JP2011517458A5 - - Google Patents

Info

Publication number

JP2011517458A5

JP2011517458A5 JP2011503082A JP2011503082A JP2011517458A5 JP 2011517458 A5 JP2011517458 A5 JP 2011517458A5 JP 2011503082 A JP2011503082 A JP 2011503082A JP 2011503082 A JP2011503082 A JP 2011503082A JP 2011517458 A5 JP2011517458 A5 JP 2011517458A5

Authority

JP

Japan

Prior art keywords

pyrimidin

benzamide

pyrazolo

hydroxypropan

tert

Prior art date

2009-03-30

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

Links

• Espacenet
• Global Dossier
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• -1 cyano, thio, oxy, carbonyloxy Chemical group 0.000 claims 116
• 150000001875 compounds Chemical class 0.000 claims 44
• 125000005842 heteroatom Chemical group 0.000 claims 37
• 125000000217 alkyl group Chemical group 0.000 claims 32
• 125000003118 aryl group Chemical group 0.000 claims 27
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims 14
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 12
• 201000010099 disease Diseases 0.000 claims 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
• 125000001424 substituent group Chemical group 0.000 claims 11
• 150000001602 bicycloalkyls Chemical group 0.000 claims 10
• 125000005843 halogen group Chemical group 0.000 claims 9
• 125000001072 heteroaryl group Chemical group 0.000 claims 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
• 239000003814 drug Substances 0.000 claims 7
• 229910052739 hydrogen Inorganic materials 0.000 claims 7
• 239000001257 hydrogen Substances 0.000 claims 7
• 125000004104 aryloxy group Chemical group 0.000 claims 6
• 125000005605 benzo group Chemical group 0.000 claims 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims 6
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
• 229940079593 drug Drugs 0.000 claims 5
• 208000028867 ischemia Diseases 0.000 claims 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
• 125000003545 alkoxy group Chemical group 0.000 claims 4
• 125000003282 alkyl amino group Chemical group 0.000 claims 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 4
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 4
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 3
• 206010007572 Cardiac hypertrophy Diseases 0.000 claims 3
• 208000006029 Cardiomegaly Diseases 0.000 claims 3
• 206010021143 Hypoxia Diseases 0.000 claims 3
• 208000002193 Pain Diseases 0.000 claims 3
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
• 239000003795 chemical substances by application Substances 0.000 claims 3
• 230000007954 hypoxia Effects 0.000 claims 3
• 208000010125 myocardial infarction Diseases 0.000 claims 3
• 230000004770 neurodegeneration Effects 0.000 claims 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims 3
• 125000005188 oxoalkyl group Chemical group 0.000 claims 3
• 230000036407 pain Effects 0.000 claims 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
• 150000003839 salts Chemical class 0.000 claims 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 3
• 229940124530 sulfonamide Drugs 0.000 claims 3
• 150000003456 sulfonamides Chemical class 0.000 claims 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
• ZJPHAQGVIJMSTQ-MRXNPFEDSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 ZJPHAQGVIJMSTQ-MRXNPFEDSA-N 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
• LWTQUQNSRBLAGG-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1C(C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 LWTQUQNSRBLAGG-UHFFFAOYSA-N 0.000 claims 2
• KVWJNXPPFSNYLH-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-oxopiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(=O)NCC2)=C1 KVWJNXPPFSNYLH-UHFFFAOYSA-N 0.000 claims 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
• QGGXIKUPMBWBTH-UHFFFAOYSA-N 4-tert-butyl-n-[7-(pyrimidin-2-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC=2N=CC=CN=2)=C1 QGGXIKUPMBWBTH-UHFFFAOYSA-N 0.000 claims 2
• 208000020084 Bone disease Diseases 0.000 claims 2
• 208000011231 Crohn disease Diseases 0.000 claims 2
• 208000002705 Glucose Intolerance Diseases 0.000 claims 2
• 206010019280 Heart failures Diseases 0.000 claims 2
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
• HRMVKGNVXHNGII-UHFFFAOYSA-N N-(2-hydroxypropan-2-yl)benzamide Chemical compound CC(C)(O)NC(=O)c1ccccc1 HRMVKGNVXHNGII-UHFFFAOYSA-N 0.000 claims 2
• 208000006011 Stroke Diseases 0.000 claims 2
• 108090000190 Thrombin Proteins 0.000 claims 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
• 150000001408 amides Chemical class 0.000 claims 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
• 239000008280 blood Substances 0.000 claims 2
• 210000004369 blood Anatomy 0.000 claims 2
• 150000003857 carboxamides Chemical class 0.000 claims 2
• 206010008118 cerebral infarction Diseases 0.000 claims 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
• 206010012601 diabetes mellitus Diseases 0.000 claims 2
• 206010020718 hyperplasia Diseases 0.000 claims 2
• 230000028993 immune response Effects 0.000 claims 2
• 208000014674 injury Diseases 0.000 claims 2
• 210000004185 liver Anatomy 0.000 claims 2
• 208000019423 liver disease Diseases 0.000 claims 2
• 125000002757 morpholinyl group Chemical group 0.000 claims 2
• 201000006417 multiple sclerosis Diseases 0.000 claims 2
• 208000031225 myocardial ischemia Diseases 0.000 claims 2
• TZGFASURQDCAHW-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-pyridin-4-ylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C2C(C2)C=2C=CN=CC=2)=NC2=CC(C)=NN12 TZGFASURQDCAHW-UHFFFAOYSA-N 0.000 claims 2
• JPKSVPDOAXTDGA-UHFFFAOYSA-N n-[7-[4-(hydroxymethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CO)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 JPKSVPDOAXTDGA-UHFFFAOYSA-N 0.000 claims 2
• 210000000056 organ Anatomy 0.000 claims 2
• 125000004043 oxo group Chemical group O=* 0.000 claims 2
• 230000001575 pathological effect Effects 0.000 claims 2
• 125000004193 piperazinyl group Chemical group 0.000 claims 2
• 125000003386 piperidinyl group Chemical group 0.000 claims 2
• 201000009104 prediabetes syndrome Diseases 0.000 claims 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims 2
• 125000004076 pyridyl group Chemical group 0.000 claims 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
• 230000010410 reperfusion Effects 0.000 claims 2
• 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
• 229960004072 thrombin Drugs 0.000 claims 2
• 230000008736 traumatic injury Effects 0.000 claims 2
• 125000004306 triazinyl group Chemical group 0.000 claims 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
• 230000002792 vascular Effects 0.000 claims 2
• XLOOFDPJOQWACG-RBUKOAKNSA-N (1r,2r)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@@H]2C[C@H]2C(=O)NC2=NC3=CC(=NN3C(C=3C=CC=CC=3)=C2)C)=CC=CC=C1 XLOOFDPJOQWACG-RBUKOAKNSA-N 0.000 claims 1
• BAQLCCJCNPZGRP-VQTJNVASSA-N (1r,2r)-n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)[C@H]2[C@@H](C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 BAQLCCJCNPZGRP-VQTJNVASSA-N 0.000 claims 1
• IPILMVZMVZJPLW-ZWKOTPCHSA-N (1r,2r)-n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@@H]2C[C@H]2C(=O)NC2=NC3=CC(=NN3C(N3CCC(CC3)NC(N)=O)=C2)C)=CC=CC=C1 IPILMVZMVZJPLW-ZWKOTPCHSA-N 0.000 claims 1
• XLOOFDPJOQWACG-RTBURBONSA-N (1r,2s)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@H]2C[C@H]2C(=O)NC2=NC3=CC(=NN3C(C=3C=CC=CC=3)=C2)C)=CC=CC=C1 XLOOFDPJOQWACG-RTBURBONSA-N 0.000 claims 1
• XLOOFDPJOQWACG-MOPGFXCFSA-N (1s,2s)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@H]2C[C@@H]2C(=O)NC2=NC3=CC(=NN3C(C=3C=CC=CC=3)=C2)C)=CC=CC=C1 XLOOFDPJOQWACG-MOPGFXCFSA-N 0.000 claims 1
• BAQLCCJCNPZGRP-UXHICEINSA-N (1s,2s)-n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)[C@@H]2[C@H](C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 BAQLCCJCNPZGRP-UXHICEINSA-N 0.000 claims 1
• RZQSKBIYHQMWIB-QGZVFWFLSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 RZQSKBIYHQMWIB-QGZVFWFLSA-N 0.000 claims 1
• LTFBCTANUOPSBW-GOSISDBHSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-propan-2-ylpiperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NC(C)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 LTFBCTANUOPSBW-GOSISDBHSA-N 0.000 claims 1
• BKCNNMYHBNECKH-OAHLLOKOSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxylic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@@H](CCC2)C(O)=O)=C1 BKCNNMYHBNECKH-OAHLLOKOSA-N 0.000 claims 1
• GPXQNYUONOMDOY-QGZVFWFLSA-N (3r)-n-ethyl-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NCC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 GPXQNYUONOMDOY-QGZVFWFLSA-N 0.000 claims 1
• ZJPHAQGVIJMSTQ-INIZCTEOSA-N (3s)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-3-carboxamide Chemical compound C1[C@@H](C(=O)NC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 ZJPHAQGVIJMSTQ-INIZCTEOSA-N 0.000 claims 1
• BKCNNMYHBNECKH-HNNXBMFYSA-N (3s)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxylic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@H](CCC2)C(O)=O)=C1 BKCNNMYHBNECKH-HNNXBMFYSA-N 0.000 claims 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
• ZGCWHLPQHRVEKW-UHFFFAOYSA-N 1-[4-[(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)carbamoyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(C(=O)NC2=NC3=CC=NN3C(N3CCOCC3)=C2)C=CC=1C1(C(=O)O)CC1 ZGCWHLPQHRVEKW-UHFFFAOYSA-N 0.000 claims 1
• YUISYQIJJQLJCV-UHFFFAOYSA-N 1-[5-[(4-tert-butylbenzoyl)amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(CCC2)C(O)=O)=C1 YUISYQIJJQLJCV-UHFFFAOYSA-N 0.000 claims 1
• KSSDNVNCLYKHCQ-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 KSSDNVNCLYKHCQ-UHFFFAOYSA-N 0.000 claims 1
• XXVGSBPYGOMYKH-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 XXVGSBPYGOMYKH-UHFFFAOYSA-N 0.000 claims 1
• RHGCWVWHOXYCMZ-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]piperidine-4-carboxylic acid Chemical compound C1=C(N2CCC(CC2)C(O)=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 RHGCWVWHOXYCMZ-UHFFFAOYSA-N 0.000 claims 1
• ZYJXXPCIMQNSQF-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 ZYJXXPCIMQNSQF-UHFFFAOYSA-N 0.000 claims 1
• MNISJJFFUWARPH-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-propan-2-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC(C)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 MNISJJFFUWARPH-UHFFFAOYSA-N 0.000 claims 1
• PYVKMUJGAZLWQH-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-4-carboxylic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CC2)C(O)=O)=C1 PYVKMUJGAZLWQH-UHFFFAOYSA-N 0.000 claims 1
• KCONEQZFBFDXJP-UHFFFAOYSA-N 1-hydroxy-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)naphthalene-2-carboxamide Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 KCONEQZFBFDXJP-UHFFFAOYSA-N 0.000 claims 1
• WAEGCCBZAWXMOP-UHFFFAOYSA-N 2-[3-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]phenoxy]acetic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(OCC(O)=O)C=CC=2)=C1 WAEGCCBZAWXMOP-UHFFFAOYSA-N 0.000 claims 1
• PYYFYZRKFYCTAZ-UHFFFAOYSA-N 2-[[2-methyl-2-[4-[(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)carbamoyl]phenyl]propyl]amino]-2-oxoacetic acid Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CNC(=O)C(O)=O)C=C1 PYYFYZRKFYCTAZ-UHFFFAOYSA-N 0.000 claims 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
• VMHHMQQXKJBDGE-UHFFFAOYSA-N 4-(1-amino-2-methylpropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CN)C=C1 VMHHMQQXKJBDGE-UHFFFAOYSA-N 0.000 claims 1
• BOOKHCVZOHXOLE-UHFFFAOYSA-N 4-(1-hydroxy-2-methylpropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CO)C=C1 BOOKHCVZOHXOLE-UHFFFAOYSA-N 0.000 claims 1
• JCHMBIBDBRODQQ-UHFFFAOYSA-N 4-(1-hydroxy-2-methylpropan-2-yl)-n-(2-methyl-7-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CO)C=C1 JCHMBIBDBRODQQ-UHFFFAOYSA-N 0.000 claims 1
• ODJOUCPQPQRYRQ-UHFFFAOYSA-N 4-(1-hydroxy-2-methylpropan-2-yl)-n-[7-[3-(methoxymethyl)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COCC1=CC=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)CO)C=2)=C1 ODJOUCPQPQRYRQ-UHFFFAOYSA-N 0.000 claims 1
• XTSRLYKXOHTBGF-UHFFFAOYSA-N 4-(2-cyanopropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)C#N)C=C1 XTSRLYKXOHTBGF-UHFFFAOYSA-N 0.000 claims 1
• OSDDNNPBRQNISI-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCOCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 OSDDNNPBRQNISI-UHFFFAOYSA-N 0.000 claims 1
• NGZAJKWVMZWUFX-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 NGZAJKWVMZWUFX-UHFFFAOYSA-N 0.000 claims 1
• OVPICIBYTKOPMZ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-piperidin-1-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCCCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 OVPICIBYTKOPMZ-UHFFFAOYSA-N 0.000 claims 1
• HKHIVSYMVWKKEA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-thiomorpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCSCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 HKHIVSYMVWKKEA-UHFFFAOYSA-N 0.000 claims 1
• YTWQRKMZEKXYSV-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-methoxypyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound N=1C2=CC=NN2C(OC)=CC=1NC(=O)C1=CC=C(C(C)(C)O)C=C1 YTWQRKMZEKXYSV-UHFFFAOYSA-N 0.000 claims 1
• URFCAOPDTOXVIT-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCOCC2)=C1 URFCAOPDTOXVIT-UHFFFAOYSA-N 0.000 claims 1
• OXVBTSJFGMBZFV-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-phenoxypyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(OC=2C=CC=CC=2)=C1 OXVBTSJFGMBZFV-UHFFFAOYSA-N 0.000 claims 1
• YLYLLTNGHOFLIG-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC=CC=2)=C1 YLYLLTNGHOFLIG-UHFFFAOYSA-N 0.000 claims 1
• APLAAFISJBTNIA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-thiophen-3-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C2=CSC=C2)=C1 APLAAFISJBTNIA-UHFFFAOYSA-N 0.000 claims 1
• VNEYGCYWOLROCZ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(1,4-oxazepan-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2CCOCCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 VNEYGCYWOLROCZ-UHFFFAOYSA-N 0.000 claims 1
• KOGIONJHVPHPIB-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2CCC3(C(NCC3)=O)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 KOGIONJHVPHPIB-UHFFFAOYSA-N 0.000 claims 1
• ITKXZGZKFZXPLB-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(4-phenylsulfanylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2CCC(CC2)SC=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 ITKXZGZKFZXPLB-UHFFFAOYSA-N 0.000 claims 1
• BIWGPJYGUGRDLO-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(4-propylsulfonylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 BIWGPJYGUGRDLO-UHFFFAOYSA-N 0.000 claims 1
• KLJNBSULFBQFJK-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(6-propan-2-yloxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=NC(OC(C)C)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 KLJNBSULFBQFJK-UHFFFAOYSA-N 0.000 claims 1
• ANKJBSSCXNQEKJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C3CNCCC3=CC=2)=C1 ANKJBSSCXNQEKJ-UHFFFAOYSA-N 0.000 claims 1
• NOVFWODZQVVUGJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(2-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound CC1CCCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 NOVFWODZQVVUGJ-UHFFFAOYSA-N 0.000 claims 1
• PJYCQQGNLHYTHL-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(2-methylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound CC1CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 PJYCQQGNLHYTHL-UHFFFAOYSA-N 0.000 claims 1
• UTQFIAIILHWSTK-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)CC2)=C1 UTQFIAIILHWSTK-UHFFFAOYSA-N 0.000 claims 1
• DREIQYKBZWYTTC-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 DREIQYKBZWYTTC-UHFFFAOYSA-N 0.000 claims 1
• SRXIBYPKYPCTMH-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 SRXIBYPKYPCTMH-UHFFFAOYSA-N 0.000 claims 1
