KR20170053638A - 예를 들면 섬유화 질환의 치료를 위한 알파 v 베타 6 인테그린 길항제로서 나프티리딘 유도체 - Google Patents

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Publication number

KR20170053638A

KR20170053638A KR1020177007736A KR20177007736A KR20170053638A KR 20170053638 A KR20170053638 A KR 20170053638A KR 1020177007736 A KR1020177007736 A KR 1020177007736A KR 20177007736 A KR20177007736 A KR 20177007736A KR 20170053638 A KR20170053638 A KR 20170053638A

Authority

KR

South Korea

Prior art keywords

compound

methyl

mmol

pharmaceutically acceptable

formula

Prior art date

2014-09-26

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.)

Withdrawn

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 37
• 201000010099 disease Diseases 0.000 title claims description 34
• 238000011282 treatment Methods 0.000 title claims description 33
• 230000003176 fibrotic effect Effects 0.000 title claims description 6
• 239000005557 antagonist Substances 0.000 title description 24
• 108010021309 integrin beta6 Proteins 0.000 title 1
• 150000005054 naphthyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 212
• -1 di-substituted pyrazole Chemical class 0.000 claims abstract description 158
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 25
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 8
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 5
• 150000003839 salts Chemical class 0.000 claims description 88
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 46
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 40
• 238000000034 method Methods 0.000 claims description 37
• 239000008194 pharmaceutical composition Substances 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• 238000002560 therapeutic procedure Methods 0.000 claims description 14
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 13
• 206010016654 Fibrosis Diseases 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 13
• 230000004761 fibrosis Effects 0.000 claims description 13
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 12
• 229940123038 Integrin antagonist Drugs 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
• 230000004060 metabolic process Effects 0.000 claims description 6
• 102000005962 receptors Human genes 0.000 claims description 6
• 108020003175 receptors Proteins 0.000 claims description 6
• 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 claims description 4
• 230000008485 antagonism Effects 0.000 claims description 3
• 230000009286 beneficial effect Effects 0.000 claims 2
• 150000003852 triazoles Chemical class 0.000 claims 1
• 239000000203 mixture Substances 0.000 description 93
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 92
• 239000000243 solution Substances 0.000 description 85
• 239000000543 intermediate Substances 0.000 description 82
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 80
• 235000002639 sodium chloride Nutrition 0.000 description 78
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 42
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 33
• 108010044426 integrins Proteins 0.000 description 32
• 102000006495 integrins Human genes 0.000 description 32
• 238000004296 chiral HPLC Methods 0.000 description 31
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• 235000019439 ethyl acetate Nutrition 0.000 description 29
• 239000002904 solvent Substances 0.000 description 28
• 238000006243 chemical reaction Methods 0.000 description 27
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 27
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
• 230000002829 reductive effect Effects 0.000 description 25
• 239000007787 solid Substances 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• 229910052757 nitrogen Inorganic materials 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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• 239000000843 powder Substances 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• 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 16
• 239000008101 lactose Substances 0.000 description 16
• 229960001375 lactose Drugs 0.000 description 16
• 125000000217 alkyl group Chemical group 0.000 description 15
• 239000002585 base Substances 0.000 description 15
• 239000012530 fluid Substances 0.000 description 15
• 239000000741 silica gel Substances 0.000 description 15
• 229910002027 silica gel Inorganic materials 0.000 description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 13
• 238000009472 formulation Methods 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
• 102000004887 Transforming Growth Factor beta Human genes 0.000 description 12
• 108090001012 Transforming Growth Factor beta Proteins 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 235000019441 ethanol Nutrition 0.000 description 12
• 238000001819 mass spectrum Methods 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• 239000002245 particle Substances 0.000 description 12
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 150000001413 amino acids Chemical class 0.000 description 11
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• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
• 229940024606 amino acid Drugs 0.000 description 10
• 235000001014 amino acid Nutrition 0.000 description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
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• IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 9
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 9
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• 239000000377 silicon dioxide Substances 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 239000004480 active ingredient Substances 0.000 description 8
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
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