RU2008148902A - Производные имидазол-пиримидина для лечения заболеваний, связанных с киназой гликогенсинтазы 3 (gsk3) - Google Patents
Производные имидазол-пиримидина для лечения заболеваний, связанных с киназой гликогенсинтазы 3 (gsk3) Download PDFInfo
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- RU2008148902A RU2008148902A RU2008148902/04A RU2008148902A RU2008148902A RU 2008148902 A RU2008148902 A RU 2008148902A RU 2008148902/04 A RU2008148902/04 A RU 2008148902/04A RU 2008148902 A RU2008148902 A RU 2008148902A RU 2008148902 A RU2008148902 A RU 2008148902A
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- Prior art keywords
- methyl
- alkyl
- imidazol
- fluoro
- amino
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims 4
- 201000010099 disease Diseases 0.000 title claims 3
- 102000001267 GSK3 Human genes 0.000 title 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 title 2
- KNDAOVHRTCJABP-UHFFFAOYSA-N 1h-imidazole;pyrimidine Chemical class C1=CNC=N1.C1=CN=CN=C1 KNDAOVHRTCJABP-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 55
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 36
- -1 3-tetrahydropyranyl Chemical group 0.000 claims abstract 29
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 125000005843 halogen group Chemical group 0.000 claims abstract 26
- 229910052799 carbon Inorganic materials 0.000 claims abstract 25
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
- 239000001257 hydrogen Substances 0.000 claims abstract 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 15
- 150000002829 nitrogen Chemical class 0.000 claims abstract 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 11
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 239000001301 oxygen Substances 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 7
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 3
- 210000000988 bone and bone Anatomy 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 3
- 208000024714 major depressive disease Diseases 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
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- 238000004519 manufacturing process Methods 0.000 claims 2
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- 230000002265 prevention Effects 0.000 claims 2
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- 239000012453 solvate Substances 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- VMGUWFGUMZRWDD-UHFFFAOYSA-N (2,6-dimethylpiperidin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound CC1CCCC(C)N1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 VMGUWFGUMZRWDD-UHFFFAOYSA-N 0.000 claims 1
- WWGYXDWUEUVJCI-UHFFFAOYSA-N (3,3-difluoropyrrolidin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N1CCC(F)(F)C1 WWGYXDWUEUVJCI-UHFFFAOYSA-N 0.000 claims 1
- HKDAFXBCUWUUQP-UHFFFAOYSA-N (3,5-dimethylpiperidin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1C(C)CC(C)CN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 HKDAFXBCUWUUQP-UHFFFAOYSA-N 0.000 claims 1
- PIABFBSAORAFPU-UHFFFAOYSA-N (4-benzylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N(CC1)CCN1CC1=CC=CC=C1 PIABFBSAORAFPU-UHFFFAOYSA-N 0.000 claims 1
- FLFRWPXYPISNIH-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 FLFRWPXYPISNIH-UHFFFAOYSA-N 0.000 claims 1
- GMQLLYIFZSEJPL-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 GMQLLYIFZSEJPL-UHFFFAOYSA-N 0.000 claims 1
- OYCCDNYVHVFKKN-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 OYCCDNYVHVFKKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- LQEOPALZMNEMPG-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n,n-di(propan-2-yl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C(C)C)C(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 LQEOPALZMNEMPG-UHFFFAOYSA-N 0.000 claims 1
- LRMNPLYTCUDBFE-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n,n-dipropylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(CCC)CCC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 LRMNPLYTCUDBFE-UHFFFAOYSA-N 0.000 claims 1
- YMKZRCIUZLIOHS-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n-methyl-n-(2-methylpropyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C)CC(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 YMKZRCIUZLIOHS-UHFFFAOYSA-N 0.000 claims 1
