PH26153A - Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof - Google Patents
Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof Download PDFInfo
- Publication number
- PH26153A PH26153A PH36982A PH36982A PH26153A PH 26153 A PH26153 A PH 26153A PH 36982 A PH36982 A PH 36982A PH 36982 A PH36982 A PH 36982A PH 26153 A PH26153 A PH 26153A
- Authority
- PH
- Philippines
- Prior art keywords
- benzopyran
- compound
- dihydro
- acetyl
- methoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 159
- 238000000034 method Methods 0.000 title claims description 48
- 239000008194 pharmaceutical composition Substances 0.000 title claims 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- -1 propoxyl-1,2,3,4-tetrahydro-8-propyl-2-naphthalene- carboxylate Chemical compound 0.000 claims description 22
- 208000027866 inflammatory disease Diseases 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- 241000124008 Mammalia Species 0.000 claims description 16
- 150000002617 leukotrienes Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 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 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- HMXJOWDZAJWLTF-UHFFFAOYSA-N 2h-chromene-2-carboxylic acid Chemical compound C1=CC=C2C=CC(C(=O)O)OC2=C1 HMXJOWDZAJWLTF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 201000005569 Gout Diseases 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 41
- 239000003937 drug carrier Substances 0.000 claims 14
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 47
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- 239000000047 product Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- 239000005557 antagonist Substances 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 125000004122 cyclic group Chemical group 0.000 description 16
- 239000003039 volatile agent Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 15
- 238000004452 microanalysis Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 230000027455 binding Effects 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 210000000440 neutrophil Anatomy 0.000 description 13
- 238000002390 rotary evaporation Methods 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 241000700199 Cavia porcellus Species 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 102000003896 Myeloperoxidases Human genes 0.000 description 9
- 108090000235 Myeloperoxidases Proteins 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 210000003405 ileum Anatomy 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000012981 Hank's balanced salt solution Substances 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000000556 agonist Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 230000009870 specific binding Effects 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 231100000673 dose–response relationship Toxicity 0.000 description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- LMQBMWHHGVZWMR-UHFFFAOYSA-N 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propyl-1-benzopyran-2-carboxylic acid Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1CCC LMQBMWHHGVZWMR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 230000035605 chemotaxis Effects 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- MWVNSXPNTJYJDR-DHIUTWEWSA-N n-[(2r,4r)-1,4-dihydroxy-4-phenylbutan-2-yl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)N[C@@H](CO)C[C@@H](O)C1=CC=CC=C1 MWVNSXPNTJYJDR-DHIUTWEWSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 102000010918 Cysteinyl leukotriene receptors Human genes 0.000 description 3
- 108050001116 Cysteinyl leukotriene receptors Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 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 3
- 239000012131 assay buffer Substances 0.000 description 3
- NBLAIKHFQBOVPV-UHFFFAOYSA-N bis(ethoxycarbonyl)azaniumylideneazanide Chemical compound CCOC(=O)[N+](=[N-])C(=O)OCC NBLAIKHFQBOVPV-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 230000002860 competitive effect Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000002464 receptor antagonist Substances 0.000 description 3
- 229940044551 receptor antagonist Drugs 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- PJNRUGKIQVSYDN-UHFFFAOYSA-N 3-(2h-chromen-2-yl)propanoic acid Chemical compound C1=CC=C2C=CC(CCC(=O)O)OC2=C1 PJNRUGKIQVSYDN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000206607 Porphyra umbilicalis Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920004890 Triton X-100 Polymers 0.000 description 2
- 239000013504 Triton X-100 Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- PRQROPMIIGLWRP-BZSNNMDCSA-N chemotactic peptide Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-BZSNNMDCSA-N 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HCZKYJDFEPMADG-TXEJJXNPSA-N masoprocol Chemical compound C([C@H](C)[C@H](C)CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-TXEJJXNPSA-N 0.000 description 2
- WVJJHBQRPIZGPT-UHFFFAOYSA-N methyl 7-hydroxy-4-oxochromene-2-carboxylate Chemical compound C1=C(O)C=C2OC(C(=O)OC)=CC(=O)C2=C1 WVJJHBQRPIZGPT-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 230000016160 smooth muscle contraction Effects 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- SLTBMTIRYMGWLX-XMMPIXPASA-N (2r)-2-[(4-chloroanilino)carbamoylamino]-3-(1h-indol-3-yl)-n-(2-phenylethyl)propanamide Chemical compound C1=CC(Cl)=CC=C1NNC(=O)N[C@@H](C(=O)NCCC=1C=CC=CC=1)CC1=CNC2=CC=CC=C12 SLTBMTIRYMGWLX-XMMPIXPASA-N 0.000 description 1
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 1
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 1
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 1
- UXKLQDCALAWFIU-VKNDCNMPSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-tetradecoxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@H](O)[C@H](C(O2)(C(O)=O)C(O)(C(O1)C(O)=O)C(O)=O)OCCCCCCCCCCCCCC)C1=CC=CC=C1 UXKLQDCALAWFIU-VKNDCNMPSA-N 0.000 description 1
- ITBCLTJCRPERNE-UHFFFAOYSA-N 1-[2-hydroxy-4-(3-iodopropoxy)-3-propylphenyl]ethanone Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCI ITBCLTJCRPERNE-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- BDLWRIAFNYVGTC-UHFFFAOYSA-N 2-[bis(2-chloroethyl)amino]ethyl 3-(acridin-9-ylamino)propanoate Chemical compound C1=CC=C2C(NCCC(=O)OCCN(CCCl)CCCl)=C(C=CC=C3)C3=NC2=C1 BDLWRIAFNYVGTC-UHFFFAOYSA-N 0.000 description 1
- QLVGHFBUSGYCCG-UHFFFAOYSA-N 2-amino-n-(1-cyano-2-phenylethyl)acetamide Chemical compound NCC(=O)NC(C#N)CC1=CC=CC=C1 QLVGHFBUSGYCCG-UHFFFAOYSA-N 0.000 description 1
- YNWNIOBEIYEXGI-UHFFFAOYSA-N 2-propoxy-8-propyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound C(CC)OC1(OC2=C(CC1)C=CC=C2CCC)C(=O)O YNWNIOBEIYEXGI-UHFFFAOYSA-N 0.000 description 1
- GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FTGYJUQWKWGXAN-UHFFFAOYSA-N 8-propyl-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid Chemical compound C(CC)C=1C=CC=C2CCC(CC=12)C(=O)O FTGYJUQWKWGXAN-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100130927 Caenorhabditis elegans moa-2 gene Proteins 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 101710091342 Chemotactic peptide Proteins 0.000 description 1
- 241000196224 Codium Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 239000012998 Hepes-buffered hanks’ balanced salt solution Substances 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000004201 L-cysteine Substances 0.000 description 1
- 235000013878 L-cysteine Nutrition 0.000 description 1
- 102000003680 Leukotriene B4 receptors Human genes 0.000 description 1
- 108090000093 Leukotriene B4 receptors Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 108010008211 N-Formylmethionine Leucyl-Phenylalanine Proteins 0.000 description 1
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241000428533 Rhis Species 0.000 description 1
- 229940125907 SJ995973 Drugs 0.000 description 1
- 102000051619 SUMO-1 Human genes 0.000 description 1
- 108700038981 SUMO-1 Proteins 0.000 description 1
- 101100481761 Sus scrofa LTB gene Proteins 0.000 description 1
- GBOGMAARMMDZGR-UHFFFAOYSA-N UNPD149280 Natural products N1C(=O)C23OC(=O)C=CC(O)CCCC(C)CC=CC3C(O)C(=C)C(C)C2C1CC1=CC=CC=C1 GBOGMAARMMDZGR-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125796 compound 3d Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NUUPJBRGQCEZSI-UHFFFAOYSA-N cyclopentane-1,3-diol Chemical compound OC1CCC(O)C1 NUUPJBRGQCEZSI-UHFFFAOYSA-N 0.000 description 1
- GBOGMAARMMDZGR-JREHFAHYSA-N cytochalasin B Natural products C[C@H]1CCC[C@@H](O)C=CC(=O)O[C@@]23[C@H](C=CC1)[C@H](O)C(=C)[C@@H](C)[C@@H]2[C@H](Cc4ccccc4)NC3=O GBOGMAARMMDZGR-JREHFAHYSA-N 0.000 description 1
- GBOGMAARMMDZGR-TYHYBEHESA-N cytochalasin B Chemical compound C([C@H]1[C@@H]2[C@@H](C([C@@H](O)[C@@H]3/C=C/C[C@H](C)CCC[C@@H](O)/C=C/C(=O)O[C@@]23C(=O)N1)=C)C)C1=CC=CC=C1 GBOGMAARMMDZGR-TYHYBEHESA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- HCZKYJDFEPMADG-UHFFFAOYSA-N erythro-nordihydroguaiaretic acid Natural products C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000012997 ficoll-paque Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- ZFKJVJIDPQDDFY-UHFFFAOYSA-N fluorescamine Chemical compound C12=CC=CC=C2C(=O)OC1(C1=O)OC=C1C1=CC=CC=C1 ZFKJVJIDPQDDFY-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 229960003951 masoprocol Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- HFVLZHKZIOAKKF-UHFFFAOYSA-N methyl 3-[7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-hydroxy-8-propyl-3,4-dihydro-2h-chromen-2-yl]propanoate Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCOC1=CC=C(C(O)CC(CCC(=O)OC)O2)C2=C1CCC HFVLZHKZIOAKKF-UHFFFAOYSA-N 0.000 description 1
- IOIBGQAXCVOBST-UHFFFAOYSA-N methyl 7-hydroxy-3,4-dihydro-2h-chromene-2-carboxylate Chemical compound C1=C(O)C=C2OC(C(=O)OC)CCC2=C1 IOIBGQAXCVOBST-UHFFFAOYSA-N 0.000 description 1
- SDXZTLQUOWTUJF-UHFFFAOYSA-N methyl 7-hydroxy-6-prop-2-enyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate Chemical compound C=CCC1=C(O)C=C2CC(C(=O)OC)CCC2=C1 SDXZTLQUOWTUJF-UHFFFAOYSA-N 0.000 description 1
- BKUUNCCUXBWJHM-UHFFFAOYSA-N methyl 7-hydroxy-8-prop-2-enyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate Chemical compound C1=C(O)C(CC=C)=C2CC(C(=O)OC)CCC2=C1 BKUUNCCUXBWJHM-UHFFFAOYSA-N 0.000 description 1
- VEBYVTATZDIXTO-UHFFFAOYSA-N methyl 7-hydroxy-8-propyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate Chemical compound C1CC(C(=O)OC)CC2=C1C=CC(O)=C2CCC VEBYVTATZDIXTO-UHFFFAOYSA-N 0.000 description 1
- FUVJIQFJMZSDRZ-UHFFFAOYSA-N methyl 7-prop-2-enoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate Chemical compound C1=C(OCC=C)C=C2CC(C(=O)OC)CCC2=C1 FUVJIQFJMZSDRZ-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- BDMBWENRFFKJON-JWQCQUIFSA-N n-[(2r,4r)-1,4-dihydroxy-4-phenylbutan-2-yl]hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)C[C@@H](O)C1=CC=CC=C1 BDMBWENRFFKJON-JWQCQUIFSA-N 0.000 description 1
- XZMHJYWMCRQSSI-UHFFFAOYSA-N n-[5-[2-(3-acetylanilino)-1,3-thiazol-4-yl]-4-methyl-1,3-thiazol-2-yl]benzamide Chemical compound CC(=O)C1=CC=CC(NC=2SC=C(N=2)C2=C(N=C(NC(=O)C=3C=CC=CC=3)S2)C)=C1 XZMHJYWMCRQSSI-UHFFFAOYSA-N 0.000 description 1
- 230000010807 negative regulation of binding Effects 0.000 description 1
- 230000031990 negative regulation of inflammatory response Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 210000003492 pulmonary vein Anatomy 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/66—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 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 in position 2
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5713687A | 1987-05-29 | 1987-05-29 | |
| US07/188,708 US4889871A (en) | 1987-05-29 | 1988-05-12 | Alkoxy-substituted dihydrobenzopyran-2-carboxylate derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26153A true PH26153A (en) | 1992-03-18 |
Family
ID=26736113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH36982A PH26153A (en) | 1987-05-29 | 1988-05-26 | Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4889871A (fr) |
| EP (1) | EP0292977B1 (fr) |
| JP (1) | JP2758902B2 (fr) |
| KR (1) | KR880013914A (fr) |
| AU (1) | AU611153B2 (fr) |
| CA (1) | CA1337660C (fr) |
| DE (1) | DE3864582D1 (fr) |
| DK (1) | DK290188A (fr) |
| ES (1) | ES2051796T3 (fr) |
| FI (1) | FI882505A (fr) |
| GR (1) | GR3003177T3 (fr) |
| IE (1) | IE60687B1 (fr) |
| IL (1) | IL86502A (fr) |
| NO (1) | NO171063C (fr) |
| NZ (1) | NZ224807A (fr) |
| PH (1) | PH26153A (fr) |
| PT (1) | PT87603B (fr) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0300404A3 (fr) * | 1987-07-20 | 1990-07-18 | G.D. Searle & Co. | Dérivés di- et tétrahydronaphtyliques comme agents anti-allergiques |
| IL89713A0 (en) * | 1988-03-29 | 1989-09-28 | Ciba Geigy Ag | Novel alkanophenones |
| IL89840A (en) * | 1988-04-06 | 1996-10-31 | Lipha | Substituted flavonoid compounds and salts thereof their preparation and pharmaceutical composition containing them |
| US5219883A (en) * | 1988-05-20 | 1993-06-15 | G. D. Searle & Co. | 2,2-di-substituted benzopyran leukotriene-D4 antagonists |
| US4931574A (en) * | 1988-08-23 | 1990-06-05 | Hoffmann-La Roche Inc. | Process for the preparation of benzopyrans |
| WO1990012010A1 (fr) * | 1989-04-07 | 1990-10-18 | Pfizer Inc. | Chromans substitues pour le traitement de l'asthme, de l'arthrite et de maladies apparentees |
| US5212198A (en) * | 1990-05-10 | 1993-05-18 | G. D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-carboxylic acids and derivatives thereof |
| US5192782A (en) * | 1990-05-10 | 1993-03-09 | G. D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-carboxylic acids and derivatives thereof |
| US5073562A (en) * | 1990-05-10 | 1991-12-17 | G. D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-carboxylic acids and derivatives thereof |
| US5051438A (en) * | 1990-05-16 | 1991-09-24 | G. D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-carboxylic acids and derivatives thereof, compositions and use |
| US5124350A (en) * | 1990-06-28 | 1992-06-23 | G. D. Searle & Co. | Leukotriene b4 antagonists |
| FR2665159B1 (fr) * | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| EP0548250B1 (fr) * | 1990-09-10 | 1996-03-27 | Rhone-Poulenc Rorer International (Holdings) Inc. | Composes aryles bicycliques substitues presentant une activite selective antagoniste contre les leucotrienes b4 |
| US5488160A (en) * | 1991-06-11 | 1996-01-30 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and method of treatment |
| US5451700A (en) * | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
| US5273999A (en) * | 1991-09-10 | 1993-12-28 | Hoffmann-La Roche Inc. | Carboxylic acid leukotriene B4 antagonists |
| WO1993012783A1 (fr) * | 1991-12-27 | 1993-07-08 | Kureha Chemical Industry Co., Ltd. | Pommade oleagineuse |
| WO1993015066A1 (fr) * | 1992-01-23 | 1993-08-05 | Pfizer Inc. | Benzopyranne et antagonistes du ltb4 apparentes |
| CZ287209B6 (en) * | 1992-02-05 | 2000-10-11 | Boehringer Ingelheim Kg | Amidine derivatives, process of their preparation and pharmaceutical preparations containing thereof |
| US5352690A (en) * | 1992-07-01 | 1994-10-04 | Eli Lilly And Company | 1,2,4-trioxygenated benzene derivatives useful as leukotriene antagonists |
| JPH0625764A (ja) * | 1992-07-08 | 1994-02-01 | Sumitomo Metal Ind Ltd | フェロスクラップ中の銅の除去・回収方法 |
| US5324743A (en) * | 1992-12-10 | 1994-06-28 | Eli Lilly And Company | Leukotriene B4 antagonists |
| DE4309285A1 (de) * | 1993-03-23 | 1994-09-29 | Boehringer Ingelheim Kg | Heterocyclen enthaltende Amidinderivate, ihre Herstellung und Verwendung |
| US5380740A (en) * | 1993-04-28 | 1995-01-10 | G. D. Searle & Co. | Anti-inflammatory compounds, compositions and method of use thereof |
| ES2084547B1 (es) * | 1993-07-12 | 1997-01-16 | Pfizer | Antagonistas benzopiranicos y relacionados de leucotrieno b4. |
| US5457124A (en) * | 1993-12-07 | 1995-10-10 | Hoffmann-La Roche Inc. | Carboxylic acid Leukotriene B4 antagonists |
| AU2585595A (en) * | 1994-05-25 | 1995-12-18 | G.D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-sulfonimides derivatives, their preparation and their use as leukotriene b4 antagonists |
| US5516917A (en) * | 1994-06-08 | 1996-05-14 | G. D. Searle & Co. | Leukotriene B4 antagonists |
| EP0777472A2 (fr) | 1994-08-31 | 1997-06-11 | Eli Lilly And Company | Procedes d'identification et de traitement de tumeurs resistantes |
| US5543428A (en) * | 1994-08-31 | 1996-08-06 | Eli Lilly And Company | Method for treating resistant tumors |
| CA2202056A1 (fr) * | 1994-10-13 | 1996-04-25 | Mark A. Dombroski | Composes de benzopyranne et composes benzo-fusionnes, leur preparation et leur utilisation comme antagonistes du leucotriene b4' (ltb4) |
| MX9702731A (es) * | 1994-10-13 | 1997-06-28 | Pfizer | Compuestos de benzopirano y benzo fusionados, composiciones que los contienen y uso de los mismos. |
| EP0836850A3 (fr) * | 1996-10-17 | 2000-11-29 | Pfizer Inc. | Méthode pour prévenir le rejet d'allogreffes |
| CA2339947A1 (fr) * | 1998-08-28 | 2000-03-09 | Biomedicines, Inc. | Procede d'attenuation des effets secondaires de l'interleukine-2 |
| US6436987B1 (en) | 2000-06-08 | 2002-08-20 | Pfizer Inc. | Crystalline forms of (3S-trans)-2-[3,4-dihydro-4-hydroxy-3-(phenylmethyl)-2H-1-benzopyran-7-yl]-4-(trifluoromethyl)-benzoic acid |
| EP1324995A2 (fr) * | 2000-09-27 | 2003-07-09 | Merck & Co., Inc. | Derives d'acide benzopyrancarboxylique utilises pour le traitement du diabete et des troubles lipidiques |
| EP1347755A2 (fr) | 2000-10-31 | 2003-10-01 | Merck & Co., Inc. | Derives d'acide benzopyranocarboxylique pour traiter le diabete et d'autres troubles lipidiques |
| US20040242676A1 (en) * | 2003-05-30 | 2004-12-02 | Alessi Thomas R. | Method of mitigating the adverse effects of IL-2 |
| US8093253B2 (en) * | 2008-03-06 | 2012-01-10 | Hoffmann-La Roche Inc. | Leukotriene B4 inhibitors |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006245A (en) * | 1971-07-29 | 1977-02-01 | Fisons Limited | Chemical compounds |
| GB1384530A (en) * | 1971-07-29 | 1975-02-19 | Fisons Ltd | Chromone derivatives |
| DE3070912D1 (en) * | 1979-03-20 | 1985-09-05 | Fisons Plc | Pharmaceutical heterocyclic compounds, processes for their preparation and compositions containing them |
| US4474788A (en) * | 1981-11-12 | 1984-10-02 | Fisons Plc | Anti-SRSA quinoline carboxylic acid derivatives |
| ZA844519B (en) * | 1983-06-24 | 1985-02-27 | Hoffmann La Roche | Dihydrobenzopyran derivatives |
| US4665203A (en) * | 1983-08-08 | 1987-05-12 | G. D. Searle & Co. | Substituted dihydrobenzopyrans useful as leukotriene D4 inhibitors |
| AU548450B2 (en) * | 1983-08-08 | 1985-12-12 | G.D. Searle & Co. | Substituted dihydrobenzopyrans |
| US4565882A (en) * | 1984-01-06 | 1986-01-21 | G. D. Searle & Co. | Substituted dihydrobenzopyran-2-carboxylates |
| US4546194A (en) * | 1984-05-29 | 1985-10-08 | G. D. Searle & Co. | Substituted chromanon-2-yl alkanols and derivatives thereof |
| DE3569062D1 (en) * | 1985-06-28 | 1989-04-27 | Ibm | Shadow mask colour crt with enhanced resolution and/or brightness |
| ZA873745B (en) * | 1986-06-04 | 1988-10-26 | Daiichi Seiyaku Co | Benzopyran derivatives |
| US4885309A (en) * | 1986-08-01 | 1989-12-05 | Hoffmann-La Roche Inc. | Therapeutic treatment of leukotriene-mediated dermal inflammation by topical administration of 3,4-dihydro-2H-1-benzopyran derivatives |
-
1988
- 1988-05-12 US US07/188,708 patent/US4889871A/en not_active Expired - Lifetime
- 1988-05-26 CA CA000567806A patent/CA1337660C/fr not_active Expired - Fee Related
- 1988-05-26 PH PH36982A patent/PH26153A/en unknown
- 1988-05-26 AU AU16681/88A patent/AU611153B2/en not_active Ceased
- 1988-05-26 NZ NZ224807A patent/NZ224807A/xx unknown
- 1988-05-26 IL IL8650288A patent/IL86502A/en unknown
- 1988-05-26 NO NO882317A patent/NO171063C/no unknown
- 1988-05-27 PT PT87603A patent/PT87603B/pt not_active IP Right Cessation
- 1988-05-27 DK DK290188A patent/DK290188A/da not_active Application Discontinuation
- 1988-05-27 FI FI882505A patent/FI882505A/fi not_active IP Right Cessation
- 1988-05-27 DE DE8888108449T patent/DE3864582D1/de not_active Expired - Fee Related
- 1988-05-27 IE IE161188A patent/IE60687B1/en not_active IP Right Cessation
- 1988-05-27 JP JP63130037A patent/JP2758902B2/ja not_active Expired - Fee Related
- 1988-05-27 EP EP88108449A patent/EP0292977B1/fr not_active Expired - Lifetime
- 1988-05-27 ES ES88108449T patent/ES2051796T3/es not_active Expired - Lifetime
- 1988-05-27 KR KR1019880006263A patent/KR880013914A/ko not_active Application Discontinuation
-
1991
- 1991-11-22 GR GR91401338T patent/GR3003177T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2758902B2 (ja) | 1998-05-28 |
| DE3864582D1 (de) | 1991-10-10 |
| NO882317L (no) | 1988-11-30 |
| NO171063B (no) | 1992-10-12 |
| JPS6438045A (en) | 1989-02-08 |
| EP0292977A1 (fr) | 1988-11-30 |
| FI882505A0 (fi) | 1988-05-27 |
| PT87603B (pt) | 1992-12-31 |
| ES2051796T3 (es) | 1994-07-01 |
| CA1337660C (fr) | 1995-11-28 |
| AU1668188A (en) | 1988-12-01 |
| GR3003177T3 (en) | 1993-02-17 |
| IL86502A (en) | 1994-07-31 |
| IE60687B1 (en) | 1994-08-10 |
| NO171063C (no) | 1993-01-20 |
| NO882317D0 (no) | 1988-05-26 |
| KR880013914A (ko) | 1988-12-22 |
| FI882505A (fi) | 1988-11-30 |
| IE881611L (en) | 1988-11-29 |
| DK290188A (da) | 1988-11-30 |
| DK290188D0 (da) | 1988-05-27 |
| PT87603A (pt) | 1988-06-01 |
| US4889871A (en) | 1989-12-26 |
| NZ224807A (en) | 1991-03-26 |
| AU611153B2 (en) | 1991-06-06 |
| EP0292977B1 (fr) | 1991-09-04 |
| IL86502A0 (en) | 1988-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PH26153A (en) | Alkoxy-substituted dihydro-benzopyran-2-carboxylate derivatives pharmaceutical composition containing said compound and method of use thereof | |
| US5439937A (en) | Leukotriene B4 antagonists | |
| EP0150447B1 (fr) | Dihydrobenzopyrannes 2-carboxylates substitués | |
| US5047431A (en) | 1,1,2-triphenylbut-1-ene derivatives | |
| US4388312A (en) | Quinone derivatives, their production and use | |
| US4565818A (en) | Pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline derivatives | |
| GB2196964A (en) | (6a s, 10a s)-1-hydroxy- 8-thc derivatives | |
| JPH0678257B2 (ja) | 新規なアルケン誘導体の製造法 | |
| EP0717620A1 (fr) | 2-aminotetralines substituees | |
| Salman et al. | Studies in antifertility agents. 50. Stereoselective binding of d-and l-centchromans to estrogen receptors and their antifertility activity | |
| DE69104719T2 (de) | Alkoxy-substituierte dihydrobenzopyran-2-carbonsäure und deren derivate. | |
| EP0235452A2 (fr) | Composés organiques et leur application pharmaceutique | |
| US4533554A (en) | Quinone derivatives and use | |
| US4312861A (en) | Pharmaceutical compositions containing N-alkyl-N-(nuclearly-substituted) benzylamines having vasotonia-regulating activity | |
| IE55991B1 (en) | Bicyclic benzo fused compounds | |
| CA1326675C (fr) | Derives trieniques de structure chromenique, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent | |
| WO1990012795A1 (fr) | 3-amino chromanes substitues | |
| NZ236534A (en) | Method of treating inflammatory diseases | |
| US4192868A (en) | Novel aryl-hexafuranosides and processes for their preparation | |
| PL125297B1 (en) | Process for preparing novel dibenzo/b,d/-pyranes | |
| CA1220787A (fr) | Derives de 1,1,2-triphenyl-but-1-ene possedant un pouvoir anti-oestrogenique | |
| WO1981003021A1 (fr) | Derives de bis-hydroxybenzyle, leur procede de preparation et composition pharmaceutique les contenant | |
| EP0108822B1 (fr) | Composés contre le glaucome | |
| US3707551A (en) | Pharmaceutically active derivatives of ethanooctahydrophenanthrene | |
| US4971997A (en) | Furyl, phenylene, and thienyl leukotriene B4 analogues |