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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Family Cites Families (43)
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| NZ555911A (en) | 2002-01-07 | 2008-07-31 | Eisai R&D Man Co Ltd | Deazapurines and uses thereof |
| EA200600069A1 (ru) | 2003-06-20 | 2006-08-25 | Коли Фармасьютикал Гмбх | Низкомолекулярные антагонисты toll-подобных рецепторов (tlr) |
| WO2006113458A1 (en) | 2005-04-15 | 2006-10-26 | Bristol-Myers Squibb Company | Heterocyclic inhibitors of protein arginine methyl transferases |
| CN101460164A (zh) | 2006-04-04 | 2009-06-17 | 美瑞德生物工程公司 | 用于疾病和障碍的化合物 |
| GB0610322D0 (en) | 2006-05-24 | 2006-07-05 | Karobio Ab | Novel pharmaceutical compositions |
| DE102006033109A1 (de) | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| US8027888B2 (en) | 2006-08-31 | 2011-09-27 | Experian Interactive Innovation Center, Llc | Online credit card prescreen systems and methods |
| JP2010511018A (ja) | 2006-12-01 | 2010-04-08 | ガラパゴス・ナムローゼ・フェンノートシャップ | 変性疾患及び炎症性疾患の治療に有用なトリアゾロピリジン化合物 |
| WO2008152471A1 (en) | 2007-06-12 | 2008-12-18 | Coley Pharmaceutical Group, Inc. | Quinazoline derivative useful as toll-like receptor antagonist |
| WO2009030996A1 (en) | 2007-09-05 | 2009-03-12 | Coley Pharmaceutical Group, Inc. | Triazole compounds as toll-like receptor (tlr) agonists |
| WO2009042092A1 (en) | 2007-09-25 | 2009-04-02 | Merck & Co., Inc. | 2-aryl or heteroaryl indole derivatives |
| EP2350032B1 (en) | 2008-09-26 | 2016-05-25 | Eisai R&D Management Co., Ltd. | Benzoxazole compounds and methods of use |
| JP5529876B2 (ja) | 2008-10-17 | 2014-06-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｍｍｐ−１３阻害剤として有用なヘテロアリール置換インドール化合物 |
| TWI462920B (zh) | 2009-06-26 | 2014-12-01 | 葛萊伯格有限公司 | 用於治療退化性及發炎疾病之新穎化合物 |
| US20110015219A1 (en) | 2009-07-16 | 2011-01-20 | Mallinckrodt Inc. | (+)-Morphinans as Antagonists of Toll-Like Receptor 9 and Therapeutic Uses Thereof |
| KR20120068947A (ko) | 2009-09-24 | 2012-06-27 | 에프. 호프만-라 로슈 아게 | Ｃｒａｃ 조절제로서의 인돌 유도체 |
| EP2813227A1 (en) | 2009-10-22 | 2014-12-17 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
| US9241991B2 (en) | 2010-10-21 | 2016-01-26 | The Brigham And Women's Hospital, Inc. | Agents, compositions, and methods for treating pruritus and related skin conditions |
| BR112013017943A2 (pt) | 2011-01-12 | 2018-12-18 | Array Biopharma Inc | benzoazepinas substituídas como moduladores receptores do tipo toll |
| WO2012097177A2 (en) | 2011-01-12 | 2012-07-19 | Ventirx Pharmaceuticals, Inc. | Substituted benzoazepines as toll-like receptor modulators |
| WO2012167053A1 (en) | 2011-06-01 | 2012-12-06 | Janus Biotherapeutics, Inc. | Novel immune system modulators |
| AU2012262014B2 (en) | 2011-06-01 | 2016-07-14 | Janus Biotherapeutics, Inc. | Novel immune system modulators |
| WO2012170867A1 (en) | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| EA023045B1 (ru) | 2011-07-15 | 2016-04-29 | Янссен Фармасьютикалз, Инк. | Новые замещенные производные индола в качестве модуляторов гамма-секретазы |
| CA2850932A1 (en) | 2011-10-04 | 2013-04-11 | Janus Biotherapeutics, Inc. | Novel imidazole quinoline-based immune system modulators |
| AU2013261267B2 (en) | 2012-05-18 | 2017-06-29 | Sumitomo Pharma Co., Ltd. | Carboxylic acid compounds |
| JO3407B1 (ar) * | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| MY192489A (en) | 2013-10-14 | 2022-08-23 | Eisai R&D Man Co Ltd | Selectively substituted quinoline compounds |
| CA2933466A1 (en) | 2013-12-13 | 2015-06-18 | Takeda Pharmaceutical Company Limited | Pyrrolo[3,2-c]pyridine derivatives as tlr inhibitors |
| LT3190113T (lt) | 2014-08-15 | 2021-08-25 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pirolopirimidino junginiai, naudotini kaip tlr7 agonistai |
| EP3398948A3 (en) | 2014-08-22 | 2018-12-05 | Janus Biotherapeutics, Inc. | 2,4,6,7-tetrasubstituted pteridine compounds and methods of synthesis and use thereof |
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| CA3031675A1 (en) * | 2016-07-30 | 2018-02-08 | Bristol-Myers Squibb Company | Dimethoxyphenyl substituted indole compounds as tlr7, tlr8 or tlr9 inhibitors |
| US10660877B2 (en) * | 2016-09-09 | 2020-05-26 | Bristol-Myers Squibb Company | Pyridyl substituted indole compounds |
-
2018
- 2018-12-14 EA EA202091477A patent/EA202091477A1/ru unknown
- 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 BR BR112020011668-8A patent/BR112020011668A2/pt not_active Application Discontinuation
- 2018-12-14 MX MX2020006093A patent/MX2020006093A/es unknown
- 2018-12-14 US US16/772,192 patent/US12030878B2/en active Active
- 2018-12-14 JP JP2020532884A patent/JP7287964B2/ja active Active
- 2018-12-14 SG SG11202005513TA patent/SG11202005513TA/en unknown
- 2018-12-14 KR KR1020207020047A patent/KR102781141B1/ko active Active
- 2018-12-14 WO PCT/US2018/065591 patent/WO2019118799A1/en not_active Ceased
- 2018-12-14 CN CN201880080658.4A patent/CN111527080B/zh active Active
- 2018-12-14 ES ES18830612T patent/ES2927960T3/es active Active
- 2018-12-14 CA CA3085333A patent/CA3085333A1/en active Pending
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2020
- 2020-06-14 IL IL275342A patent/IL275342A/en unknown
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