DE2112840A1 - Neue 4-(4-Biphenylyl)-buttersaeuren,ihre Salze und Ester - Google Patents
Neue 4-(4-Biphenylyl)-buttersaeuren,ihre Salze und EsterInfo
- Publication number
- DE2112840A1 DE2112840A1 DE19712112840 DE2112840A DE2112840A1 DE 2112840 A1 DE2112840 A1 DE 2112840A1 DE 19712112840 DE19712112840 DE 19712112840 DE 2112840 A DE2112840 A DE 2112840A DE 2112840 A1 DE2112840 A1 DE 2112840A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- biphenylyl
- acid
- outset
- butyric acid
- 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.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims description 17
- 150000003839 salts Chemical class 0.000 title claims description 16
- XSFAQQLHYUBFKV-UHFFFAOYSA-N 4-(4-phenylphenyl)butanoic acid Chemical class C1=CC(CCCC(=O)O)=CC=C1C1=CC=CC=C1 XSFAQQLHYUBFKV-UHFFFAOYSA-N 0.000 title claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 47
- -1 4- (2-Fluoro-4-biphenylyl) -butyric acid Chemical compound 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000007530 organic bases Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 239000007868 Raney catalyst Substances 0.000 claims description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- GBDYPDLPBPYQMN-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=CC=C1Cl GBDYPDLPBPYQMN-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 238000006477 desulfuration reaction Methods 0.000 claims description 3
- 230000023556 desulfurization Effects 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- 150000002596 lactones Chemical class 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 235000011007 phosphoric acid Nutrition 0.000 claims description 3
- TYLDGEVEWDNUTE-ZHACJKMWSA-N (e)-4-hydroxy-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(\C=C\C(O)=O)O)=CC=C1C1=CC=CC=C1 TYLDGEVEWDNUTE-ZHACJKMWSA-N 0.000 claims description 2
- KFQGOLUWWNZVAS-ZHACJKMWSA-N (e)-4-oxo-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(=O)/C=C/C(=O)O)=CC=C1C1=CC=CC=C1 KFQGOLUWWNZVAS-ZHACJKMWSA-N 0.000 claims description 2
- NJGRSTRMISTCEB-UHFFFAOYSA-N 4-hydroxy-4-(4-phenylphenyl)butanoic acid Chemical compound C1=CC(C(CCC(O)=O)O)=CC=C1C1=CC=CC=C1 NJGRSTRMISTCEB-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- GBUMEGLMTNAXOM-UHFFFAOYSA-N 1,4-diphenylbutan-1-one Chemical compound C=1C=CC=CC=1C(=O)CCCC1=CC=CC=C1 GBUMEGLMTNAXOM-UHFFFAOYSA-N 0.000 claims 1
- NKHWEMUBLJRIAO-UHFFFAOYSA-N 4-[4-(4-nitrophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=C([N+]([O-])=O)C=C1 NKHWEMUBLJRIAO-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000001989 diazonium salts Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 48
- 150000003946 cyclohexylamines Chemical class 0.000 description 27
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000012362 glacial acetic acid Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- KTBYOYWDJLVJTL-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=CC=C1F KTBYOYWDJLVJTL-UHFFFAOYSA-N 0.000 description 13
- 239000000155 melt Substances 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000829 suppository Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 229920002261 Corn starch Polymers 0.000 description 9
- 239000008120 corn starch Substances 0.000 description 9
- 229940099112 cornstarch Drugs 0.000 description 9
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 9
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QJXYFMHMLHXAGW-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=C(F)C=C1 QJXYFMHMLHXAGW-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000001582 butter acid Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 229940006015 4-hydroxybutyric acid Drugs 0.000 description 4
- 229910002012 Aerosil® Inorganic materials 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- HSJPKVMKFNANOV-UHFFFAOYSA-N NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CCC(=O)O)=O Chemical compound NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CCC(=O)O)=O HSJPKVMKFNANOV-UHFFFAOYSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
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- 239000008298 dragée Substances 0.000 description 4
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- 229920000159 gelatin Polymers 0.000 description 4
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- 239000012074 organic phase Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- IIIKDGJYYBWVJZ-MDZDMXLPSA-N (e)-4-[4-(2-fluorophenyl)phenyl]-4-hydroxybut-2-enoic acid Chemical compound C1=CC(C(\C=C\C(O)=O)O)=CC=C1C1=CC=CC=C1F IIIKDGJYYBWVJZ-MDZDMXLPSA-N 0.000 description 3
- CYPQRTFAWYCOQE-MDZDMXLPSA-N (e)-4-[4-(2-fluorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C1=CC(C(=O)/C=C/C(=O)O)=CC=C1C1=CC=CC=C1F CYPQRTFAWYCOQE-MDZDMXLPSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 230000003110 anti-inflammatory effect Effects 0.000 description 3
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- WOFNMZNJGZJHJO-UHFFFAOYSA-N 1-(4-phenylphenyl)butan-1-one Chemical compound C1=CC(C(=O)CCC)=CC=C1C1=CC=CC=C1 WOFNMZNJGZJHJO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- STWPKTWKKONLHD-UHFFFAOYSA-N 4-[4-(4-amino-3-bromophenyl)phenyl]butanoic acid Chemical compound C1=C(Br)C(N)=CC=C1C1=CC=C(CCCC(O)=O)C=C1 STWPKTWKKONLHD-UHFFFAOYSA-N 0.000 description 2
- LIXJWLMDIDCEBN-UHFFFAOYSA-N 4-[4-(4-bromophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=C(Br)C=C1 LIXJWLMDIDCEBN-UHFFFAOYSA-N 0.000 description 2
- IYWPCNIEUKBHQZ-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=C(F)C=C1 IYWPCNIEUKBHQZ-UHFFFAOYSA-N 0.000 description 2
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical class C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
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- 239000012166 beeswax Substances 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
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- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
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- 239000008273 gelatin Substances 0.000 description 2
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- 229910052742 iron Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
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- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 229960001462 sodium cyclamate Drugs 0.000 description 2
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
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- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 2
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- 230000003612 virological effect Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- DMJDEZUEYXVYNO-DHZHZOJOSA-N (e)-3-(4-phenylphenyl)prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C1=CC=CC=C1 DMJDEZUEYXVYNO-DHZHZOJOSA-N 0.000 description 1
- ZOIRMVZWDRLJPI-OWOJBTEDSA-N (e)-4-oxobut-2-enoic acid Chemical class OC(=O)\C=C\C=O ZOIRMVZWDRLJPI-OWOJBTEDSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
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- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
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- MVFHRQWYCXYYMU-UHFFFAOYSA-N 3-(4-phenylphenyl)propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1C1=CC=CC=C1 MVFHRQWYCXYYMU-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- VEMDPYRYZFUHOO-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-phenylbutan-1-one Chemical compound C1=CC(Cl)=CC=C1CCCC(=O)C1=CC=CC=C1 VEMDPYRYZFUHOO-UHFFFAOYSA-N 0.000 description 1
- ZVMXCNFUJPLQFT-UHFFFAOYSA-N 4-(4-fluorophenyl)benzaldehyde Chemical compound C1=CC(F)=CC=C1C1=CC=C(C=O)C=C1 ZVMXCNFUJPLQFT-UHFFFAOYSA-N 0.000 description 1
- DOVGOCNFMULPHD-UHFFFAOYSA-N 4-[4-(2-aminophenyl)phenyl]butanoic acid Chemical compound NC1=CC=CC=C1C1=CC=C(CCCC(O)=O)C=C1 DOVGOCNFMULPHD-UHFFFAOYSA-N 0.000 description 1
- QTOGXZQXFICUCE-UHFFFAOYSA-N 4-[4-(2-fluoro-4-nitrophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=C([N+]([O-])=O)C=C1F QTOGXZQXFICUCE-UHFFFAOYSA-N 0.000 description 1
- YRTUFFFNUSJOBZ-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1F YRTUFFFNUSJOBZ-UHFFFAOYSA-N 0.000 description 1
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- KGUJGPMQGBFEPK-UHFFFAOYSA-N 4-[4-(4-amino-2-fluorophenyl)phenyl]butanoic acid Chemical compound FC1=CC(N)=CC=C1C1=CC=C(CCCC(O)=O)C=C1 KGUJGPMQGBFEPK-UHFFFAOYSA-N 0.000 description 1
- HABPRAIEBWKFRR-UHFFFAOYSA-N 4-[4-(4-aminophenyl)phenyl]butanoic acid Chemical compound C1=CC(N)=CC=C1C1=CC=C(CCCC(O)=O)C=C1 HABPRAIEBWKFRR-UHFFFAOYSA-N 0.000 description 1
- BWQGLYYHMAKCJD-UHFFFAOYSA-N 4-[4-(4-chloro-2-fluorophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=C(Cl)C=C1F BWQGLYYHMAKCJD-UHFFFAOYSA-N 0.000 description 1
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- JWZSTJYFEBRUAE-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=C(Cl)C=C1 JWZSTJYFEBRUAE-UHFFFAOYSA-N 0.000 description 1
- BDFLUKICTBVNKJ-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=C(Cl)C=C1 BDFLUKICTBVNKJ-UHFFFAOYSA-N 0.000 description 1
- BECLFIRSTVQHDJ-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)phenyl]-4-hydroxybutanoic acid Chemical compound C1=CC(C(CCC(O)=O)O)=CC=C1C1=CC=C(F)C=C1 BECLFIRSTVQHDJ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- JPULPPHTZRNRMD-UHFFFAOYSA-N C(CCC)(=O)O.C1(CCCCC1)N Chemical compound C(CCC)(=O)O.C1(CCCCC1)N JPULPPHTZRNRMD-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 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 1
- 229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 238000006350 Schiemann fluorination reaction Methods 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WJYHCYBNUJVCEH-UHFFFAOYSA-N cyclohexane;ethoxyethane Chemical compound CCOCC.C1CCCCC1 WJYHCYBNUJVCEH-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- HMOJUCUJIXEKOH-UHFFFAOYSA-N dicyanoalumanylformonitrile Chemical compound N#C[Al](C#N)C#N HMOJUCUJIXEKOH-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- LJWKFGGDMBPPAZ-UHFFFAOYSA-N ethoxyethane;toluene Chemical compound CCOCC.CC1=CC=CC=C1 LJWKFGGDMBPPAZ-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CBADACBTCCDCBI-UHFFFAOYSA-N methyl 4-[4-(2-chlorophenyl)phenyl]-4-oxobutanoate Chemical compound C1=CC(C(=O)CCC(=O)OC)=CC=C1C1=CC=CC=C1Cl CBADACBTCCDCBI-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- ZJVTYKZWDWVIFD-UHFFFAOYSA-N zinc;hydrochloride Chemical compound Cl.[Zn] ZJVTYKZWDWVIFD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (50)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112840 DE2112840A1 (de) | 1971-03-17 | 1971-03-17 | Neue 4-(4-Biphenylyl)-buttersaeuren,ihre Salze und Ester |
| CH728975A CH573893A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH728675A CH573889A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH728475A CH580050A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH729475A CH573894A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH729575A CH573895A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH728575A CH566956A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH729175A CH566958A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH729275A CH566959A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH728875A CH574386A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH371772A CH574385A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH728775A CH573890A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH729075A CH566957A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| CH729375A CH566960A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-14 | |
| ES400792A ES400792A1 (es) | 1971-03-17 | 1972-03-15 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil)-butiricos y sus esteres. |
| NL7203400A NL7203400A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-15 | |
| AT1055172A AT316524B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| AT1055072A AT315824B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| IE338/72A IE36174B1 (en) | 1971-03-17 | 1972-03-16 | 4-(4-biphenylyl)-butyric acid derivatives |
| AT1055372A AT317873B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| AT1055472A AT317874B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| BE780821A BE780821A (fr) | 1971-03-17 | 1972-03-16 | Nouveaux derives de l'acide 4-(4-biphenylyl) butyrique |
| GB1241672A GB1390091A (en) | 1971-03-17 | 1972-03-16 | 4-4-biphenylyl-butyric acid derivatives |
| AT1055572A AT316526B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| AT1055872A AT316527B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| AT1055272A AT316525B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| AT1055772A AT321287B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| AT1055972A AT316528B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| IL38999A IL38999A (en) | 1971-03-17 | 1972-03-16 | 4-(4-biphenyl)-butyric acids and derivatives thereof and the preparation of such compounds |
| AT222372A AT310725B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| SE342172A SE393101B (sv) | 1971-03-17 | 1972-03-16 | Forfarande for framstellning av nya 4-(4-bifenylyl)-smorsyror med farmakologiska egenskaper |
| AT1055672A AT318584B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| AT1056172A AT316530B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| DK124172A DK132942C (da) | 1971-03-17 | 1972-03-16 | Analogifremgangsmade til fremstilling af 4-(4-biphenylyl)-smorsyrer eller estere eller salte heraf |
| AT1056072A AT316529B (de) | 1959-06-05 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-buttersäuren, ihren Salzen und Estern |
| FR7209420A FR2130390A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1972-03-17 | |
| AU40115/72A AU472025B2 (en) | 1971-03-17 | 1972-03-17 | 4-(4-biphenylyl)-butyric acids and derivatives thereof |
| ES406128A ES406128A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de 4 - (4 - bifenilil) - butiricos y sus esteres. |
| ES406131A ES406131A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de acidos 4-(4-bifeni- lil)-butiricos y sus esteres. |
| ES406123A ES406123A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de acidos 4-(4-bifeni- lil)-butiricos y sus esteres. |
| ES406124A ES406124A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de acidos 4-(4-bifeni- lil)-butiricos y sus esteres. |
| ES406126A ES406126A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de 4 - (4 - bifenilil) - butiricos y sus esteres. |
| ES406127A ES406127A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de 4 - (4 - bifenilil) - butiricos y sus esteres. |
