EA037299B1 - Ингибиторы mk2 и их применения - Google Patents

Info

Publication number

EA037299B1

EA037299B1 EA201790380A EA201790380A EA037299B1 EA 037299 B1 EA037299 B1 EA 037299B1 EA 201790380 A EA201790380 A EA 201790380A EA 201790380 A EA201790380 A EA 201790380A EA 037299 B1 EA037299 B1 EA 037299B1

Authority

EA

Eurasian Patent Office

Prior art keywords

compound

mmol

int

present

optionally substituted

Prior art date

2014-09-17

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• 229940124789 MK2 inhibitor Drugs 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 485
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 79
• 208000035475 disorder Diseases 0.000 claims abstract description 42
• 238000000034 method Methods 0.000 claims abstract description 40
• 201000010099 disease Diseases 0.000 claims abstract description 37
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 230000001404 mediated effect Effects 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 6
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims abstract description 5
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 5
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims abstract description 5
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims abstract description 5
• 239000000203 mixture Substances 0.000 claims description 123
• 108010041955 MAP-kinase-activated kinase 2 Proteins 0.000 claims description 13
• 102100034069 MAP kinase-activated protein kinase 2 Human genes 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 7
• 239000003981 vehicle Substances 0.000 claims description 4
• 239000011541 reaction mixture Substances 0.000 description 201
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 191
• 229910052757 nitrogen Inorganic materials 0.000 description 167
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 166
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• 238000001819 mass spectrum Methods 0.000 description 143
• 229920006395 saturated elastomer Polymers 0.000 description 138
• 125000005842 heteroatom Chemical group 0.000 description 134
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 133
• 229910052717 sulfur Chemical group 0.000 description 133
• 239000011593 sulfur Chemical group 0.000 description 133
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• 125000000623 heterocyclic group Chemical group 0.000 description 60
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• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
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• RSWJZQPZLNLWGF-UHFFFAOYSA-N 2H-thieno[3,2-f]quinolin-8-one Chemical compound C=1CSC=2C=1C1=CC(C=NC1=CC=2)=O RSWJZQPZLNLWGF-UHFFFAOYSA-N 0.000 description 37
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• 125000002618 bicyclic heterocycle group Chemical group 0.000 description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 125000002619 bicyclic group Chemical group 0.000 description 26
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• 239000000543 intermediate Substances 0.000 description 25
• 125000004433 nitrogen atom Chemical group N* 0.000 description 25
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
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• 239000012267 brine Substances 0.000 description 22
• 239000007788 liquid Substances 0.000 description 22
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• 125000002947 alkylene group Chemical group 0.000 description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 21
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• 229910002027 silica gel Inorganic materials 0.000 description 20
• 229910052799 carbon Inorganic materials 0.000 description 19
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
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• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 17
• 150000002431 hydrogen Chemical class 0.000 description 17
• HNDGEYCCZGRMTN-UHFFFAOYSA-N thieno[3,2-f:4,5-f]bis[1]benzothiophene Chemical compound S1C2=CC=3SC=CC=3C=C2C2=C1C=C(SC=C1)C1=C2 HNDGEYCCZGRMTN-UHFFFAOYSA-N 0.000 description 17
• 150000001721 carbon Chemical group 0.000 description 16
• 125000001072 heteroaryl group Chemical group 0.000 description 16
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 16
• NFTNYEQPGPAENQ-UHFFFAOYSA-N CN(CCOC1=NC(=CC(=N1)N)F)C Chemical compound CN(CCOC1=NC(=CC(=N1)N)F)C NFTNYEQPGPAENQ-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 238000004440 column chromatography Methods 0.000 description 15
• 230000000694 effects Effects 0.000 description 15
• 150000002430 hydrocarbons Chemical group 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
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• 102000001253 Protein Kinase Human genes 0.000 description 14
• 125000000217 alkyl group Chemical group 0.000 description 14
• OVJIHFBAXJKTRF-SSDOTTSWSA-N chembl556392 Chemical compound O=C1N[C@H](C)CNC2=C1SC1=CC=C(N=C(Cl)C=C3)C3=C21 OVJIHFBAXJKTRF-SSDOTTSWSA-N 0.000 description 14
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• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
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• 230000002401 inhibitory effect Effects 0.000 description 11
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
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