JP2012532888A5 - - Google Patents
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- JP2012532888A5 JP2012532888A5 JP2012519764A JP2012519764A JP2012532888A5 JP 2012532888 A5 JP2012532888 A5 JP 2012532888A5 JP 2012519764 A JP2012519764 A JP 2012519764A JP 2012519764 A JP2012519764 A JP 2012519764A JP 2012532888 A5 JP2012532888 A5 JP 2012532888A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidin
- pyrazolo
- carboxamide
- pyrimidine
- alkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 254
- 150000001875 compounds Chemical class 0.000 claims description 104
- -1 2,5-difluorophenyl Chemical group 0.000 claims description 95
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 7
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 2
- 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 47
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims 3
- 201000008937 atopic dermatitis Diseases 0.000 claims 3
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 3
- UEHKWTJSMNTTCC-SJKOYZFVSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-N-[(2R)-2-hydroxypropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C[C@@H](O)CNC(=O)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=C(F)C=CC(F)=C1 UEHKWTJSMNTTCC-SJKOYZFVSA-N 0.000 claims 2
- 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 2
- 208000015181 infectious disease Diseases 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
- GNFIVOXDMLGGJJ-MRXNPFEDSA-N 1-[2-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazol-1-yl]ethyl]imidazolidin-2-one Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=CC=NN1CCN1C(NCC1)=O GNFIVOXDMLGGJJ-MRXNPFEDSA-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
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[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
- PEUXFCOIQKEZCE-CQSZACIVSA-N 5-[(2r)-2-(2-chloro-5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(2-hydroxyethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NOCCO)=CC(F)=CN=C1Cl PEUXFCOIQKEZCE-CQSZACIVSA-N 0.000 claims 1
- CXFMNHBMKOIQLW-QGZVFWFLSA-N 5-[(2r)-2-(2-chloro-5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[2-[(2-methylpropan-2-yl)oxy]ethoxy]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NOCCOC(C)(C)C)=CC(F)=CN=C1Cl CXFMNHBMKOIQLW-QGZVFWFLSA-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
- LZJSAQIUAQDIAJ-CQSZACIVSA-N 5-[(2r)-2-(3-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=CC(F)=C1 LZJSAQIUAQDIAJ-CQSZACIVSA-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
- 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 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
- YLAKIDRGVDYWAA-OAHLLOKOSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NCCO)C=NN3C=C2)CCC1 YLAKIDRGVDYWAA-OAHLLOKOSA-N 0.000 claims 1
- VTUVGNKQBUVKIW-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(3-hydroxypropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NCCCO)C=NN3C=C2)CCC1 VTUVGNKQBUVKIW-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
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- ZOHMFCHQNJCASG-RHSMWYFYSA-N n-[(2r)-2,3-dihydroxypropyl]-5-[(2r)-2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC[C@@H](O)CO)C=NN3C=C2)CCC1 ZOHMFCHQNJCASG-RHSMWYFYSA-N 0.000 claims 1
- IVHDXWQQZJTUMV-CXAGYDPISA-N n-[(2r)-2,3-dihydroxypropyl]-5-[(2r)-2-[5-fluoro-2-(trifluoromethyl)phenyl]pyrrolidin-1-yl]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=C1C(F)(F)F IVHDXWQQZJTUMV-CXAGYDPISA-N 0.000 claims 1
- ZOHMFCHQNJCASG-WMLDXEAASA-N n-[(2s)-2,3-dihydroxypropyl]-5-[(2r)-2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC[C@H](O)CO)C=NN3C=C2)CCC1 ZOHMFCHQNJCASG-WMLDXEAASA-N 0.000 claims 1
- HGBUMXKTCONBMP-XJKSGUPXSA-N n-[(2s)-2,3-dihydroxypropyl]-5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-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@H](O)CO)C=NN3C=C2)CCC1 HGBUMXKTCONBMP-XJKSGUPXSA-N 0.000 claims 1
- IVHDXWQQZJTUMV-SUMWQHHRSA-N n-[(2s)-2,3-dihydroxypropyl]-5-[(2r)-2-[5-fluoro-2-(trifluoromethyl)phenyl]pyrrolidin-1-yl]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=C1C(F)(F)F IVHDXWQQZJTUMV-SUMWQHHRSA-N 0.000 claims 1
- FZWUREXRAHZCKC-CZUORRHYSA-N n-[(2s)-3-chloro-2-hydroxypropyl]-5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-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@H](O)CCl)C=NN3C=C2)CCC1 FZWUREXRAHZCKC-CZUORRHYSA-N 0.000 claims 1
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- QVEBEDUBSUAZSH-UHFFFAOYSA-N n-cyclobutyl-5-[2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CN=CC(C2N(CCC2)C2=NC3=C(C(=O)NC4CCC4)C=NN3C=C2)=C1 QVEBEDUBSUAZSH-UHFFFAOYSA-N 0.000 claims 1
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- MQONFTAVRMZHBN-QGZVFWFLSA-N n-cyclopropyl-5-[(2r)-2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)CCC1 MQONFTAVRMZHBN-QGZVFWFLSA-N 0.000 claims 1
- JKTPHVQLCMLNMW-MRXNPFEDSA-N n-cyclopropyl-5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)CCC1 JKTPHVQLCMLNMW-MRXNPFEDSA-N 0.000 claims 1
- ZBJDRRTVBWHVAP-MRXNPFEDSA-N n-cyclopropyl-5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CN=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)=C1 ZBJDRRTVBWHVAP-MRXNPFEDSA-N 0.000 claims 1
- ZGPOATYOAANSTK-LRTDYKAYSA-N n-cyclopropyl-5-[(2r)-2-[2-(2,3-dihydroxypropoxy)-5-fluorophenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound OCC(O)COC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)CCC1 ZGPOATYOAANSTK-LRTDYKAYSA-N 0.000 claims 1
- SVIHXEVVNNRVEM-BDPMCISCSA-N n-cyclopropyl-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(=O)NC4CC4)C=NN3C=C2)CCC1 SVIHXEVVNNRVEM-BDPMCISCSA-N 0.000 claims 1
- YDZSAJWQPHVDHL-UUSAFJCLSA-N n-cyclopropyl-5-[(2r)-2-[3-(2,3-dihydroxypropoxy)-5-fluorophenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound OCC(O)COC1=CC(F)=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)=C1 YDZSAJWQPHVDHL-UUSAFJCLSA-N 0.000 claims 1
- HLAYAPGHRGSWFL-LWMIZPGFSA-N n-cyclopropyl-5-[(2r)-2-[3-[(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(F)=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)=C1 HLAYAPGHRGSWFL-LWMIZPGFSA-N 0.000 claims 1
- DXRCURBJOZPWHE-JOCHJYFZSA-N n-cyclopropyl-5-[(2r)-2-[5-fluoro-2-(2-morpholin-4-ylethoxy)phenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)=CC(F)=CC=C1OCCN1CCOCC1 DXRCURBJOZPWHE-JOCHJYFZSA-N 0.000 claims 1
- DHEFBJXZYSKWIF-NVXWUHKLSA-N n-cyclopropyl-5-[(2r,4r)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N1([C@H](C[C@H](C1)O)C=1C=C(F)C=CC=1)C(=NC1=2)C=CN1N=CC=2C(=O)NC1CC1 DHEFBJXZYSKWIF-NVXWUHKLSA-N 0.000 claims 1
- HQCZHKJSSABUNL-GOSISDBHSA-N n-cyclopropyl-5-[(5r)-5-(2,5-difluorophenyl)-2,2-dimethylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N1([C@H](CCC1(C)C)C=1C(=CC=C(F)C=1)F)C(=NC1=2)C=CN1N=CC=2C(=O)NC1CC1 HQCZHKJSSABUNL-GOSISDBHSA-N 0.000 claims 1
- HNJJBTOZBLOWTO-UHFFFAOYSA-N n-cyclopropyl-5-[2-(2-ethyl-5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CCC1=NC=C(F)C=C1C1N(C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)CCC1 HNJJBTOZBLOWTO-UHFFFAOYSA-N 0.000 claims 1
- XCCJJNIKWGXTSP-UHFFFAOYSA-N n-cyclopropyl-5-[2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NC=C(F)C=C1C1N(C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)CCC1 XCCJJNIKWGXTSP-UHFFFAOYSA-N 0.000 claims 1
- XDTRTPIHJGKMHO-QGZVFWFLSA-N n-tert-butyl-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)NC(C)(C)C)=CC(F)=CC=C1F XDTRTPIHJGKMHO-QGZVFWFLSA-N 0.000 claims 1
- CABSRBXIZHPYSN-MRXNPFEDSA-N n-tert-butyl-5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound O=C1N(C)C=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC(C)(C)C)C=NN3C=C2)CCC1 CABSRBXIZHPYSN-MRXNPFEDSA-N 0.000 claims 1
- ACAZGFYJHFUFNU-MRXNPFEDSA-N n-tert-butyl-5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-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)C)C=NN3C=C2)CCC1 ACAZGFYJHFUFNU-MRXNPFEDSA-N 0.000 claims 1
- SPGMDULIPMJULM-OAHLLOKOSA-N n-tert-butyl-5-[(2r)-2-(5-fluoro-2-oxo-1h-pyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)(C)C)=CC(F)=CNC1=O SPGMDULIPMJULM-OAHLLOKOSA-N 0.000 claims 1
- BOGXBCHXRCHFDS-MRXNPFEDSA-N n-tert-butyl-5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)(C)C)=CN=CC(F)=C1 BOGXBCHXRCHFDS-MRXNPFEDSA-N 0.000 claims 1
- JSSACTCBXIXNAA-NVXWUHKLSA-N n-tert-butyl-5-[(2r,4r)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2C[C@@H](O)CN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)(C)C)=CC=CC(F)=C1 JSSACTCBXIXNAA-NVXWUHKLSA-N 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 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 description 4
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| SG10201914059WA (en) | 2008-10-22 | 2020-03-30 | Array Biopharma Inc | Substituted pyrazolo[1,5-a]pyrimidine compounds as trk kinase inhibitors |
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| WO2012034095A1 (en) * | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| JP5959541B2 (ja) * | 2011-02-25 | 2016-08-02 | ノバルティス アーゲー | Ｔｒｋ阻害剤としてのピラゾロ［１，５−ａ］ピリジン |
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| SG11201401095YA (en) | 2011-09-30 | 2014-04-28 | Vertex Pharma | Treating pancreatic cancer and non-small cell lung cancer with atr inhibitors |
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| PL2834243T3 (pl) * | 2012-03-09 | 2018-09-28 | Lexicon Pharmaceuticals, Inc. | Związki na bazie pirazolo[1,5-a]pirymidyny, zawierające je kompozycje i sposoby ich zastosowania |
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| EP2841428B1 (en) | 2012-04-24 | 2018-08-22 | Vertex Pharmaceuticals Incorporated | Dna-pk inhibitors |
| JOP20130273B1 (ar) * | 2012-09-11 | 2021-08-17 | Genzyme Corp | مثبطات انزيم (سينثاز) غلوكوسيل سيراميد |
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| RU2664541C2 (ru) * | 2012-11-13 | 2018-08-20 | Эррэй Биофарма Инк. | Бициклические соединения мочевины, тиомочевины, гуанидина и цианогуанидина, пригодные для лечения боли |
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| WO2014078331A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| ES2664331T3 (es) * | 2012-11-13 | 2018-04-19 | Array Biopharma, Inc. | Compuestos de N-pirrolidinilo, N'-pirazolilurea, tiourea, guanidina y cianoguanidina como inhibidores de la cinasa Trka |
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| PT4190786T (pt) | 2012-12-07 | 2025-05-29 | Vertex Pharma | Compostos úteis como inibidores da quinase atr |
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2015
- 2015-01-09 JP JP2015002767A patent/JP6114765B2/ja not_active Expired - Fee Related
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2017
- 2017-01-09 US US15/401,895 patent/US9796724B2/en active Active
- 2017-01-09 US US15/401,913 patent/US9782415B2/en active Active
- 2017-02-08 JP JP2017020927A patent/JP2017082004A/ja not_active Withdrawn
- 2017-10-04 US US15/724,601 patent/US10251889B2/en active Active
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2019
- 2019-04-08 US US16/377,514 patent/US10758542B2/en active Active
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