HRP20090495T1 - Heterobiciklički inhibitori protein kinaze supstituirani 6,6-bicikličkim prstenom - Google Patents
Heterobiciklički inhibitori protein kinaze supstituirani 6,6-bicikličkim prstenom Download PDFInfo
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- HRP20090495T1 HRP20090495T1 HR20090495T HRP20090495T HRP20090495T1 HR P20090495 T1 HRP20090495 T1 HR P20090495T1 HR 20090495 T HR20090495 T HR 20090495T HR P20090495 T HRP20090495 T HR P20090495T HR P20090495 T1 HRP20090495 T1 HR P20090495T1
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- Prior art keywords
- imidazo
- pyrazin
- image
- 10alkyl
- amino
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- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title 1
- 239000003909 protein kinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 48
- 125000001424 substituent group Chemical group 0.000 claims abstract 37
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 22
- 150000003839 salts Chemical class 0.000 claims abstract 15
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract 11
- 125000003118 aryl group Chemical group 0.000 claims abstract 9
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- 125000005843 halogen group Chemical group 0.000 claims 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 24
- 102000001253 Protein Kinase Human genes 0.000 claims 11
- 108060006633 protein kinase Proteins 0.000 claims 11
- 230000000694 effects Effects 0.000 claims 9
- -1 C2-10alkynyl Chemical group 0.000 claims 8
- 230000001404 mediated effect Effects 0.000 claims 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- FUGZYLOFWXVFQU-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 FUGZYLOFWXVFQU-UHFFFAOYSA-N 0.000 claims 4
- CRXFZICQPIJJRJ-UHFFFAOYSA-N 3-[4-(aminomethyl)cyclohexyl]-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1CC(CN)CCC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N CRXFZICQPIJJRJ-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QNQAPXGKMZTEPB-UHFFFAOYSA-N 3-cyclobutyl-1-(2-phenylquinolin-7-yl)-2,3-dihydroimidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 QNQAPXGKMZTEPB-UHFFFAOYSA-N 0.000 claims 3
- AWARRGOPBGTLFG-MXVIHJGJSA-N C1C[C@@H](C(=O)N)CC[C@@H]1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N Chemical compound C1C[C@@H](C(=O)N)CC[C@@H]1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N AWARRGOPBGTLFG-MXVIHJGJSA-N 0.000 claims 3
- LJWGLPMHPKZOPY-MEMLXQNLSA-N C1C[C@@H](C(=O)NC)CC[C@@H]1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N Chemical compound C1C[C@@H](C(=O)NC)CC[C@@H]1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N LJWGLPMHPKZOPY-MEMLXQNLSA-N 0.000 claims 3
- VNDZFEOMLUNBNZ-MXVIHJGJSA-N C=12C(N)=NC=CN2C([C@@H]2CC[C@H](CC2)C(O)=O)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 Chemical compound C=12C(N)=NC=CN2C([C@@H]2CC[C@H](CC2)C(O)=O)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 VNDZFEOMLUNBNZ-MXVIHJGJSA-N 0.000 claims 3
- SWCIISDMFBNTHC-RZFKFIIISA-N Nc1nccn2c(nc(-c3ccc4ccc(nc4c3)-c3ccccc3)c12)[C@H]1CC[C@H](CN2C(=O)c3ccccc3C2=O)CC1 Chemical compound Nc1nccn2c(nc(-c3ccc4ccc(nc4c3)-c3ccccc3)c12)[C@H]1CC[C@H](CN2C(=O)c3ccccc3C2=O)CC1 SWCIISDMFBNTHC-RZFKFIIISA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 208000025865 Ulcer Diseases 0.000 claims 3
- MEBFFPWZDJFILV-UHFFFAOYSA-N [3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutyl]methanol Chemical compound C=12C(N)=NC=CN2C(C2CC(CO)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 MEBFFPWZDJFILV-UHFFFAOYSA-N 0.000 claims 3
- KQLFRRPQNLZQFD-UHFFFAOYSA-N [4-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclohexyl]methanol Chemical compound C=12C(N)=NC=CN2C(C2CCC(CO)CC2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 KQLFRRPQNLZQFD-UHFFFAOYSA-N 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- PABMBMQQWJOHIS-UHFFFAOYSA-N methyl 4-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N PABMBMQQWJOHIS-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 231100000397 ulcer Toxicity 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 230000006907 apoptotic process Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- ZNJRINDKQVUSQJ-UHFFFAOYSA-N 1-(2-phenylquinolin-7-yl)-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C(C)C)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 ZNJRINDKQVUSQJ-UHFFFAOYSA-N 0.000 claims 1
- JZMFTFDSJSFVTH-UHFFFAOYSA-N 1-(6-chloro-2-phenoxyquinolin-7-yl)-3-[3-[(dimethylamino)methyl]cyclobutyl]imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C(=CC3=CC=C(OC=4C=CC=CC=4)N=C3C=2)Cl)=C2N1C=CN=C2N JZMFTFDSJSFVTH-UHFFFAOYSA-N 0.000 claims 1
- FTNNJHIGEKILDE-UHFFFAOYSA-N 1-(6-chloro-2-phenoxyquinolin-7-yl)-3-cyclobutylimidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2OC1=CC=CC=C1 FTNNJHIGEKILDE-UHFFFAOYSA-N 0.000 claims 1
- XIQPRISBXRBPMP-UHFFFAOYSA-N 1-(6-chloro-2-phenylquinolin-7-yl)-3-[3-(2-methoxyethoxy)cyclobutyl]imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(OCCOC)CC1C1=NC(C=2C(=CC3=CC=C(N=C3C=2)C=2C=CC=CC=2)Cl)=C2N1C=CN=C2N XIQPRISBXRBPMP-UHFFFAOYSA-N 0.000 claims 1
- NPJOPWWUNCTQSY-UHFFFAOYSA-N 1-(6-chloro-2-phenylquinolin-7-yl)-3-[3-[(dimethylamino)methyl]cyclobutyl]imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C(=CC3=CC=C(N=C3C=2)C=2C=CC=CC=2)Cl)=C2N1C=CN=C2N NPJOPWWUNCTQSY-UHFFFAOYSA-N 0.000 claims 1
- IGWCMCHNENNYMS-UHFFFAOYSA-N 1-(6-chloro-2-phenylquinolin-7-yl)-3-cyclobutylimidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CC=C1 IGWCMCHNENNYMS-UHFFFAOYSA-N 0.000 claims 1
- CTTWBPHWZRHMJY-UHFFFAOYSA-N 1-(6-chloro-2-pyridin-2-ylquinolin-7-yl)-3-[3-[(dimethylamino)methyl]cyclobutyl]imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C(=CC3=CC=C(N=C3C=2)C=2N=CC=CC=2)Cl)=C2N1C=CN=C2N CTTWBPHWZRHMJY-UHFFFAOYSA-N 0.000 claims 1
- QOEGQGDHIOECBA-UHFFFAOYSA-N 1-(6-chloro-2-pyridin-2-ylquinolin-7-yl)-3-cyclobutylimidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CC=N1 QOEGQGDHIOECBA-UHFFFAOYSA-N 0.000 claims 1
- JSTPUNDUDLHYSG-UHFFFAOYSA-N 1-(6-chloro-2-thiophen-2-ylquinolin-7-yl)-3-[3-[(dimethylamino)methyl]cyclobutyl]imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C(=CC3=CC=C(N=C3C=2)C=2SC=CC=2)Cl)=C2N1C=CN=C2N JSTPUNDUDLHYSG-UHFFFAOYSA-N 0.000 claims 1
- NSPUAURZKYEZAQ-UHFFFAOYSA-N 1-(6-chloro-2-thiophen-2-ylquinolin-7-yl)-3-cyclobutylimidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CS1 NSPUAURZKYEZAQ-UHFFFAOYSA-N 0.000 claims 1
- LNENPGOMBMAEJP-UHFFFAOYSA-N 1-[4-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC(C=2N3C=CN=C(N)C3=C(C=3C=C4N=C(C=CC4=CC=3)C=3C=CC=CC=3)N=2)=C1 LNENPGOMBMAEJP-UHFFFAOYSA-N 0.000 claims 1
- BSPTWZDFLDXPKA-UHFFFAOYSA-N 3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1N(C)CCC(C=2N3C=CN=C(N)C3=C(C=3C=C4N=C(C=CC4=CC=3)C=3C=CC=CC=3)N=2)=C1 BSPTWZDFLDXPKA-UHFFFAOYSA-N 0.000 claims 1
- RCWDNTWEIXTBTG-UHFFFAOYSA-N 3-(6-bicyclo[3.1.0]hexanyl)-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2C3CCCC32)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 RCWDNTWEIXTBTG-UHFFFAOYSA-N 0.000 claims 1
- LLJPAIVIVLSZJV-UHFFFAOYSA-N 3-[3-(2-methoxyethoxy)cyclobutyl]-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(OCCOC)CC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N LLJPAIVIVLSZJV-UHFFFAOYSA-N 0.000 claims 1
- DXKBLTMTTDDSQV-UHFFFAOYSA-N 3-[3-(2-methoxyethoxy)cyclobutyl]-1-(4-methyl-2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(OCCOC)CC1C1=NC(C=2C=C3N=C(C=C(C)C3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N DXKBLTMTTDDSQV-UHFFFAOYSA-N 0.000 claims 1
- KTRLKEPQWZPLLL-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2OC1=CC=CC=C1 KTRLKEPQWZPLLL-UHFFFAOYSA-N 0.000 claims 1
- KCDLRDXYMVNZPG-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(2-phenylquinazolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C=C1N=2)=CC=C1C=NC=2C1=CC=CC=C1 KCDLRDXYMVNZPG-UHFFFAOYSA-N 0.000 claims 1
- IYTNOAIKJAKOBQ-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=N1 IYTNOAIKJAKOBQ-UHFFFAOYSA-N 0.000 claims 1
- BPQDPJNGZRONGX-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CS1 BPQDPJNGZRONGX-UHFFFAOYSA-N 0.000 claims 1
- SYJUORNLAUSPHR-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(3-phenylquinoxalin-6-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C=C1N=2)=CC=C1N=CC=2C1=CC=CC=C1 SYJUORNLAUSPHR-UHFFFAOYSA-N 0.000 claims 1
- ZHKAOBNTJHXVSR-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(4-methyl-2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound N=1C2=CC(C3=C4C(N)=NC=CN4C(C4CC(CN5CCC5)C4)=N3)=CC=C2C(C)=CC=1OC1=CC=CC=C1 ZHKAOBNTJHXVSR-UHFFFAOYSA-N 0.000 claims 1
- FXRPEGTVXBMEDQ-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(4-methyl-2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=1C=C2C(C)=CC(C=3C=CC=CC=3)=NC2=CC=1C(=C1C(N)=NC=CN11)N=C1C(C1)CC1CN1CCC1 FXRPEGTVXBMEDQ-UHFFFAOYSA-N 0.000 claims 1
- BLKIKWVZRFFMSI-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(4-methyl-2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=1C=C2C(C)=CC(C=3N=CC=CC=3)=NC2=CC=1C(=C1C(N)=NC=CN11)N=C1C(C1)CC1CN1CCC1 BLKIKWVZRFFMSI-UHFFFAOYSA-N 0.000 claims 1
- ZXSMEAMNZCPABU-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(4-methyl-2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=1C=C2C(C)=CC(C=3SC=CC=3)=NC2=CC=1C(=C1C(N)=NC=CN11)N=C1C(C1)CC1CN1CCC1 ZXSMEAMNZCPABU-UHFFFAOYSA-N 0.000 claims 1
- WNZJXGHVWGHWBZ-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(6-chloro-2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2OC1=CC=CC=C1 WNZJXGHVWGHWBZ-UHFFFAOYSA-N 0.000 claims 1
- HAFVYVTYISTQCA-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(6-chloro-2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CC=C1 HAFVYVTYISTQCA-UHFFFAOYSA-N 0.000 claims 1
- BBUMOKGWHZSDSV-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(6-chloro-2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CC=N1 BBUMOKGWHZSDSV-UHFFFAOYSA-N 0.000 claims 1
- IGQGOZJQNANYAA-UHFFFAOYSA-N 3-[3-(azetidin-1-ylmethyl)cyclobutyl]-1-(6-chloro-2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CC(CN3CCC3)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CS1 IGQGOZJQNANYAA-UHFFFAOYSA-N 0.000 claims 1
- AGAUBSNLJPHZHW-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(OC=4C=CC=CC=4)C=CC3=CC=2)=C2N1C=CN=C2N AGAUBSNLJPHZHW-UHFFFAOYSA-N 0.000 claims 1
- FSYHSNLAYZLREB-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N FSYHSNLAYZLREB-UHFFFAOYSA-N 0.000 claims 1
- IURNCGNYCSSLFG-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2N=CC=CC=2)=C2N1C=CN=C2N IURNCGNYCSSLFG-UHFFFAOYSA-N 0.000 claims 1
- PTOFUBGVEVTDOA-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2SC=CC=2)=C2N1C=CN=C2N PTOFUBGVEVTDOA-UHFFFAOYSA-N 0.000 claims 1
- MLXBGVQCKOFVTE-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(4-methyl-2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(OC=4C=CC=CC=4)C=C(C)C3=CC=2)=C2N1C=CN=C2N MLXBGVQCKOFVTE-UHFFFAOYSA-N 0.000 claims 1
- QAEFNWNIDUIYLU-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(4-methyl-2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(C=C(C)C3=CC=2)C=2C=CC=CC=2)=C2N1C=CN=C2N QAEFNWNIDUIYLU-UHFFFAOYSA-N 0.000 claims 1
- UEPKBNLLPLXRBW-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(4-methyl-2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(C=C(C)C3=CC=2)C=2N=CC=CC=2)=C2N1C=CN=C2N UEPKBNLLPLXRBW-UHFFFAOYSA-N 0.000 claims 1
- FLYYUFXEANIZJX-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]cyclobutyl]-1-(4-methyl-2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1C(CN(C)C)CC1C1=NC(C=2C=C3N=C(C=C(C)C3=CC=2)C=2SC=CC=2)=C2N1C=CN=C2N FLYYUFXEANIZJX-UHFFFAOYSA-N 0.000 claims 1
- SHDOYMJQFXSBEK-UHFFFAOYSA-N 3-[4-(aminomethyl)cyclohexyl]-1-(2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1CC(CN)CCC1C1=NC(C=2C=C3N=C(OC=4C=CC=CC=4)C=CC3=CC=2)=C2N1C=CN=C2N SHDOYMJQFXSBEK-UHFFFAOYSA-N 0.000 claims 1
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- HAZNXCGIXJLHAL-UHFFFAOYSA-N 3-[4-(aminomethyl)cyclohexyl]-1-(2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C1CC(CN)CCC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2SC=CC=2)=C2N1C=CN=C2N HAZNXCGIXJLHAL-UHFFFAOYSA-N 0.000 claims 1
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- OTEYCFHTSSWJMC-UHFFFAOYSA-N 3-[4-amino-5-(2-phenylquinolin-7-yl)imidazo[5,1-f][1,2,4]triazin-7-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=NN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 OTEYCFHTSSWJMC-UHFFFAOYSA-N 0.000 claims 1
- CNHWBZDZZFOUCS-UHFFFAOYSA-N 3-[4-amino-5-(2-pyridin-2-ylquinolin-7-yl)imidazo[5,1-f][1,2,4]triazin-7-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=NN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=N1 CNHWBZDZZFOUCS-UHFFFAOYSA-N 0.000 claims 1
- UMZJQOGWEHNJSW-UHFFFAOYSA-N 3-[4-amino-5-(2-thiophen-2-ylquinolin-7-yl)imidazo[5,1-f][1,2,4]triazin-7-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=NN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CS1 UMZJQOGWEHNJSW-UHFFFAOYSA-N 0.000 claims 1
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- SIEHWDBFIIYBOG-UHFFFAOYSA-N 3-[8-amino-1-(2-anilino-8-fluoro-4-methylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound N=1C2=C(F)C(C3=C4C(N)=NC=CN4C(C4CC(O)C4)=N3)=CC=C2C(C)=CC=1NC1=CC=CC=C1 SIEHWDBFIIYBOG-UHFFFAOYSA-N 0.000 claims 1
- HORASWPXVYMFDE-UHFFFAOYSA-N 3-[8-amino-1-(2-anilino-8-fluoroquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=C1N=2)F)=CC=C1C=CC=2NC1=CC=CC=C1 HORASWPXVYMFDE-UHFFFAOYSA-N 0.000 claims 1
- KNNNVAYJYWJUJS-UHFFFAOYSA-N 3-[8-amino-1-(2-anilinoquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2NC1=CC=CC=C1 KNNNVAYJYWJUJS-UHFFFAOYSA-N 0.000 claims 1
- FTZQWHBTSPATPY-UHFFFAOYSA-N 3-[8-amino-1-(2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2OC1=CC=CC=C1 FTZQWHBTSPATPY-UHFFFAOYSA-N 0.000 claims 1
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- OEONHNQCPJBVRI-UHFFFAOYSA-N 3-[8-amino-1-(2-phenylquinazolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=NC=2C1=CC=CC=C1 OEONHNQCPJBVRI-UHFFFAOYSA-N 0.000 claims 1
- XIGQKXNIOIKTTM-UHFFFAOYSA-N 3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=C1 XIGQKXNIOIKTTM-UHFFFAOYSA-N 0.000 claims 1
- JXCXKCPTKOPYKT-UHFFFAOYSA-N 3-[8-amino-1-(2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=N1 JXCXKCPTKOPYKT-UHFFFAOYSA-N 0.000 claims 1
- SJIHLZCTWLBOEX-UHFFFAOYSA-N 3-[8-amino-1-(2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CS1 SJIHLZCTWLBOEX-UHFFFAOYSA-N 0.000 claims 1
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- NGUMIDBSGGXFJK-UHFFFAOYSA-N 3-[8-amino-1-(6-chloro-2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2OC1=CC=CC=C1 NGUMIDBSGGXFJK-UHFFFAOYSA-N 0.000 claims 1
- VFMSUJWZZRHUCC-UHFFFAOYSA-N 3-[8-amino-1-(6-chloro-2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CC=C1 VFMSUJWZZRHUCC-UHFFFAOYSA-N 0.000 claims 1
- GMWAJVNZYVRKSB-UHFFFAOYSA-N 3-[8-amino-1-(6-chloro-2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CC=N1 GMWAJVNZYVRKSB-UHFFFAOYSA-N 0.000 claims 1
- WTNLZLHHVBFFSL-UHFFFAOYSA-N 3-[8-amino-1-(6-chloro-2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=CC1=CC=2)Cl)=CC1=NC=2C1=CC=CS1 WTNLZLHHVBFFSL-UHFFFAOYSA-N 0.000 claims 1
- NDRZZIJTNDXFKZ-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=C1N=2)F)=CC=C1C=CC=2OC1=CC=CC=C1 NDRZZIJTNDXFKZ-UHFFFAOYSA-N 0.000 claims 1
- VDDQUSUVKJGVCE-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=C1N=2)F)=CC=C1C=CC=2C1=CC=CC=C1 VDDQUSUVKJGVCE-UHFFFAOYSA-N 0.000 claims 1
- OIWSHRFQGPWBTG-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=C1N=2)F)=CC=C1C=CC=2C1=CC=CC=N1 OIWSHRFQGPWBTG-UHFFFAOYSA-N 0.000 claims 1
- XJOUBTVPJCMYSW-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=12C(N)=NC=CN2C(C2CC(O)C2)=NC=1C(C(=C1N=2)F)=CC=C1C=CC=2C1=CC=CS1 XJOUBTVPJCMYSW-UHFFFAOYSA-N 0.000 claims 1
- CLMNYETVRVPFNQ-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-4-methyl-2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound N=1C2=C(F)C(C3=C4C(N)=NC=CN4C(C4CC(O)C4)=N3)=CC=C2C(C)=CC=1OC1=CC=CC=C1 CLMNYETVRVPFNQ-UHFFFAOYSA-N 0.000 claims 1
- JSFZRMQPAZXPJZ-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-4-methyl-2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=1C=C2C(C)=CC(C=3C=CC=CC=3)=NC2=C(F)C=1C(=C1C(N)=NC=CN11)N=C1C1CC(O)C1 JSFZRMQPAZXPJZ-UHFFFAOYSA-N 0.000 claims 1
- ADFOUEFAROFAPA-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-4-methyl-2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=1C=C2C(C)=CC(C=3N=CC=CC=3)=NC2=C(F)C=1C(=C1C(N)=NC=CN11)N=C1C1CC(O)C1 ADFOUEFAROFAPA-UHFFFAOYSA-N 0.000 claims 1
- FCCPCXYUVSJPMH-UHFFFAOYSA-N 3-[8-amino-1-(8-fluoro-4-methyl-2-thiophen-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutan-1-ol Chemical compound C=1C=C2C(C)=CC(C=3SC=CC=3)=NC2=C(F)C=1C(=C1C(N)=NC=CN11)N=C1C1CC(O)C1 FCCPCXYUVSJPMH-UHFFFAOYSA-N 0.000 claims 1
- KJEIFAVPAAICFH-UHFFFAOYSA-N 3-cyclobutyl-1-(2-phenoxyquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)=NC=1C(C=C1N=2)=CC=C1C=CC=2OC1=CC=CC=C1 KJEIFAVPAAICFH-UHFFFAOYSA-N 0.000 claims 1
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- RXACVQGKQQDPHW-UHFFFAOYSA-N 3-cyclobutyl-1-(2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)=NC=1C(C=C1N=2)=CC=C1C=CC=2C1=CC=CC=N1 RXACVQGKQQDPHW-UHFFFAOYSA-N 0.000 claims 1
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- APIFMUCUEBBRIL-UHFFFAOYSA-N 3-cyclobutyl-1-(8-fluoro-2-pyridin-2-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine Chemical compound C=12C(N)=NC=CN2C(C2CCC2)=NC=1C(C(=C1N=2)F)=CC=C1C=CC=2C1=CC=CC=N1 APIFMUCUEBBRIL-UHFFFAOYSA-N 0.000 claims 1
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- XFAUYDLYCUJYSV-UHFFFAOYSA-N 4-[4-amino-5-(2-phenoxyquinolin-7-yl)imidazo[5,1-f][1,2,4]triazin-7-yl]-n-methylcyclohexane-1-carboxamide Chemical compound C1CC(C(=O)NC)CCC1C1=NC(C=2C=C3N=C(OC=4C=CC=CC=4)C=CC3=CC=2)=C2N1N=CN=C2N XFAUYDLYCUJYSV-UHFFFAOYSA-N 0.000 claims 1
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- UAQXWZIQHXZCJM-UHFFFAOYSA-N 4-[4-amino-5-(2-phenylquinolin-7-yl)imidazo[5,1-f][1,2,4]triazin-7-yl]-n-methylcyclohexane-1-carboxamide Chemical compound C1CC(C(=O)NC)CCC1C1=NC(C=2C=C3N=C(C=CC3=CC=2)C=2C=CC=CC=2)=C2N1N=CN=C2N UAQXWZIQHXZCJM-UHFFFAOYSA-N 0.000 claims 1
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EP (4) | EP2305682A1 (fr) |
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US7429596B2 (en) * | 2003-06-20 | 2008-09-30 | The Regents Of The University Of California | 1H-pyrrolo [2,3-D] pyrimidine derivatives and methods of use thereof |
CN1898240B (zh) * | 2003-10-15 | 2011-08-03 | Osi制药公司 | 咪唑并吡嗪类酪氨酸激酶抑制剂 |
BRPI0509576A (pt) | 2004-04-02 | 2007-05-29 | Osi Pharm Inc | composto, método de tratamento de um paciente tendo uma condição que é mediada pela atividade de proteìna quinase, e, composição farmacêutica |
TW200613306A (en) * | 2004-07-20 | 2006-05-01 | Osi Pharm Inc | Imidazotriazines as protein kinase inhibitors |
JP2008520744A (ja) * | 2004-11-19 | 2008-06-19 | ザ・レジェンツ・オブ・ザ・ユニバーシティ・オブ・カリフォルニア | 抗炎症性ピラゾロピリミジン |
EP2385053B1 (fr) * | 2005-11-17 | 2013-10-02 | OSI Pharmaceuticals, Inc. | Intermédiaires pour la préparation de composés bicycliques condensés comme inhibiteurs mTOR |
AR057960A1 (es) | 2005-12-02 | 2007-12-26 | Osi Pharm Inc | Inhibidores de proteina quinasa biciclicos |
TW200730529A (en) * | 2005-12-07 | 2007-08-16 | Osi Pharm Inc | Process to prepare substituted imidazopyrazine compounds |
US8575164B2 (en) * | 2005-12-19 | 2013-11-05 | OSI Pharmaceuticals, LLC | Combination cancer therapy |
JP2009520028A (ja) * | 2005-12-19 | 2009-05-21 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | Igfr抑制剤および抗癌剤の併用 |
ES2545907T3 (es) * | 2005-12-29 | 2015-09-16 | Abbvie Inc. | Inhibidores de proteína quinasa |
CN101003537A (zh) * | 2006-01-17 | 2007-07-25 | 上海恒瑞医药有限公司 | 吡咯并哒嗪类衍生物及其制备方法和用途 |
EP1981890A2 (fr) * | 2006-01-25 | 2008-10-22 | OSI Pharmaceuticals, Inc. | INHIBITEURS DE mTOR INSATURES |
NZ571182A (en) * | 2006-04-04 | 2010-09-30 | Univ California | Pyrazolo[3,4-d]pyrimidines |
DE102006016426A1 (de) * | 2006-04-07 | 2007-10-11 | Merck Patent Gmbh | Neuartige Cyclobutyl-Verbindungen als Kinase-Inhibitoren |
WO2007132307A1 (fr) * | 2006-05-09 | 2007-11-22 | Pfizer Products Inc. | Dérivés d'acide cycloalkylaminé et compositions pharmaceutiques à base de ceux-ci |
WO2008021781A1 (fr) | 2006-08-07 | 2008-02-21 | Incyte Corporation | Utilisation de triazolotriazines en tant qu'inhibiteurs des kinases |
DE102006043443A1 (de) * | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
ES2689444T3 (es) * | 2006-11-22 | 2018-11-14 | Incyte Holdings Corporation | Imidazotriazinas e imidazopirimidinas como inhibidores de la quinasa |
WO2008076143A1 (fr) * | 2006-12-18 | 2008-06-26 | Osi Pharmaceuticals, Inc. | Combinaison d'un inhibiteur de l'igfr et d'un agent anticancéreux |
TW200900070A (en) * | 2007-02-27 | 2009-01-01 | Osi Pharm Inc | Combination cancer therapy |
US8124759B2 (en) | 2007-05-09 | 2012-02-28 | Abbott Laboratories | Inhibitors of protein kinases |
WO2008141140A1 (fr) * | 2007-05-09 | 2008-11-20 | Abbott Laboratories | Composés hétérocycliques condensés utilisés en tant qu'inhibiteurs de protéines kinases |
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