RU2724345C2 - N-СУЛЬФОНИЛИРОВАННЫЕ ПИРАЗОЛО[3,4-b]ПИРИДИН-6-КАРБОКСАМИДЫ И СПОСОБ ИХ ПРИМЕНЕНИЯ - Google Patents

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Publication number

RU2724345C2

RU2724345C2 RU2018115722A RU2018115722A RU2724345C2 RU 2724345 C2 RU2724345 C2 RU 2724345C2 RU 2018115722 A RU2018115722 A RU 2018115722A RU 2018115722 A RU2018115722 A RU 2018115722A RU 2724345 C2 RU2724345 C2 RU 2724345C2

Authority

RU

Russia

Prior art keywords

pyrazolo

carboxamide

pyridin

phenyl

cyclobutyl

Prior art date

2015-10-09

Links

• Espacenet
• Global Dossier
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• JKFBIZUZFKODCG-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine-6-carboxamide Chemical class N1C(C(=O)N)=CC=C2C=NN=C21 JKFBIZUZFKODCG-UHFFFAOYSA-N 0.000 title claims 2
• 238000000034 method Methods 0.000 title description 111
• 150000001875 compounds Chemical class 0.000 claims abstract description 270
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 244
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 127
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 86
• 239000001257 hydrogen Substances 0.000 claims abstract description 86
• 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 58
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 58
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 48
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 46
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 41
• 125000001424 substituent group Chemical group 0.000 claims abstract description 41
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 40
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 39
• 230000000694 effects Effects 0.000 claims abstract description 35
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 33
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
• 150000002367 halogens Chemical class 0.000 claims abstract description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 18
• 208000035475 disorder Diseases 0.000 claims abstract description 16
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 16
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 15
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
• 239000012634 fragment Substances 0.000 claims abstract description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
• HEYSFDAMRDTCJM-UUOKFMHZSA-N [(2r,3s,4r,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl phosphono hydrogen phosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O HEYSFDAMRDTCJM-UUOKFMHZSA-N 0.000 claims abstract description 6
• 229910052702 rhenium Inorganic materials 0.000 claims abstract description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 4
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims abstract 2
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims abstract 2
• -1 ethanesulfonyl Chemical group 0.000 claims description 311
• 125000005466 alkylenyl group Chemical group 0.000 claims description 204
• 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 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 43
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 40
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 38
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 25
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 239000003937 drug carrier Substances 0.000 claims description 12
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 12
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 8
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• 102000034356 gene-regulatory proteins Human genes 0.000 claims description 4
• 108091006104 gene-regulatory proteins Proteins 0.000 claims description 4
• 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 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• RTWUWAJYMQYSRX-UHFFFAOYSA-N C1(CCC1)C1=NN(C2=NC(=CC(=C21)N1CCC(CC1)N1CCC(CC1)OC)C(=O)NS(NC)(=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(NC)(=O)=O)C1=CC=C(C=C1)F RTWUWAJYMQYSRX-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
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])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
• ZGDPLFLKAAHUNT-UHFFFAOYSA-N C(#N)C1(CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C(C)C)C1CCCCC1)C Chemical compound C(#N)C1(CCN(CC1)C1=CC=C(C=N1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C(C)C)C1CCCCC1)C ZGDPLFLKAAHUNT-UHFFFAOYSA-N 0.000 claims description 2
• CTYIYWGTRPWCJA-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C(C)C)C1=CC=C(C=C1)F Chemical compound C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C(C)C)C1=CC=C(C=C1)F CTYIYWGTRPWCJA-UHFFFAOYSA-N 0.000 claims description 2
• VFXUCFYREUJPRG-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C1CCC1)C1=CC=CC=C1 Chemical compound C(#N)C1CCN(CC1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C1CCC1)C1=CC=CC=C1 VFXUCFYREUJPRG-UHFFFAOYSA-N 0.000 claims description 2
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• CFSAVZFLPCFYPQ-UHFFFAOYSA-N C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C(C)C)C1=CC(=CC(=C1)F)F Chemical compound C(#N)C1CCN(CC1)C1=CC=C(C=C1)C1=C2C(=NC(=C1)C(=O)NS(=O)(=O)C)N(N=C2C(C)C)C1=CC(=CC(=C1)F)F CFSAVZFLPCFYPQ-UHFFFAOYSA-N 0.000 claims description 2
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