SG184062A1 - Spirocyclic compounds and their use as therapeutic agents and diagnostic probes - Google Patents

Info

Publication number

SG184062A1

SG184062A1 SG2012068094A SG2012068094A SG184062A1 SG 184062 A1 SG184062 A1 SG 184062A1 SG 2012068094 A SG2012068094 A SG 2012068094A SG 2012068094 A SG2012068094 A SG 2012068094A SG 184062 A1 SG184062 A1 SG 184062A1

Authority

SG

Singapore

Prior art keywords

oxa

heptan

morpholino

azaspiro

triazin

Prior art date

2010-03-15

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 186
• 239000003814 drug Substances 0.000 title abstract description 16
• 229940124597 therapeutic agent Drugs 0.000 title abstract description 7
• 239000000523 sample Substances 0.000 title abstract description 5
• 238000000034 method Methods 0.000 claims abstract description 53
• 125000001424 substituent group Chemical group 0.000 claims abstract description 41
• 238000011282 treatment Methods 0.000 claims abstract description 29
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 14
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims abstract description 9
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims abstract description 9
• -1 methacryloyl Chemical group 0.000 claims description 415
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 125000005647 linker group Chemical group 0.000 claims description 29
• 229940002612 prodrug Drugs 0.000 claims description 29
• 239000000651 prodrug Substances 0.000 claims description 29
• 208000035475 disorder Diseases 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 27
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 23
• 201000010099 disease Diseases 0.000 claims description 22
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
• 125000004076 pyridyl group Chemical group 0.000 claims description 20
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 18
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 18
• 239000012453 solvate Substances 0.000 claims description 18
• 241000124008 Mammalia Species 0.000 claims description 17
• 150000001413 amino acids Chemical class 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
• 239000002207 metabolite Substances 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 230000000694 effects Effects 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 108091000080 Phosphotransferase Proteins 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 239000005864 Sulphur Substances 0.000 claims description 9
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 9
• 229960002685 biotin Drugs 0.000 claims description 9
• 235000020958 biotin Nutrition 0.000 claims description 9
• 239000011616 biotin Substances 0.000 claims description 9
• 229910052792 caesium Inorganic materials 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
• 125000001041 indolyl group Chemical group 0.000 claims description 9
• 102000020233 phosphotransferase Human genes 0.000 claims description 9
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
• 239000005977 Ethylene Substances 0.000 claims description 8
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 8
• XZPIJSOWXMUXIA-UHFFFAOYSA-N 1-[6-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-2,6-diazaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CC3(CN(C3)C(=O)C=C)C2)=NC=1N1CCOCC1 XZPIJSOWXMUXIA-UHFFFAOYSA-N 0.000 claims description 7
• FGWDPDRVMALKQQ-UHFFFAOYSA-N 4-[4-(2,6-diazaspiro[3.3]heptan-2-yl)-6-[2-(difluoromethyl)benzimidazol-1-yl]-1,3,5-triazin-2-yl]morpholine Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CC3(CNC3)C2)=NC=1N1CCOCC1 FGWDPDRVMALKQQ-UHFFFAOYSA-N 0.000 claims description 7
• 108090001008 Avidin Proteins 0.000 claims description 7
• 108010090804 Streptavidin Proteins 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 7
• 125000002228 disulfide group Chemical group 0.000 claims description 7
• 239000003550 marker Substances 0.000 claims description 7
