ES2475091T3 - Imidazopirazinas como inhibidores de proteína cinasas - Google Patents

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Publication number

ES2475091T3

ES2475091T3 ES10716002.0T ES10716002T ES2475091T3 ES 2475091 T3 ES2475091 T3 ES 2475091T3 ES 10716002 T ES10716002 T ES 10716002T ES 2475091 T3 ES2475091 T3 ES 2475091T3

Authority

ES

Spain

Prior art keywords

imidazo

morpholin

pyrazine

methyl

pyrazin

Prior art date

2009-04-16

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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• 150000005235 imidazopyrazines Chemical class 0.000 title claims description 20
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
• 239000003909 protein kinase inhibitor Substances 0.000 title description 2
• 125000001424 substituent group Chemical group 0.000 claims abstract description 271
• 150000001875 compounds Chemical class 0.000 claims abstract description 244
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 129
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 95
• 239000001257 hydrogen Substances 0.000 claims abstract description 95
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 92
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 82
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 81
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 55
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 51
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 27
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 24
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
• 239000012634 fragment Substances 0.000 claims abstract description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
• -1 indolonyl Chemical group 0.000 claims description 214
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 112
• 238000006243 chemical reaction Methods 0.000 claims description 112
• 229910052736 halogen Inorganic materials 0.000 claims description 109
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 106
• 150000002367 halogens Chemical group 0.000 claims description 104
• 238000000034 method Methods 0.000 claims description 82
• 125000003118 aryl group Chemical group 0.000 claims description 71
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
• 239000000460 chlorine Substances 0.000 claims description 44
• 229910052760 oxygen Inorganic materials 0.000 claims description 44
• 239000001301 oxygen Substances 0.000 claims description 43
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 229910052717 sulfur Inorganic materials 0.000 claims description 32
• 150000002148 esters Chemical class 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 229910052801 chlorine Inorganic materials 0.000 claims description 30
• 201000010099 disease Diseases 0.000 claims description 30
• 125000001153 fluoro group Chemical group F* 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 27
• 239000011593 sulfur Substances 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 27
• 206010028980 Neoplasm Diseases 0.000 claims description 26
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
• 150000001408 amides Chemical class 0.000 claims description 25
• 125000004122 cyclic group Chemical group 0.000 claims description 25
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 24
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
• 125000002757 morpholinyl group Chemical group 0.000 claims description 23
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 22
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 239000011737 fluorine Substances 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 21
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
• 125000002619 bicyclic group Chemical group 0.000 claims description 20
• 201000011510 cancer Diseases 0.000 claims description 19
• 239000003153 chemical reaction reagent Substances 0.000 claims description 19
• 125000003386 piperidinyl group Chemical group 0.000 claims description 18
• 229910052740 iodine Inorganic materials 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 16
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 15
• 239000011630 iodine Substances 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 239000002671 adjuvant Substances 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 125000002837 carbocyclic group Chemical group 0.000 claims description 10
• WOQWZFFDMVYHSZ-UHFFFAOYSA-N ethyl 6-(1h-indazol-4-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazine-2-carboxylate Chemical compound C12=NC(C(=O)OCC)=CN2C=C(C=2C=3C=NNC=3C=CC=2)N=C1N1CCOCC1 WOQWZFFDMVYHSZ-UHFFFAOYSA-N 0.000 claims description 10
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 229940124597 therapeutic agent Drugs 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 230000002062 proliferating effect Effects 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
• WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 7
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 6
• NVRQQWOJYDZFJR-UHFFFAOYSA-N 3-(2-methyl-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl)phenol Chemical compound C12=NC(C)=CN2C=C(C=2C=C(O)C=CC=2)N=C1N1CCOCC1 NVRQQWOJYDZFJR-UHFFFAOYSA-N 0.000 claims description 6
• FPARKAYQUPWGIJ-UHFFFAOYSA-N 4-[2-cyclopropyl-6-(1h-indazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CC1C1=CN(C=C(N=C2N3CCOCC3)C=3C=4C=NNC=4C=CC=3)C2=N1 FPARKAYQUPWGIJ-UHFFFAOYSA-N 0.000 claims description 6
• NBIPXSFGOGNXNE-UHFFFAOYSA-N 4-[3-bromo-6-(1h-indazol-4-yl)-2-methylimidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound N=1C(C=2C=3C=NNC=3C=CC=2)=CN2C(Br)=C(C)N=C2C=1N1CCOCC1 NBIPXSFGOGNXNE-UHFFFAOYSA-N 0.000 claims description 6
• JVNJYXWPNGPRNB-UHFFFAOYSA-N 4-[6-(1h-indazol-4-yl)-2-(trifluoromethyl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C12=NC(C(F)(F)F)=CN2C=C(C=2C=3C=NNC=3C=CC=2)N=C1N1CCOCC1 JVNJYXWPNGPRNB-UHFFFAOYSA-N 0.000 claims description 6
• 125000005647 linker group Chemical group 0.000 claims description 6
• IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 6
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 5
• WRIUXURXTZPENY-UHFFFAOYSA-N 4-(2-methyl-6-pyridin-4-ylimidazo[1,2-a]pyrazin-8-yl)morpholine Chemical compound C12=NC(C)=CN2C=C(C=2C=CN=CC=2)N=C1N1CCOCC1 WRIUXURXTZPENY-UHFFFAOYSA-N 0.000 claims description 5
• PJQDHKDXJGGTDR-UHFFFAOYSA-N 4-(5-iodo-2-methyl-6-pyridin-3-ylimidazo[1,2-a]pyrazin-8-yl)morpholine Chemical compound C12=NC(C)=CN2C(I)=C(C=2C=NC=CC=2)N=C1N1CCOCC1 PJQDHKDXJGGTDR-UHFFFAOYSA-N 0.000 claims description 5
• DALRFNXYGPODSX-UHFFFAOYSA-N 4-[5-chloro-6-(1h-indazol-4-yl)-2-[[4-(sulfonylmethyl)piperazin-1-yl]methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C12=NC(CN3CCN(CC3)C=S(=O)=O)=CN2C(Cl)=C(C=2C=3C=NNC=3C=CC=2)N=C1N1CCOCC1 DALRFNXYGPODSX-UHFFFAOYSA-N 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 230000004663 cell proliferation Effects 0.000 claims description 5
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 5
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
• RBYSGMDJXWSYMG-UHFFFAOYSA-N 1-methyl-3-[4-(2-methyl-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2CCOCC2)=CN2C1=NC(C)=C2 RBYSGMDJXWSYMG-UHFFFAOYSA-N 0.000 claims description 4
• CENUCRXUCXKMFP-UHFFFAOYSA-N 4-(5-chloro-2-methyl-6-pyridin-3-ylimidazo[1,2-a]pyrazin-8-yl)morpholine Chemical compound C12=NC(C)=CN2C(Cl)=C(C=2C=NC=CC=2)N=C1N1CCOCC1 CENUCRXUCXKMFP-UHFFFAOYSA-N 0.000 claims description 4
• ZALQLJINEGWSSO-UHFFFAOYSA-N 4-(5-chloro-2-methyl-6-pyridin-4-ylimidazo[1,2-a]pyrazin-8-yl)morpholine Chemical compound C12=NC(C)=CN2C(Cl)=C(C=2C=CN=CC=2)N=C1N1CCOCC1 ZALQLJINEGWSSO-UHFFFAOYSA-N 0.000 claims description 4
• YTWBUNPLVBLAQP-UHFFFAOYSA-N 4-[5-bromo-6-(1h-indazol-4-yl)-2-methylimidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C12=NC(C)=CN2C(Br)=C(C=2C=3C=NNC=3C=CC=2)N=C1N1CCOCC1 YTWBUNPLVBLAQP-UHFFFAOYSA-N 0.000 claims description 4
• WGUOOXZDVCRLGF-UHFFFAOYSA-N 4-[5-chloro-6-(1h-indazol-4-yl)-2-methylimidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C12=NC(C)=CN2C(Cl)=C(C=2C=3C=NNC=3C=CC=2)N=C1N1CCOCC1 WGUOOXZDVCRLGF-UHFFFAOYSA-N 0.000 claims description 4
• LQFKXENZXPRCPB-UHFFFAOYSA-N 4-[5-chloro-6-(3-methoxyphenyl)-2-methylimidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound COC1=CC=CC(C2=C(N3C=C(C)N=C3C(N3CCOCC3)=N2)Cl)=C1 LQFKXENZXPRCPB-UHFFFAOYSA-N 0.000 claims description 4
• 208000020084 Bone disease Diseases 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• HFPMUAILHNYPFP-UHFFFAOYSA-N n-ethyl-6-(1h-indazol-4-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazine-2-carboxamide Chemical compound C12=NC(C(=O)NCC)=CN2C=C(C=2C=3C=NNC=3C=CC=2)N=C1N1CCOCC1 HFPMUAILHNYPFP-UHFFFAOYSA-N 0.000 claims description 4
• HQSUDCCNUKPXGF-UHFFFAOYSA-N 1-[4-[[6-(3-hydroxyphenyl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=C(O)C=CC=3)C2=N1 HQSUDCCNUKPXGF-UHFFFAOYSA-N 0.000 claims description 3
• GVAQWGWCASRLAD-UHFFFAOYSA-N 4-(2-methyl-6-pyridin-3-ylimidazo[1,2-a]pyrazin-8-yl)morpholine Chemical compound C12=NC(C)=CN2C=C(C=2C=NC=CC=2)N=C1N1CCOCC1 GVAQWGWCASRLAD-UHFFFAOYSA-N 0.000 claims description 3
• LEJBBVDMHSVUFT-UHFFFAOYSA-N 4-[5-iodo-6-(3-methoxyphenyl)-2-methylimidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound COC1=CC=CC(C2=C(N3C=C(C)N=C3C(N3CCOCC3)=N2)I)=C1 LEJBBVDMHSVUFT-UHFFFAOYSA-N 0.000 claims description 3
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
• 206010061218 Inflammation Diseases 0.000 claims description 3
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 3
• 208000009905 Neurofibromatoses Diseases 0.000 claims description 3
• 208000031481 Pathologic Constriction Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 208000026935 allergic disease Diseases 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• 239000013066 combination product Substances 0.000 claims description 3
• 229940127555 combination product Drugs 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 230000004054 inflammatory process Effects 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 201000004931 neurofibromatosis Diseases 0.000 claims description 3
