JP2004529926A5 - - Google Patents
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- Publication number
- JP2004529926A5 JP2004529926A5 JP2002581427A JP2002581427A JP2004529926A5 JP 2004529926 A5 JP2004529926 A5 JP 2004529926A5 JP 2002581427 A JP2002581427 A JP 2002581427A JP 2002581427 A JP2002581427 A JP 2002581427A JP 2004529926 A5 JP2004529926 A5 JP 2004529926A5
- Authority
- JP
- Japan
- Prior art keywords
- het
- pyridin
- cyclopentylamino
- pyrazolo
- amine
- 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
Links
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- FPZNHXIUFKJEHG-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-(2-methoxyethyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(NCCOC)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 FPZNHXIUFKJEHG-UHFFFAOYSA-N 0.000 claims 1
- FDXDGPUMMWYVHH-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(NC(C)C)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 FDXDGPUMMWYVHH-UHFFFAOYSA-N 0.000 claims 1
- ZBASGXKVNVIJCM-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-6-amine Chemical compound N=1N2C=C(NC(C)C)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 ZBASGXKVNVIJCM-UHFFFAOYSA-N 0.000 claims 1
- OUZIVEFGDDPQGR-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(N)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 OUZIVEFGDDPQGR-UHFFFAOYSA-N 0.000 claims 1
- FEIKULOVKMOBGQ-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-amine Chemical compound N=1N2C=C(N)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 FEIKULOVKMOBGQ-UHFFFAOYSA-N 0.000 claims 1
- RMANLZQDOIEBGU-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC(C)C)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RMANLZQDOIEBGU-UHFFFAOYSA-N 0.000 claims 1
- NUKYEHFDVLNGFZ-UHFFFAOYSA-N 4-[5-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 NUKYEHFDVLNGFZ-UHFFFAOYSA-N 0.000 claims 1
- HZRFMJKFCUASOU-UHFFFAOYSA-N 4-bromo-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Br)C2=C1C1=CC=NC(NC2CCCC2)=N1 HZRFMJKFCUASOU-UHFFFAOYSA-N 0.000 claims 1
- KCKHDUBDEHXGJB-UHFFFAOYSA-N 4-bromo-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Br)C2=C1C1=CC=NC(NC2CCCC2)=N1 KCKHDUBDEHXGJB-UHFFFAOYSA-N 0.000 claims 1
- KOWHYEFJCNLWGI-UHFFFAOYSA-N 4-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Cl)C2=C1C1=CC=NC(NC2CCCC2)=N1 KOWHYEFJCNLWGI-UHFFFAOYSA-N 0.000 claims 1
- WHOWUHRMZQLXRB-UHFFFAOYSA-N 4-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Cl)C2=C1C1=CC=NC(NC2CCCC2)=N1 WHOWUHRMZQLXRB-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- SQOVLUIXVMRKMK-UHFFFAOYSA-N n-[3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]methanesulfonamide Chemical compound C=12C=C(NS(=O)(=O)C)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 SQOVLUIXVMRKMK-UHFFFAOYSA-N 0.000 claims 1
- LNVZHPGLGRXNAI-UHFFFAOYSA-N n-butyl-3-[2-(butylamino)pyridin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-4-amine Chemical compound C1=NC(NCCCC)=CC(C2=C3C(NCCCC)=CC=CN3N=C2C=2C=CC(F)=CC=2)=C1 LNVZHPGLGRXNAI-UHFFFAOYSA-N 0.000 claims 1
- SQQVANPMGGBYDX-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 SQQVANPMGGBYDX-UHFFFAOYSA-N 0.000 claims 1
- XDGMTTPBMWQFBC-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=C(NC2CCCC2)C=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 XDGMTTPBMWQFBC-UHFFFAOYSA-N 0.000 claims 1
- URUUOQUMOPTRRE-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 URUUOQUMOPTRRE-UHFFFAOYSA-N 0.000 claims 1
- NLKACQGBKCKERK-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OCC(C)C)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 NLKACQGBKCKERK-UHFFFAOYSA-N 0.000 claims 1
- GBVRWXQLLMGEQJ-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1CC1COC(C=C1)=CC=C1C(C(=C1C=2)C=3N=C(NC4CCCC4)N=CC=3)=NN1C=CC=2NC1CCCC1 GBVRWXQLLMGEQJ-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28274901P | 2001-04-10 | 2001-04-10 | |
| PCT/US2002/008793 WO2002083672A1 (en) | 2001-04-10 | 2002-03-21 | Antiviral pyrazolopyridine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004529926A JP2004529926A (ja) | 2004-09-30 |
| JP2004529926A5 true JP2004529926A5 (cg-RX-API-DMAC10.html) | 2005-07-28 |
| JP4219171B2 JP4219171B2 (ja) | 2009-02-04 |
Family
ID=23082954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002581427A Expired - Fee Related JP4219171B2 (ja) | 2001-04-10 | 2002-03-21 | 抗ウイルス性ピラゾロピリジン化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7141569B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1377575B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP4219171B2 (cg-RX-API-DMAC10.html) |
| AT (1) | ATE332301T1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE60212949T2 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2266487T3 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2002083672A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2286272T3 (es) * | 2001-09-07 | 2007-12-01 | Smithkline Beecham Corporation | Pirizolo-piridinas para el tratamiento de infecciones por herpes. |
| WO2003076441A1 (en) | 2002-03-07 | 2003-09-18 | Smithkline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| WO2004033454A1 (en) * | 2002-10-03 | 2004-04-22 | Smithkline Beecham Corporation | Therapeutic compounds based on pyrazolopyridine derivatives |
| US7812022B2 (en) * | 2004-12-21 | 2010-10-12 | Glaxosmithkline Llc | 2-pyrimidinyl pyrazolopyridine ErbB kinase inhibitors |
| ES2421450T3 (es) * | 2005-12-05 | 2013-09-02 | Glaxosmithkline Llc | 2-Pirimidinil-pirazolopiridinas inhibidoras de la quinasa ErbB |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| EP2402335A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| EP2402336A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| CN113121450A (zh) | 2014-08-29 | 2021-07-16 | Tes制药有限责任公司 | α-氨基-β-羧基粘康酸半醛脱羧酶抑制剂 |
| WO2017041005A1 (en) | 2015-09-03 | 2017-03-09 | Abbott Molecular Inc. | Hybridization buffers comprising an alkyl diester |
| TW201718581A (zh) | 2015-10-19 | 2017-06-01 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| SG10202004618TA (en) | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| US20170174671A1 (en) | 2015-12-17 | 2017-06-22 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SI3394033T1 (sl) | 2015-12-22 | 2021-03-31 | Incyte Corporation | Heterociklične spojine kot imunomodulatorji |
| CN108779490A (zh) * | 2016-01-08 | 2018-11-09 | 雅培分子公司 | 包含硫氰酸胍的杂交缓冲液 |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| MA45116A (fr) | 2016-05-26 | 2021-06-02 | Incyte Corp | Composés hétérocycliques comme immunomodulateurs |
| ES2927984T3 (es) | 2016-06-20 | 2022-11-14 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| ES2930092T3 (es) | 2016-07-14 | 2022-12-07 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| US20180057486A1 (en) | 2016-08-29 | 2018-03-01 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| MX391981B (es) | 2016-12-22 | 2025-03-21 | Incyte Corp | Derivados de benzooxazol como inmunomoduladores. |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| ES2929193T3 (es) | 2016-12-22 | 2022-11-25 | Incyte Corp | Derivados de tetrahidro imidazo[4,5-c]piridina como inductores de la internalización de PD-L1 |
| SMT202300065T1 (it) | 2018-03-30 | 2023-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| PL3790877T3 (pl) | 2018-05-11 | 2023-06-12 | Incyte Corporation | Pochodne tetrahydroimidazo[4,5-c]pirydyny jako immunomodulatory pd-l1 |
| WO2021030162A1 (en) | 2019-08-09 | 2021-02-18 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
| IL291471B2 (en) | 2019-09-30 | 2025-04-01 | Incyte Corp | Pyrimido[3,2–D]pyrimidine compounds as immunomodulators |
| CN114829366A (zh) | 2019-11-11 | 2022-07-29 | 因赛特公司 | Pd-1/pd-l1抑制剂的盐及结晶形式 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| US11866434B2 (en) | 2020-11-06 | 2024-01-09 | Incyte Corporation | Process for making a PD-1/PD-L1 inhibitor and salts and crystalline forms thereof |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
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| GB8404584D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| GB8404586D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
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| FR2757166B1 (fr) | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
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-
2002
- 2002-03-21 DE DE60212949T patent/DE60212949T2/de not_active Expired - Fee Related
- 2002-03-21 US US10/473,491 patent/US7141569B2/en not_active Expired - Fee Related
- 2002-03-21 EP EP02723554A patent/EP1377575B1/en not_active Expired - Lifetime
- 2002-03-21 ES ES02723554T patent/ES2266487T3/es not_active Expired - Lifetime
- 2002-03-21 JP JP2002581427A patent/JP4219171B2/ja not_active Expired - Fee Related
- 2002-03-21 WO PCT/US2002/008793 patent/WO2002083672A1/en not_active Ceased
- 2002-03-21 AT AT02723554T patent/ATE332301T1/de not_active IP Right Cessation
-
2006
- 2006-06-06 US US11/422,357 patent/US20060235043A1/en not_active Abandoned