NO310109B1 - Naftalenderivater og mellomprodukter ved deres fremstilling - Google Patents
Naftalenderivater og mellomprodukter ved deres fremstilling Download PDFInfo
- Publication number
- NO310109B1 NO310109B1 NO962527A NO962527A NO310109B1 NO 310109 B1 NO310109 B1 NO 310109B1 NO 962527 A NO962527 A NO 962527A NO 962527 A NO962527 A NO 962527A NO 310109 B1 NO310109 B1 NO 310109B1
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- group
- bis
- hydroxymethyl
- dimethoxynaphthalene
- Prior art date
Links
- 150000002790 naphthalenes Chemical class 0.000 title claims description 7
- 239000000543 intermediate Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 110
- -1 hydroxy-substituted methyl group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical class 0.000 claims description 10
- 238000006722 reduction reaction Methods 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- IQKXFSXPCZEULC-UHFFFAOYSA-N 1-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]quinolin-2-one Chemical group C12=CC=CC=C2C=CC(=O)N1C1=CC(C=2C(CO)=C(CO)C=C3C=C(C(=CC3=2)OC)OC)=CC=N1 IQKXFSXPCZEULC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- OEZADIAHVKNQKD-UHFFFAOYSA-N 2-[4-[6,7-diethoxy-2,3-bis(hydroxymethyl)naphthalen-1-yl]pyridin-2-yl]-4-pyridin-3-ylphthalazin-1-one Chemical group C=12C=C(OCC)C(OCC)=CC2=CC(CO)=C(CO)C=1C(C=1)=CC=NC=1N(C(C1=CC=CC=C11)=O)N=C1C1=CC=CN=C1 OEZADIAHVKNQKD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- UVMVAOPVBJYROX-UHFFFAOYSA-N 1-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]-3-morpholin-4-ylquinolin-2-one Chemical group C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C(C=1)=CC=NC=1N(C1=O)C2=CC=CC=C2C=C1N1CCOCC1 UVMVAOPVBJYROX-UHFFFAOYSA-N 0.000 claims description 2
- AEHOWOKEYBPBBY-UHFFFAOYSA-N 1-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]-4-(2-piperidin-1-ylethylamino)quinolin-2-one Chemical group C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C(C=1)=CC=NC=1N(C(C=1)=O)C2=CC=CC=C2C=1NCCN1CCCCC1 AEHOWOKEYBPBBY-UHFFFAOYSA-N 0.000 claims description 2
- KMRIEMBRWALTMW-UHFFFAOYSA-N 1-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]-4-pyridin-4-ylquinolin-2-one Chemical group C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C(C=1)=CC=NC=1N(C(C=1)=O)C2=CC=CC=C2C=1C1=CC=NC=C1 KMRIEMBRWALTMW-UHFFFAOYSA-N 0.000 claims description 2
- IZUATTIJAMMFOW-UHFFFAOYSA-N 2-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]-4-(pyridin-3-ylmethyl)phthalazin-1-one Chemical group C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C(C=1)=CC=NC=1N(C(C1=CC=CC=C11)=O)N=C1CC1=CC=CN=C1 IZUATTIJAMMFOW-UHFFFAOYSA-N 0.000 claims description 2
- ALGYAXVEWGTXDA-UHFFFAOYSA-N 2-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]-4-pyridin-3-ylphthalazin-1-one Chemical group C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C(C=1)=CC=NC=1N(C(C1=CC=CC=C11)=O)N=C1C1=CC=CN=C1 ALGYAXVEWGTXDA-UHFFFAOYSA-N 0.000 claims description 2
- MZWIXTAQIAHGBV-UHFFFAOYSA-N 2-[4-[7-ethoxy-2,3-bis(hydroxymethyl)-6-methoxynaphthalen-1-yl]pyridin-2-yl]-4-pyridin-3-ylphthalazin-1-one Chemical group OCC1=C(CO)C=C2C=C(OC)C(OCC)=CC2=C1C(C=1)=CC=NC=1N(C(C1=CC=CC=C11)=O)N=C1C1=CC=CN=C1 MZWIXTAQIAHGBV-UHFFFAOYSA-N 0.000 claims description 2
- 230000036961 partial effect Effects 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- WXAFHEBLXXIUAA-UHFFFAOYSA-N 2-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]-6,7-dimethoxy-4-pyridin-3-ylphthalazin-1-one Chemical group C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C(C=1)=CC=NC=1N(C(C1=CC(OC)=C(OC)C=C11)=O)N=C1C1=CC=CN=C1 WXAFHEBLXXIUAA-UHFFFAOYSA-N 0.000 claims 1
- 229940000425 combination drug Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 184
