JP2013544256A5

JP2013544256A5 -

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Publication number: JP2013544256A5
Authority: JP; Japan
Prior art keywords: pyridin; thiazol; amino; methyl; amine
Prior art date: 2011-11-18
Legal status : Granted

Application number

JP2013540089A

Other languages

English (en)

Japanese (ja)

Other versions

JP2013544256A (ja

JP6005050B2 (ja

Filing date

2011-11-18

Publication date

2016-03-24

2011-11-18 Application filed filed Critical

2011-11-18 Priority claimed from PCT/US2011/061532 external-priority patent/WO2012068546A1/en

2013-12-12 Publication of JP2013544256A publication Critical patent/JP2013544256A/ja

2016-03-24 Publication of JP2013544256A5 publication Critical patent/JP2013544256A5/ja

2016-10-12 Application granted granted Critical

2016-10-12 Publication of JP6005050B2 publication Critical patent/JP6005050B2/ja

Status Active legal-status Critical Current

2031-11-18 Anticipated expiration legal-status Critical

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-1 heterohaloalkyl Chemical group 0.000 claims description 45
125000001072 heteroaryl group Chemical group 0.000 claims description 12
125000006574 non-aromatic ring group Chemical group 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000004404 heteroalkyl group Chemical group 0.000 claims description 4
229940124530 sulfonamide Drugs 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
125000005152 trihalomethanesulfonyl group Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 19
229910052739 hydrogen Inorganic materials 0.000 claims 15
150000002431 hydrogen Chemical class 0.000 claims 15
239000001257 hydrogen Substances 0.000 claims 15
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 13
229910052736 halogen Inorganic materials 0.000 claims 13
150000002367 halogens Chemical class 0.000 claims 13
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 12
WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 claims 11
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 10
239000008194 pharmaceutical composition Substances 0.000 claims 9
125000003107 substituted aryl group Chemical group 0.000 claims 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 7
150000001412 amines Chemical class 0.000 claims 7
150000001408 amides Chemical class 0.000 claims 5
125000005605 benzo group Chemical group 0.000 claims 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
208000035475 disorder Diseases 0.000 claims 5
150000002148 esters Chemical class 0.000 claims 5
239000000651 prodrug Substances 0.000 claims 5
229940002612 prodrug Drugs 0.000 claims 5
150000003839 salts Chemical class 0.000 claims 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 4
125000003226 pyrazolyl group Chemical group 0.000 claims 4
125000002971 oxazolyl group Chemical group 0.000 claims 3
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
XSRGQCCPPSPRPC-UHFFFAOYSA-N 2-[[4-(pyrrolidin-3-ylamino)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound S1C2=CC(C#N)=CC=C2N=C1NC(N=CC=1)=CC=1NC1CCNC1 XSRGQCCPPSPRPC-UHFFFAOYSA-N 0.000 claims 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
206010047115 Vasculitis Diseases 0.000 claims 2
208000027866 inflammatory disease Diseases 0.000 claims 2
VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 2
125000000842 isoxazolyl group Chemical group 0.000 claims 2
KOTCOWRINSHGFU-ZDUSSCGKSA-N n-[4-[(3s)-3-methyl-4-methylsulfonylpiperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(C)(=O)=O)[C@@H](C)CN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 KOTCOWRINSHGFU-ZDUSSCGKSA-N 0.000 claims 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
208000023504 respiratory system disease Diseases 0.000 claims 2
208000017520 skin disease Diseases 0.000 claims 2
IDSQZSVPXSRFKP-UHFFFAOYSA-N 1,1-dimethyl-3-[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]urea Chemical compound CN(C)C(=O)NC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 IDSQZSVPXSRFKP-UHFFFAOYSA-N 0.000 claims 1
SNBLVPRQFOVVCG-UHFFFAOYSA-N 1,1-dimethyl-3-[[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl]urea Chemical compound CN(C)C(=O)NCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 SNBLVPRQFOVVCG-UHFFFAOYSA-N 0.000 claims 1
WENWRIYPUANIPL-UHFFFAOYSA-N 1-(3-hydroxypyrrolidin-1-yl)-2-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]ethanone Chemical compound C1C(O)CCN1C(=O)CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 WENWRIYPUANIPL-UHFFFAOYSA-N 0.000 claims 1
NELLQXIOFPPIEX-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-2-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 NELLQXIOFPPIEX-UHFFFAOYSA-N 0.000 claims 1
SAIXTPCXJSUVKN-UHFFFAOYSA-N 1-[2-[[6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]pyridin-4-yl]ethanol Chemical compound CC(O)C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 SAIXTPCXJSUVKN-UHFFFAOYSA-N 0.000 claims 1
TURDAOZUTMNUNK-UHFFFAOYSA-N 1-[4-[2-[(5-ethyl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]-2-methoxyethanone Chemical compound S1C2=NC(CC)=CC=C2N=C1NC(N=CC=1)=CC=1N1CCN(C(=O)COC)CC1 TURDAOZUTMNUNK-UHFFFAOYSA-N 0.000 claims 1
RWMWODLWWARHNY-UHFFFAOYSA-N 1-[4-[2-[(5-ethynyl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C#C)=C1 RWMWODLWWARHNY-UHFFFAOYSA-N 0.000 claims 1
FCPPKGCNNQKOJO-UHFFFAOYSA-N 1-[4-[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]-3-pyrrolidin-1-ylpropan-1-one Chemical compound C1CN(C=2C=C(NC=3SC4=NC(=CC=C4N=3)C3=CNN=C3)N=CC=2)CCN1C(=O)CCN1CCCC1 FCPPKGCNNQKOJO-UHFFFAOYSA-N 0.000 claims 1
YGAUTMIBMNFAMU-UHFFFAOYSA-N 1-[4-[2-[[5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]-2-propan-2-yloxyethanone Chemical compound C1CN(C(=O)COC(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 YGAUTMIBMNFAMU-UHFFFAOYSA-N 0.000 claims 1
WLCAXWSNDMLLQZ-UHFFFAOYSA-N 1-[4-[[2-[(6-bromo-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=NC(NC=2SC3=CC(Br)=CC=C3N=2)=C1 WLCAXWSNDMLLQZ-UHFFFAOYSA-N 0.000 claims 1
UXIXQKWFZMRQAY-UHFFFAOYSA-N 1-[4-[[2-[(6-pyridin-3-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=NC=CC=2)=C1 UXIXQKWFZMRQAY-UHFFFAOYSA-N 0.000 claims 1
CCSVTCSFJHSGAZ-UHFFFAOYSA-N 1-[4-[[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 CCSVTCSFJHSGAZ-UHFFFAOYSA-N 0.000 claims 1
UVNOZNSJQYLLSG-UHFFFAOYSA-N 1-[4-[[2-[(6-pyridin-4-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=C1 UVNOZNSJQYLLSG-UHFFFAOYSA-N 0.000 claims 1
AAPNZXVKSMYVFE-UHFFFAOYSA-N 1-[4-[[2-[[6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 AAPNZXVKSMYVFE-UHFFFAOYSA-N 0.000 claims 1
SKHLURGCDSPHMG-UHFFFAOYSA-N 1-[[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]methyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 SKHLURGCDSPHMG-UHFFFAOYSA-N 0.000 claims 1
PMIGEWCHTZHTGA-UHFFFAOYSA-N 1-[[2-[(6-bromo-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=NC(NC=2SC3=CC(Br)=CC=C3N=2)=C1 PMIGEWCHTZHTGA-UHFFFAOYSA-N 0.000 claims 1
YNNBBESJXOSUFG-UHFFFAOYSA-N 1-[[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 YNNBBESJXOSUFG-UHFFFAOYSA-N 0.000 claims 1
UPOIOGLOWQJNQI-UHFFFAOYSA-N 1-[[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]methyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 UPOIOGLOWQJNQI-UHFFFAOYSA-N 0.000 claims 1
SNPZDJVNVCJDPX-UHFFFAOYSA-N 1-[[2-[[5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]methyl]pyrrolidin-3-ol Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN5CC(O)CC5)C=4)=NC3=CC=2)=C1C SNPZDJVNVCJDPX-UHFFFAOYSA-N 0.000 claims 1
