JP2008535834A5 - - Google Patents
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- Publication number
- JP2008535834A5 JP2008535834A5 JP2008505261A JP2008505261A JP2008535834A5 JP 2008535834 A5 JP2008535834 A5 JP 2008535834A5 JP 2008505261 A JP2008505261 A JP 2008505261A JP 2008505261 A JP2008505261 A JP 2008505261A JP 2008535834 A5 JP2008535834 A5 JP 2008535834A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- thiazolo
- hydroxymethyl
- amino
- 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
- 150000001875 compounds Chemical class 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 17
- 239000003814 drug Substances 0.000 claims 10
- 201000001320 Atherosclerosis Diseases 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000003902 lesion Effects 0.000 claims 4
- -1 7-{[(1R) -1- (hydroxymethyl) -3-methylbutyl] amino} -2-oxo-2,3-dihydro [1,3] thiazolo [4 , 5-d] pyrimidin-5-yl Chemical group 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- GMGXIHSSDANFNY-PIJUOVFKSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-[1-[2-(trifluoromethyl)phenyl]ethylsulfanyl]-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound N=1C=2NC(=O)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC=C1C(F)(F)F GMGXIHSSDANFNY-PIJUOVFKSA-N 0.000 claims 2
- RZURGDRYOMQZSH-SBXXRYSUSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-[1-[3-(trifluoromethyl)phenyl]ethylsulfanyl]-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound N=1C=2NC(=O)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC(C(F)(F)F)=C1 RZURGDRYOMQZSH-SBXXRYSUSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000016192 Demyelinating disease Diseases 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims 2
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims 2
- 230000008485 antagonism Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000003143 atherosclerotic effect Effects 0.000 claims 2
- 230000007214 atherothrombosis Effects 0.000 claims 2
- 230000009286 beneficial effect Effects 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- XKANTJCXJIVELF-SWLSCSKDSA-N 3-[(1s)-1-[[7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-2-oxo-3h-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]sulfanyl]ethyl]benzonitrile Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(C#N)=C1 XKANTJCXJIVELF-SWLSCSKDSA-N 0.000 claims 1
- COQNFUICOUPODA-SMDDNHRTSA-N 3-[(1s)-1-[[7-[[(2r)-1-hydroxypentan-2-yl]amino]-2-oxo-3h-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]sulfanyl]ethyl]benzonitrile Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CCC)=CC=CC(C#N)=C1 COQNFUICOUPODA-SMDDNHRTSA-N 0.000 claims 1
- DCSLKYLPOSSKFY-UHFFFAOYSA-N 3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1=NC=C2SC(=O)NC2=N1 DCSLKYLPOSSKFY-UHFFFAOYSA-N 0.000 claims 1
- LRSCFMSLOWYTCH-NWDGAFQWSA-N 5-[(1s)-1-(2-fluorophenyl)ethyl]sulfanyl-7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC=C1F LRSCFMSLOWYTCH-NWDGAFQWSA-N 0.000 claims 1
- ZVIACZROZIDZJK-WDEREUQCSA-N 5-[(1s)-1-(2-fluorophenyl)ethyl]sulfanyl-7-[[(2r)-1-hydroxypentan-2-yl]amino]-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CCC)=CC=CC=C1F ZVIACZROZIDZJK-WDEREUQCSA-N 0.000 claims 1
- PRVKPDUKMNAZID-SMDDNHRTSA-N 5-[(1s)-1-(3-fluorophenyl)ethyl]sulfanyl-7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(F)=C1 PRVKPDUKMNAZID-SMDDNHRTSA-N 0.000 claims 1
- HWDVOYPLQLJXFV-TZMCWYRMSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-[(1r)-1-(3-methylsulfonylphenyl)ethyl]sulfanyl-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(S(C)(=O)=O)=C1 HWDVOYPLQLJXFV-TZMCWYRMSA-N 0.000 claims 1
- IAGWEZFSRRPOSS-TZMCWYRMSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-[(1r)-1-phenylethyl]sulfanyl-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC=C1 IAGWEZFSRRPOSS-TZMCWYRMSA-N 0.000 claims 1
- HWDVOYPLQLJXFV-GXTWGEPZSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-[(1s)-1-(3-methylsulfonylphenyl)ethyl]sulfanyl-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(S(C)(=O)=O)=C1 HWDVOYPLQLJXFV-GXTWGEPZSA-N 0.000 claims 1
- IAGWEZFSRRPOSS-GXTWGEPZSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-[(1s)-1-phenylethyl]sulfanyl-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC=C1 IAGWEZFSRRPOSS-GXTWGEPZSA-N 0.000 claims 1
- HWDVOYPLQLJXFV-TYZXPVIJSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-[1-(3-methylsulfonylphenyl)ethylsulfanyl]-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound N=1C=2NC(=O)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC(S(C)(=O)=O)=C1 HWDVOYPLQLJXFV-TYZXPVIJSA-N 0.000 claims 1
- QEGZCVZSDLFVEI-WCQYABFASA-N 7-[[(2r)-1-hydroxypentan-2-yl]amino]-5-[(1s)-1-(3-methylsulfonylphenyl)ethyl]sulfanyl-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CCC)=CC=CC(S(C)(=O)=O)=C1 QEGZCVZSDLFVEI-WCQYABFASA-N 0.000 claims 1
- PXNWVUZRDQBWJQ-WCQYABFASA-N 7-[[(2r)-1-hydroxypentan-2-yl]amino]-5-[(1s)-1-phenylethyl]sulfanyl-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@H](C)SC=2N=C(C=3SC(=O)NC=3N=2)N[C@@H](CO)CCC)=CC=CC=C1 PXNWVUZRDQBWJQ-WCQYABFASA-N 0.000 claims 1
- LADKJDZUKIBRHC-WDEREUQCSA-N 7-[[(2r)-4-fluoro-1-hydroxy-4-methylpentan-2-yl]amino]-5-[(1s)-1-(2-fluorophenyl)ethyl]sulfanyl-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1([C@@H](SC=2N=C3NC(=O)SC3=C(N[C@@H](CO)CC(C)(C)F)N=2)C)=CC=CC=C1F LADKJDZUKIBRHC-WDEREUQCSA-N 0.000 claims 1
- 108010024114 Complement 3b Receptors Proteins 0.000 claims 1
- 102000015612 Complement 3b Receptors Human genes 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0500768 | 2005-04-06 | ||
| PCT/SE2006/000398 WO2006107257A1 (en) | 2005-04-06 | 2006-04-03 | Novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3h)-one derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008535834A JP2008535834A (ja) | 2008-09-04 |
| JP2008535834A5 true JP2008535834A5 (https=) | 2009-06-04 |
Family
ID=37073738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008505261A Pending JP2008535834A (ja) | 2005-04-06 | 2006-04-03 | 新規な５，７−二置換された［１，３］チアゾロ［４，５−ｄ］ピリミジン−２（３ｈ）−オン誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8088780B2 (https=) |
| EP (1) | EP1869055A1 (https=) |
| JP (1) | JP2008535834A (https=) |
| KR (1) | KR20080004484A (https=) |
| CN (1) | CN101193898B (https=) |
| AR (1) | AR053347A1 (https=) |
| AU (1) | AU2006231835B8 (https=) |
| BR (1) | BRPI0609736A2 (https=) |
| CA (1) | CA2604016A1 (https=) |