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 153
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 104
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 239000002904 solvent Substances 0.000 description 90
- 239000000243 solution Substances 0.000 description 76
- 230000002829 reductive effect Effects 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000010410 layer Substances 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 238000010898 silica gel chromatography Methods 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 238000001816 cooling Methods 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000000725 suspension Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 206010006482 Bronchospasm Diseases 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000007885 bronchoconstriction Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- MRRCJRBPQFRKNX-UHFFFAOYSA-N [4-(2-chloropyridin-4-yl)-3-(hydroxymethyl)-6,7-dimethoxynaphthalen-2-yl]methanol Chemical compound C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C1=CC=NC(Cl)=C1 MRRCJRBPQFRKNX-UHFFFAOYSA-N 0.000 description 9
- 239000003638 chemical reducing agent Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 7
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 7
- ZIFYCOQRDIDBMN-UHFFFAOYSA-N [4-(2-bromopyridin-4-yl)-3-(hydroxymethyl)-6,7-dimethoxynaphthalen-2-yl]methanol Chemical compound C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C1=CC=NC(Br)=C1 ZIFYCOQRDIDBMN-UHFFFAOYSA-N 0.000 description 7
- LOPOFNPBGOUOAH-UHFFFAOYSA-N dimethyl 1-(2-bromopyridin-4-yl)-6,7-dimethoxynaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=CC2=CC(OC)=C(OC)C=C2C=1C1=CC=NC(Br)=C1 LOPOFNPBGOUOAH-UHFFFAOYSA-N 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000427 antigen Substances 0.000 description 6
- 108091007433 antigens Proteins 0.000 description 6
- 102000036639 antigens Human genes 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- QVUVEEKONLXEOI-UHFFFAOYSA-N 1-bromo-2-(dimethoxymethyl)-4,5-dimethoxybenzene Chemical compound COC(OC)C1=CC(OC)=C(OC)C=C1Br QVUVEEKONLXEOI-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- TUMOQBXJOOBHCS-UHFFFAOYSA-N [6,7-diethoxy-4-(2-hydrazinylpyridin-4-yl)naphthalen-2-yl]methanol Chemical compound C=12C=C(OCC)C(OCC)=CC2=CC(CO)=CC=1C1=CC=NC(NN)=C1 TUMOQBXJOOBHCS-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
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- 239000003377 acid catalyst Substances 0.000 description 4
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- 150000008064 anhydrides Chemical class 0.000 description 4
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- 239000003054 catalyst Substances 0.000 description 4
- SQTHNXSOZXQVPF-UHFFFAOYSA-N dimethyl 6,7-dimethoxy-1-pyridin-4-ylnaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=CC2=CC(OC)=C(OC)C=C2C=1C1=CC=NC=C1 SQTHNXSOZXQVPF-UHFFFAOYSA-N 0.000 description 4
- JWFKPRAZXUWSQL-UHFFFAOYSA-N dimethyl 6-hydroxy-7-methoxy-1-pyridin-4-ylnaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=CC2=CC(O)=C(OC)C=C2C=1C1=CC=NC=C1 JWFKPRAZXUWSQL-UHFFFAOYSA-N 0.000 description 4
- 238000011597 hartley guinea pig Methods 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 238000011282 treatment Methods 0.000 description 4
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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- BXKJSYCGIVLVLA-UHFFFAOYSA-N [2-(dimethoxymethyl)-5,6-dimethoxy-3-pyridin-4-ylphenyl]methanol Chemical compound COC(OC)C1=C(CO)C(OC)=C(OC)C=C1C1=CC=NC=C1 BXKJSYCGIVLVLA-UHFFFAOYSA-N 0.000 description 3
- JYKUEROHAVHHNS-UHFFFAOYSA-N [6,7-diethoxy-4-(2-hydrazinylpyridin-4-yl)-3-(hydroxymethyl)naphthalen-2-yl]methanol Chemical compound C=12C=C(OCC)C(OCC)=CC2=CC(CO)=C(CO)C=1C1=CC=NC(NN)=C1 JYKUEROHAVHHNS-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 230000001088 anti-asthma Effects 0.000 description 3
- 239000000924 antiasthmatic agent Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical group I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
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- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 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 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
- ZXPSQKRROVSYQU-UHFFFAOYSA-N methyl 1-(2-bromopyridin-4-yl)-6,7-dimethoxynaphthalene-2-carboxylate Chemical compound COC(=O)C1=CC=C2C=C(OC)C(OC)=CC2=C1C1=CC=NC(Br)=C1 ZXPSQKRROVSYQU-UHFFFAOYSA-N 0.000 description 1
- LKTNTVLSNXCIGY-UHFFFAOYSA-N methyl 4-(2-chloropyridin-4-yl)-6,7-dimethoxynaphthalene-2-carboxylate Chemical compound C=12C=C(OC)C(OC)=CC2=CC(C(=O)OC)=CC=1C1=CC=NC(Cl)=C1 LKTNTVLSNXCIGY-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- VPIDIRFWWJRYED-UHFFFAOYSA-N n'-[4-[2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]pyridin-2-yl]acetohydrazide Chemical compound C=12C=C(OC)C(OC)=CC2=CC(CO)=C(CO)C=1C1=CC=NC(NNC(C)=O)=C1 VPIDIRFWWJRYED-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004648 relaxation of smooth muscle Effects 0.000 description 1
- 230000033904 relaxation of vascular smooth muscle Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14928895 | 1995-06-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962527D0 NO962527D0 (no) | 1996-06-14 |
| NO962527L NO962527L (no) | 1996-12-16 |
| NO310109B1 true NO310109B1 (no) | 2001-05-21 |
Family
ID=15471914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO962527A NO310109B1 (no) | 1995-06-15 | 1996-06-14 | Naftalenderivater og mellomprodukter ved deres fremstilling |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US6005106A (es) |
| EP (1) | EP0748805B1 (es) |
| KR (1) | KR100435247B1 (es) |
| CN (1) | CN1063748C (es) |
| AR (1) | AR002483A1 (es) |
| AT (1) | ATE164843T1 (es) |
| AU (1) | AU706156B2 (es) |
| BG (1) | BG62521B1 (es) |
| BR (1) | BR9602802A (es) |
| CA (1) | CA2178974C (es) |
| DE (1) | DE69600221T2 (es) |
| ES (1) | ES2116131T3 (es) |
| HK (1) | HK1010116A1 (es) |
| HU (1) | HU222340B1 (es) |
| IL (1) | IL118469A (es) |
| MY (1) | MY121606A (es) |
| NO (1) | NO310109B1 (es) |
| RU (1) | RU2129120C1 (es) |
| SG (1) | SG47152A1 (es) |
| TW (1) | TW349098B (es) |
| ZA (1) | ZA964652B (es) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ID19155A (id) * | 1996-12-13 | 1998-06-18 | Tanabe Seiyaku Co | Turunan-turunan piridin, pembuatannya dan intermediet untuk pembuatannya |
| WO2001013953A2 (en) | 1999-08-21 | 2001-03-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Synergistic combination of pde inhibitors and beta 2 adrenoceptor agonist |
| JPH1171351A (ja) * | 1997-08-29 | 1999-03-16 | Ss Pharmaceut Co Ltd | 置換キノロン誘導体及びこれを含有する医薬 |
| US20050147534A1 (en) | 1998-05-05 | 2005-07-07 | Massachusetts Institute Of Technology | Emissive sensors and devices incorporating these sensors |
| WO1999057222A1 (en) | 1998-05-05 | 1999-11-11 | Massachusetts Institute Of Technology | Emissive polymers and devices incorporating these polymers |
| CN1520313A (zh) * | 2001-05-23 | 2004-08-11 | ������ҩ��ʽ���� | 一种加速骨折愈合的组合物 |
| CA2447618A1 (en) * | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | A composition for regenerative treatment of cartilage disease |
| TWI221838B (en) | 2001-08-09 | 2004-10-11 | Tanabe Seiyaku Co | Pyrazinoisoquinoline compound or naphthalene compound |
