JP2004527560A5 - - Google Patents
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- Publication number
- JP2004527560A5 JP2004527560A5 JP2002585423A JP2002585423A JP2004527560A5 JP 2004527560 A5 JP2004527560 A5 JP 2004527560A5 JP 2002585423 A JP2002585423 A JP 2002585423A JP 2002585423 A JP2002585423 A JP 2002585423A JP 2004527560 A5 JP2004527560 A5 JP 2004527560A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopentylamino
- pyrazolo
- pyridin
- pyrimidinyl
- fluorophenyl
- 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.)
- Pending
Links
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 30
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 23
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 21
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- -1 1-pyrrolidinylcarbonyl Chemical group 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- RJAIATRJLAYBKS-UHFFFAOYSA-N 4-[5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-7-(cyclopropylamino)pyrazolo[1,5-a]pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NN(C(NC2CC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RJAIATRJLAYBKS-UHFFFAOYSA-N 0.000 claims 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- CNMBLWDXHYWTLA-UHFFFAOYSA-N 5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopropyl-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 CNMBLWDXHYWTLA-UHFFFAOYSA-N 0.000 claims 1
- WCKXXYWOSVAGLZ-UHFFFAOYSA-N 5-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopropyl-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-7-amine Chemical compound N12N=C(C=3C=CC(OCC4CC4)=CC=3)C(C=3N=C(NC4CCCC4)N=CC=3)=C2C=C(Cl)C=C1NC1CC1 WCKXXYWOSVAGLZ-UHFFFAOYSA-N 0.000 claims 1
- GLKWTXUVFUJIGX-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-2-(4-methoxyphenyl)-3-(2-methylsulfanylpyrimidin-4-yl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(SC)=N1 GLKWTXUVFUJIGX-UHFFFAOYSA-N 0.000 claims 1
- KMUNEVPPFFIIAM-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-2-(4-methoxyphenyl)-3-(2-methylsulfinylpyrimidin-4-yl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(S(C)=O)=N1 KMUNEVPPFFIIAM-UHFFFAOYSA-N 0.000 claims 1
- FVDIJBUKMLLPCL-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 FVDIJBUKMLLPCL-UHFFFAOYSA-N 0.000 claims 1
- ARFXCYCTFNKRNL-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 ARFXCYCTFNKRNL-UHFFFAOYSA-N 0.000 claims 1
- KVWGXHFUCADPDK-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-3-[2-(cyclopropylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(NC2CCCC2)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CC2)=N1 KVWGXHFUCADPDK-UHFFFAOYSA-N 0.000 claims 1
- ZIDVGKZMRABSOF-UHFFFAOYSA-N 7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-hydroxypyrazolo[1,5-a]pyridine-6-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 ZIDVGKZMRABSOF-UHFFFAOYSA-N 0.000 claims 1
- RWOYMYIYXMICCH-UHFFFAOYSA-N 7-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(Cl)=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RWOYMYIYXMICCH-UHFFFAOYSA-N 0.000 claims 1
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims 1
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 claims 1
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- FQNJTEQMAQMIMU-UHFFFAOYSA-N [7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]methanol Chemical compound OCC=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 FQNJTEQMAQMIMU-UHFFFAOYSA-N 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- JQTSLEMPHVXCDY-UHFFFAOYSA-N ethyl 7-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carboxylate Chemical compound CCOC(=O)C=1C=CC2=C(C=3N=C(NC4CCCC4)N=CC=3)C(C=3C=CC(F)=CC=3)=NN2C=1NC1CCCC1 JQTSLEMPHVXCDY-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- OJDKXSZDDHEORF-UHFFFAOYSA-N n-cyclopentyl-2-(4-fluorophenyl)-3-(2-pyrrolidin-1-ylpyrimidin-4-yl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(NC2CCCC2)=C(C=C2)C(F)(F)F)C2=C1C1=CC=NC(N2CCCC2)=N1 OJDKXSZDDHEORF-UHFFFAOYSA-N 0.000 claims 1
- ZKYXVDDZBFULBP-UHFFFAOYSA-N n-cyclopentyl-4-[5,7-dichloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(Cl)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 ZKYXVDDZBFULBP-UHFFFAOYSA-N 0.000 claims 1
- UPURSWNGJDCEHG-UHFFFAOYSA-N n-cyclopentyl-4-[5,7-dichloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C(Cl)=CC(Cl)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 UPURSWNGJDCEHG-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28694801P | 2001-04-27 | 2001-04-27 | |
| PCT/US2002/010687 WO2002088124A2 (en) | 2001-04-27 | 2002-04-05 | Pyrazolo'1,5-a!pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004527560A JP2004527560A (ja) | 2004-09-09 |
| JP2004527560A5 true JP2004527560A5 (cg-RX-API-DMAC10.html) | 2005-08-18 |
Family
ID=23100830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002585423A Pending JP2004527560A (ja) | 2001-04-27 | 2002-04-05 | ピラゾロ［１，５−α］ピリジン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6962914B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1385847B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2004527560A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE296826T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU2002305143A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE60204452T2 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2242028T3 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2002088124A2 (cg-RX-API-DMAC10.html) |
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| WO2003076441A1 (en) | 2002-03-07 | 2003-09-18 | Smithkline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| WO2006055245A2 (en) * | 2004-11-17 | 2006-05-26 | Smithkline Beecham Corporation | Process for preparing pyrazolopyridine compounds |
| 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 |
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| CN104945420A (zh) | 2009-06-29 | 2015-09-30 | 因塞特公司 | 作为pi3k抑制剂的嘧啶酮类 |
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| US20140206678A1 (en) * | 2011-01-27 | 2014-07-24 | Kadmon Corporation, Llc | Inhibitors of mtor kinase as anti -viral agent |
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| US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
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| PT3831833T (pt) | 2015-02-27 | 2023-02-06 | Incyte Corp | Processos para a preparação de um inibidor pi3k |
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| SI3394033T1 (sl) | 2015-12-22 | 2021-03-31 | Incyte Corporation | Heterociklične spojine kot imunomodulatorji |
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| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
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| SMT202300065T1 (it) | 2018-03-30 | 2023-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
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| 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 |
| 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 |
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| 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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-
2002
- 2002-04-05 EP EP02733945A patent/EP1385847B1/en not_active Expired - Lifetime
- 2002-04-05 AT AT02733945T patent/ATE296826T1/de not_active IP Right Cessation
- 2002-04-05 AU AU2002305143A patent/AU2002305143A1/en not_active Abandoned
- 2002-04-05 WO PCT/US2002/010687 patent/WO2002088124A2/en not_active Ceased
- 2002-04-05 US US10/473,751 patent/US6962914B2/en not_active Expired - Fee Related
- 2002-04-05 JP JP2002585423A patent/JP2004527560A/ja active Pending
- 2002-04-05 ES ES02733945T patent/ES2242028T3/es not_active Expired - Lifetime
- 2002-04-05 DE DE60204452T patent/DE60204452T2/de not_active Expired - Fee Related
-
2005
- 2005-03-31 US US11/095,361 patent/US20050192295A1/en not_active Abandoned
- 2005-03-31 US US11/095,212 patent/US7030134B2/en not_active Expired - Fee Related
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