DK141483B - Analogifremgangsmåde til fremstilling af as-triazino-(6,5-c)quinolinderivater. - Google Patents
Analogifremgangsmåde til fremstilling af as-triazino-(6,5-c)quinolinderivater. Download PDFInfo
- Publication number
- DK141483B DK141483B DK247173AA DK247173A DK141483B DK 141483 B DK141483 B DK 141483B DK 247173A A DK247173A A DK 247173AA DK 247173 A DK247173 A DK 247173A DK 141483 B DK141483 B DK 141483B
- Authority
- DK
- Denmark
- Prior art keywords
- triazino
- quinoline
- nitroquinoline
- dihydro
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- ARFYZKAYDRJATN-UHFFFAOYSA-N [1,2,4]triazino[5,6-c]quinoline Chemical class C1=NN=C2C3=CC=CC=C3N=CC2=N1 ARFYZKAYDRJATN-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- -1 hydrazino compound Chemical class 0.000 description 5
- SKRZKNWOHLTARM-UHFFFAOYSA-N (3-nitroquinolin-4-yl)hydrazine Chemical compound C1=CC=C2C(NN)=C([N+]([O-])=O)C=NC2=C1 SKRZKNWOHLTARM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- YIEHFGMYLXAXMX-UHFFFAOYSA-N N(N)C=1C(=NC2=CC=CC=C2C1)[N+](=O)[O-] Chemical compound N(N)C=1C(=NC2=CC=CC=C2C1)[N+](=O)[O-] YIEHFGMYLXAXMX-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- DERASAFMHXNKGC-UHFFFAOYSA-N (3-nitroquinolin-2-yl)hydrazine Chemical compound C1=CC=C2C=C([N+]([O-])=O)C(NN)=NC2=C1 DERASAFMHXNKGC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
141483 i
Opfindelsen angår en analogifremgangsmåde til fremstilling af hidtil ukendte as-triazino[5,6-c]quinolin-derivater med den almene formel (I) R2 5 ^ N \-R (I) 10 hvor R betyder hydrogen, alkyl med 1-4 C-atømer eller phenyl, 1 2 og R og R betyder hydrogen eller sammen danner en kemisk binding. Disse forbindelser har en betydelig betændelseshæra-mende og antimikrobisk virkning.
15 Fremgangsmåden ifølge opfindelsen er ejendommelig ved, at 4-hydrazino-3-nitroquinolin bringes til reaktion med en orthocarboxylsyrealkylester med den almfene formel (II) R-CS(0R1]-. (II)
3 J
hvori R betyder alkyl med 1-3 C-atomer, og R har den ovenfor 20 angivne betydning, den opnåede alkoxymethylenhydrazino-nitro-quinolin med den almene formel (III)
R
^,N=C-0R^
NH
^ ' N0o (III) hvor R og R har den ovenfor angivne betydning, omsættes ved ringslutningsreaktion under reducerende betingelser til even-30 tuelt 3-substitueret l,2-dihydro-as-triazlno[5,6-»c]quinolin, og denne isoleres eventuelt i form af sit salt, og quinolinen eller dens salt omsættes ved påfølgende oxidation til et as--triazino[5,6-c]quinolin-derivat med den almene formel (I).
Fremgangsmåden ifølge opfindelsen beror på den overra-35 skende erkendelse, at dannelsen af alkoxymethylenhydrazino--forbindelsen med den almene formel (III) ud fra udgangs-hy- 2 141483 drazinforbindelsen forløber éntydigt og uden dannelse af hy-drazidinagtige biprodukter, og under reducerende betingelser er tendensen hos den dannede forbindelse til ringslutning overordentlig stor.
5 Reaktionen mellem 4-hydrazino-3-nitroquinolin og or- thocarboxylsyrealkylesteren udføres almindeligvis ved blandingens kogepunkt i nærværelse af en sur katalysator. Den dannede alkoxymethylenhydrazino-nitroquinolin hydrogeneres katalytisk. Ringslutningen foregår allerede under reduktionen, 10 da den sig ud fra nitrogruppen dannende aminogruppe reagerer in situ med den meget reaktionsdygtige alkoxymethylenhydrazi-no-gruppe. Ved den intramolekylære ringslutning dannes den tilsvarende l,2-hydro-as-triazino[5,6-c]quinolin, som ved oxidation omsættes til den aromatiske forbindelse med den almene 15 formel (I).
Tendensen hos dihydro-forbindelsen til oxidation er almindeligvis temmelig høj, hvorfor det normalt er tilstrækkeligt efter den reduktive ringslutning af inddampe opløsningen i luften. Når tendensen til oxidation ikke er tilstrækkelig, 20 isoleres dihydroforbindelsen i form af f.eks. sit hydrochlorid, og dette oxideres i alkalisk medium ved hjælp af et oxidationsmiddel, f.eks. kaliumhexacyanoferrat, til den tilsvarende as--triazino[5,6-c]quinolin-forbindelse. De let oxiderbare dihy-dro-intermediære kan isoleres, idet den efter reduktionen op-25 nåede opløsning filtreres under indifferent gasatmosfære, og forbindelsens hydrochlorid kan fraskilles med saltsur alkohol.
De omhandlede as-triazinoquinoliner samt de tilsvarende dihydro-forbindelser har foruden en betydelig betændelseshæmmende virkning også en svag smertelindrende og antimikrobisk 30 virkning. Resultaterne fra den farmakologiske undersøgelse er sammenstillet nedenfor.
Toksiciteten undersøges på mus af stammen CFLP ved indgivelse af en ved hjælp af "Tween 80" tilberedt suspension. De stoffer, der skal undersøges, indgives i et volumen på 20-30 ml/kg.
35 Den ved per os-indgivelse bestemte toksicitet er angivet i nedenstående tabel: 3 UU83
Forbindelse DL50 as-Triazino[5,6-c]quinolin 90 3-Phenyl-as-triazino[5,6-c]quinolin 3000 3-Phenyl-l,2-dihydro-as-triazino[5,6-c]quinolin,HCl > 3000 5 Aspirin 1500
Indomethacin 24,3
Phenylbutazon 1000
Den betændelseshæmmende virkning undersøges ifølge Winter (J. Pharmacol. Exp. Ther. 141 (1963) p. 369) ved carrage-2o nin-ødem-forsøget på hanrotter med en vægt på 150-180 g. Rotterne får i et bagben plantart og subcutant indgivet 0,1 ml carragenin-suspension. Det dannede ødem måles med et plethys-mometer. De værdier, der er målt ved per os-indgivelse af det stof, som skal undersøges, udtrykt i procent af kontrolværdi-25 erne, er angivet i nedenstående tabel:
Dosis Hamming
Forbindelse mg/kg % as-Triazino[5,6-c]quinolin 0,87 24,3 1,75 32,8 20 3'5 43'5 3-Phenyl-as-triazino[5,6-c]quinolin 200 15,7 400 20,3 3-Phenyl-l,2-dihydro-as-triazino[6,5-c]- quinolin-hydrochlorid 200 31,3 25 400 31,8
Aspirin 180 39,0
Phenylbutazon 30 33,0 90 45,0
Indomethacin 9 44,0 30 3 30
Den betændelseshaanmende virkning suppleres ved en svag smertestillende virkning.
Fremgangsmåden ifølge opfindelsen belyses nærmere ved nedenstående eksempler.
35 Den som udgangsforbindelse anvendte 4-hydrazino-3-ni- troquinolin fremstilles ifølge J. Chem. Soc. (C) (1969) p. 1758.
4 141483
Eksempel 1 a) 4-p-Ethoxymethylenhydrazino-3-nitroquinolin.
20,4 g (0,1 mol) 4-hydrazino-3-nitroquinolin og 0,2 g p-toluensulfonsyre suspenderes i 100 ml orthomyresyre-ethyl-5 ester, og suspensionen holdes i 4 timer ved 120-130°C. Den ved reaktionen dannede ethanol afdestilleres, og derefter afkøles reaktionsblandingen. 22,3 g (86%) 4-3-ethoxymethylenhydrazino--3-nitroquinolin udskilles. Produktet er gult og smelter ved 150-152°C (benzen).
10 På samme måde fås nedenstående forbindelser.
4-3-ethoxymethyl-methylenhydrazino-3-nitroquinolin, smp.: 131-133°C
4-b-ethoxyethyl-methylenhydrazino-3-nitroquinolin, smp.: 170-172°C
15 4-3-ethoxyphenyl-methylenhydrazino-3-nitroquinolin, smp.: 127-128°C.
b) as-Triazino[5,6-c]quinolin 13.0 g (0,05 mol)4-fi-ethoxymethylenhydrazino-3-nitro- 20 quinolin hydrogeneres i ethanolisk medium i nærværelse af en palladiumkatalysator. Den efter afslutningen af hydrogenoptagelsen opnåede opløsning inddampes. Der fås 7,7 g (85%) as--triazino[5,6-c]quinolin i form af gule krystaller. Produktet smelter ved 162-164°C.
25 På analog måde fås nedenstående forbindelser:
3-methyl-as-triazino[5,6-c]quinolin, smp.: 137-138°C
3-ethyl-as-triazino[5,6-c]quinolin, smp.: 106-108°C
3-phenyl-as-triazino[5,6-c]quinolin, smp.: 203-204°C.
30 Eksempel 2 1,2-Dihydro-as-triazino[5,6-c]quinolin-hydrochlorid.
26.0 g (0,1 mol) 4-fi-ethoxymethylenhydrazino-3-nitror-quinolin hydrogeneres i et ethanolisk medium i nærværelse af palladiumkatalysator. Efter afslutning af hydrogenoptagelsen 35 fjernes katalysatoren ved filtrering, og filtratet får tilsat 200 ml 15%'s saltsurt ethylalkohol. Ved inddampning af opløs- 5 UU83 ningen opnås 21,0 g (95,5%) 1,2-dihydro-as-triazino[5,6-c]-quinolin-hydrochlorid, som smelter ved 285-287°C.
På den ovenfor beskrevne måde fremstilles også 3-phe-nyl-1,2-dihydro-as-triazino[5,6-c]quinolin-hydrochlorid, hvis 5 smeltepunkt ligger ved 297-298°C.
Eksempel 3 as-Triazino[5,6-c]quinolin.
11,0 g (0,05 mol) 1,2-dihydro-as-triazino[5,6-c]quino-10 lin-hydrochlorid behandles ved 0°G med 100 ml 36%'s kalium- j.
hexacyanoferratopløsnlng, hvis pH-værdi i forvejen er indstillet med koncentreret ammoniumhydroxid på 9. Der fås 8,2 g (90%) as-triazino[5,6-c]quinolin, som i sine egenskaber stemmer overens med det ifølge eksempel 1 opnåede produkt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE002021 | 1972-05-05 | ||
| HUEE2021A HU165677B (da) | 1972-05-05 | 1972-05-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141483B true DK141483B (da) | 1980-03-24 |
| DK141483C DK141483C (da) | 1980-09-22 |
Family
ID=10995439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK247173AA DK141483B (da) | 1972-05-05 | 1973-05-04 | Analogifremgangsmåde til fremstilling af as-triazino-(6,5-c)quinolinderivater. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3873541A (da) |
| JP (1) | JPS563872B2 (da) |
| AT (1) | AT323749B (da) |
| CA (1) | CA978188A (da) |
| CH (1) | CH580627A5 (da) |
| CS (1) | CS174879B2 (da) |
| DD (1) | DD106844A5 (da) |
| DE (1) | DE2322394A1 (da) |
| DK (1) | DK141483B (da) |
| FR (1) | FR2183801B1 (da) |
| GB (1) | GB1382781A (da) |
| HU (1) | HU165677B (da) |
| NL (1) | NL7306160A (da) |
| PL (1) | PL85376B1 (da) |
| SE (1) | SE403615B (da) |
| YU (1) | YU36701B (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU181689B (en) * | 1980-04-18 | 1983-11-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new dihydro-as-triazino-square bracket-5,6-c-square bracket closed-quinoline derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3597427A (en) * | 1969-01-13 | 1971-08-03 | American Cyanamid Co | 1,2-dihydropyrido(3,4-e)-as-triazines |
| US3721670A (en) * | 1971-04-05 | 1973-03-20 | Morton Norwich Products Inc | 3-substituted-as-triazino(5,6-c)quinolines |
| HU164031B (da) * | 1971-08-02 | 1973-12-28 |
-
1972
- 1972-05-05 HU HUEE2021A patent/HU165677B/hu not_active IP Right Cessation
-
1973
- 1973-04-30 CH CH617873A patent/CH580627A5/xx not_active IP Right Cessation
- 1973-05-01 US US356174A patent/US3873541A/en not_active Expired - Lifetime
- 1973-05-03 NL NL7306160A patent/NL7306160A/xx not_active Application Discontinuation
- 1973-05-04 CA CA170,469A patent/CA978188A/en not_active Expired
- 1973-05-04 CS CS3184A patent/CS174879B2/cs unknown
- 1973-05-04 DE DE2322394A patent/DE2322394A1/de active Pending
- 1973-05-04 FR FR7316126A patent/FR2183801B1/fr not_active Expired
- 1973-05-04 JP JP5022973A patent/JPS563872B2/ja not_active Expired
- 1973-05-04 AT AT394373A patent/AT323749B/de not_active IP Right Cessation
- 1973-05-04 GB GB2125373A patent/GB1382781A/en not_active Expired
- 1973-05-04 SE SE7306317A patent/SE403615B/xx unknown
- 1973-05-04 PL PL1973162336D patent/PL85376B1/pl unknown
- 1973-05-04 DD DD170617A patent/DD106844A5/xx unknown
- 1973-05-04 YU YU1192/73A patent/YU36701B/xx unknown
- 1973-05-04 DK DK247173AA patent/DK141483B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2183801B1 (da) | 1976-05-14 |
| YU36701B (en) | 1984-08-31 |
| SE403615B (sv) | 1978-08-28 |
| FR2183801A1 (da) | 1973-12-21 |
| US3873541A (en) | 1975-03-25 |
| YU119273A (en) | 1982-02-25 |
| DD106844A5 (da) | 1974-07-05 |
| DK141483C (da) | 1980-09-22 |
| JPS4947396A (da) | 1974-05-08 |
| PL85376B1 (en) | 1976-04-30 |
| JPS563872B2 (da) | 1981-01-27 |
| NL7306160A (da) | 1973-11-07 |
| AT323749B (de) | 1975-07-25 |
| HU165677B (da) | 1974-10-28 |
| CS174879B2 (da) | 1977-04-29 |
| CA978188A (en) | 1975-11-18 |
| CH580627A5 (da) | 1976-10-15 |
| GB1382781A (en) | 1975-02-05 |
| DE2322394A1 (de) | 1973-11-15 |
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