CS417691A3 - Substituted di-tert-butylphenols - Google Patents
Substituted di-tert-butylphenols Download PDFInfo
- Publication number
- CS417691A3 CS417691A3 CS914176A CS417691A CS417691A3 CS 417691 A3 CS417691 A3 CS 417691A3 CS 914176 A CS914176 A CS 914176A CS 417691 A CS417691 A CS 417691A CS 417691 A3 CS417691 A3 CS 417691A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carbon
- compound
- tert
- bond
- tetrazolyl
- Prior art date
Links
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical class CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 68
- -1 N-methyltetrazolyl Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 21
- 150000002617 leukotrienes Chemical class 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 230000003266 anti-allergic effect Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 102000003820 Lipoxygenases Human genes 0.000 claims description 8
- 108090000128 Lipoxygenases Proteins 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 230000007885 bronchoconstriction Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000282320 Panthera leo Species 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 106
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- 239000007787 solid Substances 0.000 description 49
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- 239000000463 material Substances 0.000 description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 239000005711 Benzoic acid Substances 0.000 description 14
- 229960004132 diethyl ether Drugs 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 235000010233 benzoic acid Nutrition 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 229910052700 potassium Inorganic materials 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- DOBUKWPISJBXBD-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyanilino)benzoic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(NC=2C=C(C=CC=2)C(O)=O)=C1 DOBUKWPISJBXBD-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- RDQSIADLBQFVMY-UHFFFAOYSA-N 2,6-Di-tert-butylbenzoquinone Chemical compound CC(C)(C)C1=CC(=O)C=C(C(C)(C)C)C1=O RDQSIADLBQFVMY-UHFFFAOYSA-N 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 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 6
- 239000002585 base Substances 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 201000004681 Psoriasis Diseases 0.000 description 5
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 210000003630 histaminocyte Anatomy 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 235000013985 cinnamic acid Nutrition 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 208000017520 skin disease Diseases 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- UXOUMJXSKFRVRG-UHFFFAOYSA-N 4-[(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino]benzoic acid Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=NC1=CC=C(C(O)=O)C=C1 UXOUMJXSKFRVRG-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000000043 antiallergic agent Substances 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- LNGNZSMIUVQZOX-UHFFFAOYSA-L disodium;dioxido(sulfanylidene)-$l^{4}-sulfane Chemical compound [Na+].[Na+].[O-]S([O-])=S LNGNZSMIUVQZOX-UHFFFAOYSA-L 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000000241 respiratory effect Effects 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- KXKZJOLDANDADG-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxy-n-(2,2,2-trifluoroacetyl)anilino)benzoic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(N(C(=O)C(F)(F)F)C=2C=C(C=CC=2)C(O)=O)=C1 KXKZJOLDANDADG-UHFFFAOYSA-N 0.000 description 2
- DTIDBCWGPOHKNT-UHFFFAOYSA-N 3-[(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino]benzoic acid Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=NC1=CC=CC(C(O)=O)=C1 DTIDBCWGPOHKNT-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- SNQMRDLTUGIUCC-UHFFFAOYSA-N 4-(3,5-ditert-butyl-4-hydroxyanilino)benzoic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(NC=2C=CC(=CC=2)C(O)=O)=C1 SNQMRDLTUGIUCC-UHFFFAOYSA-N 0.000 description 2
- JVFMHVNMKWRCLN-UHFFFAOYSA-N C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=NC1=CC(C(O)=O)=CC=C1O Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=NC1=CC(C(O)=O)=CC=C1O JVFMHVNMKWRCLN-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000000890 antigenic effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000003979 eosinophil Anatomy 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 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 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75735885A | 1985-07-22 | 1985-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS417691A3 true CS417691A3 (en) | 1992-10-14 |
Family
ID=25047508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS914176A CS417691A3 (en) | 1985-07-22 | 1991-12-30 | Substituted di-tert-butylphenols |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US5347036A (es) |
| EP (1) | EP0212848B1 (es) |
| JP (2) | JPH0667884B2 (es) |
| KR (1) | KR900007271B1 (es) |
| AU (1) | AU585626B2 (es) |
| CA (2) | CA1283419C (es) |
| CS (1) | CS417691A3 (es) |
| DE (1) | DE3676008D1 (es) |
| DK (1) | DK170666B1 (es) |
| ES (1) | ES2000368A6 (es) |
| IL (1) | IL79376A (es) |
| NO (1) | NO172230C (es) |
| NZ (1) | NZ216854A (es) |
| ZA (1) | ZA865090B (es) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0254259A3 (en) * | 1986-07-21 | 1989-11-23 | Otsuka Pharmaceutical Factory, Inc. | P-aminophenol derivatives |
| 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 |
| JPS63185923A (ja) * | 1987-01-28 | 1988-08-01 | Otsuka Pharmaceut Factory Inc | 抗炎症剤 |
| JPS63185924A (ja) * | 1987-01-28 | 1988-08-01 | Otsuka Pharmaceut Factory Inc | リポキシゲナ−ゼ阻害剤 |
| ZA882251B (en) * | 1987-04-06 | 1989-11-29 | Riker Laboratories Inc | Substituted di-t-butylphenols |
| NZ226621A (en) * | 1987-11-13 | 1991-12-23 | Riker Laboratories Inc | Di-tert butyl phenols substituted by alkoxy, benzyloxy, or benzylthio groups; pharmaceutical compositions containing them |
| AU633263B2 (en) * | 1988-07-25 | 1993-01-28 | Libbey-Owens-Ford Co. | Sputtered multi-layer color compatible solar control coating |
| JP2824387B2 (ja) * | 1994-03-18 | 1998-11-11 | 関西電力株式会社 | ガス中の硫化水素と二酸化炭素を除去する方法 |
| US5578639A (en) * | 1994-07-01 | 1996-11-26 | Warner-Lambert Company | PLA2 inhibitors and their use for inhibition of intestinal cholesterol absorption |
| US5684204A (en) * | 1995-11-15 | 1997-11-04 | The Procter & Gamble Company | Sulfur containing di-tert-butylphenol compounds useful as anti-inflammatory agents |
| DE19608006A1 (de) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Salze von phosphonigen Säuren und deren Verwendung als Flammschutzmittel in Kunststoffen |
| US6218437B1 (en) * | 1996-09-30 | 2001-04-17 | The Regents Of The University Of California | Treatment and prevention of hepatic disorders |
| WO1999038829A1 (en) * | 1998-01-28 | 1999-08-05 | Shionogi & Co., Ltd. | Novel tricyclic compound |
| GB2349880A (en) * | 1999-05-10 | 2000-11-15 | Secr Defence | (Thio)morpholinium salts having SHG activity |
| EP1127882A1 (en) | 2000-01-25 | 2001-08-29 | Pfizer Products Inc. | Tetrazole compounds as thyroid receptor ligands |
| FR2818656A1 (fr) * | 2000-12-22 | 2002-06-28 | Rhodia Chimie Sa | Composition et procede d'inhibition de la polymerisation radicalaire de monomeres aromatiques a insaturation ethylenique |
| WO2004064781A2 (en) * | 2003-01-14 | 2004-08-05 | Adam Heller | Anti-inflammatory substituted phenols and elastomeric compositions for oral delivery of drugs |
| MY141255A (en) * | 2003-12-11 | 2010-03-31 | Memory Pharm Corp | Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs |
| GB0813403D0 (en) | 2008-07-22 | 2008-08-27 | Lectus Therapeutics Ltd | Potassium ion channel modulators & uses thereof |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH7213A (de) * | 1893-07-03 | 1894-02-15 | Mueller Dr Eugen | Feldflasche |
| US3318848A (en) * | 1963-06-20 | 1967-05-09 | Celanese Corp | Melt hydrolysis of oxymethylene copolymers |
| US3313848A (en) * | 1964-06-18 | 1967-04-11 | Parke Davis & Co | Anthranilic acids and derivatives |
| US3413313A (en) * | 1964-06-18 | 1968-11-26 | Parke Davis & Co | Anthranilic acid compounds and methods for their production |
| NL133740C (es) * | 1965-04-08 | |||
| US3558690A (en) * | 1965-04-08 | 1971-01-26 | Gelgy Chemical Corp | Substituted derivatives of 2-anilinophenylacetic acids and a process of preparation |
| US3895063A (en) * | 1965-04-08 | 1975-07-15 | Ciba Geigy Corp | Substituted Anilino Benzyl Alcohols |
| CH475198A (de) * | 1966-10-07 | 1969-07-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen substituierten Phenylessigsäuren |
| CH478762A (de) * | 1966-10-07 | 1969-09-30 | Geigy Ag J R | Verfahren zur Herstellung von neuen substituierten Zimtsäuren |
| US3673243A (en) * | 1968-05-08 | 1972-06-27 | Sumitomo Chemical Co | Novel process for producing o-anilinophenylaliphatic acid derivatives |
| US3773936A (en) * | 1969-06-25 | 1973-11-20 | Merck & Co Inc | Method of treating inflammation with substituted anilino salicylic acids |
| US3778470A (en) * | 1972-08-23 | 1973-12-11 | A Sallman | Chemical intermediates for the production of substituted 2-anilinophenylacetic acids and esters |
| US4070484A (en) * | 1973-01-18 | 1978-01-24 | Kissei Pharmaceutical Co., Ltd. | Antiallergic composition containing aromatic carboxylic amide derivatives and method of using the same |
| JPS6039262B2 (ja) * | 1977-05-11 | 1985-09-05 | ウェルファイド株式会社 | 第３級ブチルフェノ−ル誘導体 |
| US4172151A (en) | 1977-05-16 | 1979-10-23 | Riker Laboratories, Inc. | Anti-inflammatory method |
| JPS55145648A (en) * | 1979-05-02 | 1980-11-13 | Hisamitsu Pharmaceut Co Inc | New derivative of anthranylic acid |
| US4496390A (en) * | 1980-02-26 | 1985-01-29 | May & Baker Limited | N-Phenylpyrazole derivatives |
| US4496590A (en) * | 1983-04-18 | 1985-01-29 | Sterling Drug Inc. | Benzyl alcohol derivatives, their preparation and use |
| US4515980A (en) * | 1983-07-11 | 1985-05-07 | Sterling Drug Inc. | Substituted aminobenzoates, their preparation and use |
| US4510139A (en) * | 1984-01-06 | 1985-04-09 | Sterling Drug Inc. | Substituted aminobenzamides and their use as agents which inhibit lipoxygenase activity |
| JPS60168175A (ja) * | 1984-02-13 | 1985-08-31 | Konishiroku Photo Ind Co Ltd | 複写機 |
| US4528392A (en) * | 1984-04-18 | 1985-07-09 | American Home Products Corporation | Aromatic compounds as antiallergic agents |