| IL (1) | IL185913A0 (https=) |
| MX (1) | MX2007012067A (https=) |
| NO (1) | NO20075610L (https=) |
| NZ (1) | NZ561462A (https=) |
| RU (1) | RU2411245C9 (https=) |
| TW (1) | TW200720279A (https=) |
| UY (1) | UY29451A1 (https=) |
| WO (1) | WO2006107257A1 (https=) |
| ZA (1) | ZA200708182B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1806145B1 (en) | 2004-10-29 | 2017-08-16 | Eisai R&D Management Co., Ltd. | Remedy for inflammatory diseases |
| UA90707C2 (en) * | 2005-04-06 | 2010-05-25 | Астразенека Аб | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
| TW200820973A (en) * | 2006-09-29 | 2008-05-16 | Astrazeneca Ab | Novel compounds 480 |
| WO2009109613A2 (en) | 2008-03-07 | 2009-09-11 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1, cx3cr1 and p40 |
| EP2262777B8 (en) | 2008-03-07 | 2016-05-04 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A. | 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1 and cx3cr1 |
| HRP20191953T8 (hr) | 2008-03-07 | 2021-06-25 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | DERIVATI 1-BENZIL-3-HIDROKSIMETILINDAZOLA I NJIHOVA UPORABA U LIJEČENJU BOLESTI KOJE SE BAZIRAJU NA EKSPRESIJI MCP-1, CX3CR1 i P40 |
| AR071036A1 (es) * | 2008-03-26 | 2010-05-19 | Astrazeneca Ab | Derivados 5, 7-disustituidos de [1, 3]tiazolo[4, 5-d]pirimidin-2 (3h)-ona, una composicion farmaceutica que los comprende y su uso en el tratamiento de enfermedades mediadas por el receptor cx3cr1. |
| EP2432776B1 (en) | 2009-05-21 | 2019-09-11 | Universite Laval | Methyl sulfanyl pyrimidines useful as antiinflammatories, analgesics, and antiepileptics |
| JO3437B1 (ar) | 2009-10-30 | 2019-10-20 | Esai R & D Man Co Ltd | أجسام مضادة محسنة مضادة للفراكتالكين البشري واستخداماتها |
| US8476301B2 (en) | 2011-09-13 | 2013-07-02 | Eisai R&D Management Co., Ltd. | Pyrrolidin-3-ylacetic acid derivative |
| TWI543975B (zh) * | 2011-09-13 | 2016-08-01 | Eisai R&D Man Co Ltd | Pyrrolidin-3-yl acetic acid derivatives |
| US9550732B2 (en) | 2013-03-12 | 2017-01-24 | Eisai R&D Management Co., Ltd. | Salt of pyrrolidin-3-yl acetic acid derivative and crystals thereof |
| WO2014142086A1 (ja) * | 2013-03-13 | 2014-09-18 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピロリジン－３－イル酢酸誘導体およびピペリジン－３－イル酢酸誘導体 |
| CN107743491B (zh) * | 2015-05-08 | 2020-08-21 | 豪夫迈·罗氏有限公司 | 用于治疗和预防病毒感染的新的氧硫杂环戊烷甲酸及其衍生物 |
| GB201811169D0 (en) * | 2018-07-06 | 2018-08-29 | Kancera Ab | New compounds |
| JP2025537492A (ja) | 2022-10-19 | 2025-11-18 | アストラゼネカ・アクチエボラーグ | ＣＸｓｕｂ３ＣＲ１のモジュレーターとしての２，４，６－三置換１，３，５－トリアジン |
| WO2025219939A1 (en) | 2024-04-17 | 2025-10-23 | Astrazeneca Ab | Salts and polymorphs of cx3cr1 modulators |
| WO2025219950A1 (en) | 2024-04-18 | 2025-10-23 | Astrazeneca Ab | Small molecule cx3cr1 modulators |
| WO2025219947A1 (en) | 2024-04-18 | 2025-10-23 | Astrazeneca Ab | Thio-substituted 1,3,5-triazine cx3cr1 modulators |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543978A (https=) * | 1955-01-03 | |||
| US4698327A (en) * | 1985-04-25 | 1987-10-06 | Eli Lilly And Company | Novel glycopeptide derivatives |
| US4639433A (en) * | 1985-08-14 | 1987-01-27 | Eli Lilly And Company | Glycopeptide derivatives |