| EP1463714A4 (en) * | 2001-12-10 | 2005-10-19 | Amgen Inc | VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS |
| WO2003057689A1 (en) * | 2002-01-02 | 2003-07-17 | Fujisawa Pharmaceutical Co., Ltd. | Aminopyrimidine compounds, processes for their preparation and pharmaceutical compositions containing them |
| PL375552A1 (en) * | 2002-05-22 | 2005-11-28 | Amgen Inc. | Vanilloid receptor ligands and their medical applications |
| EP1717220A3 (en) * | 2002-08-08 | 2007-08-22 | Amgen, Inc | Vanilloid receptor ligands and their use in treatments |
| CA2517888C (en) | 2003-03-14 | 2012-05-01 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic derivatives and drugs containing the same as the active ingredient |
| BRPI0409229A (pt) | 2003-04-01 | 2006-03-28 | Applied Research Systems | inibidores das fosfodiesterases na infertilidade |
| KR20060030467A (ko) * | 2003-05-16 | 2006-04-10 | 더 유니버시티 오브 시카고 | 광학 분류 방법 및 장치 |
| EP1670794A2 (en) * | 2003-09-30 | 2006-06-21 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| WO2005077938A1 (en) | 2004-02-11 | 2005-08-25 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| MY139645A (en) * | 2004-02-11 | 2009-10-30 | Amgen Inc | Vanilloid receptor ligands and their use in treatments |
| RU2409565C2 (ru) | 2004-09-13 | 2011-01-20 | Оно Фармасьютикал Ко., Лтд. | Азотистые гетероциклические производные и лекарственные средства, содержащие их в качестве активного ингредиента |
| US8617819B2 (en) | 2004-09-17 | 2013-12-31 | Massachusetts Institute Of Technology | Polymers for analyte detection |
| TWI339578B (en) | 2004-10-29 | 2011-04-01 | Mitsubishi Tanabe Pharma Corp | Use of a pyridine compound for the preparation of a medicament for the treatment of skin lesions |
| WO2006089311A1 (en) * | 2005-02-15 | 2006-08-24 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US20060235036A1 (en) * | 2005-04-15 | 2006-10-19 | Doherty Elizabeth M | Vanilloid receptor ligands and their use in treatments |
| WO2007040238A1 (ja) | 2005-10-04 | 2007-04-12 | Mitsubishi Tanabe Pharma Corporation | 光学活性４－ヒドロキシ－１，２，３，４－テトラヒドロキノリン化合物の製法 |
| PT1944291E (pt) | 2005-10-04 | 2012-08-10 | Mitsubishi Tanabe Pharma Corp | Álcool cíclico opticamente activo e método para a sua produção |
| JP4767968B2 (ja) * | 2005-10-05 | 2011-09-07 | 田辺三菱製薬株式会社 | 皮膚炎治療剤 |
| JPWO2007105637A1 (ja) | 2006-03-10 | 2009-07-30 | 小野薬品工業株式会社 | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| WO2007112347A1 (en) * | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8283423B2 (en) | 2006-09-29 | 2012-10-09 | Massachusetts Institute Of Technology | Polymer synthetic technique |
| US8802447B2 (en) | 2006-10-05 | 2014-08-12 | Massachusetts Institute Of Technology | Emissive compositions with internal standard and related techniques |
| US20090215189A1 (en) | 2006-10-27 | 2009-08-27 | Massachusetts Institute Of Technology | Sensor of species including toxins and chemical warfare agents |
| EP1958947A1 (en) * | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
| JP2010524857A (ja) * | 2007-04-10 | 2010-07-22 | ザ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・ペンシルバニア | フェン−ナフタレン及びフェン−キノリン誘導体、及びアミロイドプラークに結合させ、そして造影するための使用 |
| US9125807B2 (en) | 2007-07-09 | 2015-09-08 | Incept Llc | Adhesive hydrogels for ophthalmic drug delivery |
| ES2659458T3 (es) * | 2011-06-28 | 2018-03-15 | Mitsubishi Tanabe Pharma Corporation | Compuestos de naftaleno para tratar el prurito |
| US9181217B2 (en) | 2011-08-25 | 2015-11-10 | Mitsubishi Tanabe Pharma Corporation | Method for producing optically active naphthalene compound |
| US11970440B1 (en) | 2023-10-30 | 2024-04-30 | King Faisal University | 8-(3-chlorobenzylideneamino)naphthalene-1,3-disulfonic acid as an antioxidant compound |
| US11932593B1 (en) | 2023-10-31 | 2024-03-19 | King Faisal University | 8-(3-bromobenzylideneamino)naphthalene-1,3-disulfonic acid as an antioxidant compound |
| US11987543B1 (en) | 2023-10-31 | 2024-05-21 | King Faisal University | 8-(4-bromobenzylideneamino)naphthalene-1,3-disulfonic acid as an antioxidant compound |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3042156B2 (ja) * | 1992-02-20 | 2000-05-15 | 田辺製薬株式会社 | ナフタレン誘導体、その製法及びその合成中間体 |
| US5342841A (en) * | 1992-03-12 | 1994-08-30 | Kyowa Hakko Kogyo Co., Ltd. | Xanthine derivatives |
| DE59609705D1 (de) * | 1995-03-03 | 2002-10-31 | Rolic Ag Zug | Photovernetzbare Naphthylderivate |
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1996
- 1996-05-30 IL IL11846996A patent/IL118469A/xx not_active IP Right Cessation
- 1996-05-31 TW TW085106502A patent/TW349098B/zh not_active IP Right Cessation
- 1996-06-03 MY MYPI96002135A patent/MY121606A/en unknown
- 1996-06-04 DE DE69600221T patent/DE69600221T2/de not_active Expired - Lifetime
- 1996-06-04 AT AT96304033T patent/ATE164843T1/de active
- 1996-06-04 ES ES96304033T patent/ES2116131T3/es not_active Expired - Lifetime
- 1996-06-04 AU AU54693/96A patent/AU706156B2/en not_active Expired
- 1996-06-04 EP EP96304033A patent/EP0748805B1/en not_active Expired - Lifetime
- 1996-06-11 SG SG1996010041A patent/SG47152A1/en unknown
- 1996-06-12 BG BG100656A patent/BG62521B1/bg unknown
- 1996-06-14 CA CA002178974A patent/CA2178974C/en not_active Expired - Lifetime
- 1996-06-14 AR ARP960103158A patent/AR002483A1/es not_active Application Discontinuation
- 1996-06-14 NO NO962527A patent/NO310109B1/no not_active IP Right Cessation
- 1996-06-14 RU RU96112130A patent/RU2129120C1/ru active
- 1996-06-14 HU HU9601652A patent/HU222340B1/hu active IP Right Grant
- 1996-06-14 BR BRPI9602802-5A patent/BR9602802A/pt not_active IP Right Cessation
- 1996-06-14 US US08/663,991 patent/US6005106A/en not_active Expired - Lifetime
- 1996-06-15 KR KR1019960021677A patent/KR100435247B1/ko active IP Right Grant
- 1996-06-15 ZA ZA964652A patent/ZA964652B/xx unknown
- 1996-06-17 CN CN96106608A patent/CN1063748C/zh not_active Expired - Lifetime
-
1998
- 1998-07-02 US US09/109,099 patent/US5969140A/en not_active Expired - Lifetime
- 1998-09-24 HK HK98110940A patent/HK1010116A1/xx not_active IP Right Cessation
- 1998-12-01 US US09/201,820 patent/US6214996B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HU9601652D0 (en) | 1996-08-28 |
| ATE164843T1 (de) | 1998-04-15 |
| DE69600221T2 (de) | 1998-08-06 |
| CN1063748C (zh) | 2001-03-28 |
| CN1142497A (zh) | 1997-02-12 |
| US6214996B1 (en) | 2001-04-10 |
| HK1010116A1 (en) | 1999-06-11 |
| TW349098B (en) | 1999-01-01 |
| ES2116131T3 (es) | 1998-07-01 |
| AU5469396A (en) | 1997-01-02 |
| KR100435247B1 (ko) | 2004-09-10 |
| CA2178974A1 (en) | 1996-12-16 |
| BG62521B1 (bg) | 2000-01-31 |
| ZA964652B (en) | 1996-12-12 |
| US6005106A (en) | 1999-12-21 |
| HUP9601652A1 (en) | 1997-09-29 |
| NO962527L (no) | 1996-12-16 |
| CA2178974C (en) | 2006-06-06 |
| SG47152A1 (en) | 1998-03-20 |
| MY121606A (en) | 2006-02-28 |
| EP0748805A1 (en) | 1996-12-18 |
| DE69600221D1 (de) | 1998-05-14 |
| BG100656A (en) | 1997-09-30 |
| NO962527D0 (no) | 1996-06-14 |
| KR970001343A (ko) | 1997-01-24 |
| BR9602802A (pt) | 1998-10-06 |
| US5969140A (en) | 1999-10-19 |
| AR002483A1 (es) | 1998-03-25 |
| RU2129120C1 (ru) | 1999-04-20 |
| HU222340B1 (hu) | 2003-06-28 |
| AU706156B2 (en) | 1999-06-10 |
| IL118469A0 (en) | 1996-09-12 |
| EP0748805B1 (en) | 1998-04-08 |
| IL118469A (en) | 2000-08-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |