GB2359081A - Pharmaceutically active thiazolopyrimidines - Google Patents
Pharmaceutically active thiazolopyrimidines Download PDFInfo
- Publication number
- GB2359081A GB2359081A GB0003025A GB0003025A GB2359081A GB 2359081 A GB2359081 A GB 2359081A GB 0003025 A GB0003025 A GB 0003025A GB 0003025 A GB0003025 A GB 0003025A GB 2359081 A GB2359081 A GB 2359081A
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- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- compound
- optionally substituted
- independently selected
- 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.)
- Withdrawn
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- 150000008634 thiazolopyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000012453 solvate Substances 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 102000019034 Chemokines Human genes 0.000 claims description 9
- 108010012236 Chemokines Proteins 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- OILVGVUQLKTWFG-UHFFFAOYSA-N 2-[[2-amino-5-(1h-benzimidazol-2-ylmethylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methylpropan-1-ol Chemical compound C1=CC=C2NC(CSC=3N=C(C=4SC(N)=NC=4N=3)NC(C)(CO)C)=NC2=C1 OILVGVUQLKTWFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- DNIDZDOUIBMVCS-UHFFFAOYSA-N 2-[[2-amino-5-(1-thiophen-2-ylethylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methylpropan-1-ol Chemical compound N=1C(NC(C)(C)CO)=C2SC(N)=NC2=NC=1SC(C)C1=CC=CS1 DNIDZDOUIBMVCS-UHFFFAOYSA-N 0.000 claims description 3
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- NJGJIFFXQVCHPF-ZCFIWIBFSA-N (2r)-2-[[2-amino-5-[(2-methyl-1,3-thiazol-4-yl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]propan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(N[C@@H](CO)C)=NC=1SCC1=CSC(C)=N1 NJGJIFFXQVCHPF-ZCFIWIBFSA-N 0.000 claims description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 230000000694 effects Effects 0.000 abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
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- -1 thiazolopyrimidine compounds Chemical class 0.000 description 5
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
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- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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- 229960000583 acetic acid Drugs 0.000 description 4
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 4
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Landscapes
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0003025A GB2359081A (en) | 2000-02-11 | 2000-02-11 | Pharmaceutically active thiazolopyrimidines |
| JP2001558056A JP2003522192A (ja) | 2000-02-11 | 2001-02-07 | ケモカインレセプター活性のモジュレーターとしてのチアゾロピリミジンおよびそれらの使用 |
| EP01906447A EP1257556B1 (en) | 2000-02-11 | 2001-02-07 | Thiazolopyrimidines and their use as modulators of chemokine receptor activity |
| AT01906447T ATE269340T1 (de) | 2000-02-11 | 2001-02-07 | Thiazolopyrimidine und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
| US10/203,580 US6958343B2 (en) | 2000-02-11 | 2001-02-07 | Thiazolopyrimidines and their use as modulators of chemokine receptor activity |
| AU2001234273A AU2001234273A1 (en) | 2000-02-11 | 2001-02-07 | Thiazolopyrimidines and their use as modulators of chemokine receptor activity |
| PCT/SE2001/000247 WO2001058907A1 (en) | 2000-02-11 | 2001-02-07 | Thiazolopyrimidines and their use as modulators of chemokine receptor activity |
| DE60103856T DE60103856T2 (de) | 2000-02-11 | 2001-02-07 | Thiazolopyrimidine und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0003025A GB2359081A (en) | 2000-02-11 | 2000-02-11 | Pharmaceutically active thiazolopyrimidines |
Publications (2)
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|---|---|
| GB0003025D0 GB0003025D0 (en) | 2000-03-29 |
| GB2359081A true GB2359081A (en) | 2001-08-15 |
Family
ID=9885290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0003025A Withdrawn GB2359081A (en) | 2000-02-11 | 2000-02-11 | Pharmaceutically active thiazolopyrimidines |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6958343B2 (enExample) |
| EP (1) | EP1257556B1 (enExample) |
| JP (1) | JP2003522192A (enExample) |
| AT (1) | ATE269340T1 (enExample) |
| AU (1) | AU2001234273A1 (enExample) |
| DE (1) | DE60103856T2 (enExample) |
| GB (1) | GB2359081A (enExample) |
| WO (1) | WO2001058907A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9903544D0 (sv) * | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| DE60101372T2 (de) * | 2000-02-11 | 2004-10-14 | Astrazeneca Ab | Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
| GB2359078A (en) * | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| GB2359551A (en) * | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| SE0003828D0 (sv) | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Novel compounds |
| SE0101082D0 (sv) * | 2001-03-27 | 2001-03-27 | Astrazeneca Ab | Novel use |
| SE0101322D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
| SE0102716D0 (sv) * | 2001-08-14 | 2001-08-14 | Astrazeneca Ab | Novel compounds |
| AU2003246972A1 (en) | 2002-08-06 | 2004-02-23 | Astrazeneca Ab | Condensed pyridines and pyrimidines with tie2 (tek) activity |
| GB0221829D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0221828D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0328243D0 (en) * | 2003-12-05 | 2004-01-07 | Astrazeneca Ab | Methods |
| 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 |
| 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 |
| RU2437889C2 (ru) * | 2006-09-29 | 2011-12-27 | Астразенека Аб | НОВЫЕ 5,7-ДИЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ [1,3]ТИАЗОЛО[4,5-d]ПИРИМИДИН-2-(3Н)-АМИНА И ИХ ПРИМЕНЕНИЕ В ТЕРАПИИ |
| AR076601A1 (es) | 2009-05-21 | 2011-06-22 | Chlorion Pharma Inc | Pirimidinas como agentes terapeuticos |
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| WO2000009511A1 (en) * | 1998-08-13 | 2000-02-24 | Astrazeneca Ab | Novel thiazolopyrimidine compounds |
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| US4120521A (en) | 1975-08-28 | 1978-10-17 | Rieber & Son Plastic-Industri A/S | Combined mould element and sealing ring |
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| FR2547888B1 (fr) | 1983-06-22 | 1985-12-13 | Sabla Sa | Bague d'etancheite a implants pour tuyaux a emboitement |
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| DE4119767A1 (de) | 1991-06-15 | 1992-12-17 | Dresden Arzneimittel | Verfahren zur herstellung von (pyrimid-2-yl-thio- bzw. seleno)-essigsaeurederivaten |
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| US5521197A (en) | 1994-12-01 | 1996-05-28 | Eli Lilly And Company | 3-<1-alkylenearyl>-4-<1,2,3,6-tetrahydropyridinyl>-and 3-<1-alkylenearyl>-4-piperidinyl-1h-indoles: new 5-HT1F agonists |
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| AR013669A1 (es) | 1997-10-07 | 2001-01-10 | Smithkline Beecham Corp | Compuestos y metodos |
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| 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 |
| MA26659A1 (fr) | 1998-08-06 | 2004-12-20 | Pfizer | Dérivés de benzimidazole nouveaux, compositions pharmaceutiques les contenant et procédé pour leur préparation. |
| US5988695A (en) | 1998-08-26 | 1999-11-23 | S&B Technical Products, Inc. | Pipe gasket with embedded ring |
| PE20001420A1 (es) | 1998-12-23 | 2000-12-18 | Pfizer | Moduladores de ccr5 |
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| JP2002536320A (ja) | 1999-02-02 | 2002-10-29 | カー・イュー・ルーベン・リサーチ・アンド・ディベロップメント | プテリジン誘導体の免疫抑制作用 |
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| ATE306488T1 (de) | 2000-01-05 | 2005-10-15 | Pfizer | Benzimidazol-verbindungen zur verwendung als orl1-rezeptor-antagonisten |
| DE60101372T2 (de) | 2000-02-11 | 2004-10-14 | Astrazeneca Ab | Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
| GB2359079A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| GB2359078A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| GB2359551A (en) | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
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| SE0102716D0 (sv) | 2001-08-14 | 2001-08-14 | Astrazeneca Ab | Novel compounds |
-
2000
- 2000-02-11 GB GB0003025A patent/GB2359081A/en not_active Withdrawn
-
2001
- 2001-02-07 EP EP01906447A patent/EP1257556B1/en not_active Expired - Lifetime
- 2001-02-07 US US10/203,580 patent/US6958343B2/en not_active Expired - Fee Related
- 2001-02-07 JP JP2001558056A patent/JP2003522192A/ja active Pending
- 2001-02-07 WO PCT/SE2001/000247 patent/WO2001058907A1/en not_active Ceased
- 2001-02-07 AT AT01906447T patent/ATE269340T1/de not_active IP Right Cessation
- 2001-02-07 AU AU2001234273A patent/AU2001234273A1/en not_active Abandoned
- 2001-02-07 DE DE60103856T patent/DE60103856T2/de not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB713652A (en) * | 1951-06-04 | 1954-08-18 | Wellcome Found | Improvements in or relating to heterocyclic compounds and their manufacture |
| WO2000009511A1 (en) * | 1998-08-13 | 2000-02-24 | Astrazeneca Ab | Novel thiazolopyrimidine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60103856D1 (de) | 2004-07-22 |
| EP1257556A1 (en) | 2002-11-20 |
| US20030032642A1 (en) | 2003-02-13 |
| AU2001234273A1 (en) | 2001-08-20 |
| US6958343B2 (en) | 2005-10-25 |
| EP1257556B1 (en) | 2004-06-16 |
| DE60103856T2 (de) | 2005-07-14 |
| GB0003025D0 (en) | 2000-03-29 |
| ATE269340T1 (de) | 2004-07-15 |
| WO2001058907A1 (en) | 2001-08-16 |
| JP2003522192A (ja) | 2003-07-22 |
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Legal Events
| Date | Code | Title | Description |
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| COOA | Change in applicant's name or ownership of the application | ||
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |