FI83520C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-fenylpyrano/2,3-b/pyridiner. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-fenylpyrano/2,3-b/pyridiner. Download PDFInfo
- Publication number
- FI83520C FI83520C FI854026A FI854026A FI83520C FI 83520 C FI83520 C FI 83520C FI 854026 A FI854026 A FI 854026A FI 854026 A FI854026 A FI 854026A FI 83520 C FI83520 C FI 83520C
- Authority
- FI
- Finland
- Prior art keywords
- pyrano
- pyridine
- dihydro
- dichlorophenyl
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 57
- 238000002360 preparation method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 19
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 79
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- -1 di- or trichloro Chemical group 0.000 claims description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000007868 Raney catalyst Substances 0.000 claims description 10
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
- 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 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical class COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 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 4
- CTNGDWICKTYOND-UHFFFAOYSA-N 2h-pyrano[2,3-b]pyridine Chemical compound C1=CC=C2C=CCOC2=N1 CTNGDWICKTYOND-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 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
- 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 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 1
- 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
- GDUYTLCVIKYLSL-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(2-methoxy-5-methylsulfonylpyridin-3-yl)propan-1-ol Chemical compound COC1=NC=C(S(C)(=O)=O)C=C1CCC(O)C1=CC=C(Cl)C(Cl)=C1 GDUYTLCVIKYLSL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- AFXKBGWIJHWUNU-UHFFFAOYSA-N 3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Chemical compound COC1=NC=C(Br)C=C1C=CC(O)C1=CC=C(Cl)C(Cl)=C1 AFXKBGWIJHWUNU-UHFFFAOYSA-N 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 64
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 36
- 239000007787 solid Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 24
- 241000700605 Viruses Species 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 18
- 150000002642 lithium compounds Chemical class 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 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
- 230000000840 anti-viral effect Effects 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052744 lithium Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000003937 drug carrier 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
- 239000002904 solvent Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000003612 virological effect Effects 0.000 description 5
- FEAVXMPFTQROEI-UHFFFAOYSA-N 2h-pyrano[3,2-b]pyridine Chemical group C1=CN=C2C=CCOC2=C1 FEAVXMPFTQROEI-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-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
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 235000005513 chalcones Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- IDBJDLSTIJLZJB-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)prop-2-en-1-ol Chemical compound C=CC(O)C1=CC=C(Cl)C(Cl)=C1 IDBJDLSTIJLZJB-UHFFFAOYSA-N 0.000 description 3
- 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
- MBMQYTQCUCQJEH-UHFFFAOYSA-N 3,5-dibromo-2-methoxypyridine Chemical compound COC1=NC=C(Br)C=C1Br MBMQYTQCUCQJEH-UHFFFAOYSA-N 0.000 description 3
- KRIZSOUMJXQNGU-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)prop-2-enal Chemical compound ClC1=CC=C(C=CC=O)C=C1Cl KRIZSOUMJXQNGU-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000709664 Picornaviridae Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012044 organic layer Substances 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
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- DVTOGQQAXKRFAY-BQYQJAHWSA-N (e)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(4-methylphenyl)prop-2-en-1-one Chemical compound COC1=NC=C(Br)C=C1\C=C\C(=O)C1=CC=C(C)C=C1 DVTOGQQAXKRFAY-BQYQJAHWSA-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
- 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 2
- 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 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- NPYYXUYLIHZYOU-UHFFFAOYSA-N 5-chloro-2-methoxypyridine Chemical compound COC1=CC=C(Cl)C=N1 NPYYXUYLIHZYOU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HAWPOVRQHFBASB-UHFFFAOYSA-N 6-bromo-2-phenyl-2h-pyrano[2,3-b]pyridine Chemical compound C1=CC2=CC(Br)=CN=C2OC1C1=CC=CC=C1 HAWPOVRQHFBASB-UHFFFAOYSA-N 0.000 description 2
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- 239000012894 fetal calf serum Substances 0.000 description 1
- QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical class C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000012336 iodinating agent Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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 (2)
| 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 |
| US66302084 | 1984-10-19 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI854026A0 FI854026A0 (fi) | 1985-10-16 |
| FI854026L FI854026L (fi) | 1986-04-20 |
| FI83520B FI83520B (fi) | 1991-04-15 |
| FI83520C true FI83520C (fi) | 1991-07-25 |
Family
ID=24660185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI854026A FI83520C (fi) | 1984-10-19 | 1985-10-16 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-fenylpyrano/2,3-b/pyridiner. |
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 |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: MERRELL DOW PHARMACEUTICALS INC. |