| US4643987A (en) * | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| ZA909847B (en) * | 1989-12-13 | 1992-08-26 | Lilly Co Eli | Glycopeptide derivatives |
| US5202328A (en) * | 1991-03-06 | 1993-04-13 | Merck & Co., Inc. | Substituted fused pyrimidinones |
| US5840684A (en) * | 1994-01-28 | 1998-11-24 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| ATE214704T1 (de) * | 1997-07-18 | 2002-04-15 | Hoffmann La Roche | 5h-thiazolo(3,2-a)pyrimidinderivate |
| JP2002510695A (ja) * | 1998-04-03 | 2002-04-09 | デュポン ファーマシューティカルズ カンパニー | 副腎皮質刺激ホルモン放出因子（ＣＲＦ）拮抗剤としてのチアゾロ［４，５−ｄ］ピリミジンおよびピリジン |
| WO1999056760A1 (en) | 1998-05-01 | 1999-11-11 | Eli Lilly And Company | N1-modified glycopeptides |
| SE9802729D0 (sv) * | 1998-08-13 | 1998-08-13 | Astra Pharma Prod | Novel Compounds |
| SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| GB2359081A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active thiazolopyrimidines |
| JP2003522191A (ja) * | 2000-02-11 | 2003-07-22 | アストラゼネカ・アクチエボラーグ | ケモカイン受容体活性のモジュレーターとしてのピリミジン化合物およびそれらの使用 |
| GB2359551A (en) | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| SE0004110L (sv) * | 2000-11-10 | 2002-05-11 | Forsheda Ab | Tätningsring |
| SE0101082D0 (sv) * | 2001-03-27 | 2001-03-27 | Astrazeneca Ab | Novel use |
| SE0101322D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
| GB0221828D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0221829D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| EP1675862A1 (en) * | 2003-10-07 | 2006-07-05 | AstraZeneca AB | New 2-substituted, 4-amino-thiazolo 4,5-d pyrimidines, useful as chemokine receptor antagonists, esp. cx3cr1 |
| UA90707C2 (en) | 2005-04-06 | 2010-05-25 | Астразенека Аб | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
-
2006
- 2006-03-27 AR ARP060101170A patent/AR053347A1/es not_active Application Discontinuation
- 2006-03-28 TW TW095110787A patent/TW200720279A/zh unknown
- 2006-04-03 AU AU2006231835A patent/AU2006231835B8/en not_active Ceased
- 2006-04-03 CA CA002604016A patent/CA2604016A1/en not_active Abandoned
- 2006-04-03 RU RU2007140552/04A patent/RU2411245C9/ru not_active IP Right Cessation
- 2006-04-03 US US11/910,781 patent/US8088780B2/en not_active Expired - Fee Related
- 2006-04-03 EP EP06717077A patent/EP1869055A1/en not_active Withdrawn
- 2006-04-03 CN CN2006800200730A patent/CN101193898B/zh not_active Expired - Fee Related
- 2006-04-03 BR BRPI0609736-7A patent/BRPI0609736A2/pt not_active Application Discontinuation
- 2006-04-03 JP JP2008505261A patent/JP2008535834A/ja active Pending
- 2006-04-03 WO PCT/SE2006/000398 patent/WO2006107257A1/en not_active Ceased
- 2006-04-03 MX MX2007012067A patent/MX2007012067A/es not_active Application Discontinuation
- 2006-04-03 KR KR1020077022814A patent/KR20080004484A/ko not_active Withdrawn
- 2006-04-03 NZ NZ561462A patent/NZ561462A/en not_active IP Right Cessation
- 2006-04-04 UY UY29451A patent/UY29451A1/es unknown
-
2007
- 2007-09-11 IL IL185913A patent/IL185913A0/en unknown
- 2007-09-25 ZA ZA200708182A patent/ZA200708182B/xx unknown
- 2007-11-05 NO NO20075610A patent/NO20075610L/no not_active Application Discontinuation
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