• 150000002829 nitrogen Chemical class 0.000 claims description 7
• 239000007790 solid phase Substances 0.000 claims description 7
• BLEQDYDNIVRHMS-VMPITWQZSA-N (e)-1-[6-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-2,6-diazaspiro[3.3]heptan-2-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound C1N(C(=O)/C=C/CN(C)C)CC21CN(C=1N=C(N=C(N=1)N1CCOCC1)N1C3=CC=CC=C3N=C1C(F)F)C2 BLEQDYDNIVRHMS-VMPITWQZSA-N 0.000 claims description 6
• ZYKTZBLUXBSTGQ-UHFFFAOYSA-N 1-[6-[4-(2-aminopyrimidin-5-yl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]-2,6-diazaspiro[3.3]heptan-2-yl]-2-chloroethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CC3(CN(C3)C(=O)CCl)C2)=NC(N2CCOCC2)=N1 ZYKTZBLUXBSTGQ-UHFFFAOYSA-N 0.000 claims description 6
• QKSBOAKCHDBTJX-UHFFFAOYSA-N 1-ethyl-3-[5-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]pyrimidin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 QKSBOAKCHDBTJX-UHFFFAOYSA-N 0.000 claims description 6
• ZJIRZCFRTHNFEC-UHFFFAOYSA-N 2-chloro-n-[2-[2-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-2,6-diazaspiro[3.3]heptan-6-yl]ethyl]acetamide Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CC3(CN(CCNC(=O)CCl)C3)C2)=NC=1N1CCOCC1 ZJIRZCFRTHNFEC-UHFFFAOYSA-N 0.000 claims description 6
• RTDVHLWDOSQRBM-UHFFFAOYSA-N 5-[4-(6-methyl-2,6-diazaspiro[3.3]heptan-2-yl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]pyrimidin-2-amine Chemical compound C1N(C)CC21CN(C=1N=C(N=C(N=1)N1CCOCC1)C=1C=NC(N)=NC=1)C2 RTDVHLWDOSQRBM-UHFFFAOYSA-N 0.000 claims description 6
• NCWCRJGZBXZSFU-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=NC(N)=CC(C(F)(F)F)=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 NCWCRJGZBXZSFU-UHFFFAOYSA-N 0.000 claims description 6
• FDCFWOLVSCPZPM-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 FDCFWOLVSCPZPM-UHFFFAOYSA-N 0.000 claims description 6
• BENZYCCSYXXLCM-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-2-yl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=NC(N)=CC(C(F)(F)F)=C1C1=NC(N2CC3(COC3)C2)=CC(N2CCOCC2)=N1 BENZYCCSYXXLCM-UHFFFAOYSA-N 0.000 claims description 6
• NYFQPEZMHRTICP-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=CC(N2CCOCC2)=N1 NYFQPEZMHRTICP-UHFFFAOYSA-N 0.000 claims description 6
• HQEPONXNCLIYJB-UHFFFAOYSA-N 5-[6-morpholin-4-yl-2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-4-yl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=NC(N)=CC(C(F)(F)F)=C1C1=CC(N2CCOCC2)=NC(N2CC3(COC3)C2)=N1 HQEPONXNCLIYJB-UHFFFAOYSA-N 0.000 claims description 6
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
• 230000003463 hyperproliferative effect Effects 0.000 claims description 6
• PZHVESCGRQYYCR-UHFFFAOYSA-N methyl n-[4-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 PZHVESCGRQYYCR-UHFFFAOYSA-N 0.000 claims description 6
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• OQEYBFLDTBSKDT-UHFFFAOYSA-N 1-[4-[4-(dimethylamino)piperidine-1-carbonyl]phenyl]-3-[4-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C1CC(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(N=C(N=2)N2CC3(COC3)C2)N2CCOCC2)C=C1 OQEYBFLDTBSKDT-UHFFFAOYSA-N 0.000 claims description 5
• SLWFMROOKYNKCW-UHFFFAOYSA-N 1-[4-[4-(dimethylamino)piperidine-1-carbonyl]phenyl]-3-[5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]pyridin-2-yl]urea Chemical compound C1CC(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C(N=C(N=2)N2CC3(COC3)C2)N2CCOCC2)C=N1 SLWFMROOKYNKCW-UHFFFAOYSA-N 0.000 claims description 5
• KTRSMJFXBRUEOW-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 KTRSMJFXBRUEOW-UHFFFAOYSA-N 0.000 claims description 5
• MMYZWPPNBQYXHH-UHFFFAOYSA-N 4-methyl-5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]pyridin-2-amine Chemical compound CC1=CC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 MMYZWPPNBQYXHH-UHFFFAOYSA-N 0.000 claims description 5
• XHEPEPWLWYVDET-UHFFFAOYSA-N 4-methyl-5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]pyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 XHEPEPWLWYVDET-UHFFFAOYSA-N 0.000 claims description 5
• IHLJZIDKFWNTGW-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 IHLJZIDKFWNTGW-UHFFFAOYSA-N 0.000 claims description 5
• 229910052770 Uranium Inorganic materials 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• VJIDXSVVJSNPED-UHFFFAOYSA-N methyl n-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 VJIDXSVVJSNPED-UHFFFAOYSA-N 0.000 claims description 5
• YMLFLHPTLQISNU-QDEBKDIKSA-N (e)-3-[[6-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-2,6-diazaspiro[3.3]heptan-2-yl]sulfonyl]prop-2-en-1-amine Chemical compound C1N(S(=O)(=O)/C=C/CN)CC11CN(C=2N=C(N=C(N=2)N2CCOCC2)N2C3=CC=CC=C3N=C2C(F)F)C1 YMLFLHPTLQISNU-QDEBKDIKSA-N 0.000 claims description 4
• PCCJBPIMDYFIGG-UHFFFAOYSA-N 2,6-dimethoxy-4-[1-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]imidazol-4-yl]phenol Chemical compound COC1=C(O)C(OC)=CC(C=2N=CN(C=2)C=2N=C(N=C(N=2)N2CC3(COC3)C2)N2CCOCC2)=C1 PCCJBPIMDYFIGG-UHFFFAOYSA-N 0.000 claims description 4
• MHJOLISBSJBKTP-UHFFFAOYSA-N 2,6-dimethoxy-4-[5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]furan-2-yl]phenol Chemical compound COC1=C(O)C(OC)=CC(C=2OC(=CC=2)C=2N=C(N=C(N=2)N2CC3(COC3)C2)N2CCOCC2)=C1 MHJOLISBSJBKTP-UHFFFAOYSA-N 0.000 claims description 4
• VCWVXIDQILXJFE-UHFFFAOYSA-N 3-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]-8-oxa-3-azabicyclo[3.2.1]octane Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=C(N=1)N2CC3CCC(O3)C2)=NC=1N(C1)CC21COC2 VCWVXIDQILXJFE-UHFFFAOYSA-N 0.000 claims description 4
• GVPHOBKSUXHPRY-UHFFFAOYSA-N 4-[3-(trifluoromethyl)diazirin-3-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1(C(F)(F)F)N=N1 GVPHOBKSUXHPRY-UHFFFAOYSA-N 0.000 claims description 4
• LICNKXQJGKHBKB-UHFFFAOYSA-N 4-methyl-5-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]pyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 LICNKXQJGKHBKB-UHFFFAOYSA-N 0.000 claims description 4
• ZOOWSWDXGKELIV-UHFFFAOYSA-N 5-[2-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-4-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 ZOOWSWDXGKELIV-UHFFFAOYSA-N 0.000 claims description 4
• CERXSOIRDZZUGF-UHFFFAOYSA-N 5-[4-(6-methyl-2,6-diazaspiro[3.3]heptan-2-yl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1N(C)CC21CN(C=1N=C(N=C(N=1)N1CCOCC1)C=1C(=CC(N)=NC=1)C(F)(F)F)C2 CERXSOIRDZZUGF-UHFFFAOYSA-N 0.000 claims description 4
• FHKRRGHQZSKAQR-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-2-yl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound FC(F)(F)C1=NC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=CC(N2CCOCC2)=N1 FHKRRGHQZSKAQR-UHFFFAOYSA-N 0.000 claims description 4
• ZPOWJPOMPUHKPW-UHFFFAOYSA-N 5-[6-morpholin-4-yl-2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-4-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC(N2CCOCC2)=NC(N2CC3(COC3)C2)=N1 ZPOWJPOMPUHKPW-UHFFFAOYSA-N 0.000 claims description 4
• LADGLKYBJPIKID-UHFFFAOYSA-N 6-amino-n-[3-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]phenyl]pyridine-3-carboxamide Chemical compound C1=NC(N)=CC=C1C(=O)NC1=CC=CC(C=2N=C(N=C(N=2)N2CC3(COC3)C2)N2CCOCC2)=C1 LADGLKYBJPIKID-UHFFFAOYSA-N 0.000 claims description 4
• PUHKUSYCOPZBGL-UHFFFAOYSA-N [2-methoxy-5-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrido[2,3-d]pyrimidin-7-yl]phenyl]methanol Chemical compound C1=C(CO)C(OC)=CC=C1C1=CC=C(C(=NC(=N2)N3CC4(COC4)C3)N3CC4CCC(O4)C3)C2=N1 PUHKUSYCOPZBGL-UHFFFAOYSA-N 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• UFWUDFNZMQIODW-UHFFFAOYSA-N n-[3-[4-morpholin-4-yl-6-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,3,5-triazin-2-yl]phenyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C=1)=CC=CC=1C(N=1)=NC(N2CC3(COC3)C2)=NC=1N1CCOCC1 UFWUDFNZMQIODW-UHFFFAOYSA-N 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
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