HRP20160273T1 - Derivati pirazolokinolina kao inhibitori pde9 - Google Patents
Derivati pirazolokinolina kao inhibitori pde9 Download PDFInfo
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- HRP20160273T1 HRP20160273T1 HRP20160273TT HRP20160273T HRP20160273T1 HR P20160273 T1 HRP20160273 T1 HR P20160273T1 HR P20160273T T HRP20160273T T HR P20160273TT HR P20160273 T HRP20160273 T HR P20160273T HR P20160273 T1 HRP20160273 T1 HR P20160273T1
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- pyrazolo
- methoxy
- dimethylpyridin
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- 229940076380 PDE9 inhibitor Drugs 0.000 title claims 2
- UXYHZIYEDDINQH-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=NN=C3C=CC2=C1 UXYHZIYEDDINQH-UHFFFAOYSA-N 0.000 title 1
- -1 3-pyridinyl group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- ADEJACPCTOIQLO-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]quinoline Chemical group C1=NC2=CC=CC=C2C2=C1C=NN2 ADEJACPCTOIQLO-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052731 fluorine Chemical group 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- SORUKOYGEBDKBE-ZDUSSCGKSA-N 8-fluoro-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-[(3S)-oxolan-3-yl]-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC=C(C)C(C=2C(=CC=3C=4N([C@@H]5COCC5)N=CC=4C(=O)NC=3C=2)F)=C1C SORUKOYGEBDKBE-ZDUSSCGKSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- MTDOVWNESOFCFP-UHFFFAOYSA-N 1-(1,4-dioxepan-6-yl)-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC=C(C)C(C=2C=C3NC(=O)C=4C=NN(C=4C3=CC=2)C2COCCOC2)=C1C MTDOVWNESOFCFP-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
- NUKIGRUOENPLQU-UHFFFAOYSA-N 7-(2,4-dimethyl-6-propan-2-yloxypyridin-3-yl)-1-(oxolan-3-yl)-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound CC1=NC(OC(C)C)=CC(C)=C1C1=CC=C(C2=C(C=NN2C2COCC2)C(=O)N2)C2=C1 NUKIGRUOENPLQU-UHFFFAOYSA-N 0.000 claims 1
- NUKIGRUOENPLQU-KRWDZBQOSA-N 7-(2,4-dimethyl-6-propan-2-yloxypyridin-3-yl)-1-[(3S)-oxolan-3-yl]-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound CC1=NC(OC(C)C)=CC(C)=C1C1=CC=C(C2=C(C=NN2[C@@H]2COCC2)C(=O)N2)C2=C1 NUKIGRUOENPLQU-KRWDZBQOSA-N 0.000 claims 1
- CKJDCNZBABIEBZ-UHFFFAOYSA-N 7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(oxolan-3-yl)-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC=C(C)C(C=2C=C3NC(=O)C=4C=NN(C=4C3=CC=2)C2COCC2)=C1C CKJDCNZBABIEBZ-UHFFFAOYSA-N 0.000 claims 1
- CKJDCNZBABIEBZ-HNNXBMFYSA-N 7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-[(3S)-oxolan-3-yl]-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC=C(C)C(C=2C=C3NC(=O)C=4C=NN(C=4C3=CC=2)[C@@H]2COCC2)=C1C CKJDCNZBABIEBZ-HNNXBMFYSA-N 0.000 claims 1
- SORUKOYGEBDKBE-UHFFFAOYSA-N 8-fluoro-7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-(oxolan-3-yl)-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC=C(C)C(C=2C(=CC=3C=4N(C5COCC5)N=CC=4C(=O)NC=3C=2)F)=C1C SORUKOYGEBDKBE-UHFFFAOYSA-N 0.000 claims 1
- HKUJJFZTJXCSPK-UHFFFAOYSA-N 8-fluoro-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(oxan-4-yl)-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC(C)=CC(C)=C1C(C(=C1)F)=CC2=C1C(N(C1CCOCC1)N=C1)=C1C(=O)N2 HKUJJFZTJXCSPK-UHFFFAOYSA-N 0.000 claims 1
- JVAMGWNWZZUNCI-ZDUSSCGKSA-N 8-fluoro-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-[(3S)-oxolan-3-yl]-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC(C)=CC(C)=C1C(C(=C1)F)=CC2=C1C(N([C@@H]1COCC1)N=C1)=C1C(=O)N2 JVAMGWNWZZUNCI-ZDUSSCGKSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- RVEJWGYZBXCGGM-DNVCBOLYSA-N chembl2179094 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CC=C1 RVEJWGYZBXCGGM-DNVCBOLYSA-N 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000003551 oxepanyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (17)
1. Spoj ili njegova farmakološki prihvatljiva sol koja je prikazana s formulom (1):
[image]
naznačen time da
R1 je atom vodika;
R2 je skupina aromatskog prstena odabrana iz skupine koju čine fenilna skupina, piridinil skupina, i pirimidinil skupina, gdje su dva atoma na aromatskom prstenu, koji su susjedni ugljikovom atomu spojeni na pirazolo[4,3-c]kinolinski prsten svaki neovisno ima supstituent odabran iz Skupine A1, dok ostali atomi na aromatskom prstenu neovisno proizvoljno imaju supstituent odabran iz skupine B1;
R3 je atom vodika, ili atom fluora;
R4 je atom vodika;
R5 je oksepanil skupina, dioksepanil skupina, tetrahidropiranil skupina, ili tetrahidrofuranil skupina koja proizvoljno ima metoksi skupinu;
R6 je atom vodika;
skupina A1 sadrži halogeni atom, skupinu C1-6 alkil koja proizvoljno ima 1 do 3 halogenih atoma, i skupinu C1-6 alkoksi; i
Skupina B1 sadrži halogeni atom, cijano skupinu, skupinu C1-6 alkil koja proizvoljno ima 1 do 3 halogenih atoma, skupinu C1-6 alkoksi-C1-6 alkil, skupinu C1-6 alkoksi koja proizvoljno ima 1 do 3 halogenih atoma, i skupinu tetrahidropiranil, uz uvjet da kada R2 je skupina 3-piridinil, supstituent na 4-položaju je halogeni atom, ili skupina C1-6 alkil koja proizvoljno ima 1 do 3 halogenih atoma.
2. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 1, naznačen time da
R2 je skupina aromatskog prstena odabrana iz skupine koju čine fenil skupina, skupina 3-piridinil, skupina 4-piridinil, i skupina 5-pirimidinil, gdje su dva atoma na aromatskom prstenu, koji su susjedni ugljikovom atomu spojeni na pirazolo[4,3-c]kinolinski prsten svaki neovisno ima supstituent odabran iz Skupine A2, dok ostali atomi na aromatskom prstenu neovisno proizvoljno imaju supstituent odabran iz Skupine B2;
R5 je skupina 4-oksepanil, skupina 1,4-dioksepan-6-il, skupina 3,4,5,6-tetrahidro-2H-3-piranil, skupina 3,4,5,6-tetrahidro-2H-4-piranil, ili skupina 3-tetrahidrofuranil;
Skupina A2 sadrži atom klora, i metil skupinu koja proizvoljno ima 1 do 2 atoma fluora, etil skupinu, metoksi skupinu, i etoksi skupinu; te
Skupina B2 sadrži atom fluora, atom klora, cijano skupinu, metil skupinu koja proizvoljno ima 1 do 3 atoma fluora, etil skupinu, metoksimetil skupinu, metoksi skupinu koja proizvoljno ima 1 do 3 atoma fluora, etoksi skupinu, izopropiloksi skupinu, te skupinu 3,4,5,6-tetrahidro-2H-4-piranil.
3. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 2, naznačen time da R3 je atom fluora.
4. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 1, naznačen time da
R3 je atom vodika; i
R5 je skupina tetrahidropiranil, ili skupina tetrahidrofuranil koja proizvoljno ima metoksi skupinu.
5. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 2, naznačen time da R3 je atom vodika; i R5 je skupina 3,4,5,6-tetrahidro-2H-3-piranil, skupina 3,4,5,6-tetrahidro-2H-4-piranil, ili skupina 3-tetrahidrofuranil. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 1, naznačen time da R2 je skupina aromatskog prstena odabrana iz skupine koju čine fenil skupina, skupina 3-piridinil, i skupina 4-piridinil, gdje su dva atoma na aromatskom prstenu, koji su susjedni ugljikovom atomu spojeni na pirazolo[4,3-c]kinolinski prsten svaki neovisno ima supstituent odabran iz Skupine A3, dok ostali atomi na aromatskom prstenu neovisno proizvoljno imaju supstituent odabran iz Skupine B3;
R3 je atom vodika;
R4 je atom vodika;
R5 je skupina 3,4,5,6-tetrahidro-2H-4-piranil, ili skupina 3-tetrahidrofuranil;
Skupina A3 sadrži metil skupinu, i metoksi skupinu; i
Skupina B3 sadrži metil skupinu, metoksi skupinu, te metoksimetil skupinu.
6. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 1 naznačen time da je odabran iz slijedeće skupine:
1) 7-(6-metoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidro-2H-piran-4-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
2) 7-(2-metoksi-4,6-dimetilpiridin-3-il)-1-(tetrahidro-2H-piran-4-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
3) (S)-7-(6-izopropiloksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
4) 8-fluoro-7-(2-metoksi-4,6-dimetilpiridin-3-il)-1-(tetrahidro-2H-piran-4-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
5) 1-(1,4-dioksepan-6-il)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
6) 1-(1,4-dioksepan-6-il)-7-(2-metoksi-4,6-dimetilpiridin-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
7) (S)-8-fluoro-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
8) 7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidro-2H-piran-4-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
9) (-)-7-(2-metoksi-4,6-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
10) (-)-7-(6-metoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on,
11) (S)-8-fluoro-7-(2-metoksi-4,6-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on
12) (S)-7-(6-etoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on
13) (S)-8-fluoro-7-(6-metoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-((5H)-on i
14) (S)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on.
7. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 7 naznačen time da je 7-(6-izopropiloksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on.
8. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 7 naznačen time da je (S)-7-(6-izopropiloksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on:
[image]
9. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 7 naznačen time da je 8-fluoro-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on.
10. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 7 naznačen time da je (S)-8-fluoro-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on:
[image]
11. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 7 naznačen time da je 7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on.
12. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 7 naznačen time da je (S)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on:
[image]
13. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 7 naznačen time da je 1-(1,4-dioksepan-6-il)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1H-pirazolo[4,3-c]kinolin-4(5H)-on:
[image]
14. Farmaceutski pripravak naznačen time da kao aktivni sastojak sadrži spoj ili njegovu farmakološki prihvatljivu sol prema zahtjevu 1.
15. Farmaceutski pripravak prema zahtjevu 15 naznačen time da je za uporabu kao inhibitor PDE9.
16. Farmaceutski pripravak prema zahtjevu 15 naznačen time da je za uporabu u postupku povećanja intracerebralne koncentracije cGMP.
17. Spoj ili njegova farmakološki prihvatljiva sol prema zahtjevu 1 naznačen time da je za uporabu za poboljšanje kognitivnog poremećaja kod Alzheimerove bolesti.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161544860P | 2011-10-07 | 2011-10-07 | |
| US201161550623P | 2011-10-24 | 2011-10-24 | |
| US201161558110P | 2011-11-10 | 2011-11-10 | |
| US201161580903P | 2011-12-28 | 2011-12-28 | |
| EP12837953.4A EP2769980B1 (en) | 2011-10-07 | 2012-10-04 | Pyrazoloquinoline derivative as pde9 inhibitors |
| PCT/JP2012/075748 WO2013051639A1 (ja) | 2011-10-07 | 2012-10-04 | ピラゾロキノリン誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160273T1 true HRP20160273T1 (hr) | 2016-04-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160273TT HRP20160273T1 (hr) | 2011-10-07 | 2016-03-17 | Derivati pirazolokinolina kao inhibitori pde9 |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US8563565B2 (hr) |
| EP (1) | EP2769980B1 (hr) |
| JP (1) | JP5546693B2 (hr) |
| KR (1) | KR101943680B1 (hr) |
| CN (1) | CN103930423B (hr) |
| AR (1) | AR088235A1 (hr) |
| AU (1) | AU2012319549B2 (hr) |
| BR (1) | BR112014007912B1 (hr) |
| CA (1) | CA2861795C (hr) |
| CL (1) | CL2014000821A1 (hr) |
| CO (1) | CO6910200A2 (hr) |
| CY (1) | CY1117427T1 (hr) |
| DK (1) | DK2769980T3 (hr) |
| ES (1) | ES2568015T3 (hr) |
| HK (1) | HK1199018A1 (hr) |
| HR (1) | HRP20160273T1 (hr) |
| HU (1) | HUE028555T2 (hr) |
| IL (1) | IL231650A (hr) |
| IN (1) | IN2014CN02463A (hr) |
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| ZA (1) | ZA201402439B (hr) |
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| CN106905324B (zh) | 2011-10-10 | 2018-09-25 | H.隆德贝克有限公司 | 具有咪唑并吡嗪酮骨架的pde9抑制剂 |
| US9550776B2 (en) * | 2013-04-05 | 2017-01-24 | Eisai R&D Management Co., Ltd. | Pyridinylpyrazoloquinoline compounds |
| KR101997955B1 (ko) * | 2013-04-05 | 2019-07-08 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 피라졸로퀴놀린 유도체의 염, 및 이의 결정 |
| GB201406486D0 (en) | 2014-04-10 | 2014-05-28 | Redx Pharma Ltd | Antibacterial compounds |
| WO2016021192A1 (en) * | 2014-08-08 | 2016-02-11 | Eisai R&D Management Co., Ltd. | Process for production of (s)-(tetrahydrofuran-3-yl)hydrazine |
| DK3303339T3 (da) | 2015-07-07 | 2021-04-12 | H Lundbeck As | Pde9-inhibitorer med imidazotriazinonskelet og imidazopyrazinonskelet til behandling af perifere sygdomme |
| WO2017046606A1 (en) * | 2015-09-18 | 2017-03-23 | Redx Pharma Plc | Antibacterial compounds |
| CN107056690A (zh) * | 2017-03-22 | 2017-08-18 | 上海康鹏科技有限公司 | 一种6‑溴吡啶‑3‑甲醛的制备方法 |
| JP7293129B2 (ja) * | 2017-06-01 | 2023-06-19 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Ｐｄｅ９阻害剤を含む医薬組成物 |
| MX2019013383A (es) * | 2017-06-01 | 2020-02-20 | Eisai R&D Man Co Ltd | Agente terapeutico para la demencia que combina derivado de pirazoloquinolina y memantina. |
| EP3632439B1 (en) * | 2017-06-01 | 2024-03-27 | Eisai R&D Management Co., Ltd. | Dementia therapeutic agent combining pyrazoloquinoline derivative and donepezil |
| CA3061884A1 (en) | 2017-06-01 | 2019-10-29 | Eisai R&D Management Co., Ltd. | Lewy body disease therapeutic agent containing pyrazoloquinoline derivative |
| US11591312B2 (en) | 2018-01-23 | 2023-02-28 | Basf Se | Halogenation of pyridine derivatives |
| JP2021526134A (ja) | 2018-05-25 | 2021-09-30 | イマラ インク． | ６−［（３Ｓ，４Ｓ）−４−メチル−ｌ−（ピリミジン−２−イルメチル）ピロリジン−３−イル］−３−テトラヒドロピラン−４−イル−７Ｈ−イミダゾ［ｌ，５−Ａ］ピラジン−８−オンの一水和物および結晶形態 |
| BR112021003686A2 (pt) * | 2018-08-31 | 2021-05-18 | Imara Inc. | inibidores de pde9 para tratar doença falciforme |
| BR112021011084A2 (pt) * | 2018-12-13 | 2021-08-31 | Intervet International B.V. | Processo para preparar 1-[(3r,4s)-4-cianotetrahidropiran-3-il]-3-[(2-fluoro-6-metoxi-4-piridil)amino]pirazol-4-carboxamida |
| US11883461B2 (en) | 2019-05-09 | 2024-01-30 | The Feinstein Institutes For Medical Research | HMGB1 antagonist treatment of severe sepsis |
| EP3965792A4 (en) | 2019-05-09 | 2023-01-18 | The Feinstein Institutes for Medical Research | HMGB1 ANTAGONIST |
| WO2020227592A1 (en) | 2019-05-09 | 2020-11-12 | The Feinstein Institutes For Medical Research | Thiosemicarbazates and uses thereof |
| AU2020268409A1 (en) * | 2019-05-09 | 2021-11-25 | The Feinstein Institutes For Medical Research | Compounds for use in synthesis of peptidomimetics |
| US11530218B2 (en) | 2020-01-20 | 2022-12-20 | Incyte Corporation | Spiro compounds as inhibitors of KRAS |
| CR20220584A (es) * | 2020-04-16 | 2023-02-15 | Incyte Corp | Inhibidores de kras tricíclicos fusionados |
| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
| US20230303549A1 (en) | 2020-06-30 | 2023-09-28 | Bayer Aktiengesellschaft | Substituted heteroaryloxypyridines, the salts thereof and their use as herbicidal agents |
| WO2022047093A1 (en) | 2020-08-28 | 2022-03-03 | Incyte Corporation | Vinyl imidazole compounds as inhibitors of kras |
| US11767320B2 (en) | 2020-10-02 | 2023-09-26 | Incyte Corporation | Bicyclic dione compounds as inhibitors of KRAS |
| WO2023064857A1 (en) | 2021-10-14 | 2023-04-20 | Incyte Corporation | Quinoline compounds as inhibitors of kras |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2426734C2 (ru) * | 2003-10-03 | 2011-08-20 | Зм Инновейтив Пропертиз Компани | Пиразолопиридины и их аналоги |
| WO2005118583A1 (en) * | 2004-05-28 | 2005-12-15 | Millennium Pharmaceuticals, Inc. | 2, 5-dihydro-pyrazolo`4, 3-c!quinolin-4-ones as chk-1 inhibitors |
| KR20080046728A (ko) * | 2005-09-15 | 2008-05-27 | 아스카 세이야쿠 가부시키가이샤 | 복소환 화합물, 그의 제조 방법 및 용도 |
| JP2009184924A (ja) | 2006-05-31 | 2009-08-20 | Eisai R & D Management Co Ltd | 生物学的試薬用化合物 |
| EP2103613B1 (en) * | 2006-12-13 | 2016-02-17 | ASKA Pharmaceutical Co., Ltd. | Quinoxaline derivative |
| ME00954B (me) | 2007-05-11 | 2012-06-20 | Pfizer | Aminoheterociklični spojevi |
| 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 |
| ES2612954T3 (es) * | 2009-03-05 | 2017-05-19 | Astellas Pharma Inc. | Compuestos de quinoxalina |
| NZ594567A (en) | 2009-03-31 | 2013-12-20 | Boehringer Ingelheim Int | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| US8880976B2 (en) | 2009-09-25 | 2014-11-04 | Stmicroelectronics, Inc. | Method and apparatus for encoding LBA information into the parity of a LDPC system |
| ES2583528T3 (es) * | 2010-09-07 | 2016-09-21 | Astellas Pharma Inc. | Compuesto de pirazoloquinolina |
| JP6042060B2 (ja) * | 2011-09-26 | 2016-12-14 | サノフイ | ピラゾロキノリノン誘導体、その調製および治療上の使用 |
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