JP2015520232A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015520232A5 JP2015520232A5 JP2015518471A JP2015518471A JP2015520232A5 JP 2015520232 A5 JP2015520232 A5 JP 2015520232A5 JP 2015518471 A JP2015518471 A JP 2015518471A JP 2015518471 A JP2015518471 A JP 2015518471A JP 2015520232 A5 JP2015520232 A5 JP 2015520232A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- triazine
- carboxamide
- aminocyclohexyl
- oxobutan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 150000003839 salts Chemical class 0.000 claims description 84
- 125000005843 halogen group Chemical group 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000005842 heteroatom Chemical group 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- -1 2-aminocyclohexyl Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 7
- HNUXGKGGWIBQRA-JGVFFNPUSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(1,3-thiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2SC=NC=2)=N1 HNUXGKGGWIBQRA-JGVFFNPUSA-N 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 210000004027 cell Anatomy 0.000 claims description 5
- DEFDSCVFDCEKRD-CQSZACIVSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 DEFDSCVFDCEKRD-CQSZACIVSA-N 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000028622 Immune thrombocytopenia Diseases 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 102000000551 Syk Kinase Human genes 0.000 claims description 4
- 108010016672 Syk Kinase Proteins 0.000 claims description 4
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- DXFZQDKXRIAXCS-UHFFFAOYSA-N triazine-4-carboxamide Chemical compound NC(=O)C1=CC=NN=N1 DXFZQDKXRIAXCS-UHFFFAOYSA-N 0.000 claims description 4
- 230000002062 proliferating effect Effects 0.000 claims description 3
- PQKKCWZAVROFQE-CQSZACIVSA-N 3-[[(1R)-2-amino-2-oxo-1-phenylethyl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@@H](C(N)=O)C=2C=CC=CC=2)=NN=C1C(N)=O PQKKCWZAVROFQE-CQSZACIVSA-N 0.000 claims description 2
- CJSRBVUNMJDWMX-ZWNOBZJWSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(1,3-benzothiazol-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3SC=NC3=CC=2)=N1 CJSRBVUNMJDWMX-ZWNOBZJWSA-N 0.000 claims description 2
- BDPFQPDNLKMIRN-UKRRQHHQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3,4-dihydro-1H-isochromen-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3CCOCC3=CC=2)=N1 BDPFQPDNLKMIRN-UKRRQHHQSA-N 0.000 claims description 2
- OSCMRAHNENPVLT-UKRRQHHQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3,4-dihydro-1H-isochromen-7-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3COCCC3=CC=2)=N1 OSCMRAHNENPVLT-UKRRQHHQSA-N 0.000 claims description 2
- MIUDQKHEQLFZDL-ZYHUDNBSSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C=CC=2)=N1 MIUDQKHEQLFZDL-ZYHUDNBSSA-N 0.000 claims description 2
- VCJFEQDOPCFCLU-TZMCWYRMSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-cyano-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C#N)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=NN=C1C(N)=O VCJFEQDOPCFCLU-TZMCWYRMSA-N 0.000 claims description 2
- NBMOCOIZELAEOS-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-fluoro-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(F)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=NN=C1C(N)=O NBMOCOIZELAEOS-DGCLKSJQSA-N 0.000 claims description 2
- RKXKXSVTGYIPFR-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-fluoro-5-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC(F)=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 RKXKXSVTGYIPFR-DGCLKSJQSA-N 0.000 claims description 2
- NOMBWPRYIHPSJP-BXUZGUMPSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-methoxy-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C)C(OC)=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 NOMBWPRYIHPSJP-BXUZGUMPSA-N 0.000 claims description 2
- KKBWWFNLCNYCPL-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 KKBWWFNLCNYCPL-DGCLKSJQSA-N 0.000 claims description 2
- VOKZNAYAXGUXNN-ZWNOBZJWSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(4-chloro-3-methoxyanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 VOKZNAYAXGUXNN-ZWNOBZJWSA-N 0.000 claims description 2
- REYYDCRADMMODN-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=NN=C1C(N)=O REYYDCRADMMODN-DGCLKSJQSA-N 0.000 claims description 2
- HPBIFDFZFXESSX-UKRRQHHQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 HPBIFDFZFXESSX-UKRRQHHQSA-N 0.000 claims description 2
- VCKQCHJOYBTTEN-BXKDBHETSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-(thieno[2,3-b]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C3=CC=CN=C3SC=2)=N1 VCKQCHJOYBTTEN-BXKDBHETSA-N 0.000 claims description 2
- QHDISYZLXHMZSG-BXUZGUMPSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-methylindazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)N=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N QHDISYZLXHMZSG-BXUZGUMPSA-N 0.000 claims description 2
- SSRKQGJJCKUAOW-IUODEOHRSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=CC2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N SSRKQGJJCKUAOW-IUODEOHRSA-N 0.000 claims description 2
- VRJOHUABISCHSG-DGCLKSJQSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-methylpyrrolo[2,3-b]pyridin-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C=1N=C2N(C)C=CC2=CC=1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N VRJOHUABISCHSG-DGCLKSJQSA-N 0.000 claims description 2
- JKXVQLLPGGEPAF-IUODEOHRSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-oxidoquinolin-1-ium-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=[N+]([O-])C3=CC=2)=N1 JKXVQLLPGGEPAF-IUODEOHRSA-N 0.000 claims description 2
- YGPZKVFXMSUASF-CZUORRHYSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=C(C#N)C2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N YGPZKVFXMSUASF-CZUORRHYSA-N 0.000 claims description 2
- JLXTZYUHNQKVCP-TZMCWYRMSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[3-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2OC=CN=2)=N1 JLXTZYUHNQKVCP-TZMCWYRMSA-N 0.000 claims description 2
- VZLDOVQMBPXEET-TZMCWYRMSA-N 3-[[(1R,2R)-2-amino-3,3-difluorocyclohexyl]amino]-5-[4-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C=2OC=CN=2)=N1 VZLDOVQMBPXEET-TZMCWYRMSA-N 0.000 claims description 2
- LOWCUSYAFWXQOY-VHSXEESVSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(1,3-benzothiazol-7-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=3SC=NC=3C=CC=2)=N1 LOWCUSYAFWXQOY-VHSXEESVSA-N 0.000 claims description 2
- ACPFBGHGHDRKKQ-WCQYABFASA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(2-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C(=CC=CC=2)C#N)=N1 ACPFBGHGHDRKKQ-WCQYABFASA-N 0.000 claims description 2
- GZMMACCMYHRVBG-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-chloro-5-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C=C(F)C=2)=N1 GZMMACCMYHRVBG-NWDGAFQWSA-N 0.000 claims description 2
- UZGHIRRQDQJKMH-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C#N)=N1 UZGHIRRQDQJKMH-QWHCGFSZSA-N 0.000 claims description 2
- IMHGLGQUEBDRKS-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-fluoro-5-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC(F)=CC(NC=2C(=NN=C(N[C@H]3[C@H](CCCC3)N)N=2)C(N)=O)=C1 IMHGLGQUEBDRKS-QWHCGFSZSA-N 0.000 claims description 2
- LCHIDYRCIZWTGU-LSDHHAIUSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(3-pyrazol-1-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CC=C2)=N1 LCHIDYRCIZWTGU-LSDHHAIUSA-N 0.000 claims description 2
- ZDYDGWOIXLZZOV-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(Cl)=CC=2)=N1 ZDYDGWOIXLZZOV-NWDGAFQWSA-N 0.000 claims description 2
- CMQIMQMMVHHQED-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-cyano-3-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(C#N)=CC=2)=N1 CMQIMQMMVHHQED-QWHCGFSZSA-N 0.000 claims description 2
- PHRQFJRAMFZEQK-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C#N)=N1 PHRQFJRAMFZEQK-QWHCGFSZSA-N 0.000 claims description 2
