CA2767648C - Substituted pyrazolo[1,5-a]pyrimidine compounds as trk kinase inhibitors - Google Patents

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Publication number

CA2767648C

CA2767648C CA2767648A CA2767648A CA2767648C CA 2767648 C CA2767648 C CA 2767648C CA 2767648 A CA2767648 A CA 2767648A CA 2767648 A CA2767648 A CA 2767648A CA 2767648 C CA2767648 C CA 2767648C

Authority

CA

Canada

Prior art keywords

pyrimidine

pyrrolidin

pyrazolo

carboxamide

alkyl

Prior art date

2009-07-09

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.)

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• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title description 4
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 427
• 150000003839 salts Chemical class 0.000 claims abstract description 78
• 208000002193 Pain Diseases 0.000 claims abstract description 52
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 40
• 201000011510 cancer Diseases 0.000 claims abstract description 31
• 238000011282 treatment Methods 0.000 claims abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 201000010099 disease Diseases 0.000 claims abstract description 18
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 17
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 17
• 206010061218 Inflammation Diseases 0.000 claims abstract description 16
• 230000004054 inflammatory process Effects 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 555
• -1 -OH Chemical group 0.000 claims description 313
• 238000002360 preparation method Methods 0.000 claims description 194
• LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims description 164
• 125000001424 substituent group Chemical group 0.000 claims description 164
• 238000000034 method Methods 0.000 claims description 149
• 239000000203 mixture Substances 0.000 claims description 142
• 229910052736 halogen Inorganic materials 0.000 claims description 94
• 150000002367 halogens Chemical group 0.000 claims description 94
• 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 description 88
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 71
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 67
• 125000003545 alkoxy group Chemical group 0.000 claims description 57
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 51
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
• 125000005842 heteroatom Chemical group 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 47
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 43
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 41
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 32
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 32
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 28
• 125000004076 pyridyl group Chemical group 0.000 claims description 28
• 125000000565 sulfonamide group Chemical group 0.000 claims description 25
• 241000124008 Mammalia Species 0.000 claims description 23
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 19
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 17
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 15
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 15
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 14
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 12
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 206010001935 American trypanosomiasis Diseases 0.000 claims description 11
• 208000024699 Chagas disease Diseases 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• LKKQICCORQINHH-UHFFFAOYSA-N 3-fluoro-3H-pyridin-6-one Chemical group FC1C=CC(=O)N=C1 LKKQICCORQINHH-UHFFFAOYSA-N 0.000 claims description 10
• 206010009944 Colon cancer Diseases 0.000 claims description 10
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000004965 chloroalkyl group Chemical group 0.000 claims description 8
• 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 208000024891 symptom Diseases 0.000 claims description 7
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 6
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 6
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 6
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 6
• 206010029260 Neuroblastoma Diseases 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 6
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
• 230000004913 activation Effects 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• 230000003321 amplification Effects 0.000 claims description 5
