TWI720032B - Ｎ－磺醯化吡唑并﹝３，４－ｂ﹞吡啶－６－甲醯胺及其使用方法 - Google Patents

Info

Publication number

TWI720032B

TWI720032B TW105132676A TW105132676A TWI720032B TW I720032 B TWI720032 B TW I720032B TW 105132676 A TW105132676 A TW 105132676A TW 105132676 A TW105132676 A TW 105132676A TW I720032 B TWI720032 B TW I720032B

Authority

TW

Taiwan

Prior art keywords

pyrazolo

pyridine

phenyl

cyclobutyl

formamide

Prior art date

2015-10-09

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title description 118
• 150000001875 compounds Chemical class 0.000 claims abstract description 282
• 150000003839 salts Chemical class 0.000 claims abstract description 87
• 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 57
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 30
• 238000011282 treatment Methods 0.000 claims abstract description 29
• -1 ethanesulfonyl Chemical group 0.000 claims description 266
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 149
• 239000000203 mixture Substances 0.000 claims description 110
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 239000001257 hydrogen Substances 0.000 claims description 83
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 83
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 74
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 73
• 125000002950 monocyclic group Chemical group 0.000 claims description 70
• 125000000623 heterocyclic group Chemical group 0.000 claims description 69
• 239000003814 drug Substances 0.000 claims description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims description 55
• 229910052760 oxygen Inorganic materials 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
• 229910052717 sulfur Inorganic materials 0.000 claims description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims description 39
• 125000005842 heteroatom Chemical group 0.000 claims description 39
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 238000006467 substitution reaction Methods 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 30
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 27
• 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 27
• 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 25
• 239000003795 chemical substances by application Substances 0.000 claims description 23
• 150000003857 carboxamides Chemical class 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000001188 haloalkyl group Chemical group 0.000 claims description 21
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 18
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 239000003937 drug carrier Substances 0.000 claims description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 230000003321 amplification Effects 0.000 claims description 8
• 238000003199 nucleic acid amplification method Methods 0.000 claims description 8
• 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 8
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• NMWGIPMCPKCUIW-UHFFFAOYSA-N C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)COC)C(=O)NS(=O)(=O)C)C1=CC=C(C=C1)F Chemical compound C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)COC)C(=O)NS(=O)(=O)C)C1=CC=C(C=C1)F NMWGIPMCPKCUIW-UHFFFAOYSA-N 0.000 claims description 4
• WCGYDRKYWBLLKE-UHFFFAOYSA-N C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)N1CCC(CC1)OC)C(=O)NS(=O)(=O)C)C1=CC=C(C=C1)F Chemical compound C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)N1CCC(CC1)OC)C(=O)NS(=O)(=O)C)C1=CC=C(C=C1)F WCGYDRKYWBLLKE-UHFFFAOYSA-N 0.000 claims description 4
• DHLJRIROJYHJQA-UHFFFAOYSA-N C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)N1CCN(CC1)C1CC1)C(=O)NS(=O)(=O)C)C1=CC=CC=C1 Chemical compound C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)N1CCN(CC1)C1CC1)C(=O)NS(=O)(=O)C)C1=CC=CC=C1 DHLJRIROJYHJQA-UHFFFAOYSA-N 0.000 claims description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
• JPIAJLPRTOWAEC-UHFFFAOYSA-N C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)N1CCC(CC1)OC)C(=O)NS(N(C)C)(=O)=O)C1=CC=C(C=C1)F Chemical compound C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)N1CCC(CC1)OC)C(=O)NS(N(C)C)(=O)=O)C1=CC=C(C=C1)F JPIAJLPRTOWAEC-UHFFFAOYSA-N 0.000 claims description 3
• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 2
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 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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