PL139498B1 - Process for preparing novel derivatives of 4-amino-6,7-dimethoxyquinoline - Google Patents
Process for preparing novel derivatives of 4-amino-6,7-dimethoxyquinoline Download PDFInfo
- Publication number
- PL139498B1 PL139498B1 PL1983243131A PL24313183A PL139498B1 PL 139498 B1 PL139498 B1 PL 139498B1 PL 1983243131 A PL1983243131 A PL 1983243131A PL 24313183 A PL24313183 A PL 24313183A PL 139498 B1 PL139498 B1 PL 139498B1
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- PL
- Poland
- Prior art keywords
- formula
- group
- alkyl
- aryl
- cycloalkyl
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Claims (2)
1. Zastrzezenia patentowe 1. , Sposób wytwarzania nowych pochodnych 4-amino-6,7-dwumetoksychinoliny o ogólnym wzorze 1, w którym R oznacza grupe -M/C^-C^-alkil/2, grupe piperydynowa, grupe 6,7-dwu- metoksy-1,,2,3,4-tetrahydroizochinolilov/a-2 lub grupe o ogólnym wzorze 2, w którym Y ozna¬ cza atom wodoru, grupe Cj-C^-alkilowa, grupe arylowa, grupe C^ ^C^-alkilowa podstawiona rodnikiem arylowym lub aromatyczna grupe heterocykliczna zawierajaca azot i zwiazana z sasiednim atomem azot1.1 Tru^y niperazynylowe j ooorzez atom wegla albo Y oznacza ^rure o wzorze ~C0R , w którym R oznacza grupe C^-Cr-alkilowa, C^-C^-alkilowa, podstawiony rod¬ nikiem arylowym, grupe C^-C^-cykloalkilowa, grupe CT-C^-cykloalkilo/metylowa, grape ary¬ lowa, grupe styrylowa lub grupe heterocykliczna, albo Y oznacza grupe o wzorze -CONHR , w którym R oznacza £rupe C^-C^-alkilowa, grupe arylowa, grupe C^-C^-alkilowa podstawio¬ na rodnikiem arylowym, grupe /C2-CZf-alkenylo/metylowa, grupe C^-Cc-cykloalkilowa lub /c^-Cg-cykloalkilo/metylowa, albo Y oznacza grupe o wzorze -C00R -, w którym ?? oznacza grupe C^-C^-alkilowa, grupe C^-C^-alkilowa podstawiona rodnikiem arylowym, grupe ^-C^- alkilowa podstawiona grupa hydroksylowa w pozycji innej niz przy atomie wegla <£ , grupe C^-Cg-cykloalkilowa, gr^pe /C^-C^-cykloalkilo/metylowa, grupe /C2*C^-alkenylo/metylowa lub grupe arylowa, oraz farmakologicznie dopuszczalnych soli addycyjnych tych zwiazków z kwasami, znamienny tym, ze cyklizuje sie zwiazek o ogólnym wzorze 24, w którym R ma wyzej podane znaczenie, i otrzymany produkt ewentualnie przeprowadza sie w farmakologicznie dopuszczalna sól,
2. Sposób wedlug zastrz, 1, znamienny tym, ze w przypadku wytwa¬ rzania 4-amino-6,7-dwumetoksy-2-/6,7-dwumetoksy-1,2,3,4-tetrahydroizochinolinylo-2/chi¬ noliny cyklizuje sie K-/1-/6,7-dwumetoksy-1,2,3,4-tetrahydroizochinolinylo-2/etylideno]- -2-cyjano-4,5-dwumetoksyaniline.139 498 Nx/R -kRj-y Wzór 2 Wzór 1 Wzór 7 -U IH™3 N(CH^ N Wzór9 Ylzór 10 N-N VS CH3 Wzór 8 N=/ CK WaJr /2 7/ N N Wzór 13139 498 N< OCH, OCH3 1/1zór 14 N-N " VCl ^ M-CjH, 0K0 N Wzór 17 X) WzcV 2"6 NHC^j Wzór 15 Wzór 16 N-N '/ \\ N-N -^J-O-n-Cjft Wzór 19 < M CH 3 WZ(5f22 chp^\nCH5 Wzór 24139 496 i Wzór 25 Wzór 28 N NH \ / Wzór 26 -C- ii o // \\ Wzór 27 O ^ Wzór 29 O Wzór 30 AAn/ v^0 O Wzór 33 // W u O Wzór 3^ O Wzór 36139 498 ,C/NH-CH ii O Wzór 37 N CH N =J Wzór 39 n^°<3 =J N Wzór 38 -COO // \\ Wzór 40 COO-CHff X Wzór M \_N-C6H5 Wzór 42 -rQjcocF, Wzór Wi . OCH3 Wzór UU139 498 o: o o 9) qt c8 Q X X o o o X o O)139 ^93 CH£ NfvNv^L_NC6H5 ¦ _LDA^ CHp- CHjO NHZ Schemat 3 ^W^O«* |& WC^AjP* / !V^ WHfeH5 Schemat 4-139 498 O ro -SO' -r X X|0 co X O Osi So OJ Mo OJ to139 498 cO i O CS So CU 3 U O ta x x o o OD Sj S OJ 3 Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 130 zl PL PL
