KR20120114355A - 화합물 및 방법 - Google Patents
화합물 및 방법 Download PDFInfo
- Publication number
- KR20120114355A KR20120114355A KR1020127021083A KR20127021083A KR20120114355A KR 20120114355 A KR20120114355 A KR 20120114355A KR 1020127021083 A KR1020127021083 A KR 1020127021083A KR 20127021083 A KR20127021083 A KR 20127021083A KR 20120114355 A KR20120114355 A KR 20120114355A
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- methyl
- pyrimidinyl
- benzenesulfonamide
- alkyl
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 189
- 238000000034 method Methods 0.000 title claims abstract description 116
- -1 nitro, amino Chemical group 0.000 claims description 568
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 294
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 226
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 223
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 74
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 64
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 61
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 43
- 125000004043 oxo group Chemical group O=* 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 206010019280 Heart failures Diseases 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000002757 morpholinyl group Chemical group 0.000 claims description 25
- 125000004193 piperazinyl group Chemical group 0.000 claims description 24
- 125000003386 piperidinyl group Chemical group 0.000 claims description 24
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 23
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 18
- 150000002431 hydrogen Chemical class 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 13
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 10
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 9
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 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 7
- DMASLYFJBBMGRU-UHFFFAOYSA-N 4-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]benzoic acid Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(O)=O)C=2)=C1 DMASLYFJBBMGRU-UHFFFAOYSA-N 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=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
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 7
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- 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 description 5
- IXKSSFAHOTXHEB-UHFFFAOYSA-N 3-[[6-[3-[6-(dimethylamino)pyridin-3-yl]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=NC(=CC=3)N(C)C)C=2)=C1 IXKSSFAHOTXHEB-UHFFFAOYSA-N 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 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 description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- MFGDYDHJSATONH-UHFFFAOYSA-N n,n-dimethyl-4-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]benzamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(=O)N(C)C)C=2)=C1 MFGDYDHJSATONH-UHFFFAOYSA-N 0.000 claims description 4
- PCXQHJSZGKQFAE-UHFFFAOYSA-N n-methyl-3-[[6-[3-(6-oxo-1h-pyridin-3-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C3=CNC(=O)C=C3)C=2)=C1 PCXQHJSZGKQFAE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 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 3
- 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 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 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 3
- 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
- HKFBRJUIUDXVRE-UHFFFAOYSA-N 3-[[6-(3-bromo-5-methylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Br)C=C(C)C=3)C=2)=C1 HKFBRJUIUDXVRE-UHFFFAOYSA-N 0.000 claims description 3
- KHOWHDRBCPRISN-UHFFFAOYSA-N 3-[[6-(3-hydroxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(O)C=CC=3)C=2)=C1 KHOWHDRBCPRISN-UHFFFAOYSA-N 0.000 claims description 3
- XXEWYYSMCBLKPD-UHFFFAOYSA-N 3-[[6-[3-(6-methoxypyridin-3-yl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=NC(OC)=CC=3)C=2)=C1 XXEWYYSMCBLKPD-UHFFFAOYSA-N 0.000 claims description 3
- HJNKOSNGIFVOOP-UHFFFAOYSA-N 4-[[6-[5-(methylsulfamoyl)-2-methylsulfanylanilino]pyrimidin-4-yl]amino]benzoic acid Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=CC(=CC=3)C(O)=O)C=2)=C1 HJNKOSNGIFVOOP-UHFFFAOYSA-N 0.000 claims description 3
- ZQBRJADKMDNWJR-UHFFFAOYSA-N 4-amino-3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 ZQBRJADKMDNWJR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 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 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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
- 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 description 2
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 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
- 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 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
- 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
- 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 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- LXBDNFUXIHOYIX-UHFFFAOYSA-N 3-[[6-(3,4-dimethoxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(OC)C(OC)=CC=3)C=2)=C1 LXBDNFUXIHOYIX-UHFFFAOYSA-N 0.000 claims description 2
- XBKFTXOLFMUIBI-UHFFFAOYSA-N 3-[[6-(3,4-dimethylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C)C(C)=CC=3)C=2)=C1 XBKFTXOLFMUIBI-UHFFFAOYSA-N 0.000 claims description 2
- INWYUJWIJPDEIA-UHFFFAOYSA-N 3-[[6-(3,5-dichloro-4-hydroxyanilino)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(Cl)C(O)=C(Cl)C=3)C=2)=C1 INWYUJWIJPDEIA-UHFFFAOYSA-N 0.000 claims description 2
- ZACCVFPQIPVIRN-UHFFFAOYSA-N 3-[[6-(3,5-dichloro-4-hydroxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Cl)C(O)=C(Cl)C=3)C=2)=C1 ZACCVFPQIPVIRN-UHFFFAOYSA-N 0.000 claims description 2
- JQZGGFKCNGUKII-UHFFFAOYSA-N 3-[[6-(3,5-dichloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Cl)C=C(Cl)C=3)C=2)=C1 JQZGGFKCNGUKII-UHFFFAOYSA-N 0.000 claims description 2
- FMTYFLJVCBHAGC-UHFFFAOYSA-N 3-[[6-(3,5-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=C(OC)C=3)C=2)=C1 FMTYFLJVCBHAGC-UHFFFAOYSA-N 0.000 claims description 2
- ZHRFRMNOICTUKI-UHFFFAOYSA-N 3-[[6-(3,5-dimethoxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(OC)C=C(OC)C=3)C=2)=C1 ZHRFRMNOICTUKI-UHFFFAOYSA-N 0.000 claims description 2
- IPLIVRONTBHTAK-UHFFFAOYSA-N 3-[[6-(3,5-dimethylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C)C=C(C)C=3)C=2)=C1 IPLIVRONTBHTAK-UHFFFAOYSA-N 0.000 claims description 2
- HFZATVIHGAHNAJ-UHFFFAOYSA-N 3-[[6-(3-acetylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C(C)=O)C=2)=C1 HFZATVIHGAHNAJ-UHFFFAOYSA-N 0.000 claims description 2
- NSNLJUVRXKVJQD-UHFFFAOYSA-N 3-[[6-(3-bromo-5-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Br)C=C(Cl)C=3)C=2)=C1 NSNLJUVRXKVJQD-UHFFFAOYSA-N 0.000 claims description 2
- PGELRFQDUNLIMB-UHFFFAOYSA-N 3-[[6-(3-chloro-4-cyanoanilino)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(Cl)C(C#N)=CC=3)C=2)=C1 PGELRFQDUNLIMB-UHFFFAOYSA-N 0.000 claims description 2
- JXJLUFZUZLBRSO-UHFFFAOYSA-N 3-[[6-(3-chloro-4-hydroxyanilino)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(Cl)C(O)=CC=3)C=2)=C1 JXJLUFZUZLBRSO-UHFFFAOYSA-N 0.000 claims description 2
- GXISVLOJWNJMJR-UHFFFAOYSA-N 3-[[6-(3-chloro-4-hydroxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Cl)C(O)=CC=3)C=2)=C1 GXISVLOJWNJMJR-UHFFFAOYSA-N 0.000 claims description 2
- XWXRTVNNDOXVEK-UHFFFAOYSA-N 3-[[6-(3-chloro-4-methoxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Cl)C(OC)=CC=3)C=2)=C1 XWXRTVNNDOXVEK-UHFFFAOYSA-N 0.000 claims description 2
- PCISBQXGUUSKII-UHFFFAOYSA-N 3-[[6-(3-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(Cl)C=CC=3)C=2)=C1 PCISBQXGUUSKII-UHFFFAOYSA-N 0.000 claims description 2
- OGNLBVXNUPLZKC-UHFFFAOYSA-N 3-[[6-(3-ethoxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CCOC1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)S(=O)(=O)NC)C=2)=C1 OGNLBVXNUPLZKC-UHFFFAOYSA-N 0.000 claims description 2
- FQAJYLRCNVLNEH-UHFFFAOYSA-N 3-[[6-(3-ethynylanilino)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(C=CC=3)C#C)C=2)=C1 FQAJYLRCNVLNEH-UHFFFAOYSA-N 0.000 claims description 2
- RZHYGPUJQHNYSS-UHFFFAOYSA-N 3-[[6-(3-ethynylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C#C)C=2)=C1 RZHYGPUJQHNYSS-UHFFFAOYSA-N 0.000 claims description 2
- SBRKUBKCZPDING-UHFFFAOYSA-N 3-[[6-(3-fluoro-4-methoxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(F)C(OC)=CC=3)C=2)=C1 SBRKUBKCZPDING-UHFFFAOYSA-N 0.000 claims description 2
- QZBHVZJWPHTRLI-UHFFFAOYSA-N 3-[[6-(3-fluoro-4-methylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(F)C(C)=CC=3)C=2)=C1 QZBHVZJWPHTRLI-UHFFFAOYSA-N 0.000 claims description 2
- ONPQPTATZFRRIR-UHFFFAOYSA-N 3-[[6-(3-fluoroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(F)C=CC=3)C=2)=C1 ONPQPTATZFRRIR-UHFFFAOYSA-N 0.000 claims description 2
- UQRDFVIQXQYGGX-UHFFFAOYSA-N 3-[[6-(3-tert-butylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C(C)(C)C)C=2)=C1 UQRDFVIQXQYGGX-UHFFFAOYSA-N 0.000 claims description 2
- CXAAAAQJEIHXSS-UHFFFAOYSA-N 3-[[6-(4-acetylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(C)=O)C=2)=C1 CXAAAAQJEIHXSS-UHFFFAOYSA-N 0.000 claims description 2
- JEYOVDUEUBJFCI-UHFFFAOYSA-N 3-[[6-(4-bromoanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(Br)=CC=3)C=2)=C1 JEYOVDUEUBJFCI-UHFFFAOYSA-N 0.000 claims description 2
- QZIVDDVIEJXWED-UHFFFAOYSA-N 3-[[6-(4-chloro-3-fluoroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(F)C(Cl)=CC=3)C=2)=C1 QZIVDDVIEJXWED-UHFFFAOYSA-N 0.000 claims description 2
- LTFLDFTVMJMXNE-UHFFFAOYSA-N 3-[[6-(4-chloro-3-methoxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(OC)C(Cl)=CC=3)C=2)=C1 LTFLDFTVMJMXNE-UHFFFAOYSA-N 0.000 claims description 2
- DBJLMYSTIOHITF-UHFFFAOYSA-N 3-[[6-(4-chloro-3-methylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C)C(Cl)=CC=3)C=2)=C1 DBJLMYSTIOHITF-UHFFFAOYSA-N 0.000 claims description 2
- HSEWBJZULFBMFP-UHFFFAOYSA-N 3-[[6-(4-chloro-3-pyridin-3-ylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C(Cl)=CC=3)C=3C=NC=CC=3)C=2)=C1 HSEWBJZULFBMFP-UHFFFAOYSA-N 0.000 claims description 2
- BIAVCXZCQOKVLE-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-(2,5-dimethylpyrrolidin-1-yl)-n-methylbenzenesulfonamide Chemical compound C=1C(NC=2C=CC(Cl)=CC=2)=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1N1C(C)CCC1C BIAVCXZCQOKVLE-UHFFFAOYSA-N 0.000 claims description 2
- CSNMREFDBOENSS-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-(3,3-difluoropiperidin-1-yl)-n-methylbenzenesulfonamide Chemical compound C=1C(NC=2C=CC(Cl)=CC=2)=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCCC(F)(F)C1 CSNMREFDBOENSS-UHFFFAOYSA-N 0.000 claims description 2
- PKSHLLDOWQDSGU-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-(3,3-difluoropyrrolidin-1-yl)-n-methylbenzenesulfonamide Chemical compound C=1C(NC=2C=CC(Cl)=CC=2)=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1N1CCC(F)(F)C1 PKSHLLDOWQDSGU-UHFFFAOYSA-N 0.000 claims description 2
- VLIPFLVOGBHVLD-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-(diethylamino)-n-methylbenzenesulfonamide Chemical compound CCN(CC)C1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2C=CC(Cl)=CC=2)=NC=N1 VLIPFLVOGBHVLD-UHFFFAOYSA-N 0.000 claims description 2
- ZOUUXVXDAMYMBY-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 ZOUUXVXDAMYMBY-UHFFFAOYSA-N 0.000 claims description 2
- XBZQXNSFWLLRIG-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-[ethyl(methyl)amino]-n-methylbenzenesulfonamide Chemical compound CCN(C)C1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2C=CC(Cl)=CC=2)=NC=N1 XBZQXNSFWLLRIG-UHFFFAOYSA-N 0.000 claims description 2
- LUGYCKJYXLYTLU-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-cyclohexyloxy-n-methylbenzenesulfonamide Chemical compound C=1C(NC=2C=CC(Cl)=CC=2)=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1OC1CCCCC1 LUGYCKJYXLYTLU-UHFFFAOYSA-N 0.000 claims description 2
- JDKYXRBXMCZINC-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-cyclopentyloxy-n-methylbenzenesulfonamide Chemical compound C=1C(NC=2C=CC(Cl)=CC=2)=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1OC1CCCC1 JDKYXRBXMCZINC-UHFFFAOYSA-N 0.000 claims description 2
- GQLFXJQBKCWVBN-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-ethoxy-n-methylbenzenesulfonamide Chemical compound CCOC1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2C=CC(Cl)=CC=2)=NC=N1 GQLFXJQBKCWVBN-UHFFFAOYSA-N 0.000 claims description 2
- DHPCOHXYNFUHNV-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-ethylsulfanyl-n-methylbenzenesulfonamide Chemical compound CCSC1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2C=CC(Cl)=CC=2)=NC=N1 DHPCOHXYNFUHNV-UHFFFAOYSA-N 0.000 claims description 2
- UFMHTWBYFHWQRA-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-ethylsulfonyl-n-methylbenzenesulfonamide Chemical compound CCS(=O)(=O)C1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2C=CC(Cl)=CC=2)=NC=N1 UFMHTWBYFHWQRA-UHFFFAOYSA-N 0.000 claims description 2
- BEGGCRSAEDQFNP-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 BEGGCRSAEDQFNP-UHFFFAOYSA-N 0.000 claims description 2
- STECVPWMZQHSEA-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-hydroxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(O)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 STECVPWMZQHSEA-UHFFFAOYSA-N 0.000 claims description 2
- RFILSSYVEZFKMV-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-5-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CN(C)C1=CC(S(=O)(=O)NC)=CC(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 RFILSSYVEZFKMV-UHFFFAOYSA-N 0.000 claims description 2
- AHFLYDUGDUTYTN-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n,4-dimethylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(C)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 AHFLYDUGDUTYTN-UHFFFAOYSA-N 0.000 claims description 2
- KYZUCJJGVPFWBY-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 KYZUCJJGVPFWBY-UHFFFAOYSA-N 0.000 claims description 2
- UQLBIBTVOXJUQJ-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-(2-methylpropylsulfanyl)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SCC(C)C)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 UQLBIBTVOXJUQJ-UHFFFAOYSA-N 0.000 claims description 2
- IWKHWBZYGUILBG-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-(2-methylpropylsulfonyl)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(=O)(=O)CC(C)C)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 IWKHWBZYGUILBG-UHFFFAOYSA-N 0.000 claims description 2
- JUBMHNHUGZDLBO-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-(3,3,3-trifluoropropoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCCC(F)(F)F)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 JUBMHNHUGZDLBO-UHFFFAOYSA-N 0.000 claims description 2
- ZATBHXMBMGYNJT-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-(3-methylbutan-2-yloxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C(C)C)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 ZATBHXMBMGYNJT-UHFFFAOYSA-N 0.000 claims description 2
- QONXSOOGQMMQLC-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-pentan-3-yloxybenzenesulfonamide Chemical compound CCC(CC)OC1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2C=CC(Cl)=CC=2)=NC=N1 QONXSOOGQMMQLC-UHFFFAOYSA-N 0.000 claims description 2
- AAOSTHUYAHBMNL-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 AAOSTHUYAHBMNL-UHFFFAOYSA-N 0.000 claims description 2
- YLQUZGDOLIQJBC-UHFFFAOYSA-N 3-[[6-(4-cyanoanilino)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(=CC=3)C#N)C=2)=C1 YLQUZGDOLIQJBC-UHFFFAOYSA-N 0.000 claims description 2
- IDTMMSADLPJXBG-UHFFFAOYSA-N 3-[[6-(4-cyanoanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C#N)C=2)=C1 IDTMMSADLPJXBG-UHFFFAOYSA-N 0.000 claims description 2
- AWQIFTKCENSDLD-UHFFFAOYSA-N 3-[[6-(4-cyclopropylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C3CC3)C=2)=C1 AWQIFTKCENSDLD-UHFFFAOYSA-N 0.000 claims description 2
- JVXNANPQLFCVKY-UHFFFAOYSA-N 3-[[6-(4-fluoro-3-methylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C)C(F)=CC=3)C=2)=C1 JVXNANPQLFCVKY-UHFFFAOYSA-N 0.000 claims description 2
- QPKIMDBSBHCPJO-UHFFFAOYSA-N 3-[[6-(4-fluoroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(F)=CC=3)C=2)=C1 QPKIMDBSBHCPJO-UHFFFAOYSA-N 0.000 claims description 2
- KXNVQVWXRADLCV-UHFFFAOYSA-N 3-[[6-(4-tert-butylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(C)(C)C)C=2)=C1 KXNVQVWXRADLCV-UHFFFAOYSA-N 0.000 claims description 2
- ZCZKZCPSQHCBEE-UHFFFAOYSA-N 3-[[6-(ethylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound C1=NC(NCC)=CC(NC=2C=C(C=CC=2)S(=O)(=O)NC)=N1 ZCZKZCPSQHCBEE-UHFFFAOYSA-N 0.000 claims description 2
- MCVRDRAOECTBKR-UHFFFAOYSA-N 3-[[6-(isoquinolin-3-ylamino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3N=CC4=CC=CC=C4C=3)C=2)=C1 MCVRDRAOECTBKR-UHFFFAOYSA-N 0.000 claims description 2
- HPYCONDQKCIATF-UHFFFAOYSA-N 3-[[6-[(1,1-dioxo-2,3-dihydro-1,2-benzothiazol-6-yl)amino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4S(=O)(=O)NCC4=CC=3)C=2)=C1 HPYCONDQKCIATF-UHFFFAOYSA-N 0.000 claims description 2
- GFOVIJIHKDDMPY-UHFFFAOYSA-N 3-[[6-[(1-acetyl-2,3-dihydroindol-6-yl)amino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4N(C(C)=O)CCC4=CC=3)C=2)=C1 GFOVIJIHKDDMPY-UHFFFAOYSA-N 0.000 claims description 2
- OEDGERSSZUMLBI-UHFFFAOYSA-N 3-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-4-ethylsulfonyl-n-methylbenzenesulfonamide Chemical compound CCS(=O)(=O)C1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2N=CC(Cl)=CC=2)=NC=N1 OEDGERSSZUMLBI-UHFFFAOYSA-N 0.000 claims description 2
- OGYZBVDWCPENCZ-UHFFFAOYSA-N 3-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-4-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C(NC=2N=CN=C(NC=3N=CC(Cl)=CC=3)C=2)=C1 OGYZBVDWCPENCZ-UHFFFAOYSA-N 0.000 claims description 2
- QRBOUAQFSFWZNI-UHFFFAOYSA-N 3-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-n-methyl-4-propan-2-ylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(=O)(=O)C(C)C)C(NC=2N=CN=C(NC=3N=CC(Cl)=CC=3)C=2)=C1 QRBOUAQFSFWZNI-UHFFFAOYSA-N 0.000 claims description 2
- IRQFZJPZSCQTJK-UHFFFAOYSA-N 3-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3N=CC(Cl)=CC=3)C=2)=C1 IRQFZJPZSCQTJK-UHFFFAOYSA-N 0.000 claims description 2
- JRPQDJFYVIAXHC-UHFFFAOYSA-N 3-[[6-[3-(4-methoxypyridin-3-yl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C(=CC=NC=3)OC)C=2)=C1 JRPQDJFYVIAXHC-UHFFFAOYSA-N 0.000 claims description 2
- YPUVLDQAFSUSLU-UHFFFAOYSA-N 3-[[6-[3-(5-methoxypyridin-3-yl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=C(OC)C=NC=3)C=2)=C1 YPUVLDQAFSUSLU-UHFFFAOYSA-N 0.000 claims description 2
- GGQMFUUQKOUMNA-UHFFFAOYSA-N 3-[[6-[3-(dimethylamino)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)N(C)C)C=2)=C1 GGQMFUUQKOUMNA-UHFFFAOYSA-N 0.000 claims description 2
- YASTVMFFSPOXQJ-UHFFFAOYSA-N 3-[[6-[3-(dimethylsulfamoyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)S(=O)(=O)N(C)C)C=2)=C1 YASTVMFFSPOXQJ-UHFFFAOYSA-N 0.000 claims description 2
- DUOCFNHZWAAREM-UHFFFAOYSA-N 3-[[6-[3-(ethylsulfamoyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)S(=O)(=O)NC)C=2)=C1 DUOCFNHZWAAREM-UHFFFAOYSA-N 0.000 claims description 2
- MBUGNKDYZPVCEV-UHFFFAOYSA-N 3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]-n-phenylbenzamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C(=O)NC=3C=CC=CC=3)C=2)=C1 MBUGNKDYZPVCEV-UHFFFAOYSA-N 0.000 claims description 2
- XPROJVDJKLIYNG-UHFFFAOYSA-N 3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)S(N)(=O)=O)C=2)=C1 XPROJVDJKLIYNG-UHFFFAOYSA-N 0.000 claims description 2
- GQYVCSYVUHIELB-UHFFFAOYSA-N 3-[[6-[3-[3-(dimethylamino)phenyl]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=C(C=CC=3)N(C)C)C=2)=C1 GQYVCSYVUHIELB-UHFFFAOYSA-N 0.000 claims description 2
- DUHTUDRVXQKOAU-UHFFFAOYSA-N 3-[[6-[3-[4-(dimethylamino)phenyl]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=CC(=CC=3)N(C)C)C=2)=C1 DUHTUDRVXQKOAU-UHFFFAOYSA-N 0.000 claims description 2
- WZJRQRZNQZBBHD-UHFFFAOYSA-N 3-[[6-[3-[4-(methanesulfonamido)phenyl]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=CC(NS(C)(=O)=O)=CC=3)C=2)=C1 WZJRQRZNQZBBHD-UHFFFAOYSA-N 0.000 claims description 2
- RGGOCHDRDGKTFA-UHFFFAOYSA-N 3-[[6-[3-fluoro-4-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(F)C(=CC=3)C(F)(F)F)C=2)=C1 RGGOCHDRDGKTFA-UHFFFAOYSA-N 0.000 claims description 2
- HIBOHPSDXHKUTA-UHFFFAOYSA-N 3-[[6-[3-methoxy-5-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=C(OC)C=3)C(F)(F)F)C=2)=C1 HIBOHPSDXHKUTA-UHFFFAOYSA-N 0.000 claims description 2
- FCZWZPAMXLVKRA-UHFFFAOYSA-N 3-[[6-[4-(3,5-dimethylpyrazol-1-yl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)N3C(=CC(C)=N3)C)C=2)=C1 FCZWZPAMXLVKRA-UHFFFAOYSA-N 0.000 claims description 2
- YCGUDRDYNAILPQ-UHFFFAOYSA-N 3-[[6-[4-(4,4-difluoropiperidine-1-carbonyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(=O)N3CCC(F)(F)CC3)C=2)=C1 YCGUDRDYNAILPQ-UHFFFAOYSA-N 0.000 claims description 2
- VGPFGNIVPMOBPN-UHFFFAOYSA-N 3-[[6-[4-(cyanomethyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(CC#N)=CC=3)C=2)=C1 VGPFGNIVPMOBPN-UHFFFAOYSA-N 0.000 claims description 2
- VNAACLPLKXJSFQ-UHFFFAOYSA-N 3-[[6-[4-(difluoromethoxy)anilino]pyrimidin-4-yl]amino]-4-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C(NC=2N=CN=C(NC=3C=CC(OC(F)F)=CC=3)C=2)=C1 VNAACLPLKXJSFQ-UHFFFAOYSA-N 0.000 claims description 2
- SPKLUEZXYTWKQK-UHFFFAOYSA-N 3-[[6-[4-(difluoromethoxy)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(OC(F)F)=CC=3)C=2)=C1 SPKLUEZXYTWKQK-UHFFFAOYSA-N 0.000 claims description 2
- KVCCWJHDBKTBSQ-UHFFFAOYSA-N 3-[[6-[4-(dimethylamino)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)N(C)C)C=2)=C1 KVCCWJHDBKTBSQ-UHFFFAOYSA-N 0.000 claims description 2
- VXLXCUMOVMTMPG-HXUWFJFHSA-N 3-[[6-[4-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical class CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(=O)N3C[C@@H](CC3)N(C)C)C=2)=C1 VXLXCUMOVMTMPG-HXUWFJFHSA-N 0.000 claims description 2
- VXLXCUMOVMTMPG-FQEVSTJZSA-N 3-[[6-[4-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical class CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(=O)N3C[C@H](CC3)N(C)C)C=2)=C1 VXLXCUMOVMTMPG-FQEVSTJZSA-N 0.000 claims description 2
- UHPGZIFHTHUFOB-UHFFFAOYSA-N 3-[[6-[4-[2-(diethylamino)ethoxy]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=CC(NC=2C=C(C=CC=2)S(=O)(=O)NC)=NC=N1 UHPGZIFHTHUFOB-UHFFFAOYSA-N 0.000 claims description 2
- FGRFULVLVCSZNT-UHFFFAOYSA-N 3-[[6-[4-[2-(dimethylamino)ethoxy]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(OCCN(C)C)=CC=3)C=2)=C1 FGRFULVLVCSZNT-UHFFFAOYSA-N 0.000 claims description 2
- YZMPHCQUQMMJLO-UHFFFAOYSA-N 3-[[6-[4-chloro-3-(3-morpholin-4-ylphenyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide 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)N3CCOCC3)C=2)=C1 YZMPHCQUQMMJLO-UHFFFAOYSA-N 0.000 claims description 2
- UVMSPYAPMZCHJJ-UHFFFAOYSA-N 3-[[6-[4-chloro-3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C(Cl)=CC=3)C(F)(F)F)C=2)=C1 UVMSPYAPMZCHJJ-UHFFFAOYSA-N 0.000 claims description 2
- IVCSEVWQEHXUJV-UHFFFAOYSA-N 3-chloro-5-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(Cl)=CC(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 IVCSEVWQEHXUJV-UHFFFAOYSA-N 0.000 claims description 2
- FOBZAJHWKNKFSN-UHFFFAOYSA-N 4-(dimethylamino)-3-[[6-(3-fluoroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2N=CN=C(NC=3C=C(F)C=CC=3)C=2)=C1 FOBZAJHWKNKFSN-UHFFFAOYSA-N 0.000 claims description 2
- SXVDJUYMANZEAH-UHFFFAOYSA-N 4-[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=CC(=CC=3)C(N)=O)C=2)=C1 SXVDJUYMANZEAH-UHFFFAOYSA-N 0.000 claims description 2
- KQYMCFXAYGIEND-UHFFFAOYSA-N 4-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]-n-phenylbenzamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)C(=O)NC=3C=CC=CC=3)C=2)=C1 KQYMCFXAYGIEND-UHFFFAOYSA-N 0.000 claims description 2
- XJAMSALTZIVTMV-UHFFFAOYSA-N 4-chloro-3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Cl)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 XJAMSALTZIVTMV-UHFFFAOYSA-N 0.000 claims description 2
- AVZCCMMGSORHQI-UHFFFAOYSA-N 4-chloro-3-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Cl)C(NC=2N=CN=C(NC=3N=CC(Cl)=CC=3)C=2)=C1 AVZCCMMGSORHQI-UHFFFAOYSA-N 0.000 claims description 2
- XWAXLAMQFSGHKV-UHFFFAOYSA-N 4-ethylsulfanyl-n-methyl-3-[[6-(4-propan-2-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CCSC1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(NC=2C=CC(=CC=2)C(C)C)=NC=N1 XWAXLAMQFSGHKV-UHFFFAOYSA-N 0.000 claims description 2
- QOSWGLVBDNXTQK-UHFFFAOYSA-N 4-tert-butylsulfonyl-3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(=O)(=O)C(C)(C)C)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 QOSWGLVBDNXTQK-UHFFFAOYSA-N 0.000 claims description 2
- UEKVYLMUTALQGM-UHFFFAOYSA-N 4-tert-butylsulfonyl-3-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(=O)(=O)C(C)(C)C)C(NC=2N=CN=C(NC=3N=CC(Cl)=CC=3)C=2)=C1 UEKVYLMUTALQGM-UHFFFAOYSA-N 0.000 claims description 2
- MEEZEVULYGOZNK-UHFFFAOYSA-N 5-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-2-fluoro-4-methoxy-n-methylbenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)NC)=CC(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1OC MEEZEVULYGOZNK-UHFFFAOYSA-N 0.000 claims description 2
- PROKIRPBZHLPJL-UHFFFAOYSA-N 5-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-2-fluoro-n-methylbenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)NC)=CC(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 PROKIRPBZHLPJL-UHFFFAOYSA-N 0.000 claims description 2
- UNDHXTIMUNLCHG-UHFFFAOYSA-N 5-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-4-(dimethylamino)-2-fluoro-n-methylbenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)NC)=CC(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1N(C)C UNDHXTIMUNLCHG-UHFFFAOYSA-N 0.000 claims description 2
- KEUAZHPVAPTJEZ-UHFFFAOYSA-N 5-[[6-[(5-chloropyridin-2-yl)amino]pyrimidin-4-yl]amino]-2-fluoro-n-methyl-4-methylsulfonylbenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)NC)=CC(NC=2N=CN=C(NC=3N=CC(Cl)=CC=3)C=2)=C1S(C)(=O)=O KEUAZHPVAPTJEZ-UHFFFAOYSA-N 0.000 claims description 2
- VKJGBAJNNALVAV-UHFFFAOYSA-M Berberine chloride (TN) Chemical compound [Cl-].C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 VKJGBAJNNALVAV-UHFFFAOYSA-M 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- BHJSAWXELQIZPP-UHFFFAOYSA-N n-[3-[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=C(NC(C)=O)C=CC=3)C=2)=C1 BHJSAWXELQIZPP-UHFFFAOYSA-N 0.000 claims description 2
- AFYCYPXTAGREIM-UHFFFAOYSA-N n-[3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]acetamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(C)=O)C=CC=3)C=2)=C1 AFYCYPXTAGREIM-UHFFFAOYSA-N 0.000 claims description 2
- URSMQDIQMUPRGV-UHFFFAOYSA-N n-[3-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)S(=O)(=O)NC)C=2)=C1 URSMQDIQMUPRGV-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- ATNCURGERCDUBM-UHFFFAOYSA-N n-[4-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]acetamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(NC(C)=O)=CC=3)C=2)=C1 ATNCURGERCDUBM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- RQKLQVRPEWCOJR-UHFFFAOYSA-N n-methyl-3-[[6-(4-piperidin-1-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)C=2)=C1 RQKLQVRPEWCOJR-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- CYNROJZPSCKOED-UHFFFAOYSA-N n-methyl-3-[[6-[(2-methyl-1,3-benzothiazol-5-yl)amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4N=C(C)SC4=CC=3)C=2)=C1 CYNROJZPSCKOED-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- HLBOITFNEOFRHC-UHFFFAOYSA-N n-methyl-3-[[6-[(4-methyl-2-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=C4OC(=O)C=C(C)C4=CC=3)C=2)=C1 HLBOITFNEOFRHC-UHFFFAOYSA-N 0.000 claims description 2
- UXCOOVLQRPJMPZ-UHFFFAOYSA-N n-methyl-3-[[6-[(4-methyl-2-oxochromen-7-yl)amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4OC(=O)C=C(C)C4=CC=3)C=2)=C1 UXCOOVLQRPJMPZ-UHFFFAOYSA-N 0.000 claims description 2
- GNKZOLLOBBSQRD-UHFFFAOYSA-N n-methyl-3-[[6-[(5-oxo-7,8-dihydro-6h-naphthalen-2-yl)amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C4CCCC(=O)C4=CC=3)C=2)=C1 GNKZOLLOBBSQRD-UHFFFAOYSA-N 0.000 claims description 2
- WEMNZZYEACGXCH-UHFFFAOYSA-N n-methyl-3-[[6-[3-(2-methyl-1,3-thiazol-4-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3N=C(C)SC=3)C=2)=C1 WEMNZZYEACGXCH-UHFFFAOYSA-N 0.000 claims description 2
- UKJZNTDEBCAYJW-UHFFFAOYSA-N n-methyl-3-[[6-[3-(4-morpholin-4-ylphenyl)anilino]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)N3CCOCC3)C=2)=C1 UKJZNTDEBCAYJW-UHFFFAOYSA-N 0.000 claims description 2
- YPYXNFDSPCTGOV-UHFFFAOYSA-N n-methyl-3-[[6-[3-[4-(methylsulfamoyl)phenyl]anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)S(=O)(=O)NC)C=2)=C1 YPYXNFDSPCTGOV-UHFFFAOYSA-N 0.000 claims description 2
- XIMFRFFFUGBTNE-UHFFFAOYSA-N n-methyl-4-(2-methylpropylsulfanyl)-3-[[6-(4-propan-2-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SCC(C)C)C(NC=2N=CN=C(NC=3C=CC(=CC=3)C(C)C)C=2)=C1 XIMFRFFFUGBTNE-UHFFFAOYSA-N 0.000 claims description 2
- QYMWIXHBYLBHNH-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-(3,4,5-trifluoroanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C(F)C(F)=C(F)C=3)C=2)=C1 QYMWIXHBYLBHNH-UHFFFAOYSA-N 0.000 claims description 2
- SMBFYBRSUUBIBO-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C(OC)C(OC)=C(OC)C=3)C=2)=C1 SMBFYBRSUUBIBO-UHFFFAOYSA-N 0.000 claims description 2
- FGXMUTUKIOPWKZ-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-(4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)C=2)=C1 FGXMUTUKIOPWKZ-UHFFFAOYSA-N 0.000 claims description 2
- CESOAKGRMUATHX-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-(4-piperidin-1-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)C=2)=C1 CESOAKGRMUATHX-UHFFFAOYSA-N 0.000 claims description 2
- JSKDNTQOVUQFDU-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-(quinolin-6-ylamino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=C4C=CC=NC4=CC=3)C=2)=C1 JSKDNTQOVUQFDU-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- DDAAXBMCZOIXBQ-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-[[6-[4-(1,2,4-triazol-4-ylmethyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(NC=3C=CC(CN4C=NN=C4)=CC=3)C=2)=C1 DDAAXBMCZOIXBQ-UHFFFAOYSA-N 0.000 claims description 2
- WMNNNGYZTIDYPU-UHFFFAOYSA-N n-methyl-4-propan-2-ylsulfonyl-3-[[6-[[5-(trifluoromethyl)pyridin-2-yl]amino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(=O)(=O)C(C)C)C(NC=2N=CN=C(NC=3N=CC(=CC=3)C(F)(F)F)C=2)=C1 WMNNNGYZTIDYPU-UHFFFAOYSA-N 0.000 claims description 2
- CDTKKGVPCRKSAA-UHFFFAOYSA-N n-methyl-5-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]pyridine-3-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=NC=3)S(=O)(=O)NC)C=2)=C1 CDTKKGVPCRKSAA-UHFFFAOYSA-N 0.000 claims description 2
- SVDVKEBISAOWJT-UHFFFAOYSA-N n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1 SVDVKEBISAOWJT-UHFFFAOYSA-N 0.000 claims description 2
- LQPOXJPCDJENTN-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-N-methyl-4-propan-2-ylsulfonylbenzenesulfonamide 3-[[6-(2,3-dihydro-1H-inden-5-ylamino)pyrimidin-4-yl]amino]-N-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)c1cccc(Nc2cc(Nc3ccc4CCCc4c3)ncn2)c1.CNS(=O)(=O)c1ccc(c(Nc2cc(Nc3ccc(Cl)cc3)ncn2)c1)S(=O)(=O)C(C)C LQPOXJPCDJENTN-UHFFFAOYSA-N 0.000 claims 1
- 241000534944 Thia Species 0.000 claims 1
- DJUMGKIMDKFAKI-UHFFFAOYSA-N n-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 DJUMGKIMDKFAKI-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
- 239000000203 mixture Substances 0.000 description 119
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 118
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- 239000007787 solid Substances 0.000 description 94
- 239000000243 solution Substances 0.000 description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- 239000012458 free base Substances 0.000 description 72
- 235000019439 ethyl acetate Nutrition 0.000 description 58
- 239000000460 chlorine Substances 0.000 description 56
- 150000003840 hydrochlorides Chemical group 0.000 description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000002904 solvent Substances 0.000 description 32
- 150000001412 amines Chemical class 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000003818 flash chromatography Methods 0.000 description 27
- 238000004519 manufacturing process Methods 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 239000011734 sodium Substances 0.000 description 24
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 23
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- 239000003208 petroleum Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000012267 brine Substances 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 13
- PRTLSVYSOPRSIX-UHFFFAOYSA-N 4-fluoro-n-methyl-3-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 PRTLSVYSOPRSIX-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- RZEQIKONIAPHOI-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(Cl)C=2)=C1 RZEQIKONIAPHOI-UHFFFAOYSA-N 0.000 description 9
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 9
- 208000006029 Cardiomegaly Diseases 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 239000012453 solvate Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000003643 water by type Substances 0.000 description 8
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 8
- 101000662993 Homo sapiens Serine/threonine-protein kinase TNNI3K Proteins 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 150000004677 hydrates Chemical class 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- IRPVDRJOTNPMFM-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-n-methyl-4-methylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C(NC=2N=CN=C(Cl)C=2)=C1 IRPVDRJOTNPMFM-UHFFFAOYSA-N 0.000 description 6
- XWLTXNUHPJFIJM-UHFFFAOYSA-N 4-amino-n-(2-methoxyethyl)benzamide Chemical compound COCCNC(=O)C1=CC=C(N)C=C1 XWLTXNUHPJFIJM-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- UZPUUYBBKZVODX-UHFFFAOYSA-N benzyl N-[(4-fluoro-3-nitrophenyl)sulfonylmethyl]carbamate Chemical compound C1(=CC=CC=C1)COC(NCS(=O)(=O)C1=CC(=C(C=C1)F)[N+](=O)[O-])=O UZPUUYBBKZVODX-UHFFFAOYSA-N 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- 102000049185 human TNNI3K Human genes 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- FVLCMZSARFTYBY-UHFFFAOYSA-N n-methyl-2,3-dihydro-1h-indole-6-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2CCNC2=C1 FVLCMZSARFTYBY-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- BBNCAUCNCDIBQL-UHFFFAOYSA-N 2,4-difluoro-n-methyl-5-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC([N+]([O-])=O)=C(F)C=C1F BBNCAUCNCDIBQL-UHFFFAOYSA-N 0.000 description 5
- ZBGSSQPURNEVRF-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(NC=2N=CN=C(Cl)C=2)=C1 ZBGSSQPURNEVRF-UHFFFAOYSA-N 0.000 description 5
- WESGDTGMPMETLO-UHFFFAOYSA-N 3-chloro-n-methyl-5-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1 WESGDTGMPMETLO-UHFFFAOYSA-N 0.000 description 5
- OLIKUFFCLVIJHD-UHFFFAOYSA-N 6-chloro-n-(4-chlorophenyl)pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1NC1=CC(Cl)=NC=N1 OLIKUFFCLVIJHD-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- CHKFOGJYAICJSR-UHFFFAOYSA-N benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NS(=O)(=O)C1=CC=CC=C1 CHKFOGJYAICJSR-UHFFFAOYSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000004007 reversed phase HPLC Methods 0.000 description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 4
- RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 4
- XAZYVFJSHFBTTM-UHFFFAOYSA-N 2,4-difluoro-5-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=C(F)C=C1F XAZYVFJSHFBTTM-UHFFFAOYSA-N 0.000 description 4
- VQHGELUKJYOETQ-UHFFFAOYSA-N 2-fluoro-5-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(F)C(S(Cl)(=O)=O)=C1 VQHGELUKJYOETQ-UHFFFAOYSA-N 0.000 description 4
- ZFFUFWXJBDZZFV-UHFFFAOYSA-N 2-fluoro-n-methyl-5-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1F ZFFUFWXJBDZZFV-UHFFFAOYSA-N 0.000 description 4
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 4
- IOAJGLCYPCJWFC-UHFFFAOYSA-N 3-(6-chloropyrimidin-4-yl)-n-methylbenzimidazole-5-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2N=CN1C1=CC(Cl)=NC=N1 IOAJGLCYPCJWFC-UHFFFAOYSA-N 0.000 description 4
- DJJFJERPVZXIBX-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2N=CN=C(Cl)C=2)=C1 DJJFJERPVZXIBX-UHFFFAOYSA-N 0.000 description 4
- WFOSGTNBNISVKE-UHFFFAOYSA-N 4-(dimethylamino)-2-fluoro-n-methyl-5-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC([N+]([O-])=O)=C(N(C)C)C=C1F WFOSGTNBNISVKE-UHFFFAOYSA-N 0.000 description 4
- HAFZZEDCXBSLLC-UHFFFAOYSA-N 5-amino-2-fluoro-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N)=C(SC)C=C1F HAFZZEDCXBSLLC-UHFFFAOYSA-N 0.000 description 4
- PFEAQGIRENOXFR-UHFFFAOYSA-N 5-amino-2-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N)=CC=C1F PFEAQGIRENOXFR-UHFFFAOYSA-N 0.000 description 4
- BTBJBAAVDLVBFK-UHFFFAOYSA-N 5-amino-4-(dimethylamino)-2-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N)=C(N(C)C)C=C1F BTBJBAAVDLVBFK-UHFFFAOYSA-N 0.000 description 4
- OTEWKDZPCPCAOI-UHFFFAOYSA-N 6-chloro-n-(3-methylphenyl)pyrimidin-4-amine Chemical compound CC1=CC=CC(NC=2N=CN=C(Cl)C=2)=C1 OTEWKDZPCPCAOI-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 238000002875 fluorescence polarization Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000005984 hexahydro-1H-1,4-diazepinyl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 0 *c1c(*)c(S(N*)(=O)=O)cc(N(*)c2cc(Cl)ncn2)c1* Chemical compound *c1c(*)c(S(N*)(=O)=O)cc(N(*)c2cc(Cl)ncn2)c1* 0.000 description 3
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 3
- PYWPWPPRAYOLIB-UHFFFAOYSA-N 1-(3,3-dimethyl-2h-indol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CC(C)(C)C2=C1 PYWPWPPRAYOLIB-UHFFFAOYSA-N 0.000 description 3
- CLHHJCMRNFFCPN-UHFFFAOYSA-N 1-acetyl-2,3-dihydroindole-6-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2N(C(=O)C)CCC2=C1 CLHHJCMRNFFCPN-UHFFFAOYSA-N 0.000 description 3
- FTWAILLGJAETPR-UHFFFAOYSA-N 1-acetyl-2,3-dihydroindole-6-sulfonyl chloride Chemical compound C1=C(S(Cl)(=O)=O)C=C2N(C(=O)C)CCC2=C1 FTWAILLGJAETPR-UHFFFAOYSA-N 0.000 description 3
- NUSHNFQIOINGFS-UHFFFAOYSA-N 1-acetyl-3,3-dimethyl-2h-indole-6-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2N(C(=O)C)CC(C)(C)C2=C1 NUSHNFQIOINGFS-UHFFFAOYSA-N 0.000 description 3
- HMFHDKLYJLEKDU-UHFFFAOYSA-N 1-acetyl-3,3-dimethyl-2h-indole-6-sulfonyl chloride Chemical compound C1=C(S(Cl)(=O)=O)C=C2N(C(=O)C)CC(C)(C)C2=C1 HMFHDKLYJLEKDU-UHFFFAOYSA-N 0.000 description 3
- YTFIIXYVQCRCIP-UHFFFAOYSA-N 1-acetyl-n,3,3-trimethyl-2h-indole-6-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2C(C)(C)CN(C(C)=O)C2=C1 YTFIIXYVQCRCIP-UHFFFAOYSA-N 0.000 description 3
- OCRSQXXPDMMEQV-UHFFFAOYSA-N 1-acetyl-n-methyl-2,3-dihydroindole-6-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2CCN(C(C)=O)C2=C1 OCRSQXXPDMMEQV-UHFFFAOYSA-N 0.000 description 3
- SNRSKXDRZWSQKH-UHFFFAOYSA-N 2,3-dihydro-1h-indole-6-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2CCNC2=C1 SNRSKXDRZWSQKH-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- XJBHIZXBVPGRHH-UHFFFAOYSA-N 2-fluoro-5-nitro-4-(2,2,2-trifluoroethoxy)benzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=C(F)C=C1OCC(F)(F)F XJBHIZXBVPGRHH-UHFFFAOYSA-N 0.000 description 3
- RJEYXRJFAIYPDD-UHFFFAOYSA-N 2-fluoro-n-methyl-5-nitro-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC([N+]([O-])=O)=C(OCC(F)(F)F)C=C1F RJEYXRJFAIYPDD-UHFFFAOYSA-N 0.000 description 3
- VRKLIVSHUQSRNF-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinolin-7-amine Chemical compound C1=C(N)C=C2CN(C)CCC2=C1 VRKLIVSHUQSRNF-UHFFFAOYSA-N 0.000 description 3
- PUMCPMLEPPOZRX-UHFFFAOYSA-N 2-methyl-7-nitro-3,4-dihydro-1h-isoquinoline Chemical compound C1=C([N+]([O-])=O)C=C2CN(C)CCC2=C1 PUMCPMLEPPOZRX-UHFFFAOYSA-N 0.000 description 3
- SRCCLYMWDRNUAF-UHFFFAOYSA-N 3,3-dimethyl-1,2-dihydroindole Chemical compound C1=CC=C2C(C)(C)CNC2=C1 SRCCLYMWDRNUAF-UHFFFAOYSA-N 0.000 description 3
- KFEPPZBGGHMGSD-UHFFFAOYSA-N 3,3-dimethyl-1,2-dihydroindole-6-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(C)(C)CNC2=C1 KFEPPZBGGHMGSD-UHFFFAOYSA-N 0.000 description 3
- GSTCLLCEBJUOLB-UHFFFAOYSA-N 3,5-dinitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC(S(Cl)(=O)=O)=C1 GSTCLLCEBJUOLB-UHFFFAOYSA-N 0.000 description 3
- IMKVRIVVWMTHRB-UHFFFAOYSA-N 3-(dimethylamino)-n-methyl-5-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N(C)C)=CC([N+]([O-])=O)=C1 IMKVRIVVWMTHRB-UHFFFAOYSA-N 0.000 description 3
- QZPQMUQYVGDXFA-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(NC=2N=CN=C(Cl)C=2)=C1 QZPQMUQYVGDXFA-UHFFFAOYSA-N 0.000 description 3
- HQCSMPOAVQPAQQ-UHFFFAOYSA-N 3-amino-4-chloro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Cl)C(N)=C1 HQCSMPOAVQPAQQ-UHFFFAOYSA-N 0.000 description 3
- CFROADZUAUHGQE-UHFFFAOYSA-N 3-amino-4-ethylsulfanyl-n-methylbenzenesulfonamide Chemical compound CCSC1=CC=C(S(=O)(=O)NC)C=C1N CFROADZUAUHGQE-UHFFFAOYSA-N 0.000 description 3
- UXLLDUXIDDMANK-UHFFFAOYSA-N 3-amino-4-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C(N)=C1 UXLLDUXIDDMANK-UHFFFAOYSA-N 0.000 description 3
- NFNLMGYLSDEJKS-UHFFFAOYSA-N 3-amino-4-hydroxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(O)C(N)=C1 NFNLMGYLSDEJKS-UHFFFAOYSA-N 0.000 description 3
- FQSRDQCSGSDBMQ-UHFFFAOYSA-N 3-amino-5-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N)=CC(N(C)C)=C1 FQSRDQCSGSDBMQ-UHFFFAOYSA-N 0.000 description 3
- XQEDHQMPIHJWMV-UHFFFAOYSA-N 3-amino-n-methyl-4-[methyl(2,2,2-trifluoroethyl)amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)CC(F)(F)F)C(N)=C1 XQEDHQMPIHJWMV-UHFFFAOYSA-N 0.000 description 3
- BJJFJTDSMDVFIJ-UHFFFAOYSA-N 3-amino-n-methyl-4-methylsulfanylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C(N)=C1 BJJFJTDSMDVFIJ-UHFFFAOYSA-N 0.000 description 3
- XVQMWFGOFRXMHE-UHFFFAOYSA-N 3-amino-n-methyl-4-morpholin-4-ylbenzenesulfonamide Chemical compound NC1=CC(S(=O)(=O)NC)=CC=C1N1CCOCC1 XVQMWFGOFRXMHE-UHFFFAOYSA-N 0.000 description 3
- NFUZPVIWFUFFJA-UHFFFAOYSA-N 3-amino-n-methyl-4-propan-2-yloxybenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C)C(N)=C1 NFUZPVIWFUFFJA-UHFFFAOYSA-N 0.000 description 3
- HENXFXNTEWRTRE-UHFFFAOYSA-N 3-amino-n-methyl-5-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N)=CC([N+]([O-])=O)=C1 HENXFXNTEWRTRE-UHFFFAOYSA-N 0.000 description 3
- UMNGEAKUUOJPAX-UHFFFAOYSA-N 4-chloro-n-methyl-3-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 UMNGEAKUUOJPAX-UHFFFAOYSA-N 0.000 description 3
- CPAUEFVZMODCHU-UHFFFAOYSA-N 4-ethylsulfanyl-n-methyl-3-nitrobenzenesulfonamide Chemical compound CCSC1=CC=C(S(=O)(=O)NC)C=C1[N+]([O-])=O CPAUEFVZMODCHU-UHFFFAOYSA-N 0.000 description 3
- RRONENSZKCGROA-UHFFFAOYSA-N 4-fluoro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1F RRONENSZKCGROA-UHFFFAOYSA-N 0.000 description 3
- ORCOFVZAETWNGU-UHFFFAOYSA-N 4-hydroxy-n-methyl-3-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 ORCOFVZAETWNGU-UHFFFAOYSA-N 0.000 description 3
- CLATWDTWMVIPHK-UHFFFAOYSA-N 5-[2-[[3-[[4-(5-hydroxy-2-methylanilino)pyrimidin-2-yl]amino]benzoyl]amino]ethylcarbamoyl]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid Chemical compound CC1=CC=C(O)C=C1NC1=CC=NC(NC=2C=C(C=CC=2)C(=O)NCCNC(=O)C=2C=C(C(=CC=2)C2=C3C=CC(=O)C=C3OC3=CC(O)=CC=C32)C(O)=O)=N1 CLATWDTWMVIPHK-UHFFFAOYSA-N 0.000 description 3
- DGQAPUDRPYXACW-UHFFFAOYSA-N 5-amino-2-fluoro-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N)=C(OCC(F)(F)F)C=C1F DGQAPUDRPYXACW-UHFFFAOYSA-N 0.000 description 3
- NEHUMJFYLVDBBE-UHFFFAOYSA-N 5-amino-n-methylpyridine-3-sulfonamide Chemical compound CNS(=O)(=O)C1=CN=CC(N)=C1 NEHUMJFYLVDBBE-UHFFFAOYSA-N 0.000 description 3
- SNFZSCOGEYEYJG-UHFFFAOYSA-N 5-bromo-n-methylpyridine-3-sulfonamide Chemical compound CNS(=O)(=O)C1=CN=CC(Br)=C1 SNFZSCOGEYEYJG-UHFFFAOYSA-N 0.000 description 3
- ZIDASXSLFQERPA-UHFFFAOYSA-N 6-chloro-n-(3,5-dichloropyridin-2-yl)pyrimidin-4-amine Chemical compound ClC1=CC(Cl)=CN=C1NC1=CC(Cl)=NC=N1 ZIDASXSLFQERPA-UHFFFAOYSA-N 0.000 description 3
- ADDHBGDKAUORNP-UHFFFAOYSA-N 6-chloro-n-(4-chlorophenyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1NC1=CC(Cl)=NC=N1 ADDHBGDKAUORNP-UHFFFAOYSA-N 0.000 description 3
- 239000005541 ACE inhibitor Substances 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 101100189356 Mus musculus Papolb gene Proteins 0.000 description 3
- 108091000080 Phosphotransferase Proteins 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 102100037670 Serine/threonine-protein kinase TNNI3K Human genes 0.000 description 3
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 3
- 229940125364 angiotensin receptor blocker Drugs 0.000 description 3
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 3
- IKTHZOFWYDWIRA-UHFFFAOYSA-N benzyl N-[(3,4-diaminophenyl)sulfonylmethyl]carbamate Chemical compound C1(=CC=CC=C1)COC(NCS(=O)(=O)C1=CC(=C(C=C1)N)N)=O IKTHZOFWYDWIRA-UHFFFAOYSA-N 0.000 description 3
- MGSRRJIXSRBPDW-UHFFFAOYSA-N benzyl n-methyl-n-[3-nitro-4-(2,2,2-trifluoroethylamino)phenyl]sulfonylcarbamate Chemical compound C=1C=C(NCC(F)(F)F)C([N+]([O-])=O)=CC=1S(=O)(=O)N(C)C(=O)OCC1=CC=CC=C1 MGSRRJIXSRBPDW-UHFFFAOYSA-N 0.000 description 3
- MFEBBYPCFNOSQB-UHFFFAOYSA-N benzyl n-methyl-n-[4-[methyl(2,2,2-trifluoroethyl)amino]-3-nitrophenyl]sulfonylcarbamate Chemical compound C1=C([N+]([O-])=O)C(N(CC(F)(F)F)C)=CC=C1S(=O)(=O)N(C)C(=O)OCC1=CC=CC=C1 MFEBBYPCFNOSQB-UHFFFAOYSA-N 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 230000009977 dual effect Effects 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000002032 methanolic fraction Substances 0.000 description 3
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- 208000031225 myocardial ischemia Diseases 0.000 description 3
- GDRBGHXWHDMLEM-UHFFFAOYSA-N n-(2-methoxyethyl)-4-nitrobenzamide Chemical compound COCCNC(=O)C1=CC=C([N+]([O-])=O)C=C1 GDRBGHXWHDMLEM-UHFFFAOYSA-N 0.000 description 3
- DPEDJYXBXHDIOQ-UHFFFAOYSA-N n-(2-methylprop-2-enyl)-n-phenylacetamide Chemical compound CC(=C)CN(C(C)=O)C1=CC=CC=C1 DPEDJYXBXHDIOQ-UHFFFAOYSA-N 0.000 description 3
- JFJZUXBRSGEOTE-UHFFFAOYSA-N n-methyl-1h-indole-6-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2C=CNC2=C1 JFJZUXBRSGEOTE-UHFFFAOYSA-N 0.000 description 3
- MPUBVHFGDNPNCL-UHFFFAOYSA-N n-methyl-3,5-dinitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 MPUBVHFGDNPNCL-UHFFFAOYSA-N 0.000 description 3
- AQSFJSXSHHVVPT-UHFFFAOYSA-N n-methyl-3-nitro-4-propan-2-yloxybenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OC(C)C)C([N+]([O-])=O)=C1 AQSFJSXSHHVVPT-UHFFFAOYSA-N 0.000 description 3
- VZODTLCCJGMYTG-UHFFFAOYSA-N n-methyl-4-methylsulfanyl-3-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(SC)C([N+]([O-])=O)=C1 VZODTLCCJGMYTG-UHFFFAOYSA-N 0.000 description 3
- ZDUSNUAEXDDJAQ-UHFFFAOYSA-N n-methyl-4-morpholin-4-yl-3-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC)=CC=C1N1CCOCC1 ZDUSNUAEXDDJAQ-UHFFFAOYSA-N 0.000 description 3
- 239000008184 oral solid dosage form Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 102000020233 phosphotransferase Human genes 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 2
- KFHQOZXAFUKFNB-UHFFFAOYSA-N 1,3-oxathiolanyl Chemical group [CH]1OCCS1 KFHQOZXAFUKFNB-UHFFFAOYSA-N 0.000 description 2
- UZGZNXKYFCCVNC-UHFFFAOYSA-N 1-(6-chloropyrimidin-4-yl)-n-methyl-2,3-dihydroindole-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2CCN1C1=CC(Cl)=NC=N1 UZGZNXKYFCCVNC-UHFFFAOYSA-N 0.000 description 2
- LCXJMRMGDVGCCI-UHFFFAOYSA-N 1-[6-(4-chloroanilino)pyrimidin-4-yl]-n-methyl-2,3-dihydroindole-6-sulfonamide;hydrochloride Chemical compound Cl.C12=CC(S(=O)(=O)NC)=CC=C2CCN1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 LCXJMRMGDVGCCI-UHFFFAOYSA-N 0.000 description 2
- ZFUIQSMQPWRIIZ-UHFFFAOYSA-N 1-[6-(4-chloroanilino)pyrimidin-4-yl]-n-methylindole-6-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(S(=O)(=O)NC)=CC=C2C=CN1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 ZFUIQSMQPWRIIZ-UHFFFAOYSA-N 0.000 description 2
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
- QTVKEWYIQMCPLS-UHFFFAOYSA-N 2-fluoro-n-methyl-4-methylsulfanyl-5-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC([N+]([O-])=O)=C(SC)C=C1F QTVKEWYIQMCPLS-UHFFFAOYSA-N 0.000 description 2
- WDDNAQHWWYFRLE-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-4-fluoro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(F)C(NC=2N=CN=C(Cl)C=2)=C1 WDDNAQHWWYFRLE-UHFFFAOYSA-N 0.000 description 2
- WLKNTUJYSYAPFR-UHFFFAOYSA-N 3-[[6-(3-hydroxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(O)C=CC=3)C=2)=C1 WLKNTUJYSYAPFR-UHFFFAOYSA-N 0.000 description 2
- SIPXYJMDQPGBNX-UHFFFAOYSA-N 3-amino-5-chloro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(N)=CC(Cl)=C1 SIPXYJMDQPGBNX-UHFFFAOYSA-N 0.000 description 2
- SFCWILLFDXUKRB-UHFFFAOYSA-N 3-amino-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(N)=C1 SFCWILLFDXUKRB-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 2
- BRXLFFREFWYUOJ-UHFFFAOYSA-N 4-chloro-3-[(6-chloropyrimidin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Cl)C(NC=2N=CN=C(Cl)C=2)=C1 BRXLFFREFWYUOJ-UHFFFAOYSA-N 0.000 description 2
- USOVRXNIZFSGEU-UHFFFAOYSA-N 4-fluoro-1-nitro-2-(2,2,2-trifluoroethoxy)benzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1OCC(F)(F)F USOVRXNIZFSGEU-UHFFFAOYSA-N 0.000 description 2
- NNIQJVISWXXUFN-UHFFFAOYSA-N 4-tert-butylsulfonyl-3-[(6-chloropyrimidin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(=O)(=O)C(C)(C)C)C(NC=2N=CN=C(Cl)C=2)=C1 NNIQJVISWXXUFN-UHFFFAOYSA-N 0.000 description 2
- AVILRJQPDYPXFQ-UHFFFAOYSA-N 5-bromopyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CN=CC(Br)=C1 AVILRJQPDYPXFQ-UHFFFAOYSA-N 0.000 description 2
- DYUUYJZZPDLBAZ-UHFFFAOYSA-N 6-chloro-n-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OCC(F)(F)F)=CC=C1NC1=CC(Cl)=NC=N1 DYUUYJZZPDLBAZ-UHFFFAOYSA-N 0.000 description 2
- IECNBQLAQJXRHB-UHFFFAOYSA-N 6-chloro-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=CC(Cl)=NC=N1 IECNBQLAQJXRHB-UHFFFAOYSA-N 0.000 description 2
- YPRWYZSUBZXORL-UHFFFAOYSA-N 7-nitro-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=CC([N+](=O)[O-])=CC=C21 YPRWYZSUBZXORL-UHFFFAOYSA-N 0.000 description 2
- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 description 2
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WBEYAUJYYCOROY-UHFFFAOYSA-N C1(=CC=CC=C1)COC(NCS(=O)(=O)C1=CC(=C(C=C1)N)[N+](=O)[O-])=O Chemical compound C1(=CC=CC=C1)COC(NCS(=O)(=O)C1=CC(=C(C=C1)N)[N+](=O)[O-])=O WBEYAUJYYCOROY-UHFFFAOYSA-N 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 101150048270 DHPS gene Proteins 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 108010061435 Enalapril Proteins 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 206010020880 Hypertrophy Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 102000003979 Mineralocorticoid Receptors Human genes 0.000 description 2
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229960004530 benazepril Drugs 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 229940097320 beta blocking agent Drugs 0.000 description 2
- CHDPSNLJFOQTRK-UHFFFAOYSA-N betaxolol hydrochloride Chemical compound [Cl-].C1=CC(OCC(O)C[NH2+]C(C)C)=CC=C1CCOCC1CC1 CHDPSNLJFOQTRK-UHFFFAOYSA-N 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000000480 calcium channel blocker Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 description 2
- OGHNVEJMJSYVRP-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229960000873 enalapril Drugs 0.000 description 2
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 2
- 238000003821 enantio-separation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- HGOIUNNGTCPJHF-UHFFFAOYSA-N ethyl 2-[[4-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]benzoyl]amino]acetate Chemical compound C1=CC(C(=O)NCC(=O)OCC)=CC=C1NC1=CC(NC=2C=C(C=CC=2)S(=O)(=O)NC)=NC=N1 HGOIUNNGTCPJHF-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 210000005003 heart tissue Anatomy 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- HZMWOZPWGBUWQL-UHFFFAOYSA-N methyl 2-[[6-[3-(methylsulfamoyl)anilino]pyrimidin-4-yl]amino]-1,3-thiazole-5-carboxylate Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3SC(=CN=3)C(=O)OC)C=2)=C1 HZMWOZPWGBUWQL-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- XGALZACYMHSUMH-UHFFFAOYSA-N n,3,3-trimethyl-1,2-dihydroindole-6-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2C(C)(C)CNC2=C1 XGALZACYMHSUMH-UHFFFAOYSA-N 0.000 description 2
- DHWNQDSYEQBISM-UHFFFAOYSA-N n-methyl-3-[[6-(3-phenylanilino)pyrimidin-4-yl]amino]benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(C=CC=3)C=3C=CC=CC=3)C=2)=C1 DHWNQDSYEQBISM-UHFFFAOYSA-N 0.000 description 2
- GYDNASZBWNKJFU-UHFFFAOYSA-N n-methyl-4-(2,2,2-trifluoroethoxy)-3-[[6-[[5-(trifluoromethyl)pyridin-2-yl]amino]pyrimidin-4-yl]amino]benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(NC=2N=CN=C(NC=3N=CC(=CC=3)C(F)(F)F)C=2)=C1 GYDNASZBWNKJFU-UHFFFAOYSA-N 0.000 description 2
- VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 2
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000005968 oxazolinyl group Chemical group 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 description 2
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 2
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229960001455 quinapril Drugs 0.000 description 2
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 2
- 229960003401 ramipril Drugs 0.000 description 2
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000002461 renin inhibitor Substances 0.000 description 2
- 229940086526 renin-inhibitors Drugs 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 2
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 229940032147 starch Drugs 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000007910 systemic administration Methods 0.000 description 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000002769 thiazolinyl group Chemical group 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 description 1
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 1
- SOCAXRLFGRNEPK-IFZYUDKTSA-N (1r,3s,5r)-2-n-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)NC1=CN(C2=CC=C(OCC#N)C=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F SOCAXRLFGRNEPK-IFZYUDKTSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
- SVJMLYUFVDMUHP-XIFFEERXSA-N (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid O5-[3-(4,4-diphenyl-1-piperidinyl)propyl] ester O3-methyl ester Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCCN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=CC([N+]([O-])=O)=C1 SVJMLYUFVDMUHP-XIFFEERXSA-N 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 description 1
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
- KOHIRBRYDXPAMZ-YHBROIRLSA-N (S,R,R,R)-nebivolol Chemical compound C1CC2=CC(F)=CC=C2O[C@H]1[C@H](O)CNC[C@@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 KOHIRBRYDXPAMZ-YHBROIRLSA-N 0.000 description 1
- BRIPGNJWPCKDQZ-WXXKFALUSA-N (e)-but-2-enedioic acid;1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound OC(=O)\C=C\C(O)=O.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 BRIPGNJWPCKDQZ-WXXKFALUSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
- VFWXMBFKFGIGPJ-UHFFFAOYSA-N 1-(6-chloropyrimidin-4-yl)-n,3,3-trimethyl-2h-indole-6-sulfonamide Chemical group C=1C(S(=O)(=O)NC)=CC=C(C(C2)(C)C)C=1N2C1=CC(Cl)=NC=N1 VFWXMBFKFGIGPJ-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
- IQKOVLZJPVVLOZ-UHFFFAOYSA-N 1-o-tert-butyl 3-o-ethyl piperazine-1,3-dicarboxylate Chemical compound CCOC(=O)C1CN(C(=O)OC(C)(C)C)CCN1 IQKOVLZJPVVLOZ-UHFFFAOYSA-N 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical class NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- ULSLZZKKTPQNNJ-UHFFFAOYSA-N 2-methyl-1-(2-methylpropylsulfonyl)propane Chemical compound CC(C)CS(=O)(=O)CC(C)C ULSLZZKKTPQNNJ-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- SPJQDMKTFSPPLO-UHFFFAOYSA-N 2-tert-butylsulfonyl-2-methylpropane Chemical compound CC(C)(C)S(=O)(=O)C(C)(C)C SPJQDMKTFSPPLO-UHFFFAOYSA-N 0.000 description 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- OCWBGKZFOYMCCN-UHFFFAOYSA-N 3,5-dichloropyridin-2-amine Chemical compound NC1=NC=C(Cl)C=C1Cl OCWBGKZFOYMCCN-UHFFFAOYSA-N 0.000 description 1
- MPBZUKLDHPOCLS-UHFFFAOYSA-N 3,5-dinitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 MPBZUKLDHPOCLS-UHFFFAOYSA-N 0.000 description 1
- QUNDKHDVWBRKSA-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-4-(2,5-dimethylpyrrolidin-1-yl)-n-methylbenzenesulfonamide Chemical compound C=1C(Cl)=NC=NC=1NC1=CC(S(=O)(=O)NC)=CC=C1N1C(C)CCC1C QUNDKHDVWBRKSA-UHFFFAOYSA-N 0.000 description 1
- WNTXAWUUTFQMDB-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-4-(diethylamino)-n-methylbenzenesulfonamide Chemical compound CCN(CC)C1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(Cl)=NC=N1 WNTXAWUUTFQMDB-UHFFFAOYSA-N 0.000 description 1
- RNNMLILUVYDPLB-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-4-ethylsulfanyl-n-methylbenzenesulfonamide Chemical compound CCSC1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(Cl)=NC=N1 RNNMLILUVYDPLB-UHFFFAOYSA-N 0.000 description 1
- JDPRJMUBURLAKX-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-4-ethylsulfonyl-n-methylbenzenesulfonamide Chemical compound CCS(=O)(=O)C1=CC=C(S(=O)(=O)NC)C=C1NC1=CC(Cl)=NC=N1 JDPRJMUBURLAKX-UHFFFAOYSA-N 0.000 description 1
- VDMKTZNDXMMTDA-UHFFFAOYSA-N 3-[(6-chloropyrimidin-4-yl)amino]-n,4-dimethylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(C)C(NC=2N=CN=C(Cl)C=2)=C1 VDMKTZNDXMMTDA-UHFFFAOYSA-N 0.000 description 1
- NZSAHQSOAHGORN-UHFFFAOYSA-N 3-[6-(4-chloroanilino)pyrimidin-4-yl]-n-methyl-2-oxo-1h-benzimidazole-5-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(S(=O)(=O)NC)=CC=C2NC(=O)N1C(N=CN=1)=CC=1NC1=CC=C(Cl)C=C1 NZSAHQSOAHGORN-UHFFFAOYSA-N 0.000 description 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 description 1
- UUJVCLCXQXXGNF-UHFFFAOYSA-N 3-[[6-(3,4-dimethoxyanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CNS(=O)(=O)C1=CC=CC(NC=2N=CN=C(NC=3C=C(OC)C(OC)=CC=3)C=2)=C1 UUJVCLCXQXXGNF-UHFFFAOYSA-N 0.000 description 1
- IFRASVQNUKAXOF-UHFFFAOYSA-N 3-[[6-(4-chloroanilino)pyrimidin-4-yl]amino]-n-methyl-4-propan-2-ylsulfonylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(S(=O)(=O)C(C)C)C(NC=2N=CN=C(NC=3C=CC(Cl)=CC=3)C=2)=C1 IFRASVQNUKAXOF-UHFFFAOYSA-N 0.000 description 1
- ZILWXFNOASEMQZ-UHFFFAOYSA-N 3-[[6-[4-(cyanomethyl)anilino]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(CC#N)=CC=3)C=2)=C1 ZILWXFNOASEMQZ-UHFFFAOYSA-N 0.000 description 1
- WSLMCPFAPFZVIY-UHFFFAOYSA-N 3-amino-4-(dimethylamino)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N(C)C)C(N)=C1 WSLMCPFAPFZVIY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UVSNSICXRVZAJR-UHFFFAOYSA-N 3-bromo-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(Br)=C1 UVSNSICXRVZAJR-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- IYTJRMRETHPZAC-UHFFFAOYSA-N 4,4-dibenzylpiperidine Chemical compound C1CNCCC1(CC=1C=CC=CC=1)CC1=CC=CC=C1 IYTJRMRETHPZAC-UHFFFAOYSA-N 0.000 description 1
- TZJVIARHKFQXNT-UHFFFAOYSA-N 4,6-dichloropyridine Chemical compound ClC1=C=C(Cl)N=C[CH]1 TZJVIARHKFQXNT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- FRIDVSSBTNZNJD-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzenesulfonyl chloride Chemical compound OC1=CC=C(S(Cl)(=O)=O)C=C1[N+]([O-])=O FRIDVSSBTNZNJD-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- RSGVKIIEIXOMPY-UHFFFAOYSA-N 5-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC=C(C(F)(F)F)C=N1 RSGVKIIEIXOMPY-UHFFFAOYSA-N 0.000 description 1
- NTNJMLBZGINDBS-UHFFFAOYSA-N 5-[(6-chloropyrimidin-4-yl)amino]-2-fluoro-n-methylbenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)NC)=CC(NC=2N=CN=C(Cl)C=2)=C1 NTNJMLBZGINDBS-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
- ABYCTYJDRLQBMT-UHFFFAOYSA-N 6-bromo-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(Br)=C1 ABYCTYJDRLQBMT-UHFFFAOYSA-N 0.000 description 1
- GVSLZUKQTPCNNU-UHFFFAOYSA-N 6-chloro-n-(3,4-difluorophenyl)pyrimidin-4-amine Chemical compound C1=C(F)C(F)=CC=C1NC1=CC(Cl)=NC=N1 GVSLZUKQTPCNNU-UHFFFAOYSA-N 0.000 description 1
- ZJZWAZPJQYYVJM-UHFFFAOYSA-N 6-chloro-n-(3-chloro-4-methoxyphenyl)pyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=CC(Cl)=NC=N1 ZJZWAZPJQYYVJM-UHFFFAOYSA-N 0.000 description 1
- XNFSCKQEUIDUEX-UHFFFAOYSA-N 6-chloro-n-(3-fluorophenyl)pyrimidin-4-amine Chemical compound FC1=CC=CC(NC=2N=CN=C(Cl)C=2)=C1 XNFSCKQEUIDUEX-UHFFFAOYSA-N 0.000 description 1
- QECWXEKMOKKSNA-UHFFFAOYSA-N 6-chloro-n-(4-propan-2-ylphenyl)pyrimidin-4-amine Chemical compound C1=CC(C(C)C)=CC=C1NC1=CC(Cl)=NC=N1 QECWXEKMOKKSNA-UHFFFAOYSA-N 0.000 description 1
- AYROZJOJRPYKFB-UHFFFAOYSA-N 6-chloro-n-(4-pyrazol-1-ylphenyl)pyrimidin-4-amine Chemical compound C1=NC(Cl)=CC(NC=2C=CC(=CC=2)N2N=CC=C2)=N1 AYROZJOJRPYKFB-UHFFFAOYSA-N 0.000 description 1
- AKLFCMYFFRILEY-UHFFFAOYSA-N 6-chloro-n-[4-(2,2,2-trifluoroethyl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(CC(F)(F)F)=CC=C1NC1=CC(Cl)=NC=N1 AKLFCMYFFRILEY-UHFFFAOYSA-N 0.000 description 1
- XHEOEDNFAUZYQW-UHFFFAOYSA-N 6-chloro-n-[4-(2-methoxyethoxy)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OCCOC)=CC=C1NC1=CC(Cl)=NC=N1 XHEOEDNFAUZYQW-UHFFFAOYSA-N 0.000 description 1
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
- 239000002081 C09CA05 - Tasosartan Substances 0.000 description 1
- 239000002053 C09CA06 - Candesartan Substances 0.000 description 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
- CFPJJOWVIYEDIH-UHFFFAOYSA-O CNS(c(cc1)cc(Nc2cc(Cl)ncn2)c1SC)([OH2+])=O Chemical compound CNS(c(cc1)cc(Nc2cc(Cl)ncn2)c1SC)([OH2+])=O CFPJJOWVIYEDIH-UHFFFAOYSA-O 0.000 description 1
- BHGWFSUYIDPJHV-UHFFFAOYSA-N CNS(c1cc(Nc2cc(Nc3cccc(OC)c3)ncn2)ccc1)(=O)=O Chemical compound CNS(c1cc(Nc2cc(Nc3cccc(OC)c3)ncn2)ccc1)(=O)=O BHGWFSUYIDPJHV-UHFFFAOYSA-N 0.000 description 1
- JZJGUFOXUUCASI-UHFFFAOYSA-N CNSc(cc1)cc(Nc2cc(Nc(cc3)cc(OC)c3OC)ncn2)c1SC Chemical compound CNSc(cc1)cc(Nc2cc(Nc(cc3)cc(OC)c3OC)ncn2)c1SC JZJGUFOXUUCASI-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JOATXPAWOHTVSZ-UHFFFAOYSA-N Celiprolol Chemical compound CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C(C)=O)=C1 JOATXPAWOHTVSZ-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 206010052337 Diastolic dysfunction Diseases 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- XQLWNAFCTODIRK-UHFFFAOYSA-N Gallopamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C(OC)=C1 XQLWNAFCTODIRK-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- WDZVGELJXXEGPV-YIXHJXPBSA-N Guanabenz Chemical compound NC(N)=N\N=C\C1=C(Cl)C=CC=C1Cl WDZVGELJXXEGPV-YIXHJXPBSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010049694 Left Ventricular Dysfunction Diseases 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CESYKOGBSMNBPD-UHFFFAOYSA-N Methyclothiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CCl)NC2=C1 CESYKOGBSMNBPD-UHFFFAOYSA-N 0.000 description 1
- UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
- FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005480 Olmesartan Substances 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 101710178685 Serine/threonine-protein kinase TNNI3K Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 102000013394 Troponin I Human genes 0.000 description 1
- 108010065729 Troponin I Proteins 0.000 description 1
- 241001660687 Xantho Species 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- UXRDAJMOOGEIAQ-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 UXRDAJMOOGEIAQ-CKOZHMEPSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960002122 acebutolol Drugs 0.000 description 1
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- YTIVTFGABIZHHX-UHFFFAOYSA-L acetylenedicarboxylate(2-) Chemical compound [O-]C(=O)C#CC([O-])=O YTIVTFGABIZHHX-UHFFFAOYSA-L 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 229960000528 amlodipine Drugs 0.000 description 1
- ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229960002932 anastrozole Drugs 0.000 description 1
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- PHFDAOXXIZOUIX-UHFFFAOYSA-N anipamil Chemical compound C=1C=CC(OC)=CC=1C(CCCCCCCCCCCC)(C#N)CCCN(C)CCC1=CC=CC(OC)=C1 PHFDAOXXIZOUIX-UHFFFAOYSA-N 0.000 description 1
- 229950011530 anipamil Drugs 0.000 description 1
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 229960002274 atenolol Drugs 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229960004324 betaxolol Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- OWMVSZAMULFTJU-UHFFFAOYSA-N bis-tris Chemical compound OCCN(CCO)C(CO)(CO)CO OWMVSZAMULFTJU-UHFFFAOYSA-N 0.000 description 1
- 229960002781 bisoprolol Drugs 0.000 description 1
- VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000005621 boronate group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- OAOXPQKIXSVSRH-UHFFFAOYSA-N butanedioic acid;propanedioic acid Chemical compound OC(=O)CC(O)=O.OC(=O)CCC(O)=O OAOXPQKIXSVSRH-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- GJYLKIZKRHDRER-UHFFFAOYSA-N calcium;sulfuric acid Chemical compound [Ca].OS(O)(=O)=O GJYLKIZKRHDRER-UHFFFAOYSA-N 0.000 description 1
- 229960000932 candesartan Drugs 0.000 description 1
- SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 description 1
- 239000007894 caplet Substances 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 210000004413 cardiac myocyte Anatomy 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 229960001222 carteolol Drugs 0.000 description 1
- 229960004195 carvedilol Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960002320 celiprolol Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960002155 chlorothiazide Drugs 0.000 description 1
- 229960001523 chlortalidone Drugs 0.000 description 1
- JIVPVXMEBJLZRO-UHFFFAOYSA-N chlorthalidone Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000001447 compensatory effect Effects 0.000 description 1
- 230000009091 contractile dysfunction Effects 0.000 description 1
- 229940069210 coreg Drugs 0.000 description 1
- 229940097488 corgard Drugs 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000005534 decanoate group Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229960005227 delapril Drugs 0.000 description 1
- WOUOLAUOZXOLJQ-MBSDFSHPSA-N delapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 WOUOLAUOZXOLJQ-MBSDFSHPSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
- 229960004166 diltiazem Drugs 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229960001208 eplerenone Drugs 0.000 description 1
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 1
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 1
- 229960004563 eprosartan Drugs 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 229960003745 esmolol Drugs 0.000 description 1
- AQNDDEOPVVGCPG-UHFFFAOYSA-N esmolol Chemical compound COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1 AQNDDEOPVVGCPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229960000255 exemestane Drugs 0.000 description 1
- 229960003580 felodipine Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- SMANXXCATUTDDT-QPJJXVBHSA-N flunarizine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C\C=C\C=2C=CC=CC=2)CC1 SMANXXCATUTDDT-QPJJXVBHSA-N 0.000 description 1
- 229960000326 flunarizine Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960000457 gallopamil Drugs 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 229960004553 guanabenz Drugs 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940120120 innopran Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229960002198 irbesartan Drugs 0.000 description 1
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 229960004427 isradipine Drugs 0.000 description 1
- 229940072289 kerlone Drugs 0.000 description 1
- 229960001632 labetalol Drugs 0.000 description 1
- 229960004340 lacidipine Drugs 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940096773 levatol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229940089504 lopressor Drugs 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- UJNNCGWBDJHCEM-UHFFFAOYSA-N methyl 2-amino-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C1=CN=C(N)S1 UJNNCGWBDJHCEM-UHFFFAOYSA-N 0.000 description 1
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
- IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229960005170 moexipril Drugs 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 230000037257 muscle growth Effects 0.000 description 1
- KSAMKARQFVLMFC-UHFFFAOYSA-N n,n-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine Chemical compound C1=NC(N(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 KSAMKARQFVLMFC-UHFFFAOYSA-N 0.000 description 1
- UVYOCMYQOSFCNZ-UHFFFAOYSA-N n-(3-bromo-5-methylphenyl)-6-chloropyrimidin-4-amine Chemical compound CC1=CC(Br)=CC(NC=2N=CN=C(Cl)C=2)=C1 UVYOCMYQOSFCNZ-UHFFFAOYSA-N 0.000 description 1
- DGRBAINVOAYLHV-UHFFFAOYSA-N n-(5-bromo-6-methylpyridin-2-yl)-6-chloropyrimidin-4-amine Chemical compound C1=C(Br)C(C)=NC(NC=2N=CN=C(Cl)C=2)=C1 DGRBAINVOAYLHV-UHFFFAOYSA-N 0.000 description 1
- WMLWDPNAIOLAPX-UHFFFAOYSA-N n-(6-bromo-4-methylpyridin-2-yl)-6-chloropyrimidin-4-amine Chemical compound CC1=CC(Br)=NC(NC=2N=CN=C(Cl)C=2)=C1 WMLWDPNAIOLAPX-UHFFFAOYSA-N 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YIIPTCFKYOTDME-UHFFFAOYSA-N n-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1 YIIPTCFKYOTDME-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004255 nadolol Drugs 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229960000619 nebivolol Drugs 0.000 description 1
- 230000002644 neurohormonal effect Effects 0.000 description 1
- 229960001783 nicardipine Drugs 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229950010800 niguldipine Drugs 0.000 description 1
- 229950000109 niludipine Drugs 0.000 description 1
- VZWXXKDFACOXNT-UHFFFAOYSA-N niludipine Chemical compound CCCOCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOCCC)C1C1=CC=CC([N+]([O-])=O)=C1 VZWXXKDFACOXNT-UHFFFAOYSA-N 0.000 description 1
- 229960005366 nilvadipine Drugs 0.000 description 1
- 229960000715 nimodipine Drugs 0.000 description 1
- 229960000227 nisoldipine Drugs 0.000 description 1
- 229960005425 nitrendipine Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- VTRAEEWXHOVJFV-UHFFFAOYSA-N olmesartan Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 VTRAEEWXHOVJFV-UHFFFAOYSA-N 0.000 description 1
- 229960005117 olmesartan Drugs 0.000 description 1
- LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 description 1
- 229950000973 omapatrilat Drugs 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 229960004570 oxprenolol Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000004963 pathophysiological condition Effects 0.000 description 1
- FEDSNBHHWZEYTP-ZFQYHYQMSA-N penbutolol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 FEDSNBHHWZEYTP-ZFQYHYQMSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229960002582 perindopril Drugs 0.000 description 1
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
- 230000036513 peripheral conductance Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960002508 pindolol Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 229960001989 prenylamine Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000036593 pulmonary vascular resistance Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- VIVPWOMJFLICOZ-UHFFFAOYSA-N pyridine-3-sulfonyl chloride;hydrochloride Chemical compound Cl.ClS(=O)(=O)C1=CC=CN=C1 VIVPWOMJFLICOZ-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229960002909 spirapril Drugs 0.000 description 1
- HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 description 1
- 108700035424 spirapril Proteins 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960000651 tasosartan Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- 229960004084 temocapril Drugs 0.000 description 1
- FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 1
- 229940108485 tenormin Drugs 0.000 description 1
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940083085 thiazide derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- BAVYZALUXZFZLV-FIBGUPNXSA-N trideuteriomethanamine Chemical compound [2H]C([2H])([2H])N BAVYZALUXZFZLV-FIBGUPNXSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-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=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940063670 visken Drugs 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29463710P | 2010-01-13 | 2010-01-13 | |
| US61/294,637 | 2010-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20120114355A true KR20120114355A (ko) | 2012-10-16 |
Family
ID=44304601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127021083A Withdrawn KR20120114355A (ko) | 2010-01-13 | 2011-01-11 | 화합물 및 방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20120329784A1 (enExample) |
| EP (1) | EP2523559A4 (enExample) |
| JP (1) | JP2013517273A (enExample) |
| KR (1) | KR20120114355A (enExample) |
| CN (1) | CN102791131A (enExample) |
| AU (1) | AU2011205485B2 (enExample) |
| BR (1) | BR112012017277A2 (enExample) |
| CA (1) | CA2786999A1 (enExample) |
| EA (1) | EA201290642A1 (enExample) |
| IL (1) | IL220812A0 (enExample) |
| MX (1) | MX2012008141A (enExample) |
| SG (1) | SG182351A1 (enExample) |
| WO (1) | WO2011088027A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112014027117B1 (pt) * | 2012-05-03 | 2022-09-06 | Genentech, Inc | Derivados de pirazol aminopirimidina como moduladores de lrrk2, seus usos, e composição |
| WO2014134391A1 (en) | 2013-02-28 | 2014-09-04 | 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 |
| AU2014233185B2 (en) | 2013-03-15 | 2018-03-15 | University Of Southern California | Methods, compounds, and compositions for the treatment of angiotensin-related 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 |
| AU2018274723B2 (en) * | 2017-05-26 | 2024-01-18 | Cancer Research Technology Limited | Benzimidazolone derived inhibitors of BCL6 |
| AU2019253510B2 (en) | 2018-04-13 | 2023-08-10 | Cancer Research Technology Limited | BCL6 inhibitors |
| 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 |
| WO2023196714A2 (en) * | 2022-02-23 | 2023-10-12 | President And Fellows Of Harvard College | Inhibitors of ddr1 and ddr2 for the treatment of arthritis |
| AR128846A1 (es) | 2022-03-23 | 2024-06-19 | Ideaya Biosciences Inc | Compuestos de indazol sustituidos con piperazina como inhibidores de parg |
| US11891362B1 (en) * | 2023-04-14 | 2024-02-06 | King Faisal University | N2,N4-disubstituted pyrimidine-2,4-diamine compounds as antibacterial agents |
| EP4716532A2 (en) * | 2023-05-23 | 2026-04-01 | Quantx Biosciences US, Inc. | Bicyclic heteroaryl compounds |
| US12358904B2 (en) * | 2023-06-02 | 2025-07-15 | Atomwise Inc. | Inhibitors of TYK2 |
| WO2024249831A2 (en) * | 2023-06-02 | 2024-12-05 | Unogen Biotech Ltd. | Triple kinase inhibitors |
| WO2025096550A1 (en) * | 2023-10-31 | 2025-05-08 | Twine Therapeutics, Inc. | Methods of treating cardiomyopathy |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW504510B (en) * | 1996-05-10 | 2002-10-01 | Janssen Pharmaceutica Nv | 2,4-diaminopyrimidine derivatives |
| CA2451128A1 (en) * | 2001-06-26 | 2003-01-09 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of tnf-alpha expression |
| US20070179161A1 (en) * | 2003-03-31 | 2007-08-02 | Vernalis (Cambridge) Limited. | Pyrazolopyrimidine compounds and their use in medicine |
| EP1678147B1 (en) * | 2003-09-15 | 2012-08-08 | Lead Discovery Center GmbH | Pharmaceutically active 4,6-disubstituted aminopyrimidine derivatives as modulators of protein kinases |
| EP1727806A1 (en) * | 2004-01-16 | 2006-12-06 | Novartis AG | 2,4-diaminopyrimidines and their use for inducing cardiomyogenesis |
| CA2553513A1 (en) * | 2004-01-22 | 2005-08-04 | Altana Pharma Ag | N-4-(6- (heteo) aryl-pyrimidin-4-ylaminophenyl) -bezenesulfonamides as kinase inhibitors |
| US20070203161A1 (en) * | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US7528143B2 (en) * | 2005-11-01 | 2009-05-05 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| ZA200804083B (en) * | 2005-11-01 | 2009-09-30 | Targegen Inc | Bi-aryl meta-pyrimidine inhibitors of kinases |
| EP2054392A2 (en) * | 2006-06-15 | 2009-05-06 | 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 |
| US7982036B2 (en) * | 2007-10-19 | 2011-07-19 | Avila Therapeutics, Inc. | 4,6-disubstitued pyrimidines useful as kinase inhibitors |
-
2011
- 2011-01-11 EA EA201290642A patent/EA201290642A1/ru unknown
- 2011-01-11 US US13/520,861 patent/US20120329784A1/en not_active Abandoned
- 2011-01-11 KR KR1020127021083A patent/KR20120114355A/ko not_active Withdrawn
- 2011-01-11 EP EP11733258.5A patent/EP2523559A4/en not_active Withdrawn
- 2011-01-11 JP JP2012549000A patent/JP2013517273A/ja active Pending
- 2011-01-11 MX MX2012008141A patent/MX2012008141A/es unknown
- 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 CN CN2011800138247A patent/CN102791131A/zh active Pending
- 2011-01-11 SG SG2012049409A patent/SG182351A1/en unknown
- 2011-01-11 CA CA2786999A patent/CA2786999A1/en not_active Abandoned
- 2011-01-11 WO PCT/US2011/020798 patent/WO2011088027A1/en not_active Ceased
-
2012
- 2012-07-05 IL IL220812A patent/IL220812A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2786999A1 (en) | 2011-07-21 |
| EA201290642A1 (ru) | 2013-05-30 |
| WO2011088027A1 (en) | 2011-07-21 |
| WO2011088027A8 (en) | 2012-08-30 |
| SG182351A1 (en) | 2012-08-30 |
| JP2013517273A (ja) | 2013-05-16 |
| AU2011205485A1 (en) | 2012-08-02 |
| MX2012008141A (es) | 2012-08-03 |
| BR112012017277A2 (pt) | 2017-10-03 |
| CN102791131A (zh) | 2012-11-21 |
| AU2011205485B2 (en) | 2014-09-25 |
| EP2523559A1 (en) | 2012-11-21 |
| EP2523559A4 (en) | 2013-11-06 |
| IL220812A0 (en) | 2012-08-30 |
| US20120329784A1 (en) | 2012-12-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013517273A (ja) | 化合物および方法 | |
| CA2827072C (en) | Diaminopyrimidine derivatives and processes for the preparation thereof | |
| JP4944286B1 (ja) | シクロプロパン化合物 | |
| KR20130138734A (ko) | 트라이아진 유도체 및 그것을 함유하는 진통 작용을 갖는 의약 조성물 | |
| MXPA04005862A (es) | Compuestos antagonistas selectivos de pirimidina a2b, su sintesis y uso. | |
| EP2552211A1 (en) | Indazolyl-pyrimidines as kinase inhibitors | |
| JP2009523797A (ja) | 炎症性障害の処置のためのヒダントイン化合物 | |
| US20100105674A1 (en) | Chemical Compounds | |
| MX2013000997A (es) | Compuestos de 1, 4, 5, 6-tetrahidro-pirimidin-2-ilamina. | |
| KR20120093428A (ko) | 스핑고신 키나아제 저해제 | |
| JP5836963B2 (ja) | キナゾリン化合物 | |
| CN105658644B (zh) | 取代咪唑用作n型钙通道阻滞剂 | |
| JP2013503170A (ja) | 化合物および方法 | |
| WO2011088031A1 (en) | Compounds and methods | |
| JP4834441B2 (ja) | ピリミジニルアルキルチオ基を有する新規環式化合物 | |
| RU2587981C2 (ru) | Производные диаминопиримидина и способы их получения | |
| AU2008240084A1 (en) | Pyrimidine derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20120810 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |