JP2004533454A5 - - Google Patents
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- Publication number
- JP2004533454A5 JP2004533454A5 JP2002589483A JP2002589483A JP2004533454A5 JP 2004533454 A5 JP2004533454 A5 JP 2004533454A5 JP 2002589483 A JP2002589483 A JP 2002589483A JP 2002589483 A JP2002589483 A JP 2002589483A JP 2004533454 A5 JP2004533454 A5 JP 2004533454A5
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- amino
- phenyl
- pyrrolo
- benzyloxy
- 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 234
- 150000001875 compounds Chemical class 0.000 claims 71
- 125000000623 heterocyclic group Chemical group 0.000 claims 38
- -1 di-substituted amino Chemical group 0.000 claims 36
- 229910052757 nitrogen Inorganic materials 0.000 claims 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 20
- 239000001301 oxygen Substances 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 239000011593 sulfur Chemical group 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- MINLECAKOASWQA-UHFFFAOYSA-N 7-[3-(aminomethyl)cyclobutyl]-5-(3-phenylmethoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1C(CN)CC1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 MINLECAKOASWQA-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 229950001413 metamfepramone Drugs 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- CZAXYMOAFIXZDY-UHFFFAOYSA-N 1-[[3-[4-amino-5-(3-phenylmethoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]cyclobutyl]methyl]-3-propan-2-ylurea Chemical compound C1C(CNC(=O)NC(C)C)CC1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 CZAXYMOAFIXZDY-UHFFFAOYSA-N 0.000 claims 1
- GQGMUKOYILWOIQ-UHFFFAOYSA-N 6-methyl-5-(3-phenylmethoxyphenyl)-7-[3-(pyrrolidin-1-ylmethyl)cyclobutyl]pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C12=C(N)N=CN=C2N(C2CC(CN3CCCC3)C2)C(C)=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 GQGMUKOYILWOIQ-UHFFFAOYSA-N 0.000 claims 1
- AECDBHGVIIRMOI-UHFFFAOYSA-N 7-[3-(azetidin-1-ylmethyl)cyclobutyl]-5-(3-phenylmethoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CC(CN3CCC3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 AECDBHGVIIRMOI-UHFFFAOYSA-N 0.000 claims 1
- ICHGNLVHYDFSAR-RZFKFIIISA-N C12=C(N)N=CN=C2N([C@@H]2C[C@@H](CNC3CCOCC3)C2)C(C)=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 Chemical compound C12=C(N)N=CN=C2N([C@@H]2C[C@@H](CNC3CCOCC3)C2)C(C)=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 ICHGNLVHYDFSAR-RZFKFIIISA-N 0.000 claims 1
- XQMSYQDZIAGQPB-MXVIHJGJSA-N C12=C(N)N=CN=C2N([C@@H]2C[C@H](C2)C(=O)OC)C(CC)=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 Chemical compound C12=C(N)N=CN=C2N([C@@H]2C[C@H](C2)C(=O)OC)C(CC)=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 XQMSYQDZIAGQPB-MXVIHJGJSA-N 0.000 claims 1
- AECDBHGVIIRMOI-AQYVVDRMSA-N C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCC3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCC3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 AECDBHGVIIRMOI-AQYVVDRMSA-N 0.000 claims 1
- IONLBUKCCPUJIH-HCGLCNNCSA-N C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCCCC3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCCCC3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 IONLBUKCCPUJIH-HCGLCNNCSA-N 0.000 claims 1
- IPUIQYUWBBQMLR-DUYHBEBVSA-N C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCN(CC3)C=3N=CC=CC=3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCN(CC3)C=3N=CC=CC=3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 IPUIQYUWBBQMLR-DUYHBEBVSA-N 0.000 claims 1
- KUUHULDUODEQHB-AFARHQOCSA-N C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCOCC3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2C[C@@H](CN3CCOCC3)C2)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 KUUHULDUODEQHB-AFARHQOCSA-N 0.000 claims 1
- ZXYAKTRUTLRFEX-YFJLJUBXSA-N C1C(C)OC(C)CN1C[C@@H]1C[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)=C2)C1 Chemical compound C1C(C)OC(C)CN1C[C@@H]1C[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)=C2)C1 ZXYAKTRUTLRFEX-YFJLJUBXSA-N 0.000 claims 1
- REXRZICSDNALRF-HCGLCNNCSA-N C1CN(C)CCN1C[C@@H]1C[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)=C2)C1 Chemical compound C1CN(C)CCN1C[C@@H]1C[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)=C2)C1 REXRZICSDNALRF-HCGLCNNCSA-N 0.000 claims 1
- LDRXGQRNDOVOLA-MXVIHJGJSA-N C1[C@@H](C(=O)N(C)C)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 Chemical compound C1[C@@H](C(=O)N(C)C)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 LDRXGQRNDOVOLA-MXVIHJGJSA-N 0.000 claims 1
- FITJQXRHQKAHRQ-WGSAOQKQSA-N C1[C@@H](C(=O)NC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 Chemical compound C1[C@@H](C(=O)NC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 FITJQXRHQKAHRQ-WGSAOQKQSA-N 0.000 claims 1
- NTMLQBGOQOGFFT-IYARVYRRSA-N C1[C@@H](C(=O)OC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1Br Chemical compound C1[C@@H](C(=O)OC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1Br NTMLQBGOQOGFFT-IYARVYRRSA-N 0.000 claims 1
- MGADSANUGJPJTF-MXVIHJGJSA-N C1[C@@H](C(=O)OC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1C Chemical compound C1[C@@H](C(=O)OC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1C MGADSANUGJPJTF-MXVIHJGJSA-N 0.000 claims 1
- MINLECAKOASWQA-UAPYVXQJSA-N C1[C@@H](CN)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 Chemical compound C1[C@@H](CN)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 MINLECAKOASWQA-UAPYVXQJSA-N 0.000 claims 1
- WBYYXJHMBIEJCC-AFARHQOCSA-N C1[C@@H](CNC(=O)N(CC)CC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 Chemical compound C1[C@@H](CNC(=O)N(CC)CC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 WBYYXJHMBIEJCC-AFARHQOCSA-N 0.000 claims 1
- CQQQRDIANWGYBY-KESTWPANSA-N C1[C@@H](CNC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 Chemical compound C1[C@@H](CNC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 CQQQRDIANWGYBY-KESTWPANSA-N 0.000 claims 1
- XRMMWXGVGDPTGL-AQYVVDRMSA-N CC(C)(C)NC(=O)NC[C@H]1C[C@@H](C1)n1cc(-c2cccc(OCc3ccccc3)c2)c2c(N)ncnc12 Chemical compound CC(C)(C)NC(=O)NC[C@H]1C[C@@H](C1)n1cc(-c2cccc(OCc3ccccc3)c2)c2c(N)ncnc12 XRMMWXGVGDPTGL-AQYVVDRMSA-N 0.000 claims 1
- JSOCIINBZIRFJJ-AQYVVDRMSA-N CC(C)C(=O)NC[C@H]1C[C@@H](C1)n1cc(-c2cccc(OCc3ccccc3)c2)c2c(N)ncnc12 Chemical compound CC(C)C(=O)NC[C@H]1C[C@@H](C1)n1cc(-c2cccc(OCc3ccccc3)c2)c2c(N)ncnc12 JSOCIINBZIRFJJ-AQYVVDRMSA-N 0.000 claims 1
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- CZOJVEPPEOWDQJ-YFJLJUBXSA-N CC1CCC(C)N1C[C@@H]1C[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)=C2)C1 Chemical compound CC1CCC(C)N1C[C@@H]1C[C@@H](N2C3=NC=NC(N)=C3C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)=C2)C1 CZOJVEPPEOWDQJ-YFJLJUBXSA-N 0.000 claims 1
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| CN100536850C (zh) * | 2003-08-08 | 2009-09-09 | 诺瓦提斯公司 | 包含星孢素的组合 |
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| ES2652440T3 (es) | 2004-04-02 | 2018-02-02 | OSI Pharmaceuticals, LLC | Inhibidores de proteína cinasa heterobicíclicos sustituidos con anillo 6,6-bicíclico |
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| CN101340909B (zh) | 2005-10-18 | 2012-01-11 | 詹森药业有限公司 | 抑制flt3激酶的方法 |
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