JP2021506816A5 - - Google Patents
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- Publication number
- JP2021506816A5 JP2021506816A5 JP2020532884A JP2020532884A JP2021506816A5 JP 2021506816 A5 JP2021506816 A5 JP 2021506816A5 JP 2020532884 A JP2020532884 A JP 2020532884A JP 2020532884 A JP2020532884 A JP 2020532884A JP 2021506816 A5 JP2021506816 A5 JP 2021506816A5
- Authority
- JP
- Japan
- Prior art keywords
- indole
- isopropyl
- oxy
- piperidine
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 dioxothiomorpholinyl Chemical group 0.000 claims 53
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 17
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 7
- 150000001204 N-oxides Chemical class 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 6
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 4
- GBNFVCWXAKUEQO-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(OC3CCNCC3)C=C12)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(OC3CCNCC3)C=C12)C1=CN(C)C(=O)C(C)=C1 GBNFVCWXAKUEQO-UHFFFAOYSA-N 0.000 claims 4
- MYXJKVXKOYROEW-UHFFFAOYSA-N CC(C)N1CCC(CC1)OC1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1C Chemical compound CC(C)N1CCC(CC1)OC1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1C MYXJKVXKOYROEW-UHFFFAOYSA-N 0.000 claims 4
- AXZIMGKXFJEORZ-UHFFFAOYSA-N N1C=NC(=C1)COC=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C Chemical compound N1C=NC(=C1)COC=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C AXZIMGKXFJEORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000003566 oxetanyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- IGVQKVGULJIYOL-QHCPKHFHSA-N 1,3-dimethyl-5-[5-[(3S)-1-(oxan-4-yl)piperidin-3-yl]oxy-3-propan-2-yl-1H-indol-2-yl]pyridin-2-one Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)O[C@@H]1CN(CCC1)C1CCOCC1)C=1C=C(C(N(C=1)C)=O)C IGVQKVGULJIYOL-QHCPKHFHSA-N 0.000 claims 2
- HQORLYNFFTYKCM-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[[1-(2-methoxyethyl)piperidin-4-yl]methoxy]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)OCC1CCN(CC1)CCOC)C HQORLYNFFTYKCM-UHFFFAOYSA-N 0.000 claims 2
- IJUXRWWUEGWFKY-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-(1-propan-2-ylpiperidin-4-yl)oxy-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OC1CCN(CC1)C(C)C)C1=CC(=NC=C1)C IJUXRWWUEGWFKY-UHFFFAOYSA-N 0.000 claims 2
- KXKRXYVGNCNJTA-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-(pyridin-3-ylmethoxy)-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OCC=1C=NC=CC=1)C1=CC(=NC=C1)C KXKRXYVGNCNJTA-UHFFFAOYSA-N 0.000 claims 2
- XKDYUGRGCOSNNH-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-[(1-propan-2-ylpiperidin-4-yl)methoxy]-1H-indole Chemical compound CC(C)N1CCC(COC2=CC=C3NC(=C(C(C)C)C3=C2)C2=CC(C)=NC=C2)CC1 XKDYUGRGCOSNNH-UHFFFAOYSA-N 0.000 claims 2
- FCORTZPXBNKKSL-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-5-(4-piperidin-4-yloxycyclohexyl)oxy-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OC1CCC(CC1)OC1CCNCC1)C1=CC(=NC=C1)C FCORTZPXBNKKSL-UHFFFAOYSA-N 0.000 claims 2
- LQIJWBMLUSXRFS-GOSISDBHSA-N 2-(2-methylpyridin-4-yl)-5-[(3R)-1-methylpyrrolidin-3-yl]oxy-3-propan-2-yl-1H-indole Chemical compound CC(C)C1=C(NC2=CC=C(O[C@@H]3CCN(C)C3)C=C12)C1=CC(C)=NC=C1 LQIJWBMLUSXRFS-GOSISDBHSA-N 0.000 claims 2
- NOPVILOMBGFUQM-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]oxymethyl]azetidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CC(C1)COC=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C)C NOPVILOMBGFUQM-UHFFFAOYSA-N 0.000 claims 2
- SKTOKAOZMZYUPT-NRFANRHFSA-N 2-[(3S)-3-[[2-(1,5-dimethyl-6-oxopyridin-3-yl)-3-propan-2-yl-1H-indol-5-yl]oxy]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound CN1C=C(C=C(C1=O)C)C=1NC2=CC=C(C=C2C=1C(C)C)O[C@@H]1CN(CCC1)CC(=O)N(C)C SKTOKAOZMZYUPT-NRFANRHFSA-N 0.000 claims 2
- FUCHPWOOZNUVDL-UHFFFAOYSA-N 2-[4-[[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]oxy]piperidin-1-yl]ethanol Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)OC1CCN(CC1)CCO)C FUCHPWOOZNUVDL-UHFFFAOYSA-N 0.000 claims 2
- UHYNCDRSNNULBL-UHFFFAOYSA-N 2-[4-[[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]oxymethyl]piperidin-1-yl]-N-methylacetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)OCC1CCN(CC1)CC(=O)NC)C UHYNCDRSNNULBL-UHFFFAOYSA-N 0.000 claims 2
- RTIUBLBRAJNGNQ-UHFFFAOYSA-N 2-[4-[[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]oxy]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OC1CCN(CC1)CC(=O)N(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC RTIUBLBRAJNGNQ-UHFFFAOYSA-N 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- BDGFQPOVEFIVDH-UHFFFAOYSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-(1-propan-2-ylpyrrolidin-3-yl)oxy-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)OC1CN(CC1)C(C)C)C1=CC(=NC=C1)C BDGFQPOVEFIVDH-UHFFFAOYSA-N 0.000 claims 2
- FSVZUXBJBFUXSH-UHFFFAOYSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-(piperidin-4-ylmethoxy)-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)OCC1CCNCC1)C1=CC(=NC=C1)C FSVZUXBJBFUXSH-UHFFFAOYSA-N 0.000 claims 2
- WGDHQNHMWWIWPA-INIZCTEOSA-N 3-ethyl-2-(2-methylpyridin-4-yl)-5-[(3S)-pyrrolidin-3-yl]oxy-1H-indole Chemical compound C(C)C1=C(NC2=CC=C(C=C12)O[C@@H]1CNCC1)C1=CC(=NC=C1)C WGDHQNHMWWIWPA-INIZCTEOSA-N 0.000 claims 2
- UUDIVBIGXRDPGR-UHFFFAOYSA-N 4-[4-[[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]oxymethyl]phenyl]morpholine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OCC1=CC=C(C=C1)N1CCOCC1)C1=CC(=NC=C1)C UUDIVBIGXRDPGR-UHFFFAOYSA-N 0.000 claims 2
- QWRPBQYXOIYKMZ-UHFFFAOYSA-N 5-(1-methylpiperidin-4-yl)oxy-2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OC1CCN(CC1)C)C1=CC(=NC=C1)C QWRPBQYXOIYKMZ-UHFFFAOYSA-N 0.000 claims 2
- HMTZBFWRPNGHEF-UHFFFAOYSA-N 7,8-dimethyl-6-[3-propan-2-yl-5-(1-propylpiperidin-4-yl)oxy-1H-indol-2-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OC1CCN(CC1)CCC)C=1C(=C(C=2N(C=1)C=NN=2)C)C HMTZBFWRPNGHEF-UHFFFAOYSA-N 0.000 claims 2
- BNVGFKYDSRUZAR-UHFFFAOYSA-N 8-methoxy-6-(5-piperidin-4-yloxy-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(OC3CCNCC3)=CC=C2N1 BNVGFKYDSRUZAR-UHFFFAOYSA-N 0.000 claims 2
- TVINEYGTXWKTHF-UHFFFAOYSA-N 8-methyl-6-[3-propan-2-yl-5-(2-pyrrolidin-1-ylethoxy)-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OCCN1CCCC1)C=1C=C(C=2N(C=1)N=CN=2)C TVINEYGTXWKTHF-UHFFFAOYSA-N 0.000 claims 2
- VCHSYPIPKYMRNX-UHFFFAOYSA-N 8-methyl-6-[3-propan-2-yl-5-[(1-propan-2-ylpiperidin-4-yl)methoxy]-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OCC1CCN(CC1)C(C)C)C=1C=C(C=2N(C=1)N=CN=2)C VCHSYPIPKYMRNX-UHFFFAOYSA-N 0.000 claims 2
- JPMRJXMTVRAESE-UHFFFAOYSA-N 8-methyl-6-[5-(piperidin-4-ylmethoxy)-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)OCC1CCNCC1)C=1C=C(C=2N(C=1)N=CN=2)C JPMRJXMTVRAESE-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- GBCKAYXDFLTSEV-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)OC1CCN(CC1)CCC(F)(F)F)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)OC1CCN(CC1)CCC(F)(F)F)C1=CC(=NC=C1)C GBCKAYXDFLTSEV-UHFFFAOYSA-N 0.000 claims 2
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2018
- 2018-12-14 KR KR1020207020047A patent/KR102781141B1/ko active Active
- 2018-12-14 SG SG11202005513TA patent/SG11202005513TA/en unknown
- 2018-12-14 WO PCT/US2018/065591 patent/WO2019118799A1/en not_active Ceased
- 2018-12-14 MX MX2020006093A patent/MX2020006093A/es unknown
- 2018-12-14 JP JP2020532884A patent/JP7287964B2/ja active Active
- 2018-12-14 CN CN201880080658.4A patent/CN111527080B/zh active Active
- 2018-12-14 AU AU2018386201A patent/AU2018386201A1/en not_active Abandoned
- 2018-12-14 EP EP18830612.0A patent/EP3724183B1/en active Active
- 2018-12-14 CA CA3085333A patent/CA3085333A1/en active Pending
- 2018-12-14 US US16/772,192 patent/US12030878B2/en active Active
- 2018-12-14 EA EA202091477A patent/EA202091477A1/ru unknown
- 2018-12-14 ES ES18830612T patent/ES2927960T3/es active Active
- 2018-12-14 BR BR112020011668-8A patent/BR112020011668A2/pt not_active Application Discontinuation
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2020
- 2020-06-14 IL IL275342A patent/IL275342A/en unknown
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