SK284715B6 - Deriváty hydroxyfenylsulfanylbenzoových a hydroxyfenylsulfanylaryloctových kyselín - Google Patents
Deriváty hydroxyfenylsulfanylbenzoových a hydroxyfenylsulfanylaryloctových kyselín Download PDFInfo
- Publication number
- SK284715B6 SK284715B6 SK1938-2000A SK19382000A SK284715B6 SK 284715 B6 SK284715 B6 SK 284715B6 SK 19382000 A SK19382000 A SK 19382000A SK 284715 B6 SK284715 B6 SK 284715B6
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- formula
- phenylsulfanyl
- benzoic acid
- yield
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 71
- 150000007513 acids Chemical class 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 23
- -1 4-acetyl-3-hydroxy-2-propylphenoxy Chemical group 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 230000008569 process Effects 0.000 claims abstract description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
- 230000005764 inhibitory process Effects 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- 206010006482 Bronchospasm Diseases 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 6
- 208000014181 Bronchial disease Diseases 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- OXZOHZCQSYOMJR-UHFFFAOYSA-N 4-[3-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]phenyl]sulfanylbenzoic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCCOC1=CC=CC(SC=2C=CC(=CC=2)C(O)=O)=C1 OXZOHZCQSYOMJR-UHFFFAOYSA-N 0.000 claims description 4
- 230000001088 anti-asthma Effects 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 4
- 229960001340 histamine Drugs 0.000 claims 2
- XBXVEIDWEUQFPX-UHFFFAOYSA-N 2-[4-[3-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]propoxy]phenyl]sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC(C=C1)=CC=C1OCCCN1CCN(CC=2C=CC(Cl)=CC=2)CC1 XBXVEIDWEUQFPX-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 description 78
- 229910052739 hydrogen Inorganic materials 0.000 description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- 229910052717 sulfur Inorganic materials 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 60
- 239000000243 solution Substances 0.000 description 41
- 150000004702 methyl esters Chemical class 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 238000009835 boiling Methods 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 229940095102 methyl benzoate Drugs 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000020477 pH reduction Effects 0.000 description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 8
- 206010030113 Oedema Diseases 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 150000002617 leukotrienes Chemical class 0.000 description 7
- WPKSAAFQGCMSRC-UHFFFAOYSA-N methyl 2-[2-(4-hydroxyphenyl)sulfanylphenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1SC1=CC=C(O)C=C1 WPKSAAFQGCMSRC-UHFFFAOYSA-N 0.000 description 7
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 7
- 150000003248 quinolines Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 108010058846 Ovalbumin Proteins 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229940114079 arachidonic acid Drugs 0.000 description 5
- 235000021342 arachidonic acid Nutrition 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229940092253 ovalbumin Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- GSJXJZOWHSTWOX-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]piperazine Chemical compound C1=CC(Cl)=CC=C1CN1CCNCC1 GSJXJZOWHSTWOX-UHFFFAOYSA-N 0.000 description 4