• 201000008937 atopic dermatitis Diseases 0.000 claims description 5
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
• 230000035772 mutation Effects 0.000 claims description 5
• 238000003199 nucleic acid amplification method Methods 0.000 claims description 5
• 230000002018 overexpression Effects 0.000 claims description 5
• 201000002528 pancreatic cancer Diseases 0.000 claims description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
• 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 5
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 4
• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• XIDPBDLUUJOTDD-CYBMUJFWSA-N 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(N)=O)C=NN3C=C2)CCC1 XIDPBDLUUJOTDD-CYBMUJFWSA-N 0.000 claims description 3
• 101100063435 Caenorhabditis elegans din-1 gene Proteins 0.000 claims description 3
• 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 description 2
• CZZPKZAXQSRAJE-LJQANCHMSA-N 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]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N)=CC(F)=CC=C1OCCN1CCOCC1 CZZPKZAXQSRAJE-LJQANCHMSA-N 0.000 claims description 2
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 2
• VFMSIBXMZDZEJB-GOSISDBHSA-N tert-butyl n-[3-[[5-[(2r)-2-(2-chloro-5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonyl]amino]propyl]carbamate Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NCCCNC(=O)OC(C)(C)C)=CC(F)=CN=C1Cl VFMSIBXMZDZEJB-GOSISDBHSA-N 0.000 claims description 2
• 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 8
• 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 7
• CTGZXMASDOJLIY-QGZVFWFLSA-N n-(cyclopropylmethyl)-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)NCC4CC4)C=NN3C=C2)CCC1 CTGZXMASDOJLIY-QGZVFWFLSA-N 0.000 claims 7
• 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 6
• NZFWYKNHDNDHFJ-HXUWFJFHSA-N n-cyclopropyl-5-[(2r)-2-[3-fluoro-5-(2-methoxyethoxy)phenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COCCOC1=CC(F)=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)=C1 NZFWYKNHDNDHFJ-HXUWFJFHSA-N 0.000 claims 6
• 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 5
• CNSDQPQILIEBIM-UHFFFAOYSA-N 5-[2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(4-hydroxycyclohexyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CC(O)CCC1NC(=O)C1=C2N=C(N3C(CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 CNSDQPQILIEBIM-UHFFFAOYSA-N 0.000 claims 5
• WTGWCKJMZHWOAA-JXXFODFXSA-N C1C[C@@H](O)CC[C@@H]1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 Chemical compound C1C[C@@H](O)CC[C@@H]1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 WTGWCKJMZHWOAA-JXXFODFXSA-N 0.000 claims 5
• HRNZKBRSPYYSBU-PQJIZZRHSA-N n-(1-cyclopropylethyl)-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)C2CC2)=CN=CC(F)=C1 HRNZKBRSPYYSBU-PQJIZZRHSA-N 0.000 claims 5
• BCFGWXGYMCPFQX-QGZVFWFLSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[1-(hydroxymethyl)cyclopropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C=CC(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)=NC2=C1C(=O)NC1(CO)CC1 BCFGWXGYMCPFQX-QGZVFWFLSA-N 0.000 claims 4
• COJJJJKXTCQCLW-UHFFFAOYSA-N 5-[2-(2-ethyl-5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(4-hydroxycyclohexyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CCC1=NC=C(F)C=C1C1N(C2=NC3=C(C(=O)NC4CCC(O)CC4)C=NN3C=C2)CCC1 COJJJJKXTCQCLW-UHFFFAOYSA-N 0.000 claims 4
• 206010005003 Bladder cancer Diseases 0.000 claims 4
• 208000026310 Breast neoplasm Diseases 0.000 claims 4
• 208000008839 Kidney Neoplasms Diseases 0.000 claims 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims 4
• 208000015634 Rectal Neoplasms Diseases 0.000 claims 4
• 206010038389 Renal cancer Diseases 0.000 claims 4
• 208000005718 Stomach Neoplasms Diseases 0.000 claims 4
• 208000024770 Thyroid neoplasm Diseases 0.000 claims 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 4
• 208000002495 Uterine Neoplasms Diseases 0.000 claims 4
• 208000029742 colonic neoplasm Diseases 0.000 claims 4
• 206010017758 gastric cancer Diseases 0.000 claims 4
• 201000010982 kidney cancer Diseases 0.000 claims 4
• 201000005202 lung cancer Diseases 0.000 claims 4
• 208000020816 lung neoplasm Diseases 0.000 claims 4
• 206010038038 rectal cancer Diseases 0.000 claims 4
• 201000001275 rectum cancer Diseases 0.000 claims 4
• 201000011549 stomach cancer Diseases 0.000 claims 4
• 201000002510 thyroid cancer Diseases 0.000 claims 4
