ES2614872T3 - Derivados de 9-(aril o heteroaril)-2-(pirazolilo, pirrolidinilo o ciclopentilo) aminopurina como agentes anticancer - Google Patents
Derivados de 9-(aril o heteroaril)-2-(pirazolilo, pirrolidinilo o ciclopentilo) aminopurina como agentes anticancer Download PDFInfo
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- ES2614872T3 ES2614872T3 ES14705029.8T ES14705029T ES2614872T3 ES 2614872 T3 ES2614872 T3 ES 2614872T3 ES 14705029 T ES14705029 T ES 14705029T ES 2614872 T3 ES2614872 T3 ES 2614872T3
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- Prior art keywords
- pyrazol
- purin
- phenyl
- ylamino
- amine
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- 125000003226 pyrazolyl group Chemical group 0.000 title abstract 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 title abstract 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title abstract 2
- 150000005018 aminopurines Chemical class 0.000 title 1
- 239000002246 antineoplastic agent Substances 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 title 1
- 125000001072 heteroaryl group Chemical group 0.000 title 1
- -1 [9- (3-fluoro-4-iodo-phenyl) -9H-purin-2-ylamino] -cyclopentanol Chemical compound 0.000 claims description 8
- PRZZMYNUPXZJAM-RDJZCZTQSA-N (1S,3S)-3-[[9-[4-(1-methylpyrazol-4-yl)phenyl]purin-2-yl]amino]cyclopentan-1-ol Chemical compound CN1N=CC(=C1)C1=CC=C(C=C1)N1C2=NC(=NC=C2N=C1)N[C@@H]1C[C@H](CC1)O PRZZMYNUPXZJAM-RDJZCZTQSA-N 0.000 claims 1
- TXVYDEAEWZVJRU-HUUCEWRRSA-N (1r,3r)-3-[[9-(2-methylquinolin-6-yl)purin-2-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=CC2=NC(C)=CC=C2C=C1N(C1=N2)C=NC1=CN=C2N[C@@H]1CC[C@@H](C(N)=O)C1 TXVYDEAEWZVJRU-HUUCEWRRSA-N 0.000 claims 1
- BVDJAGLMXYRQGS-NXEZZACHSA-N (1r,3r)-3-[[9-(3-fluoro-4-iodophenyl)purin-2-yl]amino]cyclopentane-1-carboxamide Chemical compound C1[C@H](C(=O)N)CC[C@H]1NC1=NC=C(N=CN2C=3C=C(F)C(I)=CC=3)C2=N1 BVDJAGLMXYRQGS-NXEZZACHSA-N 0.000 claims 1
- ROBITDPCAFYULM-CHWSQXEVSA-N (1r,3r)-3-[[9-(4-ethoxyphenyl)purin-2-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=CC(OCC)=CC=C1N1C2=NC(N[C@H]3C[C@@H](CC3)C(N)=O)=NC=C2N=C1 ROBITDPCAFYULM-CHWSQXEVSA-N 0.000 claims 1
- ZRKGKHIWUNEAPV-ZYHUDNBSSA-N (1r,3r)-3-[[9-(4-iodophenyl)purin-2-yl]amino]cyclopentane-1-carboxamide Chemical compound C1[C@H](C(=O)N)CC[C@H]1NC1=NC=C(N=CN2C=3C=CC(I)=CC=3)C2=N1 ZRKGKHIWUNEAPV-ZYHUDNBSSA-N 0.000 claims 1
- ZVWOHLIYSAAKLS-ZIAGYGMSSA-N (1r,3r)-3-[[9-[4-(2-methoxyethoxy)phenyl]purin-2-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=CC(OCCOC)=CC=C1N1C2=NC(N[C@H]3C[C@@H](CC3)C(N)=O)=NC=C2N=C1 ZVWOHLIYSAAKLS-ZIAGYGMSSA-N 0.000 claims 1
- IAQAFVNJDDMTIX-IEBWSBKVSA-N (1r,3r)-3-[[9-[4-[1-(2-ethoxyethyl)pyrazol-4-yl]phenyl]purin-2-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=NN(CCOCC)C=C1C1=CC=C(N2C3=NC(N[C@H]4C[C@@H](CC4)C(N)=O)=NC=C3N=C2)C=C1 IAQAFVNJDDMTIX-IEBWSBKVSA-N 0.000 claims 1
- MIGIFQORLNWZLJ-JSGCOSHPSA-N (1s,3s)-3-[[9-(4-ethoxyphenyl)purin-2-yl]amino]cyclopentan-1-ol Chemical compound C1=CC(OCC)=CC=C1N1C2=NC(N[C@@H]3C[C@@H](O)CC3)=NC=C2N=C1 MIGIFQORLNWZLJ-JSGCOSHPSA-N 0.000 claims 1
- YCILNVKXUYRVDU-RDJZCZTQSA-N (1s,3s)-3-[[9-[3-fluoro-4-[1-(2-methoxyethyl)pyrazol-4-yl]phenyl]purin-2-yl]amino]cyclopentan-1-ol Chemical compound C1=NN(CCOC)C=C1C1=CC=C(N2C3=NC(N[C@@H]4C[C@@H](O)CC4)=NC=C3N=C2)C=C1F YCILNVKXUYRVDU-RDJZCZTQSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- QHJWYFRXENTYJU-UHFFFAOYSA-N 2-n,9-bis(1-ethylpyrazol-4-yl)purine-2,8-diamine Chemical compound C1=NN(CC)C=C1NC1=NC=C(N=C(N)N2C3=CN(CC)N=C3)C2=N1 QHJWYFRXENTYJU-UHFFFAOYSA-N 0.000 claims 1
- KXWFVWYEESKSLS-UHFFFAOYSA-N 2-n-(1-methylpyrazol-4-yl)-9-[4-(1-methylpyrazol-4-yl)phenyl]purine-2,8-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(N=C(N)N2C=3C=CC(=CC=3)C3=CN(C)N=C3)C2=N1 KXWFVWYEESKSLS-UHFFFAOYSA-N 0.000 claims 1
- RFNPGMWNFYYONM-UHFFFAOYSA-N 2-n-(1-methylpyrazol-4-yl)-9-[4-(1-piperidin-4-ylpyrazol-4-yl)phenyl]purine-2,8-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(N=C(N)N2C=3C=CC(=CC=3)C3=CN(N=C3)C3CCNCC3)C2=N1 RFNPGMWNFYYONM-UHFFFAOYSA-N 0.000 claims 1
- LAPVVWFVGSUTJV-UHFFFAOYSA-N 4-[8-amino-2-[(1-ethylpyrazol-4-yl)amino]purin-9-yl]-n-(2-hydroxyethyl)benzamide Chemical compound C1=NN(CC)C=C1NC1=NC=C(N=C(N)N2C=3C=CC(=CC=3)C(=O)NCCO)C2=N1 LAPVVWFVGSUTJV-UHFFFAOYSA-N 0.000 claims 1
- GWBJUNURYOAWOC-UHFFFAOYSA-N 6-[2-[(1-ethylpyrazol-4-yl)amino]purin-9-yl]-3,3-dimethyl-1h-indol-2-one Chemical compound C1=NN(CC)C=C1NC1=NC=C(N=CN2C=3C=C4C(C(C(=O)N4)(C)C)=CC=3)C2=N1 GWBJUNURYOAWOC-UHFFFAOYSA-N 0.000 claims 1
- FGPWCYOYIFSJDF-UHFFFAOYSA-N 9-(4-chloro-3-fluorophenyl)-n-[1-(oxan-4-yl)pyrazol-4-yl]purin-2-amine Chemical compound C1=C(Cl)C(F)=CC(N2C3=NC(NC4=CN(N=C4)C4CCOCC4)=NC=C3N=C2)=C1 FGPWCYOYIFSJDF-UHFFFAOYSA-N 0.000 claims 1
- ZTAPXBTXZVFYEF-UHFFFAOYSA-N 9-(4-ethoxyphenyl)-2-n-[1-(2-pyrazol-1-ylethyl)pyrazol-4-yl]purine-2,8-diamine Chemical compound C1=CC(OCC)=CC=C1N1C2=NC(NC3=CN(CCN4N=CC=C4)N=C3)=NC=C2N=C1N ZTAPXBTXZVFYEF-UHFFFAOYSA-N 0.000 claims 1
- ZILRVMJSLJRMLI-UHFFFAOYSA-N 9-(4-ethoxyphenyl)-n-[1-(2-pyrazol-1-ylethyl)pyrazol-4-yl]purin-2-amine Chemical compound C1=CC(OCC)=CC=C1N1C2=NC(NC3=CN(CCN4N=CC=C4)N=C3)=NC=C2N=C1 ZILRVMJSLJRMLI-UHFFFAOYSA-N 0.000 claims 1
- UDFSOSKASDGAHL-UHFFFAOYSA-N 9-(4-ethoxyphenyl)-n-[1-(3-piperidin-4-ylpropyl)pyrazol-4-yl]purin-2-amine Chemical compound C1=CC(OCC)=CC=C1N1C2=NC(NC3=CN(CCCC4CCNCC4)N=C3)=NC=C2N=C1 UDFSOSKASDGAHL-UHFFFAOYSA-N 0.000 claims 1
- GVXSTQBYRUMOBA-UHFFFAOYSA-N 9-(4-methoxyphenyl)-n-(1-methylpyrazol-3-yl)purin-2-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC3=NN(C)C=C3)=NC=C2N=C1 GVXSTQBYRUMOBA-UHFFFAOYSA-N 0.000 claims 1
