JP2021503004A5

JP2021503004A5 -

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Publication number: JP2021503004A5
Authority: JP; Japan
Prior art keywords: isopropyl; indole; piperidine; pyridine; methyl
Prior art date: 2018-11-13
Legal status : Granted

Application number

JP2020544372A

Other languages

English (en)

Japanese (ja)

Other versions

JP2021503004A (ja

JP7265554B2 (ja

Filing date

2018-11-13

Publication date

2021-12-16

2018-11-13 Application filed filed Critical

2018-11-13 Priority claimed from PCT/US2018/060590 external-priority patent/WO2019099336A1/en

2021-02-04 Publication of JP2021503004A publication Critical patent/JP2021503004A/ja

2021-12-16 Publication of JP2021503004A5 publication Critical patent/JP2021503004A5/ja

2023-04-26 Application granted granted Critical

2023-04-26 Publication of JP7265554B2 publication Critical patent/JP7265554B2/ja

Status Active legal-status Critical Current

2038-11-13 Anticipated expiration legal-status Critical

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-1 2 -cyclopropyl Chemical group 0.000 claims 484
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 198
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 121
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 68
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 67
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 59
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 56
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 50
125000000217 alkyl group Chemical group 0.000 claims 44
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 38
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 29
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 28
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 28
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 26
UXVCEKRAZBZVSL-UHFFFAOYSA-N 2-pyridin-2-ylacetamide Chemical compound NC(=O)CC1=CC=CC=N1 UXVCEKRAZBZVSL-UHFFFAOYSA-N 0.000 claims 22
125000003709 fluoroalkyl group Chemical group 0.000 claims 22
125000002768 hydroxyalkyl group Chemical group 0.000 claims 21
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 19
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 16
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 16
229910052757 nitrogen Inorganic materials 0.000 claims 16
LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims 16
125000004966 cyanoalkyl group Chemical group 0.000 claims 15
125000004076 pyridyl group Chemical group 0.000 claims 14
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 11
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 11
229910052799 carbon Inorganic materials 0.000 claims 11
150000001875 compounds Chemical class 0.000 claims 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
150000003839 salts Chemical class 0.000 claims 11
QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims 10
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 9
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 9
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims 8
LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims 8
BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 8
125000002757 morpholinyl group Chemical group 0.000 claims 7
CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims 7
YDHIMEXEGOCNHU-UHFFFAOYSA-N 2-pyridin-3-ylacetamide Chemical compound NC(=O)CC1=CC=CN=C1 YDHIMEXEGOCNHU-UHFFFAOYSA-N 0.000 claims 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 6
125000000714 pyrimidinyl group Chemical group 0.000 claims 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 5
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 5
125000003386 piperidinyl group Chemical group 0.000 claims 5
ZXIXQISOZCXHKO-UHFFFAOYSA-N 4-[3-ethyl-5-(3-fluoropiperidin-4-yl)-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1C(CNCC1)F)C1=C2C(=NC=C1)NN=C2 ZXIXQISOZCXHKO-UHFFFAOYSA-N 0.000 claims 4
WHDWZXKVCFANBQ-UHFFFAOYSA-N 8-methyl-4-oxo-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-quinoline-3-carbonitrile Chemical compound OC1=C(C=NC2=C(C=C(C=C12)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)C#N WHDWZXKVCFANBQ-UHFFFAOYSA-N 0.000 claims 4
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
125000000623 heterocyclic group Chemical group 0.000 claims 4
VTVRXITWWZGKHV-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=CC=CC2=NC=CN21 VTVRXITWWZGKHV-UHFFFAOYSA-N 0.000 claims 4
125000002883 imidazolyl group Chemical group 0.000 claims 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 4
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 4
125000001424 substituent group Chemical group 0.000 claims 4
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
125000000335 thiazolyl group Chemical group 0.000 claims 4
125000001425 triazolyl group Chemical group 0.000 claims 4
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims 3
BWFYJNIJELCOPW-UHFFFAOYSA-N 4-(3,4-dimethyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-pyrazolo[3,4-b]pyridine Chemical compound CC1=C(NC2=CC=C(C(=C12)C)C1CCNCC1)C1=C2C(=NC=C1)NN=C2 BWFYJNIJELCOPW-UHFFFAOYSA-N 0.000 claims 3
FKGQPSYLXOHMJZ-UHFFFAOYSA-N 4-piperidin-1-yl-1-propan-2-ylpiperidine Chemical compound C1CN(C(C)C)CCC1N1CCCCC1 FKGQPSYLXOHMJZ-UHFFFAOYSA-N 0.000 claims 3
YXSUIVZFLAJASX-UHFFFAOYSA-N 5-methoxy-1h-imidazole Chemical compound COC1=CN=CN1 YXSUIVZFLAJASX-UHFFFAOYSA-N 0.000 claims 3
ZCPMWJQPYHKTOJ-UHFFFAOYSA-N 5-methoxy-2-methyl-1h-imidazole Chemical compound COC1=CN=C(C)N1 ZCPMWJQPYHKTOJ-UHFFFAOYSA-N 0.000 claims 3
GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims 3
SMCVFCDQVIJYKV-UHFFFAOYSA-N 8-methyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)quinoline Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C=CC=NC2=C(C=1)C SMCVFCDQVIJYKV-UHFFFAOYSA-N 0.000 claims 3
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 3
125000003545 alkoxy group Chemical group 0.000 claims 3
125000003725 azepanyl group Chemical group 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 3
125000004965 chloroalkyl group Chemical group 0.000 claims 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
125000000842 isoxazolyl group Chemical group 0.000 claims 3
125000001715 oxadiazolyl group Chemical group 0.000 claims 3
125000002971 oxazolyl group Chemical group 0.000 claims 3
125000003566 oxetanyl group Chemical group 0.000 claims 3
239000008194 pharmaceutical composition Substances 0.000 claims 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 3
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 3
125000003226 pyrazolyl group Chemical group 0.000 claims 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
QPKQSAVVUUHAJP-INIZCTEOSA-N (3S)-3-amino-1-[4-[3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]butan-1-one Chemical compound N[C@H](CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C)C QPKQSAVVUUHAJP-INIZCTEOSA-N 0.000 claims 2
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 2
NLMVYUBGWZWUGB-UHFFFAOYSA-N 1,2-benzoxazol-3-amine Chemical compound C1=CC=C2C(N)=NOC2=C1 NLMVYUBGWZWUGB-UHFFFAOYSA-N 0.000 claims 2
FPYJATIGAMFLSU-UHFFFAOYSA-N 1,2-dimethyl-3-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(N(C2=NC=CC=C21)C)C FPYJATIGAMFLSU-UHFFFAOYSA-N 0.000 claims 2
125000005960 1,4-diazepanyl group Chemical group 0.000 claims 2
BQRMCPMZVZWZNY-UHFFFAOYSA-N 1-[4-(2-imidazo[1,2-a]pyrimidin-6-yl-3-propan-2-yl-1H-indol-5-yl)piperidin-1-yl]-2-methylpropan-2-ol Chemical compound N=1C=CN2C=1N=CC(=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(C)(O)C BQRMCPMZVZWZNY-UHFFFAOYSA-N 0.000 claims 2
SWURTWPVHAYVJU-UHFFFAOYSA-N 1-[4-[2-(8-chloroquinolin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound ClC=1C=C(C=C2C=CC=NC=12)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)C)=O SWURTWPVHAYVJU-UHFFFAOYSA-N 0.000 claims 2
XLFDROMJRMYJQH-PSWAGMNNSA-N 1-[4-[2-(8-methyltetrazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound [C@H]12CN(C[C@H](CC1)O2)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=NN=2)C)C(C)C XLFDROMJRMYJQH-PSWAGMNNSA-N 0.000 claims 2
PDORURBXSKULFI-PSWAGMNNSA-N 1-[4-[2-(8-methyltetrazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-[(1S,5R)-3-oxa-8-azabicyclo[3.2.1]octan-8-yl]ethanone Chemical compound [C@H]12COC[C@H](CC1)N2CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=NN=2)C)C(C)C PDORURBXSKULFI-PSWAGMNNSA-N 0.000 claims 2
ZDSPKALDRJYJKA-UHFFFAOYSA-N 1-[4-[3-ethyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CNC)=O)C1=C2C(=NC=C1)NN=C2 ZDSPKALDRJYJKA-UHFFFAOYSA-N 0.000 claims 2
MWZDIEIXRBWPLG-UHFFFAOYSA-N 1-methyl-1,2,4-triazole Chemical compound CN1C=NC=N1 MWZDIEIXRBWPLG-UHFFFAOYSA-N 0.000 claims 2
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 2
YTRUWKGBKZWORO-UHFFFAOYSA-N 1-methyl-3-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C2=NC=CC=C21)C YTRUWKGBKZWORO-UHFFFAOYSA-N 0.000 claims 2
UAMNEZHTDCQXEE-UHFFFAOYSA-N 1-methyl-3-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CN(C2=NC=CC=C21)C UAMNEZHTDCQXEE-UHFFFAOYSA-N 0.000 claims 2
OSARPQDGQMWWKD-UHFFFAOYSA-N 1-methyl-3-[5-[1-[(2-methylpyrimidin-5-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1C=NC(=NC=1)C)C1=CN(C2=NC=CC=C21)C OSARPQDGQMWWKD-UHFFFAOYSA-N 0.000 claims 2
DCSYEYMITPSHHP-UHFFFAOYSA-N 1-methyl-4-[3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]pyrazolo[3,4-d]pyrimidine Chemical compound C(C)(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=N1)N(N=C2)C)C DCSYEYMITPSHHP-UHFFFAOYSA-N 0.000 claims 2
NPQQYYWDKJWZHM-UHFFFAOYSA-N 1-methyl-4-[3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)N(C=C2)C)C NPQQYYWDKJWZHM-UHFFFAOYSA-N 0.000 claims 2
USGZLOGRKROIDB-UHFFFAOYSA-N 1-methyl-4-[4-[2-(2-methylquinolin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidine-1-carbonyl]pyrrolidin-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O)C1=CC(=NC2=CC=CC=C12)C USGZLOGRKROIDB-UHFFFAOYSA-N 0.000 claims 2
KQQCYOFFBIJWIV-UHFFFAOYSA-N 1-methyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C(=NC=1)N(N=C2)C KQQCYOFFBIJWIV-UHFFFAOYSA-N 0.000 claims 2
GKIDPKQAUSZEFO-UHFFFAOYSA-N 1-methyl-7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[4,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)C=NN2C GKIDPKQAUSZEFO-UHFFFAOYSA-N 0.000 claims 2
UICSWVYUZXNNTJ-UHFFFAOYSA-N 1-methylsulfonyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)N(C=C2)S(=O)(=O)C UICSWVYUZXNNTJ-UHFFFAOYSA-N 0.000 claims 2
ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical compound O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 claims 2
LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 claims 2
QGVBBDCVPNXOFA-UHFFFAOYSA-N 2,5-dimethyl-8-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=2N(C(=CC=1)C)N=C(N=2)C QGVBBDCVPNXOFA-UHFFFAOYSA-N 0.000 claims 2
JRCZROFTUZWJGY-UHFFFAOYSA-N 2,7-dimethyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C(=C1)C)N=C(C=2)C JRCZROFTUZWJGY-UHFFFAOYSA-N 0.000 claims 2
TUNBEABBBHWMSP-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-3-ethyl-5-piperidin-4-yl-1H-indole Chemical compound O1C(=CC2=C1C=CC=C2)C=1NC2=CC=C(C=C2C=1CC)C1CCNCC1 TUNBEABBBHWMSP-UHFFFAOYSA-N 0.000 claims 2
QWFNPPGDOSYBMQ-UHFFFAOYSA-N 2-(1-benzofuran-5-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound O1C=CC2=C1C=CC(=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 QWFNPPGDOSYBMQ-UHFFFAOYSA-N 0.000 claims 2
FQIBOTQVKSDIJH-UHFFFAOYSA-N 2-(1H-indol-6-yl)-5-piperidin-4-yl-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=C2C=CNC2=C1 FQIBOTQVKSDIJH-UHFFFAOYSA-N 0.000 claims 2
ONNMCWPWRIXQQU-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-1-[4-[2-(8-methyltetrazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound FC1(CCN(CC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=NN=2)C)C(C)C)F ONNMCWPWRIXQQU-UHFFFAOYSA-N 0.000 claims 2
QWAIDTPIGMLBKY-UHFFFAOYSA-N 2-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1SC=2CNCCC=2N=1 QWAIDTPIGMLBKY-UHFFFAOYSA-N 0.000 claims 2
KKPZLGBTNWCJET-UHFFFAOYSA-N 2-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(CNCC2)S1 KKPZLGBTNWCJET-UHFFFAOYSA-N 0.000 claims 2
KIIAYWPQDGMXMX-UHFFFAOYSA-N 2-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=NN2C(C=NC=C2)=N1 KIIAYWPQDGMXMX-UHFFFAOYSA-N 0.000 claims 2
WKQPEFQRFCAZEK-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-(2-imidazo[1,2-a]pyridin-6-yl-3-propan-2-yl-1H-indol-5-yl)piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=CC=2N(C=1)C=CN=2)C(C)C)C WKQPEFQRFCAZEK-UHFFFAOYSA-N 0.000 claims 2
WQYOYBXRBDEMRV-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(3-methyltriazolo[1,5-a]pyridin-5-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=2N(C=C1)N=NC=2C)C(C)C)C WQYOYBXRBDEMRV-UHFFFAOYSA-N 0.000 claims 2
YPDKVZQPBGWMTN-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(4-methyltriazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=NC=2)C)C(C)C)C YPDKVZQPBGWMTN-UHFFFAOYSA-N 0.000 claims 2
MBDHAQSMZXUIBE-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=2N(C(=C1)OC)N=CN=2)C(C)C)C MBDHAQSMZXUIBE-UHFFFAOYSA-N 0.000 claims 2
CROMTWHEQLXMIA-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(5-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=2N(C(=C1)C)N=CN=2)C(C)C)C CROMTWHEQLXMIA-UHFFFAOYSA-N 0.000 claims 2
NAJNWGAGPMSCLX-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(7,8-dimethyltetrazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C(=C(C=2N(C=1)N=NN=2)C)C)C(C)C)C NAJNWGAGPMSCLX-UHFFFAOYSA-N 0.000 claims 2
SBZYWRUXDVGGTC-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(7-methylpyrazolo[1,5-a]pyridin-5-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=2N(C(=C1)C)N=CC=2)C(C)C)C SBZYWRUXDVGGTC-UHFFFAOYSA-N 0.000 claims 2
NIOKWBYUQINPEQ-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[3-propan-2-yl-2-([1,2,4]triazolo[1,5-b]pyridazin-6-yl)-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound N=1C=NN2N=C(C=CC2=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)C)=O NIOKWBYUQINPEQ-UHFFFAOYSA-N 0.000 claims 2
WLCPWIGMCYTESL-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[3-propan-2-yl-2-([1,2,4]triazolo[4,3-a]pyridin-7-yl)-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound N=1N=CN2C=1C=C(C=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)C)=O WLCPWIGMCYTESL-UHFFFAOYSA-N 0.000 claims 2
CNRUYEWZMKDDKO-UHFFFAOYSA-N 2-(methylamino)-1-[4-[2-(8-methylquinolin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CNC)=O)C=1C=C2C=CC=NC2=C(C=1)C CNRUYEWZMKDDKO-UHFFFAOYSA-N 0.000 claims 2
VSIDCRQWHURQQN-UHFFFAOYSA-N 2-(methylamino)-1-[4-[3-propan-2-yl-2-([1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound N1=CN=C2N1C=C(C=N2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC)=O VSIDCRQWHURQQN-UHFFFAOYSA-N 0.000 claims 2
ZXUYLPZBCSIEAF-QFIPXVFZSA-N 2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-1-[4-[3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN([C@@H]1CN(CC1)CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C)C ZXUYLPZBCSIEAF-QFIPXVFZSA-N 0.000 claims 2
DHPNZXOJCFHDEG-UHFFFAOYSA-N 2-[3-fluoro-4-[3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound FC1CN(CCC1C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C)CCNC DHPNZXOJCFHDEG-UHFFFAOYSA-N 0.000 claims 2
HPWZBOYDFYXUKN-UHFFFAOYSA-N 2-[4-(2-imidazo[1,2-a]pyrimidin-3-yl-3-propan-2-yl-1H-indol-5-yl)piperidin-1-yl]-N,N-dimethylacetamide Chemical compound N=1C=C(N2C=1N=CC=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C HPWZBOYDFYXUKN-UHFFFAOYSA-N 0.000 claims 2
AIWQDNZVBKJMKC-UHFFFAOYSA-N 2-[4-[2-(1,3-benzoxazol-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound O1C=NC2=C1C=C(C=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C AIWQDNZVBKJMKC-UHFFFAOYSA-N 0.000 claims 2
XZSVFLXFKGQLTP-UHFFFAOYSA-N 2-[4-[2-(1-methylpyrrolo[2,3-b]pyridin-3-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]acetonitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC#N)C1=CN(C2=NC=CC=C21)C XZSVFLXFKGQLTP-UHFFFAOYSA-N 0.000 claims 2
NJHPUORPLLRJTM-UHFFFAOYSA-N 2-[4-[2-(2,7-dimethyl-1,3-benzoxazol-5-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound CC=1OC2=C(N=1)C=C(C=C2C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C NJHPUORPLLRJTM-UHFFFAOYSA-N 0.000 claims 2
OCYADJPCGDSQEP-UHFFFAOYSA-N 2-[4-[2-(3-fluoro-2-methylpyrazolo[1,5-a]pyridin-5-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound FC=1C(=NN2C=1C=C(C=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C)C OCYADJPCGDSQEP-UHFFFAOYSA-N 0.000 claims 2
AAVNPNFDHKYTST-UHFFFAOYSA-N 2-[4-[2-(3-fluoro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound FC=1C(=NN2C=1N=C(C=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C)C AAVNPNFDHKYTST-UHFFFAOYSA-N 0.000 claims 2
ZFGIDOQFERCRCI-UHFFFAOYSA-N 2-[4-[2-(5-methoxy-1-benzofuran-2-yl)-3-methyl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=CC2=C(C=C(O2)C=2NC3=CC=C(C=C3C=2C)C2CCN(CC2)CCNC)C=1 ZFGIDOQFERCRCI-UHFFFAOYSA-N 0.000 claims 2
PSHSSNYLPKUPHU-UHFFFAOYSA-N 2-[4-[2-(5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(=O)N(C)C)C1=CC=2N(C(=C1)OC)N=CN=2 PSHSSNYLPKUPHU-UHFFFAOYSA-N 0.000 claims 2
RPEMWHDRFFIVTD-UHFFFAOYSA-N 2-[4-[2-(6-fluoro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound FC=1C(=NC=2N(C=1)N=C(C=2)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C RPEMWHDRFFIVTD-UHFFFAOYSA-N 0.000 claims 2
SSZGMIGAZHZKJY-UHFFFAOYSA-N 2-[4-[2-(7,8-dimethyltetrazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CCN(CC1)CC(=O)N(C)C)N=NN=2)C SSZGMIGAZHZKJY-UHFFFAOYSA-N 0.000 claims 2
YFHLQPGKPWQOSG-UHFFFAOYSA-N 2-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-b]pyridazin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(=O)N(C)C)C=1C=C(C=2N(N=1)N=CN=2)OC YFHLQPGKPWQOSG-UHFFFAOYSA-N 0.000 claims 2
OFQIILJPTKJEJR-UHFFFAOYSA-N 2-[4-[3-(2,2-difluoroethyl)-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(=O)NC)C1=C2C(=NC=C1)NN=C2)F OFQIILJPTKJEJR-UHFFFAOYSA-N 0.000 claims 2
BKOTZCLKFQZBAE-UHFFFAOYSA-N 2-[4-[3-(2,2-difluoroethyl)-2-imidazo[1,2-a]pyridin-6-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCNC)C=1C=CC=2N(C=1)C=CN=2)F BKOTZCLKFQZBAE-UHFFFAOYSA-N 0.000 claims 2
IDWZZDLHTGXQJT-UHFFFAOYSA-N 2-[4-[3-ethyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCNC)C1=C2C(=NC=C1)NN=C2 IDWZZDLHTGXQJT-UHFFFAOYSA-N 0.000 claims 2
WRIBACUHWNLHEG-UHFFFAOYSA-N 2-[4-[3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]ethanamine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCN)C1=C2C(=NC=C1)NN=C2 WRIBACUHWNLHEG-UHFFFAOYSA-N 0.000 claims 2
VDTQSJFSFHVURV-UHFFFAOYSA-N 2-[methyl(propan-2-yl)amino]-1-[4-[3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound C(C)(C)N(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C)C VDTQSJFSFHVURV-UHFFFAOYSA-N 0.000 claims 2
UCFALXKLKXEGNW-UHFFFAOYSA-N 2-amino-1-[4-[3-ethyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound NCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)CC UCFALXKLKXEGNW-UHFFFAOYSA-N 0.000 claims 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
HDRNLWJYQQEDIP-UHFFFAOYSA-N 2-chloro-8-methyl-3-[[4-[3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]methyl]quinoline Chemical compound ClC1=NC2=C(C=CC=C2C=C1CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C)C HDRNLWJYQQEDIP-UHFFFAOYSA-N 0.000 claims 2
YHMWJBYVQRKTJM-UHFFFAOYSA-N 2-methoxy-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)quinoline Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC2=CC=CC=C12)OC YHMWJBYVQRKTJM-UHFFFAOYSA-N 0.000 claims 2
MJWPBTCZMCEOLZ-UHFFFAOYSA-N 2-methyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)quinoline Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC2=CC=CC=C12)C MJWPBTCZMCEOLZ-UHFFFAOYSA-N 0.000 claims 2
XVWKBEZUIFDJLR-UHFFFAOYSA-N 2-methyl-4-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]quinoline Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC(=NC2=CC=CC=C12)C XVWKBEZUIFDJLR-UHFFFAOYSA-N 0.000 claims 2
YBZAVCGJSIGADD-UHFFFAOYSA-N 2-methyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C=C1)N=C(C=2)C YBZAVCGJSIGADD-UHFFFAOYSA-N 0.000 claims 2
OZLGCMKLCOGDDC-UHFFFAOYSA-N 2-methyl-5-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]pyrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC=2N(C=C1)N=C(C=2)C OZLGCMKLCOGDDC-UHFFFAOYSA-N 0.000 claims 2
LOPSWDRRKQKJPC-UHFFFAOYSA-N 2-methyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1,3-benzoxazole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(N=C(O2)C)C=C1 LOPSWDRRKQKJPC-UHFFFAOYSA-N 0.000 claims 2
FDGMSHUVSPJBII-UHFFFAOYSA-N 2-methyl-7-(2-methylpropyl)-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[1,5-a]pyridine Chemical compound C(C(C)C)C1=CC(=CC=2N1N=C(C=2)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 FDGMSHUVSPJBII-UHFFFAOYSA-N 0.000 claims 2
JZXXVODYJKIBOK-UHFFFAOYSA-N 2-methyl-7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C=C1)N=C(N=2)C JZXXVODYJKIBOK-UHFFFAOYSA-N 0.000 claims 2
SDCFGFIEROWAQG-UHFFFAOYSA-N 2-methyl-7-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC=2N(C=C1)N=C(N=2)C SDCFGFIEROWAQG-UHFFFAOYSA-N 0.000 claims 2
XRQYPEXMFCFBEK-UHFFFAOYSA-N 2-methyl-8-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=2N(C=CC=1)N=C(N=2)C XRQYPEXMFCFBEK-UHFFFAOYSA-N 0.000 claims 2
DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-UHFFFAOYSA-N 0.000 claims 2
HBKYFQUAFRXSSO-UHFFFAOYSA-N 2-piperidin-3-ylacetamide Chemical compound NC(=O)CC1CCCNC1 HBKYFQUAFRXSSO-UHFFFAOYSA-N 0.000 claims 2
OFMALDSHFYWVKM-UHFFFAOYSA-N 2-pyrrolidin-2-ylacetamide Chemical compound NC(=O)CC1CCCN1 OFMALDSHFYWVKM-UHFFFAOYSA-N 0.000 claims 2
GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 2
NWZXAAOTMBDUQY-UHFFFAOYSA-N 3,4-dihydro-1,4-oxazin-2-one Chemical compound O=C1CNC=CO1 NWZXAAOTMBDUQY-UHFFFAOYSA-N 0.000 claims 2
STBJPEFXFQMSQY-UHFFFAOYSA-N 3,7-dimethyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1,3-benzoxazol-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C2=C(N(C(O2)=O)C)C=1)C STBJPEFXFQMSQY-UHFFFAOYSA-N 0.000 claims 2
AVHCXRTWEQSKJP-UHFFFAOYSA-N 3-(3,3-difluoropyrrolidin-1-yl)-1-[4-[2-(8-methyltetrazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]propan-1-one Chemical compound FC1(CN(CC1)CCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=NN=2)C)C(C)C)F AVHCXRTWEQSKJP-UHFFFAOYSA-N 0.000 claims 2
NRNAXDZZKZGAAJ-UHFFFAOYSA-N 3-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CNC2=NC=CC=C21 NRNAXDZZKZGAAJ-UHFFFAOYSA-N 0.000 claims 2
IKKMMJIQCGGFJJ-UHFFFAOYSA-N 3-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)imidazo[1,2-a]pyrazine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN=C2N1C=CN=C2 IKKMMJIQCGGFJJ-UHFFFAOYSA-N 0.000 claims 2
NVECBSZKUBMZKW-UHFFFAOYSA-N 3-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)imidazo[1,2-a]pyrimidine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN=C2N1C=CC=N2 NVECBSZKUBMZKW-UHFFFAOYSA-N 0.000 claims 2
OSBMJJNAEWFVGQ-UHFFFAOYSA-N 3-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrrolo[2,3-c]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CNC2=CN=CC=C21 OSBMJJNAEWFVGQ-UHFFFAOYSA-N 0.000 claims 2
RVTLAQFUIGIQAP-UHFFFAOYSA-N 3-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrrolo[3,2-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CNC=2C1=NC=CC=2 RVTLAQFUIGIQAP-UHFFFAOYSA-N 0.000 claims 2
ASWHZBYKXOFPCQ-UHFFFAOYSA-N 3-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-2,5-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=NNC=2N=CNC(C=21)=O ASWHZBYKXOFPCQ-UHFFFAOYSA-N 0.000 claims 2
SCZYOTRFMDUWCZ-UHFFFAOYSA-N 3-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-2H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=NNC2=NC=CC=C21 SCZYOTRFMDUWCZ-UHFFFAOYSA-N 0.000 claims 2
ZTZSLMLFNNMFGF-UHFFFAOYSA-N 3-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyrimidine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN=C2N1C=CC=N2 ZTZSLMLFNNMFGF-UHFFFAOYSA-N 0.000 claims 2
RJQCTUGYKVWNQN-UHFFFAOYSA-N 3-[4-[6-fluoro-3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylpropan-1-amine Chemical compound FC1=C(C=C2C(=C(NC2=C1)C1=C2C(=NC=C1)NN=C2)C(C)C)C1CCN(CC1)CCCN(C)C RJQCTUGYKVWNQN-UHFFFAOYSA-N 0.000 claims 2
GQUXSIJFVLPCMY-UHFFFAOYSA-N 3-[[4-[3-ethyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]methyl]-5-phenyl-1,2-oxazole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=NOC(=C1)C1=CC=CC=C1)C1=C2C(=NC=C1)NN=C2 GQUXSIJFVLPCMY-UHFFFAOYSA-N 0.000 claims 2
GWLLJIUUAJBWIX-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-1-[4-[2-(8-methyltetrazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]propan-1-one Chemical compound C(C)(C)N(CCC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=NN=2)C)C(C)C)C GWLLJIUUAJBWIX-UHFFFAOYSA-N 0.000 claims 2
HBPSGTYPSZIWJO-UHFFFAOYSA-N 3-chloro-4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine Chemical compound ClC1=CNC2=NC=CC(=C21)C=1NC2=CC=C(C=C2C=1CC)C1CCNCC1 HBPSGTYPSZIWJO-UHFFFAOYSA-N 0.000 claims 2
PGRFEAOMNLBFHQ-UHFFFAOYSA-N 3-chloro-4-[3-ethyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound ClC1=CNC2=NC=CC(=C21)C=1NC2=CC=C(C=C2C=1CC)C1CCN(CC1)C1CCN(CC1)C(C)C PGRFEAOMNLBFHQ-UHFFFAOYSA-N 0.000 claims 2
CXSOIAVNPXNMEV-UHFFFAOYSA-N 3-ethyl-4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)C1=CNC2=NC=CC(=C21)C=1NC2=CC=C(C=C2C=1CC)C1CCNCC1 CXSOIAVNPXNMEV-UHFFFAOYSA-N 0.000 claims 2
ZEEFQZXFWPNUQX-UHFFFAOYSA-N 3-ethyl-4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-2H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=NNC2=NC=CC(=C21)C=1NC2=CC=C(C=C2C=1CC)C1CCNCC1 ZEEFQZXFWPNUQX-UHFFFAOYSA-N 0.000 claims 2
MDLYHSUJKJKCRM-UHFFFAOYSA-N 3-ethyl-4-(3-methyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine Chemical compound CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NC=C2CC MDLYHSUJKJKCRM-UHFFFAOYSA-N 0.000 claims 2
XPEVBLYPDIDHJQ-UHFFFAOYSA-N 3-fluoro-2-methyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[1,5-a]pyridine Chemical compound FC=1C(=NN2C=1C=C(C=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C XPEVBLYPDIDHJQ-UHFFFAOYSA-N 0.000 claims 2
SRWRDQFXIONONJ-UHFFFAOYSA-N 3-fluoro-2-methyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC=1C(=NN2C=1N=C(C=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C SRWRDQFXIONONJ-UHFFFAOYSA-N 0.000 claims 2
XMBRICPTGDTKJA-UHFFFAOYSA-N 3-hydroxy-3-methyl-1-[4-[2-(2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]butan-1-one Chemical compound OC(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=2N(C=C1)N=C(N=2)C)C(C)C)(C)C XMBRICPTGDTKJA-UHFFFAOYSA-N 0.000 claims 2
XUZRZBJGSDEBEJ-UHFFFAOYSA-N 3-methyl-4-(3-methyl-5-piperidin-4-yl-1H-indol-2-yl)-2H-pyrazolo[3,4-b]pyridine Chemical compound CC1=NNC2=NC=CC(=C21)C=1NC2=CC=C(C=C2C=1C)C1CCNCC1 XUZRZBJGSDEBEJ-UHFFFAOYSA-N 0.000 claims 2
IXJZDJSBDLXZSS-UHFFFAOYSA-N 3-methyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NC=C2C IXJZDJSBDLXZSS-UHFFFAOYSA-N 0.000 claims 2
JYLYVGXLSRLARE-UHFFFAOYSA-N 3-methyl-4-[5-[1-[(2-methyl-1H-imidazol-5-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-2H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=CN=C(N1)C)C1=C2C(=NC=C1)NN=C2C JYLYVGXLSRLARE-UHFFFAOYSA-N 0.000 claims 2
KGZHVKKUKACNMW-UHFFFAOYSA-N 3-methyl-5-[5-[1-(2-methylsulfonylethyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCS(=O)(=O)C)C1=CC=2N(C=C1)N=NC=2C KGZHVKKUKACNMW-UHFFFAOYSA-N 0.000 claims 2
GBUGSXJMEYTUJS-UHFFFAOYSA-N 3-methyl-5-[5-[1-[(1-methylpyrazol-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=NN(C=C1)C)C1=CC=2N(C=C1)N=NC=2C GBUGSXJMEYTUJS-UHFFFAOYSA-N 0.000 claims 2
XQIDQLGEQAAHQU-UHFFFAOYSA-N 3-methyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1,3-benzoxazol-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(N(C(O2)=O)C)C=C1 XQIDQLGEQAAHQU-UHFFFAOYSA-N 0.000 claims 2
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 2
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims 2
XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims 2
SHTJLYVJXTYJFQ-UHFFFAOYSA-N 4-(3-ethyl-4-methyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C(=C12)C)C1CCNCC1)C1=C2C(=NC=C1)NN=C2 SHTJLYVJXTYJFQ-UHFFFAOYSA-N 0.000 claims 2
QTHRCBVQBMESSM-UHFFFAOYSA-N 4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1-methylindazole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C=NN(C2=CC=C1)C QTHRCBVQBMESSM-UHFFFAOYSA-N 0.000 claims 2
JELXQPFVAZMOPG-UHFFFAOYSA-N 4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-indazole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C=NNC2=CC=C1 JELXQPFVAZMOPG-UHFFFAOYSA-N 0.000 claims 2
XQVVOFKJEDIMSV-UHFFFAOYSA-N 4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-3-methyl-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NC=C2C XQVVOFKJEDIMSV-UHFFFAOYSA-N 0.000 claims 2
JBYAXPLCUJFCCD-UHFFFAOYSA-N 4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-3-methyl-2H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NN=C2C JBYAXPLCUJFCCD-UHFFFAOYSA-N 0.000 claims 2
CRKFYJISAZCBSK-UHFFFAOYSA-N 4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-5-methyl-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1C)NC=C2 CRKFYJISAZCBSK-UHFFFAOYSA-N 0.000 claims 2
JUNAUDWZDDIALQ-UHFFFAOYSA-N 4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-7H-pyrrolo[2,3-c]pyridazine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C2=C(N=NC=1)NC=C2 JUNAUDWZDDIALQ-UHFFFAOYSA-N 0.000 claims 2
BQVOLSAQCXKAGP-UHFFFAOYSA-N 4-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C2=C(N=CN=1)NC=C2 BQVOLSAQCXKAGP-UHFFFAOYSA-N 0.000 claims 2
YGUKOVMUGYCOSH-UHFFFAOYSA-N 4-(3-methyl-5-piperidin-4-yl-1H-indol-2-yl)-1H-pyrazolo[3,4-b]pyridine Chemical compound CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NN=C2 YGUKOVMUGYCOSH-UHFFFAOYSA-N 0.000 claims 2
NPKJZFLUCXJGPN-UHFFFAOYSA-N 4-(3-methyl-5-piperidin-4-yl-1H-indol-2-yl)-3-phenyl-1H-pyrrolo[2,3-b]pyridine Chemical compound CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NC=C2C1=CC=CC=C1 NPKJZFLUCXJGPN-UHFFFAOYSA-N 0.000 claims 2
HHWDQFGZKQKATG-UHFFFAOYSA-N 4-(3-methyl-5-piperidin-4-yl-1H-indol-2-yl)-3-propan-2-yl-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=CNC2=NC=CC(=C21)C=1NC2=CC=C(C=C2C=1C)C1CCNCC1 HHWDQFGZKQKATG-UHFFFAOYSA-N 0.000 claims 2
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 2
OOUJCNVECGABRD-UHFFFAOYSA-N 4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-indazole-7-carbonitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C=NNC2=C(C=C1)C#N OOUJCNVECGABRD-UHFFFAOYSA-N 0.000 claims 2
WSSXDMFZUVJPQP-UHFFFAOYSA-N 4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrrolo[2,1-f][1,2,4]triazine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=NC=NN2C1=CC=C2 WSSXDMFZUVJPQP-UHFFFAOYSA-N 0.000 claims 2
VRFXCPIPSDBHQI-UHFFFAOYSA-N 4-(6-chloro-5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrazolo[3,4-b]pyridine Chemical compound ClC1=C(C=C2C(=C(NC2=C1)C1=C2C(=NC=C1)NN=C2)C(C)C)C1CCNCC1 VRFXCPIPSDBHQI-UHFFFAOYSA-N 0.000 claims 2
JERNLYZBJHFMJB-UHFFFAOYSA-N 4-(6-methoxy-5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC(=C(C=C12)C1CCNCC1)OC)C1=C2C(=NC=C1)NN=C2 JERNLYZBJHFMJB-UHFFFAOYSA-N 0.000 claims 2
SRPYPPGFAGNJSW-UHFFFAOYSA-N 4-(6-methyl-5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC(=C(C=C12)C1CCNCC1)C)C1=C2C(=NC=C1)NN=C2 SRPYPPGFAGNJSW-UHFFFAOYSA-N 0.000 claims 2
KOKKZYINAYGPAJ-UHFFFAOYSA-N 4-[3-(2,2-difluoroethyl)-5-piperidin-4-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NN=C2)F KOKKZYINAYGPAJ-UHFFFAOYSA-N 0.000 claims 2
TVPOVHHSXYZFEW-UHFFFAOYSA-N 4-[3-(2,2-difluoroethyl)-5-piperidin-4-yl-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NC=C2)F TVPOVHHSXYZFEW-UHFFFAOYSA-N 0.000 claims 2
QOMVTARMHYWWGP-UHFFFAOYSA-N 4-[3-ethyl-5-(1-propan-2-ylpiperidin-4-yl)-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C1=C2C(=NC=C1)NN=C2 QOMVTARMHYWWGP-UHFFFAOYSA-N 0.000 claims 2
QUYBIDXXJJUIJJ-UHFFFAOYSA-N 4-[3-ethyl-5-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)CC)C1=C2C(=NC=C1)NC=C2 QUYBIDXXJJUIJJ-UHFFFAOYSA-N 0.000 claims 2
RXIQJVDEOOXQHS-UHFFFAOYSA-N 4-[3-ethyl-5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=C2C(=NC=C1)NC=C2 RXIQJVDEOOXQHS-UHFFFAOYSA-N 0.000 claims 2
WVRZVZAAMDMIPA-UHFFFAOYSA-N 4-[3-ethyl-5-[1-(2,2,6,6-tetramethylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CC(NC(C1)(C)C)(C)C)C1=C2C(=NC=C1)NC=C2 WVRZVZAAMDMIPA-UHFFFAOYSA-N 0.000 claims 2
MUMNWKXNMOCLCQ-UHFFFAOYSA-N 4-[3-ethyl-5-[1-[(2-phenyl-1H-imidazol-5-yl)methyl]piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1N=C(NC=1)C1=CC=CC=C1)C1=C2C(=NC=C1)NN=C2 MUMNWKXNMOCLCQ-UHFFFAOYSA-N 0.000 claims 2
VJYUJGDBKXIUJV-UHFFFAOYSA-N 4-[3-ethyl-5-[1-[(5-methyl-1H-imidazol-4-yl)methyl]piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=C(N=CN1)C)C1=C2C(=NC=C1)NN=C2 VJYUJGDBKXIUJV-UHFFFAOYSA-N 0.000 claims 2
WPNOEXFSKNYZRP-UHFFFAOYSA-N 4-[3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-d]pyrimidine Chemical compound C(C)(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=N1)NN=C2)C WPNOEXFSKNYZRP-UHFFFAOYSA-N 0.000 claims 2
OLRQJWZDBIFLHI-UHFFFAOYSA-N 4-[3-methyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NC=C2)C OLRQJWZDBIFLHI-UHFFFAOYSA-N 0.000 claims 2
ZZIVWVVZTPKRAS-UHFFFAOYSA-N 4-[3-methyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C(C)C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NC=C2)C ZZIVWVVZTPKRAS-UHFFFAOYSA-N 0.000 claims 2
ROGZOTINPWTWLZ-UHFFFAOYSA-N 4-[3-propan-2-yl-5-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=NC=CC=C1)C1=C2C(=NC=C1)NN=C2 ROGZOTINPWTWLZ-UHFFFAOYSA-N 0.000 claims 2
WDSLTWAYGUGZGL-UHFFFAOYSA-N 4-[3-propan-2-yl-5-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1C=NC=CC=1)C1=C2C(=NC=C1)NN=C2 WDSLTWAYGUGZGL-UHFFFAOYSA-N 0.000 claims 2
MULMWXHFZQJNGY-UHFFFAOYSA-N 4-[3-propan-2-yl-5-[1-[(1-propan-2-ylpyrrolidin-3-yl)methyl]piperidin-4-yl]-6-(trifluoromethyl)-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC(=C(C=C12)C1CCN(CC1)CC1CN(CC1)C(C)C)C(F)(F)F)C1=C2C(=NC=C1)NN=C2 MULMWXHFZQJNGY-UHFFFAOYSA-N 0.000 claims 2
UUZZFKFSKFGXKG-UHFFFAOYSA-N 4-[3-propan-2-yl-5-[1-[(4-pyrimidin-2-yloxyphenyl)methyl]piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=CC=C(C=C1)OC1=NC=CC=N1)C1=C2C(=NC=C1)NN=C2 UUZZFKFSKFGXKG-UHFFFAOYSA-N 0.000 claims 2
ORJPJRATTHICEC-UHFFFAOYSA-N 4-[3-propan-2-yl-5-[1-[(4-pyrrolidin-1-ylphenyl)methyl]piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=CC=C(C=C1)N1CCCC1)C1=C2C(=NC=C1)NN=C2 ORJPJRATTHICEC-UHFFFAOYSA-N 0.000 claims 2
QCUCMHONDQHDEX-UHFFFAOYSA-N 4-[4-(2-imidazo[1,2-a]pyridin-6-yl-3-propan-2-yl-1H-indol-5-yl)piperidine-1-carbonyl]-1-methylpyrrolidin-2-one Chemical compound N=1C=CN2C=1C=CC(=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O QCUCMHONDQHDEX-UHFFFAOYSA-N 0.000 claims 2
PARCYMCPPGMYLZ-UHFFFAOYSA-N 4-[4-[2-(3-methyltriazolo[1,5-a]pyridin-5-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]thiane 1,1-dioxide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCS(CC1)(=O)=O)C1=CC=2N(C=C1)N=NC=2C PARCYMCPPGMYLZ-UHFFFAOYSA-N 0.000 claims 2
CAPDXDHGIPUCDM-UHFFFAOYSA-N 4-[5-(1-piperidin-3-ylpiperidin-4-yl)-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound N1(CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C)C1CNCCC1 CAPDXDHGIPUCDM-UHFFFAOYSA-N 0.000 claims 2
KHLQLQHCJXTMOJ-UHFFFAOYSA-N 4-[5-[1-(1-ethylpiperidin-4-yl)piperidin-4-yl]-3-methyl-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NC=C2)C KHLQLQHCJXTMOJ-UHFFFAOYSA-N 0.000 claims 2
DAVMFPQGFDURMA-UHFFFAOYSA-N 4-[5-[1-(2-methylpiperidin-4-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CC(NCC1)C)C1=C2C(=NC=C1)NN=C2 DAVMFPQGFDURMA-UHFFFAOYSA-N 0.000 claims 2
XTXJMIDYLUSGPK-UHFFFAOYSA-N 4-[5-[1-(3-fluoropiperidin-4-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound FC1CNCCC1N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C XTXJMIDYLUSGPK-UHFFFAOYSA-N 0.000 claims 2
UXQGYKYGDFPBLV-UHFFFAOYSA-N 4-[5-[1-(3-piperidin-1-ylpropyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCCN1CCCCC1)C1=C2C(=NC=C1)NN=C2 UXQGYKYGDFPBLV-UHFFFAOYSA-N 0.000 claims 2
JGGQUWDGGJRDSG-UHFFFAOYSA-N 4-[5-[1-(azepan-4-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound N1CCC(CCC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C JGGQUWDGGJRDSG-UHFFFAOYSA-N 0.000 claims 2
LBXMLZUTGIZFTD-UHFFFAOYSA-N 4-[5-[1-(imidazo[1,2-a]pyridin-2-ylmethyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound N=1C(=CN2C=1C=CC=C2)CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C LBXMLZUTGIZFTD-UHFFFAOYSA-N 0.000 claims 2
GYVIXEMYQIHHLX-UHFFFAOYSA-N 4-[5-[1-[(1-methylimidazol-4-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1N=CN(C=1)C)C1=C2C(=NC=C1)NN=C2 GYVIXEMYQIHHLX-UHFFFAOYSA-N 0.000 claims 2
RPCOBXZDXHSNMP-AIZNXBIQSA-N 4-[5-[1-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1C[C@H]2CC[C@@H](C1)N2C)C1=C2C(=NC=C1)NN=C2 RPCOBXZDXHSNMP-AIZNXBIQSA-N 0.000 claims 2
XQRVNACPHCEFIC-UHFFFAOYSA-N 4-[5-[1-[(3-chloropyridin-4-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound ClC=1C=NC=CC=1CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C XQRVNACPHCEFIC-UHFFFAOYSA-N 0.000 claims 2
MUKSVETVTGSDCK-UHFFFAOYSA-N 4-[6-fluoro-3-propan-2-yl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound FC1=C(C=C2C(=C(NC2=C1)C1=C2C(=NC=C1)NN=C2)C(C)C)C1CCN(CC1)C1CCN(CC1)C(C)C MUKSVETVTGSDCK-UHFFFAOYSA-N 0.000 claims 2
URKACEIWWKUJPL-UHFFFAOYSA-N 4-[6-fluoro-3-propan-2-yl-5-[1-(pyrrolidin-3-ylmethyl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound FC1=C(C=C2C(=C(NC2=C1)C1=C2C(=NC=C1)NN=C2)C(C)C)C1CCN(CC1)CC1CNCC1 URKACEIWWKUJPL-UHFFFAOYSA-N 0.000 claims 2
MFVDTDKXGGMBRF-UHFFFAOYSA-N 4-[[4-[3-ethyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]methyl]-1,3-thiazole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1N=CSC=1)C1=C2C(=NC=C1)NN=C2 MFVDTDKXGGMBRF-UHFFFAOYSA-N 0.000 claims 2
ABRVLEMSEAJDDU-UHFFFAOYSA-N 4-[[4-[3-ethyl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]methyl]-2,5-dimethyl-1,3-oxazole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1N=C(OC=1C)C)C1=C2C(=NC=C1)NN=C2 ABRVLEMSEAJDDU-UHFFFAOYSA-N 0.000 claims 2
CYUPNLCYVXTRLV-UHFFFAOYSA-N 4-methyl-6-[3-propan-2-yl-5-[1-(4,4,4-trifluorobutyl)piperidin-4-yl]-1H-indol-2-yl]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCCC(F)(F)F)C=1C=C(C=2N(C=1)N=NC=2)C CYUPNLCYVXTRLV-UHFFFAOYSA-N 0.000 claims 2
TVDJCHSDCRHCQJ-UHFFFAOYSA-N 4-methyl-6-[5-[1-(2-methylpropyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-benzimidazole Chemical compound C(C(C)C)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C2=C(NC=N2)C=1)C)C(C)C TVDJCHSDCRHCQJ-UHFFFAOYSA-N 0.000 claims 2
YDUYRCRZPJJNOD-UHFFFAOYSA-N 4-methyl-6-[5-[1-(2-methylsulfonylethyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCS(=O)(=O)C)C=1C=C(C=2N(C=1)N=NC=2)C YDUYRCRZPJJNOD-UHFFFAOYSA-N 0.000 claims 2
ABYLEWFNPPHLCN-UHFFFAOYSA-N 5-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1,3-dihydrobenzimidazol-2-one Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(NC(N2)=O)C=C1 ABYLEWFNPPHLCN-UHFFFAOYSA-N 0.000 claims 2
MHYRPXCCJSSCSL-UHFFFAOYSA-N 5-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1-methylpyrazolo[3,4-c]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C(=CN=1)N(N=C2)C MHYRPXCCJSSCSL-UHFFFAOYSA-N 0.000 claims 2
BXTFHVVLEWUIMU-UHFFFAOYSA-N 5-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-2-methylpyrazolo[3,4-c]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2C(C=N1)=NN(C=2)C BXTFHVVLEWUIMU-UHFFFAOYSA-N 0.000 claims 2
JOKRILCEROWYLO-UHFFFAOYSA-N 5-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-3H-1,3-benzoxazol-2-one Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC2=C(NC(O2)=O)C=1 JOKRILCEROWYLO-UHFFFAOYSA-N 0.000 claims 2
URIZFUJQPVCWGX-UHFFFAOYSA-N 5-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CNC=2N=CN=CC=21 URIZFUJQPVCWGX-UHFFFAOYSA-N 0.000 claims 2
PCJHFQDKCQCXIB-UHFFFAOYSA-N 5-(3-methyl-5-piperidin-4-yl-1H-indol-2-yl)-2H-benzotriazole Chemical compound CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(NN=N2)C=C1 PCJHFQDKCQCXIB-UHFFFAOYSA-N 0.000 claims 2
QJKSWNHIVNTNNG-UHFFFAOYSA-N 5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1,2-benzoxazol-3-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC2=C(C(=NO2)N)C=1 QJKSWNHIVNTNNG-UHFFFAOYSA-N 0.000 claims 2
KZBLSBLCLHQDID-UHFFFAOYSA-N 5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-indazol-3-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C(=NNC2=CC=1)N KZBLSBLCLHQDID-UHFFFAOYSA-N 0.000 claims 2
BNPZGFLLKBLMQM-UHFFFAOYSA-N 5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-indazole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C=NNC2=CC=1 BNPZGFLLKBLMQM-UHFFFAOYSA-N 0.000 claims 2
CTXCPBPUTMGHCV-UHFFFAOYSA-N 5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-3H-1,3-benzoxazol-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC2=C(NC(O2)=O)C=1 CTXCPBPUTMGHCV-UHFFFAOYSA-N 0.000 claims 2
ZRWOELDXFHHYQB-UHFFFAOYSA-N 5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CNC=2N=CN=CC=21 ZRWOELDXFHHYQB-UHFFFAOYSA-N 0.000 claims 2
QSGZFOAVHTWRDK-UHFFFAOYSA-N 5-[3-ethyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C(C)C)C=1C=C2C(=NC=1)NN=C2 QSGZFOAVHTWRDK-UHFFFAOYSA-N 0.000 claims 2
SAOYUKKYOGAGTG-UHFFFAOYSA-N 5-[3-propan-2-yl-5-(1-propan-2-ylpiperidin-4-yl)-1H-indol-2-yl]quinoline-8-carbonitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C1=C2C=CC=NC2=C(C=C1)C#N SAOYUKKYOGAGTG-UHFFFAOYSA-N 0.000 claims 2
BAGSIIZKFROHBN-UHFFFAOYSA-N 5-[3-propan-2-yl-5-(1-propylpiperidin-4-yl)-1H-indol-2-yl]-3H-2-benzofuran-1-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C2COC(C2=CC=1)=O BAGSIIZKFROHBN-UHFFFAOYSA-N 0.000 claims 2
FAUMTQZQLITLAM-UHFFFAOYSA-N 5-[5-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C=1C=C2C(=NC=1)NC=C2 FAUMTQZQLITLAM-UHFFFAOYSA-N 0.000 claims 2
PSVUWZZAKHIMJZ-UHFFFAOYSA-N 5-[5-[1-(2-methoxyethyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]quinoline-8-carbonitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCOC)C1=C2C=CC=NC2=C(C=C1)C#N PSVUWZZAKHIMJZ-UHFFFAOYSA-N 0.000 claims 2
QXQJBHIJOHIUKP-UHFFFAOYSA-N 5-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]quinoline-8-carbonitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=C2C=CC=NC2=C(C=C1)C#N QXQJBHIJOHIUKP-UHFFFAOYSA-N 0.000 claims 2
DTWXOKHABNUBSR-UHFFFAOYSA-N 5-[5-[1-[2-(dimethylamino)acetyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-3,7-dimethyl-1,3-benzoxazol-2-one Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C2=C(N(C(O2)=O)C)C=1)C)C(C)C)C DTWXOKHABNUBSR-UHFFFAOYSA-N 0.000 claims 2
QTGZCOLEFIIOPB-UHFFFAOYSA-N 5-[5-[1-[2-(dimethylamino)acetyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]quinoline-8-carbonitrile Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C=CC=NC2=C(C=C1)C#N)C(C)C)C QTGZCOLEFIIOPB-UHFFFAOYSA-N 0.000 claims 2
OSCVLDFFJOEYCV-UHFFFAOYSA-N 5-[[4-[3-propan-2-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)-1H-indol-5-yl]piperidin-1-yl]methyl]-1,3-thiazol-2-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1=CN=C(S1)N)C1=C2C(=NC=C1)NN=C2 OSCVLDFFJOEYCV-UHFFFAOYSA-N 0.000 claims 2
GPIHZMXZZBPVKC-UHFFFAOYSA-N 5-ethoxy-7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)OC1=CC(=CC=2N1N=CN=2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 GPIHZMXZZBPVKC-UHFFFAOYSA-N 0.000 claims 2
FMXOEKGKVLNNGW-UHFFFAOYSA-N 5-methoxy-7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C(=C1)OC)C=CN=2 FMXOEKGKVLNNGW-UHFFFAOYSA-N 0.000 claims 2
SIZJFHXAVLFTKP-UHFFFAOYSA-N 5-methoxy-7-[5-[1-(2-methoxyethyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCOC)C1=CC=2N(C(=C1)OC)N=CN=2 SIZJFHXAVLFTKP-UHFFFAOYSA-N 0.000 claims 2
NVYBKEICGTTXDC-UHFFFAOYSA-N 5-methoxy-7-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC=2N(C(=C1)OC)N=CN=2 NVYBKEICGTTXDC-UHFFFAOYSA-N 0.000 claims 2
HFISXCJOISYSAJ-UHFFFAOYSA-N 5-methyl-4-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1C)NN=C2 HFISXCJOISYSAJ-UHFFFAOYSA-N 0.000 claims 2
GFPXTTACEUDFPP-UHFFFAOYSA-N 5-methyl-7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrazolo[4,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC(=C1)C)C=NN2 GFPXTTACEUDFPP-UHFFFAOYSA-N 0.000 claims 2
CPEWYSADTPFJED-UHFFFAOYSA-N 5-methyl-7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C(=C1)C)N=CN=2 CPEWYSADTPFJED-UHFFFAOYSA-N 0.000 claims 2
ZYVHXXAMXYEICM-UHFFFAOYSA-N 5-methyl-7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)quinoxaline Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=C2N=CC=NC2=C1)C ZYVHXXAMXYEICM-UHFFFAOYSA-N 0.000 claims 2
HBMZUGVZGHGHEE-UHFFFAOYSA-N 5-methyl-7-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC=2N(C(=C1)C)N=CN=2 HBMZUGVZGHGHEE-UHFFFAOYSA-N 0.000 claims 2
ZLYVVHYLKCZFPY-UHFFFAOYSA-N 6-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-1,2-dihydroindazol-3-one Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=C2C(=NNC2=C1)O ZLYVVHYLKCZFPY-UHFFFAOYSA-N 0.000 claims 2
JHXPSCGHNXKPON-UHFFFAOYSA-N 6-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-3H-1,3-benzoxazol-2-one Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(NC(O2)=O)C=C1 JHXPSCGHNXKPON-UHFFFAOYSA-N 0.000 claims 2
SOUKDNOJPNHUHZ-UHFFFAOYSA-N 6-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(N=1)C=NN=2 SOUKDNOJPNHUHZ-UHFFFAOYSA-N 0.000 claims 2
MVIGXFTZDPBKHL-UHFFFAOYSA-N 6-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(N=1)C(=CN=2)C#N MVIGXFTZDPBKHL-UHFFFAOYSA-N 0.000 claims 2
KDISZOCAAMJMAK-UHFFFAOYSA-N 6-(4-fluoro-5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyridine Chemical compound FC1=C2C(=C(NC2=CC=C1C1CCNCC1)C=1C=CC=2N(C=1)C=CN=2)C(C)C KDISZOCAAMJMAK-UHFFFAOYSA-N 0.000 claims 2
ZSTUQQCHQQMHNX-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1,2-benzoxazol-3-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(C(=NO2)N)C=C1 ZSTUQQCHQQMHNX-UHFFFAOYSA-N 0.000 claims 2
OXDSXQXPFFTNAT-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1,2-benzoxazol-3-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(C(=NO2)O)C=C1 OXDSXQXPFFTNAT-UHFFFAOYSA-N 0.000 claims 2
XBDWIHHTHKSATM-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1,3-benzothiazole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(N=CS2)C=C1 XBDWIHHTHKSATM-UHFFFAOYSA-N 0.000 claims 2
FUJHNMFUJXWRNR-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-benzimidazole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC2=C(NC=N2)C=C1 FUJHNMFUJXWRNR-UHFFFAOYSA-N 0.000 claims 2
LZBJGTVVUNLMAC-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrazolo[4,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C(=NC=1)C=NN2 LZBJGTVVUNLMAC-UHFFFAOYSA-N 0.000 claims 2
AKUUCWKPTYHFAO-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-3H-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C(=NC=1)NC(O2)=O AKUUCWKPTYHFAO-UHFFFAOYSA-N 0.000 claims 2
HKZTZECHIZYVFJ-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C(=CC=2N(C=1)C=CN=2)C(F)(F)F HKZTZECHIZYVFJ-UHFFFAOYSA-N 0.000 claims 2
QZZOPPCXFVFVRD-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-b]pyridazine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(N=1)N=CN=2 QZZOPPCXFVFVRD-UHFFFAOYSA-N 0.000 claims 2
KOQLQTDNXXQDGE-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(N=1)C=NN=2 KOQLQTDNXXQDGE-UHFFFAOYSA-N 0.000 claims 2
JSJQXCYGLXDLFB-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(C=1)C=CN=2 JSJQXCYGLXDLFB-UHFFFAOYSA-N 0.000 claims 2
GFVJUYFJADSCFV-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(C=1)C(=CN=2)C#N GFVJUYFJADSCFV-UHFFFAOYSA-N 0.000 claims 2
XYZCIJUMTGIOCD-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-b]pyridazin-2-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(N=1)C=C(N=2)N XYZCIJUMTGIOCD-UHFFFAOYSA-N 0.000 claims 2
FTHQHAFVBSSKPP-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(C=1)C=NC=2 FTHQHAFVBSSKPP-UHFFFAOYSA-N 0.000 claims 2
ZBKMXBUCSJTDID-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[1,5-a]pyrimidine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=NC=2N(C=1)N=CC=2 ZBKMXBUCSJTDID-UHFFFAOYSA-N 0.000 claims 2
AWQRPPSGCCJZLM-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)quinoline Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C=CC=NC2=CC=1 AWQRPPSGCCJZLM-UHFFFAOYSA-N 0.000 claims 2
HMHCQLHSDGXIET-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)tetrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(C=1)N=NN=2 HMHCQLHSDGXIET-UHFFFAOYSA-N 0.000 claims 2
FYLYMGAGOXCHDP-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(C=1)N=NC=2 FYLYMGAGOXCHDP-UHFFFAOYSA-N 0.000 claims 2
YFOFZITZCUJQQA-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(1-propan-2-ylpiperidin-4-yl)-1H-indol-2-yl]imidazo[1,2-a]pyridine Chemical compound FC(CC1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C=1C=CC=2N(C=1)C=CN=2)F YFOFZITZCUJQQA-UHFFFAOYSA-N 0.000 claims 2
SSMHTYBBFROFCT-UHFFFAOYSA-N 6-[3-ethyl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]-1H-indol-2-yl]-1H-pyrazolo[4,3-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C(C)C)C=1C=C2C(=NC=1)C=NN2 SSMHTYBBFROFCT-UHFFFAOYSA-N 0.000 claims 2
PTFFGHLCXTUNEH-UHFFFAOYSA-N 6-[5-(1-methylpiperidin-4-yl)-3-propan-2-yl-1H-indol-2-yl]imidazo[1,2-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C)C=1C=CC=2N(C=1)C=CN=2 PTFFGHLCXTUNEH-UHFFFAOYSA-N 0.000 claims 2
LHMAXNDNTNIWSO-UHFFFAOYSA-N 6-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C=NC=2N(C=1)N=CN=2 LHMAXNDNTNIWSO-UHFFFAOYSA-N 0.000 claims 2
YWVOAPYMMGILMA-UHFFFAOYSA-N 6-[5-[1-[(6-methoxypyridin-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]imidazo[1,2-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC=1C=NC(=CC=1)OC)C=1C=CC=2N(C=1)C=CN=2 YWVOAPYMMGILMA-UHFFFAOYSA-N 0.000 claims 2
PZXQDXHTLCKBJM-UHFFFAOYSA-N 6-fluoro-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC=1C(=NC=2N(C=1)N=CC=2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 PZXQDXHTLCKBJM-UHFFFAOYSA-N 0.000 claims 2
WPWAYEPZBRNHAG-UHFFFAOYSA-N 7,8-dimethyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-b]pyridazine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C(=C(C=2N(N=1)N=CN=2)C)C WPWAYEPZBRNHAG-UHFFFAOYSA-N 0.000 claims 2
OKMSSZPQFHAKDH-UHFFFAOYSA-N 7,8-dimethyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)tetrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C(=C(C=2N(C=1)N=NN=2)C)C OKMSSZPQFHAKDH-UHFFFAOYSA-N 0.000 claims 2
PAKDSFCYXYANDE-UHFFFAOYSA-N 7,8-dimethyl-6-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-b]pyridazine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C(=C(C=2N(N=1)N=CN=2)C)C PAKDSFCYXYANDE-UHFFFAOYSA-N 0.000 claims 2
SEBWFEFDLXGKRY-UHFFFAOYSA-N 7,8-dimethyl-6-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]tetrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C(=C(C=2N(C=1)N=NN=2)C)C SEBWFEFDLXGKRY-UHFFFAOYSA-N 0.000 claims 2
WZDWHKANMLPXBZ-UHFFFAOYSA-N 7-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-2H-triazolo[4,5-b]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)N=NN2 WZDWHKANMLPXBZ-UHFFFAOYSA-N 0.000 claims 2
ZXHBMNMVTPLYLS-UHFFFAOYSA-N 7-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C=C1)N=CN=2 ZXHBMNMVTPLYLS-UHFFFAOYSA-N 0.000 claims 2
FUOCYCRZENGXLP-UHFFFAOYSA-N 7-(3-ethyl-5-piperidin-4-yl-1H-indol-2-yl)-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C=C1)C=NN=2 FUOCYCRZENGXLP-UHFFFAOYSA-N 0.000 claims 2
RWIPDSSBFLLPQK-UHFFFAOYSA-N 7-(3-methyl-5-piperidin-4-yl-1H-indol-2-yl)-2H-triazolo[4,5-b]pyridine Chemical compound CC1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NN=N2 RWIPDSSBFLLPQK-UHFFFAOYSA-N 0.000 claims 2
DWOTVTYFIIOZIY-UHFFFAOYSA-N 7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-1H-pyrazolo[4,3-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)C=NN2 DWOTVTYFIIOZIY-UHFFFAOYSA-N 0.000 claims 2
OWROUSQDBCPSJA-UHFFFAOYSA-N 7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-3H-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C2C(=NC=C1)NC(O2)=O OWROUSQDBCPSJA-UHFFFAOYSA-N 0.000 claims 2
VQNHRQXIXUUQHG-UHFFFAOYSA-N 7-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC=2N(C=C1)N=CN=2 VQNHRQXIXUUQHG-UHFFFAOYSA-N 0.000 claims 2
KXZPNEOXDHOGAB-UHFFFAOYSA-N 7-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC=2N(C=C1)C=NN=2 KXZPNEOXDHOGAB-UHFFFAOYSA-N 0.000 claims 2
BQBZAFGGUPWRGV-UHFFFAOYSA-N 7-chloro-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyridine Chemical compound ClC1=CC=2N(C(=C1)C=1NC3=CC=C(C=C3C=1C(C)C)C1CCNCC1)C=CN=2 BQBZAFGGUPWRGV-UHFFFAOYSA-N 0.000 claims 2
SIONSTUPCVIFHH-UHFFFAOYSA-N 7-methyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-3H-1,3-benzoxazol-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C2=C(NC(O2)=O)C=1)C SIONSTUPCVIFHH-UHFFFAOYSA-N 0.000 claims 2
ZCDCYQLRVKODCM-UHFFFAOYSA-N 7-methyl-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=C2C(=N1)SC=N2)C ZCDCYQLRVKODCM-UHFFFAOYSA-N 0.000 claims 2
PMPYXSFYEPVSKG-UHFFFAOYSA-N 7-methyl-5-[5-[1-(2-methylsulfonylethyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCS(=O)(=O)C)C1=CC=2N(C(=C1)C)N=NC=2 PMPYXSFYEPVSKG-UHFFFAOYSA-N 0.000 claims 2
PSZZEQAEXCUDJF-UHFFFAOYSA-N 7-methyl-5-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC=2N(C(=C1)C)N=NC=2 PSZZEQAEXCUDJF-UHFFFAOYSA-N 0.000 claims 2
CXWJBVVMRBOVDJ-UHFFFAOYSA-N 7-methyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-8-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1N(C(C=2N(C=1)C=NN=2)=O)C CXWJBVVMRBOVDJ-UHFFFAOYSA-N 0.000 claims 2
DZIDBIKGPBRMFA-UHFFFAOYSA-N 7-methyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)quinoline Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C2C=CC=NC2=CC=1C DZIDBIKGPBRMFA-UHFFFAOYSA-N 0.000 claims 2
BWLADVLDNHJGDG-UHFFFAOYSA-N 7-methyl-6-[5-[1-(2-methylsulfonylethyl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]tetrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCS(=O)(=O)C)C=1C(=CC=2N(C=1)N=NN=2)C BWLADVLDNHJGDG-UHFFFAOYSA-N 0.000 claims 2
OZJQLHXTYIEEAQ-UHFFFAOYSA-N 7-methyl-6-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]tetrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C(=CC=2N(C=1)N=NN=2)C OZJQLHXTYIEEAQ-UHFFFAOYSA-N 0.000 claims 2
QPVPUKNEJJGKSS-UHFFFAOYSA-N 8-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=2N(C=CC=1)N=CN=2 QPVPUKNEJJGKSS-UHFFFAOYSA-N 0.000 claims 2
XXVSSFVRKSNYTP-UHFFFAOYSA-N 8-[5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C=2N(C=CC=1)N=CN=2 XXVSSFVRKSNYTP-UHFFFAOYSA-N 0.000 claims 2
GRBMJPJTUSNXPC-UHFFFAOYSA-N 8-fluoro-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyridine Chemical compound FC=1C=2N(C=C(C=1)C=1NC3=CC=C(C=C3C=1C(C)C)C1CCNCC1)C=CN=2 GRBMJPJTUSNXPC-UHFFFAOYSA-N 0.000 claims 2
BHKXZOTXQZDDKD-UHFFFAOYSA-N 8-methoxy-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-b]pyridazine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C=2N(N=1)N=CN=2)OC BHKXZOTXQZDDKD-UHFFFAOYSA-N 0.000 claims 2
GRLJYHSQWVSKQY-UHFFFAOYSA-N 8-methoxy-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)imidazo[1,2-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C=2N(C=1)C=CN=2)OC GRLJYHSQWVSKQY-UHFFFAOYSA-N 0.000 claims 2
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CZTBZSWQRNQTSY-UHFFFAOYSA-N 8-methyl-6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)tetrazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C=2N(C=1)N=NN=2)C CZTBZSWQRNQTSY-UHFFFAOYSA-N 0.000 claims 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
208000021386 Sjogren Syndrome Diseases 0.000 claims 1
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
125000000168 pyrrolyl group Chemical group 0.000 claims 1
206010039073 rheumatoid arthritis Diseases 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
229940124530 sulfonamide Drugs 0.000 claims 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
125000003831 tetrazolyl group Chemical group 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1

JP2020544372A 2017-11-14 2018-11-13 置換インドール化合物 Active JP7265554B2 (ja)