| ES406130A ES406130A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de 4 - (4 - bifenilil) - butiricos y sus esteres. |
| ES406125A ES406125A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de acidos 4-(4-bifeni- lil)-butiricos y sus esteres. |
| ES406132A ES406132A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de 4 - (4 - bifenilil) - butiricos y sus esteres. |
| ES406129A ES406129A1 (es) | 1971-03-17 | 1972-08-26 | Procedimiento para la preparacion de 4 - (4 - bifenilil) - butiricos y sus esteres. |
| US05/406,196 US4021479A (en) | 1971-03-17 | 1973-10-15 | Derivatives of 4-(4-biphenylyl)-butyric acid |
| FR7442066A FR2282866A1 (fr) | 1971-03-17 | 1974-12-19 | Nouveaux derives de l'acide 4-(4-biphenylyl)-butyrique |
| US05/543,266 US3997589A (en) | 1971-03-17 | 1975-01-23 | 4-(2'-Fluoro-4-biphenylylr-4-oxo-butyric acid and esters and salts thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112840 DE2112840A1 (de) | 1971-03-17 | 1971-03-17 | Neue 4-(4-Biphenylyl)-buttersaeuren,ihre Salze und Ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2112840A1 true DE2112840A1 (de) | 1972-10-05 |
Family
ID=5801828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712112840 Pending DE2112840A1 (de) | 1959-06-05 | 1971-03-17 | Neue 4-(4-Biphenylyl)-buttersaeuren,ihre Salze und Ester |
Country Status (7)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6420396B1 (en) * | 1998-12-16 | 2002-07-16 | Beiersdorf Ag | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
| US6677360B2 (en) * | 1998-12-16 | 2004-01-13 | Bayer Aktiengesellschaft | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
| US7091228B2 (en) | 2003-05-09 | 2006-08-15 | Bayer Pharmaceuticals Corporation | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
-
1971
- 1971-03-17 DE DE19712112840 patent/DE2112840A1/de active Pending
-
1972
- 1972-03-14 CH CH729175A patent/CH566958A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH729375A patent/CH566960A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH729575A patent/CH573895A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH728775A patent/CH573890A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH728975A patent/CH573893A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH729475A patent/CH573894A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH728875A patent/CH574386A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH371772A patent/CH574385A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH728475A patent/CH580050A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH728675A patent/CH573889A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH729075A patent/CH566957A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH729275A patent/CH566959A5/xx not_active IP Right Cessation
- 1972-03-14 CH CH728575A patent/CH566956A5/xx not_active IP Right Cessation
- 1972-03-15 ES ES400792A patent/ES400792A1/es not_active Expired
- 1972-03-16 DK DK124172A patent/DK132942C/da active
- 1972-03-16 SE SE342172A patent/SE393101B/xx unknown
- 1972-03-16 AT AT222372A patent/AT310725B/de not_active IP Right Cessation
- 1972-03-16 AT AT1055772A patent/AT321287B/de active
- 1972-08-26 ES ES406128A patent/ES406128A1/es not_active Expired
- 1972-08-26 ES ES406131A patent/ES406131A1/es not_active Expired
- 1972-08-26 ES ES406124A patent/ES406124A1/es not_active Expired
- 1972-08-26 ES ES406126A patent/ES406126A1/es not_active Expired
- 1972-08-26 ES ES406127A patent/ES406127A1/es not_active Expired
- 1972-08-26 ES ES406125A patent/ES406125A1/es not_active Expired
- 1972-08-26 ES ES406132A patent/ES406132A1/es not_active Expired
- 1972-08-26 ES ES406123A patent/ES406123A1/es not_active Expired
- 1972-08-26 ES ES406129A patent/ES406129A1/es not_active Expired
- 1972-08-26 ES ES406130A patent/ES406130A1/es not_active Expired
-
1974
- 1974-12-19 FR FR7442066A patent/FR2282866A1/fr active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6420396B1 (en) * | 1998-12-16 | 2002-07-16 | Beiersdorf Ag | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
| US6677360B2 (en) * | 1998-12-16 | 2004-01-13 | Bayer Aktiengesellschaft | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
| US7094911B2 (en) | 1998-12-16 | 2006-08-22 | Bayer Aktiengesellschaft | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
| US7091228B2 (en) | 2003-05-09 | 2006-08-15 | Bayer Pharmaceuticals Corporation | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| US7423156B2 (en) | 2003-05-09 | 2008-09-09 | Bayer Pharmaceuticals Corporation | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| US7968576B2 (en) | 2003-05-09 | 2011-06-28 | Smith Roger A | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| US8013166B2 (en) | 2003-05-09 | 2011-09-06 | Bayer Healthcare Llc | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
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