JP2004523585A5 - - Google Patents
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- JP2004523585A5 JP2004523585A5 JP2002573783A JP2002573783A JP2004523585A5 JP 2004523585 A5 JP2004523585 A5 JP 2004523585A5 JP 2002573783 A JP2002573783 A JP 2002573783A JP 2002573783 A JP2002573783 A JP 2002573783A JP 2004523585 A5 JP2004523585 A5 JP 2004523585A5
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- Prior art keywords
- alkyl
- het
- substituents
- group
- halo
- Prior art date
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- 125000001424 substituent group Chemical group 0.000 claims 84
- 125000005843 halogen group Chemical group 0.000 claims 37
- 125000003118 aryl group Chemical group 0.000 claims 28
- 229910052799 carbon Inorganic materials 0.000 claims 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 239000000203 mixture Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- PIKPOIQYNGBWCI-UHFFFAOYSA-N 1-[2-[di(propan-2-yl)amino]ethyl]-3-ethyl-5-(5-methylsulfonyl-2-propoxyphenyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(C)(=O)=O)C=C1C(NC1=O)=NC2=C1N(CCN(C(C)C)C(C)C)N=C2CC PIKPOIQYNGBWCI-UHFFFAOYSA-N 0.000 claims 1
- YVUSUVMJHKDRDZ-UHFFFAOYSA-N 2-(cyclopropylmethyl)-3-ethyl-5-(5-methylsulfonyl-2-propoxyphenyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(C)(=O)=O)C=C1C(NC(=O)C1=N2)=NC1=C(CC)N2CC1CC1 YVUSUVMJHKDRDZ-UHFFFAOYSA-N 0.000 claims 1
- IVBLNBSQGVIIHC-UHFFFAOYSA-N 2-[2-[di(propan-2-yl)amino]ethyl]-3-ethyl-5-(5-methylsulfonyl-2-propoxyphenyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(C)(=O)=O)C=C1C1=NC2=C(CC)N(CCN(C(C)C)C(C)C)N=C2C(=O)N1 IVBLNBSQGVIIHC-UHFFFAOYSA-N 0.000 claims 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims 1
- QWJYUFUNAUMBLH-UHFFFAOYSA-N 3-ethyl-1-[(1-methylimidazol-2-yl)methyl]-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C=2C(=CC=C(C=2)S(C)(=O)=O)OCC(C)C)NC(=O)C2=C1C(CC)=NN2CC1=NC=CN1C QWJYUFUNAUMBLH-UHFFFAOYSA-N 0.000 claims 1
- WNGQRPDJJMNTGZ-INIZCTEOSA-N 3-ethyl-1-[[(2s)-1-methylpiperidin-2-yl]methyl]-5-(5-methylsulfonyl-2-propoxyphenyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(C)(=O)=O)C=C1C(NC1=O)=NC2=C1N(C[C@H]1N(CCCC1)C)N=C2CC WNGQRPDJJMNTGZ-INIZCTEOSA-N 0.000 claims 1
- WWQWUKGFSVJWGQ-HNNXBMFYSA-N 3-ethyl-1-[[(2s)-1-methylpyrrolidin-2-yl]methyl]-5-(5-methylsulfonyl-2-propoxyphenyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(C)(=O)=O)C=C1C(NC1=O)=NC2=C1N(C[C@H]1N(CCC1)C)N=C2CC WWQWUKGFSVJWGQ-HNNXBMFYSA-N 0.000 claims 1
- VWDAVCYECNRGMJ-UHFFFAOYSA-N 3-ethyl-2-(1-methylpiperidin-4-yl)-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCC=1N(C2CCN(C)CC2)N=C(C(N2)=O)C=1N=C2C1=CC(S(C)(=O)=O)=CC=C1OCC(C)C VWDAVCYECNRGMJ-UHFFFAOYSA-N 0.000 claims 1
- SBLQIIKQJKOYSF-UHFFFAOYSA-N 3-ethyl-2-[(1-methylimidazol-2-yl)methyl]-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C(NC(=N2)C=3C(=CC=C(C=3)S(C)(=O)=O)OCC(C)C)=O)C2=C(CC)N1CC1=NC=CN1C SBLQIIKQJKOYSF-UHFFFAOYSA-N 0.000 claims 1
- QHDKLOVUZYGQFQ-INIZCTEOSA-N 3-ethyl-5-(5-ethylsulfonyl-2-propoxyphenyl)-1-[[(2s)-1-methylpyrrolidin-2-yl]methyl]-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)CC)C=C1C(NC1=O)=NC2=C1N(C[C@H]1N(CCC1)C)N=C2CC QHDKLOVUZYGQFQ-INIZCTEOSA-N 0.000 claims 1
- GGJDBGQWIQPMOD-UHFFFAOYSA-N 3-ethyl-5-(5-methylsulfonyl-2-propoxyphenyl)-1-(pyridin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(C)(=O)=O)C=C1C(NC1=O)=NC2=C1N(CC=1N=CC=CC=1)N=C2CC GGJDBGQWIQPMOD-UHFFFAOYSA-N 0.000 claims 1
- SBVCLWYADDSRFV-UHFFFAOYSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-1-(1-propan-2-ylazetidin-3-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C=2C(=CC=C(C=2)S(C)(=O)=O)OCC(C)C)NC(=O)C2=C1C(CC)=NN2C1CN(C(C)C)C1 SBVCLWYADDSRFV-UHFFFAOYSA-N 0.000 claims 1
- MCBPCZHOJMXQNQ-UHFFFAOYSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-1-(pyridazin-3-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C=2C(=CC=C(C=2)S(C)(=O)=O)OCC(C)C)NC(=O)C2=C1C(CC)=NN2CC1=CC=CN=N1 MCBPCZHOJMXQNQ-UHFFFAOYSA-N 0.000 claims 1
- QHCIJIWDKIAJKV-INIZCTEOSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-1-[[(2s)-1-methylpyrrolidin-2-yl]methyl]-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C=2C(=CC=C(C=2)S(C)(=O)=O)OCC(C)C)NC(=O)C2=C1C(CC)=NN2C[C@@H]1CCCN1C QHCIJIWDKIAJKV-INIZCTEOSA-N 0.000 claims 1
- PDYRLQIFHRDIOM-UHFFFAOYSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-2-(1-propan-2-ylpiperidin-4-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCC=1N(C2CCN(CC2)C(C)C)N=C(C(N2)=O)C=1N=C2C1=CC(S(C)(=O)=O)=CC=C1OCC(C)C PDYRLQIFHRDIOM-UHFFFAOYSA-N 0.000 claims 1
- MJQTUQXKHJMTSP-UHFFFAOYSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-2-(2-morpholin-4-ylethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C(NC(=N2)C=3C(=CC=C(C=3)S(C)(=O)=O)OCC(C)C)=O)C2=C(CC)N1CCN1CCOCC1 MJQTUQXKHJMTSP-UHFFFAOYSA-N 0.000 claims 1
- JVYCVEJUZOOADZ-UHFFFAOYSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-2-(pyridazin-3-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C(NC(=N2)C=3C(=CC=C(C=3)S(C)(=O)=O)OCC(C)C)=O)C2=C(CC)N1CC1=CC=CN=N1 JVYCVEJUZOOADZ-UHFFFAOYSA-N 0.000 claims 1
- DYOXXYIEPSTIBL-UHFFFAOYSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-2-(pyridin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C(NC(=N2)C=3C(=CC=C(C=3)S(C)(=O)=O)OCC(C)C)=O)C2=C(CC)N1CC1=CC=CC=N1 DYOXXYIEPSTIBL-UHFFFAOYSA-N 0.000 claims 1
- AIWNYWDOCHMLND-MRXNPFEDSA-N 3-ethyl-5-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]-2-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1=C(C(NC(=N2)C=3C(=CC=C(C=3)S(C)(=O)=O)OCC(C)C)=O)C2=C(CC)N1C[C@H]1CCCN1C AIWNYWDOCHMLND-MRXNPFEDSA-N 0.000 claims 1
- JHNISIYCOASGJZ-UHFFFAOYSA-N 5-(2-butoxy-5-methylsulfonylphenyl)-3-ethyl-1-(pyridin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCCOC1=CC=C(S(C)(=O)=O)C=C1C(NC1=O)=NC2=C1N(CC=1N=CC=CC=1)N=C2CC JHNISIYCOASGJZ-UHFFFAOYSA-N 0.000 claims 1
- ZKPGDHFFXKOUDE-UHFFFAOYSA-N 5-(2-butoxy-5-methylsulfonylphenyl)-3-ethyl-2-(1-propan-2-ylazetidin-3-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCCOC1=CC=C(S(C)(=O)=O)C=C1C1=NC2=C(CC)N(C3CN(C3)C(C)C)N=C2C(=O)N1 ZKPGDHFFXKOUDE-UHFFFAOYSA-N 0.000 claims 1
- WIKKCYQPPMXKAY-UHFFFAOYSA-N 5-(2-butoxy-5-methylsulfonylphenyl)-3-ethyl-2-(2-methoxyethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCCOC1=CC=C(S(C)(=O)=O)C=C1C1=NC2=C(CC)N(CCOC)N=C2C(=O)N1 WIKKCYQPPMXKAY-UHFFFAOYSA-N 0.000 claims 1
- FYJHRHOEHOZHEH-UHFFFAOYSA-N 5-(2-butoxy-5-methylsulfonylphenyl)-3-ethyl-2-(2-morpholin-4-ylethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCCOC1=CC=C(S(C)(=O)=O)C=C1C(NC(=O)C1=N2)=NC1=C(CC)N2CCN1CCOCC1 FYJHRHOEHOZHEH-UHFFFAOYSA-N 0.000 claims 1
- JWQFBJQJGITHSY-UHFFFAOYSA-N 5-(2-ethoxy-5-methylsulfonylphenyl)-1-methyl-3-propyl-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C1=CC(S(C)(=O)=O)=CC=C1OCC JWQFBJQJGITHSY-UHFFFAOYSA-N 0.000 claims 1
- 101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 208000021663 Female sexual arousal disease Diseases 0.000 claims 1
- 101150098694 PDE5A gene Proteins 0.000 claims 1
- 208000027520 Somatoform disease Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- -1 are independently H Chemical group 0.000 claims 1
- 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 208000027753 pain disease Diseases 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- QYCUDRKEQFHGDK-UHFFFAOYSA-N spiro[1,3-oxazolidine-5,9'-fluorene]-2,4-dione Chemical compound O1C(=O)NC(=O)C21C1=CC=CC=C1C1=CC=CC=C12 QYCUDRKEQFHGDK-UHFFFAOYSA-N 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0106661.2A GB0106661D0 (en) | 2001-03-16 | 2001-03-16 | Pharmaceutically active compounds |
| PCT/IB2002/000659 WO2002074774A1 (en) | 2001-03-16 | 2002-03-04 | Cyclic guanosine 3',5'-monophosphate phosphodiesterase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004523585A JP2004523585A (ja) | 2004-08-05 |
| JP2004523585A5 true JP2004523585A5 (enExample) | 2005-12-22 |
Family
ID=9910932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002573783A Pending JP2004523585A (ja) | 2001-03-16 | 2002-03-04 | サイクリックグアノシン３’，５’−モノホスフェートホスホジエステラーゼ阻害剤 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1368352B1 (enExample) |
| JP (1) | JP2004523585A (enExample) |
| AT (1) | ATE283856T1 (enExample) |
| BR (1) | BR0208154A (enExample) |
| CA (1) | CA2439528A1 (enExample) |
| DE (1) | DE60202134T2 (enExample) |
| ES (1) | ES2231667T3 (enExample) |
| GB (1) | GB0106661D0 (enExample) |
| MX (1) | MXPA03005937A (enExample) |
| WO (1) | WO2002074774A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1348707B1 (en) * | 2002-03-28 | 2010-08-25 | Ustav Experimentalni Botaniky AV CR, v.v.i. (Institute of Experimental Botany Academy of Sciences of the Czech Republic, PRO) | Pyrazolo[4,3-d]pyrimidines, processes for their preparation and methods for therapy |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| ES2341240T3 (es) | 2002-12-13 | 2010-06-17 | Warner-Lambert Company Llc | Ligando alfa-2-delta para tratar los sintomas del tracto urinario inferior. |
| CN100374441C (zh) * | 2003-06-06 | 2008-03-12 | 天津倍方科技发展有限公司 | 二氢吡咯[2，3-d]嘧啶-4-酮衍生物，其制备方法及其制药用途 |
| JP2006219374A (ja) | 2003-06-13 | 2006-08-24 | Daiichi Asubio Pharma Co Ltd | Ｐｄｅ７阻害作用を有するイミダゾトリアジノン誘導体 |
| NZ544756A (en) | 2003-07-22 | 2009-09-25 | Astex Therapeutics Ltd | 3,4-Disubstituted 1H-pyrazole compounds and their use as cyclin dependent kinases (CDK) and glycogen synthase kinase-3 (GSK-3) modulators |
| WO2005028480A2 (en) * | 2003-09-03 | 2005-03-31 | Neurogen Corporation | 5-aryl-pyrazolo[4,3-d]pyrimidines, pyridines, and pyrazines and related compounds |
| US7485637B2 (en) | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
| AR054425A1 (es) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
| CN101119968B (zh) | 2005-02-07 | 2011-08-31 | 弗·哈夫曼-拉罗切有限公司 | 作为甘氨酸转运蛋白1抑制剂的杂环取代的苯基甲酮衍生物 |
| AU2006213985C1 (en) * | 2005-02-18 | 2012-03-15 | Surface Logix, Inc. | Pharmacokinetically improved compounds |
| EP2514751A1 (en) | 2005-11-15 | 2012-10-24 | Vertex Pharmaceuticals, Inc. | Azaindazoles useful as inhibitor of kinases |
| ES2343141T3 (es) * | 2005-11-16 | 2010-07-23 | F. Hoffmann-La Roche Ag | Nuevo procedimiento para la preparacion de thoc. |
| WO2008074194A1 (en) * | 2006-12-21 | 2008-06-26 | Topharman Shanghai Co., Ltd. | A process for the preparation of sildenafil and the intermediates thereof |
| WO2008140051A1 (ja) * | 2007-05-11 | 2008-11-20 | Santen Pharmaceutical Co., Ltd. | 非麦角系の選択的ｄ２受容体アゴニストを有効成分として含有する後眼部疾患の予防又は治療剤 |
| EP2217602B1 (en) | 2007-11-30 | 2018-08-29 | Boehringer Ingelheim International GmbH | 1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one derivatives and their use as pde9a modulators for the treatment of cns disorders |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| PE20110383A1 (es) | 2008-09-08 | 2011-07-15 | Boehringer Ingelheim Int | Pirazolopirimidinonas como inhibidores de la fosfodiesterasa 9a (pde9a) |
| EP2379076B1 (en) | 2008-12-23 | 2014-11-12 | The Trustees of Columbia University in the City of New York | Phosphodiesterase inhibitors and uses thereof |
| CA2757231A1 (en) | 2009-03-31 | 2010-10-07 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| TWI393578B (zh) | 2009-07-07 | 2013-04-21 | Shl Group Ab | 注射裝置 |
