ME02394B - Pirazolohinolinski derivati kao inhibitori pde9 - Google Patents
Pirazolohinolinski derivati kao inhibitori pde9Info
- Publication number
- ME02394B ME02394B MEP-2016-65A MEP201665A ME02394B ME 02394 B ME02394 B ME 02394B ME P201665 A MEP201665 A ME P201665A ME 02394 B ME02394 B ME 02394B
- Authority
- ME
- Montenegro
- Prior art keywords
- group
- pyrazolo
- methoxy
- dimethylpyridin
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- -1 4-oxepanyl group Chemical group 0.000 claims 12
- 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
- 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
- 239000008194 pharmaceutical composition 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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 group 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 group 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 group 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 group 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 group 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 group 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
- 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 group 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 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 229940076380 PDE9 inhibitor Drugs 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
- 125000003551 oxepanyl group Chemical group 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 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
- UXYHZIYEDDINQH-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=NN=C3C=CC2=C1 UXYHZIYEDDINQH-UHFFFAOYSA-N 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
Description
LISTA SEKVENCI
<110> Eisai R&D Management Co., Ltd.
<120> Derivati pirazolohinolina
<130> ECL11-020
<150> US 61/544860
< 151> 2011-10-07
<150> US 61/550623
< 151> 2011-10-24
<150> US 61/558110
< 151> 2011-11-10
<150> US 61/580903
< 151> 2011-12-28
<160> 2
<170> PatentIn verzija 3.1
<210> 1
< 211> 22
< 212> DNA
< 213> Veštačka
<220>
< 223> hPDE9-1
<400> 1
aggatgggat ccggctcctc ca 22
<210> 2
< 211> 21
< 212> DNA
< 213> Veštačka
<220>
< 223> hPDE9A-3
<400> 2
caggcacagt ctccttcact g 21
Claims (18)
1.Jedinjenje ili njegova farmakološki prihvatljiva so, naznačeno time, što je predstavljeno sa formulom (1):u kojojR1 je atom vodonika;R2 je aromatska prstenska grupa koja je izabrana iz grupe koja obuhvata fenilnu grupu, piridilnu grupu, i pirimidinilnu grupu, pri čemu dva atoma u aromatskom prstenu, koja su susedna atomu ugljenika koji je spojen na pirazolo[4,3-c]hinolinski prsten, svaki nezavisno poseduju supstituent koji je izabran iz Grupe A1, a ostali atomi na aromatskom prstenu nezavisno ponekad sadrže supstituent koji je izabran iz Grupe B1;R3 je atom vodonika, ili atom fluora;R4 je atom vodonika;R5 je oksepanilna grupa, dioksepanilna grupa, tetrahidropiranilna grupa, ili tetrahidrofuranilna grupa koja ponekad sadrži metoksi grupu;R6 je atom vodonika;Grupa A1 sadrži halogen atom, C1-6 alkilnu grupa koja ponekad sadrži 1 do 3 halogena atom, i C1-6 alkoksi grupu; aGrupa B1 se sastoji od halogenog atoma, cijano grupe, C1-6 alkilne grupe koja ponekad sadrži 1 do 3 halogena atoma, C1-6 alkoksi-C1-6 alkilne grupe, C1-6 alkoksi grupe koja ponekad sadrži 1 do 3 halogena atoma, i tetrahidropiranilne grupe,pod uslovom da kada R2 je 3-piridilna grupa, supstituent na poziciji 4 je halogeni atom, ili C1-6 alkilna grupa koja ponekad sadrži 1 do 3 halogena atoma.
2.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 1, naznačeno time, što R2 je aromatska prstenska grupa koja je izabrana iz grupe koja obuhvata fenilnu grupu, 3-piridilnu grupu, 4-piridilnu grupu, i 5-pirimidinilnu grupu, pri čemu dva atoma u aromatskom prstenu koja su susedna atomu ugljenika, koji je spojen na pirazolo[4,3-c]hinolinski prsten, svaki nezavisno sadrže supstituent koji je izabran iz Grupe A2, a ostali atomi u aromatskom prstenu nezavisno ponekad sadrže supstituent koji je izabran iz Grupe B2; R5 je 4-oksepanilna grupa, 1,4-dioksepan-6-il grupa, 3,4,5,6-tetrahidro-2H-3-piranilna grupa, 3,4,5,6-tetrahidro-2H-4-piranilna grupa, ili 3-tetrahidrofuranilna grupa; Grupa A2 se sastoji od atoma hlora, i metilne grupe koja ponekad sadrži 1 do 2 atoma fluora, etilne grupe, metoksi grupe, i etoksi grupe; a Grupa B2 se sastoji od atoma fluora, atoma hlora, cijano grupe, metilne grupe koja ponekad sadrži 1 do 3 atoma fluora, etilne grupe, metoksimetilne grupe, metoksi grupe koja ponekad sadrži 1 do 3 atoma fluora, etoksi grupe, izopropiloksi grupe, i 3,4,5,6-tetrahidro-2H-4-piranilne grupe.
3.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 2, naznačeno time, što R3 je atom fluora.
4.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 1, naznačeno time, što R3 je atom vodonika; a R5 je tetrahidropiranilna grupa, ili tetrahidrofuranilna grupa koja ponekad sadrži metoksi grupu.
5.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 2, naznačeno time, što R3 je atom vodonika; a R5 je 3,4,5,6-tetrahidro-2H-3-piranilna grupa, 3,4,5,6-tetrahidro-2H-4-piranilna grupa, ili 3-tetrahidrofuranilna grupa.
6.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 1, naznačeno time, što R2 je aromatska prstenska grupa koja je izabrana iz grupe koja obuhvata fenilnu grupu, 3-piridilnu grupu, i 4-piridilnu grupu, pri čemu dva atoma u aromatskom prstenu koja su susedna atomu ugljenika, koji je spojen na pirazolo[4,3-c]hinolinski prsten, svaki nezavisno sadrže supstituent koji je izabran iz Grupe A3, a ostali atomi u aromatskom prstenu nezavisno ponekad sadrže supstituent koji je izabran iz Grupe B3; R3 je atom vodonika; R4 je atom vodonika; R5 je 3,4,5,6-tetrahidro-2H-4-piranilna grupa, ili 3-tetrahidrofuranilna grupa; Grupa A3 se sastoji od metilne grupe, i metoksi grupe; a Grupa B3 se sastoji od metilne grupe, metoksi grupe, i metoksimetilne grupe.
7.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 1, naznačeno time, što je izabrano iz sledeće grupe: 1)7-(6-metoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidro-2H-piran-4-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 2)7-(2-metoksi-4,6-dimetilpiridin-3-il)-1-(tetrahidro-2H-piran-4-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 3)(S)-7-(6-izopropiloksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-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]hinolin-4(5H)-on, 5)1-(1,4-dioksepan-6-il)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 6)1-(1,4-dioksepan-6-il)-7-(2-metoksi-4,6-dimetilpiridin-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 7)(S)-8-fluoro-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 8)7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidro-2H-piran-4-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 9)(-)-7-(2-metoksi-4,6-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 10)(-)-7-(6-metoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 11)(S)-8-fluoro-7-(2-metoksi-4,6-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 12)(S)-7-(6-etoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on, 13)(S)-8-fluoro-7-(6-metoksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-((5H)-on, i 14)(S)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on.
8.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 7, naznačeno time, što predstavlja 7-(6-izopropiloksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on.
9.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 7, naznačeno time, što predstavlja (S)-7-(6-izopropiloksi-2,4-dimetilpiridin-3-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on
10.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 7, naznačeno time, što predstavlja 8-fluoro-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on.
11.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 7, naznačeno time, što predstavlja (S)-8-fluoro-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on:
12.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 7, naznačeno time, što predstavlja 7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on.
13.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 7, naznačeno time, što predstavlja (S)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1-(tetrahidrofuran-3-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on:
14.Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 7, naznačeno time, što predstavlja 1-(1,4-dioksepan-6-il)-7-(2-metoksi-3,5-dimetilpiridin-4-il)-1H-pirazolo[4,3-c]hinolin-4(5H)-on:
15.Farmaceutska kompozicija, naznačena time, što sadrži jedinjenje ili njegovu farmakološki prihvatljivu so u skladu sa zahtevom 1 kao aktivni sastojak.
16.Farmaceutska kompozicija u skladu sa zahtevom 15, naznačena time, što se upotrebljava kao inhibitor PDE9.
17.Farmaceutska kompozicija u skladu sa zahtevom 15, naznačena time, što se upotrebljava u postupku za povećavanje koncentracije intracerebralnog cGMP.
18. Jedinjenje ili njegova farmakološki prihvatljiva so u skladu sa zahtevom 1, naznačeno time, što se upotrebljava za poboljšanje kognitivnih poremećaja kod Alzheimer-ove 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 |
|---|---|
| ME02394B true ME02394B (me) | 2016-09-20 |
Family
ID=48043792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-65A ME02394B (me) | 2011-10-07 | 2012-10-04 | Pirazolohinolinski derivati kao inhibitori pde9 |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US8563565B2 (me) |
| EP (1) | EP2769980B1 (me) |
| JP (1) | JP5546693B2 (me) |
| KR (1) | KR101943680B1 (me) |
| CN (1) | CN103930423B (me) |
| AR (1) | AR088235A1 (me) |
| AU (1) | AU2012319549B2 (me) |
| BR (1) | BR112014007912B1 (me) |
| CA (1) | CA2861795C (me) |
| CL (1) | CL2014000821A1 (me) |
| CO (1) | CO6910200A2 (me) |
| CY (1) | CY1117427T1 (me) |
| DK (1) | DK2769980T3 (me) |
| ES (1) | ES2568015T3 (me) |
| HR (1) | HRP20160273T1 (me) |
| HU (1) | HUE028555T2 (me) |
| IL (1) | IL231650A (me) |
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| KR101997955B1 (ko) * | 2013-04-05 | 2019-07-08 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 피라졸로퀴놀린 유도체의 염, 및 이의 결정 |
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| WO2016021192A1 (en) * | 2014-08-08 | 2016-02-11 | Eisai R&D Management Co., Ltd. | Process for production of (s)-(tetrahydrofuran-3-yl)hydrazine |
| IL280619B2 (en) | 2015-07-07 | 2023-10-01 | H Lundbeck As | Phosphodiesterase 9 inhibitors with an imidazo triazinon or imidazo pyrazinone skeleton for the treatment of peripheral diseases |
| 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 |
| CN116585316A (zh) | 2017-06-01 | 2023-08-15 | 卫材R&D管理有限公司 | 包含pde9抑制剂的药物组合物 |
| AU2018276565A1 (en) * | 2017-06-01 | 2019-11-07 | Eisai R&D Management Co., Ltd. | Dementia therapeutic agent combining pyrazoloquinoline derivative and donepezil |
| JP7177772B2 (ja) * | 2017-06-01 | 2022-11-24 | 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 |
| ES2961554T3 (es) * | 2017-06-01 | 2024-03-12 | Eisai R&D Man Co Ltd | Agente terapéutico para enfermedad con cuerpos de Lewy que contiene derivado de pirazoloquinolina |
| US11591312B2 (en) | 2018-01-23 | 2023-02-28 | Basf Se | Halogenation of pyridine derivatives |
| EP4349403A3 (en) | 2018-05-25 | 2024-06-05 | Cardurion Pharmaceuticals, Inc. | Monohydrate and crystalline forms of 6-[(3s,4s)-4-methyl-1- (pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-3-tetrahydropyran-4-yl- 7h-imid azo [1,5- a] pyrazin-8-one |
| MA53501A (fr) | 2018-08-31 | 2021-07-07 | Imara Inc | Inhibiteurs de pde9 pour le traitement de la drépanocytose |
| EP3894403A1 (en) | 2018-12-13 | 2021-10-20 | Intervet International B.V. | Process for preparing 1-[(3r,4s)-4-cyanotetrahydropyran-3-yl]-3-[(2-fluoro-6-methoxy-4-pyridyl)amino]p yrazole-4-carboxamide |
| IL287617B2 (en) | 2019-05-09 | 2024-11-01 | Feinstein Institutes For Medical Research | Hmgb1 antagonist |
| US10919882B2 (en) | 2019-05-09 | 2021-02-16 | The Feinstein Institutes For Medical Research | Compounds for use in synthesis of peptidomimetics |
| US11883461B2 (en) | 2019-05-09 | 2024-01-30 | The Feinstein Institutes For Medical Research | HMGB1 antagonist treatment of severe sepsis |
| EP3966201A4 (en) | 2019-05-09 | 2023-01-18 | The Feinstein Institutes for Medical Research | THIOSEMICARBAZATE AND THEIR USES |
| WO2021150613A1 (en) | 2020-01-20 | 2021-07-29 | Incyte Corporation | Spiro compounds as inhibitors of kras |
| IL297165A (en) * | 2020-04-16 | 2022-12-01 | Incyte Corp | Soysag tricyclic CRS inhibitors |
| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
| CA3188782A1 (en) | 2020-06-30 | 2022-01-06 | 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 |
| WO2022204112A1 (en) | 2021-03-22 | 2022-09-29 | Incyte Corporation | Imidazole and triazole kras inhibitors |
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| RU2426734C2 (ru) * | 2003-10-03 | 2011-08-20 | Зм Инновейтив Пропертиз Компани | Пиразолопиридины и их аналоги |
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| CN101268073B (zh) | 2005-09-15 | 2011-10-19 | Aska制药株式会社 | 杂环化合物、制备方法及其用途 |
| JP2009184924A (ja) | 2006-05-31 | 2009-08-20 | Eisai R & D Management Co Ltd | 生物学的試薬用化合物 |
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| ES2612954T3 (es) * | 2009-03-05 | 2017-05-19 | Astellas Pharma Inc. | Compuestos de quinoxalina |
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| US8880976B2 (en) | 2009-09-25 | 2014-11-04 | Stmicroelectronics, Inc. | Method and apparatus for encoding LBA information into the parity of a LDPC system |
| EP2615089B1 (en) * | 2010-09-07 | 2016-04-27 | Astellas Pharma Inc. | Pyrazoloquinoline compounds |
| 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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