- FEQOCZZXMBAWLC-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-fluoro-3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(F)C(C)=CC(NC=2C(=NN=C(N[C@H]3[C@H](CCCC3)N)N=2)C(N)=O)=C1 FEQOCZZXMBAWLC-QWHCGFSZSA-N 0.000 claims description 2
- REURUSXMYWMZJD-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(F)=CC=2)=N1 REURUSXMYWMZJD-NWDGAFQWSA-N 0.000 claims description 2
- XBCHLHAAWPFOHD-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O XBCHLHAAWPFOHD-QWHCGFSZSA-N 0.000 claims description 2
- OIWFJDIUCRBTGQ-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(imidazo[1,2-a]pyridin-7-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2=CC3=NC=CN3C=C2)=N1 OIWFJDIUCRBTGQ-NWDGAFQWSA-N 0.000 claims description 2
- AFEVUZLPGUTJEX-WDEREUQCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-(pyrazolo[1,5-a]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2=C3C=CC=CN3N=C2)=N1 AFEVUZLPGUTJEX-WDEREUQCSA-N 0.000 claims description 2
- YHKAHEUHVDHAHC-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(1-methylindazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N YHKAHEUHVDHAHC-QWHCGFSZSA-N 0.000 claims description 2
- AWMHYLZKQLCXFK-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(1-methylpyrrolo[2,3-c]pyridin-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=NC=C2N(C)C=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N AWMHYLZKQLCXFK-NWDGAFQWSA-N 0.000 claims description 2
- QZHWAWCKFNNRET-WDEREUQCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(2-methoxypyridin-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=NC(OC)=CC(NC=2C(=NN=C(N[C@H]3[C@H](CCCC3)N)N=2)C(N)=O)=C1 QZHWAWCKFNNRET-WDEREUQCSA-N 0.000 claims description 2
- JELUIACODZYMFB-LSDHHAIUSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=C(C#N)C2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N JELUIACODZYMFB-LSDHHAIUSA-N 0.000 claims description 2
- VWVLRQSCZNBNIE-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(3-phenyl-1,2,4-oxadiazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2ON=C(N=2)C=2C=CC=CC=2)=N1 VWVLRQSCZNBNIE-NWDGAFQWSA-N 0.000 claims description 2
- UBSXBZOWHDCART-WDEREUQCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(5-fluoropyridin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=NC=2)=N1 UBSXBZOWHDCART-WDEREUQCSA-N 0.000 claims description 2
- QXLFUYGITUBBPW-VHSXEESVSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(6-fluoropyridin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=NC(F)=CC=2)=N1 QXLFUYGITUBBPW-VHSXEESVSA-N 0.000 claims description 2
- SBIJHNZIRKOTDP-DZGCQCFKSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[(6-fluoroquinolin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=C(F)C=CC3=NC=2)=N1 SBIJHNZIRKOTDP-DZGCQCFKSA-N 0.000 claims description 2
- CGPCLXAGIFELSI-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[3-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2OC=CN=2)=N1 CGPCLXAGIFELSI-UONOGXRCSA-N 0.000 claims description 2
- WPCQGAGVKSOZNX-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C(F)(F)F)=N1 WPCQGAGVKSOZNX-NWDGAFQWSA-N 0.000 claims description 2
- RQRDEGAALIJFDE-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[3-fluoro-4-(3-oxomorpholin-4-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(N3C(COCC3)=O)=CC=2)=N1 RQRDEGAALIJFDE-UONOGXRCSA-N 0.000 claims description 2
- RLRPPGGWMWHWIE-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(1,2,4-triazol-1-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)N2N=CN=C2)=N1 RLRPPGGWMWHWIE-UONOGXRCSA-N 0.000 claims description 2
- GYKTYEVNORPXBF-ZAGLGSKWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(1-methyl-1-oxidopiperidin-1-ium-4-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1C[N+](C)([O-])CCC1C(C=C1)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O GYKTYEVNORPXBF-ZAGLGSKWSA-N 0.000 claims description 2
- OQJJAWMFUMTGEQ-RBUKOAKNSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(1-propanoylpiperidin-4-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CN(C(=O)CC)CCC1C(C=C1)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O OQJJAWMFUMTGEQ-RBUKOAKNSA-N 0.000 claims description 2
- MZUJIEIUQVCPLD-LSDHHAIUSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(azetidine-1-carbonyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C(=O)N2CCC2)=N1 MZUJIEIUQVCPLD-LSDHHAIUSA-N 0.000 claims description 2
- CQLPUHUAFIQJHP-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(dimethylcarbamoyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O CQLPUHUAFIQJHP-UONOGXRCSA-N 0.000 claims description 2
- OMWSSROGEUAMKM-UONOGXRCSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(triazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)N2N=CC=N2)=N1 OMWSSROGEUAMKM-UONOGXRCSA-N 0.000 claims description 2
- JBSJZPVXBNNOEX-NWDGAFQWSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[4-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C(F)(F)F)=N1 JBSJZPVXBNNOEX-NWDGAFQWSA-N 0.000 claims description 2
- BFPHBWPZQPCUJP-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[[5-(4-fluorophenyl)-1,2-oxazol-3-yl]amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2=NOC(=C2)C=2C=CC(F)=CC=2)=N1 BFPHBWPZQPCUJP-QWHCGFSZSA-N 0.000 claims description 2
- FDZWLWQQZJHNPG-QWHCGFSZSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[[6-(azetidine-1-carbonyl)pyridin-3-yl]amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=NC(=CC=2)C(=O)N2CCC2)=N1 FDZWLWQQZJHNPG-QWHCGFSZSA-N 0.000 claims description 2
- ZVBIERORAMJXRJ-NOZJJQNGSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(1,3-benzothiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3N=CSC3=CC=2)=N1 ZVBIERORAMJXRJ-NOZJJQNGSA-N 0.000 claims description 2
- VPYMGMRGRCRZJW-UKRRQHHQSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(2,3-dihydro-1h-inden-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3CCCC3=CC=2)=N1 VPYMGMRGRCRZJW-UKRRQHHQSA-N 0.000 claims description 2
- VUJBTWVSVYPNIW-ZYHUDNBSSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3,4-dichloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(Cl)=CC=2)=N1 VUJBTWVSVYPNIW-ZYHUDNBSSA-N 0.000 claims description 2
- WJDDIZSXJIEKOX-TZMCWYRMSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3,4-dimethylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=NN=C1C(N)=O WJDDIZSXJIEKOX-TZMCWYRMSA-N 0.000 claims description 2
- ZWJYVYNHKKLEML-UKRRQHHQSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(3-pyrimidin-2-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2N=CC=CN=2)=N1 ZWJYVYNHKKLEML-UKRRQHHQSA-N 0.000 claims description 2
- XUZNZAGFFADSQX-DGCLKSJQSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(4-chloro-3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(C)=CC(NC=2C(=NN=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)C(N)=O)=C1 XUZNZAGFFADSQX-DGCLKSJQSA-N 0.000 claims description 2
- ZXZJQXVGLXVUIB-ZYHUDNBSSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(4-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(Cl)=CC=2)=N1 ZXZJQXVGLXVUIB-ZYHUDNBSSA-N 0.000 claims description 2
- HRXCSCRLWOPNER-GDBMZVCRSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(5,6,7,8-tetrahydronaphthalen-2-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3CCCCC3=CC=2)=N1 HRXCSCRLWOPNER-GDBMZVCRSA-N 0.000 claims description 2
- GRKJSEWZRQXVDC-NOZJJQNGSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-(pyrazolo[1,5-a]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC2=C3C=CC=CN3N=C2)=N1 GRKJSEWZRQXVDC-NOZJJQNGSA-N 0.000 claims description 2
- DQPYLCFCPOUZNE-IUODEOHRSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-[(1-methylindol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)C=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC(F)(F)[C@@H]1N DQPYLCFCPOUZNE-IUODEOHRSA-N 0.000 claims description 2
- KVMWGQOHPRNIJP-ZYHUDNBSSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-[3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C(F)(F)F)=N1 KVMWGQOHPRNIJP-ZYHUDNBSSA-N 0.000 claims description 2
- WMJCUQRFRVDHOJ-ZYHUDNBSSA-N 3-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-5-[4-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C(F)(F)F)=N1 WMJCUQRFRVDHOJ-ZYHUDNBSSA-N 0.000 claims description 2
- YRRJXVQAIUEAOB-MERJSTESSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,2,3,4-tetrahydronaphthalen-2-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2CC3=CC=CC=C3CC2)=N1 YRRJXVQAIUEAOB-MERJSTESSA-N 0.000 claims description 2
- DIXOLQVHMWYDKN-WDEREUQCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,3-benzothiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3N=CSC3=CC=2)=N1 DIXOLQVHMWYDKN-WDEREUQCSA-N 0.000 claims description 2
- DXJDHIQZTRGKBX-WDEREUQCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,3-benzothiazol-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3SC=NC3=CC=2)=N1 DXJDHIQZTRGKBX-WDEREUQCSA-N 0.000 claims description 2
- DZAPLSLRQLBYMB-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,5-naphthyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=NC=2)=N1 DZAPLSLRQLBYMB-NWDGAFQWSA-N 0.000 claims description 2
- KCOICATWZFXLGO-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1,8-naphthyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=NC=2)=N1 KCOICATWZFXLGO-QWHCGFSZSA-N 0.000 claims description 2
- LZGMSBDCJXPVQV-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(1h-indazol-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3NN=CC3=CC=2)=N1 LZGMSBDCJXPVQV-NWDGAFQWSA-N 0.000 claims description 2
- DUFXKLJOXRIASW-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3,4-difluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(F)=CC=2)=N1 DUFXKLJOXRIASW-NWDGAFQWSA-N 0.000 claims description 2
- KGXGRDRRHBKPJE-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3,4-dimethylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O KGXGRDRRHBKPJE-UONOGXRCSA-N 0.000 claims description 2
- CWMZXHYLOWBPQH-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3,5-difluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=C(F)C=2)=N1 CWMZXHYLOWBPQH-NWDGAFQWSA-N 0.000 claims description 2
- JBACHQACXOJEBU-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3-chloro-4-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(F)=CC=2)=N1 JBACHQACXOJEBU-NWDGAFQWSA-N 0.000 claims description 2
- SVXUVFHLRLELNY-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3-chloro-4-methoxyanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O SVXUVFHLRLELNY-NWDGAFQWSA-N 0.000 claims description 2
- ZSFFITPMKGIELZ-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C=CC=2)=N1 ZSFFITPMKGIELZ-NWDGAFQWSA-N 0.000 claims description 2
- OFJGAIFPYRBRPR-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3-fluoro-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(F)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O OFJGAIFPYRBRPR-QWHCGFSZSA-N 0.000 claims description 2
- JZEFVZIMQZRCST-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=CC=2)=N1 JZEFVZIMQZRCST-NWDGAFQWSA-N 0.000 claims description 2
- AEUVEWUNZGHHIV-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC=CC(NC=2C(=NN=C(N[C@H]3[C@H](CCCC3)N)N=2)C(N)=O)=C1 AEUVEWUNZGHHIV-QWHCGFSZSA-N 0.000 claims description 2
- PGLFSEGLAXPQJW-LSDHHAIUSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(3-pyrimidin-2-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2N=CC=CN=2)=N1 PGLFSEGLAXPQJW-LSDHHAIUSA-N 0.000 claims description 2
- GPHRYZRGGGLZPF-LSDHHAIUSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(4-pyrimidin-2-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C=2N=CC=CN=2)=N1 GPHRYZRGGGLZPF-LSDHHAIUSA-N 0.000 claims description 2
- JXOWSEQICYZREV-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(imidazo[1,2-a]pyridin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC2=CN3C=CN=C3C=C2)=N1 JXOWSEQICYZREV-NWDGAFQWSA-N 0.000 claims description 2
- DJPKDVIPVABPIZ-WDEREUQCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=NC=CC=2)=N1 DJPKDVIPVABPIZ-WDEREUQCSA-N 0.000 claims description 2
- YOYCPOFXMNUXKS-DZGCQCFKSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(quinolin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=CC3=NC=2)=N1 YOYCPOFXMNUXKS-DZGCQCFKSA-N 0.000 claims description 2
- HEFUKPNHXUIESH-SWLSCSKDSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(quinolin-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C3=CC=CN=C3C=CC=2)=N1 HEFUKPNHXUIESH-SWLSCSKDSA-N 0.000 claims description 2
- LQJGRJQMPDAGSF-DZGCQCFKSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 LQJGRJQMPDAGSF-DZGCQCFKSA-N 0.000 claims description 2
- VBQXOKGMXNJYLC-WDEREUQCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-(thieno[2,3-b]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C3=CC=CN=C3SC=2)=N1 VBQXOKGMXNJYLC-WDEREUQCSA-N 0.000 claims description 2
- HGJHRMSEHCXAOV-WCQYABFASA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylindazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)N=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N HGJHRMSEHCXAOV-WCQYABFASA-N 0.000 claims description 2
- ZEDCUHFICWPSEY-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)N=CC2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N ZEDCUHFICWPSEY-QWHCGFSZSA-N 0.000 claims description 2
- PHRFJJCZJANURI-GXTWGEPZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylindol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)C=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N PHRFJJCZJANURI-GXTWGEPZSA-N 0.000 claims description 2
- NEWJTVVHTBOYKF-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylindol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C=1C=C2N(C)C=CC2=CC=1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N NEWJTVVHTBOYKF-UONOGXRCSA-N 0.000 claims description 2
- MMRQTMXTTUQLPS-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=CC2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N MMRQTMXTTUQLPS-UONOGXRCSA-N 0.000 claims description 2
- ZQZMYJFSYZGLJG-VHSXEESVSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylpyrazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O ZQZMYJFSYZGLJG-VHSXEESVSA-N 0.000 claims description 2
- AYGJTSFJHOLDHC-CMPLNLGQSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylpyrazolo[3,4-b]pyridin-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CN=C2N(C)N=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N AYGJTSFJHOLDHC-CMPLNLGQSA-N 0.000 claims description 2
- FVNBCTYGQPADBV-WCQYABFASA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-methylpyrrolo[2,3-b]pyridin-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CN=C2N(C)C=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N FVNBCTYGQPADBV-WCQYABFASA-N 0.000 claims description 2
- RJQIJLQWTGXXCC-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(1-oxidoquinolin-1-ium-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=[N+]([O-])C3=CC=2)=N1 RJQIJLQWTGXXCC-UONOGXRCSA-N 0.000 claims description 2
- FRMYPAINHTYHGY-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(2-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C=1C2=NN(C)C=C2C=CC=1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCCC[C@@H]1N FRMYPAINHTYHGY-QWHCGFSZSA-N 0.000 claims description 2
- YYNJHBIRIQINPT-DTWKUNHWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(3-methyl-1,2-thiazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound S1N=C(C)C=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O YYNJHBIRIQINPT-DTWKUNHWSA-N 0.000 claims description 2
- DIJFKLJESOSCDW-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(7-fluoroquinolin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC(F)=CC3=NC=2)=N1 DIJFKLJESOSCDW-UONOGXRCSA-N 0.000 claims description 2
- LUPMZTYJBDKPKS-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(8-chloroquinolin-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=C(Cl)C=2)=N1 LUPMZTYJBDKPKS-UONOGXRCSA-N 0.000 claims description 2
- JCKOVSWBRCZXHQ-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[(8-fluoroquinolin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=C(F)C3=NC=2)=N1 JCKOVSWBRCZXHQ-UONOGXRCSA-N 0.000 claims description 2
- KIBPHJNTDHNRRV-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[3-(1,2,4-triazol-1-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CN=C2)=N1 KIBPHJNTDHNRRV-UONOGXRCSA-N 0.000 claims description 2
- OMJJIGXALGBEDL-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[3-(difluoromethoxy)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(OC(F)F)C=CC=2)=N1 OMJJIGXALGBEDL-NWDGAFQWSA-N 0.000 claims description 2
- QYUNZLTYDOGJCE-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[3-(triazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CC=N2)=N1 QYUNZLTYDOGJCE-UONOGXRCSA-N 0.000 claims description 2
- FJKVANSWLNEJGL-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[3-chloro-4-(dimethylamino)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(N(C)C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O FJKVANSWLNEJGL-QWHCGFSZSA-N 0.000 claims description 2
- YEGXXDTXDZOTPU-UONOGXRCSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[4-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C=2OC=CN=2)=N1 YEGXXDTXDZOTPU-UONOGXRCSA-N 0.000 claims description 2
- AIHPINZMKDSYIY-QWHCGFSZSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[4-(dimethylamino)-3-fluoroanilino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C(F)C(N(C)C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O AIHPINZMKDSYIY-QWHCGFSZSA-N 0.000 claims description 2
- NBJYFETWTAMRJW-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[4-methoxy-3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O NBJYFETWTAMRJW-NWDGAFQWSA-N 0.000 claims description 2
- BVILEBWDRRXLJC-NWDGAFQWSA-N 3-[[(1r,2s)-2-aminocyclohexyl]amino]-5-[[6-(dimethylcarbamoyl)pyridin-3-yl]amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=NC(C(=O)N(C)C)=CC=C1NC1=NC(N[C@H]2[C@H](CCCC2)N)=NN=C1C(N)=O BVILEBWDRRXLJC-NWDGAFQWSA-N 0.000 claims description 2
- PEPTYSVDAHTANL-MRVPVSSYSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(1,3-benzothiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3N=CSC3=CC=2)=N1 PEPTYSVDAHTANL-MRVPVSSYSA-N 0.000 claims description 2
- WBBKHTGOJTWQNO-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(1,3-dihydro-2-benzofuran-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3COCC3=CC=2)=N1 WBBKHTGOJTWQNO-LLVKDONJSA-N 0.000 claims description 2
- YLNIZSHPTFQALC-RXMQYKEDSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(1,3-thiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2SC=NC=2)=N1 YLNIZSHPTFQALC-RXMQYKEDSA-N 0.000 claims description 2
- HHMSCHRYOIWPQM-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(1,5-naphthyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=NC=2)=N1 HHMSCHRYOIWPQM-SECBINFHSA-N 0.000 claims description 2
- GVZZNFGDPROQRL-SNVBAGLBSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(1H-indol-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3NC=CC3=CC=2)=N1 GVZZNFGDPROQRL-SNVBAGLBSA-N 0.000 claims description 2
- BQPIBPGPWXRGDT-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3,4-dichloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(Cl)=CC=2)=N1 BQPIBPGPWXRGDT-SECBINFHSA-N 0.000 claims description 2
- UVFIYERUUVMGJX-GFCCVEGCSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3,4-dihydro-1H-isochromen-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3CCOCC3=CC=2)=N1 UVFIYERUUVMGJX-GFCCVEGCSA-N 0.000 claims description 2
- ZHTOUNLNFLHASV-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3,4-dimethylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C)C(C)=CC=2)=N1 ZHTOUNLNFLHASV-LLVKDONJSA-N 0.000 claims description 2
- OHQQKBQZIHVMKA-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3-chloro-4-methoxyanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(OC)=CC=2)=N1 OHQQKBQZIHVMKA-SECBINFHSA-N 0.000 claims description 2
- YPNPLXLBSSFJLV-SNVBAGLBSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3-chloro-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(C)=CC=2)=N1 YPNPLXLBSSFJLV-SNVBAGLBSA-N 0.000 claims description 2
- VXFPNZOLLBDMKJ-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3-cyano-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C(C)=CC=2)C#N)=N1 VXFPNZOLLBDMKJ-LLVKDONJSA-N 0.000 claims description 2
- SENFNVRMEMMMQA-GFCCVEGCSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3-fluoro-4-morpholin-4-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(N3CCOCC3)=CC=2)=N1 SENFNVRMEMMMQA-GFCCVEGCSA-N 0.000 claims description 2
- CXWMNWIBPALLTH-SNVBAGLBSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C)C=CC=2)=N1 CXWMNWIBPALLTH-SNVBAGLBSA-N 0.000 claims description 2
- YUSFWQXNQMUQSK-GFCCVEGCSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(3-pyrimidin-2-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2N=CC=CN=2)=N1 YUSFWQXNQMUQSK-GFCCVEGCSA-N 0.000 claims description 2
- BIPCGJBSKDGTRY-SNVBAGLBSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(4-chloro-3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C)C(Cl)=CC=2)=N1 BIPCGJBSKDGTRY-SNVBAGLBSA-N 0.000 claims description 2
- KLBJHFONTOFSSG-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(4-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(Cl)=CC=2)=N1 KLBJHFONTOFSSG-SECBINFHSA-N 0.000 claims description 2
- OTELZKWMLPMSBS-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(quinolin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=CC3=NC=2)=N1 OTELZKWMLPMSBS-LLVKDONJSA-N 0.000 claims description 2
- OAMMGVAVEHAUNP-MRVPVSSYSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-(thieno[2,3-b]pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C3=CC=CN=C3SC=2)=N1 OAMMGVAVEHAUNP-MRVPVSSYSA-N 0.000 claims description 2
- DEHLWSRRRZYJCS-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(1-methylindazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=3C=NN(C)C=3C=CC=2)=N1 DEHLWSRRRZYJCS-SECBINFHSA-N 0.000 claims description 2
- ITAJRSCJALRPPJ-SNVBAGLBSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(1-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3N(C)N=CC3=CC=2)=N1 ITAJRSCJALRPPJ-SNVBAGLBSA-N 0.000 claims description 2
- HUURYEYDRVWOFN-SNVBAGLBSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(1-methylindol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=3C=CN(C)C=3C=CC=2)=N1 HUURYEYDRVWOFN-SNVBAGLBSA-N 0.000 claims description 2
- METUXPOGPQIGPJ-SNVBAGLBSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(2-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC2=CC3=NN(C)C=C3C=C2)=N1 METUXPOGPQIGPJ-SNVBAGLBSA-N 0.000 claims description 2
- BWFWMWGBXCWFFA-GFCCVEGCSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(3-cyano-1-methylindol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C(C#N)=CN(C)C3=CC=2)=N1 BWFWMWGBXCWFFA-GFCCVEGCSA-N 0.000 claims description 2
- XMJJUIQAIGMTBQ-GFCCVEGCSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3N(C)C=C(C3=CC=2)C#N)=N1 XMJJUIQAIGMTBQ-GFCCVEGCSA-N 0.000 claims description 2
- TYIPFYJZZQDVMM-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(3-iodo-1-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3N(C)N=C(I)C3=CC=2)=N1 TYIPFYJZZQDVMM-SECBINFHSA-N 0.000 claims description 2
- YWVIQSORQXPBCS-ZCFIWIBFSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(3-methyl-1,2-thiazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2SN=C(C)C=2)=N1 YWVIQSORQXPBCS-ZCFIWIBFSA-N 0.000 claims description 2
- JYNXEYNLXPRETQ-MRVPVSSYSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(5-fluoropyridin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=NC=2)=N1 JYNXEYNLXPRETQ-MRVPVSSYSA-N 0.000 claims description 2
- OMYHMEOOSDKOPN-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(5-iodo-1-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C(=CC=3C=NN(C)C=3C=2)I)=N1 OMYHMEOOSDKOPN-SECBINFHSA-N 0.000 claims description 2
- IXXQQKMAPCEQNE-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(6-fluoroquinolin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=C(F)C=CC3=NC=2)=N1 IXXQQKMAPCEQNE-LLVKDONJSA-N 0.000 claims description 2
- IISSXDYJXILUFW-MRVPVSSYSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(7-iodo-1-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C(=C3N(C)N=CC3=CC=2)I)=N1 IISSXDYJXILUFW-MRVPVSSYSA-N 0.000 claims description 2
- DVXIHIHONBOXDK-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[(8-chloroquinolin-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=C(Cl)C=2)=N1 DVXIHIHONBOXDK-LLVKDONJSA-N 0.000 claims description 2
- HUXWMSJJJOHCMD-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[3-(triazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CC=N2)=N1 HUXWMSJJJOHCMD-LLVKDONJSA-N 0.000 claims description 2
- XHILQZZTKRBIOQ-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C(F)(F)F)=N1 XHILQZZTKRBIOQ-SECBINFHSA-N 0.000 claims description 2
- PNEFQBWYCXYRSD-LLVKDONJSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[4-(triazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)N2N=CC=N2)=N1 PNEFQBWYCXYRSD-LLVKDONJSA-N 0.000 claims description 2
- LNXMUYSIMPYWRQ-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-[4-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C(F)(F)F)=N1 LNXMUYSIMPYWRQ-SECBINFHSA-N 0.000 claims description 2
- DREDJRNJXZQZGF-SECBINFHSA-N 3-[[(2R)-1-amino-1-oxobutan-2-yl]amino]-5-anilino-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC=CC=2)=N1 DREDJRNJXZQZGF-SECBINFHSA-N 0.000 claims description 2
- WVKMLLCFXZHFSL-MRVPVSSYSA-N 3-[[(2R)-1-amino-1-oxopropan-2-yl]amino]-5-[(1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound NC(=O)[C@@H](C)NC1=NN=C(C(N)=O)C(NC=2C=C3N(C)C=CC3=CC=2)=N1 WVKMLLCFXZHFSL-MRVPVSSYSA-N 0.000 claims description 2
- XIUSLEDXHDVBEB-AWEZNQCLSA-N 3-[[(2R)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]amino]-5-[(1-methylindol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)C=CC2=C1NC1=NC(N[C@@H](C(N)=O)C(C)(C)C)=NN=C1C(N)=O XIUSLEDXHDVBEB-AWEZNQCLSA-N 0.000 claims description 2
- VRBOCDPZEZLOLM-CQSZACIVSA-N 3-[[(2R)-1-amino-3-cyclopropyl-1-oxopropan-2-yl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C([C@@H](NC=1N=C(C(=NN=1)C(N)=O)NC1=CC=C2C(C#N)=CN(C2=C1)C)C(N)=O)C1CC1 VRBOCDPZEZLOLM-CQSZACIVSA-N 0.000 claims description 2
- NNULWBRXPOYRLQ-MRVPVSSYSA-N 3-[[(2R)-1-amino-3-cyclopropyl-1-oxopropan-2-yl]amino]-5-[(3-methyl-1,2-thiazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound S1N=C(C)C=C1NC1=NC(N[C@H](CC2CC2)C(N)=O)=NN=C1C(N)=O NNULWBRXPOYRLQ-MRVPVSSYSA-N 0.000 claims description 2
- BRAVRLLQDBNHCY-GFCCVEGCSA-N 3-[[(2R)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-5-(3,4-dimethylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C)C(C)=CC=2)=N1 BRAVRLLQDBNHCY-GFCCVEGCSA-N 0.000 claims description 2
- HJPBBIUMJSGVTF-SECBINFHSA-N 3-[[(2R)-1-amino-4,4,4-trifluoro-1-oxobutan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H](CC(F)(F)F)C(N)=O)=NN=C1C(N)=O HJPBBIUMJSGVTF-SECBINFHSA-N 0.000 claims description 2
- DTQJCTBIJVQWKU-LLVKDONJSA-N 3-[[(2R)-1-amino-4,4,4-trifluoro-1-oxobutan-2-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound FC(F)(F)C[C@H](C(=O)N)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 DTQJCTBIJVQWKU-LLVKDONJSA-N 0.000 claims description 2
- KVKGIPLFGDGVKU-SECBINFHSA-N 3-[[(2R)-1-amino-4,4-difluoro-1-oxobutan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H](CC(F)F)C(N)=O)=NN=C1C(N)=O KVKGIPLFGDGVKU-SECBINFHSA-N 0.000 claims description 2
- MQGORAUPXSCDRC-LLVKDONJSA-N 3-[[(2R)-1-amino-4,4-difluoro-1-oxobutan-2-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound FC(F)C[C@H](C(=O)N)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 MQGORAUPXSCDRC-LLVKDONJSA-N 0.000 claims description 2
- KSDLUGICLFRIRF-SECBINFHSA-N 3-[[(2R)-1-amino-4,4-difluoro-1-oxobutan-2-yl]amino]-5-[(1-methylindazol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)N=CC2=CC=C1NC1=NC(N[C@H](CC(F)F)C(N)=O)=NN=C1C(N)=O KSDLUGICLFRIRF-SECBINFHSA-N 0.000 claims description 2
- QRMDCFKUQSIDHH-LLVKDONJSA-N 3-[[(2R)-1-amino-4,4-difluoro-1-oxobutan-2-yl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=C(C#N)C2=CC=C1NC1=NC(N[C@H](CC(F)F)C(N)=O)=NN=C1C(N)=O QRMDCFKUQSIDHH-LLVKDONJSA-N 0.000 claims description 2
- KQVULDODEVUALX-CYBMUJFWSA-N 3-[[(2R)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(1H-indol-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3NC=CC3=CC=2)=N1 KQVULDODEVUALX-CYBMUJFWSA-N 0.000 claims description 2
- GFZQPMYMKZGLOJ-LLVKDONJSA-N 3-[[(2R)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(4-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(Cl)=CC=2)=N1 GFZQPMYMKZGLOJ-LLVKDONJSA-N 0.000 claims description 2
- HUDSGQQFKYSACC-GFCCVEGCSA-N 3-[[(2R)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-[(1-methylindazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=3C=NN(C)C=3C=CC=2)=N1 HUDSGQQFKYSACC-GFCCVEGCSA-N 0.000 claims description 2
- UQLHMMVOTXNRIN-CYBMUJFWSA-N 3-[[(2R)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-[(1-methylindol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=3C=CN(C)C=3C=CC=2)=N1 UQLHMMVOTXNRIN-CYBMUJFWSA-N 0.000 claims description 2
- MFMZNUSGEICXMC-SNVBAGLBSA-N 3-[[(2R)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-[(5-fluoropyridin-3-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=NC=2)=N1 MFMZNUSGEICXMC-SNVBAGLBSA-N 0.000 claims description 2
- HFRLYKLOFOMMMJ-CYBMUJFWSA-N 3-[[(2R)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-[3-(triazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CC=N2)=N1 HFRLYKLOFOMMMJ-CYBMUJFWSA-N 0.000 claims description 2
- KHEOSNGDAMOTNQ-LLVKDONJSA-N 3-[[(2R)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-[4-methoxy-3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1NC1=NC(N[C@H](CC(C)C)C(N)=O)=NN=C1C(N)=O KHEOSNGDAMOTNQ-LLVKDONJSA-N 0.000 claims description 2
- CUZNLPHMCMGSEJ-CYBMUJFWSA-N 3-[[(2r)-1-amino-1-oxo-3-thiophen-2-ylpropan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H](CC=2SC=CC=2)C(N)=O)=NN=C1C(N)=O CUZNLPHMCMGSEJ-CYBMUJFWSA-N 0.000 claims description 2
- NGIWYIPFHARVLG-GFCCVEGCSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(2,3-dihydro-1h-inden-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3CCCC3=CC=2)=N1 NGIWYIPFHARVLG-GFCCVEGCSA-N 0.000 claims description 2
- XIMROFVKJBXYOZ-GFCCVEGCSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(3,4-dihydro-1h-isochromen-7-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3COCCC3=CC=2)=N1 XIMROFVKJBXYOZ-GFCCVEGCSA-N 0.000 claims description 2
- PXJASIAPXUUFDS-SECBINFHSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(3-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C=CC=2)=N1 PXJASIAPXUUFDS-SECBINFHSA-N 0.000 claims description 2
- NRDVRVKOZSUBNX-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(3-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C#N)=N1 NRDVRVKOZSUBNX-SNVBAGLBSA-N 0.000 claims description 2
- WKFVXTLAQXDEKE-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(3-fluoro-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(C)=CC=2)=N1 WKFVXTLAQXDEKE-SNVBAGLBSA-N 0.000 claims description 2
- ALRFGFZCPMYYBJ-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(3-fluoro-5-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=C(C)C=2)=N1 ALRFGFZCPMYYBJ-SNVBAGLBSA-N 0.000 claims description 2
- PMTPCGJSBZOLFM-SECBINFHSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(3-fluoroanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(F)C=CC=2)=N1 PMTPCGJSBZOLFM-SECBINFHSA-N 0.000 claims description 2
- DQALFBSYMFOQGM-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(3-methoxy-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(OC)C(C)=CC=2)=N1 DQALFBSYMFOQGM-SNVBAGLBSA-N 0.000 claims description 2
- OCUGUKOMSLCLNW-SECBINFHSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(4-chloro-3-methoxyanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(OC)C(Cl)=CC=2)=N1 OCUGUKOMSLCLNW-SECBINFHSA-N 0.000 claims description 2
- BSRSUNBXCOTZFZ-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(4-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C#N)=N1 BSRSUNBXCOTZFZ-SNVBAGLBSA-N 0.000 claims description 2
- NWBTYCSQPMQMGM-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(C)=CC=2)=N1 NWBTYCSQPMQMGM-SNVBAGLBSA-N 0.000 claims description 2
- MLSSUKCQIKDFMU-LLVKDONJSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 MLSSUKCQIKDFMU-LLVKDONJSA-N 0.000 claims description 2
- IKPILSGDZREGKL-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[(1-methylindazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=NN(C)C3=CC=2)=N1 IKPILSGDZREGKL-SNVBAGLBSA-N 0.000 claims description 2
- URJMUBNSDDFKRI-LLVKDONJSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[(1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3N(C)C=CC3=CC=2)=N1 URJMUBNSDDFKRI-LLVKDONJSA-N 0.000 claims description 2
- WUDIPLZKTFFQHL-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[(1-methylpyrrolo[2,3-b]pyridin-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CN(C)C3=NC=2)=N1 WUDIPLZKTFFQHL-SNVBAGLBSA-N 0.000 claims description 2
- RRWSRRMIFNWYDA-SECBINFHSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[3-chloro-4-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(=CC=2)C(F)(F)F)=N1 RRWSRRMIFNWYDA-SECBINFHSA-N 0.000 claims description 2
- ABKXXHSGMQZUJW-SNVBAGLBSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[4-(dimethylamino)-3-fluoroanilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(N(C)C)=CC=2)=N1 ABKXXHSGMQZUJW-SNVBAGLBSA-N 0.000 claims description 2
- RGQFSPYOOLPJBK-SECBINFHSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[4-chloro-3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C(Cl)=CC=2)C(F)(F)F)=N1 RGQFSPYOOLPJBK-SECBINFHSA-N 0.000 claims description 2
- BOGZHIUPUYYAMC-SECBINFHSA-N 3-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-5-[4-methoxy-3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C(OC)=CC=2)C(F)(F)F)=N1 BOGZHIUPUYYAMC-SECBINFHSA-N 0.000 claims description 2
- HTQLFIUQDWMMDB-OAHLLOKOSA-N 3-[[(2r)-1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H](CC=2C=C(F)C=CC=2)C(N)=O)=NN=C1C(N)=O HTQLFIUQDWMMDB-OAHLLOKOSA-N 0.000 claims description 2
- YWVUFFCFCIQUKU-LLVKDONJSA-N 3-[[(2r)-1-amino-3-cyclopropyl-1-oxopropan-2-yl]amino]-5-(3,4-dichloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound C([C@H](C(=O)N)NC=1N=C(NC=2C=C(Cl)C(Cl)=CC=2)C(C(N)=O)=NN=1)C1CC1 YWVUFFCFCIQUKU-LLVKDONJSA-N 0.000 claims description 2
- MIPCCQULGHWQBN-CYBMUJFWSA-N 3-[[(2r)-1-amino-3-cyclopropyl-1-oxopropan-2-yl]amino]-5-(3,4-dimethylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC1=NC(N[C@H](CC2CC2)C(N)=O)=NN=C1C(N)=O MIPCCQULGHWQBN-CYBMUJFWSA-N 0.000 claims description 2
- XDMFOPJHDATWKC-GFCCVEGCSA-N 3-[[(2r)-1-amino-3-cyclopropyl-1-oxopropan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C)=CC=C1NC1=NC(N[C@H](CC2CC2)C(N)=O)=NN=C1C(N)=O XDMFOPJHDATWKC-GFCCVEGCSA-N 0.000 claims description 2
- DCJOLXMAAKVKMS-SNVBAGLBSA-N 3-[[(2r)-1-amino-3-methoxy-1-oxopropan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound COC[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(C)=CC=2)=N1 DCJOLXMAAKVKMS-SNVBAGLBSA-N 0.000 claims description 2
- ISFNJYRGQSIVIB-CYBMUJFWSA-N 3-[[(2r)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 ISFNJYRGQSIVIB-CYBMUJFWSA-N 0.000 claims description 2
- YLWTYXJYRAGEEU-CYBMUJFWSA-N 3-[[(2r)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-5-[(1-methylindol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC(C)[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=3C=CN(C)C=3C=CC=2)=N1 YLWTYXJYRAGEEU-CYBMUJFWSA-N 0.000 claims description 2
- IWQZKABQQDLUIH-SNVBAGLBSA-N 3-[[(2r)-1-amino-4,4-difluoro-1-oxobutan-2-yl]amino]-5-[(8-chloroquinolin-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound FC(F)C[C@H](C(=O)N)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=C(Cl)C=2)=N1 IWQZKABQQDLUIH-SNVBAGLBSA-N 0.000 claims description 2
- VVIJUSGETJNNLU-LLVKDONJSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(3,4-dichloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(Cl)=CC=2)=N1 VVIJUSGETJNNLU-LLVKDONJSA-N 0.000 claims description 2
- WTJVEAKGKMOGTB-CYBMUJFWSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(3,4-dimethylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C)C(C)=CC=2)=N1 WTJVEAKGKMOGTB-CYBMUJFWSA-N 0.000 claims description 2
- NTLLIQJRZMNIGP-GFCCVEGCSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C)C=CC=2)=N1 NTLLIQJRZMNIGP-GFCCVEGCSA-N 0.000 claims description 2
- VYEKGOBUJCZNHM-CQSZACIVSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(3-pyrimidin-2-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2N=CC=CN=2)=N1 VYEKGOBUJCZNHM-CQSZACIVSA-N 0.000 claims description 2
- YVSBLDFMYURDFE-GFCCVEGCSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-(4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=CC(C)=CC=2)=N1 YVSBLDFMYURDFE-GFCCVEGCSA-N 0.000 claims description 2
- WXMCSXQSLDGMJE-CYBMUJFWSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-[(1-oxidoquinolin-1-ium-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=[N+]([O-])C3=CC=2)=N1 WXMCSXQSLDGMJE-CYBMUJFWSA-N 0.000 claims description 2
- WMDKKHGOQIBPOS-SNVBAGLBSA-N 3-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-[(2-methoxypyridin-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=NC(OC)=CC(NC=2C(=NN=C(N[C@H](CC(C)C)C(N)=O)N=2)C(N)=O)=C1 WMDKKHGOQIBPOS-SNVBAGLBSA-N 0.000 claims description 2
- FGJITBXSSZLDOK-GFCCVEGCSA-N 3-[[(3R)-pyrrolidin-3-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N1=C(NC=2C=C3C=CC=NC3=CC=2)C(C(=O)N)=NN=C1N[C@@H]1CCNC1 FGJITBXSSZLDOK-GFCCVEGCSA-N 0.000 claims description 2
- SAGFMRGTYNYXDC-VHSXEESVSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-(1,3-benzothiazol-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3N=CSC3=CC=2)=N1 SAGFMRGTYNYXDC-VHSXEESVSA-N 0.000 claims description 2
- CZHUQADJFVUITQ-QWHCGFSZSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-(3,4-dimethylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](COCC2)N)=NN=C1C(N)=O CZHUQADJFVUITQ-QWHCGFSZSA-N 0.000 claims description 2
- PQAMVSQUGKNYEJ-NWDGAFQWSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-(3-chloro-4-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N[C@H]2[C@H](COCC2)N)=NN=C1C(N)=O PQAMVSQUGKNYEJ-NWDGAFQWSA-N 0.000 claims description 2
- KCRKCBLLESQEMQ-UONOGXRCSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-(3-pyrimidin-2-ylanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2N=CC=CN=2)=N1 KCRKCBLLESQEMQ-UONOGXRCSA-N 0.000 claims description 2
- MDUNYYFGQNVDKU-NWDGAFQWSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-(4-cyanoanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C#N)=N1 MDUNYYFGQNVDKU-NWDGAFQWSA-N 0.000 claims description 2
- ZAJOEELYADKTBF-CMPLNLGQSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-[(1-methylindazol-4-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)N=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCOC[C@@H]1N ZAJOEELYADKTBF-CMPLNLGQSA-N 0.000 claims description 2
- QSXPIJDKVMWSLT-UONOGXRCSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-[(3-cyano-1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=C(C#N)C2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCOC[C@@H]1N QSXPIJDKVMWSLT-UONOGXRCSA-N 0.000 claims description 2
- QDUBNYFGAVHVBR-JGVFFNPUSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-[(3-methyl-1,2-thiazol-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound S1N=C(C)C=C1NC1=NC(N[C@H]2[C@H](COCC2)N)=NN=C1C(N)=O QDUBNYFGAVHVBR-JGVFFNPUSA-N 0.000 claims description 2
- VVSPNPRZBBELCZ-QWHCGFSZSA-N 3-[[(3R,4R)-3-aminooxan-4-yl]amino]-5-[3-(triazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CC=N2)=N1 VVSPNPRZBBELCZ-QWHCGFSZSA-N 0.000 claims description 2
- XEBPLNSNQVQNPP-VXGBXAGGSA-N 3-[[(3R,5R)-5-(hydroxymethyl)pyrrolidin-3-yl]amino]-5-[(1-methylpyrrolo[2,3-b]pyridin-5-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C=1N=C2N(C)C=CC2=CC=1NC(C(=NN=1)C(N)=O)=NC=1N[C@H]1CN[C@@H](CO)C1 XEBPLNSNQVQNPP-VXGBXAGGSA-N 0.000 claims description 2
- LMKPUPFDINOVMZ-WDEREUQCSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-(1,5-naphthyridin-3-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=NC=2)=N1 LMKPUPFDINOVMZ-WDEREUQCSA-N 0.000 claims description 2
- FVQIWHGIXQNGKE-UONOGXRCSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-(2,3-dihydro-1h-inden-5-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3CCCC3=CC=2)=N1 FVQIWHGIXQNGKE-UONOGXRCSA-N 0.000 claims description 2
- MGWVIDJMQNPEFC-WDEREUQCSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-(3,4-dichloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(Cl)C(Cl)=CC=2)=N1 MGWVIDJMQNPEFC-WDEREUQCSA-N 0.000 claims description 2
- MUQMAFQWOCYPDC-WDEREUQCSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-(4-chloro-3-methoxyanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=NN=C(N[C@H]3[C@H](COCC3)N)N=2)C(N)=O)=C1 MUQMAFQWOCYPDC-WDEREUQCSA-N 0.000 claims description 2
- LSULDQPAIUPWOD-NWDGAFQWSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-(4-chloro-3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound C1=C(Cl)C(C)=CC(NC=2C(=NN=C(N[C@H]3[C@H](COCC3)N)N=2)C(N)=O)=C1 LSULDQPAIUPWOD-NWDGAFQWSA-N 0.000 claims description 2
- IFEMUBHMIOLGDI-WDEREUQCSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-(4-chloroanilino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(Cl)=CC=2)=N1 IFEMUBHMIOLGDI-WDEREUQCSA-N 0.000 claims description 2
- ASVHOZFFRSJJOS-GXTWGEPZSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=N1 ASVHOZFFRSJJOS-GXTWGEPZSA-N 0.000 claims description 2
- PATRBXWRZQIPET-QWHCGFSZSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-[(1-methylindol-6-yl)amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=C2N(C)C=CC2=CC=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCOC[C@@H]1N PATRBXWRZQIPET-QWHCGFSZSA-N 0.000 claims description 2
- HQSXPKUKUMGNTP-QWHCGFSZSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-[3-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2OC=CN=2)=N1 HQSXPKUKUMGNTP-QWHCGFSZSA-N 0.000 claims description 2
- ADLUWLMATQVJDF-WDEREUQCSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-[3-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(C=CC=2)C(F)(F)F)=N1 ADLUWLMATQVJDF-WDEREUQCSA-N 0.000 claims description 2
- KBVHJIPUUHLZKC-QWHCGFSZSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-[4-(1,3-oxazol-2-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C=2OC=CN=2)=N1 KBVHJIPUUHLZKC-QWHCGFSZSA-N 0.000 claims description 2
- LOWLOWOZBOYBTP-WDEREUQCSA-N 3-[[(3r,4r)-3-aminooxan-4-yl]amino]-5-[4-(trifluoromethyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1COCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=CC(=CC=2)C(F)(F)F)=N1 LOWLOWOZBOYBTP-WDEREUQCSA-N 0.000 claims description 2
- CFCQPUVNEFYPRW-UHFFFAOYSA-N 3-amino-5-(3-methylanilino)-1,2,4-triazine-6-carboxamide Chemical compound CC1=CC=CC(NC=2C(=NN=C(N)N=2)C(N)=O)=C1 CFCQPUVNEFYPRW-UHFFFAOYSA-N 0.000 claims description 2
- OVOHYJNREWIBNL-CYBMUJFWSA-N 5-(3-pyrimidin-2-ylanilino)-3-[[(3R)-pyrrolidin-3-yl]amino]-1,2,4-triazine-6-carboxamide Chemical compound N1=C(NC=2C=C(C=CC=2)C=2N=CC=CN=2)C(C(=O)N)=NN=C1N[C@@H]1CCNC1 OVOHYJNREWIBNL-CYBMUJFWSA-N 0.000 claims description 2
- XNPIKENEFWNRMO-UHFFFAOYSA-N 5-[(1-methylindol-4-yl)amino]-3-(1h-pyrazol-5-ylmethylamino)-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)C=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1NCC=1C=CNN=1 XNPIKENEFWNRMO-UHFFFAOYSA-N 0.000 claims description 2
- JARZYXLVZZVCSC-UHFFFAOYSA-N 5-[(1-methylindol-4-yl)amino]-3-[(5-oxopyrrolidin-2-yl)methylamino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)C=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1NCC1CCC(=O)N1 JARZYXLVZZVCSC-UHFFFAOYSA-N 0.000 claims description 2
- PMVWRMAODMNEAA-SNVBAGLBSA-N 5-[(1-methylindol-4-yl)amino]-3-[[(3r)-pyrrolidin-3-yl]amino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC=C2N(C)C=CC2=C1NC(C(=NN=1)C(N)=O)=NC=1N[C@@H]1CCNC1 PMVWRMAODMNEAA-SNVBAGLBSA-N 0.000 claims description 2
- WMEUEZBREVVJJC-UHFFFAOYSA-N 5-[(2,3-difluorophenyl)methylamino]-3-[4-(1-propanoylpiperidin-4-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1CN(C(=O)CC)CCC1C(C=C1)=CC=C1NC1=NN=C(C(N)=O)C(NCC=2C(=C(F)C=CC=2)F)=N1 WMEUEZBREVVJJC-UHFFFAOYSA-N 0.000 claims description 2
- OEZIIZNEZOWTHB-UHFFFAOYSA-N 5-[(2,3-difluorophenyl)methylamino]-3-[4-(dimethylcarbamoyl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NC1=NN=C(C(N)=O)C(NCC=2C(=C(F)C=CC=2)F)=N1 OEZIIZNEZOWTHB-UHFFFAOYSA-N 0.000 claims description 2
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims description 2
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 2
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims description 2
- 206010066476 Haematological malignancy Diseases 0.000 claims description 2
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 2
- 206010062506 Heparin-induced thrombocytopenia Diseases 0.000 claims description 2
- 206010020751 Hypersensitivity Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 2
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
- 208000035868 Vascular inflammations Diseases 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 208000020832 chronic kidney disease Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000028208 end stage renal disease Diseases 0.000 claims description 2
- 201000000523 end stage renal failure Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 208000007475 hemolytic anemia Diseases 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 208000003476 primary myelofibrosis Diseases 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- 230000019491 signal transduction Effects 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- 0 Cc1c(*N=S2)c2ccc1 Chemical compound Cc1c(*N=S2)c2ccc1 0.000 description 18
- 238000000034 method Methods 0.000 description 6
- NCPZMFKSEKEGLU-JKSUJKDBSA-N 3-[[(1R,2S)-2-aminocyclohexyl]amino]-5-[3-fluoro-4-(1-oxidopiperidin-1-ium-1-yl)anilino]-1,2,4-triazine-6-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=NN=C(C(N)=O)C(NC=2C=C(F)C(=CC=2)[N+]2([O-])CCCCC2)=N1 NCPZMFKSEKEGLU-JKSUJKDBSA-N 0.000 description 1
- WLQVBFDHWAVUJN-UHFFFAOYSA-N C(C1)C1c1ccncc1 Chemical compound C(C1)C1c1ccncc1 WLQVBFDHWAVUJN-UHFFFAOYSA-N 0.000 description 1
- LVQDLURAEDSMES-UHFFFAOYSA-N CC(C)CC(N(C)C)=O Chemical compound CC(C)CC(N(C)C)=O LVQDLURAEDSMES-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N CC1CCCCC1 Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- JSIGUUUNVYUWQT-UHFFFAOYSA-N CNC1CCC1 Chemical compound CNC1CCC1 JSIGUUUNVYUWQT-UHFFFAOYSA-N 0.000 description 1
- KKTBUCVHSCATGB-UHFFFAOYSA-N CNC1CCCC1 Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
- AINBEIXHMHVGML-UHFFFAOYSA-N Cc(cc1)cc2c1[o]nc2 Chemical compound Cc(cc1)cc2c1[o]nc2 AINBEIXHMHVGML-UHFFFAOYSA-N 0.000 description 1
- SEBIXVUYSFOUEL-UHFFFAOYSA-N Cc(cc1)cc2c1[s]cn2 Chemical compound Cc(cc1)cc2c1[s]cn2 SEBIXVUYSFOUEL-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N Cc(cc1N)ccc1N Chemical compound Cc(cc1N)ccc1N DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- XKGWNLWYKSSVKG-UHFFFAOYSA-N Cc1c2[o]ncc2ccc1 Chemical compound Cc1c2[o]ncc2ccc1 XKGWNLWYKSSVKG-UHFFFAOYSA-N 0.000 description 1
- PIHVNUSWMTZFBD-UHFFFAOYSA-N Cc1c2[s]ccc2ccc1 Chemical compound Cc1c2[s]ccc2ccc1 PIHVNUSWMTZFBD-UHFFFAOYSA-N 0.000 description 1
- QRBMEWAEOHKXJG-UHFFFAOYSA-N Cc1c2[s]ncc2ccc1 Chemical compound Cc1c2[s]ncc2ccc1 QRBMEWAEOHKXJG-UHFFFAOYSA-N 0.000 description 1
- SEBRPHZZSLCDRQ-UHFFFAOYSA-N Cc1c[s]c2c1cccc2 Chemical compound Cc1c[s]c2c1cccc2 SEBRPHZZSLCDRQ-UHFFFAOYSA-N 0.000 description 1
- MTFBDBCIYNLRFH-UHFFFAOYSA-N Cc1c[s]c2c1cccn2 Chemical compound Cc1c[s]c2c1cccn2 MTFBDBCIYNLRFH-UHFFFAOYSA-N 0.000 description 1
- VZVAQLOROCVVSN-UHFFFAOYSA-N Cc1cc([o]nc2)c2cc1 Chemical compound Cc1cc([o]nc2)c2cc1 VZVAQLOROCVVSN-UHFFFAOYSA-N 0.000 description 1
- MOELJFGJWYPYPB-UHFFFAOYSA-N Cc1cc([s]nc2)c2cc1 Chemical compound Cc1cc([s]nc2)c2cc1 MOELJFGJWYPYPB-UHFFFAOYSA-N 0.000 description 1
- ITXHYKBXKRUJNO-UHFFFAOYSA-N Cc1cc(cccn2)c2[s]1 Chemical compound Cc1cc(cccn2)c2[s]1 ITXHYKBXKRUJNO-UHFFFAOYSA-N 0.000 description 1
- BLZKSRBAQDZAIX-UHFFFAOYSA-N Cc1cc2ccccc2[s]1 Chemical compound Cc1cc2ccccc2[s]1 BLZKSRBAQDZAIX-UHFFFAOYSA-N 0.000 description 1
- XDQJAYFCPRWDOL-UHFFFAOYSA-N Cc1cc2n[s]nc2cc1 Chemical compound Cc1cc2n[s]nc2cc1 XDQJAYFCPRWDOL-UHFFFAOYSA-N 0.000 description 1
- VOWZNBNDMFLQGM-UHFFFAOYSA-N Cc1ccc(C)c(N)c1 Chemical compound Cc1ccc(C)c(N)c1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 1
- WOGMIMNVXACKEB-UHFFFAOYSA-N Cc1ccc(cc[s]2)c2c1 Chemical compound Cc1ccc(cc[s]2)c2c1 WOGMIMNVXACKEB-UHFFFAOYSA-N 0.000 description 1
- GFJGRNOOYAKHNX-UHFFFAOYSA-N Cc1ccc2[s]ncc2c1 Chemical compound Cc1ccc2[s]ncc2c1 GFJGRNOOYAKHNX-UHFFFAOYSA-N 0.000 description 1
- IVKILQAPNDCUNJ-UHFFFAOYSA-N Cc1ccc2nc[s]c2c1 Chemical compound Cc1ccc2nc[s]c2c1 IVKILQAPNDCUNJ-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N Cc1ccc[s]1 Chemical compound Cc1ccc[s]1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- RPKWIZPGQZKQKY-UHFFFAOYSA-N Cc1cccc2c1cc[s]2 Chemical compound Cc1cccc2c1cc[s]2 RPKWIZPGQZKQKY-UHFFFAOYSA-N 0.000 description 1
- PIUXNZAIHQAHBY-UHFFFAOYSA-N Cc1cccc2c1nc[s]2 Chemical compound Cc1cccc2c1nc[s]2 PIUXNZAIHQAHBY-UHFFFAOYSA-N 0.000 description 1
- IYZKISWGGPKREZ-UHFFFAOYSA-N Cc1cccc2n[s]nc12 Chemical compound Cc1cccc2n[s]nc12 IYZKISWGGPKREZ-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- MYNYJERSLRKIOE-UHFFFAOYSA-N Cc1ccnc2c1cc[s]2 Chemical compound Cc1ccnc2c1cc[s]2 MYNYJERSLRKIOE-UHFFFAOYSA-N 0.000 description 1
- NMSIHVMTDKJNHH-UHFFFAOYSA-N Cc1cnc2[s]ccc2c1 Chemical compound Cc1cnc2[s]ccc2c1 NMSIHVMTDKJNHH-UHFFFAOYSA-N 0.000 description 1
- DAEGDNYLKMKZRG-UHFFFAOYSA-N Cc1n[s]c2ccccc12 Chemical compound Cc1n[s]c2ccccc12 DAEGDNYLKMKZRG-UHFFFAOYSA-N 0.000 description 1
- AOQNBQVLAHPFGC-UHFFFAOYSA-N Cc1nc([s]cc2)c2cc1 Chemical compound Cc1nc([s]cc2)c2cc1 AOQNBQVLAHPFGC-UHFFFAOYSA-N 0.000 description 1
- FVTBGGXYAATVIV-UHFFFAOYSA-N Ic1cccc2c1cn[s]2 Chemical compound Ic1cccc2c1cn[s]2 FVTBGGXYAATVIV-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261663499P | 2012-06-22 | 2012-06-22 | |
| US61/663,499 | 2012-06-22 | ||
| US13/841,472 US9040530B2 (en) | 2012-06-22 | 2013-03-15 | 1,2,4-triazine-6-carboxamide kinase inhibitors |
| US13/841,472 | 2013-03-15 | ||
| PCT/US2013/046006 WO2013192049A2 (en) | 2012-06-22 | 2013-06-14 | 1,2,4-triazine-6-carboxamide kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015520232A JP2015520232A (ja) | 2015-07-16 |
| JP2015520232A5 true JP2015520232A5 (enExample) | 2016-06-30 |
| JP6281984B2 JP6281984B2 (ja) | 2018-02-21 |
Family
ID=49769666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015518471A Active JP6281984B2 (ja) | 2012-06-22 | 2013-06-14 | １，２，４−トリアジン−６−カルボキサミドキナーゼ阻害剤 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9040530B2 (enExample) |
| EP (1) | EP2863748B1 (enExample) |
| JP (1) | JP6281984B2 (enExample) |
| CN (1) | CN104470363A (enExample) |
| AU (1) | AU2013277476B2 (enExample) |
| CA (1) | CA2876945C (enExample) |
| IL (1) | IL236057B (enExample) |
| IN (1) | IN2014KN02906A (enExample) |
| SG (2) | SG11201408232RA (enExample) |
| WO (1) | WO2013192049A2 (enExample) |
| ZA (1) | ZA201409256B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5878178B2 (ja) | 2011-09-30 | 2016-03-08 | 大鵬薬品工業株式会社 | １，２，４−トリアジン−６−カルボキサミド誘導体 |
| KR20150068484A (ko) | 2012-10-19 | 2015-06-19 | 에프. 호프만-라 로슈 아게 | Syk 억제제 |
| RS58187B1 (sr) | 2012-11-08 | 2019-03-29 | Bristol Myers Squibb Co | Amidom-supstituisana heterociklična jedinjenja korisna kao modulatori il-12, il-23 i/ili ifn-alfa |
| WO2014109414A1 (ja) * | 2013-01-11 | 2014-07-17 | 富士フイルム株式会社 | 含窒素複素環化合物またはその塩 |
| WO2014111031A1 (zh) * | 2013-01-17 | 2014-07-24 | 四川恒康发展有限责任公司 | 三嗪化合物、其药用盐、异构体或水合物及其药物组合物 |
| JP2016113366A (ja) * | 2013-03-29 | 2016-06-23 | 大鵬薬品工業株式会社 | アセトアミド基を有する１，２，４−トリアジン−６−カルボキサミド誘導体 |
| AU2014360446A1 (en) | 2013-12-05 | 2016-06-09 | Pharmacyclics, Llc | Inhibitors of Bruton's tyrosine kinase |
| MA42623A (fr) * | 2015-06-02 | 2018-06-20 | Pharmacyclics Llc | Inhibiteurs de la tyrosine kinase de bruton |
| CN109384774B (zh) * | 2017-08-11 | 2023-02-17 | 中国科学院上海药物研究所 | 一类多取代的吡嗪/三嗪酰胺类化合物及其制备方法和应用 |
| KR20220042159A (ko) | 2019-08-01 | 2022-04-04 | 인테그랄 바이오사이언스 피브이티. 엘티디. | 키나제 억제제로서의 헤테로사이클릭 화합물 및 이의 용도 |
| WO2021170046A1 (en) * | 2020-02-26 | 2021-09-02 | Beigene, Ltd. | Tyk-2 inhibitor |
| WO2022032484A1 (zh) * | 2020-08-11 | 2022-02-17 | 北京诺诚健华医药科技有限公司 | 哒嗪-3-甲酰胺类化合物、其制备方法及其在医药学上的应用 |
| WO2023108536A1 (en) * | 2021-12-16 | 2023-06-22 | Lynk Pharmaceuticals Co. Ltd. | Tyk2 inhibitors and compositions and methods thereof |
| JP2025503448A (ja) | 2021-12-16 | 2025-02-04 | リンク ファーマシューティカルズ シーオー．エルティーディー． | Ｔｙｋ２阻害剤および組成物ならびにその方法 |
| WO2024254832A1 (en) * | 2023-06-15 | 2024-12-19 | Lynk Pharmaceuticals Co. Ltd. | Tyk2 inhibitors and compositions and methods thereof |
| CN118175828B (zh) * | 2024-05-16 | 2024-08-16 | 浙江大华技术股份有限公司 | 吸波材料、制备方法和器件 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4622047B2 (ja) * | 1999-06-09 | 2011-02-02 | アステラス製薬株式会社 | 新規なヘテロ環カルボキサミド誘導体 |
| ATE288420T1 (de) * | 1999-06-09 | 2005-02-15 | Yamanouchi Pharma Co Ltd | Neuartige heterocyclische carboxamid-derivate |
| WO2000076980A1 (en) * | 1999-06-10 | 2000-12-21 | Yamanouchi Pharmaceutical Co., Ltd. | Novel nitrogen-contaiing heterocyclic derivatives or salts thereof |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| KR20100132550A (ko) * | 2008-04-16 | 2010-12-17 | 포톨라 파마슈티컬스, 인코포레이티드 | ｓｙｋ 또는 ＪＡＫ 키나제 억제제로서의 ２,６－디아미노-피리미딘－５－일－카르복스아미드 |
| JP5878178B2 (ja) * | 2011-09-30 | 2016-03-08 | 大鵬薬品工業株式会社 | １，２，４−トリアジン−６−カルボキサミド誘導体 |
| UY34807A (es) * | 2012-05-16 | 2013-12-31 | Novartis Ag | Derivados monocíclicos de heteroarilcicloalquil- diamina |
-
2013
- 2013-03-15 US US13/841,472 patent/US9040530B2/en active Active
- 2013-06-14 IN IN2906KON2014 patent/IN2014KN02906A/en unknown
- 2013-06-14 EP EP13807456.2A patent/EP2863748B1/en active Active
- 2013-06-14 SG SG11201408232RA patent/SG11201408232RA/en unknown
- 2013-06-14 CN CN201380037312.3A patent/CN104470363A/zh active Pending
- 2013-06-14 SG SG10201805392YA patent/SG10201805392YA/en unknown
- 2013-06-14 AU AU2013277476A patent/AU2013277476B2/en not_active Ceased
- 2013-06-14 CA CA2876945A patent/CA2876945C/en active Active
- 2013-06-14 WO PCT/US2013/046006 patent/WO2013192049A2/en not_active Ceased
- 2013-06-14 JP JP2015518471A patent/JP6281984B2/ja active Active
-
2014
- 2014-12-04 IL IL236057A patent/IL236057B/en active IP Right Grant
- 2014-12-15 ZA ZA2014/09256A patent/ZA201409256B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015520232A5 (enExample) | ||
| JP6281984B2 (ja) | １，２，４−トリアジン−６−カルボキサミドキナーゼ阻害剤 | |
| EP1326856B1 (en) | Pyridine derivatives with ikb-kinase (ikk-beta) inhibiting activity | |
| AU2014233414B2 (en) | N-acyl-N'-(pyridin-2-yl) ureas and analogs exhibiting anti-cancer and anti-proliferative activities | |
| US8895585B2 (en) | Nicotinamide derivative or salt thereof | |
| JP5868168B2 (ja) | 新規なニコチンアミド誘導体またはその塩 | |
| JP5847087B2 (ja) | オレキシン受容体調節因子としての縮合複素環式化合物 | |
| US20230103791A1 (en) | 2,3-dihydroquinazolin compounds as nav1.8 inhibitors | |
| RU2012126989A (ru) | 2-амино-5,5-дифтор-5,6-дигидро-4н-оксазины в качестве ингибиторов васе 1 и(или) васе 2 | |
| US20070054916A1 (en) | Aryl nitrogen-containing bicyclic compounds and methods of use | |
| TW202016094A (zh) | 週期素依賴性激酶抑制劑 | |
| JP2011518158A5 (enExample) | ||
| KR20010083055A (ko) | 글리코겐 신타제 키나제 3의 억제제 | |
| JP2016501186A (ja) | キナーゼモジュレーターとして有用なヘテロアリール置換ピリジル化合物 | |
| ES2662523T3 (es) | Benzamidas | |
| AU2017342928B2 (en) | Quinoxaline compounds as type III receptor tyrosine kinase inhibitors | |
| AU2005267884A1 (en) | Potassium channel inhibitors | |
| WO2004052880A1 (en) | Pyridine derivatives as jnk inhibitors and their use | |
| JP7114591B2 (ja) | Ｇｓｋ－３阻害剤 | |
| EP1960394A2 (en) | Pyrazolyl urea derivatives useful in the treatment of cancer | |
| AU2013302320A1 (en) | VEGFR3 inhibitors | |
| KR20210110288A (ko) | 치환된 아릴 화합물, 및 이의 제조 방법 및 이의 용도 | |
| WO2021117846A1 (ja) | Ｐｄｇｆ受容体キナーゼ阻害剤としての化合物および組成物 | |
| AU2016297037B9 (en) | Nitrogen-containing heterocyclic compound | |
| JP2015523996A5 (enExample) |