PL110780B1 - Method of producing new derivatives of quinazolone - Google Patents
Method of producing new derivatives of quinazolone Download PDFInfo
- Publication number
- PL110780B1 PL110780B1 PL1976209362A PL20936276A PL110780B1 PL 110780 B1 PL110780 B1 PL 110780B1 PL 1976209362 A PL1976209362 A PL 1976209362A PL 20936276 A PL20936276 A PL 20936276A PL 110780 B1 PL110780 B1 PL 110780B1
- Authority
- PL
- Poland
- Prior art keywords
- compounds
- quinazolone
- group
- producing new
- new derivatives
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Opis patentowy opublikowano: 27.02.1982 — i , ! U 110780 In/t, Cl.2 C07D 471/04 C07D 487/04 C07D 513/04 Twórca wynalazku: Uprawniony z patentu: C. H. Boehringer Sotai, Ingelheim n/Renem (Republika Federalna Niemiec) Sposób wytwarzania nowych pochodnych chinazolonu 1 Przedmiotem wy/nadazku jeat gpoisófo wytwarza¬ nia nowych pcchiodiniycih chinazolonu o wzorze ogólnym 1, w którym A oznacza grupe —OH = CH—, —S— i —GH = Ni—, Ri oznacza altem wo¬ doru, doikomdlerisciwafliy pierscien benzenowy, grupe aminowa lmb karibicksylowa, R2 oznacza grupe kar¬ boksylowa, cyjeinowia, tetiraizolilcwa-5 lub w przy¬ padku gdy Ri oznacza grupe karjboksyl-cwa, ozna¬ cza równiez grupe alkilowa o 1—4 atomach weigla lufo grupe alkioksylcwa o 1—4 atomach wegla lufo dokonidiensrcwany pierscien bemzemcwy, .przy czym wiazanie R* prowadzi do pozycji 2 lub 3 i przy czym co najmniej jeden z symboli Ri = R2 ozna¬ cza grupe kaifbcteylowa ora-z ich scili.Zwiajzki o wzorrze 1 moga wystepowac w po¬ staci wolnych zwiazków, a równiez w postaci soli z zasadami lub kwasami.A oznacza, zwlaszcza —S— przede wszyisitkiim Jednak grupe —CH = CH—. W ramach wyzej po¬ danej definicji Ri oznacza zwlaszcza wodór, zas Ri i R2 oznaczaja zwlaszcza diókonidtensowany pier¬ scien benzenowy, grupe tetrazoli'lowa-<5.Wedlug wynalazku nowe zwiazki wytwarza sie przez hydrolize zwiazku o wzorze 2, w którym Ri" ma znaczeniie talkie jak Ri lub oznacza grupe estrowa lub amidowa, przy czym co najmniej je- dem z symboli Ri" i R2" stanowi grupe ulegajaca h^^dTioliizie, za pomoca woidnych roztworów kwa¬ sów lwb zasa4 w tempefratutrze od 0°C do tem- 10 15 20 25 30 perailjuiry wrzenia mieszaniny reakcyjnej. Zwiazki o wzorze 2 sa zwiazkami .nowymi.Amikfly, kwas hydrcksamcwy i e/ster otrzymuje sie z amoniakiem! luib amiinafcetrazolem z odpowied¬ nim nizszym alkoholem lufo hydroksyloamina. Re¬ akcja cic|powieid'niego» nitrylu z azydkiem sodowym daje zwiazek tetrazoflilowy-S, grupe cyjanowa moz¬ na otrzymac z odpowiedniego zwiazku kanbamy- lowcigo, gnujpy kasrlboksylowe otrzymuje sie prizez zmyslenie ccipowiedmich esitrów lufo amidów lub ewentualnie przez utlenienie grup metylowych, np. nadmanganianem potasowym, grupy amino¬ we uzyskuje sie przez kwasowe lufo a'lkail;czne zmydlkinie citfpiowiedinieh grup acyloaminowych.Otrzymstne zwiazki, naiatejpnie ewentualnie prze¬ prowadza sie w sole addycyjne z kwasem, lub o ile zawieraja grupy