| CA2807687C (en) | 2010-08-12 | 2019-01-08 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-1, 5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| KR101649610B1 (ko) | 2011-04-21 | 2016-08-19 | 오리제니스 게엠베하 | 키나아제 억제제로서의 헤테로사이클릭 화합물 |
| PE20140928A1 (es) * | 2011-04-21 | 2014-08-24 | Origenis Gmbh | Pirazolo[4,3-d]pirimidinas utiles como inhibidores de cinasas |
| AU2013205306B2 (en) | 2012-03-16 | 2015-09-17 | Axikin Pharmaceuticals, Inc. | 3,5-diaminopyrazole kinase inhibitors |
| US10000482B2 (en) | 2012-10-19 | 2018-06-19 | Origenis Gmbh | Kinase inhibitors |
| US9637491B2 (en) | 2012-10-19 | 2017-05-02 | Origenis Gmbh | Pyrazolo[4,3-D]pyrimidines as kinase inhibitors |
| NZ631142A (en) | 2013-09-18 | 2016-03-31 | Axikin Pharmaceuticals Inc | Pharmaceutically acceptable salts of 3,5-diaminopyrazole kinase inhibitors |
| JP2017500333A (ja) * | 2013-12-20 | 2017-01-05 | バイエル・ファルマ・アクティエンゲゼルシャフト | グルコース輸送阻害剤 |
| CN107250116B (zh) | 2014-12-23 | 2020-10-27 | 艾士盟医疗公司 | 3,5-二氨基吡唑激酶抑制剂 |
| ES2912648T3 (es) * | 2015-11-16 | 2022-05-26 | Topadur Pharma Ag | Derivados de 2-fenil-3,4-dihidropirrolo[2,1-f] [1,2,4]triazinona como inhibidores de la fosfodiesterasa y usos de los mismos |
| CN105669680B (zh) * | 2016-03-24 | 2018-02-23 | 南京药捷安康生物科技有限公司 | 吡咯并[2,1‑f][1,2,4]三嗪‑4(1H)‑酮衍生物类PDE9A抑制剂 |
| JP2025513455A (ja) | 2022-04-22 | 2025-04-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | 疼痛の治療のためのヘテロアリール化合物 |
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| GB1493685A (en) * | 1970-12-15 | 1977-11-30 | May & Baker Ltd | 8-azapurinones |
| GB8817651D0 (en) * | 1988-07-25 | 1988-09-01 | Smith Kline French Lab | Chemical compounds |
| US6225315B1 (en) * | 1998-11-30 | 2001-05-01 | Pfizer Inc | Method of treating nitrate-induced tolerance |
| KR20020038941A (ko) * | 1999-10-11 | 2002-05-24 | 디. 제이. 우드, 스피겔 알렌 제이 | 포스포디에스테라아제 억제제로서의5-(2-치환된-5-헤테로사이클릴설포닐피리드-3-일)-디하이드로피라졸로[4,3-ｄ]피리미딘-7-온 |
-
2001
- 2001-03-16 GB GBGB0106661.2A patent/GB0106661D0/en not_active Ceased
-
2002
- 2002-03-04 JP JP2002573783A patent/JP2004523585A/ja active Pending
- 2002-03-04 AT AT02701497T patent/ATE283856T1/de not_active IP Right Cessation
- 2002-03-04 EP EP02701497A patent/EP1368352B1/en not_active Expired - Lifetime
- 2002-03-04 CA CA002439528A patent/CA2439528A1/en not_active Abandoned
- 2002-03-04 MX MXPA03005937A patent/MXPA03005937A/es unknown
- 2002-03-04 DE DE60202134T patent/DE60202134T2/de not_active Expired - Fee Related
- 2002-03-04 WO PCT/IB2002/000659 patent/WO2002074774A1/en not_active Ceased
- 2002-03-04 ES ES02701497T patent/ES2231667T3/es not_active Expired - Lifetime
- 2002-03-04 BR BR0208154-7A patent/BR0208154A/pt not_active IP Right Cessation
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