NO843453L - Fremgangsmaate til fremstilling av flavanon eller tioflavanonderivater - Google Patents

Fremgangsmaate til fremstilling av flavanon eller tioflavanonderivater

Info

Publication number: NO843453L
Authority: NO; Norway
Prior art keywords: substituted; formula; unsubstituted; compounds; alkylamino
Prior art date: 1983-08-31

Application number

NO843453A

Other languages

English (en)

Norwegian (no)

Inventor

Christian Gerard Rimbault

Original Assignee

Zyma Sa

Priority date (The priority date 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 date listed.)

1983-08-31

Filing date

1984-08-30

Publication date

1985-03-01

1984-08-30 Application filed by Zyma Sa filed Critical Zyma Sa

1985-03-01 Publication of NO843453L publication Critical patent/NO843453L/no

Links

238000000034 method Methods 0.000 title claims abstract description 34
238000002360 preparation method Methods 0.000 title claims description 15
ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 title description 5
235000011981 flavanones Nutrition 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 271
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 100
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 80
229910052736 halogen Inorganic materials 0.000 claims abstract description 68
150000002367 halogens Chemical class 0.000 claims abstract description 68
150000003839 salts Chemical class 0.000 claims abstract description 67
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 56
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 42
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 39
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 39
229910052760 oxygen Inorganic materials 0.000 claims abstract description 39
239000001301 oxygen Substances 0.000 claims abstract description 39
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 36
229910052717 sulfur Inorganic materials 0.000 claims abstract description 34
239000011593 sulfur Substances 0.000 claims abstract description 34
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 20
229930195733 hydrocarbon Natural products 0.000 claims abstract description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 17
150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 10
125000002252 acyl group Chemical group 0.000 claims abstract description 6
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract description 4
-1 methylsulfonyloxy Chemical group 0.000 claims description 342
125000003282 alkyl amino group Chemical group 0.000 claims description 102
125000000217 alkyl group Chemical group 0.000 claims description 100
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
125000003545 alkoxy group Chemical group 0.000 claims description 60
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 55
239000000203 mixture Substances 0.000 claims description 54
125000001424 substituent group Chemical group 0.000 claims description 49
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 47
125000004423 acyloxy group Chemical group 0.000 claims description 42
125000003396 thiol group Chemical class [H]S* 0.000 claims description 36
125000004093 cyano group Chemical group *C#N 0.000 claims description 29
125000004414 alkyl thio group Chemical group 0.000 claims description 28
125000001072 heteroaryl group Chemical group 0.000 claims description 28
125000004442 acylamino group Chemical group 0.000 claims description 26
125000001589 carboacyl group Chemical group 0.000 claims description 24
125000005236 alkanoylamino group Chemical group 0.000 claims description 23
125000005237 alkyleneamino group Chemical group 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 21
239000003795 chemical substances by application Substances 0.000 claims description 21
229910052796 boron Inorganic materials 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
229910052727 yttrium Inorganic materials 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 12
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
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 claims description 12
125000005210 alkyl ammonium group Chemical group 0.000 claims description 11
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
150000001721 carbon Chemical group 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000003302 alkenyloxy group Chemical group 0.000 claims description 10
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
125000005368 heteroarylthio group Chemical group 0.000 claims description 9
150000002430 hydrocarbons Chemical class 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 8
125000005241 heteroarylamino group Chemical group 0.000 claims description 8
125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
125000000547 substituted alkyl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000005864 Sulphur Substances 0.000 claims description 5
125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
125000002346 iodo group Chemical group I* 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical group CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical group CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 3
125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical group [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims 1
201000010099 disease Diseases 0.000 abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
210000002345 respiratory system Anatomy 0.000 abstract description 3
208000019423 liver disease Diseases 0.000 abstract 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
239000002253 acid Substances 0.000 description 59
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 48
238000002844 melting Methods 0.000 description 47
230000008018 melting Effects 0.000 description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
239000013078 crystal Substances 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
150000007513 acids Chemical class 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
150000003254 radicals Chemical class 0.000 description 20
239000007787 solid Substances 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 16
238000001704 evaporation Methods 0.000 description 16
230000008020 evaporation Effects 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
239000003921 oil Substances 0.000 description 14
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
239000007858 starting material Substances 0.000 description 13
BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 12
JSLCBUREUDLJKN-UHFFFAOYSA-N 3-(hydroxymethylidene)-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(=CO)C1C1=CC=CC=C1 JSLCBUREUDLJKN-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
125000001931 aliphatic group Chemical group 0.000 description 12
229910052500 inorganic mineral Inorganic materials 0.000 description 11
235000010755 mineral Nutrition 0.000 description 11
239000011707 mineral Substances 0.000 description 11
210000003097 mucus Anatomy 0.000 description 11
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
BLAOBJGLQMCVSR-UHFFFAOYSA-N OC=C1C(=S)C2=CC(C)=CC=C2OC1C1=CC=CC=C1 Chemical compound OC=C1C(=S)C2=CC(C)=CC=C2OC1C1=CC=CC=C1 BLAOBJGLQMCVSR-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000007792 addition Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
150000003973 alkyl amines Chemical class 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
150000001735 carboxylic acids Chemical class 0.000 description 8
238000001816 cooling Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
150000004820 halides Chemical class 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
125000001302 tertiary amino group Chemical group 0.000 description 7
238000012360 testing method Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
SWAJPHCXKPCPQZ-UHFFFAOYSA-N 7-hydroxyflavanone Chemical compound O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=CC=C1 SWAJPHCXKPCPQZ-UHFFFAOYSA-N 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
108010010803 Gelatin Proteins 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
238000001035 drying Methods 0.000 description 6
150000002148 esters Chemical class 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
150000002431 hydrogen Chemical class 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
150000003335 secondary amines Chemical class 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
210000003238 esophagus Anatomy 0.000 description 5
238000000605 extraction Methods 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
125000002950 monocyclic group Chemical group 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
238000003756 stirring Methods 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
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
GBEKCDWXYCETBT-UHFFFAOYSA-N 3-ethylidene-6-methyl-2-phenylchromene-4-thione Chemical compound O1C2=CC=C(C)C=C2C(=S)C(=CC)C1C1=CC=CC=C1 GBEKCDWXYCETBT-UHFFFAOYSA-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
241000700198 Cavia Species 0.000 description 4
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239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003463 sulfur Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 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
150000003512 tertiary amines Chemical class 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl 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
125000001391 thioamide group Chemical group 0.000 description 1
125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 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
210000003437 trachea Anatomy 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
230000009466 transformation 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
150000003918 triazines 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
229960002415 trichloroethylene Drugs 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
229910001935 vanadium oxide Inorganic materials 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
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Gastroenterology & Hepatology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

