PL400149A1 - Pyrazolo [3,4-d] pyrimidine-4 (5H) -one derivatives as PDE9 inhibitors - Google Patents
Pyrazolo [3,4-d] pyrimidine-4 (5H) -one derivatives as PDE9 inhibitorsInfo
- Publication number
- PL400149A1 PL400149A1 PL400149A PL40014912A PL400149A1 PL 400149 A1 PL400149 A1 PL 400149A1 PL 400149 A PL400149 A PL 400149A PL 40014912 A PL40014912 A PL 40014912A PL 400149 A1 PL400149 A1 PL 400149A1
- Authority
- PL
- Poland
- Prior art keywords
- alkyl
- group
- straight
- pyrazolo
- pyrimidine
- Prior art date
Links
- OOOBGFAUGXVKGI-UHFFFAOYSA-N 5,6-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical class O=C1NCN=C2N=NC=C12 OOOBGFAUGXVKGI-UHFFFAOYSA-N 0.000 title 1
- 229940076380 PDE9 inhibitor Drugs 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 208000028698 Cognitive impairment Diseases 0.000 abstract 1
- 101100407341 Drosophila melanogaster Pde9 gene Proteins 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 208000010877 cognitive disease Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000004770 neurodegeneration Effects 0.000 abstract 1
- 208000015122 neurodegenerative disease Diseases 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Zwiazki przedstawione wzorem ogólnym (I), w którym R1 jest wybrany z grupy skladajacej sie z fenylu niepodstawionego lub podstawionego przez 1 do 3 podstawników wybranych z F, Cl, Br, J, CN, -O-C1-C3-alkilu, fluorowanego -O-C1-C3-alkilu, -(CH2)mOH i 5-czlonowego ugrupowania heterocyklicznego majacego 1 lub 2 heteroatomy wybrane z N, O i S; i 6- lub 10-czlonowego heteroarylu, majacego 1 do 3 heteroatomów wybranych niezaleznie z O, N i S; R2 i R3 oznaczaja niezaleznie od siebie atom H lub alkil C1-C3 o lancuchu prostym lub rozgalezionym; R4 jest wybrany z grupy skladajacej sie z 4- do 6-czlonowego cykloalkilu, w którym jeden z atomów wegla pierscienia moze byc zastapiony przez atom O; i alkilu C1 do C4 o lancuchu prostym lub rozgalezionym; Q oznacza wiazanie lub grupe C1-C3-alkilenowa, która moze byc ewentualnie podstawiona przed jedna do trzech grup C1-C3-alkilowych; X jest wybrany z grupy skladajacej sie z O, NR5, i S(O)p; R5 oznacza atom H lub alkil C1-C3; m oznacza liczbe 1, 2 lub 3; p oznacza liczbe 0, 1 lub 2; oraz ich dopuszczalne farmaceutycznie sole, sa inhibitorami PDE9 i moga znalezc zastosowanie w leczeniu zaburzen funkcji poznawczej i chorób neurozwyrodnieniowych.Compounds represented by general formula (I), wherein R1 is selected from the group consisting of unsubstituted or substituted phenyl with 1 to 3 substituents selected from F, Cl, Br, J, CN, -O-C1-C3-alkyl, fluorinated - O-C1-C3-alkyl, - (CH2) mOH, and a 5-membered heterocyclic moiety having 1 or 2 heteroatoms selected from N, O and S; and a 6- or 10-membered heteroaryl having 1 to 3 heteroatoms independently selected from O, N and S; R2 and R3 are, independently of each other, H or C1-C3 alkyl of a straight or branched chain; R4 is selected from the group consisting of 4- to 6-membered cycloalkyl in which one of the ring carbon atoms may be replaced by O; and straight or branched C1 to C4 alkyl; Q is a bond or a C1-C3 alkylene group which may be optionally substituted by one to three C1-C3 alkyl groups; X is selected from the group consisting of O, NR5, and S (O) p; R5 is H or C1-C3 alkyl; m is the number 1, 2 or 3; p is 0, 1 or 2; and their pharmaceutically acceptable salts are inhibitors of PDE9 and may find use in the treatment of cognitive impairment and neurodegenerative diseases.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL400149A PL400149A1 (en) | 2012-07-26 | 2012-07-26 | Pyrazolo [3,4-d] pyrimidine-4 (5H) -one derivatives as PDE9 inhibitors |
| PCT/IB2013/056086 WO2014016789A1 (en) | 2012-07-26 | 2013-07-24 | Pyrazolo[3,4-d]pyrimidin-4(5h)-one derivatives as pde9 inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL400149A PL400149A1 (en) | 2012-07-26 | 2012-07-26 | Pyrazolo [3,4-d] pyrimidine-4 (5H) -one derivatives as PDE9 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL400149A1 true PL400149A1 (en) | 2014-02-03 |
Family
ID=49301560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL400149A PL400149A1 (en) | 2012-07-26 | 2012-07-26 | Pyrazolo [3,4-d] pyrimidine-4 (5H) -one derivatives as PDE9 inhibitors |
Country Status (2)
| Country | Link |
|---|---|
| PL (1) | PL400149A1 (en) |
| WO (1) | WO2014016789A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669680B (en) * | 2016-03-24 | 2018-02-23 | 南京药捷安康生物科技有限公司 | (1H) ketone derivatives class PDE9A inhibitor of pyrrolo- [2,1 f] [1,2,4] triazine 4 |
| KR102712818B1 (en) * | 2018-12-06 | 2024-09-30 | 한국화학연구원 | Compound for inhibiting PDE9A and medical uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040220186A1 (en) | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
| CA2524900C (en) | 2003-05-09 | 2012-03-20 | Bayer Healthcare Ag | 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines |
| 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 |
| JP5453431B2 (en) | 2008-09-08 | 2014-03-26 | 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 | Pyrazolopyrimidines and their use for the treatment of CNS disorders |
| PE20120505A1 (en) | 2009-03-31 | 2012-05-09 | Boehringer Ingelheim Int | DERIVATIVES OF 1-HETEROCICLIL-1,5-DIHIDRO-PIRAZOLO [3,4-D] PYRIMIDIN-4-ONA AS MODULATORS OF PDE9A |
| AR077859A1 (en) | 2009-08-12 | 2011-09-28 | Boehringer Ingelheim Int | COMPOUNDS FOR THE TREATMENT OF CNS DISORDERS |
| AP2012006631A0 (en) | 2010-08-12 | 2012-12-31 | Boehringer Ingelheim Int | 6-Cycloalkyl-1, 5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivatives and their use as PDE9A inhibitors |
-
2012
- 2012-07-26 PL PL400149A patent/PL400149A1/en not_active Application Discontinuation
-
2013
- 2013-07-24 WO PCT/IB2013/056086 patent/WO2014016789A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014016789A1 (en) | 2014-01-30 |
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| REFS | Decisions on refusal to grant patents (taken after the publication of the particulars of the applications) |