PL84339B1 - 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] - Google Patents
1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] Download PDFInfo
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- PL84339B1 PL84339B1 PL1970174657A PL17465770A PL84339B1 PL 84339 B1 PL84339 B1 PL 84339B1 PL 1970174657 A PL1970174657 A PL 1970174657A PL 17465770 A PL17465770 A PL 17465770A PL 84339 B1 PL84339 B1 PL 84339B1
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- formula
- hydroxy
- compound
- cyanophenoxy
- salts
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- 150000003839 salts Chemical class 0.000 title claims description 9
- MAXGKGLXEAPYGY-UHFFFAOYSA-N 2-[3-(ethylamino)-2-hydroxypropoxy]benzonitrile Chemical compound CCNCC(O)COC1=CC=CC=C1C#N MAXGKGLXEAPYGY-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- JFUBFTVIDOXELL-UHFFFAOYSA-N 2-(3-amino-2-hydroxypropoxy)benzonitrile Chemical compound NCC(O)COC1=CC=CC=C1C#N JFUBFTVIDOXELL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia l-(2-cyjanofenoksy)-2-hydroksy-3-etyloamino- propanu o wzorze 1, jak równiez jego soli addy¬ cyjnych z kwasami. Jest to zwiazek nowy i moze znalezc zastosowanie jako srodek leczniczy.Wedlug wynalazku nowy zwiazek wytwarza sie przez wprowadzanie grupy etylowej do l-(2-cyja- nofenoksy)-2-hydroksy-3-aminopropanu o wzorze 2 droga reakcji z elektrofilowym zwiazkiem o wzo¬ rze 3, w którym X oznacza latwo- odszczepialna anionowa grupe, taka jak atom chlorowca, grupa kwasu siarkowego albo grupa alkilo-, wzglednie arylosulfonyloksylowa.Produkty wyjsciowe sa czesciowo znane, czes¬ ciowo zas moga byc otrzymywane w znany spo¬ sób, zwlaszcza przy uzyciu l-(2-cyjanofenoksy)-2,3- -epoksypropanu jako zwiazku wyjsciowego. Zwia¬ zek epoksydowy o wzorze 2 mozna otrzymywac przez reakcje 2-hydroksy-benzonitrylu z epichlor- hydryna w obecnosci lugu sodowego, a przez dzia¬ lanie odpowiednim kwasem chlorowcowodorowym otrzymuje sie chlorowcohydryne o wzorze 2.Zwiazek o wzorze 2 mozna tez otrzymac z epok¬ sydu o wzorze 4 przez reakcje z ftalimidkiem po¬ tasowym i nastepne rozszczepienie hydrazyny (syn¬ teza Gabriela).Wytworzony sposobem wedlug wynalazku zwia¬ zek posiada w ugrupowaniu -CHOH- asymetrycz¬ ny atom wegla; wystepuje wiec zarówno w for¬ mie racematu, jak równiez optycznie czynnych antypodów. Optycznie czynne zwiazki mozna otrzymac albo wychodzac z optycznie czynnych produktów wyjsciowych, albo rozdzielajac otrzy- many racemat na antypody optyczne w znany spo¬ sób, na przyklad za pomoca kwasu dwubenzoilo- winowego lub bromokamforosulfonowego.Wytworzony sposobem wedlug wynalazku zwia¬ zek mozna przeprowadzic w znany sposób w fizjo- io logicznie tolerowane sole addycyjne z kwasami.Do tego celu nadaje sie, na przyklad kwas solny, bromowodorowy, siarkowy, metanosulfonowy, ma¬ leinowy, octowy, szczawiowy, mlekowy, winowy albo 8-chloro-teofilina.Wytworzony sposobem wedlug wynalazku zwia¬ zek o wzorze 1, wzglednie jego fizjologicznie tole¬ rowane sole addycyjne z kwasami, posiadaja cen¬ ne wlasciwosci terapeutyczne, szczególnie /?-adre- nolityczne i moga byc podawane leczniczo lub pro- filaktycznie w schorzeniach naczyn wiencowych serca, w leczeniu arytmii serca, szczególnie czesto¬ skurczu. Zwiazek ten wykazal w badaniach na swinkach morskich znacznie skuteczniejsze dziala¬ nie zwalniajace akcje serca i antagonistyczne w stosunku do aludryny [aludryna = l-(3,4-dwu- hydroksyfenylo)- 1- hydroksy- 2- izopropyloamino- etan] oraz mniejsza toksycznosc niz znany 1-(1- -naftoksy)-2-hydroksy-3-izopropyloaminopropan.Jednorazowa dawka otrzymanego sposobem we- dlug wynalazku zwiazku wynosi 1—150 mg, ko- 84 33984 339 rzystnie 5—50 mg (doustnie) wzglednie 1—20 mg (pozajelitowo). — Z otrzymanego sposobem wedlug wynalazku zwiazku przygotowuje sie zwykle stosowne posta¬ cie galenowe, takie jak roztwory, emulsje, tablet¬ ki, drazetki albo postacie o przedluzonym dziala¬ niu, w znany sposób przy uzyciu srodków pomoc¬ niczych, nosników, srodków rozsadzajacych, wia¬ zacych, powlekajacych albo poslizgowych, smako¬ wych^ slodzacych, srodków do osiagniecia przedlu¬ zonego dzialania albo ulatwiajacych rozpuszczanie.Nowy zwiazek moze byc równiez stosowany w polaczeniu z innymi farmakologicznie czynnymi subsialacjami rozszerzajacymi naczynia wiencowe, pobudzajacymi uklad wspólczulny, glikozydami na- sercowymi albo srodkami uspokajajacymi.Ta&lfctki mo^na na przyklad otrzymywac przez zmieszanie substancji czynnej ze znanymi substan- cjamF'pomocniczymi, na przyklad obojetnymi roz¬ cienczalnikami, takimi jak weglan wapniowy, fos¬ foran wapniowy albo cukier mlekowy, srodkami rozsadzajacymi, takimi jak skrobia kukurydziana lub kwas alginowy, srodkami wiazacymi, takimi jak skrobia albo zelatyna, srodkami poslizgowymi, takimi jak stearynian magnezowy albo talk i/lub srodkami do uzyskania przedluzonego dzialania, ta¬ kimi jak karboksypolimetylen, karboksymetyloce- luloza, ftalan acetylocelulozy albo octan poliwi- nylu.Tabletki moga równiez skladac sie z wielu warstw. Drazetki mozna otrzymywac odpowiednio przez powlekanie otrzymanych analogicznie do tabletek rdzeni w znany sposób przy uzyciu sto¬ sowanych zwykle do drazowania srodków, takich jak kolidon, szelak, guma arabska, talk, dwutlenek tytanu albo cukier. Dla uzyskania efektu przedlu¬ zonego dzialania albo unikniecia niezgodnosci rdzen moze skladac sie z kilku warstw.Podobnie dla uzyskania przedluzonego dzialania powloki drazetek moga równiez zawierac kilka warstw, przy czym stosuje sie w tym celu wymie¬ nione przy tabletkach substancje pomocnicze.Dla wytwarzania miekkich kapsulek zelatyno¬ wych albo podobnych kapsulek zamykanych, sub¬ stancje czynna mozna mieszac z olejem roslinnym.Twarde kapsulki zelatynowe moga