NO843454L - Fremgangsmaate til fremstilling av flavene- og tioflavenderivater - Google Patents
Fremgangsmaate til fremstilling av flavene- og tioflavenderivaterInfo
- Publication number
- NO843454L NO843454L NO843454A NO843454A NO843454L NO 843454 L NO843454 L NO 843454L NO 843454 A NO843454 A NO 843454A NO 843454 A NO843454 A NO 843454A NO 843454 L NO843454 L NO 843454L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compounds
- formyl
- halogen
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 182
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 44
- 150000002367 halogens Chemical class 0.000 claims abstract description 44
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 39
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
- 239000001301 oxygen Substances 0.000 claims abstract description 24
- 239000011593 sulfur Chemical group 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 12
- -1 thionyl halide Chemical class 0.000 claims description 119
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 229910052796 boron Inorganic materials 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052727 yttrium Inorganic materials 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Chemical group 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- ZOSZQJVXFONAFE-UHFFFAOYSA-N 4-chloro-3-formyl-2-phenyl-2h-chromene-6-carboxylic acid Chemical compound O=CC1=C(Cl)C2=CC(C(=O)O)=CC=C2OC1C1=CC=CC=C1 ZOSZQJVXFONAFE-UHFFFAOYSA-N 0.000 claims description 3
- AHAKPGRXBHINAM-UHFFFAOYSA-N 4-chloro-5-hydroxy-2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O=CC1=C(Cl)C=2C(O)=CC=CC=2OC1C1=CC=CC=C1 AHAKPGRXBHINAM-UHFFFAOYSA-N 0.000 claims description 3
- XIYHVHMIXIYAMX-UHFFFAOYSA-N 4-chloro-6-fluoro-2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O=CC1=C(Cl)C2=CC(F)=CC=C2OC1C1=CC=CC=C1 XIYHVHMIXIYAMX-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 230000000144 pharmacologic effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 2
- 210000002345 respiratory system Anatomy 0.000 abstract description 2
- 208000019423 liver disease Diseases 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000002253 acid Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- 230000007062 hydrolysis Effects 0.000 description 23
- 238000006460 hydrolysis reaction Methods 0.000 description 23
- 239000007787 solid Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000013543 active substance Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 230000035484 reaction time Effects 0.000 description 14
- 238000010626 work up procedure Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000003396 thiol group Chemical class [H]S* 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 210000003097 mucus Anatomy 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000002953 preparative HPLC Methods 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 6
- AIOQBOPOGHAITF-UHFFFAOYSA-N 4-chloro-2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O1C2=CC=CC=C2C(Cl)=C(C=O)C1C1=CC=CC=C1 AIOQBOPOGHAITF-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
- 229910052987 metal hydride Inorganic materials 0.000 description 5
- 150000004681 metal hydrides Chemical class 0.000 description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- JRFZSUMZAUHNSL-UHFFFAOYSA-N chrysin 5,7-dimethyl ether Chemical compound C=1C(OC)=CC(OC)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 JRFZSUMZAUHNSL-UHFFFAOYSA-N 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 210000002540 macrophage Anatomy 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
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- 229920001592 potato starch Polymers 0.000 description 4
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- 125000001302 tertiary amino group Chemical group 0.000 description 4
- 230000032258 transport Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- JEDXIZNKYBSQNX-UHFFFAOYSA-N 4-chloro-2-phenyl-2h-thiochromene-3-carbaldehyde Chemical compound S1C2=CC=CC=C2C(Cl)=C(C=O)C1C1=CC=CC=C1 JEDXIZNKYBSQNX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
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- 229950005499 carbon tetrachloride Drugs 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 3
- IAFBOKYTDSDNHV-UHFFFAOYSA-N (2S)-(-)-5,7-dimethoxyflavanone Natural products O1C2=CC(OC)=CC(OC)=C2C(=O)CC1C1=CC=CC=C1 IAFBOKYTDSDNHV-UHFFFAOYSA-N 0.000 description 2
- SHGLJXBLXNNCTE-UHFFFAOYSA-N 2-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=CC=CC=C2O1 SHGLJXBLXNNCTE-UHFFFAOYSA-N 0.000 description 2