• 201000005112 urinary bladder cancer Diseases 0.000 claims 4
• 206010046766 uterine cancer Diseases 0.000 claims 4
• 230000001747 exhibiting effect Effects 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
• WUVMWSVFIXSKDX-MRXNPFEDSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(2-sulfamoylethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NCCS(=O)(=O)N)=CC(F)=CC=C1F WUVMWSVFIXSKDX-MRXNPFEDSA-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
• OOFWNPIPNPKKSR-LJQANCHMSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[2-(1h-imidazol-5-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NCCC=4N=CNC=4)C=NN3C=C2)=C1 OOFWNPIPNPKKSR-LJQANCHMSA-N 0.000 claims 2
• VWMOKEZPLSLTCC-QGZVFWFLSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[2-(methanesulfonamido)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NCCNS(=O)(=O)C)=CC(F)=CC=C1F VWMOKEZPLSLTCC-QGZVFWFLSA-N 0.000 claims 2
• 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 2
• 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
• 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
• 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
• LQRYCJFXMJIIPW-QGZVFWFLSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(1,3-dihydroxy-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(CO)(CO)C)=CC(F)=CC=C1F LQRYCJFXMJIIPW-QGZVFWFLSA-N 0.000 claims 1
• IKIKJTPYGZRILO-QGZVFWFLSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(1,3-dihydroxypropan-2-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(CO)CO)=CC(F)=CC=C1F IKIKJTPYGZRILO-QGZVFWFLSA-N 0.000 claims 1
• AMZHEDMUKHBPBM-LJQANCHMSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(1-sulfamoylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CN(S(=O)(=O)N)CCC1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 AMZHEDMUKHBPBM-LJQANCHMSA-N 0.000 claims 1
• VQFKVNURGWYBCE-LJQANCHMSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(2-imidazol-1-ylethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NCCN4C=NC=C4)C=NN3C=C2)=C1 VQFKVNURGWYBCE-LJQANCHMSA-N 0.000 claims 1
• CWZWSPLRRXTDRE-QGZVFWFLSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(2-methoxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NCCOC)=CC(F)=CC=C1F CWZWSPLRRXTDRE-QGZVFWFLSA-N 0.000 claims 1
• RDRCKVYUJKQGJL-HXUWFJFHSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(2-morpholin-4-ylethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NCCN4CCOCC4)C=NN3C=C2)=C1 RDRCKVYUJKQGJL-HXUWFJFHSA-N 0.000 claims 1
• YVJSJUUNTJSCDD-GOSISDBHSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(3-hydroxy-2,2-dimethylpropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NCC(C)(CO)C)=CC(F)=CC=C1F YVJSJUUNTJSCDD-GOSISDBHSA-N 0.000 claims 1
• ZXDAOGSITPXTJV-LJQANCHMSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(oxan-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CCOCC4)C=NN3C=C2)=C1 ZXDAOGSITPXTJV-LJQANCHMSA-N 0.000 claims 1
• WAHDCQYLZWQRBB-LJQANCHMSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(1-methylpyrazol-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN(C)C=C1CNC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 WAHDCQYLZWQRBB-LJQANCHMSA-N 0.000 claims 1
• WDEZXSKNKVBRGN-YZVOILCLSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(1s,3s)-3-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1[C@@H](O)CC[C@@H]1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 WDEZXSKNKVBRGN-YZVOILCLSA-N 0.000 claims 1
• GSSDAQWHOJFZRE-CXAGYDPISA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2r)-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-CXAGYDPISA-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
• RURCYYRVPUXVMX-RTBURBONSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s)-1-hydroxy-3,3-dimethylbutan-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(C)(C)C)=CC(F)=CC=C1F RURCYYRVPUXVMX-RTBURBONSA-N 0.000 claims 1
• WDCXWYXCNRUVKU-RTBURBONSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s)-1-hydroxy-3-methylbutan-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(C)C)=CC(F)=CC=C1F WDCXWYXCNRUVKU-RTBURBONSA-N 0.000 claims 1
• OJEYPUNKJUVVID-KBXCAEBGSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s)-1-hydroxybutan-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)CC)=CC(F)=CC=C1F OJEYPUNKJUVVID-KBXCAEBGSA-N 0.000 claims 1
• IQIMTMWUNOWCKV-YVEFUNNKSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(2s)-1-hydroxypropan-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)=CC(F)=CC=C1F IQIMTMWUNOWCKV-YVEFUNNKSA-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
• 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
• KUSZMPYJQONYEI-HXUWFJFHSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[(5-methylfuran-2-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound O1C(C)=CC=C1CNC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 KUSZMPYJQONYEI-HXUWFJFHSA-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
• WPQQNUFDOKQHRQ-GOSISDBHSA-N 5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-pyridin-2-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC=4N=CC=CC=4)C=NN3C=C2)=C1 WPQQNUFDOKQHRQ-GOSISDBHSA-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
• UOGDTYJUQWDKKR-GOSISDBHSA-N 5-[(2r)-2-(2-ethyl-5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(2-hydroxy-2-methylpropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CCC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NCC(C)(C)O)C=NN3C=C2)CCC1 UOGDTYJUQWDKKR-GOSISDBHSA-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
• 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
• DGVVSWFLMBWPNY-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]-n-(1-methylcyclopropyl)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)NC4(C)CC4)C=NN3C=C2)CCC1 DGVVSWFLMBWPNY-MRXNPFEDSA-N 0.000 claims 1
• SICRRVUVAIRMQG-LJQANCHMSA-N 5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]-n-(6-methylpyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(N(C)C=C(F)C=3)=O)C=CN2N=C1 SICRRVUVAIRMQG-LJQANCHMSA-N 0.000 claims 1
• GNHQMDGKASSYQR-GUDVDZBRSA-N 5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]-n-[(1r,2r)-2-hydroxycyclohexyl]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)N[C@H]4[C@@H](CCCC4)O)C=NN3C=C2)CCC1 GNHQMDGKASSYQR-GUDVDZBRSA-N 0.000 claims 1
• DXCATLCGJNNZIB-QZTJIDSGSA-N 5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]-n-[(2s)-1-hydroxy-3,3-dimethylbutan-2-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)N[C@H](CO)C(C)(C)C)C=NN3C=C2)CCC1 DXCATLCGJNNZIB-QZTJIDSGSA-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
• XURYENAZODILKN-GOSISDBHSA-N 5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-3-yl)pyrrolidin-1-yl]-n-pyridin-3-ylpyrazolo[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=4C=NC=CC=4)C=NN3C=C2)CCC1 XURYENAZODILKN-GOSISDBHSA-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
• SPBLOIGTOGQHKL-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(1-methylpyrazol-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)NC4=NN(C)C=C4)C=NN3C=C2)CCC1 SPBLOIGTOGQHKL-MRXNPFEDSA-N 0.000 claims 1
• YHWLSZUFSOTFQF-GOSISDBHSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(1-propan-2-ylpyrazol-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)NC4=NN(C=C4)C(C)C)C=NN3C=C2)CCC1 YHWLSZUFSOTFQF-GOSISDBHSA-N 0.000 claims 1
• HAPDPSKWHISKDX-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-(2-hydroxy-2-methylpropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NCC(C)(C)O)C=NN3C=C2)CCC1 HAPDPSKWHISKDX-MRXNPFEDSA-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
• 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
• HREXZCUAJJCCAF-RLFYNMQTSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-[(1s,3s)-3-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=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 HREXZCUAJJCCAF-RLFYNMQTSA-N 0.000 claims 1
• MCGUMEZGZDHGBX-MLGOLLRUSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-[(2r)-2-hydroxypropyl]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](C)O)C=NN3C=C2)CCC1 MCGUMEZGZDHGBX-MLGOLLRUSA-N 0.000 claims 1
• SXFVRQSCLPLRFN-HXUWFJFHSA-N 5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]-n-[1-(2-hydroxyethyl)piperidin-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4CCN(CCO)CC4)C=NN3C=C2)CCC1 SXFVRQSCLPLRFN-HXUWFJFHSA-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
• OXVCBPXLNVQEGM-QGZVFWFLSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-(1-methylcyclopropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4(C)CC4)C=NN3C=C2)CCC1 OXVCBPXLNVQEGM-QGZVFWFLSA-N 0.000 claims 1
• MEXQNHGYJHJKCY-MRXNPFEDSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NCCO)C=NN3C=C2)CCC1 MEXQNHGYJHJKCY-MRXNPFEDSA-N 0.000 claims 1
• DGAFCFQIMXJUDW-QGZVFWFLSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-(2-methoxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NCCOC)=CC(F)=CN=C1C DGAFCFQIMXJUDW-QGZVFWFLSA-N 0.000 claims 1
• RUKGVZRSXAHREZ-TXPKVOOTSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-[(1s,3s)-3-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=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 RUKGVZRSXAHREZ-TXPKVOOTSA-N 0.000 claims 1
• KKTZVZNGYWEPCI-SJKOYZFVSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-[(2r)-2-hydroxypropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC[C@H](O)C)=CC(F)=CN=C1C KKTZVZNGYWEPCI-SJKOYZFVSA-N 0.000 claims 1
• PZGCHNDBATUPDX-QGZVFWFLSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-n-[1-(hydroxymethyl)cyclopropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4(CO)CC4)C=NN3C=C2)CCC1 PZGCHNDBATUPDX-QGZVFWFLSA-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
• ZOAPGXAKZWJIHN-CQSZACIVSA-N 5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(N)=O)C=NN3C=C2)CCC1 ZOAPGXAKZWJIHN-CQSZACIVSA-N 0.000 claims 1
• PDPJLIBDEWXTAI-LRHAYUFXSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(1-methoxypropan-2-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)COC)=CN=CC(F)=C1 PDPJLIBDEWXTAI-LRHAYUFXSA-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
• XUFRAOMXWJULLM-OAHLLOKOSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NCCO)=CN=CC(F)=C1 XUFRAOMXWJULLM-OAHLLOKOSA-N 0.000 claims 1
• NKAVBKULSDGBBI-GOSISDBHSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(oxan-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CN=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CCOCC4)C=NN3C=C2)=C1 NKAVBKULSDGBBI-GOSISDBHSA-N 0.000 claims 1
• RKRWQXHCILAOQU-RCCFBDPRSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(1s,2r)-2-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound O[C@@H]1CCC[C@@H]1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 RKRWQXHCILAOQU-RCCFBDPRSA-N 0.000 claims 1
• VGEDWYCIYWKLHV-XYJFISCASA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(1s,3s)-3-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1[C@@H](O)CC[C@@H]1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 VGEDWYCIYWKLHV-XYJFISCASA-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
• LYGAZBUPOLXLRE-ZWKOTPCHSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(2r)-1-hydroxy-3-methylbutan-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(C)C)=CN=CC(F)=C1 LYGAZBUPOLXLRE-ZWKOTPCHSA-N 0.000 claims 1
• SBVICLYVLJMIDO-MLGOLLRUSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(2r)-1-hydroxypropan-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)=CN=CC(F)=C1 SBVICLYVLJMIDO-MLGOLLRUSA-N 0.000 claims 1
• CUAZXICLJJKGFD-MLGOLLRUSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(2r)-2-hydroxypropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC[C@H](O)C)=CN=CC(F)=C1 CUAZXICLJJKGFD-MLGOLLRUSA-N 0.000 claims 1
• KJYXTMLZCPHUAV-XHDPSFHLSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(2s)-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-XHDPSFHLSA-N 0.000 claims 1
• CUAZXICLJJKGFD-BLLLJJGKSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(2s)-2-hydroxypropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)NC[C@@H](O)C)=CN=CC(F)=C1 CUAZXICLJJKGFD-BLLLJJGKSA-N 0.000 claims 1
• NRXYESAXZCGGAF-OAHLLOKOSA-N 5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[1-(trifluoromethyl)cyclopropyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CN=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4(CC4)C(F)(F)F)C=NN3C=C2)=C1 NRXYESAXZCGGAF-OAHLLOKOSA-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
• WRBFVDOQDFYXNC-CYBMUJFWSA-N 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)N)=CN=CC(F)=C1 WRBFVDOQDFYXNC-CYBMUJFWSA-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
• QXACJSRSZMVUQK-WHCXFUJUSA-N 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(N)=O)C=NN3C=C2)=C1 QXACJSRSZMVUQK-WHCXFUJUSA-N 0.000 claims 1
• GVXOANLMUATURP-QGZVFWFLSA-N 5-[(2r)-2-[3-fluoro-5-(2-methoxyethoxy)phenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COCCOC1=CC(F)=CC([C@@H]2N(CCC2)C2=NC3=C(C(N)=O)C=NN3C=C2)=C1 GVXOANLMUATURP-QGZVFWFLSA-N 0.000 claims 1
• LTPGETLXOCVLEF-HXUWFJFHSA-N 5-[(2r)-2-[3-fluoro-5-(2-morpholin-4-ylethoxy)phenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C([C@H]2CCCN2C=2C=CN3N=CC(=C3N=2)C(=O)N)=CC(F)=CC=1OCCN1CCOCC1 LTPGETLXOCVLEF-HXUWFJFHSA-N 0.000 claims 1
• OPRRDZXAVINFQM-MRXNPFEDSA-N 5-[(2r)-2-[5-fluoro-2-(2-methoxyethoxy)phenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COCCOC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(N)=O)C=NN3C=C2)CCC1 OPRRDZXAVINFQM-MRXNPFEDSA-N 0.000 claims 1
• OVDQQFSDDWEASL-CQSZACIVSA-N 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)N)=CC(F)=CC=C1C(F)(F)F OVDQQFSDDWEASL-CQSZACIVSA-N 0.000 claims 1
• TUPCMOPJDADTAY-UKRRQHHQSA-N 5-[(2r,4r)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl]-n-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2C[C@@H](O)CN2C=2C=CN3N=CC(=C3N=2)C(=O)NC)=CC=CC(F)=C1 TUPCMOPJDADTAY-UKRRQHHQSA-N 0.000 claims 1
• GZISOCBRRUTHKW-HZUKXOBISA-N 5-[(2r,4s)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl]-n-[(2s)-1,1,1-trifluoropropan-2-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)N[C@@H](C)C(F)(F)F)=CC=CC(F)=C1 GZISOCBRRUTHKW-HZUKXOBISA-N 0.000 claims 1
• TUPCMOPJDADTAY-DZGCQCFKSA-N 5-[(2r,4s)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl]-n-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2C[C@H](O)CN2C=2C=CN3N=CC(=C3N=2)C(=O)NC)=CC=CC(F)=C1 TUPCMOPJDADTAY-DZGCQCFKSA-N 0.000 claims 1
• VEFAIJAFTRTKSA-DOTOQJQBSA-N 5-[(2r,4s)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl]-n-propan-2-ylpyrazolo[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)=CC=CC(F)=C1 VEFAIJAFTRTKSA-DOTOQJQBSA-N 0.000 claims 1
• HHFHBMCHRPJYLX-DOTOQJQBSA-N 5-[(2r,5s)-2-(5-fluoropyridin-3-yl)-5-(hydroxymethyl)pyrrolidin-1-yl]-n-(1-methylcyclopropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C=CC(N3[C@H](CC[C@H]3CO)C=3C=C(F)C=NC=3)=NC2=C1C(=O)NC1(C)CC1 HHFHBMCHRPJYLX-DOTOQJQBSA-N 0.000 claims 1
• AROVXDKGPGGRBP-DIOULYMOSA-N 5-[(2r,5s)-2-(5-fluoropyridin-3-yl)-5-(hydroxymethyl)pyrrolidin-1-yl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CC[C@@H](CO)N2C=2C=CN3N=CC(=C3N=2)C(=O)N[C@H](C)C(F)(F)F)=CN=CC(F)=C1 AROVXDKGPGGRBP-DIOULYMOSA-N 0.000 claims 1
• AROVXDKGPGGRBP-HZUKXOBISA-N 5-[(2r,5s)-2-(5-fluoropyridin-3-yl)-5-(hydroxymethyl)pyrrolidin-1-yl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CC[C@@H](CO)N2C=2C=CN3N=CC(=C3N=2)C(=O)N[C@@H](C)C(F)(F)F)=CN=CC(F)=C1 AROVXDKGPGGRBP-HZUKXOBISA-N 0.000 claims 1
• YYCRCMXHHDOWEV-DOTOQJQBSA-N 5-[(2r,5s)-2-(5-fluoropyridin-3-yl)-5-(hydroxymethyl)pyrrolidin-1-yl]-n-propan-2-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CC[C@@H](CO)N2C=2C=CN3N=CC(=C3N=2)C(=O)NC(C)C)=CN=CC(F)=C1 YYCRCMXHHDOWEV-DOTOQJQBSA-N 0.000 claims 1
• JPAYSBNMHYNPLA-KRYHZZBUSA-N 5-[(2s,5r)-5-(5-fluoropyridin-3-yl)-2-(hydroxymethyl)-2-methylpyrrolidin-1-yl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@@H]2N([C@](CC2)(C)CO)C=2C=CN3N=CC(=C3N=2)C(=O)N[C@@H](C)C(F)(F)F)=CN=CC(F)=C1 JPAYSBNMHYNPLA-KRYHZZBUSA-N 0.000 claims 1
• RKVKRYPLPNWYSE-OAHLLOKOSA-N 5-[(5r)-5-(2,5-difluorophenyl)-2,2-dimethylpyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1([C@H]2CCC(N2C2=NC3=C(C(N)=O)C=NN3C=C2)(C)C)=CC(F)=CC=C1F RKVKRYPLPNWYSE-OAHLLOKOSA-N 0.000 claims 1
• XCBGRHHBQFJBBF-UHFFFAOYSA-N 5-[2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N=1C2=C(C(=O)NCCO)C=NN2C=CC=1N1CCCC1C1=CC(F)=CC=C1F XCBGRHHBQFJBBF-UHFFFAOYSA-N 0.000 claims 1
• ZYIYWAPOCQBZSM-UHFFFAOYSA-N 5-[2-(2,5-difluorophenyl)pyrrolidin-1-yl]-n-[2-(4-hydroxypiperidin-1-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CC(O)CCN1CCNC(=O)C1=C2N=C(N3C(CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 ZYIYWAPOCQBZSM-UHFFFAOYSA-N 0.000 claims 1
• GYPXDOPFEWTHRF-CTWPCTMYSA-N 5-[2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]-N-[(2R)-2-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=C(C=C(F)C=N1)C1CCCN1C1=NC2=C(C=NN2C=C1)C(=O)NC1CCC[C@H]1O GYPXDOPFEWTHRF-CTWPCTMYSA-N 0.000 claims 1
• IESPWTFFLPDHJL-UHFFFAOYSA-N 5-[2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CN=CC(C2N(CCC2)C2=NC3=C(C(=O)NCC(F)(F)F)C=NN3C=C2)=C1 IESPWTFFLPDHJL-UHFFFAOYSA-N 0.000 claims 1
• WWRZXXZWDNGWCD-UHFFFAOYSA-N 5-[2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-(3-hydroxy-2,2-dimethylpropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N=1C2=C(C(=O)NCC(C)(CO)C)C=NN2C=CC=1N1CCCC1C1=CN=CC(F)=C1 WWRZXXZWDNGWCD-UHFFFAOYSA-N 0.000 claims 1
• RKRWQXHCILAOQU-GVYDCBATSA-N 5-[2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]-n-[(1r,2r)-2-hydroxycyclopentyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound O[C@@H]1CCC[C@H]1NC(=O)C1=C2N=C(N3C(CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 RKRWQXHCILAOQU-GVYDCBATSA-N 0.000 claims 1
• CNSDQPQILIEBIM-ZHALLVOQSA-N C1C[C@@H](O)CC[C@@H]1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 Chemical compound C1C[C@@H](O)CC[C@@H]1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 CNSDQPQILIEBIM-ZHALLVOQSA-N 0.000 claims 1
• FDBFUEIJFKHRQU-MBOZVWFJSA-N CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N[C@@H]4CC[C@@H](O)CC4)C=NN3C=C2)CCC1 Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N[C@@H]4CC[C@@H](O)CC4)C=NN3C=C2)CCC1 FDBFUEIJFKHRQU-MBOZVWFJSA-N 0.000 claims 1
• FDBFUEIJFKHRQU-FUHIMQAGSA-N CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N[C@H]4CC[C@@H](O)CC4)C=NN3C=C2)CCC1 Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N[C@H]4CC[C@@H](O)CC4)C=NN3C=C2)CCC1 FDBFUEIJFKHRQU-FUHIMQAGSA-N 0.000 claims 1
• QJFLYXFEPUKNII-GPMSIDNRSA-N O=C1N(C)C=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N[C@@H]4CC[C@@H](O)CC4)C=NN3C=C2)CCC1 Chemical compound O=C1N(C)C=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N[C@@H]4CC[C@@H](O)CC4)C=NN3C=C2)CCC1 QJFLYXFEPUKNII-GPMSIDNRSA-N 0.000 claims 1
• IHXVXJVXFFLYQL-OAHLLOKOSA-N [5-[(2r)-2-(2-amino-5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-(azetidin-1-yl)methanone Chemical compound NC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N4CCC4)C=NN3C=C2)CCC1 IHXVXJVXFFLYQL-OAHLLOKOSA-N 0.000 claims 1
• OKICNWNFGLYZRW-MRXNPFEDSA-N [5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-(3-hydroxy-3-methylazetidin-1-yl)methanone Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N4CC(C)(O)C4)C=NN3C=C2)CCC1 OKICNWNFGLYZRW-MRXNPFEDSA-N 0.000 claims 1
• KEMAQYFMSWCNPP-MRXNPFEDSA-N [5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound COC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N4CC(O)C4)C=NN3C=C2)CCC1 KEMAQYFMSWCNPP-MRXNPFEDSA-N 0.000 claims 1
• DIVNKYZMVMAVDL-QGZVFWFLSA-N [5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)N4CC(O)C4)C=NN3C=C2)CCC1 DIVNKYZMVMAVDL-QGZVFWFLSA-N 0.000 claims 1
• ZBAKBPQBWVZHSS-MRXNPFEDSA-N [5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-(3-hydroxy-3-methylazetidin-1-yl)methanone Chemical compound C1C(C)(O)CN1C(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 ZBAKBPQBWVZHSS-MRXNPFEDSA-N 0.000 claims 1
• IAQOHRSJLFSNIO-MRXNPFEDSA-N [5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound C1C(O)CN1C(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 IAQOHRSJLFSNIO-MRXNPFEDSA-N 0.000 claims 1
• ZTUAEBXOYDCUHH-QGZVFWFLSA-N [5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-(3-methoxyazetidin-1-yl)methanone Chemical compound C1C(OC)CN1C(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 ZTUAEBXOYDCUHH-QGZVFWFLSA-N 0.000 claims 1
• YWPVOJJFDPUXIP-DOTOQJQBSA-N [5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-[(3s)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound C1[C@@H](O)CCN1C(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 YWPVOJJFDPUXIP-DOTOQJQBSA-N 0.000 claims 1
• VCAFMQVDMYUXAD-QGZVFWFLSA-N [5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-[3-(hydroxymethyl)azetidin-1-yl]methanone Chemical compound C1C(CO)CN1C(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 VCAFMQVDMYUXAD-QGZVFWFLSA-N 0.000 claims 1
• RFEWPNNVHIQMAM-GOSISDBHSA-N [5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-piperidin-1-ylmethanone Chemical compound FC1=CN=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)N4CCCCC4)C=NN3C=C2)=C1 RFEWPNNVHIQMAM-GOSISDBHSA-N 0.000 claims 1
• VICTZKCFLVXPBL-QGZVFWFLSA-N [5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound FC1=CN=CC([C@@H]2N(CCC2)C2=NC3=C(C(=O)N4CCCC4)C=NN3C=C2)=C1 VICTZKCFLVXPBL-QGZVFWFLSA-N 0.000 claims 1
• CJXSUHUGXGYYSY-UHFFFAOYSA-N azetidin-1-yl-[5-[2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound FC1=CN=CC(C2N(CCC2)C2=NC3=C(C(=O)N4CCC4)C=NN3C=C2)=C1 CJXSUHUGXGYYSY-UHFFFAOYSA-N 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• OCDHRWHIOLGDFC-CQSZACIVSA-N n-(2,2-difluoroethyl)-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)NCC(F)F)=CN=CC(F)=C1 OCDHRWHIOLGDFC-CQSZACIVSA-N 0.000 claims 1
• HGBUMXKTCONBMP-FQNRMIAFSA-N n-(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)NCC(O)CO)C=NN3C=C2)CCC1 HGBUMXKTCONBMP-FQNRMIAFSA-N 0.000 claims 1
• FQQIJMFIYQPLDE-QGZVFWFLSA-N n-(2-amino-2-methylpropyl)-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)NCC(C)(N)C)=CC(F)=CC=C1F FQQIJMFIYQPLDE-QGZVFWFLSA-N 0.000 claims 1
• DLSRDRNPMPGSGU-OAHLLOKOSA-N n-(2-bromoethoxy)-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)NOCCBr)C=NN3C=C2)CCC1 DLSRDRNPMPGSGU-OAHLLOKOSA-N 0.000 claims 1
• VYIVOYKEWZBJNX-OAHLLOKOSA-N n-(2-chloroethyl)-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)NCCCl)C=NN3C=C2)CCC1 VYIVOYKEWZBJNX-OAHLLOKOSA-N 0.000 claims 1
• RWIYPTPMXPGFTG-CQSZACIVSA-N n-(2-chloroethyl)-5-[(2r)-2-(5-fluoro-2-oxo-1h-pyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CNC(=O)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NCCCl)C=NN3C=C2)=C1 RWIYPTPMXPGFTG-CQSZACIVSA-N 0.000 claims 1
• OHANFWDUXHKLHO-MRXNPFEDSA-N n-(2-cyanopropan-2-yl)-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#N)=CN=CC(F)=C1 OHANFWDUXHKLHO-MRXNPFEDSA-N 0.000 claims 1
• DKIDZDUYOIVIOB-OAHLLOKOSA-N n-(3-aminopropyl)-5-[(2r)-2-(2-chloro-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)NCCCN)=CC(F)=CN=C1Cl DKIDZDUYOIVIOB-OAHLLOKOSA-N 0.000 claims 1
• QHRTXUATNCWBBL-BZSJEYESSA-N n-(3-chloro-2-fluoropropyl)-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)NCC(CCl)F)=CN=CC(F)=C1 QHRTXUATNCWBBL-BZSJEYESSA-N 0.000 claims 1
• HRXHRVGEOCMYJD-GOSISDBHSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-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=4NN=C(C=4)C4CC4)C=NN3C=C2)CCC1 HRXHRVGEOCMYJD-GOSISDBHSA-N 0.000 claims 1
• ITGKPZIBLXMPGK-QGZVFWFLSA-N n-(5-ethyl-1h-pyrazol-3-yl)-5-[(2r)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N1N=C(CC)C=C1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C(=NC=C(F)C=3)OC)C=CN2N=C1 ITGKPZIBLXMPGK-QGZVFWFLSA-N 0.000 claims 1
• TYZOVRSMZFTMCR-QGZVFWFLSA-N n-(5-fluoropyridin-2-yl)-5-[(2r)-2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N1=CC(F)=CC=C1NC(=O)C1=C2N=C(N3[C@H](CCC3)C=3C=C(F)C=NC=3)C=CN2N=C1 TYZOVRSMZFTMCR-QGZVFWFLSA-N 0.000 claims 1
• LEOYYKMTNGOPRD-MRXNPFEDSA-N n-(cyanomethyl)-5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NCC#N)C=NN3C=C2)=C1 LEOYYKMTNGOPRD-MRXNPFEDSA-N 0.000 claims 1
• GPUJXNIEEVLNGE-GOSISDBHSA-N n-(cyclopropylmethoxy)-5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NOCC4CC4)C=NN3C=C2)=C1 GPUJXNIEEVLNGE-GOSISDBHSA-N 0.000 claims 1
• YIKVOJGIIXEFHZ-QGZVFWFLSA-N n-(cyclopropylmethyl)-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)NCC4CC4)C=NN3C=C2)=C1 YIKVOJGIIXEFHZ-QGZVFWFLSA-N 0.000 claims 1
• ISCJKTYZQXHEBM-FZKQIMNGSA-N n-[(1r)-1-cyclopropylethyl]-5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-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)N[C@H](C)C2CC2)=CC(F)=CN(C)C1=O ISCJKTYZQXHEBM-FZKQIMNGSA-N 0.000 claims 1
• HRNZKBRSPYYSBU-FZKQIMNGSA-N n-[(1r)-1-cyclopropylethyl]-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)N[C@H](C)C2CC2)=CN=CC(F)=C1 HRNZKBRSPYYSBU-FZKQIMNGSA-N 0.000 claims 1
• ISCJKTYZQXHEBM-SCLBCKFNSA-N n-[(1s)-1-cyclopropylethyl]-5-[(2r)-2-(5-fluoro-1-methyl-2-oxopyridin-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)N[C@@H](C)C2CC2)=CC(F)=CN(C)C1=O ISCJKTYZQXHEBM-SCLBCKFNSA-N 0.000 claims 1
• HRNZKBRSPYYSBU-SCLBCKFNSA-N n-[(1s)-1-cyclopropylethyl]-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)N[C@@H](C)C2CC2)=CN=CC(F)=C1 HRNZKBRSPYYSBU-SCLBCKFNSA-N 0.000 claims 1
• 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
• HGBUMXKTCONBMP-CZUORRHYSA-N n-[(2r)-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-CZUORRHYSA-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
• PKQSRPZFIGJTJF-GOSISDBHSA-N n-cyclobutyl-5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CCC4)C=NN3C=C2)=C1 PKQSRPZFIGJTJF-GOSISDBHSA-N 0.000 claims 1
• KKQVKLFNDUPHNK-QGZVFWFLSA-N n-cyclobutyl-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)NC4CCC4)C=NN3C=C2)CCC1 KKQVKLFNDUPHNK-QGZVFWFLSA-N 0.000 claims 1
• PKQNMQSZDCVFLD-GOSISDBHSA-N n-cyclobutyl-5-[(2r)-2-(5-fluoro-2-methylpyridin-3-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=NC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4CCC4)C=NN3C=C2)CCC1 PKQNMQSZDCVFLD-GOSISDBHSA-N 0.000 claims 1
• 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
• XJNRYKKXKPGNHH-QGZVFWFLSA-N n-cyclopropyl-5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=C(F)C([C@@H]2N(CCC2)C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)=C1 XJNRYKKXKPGNHH-QGZVFWFLSA-N 0.000 claims 1
• AGNJXIYEGHWROL-MRXNPFEDSA-N n-cyclopropyl-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)NC4CC4)C=NN3C=C2)CCC1 AGNJXIYEGHWROL-MRXNPFEDSA-N 0.000 claims 1
• 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
• 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
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• DJADXHQZNZDUAO-LJQANCHMSA-N n-cyclopropyl-5-[(2r)-2-[5-fluoro-2-(2-methoxyethoxy)phenyl]pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound COCCOC1=CC=C(F)C=C1[C@@H]1N(C2=NC3=C(C(=O)NC4CC4)C=NN3C=C2)CCC1 DJADXHQZNZDUAO-LJQANCHMSA-N 0.000 claims 1
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