zawierac gra¬ nulat substancji czynnej w polaczeniu ze stalymi sproszkowanymi nosnikami, takimi jak laktoza, sacharoza, sorbit, mannit, skrobia, na przyklad skrobia ziemniaczana, kukurydziana albo amylo- pektyna, pochodne celulozy albo zelatyna.Syropy substancji czynnej lub tez kombinacji substancji czynnych moga zawierac jeszcze do¬ datkowo srodek slodzacy, jak sacharyna, cyklami- nian, gliceryna, albo cukier, jak równiez srodek poprawiajacy smak, na przyklad srodki zapacho¬ we, jak wanilina albo ekstrakt pomaranczowy.Oprócz tego moga zawierac jeszcze srodki ulatwia¬ jace powstawanie zawiesiny, zagestniki takie, jak sól sodowa karboksymetylocelulozy, srodki zwil¬ zajace, na przyklad produkty kondensacji alko^ holi tluszczowych z tlenkiem etylenu, albo srodki konserwujace, takie jak /?-hydroksybenzoesany.Roztwory iniekcyjne przygotowuje sie w znanym sposób, na przyklad z dodatkiem srodków konser¬ wujacych, takich jak /?-hydroksybenzoesany albo stabilizatorów, takich jak kompleksony i rozlewa do fiolek iniekcyjnych lub ampulek. Roztwory mo¬ ga zawierac równiez stabilizator i/lub srodek bu¬ forujacy.Czopki mozna przygotowywac przez mieszanie substancji czynnej wzglednie kombinacji substan- !0 cji czynnych ze znanymi nosnikami, takimi jak tluszcze obojetne albo glikol polietylenowy wzgled¬ nie jego pochodne. Mozna równiez wytwarzac do- odbytnicze kapsulki zelatynowe zawierajace ak¬ tywna substancje zmieszana z olejem roslinnym lub parafinowym.Nastepujacy przyklad blizej objasnia sposób wedlug wynalazku.Przyklad. Chlorowodorek l-(2-cyjanofenoksy)- -2-hydroksy-3-etyloaminopropanu. 1,14 g (0,005 mola) chlorowodorku l-(2-cyjanofe- noksy)-2-hydroksy-3-aminopropanu rozpuszcza sie;, w 2 ml wody i zadaje 1,06 g (0,01 mola) sody. Po dodaniu 12 ml etanolu i 1,08 g (0,01 mola) bromku etylu ogrzewa sie, mieszajac, do wrzenia pod chlodnica zwrotna. Po 1-godzinnym utrzymywania w stanie wrzenia, mieszanine zateza sie pod próz¬ nia, a pozostalosc chromatografuje na zelu krze¬ mionkowym, stosujac mieszanine skladajaca sie z 70 czesci octanu etylu, 30 czesci izopropanolu i 10 czesci amoniaku. Tak oczyszczona zasade wy¬ traca sie z etanolu w postaci chlorowodorku, tem¬ peratura topnienia wynosi 134—135,5°C. PL PL PL PL PL PL PL PL
Claims (2)
1. Zastrzezenia patentowe 1. Sposób wytwarzania l-(2-cyjanofenoksy)-2-hy- 40 droksy-3-etyloaminopropanu o wzorze 1 w postaci racemicznej lub optycznie czynnej, jak równiez je¬ go soli addycyjnych z kwasami, znamienny tym,, ze do l-(2-cyjanofenoksy)-2-hydroksy-3-aminopro- panu o wzorze 2 wprowadza sie grupe etylowa 45 dzialajac zwiazkiem o wzorze 3, w którym X ozna¬ cza latwo odszczepialna anionowa grupe i ewentu¬ alnie uzyskany racemat ewentualnie rozszczepia sie na postacie optycznie czynne i/lub zwiazek: o wzorze 1 przeprowadza sie w fizjologicznie tole- 50 rowane sole addycyjne z kwasami.