- MISPGSJZEWVEDP-UHFFFAOYSA-N 4-chloro-5,6,7-trimethoxy-2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O=CC1=C(Cl)C=2C(OC)=C(OC)C(OC)=CC=2OC1C1=CC=CC=C1 MISPGSJZEWVEDP-UHFFFAOYSA-N 0.000 description 2
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- MJOXZELXZLIYPI-UHFFFAOYSA-N titanium(2+) Chemical compound [Ti+2] MJOXZELXZLIYPI-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- BLSRSXLJVJVBIK-UHFFFAOYSA-N vanadium(2+) Chemical compound [V+2] BLSRSXLJVJVBIK-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838323292A GB8323292D0 (en) | 1983-08-31 | 1983-08-31 | Flavene and thioflavene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO843454L true NO843454L (no) | 1985-03-01 |
Family
ID=10548080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO843454A NO843454L (no) | 1983-08-31 | 1984-08-30 | Fremgangsmaate til fremstilling av flavene- og tioflavenderivater |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4935441A (de) |
| EP (1) | EP0139615B1 (de) |
| JP (1) | JPS60149580A (de) |
| AT (1) | ATE42285T1 (de) |
| AU (1) | AU578252B2 (de) |
| CA (1) | CA1237438A (de) |
| DD (1) | DD234008A5 (de) |
| DE (1) | DE3477778D1 (de) |
| DK (1) | DK416084A (de) |
| ES (2) | ES8706140A1 (de) |
| FI (1) | FI82459C (de) |
| GB (2) | GB8323292D0 (de) |
| GR (1) | GR80257B (de) |
| HU (1) | HU201919B (de) |
| IL (1) | IL72777A (de) |
| NO (1) | NO843454L (de) |
| NZ (1) | NZ209394A (de) |
| PH (1) | PH20920A (de) |
| PT (1) | PT79145B (de) |
| ZA (1) | ZA846788B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE161254T1 (de) * | 1990-07-27 | 1998-01-15 | Chugai Pharmaceutical Co Ltd | Benzopyranderivat |
| JP3076066B2 (ja) | 1996-08-27 | 2000-08-14 | 塩野義製薬株式会社 | クロメン−３−カルボン酸誘導体 |
| KR100985103B1 (ko) * | 2008-08-07 | 2010-10-05 | 덕성여자대학교 산학협력단 | 티오플라바논 유도체의 제조 방법 |
| CN110615784B (zh) * | 2019-10-25 | 2022-10-25 | 南开大学 | 具有黄酮骨架的内酯类似物的合成及应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8323293D0 (en) * | 1983-08-31 | 1983-10-05 | Zyma Sa | Substituted flavene and thioflavene derivatives |
-
1983
- 1983-08-31 GB GB838323292A patent/GB8323292D0/en active Pending
-
1984
- 1984-08-27 DE DE8484810423T patent/DE3477778D1/de not_active Expired
- 1984-08-27 FI FI843363A patent/FI82459C/fi not_active IP Right Cessation
- 1984-08-27 AT AT84810423T patent/ATE42285T1/de not_active IP Right Cessation
- 1984-08-27 IL IL72777A patent/IL72777A/xx unknown
- 1984-08-27 EP EP84810423A patent/EP0139615B1/de not_active Expired
- 1984-08-28 PT PT79145A patent/PT79145B/pt not_active IP Right Cessation
- 1984-08-29 CA CA000462006A patent/CA1237438A/en not_active Expired
- 1984-08-29 GB GB08421777A patent/GB2145719B/en not_active Expired
- 1984-08-29 DD DD84266737A patent/DD234008A5/de not_active IP Right Cessation
- 1984-08-30 HU HU843260A patent/HU201919B/hu not_active IP Right Cessation
- 1984-08-30 DK DK416084A patent/DK416084A/da not_active Application Discontinuation
- 1984-08-30 NZ NZ209394A patent/NZ209394A/en unknown
- 1984-08-30 PH PH31164A patent/PH20920A/en unknown
- 1984-08-30 AU AU32571/84A patent/AU578252B2/en not_active Ceased
- 1984-08-30 NO NO843454A patent/NO843454L/no unknown
- 1984-08-30 ZA ZA846788A patent/ZA846788B/xx unknown
- 1984-08-30 GR GR80257A patent/GR80257B/el unknown
- 1984-08-31 ES ES535589A patent/ES8706140A1/es not_active Expired
- 1984-08-31 JP JP59180891A patent/JPS60149580A/ja active Pending
-
1985
- 1985-07-30 ES ES545717A patent/ES8604556A1/es not_active Expired
-
1986
- 1986-05-28 US US06/869,458 patent/US4935441A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ZA846788B (en) | 1985-04-24 |
| FI843363A0 (fi) | 1984-08-27 |
| PT79145B (en) | 1986-11-14 |
| NZ209394A (en) | 1987-11-27 |
| ES8706140A1 (es) | 1987-06-01 |
| FI82459C (fi) | 1991-03-11 |
| ES535589A0 (es) | 1987-06-01 |
| ES8604556A1 (es) | 1986-02-01 |
| HUT36818A (en) | 1985-10-28 |
| GR80257B (en) | 1985-01-02 |
| FI843363A (fi) | 1985-03-01 |
| FI82459B (fi) | 1990-11-30 |
| GB2145719B (en) | 1987-02-04 |
| GB8323292D0 (en) | 1983-10-05 |
| DK416084D0 (da) | 1984-08-30 |
| JPS60149580A (ja) | 1985-08-07 |
| IL72777A (en) | 1988-03-31 |
| DD234008A5 (de) | 1986-03-19 |
| HU201919B (en) | 1991-01-28 |
| AU578252B2 (en) | 1988-10-20 |
| AU3257184A (en) | 1985-03-07 |
| ES545717A0 (es) | 1986-02-01 |
| CA1237438A (en) | 1988-05-31 |
| EP0139615A2 (de) | 1985-05-02 |
| PH20920A (en) | 1987-05-28 |
| PT79145A (en) | 1984-09-01 |
| EP0139615B1 (de) | 1989-04-19 |
| DE3477778D1 (en) | 1989-05-24 |
| US4935441A (en) | 1990-06-19 |
| DK416084A (da) | 1985-03-01 |
| GB2145719A (en) | 1985-04-03 |
| IL72777A0 (en) | 1984-11-30 |
| ATE42285T1 (de) | 1989-05-15 |
| EP0139615A3 (en) | 1986-01-02 |
| GB8421777D0 (en) | 1984-10-03 |
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