PUXXMYKWWIGXRI-UHFFFAOYSA-N 1-[[2-[[6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]pyridin-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 PUXXMYKWWIGXRI-UHFFFAOYSA-N 0.000 claims 1
QBSNHDLDKVSORM-UHFFFAOYSA-N 1-[[2-[[6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]pyridin-4-yl]methyl]pyrrolidin-3-ol Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CC(O)CC5)C=4)=NC3=CC=2)=C1C QBSNHDLDKVSORM-UHFFFAOYSA-N 0.000 claims 1
XRFLMTQVLOKPLS-UHFFFAOYSA-N 1-methyl-4-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]piperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 XRFLMTQVLOKPLS-UHFFFAOYSA-N 0.000 claims 1
DOIKTBWFJDUDQL-UHFFFAOYSA-N 1-methyl-4-[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 DOIKTBWFJDUDQL-UHFFFAOYSA-N 0.000 claims 1
IFFLKGMDBKQMAH-UHFFFAOYSA-N 2,4-diaminopyridine Chemical compound NC1=CC=NC(N)=C1 IFFLKGMDBKQMAH-UHFFFAOYSA-N 0.000 claims 1
PFRFFYIYTCFLCI-UHFFFAOYSA-N 2-(6-methoxy-1,3-benzothiazol-2-yl)-4-N-pyrrolidin-3-yl-1H-pyridine-2,4-diamine Chemical compound COC1=CC2=C(N=C(S2)C2(NC=CC(=C2)NC2CNCC2)N)C=C1 PFRFFYIYTCFLCI-UHFFFAOYSA-N 0.000 claims 1
MYKGVSANVDSKEH-UHFFFAOYSA-N 2-(6-pyridin-4-yl-1,3-benzothiazol-2-yl)-1H-pyridine-2,6-diamine Chemical compound N1=CC=C(C=C1)C1=CC2=C(N=C(S2)C2(NC(=CC=C2)N)N)C=C1 MYKGVSANVDSKEH-UHFFFAOYSA-N 0.000 claims 1
PKRIZBNPQXPRSY-UHFFFAOYSA-N 2-[(3-methyl-1,2-oxazol-5-yl)amino]-1,3-benzothiazole-6-carbonitrile Chemical compound O1N=C(C)C=C1NC1=NC2=CC=C(C#N)C=C2S1 PKRIZBNPQXPRSY-UHFFFAOYSA-N 0.000 claims 1
AEQXYLWTYVVDEC-UHFFFAOYSA-N 2-[(4,6-dimethylpyridin-2-yl)amino]-1,3-benzothiazole-6-carbonitrile Chemical compound CC1=CC(C)=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 AEQXYLWTYVVDEC-UHFFFAOYSA-N 0.000 claims 1
KYEOBVJLLRDROB-UHFFFAOYSA-N 2-[(4-ethylpyridin-2-yl)amino]-1,3-benzothiazole-6-carbonitrile Chemical compound CCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 KYEOBVJLLRDROB-UHFFFAOYSA-N 0.000 claims 1
SKFOFERTVDDWKT-UHFFFAOYSA-N 2-[(4-morpholin-4-ylpyridin-2-yl)amino]-1,3-benzothiazole-6-carbonitrile Chemical compound S1C2=CC(C#N)=CC=C2N=C1NC(N=CC=1)=CC=1N1CCOCC1 SKFOFERTVDDWKT-UHFFFAOYSA-N 0.000 claims 1
TZBHKXBABKUKPK-UHFFFAOYSA-N 2-[(4-piperidin-4-ylpyridin-2-yl)amino]-1,3-benzothiazole-6-carbonitrile Chemical compound S1C2=CC(C#N)=CC=C2N=C1NC(N=CC=1)=CC=1C1CCNCC1 TZBHKXBABKUKPK-UHFFFAOYSA-N 0.000 claims 1
URDYWDZGNKBLDF-UHFFFAOYSA-N 2-[(5-methyl-4-phenyl-1,3-thiazol-2-yl)amino]-1,3-benzothiazole-6-carbonitrile Chemical compound CC=1SC(NC=2SC3=CC(=CC=C3N=2)C#N)=NC=1C1=CC=CC=C1 URDYWDZGNKBLDF-UHFFFAOYSA-N 0.000 claims 1
IEJYEBZVDVWZSI-UHFFFAOYSA-N 2-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]-1-pyrrolidin-1-ylethanone Chemical compound C1CCCN1C(=O)CC(C=1)=CC=NC=1NC(SC1=C2)=NC1=CC=C2C1=CC=NC=C1 IEJYEBZVDVWZSI-UHFFFAOYSA-N 0.000 claims 1
YPYHFQMXOHKTDB-UHFFFAOYSA-N 2-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]acetic acid Chemical compound OC(=O)CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 YPYHFQMXOHKTDB-UHFFFAOYSA-N 0.000 claims 1
YNNUSGIPVFPVBX-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-UHFFFAOYSA-N 0.000 claims 1
IWDAPISSGBGLGS-UHFFFAOYSA-N 2-[3-(pyrrolidin-1-ylmethyl)anilino]-1,3-benzothiazole-6-carbonitrile Chemical compound S1C2=CC(C#N)=CC=C2N=C1NC(C=1)=CC=CC=1CN1CCCC1 IWDAPISSGBGLGS-UHFFFAOYSA-N 0.000 claims 1
PPKXTTVSQBOWQD-UHFFFAOYSA-N 2-[4-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 PPKXTTVSQBOWQD-UHFFFAOYSA-N 0.000 claims 1
LPWGHQYEYXPDCQ-UHFFFAOYSA-N 2-[4-[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 LPWGHQYEYXPDCQ-UHFFFAOYSA-N 0.000 claims 1
QWHVWWQXEJTFAD-UHFFFAOYSA-N 2-[[2-[(6-bromo-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl-methylamino]ethanol Chemical compound OCCN(C)CC1=CC=NC(NC=2SC3=CC(Br)=CC=C3N=2)=C1 QWHVWWQXEJTFAD-UHFFFAOYSA-N 0.000 claims 1
JPFITHWLJVRKKQ-UHFFFAOYSA-N 2-[[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]amino]ethanol Chemical compound OCCNC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 JPFITHWLJVRKKQ-UHFFFAOYSA-N 0.000 claims 1
HCOJWCVUFSWCSM-SNVBAGLBSA-N 2-[[2-[[4-(methylamino)-6-[[(3r)-pyrrolidin-3-yl]amino]-1,3,5-triazin-2-yl]amino]-1,3-benzothiazol-6-yl]oxy]ethanol Chemical compound N=1C(NC=2SC3=CC(OCCO)=CC=C3N=2)=NC(NC)=NC=1N[C@@H]1CCNC1 HCOJWCVUFSWCSM-SNVBAGLBSA-N 0.000 claims 1
AQAUEZYKSZBWDW-SNVBAGLBSA-N 2-[[4-(1,3-benzothiazol-2-ylamino)-6-[[(3r)-pyrrolidin-3-yl]amino]-1,3,5-triazin-2-yl]amino]ethanol Chemical compound N=1C(NC=2SC3=CC=CC=C3N=2)=NC(NCCO)=NC=1N[C@@H]1CCNC1 AQAUEZYKSZBWDW-SNVBAGLBSA-N 0.000 claims 1
WRDVZRHJXMDUJS-UHFFFAOYSA-N 2-[[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound S1C2=CC(C#N)=CC=C2N=C1NC(N=CC=1)=CC=1N(CC1)CCC21OCCO2 WRDVZRHJXMDUJS-UHFFFAOYSA-N 0.000 claims 1
FBHRADKBONQCCI-UHFFFAOYSA-N 2-[[4-(1-aminopropan-2-ylamino)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound NCC(C)NC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 FBHRADKBONQCCI-UHFFFAOYSA-N 0.000 claims 1
JPMFHYZJMWFKDS-UHFFFAOYSA-N 2-[[4-(1-benzoylpiperidin-4-yl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CC(C=2C=C(NC=3SC4=CC(=CC=C4N=3)C#N)N=CC=2)CCN1C(=O)C1=CC=CC=C1 JPMFHYZJMWFKDS-UHFFFAOYSA-N 0.000 claims 1
PDTXAEACBUPYRQ-UHFFFAOYSA-N 2-[[4-(1-ethylsulfonylpiperidin-4-yl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 PDTXAEACBUPYRQ-UHFFFAOYSA-N 0.000 claims 1
ISRLEKBJQSXJKL-UHFFFAOYSA-N 2-[[4-(1-propanoylpiperidin-4-yl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CN(C(=O)CC)CCC1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 ISRLEKBJQSXJKL-UHFFFAOYSA-N 0.000 claims 1
PEIOXIDXQABEJV-UHFFFAOYSA-N 2-[[4-(2-aminopropylamino)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound CC(N)CNC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 PEIOXIDXQABEJV-UHFFFAOYSA-N 0.000 claims 1
ACMJGWHXOKBLHX-UHFFFAOYSA-N 2-[[4-(2-methoxyethoxy)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound COCCOC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 ACMJGWHXOKBLHX-UHFFFAOYSA-N 0.000 claims 1
XTTMUSHAULPNAQ-UHFFFAOYSA-N 2-[[4-(3-aminopiperidine-1-carbonyl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1C(N)CCCN1C(=O)C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 XTTMUSHAULPNAQ-UHFFFAOYSA-N 0.000 claims 1
XTBRWELUXDUJGZ-UHFFFAOYSA-N 2-[[4-(3-bicyclo[2.2.1]heptanylamino)-6-(pyrrolidin-3-ylamino)-1,3,5-triazin-2-yl]amino]-1,3-benzothiazole-6-carboxylic acid Chemical compound S1C2=CC(C(=O)O)=CC=C2N=C1NC(N=C(NC1C2CCC(C2)C1)N=1)=NC=1NC1CCNC1 XTBRWELUXDUJGZ-UHFFFAOYSA-N 0.000 claims 1
XIQYNTUWKBHPII-UHFFFAOYSA-N 2-[[4-(4-hydroxypiperidin-1-yl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CC(O)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 XIQYNTUWKBHPII-UHFFFAOYSA-N 0.000 claims 1
CCISBUCIGHQSEA-UHFFFAOYSA-N 2-[[4-(4-oxopiperidin-1-yl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CC(=O)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 CCISBUCIGHQSEA-UHFFFAOYSA-N 0.000 claims 1
PPFJCIHOSSVOND-UHFFFAOYSA-N 2-[[4-(cyclopentylamino)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound S1C2=CC(C#N)=CC=C2N=C1NC(N=CC=1)=CC=1NC1CCCC1 PPFJCIHOSSVOND-UHFFFAOYSA-N 0.000 claims 1
HJIXHJQFJCYQFZ-UHFFFAOYSA-N 2-[[4-(hydroxymethyl)pyridin-2-yl]amino]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound OCC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C#N)=C1 HJIXHJQFJCYQFZ-UHFFFAOYSA-N 0.000 claims 1
KRWDYOHDMZMBCI-UHFFFAOYSA-N 2-[[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound S1C2=CC(C#N)=CC=C2N=C1NC(N=CC=1)=CC=1CN1CCCC1 KRWDYOHDMZMBCI-UHFFFAOYSA-N 0.000 claims 1
CQSGRBXJPFLJTQ-UHFFFAOYSA-N 2-[[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]amino]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C=1N2C=C(C#N)C=CC2=NC=1NC(N=CC=1)=CC=1CN1CCCC1 CQSGRBXJPFLJTQ-UHFFFAOYSA-N 0.000 claims 1
XISGDEABPORDIO-UHFFFAOYSA-N 2-[[4-(pyrrolidine-1-carbonyl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=CC=1C(=O)N1CCCC1 XISGDEABPORDIO-UHFFFAOYSA-N 0.000 claims 1
HZQGMJZCFWXNSR-UHFFFAOYSA-N 2-[[4-(pyrrolidine-1-carbothioyl)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=CC=1C(=S)N1CCCC1 HZQGMJZCFWXNSR-UHFFFAOYSA-N 0.000 claims 1
XJMRSUOBTYTBGI-UHFFFAOYSA-N 2-[[4-[1-(2,2,2-trifluoroacetyl)piperidin-4-yl]pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CN(C(=O)C(F)(F)F)CCC1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 XJMRSUOBTYTBGI-UHFFFAOYSA-N 0.000 claims 1
ZXVBYUIXVPALOX-UHFFFAOYSA-N 2-[[4-[1-(3-cyclopentylpropanoyl)piperidin-4-yl]pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CC(C=2C=C(NC=3SC4=CC(=CC=C4N=3)C#N)N=CC=2)CCN1C(=O)CCC1CCCC1 ZXVBYUIXVPALOX-UHFFFAOYSA-N 0.000 claims 1
DZIYICJBFDCNKU-UHFFFAOYSA-N 2-[[4-[1-(cyanomethyl)piperidin-4-yl]pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CN(CC#N)CCC1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 DZIYICJBFDCNKU-UHFFFAOYSA-N 0.000 claims 1
LZJVDVUGVPZMQF-UHFFFAOYSA-N 2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CC(C=2C=C(NC=3SC4=CC(=CC=C4N=3)C#N)N=CC=2)CCN1C(=O)C1CC1 LZJVDVUGVPZMQF-UHFFFAOYSA-N 0.000 claims 1
KGCRJKGNCLIWTO-UHFFFAOYSA-N 2-[[4-[4-(2-methoxyacetyl)piperazin-1-yl]pyridin-2-yl]amino]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C#N)=C1 KGCRJKGNCLIWTO-UHFFFAOYSA-N 0.000 claims 1
IENQONDZNCIQKU-UHFFFAOYSA-N 2-[[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C#N)=C1 IENQONDZNCIQKU-UHFFFAOYSA-N 0.000 claims 1
AHCDUFCUUSQAEY-UHFFFAOYSA-N 2-[[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]amino]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C#N)=C1 AHCDUFCUUSQAEY-UHFFFAOYSA-N 0.000 claims 1
ITCNQMFBSZZPIY-UHFFFAOYSA-N 2-[[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C1=CC(OC)=CC=C1C(S1)=NN=C1NC1=NC2=CC=C(C#N)C=C2S1 ITCNQMFBSZZPIY-UHFFFAOYSA-N 0.000 claims 1
LRYGFOAZOUJLPU-UHFFFAOYSA-N 2-[[5-methyl-4-(pyrrolidin-3-ylamino)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound CC1=CN=C(NC=2SC3=CC(=CC=C3N=2)C#N)C=C1NC1CCNC1 LRYGFOAZOUJLPU-UHFFFAOYSA-N 0.000 claims 1
FKKHWPJNBKQRGH-UHFFFAOYSA-N 2-[[6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]-n-pyrrolidin-3-ylpyrimidine-4-carboxamide Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=NC=1C(=O)NC1CCNC1 FKKHWPJNBKQRGH-UHFFFAOYSA-N 0.000 claims 1
GPDOBWIDQROHJV-UHFFFAOYSA-N 2-[[6-methyl-4-(pyrrolidin-3-ylamino)pyridin-2-yl]amino]-1,3-benzothiazole-6-carbonitrile Chemical compound C=1C(NC=2SC3=CC(=CC=C3N=2)C#N)=NC(C)=CC=1NC1CCNC1 GPDOBWIDQROHJV-UHFFFAOYSA-N 0.000 claims 1
XAALRMROBHBDTM-UHFFFAOYSA-N 2-[methyl-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]amino]ethanol Chemical compound OCCN(C)C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 XAALRMROBHBDTM-UHFFFAOYSA-N 0.000 claims 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
XVJQYUSLSDRLJT-UHFFFAOYSA-N 2-hydroxy-1-[4-[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CO)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 XVJQYUSLSDRLJT-UHFFFAOYSA-N 0.000 claims 1
RDDBNUXMGGCLIK-MRXNPFEDSA-N 2-methoxy-1-[(2r)-2-methyl-4-[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1[C@@H](C)N(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 RDDBNUXMGGCLIK-MRXNPFEDSA-N 0.000 claims 1
RDDBNUXMGGCLIK-INIZCTEOSA-N 2-methoxy-1-[(2s)-2-methyl-4-[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1[C@H](C)N(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 RDDBNUXMGGCLIK-INIZCTEOSA-N 0.000 claims 1
IRRJTVUVQNWYDN-MRXNPFEDSA-N 2-methoxy-1-[(3r)-3-methyl-4-[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C[C@@H]1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 IRRJTVUVQNWYDN-MRXNPFEDSA-N 0.000 claims 1
CRKYEHNAAZXSGE-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 CRKYEHNAAZXSGE-UHFFFAOYSA-N 0.000 claims 1
GSYOIKKIUNFJRS-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCC1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 GSYOIKKIUNFJRS-UHFFFAOYSA-N 0.000 claims 1
XGVQIVFUHOJSOY-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[(5-pyrimidin-5-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=NC=NC=2)=C1 XGVQIVFUHOJSOY-UHFFFAOYSA-N 0.000 claims 1
PVKWAQUDXSUPAQ-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 PVKWAQUDXSUPAQ-UHFFFAOYSA-N 0.000 claims 1
HTTORECBYPSUCQ-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[(6-pyridin-4-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=C1 HTTORECBYPSUCQ-UHFFFAOYSA-N 0.000 claims 1
GCIMTEMSIIURSF-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 GCIMTEMSIIURSF-UHFFFAOYSA-N 0.000 claims 1
VYUSJSVFOUTNRT-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[[5-(2-methylpyridin-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=C(C)N=CC=2)=C1 VYUSJSVFOUTNRT-UHFFFAOYSA-N 0.000 claims 1
GIIXIVZAFAUAJA-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[[6-(2,2,2-trifluoroethyl)-1,3-benzothiazol-2-yl]amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=CC(CC(F)(F)F)=CC=C3N=2)=C1 GIIXIVZAFAUAJA-UHFFFAOYSA-N 0.000 claims 1
QMRMBWAQBBXASN-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[[6-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2SC3=NC=C(C=C3N=2)C2=C(NN=C2)C)=C1 QMRMBWAQBBXASN-UHFFFAOYSA-N 0.000 claims 1
UKTKCWQNALLEHM-UHFFFAOYSA-N 2-methoxy-1-[4-[[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 UKTKCWQNALLEHM-UHFFFAOYSA-N 0.000 claims 1
VCJXKNSXLGUABK-UHFFFAOYSA-N 2-methoxy-1-[4-[[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 VCJXKNSXLGUABK-UHFFFAOYSA-N 0.000 claims 1
IUCMLXIGWGKVAC-UHFFFAOYSA-N 2-methoxy-1-[4-[[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 IUCMLXIGWGKVAC-UHFFFAOYSA-N 0.000 claims 1
RBHXOCQCXKQGJT-UHFFFAOYSA-N 2-methoxy-1-[4-[[2-[[5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 RBHXOCQCXKQGJT-UHFFFAOYSA-N 0.000 claims 1
XDARSBKZSWDAOT-UHFFFAOYSA-N 2-methoxy-1-[4-[[2-[[6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 XDARSBKZSWDAOT-UHFFFAOYSA-N 0.000 claims 1
HERACMUSBGFLTC-UHFFFAOYSA-N 2-methoxy-1-[4-[[2-[[6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 HERACMUSBGFLTC-UHFFFAOYSA-N 0.000 claims 1
HPPAALOFDWBXLV-UHFFFAOYSA-N 2-propan-2-yloxy-1-[4-[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 HPPAALOFDWBXLV-UHFFFAOYSA-N 0.000 claims 1
AYRBDRVQKCYHTN-UHFFFAOYSA-N 3-(dimethylamino)-1-[4-[2-[[5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]amino]pyridin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CCN(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 AYRBDRVQKCYHTN-UHFFFAOYSA-N 0.000 claims 1
PEIDMZBPQKFNQW-UHFFFAOYSA-N 3-[2-[[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]amino]-1,3-benzothiazol-6-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCC5)C=4)=NC3=CC=2)=C1 PEIDMZBPQKFNQW-UHFFFAOYSA-N 0.000 claims 1
PXOAILBVZDBYDY-LLVKDONJSA-N 3-[[4-(1,3-benzothiazol-2-ylamino)-6-[[(3r)-pyrrolidin-3-yl]amino]-1,3,5-triazin-2-yl]amino]propan-1-ol Chemical compound N=1C(NC=2SC3=CC=CC=C3N=2)=NC(NCCCO)=NC=1N[C@@H]1CCNC1 PXOAILBVZDBYDY-LLVKDONJSA-N 0.000 claims 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
