SU888823A3 - Способ получени производных пиридо (3,4- )-асимм-триазина или их солей - Google Patents
Способ получени производных пиридо (3,4- )-асимм-триазина или их солей Download PDFInfo
- Publication number
- SU888823A3 SU888823A3 SU772503097A SU2503097A SU888823A3 SU 888823 A3 SU888823 A3 SU 888823A3 SU 772503097 A SU772503097 A SU 772503097A SU 2503097 A SU2503097 A SU 2503097A SU 888823 A3 SU888823 A3 SU 888823A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- hydrochloride
- nitropyridine
- triazine
- ethanol
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- ZQDXEVWNBNDLPI-UHFFFAOYSA-N pyrido[3,4-e][1,2,4]triazine Chemical class N1=CN=C2C=NC=CC2=N1 ZQDXEVWNBNDLPI-UHFFFAOYSA-N 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
- -1 p-hydroxyphenyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002244 precipitate Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 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 claims description 8
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 claims description 8
- JOTRPRKONYTVBV-UHFFFAOYSA-N 4-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CN=CC=C1Cl JOTRPRKONYTVBV-UHFFFAOYSA-N 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000908 ammonium hydroxide Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 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 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 229960005322 streptomycin Drugs 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 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 claims description 4
- 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 claims description 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- 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 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002347 octyl 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])[H] 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 2
- 241000222122 Candida albicans Species 0.000 claims 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 claims description 2
- 206010030113 Oedema Diseases 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 241000223229 Trichophyton rubrum Species 0.000 claims description 2
- OIUQKKGYKMFPKW-UHFFFAOYSA-N [N+](=O)([O-])C=1C=NC=CC1.C(C1=CC=C(C=C1)OC)NN Chemical compound [N+](=O)([O-])C=1C=NC=CC1.C(C1=CC=C(C=C1)OC)NN OIUQKKGYKMFPKW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229940095731 candida albicans Drugs 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 235000010418 carrageenan Nutrition 0.000 claims description 2
- 229920001525 carrageenan Polymers 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 244000053095 fungal pathogen Species 0.000 claims description 2
- 230000030135 gastric motility Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000008991 intestinal motility Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims 2
- FPTCVTJCJMVIDV-UHFFFAOYSA-N 2-phenylacetohydrazide Chemical compound NNC(=O)CC1=CC=CC=C1 FPTCVTJCJMVIDV-UHFFFAOYSA-N 0.000 claims 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 claims 1
- AKNMBEADEAYKDS-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1=NC=CC=C1 Chemical compound Cl.[N+](=O)([O-])C1=NC=CC=C1 AKNMBEADEAYKDS-UHFFFAOYSA-N 0.000 claims 1
- 102000004867 Hydro-Lyases Human genes 0.000 claims 1
- 108090001042 Hydro-Lyases Proteins 0.000 claims 1
- 241001585714 Nola Species 0.000 claims 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical class NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000002365 anti-tubercular Effects 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000003467 diminishing effect Effects 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- FDRPZJWMPZUHBN-UHFFFAOYSA-N triazin-2-ium;chloride Chemical compound Cl.C1=CN=NN=C1 FDRPZJWMPZUHBN-UHFFFAOYSA-N 0.000 claims 1
- HWMWVURSDQRNDO-UHFFFAOYSA-N (3-nitropyridin-4-yl)hydrazine Chemical compound NNC1=CC=NC=C1[N+]([O-])=O HWMWVURSDQRNDO-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 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
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YNANGXWUZWWFKX-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethane-1,2-dione Chemical compound C1=CC(OC)=CC=C1C(=O)C(=O)C1=CC=C(OC)C=C1 YNANGXWUZWWFKX-UHFFFAOYSA-N 0.000 description 1
- CLRJRWBQIJXBIU-UHFFFAOYSA-N 6,7-dimethoxynaphthalen-1-amine;hydrochloride Chemical compound Cl.C1=CC(N)=C2C=C(OC)C(OC)=CC2=C1 CLRJRWBQIJXBIU-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 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 1
- DIETUHFZZUYVQV-UHFFFAOYSA-N NN.COC=1C=C(C(=O)O)C=C(C1OC)OC Chemical compound NN.COC=1C=C(C(=O)O)C=C(C1OC)OC DIETUHFZZUYVQV-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 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 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007363 ring formation reaction 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 (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 (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 |
|---|---|
| SU888823A3 true SU888823A3 (ru) | 1981-12-07 |
Family
ID=27578946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772503097A SU888823A3 (ru) | 1975-01-16 | 1977-07-21 | Способ получени производных пиридо (3,4- )-асимм-триазина или их солей |
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 AT AT636775A patent/AT343124B/de not_active IP Right Cessation
- 1975-08-14 FI FI752307A patent/FI57595C/fi 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 |
|---|---|
| FI752307A7 (enrdf_load_stackoverflow) | 1977-02-15 |
| FI57595C (fi) | 1980-09-10 |
| JPS5225797A (en) | 1977-02-25 |
| FI57595B (fi) | 1980-05-30 |
| SE409863B (sv) | 1979-09-10 |
| GB1483025A (en) | 1977-08-17 |
| AT343124B (de) | 1978-05-10 |
| CH612679A5 (en) | 1979-08-15 |
| ATA636775A (de) | 1977-09-15 |
| SE7508733L (sv) | 1977-02-02 |
| BE832792A (fr) | 1975-12-16 |
| DD121322A5 (enrdf_load_stackoverflow) | 1976-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1094556A (en) | Derivatives of 5,6-dihydrobenzo 5,6 cyclohepta [1,2- b]-pyrazolo[4,3-e]pyridin-11(1h)ones and 11(1h)- imines | |
| Matsumoto et al. | 1, 4-Dihydro-4-oxopyridinecarboxylic acids as antibacterial agents. 2. Synthesis and structure-activity relationships of 1, 6, 7-trisubstituted 1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acids, including enoxacin, a new antibacterial agent | |
| US3753993A (en) | 1,4-dihydro-4-oxo-7-pyridyl-3-quinoline-carboxylic acid derivatives | |
| KR900005025B1 (ko) | 퀴놀린 화합물 및 그의 제조방법 | |
| CZ99693A3 (en) | Amino quinolone derivatives substituted by aryl or aromatic heterocyclic groups | |
| Leach et al. | Reversible inhibitors of the gastric (H+/K+)-ATPase. 2. 1-Arylpyrrolo [3, 2-c] quinolines: effect of the 4-substituent | |
| US4636506A (en) | 7-heterocyclic-1,4-dihydroquinolones | |
| DK151331B (da) | Analogifremgangsmaade til fremstilling af 5-pyridinyl-2(1h)-pyridinon-forbindelser eller farmaceutisk acceptable syreadditionssalte deraf | |
| US2500131A (en) | Di-nu-oxides of amino-substituted acridines and quinolines | |
| US6162809A (en) | Pyridylthio compounds for controlling helicobacter bacteria | |
| EL‐Hashash et al. | Synthesis of 3‐cyano‐2‐pyridone derivative and its utility in the synthesis of some heterocyclic compounds with expecting antimicrobial activity | |
| CS241036B2 (en) | Method of pyrimidone derivatives production | |
| US3429887A (en) | 1,7-naphthyridine-3-carboxylic acid derivatives and their preparation | |
| SU888823A3 (ru) | Способ получени производных пиридо (3,4- )-асимм-триазина или их солей | |
| SU475768A3 (ru) | Способ получени (5-нитрофурил-2) -пиридинов | |
| IE56839B1 (en) | New 1h,3h-pyrrolo(1,2-c)thiazole derivatives,their preparation and compositions containing them | |
| US3992380A (en) | 5,8-Dihydro-5-oxo-2-(4-or 3-pyridinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acids and esters | |
| JPH06116241A (ja) | アリール基又は複素芳香環基置換アミノキノロン誘導体及びエイズ治療剤 | |
| US3873543A (en) | 3-Substituted-as-triazino(5,6-c) quinoline derivatives | |
| US2963478A (en) | 4, 7-diamino-nu-aralkyl-2-aryl-6-pteridinecarboxamides | |
| Deeba et al. | Synthesis, characterization and biological activities of 1, 3, 4-oxadiazole derivatives of nalidixic acid and their copper complexes | |
| Hermecz et al. | Nitrogen-bridgehead compounds; 401. Cyclization in phosphoryl chloride-polyphosphoric acid mixture | |
| RU2166504C2 (ru) | Кумаринхинолонкарбоновые кислоты и способ их получения | |
| US3378564A (en) | Certain pyridyl tetrazole derivatives | |
| US3506668A (en) | Method of preparing 8-hydroxy-quinolines |