JP2014530197A5 - - Google Patents
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- Publication number
- JP2014530197A5 JP2014530197A5 JP2014531240A JP2014531240A JP2014530197A5 JP 2014530197 A5 JP2014530197 A5 JP 2014530197A5 JP 2014531240 A JP2014531240 A JP 2014531240A JP 2014531240 A JP2014531240 A JP 2014531240A JP 2014530197 A5 JP2014530197 A5 JP 2014530197A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methylsulfonyl
- urea
- methylmorpholino
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 11
- -1 8-oxa-3-azabicyclo [3.2.1] octan-3-yl Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims description 5
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- WYVZYLFSFLZJLE-AWEZNQCLSA-N 1-(2,2-difluoroethyl)-3-[4-[4-(5-fluoro-2-methylsulfonylphenyl)-6-[(3s)-3-methylmorpholin-4-yl]-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC(C=2C(=CC=C(F)C=2)S(C)(=O)=O)=N1 WYVZYLFSFLZJLE-AWEZNQCLSA-N 0.000 claims description 2
- VGGRTBRWWUFDQE-HNNXBMFYSA-N 1-(2,2-difluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 VGGRTBRWWUFDQE-HNNXBMFYSA-N 0.000 claims description 2
- BTUQEGIDVUWXLY-SFHVURJKSA-N 1-(2,2-dimethylpropyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(C)(C)C)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 BTUQEGIDVUWXLY-SFHVURJKSA-N 0.000 claims description 2
- DWHLEZSBYLJWAP-INIZCTEOSA-N 1-(2-fluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCF)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 DWHLEZSBYLJWAP-INIZCTEOSA-N 0.000 claims description 2
- LGRSDZOSFNRFBX-INIZCTEOSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 LGRSDZOSFNRFBX-INIZCTEOSA-N 0.000 claims description 2
- MZIHKPPULSTVPI-BJQOMGFOSA-N 1-(3-amino-4,4,4-trifluorobutyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCC(N)C(F)(F)F)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 MZIHKPPULSTVPI-BJQOMGFOSA-N 0.000 claims description 2
- AZRCITZEGHCMJZ-IBGZPJMESA-N 1-[4-(hydroxymethyl)phenyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3C=CC(CO)=CC=3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 AZRCITZEGHCMJZ-IBGZPJMESA-N 0.000 claims description 2
- CBTGCCPITWABCX-HNNXBMFYSA-N 1-[4-[4-(5-fluoro-2-methylsulfonylphenyl)-6-[(3s)-3-methylmorpholin-4-yl]-1,3,5-triazin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC(C=2C(=CC=C(F)C=2)S(C)(=O)=O)=N1 CBTGCCPITWABCX-HNNXBMFYSA-N 0.000 claims description 2
- NQDNTFVBTMDPOY-AWEZNQCLSA-N 1-[4-[4-(5-fluoro-2-methylsulfonylphenyl)-6-[(3s)-3-methylmorpholin-4-yl]-1,3,5-triazin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=CC=C(F)C=2)S(C)(=O)=O)=N1 NQDNTFVBTMDPOY-AWEZNQCLSA-N 0.000 claims description 2
- SVVLFAXKYZRIEU-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-(2,2,2-trifluoroethyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)(F)F)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 SVVLFAXKYZRIEU-HNNXBMFYSA-N 0.000 claims description 2
- IQZVHHCWLJKABG-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-(2-methylpropyl)urea Chemical compound C1=CC(NC(=O)NCC(C)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 IQZVHHCWLJKABG-SFHVURJKSA-N 0.000 claims description 2
- OBNUCJQVVUPBMF-OOJLDXBWSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-(3,3,3-trifluoro-2-hydroxypropyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(O)C(F)(F)F)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 OBNUCJQVVUPBMF-OOJLDXBWSA-N 0.000 claims description 2
- HJYVQAWXJMKHEL-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-(3,3,3-trifluoropropyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCC(F)(F)F)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 HJYVQAWXJMKHEL-INIZCTEOSA-N 0.000 claims description 2
- FYUYLNAVOSQURC-BJQOMGFOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-(4,4,4-trifluoro-3-hydroxybutyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCC(O)C(F)(F)F)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 FYUYLNAVOSQURC-BJQOMGFOSA-N 0.000 claims description 2
- QUUFTKOHCWDTPU-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-(oxetan-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3COC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 QUUFTKOHCWDTPU-INIZCTEOSA-N 0.000 claims description 2
- DTJJNINJMPHAGI-DIMJTDRSSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-(oxolan-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3COCC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 DTJJNINJMPHAGI-DIMJTDRSSA-N 0.000 claims description 2
- WTVPWCNBRLNHIC-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 WTVPWCNBRLNHIC-KRWDZBQOSA-N 0.000 claims description 2
- NBMCWYMOBZCRCH-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 NBMCWYMOBZCRCH-KRWDZBQOSA-N 0.000 claims description 2
- GHPKGLRLNYQRBA-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3C=NC=CC=3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 GHPKGLRLNYQRBA-SFHVURJKSA-N 0.000 claims description 2
- OBQBFVXXGFPXMM-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3C=CN=CC=3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 OBQBFVXXGFPXMM-SFHVURJKSA-N 0.000 claims description 2
- SNXHGDLEEWPMMH-KRWDZBQOSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 SNXHGDLEEWPMMH-KRWDZBQOSA-N 0.000 claims description 2
- HGOXTLYZGOXGIM-IBGZPJMESA-N 1-cyclohexyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCCCC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 HGOXTLYZGOXGIM-IBGZPJMESA-N 0.000 claims description 2
- FZJLSYYBXRUXGH-SFHVURJKSA-N 1-cyclopentyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCCC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 FZJLSYYBXRUXGH-SFHVURJKSA-N 0.000 claims description 2
- LLYIELJURDPGCH-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-(2-ethylsulfonylphenyl)-6-[(3s)-3-methylmorpholin-4-yl]-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CCS(=O)(=O)C1=CC=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 LLYIELJURDPGCH-KRWDZBQOSA-N 0.000 claims description 2
- OQZKTVLGUXLLEG-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(2-methylsulfonylphenyl)-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CS(=O)(=O)C1=CC=CC=C1C1=NC(N2C3CCC2COC3)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 OQZKTVLGUXLLEG-UHFFFAOYSA-N 0.000 claims description 2
- WAMCZFZZIYHSIR-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(2-methylsulfonylphenyl)-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CS(=O)(=O)C1=CC=CC=C1C1=NC(N2CC3CCC(O3)C2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 WAMCZFZZIYHSIR-UHFFFAOYSA-N 0.000 claims description 2
- KYANJFCYCNOTEN-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(2-methylsulfonylphenyl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CS(=O)(=O)C1=CC=CC=C1C1=NC(N2CCOCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 KYANJFCYCNOTEN-UHFFFAOYSA-N 0.000 claims description 2
- WLORGJWWSIEHGH-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(3,3-dimethylmorpholin-4-yl)-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CC1(C)COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 WLORGJWWSIEHGH-UHFFFAOYSA-N 0.000 claims description 2
- RRBDAWQZDGPPKD-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(3-ethylmorpholin-4-yl)-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CCC1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 RRBDAWQZDGPPKD-UHFFFAOYSA-N 0.000 claims description 2
- PJLYVQWIEXBFKX-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(5-fluoro-2-methylsulfonylphenyl)-6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1C1=NC(N2CC3CCC(O3)C2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 PJLYVQWIEXBFKX-UHFFFAOYSA-N 0.000 claims description 2
- CEIONWZVTMNAML-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-(5-fluoro-2-methylsulfonylphenyl)-6-[(3s)-3-methylmorpholin-4-yl]-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC(C=2C(=CC=C(F)C=2)S(C)(=O)=O)=N1 CEIONWZVTMNAML-HNNXBMFYSA-N 0.000 claims description 2