HXMUBRLXBMOFFN-UHFFFAOYSA-N 4-(2-bicyclo[2.2.1]heptanyl)-6-N-(6-chloro-1,3-benzothiazol-2-yl)-2-pyrrolidin-3-ylimino-1,3-dihydro-1,3,5-triazine-4,6-diamine Chemical compound C12C(CC(CC1)C2)C2(NC(=NC(=N2)NC=2SC1=C(N2)C=CC(=C1)Cl)NC1CNCC1)N HXMUBRLXBMOFFN-UHFFFAOYSA-N 0.000 claims 1
BSZDWHQFSNHJIE-UHFFFAOYSA-N 4-(2-bicyclo[2.2.1]heptanyl)-6-N-(6-methoxy-1,3-benzothiazol-2-yl)-2-pyrrolidin-3-ylimino-1,3-dihydro-1,3,5-triazine-4,6-diamine Chemical compound C12C(CC(CC1)C2)C2(NC(=NC(=N2)NC=2SC1=C(N2)C=CC(=C1)OC)NC1CNCC1)N BSZDWHQFSNHJIE-UHFFFAOYSA-N 0.000 claims 1
WSSHTJOIOCSPSK-UHFFFAOYSA-N 4-(2-methoxyethyl)-4-N-methyl-2-N-(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)-3H-pyridine-2,4-diamine Chemical compound COCCC1(CC(=NC=C1)NC=1SC2=NC(=CC=C2N1)C1=CC=NC=C1)NC WSSHTJOIOCSPSK-UHFFFAOYSA-N 0.000 claims 1
QOWAJJSTFUNLQF-UHFFFAOYSA-N 4-N-(2-methoxyethyl)-4-N-methyl-2-[5-(1H-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]-1H-pyridine-2,4-diamine Chemical compound N1N=CC(=C1)C1=CC=C2C(=N1)SC(=N2)C2(NC=CC(=C2)N(C)CCOC)N QOWAJJSTFUNLQF-UHFFFAOYSA-N 0.000 claims 1
MZORFZDNGUVOKX-UHFFFAOYSA-N 4-[2-[(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]pyridin-4-yl]morpholin-3-one Chemical compound O=C1COCCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 MZORFZDNGUVOKX-UHFFFAOYSA-N 0.000 claims 1
NBTIQSJJNFLMSD-UHFFFAOYSA-N 4-amino-2-[3,5-bis(methoxymethyl)phenyl]-1,3-benzothiazole-6-carbonitrile Chemical compound COCC=1C=C(C=C(C=1)COC)C=1SC2=C(N=1)C(=CC(=C2)C#N)N NBTIQSJJNFLMSD-UHFFFAOYSA-N 0.000 claims 1
MBQNPSLUIVZNEX-UHFFFAOYSA-N 4-amino-2-[3-(hydroxymethyl)phenyl]-1,3-benzothiazole-6-carbonitrile Chemical compound OCC=1C=C(C=CC=1)C=1SC2=C(N=1)C(=CC(=C2)C#N)N MBQNPSLUIVZNEX-UHFFFAOYSA-N 0.000 claims 1
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 1
MYJFQLQNRSLLJH-SECBINFHSA-N 4-n-(1,3-benzothiazol-2-yl)-6-n-methyl-2-n-[(3r)-pyrrolidin-3-yl]-1,3,5-triazine-2,4,6-triamine Chemical compound N=1C(NC=2SC3=CC=CC=C3N=2)=NC(NC)=NC=1N[C@@H]1CCNC1 MYJFQLQNRSLLJH-SECBINFHSA-N 0.000 claims 1
WTJJUKWMJFNILI-UHFFFAOYSA-N 5-(1h-pyrazol-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C=1C=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=CC=1CN1CCCC1 WTJJUKWMJFNILI-UHFFFAOYSA-N 0.000 claims 1
DCYQEVOEIXWGHU-UHFFFAOYSA-N 5-(1h-pyrazol-4-yl)-n-[4-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCC(F)(F)F)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 DCYQEVOEIXWGHU-UHFFFAOYSA-N 0.000 claims 1
VOGQDIOQGMUQKA-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)-n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1=NC(C)=CC(C=2N=C3SC(NC=4N=CC=C(C=4)N4CCN(CC4)S(C)(=O)=O)=NC3=CC=2)=C1 VOGQDIOQGMUQKA-UHFFFAOYSA-N 0.000 claims 1
SIBBLBOKPDGRNO-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(C=4)N4CCN(CC4)S(C)(=O)=O)=NC3=CC=2)=C1C SIBBLBOKPDGRNO-UHFFFAOYSA-N 0.000 claims 1
AQDBZZCTYQIRON-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-(4-propan-2-ylsulfonylpiperazin-1-yl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 AQDBZZCTYQIRON-UHFFFAOYSA-N 0.000 claims 1
MZPZQOBUEWBNOU-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-(4-pyridin-2-ylpiperazin-1-yl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(C=4)N4CCN(CC4)C=4N=CC=CC=4)=NC3=CC=2)=C1C MZPZQOBUEWBNOU-UHFFFAOYSA-N 0.000 claims 1
UVTYGUMQOQQUQY-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-(morpholin-4-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN5CCOCC5)C=4)=NC3=CC=2)=C1C UVTYGUMQOQQUQY-UHFFFAOYSA-N 0.000 claims 1
ASDFTRVUWCGBDR-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-(oxan-4-yloxy)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(OC5CCOCC5)C=4)=NC3=CC=2)=C1C ASDFTRVUWCGBDR-UHFFFAOYSA-N 0.000 claims 1
KKPARWUQZNPJHN-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-(piperidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN5CCCCC5)C=4)=NC3=CC=2)=C1C KKPARWUQZNPJHN-UHFFFAOYSA-N 0.000 claims 1
MMHBYHPKSSOUAO-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-(propan-2-yloxymethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CC(C)OCC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 MMHBYHPKSSOUAO-UHFFFAOYSA-N 0.000 claims 1
JXNSAADBZDBBPZ-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-[(2-methylpyrrolidin-1-yl)methyl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CC1CCCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 JXNSAADBZDBBPZ-UHFFFAOYSA-N 0.000 claims 1
GQBVRQRVFRZRAV-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-[(3-phenylpyrrolidin-1-yl)methyl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN5CC(CC5)C=5C=CC=CC=5)C=4)=NC3=CC=2)=C1C GQBVRQRVFRZRAV-UHFFFAOYSA-N 0.000 claims 1
AGVGWCFRCOMKEN-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-[4-(2-propan-2-yloxyethyl)piperazin-1-yl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 AGVGWCFRCOMKEN-UHFFFAOYSA-N 0.000 claims 1
LZDBJWNMMGJUAE-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(C=4)N4CCN(CCC(F)(F)F)CC4)=NC3=CC=2)=C1C LZDBJWNMMGJUAE-UHFFFAOYSA-N 0.000 claims 1
KGBMBRDGAPPHFR-UHFFFAOYSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-[4-(oxan-4-yl)piperazin-1-yl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(C=4)N4CCN(CC4)C4CCOCC4)=NC3=CC=2)=C1C KGBMBRDGAPPHFR-UHFFFAOYSA-N 0.000 claims 1
JXNSAADBZDBBPZ-CYBMUJFWSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@@H]1CCCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 JXNSAADBZDBBPZ-CYBMUJFWSA-N 0.000 claims 1
JXNSAADBZDBBPZ-ZDUSSCGKSA-N 5-(5-methyl-1h-pyrazol-4-yl)-n-[4-[[(2s)-2-methylpyrrolidin-1-yl]methyl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@H]1CCCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 JXNSAADBZDBBPZ-ZDUSSCGKSA-N 0.000 claims 1
WCYGLRUBCFLZDA-UHFFFAOYSA-N 5-(propan-2-yloxymethyl)-n-(5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)-1,2-oxazol-3-amine Chemical compound O1C(COC(C)C)=CC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=N1 WCYGLRUBCFLZDA-UHFFFAOYSA-N 0.000 claims 1
HTAXPFMVHLVDHB-UHFFFAOYSA-N 5-[2-[[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]amino]-1,3-benzothiazol-6-yl]pyrimidine-2-carbonitrile Chemical compound C1=NC(C#N)=NC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 HTAXPFMVHLVDHB-UHFFFAOYSA-N 0.000 claims 1
SEUOHYMZCVHPJK-UHFFFAOYSA-N 5-[2-[[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]amino]-[1,3]thiazolo[5,4-b]pyridin-5-yl]pyrimidine-2-carbonitrile Chemical compound C1=NC(C#N)=NC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=N1 SEUOHYMZCVHPJK-UHFFFAOYSA-N 0.000 claims 1
FHXDLEXIYKUHGW-UHFFFAOYSA-N 5-cyclopropyl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C=1C=NC(NC=2SC3=NC(=CC=C3N=2)C2CC2)=CC=1CN1CCCC1 FHXDLEXIYKUHGW-UHFFFAOYSA-N 0.000 claims 1
JJRBVZOMVZWTEA-UHFFFAOYSA-N 5-ethenyl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound S1C2=NC(C=C)=CC=C2N=C1NC(N=CC=1)=CC=1CN1CCCC1 JJRBVZOMVZWTEA-UHFFFAOYSA-N 0.000 claims 1
LPTPYTHSMPSLLM-UHFFFAOYSA-N 5-ethyl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound S1C2=NC(CC)=CC=C2N=C1NC(N=CC=1)=CC=1CN1CCCC1 LPTPYTHSMPSLLM-UHFFFAOYSA-N 0.000 claims 1
UPIWVZGZMYQPAU-UHFFFAOYSA-N 5-ethynyl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound S1C2=NC(C#C)=CC=C2N=C1NC(N=CC=1)=CC=1CN1CCCC1 UPIWVZGZMYQPAU-UHFFFAOYSA-N 0.000 claims 1
UBLWCUULCPKDMM-UHFFFAOYSA-N 5-methyl-6-pyridin-4-yl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound S1C=2C=C(C=3C=CN=CC=3)C(C)=CC=2N=C1NC(N=CC=1)=CC=1CN1CCCC1 UBLWCUULCPKDMM-UHFFFAOYSA-N 0.000 claims 1
GLLOWOMLKFRMBX-UHFFFAOYSA-N 5-pyridin-4-yl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C=1C=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=CC=1CN1CCCC1 GLLOWOMLKFRMBX-UHFFFAOYSA-N 0.000 claims 1
ZEHYGGQSXPPDIM-UHFFFAOYSA-N 5-pyridin-4-yl-n-[4-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCC(F)(F)F)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 ZEHYGGQSXPPDIM-UHFFFAOYSA-N 0.000 claims 1
CWBUJALSMHHRBX-UHFFFAOYSA-N 5-pyrimidin-5-yl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C=1C=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=NC=NC=2)=CC=1CN1CCCC1 CWBUJALSMHHRBX-UHFFFAOYSA-N 0.000 claims 1
CUAFDPFZUMMEAH-UHFFFAOYSA-N 6-(1h-pyrazol-4-yl)-n-[4-(pyridin-3-yloxymethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=CC=1COC1=CC=CN=C1 CUAFDPFZUMMEAH-UHFFFAOYSA-N 0.000 claims 1
JHCTXNLRXBEPKV-UHFFFAOYSA-N 6-(1h-pyrazol-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=CC=1CN1CCCC1 JHCTXNLRXBEPKV-UHFFFAOYSA-N 0.000 claims 1
FQWGCMSZNAOHDT-UHFFFAOYSA-N 6-(1h-pyrazol-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]imidazo[1,2-a]pyridin-2-amine Chemical compound C=1C=NC(NC=2N=C3C=CC(=CN3C=2)C2=CNN=C2)=CC=1CN1CCCC1 FQWGCMSZNAOHDT-UHFFFAOYSA-N 0.000 claims 1
MQAHKEVJYIXXPJ-UHFFFAOYSA-N 6-(1h-pyrazol-5-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C=2NN=CC=2)=CC=1CN1CCCC1 MQAHKEVJYIXXPJ-UHFFFAOYSA-N 0.000 claims 1
GNIGANCZGLFLMO-UHFFFAOYSA-N 6-(2-aminopyrimidin-5-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 GNIGANCZGLFLMO-UHFFFAOYSA-N 0.000 claims 1
FTVXDBUIXWNQAC-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(Cl)=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCC5)C=4)=NC3=CC=2)=C1 FTVXDBUIXWNQAC-UHFFFAOYSA-N 0.000 claims 1
QDTSSGKMELRKSW-UHFFFAOYSA-N 6-(2-methoxypyrimidin-5-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(OC)=NC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 QDTSSGKMELRKSW-UHFFFAOYSA-N 0.000 claims 1
ZFXGGQFWKOVSAX-UHFFFAOYSA-N 6-(2-methylpyridin-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCC5)C=4)=NC3=CC=2)=C1 ZFXGGQFWKOVSAX-UHFFFAOYSA-N 0.000 claims 1
VNAWQLJOYAWDKN-UHFFFAOYSA-N 6-(3,5-dimethyl-1h-pyrazol-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound CC1=NNC(C)=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 VNAWQLJOYAWDKN-UHFFFAOYSA-N 0.000 claims 1
NEZOMDOLIDINSU-UHFFFAOYSA-N 6-(3-chloropyridin-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound ClC1=CN=CC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 NEZOMDOLIDINSU-UHFFFAOYSA-N 0.000 claims 1
NBVMTIDRLALVGR-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound FC1=CN=CC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 NBVMTIDRLALVGR-UHFFFAOYSA-N 0.000 claims 1
UAOCSNZQQQSXDU-UHFFFAOYSA-N 6-(3-methoxyphenyl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound COC1=CC=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCC5)C=4)=NC3=CC=2)=C1 UAOCSNZQQQSXDU-UHFFFAOYSA-N 0.000 claims 1
GQUUHXYTBHPWTP-UHFFFAOYSA-N 6-(3-methoxypyridin-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound COC1=CN=CC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 GQUUHXYTBHPWTP-UHFFFAOYSA-N 0.000 claims 1
WPXILVPKAPURCS-UHFFFAOYSA-N 6-(3-methylpyridin-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound CC1=CN=CC=C1C1=CC=C(N=C(NC=2N=CC=C(CN3CCCC3)C=2)S2)C2=C1 WPXILVPKAPURCS-UHFFFAOYSA-N 0.000 claims 1
UXSPFKPALKMAQI-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-(4-morpholin-4-ylpyridin-2-yl)-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(C=4)N4CCOCC4)=NC3=CC=2)=C1C UXSPFKPALKMAQI-UHFFFAOYSA-N 0.000 claims 1
WEMGGVROPSTVJR-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-(4-piperazin-1-ylpyridin-2-yl)-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(C=4)N4CCNCC4)=NC3=CC=2)=C1C WEMGGVROPSTVJR-UHFFFAOYSA-N 0.000 claims 1
OVYOCBHSXMTWCL-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(C=4)N4CCN(CC4)S(C)(=O)=O)=NC3=CC=2)=C1C OVYOCBHSXMTWCL-UHFFFAOYSA-N 0.000 claims 1
ZLBHEBQJJOLJFE-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]imidazo[1,2-a]pyridin-2-amine Chemical compound N1N=CC(C2=CN3C=C(NC=4N=CC=C(C=4)N4CCN(CC4)S(C)(=O)=O)N=C3C=C2)=C1C ZLBHEBQJJOLJFE-UHFFFAOYSA-N 0.000 claims 1
DADMOVYWLGBVQG-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-(morpholin-4-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCOCC5)C=4)=NC3=CC=2)=C1C DADMOVYWLGBVQG-UHFFFAOYSA-N 0.000 claims 1
PYYCFUSYCOUAQT-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-(piperidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCCC5)C=4)=NC3=CC=2)=C1C PYYCFUSYCOUAQT-UHFFFAOYSA-N 0.000 claims 1
YHMIGTAUUIDOED-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-(propan-2-yloxymethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound CC(C)OCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 YHMIGTAUUIDOED-UHFFFAOYSA-N 0.000 claims 1
AJDDSKYZOPQJTO-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCC5)C=4)=NC3=CC=2)=C1C AJDDSKYZOPQJTO-UHFFFAOYSA-N 0.000 claims 1
RHMDJLSVCRWDBG-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-[(2-methylpyrrolidin-1-yl)methyl]pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound CC1CCCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 RHMDJLSVCRWDBG-UHFFFAOYSA-N 0.000 claims 1
WBNBICPJYKROTL-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-[(3-phenylpyrrolidin-1-yl)methyl]pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CC(CC5)C=5C=CC=CC=5)C=4)=NC3=CC=2)=C1C WBNBICPJYKROTL-UHFFFAOYSA-N 0.000 claims 1
AUAIERONLOVSLG-UHFFFAOYSA-N 6-(5-methyl-1h-pyrazol-4-yl)-n-[4-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]pyridin-2-yl]-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(C=4)N4CCN(CCC(F)(F)F)CC4)=NC3=CC=2)=C1C AUAIERONLOVSLG-UHFFFAOYSA-N 0.000 claims 1
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HAYGCUNTEDETBM-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 HAYGCUNTEDETBM-UHFFFAOYSA-N 0.000 claims 1
TVMYKHZXSCQPOE-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-6-(1,2,4-triazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)N2C=NN=C2)=C1 TVMYKHZXSCQPOE-UHFFFAOYSA-N 0.000 claims 1
UKGMYDVZRUILOM-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 UKGMYDVZRUILOM-UHFFFAOYSA-N 0.000 claims 1
AGGHDDGTVPIEGZ-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 AGGHDDGTVPIEGZ-UHFFFAOYSA-N 0.000 claims 1
YRRSVISEIBTJGD-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 YRRSVISEIBTJGD-UHFFFAOYSA-N 0.000 claims 1
PVDGYBGNJVLHIX-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 PVDGYBGNJVLHIX-UHFFFAOYSA-N 0.000 claims 1
YGWXIEYOAMEWHX-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-5-pyridazin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=NN=CC=2)=C1 YGWXIEYOAMEWHX-UHFFFAOYSA-N 0.000 claims 1
YZGBXOBLAGHNRM-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 YZGBXOBLAGHNRM-UHFFFAOYSA-N 0.000 claims 1
CMIIJFRTVOSSCZ-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-5-pyrimidin-5-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=NC=NC=2)=C1 CMIIJFRTVOSSCZ-UHFFFAOYSA-N 0.000 claims 1
FIOLCCGYCBWGHV-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 FIOLCCGYCBWGHV-UHFFFAOYSA-N 0.000 claims 1
HAEAXHNPMCKGNW-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C2=CNN=C2)=C1 HAEAXHNPMCKGNW-UHFFFAOYSA-N 0.000 claims 1
HGSAJVLZROBLAH-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 HGSAJVLZROBLAH-UHFFFAOYSA-N 0.000 claims 1
SMBZKUOVUIECEC-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-6-pyridin-4-ylimidazo[1,2-a]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=C1 SMBZKUOVUIECEC-UHFFFAOYSA-N 0.000 claims 1
WOFXIRARRWALHQ-UHFFFAOYSA-N n-[4-(4-propan-2-ylsulfonylpiperazin-1-yl)pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 WOFXIRARRWALHQ-UHFFFAOYSA-N 0.000 claims 1
MKYADUCGNFYBML-UHFFFAOYSA-N n-[4-(4-propan-2-ylsulfonylpiperazin-1-yl)pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 MKYADUCGNFYBML-UHFFFAOYSA-N 0.000 claims 1
MRCJNUPTFVHWNJ-UHFFFAOYSA-N n-[4-(aminomethyl)pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound NCC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 MRCJNUPTFVHWNJ-UHFFFAOYSA-N 0.000 claims 1
LVJJOYVDJQELPA-UHFFFAOYSA-N n-[4-(aminomethyl)pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN)C=4)=NC3=CC=2)=C1C LVJJOYVDJQELPA-UHFFFAOYSA-N 0.000 claims 1
KFONLFBZQLGMCJ-UHFFFAOYSA-N n-[4-(aminomethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound NCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 KFONLFBZQLGMCJ-UHFFFAOYSA-N 0.000 claims 1
ZBRPGJLXKBFXDM-UHFFFAOYSA-N n-[4-(aminomethyl)pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN)C=4)=NC3=CC=2)=C1C ZBRPGJLXKBFXDM-UHFFFAOYSA-N 0.000 claims 1
SQBXZEYOIYXJAB-UHFFFAOYSA-N n-[4-(aminomethyl)pyridin-2-yl]-6-pyrimidin-5-yl-1,3-benzothiazol-2-amine Chemical compound NCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=NC=NC=2)=C1 SQBXZEYOIYXJAB-UHFFFAOYSA-N 0.000 claims 1
BGJJGVZMFWJAEH-UHFFFAOYSA-N n-[4-(azepan-1-ylmethyl)pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN5CCCCCC5)C=4)=NC3=CC=2)=C1C BGJJGVZMFWJAEH-UHFFFAOYSA-N 0.000 claims 1
HLCDDPNJENODRK-UHFFFAOYSA-N n-[4-(azepan-1-ylmethyl)pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCCCC5)C=4)=NC3=CC=2)=C1C HLCDDPNJENODRK-UHFFFAOYSA-N 0.000 claims 1
CSMZOUOTCMKWOG-UHFFFAOYSA-N n-[4-(azetidin-1-ylmethyl)pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN5CCC5)C=4)=NC3=CC=2)=C1C CSMZOUOTCMKWOG-UHFFFAOYSA-N 0.000 claims 1
SPCDSEXKDCSEIN-UHFFFAOYSA-N n-[4-(azetidin-1-ylmethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=CC=1CN1CCC1 SPCDSEXKDCSEIN-UHFFFAOYSA-N 0.000 claims 1
YTYIJBFMVCLMBX-UHFFFAOYSA-N n-[4-(azetidin-1-ylmethyl)pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCC5)C=4)=NC3=CC=2)=C1C YTYIJBFMVCLMBX-UHFFFAOYSA-N 0.000 claims 1
WRSUBEUOLOANST-UHFFFAOYSA-N n-[4-(cyclopentyloxymethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=CC=1COC1CCCC1 WRSUBEUOLOANST-UHFFFAOYSA-N 0.000 claims 1
KIRJNBXEYVKEQW-UHFFFAOYSA-N n-[4-(methoxymethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound COCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 KIRJNBXEYVKEQW-UHFFFAOYSA-N 0.000 claims 1
UTZHHQVDSLTLIN-UHFFFAOYSA-N n-[4-(methylaminomethyl)pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CNCC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 UTZHHQVDSLTLIN-UHFFFAOYSA-N 0.000 claims 1
LFEXMQVZTGFPML-UHFFFAOYSA-N n-[4-(methylaminomethyl)pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CNCC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 LFEXMQVZTGFPML-UHFFFAOYSA-N 0.000 claims 1
ZGQKXECUSYMUES-UHFFFAOYSA-N n-[4-(methylaminomethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound CNCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 ZGQKXECUSYMUES-UHFFFAOYSA-N 0.000 claims 1
WPSJUEZMOCMIHM-UHFFFAOYSA-N n-[4-(methylaminomethyl)pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound CNCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 WPSJUEZMOCMIHM-UHFFFAOYSA-N 0.000 claims 1
NCISMLXZGHTHHI-UHFFFAOYSA-N n-[4-(methylaminomethyl)pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound CNCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 NCISMLXZGHTHHI-UHFFFAOYSA-N 0.000 claims 1
UGCCBOIIZAWHBH-UHFFFAOYSA-N n-[4-(oxan-4-yloxy)pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1COCCC1OC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 UGCCBOIIZAWHBH-UHFFFAOYSA-N 0.000 claims 1
QSIKJJZUWZSNQE-UHFFFAOYSA-N n-[4-(oxan-4-yloxymethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=CC=1COC1CCOCC1 QSIKJJZUWZSNQE-UHFFFAOYSA-N 0.000 claims 1
LYNMJHLIBHMSCM-UHFFFAOYSA-N n-[4-(piperazin-1-ylmethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-amine Chemical compound C=1C=NC(NC=2N=C3C=CC(=CN3C=2)C2=CNN=C2)=CC=1CN1CCNCC1 LYNMJHLIBHMSCM-UHFFFAOYSA-N 0.000 claims 1
OPOBGJSDJQHUDH-UHFFFAOYSA-N n-[4-(piperazin-1-ylmethyl)pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=CC=1CN1CCNCC1 OPOBGJSDJQHUDH-UHFFFAOYSA-N 0.000 claims 1
YQNMCHMOOBVYAQ-UHFFFAOYSA-N n-[4-(piperazin-1-ylmethyl)pyridin-2-yl]-6-pyridin-4-ylimidazo[1,2-a]pyridin-2-amine Chemical compound C=1C=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=CC=1CN1CCNCC1 YQNMCHMOOBVYAQ-UHFFFAOYSA-N 0.000 claims 1
TVSJZOBZOASSMD-UHFFFAOYSA-N n-[4-(piperidin-1-ylmethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=CC=1CN1CCCCC1 TVSJZOBZOASSMD-UHFFFAOYSA-N 0.000 claims 1
NMTFYDCMOHHUAH-UHFFFAOYSA-N n-[4-(piperidin-1-ylmethyl)pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=CC=1CN1CCCCC1 NMTFYDCMOHHUAH-UHFFFAOYSA-N 0.000 claims 1
DNOREMNIFRBDIN-UHFFFAOYSA-N n-[4-(propan-2-yloxymethyl)pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CC(C)OCC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 DNOREMNIFRBDIN-UHFFFAOYSA-N 0.000 claims 1
NEODYYZWIVDIBP-UHFFFAOYSA-N n-[4-(propan-2-yloxymethyl)pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CC(C)OCC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 NEODYYZWIVDIBP-UHFFFAOYSA-N 0.000 claims 1
BVWDDMFSJMXRMH-UHFFFAOYSA-N n-[4-(propan-2-yloxymethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound CC(C)OCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 BVWDDMFSJMXRMH-UHFFFAOYSA-N 0.000 claims 1
ZGNHTLXEVWZCDV-UHFFFAOYSA-N n-[4-(propan-2-yloxymethyl)pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound CC(C)OCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 ZGNHTLXEVWZCDV-UHFFFAOYSA-N 0.000 claims 1
RNTUPJLFDJWFAD-UHFFFAOYSA-N n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-6-(1,2,4-triazol-1-yl)-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)N2N=CN=C2)=CC=1CN1CCCC1 RNTUPJLFDJWFAD-UHFFFAOYSA-N 0.000 claims 1
PMUWXGVQZNRIEX-UHFFFAOYSA-N n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-6-(1,2,4-triazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)N2C=NN=C2)=CC=1CN1CCCC1 PMUWXGVQZNRIEX-UHFFFAOYSA-N 0.000 claims 1
KDUWANUAVIAAAL-UHFFFAOYSA-N n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-6-(1h-pyrrol-3-yl)-1,3-benzothiazol-2-amine Chemical compound C=1C=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNC=C2)=CC=1CN1CCCC1 KDUWANUAVIAAAL-UHFFFAOYSA-N 0.000 claims 1
OHEGPHMICAMRBQ-UHFFFAOYSA-N n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-6-(2,2,2-trifluoroethyl)-1,3-benzothiazol-2-amine Chemical compound S1C2=CC(CC(F)(F)F)=CC=C2N=C1NC(N=CC=1)=CC=1CN1CCCC1 OHEGPHMICAMRBQ-UHFFFAOYSA-N 0.000 claims 1
AUMPKCFFKPSQHZ-UHFFFAOYSA-N n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-6-[2-(trifluoromethyl)pyridin-4-yl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C(F)(F)F)=CC(C=2C=C3SC(NC=4N=CC=C(CN5CCCC5)C=4)=NC3=CC=2)=C1 AUMPKCFFKPSQHZ-UHFFFAOYSA-N 0.000 claims 1
DTVINZBLJBIIIX-IRXDYDNUSA-N n-[4-[(1s,4s)-5-(2-methoxyethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)CCOC)[H])N2C(C=1)=CC=NC=1NC(SC1=N2)=NC1=CC=C2C=1C=NNC=1C DTVINZBLJBIIIX-IRXDYDNUSA-N 0.000 claims 1
AUBMKBWWJBUFGJ-CYBMUJFWSA-N n-[4-[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 AUBMKBWWJBUFGJ-CYBMUJFWSA-N 0.000 claims 1
WSBMLQQKYNSREX-OAHLLOKOSA-N n-[4-[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 WSBMLQQKYNSREX-OAHLLOKOSA-N 0.000 claims 1
NXFLYTQTRGRGMS-OAHLLOKOSA-N n-[4-[(2r)-4-(2-methoxyethyl)-2-methylpiperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@@H]1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 NXFLYTQTRGRGMS-OAHLLOKOSA-N 0.000 claims 1
RVOSZJAMTJGZFM-QGZVFWFLSA-N n-[4-[(2r)-4-(2-methoxyethyl)-2-methylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@@H]1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 RVOSZJAMTJGZFM-QGZVFWFLSA-N 0.000 claims 1
AUBMKBWWJBUFGJ-ZDUSSCGKSA-N n-[4-[(2s)-2-methyl-4-methylsulfonylpiperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@H]1CN(S(C)(=O)=O)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 AUBMKBWWJBUFGJ-ZDUSSCGKSA-N 0.000 claims 1
WSBMLQQKYNSREX-HNNXBMFYSA-N n-[4-[(2s)-2-methyl-4-methylsulfonylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@H]1CN(S(C)(=O)=O)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 WSBMLQQKYNSREX-HNNXBMFYSA-N 0.000 claims 1
NXFLYTQTRGRGMS-HNNXBMFYSA-N n-[4-[(2s)-4-(2-methoxyethyl)-2-methylpiperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@H]1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 NXFLYTQTRGRGMS-HNNXBMFYSA-N 0.000 claims 1
RVOSZJAMTJGZFM-KRWDZBQOSA-N n-[4-[(2s)-4-(2-methoxyethyl)-2-methylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C[C@H]1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 RVOSZJAMTJGZFM-KRWDZBQOSA-N 0.000 claims 1
VLPCDXCRAARRDQ-UHFFFAOYSA-N n-[4-[(3,3-dimethylpyrrolidin-1-yl)methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1N=CC(C=2N=C3SC(NC=4N=CC=C(CN5CC(C)(C)CC5)C=4)=NC3=CC=2)=C1C VLPCDXCRAARRDQ-UHFFFAOYSA-N 0.000 claims 1
IQAQBYKZIBBCFL-UHFFFAOYSA-N n-[4-[(3,3-dimethylpyrrolidin-1-yl)methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical class N1N=CC(C=2C=C3SC(NC=4N=CC=C(CN5CC(C)(C)CC5)C=4)=NC3=CC=2)=C1C IQAQBYKZIBBCFL-UHFFFAOYSA-N 0.000 claims 1
MNWJMNWPOOEEOS-UHFFFAOYSA-N n-[4-[(3-methoxypyrrolidin-1-yl)methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1C(OC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 MNWJMNWPOOEEOS-UHFFFAOYSA-N 0.000 claims 1
YLPCZXYARUYJPV-UHFFFAOYSA-N n-[4-[(3-methoxypyrrolidin-1-yl)methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1C(OC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 YLPCZXYARUYJPV-UHFFFAOYSA-N 0.000 claims 1
XOUIEKUKVGGECA-UHFFFAOYSA-N n-[4-[(3-methoxypyrrolidin-1-yl)methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1C(OC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 XOUIEKUKVGGECA-UHFFFAOYSA-N 0.000 claims 1
IDFMVBLBLREXLY-OAHLLOKOSA-N n-[4-[(3r)-3-methyl-4-methylsulfonylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(C)(=O)=O)[C@H](C)CN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 IDFMVBLBLREXLY-OAHLLOKOSA-N 0.000 claims 1
VRRDRPOCGNZUKS-OAHLLOKOSA-N n-[4-[(3r)-4-(2-methoxyethyl)-3-methylpiperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1[C@@H](C)N(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 VRRDRPOCGNZUKS-OAHLLOKOSA-N 0.000 claims 1
VFKVIEVNSXPFLH-QGZVFWFLSA-N n-[4-[(3r)-4-(2-methoxyethyl)-3-methylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1[C@@H](C)N(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 VFKVIEVNSXPFLH-QGZVFWFLSA-N 0.000 claims 1
IDFMVBLBLREXLY-HNNXBMFYSA-N n-[4-[(3s)-3-methyl-4-methylsulfonylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(C)(=O)=O)[C@@H](C)CN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 IDFMVBLBLREXLY-HNNXBMFYSA-N 0.000 claims 1
VRRDRPOCGNZUKS-HNNXBMFYSA-N n-[4-[(3s)-4-(2-methoxyethyl)-3-methylpiperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1[C@H](C)N(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 VRRDRPOCGNZUKS-HNNXBMFYSA-N 0.000 claims 1
VFKVIEVNSXPFLH-KRWDZBQOSA-N n-[4-[(3s)-4-(2-methoxyethyl)-3-methylpiperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1[C@H](C)N(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 VFKVIEVNSXPFLH-KRWDZBQOSA-N 0.000 claims 1
JBRYFNSOUCTQQY-UHFFFAOYSA-N n-[4-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 JBRYFNSOUCTQQY-UHFFFAOYSA-N 0.000 claims 1
TZPZPIDMISGOOR-UHFFFAOYSA-N n-[4-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]-6-pyrimidin-5-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=NC=NC=2)=C1 TZPZPIDMISGOOR-UHFFFAOYSA-N 0.000 claims 1
SKTDLSFGFBHFHF-UHFFFAOYSA-N n-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 SKTDLSFGFBHFHF-UHFFFAOYSA-N 0.000 claims 1
HLFYZWQWJZKMMN-UHFFFAOYSA-N n-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 HLFYZWQWJZKMMN-UHFFFAOYSA-N 0.000 claims 1
HTUHDZVHCHTBQH-UHFFFAOYSA-N n-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 HTUHDZVHCHTBQH-UHFFFAOYSA-N 0.000 claims 1
QTACCHJOQCAJLY-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CN(C)CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 QTACCHJOQCAJLY-UHFFFAOYSA-N 0.000 claims 1
VXJFIJNNFDKCFC-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CN(C)CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 VXJFIJNNFDKCFC-UHFFFAOYSA-N 0.000 claims 1
QXELBONTMAFTIR-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound CN(C)CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 QXELBONTMAFTIR-UHFFFAOYSA-N 0.000 claims 1
PEORPGARFSNFHV-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound CN(C)CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 PEORPGARFSNFHV-UHFFFAOYSA-N 0.000 claims 1
HIYFEEXXLAXRRK-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound CN(C)CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 HIYFEEXXLAXRRK-UHFFFAOYSA-N 0.000 claims 1
QCWFJSYTCAAXDB-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical class C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 QCWFJSYTCAAXDB-UHFFFAOYSA-N 0.000 claims 1
MHDAHXZZKJQJAU-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 MHDAHXZZKJQJAU-UHFFFAOYSA-N 0.000 claims 1
HGXKBSYVGLTLIF-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-5-pyridazin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=NN=CC=2)=C1 HGXKBSYVGLTLIF-UHFFFAOYSA-N 0.000 claims 1
MNYQHZJAAWZNSM-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 MNYQHZJAAWZNSM-UHFFFAOYSA-N 0.000 claims 1
SITVHEKWZAMMCA-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-5-pyrimidin-5-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=NC=NC=2)=C1 SITVHEKWZAMMCA-UHFFFAOYSA-N 0.000 claims 1
ZAFHSHDFXHUKFT-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-6-(1,3-oxazol-5-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2OC=NC=2)=C1 ZAFHSHDFXHUKFT-UHFFFAOYSA-N 0.000 claims 1
ASSSXRNXSGGGHE-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 ASSSXRNXSGGGHE-UHFFFAOYSA-N 0.000 claims 1
HNQWAJHMFBUEFA-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical class C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 HNQWAJHMFBUEFA-UHFFFAOYSA-N 0.000 claims 1
BKBYYNYAUIPFOH-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-6-methyl-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC(C)=CC=C3N=2)=C1 BKBYYNYAUIPFOH-UHFFFAOYSA-N 0.000 claims 1
PMNZXTZUCCJKMK-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-6-propan-2-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C(C)C)=C1 PMNZXTZUCCJKMK-UHFFFAOYSA-N 0.000 claims 1
WQOSEFDKXFMALR-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 WQOSEFDKXFMALR-UHFFFAOYSA-N 0.000 claims 1
YPKSWRLJYPKXQN-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyridin-2-yl]-[1,3]dioxolo[4,5-f][1,3]benzothiazol-6-amine Chemical compound C1CN(CCOC)CCN1C1=CC=NC(NC=2SC3=CC=4OCOC=4C=C3N=2)=C1 YPKSWRLJYPKXQN-UHFFFAOYSA-N 0.000 claims 1
GRZNPQMGGJJDII-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperidin-1-yl]pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical class C1CC(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 GRZNPQMGGJJDII-UHFFFAOYSA-N 0.000 claims 1
SOAQCACISLFHOC-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperidin-1-yl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CC(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 SOAQCACISLFHOC-UHFFFAOYSA-N 0.000 claims 1
XFQFANVWMJBWOM-UHFFFAOYSA-N n-[4-[4-(2-methoxyethyl)piperidin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CC(CCOC)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 XFQFANVWMJBWOM-UHFFFAOYSA-N 0.000 claims 1
LNQHZXXHXPGJGA-UHFFFAOYSA-N n-[4-[4-(2-propan-2-yloxyethyl)piperazin-1-yl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC(C)C)CCN1C1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 LNQHZXXHXPGJGA-UHFFFAOYSA-N 0.000 claims 1
NPACPWJWJNZCDM-UHFFFAOYSA-N n-[4-[4-(2-propan-2-yloxyethyl)piperazin-1-yl]pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC(C)C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 NPACPWJWJNZCDM-UHFFFAOYSA-N 0.000 claims 1
CWGFBTRLBNDMRB-UHFFFAOYSA-N n-[4-[4-(2-propan-2-yloxyethyl)piperazin-1-yl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC(C)C)CCN1C1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 CWGFBTRLBNDMRB-UHFFFAOYSA-N 0.000 claims 1
PETSBYMAXLWDMA-ZBFHGGJFSA-N n-[4-[[(1r,4s)-3-azabicyclo[2.2.1]heptan-3-yl]methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1([C@@]2([H])CC[C@](C2)(C1)[H])CC(C=1)=CC=NC=1NC(SC1=N2)=NC1=CC=C2C=1C=NNC=1C PETSBYMAXLWDMA-ZBFHGGJFSA-N 0.000 claims 1
IRCFDCAAQPHJMK-QAPCUYQASA-N n-[4-[[(1r,4s)-3-azabicyclo[2.2.1]heptan-3-yl]methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound N1([C@@]2([H])CC[C@](C2)(C1)[H])CC(C=1)=CC=NC=1NC(SC1=C2)=NC1=CC=C2C=1C=NNC=1C IRCFDCAAQPHJMK-QAPCUYQASA-N 0.000 claims 1
FYPIQBPCXKDNAF-OAHLLOKOSA-N n-[4-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical class C[C@@H]1CCCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 FYPIQBPCXKDNAF-OAHLLOKOSA-N 0.000 claims 1
HJYCLAHJUSXIEG-MRXNPFEDSA-N n-[4-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C[C@@H]1CCCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 HJYCLAHJUSXIEG-MRXNPFEDSA-N 0.000 claims 1
FYPIQBPCXKDNAF-HNNXBMFYSA-N n-[4-[[(2s)-2-methylpyrrolidin-1-yl]methyl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical class C[C@H]1CCCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 FYPIQBPCXKDNAF-HNNXBMFYSA-N 0.000 claims 1
HJYCLAHJUSXIEG-INIZCTEOSA-N n-[4-[[(2s)-2-methylpyrrolidin-1-yl]methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C[C@H]1CCCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 HJYCLAHJUSXIEG-INIZCTEOSA-N 0.000 claims 1
MNWJMNWPOOEEOS-OAHLLOKOSA-N n-[4-[[(3r)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1[C@H](OC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 MNWJMNWPOOEEOS-OAHLLOKOSA-N 0.000 claims 1
UILBCLIOZMITRR-QGZVFWFLSA-N n-[4-[[(3r)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical class C1[C@H](OC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 UILBCLIOZMITRR-QGZVFWFLSA-N 0.000 claims 1
YLPCZXYARUYJPV-QGZVFWFLSA-N n-[4-[[(3r)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1[C@H](OC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 YLPCZXYARUYJPV-QGZVFWFLSA-N 0.000 claims 1
XOUIEKUKVGGECA-LJQANCHMSA-N n-[4-[[(3r)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1[C@H](OC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 XOUIEKUKVGGECA-LJQANCHMSA-N 0.000 claims 1
MNWJMNWPOOEEOS-HNNXBMFYSA-N n-[4-[[(3s)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1[C@@H](OC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 MNWJMNWPOOEEOS-HNNXBMFYSA-N 0.000 claims 1
UILBCLIOZMITRR-KRWDZBQOSA-N n-[4-[[(3s)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-5-pyridin-4-yl-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical class C1[C@@H](OC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C=2C=CN=CC=2)=C1 UILBCLIOZMITRR-KRWDZBQOSA-N 0.000 claims 1
YLPCZXYARUYJPV-KRWDZBQOSA-N n-[4-[[(3s)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1[C@@H](OC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 YLPCZXYARUYJPV-KRWDZBQOSA-N 0.000 claims 1
XOUIEKUKVGGECA-IBGZPJMESA-N n-[4-[[(3s)-3-methoxypyrrolidin-1-yl]methyl]pyridin-2-yl]-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1[C@@H](OC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 XOUIEKUKVGGECA-IBGZPJMESA-N 0.000 claims 1
MPICMVGSZWJCMI-UHFFFAOYSA-N n-[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]-5-(1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=CNN=C2)=C1 MPICMVGSZWJCMI-UHFFFAOYSA-N 0.000 claims 1
LPZOYAXWCLYXOK-UHFFFAOYSA-N n-[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1CN(CCOC)CCN1CC1=CC=NC(NC=2SC3=NC(=CC=C3N=2)C2=C(NN=C2)C)=C1 LPZOYAXWCLYXOK-UHFFFAOYSA-N 0.000 claims 1
QRCUOMNMCSCVPX-UHFFFAOYSA-N n-[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]-6-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=CNN=C2)=C1 QRCUOMNMCSCVPX-UHFFFAOYSA-N 0.000 claims 1
YJVJKSVGNTUBBB-UHFFFAOYSA-N n-[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1CN(CCOC)CCN1CC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C2=C(NN=C2)C)=C1 YJVJKSVGNTUBBB-UHFFFAOYSA-N 0.000 claims 1
HDCUJONXMRYQJG-LUMABBESSA-N n-[4-[[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]methyl]pyridin-2-yl]-5-(5-methyl-1h-pyrazol-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1([C@@]2([H])CC[C@](C2)(C1)[H])NCC(C=1)=CC=NC=1NC(SC1=N2)=NC1=CC=C2C=1C=NNC=1C HDCUJONXMRYQJG-LUMABBESSA-N 0.000 claims 1
NNYNLKSLXQUBEH-LJWDBMQJSA-N n-[4-[[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]methyl]pyridin-2-yl]-6-(5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1([C@@]2([H])CC[C@](C2)(C1)[H])NCC(C=1)=CC=NC=1NC(SC1=C2)=NC1=CC=C2C=1C=NNC=1C NNYNLKSLXQUBEH-LJWDBMQJSA-N 0.000 claims 1
GUQXIJOCXNFAIK-UHFFFAOYSA-N n-[[2-[(6-pyridin-4-yl-1,3-benzothiazol-2-yl)amino]pyridin-4-yl]methyl]methanesulfonamide Chemical compound CS(=O)(=O)NCC1=CC=NC(NC=2SC3=CC(=CC=C3N=2)C=2C=CN=CC=2)=C1 GUQXIJOCXNFAIK-UHFFFAOYSA-N 0.000 claims 1
NPUUUHNMKWMOEW-UHFFFAOYSA-N n-pyrazin-2-yl-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C=1N=CC=NC=1NC(SC1=C2)=NC1=CC=C2C1=CC=NC=C1 NPUUUHNMKWMOEW-UHFFFAOYSA-N 0.000 claims 1
JNZKEHAPSITGDW-UHFFFAOYSA-N n-pyridin-2-yl-6-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C=1C=CC=NC=1NC(SC1=C2)=NC1=CC=C2C1=CC=NC=C1 JNZKEHAPSITGDW-UHFFFAOYSA-N 0.000 claims 1
235000020824 obesity Nutrition 0.000 claims 1
201000008482 osteoarthritis Diseases 0.000 claims 1
102000020233 phosphotransferase Human genes 0.000 claims 1
IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 claims 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
208000005069 pulmonary fibrosis Diseases 0.000 claims 1
125000002098 pyridazinyl group Chemical group 0.000 claims 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 1
206010039073 rheumatoid arthritis Diseases 0.000 claims 1
206010039083 rhinitis Diseases 0.000 claims 1
230000011664 signaling Effects 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1

JP2013540089A 2010-11-19 2011-11-18 複素環式アミンおよびその使用 Active JP6005050B2 (ja)