JP5165553B2 - 新規な５−置換された７−アミノ［１，３］チアゾロ［４，５−ｄ］ピリミジン誘導体 - Google Patents
新規な５−置換された７−アミノ［１，３］チアゾロ［４，５−ｄ］ピリミジン誘導体 Download PDFInfo
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- JP5165553B2 JP5165553B2 JP2008505262A JP2008505262A JP5165553B2 JP 5165553 B2 JP5165553 B2 JP 5165553B2 JP 2008505262 A JP2008505262 A JP 2008505262A JP 2008505262 A JP2008505262 A JP 2008505262A JP 5165553 B2 JP5165553 B2 JP 5165553B2
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- Prior art keywords
- amino
- thiazolo
- thio
- pyrimidin
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- -1 5-substituted 7-amino [1,3] thiazolo [4,5-D] pyrimidine Chemical class 0.000 title description 12
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 130
- 150000003839 salts Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- ZMQSLMZOWVGBSM-TYZXPVIJSA-N (2r)-2-[[2-amino-5-(1-phenylethylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(N[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC=C1 ZMQSLMZOWVGBSM-TYZXPVIJSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- PXGSOIQQPQSTRO-SWLSCSKDSA-N 3-[(1s)-1-[[2-amino-7-[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]sulfanyl]ethyl]benzonitrile Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(C#N)=C1 PXGSOIQQPQSTRO-SWLSCSKDSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
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- PDKBAEAFZLXVQK-AWKYBWMHSA-N (2r)-2-[[2-amino-5-(1-phenylethylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]-methylamino]-4-methylpentan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(N(C)[C@@H](CO)CC(C)C)=NC=1SC(C)C1=CC=CC=C1 PDKBAEAFZLXVQK-AWKYBWMHSA-N 0.000 claims description 4
- ZJTOCCMPRIUOGK-GXTWGEPZSA-N (2r)-2-[[2-amino-5-[(1s)-1-(3-methylsulfonylphenyl)ethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC(S(C)(=O)=O)=C1 ZJTOCCMPRIUOGK-GXTWGEPZSA-N 0.000 claims description 4
- ZMQSLMZOWVGBSM-GXTWGEPZSA-N (2r)-2-[[2-amino-5-[(1s)-1-phenylethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC=C1 ZMQSLMZOWVGBSM-GXTWGEPZSA-N 0.000 claims description 4
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- ZMMDDWBVYKJHNY-TYZXPVIJSA-N (2r)-2-[[2-amino-5-[1-(3-methoxyphenyl)ethylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound COC1=CC=CC(C(C)SC=2N=C3N=C(N)SC3=C(N[C@@H](CO)CC(C)C)N=2)=C1 ZMMDDWBVYKJHNY-TYZXPVIJSA-N 0.000 claims description 4
- PNKYTKPWPKRAKI-SMDDNHRTSA-N 3-[(1s)-1-[[2-amino-7-[[(2r)-1-hydroxypentan-2-yl]amino]-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]sulfanyl]ethyl]benzonitrile Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CCC)=CC=CC(C#N)=C1 PNKYTKPWPKRAKI-SMDDNHRTSA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0500767 | 2005-04-06 | ||
| SE0500767-9 | 2005-04-06 | ||
| PCT/SE2006/000399 WO2006107258A1 (en) | 2005-04-06 | 2006-04-03 | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008535835A JP2008535835A (ja) | 2008-09-04 |
| JP2008535835A5 JP2008535835A5 (cg-RX-API-DMAC7.html) | 2009-06-04 |
| JP5165553B2 true JP5165553B2 (ja) | 2013-03-21 |
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| WO2006046739A1 (ja) | 2004-10-29 | 2006-05-04 | Eisai R & D Management Co., Ltd. | 炎症性疾患治療剤 |
| AR053347A1 (es) | 2005-04-06 | 2007-05-02 | Astrazeneca Ab | Derivados de [1,3]tiazolo[4,5-d]pirimidin-2(3h)-ona 5,7-sustituidos |
| TW200820973A (en) | 2006-09-29 | 2008-05-16 | Astrazeneca Ab | Novel compounds 480 |
| EP2069365A4 (en) * | 2006-09-29 | 2011-11-02 | Astrazeneca Ab | NOVEL [1, 3] THIAZOLO [4,5-D] PYRIMIDIN-2 (3H) -AMINE 5,7-DISUBSTITUTED DERIVATIVES AND THEIR USE IN THERAPY |
| HRP20160457T1 (hr) | 2008-03-07 | 2016-05-20 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Derivati 1-benzil-3-hidroksimetilindazola i njihova uporaba u liječenju bolesti baziranih na ekspresiji mcp-1 i cx3cr1 |
| CA2714436C (en) | 2008-03-07 | 2017-06-27 | 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 |
| US8835481B2 (en) | 2008-03-07 | 2014-09-16 | 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, CX3CR1 and P40 |
| US9040538B2 (en) | 2009-05-21 | 2015-05-26 | Universite Laval | Pyrimidines as novel therapeutic agents |
| JO3437B1 (ar) | 2009-10-30 | 2019-10-20 | Esai R & D Man Co Ltd | أجسام مضادة محسنة مضادة للفراكتالكين البشري واستخداماتها |
| JP6076913B2 (ja) | 2010-12-07 | 2017-02-08 | ドレクセル ユニバーシティ | 癌からの転移を阻害する方法 |
| 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 |
| JP5872105B2 (ja) | 2013-03-12 | 2016-03-01 | 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 |
| EP3049086A4 (en) | 2013-09-27 | 2017-02-22 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| US20180222922A1 (en) * | 2015-06-08 | 2018-08-09 | The Johns Hopkins University | Radiofluorinated 7-amino-5-thio-thiazolo[4,5-d]pyrimidines for imaging fractalkine receptor (cx3cr1) |
| US11267817B2 (en) | 2017-05-02 | 2022-03-08 | Drexel University | Substituted pyrrolo[1,2-a]quinoxalin-4(5H)-ones as CX3CR1 antagonists |
| GB201807898D0 (en) * | 2018-05-15 | 2018-06-27 | Kancera Ab | New processes and products with increased chiral purity |
| GB201811169D0 (en) | 2018-07-06 | 2018-08-29 | Kancera Ab | New compounds |
| GB202006849D0 (en) | 2020-05-08 | 2020-06-24 | Kancera Ab | New use |
| AU2023362450A1 (en) | 2022-10-19 | 2025-05-29 | Astrazeneca Ab | 2,4,6-trisubstituted 1,3,5-triazines as modulators of cx 3 cr1 |
| 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 |
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| BE543978A (cg-RX-API-DMAC7.html) | 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 |
| PT891978E (pt) * | 1997-07-18 | 2002-07-31 | Hoffmann La Roche | Derivados de 5h-tiazolo (3,2-a) pirimidina |
| 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 |
| DE69936052T2 (de) | 1998-05-01 | 2008-01-17 | Eli Lilly And Co., Indianapolis | N1 modifizierte glycopeptide |
| 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 |
| WO2001058906A1 (en) * | 2000-02-11 | 2001-08-16 | Astrazeneca Ab | Pyrimidine compounds and their use as modulators of chemokine receptor activity |
| GB2359551A (en) | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| RU2340611C2 (ru) * | 2000-09-15 | 2008-12-10 | Вертекс Фармасьютикалз Инкорпорейтед | Производные пиразола, используемые в качестве ингибиторов протеинкиназы |
| SE0004110L (sv) | 2000-11-10 | 2002-05-11 | Forsheda Ab | Tätningsring |
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| GB0221829D0 (en) | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| EP3597262B1 (en) * | 2002-12-20 | 2023-12-27 | Xeris Pharmaceuticals, Inc. | Formulation for intracutaneous injection |
| US20070142386A1 (en) | 2003-10-07 | 2007-06-21 | Astrazeneca | New 2-substituted, 4-amino-thiazolo[4,5-d] pyrimidines, useful as chemokine receptor antagonists, esp. cx3cr1 |
| US20090239882A1 (en) * | 2004-12-17 | 2009-09-24 | Astrazeneca Ab | Thiazolopyramidine Compounds for the Modulation of Chemokine Receptor Activity |
| AR053347A1 (es) * | 2005-04-06 | 2007-05-02 | Astrazeneca Ab | Derivados de [1,3]tiazolo[4,5-d]pirimidin-2(3h)-ona 5,7-sustituidos |
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