JP6626449B2 - PDE2阻害剤としての置換[1,2,4]トリアゾロ[1,5−a]ピリミジン−7−イル化合物 - Google Patents
PDE2阻害剤としての置換[1,2,4]トリアゾロ[1,5−a]ピリミジン−7−イル化合物 Download PDFInfo
- Publication number
- JP6626449B2 JP6626449B2 JP2016549758A JP2016549758A JP6626449B2 JP 6626449 B2 JP6626449 B2 JP 6626449B2 JP 2016549758 A JP2016549758 A JP 2016549758A JP 2016549758 A JP2016549758 A JP 2016549758A JP 6626449 B2 JP6626449 B2 JP 6626449B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- triazolo
- pyrimidin
- piperidine
- carbonyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
- 0 CC1*(C)CC2(C)C1*2 Chemical compound CC1*(C)CC2(C)C1*2 0.000 description 3
- KMYGJAHNADLPSL-JQEHKKLVSA-N C/C(/C(CC(C1)(F)F)CN1C(c1c[s]c2c1cccc2)=O)=C\C(\C)=N/c1ncn[nH]1 Chemical compound C/C(/C(CC(C1)(F)F)CN1C(c1c[s]c2c1cccc2)=O)=C\C(\C)=N/c1ncn[nH]1 KMYGJAHNADLPSL-JQEHKKLVSA-N 0.000 description 1
- WEXFQZZKUYNAOU-RVDMUPIBSA-N CC(C)(/C=C(\C)/C(CCC1)CN1C(C1Oc(cccc2)c2OC1)=O)Nc1ncn[nH]1 Chemical compound CC(C)(/C=C(\C)/C(CCC1)CN1C(C1Oc(cccc2)c2OC1)=O)Nc1ncn[nH]1 WEXFQZZKUYNAOU-RVDMUPIBSA-N 0.000 description 1
- AWKRAHIVPXRBGK-UHFFFAOYSA-N CC(C)[n]1nc(C)c(CN(CCC2)CC2c2cc(C)nc3ncn[n]23)c1C Chemical compound CC(C)[n]1nc(C)c(CN(CCC2)CC2c2cc(C)nc3ncn[n]23)c1C AWKRAHIVPXRBGK-UHFFFAOYSA-N 0.000 description 1
- SLUBNTPFHPZELU-UHFFFAOYSA-N CC(C=C1C(CCC2)CN2C(c2ccc(CCC3)c3c2)=O)=NNN1/N=C\N Chemical compound CC(C=C1C(CCC2)CN2C(c2ccc(CCC3)c3c2)=O)=NNN1/N=C\N SLUBNTPFHPZELU-UHFFFAOYSA-N 0.000 description 1
- FBOVHQQMHGZRTO-UHFFFAOYSA-N CC1=NC2=N[I]=NN2C(C(C2)OCCN2C(c(cc2)cc(Br)c2F)=O)=C1 Chemical compound CC1=NC2=N[I]=NN2C(C(C2)OCCN2C(c(cc2)cc(Br)c2F)=O)=C1 FBOVHQQMHGZRTO-UHFFFAOYSA-N 0.000 description 1
- QYXIXPDPNYDFFT-UHFFFAOYSA-N CC1=NC2=N[I]=NN2C(C(CCC2)CN2C(c(cc(cc2)Cl)c2Cl)=O)=C1 Chemical compound CC1=NC2=N[I]=NN2C(C(CCC2)CN2C(c(cc(cc2)Cl)c2Cl)=O)=C1 QYXIXPDPNYDFFT-UHFFFAOYSA-N 0.000 description 1
- RAEJCXMKZBREMU-UHFFFAOYSA-N CC1Nc2ncn[n]2C(C(CC(C2)(F)F)CN2C(c(cc2Cl)ccc2F)=O)=C1 Chemical compound CC1Nc2ncn[n]2C(C(CC(C2)(F)F)CN2C(c(cc2Cl)ccc2F)=O)=C1 RAEJCXMKZBREMU-UHFFFAOYSA-N 0.000 description 1
- FFZKUKNWISMTRC-UHFFFAOYSA-N Cc(c(C(N(CCC1)CC1c1cc(C)nc2[n]cn[n]12)=O)c1)ccc1F Chemical compound Cc(c(C(N(CCC1)CC1c1cc(C)nc2[n]cn[n]12)=O)c1)ccc1F FFZKUKNWISMTRC-UHFFFAOYSA-N 0.000 description 1
- LPEFAZXZCBWJQR-UHFFFAOYSA-N Cc(cc1)cc(C(N(CC(C2)C3=CC(C)=NC4N3NCN4C)CC2(F)F)=O)c1OC Chemical compound Cc(cc1)cc(C(N(CC(C2)C3=CC(C)=NC4N3NCN4C)CC2(F)F)=O)c1OC LPEFAZXZCBWJQR-UHFFFAOYSA-N 0.000 description 1
- TVCQGAGMWNYZSJ-UHFFFAOYSA-N Cc(cc1)ncc1C(N(CCC1)CC1c1cc(C)nc2ncn[n]12)=O Chemical compound Cc(cc1)ncc1C(N(CCC1)CC1c1cc(C)nc2ncn[n]12)=O TVCQGAGMWNYZSJ-UHFFFAOYSA-N 0.000 description 1
- OMOVOASJEKHAJK-UHFFFAOYSA-N Cc(nc(CN(CCC1)CC1c1cc(C)nc2ncn[n]12)[s]1)c1Br Chemical compound Cc(nc(CN(CCC1)CC1c1cc(C)nc2ncn[n]12)[s]1)c1Br OMOVOASJEKHAJK-UHFFFAOYSA-N 0.000 description 1
- LBRGDCSDFXBJFQ-UHFFFAOYSA-N Cc1cc(C(N2CC(c3cc(C)nc4ncn[n]34)=[O]CC2)=O)ccc1F Chemical compound Cc1cc(C(N2CC(c3cc(C)nc4ncn[n]34)=[O]CC2)=O)ccc1F LBRGDCSDFXBJFQ-UHFFFAOYSA-N 0.000 description 1