- VXQXINQWXGRXMO-UHFFFAOYSA-N 9-(4-methoxyphenyl)-n-(1-phenylpyrazol-4-yl)purin-2-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC3=CN(N=C3)C=3C=CC=CC=3)=NC=C2N=C1 VXQXINQWXGRXMO-UHFFFAOYSA-N 0.000 claims 1
- FHRXKIOMIIAQAT-UHFFFAOYSA-N 9-(4-methoxyphenyl)-n-(1h-pyrazol-4-yl)purin-2-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC3=CNN=C3)=NC=C2N=C1 FHRXKIOMIIAQAT-UHFFFAOYSA-N 0.000 claims 1
- YEMQOYBTPWPSSM-UHFFFAOYSA-N 9-(4-methoxyphenyl)-n-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]purin-2-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC3=CN(N=C3)C3CCN(C)CC3)=NC=C2N=C1 YEMQOYBTPWPSSM-UHFFFAOYSA-N 0.000 claims 1
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| CA2961950A1 (en) | 2014-09-28 | 2016-03-31 | The Regents Of The University Of California | Modulation of stimulatory and non-stimulatory myeloid cells |
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| US11214565B2 (en) | 2015-11-20 | 2022-01-04 | Denali Therapeutics Inc. | Compound, compositions, and methods |
| US11028080B2 (en) | 2016-03-11 | 2021-06-08 | Denali Therapeutics Inc. | Substituted pyrimidines as LRKK2 inhibitors |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
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| CN109563095B (zh) * | 2016-06-02 | 2021-10-29 | 细胞基因公司 | 动物和人抗疟剂 |
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| FI3498693T3 (fi) | 2016-08-10 | 2025-01-15 | Takeda Pharmaceuticals Co | Heterosyklinen yhdiste |
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| SMT202100573T1 (it) | 2016-12-22 | 2021-11-12 | Calithera Biosciences Inc | Composizioni e metodi per l'inibizione dell'attivita' dell'arginasi |
| KR102383561B1 (ko) * | 2017-09-07 | 2022-04-06 | 한국화학연구원 | 테트라히드로이소퀴놀린기로 치환된 피리미딘 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 조성물 |
| CN111587114A (zh) * | 2017-11-14 | 2020-08-25 | 儿童医学中心公司 | 用于调节人免疫应答的咪唑并嘧啶的用途 |
| JP7304855B2 (ja) | 2017-11-14 | 2023-07-07 | ザ チルドレンズ メディカル センター コーポレーション | 新規イミダゾピリミジン化合物およびそれらの使用 |
| WO2019118513A1 (en) | 2017-12-12 | 2019-06-20 | Pionyr Immunotherapeutics, Inc. | Anti-trem2 antibodies and related methods |
| WO2019136466A1 (en) | 2018-01-08 | 2019-07-11 | Yale University | Compounds and methods for treating or preventing anterior segment ocular disorders and/or retinal degenerations |
| KR20200116481A (ko) * | 2018-01-29 | 2020-10-12 | 메르크 파텐트 게엠베하 | Gcn2 억제제 및 이의 용도 |
| EP3746071A4 (en) | 2018-01-29 | 2021-09-01 | Merck Patent GmbH | GCN2 INHIBITORS AND THEIR USES |
| WO2019236631A1 (en) * | 2018-06-05 | 2019-12-12 | Rapt Therapeutics, Inc. | Pyrazolo-pyrimidin-amino-cycloalkyl compounds and their therapeutic uses |
| CN111166750B (zh) * | 2018-11-09 | 2022-12-27 | 四川大学 | 一种4-氟-2-甲基吲哚类化合物的抗菌新用途 |
