JP2013517273A5 - - Google Patents
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- Publication number
- JP2013517273A5 JP2013517273A5 JP2012549000A JP2012549000A JP2013517273A5 JP 2013517273 A5 JP2013517273 A5 JP 2013517273A5 JP 2012549000 A JP2012549000 A JP 2012549000A JP 2012549000 A JP2012549000 A JP 2012549000A JP 2013517273 A5 JP2013517273 A5 JP 2013517273A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- pyrimidinyl
- benzenesulfonamide
- ylamino
- 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.)
- Pending
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- -1 nitro, amino Chemical group 0.000 claims 118
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 112
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 99
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 55
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 29
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000002971 oxazolyl group Chemical group 0.000 claims 6
- 125000000335 thiazolyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 2
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 2
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 claims 1
- SSHPGSKYPKVCEV-UHFFFAOYSA-N 1-[6-(3,4-difluoroanilino)pyrimidin-4-yl]-n,3,3-trimethyl-2h-indole-6-sulfonamide Chemical compound C=1C(S(=O)(=O)NC)=CC=C(C(C2)(C)C)C=1N2C(N=CN=1)=CC=1NC1=CC=C(F)C(F)=C1 SSHPGSKYPKVCEV-UHFFFAOYSA-N 0.000 claims 1
- YQGWKJBDGJCCHE-UHFFFAOYSA-N 1-[6-(3-bromo-5-methylanilino)pyrimidin-4-yl]-n-methyl-2,3-dihydroindole-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2CCN1C(N=CN=1)=CC=1NC1=CC(C)=CC(Br)=C1 YQGWKJBDGJCCHE-UHFFFAOYSA-N 0.000 claims 1
- XPRQOSSWVBQBSL-UHFFFAOYSA-N 1-[6-(3-fluoroanilino)pyrimidin-4-yl]-n-methyl-2,3-dihydroindole-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2CCN1C(N=CN=1)=CC=1NC1=CC=CC(F)=C1 XPRQOSSWVBQBSL-UHFFFAOYSA-N 0.000 claims 1
- YNGDGRSBALIRBW-UHFFFAOYSA-N 1-[6-(4-chloroanilino)pyrimidin-4-yl]-n,3,3-trimethyl-2h-indole-6-sulfonamide Chemical compound C=1C(S(=O)(=O)NC)=CC=C(C(C2)(C)C)C=1N2C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 YNGDGRSBALIRBW-UHFFFAOYSA-N 0.000 claims 1
- CKKAAEKWMHBVKR-UHFFFAOYSA-N 1-[6-(4-chloroanilino)pyrimidin-4-yl]-n-methyl-2,3-dihydroindole-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2CCN1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 CKKAAEKWMHBVKR-UHFFFAOYSA-N 0.000 claims 1
- JGCCSPWPKPGKRD-UHFFFAOYSA-N 1-[6-(4-chloroanilino)pyrimidin-4-yl]-n-methylindole-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2C=CN1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 JGCCSPWPKPGKRD-UHFFFAOYSA-N 0.000 claims 1
- XROVUMWBSURICL-UHFFFAOYSA-N 1-[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]-n,3,3-trimethyl-2h-indole-6-sulfonamide Chemical compound C=1C(S(=O)(=O)NC)=CC=C(C(C2)(C)C)C=1N2C(N=CN=1)=CC=1NC1=CC=C(Cl)C=N1 XROVUMWBSURICL-UHFFFAOYSA-N 0.000 claims 1
- KIJZHZJQRZOSDM-UHFFFAOYSA-N 1-[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]-n-methyl-2,3-dihydroindole-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2CCN1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=N1 KIJZHZJQRZOSDM-UHFFFAOYSA-N 0.000 claims 1
- BZUBEJPPHYVNQV-UHFFFAOYSA-N 2-[2-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3SC=C(CC(O)=O)N=3)C=2)=C1 BZUBEJPPHYVNQV-UHFFFAOYSA-N 0.000 claims 1
- FAZIYZQYPVIRKT-UHFFFAOYSA-N 2-[3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenoxy]acetic acid Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(OCC(O)=O)C=CC=3)C=2)=C1 FAZIYZQYPVIRKT-UHFFFAOYSA-N 0.000 claims 1
- GIZYDDHCEGEQNU-UHFFFAOYSA-N 2-[[4-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]benzoyl]amino]acetic acid Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(=O)NCC(O)=O)C=2)=C1 GIZYDDHCEGEQNU-UHFFFAOYSA-N 0.000 claims 1
- RLXGWEBBKRPWQR-UHFFFAOYSA-N 2-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]-1,3-thiazole-5-carboxylic acid Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3SC(=CN=3)C(O)=O)C=2)=C1 RLXGWEBBKRPWQR-UHFFFAOYSA-N 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- DOJMJCZRSVBOQU-UHFFFAOYSA-N 3-[2-chloro-5-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]benzamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C(Cl)=CC=3)C=3C=C(C=CC=3)C(N)=O)C=2)=C1 DOJMJCZRSVBOQU-UHFFFAOYSA-N 0.000 claims 1
- KUVOIVCORYNEAG-UHFFFAOYSA-N 3-[3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]benzamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=C(C=CC=3)C(N)=O)C=2)=C1 KUVOIVCORYNEAG-UHFFFAOYSA-N 0.000 claims 1
- YPWOVRWWACVZCL-UHFFFAOYSA-N 3-[6-(4-chloroanilino)pyrimidin-4-yl]-n-methyl-2-oxo-1h-benzimidazole-5-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2NC(=O)N1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 YPWOVRWWACVZCL-UHFFFAOYSA-N 0.000 claims 1
- BAIHSGCZMMSWBP-UHFFFAOYSA-N 3-[6-(4-chloroanilino)pyrimidin-4-yl]-n-methylbenzimidazole-5-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2N=CN1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 BAIHSGCZMMSWBP-UHFFFAOYSA-N 0.000 claims 1
- ZMVRNGODFXFTPO-UHFFFAOYSA-N 3-[[6-(1,3-benzodioxol-5-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4OCOC4=CC=3)C=2)=C1 ZMVRNGODFXFTPO-UHFFFAOYSA-N 0.000 claims 1
- UENCROCGCIOQEN-UHFFFAOYSA-N 3-[[6-(1,3-benzodioxol-5-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4OCOC4=CC=3)C=2)=C1 UENCROCGCIOQEN-UHFFFAOYSA-N 0.000 claims 1
- QPRDOQONEDFTAH-UHFFFAOYSA-N 3-[[6-(1,3-benzothiazol-5-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4N=CSC4=CC=3)C=2)=C1 QPRDOQONEDFTAH-UHFFFAOYSA-N 0.000 claims 1
- XZASEMGHCZZRLW-UHFFFAOYSA-N 3-[[6-(1,3-benzothiazol-6-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4SC=NC4=CC=3)C=2)=C1 XZASEMGHCZZRLW-UHFFFAOYSA-N 0.000 claims 1
- GMJKODDWBARXFJ-UHFFFAOYSA-N 3-[[6-(1,3-benzothiazol-6-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2N=CN=C(NC=3C=C4SC=NC4=CC=3)C=2)=C1 GMJKODDWBARXFJ-UHFFFAOYSA-N 0.000 claims 1
- QUJCAKSWZBOINU-UHFFFAOYSA-N 3-[[6-(1,3-benzothiazol-6-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4SC=NC4=CC=3)C=2)=C1 QUJCAKSWZBOINU-UHFFFAOYSA-N 0.000 claims 1
- WSOHSISENFLGIL-UHFFFAOYSA-N 3-[[6-(1h-indazol-5-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4C=NNC4=CC=3)C=2)=C1 WSOHSISENFLGIL-UHFFFAOYSA-N 0.000 claims 1
- CHSVYYQXPHZFRN-UHFFFAOYSA-N 3-[[6-(1h-indazol-5-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4C=NNC4=CC=3)C=2)=C1 CHSVYYQXPHZFRN-UHFFFAOYSA-N 0.000 claims 1
- RVIIUXSULDVRFS-UHFFFAOYSA-N 3-[[6-(1h-indazol-6-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4NN=CC4=CC=3)C=2)=C1 RVIIUXSULDVRFS-UHFFFAOYSA-N 0.000 claims 1
- RNMGNWUPJYUJEO-UHFFFAOYSA-N 3-[[6-(1h-indazol-6-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4NN=CC4=CC=3)C=2)=C1 RNMGNWUPJYUJEO-UHFFFAOYSA-N 0.000 claims 1
- QWNMUJUCOLVDSQ-UHFFFAOYSA-N 3-[[6-(1h-indol-5-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4C=CNC4=CC=3)C=2)=C1 QWNMUJUCOLVDSQ-UHFFFAOYSA-N 0.000 claims 1
- TVCUNJSHGDZSPI-UHFFFAOYSA-N 3-[[6-(1h-indol-5-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2N=CN=C(NC=3C=C4C=CNC4=CC=3)C=2)=C1 TVCUNJSHGDZSPI-UHFFFAOYSA-N 0.000 claims 1
- YMORECBYMVEEEN-UHFFFAOYSA-N 3-[[6-(1h-indol-5-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4C=CNC4=CC=3)C=2)=C1 YMORECBYMVEEEN-UHFFFAOYSA-N 0.000 claims 1
- WIVHBCXDQVXXBV-UHFFFAOYSA-N 3-[[6-(1h-indol-6-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4NC=CC4=CC=3)C=2)=C1 WIVHBCXDQVXXBV-UHFFFAOYSA-N 0.000 claims 1
- GWTDWARNDCMVSH-UHFFFAOYSA-N 3-[[6-(1h-indol-6-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4NC=CC4=CC=3)C=2)=C1 GWTDWARNDCMVSH-UHFFFAOYSA-N 0.000 claims 1
- QJULLOZLHYOJEP-UHFFFAOYSA-N 3-[[6-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4OCCOC4=CC=3)C=2)=C1 QJULLOZLHYOJEP-UHFFFAOYSA-N 0.000 claims 1
- TZPKEBUCUNSHPA-UHFFFAOYSA-N 3-[[6-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4OCCOC4=CC=3)C=2)=C1 TZPKEBUCUNSHPA-UHFFFAOYSA-N 0.000 claims 1
- FDMQLXAOUVNFNW-UHFFFAOYSA-N 3-[[6-(2,3-dihydro-1h-inden-5-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4CCCC4=CC=3)C=2)=C1 FDMQLXAOUVNFNW-UHFFFAOYSA-N 0.000 claims 1
- LPRSMIDGUMRXBW-UHFFFAOYSA-N 3-[[6-(2,3-dihydro-1h-inden-5-ylamino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2N=CN=C(NC=3C=C4CCCC4=CC=3)C=2)=C1 LPRSMIDGUMRXBW-UHFFFAOYSA-N 0.000 claims 1
- FRFXVBBUQSFMFC-UHFFFAOYSA-N 3-[[6-(2,3-dihydro-1h-inden-5-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4CCCC4=CC=3)C=2)=C1 FRFXVBBUQSFMFC-UHFFFAOYSA-N 0.000 claims 1
- NLMRBPNYBFJTTQ-UHFFFAOYSA-N 3-[[6-(2-fluoroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C(=CC=CC=3)F)C=2)=C1 NLMRBPNYBFJTTQ-UHFFFAOYSA-N 0.000 claims 1
- ATBXUKIYORQWPZ-UHFFFAOYSA-N 3-[[6-(3,4-dichloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Cl)C(Cl)=CC=3)C=2)=C1 ATBXUKIYORQWPZ-UHFFFAOYSA-N 0.000 claims 1
- DVUVMLOLRPYKQP-UHFFFAOYSA-N 3-[[6-(3,4-difluoroanilino)pyrimidin-4-yl]amino]-4-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C(NC=2N=CN=C(NC=3C=C(F)C(F)=CC=3)C=2)=C1 DVUVMLOLRPYKQP-UHFFFAOYSA-N 0.000 claims 1
- KMJFCLYFIOLZBD-UHFFFAOYSA-N 3-[[6-(3,4-difluoroanilino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C(F)C(F)=CC=3)C=2)=C1 KMJFCLYFIOLZBD-UHFFFAOYSA-N 0.000 claims 1
- SSIUXOVHEZSVEK-UHFFFAOYSA-N 3-[[6-(3,4-difluoroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(F)C(F)=CC=3)C=2)=C1 SSIUXOVHEZSVEK-UHFFFAOYSA-N 0.000 claims 1
- VTPLOIBJVWEBNX-UHFFFAOYSA-N 3-[[6-(3,4-dimethoxyanilino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C(OC)C(OC)=CC=3)C=2)=C1 VTPLOIBJVWEBNX-UHFFFAOYSA-N 0.000 claims 1
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- VZVZYGYRJQGAEZ-UHFFFAOYSA-N n-[4-[3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]phenyl]acetamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=CC(NC(C)=O)=CC=3)C=2)=C1 VZVZYGYRJQGAEZ-UHFFFAOYSA-N 0.000 claims 1
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- MINYLRBXEUZCKV-UHFFFAOYSA-N n-methyl-1-[6-[4-(trifluoromethyl)anilino]pyrimidin-4-yl]-2,3-dihydroindole-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2CCN1C(N=CN=1)=CC=1NC1=CC=C(C(F)(F)F)C=C1 MINYLRBXEUZCKV-UHFFFAOYSA-N 0.000 claims 1
- KCZKNGKHBWYSRW-UHFFFAOYSA-N n-methyl-3-[3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=C(C=CC=3)S(=O)(=O)NC)C=2)=C1 KCZKNGKHBWYSRW-UHFFFAOYSA-N 0.000 claims 1
- DNKSPZLPXGRTJT-UHFFFAOYSA-N n-methyl-3-[[6-(3,4,5-trifluoroanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(F)C(F)=C(F)C=3)C=2)=C1 DNKSPZLPXGRTJT-UHFFFAOYSA-N 0.000 claims 1
- KWUZMYGCFCIVLW-UHFFFAOYSA-N n-methyl-3-[[6-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(OC)C(OC)=C(OC)C=3)C=2)=C1 KWUZMYGCFCIVLW-UHFFFAOYSA-N 0.000 claims 1
- HUJZBYWWVKNVIJ-UHFFFAOYSA-N n-methyl-3-[[6-(3-phenylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=CC=CC=3)C=2)=C1 HUJZBYWWVKNVIJ-UHFFFAOYSA-N 0.000 claims 1
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- ABWOFHVAYDWSDH-UHFFFAOYSA-N n-methyl-3-[[6-[(2-methyl-1,3-benzothiazol-5-yl)amino]pyrimidin-4-yl]amino]-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4N=C(C)SC4=CC=3)C=2)=C1 ABWOFHVAYDWSDH-UHFFFAOYSA-N 0.000 claims 1
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- ITEYJDNTQKFNNT-UHFFFAOYSA-N n-methyl-3-[[6-[(2-methyl-4-oxochromen-7-yl)amino]pyrimidin-4-yl]amino]-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4C(C(C=C(C)O4)=O)=CC=3)C=2)=C1 ITEYJDNTQKFNNT-UHFFFAOYSA-N 0.000 claims 1
- DEAABRAKODYJBU-UHFFFAOYSA-N n-methyl-3-[[6-[(2-methyl-4-oxochromen-7-yl)amino]pyrimidin-4-yl]amino]-4-methylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2N=CN=C(NC=3C=C4C(C(C=C(C)O4)=O)=CC=3)C=2)=C1 DEAABRAKODYJBU-UHFFFAOYSA-N 0.000 claims 1
- UZJDGFPYFMSDQZ-UHFFFAOYSA-N n-methyl-3-[[6-[(2-methyl-4-oxochromen-7-yl)amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4C(C(C=C(C)O4)=O)=CC=3)C=2)=C1 UZJDGFPYFMSDQZ-UHFFFAOYSA-N 0.000 claims 1
- VPLAAKRJTCTETI-UHFFFAOYSA-N n-methyl-3-[[6-[(4-methyl-2-oxo-1h-quinolin-7-yl)amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4NC(=O)C=C(C)C4=CC=3)C=2)=C1 VPLAAKRJTCTETI-UHFFFAOYSA-N 0.000 claims 1
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- VLAMCKIPYKVGCA-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-[(5-oxo-7,8-dihydro-6h-naphthalen-2-yl)amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4CCCC(=O)C4=CC=3)C=2)=C1 VLAMCKIPYKVGCA-UHFFFAOYSA-N 0.000 claims 1
- KWNNKXYVCNWBEO-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-[3-(2-methyl-1,3-thiazol-4-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3N=C(C)SC=3)C=2)=C1 KWNNKXYVCNWBEO-UHFFFAOYSA-N 0.000 claims 1
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- DBWJXGZGUUWGGS-UHFFFAOYSA-N n-methyl-4-methylsulfonyl-3-[[6-[(5-oxo-7,8-dihydro-6h-naphthalen-2-yl)amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2N=CN=C(NC=3C=C4CCCC(=O)C4=CC=3)C=2)=C1 DBWJXGZGUUWGGS-UHFFFAOYSA-N 0.000 claims 1
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| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| EP3935944A1 (en) | 2013-03-15 | 2022-01-12 | University Of Southern California, USC Stevens | Compounds for the treatment of musculoskeletal diseases |
| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| CN104844526B (zh) * | 2015-04-16 | 2018-08-31 | 温州医科大学 | 一种4,6-嘧啶二胺类化合物及其制备方法和应用 |
| CN106008366A (zh) * | 2016-05-25 | 2016-10-12 | 山东大学 | 一种利匹韦林的制备方法 |
| JP6165373B1 (ja) * | 2017-02-24 | 2017-07-19 | タマ化学工業株式会社 | ピリジン−３−スルホニルクロリドの製造方法 |
| JP7202315B2 (ja) * | 2017-05-26 | 2023-01-11 | キャンサー・リサーチ・テクノロジー・リミテッド | ベンズイミダゾロン由来のｂｃｌ６阻害剤 |
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| CN108864052A (zh) * | 2018-06-07 | 2018-11-23 | 福建医科大学 | 一种针对gc33-3-1抗体具有特异性识别的荧光探针的合成以及应用 |
| GB201914860D0 (en) | 2019-10-14 | 2019-11-27 | Cancer Research Tech Ltd | Inhibitor compounds |
| EP4206196A1 (en) * | 2021-12-29 | 2023-07-05 | Almirall S.A. | Pyrimidine substituted derivatives as tyk2 inhibitors |
| US20250177391A1 (en) * | 2022-02-23 | 2025-06-05 | President And Fellows Of Harvard College | Inhibitors of ddr1 and ddr2 for the treatment of arthritis |
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| CN121548418A (zh) * | 2023-05-23 | 2026-02-17 | 康特克斯生物科技美国公司 | 二环杂芳基化合物 |
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| UA109411C2 (uk) * | 2005-11-01 | 2015-08-25 | N-трет-бутил-3-(2-хлор-5-метилпіримідин-4-іламіно)бензолсульфонамід та його застосування в способі одержання сполуки | |
| JP5191391B2 (ja) * | 2005-11-01 | 2013-05-08 | ターゲジェン インコーポレーティッド | キナーゼのビ−アリールメタ−ピリミジン阻害剤 |
| RU2008152195A (ru) * | 2006-06-15 | 2010-07-20 | БЕРИНГЕР ИНГЕЛЬХАЙМ ИНТЕРНАЦИОНАЛЬ ГмбХ (DE) | 2-анилино-4-(гетероциклил)аминопиримидины, как ингибиторы протеинкиназы с-альфа |
| CN101589036A (zh) * | 2006-12-19 | 2009-11-25 | 沃泰克斯药物股份有限公司 | 可用作蛋白激酶抑制剂的氨基嘧啶 |
| WO2008118822A1 (en) * | 2007-03-23 | 2008-10-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| EP2014657A1 (de) * | 2007-06-21 | 2009-01-14 | Bayer Schering Pharma Aktiengesellschaft | Diaminopyrimidine als Modulatoren des EP2-Rezeptors |
| TWI552752B (zh) * | 2007-10-19 | 2016-10-11 | 賽基艾維洛米斯研究股份有限公司 | 雜芳基化合物及其用途 |
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2011
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- 2011-01-11 MX MX2012008141A patent/MX2012008141A/es unknown
- 2011-01-11 CA CA2786999A patent/CA2786999A1/en not_active Abandoned
- 2011-01-11 EP EP11733258.5A patent/EP2523559A4/en not_active Withdrawn
- 2011-01-11 WO PCT/US2011/020798 patent/WO2011088027A1/en not_active Ceased
- 2011-01-11 US US13/520,861 patent/US20120329784A1/en not_active Abandoned
- 2011-01-11 EA EA201290642A patent/EA201290642A1/ru unknown
- 2011-01-11 CN CN2011800138247A patent/CN102791131A/zh active Pending
- 2011-01-11 JP JP2012549000A patent/JP2013517273A/ja active Pending
- 2011-01-11 BR BR112012017277A patent/BR112012017277A2/pt not_active IP Right Cessation
- 2011-01-11 AU AU2011205485A patent/AU2011205485B2/en not_active Expired - Fee Related
- 2011-01-11 SG SG2012049409A patent/SG182351A1/en unknown
-
2012
- 2012-07-05 IL IL220812A patent/IL220812A0/en unknown
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