- MLHNDSRGAWDMAQ-UHFFFAOYSA-N Cc1ccc(CN(CCC2)CC2C2=CC(C)=NC3N2N=CN3)c(C)n1 Chemical compound Cc1ccc(CN(CCC2)CC2C2=CC(C)=NC3N2N=CN3)c(C)n1 MLHNDSRGAWDMAQ-UHFFFAOYSA-N 0.000 description 1
- BKCNQIWNWKWQCX-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(C2)OCCN2C(c(cc2)cc3c2OCCO3)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(C2)OCCN2C(c(cc2)cc3c2OCCO3)=O)c1 BKCNQIWNWKWQCX-UHFFFAOYSA-N 0.000 description 1
- FSGAEDWCQCTQAR-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(C2)OCCN2C(c2cc(Cl)cc(Br)c2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(C2)OCCN2C(c2cc(Cl)cc(Br)c2)=O)c1 FSGAEDWCQCTQAR-UHFFFAOYSA-N 0.000 description 1
- UEFWQUJANIWJFX-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CC(C2)(F)F)CN2C(c2cc(F)cc(OC)c2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CC(C2)(F)F)CN2C(c2cc(F)cc(OC)c2)=O)c1 UEFWQUJANIWJFX-UHFFFAOYSA-N 0.000 description 1
- RZWKBDDIPFHABT-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c(cc2)c[n]3c2ncc3)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c(cc2)c[n]3c2ncc3)=O)c1 RZWKBDDIPFHABT-UHFFFAOYSA-N 0.000 description 1
- GUHUITAEUBORSY-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c(cc2)nc3c2cncc3)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c(cc2)nc3c2cncc3)=O)c1 GUHUITAEUBORSY-UHFFFAOYSA-N 0.000 description 1
- VVQDCADVVMKADM-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c(cccc2F)c2OC)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c(cccc2F)c2OC)=O)c1 VVQDCADVVMKADM-UHFFFAOYSA-N 0.000 description 1
- JJVZYPPVEXVFIL-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2cc(cccc3)c3[o]2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2cc(cccc3)c3[o]2)=O)c1 JJVZYPPVEXVFIL-UHFFFAOYSA-N 0.000 description 1
- WJUXFOUYSFBKAG-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2cc(cccc3)c3cc2OC)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2cc(cccc3)c3cc2OC)=O)c1 WJUXFOUYSFBKAG-UHFFFAOYSA-N 0.000 description 1
- LUTXGPVFTSPTNU-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ccc3N(C)CSc3c2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ccc3N(C)CSc3c2)=O)c1 LUTXGPVFTSPTNU-UHFFFAOYSA-N 0.000 description 1
- UDTOPNUYTQMIBU-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ccc3OCCc3c2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ccc3OCCc3c2)=O)c1 UDTOPNUYTQMIBU-UHFFFAOYSA-N 0.000 description 1
- IHQDGHMTKMWEKW-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ccncc2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ccncc2)=O)c1 IHQDGHMTKMWEKW-UHFFFAOYSA-N 0.000 description 1
- JCZVTTGBEBQTRR-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2nc(cccc3)c3nc2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2nc(cccc3)c3nc2)=O)c1 JCZVTTGBEBQTRR-UHFFFAOYSA-N 0.000 description 1
- UASIPENFCOFGGB-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ncccc2)=O)c1 Chemical compound Cc1nc2ncn[n]2c(C(CCC2)CN2C(c2ncccc2)=O)c1 UASIPENFCOFGGB-UHFFFAOYSA-N 0.000 description 1
- OAXZWJIDTSZAGW-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C2CN(Cc(c(F)c3)ccc3Br)CCC2)c1 Chemical compound Cc1nc2ncn[n]2c(C2CN(Cc(c(F)c3)ccc3Br)CCC2)c1 OAXZWJIDTSZAGW-UHFFFAOYSA-N 0.000 description 1
- JCRVZTMZRKFKQQ-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C2CN(Cc(cc3)cc4c3OCO4)CCC2)c1 Chemical compound Cc1nc2ncn[n]2c(C2CN(Cc(cc3)cc4c3OCO4)CCC2)c1 JCRVZTMZRKFKQQ-UHFFFAOYSA-N 0.000 description 1
- GOWPCVQXFJSDBN-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C2CN(Cc(cc3)ccc3-[n]3cncc3)CCC2)c1 Chemical compound Cc1nc2ncn[n]2c(C2CN(Cc(cc3)ccc3-[n]3cncc3)CCC2)c1 GOWPCVQXFJSDBN-UHFFFAOYSA-N 0.000 description 1
- SHLQNGRJNWIQKO-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C2CN(Cc(cc3)ccc3C#N)CCC2)c1 Chemical compound Cc1nc2ncn[n]2c(C2CN(Cc(cc3)ccc3C#N)CCC2)c1 SHLQNGRJNWIQKO-UHFFFAOYSA-N 0.000 description 1
- SYBSGIWWPYXQJB-UHFFFAOYSA-N Cc1nc2ncn[n]2c(C2CNCCC2)c1 Chemical compound Cc1nc2ncn[n]2c(C2CNCCC2)c1 SYBSGIWWPYXQJB-UHFFFAOYSA-N 0.000 description 1
- XPLDKVPANJVZKB-DLBZAZTESA-N Cc1nc2ncn[n]2c([C@@H](CCC2)CN2C([C@H](C2)COc3c2cccc3)=O)c1 Chemical compound Cc1nc2ncn[n]2c([C@@H](CCC2)CN2C([C@H](C2)COc3c2cccc3)=O)c1 XPLDKVPANJVZKB-DLBZAZTESA-N 0.000 description 1
- JIKFBOGXVCBDFJ-QAPCUYQASA-N Cc1nc2ncn[n]2c([C@H](C2)OCCN2C([C@H](C2)COc3c2cccc3)=O)c1 Chemical compound Cc1nc2ncn[n]2c([C@H](C2)OCCN2C([C@H](C2)COc3c2cccc3)=O)c1 JIKFBOGXVCBDFJ-QAPCUYQASA-N 0.000 description 1
- MJYKLHHOSPOGEE-SFHVURJKSA-N Cc1nc2ncn[n]2c([C@H](C2)OCCN2C(c2ccc(C3CC3)cc2)=O)c1 Chemical compound Cc1nc2ncn[n]2c([C@H](C2)OCCN2C(c2ccc(C3CC3)cc2)=O)c1 MJYKLHHOSPOGEE-SFHVURJKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/48—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase
- C12Q1/50—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase involving creatine phosphokinase
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pain & Pain Management (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Genetics & Genomics (AREA)
- Physics & Mathematics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461983387P | 2014-04-23 | 2014-04-23 | |
| US61/983,387 | 2014-04-23 | ||
| PCT/US2015/027102 WO2015164508A1 (en) | 2014-04-23 | 2015-04-22 | Substituted [1,2,4] triazolo [1,5-a] pyrimidin-7-yl compounds as pde2 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017513808A JP2017513808A (ja) | 2017-06-01 |
| JP2017513808A5 JP2017513808A5 (https=) | 2018-05-24 |
| JP6626449B2 true JP6626449B2 (ja) | 2019-12-25 |
Family
ID=53055118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016549758A Active JP6626449B2 (ja) | 2014-04-23 | 2015-04-22 | PDE2阻害剤としての置換[1,2,4]トリアゾロ[1,5−a]ピリミジン−7−イル化合物 |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US9932345B2 (https=) |
| EP (2) | EP3597649B8 (https=) |
| JP (1) | JP6626449B2 (https=) |
| KR (1) | KR102471058B1 (https=) |
| CN (2) | CN106459062A (https=) |
| AU (2) | AU2015249753B2 (https=) |
| BR (1) | BR112016024713B1 (https=) |
| CA (1) | CA2938294C (https=) |
| DK (2) | DK3134413T3 (https=) |
| ES (2) | ES2902806T3 (https=) |
| HR (1) | HRP20212035T1 (https=) |
| HU (1) | HUE057317T2 (https=) |
| IL (2) | IL248292A (https=) |
| MA (1) | MA50375A (https=) |
| MX (1) | MX358004B (https=) |
| NZ (1) | NZ725161A (https=) |
