NO841426L - Fenylaminobenzenalkanoler og fremgangsmaate for deres fremstilling - Google Patents
Fenylaminobenzenalkanoler og fremgangsmaate for deres fremstillingInfo
- Publication number
- NO841426L NO841426L NO841426A NO841426A NO841426L NO 841426 L NO841426 L NO 841426L NO 841426 A NO841426 A NO 841426A NO 841426 A NO841426 A NO 841426A NO 841426 L NO841426 L NO 841426L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- lower alkyl
- hydrogen
- prepared
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 4
- AZBHVSHRTSHTKQ-UHFFFAOYSA-N 2-anilinobenzaldehyde Chemical compound O=CC1=CC=CC=C1NC1=CC=CC=C1 AZBHVSHRTSHTKQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 229910052987 metal hydride Inorganic materials 0.000 claims description 9
- 150000004681 metal hydrides Chemical class 0.000 claims description 9
- JETHOROFJHJKGM-UHFFFAOYSA-N [5-methoxy-2-(4-phenylmethoxyanilino)phenyl]methanol Chemical compound OCC1=CC(OC)=CC=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 JETHOROFJHJKGM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- WELKBINNNXKQQS-UHFFFAOYSA-N 1,4-benzoquinone imine Chemical class N=C1C=CC(=O)C=C1 WELKBINNNXKQQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 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 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- -1 methylene methylene Chemical group 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 229910052727 yttrium Inorganic materials 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 102000003820 Lipoxygenases Human genes 0.000 description 7
- 108090000128 Lipoxygenases Proteins 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VBYUEKQLNUEHEN-UHFFFAOYSA-N 5-methoxy-2-(4-phenylmethoxyanilino)benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 VBYUEKQLNUEHEN-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- PTSYAGLMOWLDRC-UHFFFAOYSA-N 2-(4-phenylmethoxyanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 PTSYAGLMOWLDRC-UHFFFAOYSA-N 0.000 description 4
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 4
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 239000000924 antiasthmatic agent Substances 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- KQBDLOVXZHOAJI-UHFFFAOYSA-N (4-phenylmethoxyphenyl)azanium;chloride Chemical compound Cl.C1=CC(N)=CC=C1OCC1=CC=CC=C1 KQBDLOVXZHOAJI-UHFFFAOYSA-N 0.000 description 3
- UYQUBFWYHSVOJZ-UHFFFAOYSA-N 4-[2-(hydroxymethyl)-4-methoxyanilino]phenol Chemical compound OCC1=CC(OC)=CC=C1NC1=CC=C(O)C=C1 UYQUBFWYHSVOJZ-UHFFFAOYSA-N 0.000 description 3
- VXMNQZKPGTZZTK-UHFFFAOYSA-N 5-chloro-2-(4-hydroxyanilino)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(O)C=C1 VXMNQZKPGTZZTK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 206010006482 Bronchospasm Diseases 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 229960004217 benzyl alcohol Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
- 150000007965 phenolic acids Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 2
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 description 2
- FPIMZRVJKYCPAX-UHFFFAOYSA-N 2-(2-methoxyanilino)benzoic acid Chemical compound COC1=CC=CC=C1NC1=CC=CC=C1C(O)=O FPIMZRVJKYCPAX-UHFFFAOYSA-N 0.000 description 2
- JEWCJXLUKAHXNJ-UHFFFAOYSA-N 2-(4-hydroxy-2-methylanilino)benzoic acid Chemical compound CC1=CC(O)=CC=C1NC1=CC=CC=C1C(O)=O JEWCJXLUKAHXNJ-UHFFFAOYSA-N 0.000 description 2
- ODHJOROUCITYNF-UHFFFAOYSA-N 2-bromo-5-methoxybenzoic acid Chemical compound COC1=CC=C(Br)C(C(O)=O)=C1 ODHJOROUCITYNF-UHFFFAOYSA-N 0.000 description 2
- WJFOSEJLJIOJPN-UHFFFAOYSA-N 4-[2-(1-hydroxyethyl)anilino]phenol Chemical compound CC(O)C1=CC=CC=C1NC1=CC=C(O)C=C1 WJFOSEJLJIOJPN-UHFFFAOYSA-N 0.000 description 2
- DSWRPZOIRXVVEG-UHFFFAOYSA-N 4-[2-(hydroxymethyl)-4-methoxyphenyl]iminocyclohexa-2,5-dien-1-one Chemical compound OCC1=CC(OC)=CC=C1N=C1C=CC(=O)C=C1 DSWRPZOIRXVVEG-UHFFFAOYSA-N 0.000 description 2
- CRMIIPSCWLIADF-UHFFFAOYSA-N 4-[2-(hydroxymethyl)anilino]phenol Chemical compound OCC1=CC=CC=C1NC1=CC=C(O)C=C1 CRMIIPSCWLIADF-UHFFFAOYSA-N 0.000 description 2
- QMOXDONEDYZIED-UHFFFAOYSA-N 4-[4-chloro-2-(hydroxymethyl)anilino]phenol Chemical compound OCC1=CC(Cl)=CC=C1NC1=CC=C(O)C=C1 QMOXDONEDYZIED-UHFFFAOYSA-N 0.000 description 2
- VQJVQQSIWZBRKF-UHFFFAOYSA-N 4-chloro-2-(4-hydroxyanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=C(O)C=C1 VQJVQQSIWZBRKF-UHFFFAOYSA-N 0.000 description 2
- KAERBVZTGPZZHW-UHFFFAOYSA-N 4-chloro-2-(4-methoxyanilino)benzoic acid Chemical compound C1=CC(OC)=CC=C1NC1=CC(Cl)=CC=C1C(O)=O KAERBVZTGPZZHW-UHFFFAOYSA-N 0.000 description 2
- ISXKTCMFCWGVAH-UHFFFAOYSA-N 5-chloro-2-(4-methoxyanilino)benzoic acid Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(Cl)C=C1C(O)=O ISXKTCMFCWGVAH-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DQAODTQJDOWXBS-UHFFFAOYSA-N [2-(4-phenylmethoxyanilino)phenyl]methanol Chemical compound OCC1=CC=CC=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 DQAODTQJDOWXBS-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 201000009961 allergic asthma Diseases 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000001088 anti-asthma Effects 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 2
- 229960003291 chlorphenamine Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- KILRIAHKRJXAQT-UHFFFAOYSA-N ethyl 2-(2-hydroxyanilino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NC1=CC=CC=C1O KILRIAHKRJXAQT-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002617 leukotrienes Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XKKJKLNOCOBOPQ-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=C(O)C(Cl)=C1 XKKJKLNOCOBOPQ-UHFFFAOYSA-N 0.000 description 1
- SKGBZMKSNDBYFC-UHFFFAOYSA-N 2-(3-chloro-4-methoxyanilino)benzoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=CC=CC=C1C(O)=O SKGBZMKSNDBYFC-UHFFFAOYSA-N 0.000 description 1
- HKRPLQDFVHJIIM-UHFFFAOYSA-N 2-[2-(hydroxymethyl)anilino]phenol Chemical compound OCC1=CC=CC=C1NC1=CC=CC=C1O HKRPLQDFVHJIIM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- VNOIVXDBROIOAU-UHFFFAOYSA-N 2-chloro-4-[2-(hydroxymethyl)anilino]phenol Chemical compound OCC1=CC=CC=C1NC1=CC=C(O)C(Cl)=C1 VNOIVXDBROIOAU-UHFFFAOYSA-N 0.000 description 1
- XQVCBOLNTSUFGD-UHFFFAOYSA-N 3-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1Cl XQVCBOLNTSUFGD-UHFFFAOYSA-N 0.000 description 1
- YFEJFIBZPXJRSI-UHFFFAOYSA-N 4-(2-methylanilino)phenol Chemical compound CC1=CC=CC=C1NC1=CC=C(O)C=C1 YFEJFIBZPXJRSI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GAIAXLHKBNMOTK-UHFFFAOYSA-N 4-[2-(hydroxymethyl)anilino]-3-methylphenol Chemical compound CC1=CC(O)=CC=C1NC1=CC=CC=C1CO GAIAXLHKBNMOTK-UHFFFAOYSA-N 0.000 description 1