• CXNLSEXHNRULTH-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methyl-4-oxopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(=O)C(C)CN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 CXNLSEXHNRULTH-UHFFFAOYSA-N 0.000 claims 1
• LMMYZNOEEXDQBA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-phenylmethoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 LMMYZNOEEXDQBA-UHFFFAOYSA-N 0.000 claims 1
• NQYVHLCKYWSMSX-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 NQYVHLCKYWSMSX-UHFFFAOYSA-N 0.000 claims 1
• OYNMFNCYDOPWTG-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 OYNMFNCYDOPWTG-UHFFFAOYSA-N 0.000 claims 1
• XZYCQIFJSCKTNO-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methoxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(OC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 XZYCQIFJSCKTNO-UHFFFAOYSA-N 0.000 claims 1
• BSPRRNSOYRFXSQ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CN(C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 BSPRRNSOYRFXSQ-UHFFFAOYSA-N 0.000 claims 1
• YMTIHLQIJIRXCY-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(5-oxo-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(=O)NCC2)=C1 YMTIHLQIJIRXCY-UHFFFAOYSA-N 0.000 claims 1
• XYEWZZXJIJERKJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(6-methoxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 XYEWZZXJIJERKJ-UHFFFAOYSA-N 0.000 claims 1
• PGFAEWVVIPQMHG-QGZVFWFLSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC[C@H]1CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 PGFAEWVVIPQMHG-QGZVFWFLSA-N 0.000 claims 1
• AIQHDRCALMTPEL-MRXNPFEDSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[(3r)-3-hydroxypyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2C[C@H](O)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 AIQHDRCALMTPEL-MRXNPFEDSA-N 0.000 claims 1
• QMTVONRIZNAICT-MDWZMJQESA-N 4-(2-hydroxypropan-2-yl)-n-[7-[(e)-2-phenylethenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(\C=C\C=2C=CC=CC=2)=C1 QMTVONRIZNAICT-MDWZMJQESA-N 0.000 claims 1
• FILSZLVHAPATHA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[3-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COCC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 FILSZLVHAPATHA-UHFFFAOYSA-N 0.000 claims 1
• RWJQUEHUOPEFAJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(2-methoxyethoxy)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(OCCOC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 RWJQUEHUOPEFAJ-UHFFFAOYSA-N 0.000 claims 1
• IKFQRDUEJYZEIP-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(methoxymethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(COC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 IKFQRDUEJYZEIP-UHFFFAOYSA-N 0.000 claims 1
• HSNFRHHGMPPLLU-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(=CC=2)C(F)(F)F)=C1 HSNFRHHGMPPLLU-UHFFFAOYSA-N 0.000 claims 1
• KPAMBRUDIQVBEP-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(trifluoromethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CC2)C(F)(F)F)=C1 KPAMBRUDIQVBEP-UHFFFAOYSA-N 0.000 claims 1
• POFLOXDHDATTRX-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-phenyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C(F)(F)F)=NN2C(C=2C=CC=CC=2)=C1 POFLOXDHDATTRX-UHFFFAOYSA-N 0.000 claims 1
• VEWMKHGIRZXZKY-UHFFFAOYSA-N 4-bromo-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCOCC2)=C1 VEWMKHGIRZXZKY-UHFFFAOYSA-N 0.000 claims 1
• LBULRDWVNGYSHF-UHFFFAOYSA-N 4-tert-butyl-n-(7-imidazol-1-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C=NC=C2)=C1 LBULRDWVNGYSHF-UHFFFAOYSA-N 0.000 claims 1
• QIKBRXBBYPUZBQ-UHFFFAOYSA-N 4-tert-butyl-n-(7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC=CC=2)=C1 QIKBRXBBYPUZBQ-UHFFFAOYSA-N 0.000 claims 1
• PHILPEMWGYVCIT-UHFFFAOYSA-N 4-tert-butyl-n-[7-(1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2N=CN=C2)=C1 PHILPEMWGYVCIT-UHFFFAOYSA-N 0.000 claims 1
• GFQOGZZSSZKYHK-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2,4-dimethoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 GFQOGZZSSZKYHK-UHFFFAOYSA-N 0.000 claims 1
• JKFGYALKQVWZDY-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C(=CC=CC=2)Cl)=C1 JKFGYALKQVWZDY-UHFFFAOYSA-N 0.000 claims 1
• GAVOASGNDXRVRH-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-formylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C(=CC=CC=2)C=O)=C1 GAVOASGNDXRVRH-UHFFFAOYSA-N 0.000 claims 1
• KPJVNRMXDNWSFO-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-methoxyethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound N=1C2=CC=NN2C(NCCOC)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 KPJVNRMXDNWSFO-UHFFFAOYSA-N 0.000 claims 1
• ODPUAGJIBBRIJH-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=NC=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 ODPUAGJIBBRIJH-UHFFFAOYSA-N 0.000 claims 1
• USPWFJWYPKWCLK-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-phenoxyethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCOC=2C=CC=CC=2)=C1 USPWFJWYPKWCLK-UHFFFAOYSA-N 0.000 claims 1
• QVBVJQMPIRTUJN-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-phenylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 QVBVJQMPIRTUJN-UHFFFAOYSA-N 0.000 claims 1
• ZHTQWKPMADUEFF-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(F)C(F)=CC=2)=C1 ZHTQWKPMADUEFF-UHFFFAOYSA-N 0.000 claims 1