| PL (1) | PL3597649T3 (https=) |
| PT (1) | PT3597649T (https=) |
| RU (1) | RU2659070C9 (https=) |
| SG (1) | SG11201606216UA (https=) |
| SI (1) | SI3597649T1 (https=) |
| TW (1) | TWI664181B (https=) |
| WO (1) | WO2015164508A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK3134413T3 (da) | 2014-04-23 | 2019-10-14 | Dart Neuroscience Cayman Ltd | Substituerede [1,2,4]triazolo[1,5-a]pyrimidin-7-yl-forbindelser som pde2-inhibitorer |
| KR102043337B1 (ko) | 2014-08-28 | 2019-11-11 | 아셰뉴론 에스아 | 글리코시다제 저해제 |
| US10239882B2 (en) | 2014-11-05 | 2019-03-26 | Dart Neuroscience (Cayman) Ltd. | Substituted 5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine compounds as PDE2 inhibitors |
| CN108349979B (zh) * | 2015-11-02 | 2021-04-09 | 詹森药业有限公司 | [1,2,4]三唑并[1,5-a]嘧啶-7-基化合物 |
| AU2017222964B2 (en) | 2016-02-25 | 2020-01-02 | Asceneuron S. A. | Glycosidase inhibitors |
| KR20180132629A (ko) | 2016-02-25 | 2018-12-12 | 아셰뉴론 에스아 | 글리코시다제 저해제 |
| US11261183B2 (en) | 2016-02-25 | 2022-03-01 | Asceneuron Sa | Sulfoximine glycosidase inhibitors |
| CA3014572C (en) | 2016-02-25 | 2023-10-03 | Asceneuron S.A. | Acid addition salts of piperazine derivatives |
| CN109890824B (zh) * | 2016-11-02 | 2022-05-24 | 詹森药业有限公司 | 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物 |
| EA039102B1 (ru) * | 2016-11-02 | 2021-12-03 | Янссен Фармацевтика Нв | Соединения [1,2,4]триазоло[1,5-a]пиримидина в качестве ингибиторов pde2 |
| MY193511A (en) | 2016-11-02 | 2022-10-17 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine derivatives as pde2 inhibitors |
| US20190359609A1 (en) * | 2016-12-16 | 2019-11-28 | Janssen Pharmaceutica Nv | Bicyclic oga inhibitor compounds |
| WO2018154133A1 (en) | 2017-02-27 | 2018-08-30 | Janssen Pharmaceutica Nv | [1,2,4]-triazolo [1,5-a]-pyrimidinyl derivatives substituted with piperidine, morpholine or piperazine as oga inhibitors |
| US11213525B2 (en) | 2017-08-24 | 2022-01-04 | Asceneuron Sa | Linear glycosidase inhibitors |
| WO2020039029A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Spiro compounds as glycosidase inhibitors |
| WO2020039027A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Pyrrolidine glycosidase inhibitors |
| WO2020039028A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Tetrahydro-benzoazepine glycosidase inhibitors |
| JP7407171B2 (ja) | 2018-08-22 | 2023-12-28 | エースニューロン・ソシエテ・アノニム | グリコシダーゼ阻害剤として有用なピペラジン誘導体のコハク酸付加塩及びフマル酸付加塩 |
| EP3969639B1 (en) | 2019-05-13 | 2025-03-12 | Ecolab Usa Inc. | 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor |
| TWI907472B (zh) | 2020-08-05 | 2025-12-11 | 匈牙利商羅特格登公司 | 具藥理活性之經雜環取代的吡唑并〔1,5-a〕嘧啶衍生物 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2510111A1 (fr) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | Nouveaux derives du piperidin-3-yl indole, leurs sels, leur procede de preparation, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| HU208693B (en) | 1991-02-22 | 1993-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them |
| US5478825A (en) | 1991-02-22 | 1995-12-26 | Egis Gyogyszergyar | 5-(substituted amino)-1,2,4-triazolo (1,5-A) pyrimidine derivatives |
| US9931318B2 (en) | 2003-04-08 | 2018-04-03 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| ATE526020T1 (de) | 2000-08-10 | 2011-10-15 | Cold Spring Harbor Lab | Gesteigertes kognitives training |
| US7868015B2 (en) | 2000-08-10 | 2011-01-11 | Cold Spring Harbor Laboratory | Phosphodiesesterase 4 inhibitors for the treatment of a cognitive deficit |
| DE10064105A1 (de) | 2000-12-21 | 2002-06-27 | Bayer Ag | Neue Substituierte Imidazotriazinone |
| WO2002064211A1 (en) | 2001-02-09 | 2002-08-22 | Merck & Co., Inc. | Thrombin inhibitors |
| DE10108752A1 (de) | 2001-02-23 | 2002-09-05 | Bayer Ag | Neue Substituierte Imidazotriazinone |
| FR2832711B1 (fr) * | 2001-11-26 | 2004-01-30 | Warner Lambert Co | Derives de triazolo [4,3-a] pyrido [2,3-d] pyrimidin-5-ones, compositions les contenant, procede de preparation et utilisation |
| AU2003276220A1 (en) | 2002-11-13 | 2004-06-03 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with human phosphodiesterase 2a (pde2a) |
| WO2004108136A1 (en) | 2003-06-04 | 2004-12-16 | Vernalis (Cambridge) Limited | Triazolo `1 , 5-a!pyrimidines and their use in medicine |
| WO2005041957A1 (en) | 2003-10-29 | 2005-05-12 | Pfizer Products Inc. | Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors |
| DE10356579A1 (de) | 2003-12-04 | 2005-07-07 | Merck Patent Gmbh | Aminderivate |
| EP1548011A1 (en) | 2003-12-23 | 2005-06-29 | Neuro3D | Benzo[1,4]diazepin-2-one derivatives as phosphodiesterase PDE2 inhibitors, preparation and therapeutic use thereof |
| AU2005279221C9 (en) | 2004-09-02 | 2012-08-23 | Takeda Gmbh | Triazolophthalazines |
| EP1874775B1 (en) | 2005-01-05 | 2012-10-10 | Nycomed GmbH | Triazolophthalazines as pde2-inhibitors |
| BRPI0606379A2 (pt) | 2005-01-05 | 2009-06-23 | Nycomed Gmbh | triazolftalazinas |
| US7868016B2 (en) | 2005-07-13 | 2011-01-11 | Baxter International Inc. | Pharmaceutical formulations of endo-N-(9-methyl-9-azabicyclo[3,3.1]non-3-yl)-1-methyl-1H-indazole-3-carboxamide hydrochloride |
| CN101321758A (zh) * | 2005-10-03 | 2008-12-10 | 阿斯利康(瑞典)有限公司 | 用于治疗哮喘和慢性阻塞性肺病的新5,6-二氢吡唑并[3,4-e][1,4]二氮杂-4(1H)-酮衍生物 |
| KR100844125B1 (ko) | 2007-03-23 | 2008-07-04 | 한국화학연구원 | 7-(3′,4′-디알콕시페닐)-[1,2,4]트리아졸로[1,5-a]피리미딘 화합물, 이의 제조방법 및 이를 포함하는 천식 및만성폐쇄성 폐질환을 포함한 염증관련 질환, 관절염,아토피 피부염, 암 및 뇌질환의 치료 및 예방을 위한약제학적 조성물 |
| JP2010527243A (ja) | 2007-05-15 | 2010-08-12 | ヘリコン セラピューティクス,インコーポレイテッド | 低分子干渉RNA(siRNA)を用いた記憶形成に関わる遺伝子の同定方法 |
| TWI501965B (zh) | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為pde10a酵素抑制劑之新穎苯基咪唑衍生物 |
| WO2010054260A1 (en) | 2008-11-07 | 2010-05-14 | Biotie Therapies Gmbh | Imidazo[5,1-c][1,2,4]benzotriazine derivatives as inhibitors of phosphodiesterases |
| US20100120762A1 (en) | 2008-11-07 | 2010-05-13 | Wyeth | Triazine derivatives as inhibitors of phosphodiesterases |
| PE20120505A1 (es) | 2009-03-31 | 2012-05-09 | Boehringer Ingelheim Int | Derivados de 1-heterociclil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona como moduladores de pde9a |
| US8680116B2 (en) | 2009-07-22 | 2014-03-25 | Merck Sharp & Dohme Corp. | Quinolinone PDE2 inhibitors |