2. Sposób wedlug zastrz. 1, znamienny tym, ze w przypadku wytwarzania optycznie czynnego i-(2- cyjanofenoksy)- 2- hydroksy- 3- etyloamino- 55 propanu i jego soli, racemiczny l-(2-cyjanofeno- ksy)-2-hydroksy-3-etyloaminopropan przeprowadza sie za pomoca kwasów pomocniczych w diastereo- izomeryczne sole, które nastepnie rozdziela sie. 603. Sposób wedlug zastrz. 1, znamienny tym, ze stosuje sie zwiazek o wzorze 3, w którym X ozna¬ cza atom chlorowca, grupe kwasu siarkowego alba grupe alkilo- lub arylosulfonyloksylowa.84 339 CN 0CH2-CH0H-CH2-NHC2H5 Wzór 1 CN ^ V 0CH2-CH0H -CH2-NH2 Wzór 2 C2H5-X Wzór 3 - CH CH9 \ / 2 O Wzór 4 PL PL PL PL PL PL PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1940566A DE1940566C3 (de) | 1969-08-08 | 1969-08-08 | 1- (2-Nitrilophenoxy)-2-hydroxy-3äthylaminopropan, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL84339B1 true PL84339B1 (en) | 1976-03-31 |
Family
ID=5742361
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970174661A PL86937B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174660A PL84519B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174662A PL84357B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174658A PL84398B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174659A PL84520B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970142704A PL80550B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174656A PL84341B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174657A PL84339B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
Family Applications Before (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970174661A PL86937B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174660A PL84519B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174662A PL84357B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174658A PL84398B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174659A PL84520B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970142704A PL80550B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174656A PL84341B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3732277A (pl) |
| AT (9) | AT302996B (pl) |
| BE (1) | BE754604A (pl) |
| BG (8) | BG16739A3 (pl) |
| CH (1) | CH546223A (pl) |
| CS (8) | CS166735B2 (pl) |
| DE (1) | DE1940566C3 (pl) |
| DK (1) | DK125639B (pl) |
| ES (8) | ES382497A1 (pl) |
| FR (1) | FR2068479B1 (pl) |
| NL (1) | NL171702C (pl) |
| PL (8) | PL86937B1 (pl) |
| RO (8) | RO60084A (pl) |
| SE (1) | SE375303B (pl) |
| SU (1) | SU386506A3 (pl) |
| YU (1) | YU34515B (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT326107B (de) * | 1935-11-15 | 1975-11-25 | Boehringer Sohn Ingelheim | Verfahren zur herstellung von neuen racemischen oder optisch aktiven n,n'-bis- (3-subst. phenoxy-2-hydroxy-1-propyl) -alpha,omega- diaminoalkanen sowie deren säureadditionssalzen |
| GB1231783A (en) * | 1967-05-16 | 1971-05-12 | May & Baker Ltd | Benzene derivatives |
| GB1415505A (en) * | 1972-06-01 | 1975-11-26 | Ici Ltd | Alkanolamine derivatives |
| US4083992A (en) * | 1972-12-15 | 1978-04-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| US4131685A (en) * | 1972-12-15 | 1978-12-26 | Imperial Chemical Industries Limited | Pharmaceutical compositions and uses of alkanolamine derivatives |
| US4171374A (en) * | 1972-12-15 | 1979-10-16 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| GB1455116A (en) * | 1972-12-15 | 1976-11-10 | Ici Ltd | Pharmaceutical compositions |
| US4167581A (en) * | 1972-12-15 | 1979-09-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives and pharmaceutical compositions and uses thereof |
| GB1509527A (en) * | 1974-06-05 | 1978-05-04 | Ici Ltd | 1-(aryl-or heteroaryl)oxy-3-(substituted-amino)propan-2-ol derivatives processes for their manufacture and pharmaceutical compositions containing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL144926B (nl) * | 1963-08-26 | 1975-02-17 | Boehringer Sohn Ingelheim | Werkwijze ter bereiding van een beta-adrenolytisch werkzaam 1-(cyaanfenoxy)-2-hydroxy-3-isopropylaminopropaan en zouten daarvan. |
