PL108213B1 - Method of producing new naphthalenotriols sposob wytwarzania nowych naftalenotrioli - Google Patents
Method of producing new naphthalenotriols sposob wytwarzania nowych naftalenotrioli Download PDFInfo
- Publication number
- PL108213B1 PL108213B1 PL1977195808A PL19580877A PL108213B1 PL 108213 B1 PL108213 B1 PL 108213B1 PL 1977195808 A PL1977195808 A PL 1977195808A PL 19580877 A PL19580877 A PL 19580877A PL 108213 B1 PL108213 B1 PL 108213B1
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- PL
- Poland
- Prior art keywords
- formula
- naphthalenotriols
- producing new
- compound
- new
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- NCIAGQNZQHYKGR-UHFFFAOYSA-N naphthalene-1,2,3-triol Chemical class C1=CC=C2C(O)=C(O)C(O)=CC2=C1 NCIAGQNZQHYKGR-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- -1 1,1-dimethylethyl- Chemical group 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Plural Heterocyclic Compounds (AREA)
Description
******-*»i Twórcy wynalazku: Frederic Peter Hauck, Machael Edward Condon, Ri¬ ta Theresa Fox Uprawniony z patentu: E. R. SQUIBB and SONS, INC, Princeton (Stany Zjednoczohe Ameryki) Sposób wytwarzania nowych naftalenotrioli Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych naftalenotrioli o wzorze ogólnym 1, w którym R4 oznacza nizszy alkil, zawierajacy 1—4 atomów wegla. Zwiazki te sa stosowane w lecze¬ niu stenokardii.Zwiazki o wzorze 1 i ich farmaceutycznie do¬ puszczalne sole sa uzyteczne jako srodki antyfi- brynogenne i moga byc stosowane jako srodki po¬ wstrzymujace arytmie serca u ssaków przez ha¬ mowanie adrenergicznych beta receptorów w scho¬ rzeniach miesnia sercowego. Dla tych celów zwiaz¬ ki o wzorze 1 lub ich farmakologicznie dopusz¬ czalne sole moga byc wprowadzane w postaci konwencjonalnej, jak tabletki, kapsulki, eliksiry, roztwory do injekcji lub podobne, razem z odpo¬ wiednimi nosnikami, zarobkami, srodkami smarny¬ mi, buforami i podobnymi. Dzienna dawka wy¬ nosi okolo 5—100 mg na kilogram wagi ciala, ko¬ rzystnie okolo 5—10 mg na kilogram wagi ciala i moze byc stosowane w dawce pojedynczej lub podzielonych dawkach, jak opisano powyzej.W celu otrzymania zwiazku o wzorze 1, w któ¬ rym R4 oznacza afllkil o 1—4 atomach wegla, oksi- ran (tlenek etylenu) o wzorze 2 poddaje sie re¬ akcji z alkiloamina R4—NH2 tworzac amine o wzo¬ rze 3. Reakcje mozna prowadzic w rozpuszczalni¬ ku organicznym i najwygodniej w temperaturze pokojowej. Kwasna hydroliza zwiazku o wzorze 3 daje produkt o wzorze 1.Zwiazki o wzorze 3 sa nowymi zwiazkami po- 10 15 20 30 srednimi. Dodatkowo, zwiazki te posiadaja uzytecz¬ na aktywnosc farmakologiczna i moga byc stoso¬ wane do powstrzymywania arytmii serca u ssaków przez hamowanie adrenergicznych bet receptorów w schorzeniach miesnia sercowego.Zwiazki o wzorze 1 tworza sole addycyjne z kwa¬ sami nieorganicznymi i organicznymi. Te sole ad¬ dycyjne z kwasami czesto stanowia sposób izolo¬ wania produktów z mieszaniny reakcyjnej, przez tworzenie soli w srodowisku, w którym sa nie¬ rozpuszczalne, a nastepnie zobojetnianie tych soli zasada taka, jak wodorotlenek sodu w celu uzy¬ skania wolnej zasady. Nastepnie mozna otrzymac z wolnej zasady i odpowiedniego kwasu nieorga¬ nicznego i organicznego, kazda dowolna sól. Przy¬ kladowo wymienia sie chlorowcowodorki, zwlasz¬ cza chlorowodorek, bromowodorek, siarczany, azo¬ tany, fosforany, borany, octany, / szczawiany, wi¬ niany, maleiniany, cytryniany, bursztyniany, ben¬ zoesany, askorbiniany, salicylany, metanosulfonia- ny, benzenosulfoniany, toluenosulfoniany i po¬ dobne.Nastepujace przyklady ilustruja istote wyna¬ lazku.Przyklad, a) 8-[3-[/l,l-dwumetyloetylo/ami- no]-2-hydroksypropoksy]-3a, 9a-cis-3a, 4, 9, 9a-czte- rowodoro-2,2-dwumetylonafto [2, 3-d]-l,3-dioksolol- -5.Roztwór 3,1 g 8-[2,3-/epoksy/propoksy]-3a, 9a-cis- -3a, 4, 9, 9a-czterowodoro-2,2-dwumetylonafto-[2,3- 108213108213 3 4 -d]-l,3-dioksolol-5 w 40 ml absolutnego etanolu, 30 ml benzenu i 20 ml Ill-rzed.