KR20180083323A - N-설포닐화 피라졸로[3,4-b]피리딘-6-카복스아미드 및 사용 방법 - Google Patents

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Publication number

KR20180083323A

KR20180083323A KR1020187012937A KR20187012937A KR20180083323A KR 20180083323 A KR20180083323 A KR 20180083323A KR 1020187012937 A KR1020187012937 A KR 1020187012937A KR 20187012937 A KR20187012937 A KR 20187012937A KR 20180083323 A KR20180083323 A KR 20180083323A

Authority

KR

South Korea

Prior art keywords

pyrazolo

pyridine

carboxamide

cyclobutyl

methanesulfonyl

Prior art date

2015-10-09

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.)

Ceased

Links

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• 238000000034 method Methods 0.000 title claims description 95
• JKFBIZUZFKODCG-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine-6-carboxamide Chemical compound N1C(C(=O)N)=CC=C2C=NN=C21 JKFBIZUZFKODCG-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 214
• 150000003839 salts Chemical class 0.000 claims abstract description 85
• 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 60
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 30
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 808
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 472
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 285
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 232
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 212
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 190
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 154
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 141
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 114
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 95
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 94
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 239000001257 hydrogen Substances 0.000 claims description 83
• UDKVMASCRFDIIP-UHFFFAOYSA-N 1,7,9,11-tetrahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1CCC(C=C(C(=C3O)C(O)=O)C)=C3C1=C2 UDKVMASCRFDIIP-UHFFFAOYSA-N 0.000 claims description 73
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 67
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 57
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 52
• 239000003814 drug Substances 0.000 claims description 50
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 45
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 43
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
• 230000015572 biosynthetic process Effects 0.000 claims description 39
• 238000003786 synthesis reaction Methods 0.000 claims description 38
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 36
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 33
• 125000000623 heterocyclic group Chemical group 0.000 claims description 33
• 238000011282 treatment Methods 0.000 claims description 28
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 26
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 26
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 25
• 229940124597 therapeutic agent Drugs 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 17
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 239000005711 Benzoic acid Substances 0.000 claims description 15
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
• 235000010233 benzoic acid Nutrition 0.000 claims description 15
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 15
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 15
• 125000004043 oxo group Chemical group O=* 0.000 claims description 15
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 13
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 11
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 9
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 8
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 239000003623 enhancer Substances 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 239000003381 stabilizer Substances 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims description 5
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• SDJBJYRUUXSRMT-UHFFFAOYSA-N C(#N)C1(CCN(CC1)C)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2OC(C)C)C1CCCCC1 Chemical compound C(#N)C1(CCN(CC1)C)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2OC(C)C)C1CCCCC1 SDJBJYRUUXSRMT-UHFFFAOYSA-N 0.000 claims description 2
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