FI57595C - Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade pyrido-(3,4-e)-as-triazinderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade pyrido-(3,4-e)-as-triazinderivat Download PDFInfo
- Publication number
- FI57595C FI57595C FI752307A FI752307A FI57595C FI 57595 C FI57595 C FI 57595C FI 752307 A FI752307 A FI 752307A FI 752307 A FI752307 A FI 752307A FI 57595 C FI57595 C FI 57595C
- Authority
- FI
- Finland
- Prior art keywords
- group
- compound
- general formula
- formula
- pyrido
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 239000000126 substance Substances 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 20
- -1 potassium ferricyanide Chemical compound 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 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 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 239000001119 stannous chloride Substances 0.000 claims description 3
- 235000011150 stannous chloride Nutrition 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
- 239000002244 precipitate Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 7
- JOTRPRKONYTVBV-UHFFFAOYSA-N 4-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CN=CC=C1Cl JOTRPRKONYTVBV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BZPVREXVOZITPF-UHFFFAOYSA-N 4-methoxy-3-nitropyridine Chemical compound COC1=CC=NC=C1[N+]([O-])=O BZPVREXVOZITPF-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- PWLFEMRZJMLMSJ-UHFFFAOYSA-N 1-(3-nitropyridin-4-yl)-2-tetradecylhydrazine Chemical compound C(CCCCCCCCCCCCC)NNC1=C(C=NC=C1)[N+](=O)[O-] PWLFEMRZJMLMSJ-UHFFFAOYSA-N 0.000 description 2
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 2
- WSJAZZJVABOQPW-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)CCC(=O)NNC1=C(C=NC=C1)[N+](=O)[O-] Chemical compound Cl.C1(=CC=CC=C1)CCC(=O)NNC1=C(C=NC=C1)[N+](=O)[O-] WSJAZZJVABOQPW-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- PAQHCBQIBWFNCU-UHFFFAOYSA-N N'-(3-nitropyridin-4-yl)nonanehydrazide hydrochloride Chemical compound Cl.C(CCCCCCCC)(=O)NNC1=C(C=NC=C1)[N+](=O)[O-] PAQHCBQIBWFNCU-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- ZYUBVSGHEXRKAJ-UHFFFAOYSA-N [4-[(4-methoxyphenyl)methyl]-3-nitropyridin-2-yl]hydrazine hydrochloride Chemical compound Cl.C(C1=CC=C(C=C1)OC)C1=C(C(=NC=C1)NN)[N+](=O)[O-] ZYUBVSGHEXRKAJ-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- RRJVDMBZMAGZGE-UHFFFAOYSA-N hydron;4-methoxy-3-nitropyridine;chloride Chemical compound Cl.COC1=CC=NC=C1[N+]([O-])=O RRJVDMBZMAGZGE-UHFFFAOYSA-N 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- JGJNSNGIYJERAM-UHFFFAOYSA-N n'-(3-nitropyridin-4-yl)decanehydrazide Chemical compound CCCCCCCCCC(=O)NNC1=CC=NC=C1[N+]([O-])=O JGJNSNGIYJERAM-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000011541 reaction mixture 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
- ZHYZQXUYZJNEHD-CLFYSBASSA-N (2z)-3,7-dimethylocta-2,6-dienoic acid Chemical compound CC(C)=CCC\C(C)=C/C(O)=O ZHYZQXUYZJNEHD-CLFYSBASSA-N 0.000 description 1
- HWMWVURSDQRNDO-UHFFFAOYSA-N (3-nitropyridin-4-yl)hydrazine Chemical compound NNC1=CC=NC=C1[N+]([O-])=O HWMWVURSDQRNDO-UHFFFAOYSA-N 0.000 description 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- AJFUTCZBTOLZJK-UHFFFAOYSA-N 2-phenylpropanehydrazide Chemical compound NNC(=O)C(C)C1=CC=CC=C1 AJFUTCZBTOLZJK-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
- ZMZGIVVRBMFZSG-UHFFFAOYSA-N 4-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=C(O)C=C1 ZMZGIVVRBMFZSG-UHFFFAOYSA-N 0.000 description 1
- REKQLYUAUXYJSZ-UHFFFAOYSA-N 4-methoxybenzohydrazide Chemical compound COC1=CC=C(C(=O)NN)C=C1 REKQLYUAUXYJSZ-UHFFFAOYSA-N 0.000 description 1
- FVPYWNCAKBNRST-UHFFFAOYSA-N 4-pyrido[3,4-e][1,2,4]triazin-3-ylphenol Chemical compound OC1=CC=C(C=C1)C=1N=NC2=C(N=1)C=NC=C2 FVPYWNCAKBNRST-UHFFFAOYSA-N 0.000 description 1
- RGHDGRGJOSPDHW-UHFFFAOYSA-N 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(Cl)=CC=C1N1C2(CCN(CC=3C=CC=CC=3)CC2)C(=O)NC1 RGHDGRGJOSPDHW-UHFFFAOYSA-N 0.000 description 1
- GLMCYANHNSNDSL-UHFFFAOYSA-N C(CCCCCCCCC)(=O)[O-].[NH3+]N Chemical compound C(CCCCCCCCC)(=O)[O-].[NH3+]N GLMCYANHNSNDSL-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YHDVGLDGWPDBFD-UHFFFAOYSA-N Cl.COC=1C=C(C(=O)C2=C(C(=NC=C2)NN)[N+](=O)[O-])C=C(C1)OC Chemical compound Cl.COC=1C=C(C(=O)C2=C(C(=NC=C2)NN)[N+](=O)[O-])C=C(C1)OC YHDVGLDGWPDBFD-UHFFFAOYSA-N 0.000 description 1
- GESVFMHSJUZQMV-UHFFFAOYSA-N Cl.OC1=CC=C(C(=O)C2=C(C(=NC=C2)NN)[N+](=O)[O-])C=C1 Chemical compound Cl.OC1=CC=C(C(=O)C2=C(C(=NC=C2)NN)[N+](=O)[O-])C=C1 GESVFMHSJUZQMV-UHFFFAOYSA-N 0.000 description 1
- RLAXKSUHRPEIAM-UHFFFAOYSA-N Cl.OC1=NC=CC(=C1[N+](=O)[O-])NNC(C1=CC=CC=C1)=O Chemical compound Cl.OC1=NC=CC(=C1[N+](=O)[O-])NNC(C1=CC=CC=C1)=O RLAXKSUHRPEIAM-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZQHAUKNPTGWXBR-UHFFFAOYSA-N N'-(3-nitropyridin-4-yl)pyridine-4-carbohydrazide hydrochloride Chemical compound Cl.C(C1=CC=NC=C1)(=O)NNC1=C(C=NC=C1)[N+](=O)[O-] ZQHAUKNPTGWXBR-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 241001507673 Penicillium digitatum Species 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- ZQDXEVWNBNDLPI-UHFFFAOYSA-N pyrido[3,4-e][1,2,4]triazine Chemical class N1=CN=C2C=NC=CC2=N1 ZQDXEVWNBNDLPI-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- KXTZPAQXYKUVLD-UHFFFAOYSA-N tetradecanehydrazide Chemical compound CCCCCCCCCCCCCC(=O)NN KXTZPAQXYKUVLD-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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
-
- 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
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7508733A SE409863B (sv) | 1975-08-01 | 1975-08-01 | Analogiforfarande for framstellning av pyrido(3,4-e)-as-triazinderivat |
| GB32914/75A GB1483025A (en) | 1975-08-01 | 1975-08-06 | Pyrido(3,4-e)-as-triazine derivatives |
| CH1052075A CH612679A5 (en) | 1975-08-01 | 1975-08-13 | Process for the preparation of substituted pyrido[3,4-e]-as-triazine derivatives |
| AT636775A AT343124B (de) | 1975-08-01 | 1975-08-14 | Verfahren zur herstellung von neuen pyrido (3,4-e)-as-triazin-derivaten und von mit pharmazeutisch vertraglichen sauren gebildeten salzen dieser verbindungen |
| FI752307A FI57595C (fi) | 1975-08-01 | 1975-08-14 | Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade pyrido-(3,4-e)-as-triazinderivat |
| DD187880A DD121322A5 (enrdf_load_stackoverflow) | 1975-08-01 | 1975-08-15 | |
| DE19752536692 DE2536692A1 (de) | 1975-01-16 | 1975-08-18 | Pyrido(3,4-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben |
| JP50099879A JPS5225797A (en) | 1975-08-01 | 1975-08-19 | Production of novel derivative pyridd*3*44e** asstriazine |
| BE832792A BE832792A (fr) | 1975-08-01 | 1975-08-27 | Derives de pyrido(3,4-e)-as-triazine substitues et procede pour leur preparation. |
| SU772503097A SU888823A3 (ru) | 1975-08-01 | 1977-07-21 | Способ получени производных пиридо (3,4- )-асимм-триазина или их солей |
Applications Claiming Priority (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7508733A SE409863B (sv) | 1975-08-01 | 1975-08-01 | Analogiforfarande for framstellning av pyrido(3,4-e)-as-triazinderivat |
| SE7508733 | 1975-08-01 | ||
| GB3291475 | 1975-08-06 | ||
| GB32914/75A GB1483025A (en) | 1975-08-01 | 1975-08-06 | Pyrido(3,4-e)-as-triazine derivatives |
| CH1052075A CH612679A5 (en) | 1975-08-01 | 1975-08-13 | Process for the preparation of substituted pyrido[3,4-e]-as-triazine derivatives |
| CH1052075 | 1975-08-13 | ||
| FI752307 | 1975-08-14 | ||
| FI752307A FI57595C (fi) | 1975-08-01 | 1975-08-14 | Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade pyrido-(3,4-e)-as-triazinderivat |
| AT636775A AT343124B (de) | 1975-08-01 | 1975-08-14 | Verfahren zur herstellung von neuen pyrido (3,4-e)-as-triazin-derivaten und von mit pharmazeutisch vertraglichen sauren gebildeten salzen dieser verbindungen |
| AT636775 | 1975-08-14 | ||
| DD18788075 | 1975-08-15 | ||
| DD187880A DD121322A5 (enrdf_load_stackoverflow) | 1975-08-01 | 1975-08-15 | |
| DE19752536692 DE2536692A1 (de) | 1975-01-16 | 1975-08-18 | Pyrido(3,4-e)-as-triazinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben |
| DE2536692 | 1975-08-18 | ||
| JP9987975 | 1975-08-19 | ||
| JP50099879A JPS5225797A (en) | 1975-08-01 | 1975-08-19 | Production of novel derivative pyridd*3*44e** asstriazine |
| BE832792 | 1975-08-27 | ||
| BE832792A BE832792A (fr) | 1975-08-01 | 1975-08-27 | Derives de pyrido(3,4-e)-as-triazine substitues et procede pour leur preparation. |
| SU772503097A SU888823A3 (ru) | 1975-08-01 | 1977-07-21 | Способ получени производных пиридо (3,4- )-асимм-триазина или их солей |
| SU2503097 | 1977-07-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752307A7 FI752307A7 (enrdf_load_stackoverflow) | 1977-02-15 |
| FI57595B FI57595B (fi) | 1980-05-30 |
| FI57595C true FI57595C (fi) | 1980-09-10 |
Family
ID=27578946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752307A FI57595C (fi) | 1975-01-16 | 1975-08-14 | Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade pyrido-(3,4-e)-as-triazinderivat |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5225797A (enrdf_load_stackoverflow) |
| AT (1) | AT343124B (enrdf_load_stackoverflow) |
| BE (1) | BE832792A (enrdf_load_stackoverflow) |
| CH (1) | CH612679A5 (enrdf_load_stackoverflow) |
| DD (1) | DD121322A5 (enrdf_load_stackoverflow) |
| FI (1) | FI57595C (enrdf_load_stackoverflow) |
| GB (1) | GB1483025A (enrdf_load_stackoverflow) |
| SE (1) | SE409863B (enrdf_load_stackoverflow) |
| SU (1) | SU888823A3 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| 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 |
Family Cites Families (2)
| 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 |
| US3883526A (en) * | 1973-06-06 | 1975-05-13 | Morton Norwich Products Inc | 3-Benzylpyrido {8 3,4-e{9 -as-triazine and 1,2-dihydro-3-benzylpyrido{8 3,4-e{9 -as-triazine hydrochloride |
-
1975
- 1975-08-01 SE SE7508733A patent/SE409863B/xx unknown
- 1975-08-06 GB GB32914/75A patent/GB1483025A/en not_active Expired
- 1975-08-13 CH CH1052075A patent/CH612679A5/de not_active IP Right Cessation
- 1975-08-14 FI FI752307A patent/FI57595C/fi not_active IP Right Cessation
- 1975-08-14 AT AT636775A patent/AT343124B/de not_active IP Right Cessation
- 1975-08-15 DD DD187880A patent/DD121322A5/xx unknown
- 1975-08-19 JP JP50099879A patent/JPS5225797A/ja active Pending
- 1975-08-27 BE BE832792A patent/BE832792A/xx unknown
-
1977
- 1977-07-21 SU SU772503097A patent/SU888823A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AT343124B (de) | 1978-05-10 |
| SU888823A3 (ru) | 1981-12-07 |
| FI57595B (fi) | 1980-05-30 |
| ATA636775A (de) | 1977-09-15 |
| DD121322A5 (enrdf_load_stackoverflow) | 1976-07-20 |
| SE409863B (sv) | 1979-09-10 |
| JPS5225797A (en) | 1977-02-25 |
| SE7508733L (sv) | 1977-02-02 |
| CH612679A5 (en) | 1979-08-15 |
| BE832792A (fr) | 1975-12-16 |
| GB1483025A (en) | 1977-08-17 |
| FI752307A7 (enrdf_load_stackoverflow) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: EGYT GYOGYSZERVEGYESZETI GYAR |