CH617199A5 - Process for the preparation of pyrido[3,2-e]-as-triazine derivatives - Google Patents
Process for the preparation of pyrido[3,2-e]-as-triazine derivatives Download PDFInfo
- Publication number
- CH617199A5 CH617199A5 CH1064575A CH1064575A CH617199A5 CH 617199 A5 CH617199 A5 CH 617199A5 CH 1064575 A CH1064575 A CH 1064575A CH 1064575 A CH1064575 A CH 1064575A CH 617199 A5 CH617199 A5 CH 617199A5
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- CH
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- Prior art keywords
- general formula
- group
- compound
- formula
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- GUODQFHMIYUCLH-UHFFFAOYSA-N pyrido[3,2-e][1,2,4]triazine Chemical class N1=NC=NC2=CC=CN=C21 GUODQFHMIYUCLH-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 6
- 230000003647 oxidation Effects 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 6
- 230000000845 anti-microbial effect Effects 0.000 claims abstract description 5
- -1 aminopyridine compounds Chemical class 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- QPDGBZPNEZMTOU-UHFFFAOYSA-N (3-nitropyridin-2-yl)hydrazine Chemical class NNC1=NC=CC=C1[N+]([O-])=O QPDGBZPNEZMTOU-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 150000003927 aminopyridines Chemical class 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 239000000047 product Substances 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 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 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
- 238000001914 filtration Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- YZEFUHIDWUTUJO-UHFFFAOYSA-N 1,2-dihydropyrido[3,2-e][1,2,4]triazine Chemical class C1=CC=C2N=CNNC2=N1 YZEFUHIDWUTUJO-UHFFFAOYSA-N 0.000 description 2
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 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
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 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 2
- YSEPYBZIHDZBEE-UHFFFAOYSA-N n'-(3-aminopyridin-2-yl)benzohydrazide Chemical compound NC1=CC=CN=C1NNC(=O)C1=CC=CC=C1 YSEPYBZIHDZBEE-UHFFFAOYSA-N 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
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
- GOQQXAUFLDKFTA-UHFFFAOYSA-N 2-pyrido[3,2-e][1,2,4]triazin-3-ylphenol Chemical compound OC1=C(C=CC=C1)C=1N=NC2=C(N=1)C=CC=N2 GOQQXAUFLDKFTA-UHFFFAOYSA-N 0.000 description 1
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
- JZXKNAFHDCNAHQ-UHFFFAOYSA-N 3-(3,4,5-trimethoxyphenyl)-1,2-dihydropyrido[3,2-e][1,2,4]triazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(C=2NNC3=NC=CC=C3N=2)=C1 JZXKNAFHDCNAHQ-UHFFFAOYSA-N 0.000 description 1
- CCHYIJJFACTRTO-UHFFFAOYSA-N 3-(3,4,5-trimethoxyphenyl)pyrido[3,2-e][1,2,4]triazine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3C=CC=NC3=NN=2)=C1 CCHYIJJFACTRTO-UHFFFAOYSA-N 0.000 description 1
- GMQDBIOALKJZBM-UHFFFAOYSA-N 3-benzyl-1,2-dihydropyrido[3,2-e][1,2,4]triazine;dihydrochloride Chemical compound Cl.Cl.N=1C2=CC=CN=C2NNC=1CC1=CC=CC=C1 GMQDBIOALKJZBM-UHFFFAOYSA-N 0.000 description 1
- HNMRWJSGOYYDAX-UHFFFAOYSA-N 3-benzylpyrido[3,2-e][1,2,4]triazine Chemical compound N=1N=C2N=CC=CC2=NC=1CC1=CC=CC=C1 HNMRWJSGOYYDAX-UHFFFAOYSA-N 0.000 description 1
- CTSJESOSYYDBNW-UHFFFAOYSA-N 3-phenylpyrido[3,2-e][1,2,4]triazine Chemical compound C1=CC=CC=C1C1=NN=C(N=CC=C2)C2=N1 CTSJESOSYYDBNW-UHFFFAOYSA-N 0.000 description 1
- FYHJAYSWPGYCPF-UHFFFAOYSA-N 4-(1,2-dihydropyrido[3,2-e][1,2,4]triazin-3-yl)phenol Chemical compound OC1=CC=C(C=C1)C=1NNC2=C(N1)C=CC=N2 FYHJAYSWPGYCPF-UHFFFAOYSA-N 0.000 description 1
- PKBGHORNUFQAAW-UHFFFAOYSA-N 4-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Cl)C=C1 PKBGHORNUFQAAW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- HHQDNOXLJMIISM-UHFFFAOYSA-N pyrido[3,2-d]triazine Chemical class C1=NN=NC2=CC=CN=C21 HHQDNOXLJMIISM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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 |
|---|---|---|---|
| SE7508834A SE409456B (sv) | 1975-08-05 | 1975-08-05 | Analogiforfarande for framstellning av pyrido(3,2-e)-as-triazinderivat |
| DK356275AA DK138426B (da) | 1975-08-05 | 1975-08-05 | Analogifremgangsmåde til fremstilling af pyrido(3,2-e)-as-triazinderivater. |
| 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 |
| 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 |
| DD187881A DD121323A5 (OSRAM) | 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 (10)
| 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 |
| DK356275AA DK138426B (da) | 1975-08-05 | 1975-08-05 | Analogifremgangsmåde til fremstilling af pyrido(3,2-e)-as-triazinderivater. |
| 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 |
| 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 |
| DD187881A DD121323A5 (OSRAM) | 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. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617199A5 true CH617199A5 (en) | 1980-05-14 |
Family
ID=27578944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1064575A CH617199A5 (en) | 1975-08-05 | 1975-08-15 | Process for the preparation of pyrido[3,2-e]-as-triazine derivatives |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5225796A (OSRAM) |
| AT (1) | AT347958B (OSRAM) |
| BE (1) | BE832791A (OSRAM) |
| CH (1) | CH617199A5 (OSRAM) |
| DD (1) | DD121323A5 (OSRAM) |
| DE (1) | DE2536387A1 (OSRAM) |
| DK (1) | DK138426B (OSRAM) |
| FI (1) | FI59098C (OSRAM) |
| GB (1) | GB1492073A (OSRAM) |
| SE (1) | SE409456B (OSRAM) |
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 |
| DE69928282T2 (de) * | 1998-12-01 | 2006-06-29 | Bayer Cropscience Ag | Substituierte 1,3,5-triazine als herbizide |
| WO2024094150A1 (en) * | 2022-11-04 | 2024-05-10 | Insilico Medicine Ip Limited | Nlrp3 inflammasome inhibitors and uses thereof |
-
1975
- 1975-08-05 SE SE7508834A patent/SE409456B/xx unknown
- 1975-08-05 DK DK356275AA patent/DK138426B/da not_active IP Right Cessation
- 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 DE DE19752536387 patent/DE2536387A1/de not_active Withdrawn
- 1975-08-14 AT AT636675A patent/AT347958B/de not_active IP Right Cessation
- 1975-08-15 CH CH1064575A patent/CH617199A5/de not_active IP Right Cessation
- 1975-08-15 DD DD187881A patent/DD121323A5/xx unknown
- 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 |
|---|---|
| FI752294A7 (OSRAM) | 1977-02-14 |
| FI59098C (fi) | 1981-06-10 |
| DD121323A5 (OSRAM) | 1976-07-20 |
| DK138426C (OSRAM) | 1979-02-12 |
| FI59098B (fi) | 1981-02-27 |
| DK138426B (da) | 1978-09-04 |
| GB1492073A (en) | 1977-11-16 |
| BE832791A (fr) | 1975-12-16 |
| AT347958B (de) | 1979-01-25 |
| ATA636675A (de) | 1978-06-15 |
| DK356275A (OSRAM) | 1977-02-06 |
| JPS5225796A (en) | 1977-02-25 |
| SE7508834L (sv) | 1977-02-06 |
| DE2536387A1 (de) | 1977-02-24 |
| SE409456B (sv) | 1979-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |