KR20130086520A - 스피로시클릭 화합물 및 이들의 치료제 및 진단 프로브로서 용도 - Google Patents
스피로시클릭 화합물 및 이들의 치료제 및 진단 프로브로서 용도 Download PDFInfo
- Publication number
- KR20130086520A KR20130086520A KR1020127026689A KR20127026689A KR20130086520A KR 20130086520 A KR20130086520 A KR 20130086520A KR 1020127026689 A KR1020127026689 A KR 1020127026689A KR 20127026689 A KR20127026689 A KR 20127026689A KR 20130086520 A KR20130086520 A KR 20130086520A
- Authority
- KR
- South Korea
- Prior art keywords
- oxa
- heptan
- morpholino
- azaspiro
- triazin
- Prior art date
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 177
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 44
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 16
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 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
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- 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 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 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
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- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 208000035475 disorder Diseases 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 229940002612 prodrug Drugs 0.000 claims description 24
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- 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
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
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- 125000003118 aryl group Chemical group 0.000 claims description 17
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
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- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 9
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- 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
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- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
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- 108010090804 Streptavidin Proteins 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
- 150000002829 nitrogen Chemical class 0.000 claims description 7
- 239000007790 solid phase Substances 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- 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 6
- 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 6
- SWVYUIBQZQZMIE-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]pyrimidin-2-yl]urea Chemical compound C1CC(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(=O)NC1=NC=C(C=2N=C(N=C(N=2)N2CC3(COC3)C2)N2CCOCC2)C=N1 SWVYUIBQZQZMIE-UHFFFAOYSA-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
- RCZNKLPZXMBEOE-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]prop-2-en-1-one Chemical compound C1=NC(N)=NC=C1C1=NC(N2CC3(CN(C3)C(=O)C=C)C2)=NC(N2CCOCC2)=N1 RCZNKLPZXMBEOE-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- QOFYYRLHGYNMAY-UHFFFAOYSA-N 1-ethyl-3-[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]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 QOFYYRLHGYNMAY-UHFFFAOYSA-N 0.000 claims description 6
- 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
- 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
- HKANYLUCPXCQRZ-UHFFFAOYSA-N 1-ethyl-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 C1=NC(NC(=O)NCC)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CCOCC2)=N1 HKANYLUCPXCQRZ-UHFFFAOYSA-N 0.000 claims description 6
- YHCSLFITDABKFS-UHFFFAOYSA-N 1-ethyl-3-[5-[4-morpholin-4-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(N2CCOCC2)=N1 YHCSLFITDABKFS-UHFFFAOYSA-N 0.000 claims description 6
- WBHVIWTZHKYWMV-UHFFFAOYSA-N 1-methyl-3-[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]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3(COC3)C2)=NC(N2CC3CCC(O3)C2)=N1 WBHVIWTZHKYWMV-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
- KWOMZVDZXXUIPW-UHFFFAOYSA-N 2-chloro-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]ethanone Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CC3(CN(C3)C(=O)CCl)C2)=NC=1N1CCOCC1 KWOMZVDZXXUIPW-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
- 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 6
- 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 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
- 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
- PGPHXOGMZSAAHC-UHFFFAOYSA-N 6-[2-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-ylpyrimidin-4-yl]-2-oxa-6-azaspiro[3.3]heptane Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CC3(COC3)C2)=CC=1N1CCOCC1 PGPHXOGMZSAAHC-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 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 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
- 125000005392 carboxamide group Chemical class NC(=O)* 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 6
- HXCNWXXFEHKQMC-UHFFFAOYSA-N 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]prop-2-enamide Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CC3(CN(CCNC(=O)C=C)C3)C2)=NC=1N1CCOCC1 HXCNWXXFEHKQMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 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 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- CDJKJHUNAOLZSC-UHFFFAOYSA-N 2,6-dimethoxy-4-[1-[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]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)N2CC3CCC(O3)C2)=C1 CDJKJHUNAOLZSC-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
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
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Classifications
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- 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
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- 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 (3)
| 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 |
| GB1004200.0 | 2010-03-15 | ||
| PCT/IB2011/051047 WO2011114275A1 (en) | 2010-03-15 | 2011-03-11 | Spirocyclic compounds and their use as therapeutic agents and diagnostic probes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20130086520A true KR20130086520A (ko) | 2013-08-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127026689A Withdrawn KR20130086520A (ko) | 2010-03-15 | 2011-03-11 | 스피로시클릭 화합물 및 이들의 치료제 및 진단 프로브로서 용도 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20130040934A1 (https=) |
| EP (1) | EP2547684A1 (https=) |
| JP (1) | JP2013522286A (https=) |
| KR (1) | KR20130086520A (https=) |
| CN (1) | CN102939292A (https=) |
| AU (1) | AU2011228703A1 (https=) |
| BR (1) | BR112012023320A2 (https=) |
| CA (1) | CA2791737A1 (https=) |
| GB (1) | GB201004200D0 (https=) |
| MX (1) | MX2012010655A (https=) |
| NZ (1) | NZ602292A (https=) |
| RU (1) | RU2012143689A (https=) |
| SG (1) | SG184062A1 (https=) |
| WO (1) | WO2011114275A1 (https=) |
| ZA (1) | ZA201206580B (https=) |
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|---|---|---|---|---|
| KR20140069235A (ko) | 2011-09-27 | 2014-06-09 | 노파르티스 아게 | 돌연변이체 idh의 억제제로서의 3-피리미딘-4-일-옥사졸리딘-2-온 |
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| EP1389617B1 (en) | 2001-04-27 | 2007-01-03 | Zenyaku Kogyo Kabushiki Kaisha | Heterocyclic compound and antitumor agent containing the same as active ingredient |
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| 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 |
| WO2009140128A2 (en) * | 2008-05-13 | 2009-11-19 | Irm Llc | Compounds and compositions as kinase inhibitors |
| AP2775A (en) * | 2008-05-23 | 2013-09-30 | Wyeth Llc | Triazine compounds as P13 kinase and MTOR inhibitors |
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- 2011-03-11 AU AU2011228703A patent/AU2011228703A1/en not_active Abandoned
- 2011-03-11 KR KR1020127026689A patent/KR20130086520A/ko not_active Withdrawn
- 2011-03-11 RU RU2012143689/04A patent/RU2012143689A/ru not_active Application Discontinuation
- 2011-03-11 CA CA2791737A patent/CA2791737A1/en not_active Abandoned
- 2011-03-11 EP EP11715742A patent/EP2547684A1/en not_active Withdrawn
- 2011-03-11 US US13/635,016 patent/US20130040934A1/en not_active Abandoned
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- 2011-03-11 BR BR112012023320A patent/BR112012023320A2/pt not_active IP Right Cessation
- 2011-03-11 WO PCT/IB2011/051047 patent/WO2011114275A1/en not_active Ceased
- 2011-03-11 JP JP2012557645A patent/JP2013522286A/ja active Pending
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| US20130040934A1 (en) | 2013-02-14 |
| AU2011228703A1 (en) | 2012-09-20 |
| MX2012010655A (es) | 2012-10-05 |
| RU2012143689A (ru) | 2014-04-20 |
| NZ602292A (en) | 2014-08-29 |
| CA2791737A1 (en) | 2011-09-22 |
| GB201004200D0 (en) | 2010-04-28 |
| WO2011114275A1 (en) | 2011-09-22 |
| SG184062A1 (en) | 2012-10-30 |
| BR112012023320A2 (pt) | 2016-05-24 |
| ZA201206580B (en) | 2013-05-29 |
| JP2013522286A (ja) | 2013-06-13 |
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