• RAQNRGCLEGPOHO-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3,5-dimethylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound CC1=CC(C)=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=2)=C1 RAQNRGCLEGPOHO-UHFFFAOYSA-N 0.000 claims 1
• LSPXXOHJLRYSRV-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)CCC2)=C1 LSPXXOHJLRYSRV-UHFFFAOYSA-N 0.000 claims 1
• TZPPYSZHTGWMKS-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-hydroxypropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCCO)=C1 TZPPYSZHTGWMKS-UHFFFAOYSA-N 0.000 claims 1
• HSOYZOIVKYYGTM-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)CC2)=C1 HSOYZOIVKYYGTM-UHFFFAOYSA-N 0.000 claims 1
• HYANODCDSONKCC-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-imidazol-1-ylpropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCCN2C=NC=C2)=C1 HYANODCDSONKCC-UHFFFAOYSA-N 0.000 claims 1
• JKKIGCZARYAMFG-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=2)=C1 JKKIGCZARYAMFG-UHFFFAOYSA-N 0.000 claims 1
• MILCJMXNKSNBTK-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-nitrophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 MILCJMXNKSNBTK-UHFFFAOYSA-N 0.000 claims 1
• LXYFLKWLGKPGOG-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(Cl)=CC=2)=C1 LXYFLKWLGKPGOG-UHFFFAOYSA-N 0.000 claims 1
• MZUYCOFUVHGZFL-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-cyanophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(=CC=2)C#N)=C1 MZUYCOFUVHGZFL-UHFFFAOYSA-N 0.000 claims 1
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• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 1
• WUYMFZXQINNMDH-UHFFFAOYSA-N methyl 3-methyl-3-[4-[(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)carbamoyl]phenyl]butanoate Chemical compound C1=CC(C(C)(C)CC(=O)OC)=CC=C1C(=O)NC1=NC2=CC(C)=NN2C(C=2C=CC=CC=2)=C1 WUYMFZXQINNMDH-UHFFFAOYSA-N 0.000 claims 1
• MFHCJCXVSNXMMX-UHFFFAOYSA-N methyl 4-[[7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl]carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NC1=NC2=CC(C(F)(F)F)=NN2C(Cl)=C1 MFHCJCXVSNXMMX-UHFFFAOYSA-N 0.000 claims 1
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
• 206010028417 myasthenia gravis Diseases 0.000 claims 1
• OPUKJSNLBUTHEL-UHFFFAOYSA-N n-(2-cyclopropyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(N2CCOCC2)=C1 OPUKJSNLBUTHEL-UHFFFAOYSA-N 0.000 claims 1
• BQGFLIBCWVBNJC-UHFFFAOYSA-N n-(2-cyclopropyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(C=2C=CC=CC=2)=C1 BQGFLIBCWVBNJC-UHFFFAOYSA-N 0.000 claims 1
• ZSTMVYUUNXHVKM-UHFFFAOYSA-N n-(2-ethyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCOCC2)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 ZSTMVYUUNXHVKM-UHFFFAOYSA-N 0.000 claims 1
• MERDQKDFRBJRFH-UHFFFAOYSA-N n-(2-ethyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 MERDQKDFRBJRFH-UHFFFAOYSA-N 0.000 claims 1
• HPGFYRQOXWFXPN-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxamide Chemical compound C1=C(N2CC(CCC2)C(=O)NCCO)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 HPGFYRQOXWFXPN-UHFFFAOYSA-N 0.000 claims 1
• OTWQDHKOMSWLBH-UHFFFAOYSA-N n-(2-methyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1=C(N2CCOCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 OTWQDHKOMSWLBH-UHFFFAOYSA-N 0.000 claims 1
• ONAQJOVAGCFGNA-UHFFFAOYSA-N n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-pyridin-4-ylcyclopropane-1-carboxamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=NC=C1 ONAQJOVAGCFGNA-UHFFFAOYSA-N 0.000 claims 1
• FSOYJJCOCILNSQ-UHFFFAOYSA-N n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethylsulfanyl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(SC(F)(F)F)C=C1 FSOYJJCOCILNSQ-UHFFFAOYSA-N 0.000 claims 1
• XMCWVGPWWKKTGR-UHFFFAOYSA-N n-(7-butoxypyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound N=1C2=CC=NN2C(OCCCC)=CC=1NC(=O)C1=CC=C(C(C)(C)O)C=C1 XMCWVGPWWKKTGR-UHFFFAOYSA-N 0.000 claims 1
• BDPSQJSOSJRMOB-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-1h-imidazole-5-carboxamide Chemical compound C=1NC=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 BDPSQJSOSJRMOB-UHFFFAOYSA-N 0.000 claims 1
• NMFBQUHBWLMBSC-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-1h-indole-2-carboxamide Chemical compound C=1C2=CC=CC=C2NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 NMFBQUHBWLMBSC-UHFFFAOYSA-N 0.000 claims 1
• JLQYNJKCDXMTFU-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-1h-indole-6-carboxamide Chemical compound C=1C=C2C=CNC2=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 JLQYNJKCDXMTFU-UHFFFAOYSA-N 0.000 claims 1
• ICIIAJPTQIRTJR-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-phenylbenzamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 ICIIAJPTQIRTJR-UHFFFAOYSA-N 0.000 claims 1
• GOAKYWJNGOHUDT-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 GOAKYWJNGOHUDT-UHFFFAOYSA-N 0.000 claims 1
• YZKVXMKEPJBUOJ-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopentanecarboxamide Chemical compound C1CCCC1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 YZKVXMKEPJBUOJ-UHFFFAOYSA-N 0.000 claims 1
• BCUZRCFZMBJTLS-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 BCUZRCFZMBJTLS-UHFFFAOYSA-N 0.000 claims 1
