SE448874B - Derivat av 4-amino-5-alkylsulfonyl-orto-anisamider, farmakologisk komposition och sett att framstella amiderna - Google Patents
Derivat av 4-amino-5-alkylsulfonyl-orto-anisamider, farmakologisk komposition och sett att framstella amidernaInfo
- Publication number
- SE448874B SE448874B SE7900380A SE7900380A SE448874B SE 448874 B SE448874 B SE 448874B SE 7900380 A SE7900380 A SE 7900380A SE 7900380 A SE7900380 A SE 7900380A SE 448874 B SE448874 B SE 448874B
- Authority
- SE
- Sweden
- Prior art keywords
- amino
- methoxy
- ethyl
- pyrrolidylmethyl
- formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Description
ZS 448 874 2 coon cH ß í R o - 2 2 NHZ ~ vari R2 har tidigare angiven betydelse, eller ett av dess aktiva derivat, såsom dess syrahalogenid, alkylester, reaktíva ester, till exempel metoximetylester eller cyanometylester, aromatiska ester, N-hydroxíimidester, symmetriska anhydríd eller blandad anhydrid, bildad exempelvis från en ester av kolsyra eller en halogenmyrsyraester, azid, hydrazid, azolíd, syraisotiocyanat, trikloracetofenon eller ett derivat av trifenylfosfín, behandlas med en amin med formeln: I ' 11 _ HZN-cH¿-^\T»J (I 3 RI vari R1 har tidigare angiven betydelse, eller med ett av dess reaktiva derivat, såsom det derivat som erhålles genom reaktion mellan aminen och en fosforklorid, fosforoxiklorid, ett dialkyl, diaryl- eller ortofenylenklorfosfit, ett alkyl- eller aryldiklor- fosfít, eller ett isotiocyanat av aminen eller en substituerad karbamid eller sulfamid.
Uppfinningen är icke begränsad till de i det föregående nämn- da derivaten av syran och aminen.
Amideringsreaktíonen kan genomföras in situ eller efter det att den reaktiva mellanföreningen frånskilts.
Det är likaledes möjligt att bringa den fria syran och den fria aminen att reagera i närvaro av ett kondensationsmedel, så- som kiseltetraklorid, triklorfenylsilan, fosforsyraanhydríd, en karbodiimid eller en alkoxiacetylen.
Föreningarna med formel (I) kan likaledes framställas genom att syran med formel (II) eller ett av dess aktiva derivat enligt föregående definition bringas att reagera med en dihalogenalkyl- É amin med formeln: H2N-cH2__
Claims (4)
1. Derivat av 4-amino-5-alkylsulfonyl-orto-anísamíder, k ä n n e t e c k n a d e av formeln: coNH-CHZÅ N/I (I) ocfls \ |' 1 111 R o -s \ 2 2 NHZ vari R1 betecknar metyl, etyl, propyl eller allyl och R2 betecknar metyl, etyl, propyl eller ísopropyl, samt deras addítíonssalter med farmakologiskt godtagbara syror, deras kva- ternära ammoniumsalter, deras oxíder och deras vänstervridande och högervrídande isomerer.
2. Förening enligt krav 1, k ä n n e t e c k n a d därav, att den utgöres av någon av följande: N-(1-etyl-2-pyrrolídylmetyl)-2-metoxi-4-amino-5-etylsulfonyl- bensamíd, N-(1-metyl-2-pyrrolídylmetyl)-2-metoxi-4-amino-S-ety1sulfony1- bensamid, X-(1-a11yl-2-pyrrolidylmetyl)-2-metoxi-4-amino-5-etylsulfony1- bensamid, ñögervridande N-(1-etyl-2-pyrrolídylmetyl)-Z-metoxi-4-amínoï S-etylsulfonylbensamid-tartrat vänstervrídande N-(1-etyl-2-pyrrolidylmetyl)-2-metoxi-4- amin°-5_ etylsulfonylbensamid-tartrat, högervridande N-(1-metyl-2-pyrrolidylmetyl)-2-metoxi-4-amino- -5-etylsulfonylbensamíd, N-(1-etyl-Z-pyrrolídylmetyl)-Z-metoxi-4-amino-5-propylsu1fonyl- bensamid, N-(1-etyl-2-pyrrolidylmetyl)-2-metoxí-4-amino-5-mety1sulfonyl- bensamid, N-(1-mety1-2-pyrrolidylmetyl)-2-metoxi-4-amino-S-metylsulfonyl- bensamíd, ' ' N-Oxiden av N-(1-etyl-2-pyrrolidylmetyl)-2-metoxi-4-amino-5- etylsulfonylbensamíd och N-oxiden av N-(1-metyl-2-pyrrolídylmetyl)-2-metoxí-4-amino-5- etylsulfonylbensamíd. 448 874 20
3. Farmakologisk komposition, k ä n n e t e c k n a d därav, att den som aktiv komponent innehåller en av föreningarna enligt krav 1 eller 2, med formeln ._ coNH-cH2__I:;:] (1) ocas I R1 Rzoz-s NH2 vari R1 betecknar metyl, etyl, propyl eller allyl, och R2 be- tecknar metyl, etyl, propyl eller isopropyl, eller deras addi- tionssalter med farmakologiskt godtagbara syror, deras kvater- nära æmnniumsalter, deras oxider eller deras vänstervridande eller högervridande ísomerer, i kombination med farmakologiskt godtagbara excipienter.
4. Sätt att framställa föreningar enligt krav 1 eller 2, med formeln CONH-CH2__í:_:] (1) N ocfls Å 1 . R 0 -S ï 2 2 NH2 \ vari R1 betecknar metyl, etyl, propyl eller allyl, och R2 be- tecknar metyl, etyl, propyl eller isopropyl, eller deras addi- tionssalter med farmakologiskt godtagbara syror, deras kvater- nära ammoniumsalter, deras oxíder eller deras vänstervridande eller högervridande isomerer,.k ä n n e t e c k n a t därav, att 2-metoxi-4-amino-5-merkaptobensoesyra bringas att reagera med ett alkylsulfat, och den erhållna 2-metoxi-4-amíno-5-alkyl- tiobensoesyran oxideras, varefter den erhållna 2-met0Xi-4-amino- S-alkylsulfonylbensoesyran med formeln COOH \' (II) ä; u 448 874 vari R2 har tidigare angiven betydelse, eller ett av dess reak- tiva derivat a) behandlas med en amin med formeln HZN - cnznlï/I (III) 1 vari R1 har tidigare angiven betydelse, eller med ett av dess reaktíva derivat, eller b) behandlas med en dihalogenalkylamin med formeln HZN - cH2-_< > (lv) Hal Hal vari Hal betecknar en klor- eller bromatom, varefter den erhållna föreningen med formeln CONHCHZ--< > (V) I al Ha S_l:í:¥_0CH3 R20, *\ ~ s NH, behandlas med en amin med formeln HZN - R1 (VI) vari R1 har tidigare angiven betydelse.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7801632A FR2415099A1 (fr) | 1978-01-20 | 1978-01-20 | Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes |
Publications (2)
Publication Number | Publication Date |
---|---|
SE7900380L SE7900380L (sv) | 1979-07-21 |
SE448874B true SE448874B (sv) | 1987-03-23 |
Family
ID=9203689
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7900380A SE448874B (sv) | 1978-01-20 | 1979-01-16 | Derivat av 4-amino-5-alkylsulfonyl-orto-anisamider, farmakologisk komposition och sett att framstella amiderna |
SE8603773A SE460968B (sv) | 1978-01-20 | 1986-09-09 | Mellanfoerening, till framstaellning av terapeutiskt anvaendbara derivat av 4-amino-5-alkylsulfonyl-orto-anisamider, vilken utgoeres av 2-metoxi-4-amino-5-alkyltio- eller 2-metoxi-4-amino-5-alkylsulfonylbensoesyra |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8603773A SE460968B (sv) | 1978-01-20 | 1986-09-09 | Mellanfoerening, till framstaellning av terapeutiskt anvaendbara derivat av 4-amino-5-alkylsulfonyl-orto-anisamider, vilken utgoeres av 2-metoxi-4-amino-5-alkyltio- eller 2-metoxi-4-amino-5-alkylsulfonylbensoesyra |
Country Status (42)
Country | Link |
---|---|
US (2) | US4294828A (sv) |
JP (1) | JPS6049192B2 (sv) |
AR (2) | AR221354A1 (sv) |
AT (1) | AT377977B (sv) |
AU (1) | AU528561B2 (sv) |
BE (1) | BE872585A (sv) |
BG (2) | BG31496A3 (sv) |
CA (1) | CA1101430A (sv) |
CH (1) | CH637927A5 (sv) |
CS (1) | CS226181B2 (sv) |
CY (1) | CY1201A (sv) |
DD (1) | DD141520A5 (sv) |
DE (1) | DE2901181C2 (sv) |
DK (1) | DK158346C (sv) |
EG (1) | EG14045A (sv) |
ES (2) | ES476755A1 (sv) |
FI (1) | FI71126C (sv) |
FR (1) | FR2415099A1 (sv) |
GB (2) | GB2012765B (sv) |
GR (1) | GR64431B (sv) |
HK (1) | HK12184A (sv) |
HU (1) | HU179793B (sv) |
IE (1) | IE47798B1 (sv) |
IL (1) | IL56411A (sv) |
IN (1) | IN150226B (sv) |
IT (1) | IT1164655B (sv) |
LU (1) | LU80786A1 (sv) |
MC (1) | MC1232A1 (sv) |
MX (2) | MX5793E (sv) |
NL (1) | NL191707C (sv) |
NO (1) | NO151320C (sv) |
NZ (1) | NZ189378A (sv) |
OA (1) | OA06156A (sv) |
PH (2) | PH15725A (sv) |
PL (2) | PL116532B1 (sv) |
PT (1) | PT69068A (sv) |
RO (2) | RO76393A (sv) |
SE (2) | SE448874B (sv) |
SU (1) | SU820659A3 (sv) |
YU (2) | YU42172B (sv) |
ZA (1) | ZA79219B (sv) |
ZM (1) | ZM579A1 (sv) |
Families Citing this family (44)
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FR2440946A2 (fr) * | 1978-01-20 | 1980-06-06 | Ile De France | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
ZA818221B (en) * | 1980-12-12 | 1982-10-27 | Beecham Group Plc | Pharmaceutical compounds |
FR2550447B1 (fr) * | 1983-08-10 | 1986-01-17 | Ile De France | Application du n-(ally-2-pyrrolidinylmethyl) 2-methoxy 4-amino 5-methylsulfamoyl benzamide comme antiagregant plaquettaire |
FR2574795B1 (fr) * | 1984-12-18 | 1987-11-20 | Ile De France | Nouveau procede industriel de synthese du n-((1'-allyl 2'-pyrrolidinyl) methyl) 2-methoxy 4,5-azimido benzamide |
FR2584401B1 (fr) * | 1985-07-04 | 1987-11-20 | Ile De France | Nouveau benzamide, son procede de preparation et son application dans le domaine therapeutique |
US5260319A (en) * | 1989-12-26 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
US5227388A (en) * | 1989-12-26 | 1993-07-13 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
FR2678266A1 (fr) * | 1991-06-28 | 1992-12-31 | Delagrange Laboratoires | Nouveaux derives de 2-hydroxy 4-amino 5-ethylsulfonyl benzamide utiles comme anxiolytiques. |
FR2699533A1 (fr) * | 1992-12-21 | 1994-06-24 | Mouhtaram Mohamed | Dérivés de N-((1,4-dialkyl-6-arylpipérazine-2-yl)méthyl)benzamides. (Isomères cis et trans) Propriétés pharmacologiques et applications. |
FR2753376B1 (fr) * | 1996-09-18 | 1998-10-16 | Synthelabo | Compositions pharmaceutiques comprenant de l'amisulpride et leurs applications therapeutiques |
FR2762213B1 (fr) * | 1997-04-18 | 1999-05-14 | Synthelabo | Composition pharmaceutique a retention gastrique |
US6169094B1 (en) * | 1998-07-14 | 2001-01-02 | Sanofi-Synthelabo | Compositions of (S) (-)-amisulpride |
US20030129186A1 (en) | 2001-07-25 | 2003-07-10 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
BRPI0410271A (pt) * | 2003-05-16 | 2006-05-16 | Pfizer Prod Inc | combinações terapêuticas de antipsicóticos atìpicos com moduladores de gaba, anticonvulsivantes ou benzodiazepinas |
FR2857263B1 (fr) * | 2003-07-09 | 2005-09-09 | Sanofi Synthelabo | Nouvelle composition pharmaceutique solide comprenant de l'amisulpride |
BRPI0510942A (pt) * | 2004-05-11 | 2007-07-17 | Pfizer Prod Inc | combinação de antipsicóticos atìpicos e antagonistas do receptor 5-ht1b |
EP1879569A2 (en) * | 2005-04-22 | 2008-01-23 | Wyeth | Therapeutic combinations for the treatment or prevention of psychotic disorders |
SI1889198T1 (sl) | 2005-04-28 | 2015-02-27 | Proteus Digital Health, Inc. | Farma-informacijski sistem |
EP2063905B1 (en) | 2006-09-18 | 2014-07-30 | Raptor Pharmaceutical Inc | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
US7825156B2 (en) * | 2007-02-02 | 2010-11-02 | Copharms | Method of treating bipolar depression with a benzamide derivative |
JP2011526881A (ja) * | 2008-06-25 | 2011-10-20 | ファイザー・インク | ジアリール化合物およびそれらの使用 |
US20100105755A1 (en) * | 2008-09-12 | 2010-04-29 | Auspex Pharmaceuticals, Inc. | Substituted benzamide modulators of dopamine receptor |
DK2398500T3 (da) | 2009-02-20 | 2019-05-13 | 2 Bbb Medicines B V | Glutathion-baseret lægemiddelafgivelsessystem |
ES2942923T3 (es) | 2009-05-06 | 2023-06-07 | Laboratory Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de agente activo-partículas de fosfato de calcio y métodos de uso de las mismas |
CN101898991B (zh) * | 2009-05-31 | 2013-09-25 | 江苏天士力帝益药业有限公司 | 一种(s)(-)-氨磺必利d-(-)-酒石酸盐的合成方法 |
CN101628886B (zh) * | 2009-08-25 | 2012-12-12 | 北京紫萌同达科技有限公司 | 一种2-甲氧基-4-氨基-5-乙砜基苯甲酸的合成方法 |
GB201004020D0 (en) | 2010-03-11 | 2010-04-21 | Acacia Pharma Ltd | New therapeutic use |
AU2016216578B2 (en) * | 2010-03-11 | 2017-11-23 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
AU2014202535B2 (en) * | 2010-03-11 | 2016-05-26 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
EP2582665A1 (en) | 2010-06-17 | 2013-04-24 | Lupin Limited | An improved process for preparation of amisulpride |
US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
CN103304453A (zh) * | 2013-06-18 | 2013-09-18 | 苏州诚和医药化学有限公司 | 两步法合成2-甲氧基-4-氨基-5-乙砜基苯甲酸 |
CN103319384A (zh) * | 2013-06-18 | 2013-09-25 | 苏州诚和医药化学有限公司 | 制备2-甲氧基-4-氨基-5-乙砜基苯甲酸的方法 |
CN103450058B (zh) * | 2013-09-18 | 2015-10-14 | 广安凯特医药化工有限公司 | 一种氨磺必利酸的制备方法 |
CN104725292B (zh) * | 2015-03-23 | 2017-07-25 | 湖北荆江源制药股份有限公司 | 一种(s)(‑)‑氨磺必利的制备方法 |
GB201618425D0 (en) * | 2016-11-01 | 2016-12-14 | Acacia Pharma Ltd | method |
CN111233731B (zh) * | 2016-11-28 | 2021-05-14 | Lb制药公司 | 精神药剂及其用途 |
US11377421B2 (en) | 2016-11-28 | 2022-07-05 | Lb Pharmaceuticals Inc. | Psychotropic agents and uses thereof |
CN106995397B (zh) * | 2016-12-12 | 2020-01-14 | 河北医科大学 | R-氨磺必利药用盐、制备方法、晶型及其用途 |
GB201702250D0 (en) | 2017-02-10 | 2017-03-29 | Acacia Pharma Ltd | Method |
CN112236138B (zh) | 2017-12-05 | 2024-05-31 | 赛诺维信制药公司 | 晶体形式及其制备方法 |
CA3084953A1 (en) | 2017-12-05 | 2019-06-13 | Sunovion Pharmaceuticals Inc. | Nonracemic mixtures and uses thereof |
CN110790693A (zh) * | 2018-08-02 | 2020-02-14 | 北京万全德众医药生物技术有限公司 | 一种(s)(-)-氨磺必利的制备方法 |
SG11202113266YA (en) | 2019-06-04 | 2021-12-30 | Sunovion Pharmaceuticals Inc | Modified release formulations and uses thereof |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
FR2313935A1 (fr) * | 1975-06-10 | 1977-01-07 | Ile De France | Nouveaux benzamides substitues, leurs derives et leur procede de preparation |
US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
FR2244760B1 (sv) * | 1973-09-25 | 1980-06-27 | Ile De France | |
FR2299862B1 (fr) * | 1975-02-07 | 1978-07-21 | Ile De France | Nouveau |
FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
DE2556457C3 (de) * | 1974-12-18 | 1981-02-12 | Synthelabo S.A., Paris | N-(Pyrrolidin-2-yl-methyl)-2-methoxybenzamide, deren Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
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1978
- 1978-01-20 FR FR7801632A patent/FR2415099A1/fr active Granted
- 1978-12-07 BE BE1009179A patent/BE872585A/xx not_active IP Right Cessation
-
1979
- 1979-01-10 BG BG7942018A patent/BG31496A3/xx unknown
- 1979-01-10 AR AR275115A patent/AR221354A1/es active
- 1979-01-10 BG BG7943588A patent/BG31497A3/xx unknown
- 1979-01-11 IL IL56411A patent/IL56411A/xx unknown
- 1979-01-11 YU YU50/79A patent/YU42172B/xx unknown
- 1979-01-11 IN IN21/CAL/79A patent/IN150226B/en unknown
- 1979-01-11 ES ES476755A patent/ES476755A1/es not_active Expired
- 1979-01-12 PT PT69068A patent/PT69068A/pt unknown
- 1979-01-13 DE DE2901181A patent/DE2901181C2/de not_active Expired
- 1979-01-15 CH CH37379A patent/CH637927A5/fr active Protection Beyond IP Right Term
- 1979-01-15 AU AU43373/79A patent/AU528561B2/en not_active Expired
- 1979-01-15 LU LU80786A patent/LU80786A1/xx unknown
- 1979-01-15 GR GR58090A patent/GR64431B/el unknown
- 1979-01-15 NZ NZ189378A patent/NZ189378A/xx unknown
- 1979-01-16 RO RO7996297A patent/RO76393A/ro unknown
- 1979-01-16 SE SE7900380A patent/SE448874B/sv not_active IP Right Cessation
- 1979-01-16 RO RO79103170A patent/RO80311A/ro unknown
- 1979-01-16 MC MC791357A patent/MC1232A1/xx unknown
- 1979-01-17 CY CY1201A patent/CY1201A/xx unknown
- 1979-01-17 GB GB791690A patent/GB2012765B/en not_active Expired
- 1979-01-17 EG EG29/79A patent/EG14045A/xx active
- 1979-01-17 GB GB8118999A patent/GB2083458B/en not_active Expired
- 1979-01-18 DK DK020979A patent/DK158346C/da not_active IP Right Cessation
- 1979-01-18 US US06/004,397 patent/US4294828A/en not_active Expired - Lifetime
- 1979-01-18 IT IT47706/79A patent/IT1164655B/it active Protection Beyond IP Right Term
- 1979-01-18 NO NO790180A patent/NO151320C/no unknown
- 1979-01-18 ZM ZM5/79A patent/ZM579A1/xx unknown
- 1979-01-19 HU HU79SO1241A patent/HU179793B/hu unknown
- 1979-01-19 PL PL1979212899A patent/PL116532B1/pl unknown
- 1979-01-19 CS CS79443A patent/CS226181B2/cs unknown
- 1979-01-19 JP JP54005483A patent/JPS6049192B2/ja not_active Expired
- 1979-01-19 AT AT0039879A patent/AT377977B/de not_active IP Right Cessation
- 1979-01-19 ZA ZA79219A patent/ZA79219B/xx unknown
- 1979-01-19 NL NL7900457A patent/NL191707C/xx not_active IP Right Cessation
- 1979-01-19 PL PL1979224894A patent/PL118151B1/pl unknown
- 1979-01-19 OA OA56717A patent/OA06156A/xx unknown
- 1979-01-19 FI FI790182A patent/FI71126C/fi not_active IP Right Cessation
- 1979-01-19 CA CA319,969A patent/CA1101430A/en not_active Expired
- 1979-01-19 MX MX797669U patent/MX5793E/es unknown
- 1979-01-19 MX MX7911208U patent/MX7623E/es unknown
- 1979-01-19 SU SU792714652A patent/SU820659A3/ru active
- 1979-01-22 DD DD79210583A patent/DD141520A5/de unknown
- 1979-01-30 IE IE92/79A patent/IE47798B1/en active Protection Beyond IP Right Term
- 1979-02-16 ES ES477782A patent/ES477782A1/es not_active Expired
- 1979-08-16 AR AR277738A patent/AR220574A1/es active
- 1979-11-06 PH PH23252A patent/PH15725A/en unknown
-
1980
- 1980-08-20 PH PH24465A patent/PH22287A/en unknown
-
1981
- 1981-10-09 US US06/310,336 patent/US4401822A/en not_active Expired - Lifetime
-
1983
- 1983-02-04 YU YU254/83A patent/YU41278B/xx unknown
-
1984
- 1984-02-16 HK HK121/84A patent/HK12184A/xx not_active IP Right Cessation
-
1986
- 1986-09-09 SE SE8603773A patent/SE460968B/sv not_active IP Right Cessation
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