- SKAQUBBZLUGQFR-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridine-2-carbaldehyde Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C=O)N=C1 SKAQUBBZLUGQFR-UHFFFAOYSA-N 0.000 claims 1
- AFCZSQCTHGPWSN-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(5-methylsulfonylpyridin-2-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)C=N1 AFCZSQCTHGPWSN-UHFFFAOYSA-N 0.000 claims 1
- NBKWSGUZFJHXCL-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(6-methylsulfonylpyridin-3-yl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)N=C1 NBKWSGUZFJHXCL-UHFFFAOYSA-N 0.000 claims 1
- QKYAWVXVTSDCIM-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(6-propan-2-ylsulfonylpyridin-3-yl)pyrimidin-2-amine Chemical compound C1=NC(S(=O)(=O)C(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 QKYAWVXVTSDCIM-UHFFFAOYSA-N 0.000 claims 1
- QIZMDSPMHSHDEB-UHFFFAOYSA-N 5-fluoro-n-(2-methoxypyrimidin-5-yl)-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(OC)=NC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 QIZMDSPMHSHDEB-UHFFFAOYSA-N 0.000 claims 1
- 208000017194 Affective disease Diseases 0.000 claims 1
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- 102100038076 DNA dC->dU-editing enzyme APOBEC-3G Human genes 0.000 claims 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
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- MIIHRHZPVFFLNV-UHFFFAOYSA-N [3-chloro-5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)Cl)=NC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C)=N1 MIIHRHZPVFFLNV-UHFFFAOYSA-N 0.000 claims 1
- WXPPJJJNBYDKLN-UHFFFAOYSA-N [3-chloro-5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.CN1C(C)=NC=C1C1=NC(NC=2C=C(Cl)C(C(=O)N3CCCCC3)=NC=2)=NC=C1F WXPPJJJNBYDKLN-UHFFFAOYSA-N 0.000 claims 1
- HAFDEHIYHASOTC-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1Cl)=CN=C1C(=O)N1CCCCC1 HAFDEHIYHASOTC-UHFFFAOYSA-N 0.000 claims 1
- SKYXACSXHYZRJQ-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-(oxan-4-yl)-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)Cl)=NC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C2CCOCC2)=N1 SKYXACSXHYZRJQ-UHFFFAOYSA-N 0.000 claims 1
- COYKCXSIKZIBPX-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-(oxan-4-yl)-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.N1=C(C=2N(C(=NC=2)C(F)(F)F)C2CCOCC2)C(F)=CN=C1NC(C=C1Cl)=CN=C1C(=O)N1CCCCC1 COYKCXSIKZIBPX-UHFFFAOYSA-N 0.000 claims 1
- IMVUQMPEFGNUQU-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)Cl)=NC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C)=N1 IMVUQMPEFGNUQU-UHFFFAOYSA-N 0.000 claims 1
- VXTHKTIWGOTFAH-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.N1=C(C(F)(F)F)N(C)C(C=2C(=CN=C(NC=3C=C(Cl)C(C(=O)N4CCCCC4)=NC=3)N=2)F)=C1 VXTHKTIWGOTFAH-UHFFFAOYSA-N 0.000 claims 1
- QTBWYPYVFWMGBX-UHFFFAOYSA-N [5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C)=N1 QTBWYPYVFWMGBX-UHFFFAOYSA-N 0.000 claims 1
- GLUHCPHQUQQXHV-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(3-methylpiperidin-1-yl)methanone Chemical compound C1C(C)CCCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 GLUHCPHQUQQXHV-UHFFFAOYSA-N 0.000 claims 1
- HBZKNQHUWOKHRE-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-fluoropiperidin-1-yl)methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N1CCC(F)CC1 HBZKNQHUWOKHRE-UHFFFAOYSA-N 0.000 claims 1
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- MCSBEOQVHGWTJB-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N1CCCCC1 MCSBEOQVHGWTJB-UHFFFAOYSA-N 0.000 claims 1
- JUMYRNHMMUIHCS-UHFFFAOYSA-N [6-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C=N1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 JUMYRNHMMUIHCS-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- DVWZSIRIFYGARA-UHFFFAOYSA-N azetidin-1-yl-[3-chloro-5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound CN1C(C)=NC=C1C1=NC(NC=2C=C(Cl)C(C(=O)N3CCC3)=NC=2)=NC=C1F DVWZSIRIFYGARA-UHFFFAOYSA-N 0.000 claims 1
- IZZMQZVJRXUABE-UHFFFAOYSA-N azetidin-1-yl-[3-chloro-5-[[5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone;hydrochloride Chemical compound Cl.N1=C(C(F)(F)F)N(C)C(C=2C(=CN=C(NC=3C=C(Cl)C(C(=O)N4CCC4)=NC=3)N=2)F)=C1 IZZMQZVJRXUABE-UHFFFAOYSA-N 0.000 claims 1
- YUDLMHLYKXMDDX-UHFFFAOYSA-N azetidin-1-yl-[5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound CN1C(C)=NC=C1C1=NC(NC=2C=NC(=CC=2)C(=O)N2CCC2)=NC=C1F YUDLMHLYKXMDDX-UHFFFAOYSA-N 0.000 claims 1
- LJANEJXMXPUPBQ-UHFFFAOYSA-N azetidin-1-yl-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N1CCC1 LJANEJXMXPUPBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
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- 208000028683 bipolar I disease Diseases 0.000 claims 1
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- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
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- 208000017004 dementia pugilistica Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 208000024732 dysthymic disease Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- XQSRMCZTBCMDDX-UHFFFAOYSA-N n-(6-ethoxypyridin-3-yl)-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(OCC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 XQSRMCZTBCMDDX-UHFFFAOYSA-N 0.000 claims 1
- BFFHGFGYQRAFPQ-UHFFFAOYSA-N n-(6-ethylsulfonylpyridin-3-yl)-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(S(=O)(=O)CC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 BFFHGFGYQRAFPQ-UHFFFAOYSA-N 0.000 claims 1
- CRWPLLBQGBOONW-UHFFFAOYSA-N n-(cyclopropylmethyl)-5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n-propylpyridine-2-carboxamide Chemical compound C=1C=C(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)C=NC=1C(=O)N(CCC)CC1CC1 CRWPLLBQGBOONW-UHFFFAOYSA-N 0.000 claims 1
- IMWKNRIKTUODBG-UHFFFAOYSA-N n-butan-2-yl-5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n-propylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C(C)CC)CCC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 IMWKNRIKTUODBG-UHFFFAOYSA-N 0.000 claims 1
- 230000011164 ossification Effects 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 235000014347 soups Nutrition 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000018726 traumatic encephalopathy Diseases 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- 0 CCIC(Nc1nc(-c2cnc(C)[n]2*)c(*)cn1)=* Chemical compound CCIC(Nc1nc(-c2cnc(C)[n]2*)c(*)cn1)=* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Biomedical Technology (AREA)
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- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81675606P | 2006-06-27 | 2006-06-27 | |
| US60/816,756 | 2006-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008148902A true RU2008148902A (ru) | 2010-08-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| RU2008148902/04A RU2008148902A (ru) | 2006-06-27 | 2007-06-26 | Производные имидазол-пиримидина для лечения заболеваний, связанных с киназой гликогенсинтазы 3 (gsk3) |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20080188502A1 (enExample) |
| EP (1) | EP2046782A4 (enExample) |
| JP (1) | JP2009542638A (enExample) |
| KR (1) | KR20090024817A (enExample) |
| CN (1) | CN101511825A (enExample) |
| AR (1) | AR061652A1 (enExample) |
| AU (1) | AU2007265731A1 (enExample) |
| BR (1) | BRPI0713576A2 (enExample) |
| CA (1) | CA2655441A1 (enExample) |
| CL (1) | CL2007001881A1 (enExample) |
| CO (1) | CO6140059A2 (enExample) |
| EC (1) | ECSP088973A (enExample) |
| IL (1) | IL195666A0 (enExample) |
| MX (1) | MX2008015720A (enExample) |
| NO (1) | NO20090327L (enExample) |
| RU (1) | RU2008148902A (enExample) |
| TW (1) | TW200815418A (enExample) |
| UY (1) | UY30440A1 (enExample) |
| WO (1) | WO2008002244A2 (enExample) |
| ZA (1) | ZA200810484B (enExample) |
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| AU2006296386A1 (en) | 2005-09-30 | 2007-04-05 | Astrazeneca Ab | Imidazo [1,2-a] pyridine having anti-cell-proliferation activity |
| UY29827A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | 2-amina-pirimidina-4-(2-metil-1-(tetrahidro-2h-piran-4-il)-1-imidazol-5-y1) sustituidas y sus derivados, composiciones farmacéuticas que las contienen, procesos para su preparación y aplicaciones |
| TW200811169A (en) * | 2006-05-26 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
| TW200815417A (en) * | 2006-06-27 | 2008-04-01 | Astrazeneca Ab | New compounds II |
| AU2007265966B2 (en) * | 2006-06-27 | 2012-05-17 | Takeda Pharmaceutical Company Limited | Fused cyclic compounds |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP2406230A1 (en) | 2009-03-11 | 2012-01-18 | Pfizer Inc. | Substituted indazole amides and their use as glucokinase activators |
| EP2419425A4 (en) | 2009-04-15 | 2012-08-29 | Astrazeneca Ab | IMIDAZOLE SUBSTITUTED PYRIMIDINES USEFUL IN THE TREATMENT OF GLYCOGEN SYNTHASE KINASE 3 RELATED DISORDERS, SUCH AS ALZHEIMER'S DISEASE |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CN103724207B (zh) * | 2013-12-20 | 2016-07-06 | 北京智博高科生物技术有限公司 | 苯基苄基醚类衍生物及其制备方法和应用 |
| JP2017524739A (ja) | 2014-07-17 | 2017-08-31 | アンセルムＩｎｓｅｒｍ | 神経筋接合部関連疾患の処置方法 |
| UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
| WO2016207366A1 (en) | 2015-06-26 | 2016-12-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of viral infections |
| AR105607A1 (es) | 2015-08-07 | 2017-10-18 | Bayer Cropscience Ag | Derivados heterocíclicos condensados sustituidos por 2-(het)arilo como pesticidas |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
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| GB0021726D0 (en) * | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| US7361665B2 (en) * | 2002-07-09 | 2008-04-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases |
| JP2007500178A (ja) * | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体 |
| BRPI0415759A (pt) * | 2003-10-21 | 2006-12-19 | Cyclacel Ltd | compostos de pirimidin-4-il-3,4-tiona e uso dos mesmos na terapia |
| GB0402653D0 (en) * | 2004-02-06 | 2004-03-10 | Cyclacel Ltd | Compounds |
| US20090099160A1 (en) * | 2004-12-17 | 2009-04-16 | David Andrews | 4-(4-(Imidazol-4-Yl) Pyrimidin-2-Ylamino) Benzamides as CDK Inhibitors |
| GB0504753D0 (en) * | 2005-03-08 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| UY29827A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | 2-amina-pirimidina-4-(2-metil-1-(tetrahidro-2h-piran-4-il)-1-imidazol-5-y1) sustituidas y sus derivados, composiciones farmacéuticas que las contienen, procesos para su preparación y aplicaciones |
| TW200815417A (en) * | 2006-06-27 | 2008-04-01 | Astrazeneca Ab | New compounds II |
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2007
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- 2007-06-26 EP EP07748281A patent/EP2046782A4/en not_active Withdrawn
- 2007-06-26 CL CL200701881A patent/CL2007001881A1/es unknown
- 2007-06-26 RU RU2008148902/04A patent/RU2008148902A/ru not_active Application Discontinuation
- 2007-06-26 WO PCT/SE2007/000620 patent/WO2008002244A2/en not_active Ceased
- 2007-06-26 AR ARP070102831A patent/AR061652A1/es not_active Application Discontinuation
- 2007-06-26 AU AU2007265731A patent/AU2007265731A1/en not_active Abandoned
- 2007-06-26 BR BRPI0713576-9A patent/BRPI0713576A2/pt not_active IP Right Cessation
- 2007-06-26 CN CNA2007800322107A patent/CN101511825A/zh active Pending
- 2007-06-26 UY UY30440A patent/UY30440A1/es unknown
- 2007-06-27 US US11/769,102 patent/US20080188502A1/en not_active Abandoned
-
2008
- 2008-12-02 IL IL195666A patent/IL195666A0/en unknown
- 2008-12-10 ZA ZA200810484A patent/ZA200810484B/xx unknown
- 2008-12-12 EC EC2008008973A patent/ECSP088973A/es unknown
- 2008-12-17 CO CO08134161A patent/CO6140059A2/es unknown
-
2009
- 2009-01-21 NO NO20090327A patent/NO20090327L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CL2007001881A1 (es) | 2008-02-08 |
| JP2009542638A (ja) | 2009-12-03 |
| ECSP088973A (es) | 2009-01-30 |
| TW200815418A (en) | 2008-04-01 |
| WO2008002244A3 (en) | 2008-02-14 |
| CA2655441A1 (en) | 2008-01-03 |
| KR20090024817A (ko) | 2009-03-09 |
| CN101511825A (zh) | 2009-08-19 |
| MX2008015720A (es) | 2008-12-19 |
| IL195666A0 (en) | 2009-09-01 |
| EP2046782A4 (en) | 2010-10-13 |
| WO2008002244A2 (en) | 2008-01-03 |
| UY30440A1 (es) | 2008-01-31 |
| EP2046782A2 (en) | 2009-04-15 |
| WO2008002244A8 (en) | 2008-10-09 |
| NO20090327L (no) | 2009-02-09 |
| AU2007265731A1 (en) | 2008-01-03 |
| BRPI0713576A2 (pt) | 2012-10-23 |
| CO6140059A2 (es) | 2010-03-19 |
| AR061652A1 (es) | 2008-09-10 |
| US20080188502A1 (en) | 2008-08-07 |
| ZA200810484B (en) | 2009-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110913 |