JP2005508942A5 - - Google Patents
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- Publication number
- JP2005508942A5 JP2005508942A5 JP2003533936A JP2003533936A JP2005508942A5 JP 2005508942 A5 JP2005508942 A5 JP 2005508942A5 JP 2003533936 A JP2003533936 A JP 2003533936A JP 2003533936 A JP2003533936 A JP 2003533936A JP 2005508942 A5 JP2005508942 A5 JP 2005508942A5
- Authority
- JP
- Japan
- Prior art keywords
- furan
- triazolo
- amino
- pyridin
- bromo
- 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
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- BQRGSPQJKCXBSD-UHFFFAOYSA-N 1-[8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carbonyl]-n,n-diethylpiperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C(=O)C1=CN2N=C(C=3OC(Br)=CC=3)N=C2C(N)=C1 BQRGSPQJKCXBSD-UHFFFAOYSA-N 0.000 claims 1
- SXFIMYRGBYBUDX-UHFFFAOYSA-N 1-[8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound N1=C2C(N)=CC(C(=O)N3C(CCC3)C(O)=O)=CN2N=C1C1=CC=C(Br)O1 SXFIMYRGBYBUDX-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- YFJWZPSPCPVPFB-UHFFFAOYSA-N 8-amino-2-(5-bromofuran-2-yl)-n-[2-(dimethylamino)-2-oxoethyl]-n-methyl-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide Chemical compound N=1N2C=C(C(=O)N(C)CC(=O)N(C)C)C=C(N)C2=NC=1C1=CC=C(Br)O1 YFJWZPSPCPVPFB-UHFFFAOYSA-N 0.000 claims 1
- VKKPJYXECVYOOR-UHFFFAOYSA-N 8-amino-2-(5-bromofuran-2-yl)-n-methyl-n-(2-phenylethyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide Chemical compound C1=C(N)C2=NC(C=3OC(Br)=CC=3)=NN2C=C1C(=O)N(C)CCC1=CC=CC=C1 VKKPJYXECVYOOR-UHFFFAOYSA-N 0.000 claims 1
- CRJKDPUUJDEQAN-UHFFFAOYSA-N 8-amino-2-(5-bromofuran-2-yl)-n-methyl-n-propyl-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide Chemical compound N=1N2C=C(C(=O)N(C)CCC)C=C(N)C2=NC=1C1=CC=C(Br)O1 CRJKDPUUJDEQAN-UHFFFAOYSA-N 0.000 claims 1
- YTBLSIQUZIGOID-UHFFFAOYSA-N 8-amino-n,n-dibenzyl-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide Chemical compound N1=C2C(N)=CC(C(=O)N(CC=3C=CC=CC=3)CC=3C=CC=CC=3)=CN2N=C1C1=CC=CO1 YTBLSIQUZIGOID-UHFFFAOYSA-N 0.000 claims 1
- FEYPYIVHMWLVED-UHFFFAOYSA-N 8-amino-n,n-dibenzyl-2-thiophen-2-yl-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide Chemical compound N1=C2C(N)=CC(C(=O)N(CC=3C=CC=CC=3)CC=3C=CC=CC=3)=CN2N=C1C1=CC=CS1 FEYPYIVHMWLVED-UHFFFAOYSA-N 0.000 claims 1
- GINKFJFEXIJBQU-UHFFFAOYSA-N 8-amino-n-methyl-2-(5-methylfuran-2-yl)-n-propyl-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide Chemical compound N=1N2C=C(C(=O)N(C)CCC)C=C(N)C2=NC=1C1=CC=C(C)O1 GINKFJFEXIJBQU-UHFFFAOYSA-N 0.000 claims 1
- 102000009346 Adenosine receptors Human genes 0.000 claims 1
- 108050000203 Adenosine receptors Proteins 0.000 claims 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 1
- BRWRUOUOXMJDGU-UHFFFAOYSA-N CCNCCC1=NC=CC=C1.NC1=CC(C(O)=O)=CN2N=C(C(O3)=CC=C3Br)N=C12 Chemical compound CCNCCC1=NC=CC=C1.NC1=CC(C(O)=O)=CN2N=C(C(O3)=CC=C3Br)N=C12 BRWRUOUOXMJDGU-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VMKQFVIUGLZAGX-UHFFFAOYSA-N [8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-(3,5-dimethylpiperidin-1-yl)methanone Chemical compound C1C(C)CC(C)CN1C(=O)C1=CN2N=C(C=3OC(Br)=CC=3)N=C2C(N)=C1 VMKQFVIUGLZAGX-UHFFFAOYSA-N 0.000 claims 1
- YKCZVFYOXMAMHO-NSHDSACASA-N [8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@@H]1CCCN1C(=O)C1=CN2N=C(C=3OC(Br)=CC=3)N=C2C(N)=C1 YKCZVFYOXMAMHO-NSHDSACASA-N 0.000 claims 1
- YKCZVFYOXMAMHO-UHFFFAOYSA-N [8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-[2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COCC1CCCN1C(=O)C1=CN2N=C(C=3OC(Br)=CC=3)N=C2C(N)=C1 YKCZVFYOXMAMHO-UHFFFAOYSA-N 0.000 claims 1
- SABQIWHZZCNQTM-UHFFFAOYSA-N [8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-piperidin-1-ylmethanone Chemical compound N1=C2C(N)=CC(C(=O)N3CCCCC3)=CN2N=C1C1=CC=C(Br)O1 SABQIWHZZCNQTM-UHFFFAOYSA-N 0.000 claims 1
- UCJICYRCCGGBIG-UHFFFAOYSA-N [8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrrolidin-1-ylmethanone Chemical compound N1=C2C(N)=CC(C(=O)N3CCCC3)=CN2N=C1C1=CC=C(Br)O1 UCJICYRCCGGBIG-UHFFFAOYSA-N 0.000 claims 1
- AOZIOKRQIGVBSF-UHFFFAOYSA-N [8-amino-2-(5-bromofuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-thiomorpholin-4-ylmethanone Chemical compound N1=C2C(N)=CC(C(=O)N3CCSCC3)=CN2N=C1C1=CC=C(Br)O1 AOZIOKRQIGVBSF-UHFFFAOYSA-N 0.000 claims 1
- MPHMKIOJYJWCPR-UHFFFAOYSA-N [8-amino-2-(5-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-(2-methylpyrrolidin-1-yl)methanone Chemical compound CC1CCCN1C(=O)C1=CN2N=C(C=3OC(C)=CC=3)N=C2C(N)=C1 MPHMKIOJYJWCPR-UHFFFAOYSA-N 0.000 claims 1
- GAYRSWBLTWEKKG-UHFFFAOYSA-N [8-amino-2-(5-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-piperidin-1-ylmethanone Chemical compound O1C(C)=CC=C1C1=NN2C=C(C(=O)N3CCCCC3)C=C(N)C2=N1 GAYRSWBLTWEKKG-UHFFFAOYSA-N 0.000 claims 1
- HFXWHDXIYAZHEK-UHFFFAOYSA-N [8-amino-2-(5-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrrolidin-1-ylmethanone Chemical compound O1C(C)=CC=C1C1=NN2C=C(C(=O)N3CCCC3)C=C(N)C2=N1 HFXWHDXIYAZHEK-UHFFFAOYSA-N 0.000 claims 1
- UDWANUCVDXADNE-GFCCVEGCSA-N [8-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]methanone Chemical compound COC[C@H]1CCCN1C(=O)C1=CN2N=C(C=3OC=CC=3)N=C2C(N)=C1 UDWANUCVDXADNE-GFCCVEGCSA-N 0.000 claims 1
- WREXZRPCJAVZSW-UHFFFAOYSA-N [8-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrrolidin-1-ylmethanone Chemical compound N1=C2C(N)=CC(C(=O)N3CCCC3)=CN2N=C1C1=CC=CO1 WREXZRPCJAVZSW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229960005305 adenosine Drugs 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01123948 | 2001-10-08 | ||
| PCT/EP2002/011152 WO2003030904A1 (en) | 2001-10-08 | 2002-10-04 | 8-amino-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid amide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005508942A JP2005508942A (ja) | 2005-04-07 |
| JP2005508942A5 true JP2005508942A5 (enExample) | 2005-12-22 |
| JP4101755B2 JP4101755B2 (ja) | 2008-06-18 |
Family
ID=8178876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003533936A Expired - Fee Related JP4101755B2 (ja) | 2001-10-08 | 2002-10-04 | ８−アミノ−〔１，２，４〕トリアゾロ〔１，５−ａ〕ピリジン−６−カルボン酸アミド |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6689790B2 (enExample) |
| EP (1) | EP1435952A1 (enExample) |
| JP (1) | JP4101755B2 (enExample) |
| KR (1) | KR100614486B1 (enExample) |
| CN (1) | CN1564686A (enExample) |
| AR (1) | AR036734A1 (enExample) |
| AU (1) | AU2002347055B2 (enExample) |
| BR (1) | BR0213172A (enExample) |
| CA (1) | CA2462806A1 (enExample) |
| MX (1) | MXPA04003277A (enExample) |
| PL (1) | PL370067A1 (enExample) |
| RU (1) | RU2296763C2 (enExample) |
| WO (1) | WO2003030904A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009259853A1 (en) * | 2008-06-20 | 2009-12-23 | Genentech, Inc. | Triazolopyridine JAK inhibitor compounds and methods |
| EP2296475A4 (en) * | 2008-06-20 | 2014-03-05 | Genentech Inc | TRIAZOLOPYRIDINE COMPOUNDS JAK KINASE INHIBITORS AND METHODS |
| TWI453207B (zh) * | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| DK2455381T5 (en) * | 2009-07-17 | 2015-02-09 | Japan Tobacco Inc | Triazolopyridinforbindelse and its effect as an inhibitor of prolyl hydroxylase and induce erythropoietin production by |
| JP6122034B2 (ja) * | 2012-02-09 | 2017-04-26 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ２−フェニル−［１，２，４］トリアゾロ［１，５−ａ］ピリジン誘導体の調製方法 |
| US9048427B2 (en) * | 2013-03-06 | 2015-06-02 | National Tsing Hua University | Thin film fabrication of rubber material with piezoelectric characteristics |
| MY172600A (en) * | 2013-05-31 | 2019-12-05 | Nissan Chemical Ind Ltd | Heterocyclic amide compound |
| CN104370807B (zh) * | 2014-11-13 | 2016-10-05 | 安徽星宇化工有限公司 | 一种6-羟基-5-硝基烟酸的合成方法及其分离提纯方法 |
| CA3095839A1 (en) | 2018-04-08 | 2019-10-17 | Beigene, Ltd. | Pyrazolotriazolopyrimidine derivatives as a2a receptor antagonist |
| CN110742893B (zh) * | 2018-07-23 | 2024-04-05 | 百济神州(北京)生物科技有限公司 | A2a受体拮抗剂治疗癌症的方法 |
| WO2020054712A1 (ja) * | 2018-09-12 | 2020-03-19 | 日本化薬株式会社 | 有害生物防除剤 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE287263C (enExample) * | ||||
| HU208693B (en) * | 1991-02-22 | 1993-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them |
| ATE182332T1 (de) * | 1994-06-16 | 1999-08-15 | Pfizer | Pyrazolo und pyrrolopyridine |
| JP4195729B2 (ja) * | 1997-03-24 | 2008-12-10 | 協和醗酵工業株式会社 | ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体 |
| US6355653B1 (en) * | 1999-09-06 | 2002-03-12 | Hoffmann-La Roche Inc. | Amino-triazolopyridine derivatives |
| US6506772B1 (en) * | 2000-12-15 | 2003-01-14 | Hoffmann-La Roche Inc. | Substituted [1,2,4]triazolo[1,5a]pyridine derivatives with activity as adenosine receptor ligands |
-
2002
- 2002-10-04 WO PCT/EP2002/011152 patent/WO2003030904A1/en not_active Ceased
- 2002-10-04 MX MXPA04003277A patent/MXPA04003277A/es active IP Right Grant
- 2002-10-04 EP EP02782832A patent/EP1435952A1/en not_active Withdrawn
- 2002-10-04 PL PL02370067A patent/PL370067A1/xx not_active Application Discontinuation
- 2002-10-04 CN CNA02819912XA patent/CN1564686A/zh active Pending
- 2002-10-04 AU AU2002347055A patent/AU2002347055B2/en not_active Ceased
- 2002-10-04 RU RU2004114278/04A patent/RU2296763C2/ru not_active IP Right Cessation
- 2002-10-04 JP JP2003533936A patent/JP4101755B2/ja not_active Expired - Fee Related
- 2002-10-04 BR BR0213172-2A patent/BR0213172A/pt not_active IP Right Cessation
- 2002-10-04 KR KR1020047005091A patent/KR100614486B1/ko not_active Expired - Fee Related
- 2002-10-04 AR ARP020103749A patent/AR036734A1/es unknown
- 2002-10-04 CA CA002462806A patent/CA2462806A1/en not_active Abandoned
- 2002-10-07 US US10/265,957 patent/US6689790B2/en not_active Expired - Fee Related
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