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 4
- UXWBKJAGJJQWRS-UHFFFAOYSA-N 2-[2-[3-[(6-chloroquinolin-2-yl)methoxy]phenyl]sulfanylphenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1SC1=CC=CC(OCC=2N=C3C=CC(Cl)=CC3=CC=2)=C1 UXWBKJAGJJQWRS-UHFFFAOYSA-N 0.000 description 4
- IJTXSPDIILLCBV-UHFFFAOYSA-N 2-[3-[(6-chloroquinolin-2-yl)methoxy]phenyl]sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC1=CC=CC(OCC=2N=C3C=CC(Cl)=CC3=CC=2)=C1 IJTXSPDIILLCBV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- SGYIPNLGHASVFY-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.OC(=O)c1ccccc1Sc1ccc(OCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1 Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)c1ccccc1Sc1ccc(OCCN2CCN(Cc3ccc(Cl)cc3)CC2)cc1 SGYIPNLGHASVFY-BTJKTKAUSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000002590 anti-leukotriene effect Effects 0.000 description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 210000000416 exudates and transudate Anatomy 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QGGRBWUQXAFYEC-UHFFFAOYSA-N 1-(2,4-dihydroxy-3-propylphenyl)ethanone Chemical compound CCCC1=C(O)C=CC(C(C)=O)=C1O QGGRBWUQXAFYEC-UHFFFAOYSA-N 0.000 description 3
- ZPWOYRBOIAURRC-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)sulfanylphenyl]acetonitrile Chemical compound C1=CC(OC)=CC=C1SC1=CC=CC=C1CC#N ZPWOYRBOIAURRC-UHFFFAOYSA-N 0.000 description 3
- SYPCCEGVVLHRCA-UHFFFAOYSA-N 2-[2-[4-[(6-chloroquinolin-2-yl)methoxy]phenyl]sulfanylphenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1SC(C=C1)=CC=C1OCC1=CC=C(C=C(Cl)C=C2)C2=N1 SYPCCEGVVLHRCA-UHFFFAOYSA-N 0.000 description 3
- MZEOWLJCSMLJHU-UHFFFAOYSA-N 2-[2-[4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]phenyl]sulfanylphenyl]acetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC(C=C1)=CC=C1SC1=CC=CC=C1CC(O)=O MZEOWLJCSMLJHU-UHFFFAOYSA-N 0.000 description 3
- OEFMWVURUPUNSD-UHFFFAOYSA-N 2-[2-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]phenyl]sulfanylphenyl]acetic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCCOC(C=C1)=CC=C1SC1=CC=CC=C1CC(O)=O OEFMWVURUPUNSD-UHFFFAOYSA-N 0.000 description 3
- VFGYAMRUCXZAAI-UHFFFAOYSA-N 2-[3-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]phenyl]sulfanylbenzoic acid Chemical compound C(C)(=O)C1=C(C(=C(OCCOC=2C=C(C=CC=2)SC2=C(C(=O)O)C=CC=C2)C=C1)CCC)O VFGYAMRUCXZAAI-UHFFFAOYSA-N 0.000 description 3
- XVACDLKGUJGLRT-UHFFFAOYSA-N 2-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]phenyl]sulfanylbenzoic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=CC(SC=2C(=CC=CC=2)C(O)=O)=C1 XVACDLKGUJGLRT-UHFFFAOYSA-N 0.000 description 3
- NSMBOFAFGIWLKZ-UHFFFAOYSA-N 2-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]phenyl]sulfanyl-5-nitrobenzoic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCCOC(C=C1)=CC=C1SC1=CC=C([N+]([O-])=O)C=C1C(O)=O NSMBOFAFGIWLKZ-UHFFFAOYSA-N 0.000 description 3
- SBHUTFSYGBHIGF-UHFFFAOYSA-N 4-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]phenyl]sulfanylbenzoic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=CC(SC=2C=CC(=CC=2)C(O)=O)=C1 SBHUTFSYGBHIGF-UHFFFAOYSA-N 0.000 description 3
- VKAICVJVHLVZLJ-UHFFFAOYSA-N 4-[3-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]phenyl]sulfanyl-3-nitrobenzoic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCCOC1=CC=CC(SC=2C(=CC(=CC=2)C(O)=O)[N+]([O-])=O)=C1 VKAICVJVHLVZLJ-UHFFFAOYSA-N 0.000 description 3
