JP2011500621A - 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 - Google Patents
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 Download PDFInfo
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- JP2011500621A JP2011500621A JP2010529353A JP2010529353A JP2011500621A JP 2011500621 A JP2011500621 A JP 2011500621A JP 2010529353 A JP2010529353 A JP 2010529353A JP 2010529353 A JP2010529353 A JP 2010529353A JP 2011500621 A JP2011500621 A JP 2011500621A
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- Prior art keywords
- phenyl
- alkylene
- het
- aryl
- amino
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- -1 phenyl-substituted piperazino-dihydrothienopyrimidines Chemical class 0.000 title claims description 315
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 135
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 150000003839 salts Chemical class 0.000 claims abstract description 104
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 17
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
- 230000002093 peripheral effect Effects 0.000 claims abstract description 8
- 230000000241 respiratory effect Effects 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- 208000035475 disorder Diseases 0.000 claims abstract description 5
- 230000001079 digestive effect Effects 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 82
- 125000001072 heteroaryl group Chemical group 0.000 claims description 73
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
- 125000004043 oxo group Chemical group O=* 0.000 claims description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
- 229910052799 carbon Inorganic materials 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 51
- 239000000460 chlorine Substances 0.000 claims description 50
- 229910052801 chlorine Inorganic materials 0.000 claims description 50
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 47
- 229910052794 bromium Inorganic materials 0.000 claims description 44
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 42
- 125000002950 monocyclic group Chemical group 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 20
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- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
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- 239000005557 antagonist Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 14
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 13
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
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- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims description 8
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- 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
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 5
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 5
- 229940044601 receptor agonist Drugs 0.000 claims description 5
- 239000000018 receptor agonist Substances 0.000 claims description 5
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
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- 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
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 4
- 102100038183 Tyrosine-protein kinase SYK Human genes 0.000 claims description 4
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- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
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- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
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- 208000019693 Lung disease Diseases 0.000 claims description 3
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- 230000006931 brain damage Effects 0.000 claims description 3
- 231100000874 brain damage Toxicity 0.000 claims description 3
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- 125000004122 cyclic group Chemical group 0.000 claims description 3
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- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 230000003843 mucus production Effects 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims description 2
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims description 2
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000958 aryl methylene group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
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- 125000003367 polycyclic group Chemical group 0.000 claims description 2
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 121
- 238000000034 method Methods 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
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- 239000002253 acid Substances 0.000 description 53
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 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 30
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Landscapes
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07118897 | 2007-10-19 | ||
| PCT/EP2008/063747 WO2009053268A1 (de) | 2007-10-19 | 2008-10-13 | Neue phenyl-substituierte piperazino-dihydrothienopyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011500621A true JP2011500621A (ja) | 2011-01-06 |
| JP2011500621A5 JP2011500621A5 (enExample) | 2011-12-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2010529353A Pending JP2011500621A (ja) | 2007-10-19 | 2008-10-13 | 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 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20110028441A1 (enExample) |
| EP (1) | EP2214673B1 (enExample) |
| JP (1) | JP2011500621A (enExample) |
| CA (1) | CA2702447A1 (enExample) |
| WO (1) | WO2009053268A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021506805A (ja) * | 2017-12-15 | 2021-02-22 | レオ ファーマ アクティーゼルスカブ | 置換アゼチジンジヒドロチエノピリミジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用 |
| JP2021506806A (ja) * | 2017-12-15 | 2021-02-22 | レオ ファーマ アクティーゼルスカブ | 置換アゼチジンジヒドロチエノピリジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用 |
| JP2025534418A (ja) * | 2022-09-29 | 2025-10-15 | 蘇州愛科百発生物医薬技術有限公司 | 含窒素縮合複素環化合物、その調製方法、および医薬におけるその使用 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1847543A1 (de) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen |
| RU2500681C2 (ru) | 2007-10-19 | 2013-12-10 | Берингер Ингельхайм Интернациональ Гмбх | Замещенные гетероциклом пиперазинодигидротиенопиримидины |
| SI2610258T1 (sl) | 2007-10-19 | 2014-12-31 | Boehringer Ingelheim International Gmbh | Substituirani piperidino-dihidrotienopirimidini |
| EP2215093B1 (de) | 2007-10-19 | 2011-12-14 | Boehringer Ingelheim International GmbH | Neue piperazino-dihydrothienopyrimidin-derivate |
| WO2010097332A1 (de) * | 2009-02-27 | 2010-09-02 | 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 |
| US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
| US11365204B2 (en) | 2017-09-20 | 2022-06-21 | UNION therapeutics A/S | Substituted dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| WO2019115775A1 (en) | 2017-12-15 | 2019-06-20 | Leo Pharma A/S | Substituted tetrahydropyran dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| JP2025528779A (ja) * | 2022-08-09 | 2025-09-02 | シーザン ハイスーク ファーマシューティカル カンパニー リミテッド | Ｐｄｅ４ｂ阻害剤及びその用途 |
| WO2025162289A2 (zh) * | 2024-02-04 | 2025-08-07 | 西藏海思科制药有限公司 | 一种pde4b抑制剂的晶型及其在医药上的用途 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005503345A (ja) * | 2001-04-30 | 2005-02-03 | バイエル・コーポレーシヨン | 新規な４−アミノ−５，６−置換チオフェノ［２，３−ｄ］ピリミジン |
| WO2006111549A1 (de) * | 2005-04-21 | 2006-10-26 | Boehringer Ingelheim International Gmbh | Dihydrothienopyrimidine zur behandlung von entzündlichen erkrankungen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1847543A1 (de) * | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen |
-
2008
- 2008-10-13 CA CA2702447A patent/CA2702447A1/en not_active Abandoned
- 2008-10-13 US US12/738,412 patent/US20110028441A1/en not_active Abandoned
- 2008-10-13 EP EP08841954A patent/EP2214673B1/de active Active
- 2008-10-13 JP JP2010529353A patent/JP2011500621A/ja active Pending
- 2008-10-13 WO PCT/EP2008/063747 patent/WO2009053268A1/de not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005503345A (ja) * | 2001-04-30 | 2005-02-03 | バイエル・コーポレーシヨン | 新規な４−アミノ−５，６−置換チオフェノ［２，３−ｄ］ピリミジン |
| WO2006111549A1 (de) * | 2005-04-21 | 2006-10-26 | Boehringer Ingelheim International Gmbh | Dihydrothienopyrimidine zur behandlung von entzündlichen erkrankungen |
Non-Patent Citations (1)
| Title |
|---|
| JPN5010015139; ＣＨＡＫＲＡＢＯＲＴＩ: ＢＩＯＯＲＧＡＮＩＣ ＆ ＭＥＤＩＣＩＮＡＬ ＣＨＥＭＩＳＴＲＹ ＬＥＴＴＥＲＳ Ｖ１３ Ｎ８, 20030101, Ｐ１４０３-１４０８ * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021506805A (ja) * | 2017-12-15 | 2021-02-22 | レオ ファーマ アクティーゼルスカブ | 置換アゼチジンジヒドロチエノピリミジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用 |
| JP2021506806A (ja) * | 2017-12-15 | 2021-02-22 | レオ ファーマ アクティーゼルスカブ | 置換アゼチジンジヒドロチエノピリジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用 |
| JP7198820B2 (ja) | 2017-12-15 | 2023-01-04 | ユニオン・セラピューティクス・アクティエセルスカブ | 置換アゼチジンジヒドロチエノピリミジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用 |
| JP7203846B2 (ja) | 2017-12-15 | 2023-01-13 | ユニオン・セラピューティクス・アクティエセルスカブ | 置換アゼチジンジヒドロチエノピリジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用 |
| JP2025534418A (ja) * | 2022-09-29 | 2025-10-15 | 蘇州愛科百発生物医薬技術有限公司 | 含窒素縮合複素環化合物、その調製方法、および医薬におけるその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2214673A1 (de) | 2010-08-11 |
| CA2702447A1 (en) | 2009-04-30 |
| US20110028441A1 (en) | 2011-02-03 |
| WO2009053268A1 (de) | 2009-04-30 |
| EP2214673B1 (de) | 2012-05-30 |
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