KR20120083452A - 피롤로［2,3-ｄ］피리미딘 화합물 - Google Patents

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Publication number

KR20120083452A

KR20120083452A KR1020127012417A KR20127012417A KR20120083452A KR 20120083452 A KR20120083452 A KR 20120083452A KR 1020127012417 A KR1020127012417 A KR 1020127012417A KR 20127012417 A KR20127012417 A KR 20127012417A KR 20120083452 A KR20120083452 A KR 20120083452A

Authority

KR

South Korea

Prior art keywords

methyl

alkyl

group

hydrogen

pyrrolo

Prior art date

2009-10-15

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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• 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 204
• 238000000034 method Methods 0.000 claims abstract description 63
• 108010024121 Janus Kinases Proteins 0.000 claims abstract description 41
• 102000015617 Janus Kinases Human genes 0.000 claims abstract description 41
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• -1 R 24 Chemical compound 0.000 claims description 274
• 229910052739 hydrogen Inorganic materials 0.000 claims description 191
• 239000001257 hydrogen Substances 0.000 claims description 190
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 105
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 105
• 125000001424 substituent group Chemical group 0.000 claims description 88
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 86
• 150000002431 hydrogen Chemical class 0.000 claims description 85
• 150000003839 salts Chemical class 0.000 claims description 82
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 75
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 74
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• 201000010099 disease Diseases 0.000 claims description 44
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 43
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
• 125000004076 pyridyl group Chemical group 0.000 claims description 40
• 125000001153 fluoro group Chemical group F* 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 32
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 29
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 24
• 125000004043 oxo group Chemical group O=* 0.000 claims description 23
• 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 20
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
• 125000004193 piperazinyl group Chemical group 0.000 claims description 19
• 230000001404 mediated effect Effects 0.000 claims description 18
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
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• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 12
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 12
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
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• 125000003386 piperidinyl group Chemical group 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
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• 206010020751 Hypersensitivity Diseases 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
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• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
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• QMHIFZZTSBMKGF-NXOAAHMSSA-N C1[C@H](CO)[C@@H](C)CN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1[C@H](CO)[C@@H](C)CN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 QMHIFZZTSBMKGF-NXOAAHMSSA-N 0.000 claims description 4
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• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• XWKSFZMUCFUPJR-UHFFFAOYSA-N piperidin-3-yl dihydrogen phosphate Chemical compound OP(O)(=O)OC1CCCNC1 XWKSFZMUCFUPJR-UHFFFAOYSA-N 0.000 claims description 4
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 4
• DFVBZOPVGGDURA-MRJYIUEKSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCCC(O)C1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCCC(O)C1 DFVBZOPVGGDURA-MRJYIUEKSA-N 0.000 claims description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 3
• 206010013774 Dry eye Diseases 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 208000034578 Multiple myelomas Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 206010040047 Sepsis Diseases 0.000 claims description 3
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• 206010046851 Uveitis Diseases 0.000 claims description 3
• 230000001154 acute effect Effects 0.000 claims description 3
• 206010006451 bronchitis Diseases 0.000 claims description 3
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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• RRWIERVKMPBTBE-HPFXQQBRSA-N (3r)-1-[[(1s,3r,4s)-3-methyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound C([C@@H]1C[C@H]([C@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)C)S(=O)(=O)N1CCC[C@@H](O)C1 RRWIERVKMPBTBE-HPFXQQBRSA-N 0.000 claims description 2
• RRWIERVKMPBTBE-CVYDXHPNSA-N (3s)-1-[[(1s,3r,4s)-3-methyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound C([C@@H]1C[C@H]([C@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)C)S(=O)(=O)N1CCC[C@H](O)C1 RRWIERVKMPBTBE-CVYDXHPNSA-N 0.000 claims description 2
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 2
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• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
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