NO843453A 1983-08-31 1984-08-30 Fremgangsmaate til fremstilling av flavanon eller tioflavanonderivater NO843453L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB838323291A GB8323291D0 (en)	1983-08-31	1983-08-31	Flavanone and thioflavanone derivatives

Publications (1)

Publication Number	Publication Date
NO843453L true NO843453L (no)	1985-03-01

Family

ID=10548079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO843453A NO843453L (no)	1983-08-31	1984-08-30	Fremgangsmaate til fremstilling av flavanon eller tioflavanonderivater

Country Status (20)

Country	Link
US (1)	US4885298A (de)
EP (1)	EP0139614B1 (de)
JP (1)	JPS60155176A (de)
AT (1)	ATE55694T1 (de)
AU (1)	AU580006B2 (de)
CA (1)	CA1251213A (de)
DD (1)	DD222311A5 (de)
DE (1)	DE3483033D1 (de)
DK (1)	DK415984A (de)
ES (1)	ES8800191A1 (de)
FI (1)	FI843362A7 (de)
GB (2)	GB8323291D0 (de)
GR (1)	GR80258B (de)
HU (1)	HUT36817A (de)
IL (1)	IL72775A (de)
NO (1)	NO843453L (de)
NZ (1)	NZ209393A (de)
PH (2)	PH23456A (de)
PT (1)	PT79144B (de)
ZA (1)	ZA846785B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3431534A1 (de) *	1984-08-28	1986-03-13	Merck Patent Gmbh, 6100 Darmstadt	Flavanonderivate
EP1640371B1 (de) *	2003-06-20	2011-10-19	Pokka Corporation	Flavanonverbindung und deren verwendungen
KR100985103B1 (ko) *	2008-08-07	2010-10-05	덕성여자대학교 산학협력단	티오플라바논 유도체의 제조 방법
PL2423213T3 (pl) *	2009-04-23	2014-04-30	Yang Gengliang	Wytwarzanie i stosowanie nowych związków antybiotycznych, przeciwnowotworowych i ich pochodnych
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 (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2727057A (en) *	1952-03-01	1955-12-13	Monsanto Chemicals	Preparation of ethylene sulfonates
GB1250388A (de) *	1968-11-27	1971-10-20
US3678044A (en) *	1970-10-22	1972-07-18	Chevron Res	Substituted flavanones
US3772243A (en) *	1970-10-26	1973-11-13	Chevron Res	Polypropylene stabilized with substituted chalcones and flavanones
GB1522057A (en) *	1975-11-03	1978-08-23	Pfizer	9-hydroxydibenzo(b,d)pyrans and intermediates therefor
US4235913A (en) *	1977-06-07	1980-11-25	Pfizer Inc.	9-Hydroxyhexahydrodibeno[b,d]pyrans, 1-substituted-9-hydroxyhexahydrodibenzo]b,d]pyrans
US4162162A (en) *	1978-05-08	1979-07-24	E. I. Du Pont De Nemours And Company	Derivatives of aryl ketones and p-dialkyl-aminoarylaldehydes as visible sensitizers of photopolymerizable compositions
US4228177A (en) *	1979-08-08	1980-10-14	E. R. Squibb & Sons, Inc.	2,3-Dihydro-3-(1H-imidazol-1-ylmethylene)-4H-1-benzothiopyran-4-ones
US4241069A (en) *	1979-09-04	1980-12-23	Miles Laboratories, Inc.	3-Methylene flavanones and 3-methylene chromanones
CH648030A5 (de) *	1980-12-15	1985-02-28	Sandoz Ag	Benzopyran-allylaminderivate, verfahren zu ihrer herstellung und ihre verwendung.
GB8421801D0 (en) *	1984-08-29	1984-10-03	Unilever Plc	Detergent composition