-
0
- BE BE754604D patent/BE754604A/xx not_active IP Right Cessation
-
1969
- 1969-08-08 DE DE1940566A patent/DE1940566C3/de not_active Expired
-
1970
- 1970-07-30 SU SU701469623D patent/SU386506A3/ru active
- 1970-08-03 US US00060749A patent/US3732277A/en not_active Expired - Lifetime
- 1970-08-04 CS CS3686*[A patent/CS166735B2/cs unknown
- 1970-08-04 CS CS3688*[A patent/CS166737B2/cs unknown
- 1970-08-04 CS CS703685A patent/CS166734B2/cs unknown
- 1970-08-04 CS CS3684*[A patent/CS166733B2/cs unknown
- 1970-08-04 CS CS3689*[A patent/CS166738B2/cs unknown
- 1970-08-04 CS CS3687*[A patent/CS166736B2/cs unknown
- 1970-08-04 CS CS3683*[A patent/CS166732B2/cs unknown
- 1970-08-04 CS CS5440A patent/CS166731B2/cs unknown
- 1970-08-05 CH CH1180070A patent/CH546223A/xx not_active IP Right Cessation
- 1970-08-05 BG BG18257A patent/BG16739A3/xx unknown
- 1970-08-06 RO RO69113A patent/RO60084A/ro unknown
- 1970-08-06 RO RO69109A patent/RO60645A/ro unknown
- 1970-08-06 RO RO69108A patent/RO60644A/ro unknown
- 1970-08-06 RO RO69111A patent/RO60082A/ro unknown
- 1970-08-06 RO RO64160A patent/RO55805A/ro unknown
- 1970-08-06 RO RO69110A patent/RO60746A/ro unknown
- 1970-08-06 RO RO69112A patent/RO60083A/ro unknown
- 1970-08-06 RO RO69115A patent/RO61039A/ro unknown
- 1970-08-06 YU YU2007/70A patent/YU34515B/xx unknown
- 1970-08-06 SE SE7010830A patent/SE375303B/xx unknown
- 1970-08-06 ES ES382497A patent/ES382497A1/es not_active Expired
- 1970-08-07 FR FR7029317A patent/FR2068479B1/fr not_active Expired
- 1970-08-07 BG BG15431A patent/BG18178A3/xx unknown
- 1970-08-07 AT AT1107671A patent/AT302996B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970174661A patent/PL86937B1/pl unknown
- 1970-08-07 PL PL1970174660A patent/PL84519B1/pl unknown
- 1970-08-07 NL NLAANVRAGE7011735,A patent/NL171702C/xx not_active IP Right Cessation
- 1970-08-07 PL PL1970174662A patent/PL84357B1/pl unknown
- 1970-08-07 DK DK407670AA patent/DK125639B/da not_active IP Right Cessation
- 1970-08-07 AT AT1108071A patent/AT303013B/de not_active IP Right Cessation
- 1970-08-07 BG BG18258A patent/BG17762A3/xx unknown
- 1970-08-07 AT AT1107471A patent/AT303008B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107871A patent/AT303011B/de not_active IP Right Cessation
- 1970-08-07 BG BG18255A patent/BG17761A3/xx unknown
- 1970-08-07 AT AT1107571A patent/AT303009B/de not_active IP Right Cessation
- 1970-08-07 AT AT723670A patent/AT303006B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107971A patent/AT303012B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970174658A patent/PL84398B1/pl unknown
- 1970-08-07 PL PL1970174659A patent/PL84520B1/pl unknown
- 1970-08-07 BG BG18253A patent/BG17759A3/xx unknown
- 1970-08-07 PL PL1970142704A patent/PL80550B1/pl unknown
- 1970-08-07 BG BG18256A patent/BG18179A3/xx unknown
- 1970-08-07 BG BG18259A patent/BG17955A3/xx unknown
- 1970-08-07 PL PL1970174656A patent/PL84341B1/pl unknown
- 1970-08-07 PL PL1970174657A patent/PL84339B1/pl unknown
- 1970-08-07 AT AT1108171A patent/AT303014B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107771A patent/AT303010B/de not_active IP Right Cessation
- 1970-08-07 BG BG18254A patent/BG17760A3/xx unknown
-
1971
- 1971-03-04 ES ES388882A patent/ES388882A1/es not_active Expired
- 1971-03-04 ES ES388885A patent/ES388885A1/es not_active Expired
- 1971-03-04 ES ES388883A patent/ES388883A1/es not_active Expired
- 1971-03-04 ES ES388881A patent/ES388881A1/es not_active Expired
- 1971-03-04 ES ES388879A patent/ES388879A1/es not_active Expired
- 1971-03-04 ES ES388880A patent/ES388880A1/es not_active Expired
- 1971-03-04 ES ES388884A patent/ES388884A1/es not_active Expired
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