• HDWTWKHIJLRRQS-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)isoquinoline-1-carboxamide Chemical compound N=1C=CC2=CC=CC=C2C=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 HDWTWKHIJLRRQS-UHFFFAOYSA-N 0.000 claims 1
• JRIKQZXEEDAPST-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 JRIKQZXEEDAPST-UHFFFAOYSA-N 0.000 claims 1
• HCSUTONYMOXNKH-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 HCSUTONYMOXNKH-UHFFFAOYSA-N 0.000 claims 1
• FTIAAQOYCNRCHK-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 FTIAAQOYCNRCHK-UHFFFAOYSA-N 0.000 claims 1
• PTVYPHBQXFDCGC-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 PTVYPHBQXFDCGC-UHFFFAOYSA-N 0.000 claims 1
• DIKAUSMLHNEYTM-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 DIKAUSMLHNEYTM-UHFFFAOYSA-N 0.000 claims 1
• STQVQHAXYKGWKV-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)quinoline-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 STQVQHAXYKGWKV-UHFFFAOYSA-N 0.000 claims 1
• FKNKCEVMDPZHLL-UHFFFAOYSA-N n-[2-cyclopropyl-7-(4-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(N2CCC(O)CC2)=C1 FKNKCEVMDPZHLL-UHFFFAOYSA-N 0.000 claims 1
• ADDYBUKCSAYFCN-UHFFFAOYSA-N n-[2-cyclopropyl-7-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(C=2C=C(CO)C=CC=2)=C1 ADDYBUKCSAYFCN-UHFFFAOYSA-N 0.000 claims 1
• SQHKKZOFRSMHKZ-UHFFFAOYSA-N n-[2-ethyl-7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=CC(OC)=CC=2)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 SQHKKZOFRSMHKZ-UHFFFAOYSA-N 0.000 claims 1
• FHAQFTIPYLRUNH-UHFFFAOYSA-N n-[2-methyl-7-(4-oxo-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=C(N2CC=3C(=O)NC=NC=3CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(F)(F)F)N=C1 FHAQFTIPYLRUNH-UHFFFAOYSA-N 0.000 claims 1
• JZIJXAUJSGKFCX-UHFFFAOYSA-N n-[7-(1-benzofuran-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3C=COC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 JZIJXAUJSGKFCX-UHFFFAOYSA-N 0.000 claims 1
• OJHFPZOZLUFFNK-UHFFFAOYSA-N n-[7-(1-benzothiophen-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2SC3=CC=CC=C3C=2)=C1 OJHFPZOZLUFFNK-UHFFFAOYSA-N 0.000 claims 1
• XDPZNOYZTVTBJI-UHFFFAOYSA-N n-[7-(1-benzothiophen-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3C=CSC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 XDPZNOYZTVTBJI-UHFFFAOYSA-N 0.000 claims 1
• RCCIIPOVABHVEQ-UHFFFAOYSA-N n-[7-(1-benzylpyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C2=CN(CC=3C=CC=CC=3)N=C2)=C1 RCCIIPOVABHVEQ-UHFFFAOYSA-N 0.000 claims 1
• SRZVUWXFVSDPOH-UHFFFAOYSA-N n-[7-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3OCCOC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 SRZVUWXFVSDPOH-UHFFFAOYSA-N 0.000 claims 1
• LSQIXHYREQQVBX-UHFFFAOYSA-N n-[7-(2,3-dihydro-1-benzofuran-5-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C3CCOC3=CC=2)=C1 LSQIXHYREQQVBX-UHFFFAOYSA-N 0.000 claims 1
• FRIMYNAZEZEIHL-UHFFFAOYSA-N n-[7-(2,5-dimethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound CC1CNC(C)CN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 FRIMYNAZEZEIHL-UHFFFAOYSA-N 0.000 claims 1
• CVHOBRVTMBYFCA-UHFFFAOYSA-N n-[7-(2,6-dimethylmorpholin-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1C(C)OC(C)CN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 CVHOBRVTMBYFCA-UHFFFAOYSA-N 0.000 claims 1
• PWGUALKWLXGXAH-UHFFFAOYSA-N n-[7-(2-acetamidoethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound N=1C2=CC=NN2C(NCCNC(=O)C)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 PWGUALKWLXGXAH-UHFFFAOYSA-N 0.000 claims 1
• XTEYFWCUKBBSBT-UHFFFAOYSA-N n-[7-(2-acetamidophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound CC(=O)NC1=CC=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 XTEYFWCUKBBSBT-UHFFFAOYSA-N 0.000 claims 1
• BVTWWNVIJQQJRS-UHFFFAOYSA-N n-[7-(3,3-dimethylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(C)(C)CCC2)=C1 BVTWWNVIJQQJRS-UHFFFAOYSA-N 0.000 claims 1
• VEWKFBYPAYSZTD-UHFFFAOYSA-N n-[7-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3OCCCOC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 VEWKFBYPAYSZTD-UHFFFAOYSA-N 0.000 claims 1
• KIXKARMPHFURHJ-UHFFFAOYSA-N n-[7-(3,4-dimethoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 KIXKARMPHFURHJ-UHFFFAOYSA-N 0.000 claims 1
• IRTOZPPWXFRTRM-UHFFFAOYSA-N n-[7-(3-acetamidophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound CC(=O)NC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 IRTOZPPWXFRTRM-UHFFFAOYSA-N 0.000 claims 1
• GAOPZXNWJBZZGO-UHFFFAOYSA-N n-[7-(3-acetamidopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1C(NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 GAOPZXNWJBZZGO-UHFFFAOYSA-N 0.000 claims 1
• VJGSUTXXRJAXIU-UHFFFAOYSA-N n-[7-(3-acetylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound CC(=O)C1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=2)=C1 VJGSUTXXRJAXIU-UHFFFAOYSA-N 0.000 claims 1
• QKMOFNDOZPPJQC-UHFFFAOYSA-N n-[7-(3-chloro-4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 QKMOFNDOZPPJQC-UHFFFAOYSA-N 0.000 claims 1
• MKODGKWQJKCQRG-UHFFFAOYSA-N n-[7-(3-fluoro-4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 MKODGKWQJKCQRG-UHFFFAOYSA-N 0.000 claims 1
• ZYUKLUSFJNUMBB-UHFFFAOYSA-N n-[7-(3-fluoropyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CC(F)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 ZYUKLUSFJNUMBB-UHFFFAOYSA-N 0.000 claims 1