• 230000001575 pathological effect Effects 0.000 claims description 3
• 208000015768 polyposis Diseases 0.000 claims description 3
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• 230000036262 stenosis Effects 0.000 claims description 3
• 208000037804 stenosis Diseases 0.000 claims description 3
• 230000002792 vascular Effects 0.000 claims description 3
• WLOMDEDKZBPRTA-UHFFFAOYSA-N 4-[6-(1h-indazol-4-yl)-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound CC=1N=C2C(N3CCOCC3)=NC(C=3C=4C=NNC=4C=CC=3)=CN2C=1C1=CCNCC1 WLOMDEDKZBPRTA-UHFFFAOYSA-N 0.000 claims description 2
• QQAWPUOJQWAOJU-UHFFFAOYSA-N 4-[6-(1h-indazol-4-yl)-2-methyl-3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1N(C)CCC(C=2N3C=C(N=C(C3=NC=2C)N2CCOCC2)C=2C=3C=NNC=3C=CC=2)=C1 QQAWPUOJQWAOJU-UHFFFAOYSA-N 0.000 claims description 2
• WMXTZZHZEBYWAM-UHFFFAOYSA-N 4-[6-(1h-indazol-4-yl)-2-methyl-3-[1-(sulfonylmethyl)-3,6-dihydro-2h-pyridin-4-yl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound CC=1N=C2C(N3CCOCC3)=NC(C=3C=4C=NNC=4C=CC=3)=CN2C=1C1=CCN(C=S(=O)=O)CC1 WMXTZZHZEBYWAM-UHFFFAOYSA-N 0.000 claims description 2
• 208000012124 AIDS-related disease Diseases 0.000 claims description 2
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
• 208000035473 Communicable disease Diseases 0.000 claims description 2
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
• 206010019842 Hepatomegaly Diseases 0.000 claims description 2
• 206010062016 Immunosuppression Diseases 0.000 claims description 2
• 208000012902 Nervous system disease Diseases 0.000 claims description 2
• 208000027771 Obstructive airways disease Diseases 0.000 claims description 2
• 208000006011 Stroke Diseases 0.000 claims description 2
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 2
• 108090000190 Thrombin Proteins 0.000 claims description 2
• 208000036142 Viral infection Diseases 0.000 claims description 2
• 230000004913 activation Effects 0.000 claims description 2
• 230000030833 cell death Effects 0.000 claims description 2
• 208000015114 central nervous system disease Diseases 0.000 claims description 2
• 230000001066 destructive effect Effects 0.000 claims description 2
• 206010012601 diabetes mellitus Diseases 0.000 claims description 2
• 230000007368 endocrine function Effects 0.000 claims description 2
• 229940088597 hormone Drugs 0.000 claims description 2
• 239000005556 hormone Substances 0.000 claims description 2
• 208000026278 immune system disease Diseases 0.000 claims description 2
• 230000001506 immunosuppresive effect Effects 0.000 claims description 2
• 208000019423 liver disease Diseases 0.000 claims description 2
• 210000000056 organ Anatomy 0.000 claims description 2
• 229960004072 thrombin Drugs 0.000 claims description 2
• 238000002054 transplantation Methods 0.000 claims description 2
• 230000009385 viral infection Effects 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 5
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims 3
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
• 239000003981 vehicle Substances 0.000 claims 2
• FNWPEMZXMCMGHU-UHFFFAOYSA-N 1,2-diazaspiro[4.5]decane-8-carboxylic acid Chemical compound C1CC(C(=O)O)CCC11NNCC1 FNWPEMZXMCMGHU-UHFFFAOYSA-N 0.000 claims 1
• IBVFZMLLDLLCJY-UHFFFAOYSA-N 1-[4-(3-methyl-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl)phenyl]-3-[3-(4-methylpiperazine-1-carbonyl)phenyl]urea Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C(C3=NC=C(C)N3C=2)N2CCOCC2)=C1 IBVFZMLLDLLCJY-UHFFFAOYSA-N 0.000 claims 1
• UWDVPCJDQQUDIE-UHFFFAOYSA-N 1-[4-[6-(1h-indazol-4-yl)-2-methyl-8-morpholin-4-ylimidazo[1,2-a]pyrazin-3-yl]-3,6-dihydro-2h-pyridin-1-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)C)CCC(C=2N3C=C(N=C(C3=NC=2C)N2CCOCC2)C=2C=3C=NNC=3C=CC=2)=C1 UWDVPCJDQQUDIE-UHFFFAOYSA-N 0.000 claims 1
• MTWPXPIXNXUEFQ-UHFFFAOYSA-N 1-[4-[6-(1h-indazol-4-yl)-2-methyl-8-morpholin-4-ylimidazo[1,2-a]pyrazin-3-yl]piperidin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)C)CCC1C1=C(C)N=C2N1C=C(C=1C=3C=NNC=3C=CC=1)N=C2N1CCOCC1 MTWPXPIXNXUEFQ-UHFFFAOYSA-N 0.000 claims 1
• NJFPAGGSHFZGCM-UHFFFAOYSA-N 1-[4-[[6-(2-aminopyrimidin-5-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]methyl]piperazin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=NC(N)=NC=3)C2=N1 NJFPAGGSHFZGCM-UHFFFAOYSA-N 0.000 claims 1
• ONFNQRCINSWBIY-UHFFFAOYSA-N 1-[6-(1h-indazol-4-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-3-yl]piperidin-3-amine Chemical compound C1C(N)CCCN1C1=CN=C2N1C=C(C=1C=3C=NNC=3C=CC=1)N=C2N1CCOCC1 ONFNQRCINSWBIY-UHFFFAOYSA-N 0.000 claims 1
• IOSYKFVVXIKDRU-UHFFFAOYSA-N 1-[6-(1h-indazol-4-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-3-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CN=C2N1C=C(C=1C=3C=NNC=3C=CC=1)N=C2N1CCOCC1 IOSYKFVVXIKDRU-UHFFFAOYSA-N 0.000 claims 1
• QOMJPSUEVZZLRW-UHFFFAOYSA-N 1-[[6-(2-aminopyrimidin-5-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]methyl]piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCC(O)CC1)=C2 QOMJPSUEVZZLRW-UHFFFAOYSA-N 0.000 claims 1
• WBKVGIZHFQWXOS-UHFFFAOYSA-N 1-methyl-3-[4-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(C)(=O)=O)=C2 WBKVGIZHFQWXOS-UHFFFAOYSA-N 0.000 claims 1
• CQZCBLLPJONWCZ-UHFFFAOYSA-N 2,2-dimethylpiperazine-1-carboxylic acid Chemical compound CC1(C)CNCCN1C(O)=O CQZCBLLPJONWCZ-UHFFFAOYSA-N 0.000 claims 1
• RIEQYSDNPAAXQT-UHFFFAOYSA-N 2-[3-(1H-indazol-4-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]-4-(sulfonylmethyl)piperazine-1-carbaldehyde Chemical compound N1N=CC2=C(C=CC=C12)C1=C(N=C2N1C=CN=C2N1CCOCC1)C1CN(CCN1C=O)C=S(=O)=O RIEQYSDNPAAXQT-UHFFFAOYSA-N 0.000 claims 1
• BHVHJCSGLLNXJR-UHFFFAOYSA-N 2-[3-(1h-indazol-4-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]-4-methylpiperazine-1-carbaldehyde Chemical compound C1N(C)CCN(C=O)C1C1=C(C=2C=3C=NNC=3C=CC=2)N2C=CN=C(N3CCOCC3)C2=N1 BHVHJCSGLLNXJR-UHFFFAOYSA-N 0.000 claims 1
• CIDKPJFFRYCVSZ-UHFFFAOYSA-N 2-[3-(1h-indazol-4-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]piperazine-1-carbaldehyde Chemical compound O=CN1CCNCC1C1=C(C=2C=3C=NNC=3C=CC=2)N2C=CN=C(N3CCOCC3)C2=N1 CIDKPJFFRYCVSZ-UHFFFAOYSA-N 0.000 claims 1
• AXWHAWLGCLZLPC-UHFFFAOYSA-N 2-[3-(3-hydroxyphenyl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]-4-(sulfonylmethyl)piperazine-1-carbaldehyde Chemical compound OC=1C=C(C=CC=1)C1=C(N=C2N1C=CN=C2N1CCOCC1)C1CN(CCN1C=O)C=S(=O)=O AXWHAWLGCLZLPC-UHFFFAOYSA-N 0.000 claims 1
• AEDUHKGGPKDYDP-UHFFFAOYSA-N 2-[6-(2-aminopyrimidin-5-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-2-yl]propan-2-ol Chemical compound C12=NC(C(C)(O)C)=CN2C=C(C=2C=NC(N)=NC=2)N=C1N1CCOCC1 AEDUHKGGPKDYDP-UHFFFAOYSA-N 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• QDJVLQGGCQZARM-UHFFFAOYSA-N 3-[[4-(3-methyl-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl)phenyl]carbamoylamino]benzoic acid Chemical compound C=1N2C(C)=CN=C2C(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(O)=O)=C1 QDJVLQGGCQZARM-UHFFFAOYSA-N 0.000 claims 1
• VEXVCFUGRSITMZ-UHFFFAOYSA-N 3-fluoro-5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=C(F)C(N)=NC=3)C2=N1 VEXVCFUGRSITMZ-UHFFFAOYSA-N 0.000 claims 1
• VIIACNZKBFVXGX-UHFFFAOYSA-N 3-methyl-5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine Chemical compound N1=C(N)C(C)=CC(C=2N=C(C3=NC(CN4CCN(CC4)S(C)(=O)=O)=CN3C=2)N2CCOCC2)=C1 VIIACNZKBFVXGX-UHFFFAOYSA-N 0.000 claims 1
• RCTPWPSQTOYIPQ-UHFFFAOYSA-N 4-[2-(2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-ylmethyl)-6-(1h-indazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1C2CNCC2CN1CC(N=C12)=CN1C=C(C=1C=3C=NNC=3C=CC=1)N=C2N1CCOCC1 RCTPWPSQTOYIPQ-UHFFFAOYSA-N 0.000 claims 1
• JIUMMQVHCPEVES-UHFFFAOYSA-N 4-[2-(2,8-diazaspiro[4.5]decan-2-ylmethyl)-6-(1h-indazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C=1N2C=C(C=3C=4C=NNC=4C=CC=3)N=C(N3CCOCC3)C2=NC=1CN(C1)CCC21CCNCC2 JIUMMQVHCPEVES-UHFFFAOYSA-N 0.000 claims 1
• GQCQOSUIDRWILE-UHFFFAOYSA-N 4-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C3=CNN=C3)C2=N1 GQCQOSUIDRWILE-UHFFFAOYSA-N 0.000 claims 1
• LNZJUUJPFOWGOR-UHFFFAOYSA-N 4-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-6-pyrimidin-5-ylimidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=NC=NC=3)C2=N1 LNZJUUJPFOWGOR-UHFFFAOYSA-N 0.000 claims 1
• SQUFLFRRPODYIU-UHFFFAOYSA-N 4-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]aniline Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=CC(N)=CC=3)C2=N1 SQUFLFRRPODYIU-UHFFFAOYSA-N 0.000 claims 1
• ABOMOADQIGPATC-UHFFFAOYSA-N 4-[3-bromo-6-(1h-indazol-4-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=C(Br)N2C=C(C=3C=4C=NNC=4C=CC=3)N=C(N3CCOCC3)C2=N1 ABOMOADQIGPATC-UHFFFAOYSA-N 0.000 claims 1
• JKSUJXQHJQMPFW-UHFFFAOYSA-N 4-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-6-(1h-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=C4C=CNC4=NC=3)C2=N1 JKSUJXQHJQMPFW-UHFFFAOYSA-N 0.000 claims 1
• RXKKTWKIGDDESV-UHFFFAOYSA-N 4-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-6-pyrimidin-5-ylimidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=NC=NC=3)C2=N1 RXKKTWKIGDDESV-UHFFFAOYSA-N 0.000 claims 1
• UQLAPAIKEWTYSQ-UHFFFAOYSA-N 4-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=CC(=CC=3)C(N)=O)C2=N1 UQLAPAIKEWTYSQ-UHFFFAOYSA-N 0.000 claims 1
• ZVTBQTNUIUCOTI-UHFFFAOYSA-N 4-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=C(N)N=CC=3)C2=N1 ZVTBQTNUIUCOTI-UHFFFAOYSA-N 0.000 claims 1
• HGAMBCLDEJNZCO-UHFFFAOYSA-N 4-[5-chloro-6-(1h-indazol-6-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=C4NN=CC4=CC=3)C2=N1 HGAMBCLDEJNZCO-UHFFFAOYSA-N 0.000 claims 1
• VZMGCZGJAHWORB-UHFFFAOYSA-N 4-[5-chloro-6-(1h-indol-5-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=C4C=CNC4=CC=3)C2=N1 VZMGCZGJAHWORB-UHFFFAOYSA-N 0.000 claims 1
• DRXSBQPLFUTKFA-UHFFFAOYSA-N 4-[5-chloro-6-(2-methoxypyrimidin-5-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 DRXSBQPLFUTKFA-UHFFFAOYSA-N 0.000 claims 1
• WOBDURNUEHTHCH-UHFFFAOYSA-N 4-[5-chloro-6-(2-methylpyrimidin-5-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1=NC(C)=NC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 WOBDURNUEHTHCH-UHFFFAOYSA-N 0.000 claims 1
• ZEODDRIHDJZEQM-UHFFFAOYSA-N 4-[5-chloro-6-(3-chloro-5-fluoro-1h-indol-4-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=4C(Cl)=CNC=4C=CC=3F)C2=N1 ZEODDRIHDJZEQM-UHFFFAOYSA-N 0.000 claims 1
• XYRHZDGOWLRKKG-UHFFFAOYSA-N 4-[5-chloro-6-(4-methoxypyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound COC1=CC=NC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 XYRHZDGOWLRKKG-UHFFFAOYSA-N 0.000 claims 1
• QNZQAGCQKGEEOU-UHFFFAOYSA-N 4-[5-chloro-6-(4-methylpyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound CC1=CC=NC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 QNZQAGCQKGEEOU-UHFFFAOYSA-N 0.000 claims 1
• YNYXOCFPWNGSBK-UHFFFAOYSA-N 4-[5-chloro-6-(5-fluoro-1h-indol-4-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=4C=CNC=4C=CC=3F)C2=N1 YNYXOCFPWNGSBK-UHFFFAOYSA-N 0.000 claims 1
• NYHFRTAZHUNBJH-UHFFFAOYSA-N 4-[5-chloro-6-(6-methoxypyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1=NC(OC)=CC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 NYHFRTAZHUNBJH-UHFFFAOYSA-N 0.000 claims 1
• BMMZDWIGSTYWLJ-UHFFFAOYSA-N 4-[5-chloro-6-(6-methylpyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1=NC(C)=CC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 BMMZDWIGSTYWLJ-UHFFFAOYSA-N 0.000 claims 1
• BOWQYWJYXVGKJG-UHFFFAOYSA-N 4-[6-(2-methylpyrimidin-5-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1=NC(C)=NC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(C)(=O)=O)=C2 BOWQYWJYXVGKJG-UHFFFAOYSA-N 0.000 claims 1
• AXWYWARMZSLGRY-UHFFFAOYSA-N 4-[6-(4-methoxypyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound COC1=CC=NC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(C)(=O)=O)=C2 AXWYWARMZSLGRY-UHFFFAOYSA-N 0.000 claims 1
• CIXFKNYNSYYWSH-UHFFFAOYSA-N 4-[6-(4-methylpyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound CC1=CC=NC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(C)(=O)=O)=C2 CIXFKNYNSYYWSH-UHFFFAOYSA-N 0.000 claims 1
• PVYFRDULIUFXEQ-UHFFFAOYSA-N 4-[6-(5-methoxypyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound COC1=CN=CC(C=2N=C(C3=NC(CN4CCN(CC4)S(C)(=O)=O)=CN3C=2)N2CCOCC2)=C1 PVYFRDULIUFXEQ-UHFFFAOYSA-N 0.000 claims 1
• CYYDLZUWQIEMSJ-UHFFFAOYSA-N 4-[6-(6-methoxy-4-methylpyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1=NC(OC)=CC(C)=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(C)(=O)=O)=C2 CYYDLZUWQIEMSJ-UHFFFAOYSA-N 0.000 claims 1
• NAVNXMQAACIGMC-UHFFFAOYSA-N 4-[6-(6-methylpyridin-3-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]imidazo[1,2-a]pyrazin-8-yl]morpholine Chemical compound C1=NC(C)=CC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(C)(=O)=O)=C2 NAVNXMQAACIGMC-UHFFFAOYSA-N 0.000 claims 1
• WGBOAGRAECSQOH-UHFFFAOYSA-N 4-methyl-5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(C)(=O)=O)=C2 WGBOAGRAECSQOH-UHFFFAOYSA-N 0.000 claims 1
• CATKJAADFNDUIY-UHFFFAOYSA-N 5-[2-[(4-methylsulfonyl-1,4-diazepan-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=NC(N)=NC=3)C2=N1 CATKJAADFNDUIY-UHFFFAOYSA-N 0.000 claims 1
• SMEJBPDSDNQHFN-UHFFFAOYSA-N 5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyridine-2-carbonitrile Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=NC(=CC=3)C#N)C2=N1 SMEJBPDSDNQHFN-UHFFFAOYSA-N 0.000 claims 1
• JGMCCTDJMQSGDC-UHFFFAOYSA-N 5-[2-[(5-methylsulfonyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C1C2CN(S(=O)(=O)C)CC2CN1CC(N=C12)=CN1C=C(C=1C=NC(N)=NC=1)N=C2N1CCOCC1 JGMCCTDJMQSGDC-UHFFFAOYSA-N 0.000 claims 1
• YVSPGMBGYKAOMM-UHFFFAOYSA-N 5-[2-[(7-methylsulfonyl-2,7-diazaspiro[3.5]nonan-2-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCC11CN(CC=2N=C3C(N4CCOCC4)=NC(=CN3C=2)C=2C=NC(N)=NC=2)C1 YVSPGMBGYKAOMM-UHFFFAOYSA-N 0.000 claims 1
• KWUDNUSFJDWCTL-UHFFFAOYSA-N 5-[2-[2-(4-methylsulfonylpiperazin-1-yl)propan-2-yl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C=1N2C=C(C=3C=NC(N)=NC=3)N=C(N3CCOCC3)C2=NC=1C(C)(C)N1CCN(S(C)(=O)=O)CC1 KWUDNUSFJDWCTL-UHFFFAOYSA-N 0.000 claims 1
• BEBZIYDIUWXWRQ-IYBDPMFKSA-N 5-[2-[[(2r,6s)-2,6-dimethyl-4-methylsulfonylpiperazin-1-yl]methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C[C@H]1CN(S(C)(=O)=O)C[C@@H](C)N1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=NC(N)=NC=3)C2=N1 BEBZIYDIUWXWRQ-IYBDPMFKSA-N 0.000 claims 1
• NMVATSJIDQPOSL-UHFFFAOYSA-N 5-[2-[[4-(2-methylpropylsulfonyl)piperazin-1-yl]methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)CC(C)C)CCN1CC1=CN(C=C(N=C2N3CCOCC3)C=3C=NC(N)=NC=3)C2=N1 NMVATSJIDQPOSL-UHFFFAOYSA-N 0.000 claims 1
• BBBDDBWDQRGYCG-UHFFFAOYSA-N 5-[2-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C(N=C1N2CCOCC2)=CN2C1=NC(CN1CCN(CC1)S(=O)(=O)C=1C=CC=CC=1)=C2 BBBDDBWDQRGYCG-UHFFFAOYSA-N 0.000 claims 1
• KMOMOHJVPBJRJT-UHFFFAOYSA-N 5-[2-methyl-8-(oxan-4-yl)imidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C12=NC(C)=CN2C=C(C=2C=NC(N)=NC=2)N=C1C1CCOCC1 KMOMOHJVPBJRJT-UHFFFAOYSA-N 0.000 claims 1
• JLEBDZGGHQTFEB-UHFFFAOYSA-N 5-[3-(4-methylsulfonylpiperazin-1-yl)-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CN=C2N1C=C(C=1C=NC(N)=NC=1)N=C2N1CCOCC1 JLEBDZGGHQTFEB-UHFFFAOYSA-N 0.000 claims 1
• NSQMUBUWCVCQFY-UHFFFAOYSA-N 5-[3-bromo-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=C(Br)N2C=C(C=3C=NC(N)=NC=3)N=C(N3CCOCC3)C2=N1 NSQMUBUWCVCQFY-UHFFFAOYSA-N 0.000 claims 1
• XZMAYWPLOYTTDT-UHFFFAOYSA-N 5-[3-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyrimidin-2-amine Chemical compound N1=C2C(N3CCOCC3)=NC(C=3C=NC(N)=NC=3)=CN2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 XZMAYWPLOYTTDT-UHFFFAOYSA-N 0.000 claims 1
• GQCZPZPAKQESND-UHFFFAOYSA-N 5-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]-1,3-dihydroindol-2-one Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=C4CC(=O)NC4=CC=3)C2=N1 GQCZPZPAKQESND-UHFFFAOYSA-N 0.000 claims 1
• BDZVYKFXFAKNNB-UHFFFAOYSA-N 5-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]-4-methylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 BDZVYKFXFAKNNB-UHFFFAOYSA-N 0.000 claims 1
• IISVATQKJZBIJX-UHFFFAOYSA-N 5-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=C(Cl)N2C=C(CN3CCN(CC3)S(C)(=O)=O)N=C2C(N2CCOCC2)=N1 IISVATQKJZBIJX-UHFFFAOYSA-N 0.000 claims 1
• ZXSYYQDAJQLYQJ-UHFFFAOYSA-N 5-[5-chloro-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-8-morpholin-4-ylimidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CN(C(Cl)=C(N=C2N3CCOCC3)C=3C=NC(N)=CC=3)C2=N1 ZXSYYQDAJQLYQJ-UHFFFAOYSA-N 0.000 claims 1
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