TWI464168B - 1ｈ－咪唑并〔４，５－ｃ〕喹啉酮衍生物 - Google Patents

Info

Publication number

TWI464168B

TWI464168B TW099117977A TW99117977A TWI464168B TW I464168 B TWI464168 B TW I464168B TW 099117977 A TW099117977 A TW 099117977A TW 99117977 A TW99117977 A TW 99117977A TW I464168 B TWI464168 B TW I464168B

Authority

TW

Taiwan

Prior art keywords

group

methyl

substituted

methoxy

lower alkyl

Prior art date

2009-06-04

Links

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• IQYPSFAWXDKDBA-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-c]quinolin-2-one Chemical class C1=CC=CC2=C(NC(=O)N3)C3=CN=C21 IQYPSFAWXDKDBA-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 422
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 76
• 201000010099 disease Diseases 0.000 claims description 74
• 150000003839 salts Chemical class 0.000 claims description 59
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• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 230000002062 proliferating effect Effects 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 12
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• 238000004519 manufacturing process Methods 0.000 claims description 7
• 230000001105 regulatory effect Effects 0.000 claims description 7
• 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 6
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• 239000003937 drug carrier Substances 0.000 claims description 6
• 206010004146 Basal cell carcinoma Diseases 0.000 claims description 4
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
• 206010039710 Scleroderma Diseases 0.000 claims description 4
• 230000004064 dysfunction Effects 0.000 claims description 4
• 210000002950 fibroblast Anatomy 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• 210000003734 kidney Anatomy 0.000 claims description 4
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• 230000009826 neoplastic cell growth Effects 0.000 claims description 4
• 210000000496 pancreas Anatomy 0.000 claims description 4
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• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• 201000007815 Bannayan-Riley-Ruvalcaba syndrome Diseases 0.000 claims description 3
• 208000012609 Cowden disease Diseases 0.000 claims description 3
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• 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
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• 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
• 208000035269 cancer or benign tumor Diseases 0.000 claims 1
• 201000005202 lung cancer Diseases 0.000 claims 1
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• 201000001275 rectum cancer Diseases 0.000 claims 1
• 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
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• 125000000217 alkyl group Chemical group 0.000 description 355
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• 125000001424 substituent group Chemical group 0.000 description 86
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
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• 150000002431 hydrogen Chemical class 0.000 description 28
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
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• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 27
• 125000006413 ring segment Chemical group 0.000 description 27
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 24
• 229910052757 nitrogen Inorganic materials 0.000 description 24
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
• 239000000243 solution Substances 0.000 description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 23
• 125000003342 alkenyl group Chemical group 0.000 description 23
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 23
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 22
• 125000001153 fluoro group Chemical group F* 0.000 description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 21
• 125000001309 chloro group Chemical group Cl* 0.000 description 21
• 125000005842 heteroatom Chemical group 0.000 description 21
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 21
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• 241000208199 Buxus sempervirens Species 0.000 description 19
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 17
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