EA026730B1 - Соединения, ингибирующие киназы, и фармацевтическая композиция на их основе - Google Patents

Info

Publication number

EA026730B1

EA026730B1 EA201101341A EA201101341A EA026730B1 EA 026730 B1 EA026730 B1 EA 026730B1 EA 201101341 A EA201101341 A EA 201101341A EA 201101341 A EA201101341 A EA 201101341A EA 026730 B1 EA026730 B1 EA 026730B1

Authority

EA

Eurasian Patent Office

Prior art keywords

mmol

methyl

oxo

methylamino

phenyl

Prior art date

2006-09-14

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 385
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• -1 -CHK4K8 Chemical group 0.000 claims description 379
• 239000004202 carbamide Substances 0.000 claims description 210
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 196
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 112
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
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• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 239000000654 additive Substances 0.000 claims description 7
• 239000002671 adjuvant Substances 0.000 claims description 7
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 7
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• 125000004076 pyridyl group Chemical group 0.000 claims description 7
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• FQEIBEOBXKJAMZ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=CC(C(F)(F)F)=C1 FQEIBEOBXKJAMZ-UHFFFAOYSA-N 0.000 claims description 2
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• FGYGNBWUDFOOOY-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-phenylurea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=CC=C1 FGYGNBWUDFOOOY-UHFFFAOYSA-N 0.000 claims 3
• NDPIIWGKFWKYGT-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C=C(C(=CC=3F)C)C3=CC4=CN=C(NC)C=C4N(C3=O)CC)=CC=CC2=C1 NDPIIWGKFWKYGT-UHFFFAOYSA-N 0.000 claims 3
• VWSRPILDGFSBIY-UHFFFAOYSA-N 1-[4-chloro-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-phenylurea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=CC=C1 VWSRPILDGFSBIY-UHFFFAOYSA-N 0.000 claims 2
• POCMKRLYZZZJKE-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C(F)=CC=C(C=3)C3=CC4=CN=C(NC)C=C4N(C3=O)CC)=CC=CC2=C1 POCMKRLYZZZJKE-UHFFFAOYSA-N 0.000 claims 2
• 208000006011 Stroke Diseases 0.000 claims 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
• ADAZZRHBYOVNDP-UHFFFAOYSA-N 1-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 ADAZZRHBYOVNDP-UHFFFAOYSA-N 0.000 claims 1
• UYZSTDZANFAJHR-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F UYZSTDZANFAJHR-UHFFFAOYSA-N 0.000 claims 1
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• XXRCQUWJSONCRT-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[4-methyl-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1C XXRCQUWJSONCRT-UHFFFAOYSA-N 0.000 claims 1
• FPSIDFFYENCSKT-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 FPSIDFFYENCSKT-UHFFFAOYSA-N 0.000 claims 1
• PMZHKRHHUMHWRN-UHFFFAOYSA-N 1-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F PMZHKRHHUMHWRN-UHFFFAOYSA-N 0.000 claims 1
• JFONXTNNTJGCQE-UHFFFAOYSA-N 1-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 JFONXTNNTJGCQE-UHFFFAOYSA-N 0.000 claims 1
• CNECREPZVOYSRI-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-(3-cyanophenyl)urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=CC(C#N)=C1 CNECREPZVOYSRI-UHFFFAOYSA-N 0.000 claims 1
• YRQKNOMICTWOEA-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F YRQKNOMICTWOEA-UHFFFAOYSA-N 0.000 claims 1
• SKXZDAFGKFHEJM-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 SKXZDAFGKFHEJM-UHFFFAOYSA-N 0.000 claims 1
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• HJESIEHPUXMNDW-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C=C(C(=CC=3F)Cl)C=3C(=O)N(C)C=4C=C(N=CC=4C=3)NC)=CC=CC2=C1 HJESIEHPUXMNDW-UHFFFAOYSA-N 0.000 claims 1
• DKUXKAYWLUZKLJ-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 DKUXKAYWLUZKLJ-UHFFFAOYSA-N 0.000 claims 1
• FYVGTRITEKZXNV-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 FYVGTRITEKZXNV-UHFFFAOYSA-N 0.000 claims 1
• IRBLVQHOCDLOMH-UHFFFAOYSA-N 1-[4-chloro-3-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-cyclohexylurea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1)Cl)=CC=1NC(=O)NC1CCCCC1 IRBLVQHOCDLOMH-UHFFFAOYSA-N 0.000 claims 1
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• VEMVWTTWMSWHHM-UHFFFAOYSA-N 1-[4-chloro-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 VEMVWTTWMSWHHM-UHFFFAOYSA-N 0.000 claims 1
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• SZAZTNLBSWEIGX-UHFFFAOYSA-N 1-[5-(7-amino-1-methyl-2-oxo-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2C(N(C)C3=CC(N)=NC=C3C=2)=O)C(C)=CC(F)=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 SZAZTNLBSWEIGX-UHFFFAOYSA-N 0.000 claims 1
• GHFPWSHLGZJOGE-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 GHFPWSHLGZJOGE-UHFFFAOYSA-N 0.000 claims 1
• KRKFQJUZHAFOAZ-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F KRKFQJUZHAFOAZ-UHFFFAOYSA-N 0.000 claims 1
• GDENILKFMBNOQR-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 GDENILKFMBNOQR-UHFFFAOYSA-N 0.000 claims 1
• XSUVKPPSEXWYGN-UHFFFAOYSA-N 1-cyclohexyl-3-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC1CCCCC1 XSUVKPPSEXWYGN-UHFFFAOYSA-N 0.000 claims 1
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• UKNRWOLNLTUUGU-UHFFFAOYSA-N ethyl 2-methylsulfanyl-4-(propan-2-ylamino)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SC)N=C1NC(C)C UKNRWOLNLTUUGU-UHFFFAOYSA-N 0.000 description 2
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• HFZNNKRDKQNPAK-UHFFFAOYSA-N ethyl 4-anilino-6-chloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)C=C1NC1=CC=CC=C1 HFZNNKRDKQNPAK-UHFFFAOYSA-N 0.000 description 2
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• FHWFDOUCPPFEDI-UHFFFAOYSA-N ethyl 5-tert-butyl-2-(2-morpholin-4-yl-2-oxoethyl)pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(C(C)(C)C)=NN1CC(=O)N1CCOCC1 FHWFDOUCPPFEDI-UHFFFAOYSA-N 0.000 description 2
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• 150000003840 hydrochlorides Chemical class 0.000 description 2
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