PH25958A - Benzofurans and benzothiophenes having antiallergic activity pharmaceutical compositions containing the same and method of use thereof - Google Patents
Benzofurans and benzothiophenes having antiallergic activity pharmaceutical compositions containing the same and method of use thereof Download PDFInfo
- Publication number
- PH25958A PH25958A PH37219A PH37219A PH25958A PH 25958 A PH25958 A PH 25958A PH 37219 A PH37219 A PH 37219A PH 37219 A PH37219 A PH 37219A PH 25958 A PH25958 A PH 25958A
- Authority
- PH
- Philippines
- Prior art keywords
- compound
- thiophene
- benzo
- tetrazol
- carboxamide
- Prior art date
Links
- 230000003266 anti-allergic effect Effects 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract description 15
- 150000001907 coumarones Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
- 238000010992 reflux Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 239000002552 dosage form Substances 0.000 claims description 7
- -1 nitro, amino Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 241000282414 Homo sapiens Species 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 230000007815 allergy Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- QZHGFALVBFEAES-UHFFFAOYSA-N 5-methoxy-6-phenylmethoxy-3-propan-2-yloxy-1-benzothiophene-2-carboxylic acid Chemical compound COC1=CC=2C(OC(C)C)=C(C(O)=O)SC=2C=C1OCC1=CC=CC=C1 QZHGFALVBFEAES-UHFFFAOYSA-N 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 230000002682 anti-psoriatic effect Effects 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims 3
- XRUQMNVURXXUSZ-UHFFFAOYSA-N 5-methoxy-6-phenylmethoxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound COC1=CC=2C(OC(C)C)=C(C(=O)NC=3NN=NN=3)SC=2C=C1OCC1=CC=CC=C1 XRUQMNVURXXUSZ-UHFFFAOYSA-N 0.000 claims 1
- RTIXKCRFFJGDFG-UHFFFAOYSA-N chrysin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 0.000 claims 1
- AVBDPKLHYNAMQS-UHFFFAOYSA-N di(imidazol-1-yl)methanone 1H-imidazole Chemical compound C(=O)(N1C=NC=C1)N1C=NC=C1.N1C=NC=C1 AVBDPKLHYNAMQS-UHFFFAOYSA-N 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 abstract description 8
- 201000000028 adult respiratory distress syndrome Diseases 0.000 abstract description 7
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 abstract description 6
- KWJGNLIHELNBDN-UHFFFAOYSA-N tetrazole-2-carboxamide Chemical class NC(=O)N1N=CN=N1 KWJGNLIHELNBDN-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 101710172562 Cobra venom factor Proteins 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000006188 syrup Substances 0.000 description 7
- 235000020357 syrup Nutrition 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- DTMXTCKEPQWRPO-UHFFFAOYSA-N 3-chloro-6-methoxy-1-benzothiophene-2-carbonyl chloride Chemical compound COC1=CC=C2C(Cl)=C(C(Cl)=O)SC2=C1 DTMXTCKEPQWRPO-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 210000003630 histaminocyte Anatomy 0.000 description 4
- 210000000440 neutrophil Anatomy 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 102220498920 Transcriptional protein SWT1_C21A_mutation Human genes 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000005462 in vivo assay Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004533 oil dispersion Substances 0.000 description 3
- 238000002360 preparation method Methods 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
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 2
- FLABMTVDNODXQV-UHFFFAOYSA-N 2h-tetrazole-5-carboxamide Chemical compound NC(=O)C=1N=NNN=1 FLABMTVDNODXQV-UHFFFAOYSA-N 0.000 description 2
- RJXUGUBKNZNIJV-UHFFFAOYSA-N 5,6-dimethoxy-3-phenoxy-1-benzothiophene-2-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2SC(C(O)=O)=C1OC1=CC=CC=C1 RJXUGUBKNZNIJV-UHFFFAOYSA-N 0.000 description 2
- OAQBIFGORBKWNJ-UHFFFAOYSA-N 5-methoxy-3-phenylmethoxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound C=1C=CC=CC=1COC=1C2=CC(OC)=CC=C2SC=1C(=O)NC1=NN=NN1 OAQBIFGORBKWNJ-UHFFFAOYSA-N 0.000 description 2
- RONBWDBZMKLGTP-UHFFFAOYSA-N 6-methoxy-3-phenylmethoxy-1-benzothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC2=CC(OC)=CC=C2C=1OCC1=CC=CC=C1 RONBWDBZMKLGTP-UHFFFAOYSA-N 0.000 description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- 208000004852 Lung Injury Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 102220479482 Puromycin-sensitive aminopeptidase-like protein_C21D_mutation Human genes 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010069363 Traumatic lung injury Diseases 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000515 lung injury Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 230000019254 respiratory burst Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 1
- RYTBBLWPDBZDHT-MDZDMXLPSA-N (e)-3-(3-phenoxyphenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(OC=2C=CC=CC=2)=C1 RYTBBLWPDBZDHT-MDZDMXLPSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- LELKSZPZTRAHOA-UHFFFAOYSA-N 1h-imidazole;5-methoxy-6-phenylmethoxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound C1=CNC=N1.COC1=CC=2C(OC(C)C)=C(C(=O)NC=3NN=NN=3)SC=2C=C1OCC1=CC=CC=C1 LELKSZPZTRAHOA-UHFFFAOYSA-N 0.000 description 1
- HJBWJAPEBGSQPR-GQCTYLIASA-N 3,4-dimethoxycinnamic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1OC HJBWJAPEBGSQPR-GQCTYLIASA-N 0.000 description 1
- WSOBQOYHYGVEIR-UHFFFAOYSA-N 3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(C=CC(O)=O)=CC=C1OCC1=CC=CC=C1 WSOBQOYHYGVEIR-UHFFFAOYSA-N 0.000 description 1
- OFMOWGZEBJKDCT-UHFFFAOYSA-N 3-(3-phenylmethoxyphenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC(OCC=2C=CC=CC=2)=C1 OFMOWGZEBJKDCT-UHFFFAOYSA-N 0.000 description 1
- XWGDODCEQXQAFQ-UHFFFAOYSA-N 3-(4-phenoxyphenyl)prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1OC1=CC=CC=C1 XWGDODCEQXQAFQ-UHFFFAOYSA-N 0.000 description 1
- HCMSDYVKYZIYGA-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1OCC1=CC=CC=C1 HCMSDYVKYZIYGA-UHFFFAOYSA-N 0.000 description 1
- FPOJTIOYSDDNKZ-UHFFFAOYSA-N 3-chloro-5,6-dimethoxy-1-benzothiophene-2-carbonyl chloride Chemical compound C1=C(OC)C(OC)=CC2=C1C(Cl)=C(C(Cl)=O)S2 FPOJTIOYSDDNKZ-UHFFFAOYSA-N 0.000 description 1
- DLJHFQNHWUTVRD-UHFFFAOYSA-N 3-chloro-5-methoxy-1-benzothiophene-2-carbonyl chloride Chemical compound COC1=CC=C2SC(C(Cl)=O)=C(Cl)C2=C1 DLJHFQNHWUTVRD-UHFFFAOYSA-N 0.000 description 1
- URFOTHCXSLBNIK-UHFFFAOYSA-N 3-chloro-5-methoxy-6-phenylmethoxy-1-benzothiophene-2-carbonyl chloride Chemical compound COC1=CC=2C(Cl)=C(C(Cl)=O)SC=2C=C1OCC1=CC=CC=C1 URFOTHCXSLBNIK-UHFFFAOYSA-N 0.000 description 1
- CKNPQZSCMFMRPI-UHFFFAOYSA-N 3-chloro-5-phenylmethoxy-1-benzothiophene-2-carbonyl chloride Chemical compound C1=C2C(Cl)=C(C(=O)Cl)SC2=CC=C1OCC1=CC=CC=C1 CKNPQZSCMFMRPI-UHFFFAOYSA-N 0.000 description 1
- UBEMZHCSZYRXDN-UHFFFAOYSA-N 3-chloro-6-phenoxy-1-benzothiophene-2-carbonyl chloride Chemical compound C=1C=C2C(Cl)=C(C(=O)Cl)SC2=CC=1OC1=CC=CC=C1 UBEMZHCSZYRXDN-UHFFFAOYSA-N 0.000 description 1
