JP2006515604A5 - - Google Patents
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- Publication number
- JP2006515604A5 JP2006515604A5 JP2006500010A JP2006500010A JP2006515604A5 JP 2006515604 A5 JP2006515604 A5 JP 2006515604A5 JP 2006500010 A JP2006500010 A JP 2006500010A JP 2006500010 A JP2006500010 A JP 2006500010A JP 2006515604 A5 JP2006515604 A5 JP 2006515604A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- methyl
- carbonitrile
- thieno
- methylthieno
- 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
- -1 4- (Diethylamino) -5-methyl-2- (4-nitrophenyl) thieno [2,3-d] pyrimidine-6-carbonitrile 2- (4-chlorophenyl) -4- (diethylamino) -5-methylthieno [ 2,3-d] pyrimidine-6-carbonitrile Chemical compound 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZAQMRTFLKPRAPX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-[2-hydroxyethyl(methyl)amino]-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(N(C)CCO)=C(C(C)=C(S2)C#N)C2=N1 ZAQMRTFLKPRAPX-UHFFFAOYSA-N 0.000 description 1
- BSMFHDOOMKDRBW-UHFFFAOYSA-N 4-(diethylamino)-2-(3,4-dimethoxyphenyl)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1C1=CC=C(OC)C(OC)=C1 BSMFHDOOMKDRBW-UHFFFAOYSA-N 0.000 description 1
- AWXXKHKQDQFYMW-UHFFFAOYSA-N 4-(diethylamino)-5-methyl-2-[4-(trifluoromethyl)phenyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1C1=CC=C(C(F)(F)F)C=C1 AWXXKHKQDQFYMW-UHFFFAOYSA-N 0.000 description 1
- MYJKZQFEQHKVMG-UHFFFAOYSA-N 4-[2-hydroxyethyl(methyl)amino]-2-(4-methoxyphenyl)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NC(N(C)CCO)=C(C(C)=C(S2)C#N)C2=N1 MYJKZQFEQHKVMG-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- YSSCHKVBFGJWPV-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)-4-oxo-3h-thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N1C(=O)C=2C(C)=C(C#N)SC=2N=C1C1=CC=C(C)C=C1 YSSCHKVBFGJWPV-UHFFFAOYSA-N 0.000 description 1
- YXTLFUJDTXUANL-UHFFFAOYSA-N 5-methyl-4-(4-methylpiperazin-1-yl)-2-[4-(trifluoromethyl)phenyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1CN(C)CCN1C1=NC(C=2C=CC(=CC=2)C(F)(F)F)=NC2=C1C(C)=C(C#N)S2 YXTLFUJDTXUANL-UHFFFAOYSA-N 0.000 description 1
- KNVYMJFTTNGDHD-UHFFFAOYSA-N CC1=C(SC=2N=C(N=C(C21)N2CCOCC2)C2=CC=C(C=C2)C)C#N.COC=2C=C(C=CC2OC)C=2N=C(C1=C(N2)SC(=C1C)C#N)N1CCOCC1 Chemical compound CC1=C(SC=2N=C(N=C(C21)N2CCOCC2)C2=CC=C(C=C2)C)C#N.COC=2C=C(C=CC2OC)C=2N=C(C1=C(N2)SC(=C1C)C#N)N1CCOCC1 KNVYMJFTTNGDHD-UHFFFAOYSA-N 0.000 description 1
- IULCNODUMUBMEY-UHFFFAOYSA-N COC1=CC=C(C=C1)C=1N=C(C2=C(N1)SC(=C2C)C#N)N(CC#C)C.ClC2=CC=C(C=C2)C=2N=C(C1=C(N2)SC(=C1C)C#N)N1CCOCC1 Chemical compound COC1=CC=C(C=C1)C=1N=C(C2=C(N1)SC(=C2C)C#N)N(CC#C)C.ClC2=CC=C(C=C2)C=2N=C(C1=C(N2)SC(=C1C)C#N)N1CCOCC1 IULCNODUMUBMEY-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- CTHOBBRGWQVVGK-UHFFFAOYSA-N ethyl 2-amino-5-cyano-4-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C#N)=C1C CTHOBBRGWQVVGK-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200300172A ES2217956B1 (es) | 2003-01-23 | 2003-01-23 | Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo. |
| PCT/EP2004/000584 WO2004065391A1 (en) | 2003-01-23 | 2004-01-23 | 4-AMINOTHIENO[2,3-d]PYRIMIDINE-6-CARBONITRILE DERIVATIVES AS PDE7 INHIBITORS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006515604A JP2006515604A (ja) | 2006-06-01 |
| JP2006515604A5 true JP2006515604A5 (https=) | 2007-01-25 |
Family
ID=32749101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006500010A Pending JP2006515604A (ja) | 2003-01-23 | 2004-01-23 | Ｐｄｅ７阻害剤としての４−アミノチエノ［２，３−ｄ］ピリミジン−６−カルボニトリル誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7662814B2 (https=) |
| EP (1) | EP1590352B1 (https=) |
| JP (1) | JP2006515604A (https=) |
| CN (1) | CN100582112C (https=) |
| AT (1) | ATE365742T1 (https=) |
| DE (1) | DE602004007239T2 (https=) |
| ES (2) | ES2217956B1 (https=) |
| WO (1) | WO2004065391A1 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1610774A4 (en) * | 2003-04-09 | 2008-07-16 | Exelixis Inc | TIE-2 MODULATORS AND METHODS OF USE |
| US20060014165A1 (en) * | 2003-07-14 | 2006-01-19 | Decode Genetics Ehf. | Methods of diagnosis and treatment for asthma and other respiratory diseases based on haplotype association |
| EP1806347A4 (en) * | 2004-10-08 | 2009-07-01 | Astellas Pharma Inc | PYRIMIDINE DERIVATIVES FUSED WITH AN AROMATIC RING |
| TW200621257A (en) * | 2004-10-20 | 2006-07-01 | Astellas Pharma Inc | Pyrimidine derivative fused with nonaromatic ring |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| US20090247554A1 (en) * | 2006-03-30 | 2009-10-01 | Takeda San Diego, Inc. | Kinase inhibitors |
| TWI498332B (zh) | 2006-04-26 | 2015-09-01 | Hoffmann La Roche | 作為pi3k抑制劑之嘧啶衍生物及相關製備方法、醫藥組合物、用途、套組及產物 |
| MX2008013578A (es) | 2006-04-26 | 2009-03-23 | Hoffmann La Roche | Derivados de tieno [3,2-d]pirimidina utiles como inhibidores de fosfatidilinositol 3-cinasa(p13k). |
| CN101511840A (zh) * | 2006-04-26 | 2009-08-19 | 吉宁特有限公司 | 磷酸肌醇3-激酶抑制剂化合物及其使用方法 |
| GB0608820D0 (en) * | 2006-05-04 | 2006-06-14 | Piramed Ltd | Pharmaceutical compounds |
| EP2043654A2 (en) * | 2006-06-12 | 2009-04-08 | Vertex Pharmaceuticals, Inc. | Thienopyrimidines useful as modulators of ion channels |
| WO2008070740A1 (en) * | 2006-12-07 | 2008-06-12 | F.Hoffmann-La Roche Ag | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| ES2571028T3 (es) * | 2006-12-07 | 2016-05-23 | Genentech Inc | Compuestos inhibidores de fosfoinositida 3-cinasa y métodos de uso |
| US8637528B2 (en) | 2007-03-27 | 2014-01-28 | Omeros Corporation | Use of PDE7 inhibitors for the treatment of movement disorders |
| WO2008119057A2 (en) * | 2007-03-27 | 2008-10-02 | Omeros Corporation | The use of pde7 inhibitors for the treatment of movement disorders |
| AU2008298948B2 (en) * | 2007-09-12 | 2014-09-04 | F. Hoffmann-La Roche Ag | Combinations of phosphoinositide 3-kinase inhibitor compounds and chemotherapeutic agents, and methods of use |
| WO2009042607A1 (en) * | 2007-09-24 | 2009-04-02 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
| US8354528B2 (en) | 2007-10-25 | 2013-01-15 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| GB0721095D0 (en) | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| US20100093714A1 (en) * | 2008-10-13 | 2010-04-15 | Devraj Chakravarty | AMIDES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| US20100093702A1 (en) * | 2008-10-13 | 2010-04-15 | Barbay J Kent | METHYLENE AMINES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| ES2665277T3 (es) * | 2009-03-13 | 2018-04-25 | Katholieke Universiteit Leuven K.U. Leuven R&D | Análogos de purina y su uso como agentes inmunosupresores |
| CA2772371A1 (en) * | 2009-05-27 | 2010-12-02 | F. Hoffmann-La Roche Ag | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| CN102459272B (zh) * | 2009-05-27 | 2014-08-06 | 健泰科生物技术公司 | 对P110δ具有选择性的为PI3K抑制剂的二环嘧啶化合物和使用方法 |
| AU2011281015B2 (en) | 2010-07-23 | 2015-09-24 | President And Fellows Of Harvard College | Tricyclic proteasome activity enhancing compounds |
| US9220715B2 (en) | 2010-11-08 | 2015-12-29 | Omeros Corporation | Treatment of addiction and impulse-control disorders using PDE7 inhibitors |
| NZ628054A (en) | 2010-11-08 | 2016-03-31 | Omeros Corp | Treatment of addiction and impulse-control disorders using pde7 inhibitors |
| AR090037A1 (es) * | 2011-11-15 | 2014-10-15 | Xention Ltd | Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio |
| ES2575143T3 (es) | 2011-11-23 | 2016-06-24 | Cancer Research Technology Limited | Inhibidores de tienopiridina de la proteína quinasa C atípica |
| WO2013112699A2 (en) * | 2012-01-25 | 2013-08-01 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| CA2861464C (en) * | 2012-01-25 | 2018-03-06 | Proteostasis Therapeutics, Inc. | Proteasome activity modulating tricyclic compounds |
| AR092707A1 (es) | 2012-09-28 | 2015-04-29 | Takeda Pharmaceuticals Co | Metodo de produccion de derivado de tienopirimidina |
| FR3037957B1 (fr) * | 2015-06-23 | 2019-01-25 | Les Laboratoires Servier | Nouveaux derives d'hydroxyester, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN108135906A (zh) * | 2015-07-24 | 2018-06-08 | 路易斯维尔大学研究基金会有限公司 | 治病化合物、组合物、方法、及化合物制备方法 |
| JP2022551316A (ja) | 2019-10-10 | 2022-12-08 | ミオバント サイエンシズ ゲーエムベーハー | Ｎ－（４－（１－（２，６－ジフルオロベンジル）－５－（（ジメチルアミノ）メチル）－３－（６－メトキシ－３－ピリダジニル）－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－イル）フェニル）－Ｎ’－メトキシ尿素の結晶形 |
| CN115232146A (zh) * | 2022-08-04 | 2022-10-25 | 山东大学 | 一种2-氨基噻吩并[2,3-d]嘧啶类化合物及其制备方法和应用 |
| IL318817A (en) | 2022-08-18 | 2025-04-01 | Mitodicure Gmbh | Use of a therapeutic agent with PHOSPHODIESTERASE-7 inhibitory activity for the treatment and prevention of diseases associated with chronic fatigue, exhaustion and/or exercise intolerance |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4008726A1 (de) * | 1990-03-19 | 1991-09-26 | Basf Ag | Thieno(2,3-d)pyrimidinderivate |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| JPH1087492A (ja) * | 1996-06-25 | 1998-04-07 | Ono Pharmaceut Co Ltd | 一酸化窒素産生阻害剤 |
| DE19644228A1 (de) * | 1996-10-24 | 1998-04-30 | Merck Patent Gmbh | Thienopyrimidine |
| US6133271A (en) * | 1998-11-19 | 2000-10-17 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives |
| DE19953024A1 (de) | 1999-11-04 | 2001-05-10 | Merck Patent Gmbh | Isoxazolderivate als Phosphodiesterase VII-Hemmer |
| DE19954707A1 (de) | 1999-11-13 | 2001-05-17 | Merck Patent Gmbh | Imidazolverbindungen als Phosphodiesterase VII-Hemmer |
| KR20030034232A (ko) * | 2000-09-29 | 2003-05-01 | 닛뽕소다 가부시키가이샤 | 티에노피리미딘 화합물 및 그 염 및 제조방법 |
| EP1193261A1 (en) | 2000-10-02 | 2002-04-03 | Warner-Lambert Company | New thiadiazoles and their use as phosphodiesterase-7 inhibitors |
| US6849638B2 (en) * | 2001-04-30 | 2005-02-01 | Bayer Pharmaceuticals Corporation | 4-amino-5,6-substituted thiopheno [2,3-d] pyrimidines, pharmaceutical compositions containing the same, and their use in the treatment or prevention of pde7b-mediated diseases and conditions |
| EP1348701A1 (en) | 2002-03-28 | 2003-10-01 | Warner-Lambert Company LLC | (2,4-disubstituted-thiazol-5-yl) amine compounds as PDE7 inhibitors |
-
2003
- 2003-01-23 ES ES200300172A patent/ES2217956B1/es not_active Expired - Fee Related
-
2004
- 2004-01-23 AT AT04704579T patent/ATE365742T1/de not_active IP Right Cessation
- 2004-01-23 CN CN200480007362A patent/CN100582112C/zh not_active Expired - Fee Related
- 2004-01-23 JP JP2006500010A patent/JP2006515604A/ja active Pending
- 2004-01-23 DE DE602004007239T patent/DE602004007239T2/de not_active Expired - Lifetime
- 2004-01-23 WO PCT/EP2004/000584 patent/WO2004065391A1/en not_active Ceased
- 2004-01-23 US US10/542,940 patent/US7662814B2/en not_active Expired - Fee Related
- 2004-01-23 ES ES04704579T patent/ES2289475T3/es not_active Expired - Lifetime
- 2004-01-23 EP EP04704579A patent/EP1590352B1/en not_active Expired - Lifetime
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