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 inhibitors

Info

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
Application number
PL400149A
Other languages
Polish (pl)
Inventor
Rafal Moszczynski-Petkowski
Łukasz Bojarski
Filip Stefaniak
Maciej Wieczorek
Krzysztof Dubiel
Monika Lamparska-Przybysz
Original Assignee
Celon Pharma Spólka Z Ograniczona Odpowiedzialnoscia
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Celon Pharma Spólka Z Ograniczona Odpowiedzialnoscia filed Critical Celon Pharma Spólka Z Ograniczona Odpowiedzialnoscia
Priority to PL400149A priority Critical patent/PL400149A1/en
Priority to PCT/IB2013/056086 priority patent/WO2014016789A1/en
Publication of PL400149A1 publication Critical patent/PL400149A1/en

Links

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

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.

PL400149A 2012-07-26 2012-07-26 Pyrazolo [3,4-d] pyrimidine-4 (5H) -one derivatives as PDE9 inhibitors PL400149A1 (en)

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)

* Cited by examiner, † Cited by third party
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
KR20200068996A (en) * 2018-12-06 2020-06-16 한국화학연구원 Compound for inhibiting PDE9A and medical uses thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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
AU2004235915B2 (en) 2003-05-09 2010-08-05 Boehringer Ingelheim International Gmbh 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
NZ590788A (en) 2008-09-08 2012-11-30 Boehringer Ingelheim Int Pyrazolopyrimidines and their use for the treatment of cns disorders
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
AR077859A1 (en) 2009-08-12 2011-09-28 Boehringer Ingelheim Int COMPOUNDS FOR THE TREATMENT OF CNS DISORDERS
KR101918909B1 (en) 2010-08-12 2018-11-15 베링거 인겔하임 인터내셔날 게엠베하 6-cycloalkyl-1,5-dihydro-pyrazolo[3,4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors

Also Published As

Publication number Publication date
WO2014016789A1 (en) 2014-01-30

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