- OXFBUYSTQUUFKZ-UHFFFAOYSA-N 3-chloro-6-phenylmethoxy-1-benzothiophene-2-carbonyl chloride Chemical compound C=1C=C2C(Cl)=C(C(=O)Cl)SC2=CC=1OCC1=CC=CC=C1 OXFBUYSTQUUFKZ-UHFFFAOYSA-N 0.000 description 1
- XUPGMSOTSFAJPR-UHFFFAOYSA-N 5,6-dimethoxy-3-phenoxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound C=1C=CC=CC=1OC=1C=2C=C(OC)C(OC)=CC=2SC=1C(=O)NC1=NN=NN1 XUPGMSOTSFAJPR-UHFFFAOYSA-N 0.000 description 1
- IZTNXPQUTWNESS-UHFFFAOYSA-N 5,6-dimethoxy-3-phenylmethoxy-1-benzothiophene-2-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2SC(C(O)=O)=C1OCC1=CC=CC=C1 IZTNXPQUTWNESS-UHFFFAOYSA-N 0.000 description 1
- CIXJEDSZHYLQPK-UHFFFAOYSA-N 5,6-dimethoxy-3-phenylmethoxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound C=1C=CC=CC=1COC=1C=2C=C(OC)C(OC)=CC=2SC=1C(=O)NC1=NN=NN1 CIXJEDSZHYLQPK-UHFFFAOYSA-N 0.000 description 1
- QLPWPCCOXQQRBP-UHFFFAOYSA-N 5-hydroxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=C(O)C=C2C(OC(C)C)=C1C(=O)NC1=NN=NN1 QLPWPCCOXQQRBP-UHFFFAOYSA-N 0.000 description 1
- ZPPJJVZTISSGNZ-UHFFFAOYSA-N 5-methoxy-3-phenylmethoxy-1-benzothiophene-2-carboxylic acid Chemical compound C12=CC(OC)=CC=C2SC(C(O)=O)=C1OCC1=CC=CC=C1 ZPPJJVZTISSGNZ-UHFFFAOYSA-N 0.000 description 1
- TVVXHFWWAYXBNC-UHFFFAOYSA-N 5-methoxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound CC(C)OC=1C2=CC(OC)=CC=C2SC=1C(=O)NC=1N=NNN=1 TVVXHFWWAYXBNC-UHFFFAOYSA-N 0.000 description 1
- HGPNPRPMBQCSRQ-UHFFFAOYSA-N 5-phenylmethoxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound C1=C2C(OC(C)C)=C(C(=O)NC=3NN=NN=3)SC2=CC=C1OCC1=CC=CC=C1 HGPNPRPMBQCSRQ-UHFFFAOYSA-N 0.000 description 1
- VCOSJELVJCPVJP-UHFFFAOYSA-N 6-methoxy-3-phenoxy-1-benzothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC2=CC(OC)=CC=C2C=1OC1=CC=CC=C1 VCOSJELVJCPVJP-UHFFFAOYSA-N 0.000 description 1
- LHGKCZGVXZLMJR-UHFFFAOYSA-N 6-methoxy-3-phenoxy-n-(2h-tetrazol-5-yl)-1-benzothiophene-2-carboxamide Chemical compound N=1N=NNC=1NC(=O)C=1SC2=CC(OC)=CC=C2C=1OC1=CC=CC=C1 LHGKCZGVXZLMJR-UHFFFAOYSA-N 0.000 description 1
- MFLJZASVFAWOHX-UHFFFAOYSA-N 6-methoxy-3-propan-2-yloxy-n-(2h-tetrazol-5-yl)-1-benzofuran-2-carboxamide Chemical compound O1C2=CC(OC)=CC=C2C(OC(C)C)=C1C(=O)NC1=NN=NN1 MFLJZASVFAWOHX-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010009192 Circulatory collapse Diseases 0.000 description 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- HJBWJAPEBGSQPR-UHFFFAOYSA-N DMCA Natural products COC1=CC=C(C=CC(O)=O)C=C1OC HJBWJAPEBGSQPR-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 208000004262 Food Hypersensitivity Diseases 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 206010019909 Hernia Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010038687 Respiratory distress Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 206010039101 Rhinorrhoea Diseases 0.000 description 1
- 206010048908 Seasonal allergy Diseases 0.000 description 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 241000159241 Toxicodendron Species 0.000 description 1
- 241000159243 Toxicodendron radicans Species 0.000 description 1
- 102220498936 Transcriptional protein SWT1_C20A_mutation Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 235000005505 Ziziphus oenoplia Nutrition 0.000 description 1
- 244000104547 Ziziphus oenoplia Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000002205 allergic conjunctivitis Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 230000002460 anti-migrenic effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000024998 atopic conjunctivitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- VVTTVMMZBLGRPP-UHFFFAOYSA-N benzyl 5-methoxy-3-phenylmethoxy-1-benzothiophene-2-carboxylate Chemical compound C=1C=CC=CC=1COC=1C2=CC(OC)=CC=C2SC=1C(=O)OCC1=CC=CC=C1 VVTTVMMZBLGRPP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000020411 cell activation Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-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
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000020932 food allergy Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002518 glial effect Effects 0.000 description 1
- 210000000224 granular leucocyte Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 230000004317 lacrimation Effects 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 208000010753 nasal discharge Diseases 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000004783 oxidative metabolism Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 206010041232 sneezing Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7355487A | 1987-07-14 | 1987-07-14 | |
| US19169988A | 1988-05-17 | 1988-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH25958A true PH25958A (en) | 1992-01-13 |
Family
ID=26754606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH37219A PH25958A (en) | 1987-07-14 | 1988-07-13 | Benzofurans and benzothiophenes having antiallergic activity pharmaceutical compositions containing the same and method of use thereof |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0299457B1 (da) |
| JP (1) | JP2672980B2 (da) |
| KR (1) | KR970011580B1 (da) |
| CN (1) | CN1031084A (da) |
| AT (1) | ATE111908T1 (da) |
| AU (1) | AU605070B2 (da) |
| CA (1) | CA1330562C (da) |
| DE (1) | DE3851584T2 (da) |
| DK (1) | DK175933B1 (da) |
| ES (1) | ES2063747T3 (da) |
| FI (1) | FI91256C (da) |
| IE (1) | IE64995B1 (da) |
| NO (1) | NO170886C (da) |
| NZ (1) | NZ225378A (da) |
| PH (1) | PH25958A (da) |
| PT (1) | PT87975B (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2689129B1 (fr) * | 1992-03-27 | 1995-05-12 | Atochem Elf Sa | Nouveaux dérivés de l'acide 3-mercapto-2-thénoique et leurs procédés de préparation. |
| US5426191A (en) * | 1993-12-03 | 1995-06-20 | Warner-Lambert Company | Process for the synthesis of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides |
| US6203803B1 (en) | 1994-12-14 | 2001-03-20 | Societe L'oreal S.A. | Use of a substance P antagonist in a cosmetic composition, and the composition thus obtained |
| FR2719474B1 (fr) | 1994-05-05 | 1996-05-31 | Oreal | Utilisation d'un antagoniste de substance P dans une composition cosmétique et composition obtenue. |
| FR2719476B1 (fr) * | 1994-05-05 | 1997-05-23 | Oreal | Utilisation d'un antagoniste de substance P dans une composition cosmétique et composition obtenue. |
| FR2728166A1 (fr) | 1994-12-19 | 1996-06-21 | Oreal | Composition topique contenant un antagoniste de substance p |
| FR2728793A1 (fr) * | 1994-12-28 | 1996-07-05 | Oreal | Utilisation d'un antagoniste d'histamine, d'un antagoniste d'interleukine 1 et/ou d'un antagoniste de tnf-alpha dans une composition cosmetique, pharmaceutique ou dermatologique et composition obtenue |
| DE19620508A1 (de) * | 1996-05-22 | 1997-11-27 | Hoechst Ag | Schwefelenthaltende heterocyclische Bradykinin-Antagonisten, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP1636210A1 (en) * | 2003-06-05 | 2006-03-22 | Warner-Lambert Company LLC | Cycloalkyl and heterocycloalkyl substituted benzothiophenes as therapeutic agents |
| EP1636211A1 (en) * | 2003-06-05 | 2006-03-22 | Warner-Lambert Company | 3-arylsulfanyl and 3-heteroarylsulfanyl substituted benzo[b]thiophenes as therapeutic agents |
| EP1644360A1 (en) * | 2003-06-05 | 2006-04-12 | Warner-Lambert Company LLC | 3-substituted indoles and derivatives thereof as therapeutic agents |
| EP1636212B1 (en) * | 2003-06-05 | 2007-06-27 | Warner-Lambert Company LLC | Cycloalkylsulfanyl substituted benzo¬b|thiophenes as therapeutic agents |
| US20040259926A1 (en) * | 2003-06-05 | 2004-12-23 | Bruendl Michelle M. | 3-Aryloxy and 3-heteroaryloxy substituted benzo[b]thiophenes as therapeutic agents |
| BRPI0414171A (pt) * | 2003-09-04 | 2006-10-31 | Warner Lambert Co | benzo[b]tiofenos halossubstituìdos com atividade inibidora de pi3k como agentes terapêuticos |
| FR2862645B1 (fr) * | 2003-11-20 | 2007-06-22 | Merck Sante Sas | Composes antidiabetiques contenant des derives benzofuranes, benzothiophenes |
| US7674822B2 (en) | 2004-11-24 | 2010-03-09 | Wyeth | PTP1b inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140785A (en) * | 1978-05-08 | 1979-02-20 | E. I. Du Pont De Nemours And Company | N-(benzothienopyrazol)amide antirhinoviral agents |
| US4432986A (en) * | 1979-06-18 | 1984-02-21 | Riker Laboratories, Inc. | Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof |
| EP0146243A1 (en) * | 1983-10-31 | 1985-06-26 | Merck Frosst Canada Inc. | Lipoxygenase inhibitors |
| GB8401288D0 (en) * | 1984-01-18 | 1984-02-22 | Pfizer Ltd | Therapeutic agents |
| GB8426474D0 (en) * | 1984-10-19 | 1984-11-28 | Ici America Inc | Heterocyclic amides |
| US4675332A (en) * | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
| IE58555B1 (en) * | 1984-12-10 | 1993-10-06 | Warner Almbert Company | Novel benzothiophenes and benzofurans having antiallergy activity |
| ZA858748B (en) * | 1984-12-10 | 1987-06-24 | Warner Lambert Co | Novel benzothiophenes and benzofurans having antiallergy activity |
| US4748183A (en) * | 1986-06-13 | 1988-05-31 | Warner-Lambert Company | N-1H-tetrazol-5-yl-2-thiophene carboxamides, N-1H-tetrazol-5-yl-2-pyrrole carboxamides, N-1H-tetrazol-5-yl-2-furan carboxamides, and anti-allergic and anti-inflammatory use thereof |
| EP0253650A3 (en) * | 1986-07-18 | 1989-09-13 | Eli Lilly And Company | Improvements relating to benzothiophene derivatives |
-
1988
- 1988-06-21 IE IE187988A patent/IE64995B1/en not_active IP Right Cessation
- 1988-06-30 AU AU18577/88A patent/AU605070B2/en not_active Ceased
- 1988-06-30 CA CA000570900A patent/CA1330562C/en not_active Expired - Fee Related
- 1988-07-11 FI FI883300A patent/FI91256C/fi not_active IP Right Cessation
- 1988-07-12 DK DK198803884A patent/DK175933B1/da not_active IP Right Cessation
- 1988-07-12 NZ NZ225378A patent/NZ225378A/en unknown
- 1988-07-12 NO NO883100A patent/NO170886C/no unknown
- 1988-07-13 JP JP63172808A patent/JP2672980B2/ja not_active Expired - Fee Related
- 1988-07-13 EP EP88111224A patent/EP0299457B1/en not_active Expired - Lifetime
- 1988-07-13 PH PH37219A patent/PH25958A/en unknown
- 1988-07-13 ES ES88111224T patent/ES2063747T3/es not_active Expired - Lifetime
- 1988-07-13 PT PT87975A patent/PT87975B/pt not_active IP Right Cessation
- 1988-07-13 DE DE3851584T patent/DE3851584T2/de not_active Expired - Fee Related
- 1988-07-13 AT AT88111224T patent/ATE111908T1/de not_active IP Right Cessation
- 1988-07-14 CN CN88104422A patent/CN1031084A/zh active Pending
- 1988-07-14 KR KR1019880008717A patent/KR970011580B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0299457A3 (en) | 1989-07-19 |
| DK388488A (da) | 1989-01-15 |
| DE3851584T2 (de) | 1995-01-26 |
| EP0299457B1 (en) | 1994-09-21 |
| FI883300A0 (fi) | 1988-07-11 |
| FI91256C (fi) | 1994-06-10 |
| NO883100L (no) | 1989-01-16 |
| FI883300A (fi) | 1989-01-15 |
| NO170886B (no) | 1992-09-14 |
| NO170886C (no) | 1992-12-23 |
| DE3851584D1 (de) | 1994-10-27 |
| EP0299457A2 (en) | 1989-01-18 |
| NO883100D0 (no) | 1988-07-12 |
| NZ225378A (en) | 1992-03-26 |
| DK175933B1 (da) | 2005-07-18 |
| KR890002129A (ko) | 1989-04-08 |
| IE64995B1 (en) | 1995-09-20 |
| AU1857788A (en) | 1989-01-19 |
| IE881879L (en) | 1989-01-14 |
| CN1031084A (zh) | 1989-02-15 |
| DK388488D0 (da) | 1988-07-12 |
| PT87975A (pt) | 1989-06-30 |
| AU605070B2 (en) | 1991-01-03 |
| ES2063747T3 (es) | 1995-01-16 |
| JP2672980B2 (ja) | 1997-11-05 |
| CA1330562C (en) | 1994-07-05 |
| KR970011580B1 (ko) | 1997-07-12 |
| FI91256B (fi) | 1994-02-28 |
| ATE111908T1 (de) | 1994-10-15 |
| PT87975B (pt) | 1995-03-01 |
| JPH01110682A (ja) | 1989-04-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0299457B1 (en) | Novel benzothiophenes having antiallergic activity and both novel and other selected benzothiophenes having activity for treating acute respiratory distress syndrome | |
| US4703053A (en) | Benzothiophenes and benzofurans and antiallergic use thereof | |
| Connor et al. | Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents | |
| US4556672A (en) | 3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents | |
| US5684002A (en) | Dihydorbenzofuran and related compounds useful as anti-inflammatory agents | |
| JP2002514638A (ja) | インスリン抵抗性および高血糖症の治療に有用な１１−アリール−ベンゾ［ｂ］ナフト［２，３−ｄ］フラン類および１１−アリール−ベンゾ［ｂ］ナフト［２，３−ｄ］チオフェン類 | |
| US4910317A (en) | Benzofurans and benzothiophenes having antiallergic activity and method of use thereof | |
| KR20010102543A (ko) | 항바이러스제로서의4-옥소-4,7-디히드로-티에노[2,3-ｂ]피리딘-5-카르복스아미드 | |
| EP0187487B1 (en) | Benzothiophenes and benzofurans having antiallergic activity | |
| WO1994006789A1 (en) | Serotonin receptor agents | |
| US4931459A (en) | Method for treating acute respirator distress syndrome | |
| US5116854A (en) | Anti-inflammatory 1-heteroaryl-3-acyl-2-oxindoles | |
| US4663344A (en) | Anti-inflammatory and analgesic 3-hydroxybenzo[b]thiophene derivatives, compositions, and method of use therefor | |
| JPH10298180A (ja) | ドーパミン受容体拮抗作用を有する化合物 | |
| FI80270B (fi) | Foerfarande foer framstaellning av analgetiska och anti-inflammatoriska 1,3-diacyl-2-oxoindol-foereningar och mellanprodukter. | |
| DK175445B1 (da) | Anvendelse af benzothiophener ved fremstilling af lægemidler til behandling af akut respiratorisk distress syndrom | |
| NO178496B (no) | Kinolin-2-yl-metoksybenzylhydroksyurea | |
| IE902836A1 (en) | Substituted dibenzofurans and methods of using same | |
| AU616336B2 (en) | Anti-inflammatory 1-heteroaryl-3-acyl-2-oxindoles | |
| JPS61171479A (ja) | 新規なベンゾチオフェン | |
| JPH08208645A (ja) | キノリン誘導体 | |
| JPS62273977A (ja) | フリルチアゾ−ル化合物 | |
| JPH10182546A (ja) | アズレン誘導体およびその製造方法並びにそれを含有する薬剤 |