JP2006515604A5 - - Google Patents
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- 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
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- 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.)
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- -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 8
- 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
- LGNVAEIITHYWCG-UHFFFAOYSA-N 2-amino-4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C(N)=C1 LGNVAEIITHYWCG-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
- 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
- 239000000969 carrier Substances 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
- 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
- 239000000546 pharmaceutic aid Substances 0.000 description 1
- 239000008194 pharmaceutical composition 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000699 topical Effects 0.000 description 1
Description
４−(ジエチルアミノ)−５−メチル−２−(４−ニトロフェニル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−クロロフェニル)−４−(ジエチルアミノ)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジエチルアミノ)−２−(３,４−ジメトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジメチルアミノ)−２−(４−メトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−メトキシフェニル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−クロロフェニル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−メトキシフェニル)−５−メチル−４−[メチル(プロパ−２−イニル)アミノ]チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[(２−ヒドロキシエチル)(メチル)アミノ]−２−(４−メトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(３,４−ジメトキシフェニル)−４−[エチル(メチル)アミノ]−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
５−メチル−２−(４−メチルフェニル)−４−(４−メチルピペラジン−１−イル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジエチルアミノ)−５−メチル−２−[４−(トリフルオロメチル)フェニル]チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[アリル(メチル)アミノ]−２−(４−メトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(３,４−ジメトキシフェニル)−４−[(２−ヒドロキシエチル)(メチル)アミノ]−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(３,４−ジメトキシフェニル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
５−メチル−２−(４−メチルフェニル)−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
５−メチル−４−(４−メチルピペラジン−１−イル)−２−[４−(トリフルオロメチル)フェニル]チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(１,３−ベンゾジオキソール−５−イル)−５−メチル−４−(４−メチルピペラジン−１−イル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジエチルアミノ)−５−メチル−２−(４−メチルフェニル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(１,３−ベンゾジオキソール−５−イル)−４−(ジエチルアミノ)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(１,３−ベンゾジオキソール−５−イル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[エチル(メチル)アミノ]−５−メチル−２−ピリジン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[エチル(メチル)アミノ]−５−メチル−２−(３,４,５−トリメトキシフェニル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−ベンジル−５−メチル−４−(４−メチルピペラジン−１−イル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−クロロフェニル)−４−(ジエチルアミノ)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジエチルアミノ)−２−(３,４−ジメトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジメチルアミノ)−２−(４−メトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−メトキシフェニル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−クロロフェニル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(４−メトキシフェニル)−５−メチル−４−[メチル(プロパ−２−イニル)アミノ]チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[(２−ヒドロキシエチル)(メチル)アミノ]−２−(４−メトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(３,４−ジメトキシフェニル)−４−[エチル(メチル)アミノ]−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
５−メチル−２−(４−メチルフェニル)−４−(４−メチルピペラジン−１−イル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジエチルアミノ)−５−メチル−２−[４−(トリフルオロメチル)フェニル]チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[アリル(メチル)アミノ]−２−(４−メトキシフェニル)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(３,４−ジメトキシフェニル)−４−[(２−ヒドロキシエチル)(メチル)アミノ]−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(３,４−ジメトキシフェニル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
５−メチル−２−(４−メチルフェニル)−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
５−メチル−４−(４−メチルピペラジン−１−イル)−２−[４−(トリフルオロメチル)フェニル]チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(１,３−ベンゾジオキソール−５−イル)−５−メチル−４−(４−メチルピペラジン−１−イル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−(ジエチルアミノ)−５−メチル−２−(４−メチルフェニル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(１,３−ベンゾジオキソール−５−イル)−４−(ジエチルアミノ)−５−メチルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−(１,３−ベンゾジオキソール−５−イル)−５−メチル−４−モルホリン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[エチル(メチル)アミノ]−５−メチル−２−ピリジン−４−イルチエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
４−[エチル(メチル)アミノ]−５−メチル−２−(３,４,５−トリメトキシフェニル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
２−ベンジル−５−メチル−４−(４−メチルピペラジン−１−イル)チエノ[２,３−ｄ]ピリミジン−６−カルボニトリル
本発明はまた、有効成分として、少なくとも１個の式（Ｉ）で示される化合物またはその医薬上許容される塩を、医薬上許容される賦形剤、例えば担体または希釈剤と共に含む医薬組成物を提供する。有効成分は、処方物の性質および適用前にさらなる希釈が為されるか否かにより、重量にして０.００１％〜９９％、好ましくは重量にして０.０１％〜９０％の割合で組成物を構成し得る。好ましくは、組成物は、経口、局所、鼻、直腸、経皮または注射可能投与に適切な形態で製造される。
製造例５
５−メチル−２−(４−メチルフェニル)−４−オキソ−３,４−ジヒドロチエノ［２,３−ｄ］ピリミジン−６−カルボニトリル
製造例２記載の実験手順に従って、２−アミノ−５−シアノ−４−メチルチオフェン−３−カルボン酸エチルエステルおよび４−メチルベンゾニトリルから褐色固体（７２％）として得た。
1H-NMR (CDCl3, 200 MHz) δ 10.30 (bs, 1H), 7.97 (d, J=7.7 Hz, 2H), 7.29 (d, J= 7.7 Hz, 2H), 2.78 (s, 3H), 2.45 (s, 3H)。
５−メチル−２−(４−メチルフェニル)−４−オキソ−３,４−ジヒドロチエノ［２,３−ｄ］ピリミジン−６−カルボニトリル
1H-NMR (CDCl3, 200 MHz) δ 10.30 (bs, 1H), 7.97 (d, J=7.7 Hz, 2H), 7.29 (d, J= 7.7 Hz, 2H), 2.78 (s, 3H), 2.45 (s, 3H)。
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 (ja) | 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 (ja) |
| EP (1) | EP1590352B1 (ja) |
| JP (1) | JP2006515604A (ja) |
| CN (1) | CN100582112C (ja) |
| AT (1) | ATE365742T1 (ja) |
| DE (1) | DE602004007239T2 (ja) |
| ES (2) | ES2217956B1 (ja) |
| WO (1) | WO2004065391A1 (ja) |
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| 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 |
| CA2583259C (en) * | 2004-10-08 | 2011-08-02 | Astellas Pharma Inc. | Aromatic ring fused pyrimidine derivative |
| 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 |
| CN101472930B (zh) | 2006-04-26 | 2011-12-14 | 霍夫曼-拉罗奇有限公司 | 用作PI3K抑制剂的噻吩并[3,2-d]嘧啶的衍生物 |
| 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 |
| MX2008013584A (es) | 2006-04-26 | 2009-03-23 | Genentech Inc | Compuestos farmaceuticos. |
| GB0608820D0 (en) * | 2006-05-04 | 2006-06-14 | Piramed Ltd | Pharmaceutical compounds |
| CA2654842A1 (en) * | 2006-06-12 | 2007-12-21 | Vertex Pharmaceuticals Incorporated | Thienopyrimidines useful as modulators of ion channels |
| TW200829594A (en) * | 2006-12-07 | 2008-07-16 | Piramed Ltd | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| PE20081679A1 (es) * | 2006-12-07 | 2008-12-18 | Hoffmann La Roche | Compuestos del inhibidor de fosfoinositida 3-cinasa y metodos de uso |
| BRPI0809244A2 (pt) | 2007-03-27 | 2014-09-23 | Omeros Corp | Métodos de tratamento de uma anormalidade de movimento, e para identificação de um agente que inibe a atividade pde7. |
| US8637528B2 (en) | 2007-03-27 | 2014-01-28 | Omeros Corporation | Use of PDE7 inhibitors for the treatment of movement disorders |
| AR068402A1 (es) | 2007-09-12 | 2009-11-18 | Genentech Inc | Combinaciones de compuestos inhibidores de fosfoinositida 3-quinasa y agentes quimioterapeuticos y los metodos de uso |
| US7893059B2 (en) * | 2007-09-24 | 2011-02-22 | Genentech, Inc. | Thiazolopyrimidine PI3K inhibitor compounds and methods of use |
| ES2439705T3 (es) * | 2007-10-25 | 2014-01-24 | Genentech, Inc. | Proceso para la preparación de compuestos de tienopirimidina |
| 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 |
| WO2010103130A2 (en) * | 2009-03-13 | 2010-09-16 | Katholieke Universiteit Leuven, K.U.Leuven R&D | Novel bicyclic heterocycles |
| 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 |
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| JP6042331B2 (ja) | 2010-07-23 | 2016-12-14 | プレジデント アンド フェローズ オブ ハーバード カレッジ | プロテアソーム活性を向上させる三環系化合物 |
| AU2011326173B2 (en) | 2010-11-08 | 2015-08-27 | Omeros Corporation | Treatment of addiction and impulse-control disorders using PDE7 inhibitors |
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| 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 |
| EP3048106B1 (en) | 2011-11-23 | 2019-11-06 | Cancer Research Technology Limited | Thienopyrimidine as inhibitors of atypical protein kinase c |
| EP2806875B1 (en) | 2012-01-25 | 2017-07-19 | Proteostasis Therapeutics, Inc. | Proteasome activity modulating compounds |
| WO2013112699A2 (en) * | 2012-01-25 | 2013-08-01 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| EP4119564A1 (en) * | 2012-09-28 | 2023-01-18 | Takeda Pharmaceutical Company Limited | Production method of thienopyrimidine derivative |
| 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 |
| US11312690B2 (en) | 2015-07-24 | 2022-04-26 | University Of Lousville Research Foundation, Inc. | Compounds, compositions, methods for treating diseases, and methods for preparing compounds |
| 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 |
| WO2024038089A1 (en) | 2022-08-18 | 2024-02-22 | 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 exertional intolerance |
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| 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 |
| CN1458933A (zh) * | 2000-09-29 | 2003-11-26 | 日本曹达株式会社 | 噻吩并嘧啶化合物及其盐以及其制备方法 |
| EP1193261A1 (en) * | 2000-10-02 | 2002-04-03 | Warner-Lambert Company | New thiadiazoles and their use as phosphodiesterase-7 inhibitors |
| CN100343258C (zh) * | 2001-04-30 | 2007-10-17 | 美国拜尔公司 | 新的4－氨基－5,6－取代的噻吩并[2,3－d]嘧啶化合物 |
| 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 JP JP2006500010A patent/JP2006515604A/ja active Pending
- 2004-01-23 EP EP04704579A patent/EP1590352B1/en not_active Expired - Lifetime
- 2004-01-23 AT AT04704579T patent/ATE365742T1/de not_active IP Right Cessation
- 2004-01-23 WO PCT/EP2004/000584 patent/WO2004065391A1/en active IP Right Grant
- 2004-01-23 DE DE602004007239T patent/DE602004007239T2/de not_active Expired - Lifetime
- 2004-01-23 ES ES04704579T patent/ES2289475T3/es not_active Expired - Lifetime
- 2004-01-23 CN CN200480007362A patent/CN100582112C/zh not_active Expired - Fee Related
- 2004-01-23 US US10/542,940 patent/US7662814B2/en not_active Expired - Fee Related
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