| NZ213986A (en) * | 1984-10-30 | 1989-07-27 | Usv Pharma Corp | Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such |
| ZA865091B (en) | 1985-07-22 | 1988-02-24 | Riker Laboratories Inc | Substituted di-t-butylphenols |
| US4714776A (en) * | 1985-07-22 | 1987-12-22 | Riker Laboratories, Inc. | Antiallergic agents |
| US4716178A (en) * | 1985-07-22 | 1987-12-29 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
| JPS6229557A (ja) * | 1985-07-29 | 1987-02-07 | Otsuka Pharmaceut Factory Inc | ジ低級アルキルフエノ−ル誘導体 |
| US4677113A (en) * | 1986-04-22 | 1987-06-30 | Riker Laboratories, Inc. | Di-t-butylphenols substituted by a thenoyl group |
| 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 |
| US4710515A (en) * | 1987-03-17 | 1987-12-01 | Riker Laboratories, Inc. | Substituted biphenyl derivatives |
-
1986
- 1986-07-08 ZA ZA865090A patent/ZA865090B/xx unknown
- 1986-07-09 IL IL79376A patent/IL79376A/xx not_active IP Right Cessation
- 1986-07-11 AU AU60085/86A patent/AU585626B2/en not_active Ceased
- 1986-07-15 NZ NZ216854A patent/NZ216854A/en unknown
- 1986-07-17 DE DE8686305515T patent/DE3676008D1/de not_active Expired - Fee Related
- 1986-07-17 EP EP86305515A patent/EP0212848B1/en not_active Expired - Lifetime
- 1986-07-21 KR KR1019860005888A patent/KR900007271B1/ko not_active Expired
- 1986-07-21 NO NO862924A patent/NO172230C/no not_active IP Right Cessation
- 1986-07-21 DK DK344786A patent/DK170666B1/da not_active IP Right Cessation
- 1986-07-22 CA CA000514378A patent/CA1283419C/en not_active Expired - Fee Related
- 1986-07-22 ES ES8600457A patent/ES2000368A6/es not_active Expired
- 1986-07-22 JP JP61172657A patent/JPH0667884B2/ja not_active Expired - Fee Related
-
1990
- 1990-08-08 CA CA000615810A patent/CA1295336C/en not_active Expired - Fee Related
-
1991
- 1991-12-30 CS CS914176A patent/CS417691A3/cs unknown
-
1993
- 1993-05-26 US US08/067,636 patent/US5347036A/en not_active Expired - Lifetime
-
1994
- 1994-03-11 JP JP6041142A patent/JP2515486B2/ja not_active Expired - Fee Related
- 1994-06-22 US US08/263,390 patent/US5416113A/en not_active Expired - Lifetime
-
1995
- 1995-05-05 US US08/435,582 patent/US5498745A/en not_active Expired - Lifetime
- 1995-05-05 US US08/437,143 patent/US5527824A/en not_active Expired - Lifetime
- 1995-05-05 US US08/435,585 patent/US5495043A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR900007271B1 (ko) | 1990-10-06 |
| US5495043A (en) | 1996-02-27 |
| JP2515486B2 (ja) | 1996-07-10 |
| DK344786A (da) | 1987-01-23 |
| JPS6345243A (ja) | 1988-02-26 |
| US5498745A (en) | 1996-03-12 |
| US5416113A (en) | 1995-05-16 |
| IL79376A0 (en) | 1986-10-31 |
| ES2000368A6 (es) | 1988-02-16 |
| EP0212848A2 (en) | 1987-03-04 |
| DK344786D0 (da) | 1986-07-21 |
| NO172230B (no) | 1993-03-15 |
| EP0212848B1 (en) | 1990-12-05 |
| AU585626B2 (en) | 1989-06-22 |
| AU6008586A (en) | 1987-01-29 |
| NO862924D0 (no) | 1986-07-21 |
| ZA865090B (en) | 1988-02-24 |
| NZ216854A (en) | 1991-03-26 |
| IL79376A (en) | 1991-05-12 |
| JPH0753485A (ja) | 1995-02-28 |
| EP0212848A3 (en) | 1987-12-16 |
| DK170666B1 (da) | 1995-11-27 |
| NO862924L (no) | 1987-01-23 |
| DE3676008D1 (de) | 1991-01-17 |
| CA1295336C (en) | 1992-02-04 |
| CA1283419C (en) | 1991-04-23 |
| NO172230C (no) | 1993-06-23 |
| KR870001149A (ko) | 1987-03-11 |
| US5347036A (en) | 1994-09-13 |
| JPH0667884B2 (ja) | 1994-08-31 |
| US5527824A (en) | 1996-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic |