RU2016114128A - ЗАМЕЩЕННЫЕ СОЕДИНЕНИЯ ПИРАЗОЛО[1,5-а]ПИРИМИДИНА КАК ИНГИБИТОРЫ КИНАЗЫ TRK - Google Patents
ЗАМЕЩЕННЫЕ СОЕДИНЕНИЯ ПИРАЗОЛО[1,5-а]ПИРИМИДИНА КАК ИНГИБИТОРЫ КИНАЗЫ TRK Download PDFInfo
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- RU2016114128A RU2016114128A RU2016114128A RU2016114128A RU2016114128A RU 2016114128 A RU2016114128 A RU 2016114128A RU 2016114128 A RU2016114128 A RU 2016114128A RU 2016114128 A RU2016114128 A RU 2016114128A RU 2016114128 A RU2016114128 A RU 2016114128A
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- RU
- Russia
- Prior art keywords
- pyrrolidin
- pyrazolo
- carboxamide
- pyrimidine
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 5
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title 1
- -1 morpholinyl ethoxy, morpholinyl ethyl Chemical group 0.000 claims 149
- 125000000217 alkyl group Chemical group 0.000 claims 133
- XMRIUEGHBZTNND-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC=NC2=C(C(=O)N)C=NN21 XMRIUEGHBZTNND-UHFFFAOYSA-N 0.000 claims 57
- 238000000034 method Methods 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 8
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 4
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims 4
- CYJPVTPYPTUQAC-HYSRAYMDSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(4-hydroxy-4-methylcyclohexyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CC(C)(O)CCC1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 CYJPVTPYPTUQAC-HYSRAYMDSA-N 0.000 claims 4
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000010802 sludge Substances 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims 2
- BBRVRCQHOJGIEM-QGZVFWFLSA-N 5-[(2r)-2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl]-n-(2-hydroxy-2-methylpropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NCC(C)(C)O)C=NN3C=C2)CCC1 BBRVRCQHOJGIEM-QGZVFWFLSA-N 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- LJCJRRKKAKAKRV-UHFFFAOYSA-N (2-amino-2-methylpropyl) 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CC(C)(N)COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LJCJRRKKAKAKRV-UHFFFAOYSA-N 0.000 claims 1
- PFTUHNICIXICMP-LJQANCHMSA-N 1-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 PFTUHNICIXICMP-LJQANCHMSA-N 0.000 claims 1
- HUMIANOGLZOVBP-MRXNPFEDSA-N 1-[[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonyl]amino]cyclopropane-1-carboxylic acid Chemical compound C1=NN2C=CC(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)=NC2=C1C(=O)NC1(C(=O)O)CC1 HUMIANOGLZOVBP-MRXNPFEDSA-N 0.000 claims 1
- BNDQCVSMOIBZCI-GOSISDBHSA-N 1-cyclopropyl-5-[(2r)-2-[3-fluoro-5-(2-methoxyethoxy)phenyl]pyrrolidin-1-yl]pyrazole Chemical compound COCCOC1=CC(F)=CC([C@@H]2N(CCC2)C=2N(N=CC=2)C2CC2)=C1 BNDQCVSMOIBZCI-GOSISDBHSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- HYQUCWQCNZSJRP-HXUWFJFHSA-N 2-[1-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 HYQUCWQCNZSJRP-HXUWFJFHSA-N 0.000 claims 1
- 125000006016 2-bromoethoxy group Chemical group 0.000 claims 1
- 125000006012 2-chloroethoxy group Chemical group 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- LKKQICCORQINHH-UHFFFAOYSA-N 3-fluoro-3H-pyridin-6-one Chemical group FC1C=CC(=O)N=C1 LKKQICCORQINHH-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- ZZZONOLAOQEATF-QGZVFWFLSA-N 4-[[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazol-1-yl]methyl]-1-methylimidazole Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=CC=NN1CC=1N=CN(C=1)C ZZZONOLAOQEATF-QGZVFWFLSA-N 0.000 claims 1
- YYWBCTXPSKWIQX-QGZVFWFLSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-1-[2-(1H-imidazol-5-yl)ethyl]pyrazole Chemical compound N1C=NC(=C1)CCN1N=CC=C1N1[C@H](CCC1)C1=C(C=CC(=C1)F)F YYWBCTXPSKWIQX-QGZVFWFLSA-N 0.000 claims 1
- WGQPLEIMNLEFTL-QGZVFWFLSA-N 5-[(2R)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]-N-(5-hydroxypyridin-2-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CN1C=C(F)C=C([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)C(=O)NC2=NC=C(O)C=C2)C1=O WGQPLEIMNLEFTL-QGZVFWFLSA-N 0.000 claims 1
- OTCSCPHWCZZRDC-LBXVMSDZSA-N 5-[(2R)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-N-(4-methylsulfonylcyclohexyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@H]1CCCN1C1=NC2=C(C=NN2C=C1)C(=O)NC1CCC(CC1)S(C)(=O)=O OTCSCPHWCZZRDC-LBXVMSDZSA-N 0.000 claims 1
- DUJWGLCTYAWISR-MRXNPFEDSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n,n-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N(C)C)=CC(F)=CC=C1F DUJWGLCTYAWISR-MRXNPFEDSA-N 0.000 claims 1
- XWDLDVQSUXONBG-LJQANCHMSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(3-methylpyridin-2-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=CC=CN=C1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 XWDLDVQSUXONBG-LJQANCHMSA-N 0.000 claims 1
- IXPTZPMMOJWPBZ-JBBXEZCESA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2r,3s)-1,3-dihydroxybutan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N[C@H](CO)[C@@H](O)C)=CC(F)=CC=C1F IXPTZPMMOJWPBZ-JBBXEZCESA-N 0.000 claims 1
- PXRHKVCFGOFIIB-SUMWQHHRSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s)-2,3-dihydroxypropoxy]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NOC[C@@H](O)CO)=CC(F)=CC=C1F PXRHKVCFGOFIIB-SUMWQHHRSA-N 0.000 claims 1
- GSSDAQWHOJFZRE-SUMWQHHRSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s)-2,3-dihydroxypropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC[C@H](O)CO)=CC(F)=CC=C1F GSSDAQWHOJFZRE-SUMWQHHRSA-N 0.000 claims 1
- IXPTZPMMOJWPBZ-OCBCSQNSSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s,3r)-1,3-dihydroxybutan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N[C@@H](CO)[C@H](O)C)=CC(F)=CC=C1F IXPTZPMMOJWPBZ-OCBCSQNSSA-N 0.000 claims 1
- IXPTZPMMOJWPBZ-UYHISHBKSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s,3s)-1,3-dihydroxybutan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N[C@@H](CO)[C@@H](O)C)=CC(F)=CC=C1F IXPTZPMMOJWPBZ-UYHISHBKSA-N 0.000 claims 1
- OMWFIVWGJYQGKO-GOSISDBHSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[1-(methanesulfonamido)-2-methylpropan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)(CNS(C)(=O)=O)C)=CC(F)=CC=C1F OMWFIVWGJYQGKO-GOSISDBHSA-N 0.000 claims 1
- FUHAANUNQWUCBT-OAHLLOKOSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-methoxypyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NOC)=CC(F)=CC=C1F FUHAANUNQWUCBT-OAHLLOKOSA-N 0.000 claims 1
- MBZCRLUONJJYJU-OAHLLOKOSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC)=CC(F)=CC=C1F MBZCRLUONJJYJU-OAHLLOKOSA-N 0.000 claims 1
- JBTQGTQNCVBRNY-CQSZACIVSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N)=CC(F)=CC=C1F JBTQGTQNCVBRNY-CQSZACIVSA-N 0.000 claims 1
- YFZGYNMBIQOANX-TWOQFEAHSA-N 5-[(2r)-2-(2-ethyl-5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(1s,3s)-3-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CCC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N[C@@H]4C[C@@H](O)CC4)C=NN3C=C2)CCC1 YFZGYNMBIQOANX-TWOQFEAHSA-N 0.000 claims 1
- ISGDOVGHVRHZFY-AFMYVXGZSA-N 5-[(2r)-2-(3-fluorophenyl)pyrrolidin-1-yl]-n-(4-hydroxycyclohexyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CC(O)CCC1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=CC=3)C=CN2N=C1 ISGDOVGHVRHZFY-AFMYVXGZSA-N 0.000 claims 1
- MLIFTZTWMYPZAL-OAHLLOKOSA-N 5-[(2r)-2-(3-fluorophenyl)pyrrolidin-1-yl]-n-methoxypyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NOC)=CC=CC(F)=C1 MLIFTZTWMYPZAL-OAHLLOKOSA-N 0.000 claims 1
- GSRZAXNWBZUUOT-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]-n-propan-2-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)C)=CC(F)=CN(C)C1=O GSRZAXNWBZUUOT-MRXNPFEDSA-N 0.000 claims 1
- IHLOJSUOOQFANO-HXUWFJFHSA-N 5-[(2r)-2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl]-n-(2-morpholin-4-ylethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NCCN4CCOCC4)C=NN3C=C2)CCC1 IHLOJSUOOQFANO-HXUWFJFHSA-N 0.000 claims 1
- DCLFPTZRYFZAKO-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(1-fluoro-2-methylpropan-2-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC(C)(C)CF)C=NN3C=C2)CCC1 DCLFPTZRYFZAKO-MRXNPFEDSA-N 0.000 claims 1
- WRXZQYJJPXFOIB-LADRWXRNSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(4-hydroxycyclohexyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4CCC(O)CC4)C=NN3C=C2)CCC1 WRXZQYJJPXFOIB-LADRWXRNSA-N 0.000 claims 1
- KUMKUBXRGRIPEY-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(5-methyl-1h-pyrazol-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC=4NN=C(C)C=4)C=NN3C=C2)CCC1 KUMKUBXRGRIPEY-MRXNPFEDSA-N 0.000 claims 1
- REPYLSGOOOJRSV-CQSZACIVSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-methoxypyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NOC)=CC(F)=CN=C1OC REPYLSGOOOJRSV-CQSZACIVSA-N 0.000 claims 1
- WAAWHVXSMHHZCZ-CQSZACIVSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC)=CC(F)=CN=C1OC WAAWHVXSMHHZCZ-CQSZACIVSA-N 0.000 claims 1
- AYXUQBNBYRQZDH-OAHLLOKOSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC)=CC(F)=CN=C1C AYXUQBNBYRQZDH-OAHLLOKOSA-N 0.000 claims 1
- PMKFFRXMNWSTLH-QGZVFWFLSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-propan-2-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)C)=CC(F)=CN=C1C PMKFFRXMNWSTLH-QGZVFWFLSA-N 0.000 claims 1
- UEWLKIVHINNLJX-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(1-methylcyclopropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C=CC(N3[C@H](CCC3)C=3C=C(F)C=NC=3)=NC2=C1C(=O)NC1(C)CC1 UEWLKIVHINNLJX-MRXNPFEDSA-N 0.000 claims 1
- KJYXTMLZCPHUAV-IAQYHMDHSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N[C@H](C)C(F)(F)F)=CN=CC(F)=C1 KJYXTMLZCPHUAV-IAQYHMDHSA-N 0.000 claims 1
- ONENEBSQEBHUSO-CQSZACIVSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-methoxypyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NOC)=CN=CC(F)=C1 ONENEBSQEBHUSO-CQSZACIVSA-N 0.000 claims 1
- AOJFJIKCNFEJMA-CQSZACIVSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC)=CN=CC(F)=C1 AOJFJIKCNFEJMA-CQSZACIVSA-N 0.000 claims 1
- KOZAUWSJLNLRBA-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-propan-2-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)C)=CN=CC(F)=C1 KOZAUWSJLNLRBA-MRXNPFEDSA-N 0.000 claims 1
- LTWRCYLYOAZNPD-FQNRMIAFSA-N 5-[(2r)-2-[2-(2,3-dihydroxypropoxy)-5-fluorophenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N)=CC(F)=CC=C1OCC(O)CO LTWRCYLYOAZNPD-FQNRMIAFSA-N 0.000 claims 1
- JDIGZDKHSLPKGP-KPMSDPLLSA-N 5-[(2r)-2-[2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-5-fluorophenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound O1C(C)(C)OCC1COC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(N)=O)C=NN3C=C2)CCC1 JDIGZDKHSLPKGP-KPMSDPLLSA-N 0.000 claims 1
- UGWUALPBTGHKQH-FBMWCMRBSA-N 5-[(2r)-2-[3-(2,3-dihydroxypropoxy)-5-fluorophenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N)=CC(F)=CC(OCC(O)CO)=C1 UGWUALPBTGHKQH-FBMWCMRBSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
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| US22419609P | 2009-07-09 | 2009-07-09 | |
| US61/224,196 | 2009-07-09 | ||
| US34676710P | 2010-05-20 | 2010-05-20 | |
| US61/346,767 | 2010-05-20 |
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| RU2012104493/04A Division RU2584157C2 (ru) | 2009-07-09 | 2010-07-09 | ЗАМЕЩЕННЫЕ СОЕДИНЕНИЯ ПИРАЗОЛО[1,5-a]ПИРИМИДИНА КАК ИНГИБИТОРЫ КИНАЗЫ TRK |
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| RU2012104493/04A RU2584157C2 (ru) | 2009-07-09 | 2010-07-09 | ЗАМЕЩЕННЫЕ СОЕДИНЕНИЯ ПИРАЗОЛО[1,5-a]ПИРИМИДИНА КАК ИНГИБИТОРЫ КИНАЗЫ TRK |
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| RU2012104493/04A RU2584157C2 (ru) | 2009-07-09 | 2010-07-09 | ЗАМЕЩЕННЫЕ СОЕДИНЕНИЯ ПИРАЗОЛО[1,5-a]ПИРИМИДИНА КАК ИНГИБИТОРЫ КИНАЗЫ TRK |
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