JP2018513177A5 - - Google Patents
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- Publication number
- JP2018513177A5 JP2018513177A5 JP2017555270A JP2017555270A JP2018513177A5 JP 2018513177 A5 JP2018513177 A5 JP 2018513177A5 JP 2017555270 A JP2017555270 A JP 2017555270A JP 2017555270 A JP2017555270 A JP 2017555270A JP 2018513177 A5 JP2018513177 A5 JP 2018513177A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- pyridin
- carboxamide
- thiazole
- furan
- Prior art date
- 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.)
- Granted
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- -1 cyano, carboxyl Chemical group 0.000 claims description 607
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 82
- PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 claims description 76
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 69
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 34
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 30
- PNGWJQONBMCVTJ-UHFFFAOYSA-N S1C=NC(=C1)C(=O)NC(O)=O Chemical compound S1C=NC(=C1)C(=O)NC(O)=O PNGWJQONBMCVTJ-UHFFFAOYSA-N 0.000 claims description 28
- WUAXASOCLCTWRX-UHFFFAOYSA-N furan-2-carbonylcarbamic acid Chemical compound OC(=O)NC(=O)C1=CC=CO1 WUAXASOCLCTWRX-UHFFFAOYSA-N 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 27
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 26
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 229910019142 PO4 Inorganic materials 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 239000010452 phosphate Substances 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 16
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 239000012458 free base Substances 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- VAELWSLNTRVXQS-UHFFFAOYSA-N 1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC=N1 VAELWSLNTRVXQS-UHFFFAOYSA-N 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims description 8
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- YJTRFJIAMAMBHB-UHFFFAOYSA-N 3-[1-(3,3-difluorocyclobutyl)-3-pyridin-2-ylpyrazol-4-yl]-2-(1H-pyrazol-4-yl)-2H-1,3-thiazole Chemical compound FC1(CC(C1)N1N=C(C(=C1)N1C(SC=C1)C=1C=NNC1)C1=NC=CC=C1)F YJTRFJIAMAMBHB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- MBTOOKBKBYXTCE-UHFFFAOYSA-L disodium;methyl phosphate Chemical compound [Na+].[Na+].COP([O-])([O-])=O MBTOOKBKBYXTCE-UHFFFAOYSA-L 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000000302 ischemic effect Effects 0.000 claims description 4
- CAAULPUQFIIOTL-UHFFFAOYSA-M methyl hydrogen phosphate Chemical compound COP(O)([O-])=O CAAULPUQFIIOTL-UHFFFAOYSA-M 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000003566 oxetanyl group Chemical group 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000002519 immonomodulatory effect Effects 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- QETMRHQTVLFIPW-UHFFFAOYSA-N (1-methylcyclopropyl) 4-[4-[(1-methyl-3-pyridin-2-ylpyrazol-4-yl)carbamoyl]-1,3-thiazol-2-yl]pyrazole-1-carboxylate Chemical compound CN1N=C(C(=C1)NC(=O)C=1N=C(SC=1)C=1C=NN(C=1)C(=O)OC1(CC1)C)C1=NC=CC=C1 QETMRHQTVLFIPW-UHFFFAOYSA-N 0.000 claims description 2
- GDBALSNVRLWFEX-UHFFFAOYSA-N (1-methylcyclopropyl) 4-[5-[[1-(2-methoxyethyl)-3-pyridin-2-ylpyrazol-4-yl]carbamoyl]furan-2-yl]pyrazole-1-carboxylate Chemical compound COCCN1N=C(C(=C1)NC(=O)C1=CC=C(O1)C=1C=NN(C=1)C(=O)OC1(CC1)C)C1=NC=CC=C1 GDBALSNVRLWFEX-UHFFFAOYSA-N 0.000 claims description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- REZCJQIIJVPKAF-UHFFFAOYSA-N C1(CC1)CN1N=CC(=C1)C1OC=CN1C=1C(=NN(C1)C)C1=NC=CC=C1 Chemical compound C1(CC1)CN1N=CC(=C1)C1OC=CN1C=1C(=NN(C1)C)C1=NC=CC=C1 REZCJQIIJVPKAF-UHFFFAOYSA-N 0.000 claims description 2
- TZTVKIVBDYAXKS-UHFFFAOYSA-N CC1=C(C=NN1)C2=CC=C(O2)C(=O)N(C3=CN(N=C3C4=CC=CC=N4)CCOC)C(=O)O Chemical compound CC1=C(C=NN1)C2=CC=C(O2)C(=O)N(C3=CN(N=C3C4=CC=CC=N4)CCOC)C(=O)O TZTVKIVBDYAXKS-UHFFFAOYSA-N 0.000 claims description 2
- TXIXBWPJMNOQLG-UHFFFAOYSA-M CN(C=C1NC(C2=CSC(C(C=N3)=CN3OP([O-])(OC)=O)=N2)=O)N=C1C1=NC=CC=C1.[Na+] Chemical compound CN(C=C1NC(C2=CSC(C(C=N3)=CN3OP([O-])(OC)=O)=N2)=O)N=C1C1=NC=CC=C1.[Na+] TXIXBWPJMNOQLG-UHFFFAOYSA-M 0.000 claims description 2
- QQVAAOUFNUFDPL-UHFFFAOYSA-M CN(C=C1NC(C2=CSC(C3=CN(COP([O-])=O)N=C3)=N2)=O)N=C1C1=NC=CC=C1.[Na+] Chemical class CN(C=C1NC(C2=CSC(C3=CN(COP([O-])=O)N=C3)=N2)=O)N=C1C1=NC=CC=C1.[Na+] QQVAAOUFNUFDPL-UHFFFAOYSA-M 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000004852 Lung Injury Diseases 0.000 claims description 2
- 208000034486 Multi-organ failure Diseases 0.000 claims description 2
- 208000010718 Multiple Organ Failure Diseases 0.000 claims description 2
- VCXTZIGRKPMUMN-UHFFFAOYSA-M P(=O)(ON1N=CC(=C1)C=1OC(=CC1)C(NC=1C(=NN(C1)CCOC)C1=NC=CC=C1)=O)(OC)[O-].[Na+] Chemical compound P(=O)(ON1N=CC(=C1)C=1OC(=CC1)C(NC=1C(=NN(C1)CCOC)C1=NC=CC=C1)=O)(OC)[O-].[Na+] VCXTZIGRKPMUMN-UHFFFAOYSA-M 0.000 claims description 2
- SKDDEHAVBWKSCR-UHFFFAOYSA-M P(=O)(ON1N=CC(=C1)C=1OC(=CC1)C(NC=1C(=NN(C1)CCOCC)C1=NC=CC=C1)=O)(OC)[O-].[Na+] Chemical compound P(=O)(ON1N=CC(=C1)C=1OC(=CC1)C(NC=1C(=NN(C1)CCOCC)C1=NC=CC=C1)=O)(OC)[O-].[Na+] SKDDEHAVBWKSCR-UHFFFAOYSA-M 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- XHVMAHLWCMJJRT-UHFFFAOYSA-N [1-(3-ethoxycyclobutyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-[2-(1H-pyrazol-4-yl)-1,3-thiazol-4-yl]methanone 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC1CC(C1)n1ncc2N(CCCc12)C(=O)c1csc(n1)-c1cn[nH]c1 XHVMAHLWCMJJRT-UHFFFAOYSA-N 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 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 2
- 230000007812 deficiency Effects 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- RAKINNFKPYCWIS-UHFFFAOYSA-N ditert-butyl [4-[5-[[1-(2-methoxyethyl)-3-pyridin-2-ylpyrazol-4-yl]carbamoyl]furan-2-yl]pyrazol-1-yl]methyl phosphate Chemical compound P(=O)(OC(C)(C)C)(OC(C)(C)C)OCN1N=CC(=C1)C=1OC(=CC=1)C(NC=1C(=NN(C=1)CCOC)C1=NC=CC=C1)=O RAKINNFKPYCWIS-UHFFFAOYSA-N 0.000 claims description 2
- 210000003743 erythrocyte Anatomy 0.000 claims description 2
- XXPKIDAWGVKUBD-UHFFFAOYSA-N formaldehyde;2,2,2-trifluoroacetic acid Chemical compound O=C.OC(=O)C(F)(F)F XXPKIDAWGVKUBD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 2
- IGSSNLHDFIYOIL-UHFFFAOYSA-N furan-2-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=CO1 IGSSNLHDFIYOIL-UHFFFAOYSA-N 0.000 claims description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 231100000515 lung injury Toxicity 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 2
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
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- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 230000019100 sperm motility Effects 0.000 claims description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- DKVHSIGYVOGGES-UHFFFAOYSA-N tert-butyl 4-[5-[[1-(2-ethoxyethyl)-3-pyridin-2-ylpyrazol-4-yl]carbamoyl]furan-2-yl]pyrazole-1-carboxylate Chemical compound C(C)OCCN1N=C(C(=C1)NC(=O)C1=CC=C(O1)C=1C=NN(C=1)C(=O)OC(C)(C)C)C1=NC=CC=C1 DKVHSIGYVOGGES-UHFFFAOYSA-N 0.000 claims description 2
- LUEILWKCNRMZKG-UHFFFAOYSA-N tert-butyl [4-[5-[[1-(2-methoxyethyl)-3-pyridin-2-ylpyrazol-4-yl]carbamoyl]furan-2-yl]pyrazol-1-yl]methyl hydrogen phosphate Chemical compound P(=O)(OC(C)(C)C)(OCN1N=CC(=C1)C=1OC(=CC=1)C(NC=1C(=NN(C=1)CCOC)C1=NC=CC=C1)=O)O LUEILWKCNRMZKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
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- IMQYCAOLMXPFRY-UHFFFAOYSA-N n-(1h-pyrazol-4-yl)-1,3-thiazole-4-carboxamide Chemical compound C=1SC=NC=1C(=O)NC=1C=NNC=1 IMQYCAOLMXPFRY-UHFFFAOYSA-N 0.000 claims 1
- OSYWKBOVEOEMQD-UHFFFAOYSA-N n-(1h-pyrazol-4-yl)furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC=1C=NNC=1 OSYWKBOVEOEMQD-UHFFFAOYSA-N 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
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