- FTAQNQRTGMUQHJ-UHFFFAOYSA-N 4-[4-[(6-chloroquinolin-2-yl)methoxy]phenyl]sulfanylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC(C=C1)=CC=C1OCC1=CC=C(C=C(Cl)C=C2)C2=N1 FTAQNQRTGMUQHJ-UHFFFAOYSA-N 0.000 description 3
- YMNKBAYBJBXKCL-UHFFFAOYSA-N 4-[4-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]phenyl]sulfanylbenzoic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCOC(C=C1)=CC=C1SC1=CC=C(C(O)=O)C=C1 YMNKBAYBJBXKCL-UHFFFAOYSA-N 0.000 description 3
- QIEONRVDHLNOPJ-UHFFFAOYSA-N 4-[4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]phenyl]sulfanylbenzoic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC(C=C1)=CC=C1SC1=CC=C(C(O)=O)C=C1 QIEONRVDHLNOPJ-UHFFFAOYSA-N 0.000 description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 3
- WLGDLQDPQBOXGD-UHFFFAOYSA-N 6-chloro-2-(chloromethyl)quinoline Chemical compound C1=C(Cl)C=CC2=NC(CCl)=CC=C21 WLGDLQDPQBOXGD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RDOJCJUWZNKGOX-UHFFFAOYSA-N C(C(O)CC(=O)O)(=O)O.C(C(O)CC(=O)O)(=O)O.ClC1=CC=C(CN2CCN(CC2)CCCOC=2C=C(C=CC2)SC2=C(C(=O)O)C=CC=C2)C=C1 Chemical compound C(C(O)CC(=O)O)(=O)O.C(C(O)CC(=O)O)(=O)O.ClC1=CC=C(CN2CCN(CC2)CCCOC=2C=C(C=CC2)SC2=C(C(=O)O)C=CC=C2)C=C1 RDOJCJUWZNKGOX-UHFFFAOYSA-N 0.000 description 3
- UAHSNQVSNDKXLS-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.ClC1=CC=C(CN2CCN(CC2)CCCOC=2C=C(C=CC2)SC2=C(C=CC=C2)CC(=O)O)C=C1 Chemical compound C(\C=C/C(=O)O)(=O)O.ClC1=CC=C(CN2CCN(CC2)CCCOC=2C=C(C=CC2)SC2=C(C=CC=C2)CC(=O)O)C=C1 UAHSNQVSNDKXLS-BTJKTKAUSA-N 0.000 description 3
- JUTHKSRFGDMTKF-UHFFFAOYSA-N CS(=O)(=O)O.CS(=O)(=O)O.ClC1=CC=C(CN2CCN(CC2)CCCOC2=CC=C(C=C2)SC2=C(C(=O)O)C=CC=C2)C=C1 Chemical compound CS(=O)(=O)O.CS(=O)(=O)O.ClC1=CC=C(CN2CCN(CC2)CCCOC2=CC=C(C=C2)SC2=C(C(=O)O)C=CC=C2)C=C1 JUTHKSRFGDMTKF-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- OCLOSVWSMAAMMF-UHFFFAOYSA-N [2-(4-methoxyphenyl)sulfanylphenyl]methanol Chemical compound C1=CC(OC)=CC=C1SC1=CC=CC=C1CO OCLOSVWSMAAMMF-UHFFFAOYSA-N 0.000 description 3
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- VDRXHSDZMZUPSS-UHFFFAOYSA-N methyl 2-(3-hydroxyphenyl)sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1SC1=CC=CC(O)=C1 VDRXHSDZMZUPSS-UHFFFAOYSA-N 0.000 description 3
- AKQJCFKWXAMQHR-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)sulfanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SC1=CC=C(O)C=C1 AKQJCFKWXAMQHR-UHFFFAOYSA-N 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 3
- 229960005332 zileuton Drugs 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 2
- VNTXRGRQSRWKST-UHFFFAOYSA-N 2-(3-methoxyphenyl)sulfanylbenzoic acid Chemical compound COC1=CC=CC(SC=2C(=CC=CC=2)C(O)=O)=C1 VNTXRGRQSRWKST-UHFFFAOYSA-N 0.000 description 2
- NQQTVOYLKSYSJI-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC1=CC=C(O)C=C1 NQQTVOYLKSYSJI-UHFFFAOYSA-N 0.000 description 2
- ZECGBLVFSQQYIT-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanylbenzoic acid Chemical compound C1=CC(OC)=CC=C1SC1=CC=CC=C1C(O)=O ZECGBLVFSQQYIT-UHFFFAOYSA-N 0.000 description 2
- WDSCEPRXDTWANT-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)sulfanylphenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1SC1=CC=C(O)C=C1 WDSCEPRXDTWANT-UHFFFAOYSA-N 0.000 description 2
- RWZGZCZQOCWIFZ-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)sulfanylphenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1SC1=CC=CC=C1CC(O)=O RWZGZCZQOCWIFZ-UHFFFAOYSA-N 0.000 description 2
- HLQASTRPJAGIHQ-UHFFFAOYSA-N 2-[4-(4-hydroxyphenyl)sulfanylphenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1SC1=CC=C(O)C=C1 HLQASTRPJAGIHQ-UHFFFAOYSA-N 0.000 description 2
- VEQLAPRSSMRJRW-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfanylbenzoic acid Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C(O)=O)C=C1 VEQLAPRSSMRJRW-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 206010020565 Hyperaemia Diseases 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000005141 Otitis Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 229920002055 compound 48/80 Polymers 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 210000000624 ear auricle Anatomy 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000000411 inducer Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- IVWOXSJDHVZKEV-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)sulfanyl-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC=C(O)C=C1 IVWOXSJDHVZKEV-UHFFFAOYSA-N 0.000 description 2
- PJQFRNHZUVTAPT-UHFFFAOYSA-N methyl 2-[2-(3-hydroxyphenyl)sulfanylphenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1SC1=CC=CC(O)=C1 PJQFRNHZUVTAPT-UHFFFAOYSA-N 0.000 description 2
- MJCCVZLDTGTLCK-UHFFFAOYSA-N methyl 2-[3-(3-chloropropoxy)phenyl]sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1SC1=CC=CC(OCCCCl)=C1 MJCCVZLDTGTLCK-UHFFFAOYSA-N 0.000 description 2
- PSNVWTSJYMMRIC-UHFFFAOYSA-N methyl 2-[4-(4-hydroxyphenyl)sulfanylphenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1SC1=CC=C(O)C=C1 PSNVWTSJYMMRIC-UHFFFAOYSA-N 0.000 description 2
- ITNSIAPPOUTGHB-UHFFFAOYSA-N methyl 4-(3-hydroxyphenyl)sulfanyl-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC=C1SC1=CC=CC(O)=C1 ITNSIAPPOUTGHB-UHFFFAOYSA-N 0.000 description 2
- NTJWLXPGZGKISF-UHFFFAOYSA-N methyl 4-(3-hydroxyphenyl)sulfanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SC1=CC=CC(O)=C1 NTJWLXPGZGKISF-UHFFFAOYSA-N 0.000 description 2
- SXSIBXBSVMIEMG-UHFFFAOYSA-N methyl 4-[3-(4-bromobutoxy)phenyl]sulfanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SC1=CC=CC(OCCCCBr)=C1 SXSIBXBSVMIEMG-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- HCZKYJDFEPMADG-UHFFFAOYSA-N nordihydroguaiaretic acid Chemical compound C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 210000003281 pleural cavity Anatomy 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- RZVHXPZBFIVTLW-UHFFFAOYSA-N 1-(chloromethyl)-2-(4-methoxyphenyl)sulfanylbenzene Chemical compound C1=CC(OC)=CC=C1SC1=CC=CC=C1CCl RZVHXPZBFIVTLW-UHFFFAOYSA-N 0.000 description 1
- GCFXMTUUHMDOMG-UHFFFAOYSA-N 2-(3-hydroxyphenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC1=CC=CC(O)=C1 GCFXMTUUHMDOMG-UHFFFAOYSA-N 0.000 description 1
- OPNAPJTUDXWHIJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanyl-5-nitrobenzoic acid Chemical compound C1=CC(OC)=CC=C1SC1=CC=C([N+]([O-])=O)C=C1C(O)=O OPNAPJTUDXWHIJ-UHFFFAOYSA-N 0.000 description 1
- PARQKJJTQCMCQC-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)sulfanylphenyl]acetic acid Chemical compound COC1=CC=CC(SC=2C(=CC=CC=2)CC(O)=O)=C1 PARQKJJTQCMCQC-UHFFFAOYSA-N 0.000 description 1
- WMEZSXDRZXSLRO-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)sulfanylphenyl]acetonitrile Chemical compound COC1=CC=CC(SC=2C(=CC=CC=2)CC#N)=C1 WMEZSXDRZXSLRO-UHFFFAOYSA-N 0.000 description 1
- MEAYQEGZLRHZSI-UHFFFAOYSA-N 2-[2-[3-(3-chloropropoxy)phenyl]sulfanylphenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1SC1=CC=CC(OCCCCl)=C1 MEAYQEGZLRHZSI-UHFFFAOYSA-N 0.000 description 1
- JQJAXSWTWOZFOC-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)sulfanylphenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(CC(O)=O)C=C1 JQJAXSWTWOZFOC-UHFFFAOYSA-N 0.000 description 1
- XOIVQUHGCZAGMU-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)sulfanylphenyl]acetonitrile Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(CC#N)C=C1 XOIVQUHGCZAGMU-UHFFFAOYSA-N 0.000 description 1
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- OMIVOHMQUBUADP-UHFFFAOYSA-N 4-(3-hydroxyphenyl)sulfanylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC1=CC=CC(O)=C1 OMIVOHMQUBUADP-UHFFFAOYSA-N 0.000 description 1
- RXDZWQYRRJPSMW-UHFFFAOYSA-N 4-(3-methoxyphenyl)sulfanyl-3-nitrobenzoic acid Chemical compound COC1=CC=CC(SC=2C(=CC(=CC=2)C(O)=O)[N+]([O-])=O)=C1 RXDZWQYRRJPSMW-UHFFFAOYSA-N 0.000 description 1
- QRZAFTNIRFXLEX-UHFFFAOYSA-N 4-(3-methoxyphenyl)sulfanylbenzoic acid Chemical compound COC1=CC=CC(SC=2C=CC(=CC=2)C(O)=O)=C1 QRZAFTNIRFXLEX-UHFFFAOYSA-N 0.000 description 1
- JTUIGZQCSANURO-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfanylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC1=CC=C(O)C=C1 JTUIGZQCSANURO-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000019890 Amylum Nutrition 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
- 210000003771 C cell Anatomy 0.000 description 1
- WTSTWMXDYSLNIA-UHFFFAOYSA-N C1=CC=C(C(=C1)CC(=O)O)SC2=CC=C(C=C2)OCCCCl Chemical compound C1=CC=C(C(=C1)CC(=O)O)SC2=CC=C(C=C2)OCCCCl WTSTWMXDYSLNIA-UHFFFAOYSA-N 0.000 description 1
- NFXFTGBUIZDCEE-UHFFFAOYSA-N CC(CCCCCCC)C1=C(C=CC=C1)SC1=CC=C(C=C1)O Chemical compound CC(CCCCCCC)C1=C(C=CC=C1)SC1=CC=C(C=C1)O NFXFTGBUIZDCEE-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- HIYAVKIYRIFSCZ-CVXKHCKVSA-N Calcimycin Chemical compound CC([C@H]1OC2([C@@H](C[C@H]1C)C)O[C@H]([C@H](CC2)C)CC=1OC2=CC=C(C(=C2N=1)C(O)=O)NC)C(=O)C1=CC=CN1 HIYAVKIYRIFSCZ-CVXKHCKVSA-N 0.000 description 1
- 102100032216 Calcium and integrin-binding protein 1 Human genes 0.000 description 1
- FASDMYFVDLYMOV-UHFFFAOYSA-N ClCCCOC=1C=C(C=CC1)SC(C(C1=CC=CC=C1)C)CCCCCC Chemical compound ClCCCOC=1C=C(C=CC1)SC(C(C1=CC=CC=C1)C)CCCCCC FASDMYFVDLYMOV-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 101000943475 Homo sapiens Calcium and integrin-binding protein 1 Proteins 0.000 description 1
- 208000001718 Immediate Hypersensitivity Diseases 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- QOMNITSDVFCWSJ-UHFFFAOYSA-N OC=1C=C(C=CC1)SC(C(C1=CC=CC=C1)C)CCCCCC Chemical compound OC=1C=C(C=CC1)SC(C(C1=CC=CC=C1)C)CCCCCC QOMNITSDVFCWSJ-UHFFFAOYSA-N 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 206010045240 Type I hypersensitivity Diseases 0.000 description 1
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
- RZTPMLJRAXCWPA-UHFFFAOYSA-N [2-(3-methoxyphenyl)sulfanylphenyl]methanol Chemical compound COC1=CC=CC(SC=2C(=CC=CC=2)CO)=C1 RZTPMLJRAXCWPA-UHFFFAOYSA-N 0.000 description 1
- ICNZZCBKHVDQQC-UHFFFAOYSA-N [4-(4-methoxyphenyl)sulfanylphenyl]methanol Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(CO)C=C1 ICNZZCBKHVDQQC-UHFFFAOYSA-N 0.000 description 1
- 229940020697 accolate Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010216 atopic IgE responsiveness Diseases 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000004044 bronchoconstricting agent Substances 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- HIYAVKIYRIFSCZ-UHFFFAOYSA-N calcium ionophore A23187 Natural products N=1C2=C(C(O)=O)C(NC)=CC=C2OC=1CC(C(CC1)C)OC1(C(CC1C)C)OC1C(C)C(=O)C1=CC=CN1 HIYAVKIYRIFSCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 230000010002 chemokinesis Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 229960003943 hypromellose Drugs 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 102000003835 leukotriene receptors Human genes 0.000 description 1
- 108090000146 leukotriene receptors Proteins 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- NHFHQDAJNMNHJG-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1SC1=CC=C(O)C=C1 NHFHQDAJNMNHJG-UHFFFAOYSA-N 0.000 description 1
- YPJLEKVNRMJIGR-UHFFFAOYSA-N methyl 4-[3-(3-chloropropoxy)phenyl]sulfanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SC1=CC=CC(OCCCCl)=C1 YPJLEKVNRMJIGR-UHFFFAOYSA-N 0.000 description 1
- MEFLSACZWLYBEK-UHFFFAOYSA-N methyl 4-[4-(3-chloropropoxy)phenyl]sulfanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SC1=CC=C(OCCCCl)C=C1 MEFLSACZWLYBEK-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000004783 oxidative metabolism Effects 0.000 description 1
- KLAKIAVEMQMVBT-UHFFFAOYSA-N p-hydroxy-phenacyl alcohol Natural products OCC(=O)C1=CC=C(O)C=C1 KLAKIAVEMQMVBT-UHFFFAOYSA-N 0.000 description 1
- 230000007119 pathological manifestation Effects 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ19981941A CZ290693B6 (cs) | 1998-06-19 | 1998-06-19 | Deriváty hydroxyfenylmerkaptobenzoových a hydroxyfenylmerkaptoaryloctových kyselin s antileukotrienovou aktivitou |
| PCT/CZ1999/000019 WO1999067208A1 (en) | 1998-06-19 | 1999-06-16 | Derivatives of hydroxyphenylsulfanylbenzoic and hydroxyphenylsulfanylarylacetic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK19382000A3 SK19382000A3 (sk) | 2002-05-09 |
| SK284715B6 true SK284715B6 (sk) | 2005-09-08 |
Family
ID=5464092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1938-2000A SK284715B6 (sk) | 1998-06-19 | 1999-06-16 | Deriváty hydroxyfenylsulfanylbenzoových a hydroxyfenylsulfanylaryloctových kyselín |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6303612B1 (cs) |
| EP (1) | EP1086079B1 (cs) |
| JP (1) | JP2002518472A (cs) |
| KR (1) | KR20010071543A (cs) |
| AT (1) | ATE239699T1 (cs) |
| AU (1) | AU4129899A (cs) |
| CA (1) | CA2335373A1 (cs) |
| CZ (1) | CZ290693B6 (cs) |
| DE (1) | DE69907671D1 (cs) |
| HU (1) | HUP0105056A2 (cs) |
| PL (1) | PL345005A1 (cs) |
| SK (1) | SK284715B6 (cs) |
| WO (1) | WO1999067208A1 (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2297409C2 (ru) * | 2001-09-14 | 2007-04-20 | Эмджен Инк. | Диарильные соединения с мостиковой связью |
| GB0415320D0 (en) * | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| ITTO20060575A1 (it) * | 2006-08-02 | 2008-02-03 | Univ Pisa | Inibitori di zinco proteinasi tioaril sostituiti e loro usi |
| TW201139432A (en) * | 2010-03-18 | 2011-11-16 | Kowa Co | Monomaleate of benzothiazine compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61130271A (ja) * | 1984-11-30 | 1986-06-18 | Tokyo Tanabe Co Ltd | 芳香族カルボン酸誘導体及びその塩 |
| US5109009A (en) * | 1985-03-08 | 1992-04-28 | Leo Pharmaceutical Products Ltd. | Quinoline and pyridine compounds and inhibition of 5-lipoxygenases therewith |
| IL116942A (en) * | 1991-11-25 | 2000-02-29 | Lilly Co Eli | 2-phenyl-4,5-disubstituted phenol derivatives as chemical intermediates for substituted phenyl phenol leukotriene antagonists |
| PH30449A (en) | 1991-11-25 | 1997-05-28 | Lilly Co Eli | Substituted phenyl phenol leukotriene antagonists |
-
1998
- 1998-06-19 CZ CZ19981941A patent/CZ290693B6/cs not_active IP Right Cessation
-
1999
- 1999-06-16 SK SK1938-2000A patent/SK284715B6/sk unknown
- 1999-06-16 DE DE69907671T patent/DE69907671D1/de not_active Expired - Lifetime
- 1999-06-16 AT AT99924655T patent/ATE239699T1/de not_active IP Right Cessation
- 1999-06-16 KR KR1020007014487A patent/KR20010071543A/ko not_active Withdrawn
- 1999-06-16 US US09/736,020 patent/US6303612B1/en not_active Expired - Fee Related
- 1999-06-16 HU HU0105056A patent/HUP0105056A2/hu unknown
- 1999-06-16 CA CA002335373A patent/CA2335373A1/en not_active Abandoned
- 1999-06-16 PL PL99345005A patent/PL345005A1/xx unknown
- 1999-06-16 WO PCT/CZ1999/000019 patent/WO1999067208A1/en not_active Application Discontinuation
- 1999-06-16 JP JP2000555862A patent/JP2002518472A/ja not_active Withdrawn
- 1999-06-16 AU AU41298/99A patent/AU4129899A/en not_active Abandoned
- 1999-06-16 EP EP99924655A patent/EP1086079B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2335373A1 (en) | 1999-12-29 |
| CZ290693B6 (cs) | 2002-09-11 |
| SK19382000A3 (sk) | 2002-05-09 |
| ATE239699T1 (de) | 2003-05-15 |
| US6303612B1 (en) | 2001-10-16 |
| DE69907671D1 (en) | 2003-06-12 |
| EP1086079A1 (en) | 2001-03-28 |
| CZ194198A3 (cs) | 2000-01-12 |
| KR20010071543A (ko) | 2001-07-28 |
| EP1086079B1 (en) | 2003-05-07 |
| HUP0105056A2 (en) | 2002-06-29 |
| WO1999067208A1 (en) | 1999-12-29 |
| JP2002518472A (ja) | 2002-06-25 |
| AU4129899A (en) | 2000-01-10 |
| PL345005A1 (en) | 2001-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5811459A (en) | Ortho substituted aromatic compounds useful as antagonists of the pain enhancing effects of E-type prostaglandins | |
| CA1064933A (en) | Benzoic acids, their derivatives and process for preparing them | |
| EP1368302B1 (de) | Neuartige aminodicarbonsäurederivate | |
| JP2006517199A5 (cs) | ||
| ZA200608393B (en) | Substituted methyl aryl or heteroaryl amide compounds | |
| WO2005016862A1 (en) | Substituted arylalkanoic acid derivative and use thereof | |
| JPH01125322A (ja) | アルドース還元酵素阻害剤 | |
| NZ502669A (en) | 5-alkyl-2-arylaminophenylacetic acids and use for treating cyclooxygenase-2 dependent disorders | |
| JP2010159287A (ja) | 置換アミノフェニル酢酸、その誘導体、その製造およびシクロオキシゲナーゼ２（ｃｏｘ−２）阻害剤としてのその使用 | |
| JP3330149B2 (ja) | ベンゼン、ピリジン若しくはピリミジン誘導体 | |
| JPH0753485A (ja) | 置換ジ−ｔ−ブチルシクロヘキサジエノン類 | |
| Child et al. | Fenbufen, a new anti-inflammatory analgesic: synthesis and structure-activity relationships of analogs | |
| AU620550B2 (en) | Pharmaceutical compositions | |
| CN110305072A (zh) | 具有磷酸二酯酶4d和酸性鞘磷脂酶抑制活性的化合物及其应用 | |
| FI57594C (fi) | Foerfarande foer framstaellning av antiallergiskt verksamma n-(bentstiazol-2-yl)-oxamidsyra-derivat | |
| NO841426L (no) | Fenylaminobenzenalkanoler og fremgangsmaate for deres fremstilling | |
| SK284715B6 (sk) | Deriváty hydroxyfenylsulfanylbenzoových a hydroxyfenylsulfanylaryloctových kyselín | |
| US4515980A (en) | Substituted aminobenzoates, their preparation and use | |
| US5900426A (en) | Benzothiazole derivatives | |
| CN102234231B (zh) | 1-取代-2-取代-4-芳基取代-丁-2-烯1,4-二酮类化合物、其制备方法及其用途 | |
| NZ226621A (en) | Di-tert butyl phenols substituted by alkoxy, benzyloxy, or benzylthio groups; pharmaceutical compositions containing them | |
| JPH0672866A (ja) | 分化誘導剤 | |
| US5250541A (en) | Kynurenic acid derivatives, their preparation and pharmaceutical compositions containing them | |
| TW202435B (cs) | ||
| SK153799A3 (en) | New nitromethyl ketones, process for preparing them and compositions containing them |