MX2012010655A - Compuestos espirociclicos y su uso como agentes terapeuticos y sondas de diagnostico. - Google Patents
Compuestos espirociclicos y su uso como agentes terapeuticos y sondas de diagnostico.Info
- Publication number
- MX2012010655A MX2012010655A MX2012010655A MX2012010655A MX2012010655A MX 2012010655 A MX2012010655 A MX 2012010655A MX 2012010655 A MX2012010655 A MX 2012010655A MX 2012010655 A MX2012010655 A MX 2012010655A MX 2012010655 A MX2012010655 A MX 2012010655A
- Authority
- MX
- Mexico
- Prior art keywords
- oxa
- heptan
- morpholino
- azaspiro
- triazin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 184
- 239000003814 drug Substances 0.000 title abstract description 16
- 229940124597 therapeutic agent Drugs 0.000 title abstract description 6
- 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 42
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 13
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims abstract description 11
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims abstract description 11
- -1 halo-Ci-C6-alkyl Chemical group 0.000 claims description 502
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000005647 linker group Chemical group 0.000 claims description 31
- 208000035475 disorder Diseases 0.000 claims description 30
- 229940002612 prodrug Drugs 0.000 claims description 29
- 239000000651 prodrug Substances 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 24
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 23
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical group 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 16
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 229910052770 Uranium Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000002207 metabolite Substances 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 239000004202 carbamide Substances 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 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
- 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
- 230000000694 effects Effects 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([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
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000539 amino acid group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 8
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 8
- 108010090804 Streptavidin Proteins 0.000 claims description 7
- 125000004452 carbocyclyl 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
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 239000007790 solid phase Substances 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- FHPPGEYXCMHJPN-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]pyridin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 FHPPGEYXCMHJPN-UHFFFAOYSA-N 0.000 claims description 6
- JEICYXCIZSODCS-UHFFFAOYSA-N 2,6-dimethoxy-4-[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]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)N2CC3CCC(O3)C2)=C1 JEICYXCIZSODCS-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 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 6
- WJLMOWBUJZVEQB-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)pyrimidin-2-amine Chemical compound FC(F)(F)C1=NC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 WJLMOWBUJZVEQB-UHFFFAOYSA-N 0.000 claims description 6
- 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 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 108090001008 Avidin Proteins 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
- PGZSVGZNVSYTHM-CALCHBBNSA-N [5-[4-[(3r,5s)-3,5-dimethylmorpholin-4-yl]-2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pyrido[2,3-d]pyrimidin-7-yl]-2-methoxyphenyl]methanol Chemical compound C1=C(CO)C(OC)=CC=C1C1=CC=C(C(=NC(=N2)N3CC4(COC4)C3)N3[C@@H](COC[C@@H]3C)C)C2=N1 PGZSVGZNVSYTHM-CALCHBBNSA-N 0.000 claims description 6
- 239000007850 fluorescent dye Substances 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 6
- 150000002829 nitrogen Chemical class 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
- 125000004169 (C1-C6) alkyl group Chemical group 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
- 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 5
- 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 5
- CUEVGTVGJCCNLE-UHFFFAOYSA-N 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 C1=NC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 CUEVGTVGJCCNLE-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- VQVDZAUJPNKGQL-UHFFFAOYSA-N 6-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-2-oxa-6-azaspiro[3.3]heptane Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CC3(COC3)C2)=NC=1N1CCOCC1 VQVDZAUJPNKGQL-UHFFFAOYSA-N 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 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 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
- 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
- PPRAAQHATXGYBW-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]pyridin-2-amine Chemical compound CC1=CC(N)=NC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 PPRAAQHATXGYBW-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
- 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 4
- ZLHFHDYHFFPWEN-UHFFFAOYSA-N 5-[2-morpholin-4-yl-6-(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(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 ZLHFHDYHFFPWEN-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
- 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 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000006799 (C2-C6) alkenylamino group Chemical group 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- FAUSIKJSTFZHHX-UHFFFAOYSA-N [2-methoxy-5-[4-morpholin-4-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)N3CCOCC3)C2=N1 FAUSIKJSTFZHHX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
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- 125000003373 pyrazinyl 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
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
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Classifications
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1004200.0A GB201004200D0 (en) | 2010-03-15 | 2010-03-15 | Spirocyclic compounds and their use as therapeutic agents and diagnostic probes |
| PCT/IB2011/051047 WO2011114275A1 (en) | 2010-03-15 | 2011-03-11 | Spirocyclic compounds and their use as therapeutic agents and diagnostic probes |
Publications (1)
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| MX2012010655A true MX2012010655A (es) | 2012-10-05 |
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| MX2012010655A MX2012010655A (es) | 2010-03-15 | 2011-03-11 | Compuestos espirociclicos y su uso como agentes terapeuticos y sondas de diagnostico. |
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| BR112014007310A2 (pt) | 2011-09-27 | 2017-04-04 | Novartis Ag | 3-pirimidin-4-il-oxazolidin-2-onas como inibidores de idh mutante |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| JP6387360B2 (ja) | 2013-03-14 | 2018-09-05 | ノバルティス アーゲー | 変異ｉｄｈの阻害薬としての３−ピリミジン−４−イル−オキサゾリジン−２−オン |
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| AR096151A1 (es) * | 2013-05-01 | 2015-12-09 | Hoffmann La Roche | Compuestos de biheteroarilo y usos de los mismos |
| CN103483345B (zh) * | 2013-09-25 | 2016-07-06 | 中山大学 | Pi3k激酶抑制剂、包含其的药物组合物及其应用 |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| CN104557871B (zh) * | 2013-10-28 | 2017-05-03 | 上海汇伦生命科技有限公司 | 具有螺环取代基的芳基吗啉类化合物，其制备方法和用途 |
| PL3134432T3 (pl) | 2014-04-25 | 2020-10-19 | Bluebird Bio, Inc. | Promotor mnd chimeryczne receptory antygenowe |
| HUE049514T2 (hu) | 2014-04-25 | 2020-09-28 | Bluebird Bio Inc | Javított eljárások adoptív sejtterápiák kialakítására |
| SI3151672T1 (sl) | 2014-06-06 | 2021-03-31 | Bluebird Bio, Inc. | Izboljšani T-celični sestavki |
| ES2878449T3 (es) | 2014-07-24 | 2021-11-18 | 2Seventy Bio Inc | Receptores antigénicos quiméricos de BCMA |
| RU2017118562A (ru) | 2014-10-31 | 2018-11-30 | Индивиор ЮКей Лимитед | Соединения-антагонисты дофаминового d3-рецептора |
| HRP20191873T1 (hr) | 2014-12-12 | 2020-01-24 | Bluebird Bio, Inc. | Kimerni antigenski receptori |
| US11479755B2 (en) | 2015-12-07 | 2022-10-25 | 2Seventy Bio, Inc. | T cell compositions |
| EP3231799A1 (en) * | 2016-04-14 | 2017-10-18 | Universität Basel | 4-(azetidin-1-yl)pyrimidine derivatives with anti-mitotic and anti-proliferative activity |
| WO2018085690A1 (en) | 2016-11-04 | 2018-05-11 | Bluebird Bio, Inc. | Anti-bcma car t cell compositions |
| EP3559003B1 (en) * | 2016-12-21 | 2022-08-24 | Japan Tobacco Inc. | Crystalline forms of a janus kinase inhibitor |
| EP3573954A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| US11136308B2 (en) | 2017-01-26 | 2021-10-05 | Araxes Pharma Llc | Substituted quinazoline and quinazolinone compounds and methods of use thereof |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| WO2018140513A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
| JP7327802B2 (ja) | 2017-01-26 | 2023-08-16 | アラクセス ファーマ エルエルシー | 縮合ヘテロ－ヘテロ二環式化合物およびその使用方法 |
| WO2018218069A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| US10745385B2 (en) | 2017-05-25 | 2020-08-18 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
| JP7340519B2 (ja) * | 2017-11-06 | 2023-09-07 | メッドシャイン ディスカバリー インコーポレイテッド | ｍＴＯＲＣ１／２二重阻害剤としてのピリドピリミジン系化合物 |
| CN108191837A (zh) * | 2018-01-10 | 2018-06-22 | 贵州医科大学 | PI3Kα/mTOR双激酶抑制剂及其药物组合物和应用 |
| MX2021000887A (es) * | 2018-08-01 | 2021-03-31 | Araxes Pharma Llc | Compuestos espiroheterociclicos y metodos de uso de los mismos para el tratamiento de cancer. |
| JP7727627B2 (ja) * | 2019-12-04 | 2025-08-21 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | Ａｔｍキナーゼ阻害剤及び組成物並びにそれらの使用の方法 |
| TW202525813A (zh) * | 2019-12-19 | 2025-07-01 | 比利時商健生藥品公司 | 經取代之直鏈螺環接衍生物 |
| US20240059703A1 (en) * | 2020-10-20 | 2024-02-22 | Amgen Inc. | Heterocyclic spiro compounds and methods of use |
| WO2025137105A1 (en) * | 2023-12-22 | 2025-06-26 | Deciphera Pharmaceuticals, Llc | Dual raf and tubulin inhibitors and methods of use thereof |
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| DE60217322T2 (de) * | 2001-04-27 | 2007-10-04 | Zenyaku Kogyo K.K. | Heterocyclische verbindung und antitumormittel, das diese als wirkstoff enthält |
| CA2599320A1 (en) | 2005-02-25 | 2006-08-31 | Kudos Pharmaceuticals Limited | Hydrazinomethyl, hydr zonomethyl and 5-membered heterocylic compounds which act as mtor inhibitors and their use as anti cancer agents |
| GB0525081D0 (en) * | 2005-12-09 | 2006-01-18 | Astrazeneca Ab | Pyrimidine derivatives |
| JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| EP2064203A1 (en) * | 2006-09-14 | 2009-06-03 | AstraZeneca AB | 2-benzimidaz0lyl-6-m0rph0lin0-4-piperidin-4-ylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| WO2008032033A1 (en) | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 4-benzimidazolyl-2-morpholino-6-piperazinylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| WO2008098058A1 (en) * | 2007-02-06 | 2008-08-14 | Novartis Ag | Pi 3-kinase inhibitors and methods of their use |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| KR101324804B1 (ko) * | 2008-05-13 | 2013-11-01 | 아이알엠 엘엘씨 | 키나제 억제제로서의 질소 함유 융합 헤테로사이클 및 그의 조성물 |
| LT2294072T (lt) * | 2008-05-23 | 2017-06-12 | Wyeth Llc | Triazino junginiai, kaip p13 kinazės ir mtor inhibitoriai |
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2011
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2012
- 2012-09-03 ZA ZA2012/06580A patent/ZA201206580B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ602292A (en) | 2014-08-29 |
| RU2012143689A (ru) | 2014-04-20 |
| JP2013522286A (ja) | 2013-06-13 |
| CN102939292A (zh) | 2013-02-20 |
| US20130040934A1 (en) | 2013-02-14 |
| SG184062A1 (en) | 2012-10-30 |
| KR20130086520A (ko) | 2013-08-02 |
| CA2791737A1 (en) | 2011-09-22 |
| GB201004200D0 (en) | 2010-04-28 |
| WO2011114275A1 (en) | 2011-09-22 |
| BR112012023320A2 (pt) | 2016-05-24 |
| AU2011228703A1 (en) | 2012-09-20 |
| ZA201206580B (en) | 2013-05-29 |
| EP2547684A1 (en) | 2013-01-23 |
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