CA2604016A1 - Novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3h)-one derivatives - Google Patents
Novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3h)-one derivatives Download PDFInfo
- Publication number
- CA2604016A1 CA2604016A1 CA002604016A CA2604016A CA2604016A1 CA 2604016 A1 CA2604016 A1 CA 2604016A1 CA 002604016 A CA002604016 A CA 002604016A CA 2604016 A CA2604016 A CA 2604016A CA 2604016 A1 CA2604016 A1 CA 2604016A1
- Authority
- CA
- Canada
- Prior art keywords
- thiazolo
- pyrimidin
- amino
- thio
- formula
- 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.)
- Abandoned
Links
- -1 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3h)-one Chemical class 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 183
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 238000011321 prophylaxis Methods 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 230000003143 atherosclerotic effect Effects 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 108090000835 CX3C Chemokine Receptor 1 Proteins 0.000 claims abstract description 12
- 102100039196 CX3C chemokine receptor 1 Human genes 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 10
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- 208000016192 Demyelinating disease Diseases 0.000 claims abstract description 8
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- 208000006673 asthma Diseases 0.000 claims abstract description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
- 208000030613 peripheral artery disease Diseases 0.000 claims abstract description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 7
- 208000019693 Lung disease Diseases 0.000 claims abstract description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 15
- 201000001320 Atherosclerosis Diseases 0.000 claims description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
- 230000003902 lesion Effects 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 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 description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 230000008485 antagonism Effects 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- 230000009286 beneficial effect Effects 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- 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 description 4
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 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
- IAGWEZFSRRPOSS-TYZXPVIJSA-N 7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-5-(1-phenylethylsulfanyl)-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=C1 IAGWEZFSRRPOSS-TYZXPVIJSA-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-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
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0500768-7 | 2005-04-06 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2604016A1 true CA2604016A1 (en) | 2006-10-12 |
Family
ID=37073738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002604016A Abandoned CA2604016A1 (en) | 2005-04-06 | 2006-04-03 | Novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3h)-one derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8088780B2 (enExample) |
| EP (1) | EP1869055A1 (enExample) |
| JP (1) | JP2008535834A (enExample) |
| KR (1) | KR20080004484A (enExample) |
| CN (1) | CN101193898B (enExample) |
| AR (1) | AR053347A1 (enExample) |
| AU (1) | AU2006231835B8 (enExample) |
| BR (1) | BRPI0609736A2 (enExample) |
| CA (1) | CA2604016A1 (enExample) |
| IL (1) | IL185913A0 (enExample) |
| MX (1) | MX2007012067A (enExample) |
| NO (1) | NO20075610L (enExample) |
| NZ (1) | NZ561462A (enExample) |
| RU (1) | RU2411245C9 (enExample) |
| TW (1) | TW200720279A (enExample) |
| UY (1) | UY29451A1 (enExample) |
| WO (1) | WO2006107257A1 (enExample) |
| ZA (1) | ZA200708182B (enExample) |
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 |
| EA018185B1 (ru) | 2008-03-07 | 2013-06-28 | Ацьенде Кимике Рьюните Анджелини Франческо A.К.P.A.Ф. С.П.А. | Новые производные 1-бензил-3-гидроксиметилиндазола и их применение при лечении заболеваний, обусловленных экспрессией mcp-1 или cx3cr1 |
| MX2010009625A (es) | 2008-03-07 | 2010-09-28 | Acraf | Derivados de 1-bencil-3-hidroximetilindazol y uso de los mismos en el tratamiento de enfermedades basadas en la expresion de mcp-1, cx3cr1 y p40. |
