AU777872B2 - Novel thiazolo(4,5-D)pyrimidine compounds - Google Patents
Novel thiazolo(4,5-D)pyrimidine compounds Download PDFInfo
- Publication number
- AU777872B2 AU777872B2 AU73049/00A AU7304900A AU777872B2 AU 777872 B2 AU777872 B2 AU 777872B2 AU 73049/00 A AU73049/00 A AU 73049/00A AU 7304900 A AU7304900 A AU 7304900A AU 777872 B2 AU777872 B2 AU 777872B2
- Authority
- AU
- Australia
- Prior art keywords
- amino
- pyrimidin
- methyl
- thio
- thiazolo
- 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.)
- Ceased
Links
- YWBULOYFCXZCGF-UHFFFAOYSA-N [1,3]thiazolo[4,5-d]pyrimidine Chemical class C1=NC=C2SC=NC2=N1 YWBULOYFCXZCGF-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 137
- -1 thiazolopyrimidine compounds Chemical class 0.000 claims abstract description 111
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000012453 solvate Substances 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 102000019034 Chemokines Human genes 0.000 claims abstract description 14
- 108010012236 Chemokines Proteins 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 8
- 230000001404 mediated effect Effects 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 150
- 150000001875 compounds Chemical class 0.000 claims description 135
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 96
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- 150000003573 thiols Chemical class 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 19
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 15
- 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 13
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 9
- 102000002791 Interleukin-8B Receptors Human genes 0.000 claims description 8
- 108010018951 Interleukin-8B Receptors Proteins 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
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- 108050000299 Chemokine receptor Proteins 0.000 claims description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
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- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
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- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- LOUODJGOYJHXPS-UHFFFAOYSA-N 1h-pyrimidin-2-one;sodium Chemical compound [Na].OC1=NC=CC=N1 LOUODJGOYJHXPS-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- QNKPNNVLROGERL-UHFFFAOYSA-N 2-[(5-benzylsulfanyl-2-bromo-[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-2-methylpropan-1-ol Chemical compound N=1C=2N=C(Br)SC=2C(NC(C)(CO)C)=NC=1SCC1=CC=CC=C1 QNKPNNVLROGERL-UHFFFAOYSA-N 0.000 claims 1
- JZKUVWGFDUVZJW-UHFFFAOYSA-N 2-[[2-bromo-5-[(2,3-difluorophenyl)methylsulfanyl]-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methylpropan-1-ol Chemical compound N=1C=2N=C(Br)SC=2C(NC(C)(CO)C)=NC=1SCC1=CC=CC(F)=C1F JZKUVWGFDUVZJW-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- LTLYZBYGTQOYBR-UHFFFAOYSA-N 5-benzylsulfanyl-7-[(1-hydroxy-2-methylpropan-2-yl)amino]-3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound N=1C=2NC(=O)SC=2C(NC(C)(CO)C)=NC=1SCC1=CC=CC=C1 LTLYZBYGTQOYBR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 182
- 238000004949 mass spectrometry Methods 0.000 description 109
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 67
- 238000005481 NMR spectroscopy Methods 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
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Classifications
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- 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
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9903544 | 1999-10-01 | ||
| SE9903544A SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Novel compounds |
| PCT/GB2000/003692 WO2001025242A1 (en) | 1999-10-01 | 2000-09-26 | Novel thiazolo(4,5-d)pyrimidine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7304900A AU7304900A (en) | 2001-05-10 |
| AU777872B2 true AU777872B2 (en) | 2004-11-04 |
Family
ID=20417218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU73049/00A Ceased AU777872B2 (en) | 1999-10-01 | 2000-09-26 | Novel thiazolo(4,5-D)pyrimidine compounds |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US6790850B1 (enExample) |
| EP (2) | EP1222195B1 (enExample) |
| JP (1) | JP4824889B2 (enExample) |
| KR (1) | KR100765051B1 (enExample) |
| CN (1) | CN1210279C (enExample) |
| AT (2) | ATE384068T1 (enExample) |
| AU (1) | AU777872B2 (enExample) |
| BR (1) | BR0014334A (enExample) |
| CA (1) | CA2385269C (enExample) |
| CZ (1) | CZ20021113A3 (enExample) |
| DE (2) | DE60037836T2 (enExample) |
| DK (1) | DK1222195T3 (enExample) |
| EE (1) | EE05037B1 (enExample) |
| ES (2) | ES2213043T3 (enExample) |
| HU (1) | HUP0204246A3 (enExample) |
| IL (2) | IL148910A0 (enExample) |
| IS (1) | IS2229B (enExample) |
| MX (1) | MXPA02003263A (enExample) |
| NO (1) | NO327706B1 (enExample) |
| NZ (1) | NZ517880A (enExample) |
| PT (1) | PT1222195E (enExample) |
| SE (1) | SE9903544D0 (enExample) |
| TW (1) | TWI260324B (enExample) |
| UA (1) | UA73521C2 (enExample) |
| WO (1) | WO2001025242A1 (enExample) |
| ZA (1) | ZA200202380B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| GB2359078A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| DE60101372T2 (de) * | 2000-02-11 | 2004-10-14 | Astrazeneca Ab | Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
| GB2359081A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active thiazolopyrimidines |
| 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 |
| SE0101322D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
| SE0102716D0 (sv) * | 2001-08-14 | 2001-08-14 | Astrazeneca Ab | Novel compounds |
| JP4467979B2 (ja) | 2001-12-06 | 2010-05-26 | メルク・シャープ・エンド・ドーム・コーポレイション | 有糸分裂キネシン阻害剤 |
| WO2003049527A2 (en) | 2001-12-06 | 2003-06-19 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| GB0217431D0 (en) * | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| AU2003246972A1 (en) | 2002-08-06 | 2004-02-23 | Astrazeneca Ab | Condensed pyridines and pyrimidines with tie2 (tek) activity |
| ES2295685T3 (es) | 2002-08-24 | 2008-04-16 | Astrazeneca Ab | Derivados de pirimidina como moduladores de la actividad del receptor de quimioquinas. |
| GB0221829D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0221828D0 (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 |
| GB0328243D0 (en) * | 2003-12-05 | 2004-01-07 | Astrazeneca Ab | Methods |
| PT1809624E (pt) | 2004-08-28 | 2014-01-14 | Astrazeneca Ab | Derivados de pirimidina sulfonamida como moduladores do recetor de quimiocina |
| JP2008524186A (ja) * | 2004-12-17 | 2008-07-10 | 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調節のためのチアゾロピラミジン化合物 |
| WO2006101439A1 (en) * | 2005-03-23 | 2006-09-28 | Astrazeneca Ab | Screen |
| UA90707C2 (en) * | 2005-04-06 | 2010-05-25 | Астразенека Аб | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
| 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 |
| 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. |
| CN101671336B (zh) | 2009-09-23 | 2013-11-13 | 辽宁利锋科技开发有限公司 | 芳杂环并嘧啶衍生物和类似物及其制备方法和用途 |
| CN101899058B (zh) * | 2010-05-24 | 2012-05-23 | 中国人民解放军第四军医大学 | 一种噻唑并嘧啶化合物及其制备方法和应用 |
| CN105722972A (zh) | 2013-06-18 | 2016-06-29 | 纽约大学 | 参与金黄色葡萄球菌杀白细胞素的细胞毒性的细胞因素：新型治疗靶点 |
| JP6509851B2 (ja) * | 2013-08-02 | 2019-05-08 | シントリックス・バイオシステムズ・インコーポレイテッドＳｙｎｔｒｉｘ Ｂｉｏｓｙｓｔｅｍｓ， Ｉｎｃ． | ２−［５−［ｎ−（４−フルオロフェニル）カルバモイル］ピリミジン−２−イルスルファニルメチル］−４−（トリフルオロメトキシ）フェニル」ボロン酸 |
| US10046002B2 (en) | 2013-08-02 | 2018-08-14 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists |
| US8969365B2 (en) | 2013-08-02 | 2015-03-03 | Syntrix Biosystems, Inc. | Thiopyrimidinecarboxamides as CXCR1/2 modulators |
| US10561676B2 (en) | 2013-08-02 | 2020-02-18 | Syntrix Biosystems Inc. | Method for treating cancer using dual antagonists of CXCR1 and CXCR2 |
| WO2018073248A1 (en) | 2016-10-17 | 2018-04-26 | Icm (Institut Du Cerveau Et De La Moelle Épinière) | Prognosis of demyelinating diseases patients and treatment thereof |
| CN110172067B (zh) * | 2019-04-11 | 2021-06-15 | 河南科技大学第一附属医院 | 一种具有杀菌活性的噻唑类药物分子及其制备方法 |
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| WO2000009511A1 (en) * | 1998-08-13 | 2000-02-24 | Astrazeneca Ab | Novel thiazolopyrimidine compounds |
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| SE0003828D0 (sv) | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Novel compounds |
| SE0004110L (sv) | 2000-11-10 | 2002-05-11 | Forsheda Ab | Tätningsring |
| SE0101322D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
| SE0102716D0 (sv) | 2001-08-14 | 2001-08-14 | 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 |
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-
1999
- 1999-10-01 SE SE9903544A patent/SE9903544D0/xx unknown
-
2000
- 2000-09-26 EE EEP200200174A patent/EE05037B1/xx not_active IP Right Cessation
- 2000-09-26 DE DE60037836T patent/DE60037836T2/de not_active Expired - Lifetime
- 2000-09-26 UA UA2002032035A patent/UA73521C2/uk unknown
- 2000-09-26 WO PCT/GB2000/003692 patent/WO2001025242A1/en not_active Ceased
- 2000-09-26 CZ CZ20021113A patent/CZ20021113A3/cs unknown
- 2000-09-26 DE DE60007768T patent/DE60007768T2/de not_active Expired - Lifetime
- 2000-09-26 PT PT00960891T patent/PT1222195E/pt unknown
- 2000-09-26 EP EP00960891A patent/EP1222195B1/en not_active Expired - Lifetime
- 2000-09-26 NZ NZ517880A patent/NZ517880A/en not_active IP Right Cessation
- 2000-09-26 CN CNB008163189A patent/CN1210279C/zh not_active Expired - Fee Related
- 2000-09-26 AU AU73049/00A patent/AU777872B2/en not_active Ceased
- 2000-09-26 US US10/089,571 patent/US6790850B1/en not_active Expired - Fee Related
- 2000-09-26 AT AT03015019T patent/ATE384068T1/de not_active IP Right Cessation
- 2000-09-26 DK DK00960891T patent/DK1222195T3/da active
- 2000-09-26 JP JP2001528186A patent/JP4824889B2/ja not_active Expired - Fee Related
- 2000-09-26 EP EP03015019A patent/EP1348709B1/en not_active Expired - Lifetime
- 2000-09-26 IL IL14891000A patent/IL148910A0/xx active IP Right Grant
- 2000-09-26 KR KR1020027004180A patent/KR100765051B1/ko not_active Expired - Fee Related
- 2000-09-26 ES ES00960891T patent/ES2213043T3/es not_active Expired - Lifetime
- 2000-09-26 MX MXPA02003263A patent/MXPA02003263A/es active IP Right Grant
- 2000-09-26 AT AT00960891T patent/ATE257838T1/de active
- 2000-09-26 ES ES03015019T patent/ES2298451T3/es not_active Expired - Lifetime
- 2000-09-26 BR BR0014334-0A patent/BR0014334A/pt not_active IP Right Cessation
- 2000-09-26 HU HU0204246A patent/HUP0204246A3/hu unknown
- 2000-09-26 CA CA2385269A patent/CA2385269C/en not_active Expired - Lifetime
- 2000-10-19 TW TW089121952A patent/TWI260324B/zh not_active IP Right Cessation
-
2002
- 2002-03-18 IS IS6306A patent/IS2229B/is unknown
- 2002-03-22 NO NO20021448A patent/NO327706B1/no not_active IP Right Cessation
- 2002-03-25 ZA ZA200202380A patent/ZA200202380B/en unknown
- 2002-03-26 IL IL148910A patent/IL148910A/en not_active IP Right Cessation
-
2004
- 2004-06-09 US US10/863,995 patent/US20040224961A1/en not_active Abandoned
-
2009
- 2009-04-29 US US12/432,224 patent/US8143261B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000009511A1 (en) * | 1998-08-13 | 2000-02-24 | Astrazeneca Ab | Novel thiazolopyrimidine compounds |
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