| TWI899080B (zh) * | 2019-05-27 | 2025-10-01 | 大陸商迪哲（江蘇）醫藥股份有限公司 | Ｄｎａ依賴性蛋白激酶抑制劑 |
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| CN1255392C (zh) | 2000-07-07 | 2006-05-10 | 安吉奥金尼药品有限公司 | 作为血管生成抑制剂的秋水仙醇衍生物 |
| IL153484A0 (en) | 2000-07-07 | 2003-07-06 | Angiogene Pharm Ltd | Colchinol derivatives as angiogenesis inhibitors |
| MXPA06000540A (es) | 2003-07-16 | 2006-03-30 | Janssen Pharmaceutica Nv | Derivados de triazolopirimidinas como inhibidores de la glucogeno sintasa cinasa 3. |
| CN103251953A (zh) | 2004-07-19 | 2013-08-21 | 约翰·霍普金斯大学 | 供免疫抑制的flt3抑制剂 |
| AU2005298637B8 (en) | 2004-10-29 | 2012-12-06 | Janssen Sciences Ireland Uc | HIV inhibiting bicyclic pyrimidine derivatives |
| CN101142215A (zh) * | 2005-01-13 | 2008-03-12 | 西格诺药品有限公司 | 卤代芳基取代的氨基嘌呤、其组合物及其治疗方法 |
| US7723340B2 (en) | 2005-01-13 | 2010-05-25 | Signal Pharmaceuticals, Llc | Haloaryl substituted aminopurines, compositions thereof, and methods of treatment therewith |
| AU2006205808A1 (en) | 2005-01-14 | 2006-07-20 | Janssen Pharmaceutica N.V. | Triazolopyrimidine derivatives as glycogen synthase kinase 3 inhibitors |
| TWI398252B (zh) * | 2006-05-26 | 2013-06-11 | 諾華公司 | 吡咯并嘧啶化合物及其用途 |
| WO2011106168A1 (en) * | 2010-02-24 | 2011-09-01 | Dcam Pharma Inc | Purine compounds for treating autoimmune and demyelinating diseases |
| WO2012025186A1 (en) * | 2010-08-27 | 2012-03-01 | Merck Patent Gmbh | Triazolopyrazine derivatives |
-
2014
- 2014-02-11 AU AU2014224976A patent/AU2014224976B2/en not_active Ceased
- 2014-02-11 CA CA2903901A patent/CA2903901A1/en not_active Abandoned
- 2014-02-11 ES ES14705029.8T patent/ES2614872T3/es active Active
- 2014-02-11 WO PCT/EP2014/000371 patent/WO2014135245A1/en not_active Ceased
- 2014-02-11 CN CN201480012134.3A patent/CN105026397B/zh not_active Expired - Fee Related
- 2014-02-11 US US14/772,430 patent/US9617266B2/en not_active Expired - Fee Related
- 2014-02-11 EP EP14705029.8A patent/EP2964648B1/en not_active Not-in-force
- 2014-02-11 JP JP2015560572A patent/JP6409007B2/ja not_active Expired - Fee Related
- 2014-03-05 AR ARP140100696A patent/AR094981A1/es unknown
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2015
- 2015-08-27 IL IL240876A patent/IL240876B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP2964648A1 (en) | 2016-01-13 |
| AU2014224976A1 (en) | 2015-10-22 |
| AR094981A1 (es) | 2015-09-09 |
| AU2014224976B2 (en) | 2017-09-28 |
| WO2014135245A1 (en) | 2014-09-12 |
| CN105026397B (zh) | 2017-06-30 |
| IL240876A0 (en) | 2015-10-29 |
| IL240876B (en) | 2019-09-26 |
| US9617266B2 (en) | 2017-04-11 |
| CA2903901A1 (en) | 2014-09-12 |
| US20160002242A1 (en) | 2016-01-07 |
| CN105026397A (zh) | 2015-11-04 |
| JP6409007B2 (ja) | 2018-10-17 |
| JP2016510045A (ja) | 2016-04-04 |
| EP2964648B1 (en) | 2016-11-16 |
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