CA2702518A1 - New piperazino-dihydrothienopyrimidine derivatives - Google Patents
New piperazino-dihydrothienopyrimidine derivatives Download PDFInfo
- Publication number
- CA2702518A1 CA2702518A1 CA2702518A CA2702518A CA2702518A1 CA 2702518 A1 CA2702518 A1 CA 2702518A1 CA 2702518 A CA2702518 A CA 2702518A CA 2702518 A CA2702518 A CA 2702518A CA 2702518 A1 CA2702518 A1 CA 2702518A1
- Authority
- CA
- Canada
- Prior art keywords
- alkylene
- alkyl
- hetaryl
- het
- phenyl
- 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.)
- Abandoned
Links
- NBHGLBORHJRXFF-UHFFFAOYSA-N 1-piperazin-1-yl-2h-thieno[3,2-d]pyrimidine Chemical class C1CNCCN1N1C(C=CS2)=C2C=NC1 NBHGLBORHJRXFF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 150000003839 salts Chemical class 0.000 claims abstract description 108
- 201000010099 disease Diseases 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
- 230000000241 respiratory effect Effects 0.000 claims abstract description 11
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 9
- 230000002093 peripheral effect Effects 0.000 claims abstract description 9
- 210000001428 peripheral nervous system Anatomy 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 5
- -1 C1-6-alkanol Chemical group 0.000 claims description 166
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 116
- 125000004043 oxo group Chemical group O=* 0.000 claims description 82
- 229910052736 halogen Inorganic materials 0.000 claims description 74
- 150000002367 halogens Chemical class 0.000 claims description 74
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 125000002950 monocyclic group Chemical group 0.000 claims description 55
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 49
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 49
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 49
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 49
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 47
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 33
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 239000003112 inhibitor Substances 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 125000002619 bicyclic group Chemical group 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 239000013543 active substance Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 230000001154 acute effect Effects 0.000 claims description 16
- 239000005557 antagonist Substances 0.000 claims description 16
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 15
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 15
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 13
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229940121647 egfr inhibitor Drugs 0.000 claims description 13
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 12
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 12
- 230000003454 betamimetic effect Effects 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 239000000808 adrenergic beta-agonist Substances 0.000 claims description 11
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
- 208000020925 Bipolar disease Diseases 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- 208000028683 bipolar I disease Diseases 0.000 claims description 8
- 239000003246 corticosteroid Substances 0.000 claims description 8
- 229960001334 corticosteroids Drugs 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 230000000414 obstructive effect Effects 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 206010019196 Head injury Diseases 0.000 claims description 4
- 206010021143 Hypoxia Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 208000025307 bipolar depression Diseases 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 230000007954 hypoxia Effects 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 230000003843 mucus production Effects 0.000 claims description 3
- 210000002345 respiratory system Anatomy 0.000 claims description 3
- 125000003003 spiro group Chemical group 0.000 claims description 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 208000019693 Lung disease Diseases 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract description 2
- 150000003462 sulfoxides Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 description 124
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000002253 acid Substances 0.000 description 53
- 150000004677 hydrates Chemical class 0.000 description 47
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 44
- 239000012453 solvate Substances 0.000 description 44
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000000460 chlorine Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
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- C07D—HETEROCYCLIC COMPOUNDS
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Applications Claiming Priority (3)
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|---|---|---|---|
| EP07118906 | 2007-10-19 | ||
| EP07118906.2 | 2007-10-19 | ||
| PCT/EP2008/063970 WO2009050236A1 (de) | 2007-10-19 | 2008-10-16 | Neue piperazino-dihydrothienopyrimidin-derivate |
Publications (1)
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| CA2702518A1 true CA2702518A1 (en) | 2009-04-23 |
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| CA2702518A Abandoned CA2702518A1 (en) | 2007-10-19 | 2008-10-16 | New piperazino-dihydrothienopyrimidine derivatives |
Country Status (6)
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| US (2) | US8486948B2 (enExample) |
| EP (1) | EP2215093B1 (enExample) |
| JP (1) | JP5563466B2 (enExample) |
| AT (1) | ATE537175T1 (enExample) |
| CA (1) | CA2702518A1 (enExample) |
| WO (1) | WO2009050236A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11292799B2 (en) | 2017-12-15 | 2022-04-05 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| US11299497B2 (en) | 2017-12-15 | 2022-04-12 | UNION therapeutics A/S | Substituted tetrahydropyran dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| US11384096B2 (en) | 2017-12-15 | 2022-07-12 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyridines and their use as phosphodiesterase inhibitors |
| US11866445B2 (en) | 2017-09-20 | 2024-01-09 | UNION therapeutics A/S | Substituted dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
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| EP1847543A1 (de) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen |
| JP5563466B2 (ja) | 2007-10-19 | 2014-07-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ピペラジノ−ジヒドロチエノピリミジン誘導体 |
| DK2610258T3 (da) | 2007-10-19 | 2014-11-10 | Boehringer Ingelheim Int | Substituerede piperidindihydrothienopyrimidiner |
| CN101827853A (zh) | 2007-10-19 | 2010-09-08 | 贝林格尔.英格海姆国际有限公司 | 杂环取代的哌嗪子基-二氢噻吩并嘧啶 |
| EP3176171A1 (en) | 2010-04-02 | 2017-06-07 | Ogeda Sa | Novel nk-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in nk-3 receptors mediated disorders |
| US10065960B2 (en) | 2010-04-02 | 2018-09-04 | Ogeda Sa | NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders |
| US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
| US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
| EA029340B1 (ru) * | 2011-10-03 | 2018-03-30 | Огеда Са | ХИРАЛЬНЫЕ N-АЦИЛ-5,6,7,(8-ЗАМЕЩЕННЫЕ)-ТЕТРАГИДРО[1,2,4]ТРИАЗОЛО[4,3-a]ПИРАЗИНЫ КАК СЕЛЕКТИВНЫЕ АНТАГОНИСТЫ РЕЦЕПТОРА NK-3, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ПРИМЕНЕНИЯ ПРИ НАРУШЕНИЯХ, ОПОСРЕДОВАННЫХ NK-3 РЕЦЕПТОРАМИ, И ИХ ХИРАЛЬНЫЙ СИНТЕЗ |
| RU2637925C2 (ru) * | 2012-01-10 | 2017-12-08 | Ф. Хоффманн-Ля Рош Аг | Соединения тиенопиримидина |
| WO2014105958A2 (en) | 2012-12-26 | 2014-07-03 | Medivation Technologies, Inc. | Fused pyrimidine compounds and use thereof |
| JP5671192B2 (ja) | 2013-01-31 | 2015-02-18 | 帝人株式会社 | 圧電振動体 |
| TW201512189A (zh) * | 2013-04-16 | 2015-04-01 | Gruenenthal Chemie | 新型被取代之嘧啶縮合化合物 |
| ES2875548T3 (es) * | 2016-12-26 | 2021-11-10 | Meiji Seika Pharma Co Ltd | Compuesto novedoso y sal de este aceptable desde el punto de vista farmacológico |
| CN111961034A (zh) * | 2019-05-20 | 2020-11-20 | 浙江同源康医药股份有限公司 | 用作ret激酶抑制剂的化合物及其应用 |
| JP7772771B2 (ja) * | 2020-07-14 | 2025-11-18 | 武漢朗来科技発展有限公司 | Ｒｏｃｋ阻害剤及びその製造方法と用途 |
| CN119343352A (zh) * | 2022-06-02 | 2025-01-21 | 西藏海思科制药有限公司 | Pde4b抑制剂及其用途 |
| AU2023320795A1 (en) * | 2022-08-09 | 2025-02-27 | Xizang Haisco Pharmaceutical Co., Ltd. | Pde4b inhibitor and use thereof |
| US20260008788A1 (en) | 2022-09-29 | 2026-01-08 | Suzhou Ark Biopharmaceutical Co., Ltd. | Aza-fused ring compound, preparation method therefor, and use thereof in medicine |
| KR20250165661A (ko) | 2023-04-13 | 2025-11-26 | 상하이 이디 바이오테크놀로지 컴퍼니 리미티드 | 치환된 디히드로티오펜 병합 피리미딘류 화합물, 이의 제조 방법 및 용도 |
| WO2025038987A2 (en) * | 2023-08-17 | 2025-02-20 | Katalytic Therapeutics, Inc. | Pde4 protein degraders, pharmaceutical compositions, and therapeutic applications |
| WO2025067168A1 (zh) * | 2023-09-25 | 2025-04-03 | 苏州爱科百发生物医药技术有限公司 | 氮杂稠环类化合物及其制备方法和用途 |
| WO2025162431A1 (zh) * | 2024-02-04 | 2025-08-07 | 西藏海思科制药有限公司 | 一种pde4b抑制剂化合物的口服药物组合物及其制备方法 |
| TW202535412A (zh) * | 2024-02-04 | 2025-09-16 | 大陸商西藏海思科製藥有限公司 | Pde4b抑制劑的晶型及其在醫藥上的用途 |
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| BE754606A (fr) | 1969-08-08 | 1971-02-08 | Thomae Gmbh Dr K | Nouvelles 2-aminoalcoylamino-thieno(3,2-d)pyrimidines et leurs procedesde fabrication |
| DE2032687A1 (en) | 1970-07-02 | 1972-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Cardiovascular 2-aminoalkylamino-thienopyrimidines - and 4-morpholino derivatives from 4-diethanolamino-compounds by intramolecular cyclisa |
| DE1940572A1 (de) | 1969-08-08 | 1971-02-11 | Thomae Gmbh Dr K | Neue 2-Aminoalkylamino-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
| US3763156A (en) | 1970-01-28 | 1973-10-02 | Boehringer Sohn Ingelheim | 2-heterocyclic amino-4-morpholinothieno(3,2-d)pyrimidines |
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| DE2121950A1 (en) | 1971-05-04 | 1972-11-23 | Dr. Karl Thomae Gmbh, 7950 Biberach | Thieno(3,2-d)pyrimidine derivs - with thrombocyte aggregation inhibiting activity |
| DE2750288A1 (de) | 1977-11-10 | 1979-05-17 | Thomae Gmbh Dr K | Neue 9-(omega-heteroarylamino- alkylamino)-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
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| EP2214673B1 (de) | 2007-10-19 | 2012-05-30 | Boehringer Ingelheim International GmbH | Phenyl-substituierte piperazino-dihydrothienopyrimidine |
| JP5563466B2 (ja) | 2007-10-19 | 2014-07-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ピペラジノ−ジヒドロチエノピリミジン誘導体 |
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| FR2922550B1 (fr) | 2007-10-19 | 2009-11-27 | Sanofi Aventis | Nouveaux derives de 6-aryl/heteroalkyloxy benzothiazole et benzimidazole, application comme medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de cmet |
| TW200934771A (en) | 2007-10-19 | 2009-08-16 | Astrazeneca Ab | New compounds |
| DK2610258T3 (da) | 2007-10-19 | 2014-11-10 | Boehringer Ingelheim Int | Substituerede piperidindihydrothienopyrimidiner |
| CN101827853A (zh) | 2007-10-19 | 2010-09-08 | 贝林格尔.英格海姆国际有限公司 | 杂环取代的哌嗪子基-二氢噻吩并嘧啶 |
| WO2010097334A1 (de) | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
| JP2012519159A (ja) | 2009-02-27 | 2012-08-23 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｐｄｅ４阻害剤及びｎｓａｉｄを含有する複合薬 |
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- 2008-10-16 CA CA2702518A patent/CA2702518A1/en not_active Abandoned
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- 2008-10-16 US US12/738,425 patent/US8486948B2/en active Active
- 2008-10-16 WO PCT/EP2008/063970 patent/WO2009050236A1/de not_active Ceased
- 2008-10-16 AT AT08840365T patent/ATE537175T1/de active
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2013
- 2013-06-06 US US13/911,712 patent/US9090626B2/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11866445B2 (en) | 2017-09-20 | 2024-01-09 | UNION therapeutics A/S | Substituted dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| US11292799B2 (en) | 2017-12-15 | 2022-04-05 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| US11299497B2 (en) | 2017-12-15 | 2022-04-12 | UNION therapeutics A/S | Substituted tetrahydropyran dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| US11384096B2 (en) | 2017-12-15 | 2022-07-12 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyridines and their use as phosphodiesterase inhibitors |
| US11981681B2 (en) | 2017-12-15 | 2024-05-14 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyridines and their use as phosphodiesterase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110046096A1 (en) | 2011-02-24 |
| ATE537175T1 (de) | 2011-12-15 |
| US8486948B2 (en) | 2013-07-16 |
| EP2215093A1 (de) | 2010-08-11 |
| JP2011500638A (ja) | 2011-01-06 |
| WO2009050236A1 (de) | 2009-04-23 |
| US9090626B2 (en) | 2015-07-28 |
| EP2215093B1 (de) | 2011-12-14 |
| US20130274264A1 (en) | 2013-10-17 |
| JP5563466B2 (ja) | 2014-07-30 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20131011 |
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| FZDE | Discontinued |
Effective date: 20151016 |