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
- 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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- 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 (https=) | 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 (https=) |
| JP (1) | JP2004523585A (https=) |
| AT (1) | ATE283856T1 (https=) |
| BR (1) | BR0208154A (https=) |
| CA (1) | CA2439528A1 (https=) |
| DE (1) | DE60202134T2 (https=) |
| ES (1) | ES2231667T3 (https=) |
| GB (1) | GB0106661D0 (https=) |
| MX (1) | MXPA03005937A (https=) |
| WO (1) | WO2002074774A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE478872T1 (de) * | 2002-03-28 | 2010-09-15 | Ustav Ex Botan Av Cr V V I I O | Pyrazoloä4,3-düpyrimidine, verfahren zu ihrer herstellung und therapeutische anwendung |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| AU2003303041B2 (en) | 2002-12-13 | 2008-07-24 | Warner-Lambert Company Llc | Alpha-2-delta ligand to treat lower urinary tract symptoms |
| 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 |
| CA2532965C (en) | 2003-07-22 | 2013-05-14 | Astex Therapeutics Limited | 3, 4-disubstituted 1h-pyrazole compounds and their use as cyclin dependent kinases (cdk) and glycogen synthase kinase-3 (gsk-3) modulators |
| CA2537916A1 (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 |
| 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. |
| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
| DE602006010665D1 (en) | 2005-02-07 | 2010-01-07 | Hoffmann La Roche | Heterocyclsche substituierte phenylmethanone als inhibitoren des glycintransporters 1 |
| CN102351862A (zh) * | 2005-02-18 | 2012-02-15 | 表面线段公司 | 药动学改善的化合物 |
| WO2007059219A1 (en) | 2005-11-15 | 2007-05-24 | Vertex Pharmaceuticals Incorporated | Azaindazoles useful as inhibitors of kinases |
| ES2343141T3 (es) * | 2005-11-16 | 2010-07-23 | F. Hoffmann-La Roche Ag | Nuevo procedimiento para la preparacion de thoc. |
| CN101563348B (zh) * | 2006-12-21 | 2011-08-24 | 上海特化医药科技有限公司 | 西地那非的制备方法及其中间体 |
| RU2470635C2 (ru) * | 2007-05-11 | 2012-12-27 | Сантен Фармасьютикал Ко., Лтд. | Профилактическое или терапевтическое средство, применяемое при заболеваниях заднего отдела глаза |
| JP5498392B2 (ja) | 2007-11-30 | 2014-05-21 | 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 | １，５−ジヒドロ−ピラゾロ［３，４−ｄ］ピリミジン−４−オン誘導体及びｃｎｓ障害の治療のためのｐｄｅ９ａモジュレーターとしてのそれらの使用 |
| 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 |
| KR20110063447A (ko) | 2008-09-08 | 2011-06-10 | 베링거 인겔하임 인터내셔날 게엠베하 | 피라졸로피리미딘 및 ｃｎｓ 장애의 치료를 위한 이들의 용도 |
| JP2012513464A (ja) | 2008-12-23 | 2012-06-14 | ザ トラスティーズ オブ コロンビア ユニヴァーシティ イン ザ シティ オブ ニューヨーク | ホスホジエステラーゼ阻害剤及びその使用 |
| PT2414363E (pt) | 2009-03-31 | 2014-02-26 | Boehringer Ingelheim Int | Derivados de 1-heterociclil-1,5-di-hidro-pirazolo[3,4- d]pirimidin-4-ona e sua utilização como moduladores de pde9a |
| TWI393578B (zh) | 2009-07-07 | 2013-04-21 | Shl Group Ab | 注射裝置 |
| EP2603511B1 (en) | 2010-08-12 | 2017-03-15 | 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 |
| AU2012244549B2 (en) | 2011-04-21 | 2017-04-20 | Origenis Gmbh | Heterocyclic compounds as kinase inhibitors |
| AP2013007253A0 (en) * | 2011-04-21 | 2013-11-30 | Origenis Gmbh | Pyrazolo [4,3-D] pyrimidines useful as kinase inhibitors |
| WO2013138617A1 (en) | 2012-03-16 | 2013-09-19 | Axikin Pharmaceuticals, Inc. | 3,5-diaminopyrazole kinase inhibitors |
| WO2014060112A1 (en) | 2012-10-19 | 2014-04-24 | Origenis Gmbh | Pyrazolo[4,3-d]pyrimidines as kinase inhibitors |
| WO2014060113A1 (en) | 2012-10-19 | 2014-04-24 | Origenis Gmbh | Novel kinase inhibitors |
| NZ631142A (en) | 2013-09-18 | 2016-03-31 | Axikin Pharmaceuticals Inc | Pharmaceutically acceptable salts of 3,5-diaminopyrazole kinase inhibitors |
| US20170037028A1 (en) * | 2013-12-20 | 2017-02-09 | Bayer Pharma Aktiengesellschaft | Glucose transport inhibitors |
| TWI703133B (zh) | 2014-12-23 | 2020-09-01 | 美商艾克斯基製藥公司 | ３,５-二胺基吡唑激酶抑制劑 |
| SMT202200190T1 (it) | 2015-11-16 | 2022-07-21 | Topadur Pharma Ag | Derivati del 2-fenil-3,4-diidropirrolo[2,1-f] [1,2,4]triazinone come inibitori della fosfodesterasi e loro usi |
| 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 |
| WO2023205463A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| HK1049834A1 (zh) * | 1999-10-11 | 2003-05-30 | 辉瑞大药厂 | 用作磷酸二酯酶抑制剂的5-(2-取代的-5-杂环基磺酰基吡啶-3-基)-二氢吡唑并[4，3-d]嘧啶-7-酮类化合物 |
-
2001
- 2001-03-16 GB GBGB0106661.2A patent/GB0106661D0/en not_active Ceased
-
2002
- 2002-03-04 EP EP02701497A patent/EP1368352B1/en not_active Expired - Lifetime
- 2002-03-04 ES ES02701497T patent/ES2231667T3/es not_active Expired - Lifetime
- 2002-03-04 DE DE60202134T patent/DE60202134T2/de not_active Expired - Fee Related
- 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 CA CA002439528A patent/CA2439528A1/en not_active Abandoned
- 2002-03-04 BR BR0208154-7A patent/BR0208154A/pt not_active IP Right Cessation
- 2002-03-04 WO PCT/IB2002/000659 patent/WO2002074774A1/en not_active Ceased
- 2002-03-04 MX MXPA03005937A patent/MXPA03005937A/es unknown
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