TW445258B - Quinolinone derivative and anti-cllergic agent with said quinolinone derivative as the active ingredient - Google Patents

Info

Publication number

TW445258B

TW445258B TW086100527A TW86100527A TW445258B TW 445258 B TW445258 B TW 445258B TW 086100527 A TW086100527 A TW 086100527A TW 86100527 A TW86100527 A TW 86100527A TW 445258 B TW445258 B TW 445258B

Authority

TW

Taiwan

Prior art keywords

quinolinone

methyl

nitro

amino

hydroxy

Prior art date

1996-01-17

Links

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• 239000004480 active ingredient Substances 0.000 title claims abstract description 18
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title description 51
• 150000003839 salts Chemical class 0.000 claims abstract description 93
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 71
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 60
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 54
• DXKZKYOSLNTYKH-UHFFFAOYSA-N 7-amino-1h-quinolin-2-one Chemical class C1=CC(=O)NC2=CC(N)=CC=C21 DXKZKYOSLNTYKH-UHFFFAOYSA-N 0.000 claims abstract description 49
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
• ZZVKOBBRQRBYRF-UHFFFAOYSA-N 7-nitro-1h-quinolin-2-one Chemical class C1=CC(=O)NC2=CC([N+](=O)[O-])=CC=C21 ZZVKOBBRQRBYRF-UHFFFAOYSA-N 0.000 claims abstract description 11
• -1 alkylfluorenyl Chemical group 0.000 claims description 388
• 238000011049 filling Methods 0.000 claims description 115
• 230000002079 cooperative effect Effects 0.000 claims description 57
• 238000000034 method Methods 0.000 claims description 52
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 49
• 125000004432 carbon atom Chemical group C* 0.000 claims description 36
• 235000017803 cinnamon Nutrition 0.000 claims description 16
• 230000003266 anti-allergic effect Effects 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 4
• 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 241000894007 species Species 0.000 claims description 2
• 241000723347 Cinnamomum Species 0.000 claims 11
• 239000004382 Amylase Substances 0.000 claims 1
• 102000013142 Amylases Human genes 0.000 claims 1
• 108010065511 Amylases Proteins 0.000 claims 1
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• 235000019418 amylase Nutrition 0.000 claims 1
• PCMORTLOPMLEFB-ONEGZZNKSA-M trans-sinapate Chemical compound COC1=CC(\C=C\C([O-])=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-M 0.000 claims 1
• 239000000043 antiallergic agent Substances 0.000 abstract description 16
• 125000002252 acyl group Chemical group 0.000 abstract 2
• 150000001875 compounds Chemical class 0.000 description 166
• 125000005924 2-methylpentyloxy group Chemical group 0.000 description 73
• 235000002639 sodium chloride Nutrition 0.000 description 69
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 48
• 206010020751 Hypersensitivity Diseases 0.000 description 42
• 238000005160 1H NMR spectroscopy Methods 0.000 description 37
• 230000007815 allergy Effects 0.000 description 35
• 239000000203 mixture Substances 0.000 description 33
• 238000004458 analytical method Methods 0.000 description 31
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
• 229940126214 compound 3 Drugs 0.000 description 28
• 229940125782 compound 2 Drugs 0.000 description 27
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 24
• VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 22
• 229930185107 quinolinone Natural products 0.000 description 22
• 125000001424 substituent group Chemical group 0.000 description 22
• 239000003826 tablet Substances 0.000 description 22
• 238000012360 testing method Methods 0.000 description 22
• 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 18
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 238000000921 elemental analysis Methods 0.000 description 15
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 15
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• 238000005481 NMR spectroscopy Methods 0.000 description 13
• 239000010949 copper Substances 0.000 description 13
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 230000005764 inhibitory process Effects 0.000 description 12
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
• 229920000609 methyl cellulose Polymers 0.000 description 12
• 235000010981 methylcellulose Nutrition 0.000 description 12
• 239000001923 methylcellulose Substances 0.000 description 12
• 239000001257 hydrogen Substances 0.000 description 11
• 229910052739 hydrogen Inorganic materials 0.000 description 11
• 235000015170 shellfish Nutrition 0.000 description 11
• 239000002168 alkylating agent Substances 0.000 description 10
• 229940100198 alkylating agent Drugs 0.000 description 10
• 208000026935 allergic disease Diseases 0.000 description 10
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• 239000003981 vehicle Substances 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 125000003277 amino group Chemical group 0.000 description 9
• 229920002678 cellulose Polymers 0.000 description 9
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• 235000010980 cellulose Nutrition 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 229910052802 copper Inorganic materials 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 239000000543 intermediate Substances 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 239000000454 talc Substances 0.000 description 9
• 229910052623 talc Inorganic materials 0.000 description 9
• 235000012222 talc Nutrition 0.000 description 9
• KWMUSDDZNYHIBR-UHFFFAOYSA-N 3-amino-1h-quinolin-2-one Chemical class C1=CC=C2NC(=O)C(N)=CC2=C1 KWMUSDDZNYHIBR-UHFFFAOYSA-N 0.000 description 8
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 238000002156 mixing Methods 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical group CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 7
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
• 108010010803 Gelatin Proteins 0.000 description 7
• 241000124008 Mammalia Species 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 208000010668 atopic eczema Diseases 0.000 description 7
• 239000008273 gelatin Substances 0.000 description 7
• 229920000159 gelatin Polymers 0.000 description 7
• 235000019322 gelatine Nutrition 0.000 description 7
• 235000011852 gelatine desserts Nutrition 0.000 description 7
• 239000008187 granular material Substances 0.000 description 7
• 150000002431 hydrogen Chemical group 0.000 description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
• 239000012044 organic layer Substances 0.000 description 7
• 239000013641 positive control Substances 0.000 description 7
• 230000004044 response Effects 0.000 description 7
• QYEMNJMSULGQRD-UHFFFAOYSA-N 1-methyl-2-quinolone Chemical compound C1=CC=C2C=CC(=O)N(C)C2=C1 QYEMNJMSULGQRD-UHFFFAOYSA-N 0.000 description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• 239000001273 butane Substances 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 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 6
• 230000009610 hypersensitivity Effects 0.000 description 6
• 238000009434 installation Methods 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 235000019359 magnesium stearate Nutrition 0.000 description 6
• 238000012856 packing Methods 0.000 description 6
• 230000000144 pharmacologic effect Effects 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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• 150000003431 steroids Chemical class 0.000 description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
• 244000223760 Cinnamomum zeylanicum Species 0.000 description 5
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• 241000699670 Mus sp. Species 0.000 description 5
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• 230000000172 allergic effect Effects 0.000 description 5
• 230000037396 body weight Effects 0.000 description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 5
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• 231100000252 nontoxic Toxicity 0.000 description 3
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