CH612679A5 - Process for the preparation of substituted pyrido[3,4-e]-as-triazine derivatives - Google Patents
Process for the preparation of substituted pyrido[3,4-e]-as-triazine derivativesInfo
- Publication number
- CH612679A5 CH612679A5 CH1052075A CH1052075A CH612679A5 CH 612679 A5 CH612679 A5 CH 612679A5 CH 1052075 A CH1052075 A CH 1052075A CH 1052075 A CH1052075 A CH 1052075A CH 612679 A5 CH612679 A5 CH 612679A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- mol
- general formula
- nitropyridine
- ethanol
- Prior art date
Links
- ZQDXEVWNBNDLPI-UHFFFAOYSA-N pyrido[3,4-e][1,2,4]triazine Chemical class N1=CN=C2C=NC=CC2=N1 ZQDXEVWNBNDLPI-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 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
- HWMWVURSDQRNDO-UHFFFAOYSA-N (3-nitropyridin-4-yl)hydrazine Chemical compound NNC1=CC=NC=C1[N+]([O-])=O HWMWVURSDQRNDO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 5
- OWOZAJROCCSXPX-UHFFFAOYSA-N 1,2-dihydropyrido[3,4-e][1,2,4]triazine Chemical class C1=NC=C2N=CNNC2=C1 OWOZAJROCCSXPX-UHFFFAOYSA-N 0.000 claims description 4
- 230000000845 anti-microbial effect Effects 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 230000002165 photosensitisation Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- HHQDNOXLJMIISM-UHFFFAOYSA-N pyrido[3,2-d]triazine Chemical compound C1=NN=NC2=CC=CN=C21 HHQDNOXLJMIISM-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 115
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- 239000002244 precipitate Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- -1 pyridyl carboxylic acid Chemical class 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- 239000013078 crystal Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- 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 13
- 238000006243 chemical reaction Methods 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 239000000908 ammonium hydroxide Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- JOTRPRKONYTVBV-UHFFFAOYSA-N 4-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CN=CC=C1Cl JOTRPRKONYTVBV-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 5
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- UXABYTUUXAWSNW-UHFFFAOYSA-N 2-hydrazinylpyridin-3-amine;hydrochloride Chemical compound Cl.NNC1=NC=CC=C1N UXABYTUUXAWSNW-UHFFFAOYSA-N 0.000 description 3
- BZPVREXVOZITPF-UHFFFAOYSA-N 4-methoxy-3-nitropyridine Chemical compound COC1=CC=NC=C1[N+]([O-])=O BZPVREXVOZITPF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 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 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KEYDQLSZRPMYRB-UHFFFAOYSA-N N'-(3-aminopyridin-4-yl)pyridine-4-carbohydrazide hydrochloride Chemical compound Cl.C(C1=CC=NC=C1)(=O)NNC1=C(C=NC=C1)N KEYDQLSZRPMYRB-UHFFFAOYSA-N 0.000 description 2
- BCEFGPNXROSSFZ-UHFFFAOYSA-N N'-(3-nitropyridin-4-yl)-3-phenylpropanehydrazide Chemical compound C1(=CC=CC=C1)CCC(=O)NNC1=C(C=NC=C1)[N+](=O)[O-] BCEFGPNXROSSFZ-UHFFFAOYSA-N 0.000 description 2
- TXFJUOKIUGOLSA-UHFFFAOYSA-N N'-(3-nitropyridin-4-yl)nonanehydrazide Chemical compound C(CCCCCCCC)(=O)NNC1=C(C=NC=C1)[N+](=O)[O-] TXFJUOKIUGOLSA-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 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
- FKOJYCCLHIZHAR-UHFFFAOYSA-N (2-hydrazinyl-3-nitropyridin-4-yl)-(3,4,5-trimethoxyphenyl)methanone hydrochloride Chemical compound Cl.COC=1C=C(C(=O)C2=C(C(=NC=C2)NN)[N+](=O)[O-])C=C(C1OC)OC FKOJYCCLHIZHAR-UHFFFAOYSA-N 0.000 description 1
- QPDGBZPNEZMTOU-UHFFFAOYSA-N (3-nitropyridin-2-yl)hydrazine Chemical compound NNC1=NC=CC=C1[N+]([O-])=O QPDGBZPNEZMTOU-UHFFFAOYSA-N 0.000 description 1
- WTYZLHOECWAVEX-UHFFFAOYSA-N (3-nitropyridin-2-yl)hydrazine;hydrochloride Chemical compound Cl.NNC1=NC=CC=C1[N+]([O-])=O WTYZLHOECWAVEX-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UNRJJXFLFBUZCJ-UHFFFAOYSA-N 2-(1,2-dihydropyrido[3,4-e][1,2,4]triazin-3-yl)phenol hydrochloride Chemical compound Cl.OC1=C(C=CC=C1)C=1NNC2=C(N1)C=NC=C2 UNRJJXFLFBUZCJ-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
- YRRKASSYQRNDMG-UHFFFAOYSA-N 2-pyrido[3,4-e][1,2,4]triazin-3-ylphenol Chemical compound OC1=C(C=CC=C1)C=1N=NC2=C(N=1)C=NC=C2 YRRKASSYQRNDMG-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
- DOWVACHORBOSEF-UHFFFAOYSA-N 3,5-dimethoxybenzohydrazide Chemical compound COC1=CC(OC)=CC(C(=O)NN)=C1 DOWVACHORBOSEF-UHFFFAOYSA-N 0.000 description 1
- JSUANUKQJIYRJV-UHFFFAOYSA-N 3-(3,4,5-trimethoxyphenyl)-1,2-dihydropyrido[3,4-e][1,2,4]triazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(C=2NNC3=CC=NC=C3N=2)=C1 JSUANUKQJIYRJV-UHFFFAOYSA-N 0.000 description 1
- BBIJBOVUIVWBMG-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-1,2-dihydropyrido[3,4-e][1,2,4]triazine hydrochloride Chemical compound Cl.COC=1C=C(C=C(C1)OC)C=1NNC2=C(N1)C=NC=C2 BBIJBOVUIVWBMG-UHFFFAOYSA-N 0.000 description 1
- INNBYVOTMKCWIO-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)pyrido[3,4-e][1,2,4]triazine Chemical compound COC=1C=C(C=C(C=1)OC)C=1N=NC2=C(N=1)C=NC=C2 INNBYVOTMKCWIO-UHFFFAOYSA-N 0.000 description 1
- BAESTDWZNKBAPL-UHFFFAOYSA-N 3-benzyl-1,2-dihydropyrido[3,4-e][1,2,4]triazine;hydrochloride Chemical compound Cl.N=1C2=CN=CC=C2NNC=1CC1=CC=CC=C1 BAESTDWZNKBAPL-UHFFFAOYSA-N 0.000 description 1
- KZCXMZXYFQKQNP-UHFFFAOYSA-N 3-nonylpyrido[3,4-e][1,2,4]triazine Chemical compound C1=CN=CC2=NC(CCCCCCCCC)=NN=C21 KZCXMZXYFQKQNP-UHFFFAOYSA-N 0.000 description 1
- XISZDMXZCMGCDY-UHFFFAOYSA-N 3-octylpyrido[3,4-e][1,2,4]triazine Chemical compound C1=CN=CC2=NC(CCCCCCCC)=NN=C21 XISZDMXZCMGCDY-UHFFFAOYSA-N 0.000 description 1
- UGKWIWQDGYTGRM-UHFFFAOYSA-N 3-tridecylpyrido[3,4-e][1,2,4]triazine Chemical compound C(CCCCCCCCCCCC)C=1N=NC2=C(N1)C=NC=C2 UGKWIWQDGYTGRM-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
- 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
- BHULTRJLCXLINR-UHFFFAOYSA-N C(CC1=NC(C=NC=C2)=C2N=N1)C1=CC=CC=C1 Chemical compound C(CC1=NC(C=NC=C2)=C2N=N1)C1=CC=CC=C1 BHULTRJLCXLINR-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000186363 Mycobacterium kansasii Species 0.000 description 1
- MAQHLMYGHHFMFT-UHFFFAOYSA-N N'-(3-aminopyridin-4-yl)-2-phenylacetohydrazide hydrochloride Chemical compound Cl.C1(=CC=CC=C1)CC(=O)NNC1=C(C=NC=C1)N MAQHLMYGHHFMFT-UHFFFAOYSA-N 0.000 description 1
- QTDWORBNBNLITF-UHFFFAOYSA-N N'-(3-aminopyridin-4-yl)nonanehydrazide hydrochloride Chemical compound Cl.C(CCCCCCCC)(=O)NNC1=C(C=NC=C1)N QTDWORBNBNLITF-UHFFFAOYSA-N 0.000 description 1
- ZOIITXQUJQBDBI-UHFFFAOYSA-N N'-(3-nitropyridin-4-yl)-2-phenylacetohydrazide hydrochloride Chemical compound Cl.C1(=CC=CC=C1)CC(=O)NNC1=C(C=NC=C1)[N+](=O)[O-] ZOIITXQUJQBDBI-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ROGBVBLYGMXQRO-UHFFFAOYSA-N decanehydrazide Chemical compound CCCCCCCCCC(=O)NN ROGBVBLYGMXQRO-UHFFFAOYSA-N 0.000 description 1
- LHRXTFDXJQAGAV-UHFFFAOYSA-L disodium 3-hydroxy-4-(naphthalen-1-yldiazenyl)naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(cc2cc(ccc2c1N=Nc1cccc2ccccc12)S([O-])(=O)=O)S([O-])(=O)=O LHRXTFDXJQAGAV-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- YTQHSQQSLTYMSL-UHFFFAOYSA-N dodecanohydrazide Chemical compound CCCCCCCCCCCC(=O)NN YTQHSQQSLTYMSL-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 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 1
- LGWZHEVHVJPGMU-UHFFFAOYSA-N n'-(3-nitropyridin-4-yl)tetradecanehydrazide Chemical compound CCCCCCCCCCCCCC(=O)NNC1=CC=NC=C1[N+]([O-])=O LGWZHEVHVJPGMU-UHFFFAOYSA-N 0.000 description 1
- HMYRUXBSDBAVNN-UHFFFAOYSA-N nonanehydrazide Chemical compound CCCCCCCCC(=O)NN HMYRUXBSDBAVNN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 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
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 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 (9)
| 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 | |
| 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 (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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH612679A5 true CH612679A5 (en) | 1979-08-15 |
Family
ID=27578946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1052075A CH612679A5 (en) | 1975-08-01 | 1975-08-13 | Process for the preparation of substituted pyrido[3,4-e]-as-triazine derivatives |
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 |
| BE832792A (fr) | 1975-12-16 |
| FI57595C (fi) | 1980-09-10 |
| GB1483025A (en) | 1977-08-17 |
| FI752307A7 (enrdf_load_stackoverflow) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |