SG182351A1 - Compounds and methods - Google Patents
Compounds and methods Download PDFInfo
- Publication number
- SG182351A1 SG182351A1 SG2012049409A SG2012049409A SG182351A1 SG 182351 A1 SG182351 A1 SG 182351A1 SG 2012049409 A SG2012049409 A SG 2012049409A SG 2012049409 A SG2012049409 A SG 2012049409A SG 182351 A1 SG182351 A1 SG 182351A1
- Authority
- SG
- Singapore
- Prior art keywords
- amino
- methyl
- pyrimidinyl
- benzenesulfonamide
- ylamino
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 180
- 238000000034 method Methods 0.000 title claims abstract description 114
- -1 nitro, amino Chemical group 0.000 claims description 562
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 469
- 125000000217 alkyl group Chemical group 0.000 claims description 408
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 175
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 124
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 115
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 101
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 150000002367 halogens Chemical class 0.000 claims description 64
- 125000001188 haloalkyl group Chemical group 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 41
- 125000004076 pyridyl group Chemical group 0.000 claims description 40
- 125000004043 oxo group Chemical group O=* 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000002757 morpholinyl group Chemical group 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000003386 piperidinyl group Chemical group 0.000 claims description 31
- 125000004193 piperazinyl group Chemical group 0.000 claims description 30
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 28
- 206010019280 Heart failures Diseases 0.000 claims description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 125000002971 oxazolyl group Chemical group 0.000 claims description 18
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 239000005711 Benzoic acid Substances 0.000 claims description 11
- 235000010233 benzoic acid Nutrition 0.000 claims description 11
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 11
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- NHOYVDPQQXHYHJ-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-(1,1,1-trifluoropropan-2-yloxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C(F)(F)F)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 NHOYVDPQQXHYHJ-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- TUSOWBMKLPCSEP-UHFFFAOYSA-N 3-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-n-methyl-4-(1,1,1-trifluoropropan-2-yloxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C(F)(F)F)C(NC=2N=CN=C(NC=3N=CC(Cl)=CC=3)C=2)=C1 TUSOWBMKLPCSEP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 7
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- IGMFZMWEIHCRKO-UHFFFAOYSA-N 3-[[6-(3-bromoanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Br)C=CC=3)C=2)=C1 IGMFZMWEIHCRKO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052792 caesium Inorganic materials 0.000 claims description 6
- 125000005984 hexahydro-1H-1,4-diazepinyl group Chemical group 0.000 claims description 6
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 229910052684 Cerium Inorganic materials 0.000 claims description 5
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 5
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- MMRPIBRGLPCJOA-UHFFFAOYSA-N 3-[[6-(3-bromo-4-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Br)C(Cl)=CC=3)C=2)=C1 MMRPIBRGLPCJOA-UHFFFAOYSA-N 0.000 claims description 3
- FPJOZQHBXWAZTD-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 FPJOZQHBXWAZTD-UHFFFAOYSA-N 0.000 claims description 3
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- DXRUQQNNVBKUPK-UHFFFAOYSA-N 3-[[6-(1h-indazol-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=NNC4=CC=3)C=2)=C1 DXRUQQNNVBKUPK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- XJUMEQTZRKNKKL-UHFFFAOYSA-N 3-[[6-(1h-indol-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=C4NC=CC4=CC=3)C=2)=C1 XJUMEQTZRKNKKL-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
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- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical class CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
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- 229960002051 trandolapril Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
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- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
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- Medicinal Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| EP2961746B1 (en) | 2013-02-28 | 2018-01-03 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent rock1 and rock2 inhibitors |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| ES2834430T3 (es) * | 2013-03-15 | 2021-06-17 | Univ Southern California | Procedimientos, compuestos y composiciones para el tratamiento de enfermedades relacionadas con la angiotensina |
| 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 |
| EP3630291B9 (en) * | 2017-05-26 | 2024-05-29 | Cancer Research Technology Limited | Benzimidazolone derived inhibitors of bcl6 |
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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 |
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| PL4496795T3 (pl) | 2022-03-23 | 2026-07-20 | Ideaya Biosciences, Inc. | Związki indazolowe podstawione piperazyną jako inhibitory parg |
| US11891362B1 (en) * | 2023-04-14 | 2024-02-06 | King Faisal University | N2,N4-disubstituted pyrimidine-2,4-diamine compounds as antibacterial agents |
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| WO2004087707A1 (en) * | 2003-03-31 | 2004-10-14 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
| US8084457B2 (en) * | 2003-09-15 | 2011-12-27 | Lead Discovery Center Gmbh | Pharmaceutically active 4,6-disubstituted aminopyrimidine derivatives as modulators of protein kinases |
| BRPI0506839A (pt) * | 2004-01-16 | 2007-06-12 | Novartis Ag | composições e métodos para induzir a cardiomiogênese |
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| US20070203161A1 (en) * | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| 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 | |
| WO2007053452A1 (en) * | 2005-11-01 | 2007-05-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| AU2007257650A1 (en) * | 2006-06-15 | 2007-12-21 | Boehringer Ingelheim International Gmbh | 2-anilino-4-(heterocyclic)amino-pyrimidines as inhibitors of protein kinase C-alpha |
| 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 |
| US7947698B2 (en) * | 2007-03-23 | 2011-05-24 | 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 |
| JP5600063B2 (ja) * | 2007-10-19 | 2014-10-01 | セルジーン アビロミクス リサーチ， インコーポレイテッド | ヘテロアリール化合物およびその使用 |
-
2011
- 2011-01-11 CN CN2011800138247A patent/CN102791131A/zh active Pending
- 2011-01-11 BR BR112012017277A patent/BR112012017277A2/pt not_active IP Right Cessation
- 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 KR KR1020127021083A patent/KR20120114355A/ko not_active Withdrawn
- 2011-01-11 AU AU2011205485A patent/AU2011205485B2/en not_active Expired - Fee Related
- 2011-01-11 MX MX2012008141A patent/MX2012008141A/es unknown
- 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 SG SG2012049409A patent/SG182351A1/en unknown
- 2011-01-11 JP JP2012549000A patent/JP2013517273A/ja active Pending
- 2011-01-11 EA EA201290642A patent/EA201290642A1/ru unknown
-
2012
- 2012-07-05 IL IL220812A patent/IL220812A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20120329784A1 (en) | 2012-12-27 |
| WO2011088027A8 (en) | 2012-08-30 |
| AU2011205485B2 (en) | 2014-09-25 |
| KR20120114355A (ko) | 2012-10-16 |
| JP2013517273A (ja) | 2013-05-16 |
| MX2012008141A (es) | 2012-08-03 |
| EP2523559A1 (en) | 2012-11-21 |
| CN102791131A (zh) | 2012-11-21 |
| EA201290642A1 (ru) | 2013-05-30 |
| WO2011088027A1 (en) | 2011-07-21 |
| IL220812A0 (en) | 2012-08-30 |
| BR112012017277A2 (pt) | 2017-10-03 |
| AU2011205485A1 (en) | 2012-08-02 |
| CA2786999A1 (en) | 2011-07-21 |
| EP2523559A4 (en) | 2013-11-06 |
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