group Plc | Secondary ethanol amines, their preparation and their use in pharmaceutical compositions |
DE3161165D1 (en) * | 1980-05-08 | 1983-11-17 | Beecham Group Plc | Arylethanolamine derivatives, their preparation and use in pharmaceutical compositions |
DE3264364D1 (en) * | 1981-03-06 | 1985-08-01 | Beecham Group Plc | Arylethanol amine derivatives, their preparation and use in pharmaceutical compositions |
DE3260490D1 (en) * | 1981-03-31 | 1984-09-06 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
EP0070133B1 (en) * | 1981-07-11 | 1986-05-14 | Beecham Group Plc | Secondary phenylethanol amines, processes for their preparation and their pharmaceutical application |
EP0089154A3 (en) * | 1982-03-12 | 1984-08-08 | Beecham Group Plc | Ethanolamine derivatives, their preparation and use in pharmaceutical compositions |
CA1219865A (en) * | 1982-05-14 | 1987-03-31 | Leo Alig | Aziridine phenethanolamine derivatives |
CA1258454A (en) * | 1982-08-10 | 1989-08-15 | Leo Alig | Phenethanolamines |
JPS5980640A (ja) * | 1982-09-27 | 1984-05-10 | イーライ・リリー・アンド・カンパニー | 2−ヒドロキシ−2−フエニルエチルアミン類の製造方法 |
PL144053B1 (en) * | 1983-01-31 | 1988-04-30 | Lilly Co Eli | Method of stimulating growth of domesticated animals,improving effectivness of food utilization ba domesticated animals and improving leanness of domesticated animals and fodder pre-mixture |
CA1262729A (en) * | 1983-10-19 | 1989-11-07 | Leo Alig | Phenoxypropanolamines |
US5166218A (en) * | 1983-10-19 | 1992-11-24 | Hoffmann-La Roche Inc. | Phenoxypropanolamines and pharmaceutical compositions thereof |
US4602044A (en) * | 1983-12-19 | 1986-07-22 | Eli Lilly And Company | β-phenethanolamine antiobesity agents |
EP0151513A1 (en) * | 1984-01-12 | 1985-08-14 | Eli Lilly And Company | Inotropic agent |
GB8505284D0 (en) * | 1985-03-01 | 1985-04-03 | Beecham Group Plc | Growth promoters |
PT82120B (en) * | 1985-03-01 | 1988-06-16 | Beecham Group Plc | Process for preparing veterinary formulations containing ethanolamine derivatives |
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 |
JP2837408B2 (ja) * | 1987-05-30 | 1998-12-16 | 鐘紡株式会社 | アクリル系繊維の処理方法 |
US5135955A (en) * | 1988-04-25 | 1992-08-04 | Eli Lilly And Company | Propanamine derivatives |
FI892341A (fi) * | 1988-06-10 | 1989-12-11 | Hoffmann La Roche | Propanolaminderivat. |
US5191112A (en) * | 1989-10-17 | 1993-03-02 | Nissan Chemical Industries, Ltd. | Process for optical resolution of (±)-2-(3-benzoyl)-phenylpropionic acid |
US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
US5688938A (en) * | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
US5763569A (en) * | 1991-08-23 | 1998-06-09 | The Brigham And Women's Hospital, Inc | Calcium receptor-active molecules |
KR100251995B1 (ko) * | 1991-08-23 | 2000-06-01 | 젠센 제임스 유. | 칼슘 수용체 활성 분자 |
US5858684A (en) * | 1991-08-23 | 1999-01-12 | The Brigham And Women's Hospital, Inc. | Method of screening calcium receptor-active molecules |
US5321036A (en) * | 1993-02-10 | 1994-06-14 | Bristol-Myers Squibb Company | Thiazole and oxazole-based β3 adrenergic receptor agonists |
US5962314A (en) * | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
CN1312116C (zh) | 1994-10-21 | 2007-04-25 | Nps药物有限公司 | 钙受体活性化合物 |
DE69722934T2 (de) | 1996-05-01 | 2004-05-27 | NPS Pharmaceuticals, Inc., Salt Lake City | Verbindungen , die auf anorganische ionen-rezeptoren wirken |
US7321065B2 (en) * | 2003-04-18 | 2008-01-22 | The Regents Of The University Of California | Thyronamine derivatives and analogs and methods of use thereof |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL56308C (ru) * | 1941-03-15 | |||
GB1200886A (en) * | 1966-09-23 | 1970-08-05 | Allen & Hanburys Ltd | Phenylaminoethanol derivatives |
GB1301134A (en) | 1970-07-18 | 1972-12-29 | Pfizer Ltd | SUBSTITUTED 1-PHENYL-2-ALLYLAMINO-ALKANOLS, 1-PHENYL-2-ALLYLAMINO-ALKANES AND alpha-AMINOALKYLPHENYL KETONES |
BE788850A (fr) * | 1972-09-15 | 1973-03-15 | Hoffmann La Roche | Derives d'acide benzoique |
IE39247B1 (en) * | 1973-05-07 | 1978-08-30 | Allen & Hanburys Ltd | Substituted benzamides |
US4000192A (en) * | 1973-05-07 | 1976-12-28 | Allen & Hanburys Limited | Pharmacologically active compounds |
NZ190854A (en) * | 1978-06-28 | 1984-10-19 | Beecham Group Ltd | 2-hydroxy-2-phenyl ethylamine derivatives;pharmaceutical compositions |
CA1145766A (en) * | 1978-07-03 | 1983-05-03 | Jack Mills | Optically active phenethanolamines and method for increasing cardiac contractility |
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1979
- 1979-06-26 IL IL57671A patent/IL57671A/xx unknown
- 1979-06-26 DK DK268679A patent/DK160936C/da not_active IP Right Cessation
- 1979-06-26 IL IL57672A patent/IL57672A/xx unknown
- 1979-06-26 CA CA000330553A patent/CA1142954A/en not_active Expired
- 1979-06-26 DK DK268779A patent/DK268779A/da not_active Application Discontinuation
- 1979-06-26 CA CA000330554A patent/CA1145767A/en not_active Expired
- 1979-06-27 NZ NZ190861A patent/NZ190861A/xx unknown
- 1979-06-27 EG EG387/78A patent/EG14238A/xx active
- 1979-06-27 PH PH22702A patent/PH14522A/en unknown
- 1979-06-27 PH PH22698A patent/PH15275A/en unknown
- 1979-06-27 NZ NZ190863A patent/NZ190863A/xx unknown
- 1979-06-28 PT PT69843A patent/PT69843A/pt unknown
- 1979-06-28 AU AU48487/79A patent/AU523720B2/en not_active Expired
- 1979-06-28 PT PT69839A patent/PT69839A/pt unknown
- 1979-06-28 AU AU48489/79A patent/AU523721B2/en not_active Ceased
- 1979-06-29 HU HU79EI868A patent/HU179172B/hu not_active IP Right Cessation
- 1979-06-29 HU HU79EI867A patent/HU179171B/hu unknown
- 1979-06-29 FR FR7916993A patent/FR2430410B1/fr not_active Expired
- 1979-06-29 FR FR7916994A patent/FR2430411A1/fr active Granted
- 1979-07-02 GB GB7922952A patent/GB2028799B/en not_active Expired
- 1979-07-02 FI FI792082A patent/FI792082A/fi not_active Application Discontinuation
- 1979-07-02 CS CS794631A patent/CS208662B2/cs unknown
- 1979-07-02 BE BE1/9444A patent/BE877393A/fr not_active IP Right Cessation
- 1979-07-02 RO RO105065A patent/RO83052B/ro unknown
- 1979-07-02 LU LU81457A patent/LU81457A1/xx unknown
- 1979-07-02 CH CH616279A patent/CH643529A5/fr not_active IP Right Cessation
- 1979-07-02 BG BG7945342A patent/BG31646A3/xx unknown
- 1979-07-02 EP EP81109789A patent/EP0048037A1/en not_active Ceased
- 1979-07-02 JP JP8489179A patent/JPS559097A/ja active Pending
- 1979-07-02 GB GB7922955A patent/GB2028802B/en not_active Expired
- 1979-07-02 DE DE7979301278T patent/DE2964604D1/de not_active Expired
- 1979-07-02 FI FI792081A patent/FI792081A/fi not_active Application Discontinuation
- 1979-07-02 JP JP8489079A patent/JPS559096A/ja active Granted
- 1979-07-02 GB GB08135768A patent/GB2101582B/en not_active Expired
- 1979-07-02 LU LU81458A patent/LU81458A1/xx unknown
- 1979-07-02 EP EP79301278A patent/EP0006766B1/en not_active Expired
- 1979-07-02 CS CS794631A patent/CS208664B2/cs unknown
- 1979-07-02 BG BG7944166A patent/BG31645A3/xx unknown
- 1979-07-02 BG BG7944169A patent/BG31375A3/xx unknown
- 1979-07-02 SU SU792782302A patent/SU849997A3/ru active
- 1979-07-02 BG BG7945343A patent/BG31647A3/xx unknown
- 1979-07-02 SU SU792786202A patent/SU965350A3/ru active
- 1979-07-02 RO RO105064A patent/RO83051B/ro unknown
- 1979-07-02 CH CH616179A patent/CH642618A5/fr not_active IP Right Cessation
- 1979-07-02 CS CS794631A patent/CS208663B2/cs unknown
- 1979-07-02 GR GR59490A patent/GR72940B/el unknown
- 1979-07-02 RO RO7998013A patent/RO77732A/ro unknown
- 1979-07-02 CS CS794632A patent/CS209815B2/cs unknown
- 1979-07-02 GR GR59491A patent/GR74524B/el unknown
- 1979-07-02 BE BE1/9445A patent/BE877394A/fr not_active IP Right Cessation
- 1979-07-02 RO RO7998009A patent/RO77728A/ro unknown
- 1979-07-02 EP EP79301279A patent/EP0007204B1/en not_active Expired
- 1979-07-02 DE DE7979301279T patent/DE2964091D1/de not_active Expired
- 1979-07-03 PL PL1979216811A patent/PL121297B1/pl unknown
- 1979-07-03 AR AR277166A patent/AR225744A1/es active
- 1979-07-03 ES ES482155A patent/ES482155A1/es not_active Expired
- 1979-07-03 ES ES482156A patent/ES482156A1/es not_active Expired
- 1979-07-03 AT AT0463679A patent/AT367025B/de not_active IP Right Cessation
- 1979-07-03 DD DD79214069A patent/DD144761A5/de unknown
- 1979-07-03 PL PL1979226370A patent/PL117997B1/pl unknown
- 1979-07-03 DD DD79214070A patent/DD144762A5/de unknown
- 1979-07-03 ZA ZA793297A patent/ZA793297B/xx unknown
- 1979-07-03 PL PL1979226371A patent/PL117996B1/pl unknown
- 1979-07-03 AT AT0463579A patent/AT372937B/de not_active IP Right Cessation
- 1979-07-03 AR AR277167A patent/AR229080A1/es active
- 1979-07-03 PL PL1979216814A patent/PL117551B1/pl unknown
- 1979-07-03 ZA ZA793296A patent/ZA793296B/xx unknown
- 1979-08-08 IE IE1227/79A patent/IE48769B1/en not_active IP Right Cessation
- 1979-08-08 IE IE1228/79A patent/IE48586B1/en unknown
-
1980
- 1980-04-01 ES ES490215A patent/ES8104190A1/es not_active Expired
- 1980-04-01 ES ES490214A patent/ES8104189A1/es not_active Expired
- 1980-04-24 FR FR8009239A patent/FR2450806B1/fr not_active Expired
- 1980-08-13 SU SU802955864A patent/SU957761A3/ru active
- 1980-08-13 SU SU802957757A patent/SU1007554A3/ru active
- 1980-10-29 AR AR283050A patent/AR227165A1/es active
- 1980-10-29 AR AR283051A patent/AR231434A1/es active
-
1982
- 1982-02-12 KR KR8200619A patent/KR880002310B1/ko active
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