JP4762543B2 - インダゾールカルボキサミド誘導体、それらの製造法ならびにcdk1、cdk2およびcdk4阻害剤としての用途 - Google Patents
インダゾールカルボキサミド誘導体、それらの製造法ならびにcdk1、cdk2およびcdk4阻害剤としての用途 Download PDFInfo
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- JP4762543B2 JP4762543B2 JP2004540862A JP2004540862A JP4762543B2 JP 4762543 B2 JP4762543 B2 JP 4762543B2 JP 2004540862 A JP2004540862 A JP 2004540862A JP 2004540862 A JP2004540862 A JP 2004540862A JP 4762543 B2 JP4762543 B2 JP 4762543B2
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- Prior art keywords
- indazole
- carboxamide
- pyridin
- nhr
- phenyl
- 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.)
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- 238000000034 method Methods 0.000 title claims description 34
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical class C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
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- 239000003112 inhibitor Substances 0.000 title description 7
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 title 1
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- 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 title 1
- 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 title 1
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- 150000001875 compounds Chemical class 0.000 claims description 207
- -1 CH 2 OH Chemical group 0.000 claims description 127
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 99
- 125000001072 heteroaryl group Chemical group 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 229910052786 argon Inorganic materials 0.000 claims description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 51
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 24
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims description 3
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- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- JJTANKMFDNMIHL-UHFFFAOYSA-N 5-(1h-pyrazol-4-yl)-n-pyridin-4-yl-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C3=CNN=C3)C=C2C=1C(=O)NC1=CC=NC=C1 JJTANKMFDNMIHL-UHFFFAOYSA-N 0.000 claims description 2
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| Application Number | Priority Date | Filing Date | Title |
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| FR02/12188 | 2002-10-02 | ||
| FR0212188A FR2845382A1 (fr) | 2002-10-02 | 2002-10-02 | Derives d'indazolecarboxamides, leur preparation et leur utilisation en therapeutique |
| PCT/FR2003/002862 WO2004031158A1 (fr) | 2002-10-02 | 2003-09-30 | Derives d'indazolecarboxamides, leur preparation et leur utilisation comme inhibiteurs des cdk1, cdk2 et cdk4 |
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| JP2006504711A JP2006504711A (ja) | 2006-02-09 |
| JP2006504711A5 JP2006504711A5 (https=) | 2006-11-16 |
| JP4762543B2 true JP4762543B2 (ja) | 2011-08-31 |
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| JP (1) | JP4762543B2 (https=) |
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| AU (1) | AU2003299125A1 (https=) |
| FR (1) | FR2845382A1 (https=) |
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| WO2024073502A1 (en) * | 2022-09-28 | 2024-04-04 | Accutar Biotechnology Inc. | Heterocyclic compounds as e3 ligase inhibitors |
| WO2024109642A1 (zh) * | 2023-07-28 | 2024-05-30 | 常州大学 | 一种苯并氮杂环类化合物作为β2-肾上腺素受体别构调节剂的应用 |
| CN116874432B (zh) * | 2023-07-28 | 2025-08-05 | 常州大学 | 用作β2-肾上腺素受体拮抗剂的苯并咪唑类衍生物 |
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| US3457269A (en) * | 1967-02-24 | 1969-07-22 | Sterling Drug Inc | N-substituted phenyl and n-substituted phenylalkyl 3 - indazolecarboxamides and preparation thereof |
| JPH03118370A (ja) * | 1989-07-25 | 1991-05-20 | Duphar Internatl Res Bv | 新規な置換1h―インタゾール―3―カルボキシアミド |
| JP2006500348A (ja) * | 2002-08-10 | 2006-01-05 | アステックス テクノロジー リミテッド | サイクリン依存キナーゼ(cdk)インヒビターとしての1h−インダゾール−3−カルボキサミド化合物 |
| JP4414881B2 (ja) * | 2002-05-31 | 2010-02-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピラゾール化合物およびこれを含んでなる医薬組成物 |
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| WO1994005642A1 (en) * | 1992-08-28 | 1994-03-17 | Ciba-Geigy Ag | Indazole derivatives |
| KR100423899B1 (ko) * | 2000-05-10 | 2004-03-24 | 주식회사 엘지생명과학 | 세포 증식 억제제로 유용한 1,1-디옥소이소티아졸리딘을갖는 인다졸 |
| US20060135516A1 (en) | 2002-08-10 | 2006-06-22 | Astex Technology, Ltd. | 3-(Carbonyl) 1h-indazole compounds as cyclin dependent kinases (cdk) inhibitors |
| CN100395234C (zh) * | 2003-01-02 | 2008-06-18 | 霍夫曼-拉罗奇有限公司 | 新cb1受体反激动剂 |
-
2002
- 2002-10-02 FR FR0212188A patent/FR2845382A1/fr active Pending
-
2003
- 2003-09-30 WO PCT/FR2003/002862 patent/WO2004031158A1/fr not_active Ceased
- 2003-09-30 JP JP2004540862A patent/JP4762543B2/ja not_active Expired - Fee Related
- 2003-09-30 EP EP03798949A patent/EP1549620A1/fr not_active Withdrawn
- 2003-09-30 AU AU2003299125A patent/AU2003299125A1/en not_active Abandoned
- 2003-10-01 AR ARP030103581A patent/AR041459A1/es unknown
- 2003-10-01 TW TW092127213A patent/TWI331603B/zh not_active IP Right Cessation
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2005
- 2005-04-01 US US11/096,375 patent/US7482342B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3457269A (en) * | 1967-02-24 | 1969-07-22 | Sterling Drug Inc | N-substituted phenyl and n-substituted phenylalkyl 3 - indazolecarboxamides and preparation thereof |
| JPH03118370A (ja) * | 1989-07-25 | 1991-05-20 | Duphar Internatl Res Bv | 新規な置換1h―インタゾール―3―カルボキシアミド |
| JP4414881B2 (ja) * | 2002-05-31 | 2010-02-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピラゾール化合物およびこれを含んでなる医薬組成物 |
| JP2006500348A (ja) * | 2002-08-10 | 2006-01-05 | アステックス テクノロジー リミテッド | サイクリン依存キナーゼ(cdk)インヒビターとしての1h−インダゾール−3−カルボキサミド化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2845382A1 (fr) | 2004-04-09 |
| TW200418805A (en) | 2004-10-01 |
| JP2006504711A (ja) | 2006-02-09 |
| EP1549620A1 (fr) | 2005-07-06 |
| WO2004031158A1 (fr) | 2004-04-15 |
| US20060004000A1 (en) | 2006-01-05 |
| TWI331603B (en) | 2010-10-11 |
| US7482342B2 (en) | 2009-01-27 |
| AU2003299125A1 (en) | 2004-04-23 |
| AR041459A1 (es) | 2005-05-18 |
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