- JTWIUWYFTTUDAS-MRXNPFEDSA-N 1-cyclopropyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 JTWIUWYFTTUDAS-MRXNPFEDSA-N 0.000 claims description 2
- JTWIUWYFTTUDAS-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 JTWIUWYFTTUDAS-INIZCTEOSA-N 0.000 claims description 2
- GWYWSNIEOOQQBY-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpyridin-3-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC(C=2C(=NC=CC=2)S(C)(=O)=O)=N1 GWYWSNIEOOQQBY-HNNXBMFYSA-N 0.000 claims description 2
- DVBAKXMLTYRUSI-IBGZPJMESA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-pyrrolidin-1-ylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC(C=2C(=CC=CC=2)S(=O)(=O)N2CCCC2)=N1 DVBAKXMLTYRUSI-IBGZPJMESA-N 0.000 claims description 2
- STZUVZVOVGSFFP-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-[3-(hydroxymethyl)morpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound CS(=O)(=O)C1=CC=CC=C1C1=NC(N2C(COCC2)CO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 STZUVZVOVGSFFP-UHFFFAOYSA-N 0.000 claims description 2
- OWHWSFSRAOFWHP-HNNXBMFYSA-N 1-ethyl-3-[4-[4-(5-fluoro-2-methylsulfonylphenyl)-6-[(3s)-3-methylmorpholin-4-yl]-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=CC=C(F)C=2)S(C)(=O)=O)=N1 OWHWSFSRAOFWHP-HNNXBMFYSA-N 0.000 claims description 2
- SHEFEJGEGWCOJZ-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 SHEFEJGEGWCOJZ-INIZCTEOSA-N 0.000 claims description 2
- NVIJRBWVGIMMMD-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpyridin-3-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=NC=CC=2)S(C)(=O)=O)=N1 NVIJRBWVGIMMMD-HNNXBMFYSA-N 0.000 claims description 2
- YKIWVDVZGHLPNJ-HNNXBMFYSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylphenyl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=CC=CC=2)S(C)(=O)=O)=N1 YKIWVDVZGHLPNJ-HNNXBMFYSA-N 0.000 claims description 2
- MHPWJPNRJCISIB-AWEZNQCLSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpyridin-3-yl)-1,3,5-triazin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=NC(C=2C(=NC=CC=2)S(C)(=O)=O)=N1 MHPWJPNRJCISIB-AWEZNQCLSA-N 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 102000003954 Autophagy-Related Proteins Human genes 0.000 claims description 2
- 108010082399 Autophagy-Related Proteins Proteins 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- 230000000172 allergic effect Effects 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 230000001363 autoimmune Effects 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 208000016097 disease of metabolism Diseases 0.000 claims description 2
- 208000037765 diseases and disorders Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
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| EP2542536B1 (en) | 2010-03-04 | 2015-01-21 | Cellzome Limited | Morpholino substituted urea derivatives as mtor inhibitors |
| KR20140084130A (ko) | 2011-10-07 | 2014-07-04 | 셀좀 리미티드 | Mtor 억제제로서의 모르폴리노 치환된 바이사이클릭 피리미딘 우레아 또는 카르바메이트 유도체 |
| US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
| UY36294A (es) | 2014-09-12 | 2016-04-29 | Novartis Ag | Compuestos y composiciones como inhibidores de quinasa |
| AU2017329090B9 (en) | 2016-09-19 | 2019-09-05 | Novartis Ag | Therapeutic combinations comprising a RAF inhibitor and a ERK inhibitor |
| CA3057969A1 (en) | 2017-05-02 | 2018-11-08 | Novartis Ag | Combination therapy |
| EP3849535A4 (en) | 2018-09-10 | 2022-06-29 | Mirati Therapeutics, Inc. | Combination therapies |
| EP3969449B1 (en) | 2019-05-13 | 2025-02-12 | Novartis AG | New crystalline forms of n-(3-(2-(2-hydroxyethoxy)-6-morpholinopyridin-4-yl)-4-methvlphenyl)-2(trifluoromethyl)isonicotinamide as raf inhibitors for the treatment of cancer |
| US12576069B2 (en) | 2019-09-11 | 2026-03-17 | Yale University | Compositions and methods for treating slow-flow vascular malformations |
| CN115109049B (zh) * | 2022-08-12 | 2023-08-15 | 江西科技师范大学 | 含芳基脲结构的三嗪类化合物及其应用 |
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| EP1054004B1 (en) | 1997-12-15 | 2008-07-16 | Astellas Pharma Inc. | Novel pyrimidine-5-carboxamide derivatives |
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| KR100881105B1 (ko) | 1999-11-05 | 2009-02-02 | 아스트라제네카 아베 | Ｖｅｇｆ 억제제로서의 퀴나졸린 유도체 |
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| CN101218229A (zh) | 2005-05-05 | 2008-07-09 | 阿斯利康(瑞典)有限公司 | 吡唑基-氨基取代的嘧啶及其在癌症治疗中的应用 |
| PL1891446T3 (pl) | 2005-06-14 | 2013-08-30 | Cellzome Gmbh | Sposób identyfikacji nowych związków oddziałujących z enzymami |
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| AU2007287428B2 (en) | 2006-08-24 | 2011-08-11 | Astrazeneca Ab | Morpholino pyrimidine derivatives useful in the treatment of proliferative disorders |
| US20080234262A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Pyrazolopyrimidine analogs and their use as mtor kinase and pi3 kinase inhibitors |
| US20080233127A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Imidazolopyrimidine analogs and their use as pi3 kinase and mtor inhibitors |
| US8012986B2 (en) * | 2007-04-02 | 2011-09-06 | Hoffmann-La Roche Inc. | Pyridine and pyrimidine derivatives as MGLUR2 antagonists |
| CN101678215B (zh) | 2007-04-18 | 2014-10-01 | 辉瑞产品公司 | 用于治疗异常细胞生长的磺酰胺衍生物 |
| US20090274698A1 (en) | 2007-07-06 | 2009-11-05 | Shripad Bhagwat | Combination anti-cancer therapy |
| AU2008273889B2 (en) | 2007-07-09 | 2012-03-08 | Astrazeneca Ab | Trisubstituted pyrimidine derivatives for the treatment of proliferative diseases |
| BRPI0814503A2 (pt) | 2007-07-09 | 2017-05-16 | Astrazeneca Ab | composto, uso de um composto, métodos para produzir um efeito anti-proliferativo em um animal de sangue quente, e para tratar uma doença, e, composição farmacêutica |
| US20100261723A1 (en) | 2007-07-09 | 2010-10-14 | Astrazeneca Ab | Trisubstituted pyrimidine derivatives for the treatment of proliferative diseases |
| CN101809002B (zh) | 2007-07-09 | 2013-03-27 | 阿斯利康(瑞典)有限公司 | 用于与mtor激酶和/或pi3k相关的疾病中的吗啉代嘧啶衍生物 |
| CN101224207A (zh) | 2007-10-12 | 2008-07-23 | 中国科学院上海有机化学研究所 | 具有诱导自吞噬治疗错误折叠蛋白聚集所致疾病的药物及其筛选方法 |
| WO2009093981A1 (en) * | 2008-01-23 | 2009-07-30 | S Bio Pte Ltd | Triazine compounds as kinase inhibitors |
| DK2245181T3 (da) | 2008-02-04 | 2012-02-06 | Cellzome Ag | Selektivitetsprofilering af PI3K-interagerende molekyler med multiple mål |
| LT2294072T (lt) * | 2008-05-23 | 2017-06-12 | Wyeth Llc | Triazino junginiai, kaip p13 kinazės ir mtor inhibitoriai |
| CA2729045A1 (en) | 2008-07-31 | 2010-02-04 | Philippe Bergeron | Pyrimidine compounds, compositions and methods of use |
| GB2465405A (en) * | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| WO2010096619A1 (en) | 2009-02-23 | 2010-08-26 | Wyeth Llc | Process, purification and crystallization of 1-(4-{[4-(dimethylamino)piperidin-1-yl]carbonyl}phenyl)-3-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]urea |
| ES2529205T3 (es) | 2009-03-13 | 2015-02-17 | Cellzome Limited | Derivados de pirimidina como inhibidores de mTOR |
| JP5649643B2 (ja) | 2009-04-17 | 2015-01-07 | ワイス・エルエルシー | ピリミジン化合物、ｍＴＯＲキナーゼおよびＰＩ３キナーゼ阻害剤としてのそれらの使用、ならびにそれらの合成 |
| WO2010120994A2 (en) | 2009-04-17 | 2010-10-21 | Wyeth Llc | Ureidoaryl-and carbamoylaryl-morpholino- pyrimidine compounds, their use as mtor kinase and pi3 kinase inhibitors, and their synthesis |
| US20140018354A9 (en) | 2009-07-23 | 2014-01-16 | Nathaniel Moorman | Inhibitors of mtor kinase as anti-viral agents |
| EP2542536B1 (en) * | 2010-03-04 | 2015-01-21 | Cellzome Limited | Morpholino substituted urea derivatives as mtor inhibitors |
| WO2012136622A1 (en) | 2011-04-04 | 2012-10-11 | Cellzome Limited | Dihydropyrrolo pyrimidine derivatives as mtor inhibitors |
| KR20140084130A (ko) | 2011-10-07 | 2014-07-04 | 셀좀 리미티드 | Mtor 억제제로서의 모르폴리노 치환된 바이사이클릭 피리미딘 우레아 또는 카르바메이트 유도체 |
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- 2012-09-21 RU RU2014109747A patent/RU2616619C2/ru not_active IP Right Cessation
- 2012-09-21 KR KR1020147010624A patent/KR20140070616A/ko not_active Ceased
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