JP2004535414A5 - - Google Patents
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- Publication number
- JP2004535414A5 JP2004535414A5 JP2003500067A JP2003500067A JP2004535414A5 JP 2004535414 A5 JP2004535414 A5 JP 2004535414A5 JP 2003500067 A JP2003500067 A JP 2003500067A JP 2003500067 A JP2003500067 A JP 2003500067A JP 2004535414 A5 JP2004535414 A5 JP 2004535414A5
- Authority
- JP
- Japan
- Prior art keywords
- ylamino
- pyrimidin
- bromo
- benzenesulfonamide
- methyl
- 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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- -1 hydroxy, hydroxy Chemical group 0.000 claims 24
- 150000001408 amides Chemical class 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 208000036142 Viral infection Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- XSPDIJHMXIOAAM-CYBMUJFWSA-N 3-[[5-bromo-4-[[(2s)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]benzenesulfonyl fluoride Chemical compound C1=C(Br)C(N[C@H](CO)C(C)C)=NC(NC=2C=C(C=CC=2)S(F)(=O)=O)=N1 XSPDIJHMXIOAAM-CYBMUJFWSA-N 0.000 claims 2
- XGXLQYXQHKKNBW-UHFFFAOYSA-N 4-[[5-bromo-4-(cyclohexylamino)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NC2CCCCC2)=N1 XGXLQYXQHKKNBW-UHFFFAOYSA-N 0.000 claims 2
- SEKKALNTFPTFSU-UHFFFAOYSA-N 4-[[5-bromo-4-[(4-morpholin-4-ylcyclohexyl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NC2CCC(CC2)N2CCOCC2)=N1 SEKKALNTFPTFSU-UHFFFAOYSA-N 0.000 claims 2
- FGHMZQKPPMDGPL-HNNXBMFYSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-hydroxyethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCO)=N1 FGHMZQKPPMDGPL-HNNXBMFYSA-N 0.000 claims 2
- CAEOUNLFYKBMQK-UHFFFAOYSA-N 4-[[5-bromo-4-[[4-(1,3-dihydroxypropan-2-ylamino)cyclohexyl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NC2CCC(CC2)NC(CO)CO)=N1 CAEOUNLFYKBMQK-UHFFFAOYSA-N 0.000 claims 2
- OBAVLVDITDFXPY-UHFFFAOYSA-N 4-[[5-bromo-4-[[4-(3-hydroxypyrrolidin-1-yl)cyclohexyl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NC2CCC(CC2)N2CC(O)CC2)=N1 OBAVLVDITDFXPY-UHFFFAOYSA-N 0.000 claims 2
- BWOHFZMMQXOIOB-UHFFFAOYSA-N 4-[[5-bromo-4-[[4-(cyclopropylamino)cyclohexyl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NC2CCC(CC2)NC2CC2)=N1 BWOHFZMMQXOIOB-UHFFFAOYSA-N 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- FKWGXFQRNHMIPY-UHFFFAOYSA-N methyl 6-[[5-bromo-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]hexanoate Chemical compound C1=C(Br)C(NCCCCCC(=O)OC)=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 FKWGXFQRNHMIPY-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- NENICYIQLCYNII-AWEZNQCLSA-N (2r)-2-[[5-bromo-2-(3-methylsulfonylanilino)pyrimidin-4-yl]amino]-3-methylbutan-1-ol Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=C(C=CC=2)S(C)(=O)=O)=N1 NENICYIQLCYNII-AWEZNQCLSA-N 0.000 claims 1
- OAOMNZDRBMUIIJ-AWEZNQCLSA-N (2r)-2-[[5-bromo-2-(4-methylsulfonylanilino)pyrimidin-4-yl]amino]-3-methylbutan-1-ol Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=N1 OAOMNZDRBMUIIJ-AWEZNQCLSA-N 0.000 claims 1
- AFQIRVPDWCOXNF-GFCCVEGCSA-N (2r)-2-[[5-bromo-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]-3-methylbutanoic acid Chemical compound C1=C(Br)C(N[C@H](C(C)C)C(O)=O)=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 AFQIRVPDWCOXNF-GFCCVEGCSA-N 0.000 claims 1
- DMPLZVOZGQRKFY-HNNXBMFYSA-N (2r)-2-[[5-bromo-2-[3-(2-hydroxyethylsulfonyl)anilino]pyrimidin-4-yl]amino]-3-methylbutan-1-ol Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=C(C=CC=2)S(=O)(=O)CCO)=N1 DMPLZVOZGQRKFY-HNNXBMFYSA-N 0.000 claims 1
- BNJGHFMCPWJPNT-CQSZACIVSA-N (2r)-2-[[5-bromo-2-[4-(2-hydroxyethylsulfamoyl)anilino]pyrimidin-4-yl]amino]-3-methylbutanoic acid Chemical compound C1=C(Br)C(N[C@H](C(C)C)C(O)=O)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCO)=N1 BNJGHFMCPWJPNT-CQSZACIVSA-N 0.000 claims 1
- WDAQHQPSZNIQMH-ZDUSSCGKSA-N (2r)-2-[[5-bromo-2-[4-(trifluoromethylsulfonyl)anilino]pyrimidin-4-yl]amino]-3-methylbutan-1-ol Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)=N1 WDAQHQPSZNIQMH-ZDUSSCGKSA-N 0.000 claims 1
- XGLICGVXAPVYBI-ZETCQYMHSA-N (2s)-2-[[5-bromo-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]propanamide Chemical compound C1=C(Br)C(N[C@@H](C)C(N)=O)=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 XGLICGVXAPVYBI-ZETCQYMHSA-N 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- HFISRXLKZTXXKP-AUEPDCJTSA-N 2-[(e)-3-[[5-bromo-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]butan-2-ylideneamino]oxyacetic acid Chemical compound C1=C(Br)C(NC(C)C(\C)=N\OCC(O)=O)=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 HFISRXLKZTXXKP-AUEPDCJTSA-N 0.000 claims 1
- GUUYSULIBQOZIQ-UHFFFAOYSA-N 2-[3-[[5-bromo-4-(2-morpholin-4-ylethylamino)pyrimidin-2-yl]amino]phenyl]sulfonylethanol Chemical compound OCCS(=O)(=O)C1=CC=CC(NC=2N=C(NCCN3CCOCC3)C(Br)=CN=2)=C1 GUUYSULIBQOZIQ-UHFFFAOYSA-N 0.000 claims 1
- RJVHJGWKLQVDCX-UHFFFAOYSA-N 2-[3-[[5-bromo-4-(prop-2-ynylamino)pyrimidin-2-yl]amino]phenyl]sulfonylethanol Chemical compound OCCS(=O)(=O)C1=CC=CC(NC=2N=C(NCC#C)C(Br)=CN=2)=C1 RJVHJGWKLQVDCX-UHFFFAOYSA-N 0.000 claims 1
- CITDQBCZOBOFHG-NSHDSACASA-N 2-[3-[[5-bromo-4-[[(2s)-1-methoxypropan-2-yl]amino]pyrimidin-2-yl]amino]phenyl]sulfonylethanol Chemical compound C1=C(Br)C(N[C@@H](C)COC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)CCO)=N1 CITDQBCZOBOFHG-NSHDSACASA-N 0.000 claims 1
- MGLNAHDYUZYRJP-UHFFFAOYSA-N 2-[[5-bromo-2-[3-(2-hydroxyethylsulfonyl)anilino]pyrimidin-4-yl]amino]propane-1,3-diol Chemical compound OCCS(=O)(=O)C1=CC=CC(NC=2N=C(NC(CO)CO)C(Br)=CN=2)=C1 MGLNAHDYUZYRJP-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 claims 1
- SAERAINFZWAKGQ-UHFFFAOYSA-N 2-methylbenzenesulfonyl fluoride Chemical compound CC1=CC=CC=C1S(F)(=O)=O SAERAINFZWAKGQ-UHFFFAOYSA-N 0.000 claims 1
- FETWCXOAWZUZBR-UHFFFAOYSA-N 2-n-[3-(benzenesulfonyl)phenyl]-5-bromo-4-n-prop-2-ynylpyrimidine-2,4-diamine Chemical compound N1=C(NCC#C)C(Br)=CN=C1NC1=CC=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 FETWCXOAWZUZBR-UHFFFAOYSA-N 0.000 claims 1
- KTJVQPLZQWUAQY-UHFFFAOYSA-N 3-[[5-bromo-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]propanoic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NCCC(O)=O)=N1 KTJVQPLZQWUAQY-UHFFFAOYSA-N 0.000 claims 1
- AFKUTJOFCAOYQP-UHFFFAOYSA-N 3-[[5-bromo-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]propylphosphonic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NCCCP(O)(O)=O)=N1 AFKUTJOFCAOYQP-UHFFFAOYSA-N 0.000 claims 1
- DOEGEYSAKWHDSP-UHFFFAOYSA-N 3-[[5-bromo-4-(prop-2-ynylamino)pyrimidin-2-yl]amino]-n-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC(NC=2N=C(NCC#C)C(Br)=CN=2)=C1 DOEGEYSAKWHDSP-UHFFFAOYSA-N 0.000 claims 1
- AHTSLHIJXZTEIU-UHFFFAOYSA-N 3-[[5-bromo-4-(prop-2-ynylamino)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NCC#C)C(Br)=CN=2)=C1 AHTSLHIJXZTEIU-UHFFFAOYSA-N 0.000 claims 1
- XQMKRPIZJHEKSG-INIZCTEOSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(1,3-dihydroxypropan-2-yl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NC(CO)CO)=N1 XQMKRPIZJHEKSG-INIZCTEOSA-N 0.000 claims 1
- ALOBCOOXNZFQRZ-SFHVURJKSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(5-hydroxypentyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCCCCO)=N1 ALOBCOOXNZFQRZ-SFHVURJKSA-N 0.000 claims 1
- FCNGRYGECNKENN-HNNXBMFYSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-ethoxybenzenesulfonamide Chemical compound CCONS(=O)(=O)C1=CC=CC(NC=2N=C(N[C@@H](CO)C(C)C)C(Br)=CN=2)=C1 FCNGRYGECNKENN-HNNXBMFYSA-N 0.000 claims 1
- WMVKSRVLBYMNNR-GFCCVEGCSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-methoxyethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCOC)=N1 WMVKSRVLBYMNNR-GFCCVEGCSA-N 0.000 claims 1
- ZHRIYMCBQBKDHN-OAHLLOKOSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCN2CCOCC2)=N1 ZHRIYMCBQBKDHN-OAHLLOKOSA-N 0.000 claims 1
- DQOCEAXNGWJYOV-MRXNPFEDSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-phenoxyethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCOC=2C=CC=CC=2)=N1 DQOCEAXNGWJYOV-MRXNPFEDSA-N 0.000 claims 1
- WEFXZBPQJHRJGU-QGZVFWFLSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-phenylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCC=2C=CC=CC=2)=N1 WEFXZBPQJHRJGU-QGZVFWFLSA-N 0.000 claims 1
- CVNAOWSLMKCPDR-MRXNPFEDSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-piperidin-1-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCN2CCCCC2)=N1 CVNAOWSLMKCPDR-MRXNPFEDSA-N 0.000 claims 1
- FQDMZEONIQIPCD-OAHLLOKOSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCN2CCCC2)=N1 FQDMZEONIQIPCD-OAHLLOKOSA-N 0.000 claims 1
- PYJUMANJGQJYCC-CQSZACIVSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-methylbutyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCC(C)C)=N1 PYJUMANJGQJYCC-CQSZACIVSA-N 0.000 claims 1
- QBMQJPSFFULETH-SNVBAGLBSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NC=2NN=C(SC)N=2)=N1 QBMQJPSFFULETH-SNVBAGLBSA-N 0.000 claims 1
- DSXTVCKGNOCFHH-GOSISDBHSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-phenylpropyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCCC=2C=CC=CC=2)=N1 DSXTVCKGNOCFHH-GOSISDBHSA-N 0.000 claims 1
- NTTYBZPCDJEMGL-MRXNPFEDSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(cyclohexylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC2CCCCC2)=N1 NTTYBZPCDJEMGL-MRXNPFEDSA-N 0.000 claims 1
- XNCPLDQMRCGQLJ-CYBMUJFWSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(furan-2-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2OC=CC=2)=N1 XNCPLDQMRCGQLJ-CYBMUJFWSA-N 0.000 claims 1
- KZAIMJMQCPUPST-OAHLLOKOSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(pyridin-3-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2C=NC=CC=2)=N1 KZAIMJMQCPUPST-OAHLLOKOSA-N 0.000 claims 1
- RWMLEQMESBSDMD-OAHLLOKOSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(pyridin-4-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2C=CN=CC=2)=N1 RWMLEQMESBSDMD-OAHLLOKOSA-N 0.000 claims 1
- SLAQTACRMFNDIX-CYBMUJFWSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(thiophen-2-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2SC=CC=2)=N1 SLAQTACRMFNDIX-CYBMUJFWSA-N 0.000 claims 1
- IBIBVRHCWCQJNH-MRXNPFEDSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(2-methoxyphenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2C(=CC=CC=2)OC)=N1 IBIBVRHCWCQJNH-MRXNPFEDSA-N 0.000 claims 1
- AGKAZHMKZRTJOQ-MRXNPFEDSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(3-fluorophenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2C=C(F)C=CC=2)=N1 AGKAZHMKZRTJOQ-MRXNPFEDSA-N 0.000 claims 1
- SNTLJCJGTVYKFQ-MRXNPFEDSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(4-fluorophenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2C=CC(F)=CC=2)=N1 SNTLJCJGTVYKFQ-MRXNPFEDSA-N 0.000 claims 1
- SVAIQKVFEZHILC-QGZVFWFLSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(4-methylphenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2C=CC(C)=CC=2)=N1 SVAIQKVFEZHILC-QGZVFWFLSA-N 0.000 claims 1
- OMQITYLLWBUKKU-CQSZACIVSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(5-methylfuran-2-yl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCC=2OC(C)=CC=2)=N1 OMQITYLLWBUKKU-CQSZACIVSA-N 0.000 claims 1
- RKVDLZVPSHAYPI-LDCVWXEPSA-N 3-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[2-(1-methylpyrrolidin-2-yl)ethyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C=CC=2)S(=O)(=O)NCCC2N(CCC2)C)=N1 RKVDLZVPSHAYPI-LDCVWXEPSA-N 0.000 claims 1
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- GITZPQVLXGQOFC-ZDUSSCGKSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-hydroxybenzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NO)=N1 GITZPQVLXGQOFC-ZDUSSCGKSA-N 0.000 claims 1
- JRCIPBPLMCNNAZ-AWEZNQCLSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1NC1=NC=C(Br)C(N[C@@H](CO)C(C)C)=N1 JRCIPBPLMCNNAZ-AWEZNQCLSA-N 0.000 claims 1
- SURDDRPIORWROJ-FQEVSTJZSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-phenylmethoxybenzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NOCC=2C=CC=CC=2)=N1 SURDDRPIORWROJ-FQEVSTJZSA-N 0.000 claims 1
- DBRARTVFVQICAR-INIZCTEOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CN=2)=N1 DBRARTVFVQICAR-INIZCTEOSA-N 0.000 claims 1
- HKKPMWUXYNOAMH-ZDUSSCGKSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C(C)C)=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 HKKPMWUXYNOAMH-ZDUSSCGKSA-N 0.000 claims 1
- XXRVXBGHUKJSIE-GFCCVEGCSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC(C)C)=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 XXRVXBGHUKJSIE-GFCCVEGCSA-N 0.000 claims 1
- JYHIAVNXXAOMOP-GFCCVEGCSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-methoxyethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCOC)=N1 JYHIAVNXXAOMOP-GFCCVEGCSA-N 0.000 claims 1
- MOQOQWYFSLCRAF-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCOCC2)=N1 MOQOQWYFSLCRAF-OAHLLOKOSA-N 0.000 claims 1
- CGGQTGLIIRJICO-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-phenoxyethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCOC=2C=CC=CC=2)=N1 CGGQTGLIIRJICO-MRXNPFEDSA-N 0.000 claims 1
- CJCFZRXZAIMSEF-QGZVFWFLSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-phenylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCC=2C=CC=CC=2)=N1 CJCFZRXZAIMSEF-QGZVFWFLSA-N 0.000 claims 1
- NBYSQJLMKWONFD-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-piperidin-1-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCCCC2)=N1 NBYSQJLMKWONFD-MRXNPFEDSA-N 0.000 claims 1
- OIDQEZVDBXFHIZ-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-imidazol-1-ylpropyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCCN2C=NC=C2)=N1 OIDQEZVDBXFHIZ-OAHLLOKOSA-N 0.000 claims 1
- TYLJSCDFQRNRPP-CQSZACIVSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-methylbutyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCC(C)C)=N1 TYLJSCDFQRNRPP-CQSZACIVSA-N 0.000 claims 1
- JBYAKKJCFOWWBR-SNVBAGLBSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NC=2NN=C(SC)N=2)=N1 JBYAKKJCFOWWBR-SNVBAGLBSA-N 0.000 claims 1
- RPCBQIYZEZPTPF-GOSISDBHSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-phenylpropyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCCC=2C=CC=CC=2)=N1 RPCBQIYZEZPTPF-GOSISDBHSA-N 0.000 claims 1
- CPNHYHNOBMDVOF-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(cyclohexylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC2CCCCC2)=N1 CPNHYHNOBMDVOF-MRXNPFEDSA-N 0.000 claims 1
- JNOAGNVWSYXSPQ-CYBMUJFWSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(furan-2-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2OC=CC=2)=N1 JNOAGNVWSYXSPQ-CYBMUJFWSA-N 0.000 claims 1
- CYCCZYUADXNPOZ-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(pyridin-3-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=NC=CC=2)=N1 CYCCZYUADXNPOZ-OAHLLOKOSA-N 0.000 claims 1
- OXYBJLCZAKJBLV-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(pyridin-4-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=CN=CC=2)=N1 OXYBJLCZAKJBLV-OAHLLOKOSA-N 0.000 claims 1
- CTSAAFVAKMBXOE-CYBMUJFWSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-(thiophen-2-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2SC=CC=2)=N1 CTSAAFVAKMBXOE-CYBMUJFWSA-N 0.000 claims 1
- ZREICNPHXIRKFS-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(2-methoxyphenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C(=CC=CC=2)OC)=N1 ZREICNPHXIRKFS-MRXNPFEDSA-N 0.000 claims 1
- XKQPZMWHAHLRFF-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(3,4-dimethoxyphenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=C(OC)C(OC)=CC=2)=N1 XKQPZMWHAHLRFF-MRXNPFEDSA-N 0.000 claims 1
- JALQCMUJHPYDDR-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(3-fluorophenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=C(F)C=CC=2)=N1 JALQCMUJHPYDDR-MRXNPFEDSA-N 0.000 claims 1
- CONRSYAAHSEZNE-OFLPRAFFSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(4-cyanocyclohexyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC2CCC(CC2)C#N)=N1 CONRSYAAHSEZNE-OFLPRAFFSA-N 0.000 claims 1
- HWXKWOWZXBIKQE-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(4-fluorophenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=CC(F)=CC=2)=N1 HWXKWOWZXBIKQE-MRXNPFEDSA-N 0.000 claims 1
- OTXZJRWIKYDAFG-QGZVFWFLSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(4-methylphenyl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=CC(C)=CC=2)=N1 OTXZJRWIKYDAFG-QGZVFWFLSA-N 0.000 claims 1
- DUGZLAZIQIAHNA-CQSZACIVSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[(5-methylfuran-2-yl)methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2OC(C)=CC=2)=N1 DUGZLAZIQIAHNA-CQSZACIVSA-N 0.000 claims 1
- PVCLSBRNZFMIIL-LDCVWXEPSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[2-(1-methylpyrrolidin-2-yl)ethyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCC2N(CCC2)C)=N1 PVCLSBRNZFMIIL-LDCVWXEPSA-N 0.000 claims 1
- LLRIYDPKZNCKIW-QGZVFWFLSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[2-(4-chlorophenyl)ethyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCC=2C=CC(Cl)=CC=2)=N1 LLRIYDPKZNCKIW-QGZVFWFLSA-N 0.000 claims 1
- BZZHQAZRENPBLF-QGZVFWFLSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[2-(4-methoxyphenyl)ethyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCC=2C=CC(OC)=CC=2)=N1 BZZHQAZRENPBLF-QGZVFWFLSA-N 0.000 claims 1
- NXMZNKRQBUGKFU-CYBMUJFWSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[2-(dimethylamino)ethyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN(C)C)=N1 NXMZNKRQBUGKFU-CYBMUJFWSA-N 0.000 claims 1
- FADZTHFNEKILEE-QGZVFWFLSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[2-[di(propan-2-yl)amino]ethyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN(C(C)C)C(C)C)=N1 FADZTHFNEKILEE-QGZVFWFLSA-N 0.000 claims 1
- ZCNLIKVHFSZRMA-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[3-(2-oxopyrrolidin-1-yl)propyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCCN2C(CCC2)=O)=N1 ZCNLIKVHFSZRMA-OAHLLOKOSA-N 0.000 claims 1
- IQZPISAYENKKPK-CQSZACIVSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[3-(dimethylamino)propyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCCN(C)C)=N1 IQZPISAYENKKPK-CQSZACIVSA-N 0.000 claims 1
- QOXHCBQLRMGDND-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[[3-(trifluoromethyl)phenyl]methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=C(C=CC=2)C(F)(F)F)=N1 QOXHCBQLRMGDND-MRXNPFEDSA-N 0.000 claims 1
- NGKJZKMAMLIWOF-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[[4-(trifluoromethyl)phenyl]methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=CC(=CC=2)C(F)(F)F)=N1 NGKJZKMAMLIWOF-MRXNPFEDSA-N 0.000 claims 1
- JKAGJQIISTWTSJ-LLVKDONJSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-cyclopropylbenzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NC2CC2)=N1 JKAGJQIISTWTSJ-LLVKDONJSA-N 0.000 claims 1
- XRGNODWUWZWICO-SECBINFHSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 XRGNODWUWZWICO-SECBINFHSA-N 0.000 claims 1
- SOIDQVUTNSQPIE-SECBINFHSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]benzenesulfonyl fluoride Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=CC(=CC=2)S(F)(=O)=O)=N1 SOIDQVUTNSQPIE-SECBINFHSA-N 0.000 claims 1
- OPOIKZSKCNYCGG-LLVKDONJSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-methoxyethyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCOC)=CC=C1NC1=NC=C(Br)C(N[C@H](C)CO)=N1 OPOIKZSKCNYCGG-LLVKDONJSA-N 0.000 claims 1
- AXGKHKXXCZWGDR-CQSZACIVSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCOCC2)=N1 AXGKHKXXCZWGDR-CQSZACIVSA-N 0.000 claims 1
- GRLTVHLTFXVCDS-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-phenoxyethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCOC=2C=CC=CC=2)=N1 GRLTVHLTFXVCDS-OAHLLOKOSA-N 0.000 claims 1
- KYKYMCDWQJIZJJ-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-phenylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCC=2C=CC=CC=2)=N1 KYKYMCDWQJIZJJ-OAHLLOKOSA-N 0.000 claims 1
- OUXRNUPTKPCVAM-OAHLLOKOSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-piperidin-1-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCCCC2)=N1 OUXRNUPTKPCVAM-OAHLLOKOSA-N 0.000 claims 1
- LXIXVTKNXULCQQ-CQSZACIVSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCCC2)=N1 LXIXVTKNXULCQQ-CQSZACIVSA-N 0.000 claims 1
- CZFUEQDFLHSZDI-CQSZACIVSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-imidazol-1-ylpropyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCCN2C=NC=C2)=N1 CZFUEQDFLHSZDI-CQSZACIVSA-N 0.000 claims 1
- PJUUERIEVHJDSL-CYBMUJFWSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-methylbutyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCC(C)C)=CC=C1NC1=NC=C(Br)C(N[C@H](C)CO)=N1 PJUUERIEVHJDSL-CYBMUJFWSA-N 0.000 claims 1
- SNKRUHDRJOWIGC-SECBINFHSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzenesulfonamide Chemical compound CSC1=NNC(NS(=O)(=O)C=2C=CC(NC=3N=C(N[C@H](C)CO)C(Br)=CN=3)=CC=2)=N1 SNKRUHDRJOWIGC-SECBINFHSA-N 0.000 claims 1
- BEBSFANBTSGFFQ-MRXNPFEDSA-N 4-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-phenylpropyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCCC=2C=CC=CC=2)=N1 BEBSFANBTSGFFQ-MRXNPFEDSA-N 0.000 claims 1
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- JBRACZXUTCMBGG-GOSISDBHSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxybutan-2-yl]amino]pyrimidin-2-yl]amino]-n-[2-(4-methoxyphenyl)ethyl]-2-methylbenzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)CC)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCCC=2C=CC(OC)=CC=2)=N1 JBRACZXUTCMBGG-GOSISDBHSA-N 0.000 claims 1
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- UZACHZKCPVCRPX-OAHLLOKOSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-2-methyl-n-(2-morpholin-4-ylethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCCN2CCOCC2)=N1 UZACHZKCPVCRPX-OAHLLOKOSA-N 0.000 claims 1
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- MGGGDGAPYCYHCK-GOSISDBHSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-2-methyl-n-(4-phenylbutyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCCCCC=2C=CC=CC=2)=N1 MGGGDGAPYCYHCK-GOSISDBHSA-N 0.000 claims 1
- ZWDNLJHYDZKZSO-CQSZACIVSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-2-methyl-n-(pyridin-3-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCC=2C=NC=CC=2)=N1 ZWDNLJHYDZKZSO-CQSZACIVSA-N 0.000 claims 1
- MIQUAKWQUBUMRP-CQSZACIVSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-2-methyl-n-(pyridin-4-ylmethyl)benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCC=2C=CN=CC=2)=N1 MIQUAKWQUBUMRP-CQSZACIVSA-N 0.000 claims 1
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- SZXMCRLJQZBFGY-LDCVWXEPSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-2-methyl-n-[2-(1-methylpyrrolidin-2-yl)ethyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCCC2N(CCC2)C)=N1 SZXMCRLJQZBFGY-LDCVWXEPSA-N 0.000 claims 1
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- TYKYVNGEZLPOIP-CQSZACIVSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-2-methyl-n-[[3-(trifluoromethyl)phenyl]methyl]benzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCC=2C=C(C=CC=2)C(F)(F)F)=N1 TYKYVNGEZLPOIP-CQSZACIVSA-N 0.000 claims 1
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- GTSDKLCPGKWKNV-OAHLLOKOSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(3-imidazol-1-ylpropyl)-2-methylbenzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCCCN2C=NC=C2)=N1 GTSDKLCPGKWKNV-OAHLLOKOSA-N 0.000 claims 1
- PUBMJHHLKSAMDQ-OAHLLOKOSA-N 5-[[5-bromo-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-2-yl]amino]-n-(cyclohexylmethyl)-2-methylbenzenesulfonamide Chemical compound C1=C(Br)C(N[C@@H](CO)C)=NC(NC=2C=C(C(C)=CC=2)S(=O)(=O)NCC2CCCCC2)=N1 PUBMJHHLKSAMDQ-OAHLLOKOSA-N 0.000 claims 1
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| RU2356901C2 (ru) * | 2003-07-30 | 2009-05-27 | Райджел Фармасьютикалз, Инк. | Соединения 2, 4-пиримидиндиамина, обладающие воздействием при аутоиммунных расстройствах |
| ES2421139T3 (es) | 2003-07-30 | 2013-08-29 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para su uso en el tratamiento o la prevención de enfermedades autoinmunitarias |
| EP1663242B1 (en) * | 2003-08-07 | 2011-04-27 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents |
| DE10349423A1 (de) * | 2003-10-16 | 2005-06-16 | Schering Ag | Sulfoximinsubstituierte Parimidine als CDK- und/oder VEGF-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
| JP2007514775A (ja) * | 2003-12-19 | 2007-06-07 | ライジェル ファーマシューティカルズ, インコーポレイテッド | 1−(2,4−ピリミジンジアミノ)−2−シクロペンタンカルボキサイミド合成中間体の立体異性体および立体異性体混合物 |
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| CA2566531A1 (en) | 2004-05-18 | 2005-12-15 | Rigel Pharmaceuticals, Inc. | Cycloalkyl substituted pyrimidinediamine compounds and their uses |
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-
2002
- 2002-05-23 EP EP02738100A patent/EP1392662B1/de not_active Expired - Lifetime
- 2002-05-23 BR BR0209774-5A patent/BR0209774A/pt not_active IP Right Cessation
- 2002-05-23 RU RU2003136080/04A patent/RU2330024C2/ru active
- 2002-05-23 ES ES02738100T patent/ES2320204T3/es not_active Expired - Lifetime
- 2002-05-23 RS YUP-947/03A patent/RS94703A/sr unknown
- 2002-05-23 ME MEP-134/08A patent/MEP13408A/xx unknown
- 2002-05-23 NZ NZ529654A patent/NZ529654A/en unknown
- 2002-05-23 KR KR1020037015597A patent/KR100874791B1/ko not_active Expired - Fee Related
- 2002-05-23 CN CNB02814886XA patent/CN100480242C/zh not_active Expired - Fee Related
- 2002-05-23 AU AU2002312933A patent/AU2002312933B2/en not_active Ceased
- 2002-05-23 IL IL15912002A patent/IL159120A0/xx unknown
- 2002-05-23 AT AT02738100T patent/ATE420077T1/de not_active IP Right Cessation
- 2002-05-23 CA CA002449118A patent/CA2449118A1/en not_active Abandoned
- 2002-05-23 JP JP2003500067A patent/JP4291135B2/ja not_active Expired - Fee Related
- 2002-05-23 MX MXPA03010810A patent/MXPA03010810A/es active IP Right Grant
- 2002-05-23 HR HR20031081A patent/HRP20031081A2/hr not_active Application Discontinuation
- 2002-05-23 DE DE50213202T patent/DE50213202D1/de not_active Expired - Lifetime
- 2002-05-23 PL PL02367130A patent/PL367130A1/xx not_active Application Discontinuation
- 2002-05-23 WO PCT/EP2002/005669 patent/WO2002096888A1/de not_active Ceased
- 2002-05-29 US US10/156,759 patent/US7235561B2/en not_active Expired - Fee Related
- 2002-05-29 AR ARP020102001A patent/AR036035A1/es unknown
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2003
- 2003-11-28 NO NO20035298A patent/NO327129B1/no not_active IP Right Cessation
- 2003-12-26 CO CO03112613A patent/CO5540316A2/es not_active Application Discontinuation
-
2004
- 2004-05-11 US US10/842,419 patent/US7291624B2/en not_active Expired - Fee Related
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