KR20140084130A - Mtor 억제제로서의 모르폴리노 치환된 바이사이클릭 피리미딘 우레아 또는 카르바메이트 유도체 - Google Patents

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Publication number

KR20140084130A

KR20140084130A KR1020147012152A KR20147012152A KR20140084130A KR 20140084130 A KR20140084130 A KR 20140084130A KR 1020147012152 A KR1020147012152 A KR 1020147012152A KR 20147012152 A KR20147012152 A KR 20147012152A KR 20140084130 A KR20140084130 A KR 20140084130A

Authority

KR

South Korea

Prior art keywords

phenyl

pyrimidin

dihydrothieno

dioxido

urea

Prior art date

2011-10-07

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.)

Ceased

Links

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• 125000002619 bicyclic group Chemical group 0.000 title 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
• ZENDWEPAVHORFD-UHFFFAOYSA-N pyrimidine;urea Chemical compound NC(N)=O.C1=CN=CN=C1 ZENDWEPAVHORFD-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 179
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• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 138
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 133
• 238000000034 method Methods 0.000 claims description 112
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 105
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 13
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• 125000004076 pyridyl group Chemical group 0.000 claims description 5
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• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
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• DTRRFSMNAUOSAH-AWEZNQCLSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC2=C1SCCC2 DTRRFSMNAUOSAH-AWEZNQCLSA-N 0.000 claims description 3
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• ZVRSXMXKIYBKHA-UEWDXFNNSA-N 1-[3-fluoro-4-[5,7,7-trimethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,6-dioxo-5h-thieno[3,4-d]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound FC1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1C(C)S(=O)(=O)C2(C)C ZVRSXMXKIYBKHA-UEWDXFNNSA-N 0.000 claims description 2
• PTZJHIUMDDFCMD-KGLIPLIRSA-N 1-cyclopropyl-3-[4-[(5s)-5-methyl-4-[(3r)-3-methylmorpholin-4-yl]-6,6-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1([C@@H](S(C2)(=O)=O)C)=C2N=C(C=2C=CC(NC(=O)NC3CC3)=CC=2)N=C1N1CCOC[C@H]1C PTZJHIUMDDFCMD-KGLIPLIRSA-N 0.000 claims description 2
• SIBSISWCPBOCCQ-SFHVURJKSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7,7-dimethyl-6,6-dioxo-5h-thieno[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC2=C1CS(=O)(=O)C2(C)C SIBSISWCPBOCCQ-SFHVURJKSA-N 0.000 claims description 2
• SASGGXUCBYHSDM-MLCCFXAWSA-N 1-cyclopropyl-3-[4-[5-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,6-dioxo-7,8-dihydro-5h-thiopyrano[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC2=C1C(C)S(=O)(=O)CC2 SASGGXUCBYHSDM-MLCCFXAWSA-N 0.000 claims description 2
• IJFVQKCBLRLTQJ-AWEZNQCLSA-N 1-cyclopropyl-3-[4-[6,6-dimethyl-4-[(3s)-3-methylmorpholin-4-yl]-5,5-dioxo-7h-thieno[3,2-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC2=C1S(=O)(=O)C(C)(C)C2 IJFVQKCBLRLTQJ-AWEZNQCLSA-N 0.000 claims description 2
• ITKFZXHURONRPX-CQSZACIVSA-N 1-cyclopropyl-3-[4-[7,7-dimethyl-4-[(3r)-3-methylmorpholin-4-yl]-6,6-dioxo-5h-thieno[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC2=C1CS(=O)(=O)C2(C)C ITKFZXHURONRPX-CQSZACIVSA-N 0.000 claims description 2
• ITKFZXHURONRPX-AWEZNQCLSA-N 1-cyclopropyl-3-[4-[7,7-dimethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,6-dioxo-5h-thieno[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=NC2=C1CS(=O)(=O)C2(C)C ITKFZXHURONRPX-AWEZNQCLSA-N 0.000 claims description 2
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