KR20150130311A - 야누스 키나제 억제제로서의 n-(2-시아노 헤테로시클릴)피라졸로 피리돈 - Google Patents

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Publication number

KR20150130311A

KR20150130311A KR1020157025519A KR20157025519A KR20150130311A KR 20150130311 A KR20150130311 A KR 20150130311A KR 1020157025519 A KR1020157025519 A KR 1020157025519A KR 20157025519 A KR20157025519 A KR 20157025519A KR 20150130311 A KR20150130311 A KR 20150130311A

Authority

KR

South Korea

Prior art keywords

alkyl

amino

pyridin

pyran

dihydro

Prior art date

2013-03-19

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Withdrawn

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• 229940122245 Janus kinase inhibitor Drugs 0.000 title abstract description 3
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 121
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
• 201000010099 disease Diseases 0.000 claims abstract description 21
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 230000001404 mediated effect Effects 0.000 claims abstract description 11
• 102000042838 JAK family Human genes 0.000 claims abstract description 6
• 108091082332 JAK family Proteins 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 490
• -1 amino (oxy) Chemical class 0.000 claims description 266
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 129
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 98
• RLZJFTOYCVIYLE-UHFFFAOYSA-N oxane-4-carbonitrile Chemical compound N#CC1CCOCC1 RLZJFTOYCVIYLE-UHFFFAOYSA-N 0.000 claims description 83
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 125000001072 heteroaryl group Chemical group 0.000 claims description 55
• 125000003118 aryl group Chemical group 0.000 claims description 54
• 125000001424 substituent group Chemical group 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 48
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 37
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 36
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 25
• 125000003282 alkyl amino group Chemical group 0.000 claims description 24
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 23
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 23
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 208000006673 asthma Diseases 0.000 claims description 20
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims description 18
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 18
• 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 claims description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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 11
• 208000035475 disorder Diseases 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 208000023275 Autoimmune disease Diseases 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 230000005764 inhibitory process Effects 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 239000013543 active substance Substances 0.000 claims description 8
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 230000001668 ameliorated effect Effects 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 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
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 4
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000004889 1-methylethylamino group Chemical group CC(C)N* 0.000 claims description 3
• 208000027771 Obstructive airways disease Diseases 0.000 claims description 3
• 201000009961 allergic asthma Diseases 0.000 claims description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 3
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
• UXDBXQWOQGPDHZ-UHFFFAOYSA-N 2h-pyran-4-carbonitrile Chemical compound N#CC1=CCOC=C1 UXDBXQWOQGPDHZ-UHFFFAOYSA-N 0.000 claims description 2
• NWQCVVREYYCLTJ-UHFFFAOYSA-N 3-(3-anilino-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl)oxane-4-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccccc3)c12)C1COCCC1C#N NWQCVVREYYCLTJ-UHFFFAOYSA-N 0.000 claims description 2
• 208000000884 Airway Obstruction Diseases 0.000 claims description 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
• 230000036428 airway hyperreactivity Effects 0.000 claims description 2
• 206010006451 bronchitis Diseases 0.000 claims description 2
• 201000011510 cancer Diseases 0.000 claims description 2
• 208000023819 chronic asthma Diseases 0.000 claims description 2
• HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 2
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
• 239000000428 dust Substances 0.000 claims description 2
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
• 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 2
• 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• LKVHTVRTQUBZDN-UHFFFAOYSA-N methyl cyclohex-2-ene-1-carboxylate Chemical compound COC(=O)C1CCCC=C1 LKVHTVRTQUBZDN-UHFFFAOYSA-N 0.000 claims description 2
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
• 230000000306 recurrent effect Effects 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
• 125000004414 alkyl thio group Chemical group 0.000 claims 1
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• 125000001475 halogen functional group Chemical group 0.000 claims 1
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• 239000000203 mixture Substances 0.000 description 77
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• 235000019439 ethyl acetate Nutrition 0.000 description 54
• 239000000543 intermediate Substances 0.000 description 53
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