JP5807058B2 - 二機能キノリン誘導体 - Google Patents

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Publication number

JP5807058B2

JP5807058B2 JP2013510204A JP2013510204A JP5807058B2 JP 5807058 B2 JP5807058 B2 JP 5807058B2 JP 2013510204 A JP2013510204 A JP 2013510204A JP 2013510204 A JP2013510204 A JP 2013510204A JP 5807058 B2 JP5807058 B2 JP 5807058B2

Authority

JP

Japan

Prior art keywords

amino

phenyl

compound

pharmaceutically acceptable

hydroxy

Prior art date

2010-05-10

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 230000001588 bifunctional effect Effects 0.000 title description 9
• 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 584
• 239000000203 mixture Substances 0.000 claims description 195
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 130
• 150000003839 salts Chemical class 0.000 claims description 119
• 238000011282 treatment Methods 0.000 claims description 111
• -1 8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl Chemical group 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 79
• 238000000034 method Methods 0.000 claims description 76
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 65
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• 206010006451 bronchitis Diseases 0.000 claims description 52
• 125000004450 alkenylene group Chemical group 0.000 claims description 50
• 125000004419 alkynylene group Chemical group 0.000 claims description 50
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
• 125000005843 halogen group Chemical group 0.000 claims description 50
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 48
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 45
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• 125000006413 ring segment Chemical group 0.000 claims description 43
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• 125000001424 substituent group Chemical group 0.000 claims description 39
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• 201000009890 sinusitis Diseases 0.000 claims description 35
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 33
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• GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 3
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
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• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
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• 239000000460 chlorine Substances 0.000 description 29
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 27
• 239000011734 sodium Substances 0.000 description 27
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
• 238000012360 testing method Methods 0.000 description 25
• 125000002619 bicyclic group Chemical group 0.000 description 24
• 125000000623 heterocyclic group Chemical group 0.000 description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
• 239000003921 oil Substances 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
• 239000000443 aerosol Substances 0.000 description 23
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 210000004072 lung Anatomy 0.000 description 21
• WDCOJSGXSPGNFK-UHFFFAOYSA-N 8-aminooctan-1-ol Chemical compound NCCCCCCCCO WDCOJSGXSPGNFK-UHFFFAOYSA-N 0.000 description 20
• 239000004480 active ingredient Substances 0.000 description 20
• 238000000746 purification Methods 0.000 description 20
• 229940079593 drug Drugs 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
• 239000000725 suspension Substances 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• 239000002253 acid Substances 0.000 description 17
• 125000002993 cycloalkylene group Chemical group 0.000 description 17
• 229910052739 hydrogen Inorganic materials 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• 0 Cc1cc(Sc2cc(C(*c(cc3)ccc3-c3ccc(CCCC(OC)=O)cc3)=O)ccc2)cc2c1ncc(C(N)=O)c2Nc1cc(OC)ccc1 Chemical compound Cc1cc(Sc2cc(C(*c(cc3)ccc3-c3ccc(CCCC(OC)=O)cc3)=O)ccc2)cc2c1ncc(C(N)=O)c2Nc1cc(OC)ccc1 0.000 description 16
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• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
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• 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 14
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• IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
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• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
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