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8221457 | 1982-07-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
PL243131A1 PL243131A1 (en) | 1984-12-17 |
PL139498B1 true PL139498B1 (en) | 1987-01-31 |
Family
ID=10531886
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1983243131A PL139498B1 (en) | 1982-07-24 | 1983-07-21 | Process for preparing novel derivatives of 4-amino-6,7-dimethoxyquinoline |
Country Status (26)
Country | Link |
---|---|
US (3) | US4656174A (pl) |
EP (1) | EP0100200B1 (pl) |
JP (1) | JPS5933264A (pl) |
KR (1) | KR880001315B1 (pl) |
AU (1) | AU548036B2 (pl) |
CA (1) | CA1255670A (pl) |
CS (1) | CS247073B2 (pl) |
DD (1) | DD211555A5 (pl) |
DE (1) | DE3371336D1 (pl) |
DK (1) | DK166821B1 (pl) |
ES (1) | ES8504131A1 (pl) |
FI (1) | FI78296C (pl) |
GR (1) | GR79603B (pl) |
HK (1) | HK32289A (pl) |
HU (1) | HU190907B (pl) |
IE (1) | IE55798B1 (pl) |
IL (1) | IL69311A (pl) |
NO (1) | NO171594C (pl) |
NZ (1) | NZ204996A (pl) |
PH (1) | PH19424A (pl) |
PL (1) | PL139498B1 (pl) |
PT (1) | PT77082B (pl) |
SG (1) | SG6489G (pl) |
SU (2) | SU1251801A3 (pl) |
YU (1) | YU42628B (pl) |
ZA (1) | ZA835355B (pl) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT384218B (de) * | 1985-12-04 | 1987-10-12 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen chinazolin-derivaten |
GB8716972D0 (en) * | 1987-07-17 | 1987-08-26 | Pfizer Ltd | Treatment of cardiac arrhythmias |
GB8719378D0 (en) * | 1987-08-15 | 1987-09-23 | Pfizer Ltd | Antiarrythmic agents |
US4882337A (en) * | 1988-08-12 | 1989-11-21 | Pfizer Inc. | Tetrahydroisoquinoline antiarrhythmic agents |
US5304554A (en) * | 1990-04-27 | 1994-04-19 | Emory University | 4-[(alkyl or dialkyl)amino]quinolines and their method of preparation |
US5270323A (en) * | 1990-05-31 | 1993-12-14 | Pfizer Inc. | Method of treating impotence |
PT100905A (pt) * | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
TW304945B (pl) * | 1992-06-27 | 1997-05-11 | Hoechst Ag | |
RU2118322C1 (ru) * | 1993-07-05 | 1998-08-27 | Дюфар Интернэшнл Рисерч Б.В. | 2,3-дигидро-1,4-бензодиокси-5-ил-пиперазиновые производные или их соли |
US6143746A (en) * | 1994-01-21 | 2000-11-07 | Icos Corporation | Tetracyclic cyclic GMP-specific phosphodiesterase inhibitors, process of preparation and use |
GB9514465D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
GB9514464D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Medicaments |
GB9514473D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
GB9526546D0 (en) * | 1995-12-23 | 1996-02-28 | Pfizer Ltd | Compounds useful in therapy |
ATE215950T1 (de) * | 1996-05-10 | 2002-04-15 | Icos Corp | Carbolinderivate |
GB9700504D0 (en) * | 1997-01-11 | 1997-02-26 | Pfizer Ltd | Pharmaceutical compounds |
GB9708917D0 (en) * | 1997-05-01 | 1997-06-25 | Pfizer Ltd | Compounds useful in therapy |
GB9711650D0 (en) * | 1997-06-05 | 1997-07-30 | Pfizer Ltd | Compounds useful in therapy |
AU8066701A (en) | 2000-07-20 | 2002-02-05 | Neurogen Corp | Capsaicin receptor ligands |
DE10035928A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
EP1178036A1 (en) | 2000-08-04 | 2002-02-06 | Aventis Cropscience S.A. | Fungicidal phenylimidate derivatives |
US6900220B2 (en) | 2001-01-02 | 2005-05-31 | Syntex (U.S.A.) Llc | Quinazolone derivatives as alpha 1A/B adrenergic receptor antagonists |
KR100420663B1 (ko) * | 2001-01-09 | 2004-03-02 | 주식회사 켐온 | 퀴놀린 유도체, 그의 제조방법 및 그를 포함하는 약학적조성물 |
US6734303B2 (en) | 2001-05-18 | 2004-05-11 | Pfizer Inc. | Process for the production of quinazolines |
US7084156B2 (en) * | 2001-11-27 | 2006-08-01 | Merck & Co., Inc. | 2-Aminoquinoline compounds |
CN101304743B (zh) * | 2005-09-19 | 2012-09-05 | 诺伊罗纳森特公司 | 刺激神经形成和抑制神经元变性的方法和组合物 |
AU2013211455B2 (en) * | 2005-09-19 | 2017-12-07 | Neuronascent, Inc. | Methods and compositions for stimulating neurogenesis and inhibiting neuronal degeneration |
WO2008070121A1 (en) * | 2006-12-06 | 2008-06-12 | Cornell Research Foundation, Inc. | Intermediate duration neuromuscular blocking agents and antagonists thereof |
WO2010107488A1 (en) | 2009-03-17 | 2010-09-23 | Cornell University | Reversible nondepolarizing neuromuscular blockade agents and methods for their use |
US9220700B2 (en) | 2009-08-19 | 2015-12-29 | Cornell University | Cysteine for physiological injection |
WO2013192345A1 (en) | 2012-06-20 | 2013-12-27 | Novartis Ag | Complement pathway modulators and uses thereof |
TWI649308B (zh) * | 2013-07-24 | 2019-02-01 | 小野藥品工業股份有限公司 | 喹啉衍生物 |
Family Cites Families (17)
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GB890533A (en) * | 1959-11-09 | 1962-03-07 | Allen & Hanburys Ltd | Improvements in or relating to heterocyclic quaternary ammonium salts |
CH414637A (de) * | 1962-08-31 | 1966-06-15 | Geigy Ag J R | Verfahren zur Herstellung von Carbostyrilderivaten |
US3272824A (en) * | 1962-12-06 | 1966-09-13 | Norwich Pharma Co | 4-amino-6, 7-di(lower) alkoxyquinolines |
US3542785A (en) * | 1967-05-15 | 1970-11-24 | Ciba Geigy Corp | 2-hydroxy-4-aryl-quinolines |
US3517005A (en) * | 1967-10-26 | 1970-06-23 | Pfizer & Co C | Certain 2- and 4-substituted quinazolines |
US3511836A (en) * | 1967-12-13 | 1970-05-12 | Pfizer & Co C | 2,4,6,7-tetra substituted quinazolines |
US3629418A (en) * | 1969-02-14 | 1971-12-21 | Miles Lab | Process for producing an anti-depressant effect with piperazine quinolines |
GB1383409A (en) * | 1972-09-09 | 1974-02-12 | Pfizer Ltd | Derivatives of 2-amino- and 4-amino-quinazoline and pharmaceutical compositions containing them |
US4035367A (en) * | 1974-09-09 | 1977-07-12 | Sandoz, Inc. | Hydroxyalkyl-substituted-amino-quinolines |
US4188390A (en) * | 1977-11-05 | 1980-02-12 | Pfizer Inc. | Antihypertensive 4-amino-2-[4-(1,4-benzodioxan-2-carbonyl) piperazin-1-yl or homopiperazin-1-yl]quinazolines |
JPS54125688A (en) * | 1978-02-27 | 1979-09-29 | Mitsubishi Yuka Yakuhin Kk | Novel quinazoline derivative*its manufacture and antihypertensive drug |
JPS5480372A (en) * | 1977-12-12 | 1979-06-27 | Toray Ind Inc | Production of fishing rod made of carbon fiber-reinforced resin |
JPS54122283A (en) * | 1978-03-13 | 1979-09-21 | Sumitomo Chem Co Ltd | Novel quinazoline derivative and its preparation |
JPS54128588A (en) * | 1978-03-29 | 1979-10-05 | Dainippon Pharmaceut Co Ltd | Antidepressive drugs consisting mainly of 2-(1-piperazinyl)- 4-phenylquinoline |
JPS54128582A (en) * | 1978-03-30 | 1979-10-05 | Sumitomo Chem Co Ltd | Novel quinazoline derivative and its preparation |
US4287341A (en) * | 1979-11-01 | 1981-09-01 | Pfizer Inc. | Alkoxy-substituted-6-chloro-quinazoline-2,4-diones |
DE3034001A1 (de) * | 1980-09-10 | 1982-04-22 | Hoechst Ag, 6000 Frankfurt | Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung |
-
1983
- 1983-07-19 GR GR71969A patent/GR79603B/el unknown
- 1983-07-19 US US06/515,095 patent/US4656174A/en not_active Expired - Lifetime
- 1983-07-20 EP EP83304196A patent/EP0100200B1/en not_active Expired
- 1983-07-20 DE DE8383304196T patent/DE3371336D1/de not_active Expired
- 1983-07-21 ES ES524320A patent/ES8504131A1/es not_active Expired
- 1983-07-21 FI FI832658A patent/FI78296C/fi not_active IP Right Cessation
- 1983-07-21 PL PL1983243131A patent/PL139498B1/pl unknown
- 1983-07-22 NO NO832688A patent/NO171594C/no not_active IP Right Cessation
- 1983-07-22 SU SU833618703A patent/SU1251801A3/ru active
- 1983-07-22 ZA ZA835355A patent/ZA835355B/xx unknown
- 1983-07-22 DK DK337383A patent/DK166821B1/da not_active IP Right Cessation
- 1983-07-22 KR KR1019830003392A patent/KR880001315B1/ko not_active IP Right Cessation
- 1983-07-22 AU AU17222/83A patent/AU548036B2/en not_active Expired
- 1983-07-22 CA CA000433023A patent/CA1255670A/en not_active Expired
- 1983-07-22 HU HU832594A patent/HU190907B/hu unknown
- 1983-07-22 IL IL69311A patent/IL69311A/xx not_active IP Right Cessation
- 1983-07-22 JP JP58134244A patent/JPS5933264A/ja active Granted
- 1983-07-22 NZ NZ204996A patent/NZ204996A/en unknown
- 1983-07-22 YU YU1572/83A patent/YU42628B/xx unknown
- 1983-07-22 PT PT77082A patent/PT77082B/pt unknown
- 1983-07-22 CS CS835509A patent/CS247073B2/cs unknown
- 1983-07-22 IE IE1730/83A patent/IE55798B1/en not_active IP Right Cessation
- 1983-07-22 DD DD83253330A patent/DD211555A5/de not_active IP Right Cessation
- 1983-07-25 PH PH29286A patent/PH19424A/en unknown
-
1984
- 1984-04-26 SU SU843732816A patent/SU1340589A3/ru active
-
1986
- 1986-10-30 US US06/925,029 patent/US4686228A/en not_active Expired - Lifetime
-
1987
- 1987-05-11 US US07/048,343 patent/US4758568A/en not_active Expired - Lifetime
-
1989
- 1989-02-04 SG SG64/89A patent/SG6489G/en unknown
- 1989-04-20 HK HK322/89A patent/HK32289A/xx not_active IP Right Cessation
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