• CMJMDOYEPQELBK-UHFFFAOYSA-N n-[7-(3-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(F)CC2)=C1 CMJMDOYEPQELBK-UHFFFAOYSA-N 0.000 claims 1
• XCPSKVKLNWTWNK-UHFFFAOYSA-N n-[7-(3-hydroxyazetidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)C2)=C1 XCPSKVKLNWTWNK-UHFFFAOYSA-N 0.000 claims 1
• FPVRMLKKCXYSRT-UHFFFAOYSA-N n-[7-(4,4-difluoropiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(F)(F)CC2)=C1 FPVRMLKKCXYSRT-UHFFFAOYSA-N 0.000 claims 1
• PLUCVGXBZYKWJO-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-(4-fluorophenyl)cyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C2C(C2)C=2C=CC(F)=CC=2)=NC2=CC(C)=NN12 PLUCVGXBZYKWJO-UHFFFAOYSA-N 0.000 claims 1
• BAQLCCJCNPZGRP-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C2C(C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 BAQLCCJCNPZGRP-UHFFFAOYSA-N 0.000 claims 1
• PMHYKFSXBCPOQU-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 PMHYKFSXBCPOQU-UHFFFAOYSA-N 0.000 claims 1
• DUCDCBMKWBHRQP-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(OC(F)(F)F)=CC=2)=NC2=CC(C)=NN12 DUCDCBMKWBHRQP-UHFFFAOYSA-N 0.000 claims 1
• QVQWLKHJJGVYLZ-UHFFFAOYSA-N n-[7-(4-acetyl-1,4-diazepan-1-yl)-2-ethylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCN(CCC2)C(C)=O)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 QVQWLKHJJGVYLZ-UHFFFAOYSA-N 0.000 claims 1
• MDOVNNQNKBRACZ-UHFFFAOYSA-N n-[7-(4-acetyl-1,4-diazepan-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CN(C(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 MDOVNNQNKBRACZ-UHFFFAOYSA-N 0.000 claims 1
• GZTMBUOBNRVKPK-UHFFFAOYSA-N n-[7-(4-acetyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CN(C(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 GZTMBUOBNRVKPK-UHFFFAOYSA-N 0.000 claims 1
• CKYUAZMFSWKXPC-UHFFFAOYSA-N n-[7-(4-chloro-3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(Cl)C(OC)=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 CKYUAZMFSWKXPC-UHFFFAOYSA-N 0.000 claims 1
• RQYQCZBTJIJGFO-UHFFFAOYSA-N n-[7-(4-chloro-3-methylphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C(C)C(Cl)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 RQYQCZBTJIJGFO-UHFFFAOYSA-N 0.000 claims 1
• UFAZMLALHXATRN-UHFFFAOYSA-N n-[7-(4-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 UFAZMLALHXATRN-UHFFFAOYSA-N 0.000 claims 1
• WFFYREPHDYEYIB-UHFFFAOYSA-N n-[7-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(Cl)=CC=2)=C1 WFFYREPHDYEYIB-UHFFFAOYSA-N 0.000 claims 1
• RAVDORCIIGKVID-UHFFFAOYSA-N n-[7-(4-ethylsulfonylpiperazin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 RAVDORCIIGKVID-UHFFFAOYSA-N 0.000 claims 1
• NBTPAULWHKTYSI-UHFFFAOYSA-N n-[7-(4-fluoro-3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(F)C(OC)=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 NBTPAULWHKTYSI-UHFFFAOYSA-N 0.000 claims 1
• WVPRZQFVXLXOQW-UHFFFAOYSA-N n-[7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(F)=CC=2)=C1 WVPRZQFVXLXOQW-UHFFFAOYSA-N 0.000 claims 1
• YJFSMWYZHUWZQW-UHFFFAOYSA-N n-[7-(4-formyl-1,4-diazepan-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCN(CCC2)C=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 YJFSMWYZHUWZQW-UHFFFAOYSA-N 0.000 claims 1
• ULSTWQKCFHLIIY-UHFFFAOYSA-N n-[7-(4-formyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCN(CCC2)C=O)=C1 ULSTWQKCFHLIIY-UHFFFAOYSA-N 0.000 claims 1
• SKDLLRSDYAKYKX-UHFFFAOYSA-N n-[7-(4-formylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCN(CC2)C=O)=C1 SKDLLRSDYAKYKX-UHFFFAOYSA-N 0.000 claims 1
• ZRFVWIOXHVWPAH-UHFFFAOYSA-N n-[7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)C2C(C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 ZRFVWIOXHVWPAH-UHFFFAOYSA-N 0.000 claims 1
• MOBPYRXGYZFLLV-UHFFFAOYSA-N n-[7-(5-chlorothiophen-2-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2SC(Cl)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 MOBPYRXGYZFLLV-UHFFFAOYSA-N 0.000 claims 1
• AFSYGHSRVUTXCS-UHFFFAOYSA-N n-[7-(6-acetamidopyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 AFSYGHSRVUTXCS-UHFFFAOYSA-N 0.000 claims 1
• YMVPSNWNOCCXRQ-UHFFFAOYSA-N n-[7-(6-ethoxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=NC(OCC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 YMVPSNWNOCCXRQ-UHFFFAOYSA-N 0.000 claims 1
• ITWUICXUCZCLFG-UHFFFAOYSA-N n-[7-(benzylamino)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC=2C=CC=CC=2)=C1 ITWUICXUCZCLFG-UHFFFAOYSA-N 0.000 claims 1
• YZQMRCNHOWOGFM-UHFFFAOYSA-N n-[7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC2CC2)=C1 YZQMRCNHOWOGFM-UHFFFAOYSA-N 0.000 claims 1
• ZWBRUWNOURXXFY-UHFFFAOYSA-N n-[7-(furan-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C2=COC=C2)=C1 ZWBRUWNOURXXFY-UHFFFAOYSA-N 0.000 claims 1
• NLOZGPVCMXOSBO-UHFFFAOYSA-N n-[7-[(2-amino-2-oxoethyl)amino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC(N)=O)=C1 NLOZGPVCMXOSBO-UHFFFAOYSA-N 0.000 claims 1
• QAWAGEIDSIRFEG-UHFFFAOYSA-N n-[7-[(3-amino-3-oxopropyl)amino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCC(N)=O)=C1 QAWAGEIDSIRFEG-UHFFFAOYSA-N 0.000 claims 1
• YUIHSJPQWUJXRG-QGZVFWFLSA-N n-[7-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@H](N(C)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 YUIHSJPQWUJXRG-QGZVFWFLSA-N 0.000 claims 1
• RIXBOFJAWNSJJD-GOSISDBHSA-N n-[7-[(3r)-3-acetamidopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@H](NC(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 RIXBOFJAWNSJJD-GOSISDBHSA-N 0.000 claims 1
• YUJPRSWKBRFJBI-QGZVFWFLSA-N n-[7-[(3r)-3-acetamidopyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@H](NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 YUJPRSWKBRFJBI-QGZVFWFLSA-N 0.000 claims 1
• GAOPZXNWJBZZGO-GOSISDBHSA-N n-[7-[(3r)-3-acetamidopyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1[C@H](NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 GAOPZXNWJBZZGO-GOSISDBHSA-N 0.000 claims 1
• GWMBGNCOGKPDQP-MRXNPFEDSA-N n-[7-[(3r)-3-aminopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@H](N)CCC2)=C1 GWMBGNCOGKPDQP-MRXNPFEDSA-N 0.000 claims 1
• UAZQWXUPPLTVMK-KLAILNCOSA-N n-[7-[(3r)-3-fluoropyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=C(N2C[C@H](F)CC2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 UAZQWXUPPLTVMK-KLAILNCOSA-N 0.000 claims 1
• RIXBOFJAWNSJJD-SFHVURJKSA-N n-[7-[(3s)-3-acetamidopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@@H](NC(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 RIXBOFJAWNSJJD-SFHVURJKSA-N 0.000 claims 1
• YUJPRSWKBRFJBI-KRWDZBQOSA-N n-[7-[(3s)-3-acetamidopyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@@H](NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 YUJPRSWKBRFJBI-KRWDZBQOSA-N 0.000 claims 1
• GWMBGNCOGKPDQP-INIZCTEOSA-N n-[7-[(3s)-3-aminopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@@H](N)CCC2)=C1 GWMBGNCOGKPDQP-INIZCTEOSA-N 0.000 claims 1
• UAZQWXUPPLTVMK-GTPINHCMSA-N n-[7-[(3s)-3-fluoropyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=C(N2C[C@@H](F)CC2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 UAZQWXUPPLTVMK-GTPINHCMSA-N 0.000 claims 1
• OMDWXUAZPMBIMZ-UHFFFAOYSA-N n-[7-[2-(2-hydroxyethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C(CCCC2)CCO)=C1 OMDWXUAZPMBIMZ-UHFFFAOYSA-N 0.000 claims 1
• HGFMTDOZRMZAKE-UHFFFAOYSA-N n-[7-[2-(acetylsulfamoyl)ethyl-methylamino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound N=1C2=CC=NN2C(N(CCS(=O)(=O)NC(C)=O)C)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 HGFMTDOZRMZAKE-UHFFFAOYSA-N 0.000 claims 1
• ALXZPDICGNLWMN-UHFFFAOYSA-N n-[7-[3-(cyanomethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CC#N)C=CC=2)=C1 ALXZPDICGNLWMN-UHFFFAOYSA-N 0.000 claims 1
• WIUBDPVCYFVRGZ-UHFFFAOYSA-N n-[7-[3-(dimethylamino)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound CN(C)C1=CC=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 WIUBDPVCYFVRGZ-UHFFFAOYSA-N 0.000 claims 1
• FZVYUICXNYCBFC-UHFFFAOYSA-N n-[7-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CO)C=CC=2)=C1 FZVYUICXNYCBFC-UHFFFAOYSA-N 0.000 claims 1
• IVHRSJVMGRUVQH-UHFFFAOYSA-N n-[7-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CO)C=CC=2)=C1 IVHRSJVMGRUVQH-UHFFFAOYSA-N 0.000 claims 1
• RHRRIETVEGSRDU-UHFFFAOYSA-N n-[7-[3-(hydroxymethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(CO)CCC2)=C1 RHRRIETVEGSRDU-UHFFFAOYSA-N 0.000 claims 1
• CTTKOLYAYSHOIV-UHFFFAOYSA-N n-[7-[4-(2-amino-2-oxoethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1=C(N2CCC(CC(N)=O)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 CTTKOLYAYSHOIV-UHFFFAOYSA-N 0.000 claims 1
• PLWPTZIISYVPKO-UHFFFAOYSA-N n-[7-[4-(2-hydroxyethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=C(N2CCC(CCO)CC2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 PLWPTZIISYVPKO-UHFFFAOYSA-N 0.000 claims 1
• BHDYIUXAVFNTTA-UHFFFAOYSA-N n-[7-[4-(2-hydroxyethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CCO)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 BHDYIUXAVFNTTA-UHFFFAOYSA-N 0.000 claims 1
• LRKCSESWUGRGGP-UHFFFAOYSA-N n-[7-[4-(2-hydroxyethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CCO)CC2)=C1 LRKCSESWUGRGGP-UHFFFAOYSA-N 0.000 claims 1
• WURDOVBEVHXNIQ-UHFFFAOYSA-N n-[7-[4-(benzenesulfonyl)piperazin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 WURDOVBEVHXNIQ-UHFFFAOYSA-N 0.000 claims 1
• UHVPBXFTSUYPJN-UHFFFAOYSA-N n-[7-[4-(benzenesulfonyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CC2)S(=O)(=O)C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 UHVPBXFTSUYPJN-UHFFFAOYSA-N 0.000 claims 1
• PMRUKZBTOJVGPW-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-(4-fluorophenyl)cyclopropane-1-carboxamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=C(F)C=C1 PMRUKZBTOJVGPW-UHFFFAOYSA-N 0.000 claims 1
• FSXOIVPEFWVRPF-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-pyridin-4-ylcyclopropane-1-carboxamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=NC=C1 FSXOIVPEFWVRPF-UHFFFAOYSA-N 0.000 claims 1
• JETIGXKPROJZQI-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 JETIGXKPROJZQI-UHFFFAOYSA-N 0.000 claims 1
• ZJKBBUNBZBYKJM-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 ZJKBBUNBZBYKJM-UHFFFAOYSA-N 0.000 claims 1
• BQYRDXRGLYWNES-UHFFFAOYSA-N n-[7-[4-(cyclopropanecarbonylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CC2)NC(=O)C2CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 BQYRDXRGLYWNES-UHFFFAOYSA-N 0.000 claims 1
• UMBAFAFAXCPVTN-UHFFFAOYSA-N n-[7-[4-(hydroxymethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CO)CC2)=C1 UMBAFAFAXCPVTN-UHFFFAOYSA-N 0.000 claims 1
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