CA1294282C - 2-phenylpyrano[2,3-b]pyridine compounds and process for their preparation - Google Patents
2-phenylpyrano[2,3-b]pyridine compounds and process for their preparationInfo
- Publication number
- CA1294282C CA1294282C CA000492979A CA492979A CA1294282C CA 1294282 C CA1294282 C CA 1294282C CA 000492979 A CA000492979 A CA 000492979A CA 492979 A CA492979 A CA 492979A CA 1294282 C CA1294282 C CA 1294282C
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- pyrano
- dihydro
- bromo
- pyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 69
- 238000002360 preparation method Methods 0.000 title description 6
- 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 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 239000001257 hydrogen Substances 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- -1 di- or tri-chloro Chemical group 0.000 claims abstract description 40
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 22
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 64
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- 239000000047 product Substances 0.000 claims description 32
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 32
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 17
- 239000007868 Raney catalyst Substances 0.000 claims description 12
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 12
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 12
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
- 238000007363 ring formation reaction Methods 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 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 8
- 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 7
- 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 7
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical class COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 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 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 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 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 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 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
- 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 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- 239000000243 solution Substances 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 239000010410 layer Substances 0.000 description 25
- 241000700605 Viruses Species 0.000 description 22
- 230000000875 corresponding effect Effects 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 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
- 230000000840 anti-viral effect Effects 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000000120 cytopathologic effect Effects 0.000 description 11
- 150000002642 lithium compounds Chemical class 0.000 description 11
- 229940073584 methylene chloride Drugs 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 229960003390 magnesium sulfate Drugs 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 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
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 229960002668 sodium chloride Drugs 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 7
- 235000005513 chalcones Nutrition 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 238000012360 testing method Methods 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
- 230000000694 effects Effects 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
- 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 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229940074995 bromine Drugs 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 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 4
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 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
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 230000003612 virological effect Effects 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
- CTNGDWICKTYOND-UHFFFAOYSA-N 2h-pyrano[2,3-b]pyridine Chemical group C1=CC=C2C=CCOC2=N1 CTNGDWICKTYOND-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
- AYEVELLBDURPJW-UHFFFAOYSA-N 3-bromo-5-chloro-2-methoxypyridine Chemical compound COC1=NC=C(Cl)C=C1Br AYEVELLBDURPJW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012230 colorless oil Substances 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 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
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-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
- XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 2
- VRNOWEKCASDTFG-UHFFFAOYSA-N 5-bromo-2-methoxypyridine-3-carbaldehyde Chemical compound COC1=NC=C(Br)C=C1C=O VRNOWEKCASDTFG-UHFFFAOYSA-N 0.000 description 2
- MQYMDTXPEUFWAI-UHFFFAOYSA-N 5-chloro-2-methoxypyridine Chemical compound COC1=CC=C(Cl)[C]=N1 MQYMDTXPEUFWAI-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000709661 Enterovirus Species 0.000 description 2
- 238000007341 Heck reaction Methods 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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 2
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 1
- VLUMOWNVWOXZAU-VQHVLOKHSA-N (e)-2-methyl-3-phenylprop-2-enal Chemical compound O=CC(/C)=C/C1=CC=CC=C1 VLUMOWNVWOXZAU-VQHVLOKHSA-N 0.000 description 1
- HONRSHHPFBMLBT-OWOJBTEDSA-N (e)-3-(4-chlorophenyl)prop-2-enal Chemical compound ClC1=CC=C(\C=C\C=O)C=C1 HONRSHHPFBMLBT-OWOJBTEDSA-N 0.000 description 1
- WBPAOUHWPONFEQ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C(Cl)=C1 WBPAOUHWPONFEQ-UHFFFAOYSA-N 0.000 description 1
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
- NWQQKGMFHVBKPS-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridin-6-yl]ethanone Chemical compound C1CC2=CC(C(=O)C)=CN=C2OC1C1=CC=C(Cl)C(Cl)=C1 NWQQKGMFHVBKPS-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- GCTFDMFLLBCLPF-UHFFFAOYSA-N 2,5-dichloropyridine Chemical compound ClC1=CC=C(Cl)N=C1 GCTFDMFLLBCLPF-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical class CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- VAVGOGHLNAJECD-UHFFFAOYSA-N 2-chloro-6-methoxypyridine Chemical compound COC1=CC=CC(Cl)=N1 VAVGOGHLNAJECD-UHFFFAOYSA-N 0.000 description 1
- 150000005759 2-chloropyridine Chemical class 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- CCZWSTFVHJPCEM-UHFFFAOYSA-N 2-iodopyridine Chemical compound IC1=CC=CC=N1 CCZWSTFVHJPCEM-UHFFFAOYSA-N 0.000 description 1
- XNARZJQXBMWIQU-UHFFFAOYSA-N 3,4-dihydro-2h-pyrano[3,2-b]pyridine Chemical compound C1=CN=C2CCCOC2=C1 XNARZJQXBMWIQU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BEKQORFOHSZCLW-UHFFFAOYSA-N 6-bromo-2-(3-chlorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound ClC1=CC=CC(C2OC3=NC=C(Br)C=C3CC2)=C1 BEKQORFOHSZCLW-UHFFFAOYSA-N 0.000 description 1
- HRQMCZITRNDJHG-UHFFFAOYSA-N 6-bromo-2-(4-chlorophenyl)-2h-pyrano[2,3-b]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C=CC2=CC(Br)=CN=C2O1 HRQMCZITRNDJHG-UHFFFAOYSA-N 0.000 description 1
- OWSJDUUJDDSEFB-UHFFFAOYSA-N 6-bromo-2-(4-fluorophenyl)-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1=CC(F)=CC=C1C1OC2=NC=C(Br)C=C2CC1 OWSJDUUJDDSEFB-UHFFFAOYSA-N 0.000 description 1
- BCCMHMFSZLIYRR-UHFFFAOYSA-N 6-bromo-2-(4-methylphenyl)-2h-pyrano[2,3-b]pyridine Chemical compound C1=CC(C)=CC=C1C1C=CC2=CC(Br)=CN=C2O1 BCCMHMFSZLIYRR-UHFFFAOYSA-N 0.000 description 1
- CUTDWQGSJHHKLE-UHFFFAOYSA-N 6-bromo-3-methyl-2-phenyl-2h-pyrano[2,3-b]pyridine Chemical compound CC1=CC2=CC(Br)=CN=C2OC1C1=CC=CC=C1 CUTDWQGSJHHKLE-UHFFFAOYSA-N 0.000 description 1
- OYQTVXSDIWRLNG-UHFFFAOYSA-N 6-methylsulfanyl-2-phenyl-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(SC)=CN=C2OC1C1=CC=CC=C1 OYQTVXSDIWRLNG-UHFFFAOYSA-N 0.000 description 1
- AWCZUACANNUUIL-UHFFFAOYSA-N 6-methylsulfonyl-2-phenyl-3,4-dihydro-2h-pyrano[2,3-b]pyridine Chemical compound C1CC2=CC(S(=O)(=O)C)=CN=C2OC1C1=CC=CC=C1 AWCZUACANNUUIL-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000256844 Apis mellifera Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical compound CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241001492221 Echovirus E12 Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- SENRGCCOVBYBGK-UHFFFAOYSA-N [K].OOS(O)(=O)=O Chemical compound [K].OOS(O)(=O)=O SENRGCCOVBYBGK-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229930008407 benzylideneacetone Natural products 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 150000001788 chalcone derivatives Chemical class 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 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
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940091250 magnesium supplement Drugs 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
- 230000007886 mutagenicity Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 229940093930 potassium iodate Drugs 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
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 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
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229960001407 sodium bicarbonate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-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 |
|---|---|---|---|
| US663,020 | 1984-10-19 | ||
| US06/663,020 US4588733A (en) | 1984-10-19 | 1984-10-19 | 2-phenylpyrano[2,3-b]pyridines and their use in inhibiting viruses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1294282C true CA1294282C (en) | 1992-01-14 |
Family
ID=24660185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000492979A Expired - Lifetime CA1294282C (en) | 1984-10-19 | 1985-10-15 | 2-phenylpyrano[2,3-b]pyridine compounds and process for their preparation |
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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fowler | Synthesis of 1, 2-and 1, 4-dihydropyridines | |
| CN104854090B (zh) | 杂芳基衍生物和其用途 | |
| Potts et al. | Cycloaddition routes to azaanthraquinone derivatives. 1. Use of azadienophiles | |
| US4104275A (en) | Heteroaryl crown ethers | |
| JP2001505922A (ja) | 新規なカンプトテシン類縁体、その医薬としての使用及びそれを含有する医薬組成物 | |
| Weller et al. | Synthesis of 3-methyl-5, 6-dihydro-3H-benzofuro [3, 2-e] isoquinolin-7 (7aH)-ones | |
| Tsuge et al. | Reactions of 1, 4-bis (trimethylsilyl)-1, 4-dihydropyridines with carbonyl compounds: A new method for regioselective synthesis of 3-alkylpyridines. | |
| CA1294282C (en) | 2-phenylpyrano[2,3-b]pyridine compounds and process for their preparation | |
| US4736037A (en) | 2-halo-aryl-pyridinemethanols with analgesic or antiinflammatory activity | |
| Sanyal et al. | New. alpha.-methylene. gamma.-lactone derivatives of substituted nucleic acid bases as potential anticancer agents | |
| Litster et al. | The thermal rearrangements of 2-alkenyloxypyridine 1-oxides | |
| CA1175428A (en) | Process for preparing imidazo /1,2-a/ quinoline derivatives | |
| EP0586405B1 (de) | NEUE IN 4-STELLUNG DURCH ARYL ODER N-HETEROARYL SUBSTITUIERTE 2H-BENZO[b]PYRAN-DERIVATE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG SOWIE DIE VERBINDUNGEN ENTHALTENDE ZUBEREITUNGEN | |
| Bargar et al. | 3, 4‐Dihydro‐2‐phenyl‐2H‐pyrano [2, 3‐b] pyridines. Novel aza analogs of flavans | |
| Blache et al. | Synthesis of azacarbazoles | |
| JPS637174B2 (en, 2012) | ||
| EP0306300A2 (en) | Pyrrolo(1,2-a)imidazole and imidazo(1,2-a)pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors | |
| CN101317845B (zh) | 一类6-芳基取代吡啶类化合物的药物用途 | |
| Chaykovsky et al. | Transformation products of 2-(2-imidazolin-2-yl) benzophenone | |
| US4171371A (en) | Diketones | |
| OHTA et al. | Cleavage of CO bonds of iminoethers and methyl hydroxamates with Grignard reagents and butyllithium | |
| Ahmed et al. | A SYNTHESIS OF TAIWANIN C | |
| Soliman et al. | Syntheses of Heterocycles, 191 Reactions of β-Aminocrotononitrile with Heterocyclic Phenolic Compounds | |
| Abramovitch et al. | N‐alkoxydipyrrylmethenes | |
| Morisawa et al. | Synthesis of 4-Propenyl-α4-norpyridoxols through Claisen Rearrangement |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20010115 |