- PNCFXUKJXUAVFL-UHFFFAOYSA-N 4-[5-chloro-2-(hydroxymethyl)anilino]phenol Chemical compound OCC1=CC=C(Cl)C=C1NC1=CC=C(O)C=C1 PNCFXUKJXUAVFL-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 description 1
- KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 1
- KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 1
- LZCCQWLJOURHLI-UHFFFAOYSA-N 5-chloro-2-(4-phenylmethoxyanilino)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 LZCCQWLJOURHLI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical class C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 208000016557 Acute basophilic leukemia Diseases 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 238000006218 Arndt-Eistert homologation reaction Methods 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 description 1
- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 description 1
- 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 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KGRZXINCZSNTBK-UHFFFAOYSA-N [5-chloro-2-(4-phenylmethoxyanilino)phenyl]methanol Chemical compound OCC1=CC(Cl)=CC=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 KGRZXINCZSNTBK-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- PFWBDSHGBHACCV-UHFFFAOYSA-N benzene cyclohexane hexane Chemical compound CCCCCC.C1CCCCC1.C1=CC=CC=C1 PFWBDSHGBHACCV-UHFFFAOYSA-N 0.000 description 1
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CDGNLUSBENXDGG-UHFFFAOYSA-N meta-Cresidine Chemical compound COC1=CC=C(N)C(C)=C1 CDGNLUSBENXDGG-UHFFFAOYSA-N 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical class [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 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
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002569 water oil cream Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/82—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of another six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/485,936 US4496590A (en) | 1983-04-18 | 1983-04-18 | Benzyl alcohol derivatives, their preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841426L true NO841426L (no) | 1984-10-19 |
Family
ID=23929994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841426A NO841426L (no) | 1983-04-18 | 1984-04-10 | Fenylaminobenzenalkanoler og fremgangsmaate for deres fremstilling |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4496590A (es) |
| EP (1) | EP0122518A1 (es) |
| JP (1) | JPS6034934A (es) |
| KR (1) | KR840009062A (es) |
| AU (1) | AU2636384A (es) |
| DK (1) | DK191984A (es) |
| ES (1) | ES531550A0 (es) |
| FI (1) | FI841433A (es) |
| GR (1) | GR79845B (es) |
| IL (1) | IL71419A0 (es) |
| NO (1) | NO841426L (es) |
| PT (1) | PT78381B (es) |
| ZA (1) | ZA842202B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716178A (en) * | 1985-07-22 | 1987-12-29 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
| ZA865090B (en) * | 1985-07-22 | 1988-02-24 | Riker Laboratories Inc | Substituted di-t-butylphenols |
| US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
| CA1285951C (en) * | 1985-10-28 | 1991-07-09 | Raj N. Misra | Naphthalenyl- and quinolinyl-amino substituted phenols |
| US4843082A (en) * | 1986-05-05 | 1989-06-27 | E. R. Squibb & Sons, Inc. | 1,2,3,4-tetrahydro-8-quinolinol derivatives and anti-allergic use thereof |
| US4975461A (en) * | 1986-06-19 | 1990-12-04 | E. R. Squibb & Sons, Inc. | P-aminophenols, derivatives thereof and method of use |
| JPH0610174B2 (ja) * | 1986-09-29 | 1994-02-09 | 株式会社大塚製薬工場 | アミノフエノ−ル誘導体 |
| US4757078A (en) * | 1986-11-28 | 1988-07-12 | E. R. Squibb & Sons, Inc. | Cyclic aryl hydroxamic acids, derivatives thereof and method of use as anti-allergy agents |
| JPS63185924A (ja) * | 1987-01-28 | 1988-08-01 | Otsuka Pharmaceut Factory Inc | リポキシゲナ−ゼ阻害剤 |
| JPS63185923A (ja) * | 1987-01-28 | 1988-08-01 | Otsuka Pharmaceut Factory Inc | 抗炎症剤 |
| JP2008546204A (ja) * | 2005-06-03 | 2008-12-18 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッド | 前処理組成物 |
| EP3354645A1 (en) * | 2017-01-26 | 2018-08-01 | Patheon Austria GmbH & Co KG | Process for preparing urolithins |
| WO2019168972A1 (en) | 2018-02-27 | 2019-09-06 | Amazentis Sa | Process-scale synthesis of urolithin a |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3895063A (en) * | 1965-04-08 | 1975-07-15 | Ciba Geigy Corp | Substituted Anilino Benzyl Alcohols |
| US3513199A (en) * | 1967-05-05 | 1970-05-19 | Smithkline Corp | Substituted anilino benzyl alcohols |
| CH506480A (de) * | 1969-02-20 | 1971-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen, substituierten o-Anilino-phenäthylalkoholen |
| CH527794A (de) * | 1970-01-29 | 1972-09-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen, substituierten o-Anilino-phenäthylalkoholen |
| US3792090A (en) * | 1970-08-06 | 1974-02-12 | Oreal | P-hydroxy-diphenylamine compounds |
| US3884625A (en) * | 1970-12-21 | 1975-05-20 | Oreal | Indophenols dyes for coloring keratin fibers |
-
1983
- 1983-04-18 US US06/485,936 patent/US4496590A/en not_active Expired - Fee Related
-
1984
- 1984-03-26 ZA ZA842202A patent/ZA842202B/xx unknown
- 1984-03-27 EP EP84103379A patent/EP0122518A1/en not_active Withdrawn
- 1984-03-30 IL IL71419A patent/IL71419A0/xx unknown
- 1984-04-03 AU AU26363/84A patent/AU2636384A/en not_active Abandoned
- 1984-04-04 GR GR74311A patent/GR79845B/el unknown
- 1984-04-06 PT PT78381A patent/PT78381B/pt unknown
- 1984-04-10 NO NO841426A patent/NO841426L/no unknown
- 1984-04-11 FI FI841433A patent/FI841433A/fi not_active Application Discontinuation
- 1984-04-12 ES ES531550A patent/ES531550A0/es active Granted
- 1984-04-13 KR KR1019840001955A patent/KR840009062A/ko not_active Application Discontinuation
- 1984-04-13 DK DK191984A patent/DK191984A/da not_active Application Discontinuation
- 1984-04-13 JP JP59075684A patent/JPS6034934A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT78381B (en) | 1986-05-28 |
| DK191984A (da) | 1984-10-19 |
| EP0122518A1 (en) | 1984-10-24 |
| ES8602600A1 (es) | 1985-12-01 |
| DK191984D0 (da) | 1984-04-13 |
| JPS6034934A (ja) | 1985-02-22 |
| GR79845B (es) | 1984-10-31 |
| US4496590A (en) | 1985-01-29 |
| ZA842202B (en) | 1984-10-31 |
| KR840009062A (ko) | 1984-12-24 |
| IL71419A0 (en) | 1984-06-29 |
| FI841433A0 (fi) | 1984-04-11 |
| PT78381A (en) | 1984-05-01 |
| ES531550A0 (es) | 1985-12-01 |
| FI841433A (fi) | 1984-10-19 |
| AU2636384A (en) | 1984-10-25 |
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