1983
- 1983-08-31 GB GB838323291A patent/GB8323291D0/en active Pending
1984
- 1984-08-27 FI FI843362A patent/FI843362A7/fi not_active Application Discontinuation
- 1984-08-27 DE DE8484810422T patent/DE3483033D1/de not_active Expired - Lifetime
- 1984-08-27 IL IL72775A patent/IL72775A/xx unknown
- 1984-08-27 EP EP84810422A patent/EP0139614B1/de not_active Expired - Lifetime
- 1984-08-27 AT AT84810422T patent/ATE55694T1/de active
- 1984-08-28 PT PT79144A patent/PT79144B/pt not_active IP Right Cessation
- 1984-08-29 DD DD84266739A patent/DD222311A5/de not_active IP Right Cessation
- 1984-08-29 GB GB08421776A patent/GB2145718B/en not_active Expired
- 1984-08-29 CA CA000462000A patent/CA1251213A/en not_active Expired
- 1984-08-30 NZ NZ209393A patent/NZ209393A/en unknown
- 1984-08-30 NO NO843453A patent/NO843453L/no unknown
- 1984-08-30 AU AU32570/84A patent/AU580006B2/en not_active Ceased
- 1984-08-30 GR GR80258A patent/GR80258B/el unknown
- 1984-08-30 DK DK415984A patent/DK415984A/da not_active Application Discontinuation
- 1984-08-30 PH PH31165A patent/PH23456A/en unknown
- 1984-08-30 ZA ZA846785A patent/ZA846785B/xx unknown
- 1984-08-30 HU HU843261A patent/HUT36817A/hu unknown
- 1984-08-30 PH PH31166A patent/PH24450A/en unknown
- 1984-08-31 JP JP59180890A patent/JPS60155176A/ja active Pending
- 1984-08-31 ES ES535588A patent/ES8800191A1/es not_active Expired
1988
- 1988-08-02 US US07/229,798 patent/US4885298A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ES8800191A1 (es)	1987-11-01
FI843362A7 (fi)	1985-03-01
DE3483033D1 (de)	1990-09-27
ZA846785B (en)	1985-04-24
ATE55694T1 (de)	1990-09-15
US4885298A (en)	1989-12-05
IL72775A0 (en)	1984-11-30
DK415984D0 (da)	1984-08-30
HUT36817A (en)	1985-10-28
DK415984A (da)	1985-03-01
GB2145718B (en)	1987-02-04
PH23456A (en)	1989-08-07
GB2145718A (en)	1985-04-03
FI843362A0 (fi)	1984-08-27
GB8421776D0 (en)	1984-10-03
EP0139614B1 (de)	1990-08-22
ES535588A0 (es)	1987-11-01
EP0139614A3 (en)	1985-12-27
NZ209393A (en)	1987-11-27
DD222311A5 (de)	1985-05-15
AU580006B2 (en)	1988-12-22
PT79144A (en)	1984-09-01
PT79144B (en)	1986-11-14
JPS60155176A (ja)	1985-08-15
CA1251213A (en)	1989-03-14
EP0139614A2 (de)	1985-05-02
GB8323291D0 (en)	1983-10-05
AU3257084A (en)	1985-03-07
GR80258B (en)	1985-01-02
PH24450A (en)	1990-06-25
IL72775A (en)	1988-11-15

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US20080234327A1 (en)	2008-09-25	Dihydroindazole compounds useful in treating iron disorders
US20070149514A1 (en)	2007-06-28	Indole-phenylsulfonamide derivatives used as ppar-delta activating compounds
AU2004274328B2 (en)	2011-11-10	Cinnamoyl compound and use of the same
KR20030015242A (ko)	2003-02-20	ＴＮＦ-α시그널링의 조절물질
NO843453L (no)	1985-03-01	Fremgangsmaate til fremstilling av flavanon eller tioflavanonderivater
EP0140830B1 (de)	1989-08-30	Pharmazeutische Präparate enthaltend Flaven- oder Thioflaven-Derivate, deren Verwendung, Flavene und Thioflavene und Verfahren zu deren Herstellung
NO832314L (no)	1983-12-27	Ditioforbindelser, farmasoeytiske preparater inneholdende dem samt deres anvendelse
HU196075B (en)	1988-09-28	Process for producing thieno-benzo-pyranes and thiopyranes and pharmaceutical preparations containing same
US20100256385A1 (en)	2010-10-07	Prostaglandin e receptor antagonists
US4935441A (en)	1990-06-19	Flavene and thioflavene derivates, processes for their manufacture, pharmaceutical preparations that contain such compounds, and the use of the latter
US5145868A (en)	1992-09-08	Alkanophenones useful for treating allergies
WO2000018741A2 (en)	2000-04-06	Pyrazole compounds as cox-2 inhibitors
US4221806A (en)	1980-09-09	Novel benzothiopyran derivatives
US20110184014A1 (en)	2011-07-28	New compounds
CA2630896A1 (en)	2007-06-28	New compounds
HK40044332B (en)	2023-07-14	Sulfoximine compound as bromodomain protein inhibitor and pharmaceutical composition and medical use thereof
HK40044332A (en)	2021-09-30	Sulfoximine compound as bromodomain protein inhibitor and pharmaceutical composition and medical use thereof
WO1999007352A2 (en)	1999-02-18	Method for promoting expression of ldl receptor gene