-butyloammy od¬ stawia sie na noc w temperaturze pokojowej. Roz¬ puszczalnik usuwa sie pod próznia uzyskujac ty¬ tulowy zwaizek. b) Chlorowodorek cis-4-[3-[/l,l-dwumetyloetylo- /aminol-2- hydroksypropoksy]-5,6,7,8-czterowodóro- -1,6,7-naftalenotriolu (1 : 1). -8[3-[/l,l-dwumetyloetylo/amiino]-2-hydroksypro- poksy]-3a, 9a-cis-3a, 4, 9, 9a-czterowodoro-2,2-dwu- metylonafto [2,3-d]-l,3-dioksolol-5, otrzymany po¬ wyzej w punkcie a, rozpuszcza sie w 100 ml 5*/o fcWastr solnego *~pozostawia w temperaturze po- kójower w^ fciagfc J godziny.Nastepnie roztwót ten zateza sie pod próznia fto uzjKgkapjia piany. Rozpuszcza sie ja w goracym IzopBopaaoUfc* cjnbaifwia nerytem i rozciencza ete¬ rem. Otrzymany osad poddaje sie takiej samej ob¬ róbce, uzyskujac 1,2 g bezpostaciowego ciala sta¬ lego. Bezpostaciowa substancje (1,2 g) rekrystali- zuje sie z izopropanolu, uzyskujac 0,30 g krysta¬ licznego ciala stalego o temperaturze topnienia 178—185°C.Zastrzezenie patentowe Sposób wytwarzania nowych naftalenotrioli o wzorze ogólnym 1, w którym R4 oznacza reszte alkilowa, zawierajaca 1—4 atomów wegla oraz ich soli addycyjnych z kwasami, znamienny tym, ze zwiazek o wzorze 2 poddaje sie reakcji z amina o wzorze R4NH2, w którym R4 ma wyzej podane znaczenie po czym otrzymamy zwiazek o wzorze 3 poddaje sie kwasnej hydrolizie. i i i CH: CH 3V° 0-CH2-CH-CH2-NHR4 OH Nzórt 0-CRrCH —CH, OH Wzór 2 ch/Nd 0-CH,-CH-CHrNHR< OH OH Wzór 3 Drukarnia Narodowa, Zaklad Nr 6, zam. 258/80 Cena 45 zl 10 15 -CH I OH fta *\lp /l 6r3 i, Zakli la 45 : PL PL
Claims (1)
1. Zastrzezenie patentowe Sposób wytwarzania nowych naftalenotrioli o wzorze ogólnym 1, w którym R4 oznacza reszte alkilowa, zawierajaca 1—4 atomów wegla oraz ich soli addycyjnych z kwasami, znamienny tym, ze zwiazek o wzorze 2 poddaje sie reakcji z amina o wzorze R4NH2, w którym R4 ma wyzej podane znaczenie po czym otrzymamy zwiazek o wzorze 3 poddaje sie kwasnej hydrolizie. i i i CH: CH 3V° 0-CH2-CH-CH2-NHR4 OH Nzórt 0-CRrCH —CH, OH Wzór 2 ch/Nd 0-CH,-CH-CHrNHR< OH OH Wzór 3 Drukarnia Narodowa, Zaklad Nr 6, zam. 258/80 Cena 45 zl 10 15 -CH I OH fta *\lp /l 6r3 i, Zakli la 45 : PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/656,769 US4048231A (en) | 1976-02-09 | 1976-02-09 | 4-[3-(Substituted amino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-1,6,7-naphthalenetriols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL108213B1 true PL108213B1 (pl) | 1980-03-31 |
Family
ID=24634483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977195808A PL108213B1 (pl) | 1976-02-09 | 1977-02-04 | Method of producing new naphthalenotriols sposob wytwarzania nowych naftalenotrioli |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4048231A (pl) |
| JP (1) | JPS5943454B2 (pl) |
| AT (1) | AT349011B (pl) |
| AU (1) | AU509744B2 (pl) |
| BE (1) | BE850452A (pl) |
| CA (1) | CA1105483A (pl) |
| CH (1) | CH618676A5 (pl) |
| DE (1) | DE2701626A1 (pl) |
| DK (1) | DK51877A (pl) |
| FR (1) | FR2361335A1 (pl) |
| GB (2) | GB1564160A (pl) |
| HU (1) | HU173781B (pl) |
| IE (1) | IE45258B1 (pl) |
| NL (1) | NL7700421A (pl) |
| NO (1) | NO770415L (pl) |
| PL (1) | PL108213B1 (pl) |
| SE (1) | SE7701390L (pl) |
| ZA (1) | ZA767572B (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0003664B1 (en) * | 1978-02-08 | 1982-02-17 | Imperial Chemical Industries Plc | Alkanolamine derivatives, process for their preparation and pharmaceutical compositions containing them |
| JPS6241829Y2 (pl) * | 1980-03-28 | 1987-10-26 | ||
| FR2507181A1 (fr) | 1981-06-05 | 1982-12-10 | Sanofi Sa | Nouveaux ethers de phenol actifs sur le systeme cardiovasculaire, leur procede de preparation et leur utilisation dans des medicaments |
| KR101430838B1 (ko) * | 2009-09-11 | 2014-08-18 | 가부시키가이샤 리코 | 치환기 이탈 화합물, 유기 반도체 재료, 상기 재료를 포함하는 유기 반도체 막, 상기 막을 포함하는 유기 전자 디바이스, 막상체의 제조 방법, π-전자 공역계 화합물 및 π-전자 공역계 화합물의 제조 방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1543344A1 (de) * | 1966-04-22 | 1969-08-07 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen 1-Amino-3-aryloxypropanol-2-aethern |
| DE2130393C3 (de) * | 1970-06-22 | 1981-02-26 | E.R. Squibb & Sons Inc., New York, N.Y. (V.St.A.) | 6,7-Dihydroxy -5,6,7,8-tetrahydronaphthyloxyaminopropanole und ihre Salze mit Säuren sowie ihre Verwendung bei der Bekämpfung von Herzerkrankungen |
-
1976
- 1976-02-09 US US05/656,769 patent/US4048231A/en not_active Expired - Lifetime
- 1976-12-21 IE IE2805/76A patent/IE45258B1/en unknown
- 1976-12-21 ZA ZA767572A patent/ZA767572B/xx unknown
- 1976-12-22 CA CA268,494A patent/CA1105483A/en not_active Expired
- 1976-12-24 AU AU20890/76A patent/AU509744B2/en not_active Expired
- 1976-12-31 GB GB14546/79A patent/GB1564160A/en not_active Expired
- 1976-12-31 GB GB54410/76A patent/GB1564159A/en not_active Expired
-
1977
- 1977-01-17 DE DE19772701626 patent/DE2701626A1/de not_active Ceased
- 1977-01-17 NL NL7700421A patent/NL7700421A/xx not_active Application Discontinuation
- 1977-01-17 BE BE174133A patent/BE850452A/xx not_active IP Right Cessation
- 1977-02-04 PL PL1977195808A patent/PL108213B1/pl unknown
- 1977-02-07 AT AT77977A patent/AT349011B/de not_active IP Right Cessation
- 1977-02-07 HU HU77SU938A patent/HU173781B/hu not_active IP Right Cessation
- 1977-02-08 SE SE7701390A patent/SE7701390L/xx unknown
- 1977-02-08 JP JP52012912A patent/JPS5943454B2/ja not_active Expired
- 1977-02-08 CH CH149677A patent/CH618676A5/fr not_active IP Right Cessation
- 1977-02-08 DK DK51877A patent/DK51877A/da unknown
- 1977-02-08 NO NO770415A patent/NO770415L/no unknown
- 1977-02-09 FR FR7703602A patent/FR2361335A1/fr active Granted
- 1977-05-18 US US05/798,275 patent/US4093814A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1564160A (en) | 1980-04-02 |
| JPS5943454B2 (ja) | 1984-10-22 |
| BE850452A (fr) | 1977-07-18 |
| DK51877A (da) | 1977-08-10 |
| HU173781B (hu) | 1979-08-28 |
| FR2361335B1 (pl) | 1980-04-30 |
| AU509744B2 (en) | 1980-05-22 |
| DE2701626A1 (de) | 1977-08-11 |
| SE7701390L (sv) | 1977-08-10 |
| NL7700421A (nl) | 1977-08-11 |
| JPS5297953A (en) | 1977-08-17 |
| IE45258L (en) | 1977-08-09 |
| FR2361335A1 (fr) | 1978-03-10 |
| AU2089076A (en) | 1978-06-29 |
| US4093814A (en) | 1978-06-06 |
| ZA767572B (en) | 1977-11-30 |
| US4048231A (en) | 1977-09-13 |
| ATA77977A (de) | 1978-08-15 |
| AT349011B (de) | 1979-03-12 |
| IE45258B1 (en) | 1982-07-28 |
| CH618676A5 (pl) | 1980-08-15 |
| CA1105483A (en) | 1981-07-21 |
| GB1564159A (en) | 1980-04-02 |
| NO770415L (no) | 1977-08-10 |
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