HU193350B - Process for preparing 2-phenyl-pyrano /2,3-5/pyridines - Google Patents
Process for preparing 2-phenyl-pyrano /2,3-5/pyridines Download PDFInfo
- Publication number
- HU193350B HU193350B HU854021A HU402185A HU193350B HU 193350 B HU193350 B HU 193350B HU 854021 A HU854021 A HU 854021A HU 402185 A HU402185 A HU 402185A HU 193350 B HU193350 B HU 193350B
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- pyridine
- formula
- dichlorophenyl
- pyrano
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 238000000034 method Methods 0.000 claims abstract description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- -1 alkyl lithium Chemical compound 0.000 claims description 27
- 230000002829 reductive effect Effects 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000007858 starting material Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 11
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 11
- 229910052744 lithium Inorganic materials 0.000 claims description 11
- KPNRIVBFNMVMSS-UHFFFAOYSA-N 6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1OC2=NC=C(Br)C=C2CC1 KPNRIVBFNMVMSS-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- PLUZLNCQMIQXML-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(S(=O)(=O)C)=CN=C2OC1C1=CC=C(Cl)C(Cl)=C1 PLUZLNCQMIQXML-UHFFFAOYSA-N 0.000 claims description 5
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical class COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- HIMNTGWIQJTDRW-HWKANZROSA-N (e)-1-(5-bromo-2-methoxypyridin-3-yl)-3-(3,4-dichlorophenyl)prop-2-en-1-ol Chemical compound COC1=NC=C(Br)C=C1C(O)\C=C\C1=CC=C(Cl)C(Cl)=C1 HIMNTGWIQJTDRW-HWKANZROSA-N 0.000 claims description 2
- OHEHSISCLAMMTC-QPJJXVBHSA-N (e)-1-(5-chloro-2-methoxypyridin-3-yl)-3-(4-chlorophenyl)prop-2-en-1-ol Chemical compound COC1=NC=C(Cl)C=C1C(O)\C=C\C1=CC=C(Cl)C=C1 OHEHSISCLAMMTC-QPJJXVBHSA-N 0.000 claims description 2
- WMHPSBWSQPFYCF-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(SC)=CN=C2OC1C1=CC=C(Cl)C(Cl)=C1 WMHPSBWSQPFYCF-UHFFFAOYSA-N 0.000 claims description 2
- MYBDTGDPCIIJEQ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(S(=O)C)=CN=C2OC1C1=CC=C(Cl)C(Cl)=C1 MYBDTGDPCIIJEQ-UHFFFAOYSA-N 0.000 claims description 2
- KQMBDIMNBGUTGB-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-methylsulfanyl-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(SC)=CN=C2OC1C1=CC=C(Cl)C=C1 KQMBDIMNBGUTGB-UHFFFAOYSA-N 0.000 claims description 2
- PTCGDPJRBUOVKQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-methylsulfonyl-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(S(=O)(=O)C)=CN=C2OC1C1=CC=C(Cl)C=C1 PTCGDPJRBUOVKQ-UHFFFAOYSA-N 0.000 claims description 2
- VXZMWAICFMCFHH-UHFFFAOYSA-N 3-(5-chloro-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)propan-1-ol Chemical compound COC1=NC=C(Cl)C=C1CCC(O)C1=CC=C(Cl)C(Cl)=C1 VXZMWAICFMCFHH-UHFFFAOYSA-N 0.000 claims description 2
- XSGYDKJCYGLHOL-UHFFFAOYSA-N 6-bromo-2-(4-chlorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1=CC(Cl)=CC=C1C1OC2=NC=C(Br)C=C2CC1 XSGYDKJCYGLHOL-UHFFFAOYSA-N 0.000 claims description 2
- RDJMRYYHRVKYPL-UHFFFAOYSA-N 6-chloro-2-(4-chlorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1=CC(Cl)=CC=C1C1OC2=NC=C(Cl)C=C2CC1 RDJMRYYHRVKYPL-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 2
- RKJRCCPEDPXHFV-HWKANZROSA-N (e)-1-(5-chloro-2-methoxypyridin-3-yl)-3-(3,4-dichlorophenyl)prop-2-en-1-ol Chemical compound COC1=NC=C(Cl)C=C1C(O)\C=C\C1=CC=C(Cl)C(Cl)=C1 RKJRCCPEDPXHFV-HWKANZROSA-N 0.000 claims 1
- GSJWGBOWLSDTTJ-UHFFFAOYSA-N 3-(2-chloro-5-methylsulfonylpyridin-3-yl)-1-(3,4-dichlorophenyl)propan-1-ol Chemical compound CS(=O)(=O)C1=CN=C(Cl)C(CCC(O)C=2C=C(Cl)C(Cl)=CC=2)=C1 GSJWGBOWLSDTTJ-UHFFFAOYSA-N 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 241000700605 Viruses Species 0.000 abstract description 22
- 238000007363 ring formation reaction Methods 0.000 abstract description 6
- WZNNOTSNAIGFJA-UHFFFAOYSA-N 1-phenyl-1-pyridin-2-ylpropan-1-ol Chemical compound C=1C=CC=NC=1C(O)(CC)C1=CC=CC=C1 WZNNOTSNAIGFJA-UHFFFAOYSA-N 0.000 abstract 1
- HLAZQBRTXAHCNS-UHFFFAOYSA-N 2-phenyl-1-pyridin-2-ylprop-1-en-1-ol Chemical compound C=1C=CC=CC=1C(C)=C(O)C1=CC=CC=N1 HLAZQBRTXAHCNS-UHFFFAOYSA-N 0.000 abstract 1
- CLQKOWSHLWXKDA-UHFFFAOYSA-N 2-phenyl-2h-pyrano[2,3-b]pyridine Chemical class C1=CC2=CC=CN=C2OC1C1=CC=CC=C1 CLQKOWSHLWXKDA-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 67
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- 239000000203 mixture Substances 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 150000002642 lithium compounds Chemical class 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000000840 anti-viral effect Effects 0.000 description 11
- 230000000120 cytopathologic effect Effects 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003937 drug carrier Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000003612 virological effect Effects 0.000 description 6
- AYEVELLBDURPJW-UHFFFAOYSA-N 3-bromo-5-chloro-2-methoxypyridine Chemical compound COC1=NC=C(Cl)C=C1Br AYEVELLBDURPJW-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- CTNGDWICKTYOND-UHFFFAOYSA-N 2h-pyrano[2,3-b]pyridine Chemical class C1=CC=C2C=CCOC2=N1 CTNGDWICKTYOND-UHFFFAOYSA-N 0.000 description 4
- KUQJOQDSCMXOEJ-UHFFFAOYSA-N 6-bromo-2-(3,4-dichlorophenyl)-2h-pyrano[2,3-b]pyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C=CC2=CC(Br)=CN=C2O1 KUQJOQDSCMXOEJ-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003443 antiviral agent Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- IBEOGICJOHYRCR-UHFFFAOYSA-N 2,5-bis(methylsulfonyl)pyridine Chemical compound CS(=O)(=O)C1=CC=C(S(C)(=O)=O)N=C1 IBEOGICJOHYRCR-UHFFFAOYSA-N 0.000 description 3
- RPLNBBRNJGJWPP-UHFFFAOYSA-N 2-chloro-3-iodo-5-methylsulfonylpyridine Chemical compound CS(=O)(=O)C1=CN=C(Cl)C(I)=C1 RPLNBBRNJGJWPP-UHFFFAOYSA-N 0.000 description 3
- MBMQYTQCUCQJEH-UHFFFAOYSA-N 3,5-dibromo-2-methoxypyridine Chemical compound COC1=NC=C(Br)C=C1Br MBMQYTQCUCQJEH-UHFFFAOYSA-N 0.000 description 3
- VRNOWEKCASDTFG-UHFFFAOYSA-N 5-bromo-2-methoxypyridine-3-carbaldehyde Chemical compound COC1=NC=C(Br)C=C1C=O VRNOWEKCASDTFG-UHFFFAOYSA-N 0.000 description 3
- IIHLRAYLXPTLCO-UHFFFAOYSA-N 6-chloro-2-(3,4-dichlorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(Cl)=CN=C2OC1C1=CC=C(Cl)C(Cl)=C1 IIHLRAYLXPTLCO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000006143 cell culture medium Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- AXJWXOROGVSXJG-QPJJXVBHSA-N (e)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(4-chlorophenyl)prop-2-en-1-one Chemical compound COC1=NC=C(Br)C=C1\C=C\C(=O)C1=CC=C(Cl)C=C1 AXJWXOROGVSXJG-QPJJXVBHSA-N 0.000 description 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 2
- FEAVXMPFTQROEI-UHFFFAOYSA-N 2h-pyrano[3,2-b]pyridine Chemical class C1=CN=C2C=CCOC2=C1 FEAVXMPFTQROEI-UHFFFAOYSA-N 0.000 description 2
- NWLIVKUSZWQPPR-UHFFFAOYSA-N 3-(2-chloro-5-methylsulfonylpyridin-3-yl)-1-(3,4-dichlorophenyl)propan-1-one Chemical compound CS(=O)(=O)C1=CN=C(Cl)C(CCC(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 NWLIVKUSZWQPPR-UHFFFAOYSA-N 0.000 description 2
- HEUCJRLGRBANOQ-UHFFFAOYSA-N 3-(5-chloro-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)propan-1-one Chemical compound COC1=NC=C(Cl)C=C1CCC(=O)C1=CC=C(Cl)C(Cl)=C1 HEUCJRLGRBANOQ-UHFFFAOYSA-N 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
- ASZONYNRWWLNHR-UHFFFAOYSA-N 3-bromo-2-methoxy-5-methylsulfonylpyridine Chemical compound COC1=NC=C(S(C)(=O)=O)C=C1Br ASZONYNRWWLNHR-UHFFFAOYSA-N 0.000 description 2
- RAGAZJPMFSIDSL-UHFFFAOYSA-N 3-iodo-5-methylsulfonyl-1h-pyridin-2-one Chemical compound CS(=O)(=O)C1=CNC(=O)C(I)=C1 RAGAZJPMFSIDSL-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/663,020 US4588733A (en) | 1984-10-19 | 1984-10-19 | 2-phenylpyrano[2,3-b]pyridines and their use in inhibiting viruses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT38946A HUT38946A (en) | 1986-07-28 |
| HU193350B true HU193350B (en) | 1987-09-28 |
Family
ID=24660185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU854021A HU193350B (en) | 1984-10-19 | 1985-10-17 | Process for preparing 2-phenyl-pyrano /2,3-5/pyridines |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4588733A (en, 2012) |
| EP (1) | EP0178633B1 (en, 2012) |
| JP (1) | JPH064633B2 (en, 2012) |
| KR (1) | KR900004214B1 (en, 2012) |
| CN (1) | CN1007249B (en, 2012) |
| AR (1) | AR242956A1 (en, 2012) |
| AT (1) | ATE71379T1 (en, 2012) |
| AU (1) | AU576906B2 (en, 2012) |
| CA (1) | CA1294282C (en, 2012) |
| DE (1) | DE3585128D1 (en, 2012) |
| DK (1) | DK161328C (en, 2012) |
| ES (2) | ES8703873A1 (en, 2012) |
| FI (1) | FI83520C (en, 2012) |
| GR (1) | GR852532B (en, 2012) |
| HU (1) | HU193350B (en, 2012) |
| IE (1) | IE58145B1 (en, 2012) |
| IL (1) | IL76776A (en, 2012) |
| NO (1) | NO162908C (en, 2012) |
| NZ (1) | NZ213814A (en, 2012) |
| PH (1) | PH23586A (en, 2012) |
| PT (1) | PT81329B (en, 2012) |
| ZA (1) | ZA857872B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5034531A (en) * | 1988-12-23 | 1991-07-23 | Schering Corporation | Fused polycyclic pyranyl compounds as antiviral agents |
| WO1993017682A1 (en) * | 1992-03-04 | 1993-09-16 | Abbott Laboratories | Angiotensin ii receptor antagonists |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518273A (en) * | 1966-08-03 | 1970-06-30 | Warner Lambert Pharmaceutical | Benzopyranquinolinol derivatives and process for their production |
| EP0051061A3 (en) * | 1978-03-15 | 1982-06-09 | The Wellcome Foundation Limited | Novel intermediates and process for their preparation |
| US4801593A (en) * | 1979-09-13 | 1989-01-31 | Burroughs Wellcome Co. | Chemotherapeutic agents |
| US4563468A (en) * | 1979-09-13 | 1986-01-07 | Burroughs Wellcome Co. | Chemotherapeutic agents |
| DE3069830D1 (en) * | 1979-09-13 | 1985-01-31 | Wellcome Found | Benzopyran compounds, useful as chemotherapeutic agents |
| US4371537A (en) * | 1981-08-13 | 1983-02-01 | The Dow Chemical Company | Sulfur-substituted phenoxypyridines having antiviral activity |
-
1984
- 1984-10-19 US US06/663,020 patent/US4588733A/en not_active Expired - Lifetime
-
1985
- 1985-10-14 ZA ZA857872A patent/ZA857872B/xx unknown
- 1985-10-14 NZ NZ213814A patent/NZ213814A/en unknown
- 1985-10-15 AU AU48588/85A patent/AU576906B2/en not_active Ceased
- 1985-10-15 AT AT85113077T patent/ATE71379T1/de active
- 1985-10-15 DE DE8585113077T patent/DE3585128D1/de not_active Expired - Fee Related
- 1985-10-15 CA CA000492979A patent/CA1294282C/en not_active Expired - Lifetime
- 1985-10-15 EP EP85113077A patent/EP0178633B1/en not_active Expired - Lifetime
- 1985-10-16 FI FI854026A patent/FI83520C/fi not_active IP Right Cessation
- 1985-10-16 NO NO854110A patent/NO162908C/no not_active IP Right Cessation
- 1985-10-16 KR KR1019850007615A patent/KR900004214B1/ko not_active Expired
- 1985-10-17 HU HU854021A patent/HU193350B/hu not_active IP Right Cessation
- 1985-10-17 PT PT81329A patent/PT81329B/pt not_active IP Right Cessation
- 1985-10-17 AR AR85301972A patent/AR242956A1/es active
- 1985-10-17 ES ES547983A patent/ES8703873A1/es not_active Expired
- 1985-10-17 JP JP60230070A patent/JPH064633B2/ja not_active Expired - Lifetime
- 1985-10-17 CN CN85109303A patent/CN1007249B/zh not_active Expired
- 1985-10-18 GR GR852532A patent/GR852532B/el unknown
- 1985-10-18 IE IE259085A patent/IE58145B1/en not_active IP Right Cessation
- 1985-10-18 DK DK478685A patent/DK161328C/da not_active IP Right Cessation
- 1985-10-21 PH PH32951A patent/PH23586A/en unknown
- 1985-10-22 IL IL76776A patent/IL76776A/xx not_active IP Right Cessation
-
1986
- 1986-09-12 ES ES557062A patent/ES8801283A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |