HRP20140312T1 - Derivati 1-heterociklil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona i njihova uporaba kao modulatori za pde9a - Google Patents

Derivati 1-heterociklil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona i njihova uporaba kao modulatori za pde9a Download PDF

Info

Publication number
HRP20140312T1
HRP20140312T1 HRP20140312AT HRP20140312T HRP20140312T1 HR P20140312 T1 HRP20140312 T1 HR P20140312T1 HR P20140312A T HRP20140312A T HR P20140312AT HR P20140312 T HRP20140312 T HR P20140312T HR P20140312 T1 HRP20140312 T1 HR P20140312T1
Authority
HR
Croatia
Prior art keywords
alkyl
group
fluorine
hf2c
fh2c
Prior art date
Application number
HRP20140312AT
Other languages
English (en)
Inventor
Riccardo Giovannini
Cornelia Dorner-Ciossek
Christian Eickmeier
Dennis Fiegen
Thomas Fox
Klaus Fuchs
Niklas Heine
Holger Rosenbrock
Gerhard Schaenzle
Original Assignee
Boehringer Ingelheim International Gmbh
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
Priority claimed from PCT/EP2009/053907 external-priority patent/WO2009121919A1/en
Application filed by Boehringer Ingelheim International Gmbh filed Critical Boehringer Ingelheim International Gmbh
Publication of HRP20140312T1 publication Critical patent/HRP20140312T1/hr

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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Claims (35)

1. Spoj, naznačen time, da ima formulu (I) [image] gdje Hc predstavlja tetrahidropiranil-, pri čemu jedan ili više atoma iz njegovog ugljikovog prstena može/mogu biti po želji supstituiran/i s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je odabran iz skupine od fenila ili heteroarila; V je odabran iz skupine od fenila ili heteroarila; -* je vezna točka s kojom je W priključen na skupinu CR2R3 u formuli (I); pri čemu W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, C1-6-alkil-, F3C-, HF2C-, FH2C-, F3C-CH2-, F3C-O-, HF2C-O-, C3-7-heterocikloalkil-, H-O-C1-6-alkil-, C1-6-alkil-O-C1-6-alkil-, C3-7-cikloalkil-O-C1-6-alkil-, C3-7-cikloalkil-C1-3-alkil-O-C1-6-alkil-, fenil-O-C1-6-alkil-, benzil-O-C1-6-alkil-, H-O-, C1-6-alkil-O-, C3-7-cikloalkil-O-, C3-7-cikloalkil-C1-3-alkil-O-, fenil-O-, benzil-O-, N-morfolinil, i NC-; R2 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
2. Spoj prema zahtjevu 1, naznačen time, da Hc predstavlja tetrahidropiranil-, pri čemu jedan ili više atoma iz njegovog ugljikovog prstena može/mogu biti po želji supstituiran/i s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je odabran iz skupine od fenila ili heteroarila, pri čemu je navedeni heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, furanil, piridil, pirimidil i piridazinil, V je odabran iz skupine fenila ili heteroarila, gdje je navedeni heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, pirolil, furanil, piridil, pirimidil i piridazinil, pri čemu W i V međusobno neovisno mogu biti po želji supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, C1-6-alkil-, F3C-, HF2C-, FH2C-, F3C-CH2-, F3C-O-, HF2C-O-, C3-7-heterocikloalkil-, H-O-C1-6-alkil-, C1-6-alkil-O-C1-6-alkil-, C3-7-cikloalkil-O-C1-6-alkil-, C3-7-cikloalkil-C1-3-alkil-O-C1-6-alkil-, fenil-O-C1-6-alkil-, benzil-O-C1-6-alkil-, H-O-, C1-6-alkil-O-, C3-7-cikloalkil-O-, C3-7-cikloalkil-C1-3-alkil-O-, fenil-O-, benzil-O-, N-morfolinil, i NC-; R2 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
3. Spoj prema bilo kojem od zahtjeva 1 ili 2, naznačen time, da Hc je 4-tetrahidropiranil-.
4. Spoj prema zahtjevu i ili 3, naznačen time, da Hc predstavlja tetrahidropiranil-, pri čemu jedan ili više atoma iz njegovog ugljikovog prstena može/mogu biti po želji supstituiran/i s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je odabran iz skupine od fenila ili heteroarila, pri čemu je navedeni heteroaril odabran iz skupine koju čine: piridil, pirimidil i piridazinil, V je odabran iz skupine od fenila ili heteroarila, gdje je navedeni heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, pirolil, furanil, piridil, pirimidil i piridazinil, pri čemu W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, C1-6-alkil-, F3C-, HF2C-, FH2C-, F3C-CH2-, F3C-O-, HF2C-O-, C3-7-heterocikloalkil-, H-O-C1-6-alkil-,C1-6-alkil-O-C1-6-alkil-, C3-7-cikloalkil-O-C1-6-alkil-, C3-7-cikloalkil-C1-3-alkil-O-C1-6-alkil-, fenil-O-C1-6-alkil-, benzil-O-C1-6-alkil-, H-O-, C1-6-alkil-O-, C3-7-cikloalkil-O-, C3-7-cikloalkil-C1-3-alkil-O-, fenil-O-, benzil-O-, N-morfolinil, i NC-; R2 je odabran iz skupine koji čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
5. Spoj prema zahtjevu 1 ili 3, naznačen time, da Hc predstavlja tetrahidropiranil-, pri čemu jedan ili više atoma iz njegovog ugljikovog prstena može/mogu biti po želji supstituiran/i s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je odabran iz skupine od fenila ili piridinila, V je odabran iz skupine od fenila ili heteroarila, pri čemu je navedeni heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, furanil, piridil, pirimidil i piridazinil, pri čemu W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, C1-6-alkil-, F3C-, HF2C-, FH2C-, F3C-CH2-, F3C-O-, HF2C-O-, C3-7-heterocikloalkil-, H-O-C1-6-alkil-, C1-6-alkil-O-C1-6-alkil-, C3-7-cikloalkil-O-C1-6-alkil-, C3-7-cikloalkil-C1-3-alkil-O-C1-6-alkil-, fenil-O-C1-6-alkil-, benzil-O-C1-6-alkil-, H-O-, C1-6-alkil-O-, C3-7-cikloalkil-O-, C3-7-cikloalkil-C1-3-alkil-O-, fenil-O-, benzil-O-, N-morfolinil, i NC-; R2 je odabran iz skupine koji čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
6. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time, da W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, C1-6-alkil-, F3C-, F3C-CH2-, F3C-O-, HF2C-O-, C3-7-heterocikloalkil-, C1-6-alkil-O-, C3-6-cikloalkil-O-, C3-6-cikloalkil-CH2-O-, aril-CH2-O-, i NC-.
7. Spoj prema zahtjevu 5, naznačen time, da W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, H3C-, F3C-, CH3O-, N-morfolinil, i NC-.
8. Spoj prema zahtjevu 5, naznačen time, da W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, H3C-, F3C-, CH3O-, i NC-.
9. Spoj prema zahtjevu 1 ili 3, naznačen time, da Hc predstavlja tetrahidropiranil-, pri čemu jedan ili više atoma iz njegovog ugljikovog prstena može/mogu biti po želji supstituiran/i s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je odabran iz skupine od fenila ili piridila, V je odabran iz skupine od fenila ili heteroarila, pri čemu je navedeni heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, pirolil, furanil, piridil, pirimidil i piridazinil, gdje W po želji može biti supstituiran s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, H3C-, F3C-, CH3O-, i NC-, a poželjno odabranih iz skupine koju čine: fluor, klor i F3C-; i gdje V po želji može biti supstituiran s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, H3C-, tert-butil-, F3C-, CH3O-, ciklobutiloksi-, N-morfolinil, benzil-O-, i NC-; R2 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
10. Spoj prema zahtjevu i ili 3, naznačen time, da Hc predstavlja tetrahidropiranil-, pri čemu jedan ili više atoma iz njegovog ugljikovog prstena može/mogu biti po želji supstituiran/i s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W predstavlja fenil, pri čemu je W po želji supstituiran s fluorom, klorom ili F3C-; V je heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, pirolil, furanil, piridil, pirimidil i piridazinil, gdje je V po želji supstituiran s i do 4, poželjno i ili 2, najbolje s jednim supstituentom međusobno neovisno odabranim/a iz skupine koju čine: fluor, klor, H3C-, tert-butil-, F3C-, CH3O-, ciklobutiloksi-, N-morfolinil, benzil-O-, i NC-, pri čemu je V priključen na poziciji 2 od W, gdje je pozicija 1 od W priključna točka za W na skupinu CR2R3 u formuli (I); R2 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
11. Spoj prema zahtjevu 1, naznačen time, da Hc predstavlja 4-tetrahidropiranil-, pri čemu svaki atom iz njegovog ugljikovog prstena može biti po želji supstituiran s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je odabran iz skupine od fenila ili piridinila, V je odabran iz skupine od fenila ili heteroarila, pri čemu je navedeni heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, furanil, piridil, pirimidil i piridazinil, gdje W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, C1-6-alkil-, F3C-, HF2C-, FH2C-, F3C-CH2-, F3C-O-, HF2C-O-, C3-7-heterocikloalkil-, H-O-C1-6-alkil-, C1-6-alkil-O-C1-6-alkil-, C3-7-cikloalkil-O-C1-6-alkil-, C3-7-cikloalkil-C1-3-alkil-O-C1-6-alkil-, fenil-O-C1-6-alkil-, benzil-O-C1-6-alkil-, H-O-, C1-6-alkil-O-, C3-7-cikloalkil-O-, C3-7-cikloalkil-C1-3-alkil-O-, fenil-O-, benzil-O-, N-morfolinil, i NC-; R2 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
12. Spoj prema zahtjevu 11, naznačen time, da W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, C1-6-alkil-, F3C-, F3C-CH2-, F3C-O-, HF2C-O-, C3-7-heterocikloalkil-, C1-6-alkil-O-, C3-6-cikloalkil-O-, C3-6-cikloalkil-CH2-O-, aril-CH2-O-, i NC-.
13. Spoj prema zahtjevu 11, naznačen time, da W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, H3C-, F3C-, CH3O-, N-morfolinil, i NC-.
14. Spoj prema zahtjevu 11, naznačen time, da W i V međusobno neovisno mogu po želji biti supstituirani s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, H3C-, F3C-, CH3O-, i NC-.
15. Spoj prema zahtjevu 1, naznačen time, da Hc predstavlja 4-tetrahidropiranil-, pri čemu svaki atom iz njegovog ugljikovog prstena može biti po želji supstituiran s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je odabran iz skupine od fenila ili piridila, V je odabran iz skupine od fenila ili heteroarila, pri čemu je navedeni heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, pirolil, furanil, piridil, pirimidil i piridazinil, gdje W po želji može biti supstituiran s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, brom, H3C-, F3C-, CH3O-, i NC-, a poželjno odabranih iz skupine koju čine: fluor, klor i F3C-; i pri čemu V po želji može biti supstituiran s jednim ili više supstituenata odabranih iz skupine koju čine: fluor, klor, H3C-, tert-butil-, F3C-, CH3O-, ciklobutiloksi-, N-morfolinil, benzil-O-, i NC-; R2 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
16. Spoj prema zahtjevu 1, naznačen time, da Hc predstavlja 4-tetrahidropiranil-, pri čemu svaki atom iz njegovog ugljikovog prstena može biti po želji supstituiran s jednim ili dva supstituenta neovisno odabrana iz skupine koju čine: fluor, NC-, F3C-, HF2C-, FH2C-, F3C-CH2-, C1-6-alkil-, C1-6-alkil-O-, i samo jedan atom iz ugljikovog prstena može biti supstituiran s okso; R1 predstavlja skupinu V-W-* gdje W je fenil, pri čemu je W po želji supstituiran sa sljedećima: fluor, klor ili F3C-; V je heteroaril odabran iz skupine koju čine: oksadiazolil, triazolil, pirazolil, pirolil, furanil, piridil, pirimidil i piridazinil, gdje je V po želji supstituiran s 1 do 4, poželjno s 1 ili 2, najbolje s jednim supstituentom međusobno neovisno odabranim/a iz skupine koju čine: fluor, klor, H3C-, tert-butil-, F3C-, CH3O-, ciklobutiloksi-, N-morfolinil, benzil-O-, i NC-, V je priključen na poziciji 2 od W, pri čemu pozicija i od W je priključna točka za W na skupinu CR2R3 u formuli (I); R2 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R2 je H; R3 je odabran iz skupine koju čine: H-, fluor, F3C-, HF2C-, FH2C-, i C1-3-alkil-, poželjno R3 je H.
17. Spoj prema bilo kojem od zahtjeva 11 do 16, naznačen time, da Hc je nesupstituirani 4-tetrahidropiranil-.
18. Spoj prema bilo kojem od zahtjeva 1 do 9, 11 do 15 i 17, naznačen time, da V je priključen na poziciji 2 od W, pri čemu pozicija i od W je priključna točka za W na skupinu CR2R3 u formuli (I).
19. Spoj prema zahtjevu 1, naznačen time, da je spoj odabran iz sljedeće skupine: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] i [image]
20. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
21. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
22. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
23. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
24. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
25. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
26. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
27. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
28. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
29. Spoj prema zahtjevu 1, naznačen time, da ima sljedeću formulu [image]
30. Spoj prema bilo kojem od zahtjeva 1 do 29, naznačen time, da je u obliku svoje soli, poželjno je u obliku svoje farmaceutski prihvatljive soli.
31. Spoj prema bilo kojem od zahtjeva 1 do 30, naznačen time, da se upotrebljava kao lijek.
32. Spoj prema bilo kojem od zahtjeva 1 do 30, naznačen time, da se upotrebljava u postupku liječenja bolesti koja je pristupačna za inhibiciju od PDE9.
33. Spoj prema bilo kojem od zahtjeva 1 do 30, naznačen time, da se upotrebljava u postupku liječenja, poboljšavanja ili prevencije kognitivnih oslabljenja ili oštećenja koja se odnose na percepciju, koncentraciju, spoznaju, učenje ili pamćenje, poželjno kod pacijenata koji pate od sljedećih poremećaja: slabljenje mogućnosti učenja i pamćenja u starijoj dobi, gubitak pamćenja u starijim godinama, vaskularna demencija, kranio-cerebralna trauma, udar, demencija poslije moždanog udara (post stroke dementia), post-traumatska demencija, slabljenje opće koncentracije, nedostatak koncentracije kod djece s problemima učenja i pamćenja, Alzheimerova bolest, demencija s Lewy tijelima (DLB), demencija s degeneracijom prednjeg režnja, uključujući Pickov sindrom, Parkinsonova bolest, progresivna nuklearna paraliza, demencija s kortikobazalnom degeneracijom, amiotrofična lateralna skleroza (ALS), Huntingtonova bolest, multipla skleroza, talamična degeneracija, demencija Creutzfeld- Jacob, HlV-demencija, epilepsija, epilepsija sljepoočnog režnja, shizofrenija s demencijom ili Korsakoffa psihoza, još više za kognitivna oštećenja povezana s Alzheimerovom bolešću i najviše za kognitivna oštećenja koja se odnose na učenje i pamćenje kod pacijenata koji pate od Alzheimerove bolesti.
34. Farmaceutski sastav, naznačen time, da obuhvaća spoj prema bilo kojem od zahtjeva i do 30 i farmaceutski nosač, po želji u kombinaciji s nekim drugim djelotvornim sastojkom.
35. Farmaceutski sastav prema zahtjevu 34, naznačen time, da se upotrebljava za liječenje stanja kako je opisano prema bilo kojem od zahtjeva 3i do 33.
HRP20140312AT 2009-03-31 2014-04-01 Derivati 1-heterociklil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona i njihova uporaba kao modulatori za pde9a HRP20140312T1 (hr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
VE57409 2009-03-31
PCT/EP2009/053907 WO2009121919A1 (en) 2008-04-02 2009-04-01 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-d] pyrimidin-4-one derivatives and their use as pde9a modulators
EP09171906 2009-09-30
PCT/EP2010/054050 WO2010112437A1 (en) 2009-03-31 2010-03-26 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators

Publications (1)

Publication Number Publication Date
HRP20140312T1 true HRP20140312T1 (hr) 2014-05-09

Family

ID=42174243

Family Applications (1)

Application Number Title Priority Date Filing Date
HRP20140312AT HRP20140312T1 (hr) 2009-03-31 2014-04-01 Derivati 1-heterociklil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona i njihova uporaba kao modulatori za pde9a

Country Status (34)

Country Link
US (2) US8623901B2 (hr)
EP (1) EP2414363B1 (hr)
JP (1) JP5542196B2 (hr)
KR (1) KR20120003868A (hr)
CN (1) CN102365285B (hr)
AP (1) AP2011005819A0 (hr)
AR (1) AR076171A1 (hr)
AU (1) AU2010230290B2 (hr)
BR (1) BRPI1011533A2 (hr)
CA (1) CA2757231A1 (hr)
CL (1) CL2011002454A1 (hr)
CO (1) CO6501182A2 (hr)
DK (1) DK2414363T3 (hr)
EA (1) EA201101395A1 (hr)
EC (1) ECSP11011386A (hr)
ES (1) ES2460019T3 (hr)
GE (1) GEP20146098B (hr)
HK (1) HK1163105A1 (hr)
HR (1) HRP20140312T1 (hr)
IL (1) IL214436A0 (hr)
MA (1) MA33152B1 (hr)
MX (1) MX2011010184A (hr)
MY (1) MY156377A (hr)
NZ (1) NZ594567A (hr)
PE (1) PE20120505A1 (hr)
PL (1) PL2414363T3 (hr)
PT (1) PT2414363E (hr)
RS (1) RS53167B (hr)
SG (1) SG174964A1 (hr)
SI (1) SI2414363T1 (hr)
TN (1) TN2011000493A1 (hr)
TW (1) TW201100426A (hr)
UY (1) UY32531A (hr)
WO (1) WO2010112437A1 (hr)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10238724A1 (de) * 2002-08-23 2004-03-04 Bayer Ag Alkyl-substituierte Pyrazolpyrimidine
DE10238722A1 (de) 2002-08-23 2004-03-11 Bayer Ag Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse
DE10238723A1 (de) * 2002-08-23 2004-03-11 Bayer Ag Phenyl-substituierte Pyrazolyprimidine
DE10320785A1 (de) * 2003-05-09 2004-11-25 Bayer Healthcare Ag 6-Arylmethyl-substituierte Pyrazolopyrimidine
US8044060B2 (en) * 2003-05-09 2011-10-25 Boehringer Ingelheim International Gmbh 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory
DE102004001873A1 (de) * 2004-01-14 2005-09-29 Bayer Healthcare Ag Cyanopyrimidinone
WO2009068617A1 (en) 2007-11-30 2009-06-04 Boehringer Ingelheim International Gmbh 1, 5-dihydro-pyrazolo (3, 4-d) pyrimidin-4-one derivatives and their use as pde9a modulators for the teatment 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
WO2010026214A1 (en) 2008-09-08 2010-03-11 Boehringer Ingelheim International Gmbh Pyrazolopyrimidines and their use for the treatment of cns disorders
SI2414363T1 (sl) 2009-03-31 2014-04-30 Boehringer Ingelheim Gmbh Derivati 1-heterociklil-1,5-dihidro-pirazolo/3,4-d/pirimidin-4-ona in njihova uporaba kot modulatorji za PDE9A
MY170189A (en) 2010-08-12 2019-07-09 Boehringer Ingelheim Int 6-cycloalkyl-1, 5-dihydro-pyrazolo[3,4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors
US20130040971A1 (en) 2011-02-14 2013-02-14 Boehringer Ingelheim International Gmbh 6-cycloalkyl-pyrazolopyrimidinones for the treatment of cns disorders
US8809345B2 (en) 2011-02-15 2014-08-19 Boehringer Ingelheim International Gmbh 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders
EP2769980B1 (en) 2011-10-07 2016-02-03 Eisai R&D Management Co., Ltd. Pyrazoloquinoline derivative as pde9 inhibitors
US9199959B2 (en) * 2011-10-25 2015-12-01 Shionogi & Co., Ltd. HIV replication inhibitor
US10067547B2 (en) 2012-06-28 2018-09-04 Intel Corporation Power management control of remote servers
US9454199B2 (en) 2012-06-28 2016-09-27 Intel Corporation Power management control of remote servers
PL400149A1 (pl) 2012-07-26 2014-02-03 Celon Pharma Spólka Z Ograniczona Odpowiedzialnoscia Pochodne pirazolo[3,4-d]pirymidyno-4(5H)-onu jako inhibitory PDE9
MY194905A (en) 2013-03-15 2022-12-22 Janssen Pharmaceutica Nv Processes and Intermediates for Preparing a Medicament
US9156847B2 (en) * 2013-03-15 2015-10-13 Janssen Pharmaceutica Nv Processes and intermediates for preparing a medicament
SG11201507733YA (en) 2013-04-05 2015-10-29 Eisai R&D Man Co Ltd Pyridinylpyrazoloquinoline compound
RU2655171C2 (ru) 2013-04-05 2018-05-24 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Соль производного пиразолохинолина и ее кристалл
WO2014210456A1 (en) * 2013-06-28 2014-12-31 Emory University Pyrazoline dihydroquinolones, pharmaceutical compositions, and uses
RU2659070C9 (ru) 2014-04-23 2018-08-24 Дарт Нейросайенс (Кайман) Лтд. ЗАМЕЩЕННЫЕ [1,2,4]ТРИАЗОЛО[1,5-a]ПИРИМИДИН-7-ИЛЬНЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ PDE2
TWI568737B (zh) 2014-11-05 2017-02-01 達特神經科學（開曼）有限責任公司 作為ｐｄｅ２抑制劑之經取代的５－甲基－［１，２，４］三唑并［１，５－ａ］嘧啶－２－胺化合物
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
MX2019010003A (es) * 2017-02-23 2019-12-16 Boehringer Ingelheim Int Nuevo uso medico del compuesto iii.
KR102627787B1 (ko) 2017-06-01 2024-01-23 에자이 알앤드디 매니지먼트 가부시키가이샤 피라졸로퀴놀린 유도체와 도네페질을 병용한 치매 치료제
BR112019023557A2 (pt) 2017-06-01 2020-06-02 Eisai R&D Management Co., Ltd. Composição farmacêutica compreendendo inibidor de pde9
WO2018221550A1 (ja) 2017-06-01 2018-12-06 エーザイ・アール・アンド・ディー・マネジメント株式会社 ピラゾロキノリン誘導体とメマンチンの併用による認知症治療剤
CA3061884A1 (en) 2017-06-01 2019-10-29 Eisai R&D Management Co., Ltd. Lewy body disease therapeutic agent containing pyrazoloquinoline derivative
EP3634964B1 (en) 2017-06-08 2022-02-23 Merck Sharp & Dohme Corp. Pyrazolopyrimidine pde9 inhibitors
KR20200068996A (ko) * 2018-12-06 2020-06-16 한국화학연구원 Pde9a 저해 활성을 가지는 화합물 및 이들의 의약 용도
MX2021014245A (es) 2019-05-21 2022-01-06 Janssen Pharmaceutica Nv Procedimientos y productos intermedios para preparar un inhibidor de btk.
KR20220011668A (ko) 2019-05-21 2022-01-28 얀센 파마슈티카 엔.브이. Btk 억제제 제조를 위한 방법 및 중간체
EP3972975A4 (en) * 2019-05-23 2023-11-15 Indiana University Research and Technology Corporation METHODS FOR OBJECTIVE MEMORY ASSESSMENT, EARLY DETECTION OF RISK FOR ALZHEIMER'S DISEASE, MATCHING INDIVIDUALS TO TREATMENTS, MONITORING RESPONSE TO TREATMENT, AND NEW METHODS OF USING DRUGS
CN110339197A (zh) * 2019-06-24 2019-10-18 中山大学 一种防治血管性痴呆的磷酸二酯酶9a抑制剂的用途
CN113200987A (zh) * 2021-04-29 2021-08-03 湖南华腾制药有限公司 一种伊布替尼的制备方法

Family Cites Families (180)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3165520A (en) * 1965-01-12 Certificate of correction
US3169965A (en) * 1965-02-16 New x-mercapto-pyrazolo
DE1147234B (de) 1960-05-11 1963-04-18 Ciba Geigy Verfahren zur Herstellung von 1-Isopropyl-4-hydroxy-6-benzyl-pyrazolo[3, 4-d]pyrimidin
DE1156415B (de) 1960-05-11 1963-10-31 Ciba Geigy Verfahren zur Herstellung von 1-Isopropyl-4-hydroxy-pyrazolo [3, 4-d]-pyrimidinen
CH398626A (de) 1960-05-11 1966-03-15 Ciba Geigy Verfahren zur Herstellung neuer Pyrazolopyrimidine
CH396926A (de) 1960-05-11 1965-08-15 Ciba Geigy Verfahren zur Herstellung neuer Pyrazolopyrimidine
CH396927A (de) 1960-05-11 1965-08-15 Ciba Geigy Verfahren zur Herstellung neuer Pyrazolopyrimidine
GB973361A (en) 1960-05-11 1964-10-28 Ciba Ltd Pyrazolo-pyrimidines and process for their manufacture
DE1149013B (de) 1960-05-11 1963-05-22 Ciba Geigy Verfahren zur Herstellung von 4-Oxo-4, 5-dihydro-pyrazolo-[3, 4-d]Pyrimidinen
GB937723A (en) 1960-05-11 1963-09-25 Ciba Ltd Pyrazolo-pyrimidines and process for their manufacture
CH396923A (de) 1960-05-11 1965-08-15 Ciba Geigy Verfahren zur Herstellung von 4-Mercapto-pyrazolo(3,4-d)pyrimidinen
DE1153023B (de) 1960-05-11 1963-08-22 Ciba Geigy Verfahren zur Herstellung von 4-Hydroxy-pyrazolo[3,4-d] pyrimidinen
CH396924A (de) 1960-05-11 1965-08-15 Ciba Geigy Verfahren zur Herstellung von 4-Mercapto-pyrazolo(3,4-d)pyrimidinen
DE1161281B (de) 1960-05-11 1964-01-16 Ciba Aktiengesellschaft, Basel (Schweiz) Verfahren zur Herstellung von 1-Alkyl-6-aralkyl-pyrazoloÄ3,4-dÜ-pyrimidinen.
ES267249A1 (es) 1960-05-11 1961-11-01 Ciba Geigy Procedimiento para la obtencion de pirazolo-pirimidinas nuevas
CH396925A (de) 1960-05-11 1965-08-15 Ciba Geigy Verfahren zur Herstellung neuer Pyrazolopyrimidine
US3244328A (en) * 1964-03-23 1966-04-05 Corning Glass Works Dispensing from plural sources
US3732225A (en) 1970-07-23 1973-05-08 Squibb & Sons Inc Pyrazolo(3,4-d)pyrimidine derivatives
NL167151C (nl) * 1971-04-09 1981-11-16 Acf Chemiefarma Nv Werkwijze ter bereiding van geneesmiddelen met anti-parasitaire werking op basis van halogeen bevatten- de 2,2'-methyleendifenolderivaten, alsmede werkwijze ter bereiding van deze geneeskrachtige verbindingen.
US3847908A (en) 1973-03-05 1974-11-12 Squibb & Sons Inc 6-styrylpyrazolo(3,4-d)pyrimidinones and pyrimidines
GR82004B (hr) 1983-06-30 1984-12-12 American Home Prod
US4602023A (en) * 1985-06-03 1986-07-22 Warner-Lambert Company Diphenic acid monoamides
US6211158B1 (en) * 1987-04-10 2001-04-03 Roche Diagnostics Gmbh Desazapurine-nucleotide derivatives, processes for the preparation thereof, pharmaceutical compositions containing them and the use thereof for nucleic acid sequencing and as antiviral agents
DE3739366A1 (de) 1987-04-10 1988-10-27 Boehringer Mannheim Gmbh Desaza-purin-nucleosid-derivate, verfahren zu deren herstellung sowie deren verwendung bei der nucleinsaeure-sequenzierung sowie als antivirale mittel
US6903224B2 (en) * 1988-04-11 2005-06-07 Biochem Pharma Inc. Substituted 1,3-oxathiolanes
US6350753B1 (en) * 1988-04-11 2002-02-26 Biochem Pharma Inc. 2-Substituted-4-substituted-1,3-dioxolanes and use thereof
US6175008B1 (en) * 1988-04-11 2001-01-16 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
US7119202B1 (en) * 1989-02-08 2006-10-10 Glaxo Wellcome Inc. Substituted-1,3-oxathiolanes and substituted-1,3-dioxolanes with antiviral properties
US5047407A (en) * 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
US5041449A (en) * 1988-04-11 1991-08-20 Iaf Biochem International, Inc. 4-(nucleoside base)-substituted-1,3-dioxolanes useful for treatment of retroviral infections
US5270315A (en) * 1988-04-11 1993-12-14 Biochem Pharma Inc. 4-(purinyl bases)-substituted-1,3-dioxlanes
US5466806A (en) * 1989-02-08 1995-11-14 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
WO1994014802A1 (en) 1989-02-08 1994-07-07 Biochem Pharma Inc. Process for preparing substituted 1,3-oxathiolanes with antiviral properties
JP2619710B2 (ja) * 1989-02-27 1997-06-11 日本製紙 株式会社 ２′，３′−ジデオキシプリンヌクレオシド類の製造方法
US5113855A (en) * 1990-02-14 1992-05-19 Newhouse Michael T Powder inhaler
US5201308A (en) * 1990-02-14 1993-04-13 Newhouse Michael T Powder inhaler
US5002949A (en) * 1990-05-01 1991-03-26 American Home Products Corporation 5-substituted-6-aminopyrimidine derivatives
DE4027391A1 (de) 1990-08-30 1992-03-12 Boehringer Ingelheim Kg Treibgasfreies inhalationsgeraet
GB9027234D0 (en) * 1990-12-15 1991-02-06 Harris Pharma Ltd An inhalation device
CA2100863A1 (en) 1991-01-23 1992-07-24 David A. Bullough Adenosine kinase inhibitors
FR2676929B1 (fr) * 1991-05-30 1994-02-11 Aerosols Bouchage Ste Fse Inhalateur de poudres.
US5341801A (en) 1991-12-03 1994-08-30 Sandoz Ltd. Inhaler
US5294612A (en) * 1992-03-30 1994-03-15 Sterling Winthrop Inc. 6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and method of use thereof
FR2700279B1 (fr) * 1993-01-14 1995-03-17 Valois Dispositif portatif pour projeter des doses d'une substance fluide à l'aide d'un flux d'air comprimé.
IL108523A0 (en) 1993-02-03 1994-05-30 Gensia Inc Pharmaceutical compositions containing adenosine kinase inhibitors for preventing or treating conditions involving inflammatory responses and pain
US5256668A (en) * 1993-03-17 1993-10-26 American Home Products Corporation Aminopyrimidine derivatives as antiviral agents for respiratory syncytial virus
CA2140021C (en) * 1993-05-12 2001-09-04 Yuji Makino Multi-dose powdered medicine administering device and method thereof
ES2128535T3 (es) * 1993-05-12 1999-05-16 Novartis Ag Nucleosidos y oligonucleotidos con grupos 2'-eter.
CN1142817A (zh) 1993-10-12 1997-02-12 杜邦麦克制药有限公司 1n-烷基-n-芳基嘧啶胺及其衍生物
PT679657E (pt) * 1994-04-27 2003-11-28 Novartis Ag Nucleosidos e oligonucleotidos com grupos 2'-eter
GB9423910D0 (en) * 1994-11-26 1995-01-11 Pfizer Ltd Therapeutic agents
US5656629A (en) * 1995-03-10 1997-08-12 Sanofi Winthrop, Inc. 6-substituted pyrazolo (3,4-d)pyrimidin-4-ones and compositions and methods of use thereof
CA2235598A1 (en) 1995-11-02 1997-05-09 Hoe Joo Son Novel nucleoside derivatives and process for preparing the same
AU3029797A (en) 1996-06-06 1998-01-05 Novartis Ag 2'-substituted nucleosides and oligonucleotide derivatives
AU3340797A (en) 1996-06-28 1998-01-21 Novartis Ag Modified oligonucleotides
CA2265495A1 (en) 1996-09-13 1998-03-19 The Board Of Trustees Of The Leland Stanford Junior University Non-hormonal method of contraception
CN1233254A (zh) 1996-10-16 1999-10-27 Icn药品公司 嘌呤l－核苷、其类似物及其用途
US6509320B1 (en) * 1996-10-16 2003-01-21 Icn Pharmaceuticals, Inc. Purine L-nucleosides, analogs and uses thereof
US5985627A (en) 1997-02-28 1999-11-16 Carlsberg Laboratory Modified carboxypeptidase
DE19709877A1 (de) 1997-03-11 1998-09-17 Bayer Ag 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate
US5948812A (en) * 1997-06-09 1999-09-07 Givaudan Roure (International) Sa 1,7-dioxacycloalkan-8-one compounds
US5969499A (en) * 1997-09-10 1999-10-19 Shaffer; Randall A Controller for AC motor
US6200977B1 (en) 1998-02-17 2001-03-13 Tularik Inc. Pyrimidine derivatives
DE19838705A1 (de) 1998-08-26 2000-03-02 Bayer Ag Neue Dihydro-(1,2,3)-triazolo-[4,5-d]pyrimidin-7-one
AR023052A1 (es) 1998-09-25 2002-09-04 Mitsuharu Yoshimura Milton Derivados de pirimidona
GB9823103D0 (en) 1998-10-23 1998-12-16 Pfizer Ltd Pharmaceutically active compounds
AU759307B2 (en) * 1998-11-02 2003-04-10 Merck Sharp & Dohme Corp. Method of treating migraines and pharmaceutical compositions
US6225315B1 (en) * 1998-11-30 2001-05-01 Pfizer Inc Method of treating nitrate-induced tolerance
US6100037A (en) * 1999-01-07 2000-08-08 Incyte Pharmaceuticals, Inc. Human cyclic nucleotide PDEs
CZ27399A3 (cs) 1999-01-26 2000-08-16 Ústav Experimentální Botaniky Av Čr Substituované dusíkaté heterocyklické deriváty, způsob jejich přípravy, tyto deriváty pro použití jako léčiva, farmaceutická kompozice a kombinovaný farmaceutický přípravek tyto deriváty obsahující a použití těchto derivátů pro výrobu léčiv
US6515117B2 (en) * 1999-10-12 2003-02-04 Bristol-Myers Squibb Company C-aryl glucoside SGLT2 inhibitors and method
AU2001235278A1 (en) 2000-02-18 2001-08-27 Shire Biochem Inc Method for the treatment or prevention of flavivirus infections using nucleoside analogues
US6534651B2 (en) 2000-04-06 2003-03-18 Inotek Pharmaceuticals Corp. 7-Substituted isoindolinone inhibitors of inflammation and reperfusion injury and methods of use thereof
US6369222B1 (en) 2000-07-18 2002-04-09 Hoffmann-La Roche Inc. mGluR antagonists and a method for their synthesis
CA2417631A1 (en) * 2000-08-01 2003-01-29 Bayer Aktiengesellschaft Selective pde 2 inhibitors, used as medicaments for improving cognition
AU2001277621A1 (en) 2000-08-09 2002-03-04 Astrazeneca Ab Antiangiogenic bicyclic derivatives
SK2152003A3 (en) * 2000-08-24 2003-08-05 Novartis Ag Process for surface modifying substrates and modified substrates resulting therefrom
US6581338B2 (en) * 2000-10-20 2003-06-24 Myron N. Koenig Escapable area well cover
US20020074774A1 (en) * 2000-12-14 2002-06-20 Davin Hsu Adjustable handle of umbrella stroller by telescoping and swiveling
GB0100621D0 (en) 2001-01-10 2001-02-21 Vernalis Res Ltd Chemical compounds VI
EP1355916B1 (en) 2001-01-22 2007-01-10 Merck & Co., Inc. Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase
TWI255817B (en) 2001-02-14 2006-06-01 Kissei Pharmaceutical Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof
DE10108752A1 (de) 2001-02-23 2002-09-05 Bayer Ag Neue Substituierte Imidazotriazinone
US6936590B2 (en) * 2001-03-13 2005-08-30 Bristol Myers Squibb Company C-aryl glucoside SGLT2 inhibitors and method
GB0106661D0 (en) 2001-03-16 2001-05-09 Pfizer Ltd Pharmaceutically active compounds
HUP0600232A2 (en) * 2001-04-11 2006-08-28 Bristol Myers Squibb Co Amino acid complexes of c-aryl glucosides for treatment of diabetes and method
JPWO2002086160A1 (ja) * 2001-04-18 2004-08-12 三菱レイヨン株式会社 ハイブリダイゼーションプローブ
WO2002098864A1 (en) 2001-06-01 2002-12-12 F. Hoffmann-La Roche Ag Pyrimidine, triazine and pyrazine derivatives as glutamate receptors
WO2002100399A1 (en) * 2001-06-12 2002-12-19 Elan Pharmaceuticals, Inc. Macrocycles useful in the treatment of alzheimer's disease
EP1409562B1 (en) 2001-07-25 2006-04-12 PPG Industries Ohio, Inc. High refractive index optical resin composition
EP1283226A1 (en) 2001-07-31 2003-02-12 Resolution Research Nederland B.V. Hydroxyl-functional copolymer and coating compositions formed therewith
US6962991B2 (en) 2001-09-12 2005-11-08 Epoch Biosciences, Inc. Process for the synthesis of pyrazolopyrimidines
WO2003031458A1 (en) 2001-10-12 2003-04-17 Dana-Farber Cancer Institute Methods for synthesis of diarylmethanes
IL161155A0 (en) 2001-11-02 2004-08-31 Pfizer Prod Inc Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors
US20030195205A1 (en) * 2001-11-02 2003-10-16 Pfizer Inc. PDE9 inhibitors for treating cardiovascular disorders
HN2002000317A (es) 2001-11-02 2003-05-21 Pfizer Inhibidores de pde9 para tratamiento de trastornos cardiovasculares
DE10156249A1 (de) * 2001-11-15 2003-05-28 Bayer Ag Regulation der cGMP-spezifischen Phosphodiesterase 9A
US7285658B2 (en) 2002-02-28 2007-10-23 Biota, Inc. Nucleotide mimics and their prodrugs
DE10219435A1 (de) 2002-05-02 2003-11-13 Bayer Cropscience Ag Substituierte Pyrazolo-pyrimidin-4-one
AU2003237249A1 (en) 2002-05-24 2003-12-12 Isis Pharmaceuticals, Inc. Oligonucleotides having modified nucleoside units
RS114004A (en) 2002-06-28 2007-02-05 Idenix (Cayman) Limited, Modified 2' and 3'-nucleoside produgs for treating flaviridae infections
DE10238724A1 (de) * 2002-08-23 2004-03-04 Bayer Ag Alkyl-substituierte Pyrazolpyrimidine
EP1548008A4 (en) 2002-08-23 2008-08-06 Kirin Pharma Kk COMPOUND HAVING BETA-TRANSFORMING GROWTH FACTOR INHIBITORY ACTIVITY AND DRUG CONTAINING COMPOSITION
DE10238722A1 (de) 2002-08-23 2004-03-11 Bayer Ag Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse
DE10238725A1 (de) 2002-08-23 2004-03-04 Bayer Cropscience Ag Substituierte Heterocyclypyrimidine
DE10238723A1 (de) 2002-08-23 2004-03-11 Bayer Ag Phenyl-substituierte Pyrazolyprimidine
DE10244795A1 (de) * 2002-09-26 2004-04-08 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pulverinhalator
BR0316363A (pt) 2002-11-15 2005-10-04 Idenix Cayman Ltd Nucleosìdeos 2'-ramificado e mutação de flaviviridae
CN100391963C (zh) * 2003-01-03 2008-06-04 布里斯托尔-迈尔斯斯奎布公司 制备c-芳基葡糖苷sglt2抑制剂的方法
EP1460077B1 (en) 2003-03-18 2007-08-01 The Jordanian Pharmaceutical Manufacturing Co. Ltd. Novel pyrazolopyrimidones and their use as PDE inhibitors
US20040220186A1 (en) * 2003-04-30 2004-11-04 Pfizer Inc. PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease
US8044060B2 (en) 2003-05-09 2011-10-25 Boehringer Ingelheim International Gmbh 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory
DE10320785A1 (de) 2003-05-09 2004-11-25 Bayer Healthcare Ag 6-Arylmethyl-substituierte Pyrazolopyrimidine
EP1626971B1 (de) 2003-05-09 2011-08-10 Boehringer Ingelheim International Gmbh 6-cyclylmethyl- und 6-alkylmethyl-substituierte pyrazolopyrimidine
JP5044214B2 (ja) 2003-06-06 2012-10-10 アレクシス・アクチボラゲット 皮膚状態または癌の処置のためのｓｃｃｅ阻害剤としての縮合複素環化合物の使用
DE10328479A1 (de) * 2003-06-25 2005-01-13 Bayer Ag 6-Arylamino-5-cyano-4-pyrimidinone
ATE422204T1 (de) 2003-08-26 2009-02-15 Boehringer Ingelheim Int Glucopyranosyloxy-pyrazole, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung
US7375090B2 (en) * 2003-08-26 2008-05-20 Boehringer Ingelheim International Gmbh Glucopyranosyloxy-pyrazoles, pharmaceutical compositions containing these compounds, the use thereof and processed for the preparation thereof
US7351827B2 (en) 2003-11-21 2008-04-01 The University Of Connecticut Substituted oxetanes, method of making, and method of use thereof
US7371732B2 (en) * 2003-12-22 2008-05-13 Boehringer Ingelheim International Gmbh Glucopyranosyloxy-substituted aromatic compounds, medicaments containing such compounds, their use and process for their manufacture
DE102004001873A1 (de) * 2004-01-14 2005-09-29 Bayer Healthcare Ag Cyanopyrimidinone
DE102004012093A1 (de) * 2004-03-05 2005-09-22 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pulverinhalator mit Merkanaldüse
SI1730131T1 (sl) 2004-03-16 2012-08-31 Boehringer Ingelheim Int Glukopiranozil-substituirani benzenski derivati, zdravila, ki vsebujejo te spojine, njihova uporaba in postopek za njihovo pripravo
US7393836B2 (en) * 2004-07-06 2008-07-01 Boehringer Ingelheim International Gmbh D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
EP1773800A1 (de) * 2004-07-27 2007-04-18 Boehringer Ingelheim International GmbH D-glucopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung
DE102004048388A1 (de) * 2004-10-01 2006-04-06 Boehringer Ingelheim Pharma Gmbh & Co. Kg D-Pyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung
EP1828216B1 (en) * 2004-12-16 2008-09-10 Boehringer Ingelheim International GmbH Glucopyranosyl-substituted benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
DOP2006000009A (es) 2005-01-13 2006-08-15 Arena Pharm Inc Procedimiento para preparar eteres de pirazolo [3,4-d] pirimidina
CA2596424C (en) 2005-02-04 2016-03-29 Millennium Pharmaceuticals, Inc. Inhibitors of e1 activating enzymes
WO2006089872A1 (en) 2005-02-23 2006-08-31 Boehringer Ingelheim International Gmbh Glucopyranosyl-substituted ( (hetero)arylethynyl-benzyd-benzene derivatives and use thereof as sodium-dependent glucose cotransporter 2 (sglt2) inhibitors
WO2006091905A1 (en) 2005-02-25 2006-08-31 Gilead Sciences, Inc. Bicyclo (3.1.0) hexane derivatives as antiviral compounds
DE602006011453D1 (de) * 2005-04-15 2010-02-11 Boehringer Ingelheim Pharma Glucopyranosyl-substituierte (heteroaryloxy-benzyl)-benzen-derivate als sglt-inhibitoren
US7723309B2 (en) 2005-05-03 2010-05-25 Boehringer Ingelheim International Gmbh Crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments
UA91546C2 (uk) 2005-05-03 2010-08-10 Бьорінгер Інгельхайм Інтернаціональ Гмбх КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ
US7772191B2 (en) 2005-05-10 2010-08-10 Boehringer Ingelheim International Gmbh Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein
DE102005024493A1 (de) 2005-05-27 2006-11-30 Bayer Healthcare Ag Verwendung von Pyrazolopyrimidinen
EP1910390B1 (en) 2005-07-27 2010-05-19 Boehringer Ingelheim International GmbH Glucopyranosyl-substituted ((hetero)cycloalyklethynyl-benzyl)-benzene derivatives and use thereof as sodium-dependent glucose cotransporter (sglt) inhibitors
WO2007025043A2 (en) 2005-08-23 2007-03-01 Idenix Pharmaceuticals, Inc. Seven-membered ring nucleosides
ATE484499T1 (de) * 2005-08-30 2010-10-15 Boehringer Ingelheim Int Glucopyranosyl-substituierte benzyl-derivate, medikamente mit solchen verbindungen, ihre verwendung und herstellungsverfahren dafür
AR056195A1 (es) 2005-09-15 2007-09-26 Boehringer Ingelheim Int Procedimientos para preparar derivados de (etinil-bencil)-benceno sustituidos de glucopiranosilo y compuestos intermedios de los mismos
US7488766B2 (en) * 2005-10-06 2009-02-10 Sabic Innovative Plastics Ip B.V. Polymer composition, method, and article
TW200815361A (en) 2005-10-20 2008-04-01 Astrazeneca Ab Chemical compounds
TW200801029A (en) 2006-02-15 2008-01-01 Boehringer Ingelheim Int Glucopyranosyl-substituted benzonitrile derivatives, pharmaceutical compositions containing such compounds, their use and process for their manufacture
DE102006016903A1 (de) * 2006-04-11 2007-10-25 Boehringer Ingelheim Pharma Gmbh & Co. Kg Inhalator
EP1844805A1 (de) * 2006-04-13 2007-10-17 Boehringer Ingelheim Pharma GmbH & Co.KG Inhalator
PE20080697A1 (es) 2006-05-03 2008-08-05 Boehringer Ingelheim Int Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion
PE20110235A1 (es) * 2006-05-04 2011-04-14 Boehringer Ingelheim Int Combinaciones farmaceuticas que comprenden linagliptina y metmorfina
WO2008005542A2 (en) 2006-07-07 2008-01-10 Gilead Sciences, Inc., Antiviral phosphinate compounds
EP2054426A1 (en) 2006-08-15 2009-05-06 Boehringer Ingelheim International GmbH Glucopyranosyl-substituted cyclopropylbenzene derivatives, pharmaceutical compositions containing such compounds, their use as sglt inhibitors and process for their manufacture
DE102006044752A1 (de) 2006-09-20 2008-04-10 Boehringer Ingelheim Pharma Gmbh & Co. Kg Kolbendosierer
CA2664095A1 (en) * 2006-09-21 2008-03-27 Boehringer Ingelheim International Gmbh Glucopyranosyl-substituted difluorobenzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
CA2667550A1 (en) 2006-10-27 2008-05-02 Boehringer Ingelheim International Gmbh Crystalline form of 4-(.beta.-d-glucopyranos-1-yl)-1-methyl-2-[4-((s)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments
AR063569A1 (es) 2006-11-06 2009-02-04 Boehringer Ingelheim Int Derivados de benzil- benzonitrilo sustituidos con glucopiranosilo medicamentos que contienen a compuestos de este tipo su uso u procedimiento para su fabricacion
US20090137549A1 (en) 2006-11-09 2009-05-28 Paul John Edward Novel compounds useful for the treatment of degenerative & inflamatory diseases
US20100298243A1 (en) 2006-11-09 2010-11-25 Boehringer Ingelheim International Gmbh Combination therapy with sglt-2 inhibitors and their pharmaceutical compositions
JP2008183929A (ja) * 2007-01-26 2008-08-14 Toshiba Corp Ｖｏｒモニタ受信装置及びｖｏｒモニタ受信方法
CL2008000224A1 (es) 2007-01-26 2008-05-23 Boehringer Ingelheim Int Composicion farmaceutica que comprende un compuesto derivado glucopiranosilo; y uso para el tratamiento de uno o mas trastornos neurodegenerativos.
WO2008100447A2 (en) 2007-02-09 2008-08-21 Gilead Sciences, Inc. Nucleoside analogs for antiviral treatment
US7879807B2 (en) 2007-02-21 2011-02-01 Boehringer Ingelheim International Gmbh Tetrasubstituted glucopyranosylated benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
WO2008104077A1 (en) 2007-02-28 2008-09-04 Methylgene Inc. Small molecule inhibitors of protein arginine methyltransferases (prmts)
EP2152712B1 (en) 2007-05-11 2012-01-11 Pfizer Inc. Amino-heterocyclic compounds
CL2008002425A1 (es) 2007-08-16 2009-09-11 Boehringer Ingelheim Int Composición farmacéutica que comprende un inhibidor de sglt2 y 1-(4-metil-quinazolin-2-il)metil-3metil-7-(-2-butin-1-il)-8-(3-(r)-amino-piperidin-1il)-xantina, un inhibidor de dpp iv y su uso para el tratamiento de la obesidad y de la diabetes tipo 1 y 2 y complicaciones de esta.
EA201070611A1 (ru) 2007-11-13 2010-12-30 Айкос Корпорейшн Ингибиторы человеческой фосфатидилинозитол-3-киназы дельта
WO2009068617A1 (en) 2007-11-30 2009-06-04 Boehringer Ingelheim International Gmbh 1, 5-dihydro-pyrazolo (3, 4-d) pyrimidin-4-one derivatives and their use as pde9a modulators for the teatment of cns disorders
CA2716124A1 (en) 2008-02-20 2009-08-27 Boehringer Ingelheim International Gmbh Powder inhalers
US20090235929A1 (en) * 2008-03-19 2009-09-24 Marc Egen Powder inhalers
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
WO2010026214A1 (en) 2008-09-08 2010-03-11 Boehringer Ingelheim International Gmbh Pyrazolopyrimidines and their use for the treatment of cns disorders
UA102429C2 (ru) 2009-02-13 2013-07-10 Бьорінгер Інгельхайм Інтернаціональ Гмбх Фармацевтическая композиция, которая включает ингибитор sglt-2, ингибитор дпп-iv и другой антидиабетический агент, и ее применение
UY32427A (es) 2009-02-13 2010-09-30 Boheringer Ingelheim Internat Gmbh Composicion farmaceutica, forma farmaceutica, procedimiento para su preparacion, metodos de tratamiento y usos de la misma
WO2010092123A1 (en) 2009-02-13 2010-08-19 Boehringer Ingelheim International Gmbh Sglt-2 inhibitor for treating type 1 diabetes mellitus, type 2 diabete mellitus, impaired glucose tolerance or hyperglycemia
CN102387783A (zh) 2009-02-13 2012-03-21 贝林格尔.英格海姆国际有限公司 包含吡喃葡萄糖基二苯基甲烷衍生物的药物组合物、其药物剂型、其制备方法及其在患者中改善血糖控制的用途
SI2414363T1 (sl) 2009-03-31 2014-04-30 Boehringer Ingelheim Gmbh Derivati 1-heterociklil-1,5-dihidro-pirazolo/3,4-d/pirimidin-4-ona in njihova uporaba kot modulatorji za PDE9A
TW201118099A (en) 2009-08-12 2011-06-01 Boehringer Ingelheim Int New compounds for the treatment of CNS disorders
BR112012007085B8 (pt) 2009-09-30 2021-05-25 Boehringer Ingelheim Int processos para a preparação de derivados de benzil-benzeno substituídos com glicopiranosila
EA020798B1 (ru) 2009-09-30 2015-01-30 Бёрингер Ингельхайм Интернациональ Гмбх СПОСОБ ПОЛУЧЕНИЯ КРИСТАЛЛИЧЕСКОЙ ФОРМЫ 1-ХЛОР-4-(β-D-ГЛЮКОПИРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГИДРОФУРАН-3-ИЛОКСИ)БЕНЗИЛ]БЕНЗОЛА
UY32919A (es) 2009-10-02 2011-04-29 Boehringer Ingelheim Int Composición farmacéutica, forma de dosificación farmacéutica, procedimiento para su preparación, mé todos para su tratamiento y sus usos
MY170189A (en) 2010-08-12 2019-07-09 Boehringer Ingelheim Int 6-cycloalkyl-1, 5-dihydro-pyrazolo[3,4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors
EP2637669A4 (en) 2010-11-10 2014-04-02 Infinity Pharmaceuticals Inc Heterocyclic compounds and their use
US20130040971A1 (en) * 2011-02-14 2013-02-14 Boehringer Ingelheim International Gmbh 6-cycloalkyl-pyrazolopyrimidinones for the treatment of cns disorders

Also Published As

Publication number Publication date
ES2460019T3 (es) 2014-05-13
UY32531A (es) 2010-10-29
ECSP11011386A (es) 2011-11-30
DK2414363T3 (da) 2014-01-27
BRPI1011533A2 (pt) 2016-03-29
MX2011010184A (es) 2011-10-28
AP2011005819A0 (en) 2011-08-31
HK1163105A1 (en) 2012-09-07
PE20120505A1 (es) 2012-05-09
TN2011000493A1 (en) 2013-03-27
GEP20146098B (en) 2014-05-27
TW201100426A (en) 2011-01-01
EA201101395A1 (ru) 2012-06-29
US9102679B2 (en) 2015-08-11
SI2414363T1 (sl) 2014-04-30
NZ594567A (en) 2013-12-20
RS53167B (en) 2014-06-30
AU2010230290B2 (en) 2013-03-14
IL214436A0 (en) 2011-09-27
CL2011002454A1 (es) 2012-02-17
EP2414363B1 (en) 2014-01-08
AU2010230290A1 (en) 2011-09-01
CN102365285B (zh) 2014-08-06
MY156377A (en) 2016-02-15
SG174964A1 (en) 2011-11-28
AR076171A1 (es) 2011-05-26
PL2414363T3 (pl) 2014-06-30
JP5542196B2 (ja) 2014-07-09
CO6501182A2 (es) 2012-08-15
US20110082137A1 (en) 2011-04-07
US8623901B2 (en) 2014-01-07
CN102365285A (zh) 2012-02-29
US20140350025A1 (en) 2014-11-27
EP2414363A1 (en) 2012-02-08
CA2757231A1 (en) 2010-10-07
KR20120003868A (ko) 2012-01-11
JP2012522027A (ja) 2012-09-20
WO2010112437A1 (en) 2010-10-07
MA33152B1 (fr) 2012-03-01
PT2414363E (pt) 2014-02-26

Similar Documents

Publication Publication Date Title
HRP20140312T1 (hr) Derivati 1-heterociklil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona i njihova uporaba kao modulatori za pde9a
HRP20140011T1 (hr) Derivati oksazina i njihova uporaba u lijeäśenju neuroloških poremeä†aja
HRP20151250T1 (hr) Derivati izoksazolo-piridina
HRP20160030T1 (hr) Derivati 6,7-dihidro-pirazolo[1,5-a]pirazin-4-ilamina koji su korisni kao inhibitori beta-sekretaze (bace)
HRP20160647T1 (hr) Novi heterociklički derivati i njihova uporaba u liječenju neuroloških poremećaja
MX2007000044A (es) Compuestos, composiciones y metodos de tetrahidroquinazolin-4(3h)- ona-relacionados y tetrahidropirido [2,3-d] pirimidin-4(3h)-ona- relacionados para su uso.
HRP20210770T1 (hr) PIROLO[2,3-d]PIRIMIDINIL-, PIROLO[2,3-b]PIRAZINIL- I PIROLO[2,3-d]PIRIDINILAKRILAMIDI
NZ588245A (en) 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-d] pyrimidin-4-one derivatives and their use as pde9a modulators
HRP20191307T1 (hr) Spojevi heteroaril-piridona i aza-piridona kao inhibitori aktivnosti btk
HRP20190857T1 (hr) Inhibitori glikozidaze
ES2365692T3 (es) Medicamento para la prevención o tratamiento terapéutico de enfermedades hepáticas.
MA39162A1 (fr) Composés nicotinamide substitués par un hétéroaryle
HRP20171179T1 (hr) Amino-suostituirani imidazo[1,2-a]piridinkaboksamidi i njihova uporaba
PH12015501878A1 (en) Tetrahydroimidazo[1,5-d][1,4]oxazepine derivative
HRP20170695T1 (hr) Fenil-3-aza-biciklo[3.1.0]heks-3-il-metanoni i njihova uporaba u obliku lijeka
HRP20190748T1 (hr) Derivati policikličkog amida kao inhibitori cdk9
JP2014513139A5 (hr)
HRP20050708A2 (en) Piperidine-benzenesulfonamide derivatives
HRP20110457T1 (hr) Derivati piridina i njihova upotreba u liječenju psihotičnih poremećaja
HK1176057A1 (zh) 咪唑並 吡嗪衍生物及其預防或治療神經病、精神病和代謝性障礙和疾病的用途
EA200601192A1 (ru) ЗАМЕЩЁННЫЕ ПРОИЗВОДНЫЕ 8'-ПИРИ(МИ)ДИНИЛДИГИДРОСПИРО[ЦИКЛОАЛКИЛАМИН]ПИРИМИДО[1,2-a]ПИРИМИДИН-6-ОНА
TN2013000324A1 (en) 6 - cyclobutyl - 1, 5 - dihydro - pyrazolo [3, 4-d] pyrimidin- 4 - one derivatives their use as pde9a inhibitors
HRP20221151T1 (hr) Inhibitor urat1 i njegova upotreba
WO2009017098A1 (ja) トロンボポエチン受容体アゴニスト作用を有する光学活性な化合物を含有する医薬組成物およびその中間体
WO2003027116A3 (en) Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1h)one derivatives