JP2012512906A5 - - Google Patents
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- JP2012512906A5 JP2012512906A5 JP2011542506A JP2011542506A JP2012512906A5 JP 2012512906 A5 JP2012512906 A5 JP 2012512906A5 JP 2011542506 A JP2011542506 A JP 2011542506A JP 2011542506 A JP2011542506 A JP 2011542506A JP 2012512906 A5 JP2012512906 A5 JP 2012512906A5
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- JP
- Japan
- Prior art keywords
- alkyl
- aliphatic
- optionally substituted
- compound according
- compound
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 406
- 125000001931 aliphatic group Chemical group 0.000 claims description 404
- 150000001875 compounds Chemical class 0.000 claims description 361
- 229910052799 carbon Inorganic materials 0.000 claims description 181
- 229910052717 sulfur Inorganic materials 0.000 claims description 157
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 155
- 125000005843 halogen group Chemical group 0.000 claims description 151
- 229910052739 hydrogen Inorganic materials 0.000 claims description 147
- 229910052760 oxygen Inorganic materials 0.000 claims description 141
- 125000005842 heteroatom Chemical group 0.000 claims description 121
- 229910052757 nitrogen Inorganic materials 0.000 claims description 113
- 125000000623 heterocyclic group Chemical group 0.000 claims description 106
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 104
- 239000001301 oxygen Chemical group 0.000 claims description 104
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 103
- 239000011593 sulfur Chemical group 0.000 claims description 103
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 82
- 125000004429 atom Chemical group 0.000 claims description 64
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 63
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000003386 piperidinyl group Chemical group 0.000 claims description 57
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 54
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000004193 piperazinyl group Chemical group 0.000 claims description 51
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- 125000003725 azepanyl group Chemical group 0.000 claims description 36
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- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 125000002950 monocyclic group Chemical group 0.000 claims description 32
- -1 2 - piperidinyl Chemical group 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 125000002619 bicyclic group Chemical group 0.000 claims description 23
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- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 11
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- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
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- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 6
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 5
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 claims description 5
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 5
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 5
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 5
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 5
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 5
- KLNFSAOEKUDMFA-UHFFFAOYSA-N azanide;2-hydroxyacetic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OCC(O)=O KLNFSAOEKUDMFA-UHFFFAOYSA-N 0.000 claims description 5
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
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- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical group C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 5
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