| DK2254869T3 (en) | 2008-03-07 | 2017-09-04 | Acraf | 1-BENZYL-3-HYDROXYMETHYL INDAZOLE DERIVATIVES AND USE THEREOF IN THE TREATMENT OF DISEASES BASED ON THE EXPRESSION OF CX3CR1 AND 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. |
| CA2762680C (en) | 2009-05-21 | 2018-04-17 | Chlorion Pharma, Inc. | Methyl sulfanyl pyrmidmes 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 |
| TWI543975B (zh) * | 2011-09-13 | 2016-08-01 | Eisai R&D Man Co Ltd | Pyrrolidin-3-yl acetic acid derivatives |
| US8476301B2 (en) | 2011-09-13 | 2013-07-02 | Eisai R&D Management Co., Ltd. | Pyrrolidin-3-ylacetic acid derivative |
| WO2014142056A1 (ja) * | 2013-03-12 | 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－イル酢酸誘導体の塩およびその結晶 |
| 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 |
| EP3294745B1 (en) * | 2015-05-08 | 2020-01-01 | H. Hoffnabb-La Roche Ag | Novel oxathiolane carboxylic acids and derivatives for the treatment and prophylaxis of virus infection |
| GB201811169D0 (en) * | 2018-07-06 | 2018-08-29 | Kancera Ab | New compounds |
| PE20251587A1 (es) | 2022-10-19 | 2025-06-16 | Astrazeneca Ab | 1,3,5-triazinas 2,4,6-trisustituidas como modulares de cx3cr1 |
| WO2025219939A1 (en) | 2024-04-17 | 2025-10-23 | Astrazeneca Ab | Salts and polymorphs of cx3cr1 modulators |
| WO2025219947A1 (en) | 2024-04-18 | 2025-10-23 | Astrazeneca Ab | Thio-substituted 1,3,5-triazine cx3cr1 modulators |
| WO2025219950A1 (en) | 2024-04-18 | 2025-10-23 | Astrazeneca Ab | Small molecule cx3cr1 modulators |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543978A (enExample) | 1955-01-03 | |||
| US4698327A (en) | 1985-04-25 | 1987-10-06 | Eli Lilly And Company | Novel glycopeptide derivatives |
| US4643987A (en) | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| US4639433A (en) | 1985-08-14 | 1987-01-27 | Eli Lilly And Company | Glycopeptide derivatives |
| 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 |
| DK0891978T3 (da) * | 1997-07-18 | 2002-07-01 | Hoffmann La Roche | 5H-Thiazol(3,2-a)pyrimidinderivativer |
| WO1999051608A1 (en) | 1998-04-03 | 1999-10-14 | Du Pont Pharmaceuticals Company | THIAZOLO[4,5-d]PYRIMIDINES AND PYRIDINES AS CORTICOTROPIN RELEASING FACTOR (CRF) ANTAGONISTS |
| CA2330619A1 (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 |
| DE60101372T2 (de) * | 2000-02-11 | 2004-10-14 | Astrazeneca Ab | Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
| 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 |
| WO2005033115A1 (en) * | 2003-10-07 | 2005-04-14 | 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 US US11/910,781 patent/US8088780B2/en not_active Expired - Fee Related
- 2006-04-03 WO PCT/SE2006/000398 patent/WO2006107257A1/en not_active Ceased
- 2006-04-03 JP JP2008505261A patent/JP2008535834A/ja active Pending
- 2006-04-03 CA CA002604016A patent/CA2604016A1/en not_active Abandoned
- 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 KR KR1020077022814A patent/KR20080004484A/ko not_active Withdrawn
- 2006-04-03 AU AU2006231835A patent/AU2006231835B8/en not_active Ceased
- 2006-04-03 EP EP06717077A patent/EP1869055A1/en not_active Withdrawn
- 2006-04-03 MX MX2007012067A patent/MX2007012067A/es not_active Application Discontinuation
- 2006-04-03 NZ NZ561462A patent/NZ561462A/en not_active IP Right Cessation
- 2006-04-03 RU RU2007140552/04A patent/RU2411245C9/ru 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
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008535834A (ja) | 2008-09-04 |
| AR053347A1 (es) | 2007-05-02 |
| ZA200708182B (en) | 2008-11-26 |
| AU2006231835A1 (en) | 2006-10-12 |
| IL185913A0 (en) | 2008-01-06 |
| UY29451A1 (es) | 2006-11-30 |
| NZ561462A (en) | 2010-12-24 |
| CN101193898A (zh) | 2008-06-04 |
| WO2006107257A1 (en) | 2006-10-12 |
| RU2411245C9 (ru) | 2011-05-27 |
| AU2006231835B2 (en) | 2010-09-30 |
| RU2411245C2 (ru) | 2011-02-10 |
| US8088780B2 (en) | 2012-01-03 |
| MX2007012067A (es) | 2007-12-04 |
| RU2007140552A (ru) | 2009-05-20 |
| EP1869055A1 (en) | 2007-12-26 |
| KR20080004484A (ko) | 2008-01-09 |
| NO20075610L (no) | 2008-01-07 |
| US20090124637A1 (en) | 2009-05-14 |
| BRPI0609736A2 (pt) | 2011-10-18 |
| CN101193898B (zh) | 2010-12-01 |
| TW200720279A (en) | 2007-06-01 |
| AU2006231835B8 (en) | 2010-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140403 |