JP2009524668A5 - - Google Patents
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- Publication number
- JP2009524668A5 JP2009524668A5 JP2008552392A JP2008552392A JP2009524668A5 JP 2009524668 A5 JP2009524668 A5 JP 2009524668A5 JP 2008552392 A JP2008552392 A JP 2008552392A JP 2008552392 A JP2008552392 A JP 2008552392A JP 2009524668 A5 JP2009524668 A5 JP 2009524668A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- quinolin
- imidazo
- amine
- 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.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 102000009346 Adenosine receptors Human genes 0.000 claims description 11
- 108050000203 Adenosine receptors Proteins 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000005011 alkyl ether group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 10
- UWJVRSIGHHSDSJ-UHFFFAOYSA-N 2-cyclohexyl-n-(3,4-dichlorophenyl)-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=C(C1CCCCC1)N2 UWJVRSIGHHSDSJ-UHFFFAOYSA-N 0.000 claims description 9
- WMPDXFZIOXNJQW-UHFFFAOYSA-N 2-cyclobutyl-n-(3,4-dichlorophenyl)-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=C(C1CCC1)N2 WMPDXFZIOXNJQW-UHFFFAOYSA-N 0.000 claims description 8
- CIAWUMXIIRHASR-UHFFFAOYSA-N 2-cycloheptyl-n-(3,4-dichlorophenyl)-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=C(C1CCCCCC1)N2 CIAWUMXIIRHASR-UHFFFAOYSA-N 0.000 claims description 8
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 claims description 8
- 230000003281 allosteric effect Effects 0.000 claims description 8
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 8
- FHLIAQGQHFKJLO-UHFFFAOYSA-N 2-cyclopentyl-n-(4-methylphenyl)-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC(C)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=C(C1CCCC1)N2 FHLIAQGQHFKJLO-UHFFFAOYSA-N 0.000 claims description 6
- QNXQZORHRAILMI-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC5=C(C=C4)C=CN5)C6CC6 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC5=C(C=C4)C=CN5)C6CC6 QNXQZORHRAILMI-UHFFFAOYSA-N 0.000 claims description 6
- RQGIYFFCUYPACG-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NCC4=CC=C(C=C4)OC)C5CC5 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NCC4=CC=C(C=C4)OC)C5CC5 RQGIYFFCUYPACG-UHFFFAOYSA-N 0.000 claims description 6
- GFLSHZKQSIQGIS-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NCC4=CC=CC=C4)C5CC5 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NCC4=CC=CC=C4)C5CC5 GFLSHZKQSIQGIS-UHFFFAOYSA-N 0.000 claims description 6
- PUKKITFKLVCRDY-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NCCC4=CC=CC=C4)C5CC5 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NCCC4=CC=CC=C4)C5CC5 PUKKITFKLVCRDY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- VWLNHLFTOFSRJQ-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-1-(furan-2-yl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=CN2C1=CC=CO1 VWLNHLFTOFSRJQ-UHFFFAOYSA-N 0.000 claims description 6
- QFVMTOIWGGXICC-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-pentyl-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound N1=C2C=CC=CC2=C2NC(CCCCC)=NC2=C1NC1=CC=C(Cl)C(Cl)=C1 QFVMTOIWGGXICC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 150000001925 cycloalkenes Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000003460 sulfonic acids Chemical class 0.000 claims description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- SYNRBWNXNMPXNT-UHFFFAOYSA-N 2-cyclopentyl-n-(3,4-dichlorophenyl)-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=C(C1CCCC1)N2 SYNRBWNXNMPXNT-UHFFFAOYSA-N 0.000 claims 4
- 230000002708 enhancing effect Effects 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- UNICMRYDUGOJFV-UHFFFAOYSA-N 2-cyclopentyl-n-(1h-indazol-6-yl)-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC1C(NC1=C2C=CC=CC2=N2)=NC1=C2NC1=CC=C(C=NN2)C2=C1 UNICMRYDUGOJFV-UHFFFAOYSA-N 0.000 claims 2
- YJOOJLDFTONSNI-UHFFFAOYSA-N 2-cyclopentyl-n-(4-methoxyphenyl)-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=C(C1CCCC1)N2 YJOOJLDFTONSNI-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 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
- 239000000556 agonist Substances 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- ULXQEAQZAZBLPR-UHFFFAOYSA-N n-(4-chlorophenyl)-2-cyclopentyl-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NC2=CC=CC=C2C2=C1N=C(C1CCCC1)N2 ULXQEAQZAZBLPR-UHFFFAOYSA-N 0.000 claims 2
- 230000000638 stimulation Effects 0.000 claims 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 1
- 206010061598 Immunodeficiency Diseases 0.000 claims 1
- 229960005305 adenosine Drugs 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 238000010494 dissociation reaction Methods 0.000 claims 1
- 230000005593 dissociations Effects 0.000 claims 1
- 230000004410 intraocular pressure Effects 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- TUEGVCWMLOHZJR-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC(=C(C=C4)Cl)Cl)C5CC5 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC(=C(C=C4)Cl)Cl)C5CC5 TUEGVCWMLOHZJR-UHFFFAOYSA-N 0.000 description 4
- XVUYCOXWFOCRPF-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC5=C(C=C4)C=NN5)C6CC6 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC5=C(C=C4)C=NN5)C6CC6 XVUYCOXWFOCRPF-UHFFFAOYSA-N 0.000 description 4
- BFLUOWGTSAKSIV-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC=C(C=C4)Cl)C5CC5 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC=C(C=C4)Cl)C5CC5 BFLUOWGTSAKSIV-UHFFFAOYSA-N 0.000 description 4
- NYYJMURHRVORNF-UHFFFAOYSA-N CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC=C(C=C4)OC)C5CC5 Chemical compound CCCC(CN1C=NC2=C1C3=CC=CC=C3N=C2NC4=CC=C(C=C4)OC)C5CC5 NYYJMURHRVORNF-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 0 *c1nc(c(N*)nc2c3cccc2)c3[n]1 Chemical compound *c1nc(c(N*)nc2c3cccc2)c3[n]1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76214106P | 2006-01-26 | 2006-01-26 | |
| US60/762,141 | 2006-01-26 | ||
| PCT/US2007/001930 WO2007089507A1 (en) | 2006-01-26 | 2007-01-25 | A3 adenosine receptor allosteric modulators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013192745A Division JP2013253108A (ja) | 2006-01-26 | 2013-09-18 | Ａ３アデノシンレセプタ・アロステリックモジュレータ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009524668A JP2009524668A (ja) | 2009-07-02 |
| JP2009524668A5 true JP2009524668A5 (https=) | 2013-02-21 |
| JP5414277B2 JP5414277B2 (ja) | 2014-02-12 |
Family
ID=38116104
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008552392A Active JP5414277B2 (ja) | 2006-01-26 | 2007-01-25 | Ａ３アデノシンレセプタ・アロステリックモジュレータ |
| JP2013192745A Pending JP2013253108A (ja) | 2006-01-26 | 2013-09-18 | Ａ３アデノシンレセプタ・アロステリックモジュレータ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013192745A Pending JP2013253108A (ja) | 2006-01-26 | 2013-09-18 | Ａ３アデノシンレセプタ・アロステリックモジュレータ |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8420664B2 (https=) |
| EP (1) | EP1983990B1 (https=) |
| JP (2) | JP5414277B2 (https=) |
| KR (1) | KR101383228B1 (https=) |
| CN (1) | CN101410114B (https=) |
| AT (1) | ATE502640T1 (https=) |
| DE (1) | DE602007013359D1 (https=) |
| DK (1) | DK1983990T3 (https=) |
| ES (1) | ES2360632T3 (https=) |
| WO (1) | WO2007089507A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| EP1983990B1 (en) | 2006-01-26 | 2011-03-23 | Government of the United States of America, Represented by the Secretary, Department of Health and Human Services | A3 adenosine receptor allosteric modulators |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| PT2322525E (pt) * | 2006-04-21 | 2013-12-26 | Novartis Ag | Derivados de purina para utilização como agonistas do recetor de adenosina a2a |
| GB0607944D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| US7906518B2 (en) * | 2006-06-27 | 2011-03-15 | Cbt Development Limited | Therapeutic compounds |
| EP1889846A1 (en) | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| EP1903044A1 (en) * | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| CN101553459A (zh) * | 2006-11-10 | 2009-10-07 | 诺瓦提斯公司 | 环戊烯二醇单乙酸酯衍生物 |
| JP2012500255A (ja) * | 2008-08-19 | 2012-01-05 | ユニバーシテイト ライデン | Ａ３アデノシン受容体アロステリックモジュレーター |
| KR20120022919A (ko) * | 2009-05-17 | 2012-03-12 | 캔-파이트 바이오파마 리미티드 | 안압의 감소를 위한 ａ3 아데노신 수용체 작동제 |
| KR101971762B1 (ko) * | 2012-08-09 | 2019-08-13 | 캔-파이트 바이오파마 리미티드 | 성기능장애의 치료에 사용하기 위한 a3 아데노신 수용체 리간드 |
| CN103992310B (zh) * | 2013-05-14 | 2016-07-06 | 中国医学科学院医药生物技术研究所 | 一组取代苯并杂环胺衍生物及其制备方法和作为impdh抑制剂的相关应用 |
| ES2578363B1 (es) | 2015-01-22 | 2017-01-31 | Palobiofarma, S.L. | Moduladores de los receptores A3 de adenosina |
| IL242723B (en) | 2015-11-23 | 2019-12-31 | Can Fite Biopharma Ltd | A3 adenosine receptor ligand for the treatment of ectopic fat accumulation |
| KR20180134395A (ko) * | 2016-04-19 | 2018-12-18 | 인네이트 튜머 이뮤니티, 인코포레이티드 | Nlrp3 조정제 |
| ES2676535B1 (es) | 2017-01-20 | 2019-04-29 | Palobiofarma Sl | Moduladores de los receptores a3 de adenosina |
| IL254535A0 (en) | 2017-09-17 | 2017-11-30 | Can Fite Biopharma Ltd | Adenosine a3 receptor ligand for use in the management of cytokine release syndrome |
| IL264112A (en) | 2019-01-06 | 2020-07-30 | Fishman Pnina | An a3 adenosine receptor ligand for use for reducing level of adipocytes |
| EP4499641A1 (en) * | 2022-03-29 | 2025-02-05 | The United States of America, as represented by the Secretary, Department of Health and Human Services | A3 adenosine receptor positive allosteric modulators |
| WO2024014851A1 (ko) * | 2022-07-12 | 2024-01-18 | 주식회사 넥스트젠바이오사이언스 | Hif-1 단백질 억제제로서의 신규한 퓨린 유도체 화합물 |
| IL300132A (en) * | 2023-01-23 | 2024-08-01 | Can Fite Biopharma Ltd | Pancreatic cancer treatment |
| IT202300014340A1 (it) | 2023-07-10 | 2025-01-10 | Consiglio Nazionale Ricerche | Trattamento di malattie associate alla disfunzione del gene ocrl. |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960007566A (ko) | 1994-08-19 | 1996-03-22 | 김정규 | 신규한 퀴놀릴아민 유도체, 그의 제조방법 및 항부정맥제로서의 용도 |
| EP1034207B1 (en) | 1997-10-03 | 2005-03-02 | Macromed Inc. | BIODEGRADABLE LOW MOLECULAR WEIGHT TRIBLOCK POLY(LACTIDE-co-GLYCOLIDE) POLYETHYLENE GLYCOL COPOLYMERS HAVING REVERSE THERMAL GELATION PROPERTIES |
| KR20030076633A (ko) * | 2001-02-05 | 2003-09-26 | 가부시키 가이샤 오오쯔카 세이야쿠 고우죠우 | 트리아조로퀴나졸린 및 피라졸로 트리아조로피리미딘유도체, 의약조성물,아데노신 에이3 수용체 친화제,안압저하제, 녹내장의 예방 및 치료를 위한 제제 및안압저하 방법 |
| US20020179549A1 (en) | 2001-06-04 | 2002-12-05 | Chris Felcman | System and method for mounting a keyboard and display assembly in a 1U rack space |
| JP2006503574A (ja) | 2002-10-22 | 2006-02-02 | カン−フィテ・バイオファーマ・リミテッド | 疾患の状態に関するマーカーとしてのａ３ａｒ |
| JP2007517019A (ja) | 2003-12-29 | 2007-06-28 | カン−フィテ・バイオファーマ・リミテッド | 多発性硬化症の治療方法 |
| CA2585581A1 (en) | 2004-11-22 | 2006-05-26 | King Pharmaceuticals Research & Development Inc. | Enhancing treatment of hif-1 mediated disorders with adenosine a3 receptor agonists |
| EP1983990B1 (en) | 2006-01-26 | 2011-03-23 | Government of the United States of America, Represented by the Secretary, Department of Health and Human Services | A3 adenosine receptor allosteric modulators |
-
2007
- 2007-01-25 EP EP07763034A patent/EP1983990B1/en active Active
- 2007-01-25 WO PCT/US2007/001930 patent/WO2007089507A1/en not_active Ceased
- 2007-01-25 JP JP2008552392A patent/JP5414277B2/ja active Active
- 2007-01-25 DK DK07763034.1T patent/DK1983990T3/da active
- 2007-01-25 AT AT07763034T patent/ATE502640T1/de active
- 2007-01-25 ES ES07763034T patent/ES2360632T3/es active Active
- 2007-01-25 DE DE602007013359T patent/DE602007013359D1/de active Active
- 2007-01-25 KR KR1020087020924A patent/KR101383228B1/ko active Active
- 2007-01-25 CN CN2007800106767A patent/CN101410114B/zh active Active
-
2008
- 2008-07-28 US US12/219,772 patent/US8420664B2/en active Active
-
2013
- 2013-03-13 US US13/800,560 patent/US9326978B2/en active Active
- 2013-09-18 JP JP2013192745A patent/JP2013253108A/ja active Pending
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