DE2536387A1 - Pyrido(3,2-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben - Google Patents
Pyrido(3,2-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselbenInfo
- Publication number
- DE2536387A1 DE2536387A1 DE19752536387 DE2536387A DE2536387A1 DE 2536387 A1 DE2536387 A1 DE 2536387A1 DE 19752536387 DE19752536387 DE 19752536387 DE 2536387 A DE2536387 A DE 2536387A DE 2536387 A1 DE2536387 A1 DE 2536387A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrido
- radical
- carbon atoms
- triazine
- triazine derivatives
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 18
- 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 description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title description 2
- -1 alkyl radical Chemical group 0.000 claims description 32
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- QPDGBZPNEZMTOU-UHFFFAOYSA-N (3-nitropyridin-2-yl)hydrazine Chemical compound NNC1=NC=CC=C1[N+]([O-])=O QPDGBZPNEZMTOU-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 238000001953 recrystallisation Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 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
- 230000000844 anti-bacterial effect Effects 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 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
- 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 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
- 238000009835 boiling Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- CTSJESOSYYDBNW-UHFFFAOYSA-N 3-phenylpyrido[3,2-e][1,2,4]triazine Chemical class C1=CC=CC=C1C1=NN=C(N=CC=C2)C2=N1 CTSJESOSYYDBNW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 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
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 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
- 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
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 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
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 description 1
- FPTCVTJCJMVIDV-UHFFFAOYSA-N 2-phenylacetohydrazide Chemical compound NNC(=O)CC1=CC=CC=C1 FPTCVTJCJMVIDV-UHFFFAOYSA-N 0.000 description 1
- KQXHMNUXNHQSOW-UHFFFAOYSA-N 3,4,5-trimethoxybenzohydrazide Chemical compound COC1=CC(C(=O)NN)=CC(OC)=C1OC KQXHMNUXNHQSOW-UHFFFAOYSA-N 0.000 description 1
- UGTSPCOTKOMOJH-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC=1C=C(C(=O)O)C=C(C1OC)OC.COC=1C=C(C(=O)O)C=C(C1OC)OC UGTSPCOTKOMOJH-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
- 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
- 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
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DCKLMCVFGBDBBU-UHFFFAOYSA-N C1=CC(Cl)=CC=C1C1=NN=C(N=CC=C2)C2=N1 Chemical compound C1=CC(Cl)=CC=C1C1=NN=C(N=CC=C2)C2=N1 DCKLMCVFGBDBBU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SJSOFNCYXJUNBT-UHFFFAOYSA-N Eudesmic acid Natural products COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000009512 pharmaceutical packaging Methods 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution 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
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940055764 triaz Drugs 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 (enExample) | 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 (enExample) | 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 |
|---|---|
| DE2536387A1 true DE2536387A1 (de) | 1977-02-24 |
Family
ID=27578944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752536387 Withdrawn DE2536387A1 (de) | 1975-08-05 | 1975-08-14 | Pyrido(3,2-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5225796A (enExample) |
| AT (1) | AT347958B (enExample) |
| BE (1) | BE832791A (enExample) |
| CH (1) | CH617199A5 (enExample) |
| DD (1) | DD121323A5 (enExample) |
| DE (1) | DE2536387A1 (enExample) |
| DK (1) | DK138426B (enExample) |
| FI (1) | FI59098C (enExample) |
| GB (1) | GB1492073A (enExample) |
| SE (1) | SE409456B (enExample) |
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 (enExample) | 1977-02-14 |
| FI59098C (fi) | 1981-06-10 |
| DD121323A5 (enExample) | 1976-07-20 |
| DK138426C (enExample) | 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 (enExample) | 1977-02-06 |
| JPS5225796A (en) | 1977-02-25 |
| SE7508834L (sv) | 1977-02-06 |
| CH617199A5 (en) | 1980-05-14 |
| SE409456B (sv) | 1979-08-20 |
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| 8125 | Change of the main classification |
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| 8139 | Disposal/non-payment of the annual fee |