FI59098C - Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrido(3,2-e)-astriazinderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrido(3,2-e)-astriazinderivat Download PDFInfo
- Publication number
- FI59098C FI59098C FI752294A FI752294A FI59098C FI 59098 C FI59098 C FI 59098C FI 752294 A FI752294 A FI 752294A FI 752294 A FI752294 A FI 752294A FI 59098 C FI59098 C FI 59098C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- group
- compound
- nitropyridine
- medium
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 12
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 claims description 11
- -1 potassium ferricyanide Chemical compound 0.000 claims description 10
- QPDGBZPNEZMTOU-UHFFFAOYSA-N (3-nitropyridin-2-yl)hydrazine Chemical compound NNC1=NC=CC=C1[N+]([O-])=O QPDGBZPNEZMTOU-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- GUODQFHMIYUCLH-UHFFFAOYSA-N pyrido[3,2-e][1,2,4]triazine Chemical class N1=NC=NC2=CC=CN=C21 GUODQFHMIYUCLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229920000137 polyphosphoric acid Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- BVIVFVANPAXULX-UHFFFAOYSA-N n'-(3-aminopyridin-2-yl)-2-phenylacetohydrazide Chemical compound NC1=CC=CN=C1NNC(=O)CC1=CC=CC=C1 BVIVFVANPAXULX-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 229910000906 Bronze Inorganic materials 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000010974 bronze Substances 0.000 description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- KZEFYQXFRBTJEB-UHFFFAOYSA-N n'-(3-nitropyridin-2-yl)-2-phenylacetohydrazide Chemical compound [O-][N+](=O)C1=CC=CN=C1NNC(=O)CC1=CC=CC=C1 KZEFYQXFRBTJEB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- YNLZQSXUZWRKPF-UHFFFAOYSA-N (2-nitropyridin-3-yl)hydrazine Chemical class NNC1=CC=CN=C1[N+]([O-])=O YNLZQSXUZWRKPF-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- IDJOCJAIQSKSOP-UHFFFAOYSA-N 2,2-dichloroethanol Chemical compound OCC(Cl)Cl IDJOCJAIQSKSOP-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 description 1
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 1
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical class [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 description 1
- ZLZQFSFGPQHAFS-UHFFFAOYSA-N CCCCCCCCCCCC(CC(=O)NNC1=CC=CC=N1)N Chemical compound CCCCCCCCCCCC(CC(=O)NNC1=CC=CC=N1)N ZLZQFSFGPQHAFS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- WKJNMQCLJBXUSZ-UHFFFAOYSA-N N'-(3-nitropyridin-2-yl)heptanehydrazide Chemical compound [N+](=O)([O-])C=1C(=NC=CC=1)NNC(CCCCCC)=O WKJNMQCLJBXUSZ-UHFFFAOYSA-N 0.000 description 1
- YJSZTOTZAZBWPX-UHFFFAOYSA-N N'-(3-nitropyridin-2-yl)tetradecanehydrazide Chemical compound [N+](=O)([O-])C=1C(=NC=CC=1)NNC(CCCCCCCCCCCCC)=O YJSZTOTZAZBWPX-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- FAWGDZUNQZJISX-UHFFFAOYSA-N heptanehydrazide Chemical compound CCCCCCC(=O)NN FAWGDZUNQZJISX-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KXTZPAQXYKUVLD-UHFFFAOYSA-N tetradecanehydrazide Chemical compound CCCCCCCCCCCCCC(=O)NN KXTZPAQXYKUVLD-UHFFFAOYSA-N 0.000 description 1
- BYGOPQKDHGXNCD-UHFFFAOYSA-N tripotassium;iron(3+);hexacyanide Chemical compound [K+].[K+].[K+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] BYGOPQKDHGXNCD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK356275AA DK138426B (da) | 1975-08-05 | 1975-08-05 | Analogifremgangsmåde til fremstilling af pyrido(3,2-e)-as-triazinderivater. |
| SE7508834A SE409456B (sv) | 1975-08-05 | 1975-08-05 | Analogiforfarande for framstellning av pyrido(3,2-e)-as-triazinderivat |
| GB32908/75A GB1492073A (en) | 1975-08-05 | 1975-08-06 | Pyrido(3,2-e)-as-triazine derivatives |
| FI752294A FI59098C (fi) | 1975-08-05 | 1975-08-13 | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrido(3,2-e)-astriazinderivat |
| DE19752536387 DE2536387A1 (de) | 1975-08-05 | 1975-08-14 | Pyrido(3,2-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben |
| AT636675A AT347958B (de) | 1975-08-05 | 1975-08-14 | Verfahren zur herstellung von neuen pyrido (3,2-e) -as-triazin-derivaten und von mit pharmazeutisch vertraeglichen saeuren gebildeten salzen dieser verbindungen |
| CH1064575A CH617199A5 (en) | 1975-08-05 | 1975-08-15 | Process for the preparation of pyrido[3,2-e]-as-triazine derivatives |
| DD187881A DD121323A5 (da) | 1975-08-05 | 1975-08-15 | |
| JP50099878A JPS5225796A (en) | 1975-08-05 | 1975-08-19 | Production of pyrid *3*22e* asstriazine derivative |
| BE159502A BE832791A (fr) | 1975-08-05 | 1975-08-27 | Derives de pyrido(3,2-e)-as-triazine et procede pour leur preparation. |
Applications Claiming Priority (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7508834A SE409456B (sv) | 1975-08-05 | 1975-08-05 | Analogiforfarande for framstellning av pyrido(3,2-e)-as-triazinderivat |
| SE7508834 | 1975-08-05 | ||
| DK356275AA DK138426B (da) | 1975-08-05 | 1975-08-05 | Analogifremgangsmåde til fremstilling af pyrido(3,2-e)-as-triazinderivater. |
| DK356275 | 1975-08-05 | ||
| GB32908/75A GB1492073A (en) | 1975-08-05 | 1975-08-06 | Pyrido(3,2-e)-as-triazine derivatives |
| GB3290875 | 1975-08-06 | ||
| FI752294 | 1975-08-13 | ||
| FI752294A FI59098C (fi) | 1975-08-05 | 1975-08-13 | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrido(3,2-e)-astriazinderivat |
| AT636675 | 1975-08-14 | ||
| DE2536387 | 1975-08-14 | ||
| AT636675A AT347958B (de) | 1975-08-05 | 1975-08-14 | Verfahren zur herstellung von neuen pyrido (3,2-e) -as-triazin-derivaten und von mit pharmazeutisch vertraeglichen saeuren gebildeten salzen dieser verbindungen |
| DE19752536387 DE2536387A1 (de) | 1975-08-05 | 1975-08-14 | Pyrido(3,2-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben |
| CH1064575A CH617199A5 (en) | 1975-08-05 | 1975-08-15 | Process for the preparation of pyrido[3,2-e]-as-triazine derivatives |
| DD18788175 | 1975-08-15 | ||
| CH1064575 | 1975-08-15 | ||
| DD187881A DD121323A5 (da) | 1975-08-05 | 1975-08-15 | |
| JP50099878A JPS5225796A (en) | 1975-08-05 | 1975-08-19 | Production of pyrid *3*22e* asstriazine derivative |
| JP9987875 | 1975-08-19 | ||
| BE159502 | 1975-08-27 | ||
| BE159502A BE832791A (fr) | 1975-08-05 | 1975-08-27 | Derives de pyrido(3,2-e)-as-triazine et procede pour leur preparation. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752294A7 FI752294A7 (da) | 1977-02-14 |
| FI59098B FI59098B (fi) | 1981-02-27 |
| FI59098C true FI59098C (fi) | 1981-06-10 |
Family
ID=27578944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752294A FI59098C (fi) | 1975-08-05 | 1975-08-13 | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrido(3,2-e)-astriazinderivat |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5225796A (da) |
| AT (1) | AT347958B (da) |
| BE (1) | BE832791A (da) |
| CH (1) | CH617199A5 (da) |
| DD (1) | DD121323A5 (da) |
| DE (1) | DE2536387A1 (da) |
| DK (1) | DK138426B (da) |
| FI (1) | FI59098C (da) |
| GB (1) | GB1492073A (da) |
| SE (1) | SE409456B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL74373A0 (en) * | 1984-02-21 | 1985-05-31 | Lilly Co Eli | Process for the preparation of diaminopyridines |
| BR9916154B1 (pt) * | 1998-12-01 | 2010-09-21 | 1,3,5 triazinas substituìdas, bem como método para controle de vegetação indesejável, uso e composição herbicida compreendendo as mesmas. | |
| WO2024094150A1 (en) * | 2022-11-04 | 2024-05-10 | Insilico Medicine Ip Limited | Nlrp3 inflammasome inhibitors and uses thereof |
-
1975
- 1975-08-05 DK DK356275AA patent/DK138426B/da not_active IP Right Cessation
- 1975-08-05 SE SE7508834A patent/SE409456B/xx unknown
- 1975-08-06 GB GB32908/75A patent/GB1492073A/en not_active Expired
- 1975-08-13 FI FI752294A patent/FI59098C/fi not_active IP Right Cessation
- 1975-08-14 AT AT636675A patent/AT347958B/de not_active IP Right Cessation
- 1975-08-14 DE DE19752536387 patent/DE2536387A1/de not_active Withdrawn
- 1975-08-15 DD DD187881A patent/DD121323A5/xx unknown
- 1975-08-15 CH CH1064575A patent/CH617199A5/de not_active IP Right Cessation
- 1975-08-19 JP JP50099878A patent/JPS5225796A/ja active Pending
- 1975-08-27 BE BE159502A patent/BE832791A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH617199A5 (en) | 1980-05-14 |
| FI59098B (fi) | 1981-02-27 |
| DD121323A5 (da) | 1976-07-20 |
| BE832791A (fr) | 1975-12-16 |
| SE409456B (sv) | 1979-08-20 |
| DK356275A (da) | 1977-02-06 |
| DK138426B (da) | 1978-09-04 |
| GB1492073A (en) | 1977-11-16 |
| ATA636675A (de) | 1978-06-15 |
| DK138426C (da) | 1979-02-12 |
| FI752294A7 (da) | 1977-02-14 |
| DE2536387A1 (de) | 1977-02-24 |
| AT347958B (de) | 1979-01-25 |
| JPS5225796A (en) | 1977-02-25 |
| SE7508834L (sv) | 1977-02-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU763463B2 (en) | Tetrahydropyridoethers | |
| KR100650472B1 (ko) | 위산 분비를 억제하는 이미다조 피리딘 유도체 | |
| AU647627B2 (en) | 7-Azaisoindolinyl-quinolone- and-naphthyridonecarboxylic acid derivatives | |
| EP0971922B1 (en) | Tetrahydropyrido compounds | |
| UA43841C2 (uk) | Імідазопіридини та фармацевтична композиція на їх основі | |
| Leach et al. | Reversible inhibitors of the gastric (H+/K+)-ATPase. 2. 1-Arylpyrrolo [3, 2-c] quinolines: effect of the 4-substituent | |
| IE57874B1 (en) | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines | |
| CZ292311B6 (cs) | Pyridazinové deriváty, způsob jejich výroby a farmaceutické prostředky, které je obsahují | |
| AU3732700A (en) | Fused pyridopyridazine inhibitors of cgmp phosphodiesterase | |
| KR100823762B1 (ko) | 알킬화된 이미다조피리딘 유도체 | |
| RO118428B1 (ro) | DERIVATI DE IMIDAZO[1,2-a]PIRIDINE ALCOXIALCHILCARBAMATI, PROCEDEE DE PREPARARE ALE ACESTORA SI COMPOZITIE FARMACEUTICA CARE II CONTINE | |
| US6197783B1 (en) | Tetrahydropyrido compounds | |
| EP0874849B1 (en) | 2,7-substituted octahydro-pyrrolo 1,2-a]pyrazine derivatives | |
| EA005597B1 (ru) | Пролекарства производных имидазопиридина | |
| AU783724B2 (en) | Tricyclic imidazopyridines | |
| FI59098C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara pyrido(3,2-e)-astriazinderivat | |
| RU2147303C1 (ru) | Промежуточные продукты и способ получения солей нафтиридонкарбоновой кислоты | |
| US3873543A (en) | 3-Substituted-as-triazino(5,6-c) quinoline derivatives | |
| AU783550B2 (en) | Imidazopyridin-8-ones | |
| CA2196076A1 (en) | Acyl imidazopyridines | |
| CN100465175C (zh) | 7-位取代高喜树碱类化合物及作为药物的用途 | |
| FI57595C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade pyrido-(3,4-e)-as-triazinderivat | |
| JP2552101B2 (ja) | 新規ピリドンカルボン酸誘導体及びその調製方法 | |
| FI63401B (fi) | Nytt foerfarande foer framstaellning av 4-oxo-4h-pyrido(1,2-a)pyrimidin-3-karboxylsyra- och 1-oxo-1h-pyrimido(1,2-a)kinolin-2-karboxylsyraderivat | |
| KR100359151B1 (ko) | 2환성 아미노기로 치환된 피리돈카르복실산 유도체, 그의 에스테르 및 그의 염 및 이들의 중간체인 2환성 아민 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: E GY T GYOGYSZERVEGYESZETI GYAR |