karbciksylowe, równiez w siole z organicznymi lufo nieorganicznymi zasada¬ mi. Z otrzymanych pierwotnie soli eweinituafllnie uwalnia sie wolne zwiazki o wzorze 1, Produtety wyjsciowe otrzymuje sie znanymi jako tefcóe sposobami.Otrzymywane spcizobem w&cfclug wynalazku no¬ we zwiazki znajduja, zaistoocwainie w terapeutyce lub ..moga .sluzyc jaka produkty pcsred.ncie do wy¬ twarzania srodków leczniczych, przy czyim ns.lezy podkreslic ich dziaianje przeciwailergiczne. Leki t2 mozna wykorzystac w profilaktyce i leczeniu scho¬ rzen alergicznych, takich jak aistaa lufo goraczka sienna, zapalenie spojówek, pokrzywka, egzema, 110 7803 110 780 4 uczuleniowe zapalanie skóry. Zwiazki te wykazuja 'ponadto dzialanie bronchodylatoryjne i rozszerza¬ jace naczynia. Przy najwazniejszym sitoisowamiu, a mianowicie w profiilalkityice astmy, nalezy wymie- mic jako- zalety w stcisiuriku do prcdiukfcu handlo¬ wego kwasu kroimoglieyinowego, dftuizigzy okres dzialania i przede wiszy's Znanym produktem handlowym o podobnym dzialaniu j'eist kromoglikaminian sodowy, tak zwa¬ ny IritaiR, o wzorze A. Wczesniej, jeszcze w ho- lendleinskim opisie paltenitowyim nr 6 414 7117 omó¬ wiony jesit zwiazek oi Wzorze B.Poddajac rózne zwiazki badaniom na test PCA (hamowanie pasywnej skórnej anafilaksji) na ich dizialanie przeciwalergicznei, okazalo sie, ze zwiaz¬ ki otrzymywane spoisoibeim wedHug wynalazku w przeciwienstwie do nieczynnych doustnie znanych zwia'zlków porównawczych!, wykazuja dcfore dzia¬ lanie przy stosowaniu doustnym.Tak wiec przy ,s -piry(do[2i3|l-Ib] -ichiinaizolano-e-Ikaribcksylowego do¬ ustnie szczurom LD50 wynosi 2,7 m(g/kig przy bar¬ dzo malej toksycznosci (LD50 dla myszy, doustnie 2000 mg/kg).Równiez inne otrzymywane spcso-beim wedlbug wynalazku suffcfstancije czyinne wykazuja dobre dzialanie prizy stosowaniu douistnym, jak wskazuja daine w przy/toczonej nizej tafcliey.I. kwas ll-keto-ll-H-(pirydo[2,lHb]-(ch'iinazolino-2- -karibctoylowy,' II. kwas 12nkeltio-il2i-H^chLno{24-b]- -ka.r(boksy(Lcwy, III. Ikrwas 11 -kato-ll 1 -H-2Mmetokisypkydo[2Ji -Ib]-chi- naizclino-8-karblclkisyIowy, IV. kwas ll-«keto-H-pirydo{2,l-6]-chi'na!zolino-34car- boksylowy, V. kwais e-ke-to-e-H-ipiTymidot^l-tol-chiinazolinoi- -Q-(kairbokisydowy.T a b 1 i c a 1 Sub¬ stancja ¦A ' B I II III IV V Dawka (img/kg) 100 100 ¦ 2i,7 100,0 100,0 100,0 100,0 Zahamowaffiie 1 * PCA PL PL PL PL PL PL PL
Claims (1)
1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2557425A DE2557425C2 (de) | 1975-12-19 | 1975-12-19 | 11-Oxo-11-H-pyrido[2,1-b]-chinazolin-2-carbonsäure und ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL110780B1 true PL110780B1 (en) | 1980-07-31 |
Family
ID=5964943
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976201604A PL102308B1 (pl) | 1975-12-19 | 1976-12-18 | A method of producing new derivatives of quinazolone |
| PL1976201603A PL103556B1 (pl) | 1975-12-19 | 1976-12-18 | Sposob wytwarzania nowych pochodnych chinazolonu |
| PL1976194519A PL101141B1 (pl) | 1975-12-19 | 1976-12-18 | Sposob wytwarzania nowych pochodnych chinazolonu |
| PL1976209361A PL111422B1 (en) | 1975-12-19 | 1976-12-18 | Process for the preparation of novel derivatives of quinazolone |
| PL1976209362A PL110780B1 (en) | 1975-12-19 | 1976-12-18 | Method of producing new derivatives of quinazolone |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976201604A PL102308B1 (pl) | 1975-12-19 | 1976-12-18 | A method of producing new derivatives of quinazolone |
| PL1976201603A PL103556B1 (pl) | 1975-12-19 | 1976-12-18 | Sposob wytwarzania nowych pochodnych chinazolonu |
| PL1976194519A PL101141B1 (pl) | 1975-12-19 | 1976-12-18 | Sposob wytwarzania nowych pochodnych chinazolonu |
| PL1976209361A PL111422B1 (en) | 1975-12-19 | 1976-12-18 | Process for the preparation of novel derivatives of quinazolone |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US4083980A (pl) |
| JP (1) | JPS5831350B2 (pl) |
| AT (1) | AT352736B (pl) |
| AU (1) | AU513469B2 (pl) |
| BE (1) | BE849542A (pl) |
| BG (3) | BG25092A3 (pl) |
| CA (1) | CA1199914A (pl) |
| CH (4) | CH627754A5 (pl) |
| CS (1) | CS198222B2 (pl) |
| DD (1) | DD128812A5 (pl) |
| DE (1) | DE2557425C2 (pl) |
| DK (1) | DK149107C (pl) |
| ES (3) | ES454405A1 (pl) |
| FI (1) | FI64159C (pl) |
| FR (1) | FR2335229A1 (pl) |
| GB (1) | GB1572707A (pl) |
| GR (1) | GR62109B (pl) |
| HK (1) | HK12984A (pl) |
| HU (1) | HU172929B (pl) |
| IE (1) | IE45256B1 (pl) |
| IL (1) | IL51124A (pl) |
| LU (1) | LU76417A1 (pl) |
| MX (1) | MX4488E (pl) |
| MY (1) | MY8500078A (pl) |
| NL (1) | NL182535C (pl) |
| NO (1) | NO147450C (pl) |
| NZ (1) | NZ182915A (pl) |
| PH (1) | PH16310A (pl) |
| PL (5) | PL102308B1 (pl) |
| PT (1) | PT65981A (pl) |
| RO (3) | RO75248A (pl) |
| SE (1) | SE431456B (pl) |
| SG (1) | SG55483G (pl) |
| SU (4) | SU645571A3 (pl) |
| YU (2) | YU39048B (pl) |
| ZA (1) | ZA767490B (pl) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337255A (en) * | 1977-07-29 | 1982-06-29 | E. R. Squibb & Sons, Inc. | Pyrazolo[1,5-c]quinazoline derivatives and related compounds |
| HU182009B (en) * | 1977-08-19 | 1983-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted pirido-square bracket-1,2-a-square bracket closed-pyrimidines, pyrrolo-square bracket-1,2-a-square bracket closed-pyrimidines |
| DE2739020A1 (de) | 1977-08-26 | 1979-03-01 | Schering Ag | Pyrido eckige klammer auf 2,1-b eckige klammer zu -chinazolinon-derivate, ihre herstellung und verwendung |
| US4348396A (en) * | 1978-01-23 | 1982-09-07 | Hoffmann-La Roche Inc. | Substituted 11-oxo-11H-pyrido[2,1-b]quinazolines and method of inhibiting allergic reactions with them |
| US4168380A (en) | 1978-04-21 | 1979-09-18 | Hoffmann-La Roche Inc. | 7-Methoxy-5-oxo-5H-thiazolo[2,3-b]quinazoline-2-carboxylic acid |
| US4491587A (en) * | 1978-05-05 | 1985-01-01 | Mead Johnson & Company | Tetrazole derivatives |
| US4223031A (en) * | 1978-05-05 | 1980-09-16 | Mead Johnson & Company | Azolopyrimidinones |
| US4209620A (en) * | 1978-06-19 | 1980-06-24 | Bristol-Myers Company | Substituted 3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives having antiallergy activity |
| DE2845766A1 (de) * | 1978-10-18 | 1980-04-30 | Schering Ag | Pyrido eckige klammer auf 2,1-b eckige klammer zu -chinazolinon-derivate, ihre herstellung und verwendung |
| EP0015065B1 (en) * | 1979-01-24 | 1983-12-28 | Warner-Lambert Company | Pyrazolo (5,1-b) quinazolin-9(4h)-one derivatives, process for their preparation and pharmaceutical compositions containing them |
| US4282360A (en) * | 1979-10-12 | 1981-08-04 | Hoffmann-La Roche Inc. | 7-Methylthio or methylsulfinyl-5-oxo-5H-thiazolo[2,3-b]quinazoline-2-carboxylic acid |
| US4302585A (en) | 1980-12-22 | 1981-11-24 | American Home Products Corporation | 3-Hydroxy-3-substituted phenylthiazolo[2,3-b]quinazoline-2-alkanoic acids and their lactones |
| US4395549A (en) | 1981-10-02 | 1983-07-26 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | 6-Hydrazono-pyrido[2,1-b] quinazoline-11 ones |
| DE3142727A1 (de) * | 1981-10-28 | 1983-05-05 | Basf Ag, 6700 Ludwigshafen | Thiazolo (2,3-b)-chinazolone, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des pflanzenwachstums |
| DE3142728A1 (de) * | 1981-10-28 | 1983-05-05 | Basf Ag, 6700 Ludwigshafen | Herbizide, enthaltend thiazolo(2,3-b)-chinazolone als wirkstoffe, und ihre verwendung zur beeinflussung des pflanzenwachstums |
| ES8406476A1 (es) * | 1982-04-29 | 1984-07-01 | Erba Farmitalia | Procedimiento para preparar derivados cicloalifaticos condensados de pirido(1,2-a)pirimidinas sustituidas. |
| US4551460A (en) * | 1982-05-10 | 1985-11-05 | Hoffmann-La Roche Inc. | Pyrido[2,1-b]quinazoline derivatives useful as agents for treatment of allergic conditions and vascular disorders involving thrombosis |
| US4455312A (en) * | 1982-08-19 | 1984-06-19 | Portnyagina Vera A | 2-(o-Carboxyphenylamino)-6H-pyrimido(2,1-b)-quinazolone-6 and derivatives thereof, and application as antiphlogistics |
| DE3300477A1 (de) * | 1983-01-08 | 1984-07-12 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue heterocyclische verbindungen, ihre herstellung und verwendung |
| GB8300728D0 (en) * | 1983-01-12 | 1983-02-16 | Erba Farmitalia | Substituted carboxy-thiazolo / 3 2 - a / pyrimidine derivatives |
| EP0142057A3 (en) * | 1983-11-04 | 1988-03-30 | F. Hoffmann-La Roche Ag | Thiazoloquinazoline derivatives, their preparation and pharmaceutical compositions containing same |
| US4738964A (en) * | 1984-05-30 | 1988-04-19 | Pennwalt Corporation | Method of suppressing the immune system comprising administering 5H-thiazolo[2,3-b]quinazoline-3(2H)-one |
| US4588812A (en) * | 1984-05-30 | 1986-05-13 | Pennwalt Corporation | Substituted 2,3-dihydro-5H-thiazolo[2,3,-b]quinazoline derivatives |
| DE3634532A1 (de) * | 1986-10-10 | 1988-04-14 | Basf Ag | Verfahren zur herstellung von thiazolo-(2,3-b)chinazolonen |
| DE3704203A1 (de) * | 1987-02-11 | 1988-08-25 | Boehringer Ingelheim Kg | Verwendung von oxochinazolinderivaten bei der behandlung der hyperurikaemie |
| US4904667A (en) * | 1989-02-24 | 1990-02-27 | Ortho Pharmaceutical Corporation | 1H-1,2,4-thiadiazolo(3,4-b)quinazolin-5-one-2,2-dioxides, and a method for increasing the cardiac output of a mammal with them |
| US6800651B2 (en) | 2000-02-03 | 2004-10-05 | Eli Lilly And Company | Potentiators of glutamate receptors |
| US8946223B2 (en) | 2010-04-12 | 2015-02-03 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US8765773B2 (en) | 2010-10-18 | 2014-07-01 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US10183934B2 (en) | 2015-02-02 | 2019-01-22 | Forma Therapeutics, Inc. | Bicyclic [4,6,0] hydroxamic acids as HDAC inhibitors |
| US10239845B2 (en) | 2015-02-02 | 2019-03-26 | Forma Therapeutics, Inc. | 3-aryl-4-amido-bicyclic [4,5,0] hydroxamic acids as HDAC inhibitors |
| EP3472131B1 (en) | 2016-06-17 | 2020-02-19 | Forma Therapeutics, Inc. | 2-spiro-5- and 6-hydroxamic acid indanes as hdac inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1242863A (en) * | 1968-05-10 | 1971-08-18 | Pharmacia As | 2,3-DIHYDRO-5H-THIAZOLO[2,3-b]QUINAZOLINES AND PROCESSES FOR THE PREPARATION THEREOF |
| US3598823A (en) * | 1969-05-28 | 1971-08-10 | Sandoz Ag | Tricyclic quinazolinones |
| US3833588A (en) * | 1972-04-25 | 1974-09-03 | Sandoz Ag | Unsaturated-substituted tricyclic quinazolinones |
| JPS5752352B2 (pl) * | 1974-02-28 | 1982-11-06 | ||
| US4012387A (en) * | 1975-09-18 | 1977-03-15 | Warner-Lambert Company | Benzo-[g]pyrido[2,1-b]quinazolinones |
| US4033961A (en) * | 1975-10-07 | 1977-07-05 | Warner-Lambert Company | Pyrido[2-1-b]quinazolin-ones and their methods of preparation |
| US4142049A (en) * | 1976-10-18 | 1979-02-27 | Warner-Lambert Company | Benzo[g]pyrido[2,1-b]quinazolinones |
| US4066767A (en) * | 1976-11-01 | 1978-01-03 | Warner-Lambert Company | 8-(1H-Tetrazol-5-yl)-11H-pyrido[2,1-b]quinazolin-11-ones and method of treating bronchial asthma using them |
| MC1186A1 (fr) | 1977-03-24 | 1978-12-22 | Hoffmann La Roche | Derives de quinazoline |
| DE2739020A1 (de) * | 1977-08-26 | 1979-03-01 | Schering Ag | Pyrido eckige klammer auf 2,1-b eckige klammer zu -chinazolinon-derivate, ihre herstellung und verwendung |
| US4168380A (en) * | 1978-04-21 | 1979-09-18 | Hoffmann-La Roche Inc. | 7-Methoxy-5-oxo-5H-thiazolo[2,3-b]quinazoline-2-carboxylic acid |
-
1975
- 1975-12-19 DE DE2557425A patent/DE2557425C2/de not_active Expired
-
1976
- 1976-11-30 AT AT883976A patent/AT352736B/de not_active IP Right Cessation
- 1976-12-02 FI FI763469A patent/FI64159C/fi not_active IP Right Cessation
- 1976-12-07 GR GR52342A patent/GR62109B/el unknown
- 1976-12-14 CS CS768172A patent/CS198222B2/cs unknown
- 1976-12-15 RO RO7695226A patent/RO75248A/ro unknown
- 1976-12-15 RO RO7695227A patent/RO75734A/ro unknown
- 1976-12-15 RO RO7688735A patent/RO69411A/ro unknown
- 1976-12-15 US US05/750,725 patent/US4083980A/en not_active Expired - Lifetime
- 1976-12-16 DD DD7600196412A patent/DD128812A5/xx unknown
- 1976-12-16 SU SU762429454A patent/SU645571A3/ru active
- 1976-12-16 DK DK567376A patent/DK149107C/da not_active IP Right Cessation
- 1976-12-16 CH CH284581A patent/CH627754A5/de not_active IP Right Cessation
- 1976-12-16 CH CH1583776A patent/CH625522A5/de not_active IP Right Cessation
- 1976-12-17 AU AU20695/76A patent/AU513469B2/en not_active Expired
- 1976-12-17 LU LU76417A patent/LU76417A1/xx unknown
- 1976-12-17 HU HU76BO00001645A patent/HU172929B/hu not_active IP Right Cessation
- 1976-12-17 ZA ZA00767490A patent/ZA767490B/xx unknown
- 1976-12-17 SE SE7614258A patent/SE431456B/xx not_active IP Right Cessation
- 1976-12-17 JP JP51151051A patent/JPS5831350B2/ja not_active Expired
- 1976-12-17 IE IE2777/76A patent/IE45256B1/en not_active IP Right Cessation
- 1976-12-17 NL NLAANVRAGE7614013,A patent/NL182535C/xx not_active IP Right Cessation
- 1976-12-17 PT PT65981A patent/PT65981A/pt unknown
- 1976-12-17 FR FR7638135A patent/FR2335229A1/fr active Granted
- 1976-12-17 MX MX765246U patent/MX4488E/es unknown
- 1976-12-17 BG BG034932A patent/BG25092A3/xx unknown
- 1976-12-17 BE BE173384A patent/BE849542A/xx not_active IP Right Cessation
- 1976-12-17 BG BG035901A patent/BG24673A3/xx unknown
- 1976-12-17 YU YU03082/76A patent/YU39048B/xx unknown
- 1976-12-17 BG BG035902A patent/BG25093A3/xx unknown
- 1976-12-17 NO NO764303A patent/NO147450C/no unknown
- 1976-12-17 NZ NZ182915A patent/NZ182915A/xx unknown
- 1976-12-17 IL IL51124A patent/IL51124A/xx unknown
- 1976-12-17 CA CA000268164A patent/CA1199914A/en not_active Expired
- 1976-12-17 GB GB52857/76A patent/GB1572707A/en not_active Expired
- 1976-12-18 PL PL1976201604A patent/PL102308B1/pl unknown
- 1976-12-18 PL PL1976201603A patent/PL103556B1/pl unknown
- 1976-12-18 PL PL1976194519A patent/PL101141B1/pl unknown
- 1976-12-18 PL PL1976209361A patent/PL111422B1/pl unknown
- 1976-12-18 ES ES454405A patent/ES454405A1/es not_active Expired
- 1976-12-18 PL PL1976209362A patent/PL110780B1/pl unknown
-
1977
- 1977-09-23 SU SU772524306A patent/SU733516A3/ru active
- 1977-09-23 SU SU772524307A patent/SU652894A3/ru active
- 1977-11-15 ES ES464136A patent/ES464136A1/es not_active Expired
- 1977-11-15 ES ES464162A patent/ES464162A1/es not_active Expired
-
1978
- 1978-07-12 SU SU782633660A patent/SU784776A3/ru active
-
1980
- 1980-05-02 PH PH23979A patent/PH16310A/en unknown
- 1980-11-05 US US06/204,226 patent/US4332802A/en not_active Expired - Lifetime
- 1980-11-13 CH CH843880A patent/CH625243A5/de not_active IP Right Cessation
-
1981
- 1981-10-28 CH CH689681A patent/CH631983A5/de not_active IP Right Cessation
-
1982
- 1982-05-31 YU YU1152/82A patent/YU40078B/xx unknown
-
1983
- 1983-09-01 SG SG554/83A patent/SG55483G/en unknown
-
1984
- 1984-02-16 HK HK129/84A patent/HK12984A/xx unknown
-
1985
- 1985-12-30 MY MY78/85A patent/MY8500078A/xx unknown
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