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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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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)
| Publication Number | Publication Date |
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| CA2702518A1 true CA2702518A1 (en) | 2009-04-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2702518A Abandoned CA2702518A1 (en) | 2007-10-19 | 2008-10-16 | New piperazino-dihydrothienopyrimidine derivatives |
Country Status (6)
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| US (2) | US8486948B2 (https=) |
| EP (1) | EP2215093B1 (https=) |
| JP (1) | JP5563466B2 (https=) |
| AT (1) | ATE537175T1 (https=) |
| CA (1) | CA2702518A1 (https=) |
| WO (1) | WO2009050236A1 (https=) |
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 |
| MX2010004026A (es) * | 2007-10-19 | 2010-04-30 | Boehringer Ingelheim Int | Piperidino-dihidrotienopirimidinas sustituidas. |
| EP2205609B1 (de) | 2007-10-19 | 2017-03-29 | Boehringer Ingelheim International GmbH | Heterocyclus-substituierte piperazino-dihydrothienopyrimidine |
| ATE537175T1 (de) | 2007-10-19 | 2011-12-15 | Boehringer Ingelheim Int | Neue piperazino-dihydrothienopyrimidin-derivate |
| PL2552920T3 (pl) | 2010-04-02 | 2017-08-31 | Ogeda Sa | Nowe wybiórcze związki antagonistów receptora NK-3, farmaceutyczne kompozycje i sposoby do zastosowania w zaburzeniach pośredniczonych przez receptory NK-3 |
| 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 |
| US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
| US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
| DK2763992T3 (en) * | 2011-10-03 | 2016-04-25 | Euroscreen Sa | NOVEL CHIRAL N-acyl-5,6,7, (8-substituted) -tetrahydro [1,2,4] triazolo [4,3-a] pyrazines as selective NK-3 receptor antagonists, PHARMACEUTICAL COMPOSITION AND METHODS FOR THE use in the NK-3 receptor mediated diseases |
| EP2802590B1 (en) * | 2012-01-10 | 2017-03-01 | F. Hoffmann-La Roche AG | Thienopyrimidine compounds |
| US9499519B2 (en) | 2012-12-26 | 2016-11-22 | Medivation Technologies, Inc. | Fused pyrimidine compounds and use thereof |
| KR102151292B1 (ko) | 2013-01-31 | 2020-09-02 | 가부시키가이샤 무라타 세이사쿠쇼 | 압전 진동체 |
| TW201512189A (zh) * | 2013-04-16 | 2015-04-01 | Gruenenthal Chemie | 新型被取代之嘧啶縮合化合物 |
| TWI752141B (zh) * | 2016-12-26 | 2022-01-11 | 日商明治製菓藥業股份有限公司 | 新穎化合物以及其藥理上所容許之鹽 |
| 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 |
| CN113929678B (zh) * | 2020-07-14 | 2025-09-30 | 武汉朗来科技发展有限公司 | 一种rock抑制剂及其制备方法和用途 |
| EP4534540A4 (en) * | 2022-06-02 | 2026-04-15 | Xizang Haisco Pharmaceutical Co Ltd | PDE4B INHIBITOR AND ITS USES |
| EP4570804A1 (en) * | 2022-08-09 | 2025-06-18 | Xizang Haisco Pharmaceutical Co., Ltd. | Pde4b inhibitor and use thereof |
| WO2024067660A1 (zh) | 2022-09-29 | 2024-04-04 | 苏州爱科百发生物医药技术有限公司 | 氮杂稠环类化合物、其制备方法及其在医药上的应用 |
| WO2024213089A1 (zh) | 2023-04-13 | 2024-10-17 | 上海壹迪生物技术有限公司 | 取代的二氢噻吩并嘧啶类化合物、其制备方法和应用 |
| AU2024323358A1 (en) * | 2023-08-17 | 2026-02-26 | Katalytic Therapeutics, Inc. | Pde4 protein degraders, pharmaceutical compositions, and therapeutic applications |
| CN121889398A (zh) * | 2023-09-25 | 2026-04-17 | 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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| DE1470336A1 (de) | 1962-07-04 | 1969-03-20 | Thomae Gmbh Dr K | Neue Dihydrothieno-[3,4-d]-pyrimidine und Verfahren zu ihrer Herstellung |
| NL122810C (https=) | 1963-06-17 | |||
| DE1470356A1 (de) | 1964-01-15 | 1970-04-30 | Thomae Gmbh Dr K | Neue Thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
| 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 |
| 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 |
| BE754606A (fr) | 1969-08-08 | 1971-02-08 | Thomae Gmbh Dr K | Nouvelles 2-aminoalcoylamino-thieno(3,2-d)pyrimidines et leurs procedesde fabrication |
| US3763156A (en) | 1970-01-28 | 1973-10-02 | Boehringer Sohn Ingelheim | 2-heterocyclic amino-4-morpholinothieno(3,2-d)pyrimidines |
| FR2082496A5 (https=) | 1970-03-18 | 1971-12-10 | Westinghouse Freins & Signaux | |
| 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 |
| US4256737A (en) | 1979-06-11 | 1981-03-17 | Syntex (U.S.A.) Inc. | Long acting depot injectable formulations for LH-RH analogues |
| US5187168A (en) | 1991-10-24 | 1993-02-16 | American Home Products Corporation | Substituted quinazolines as angiotensin II antagonists |
| JPH07330777A (ja) | 1994-06-08 | 1995-12-19 | Taisho Pharmaceut Co Ltd | チエノ［３，２−ｄ］ピリミジン−４−オン誘導体 |
| JPH09301958A (ja) | 1996-05-09 | 1997-11-25 | Nippon Shoji Kk | 新規ピリミジン化合物及び抗ロタウイルス剤 |
| US6339089B2 (en) | 1997-08-13 | 2002-01-15 | Fujirebio Inc. | Pyrimidine nucleus-containing compound and a medicament containing the same for a blood oxygen partial pressure amelioration, and a method for preparing the same |
| DE10064994A1 (de) | 2000-12-23 | 2002-07-04 | Merck Patent Gmbh | Sulfamidothienopyrimidine |
| MXPA03009925A (es) * | 2001-04-30 | 2004-06-30 | Bayer Pharmaceuticals Corp | Nuevas tiofeno [2,3-d]pirimidinas 4-amino-5,6-sustituidas. |
| US6587548B2 (en) | 2001-07-17 | 2003-07-01 | Hewlett-Packard Development Co., L.P. | Method and system of using a single telephone number for multiple services |
| WO2003055890A1 (en) | 2001-12-21 | 2003-07-10 | Bayer Pharmaceuticals Corporation | Thienopyrimidine derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
| JP4505228B2 (ja) | 2002-01-10 | 2010-07-21 | バイエル・シェーリング・ファルマ・アクチェンゲゼルシャフト | Ｒｈｏ−キナーゼ阻害剤 |
| OA13050A (en) | 2003-04-29 | 2006-11-10 | Pfizer Ltd | 5,7-diaminopyrazolo [4,3-D] pyrimidines useful in the treatment of hypertension. |
| JP2005003345A (ja) | 2003-05-21 | 2005-01-06 | Showa Denko Kk | 換気兼熱交換装置および空調システム |
| JP4733043B2 (ja) | 2003-10-02 | 2011-07-27 | マーテック バイオサイエンシーズ コーポレーション | 改変された量の塩化物およびカリウムを使用した微細藻類における高レベルのｄｈａの産生法 |
| MY141220A (en) | 2003-11-17 | 2010-03-31 | Astrazeneca Ab | Pyrazole derivatives as inhibitors of receptor tyrosine kinases |
| WO2005082865A1 (ja) | 2004-02-27 | 2005-09-09 | Astellas Pharma Inc. | 縮合二環性ピリミジン誘導体 |
| RS51163B (sr) | 2006-04-19 | 2010-10-31 | Boehringer Ingelheim International Gmbh. | Dihidrotienopirimidin za lečenje zapaljenskih bolesti |
| EP1847543A1 (de) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen |
| AU2008240764C1 (en) | 2007-04-20 | 2011-10-20 | Glaxo Group Limited | Tricyclic nitrogen containing compounds as antibacterial agents |
| CA2702500A1 (en) | 2007-10-18 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Preparation of dihydrothieno [3, 2-d] pyrimidines and intermediates used therein |
| BRPI0818448A2 (pt) | 2007-10-19 | 2015-05-12 | Astrazeneca Ab | Composto, composição farmacêutica, uso de um composto, e, métodos para o tratamento ou prevenção de um distúrbio madiano pelo receptor mglur5. |
| 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 |
| MX2010004026A (es) | 2007-10-19 | 2010-04-30 | Boehringer Ingelheim Int | Piperidino-dihidrotienopirimidinas sustituidas. |
| JP2011500621A (ja) | 2007-10-19 | 2011-01-06 | 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 | 新規フェニル置換ピペラジノ−ジヒドロチエノピリミジン |
| ATE537175T1 (de) | 2007-10-19 | 2011-12-15 | Boehringer Ingelheim Int | Neue piperazino-dihydrothienopyrimidin-derivate |
| TW200934785A (en) | 2007-10-19 | 2009-08-16 | Schering Corp | Compounds for inhibiting KSP kinesin activity |
| EP2205609B1 (de) | 2007-10-19 | 2017-03-29 | Boehringer Ingelheim International GmbH | Heterocyclus-substituierte piperazino-dihydrothienopyrimidine |
| CA2753597A1 (en) | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Drug combinations containing pde4-inhibitors and nsaids |
| EP2400962B1 (de) | 2009-02-27 | 2017-11-08 | Boehringer Ingelheim International GmbH | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
| US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
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2013
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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 |
|---|---|
| EP2215093A1 (de) | 2010-08-11 |
| JP5563466B2 (ja) | 2014-07-30 |
| JP2011500638A (ja) | 2011-01-06 |
| ATE537175T1 (de) | 2011-12-15 |
| EP2215093B1 (de) | 2011-12-14 |
| WO2009050236A1 (de) | 2009-04-23 |
| US20130274264A1 (en) | 2013-10-17 |
| US9090626B2 (en) | 2015-07-28 |
| US20110046096A1 (en) | 2011-02-24 |
| US8486948B2 (en) | 2013-07-16 |
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Legal Events
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| EEER | Examination request |
Effective date: 20131011 |
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| FZDE | Discontinued |
Effective date: 20151016 |