| EP2651405A2 (en) * | 2010-12-14 | 2013-10-23 | Electrophoretics Limited | Casein kinase 1 (ck1 ) inhibitors |
| US9540379B2 (en) | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| KR101548443B1 (ko) | 2011-02-23 | 2015-08-28 | 화이자 인코포레이티드 | 신경 장애의 치료를 위한 이미다조[5,1-f][1,2,4]트라이아진 |
| SG195085A1 (en) | 2011-06-07 | 2013-12-30 | Pfizer | Pyrazolo[3,4-d]pyrimidine compounds and their use as pde2 inhibitors and/or cyp3a4 inhibitors |
| BR112013033375B1 (pt) | 2011-06-27 | 2022-05-10 | Janssen Pharmaceutica N.V | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário |
| JP2014526453A (ja) | 2011-09-09 | 2014-10-06 | ハー・ルンドベック・アクチエゼルスカベット | ピリジン化合物およびそれらの使用 |
| WO2013034758A1 (en) | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Substituted triazolopyrazines and uses thereof |
| WO2013034755A1 (en) | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Triazolopyrazine derivatives and their use for treating neurological and psychiatric disorders |
| US20130116241A1 (en) * | 2011-11-09 | 2013-05-09 | Abbvie Inc. | Novel inhibitor compounds of phosphodiesterase type 10a |
| CN103183675A (zh) * | 2011-12-27 | 2013-07-03 | 山东轩竹医药科技有限公司 | 磷酸二酯酶-4抑制剂 |
| JPWO2015012328A1 (ja) | 2013-07-24 | 2017-03-02 | 武田薬品工業株式会社 | 複素環化合物 |
| DK3134413T3 (da) | 2014-04-23 | 2019-10-14 | Dart Neuroscience Cayman Ltd | Substituerede [1,2,4]triazolo[1,5-a]pyrimidin-7-yl-forbindelser som pde2-inhibitorer |
| US10239882B2 (en) | 2014-11-05 | 2019-03-26 | Dart Neuroscience (Cayman) Ltd. | Substituted 5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine compounds as PDE2 inhibitors |
-
2015
- 2015-04-22 DK DK15721086.5T patent/DK3134413T3/da active
- 2015-04-22 EP EP19194930.4A patent/EP3597649B8/en active Active
- 2015-04-22 US US15/306,069 patent/US9932345B2/en active Active
- 2015-04-22 MX MX2016013860A patent/MX358004B/es active IP Right Grant
- 2015-04-22 SI SI201531770T patent/SI3597649T1/sl unknown
- 2015-04-22 CN CN201580030165.6A patent/CN106459062A/zh active Pending
- 2015-04-22 CA CA2938294A patent/CA2938294C/en active Active
- 2015-04-22 HU HUE19194930A patent/HUE057317T2/hu unknown
- 2015-04-22 MA MA050375A patent/MA50375A/fr unknown
- 2015-04-22 CN CN201910367854.6A patent/CN110092788B/zh active Active
- 2015-04-22 KR KR1020167032113A patent/KR102471058B1/ko active Active
- 2015-04-22 PT PT191949304T patent/PT3597649T/pt unknown
- 2015-04-22 NZ NZ725161A patent/NZ725161A/en unknown
- 2015-04-22 BR BR112016024713-2A patent/BR112016024713B1/pt active IP Right Grant
- 2015-04-22 DK DK19194930.4T patent/DK3597649T3/da active
- 2015-04-22 JP JP2016549758A patent/JP6626449B2/ja active Active
- 2015-04-22 ES ES19194930T patent/ES2902806T3/es active Active
- 2015-04-22 AU AU2015249753A patent/AU2015249753B2/en active Active
- 2015-04-22 HR HRP20212035TT patent/HRP20212035T1/hr unknown
- 2015-04-22 WO PCT/US2015/027102 patent/WO2015164508A1/en not_active Ceased
- 2015-04-22 SG SG11201606216UA patent/SG11201606216UA/en unknown
- 2015-04-22 PL PL19194930T patent/PL3597649T3/pl unknown
- 2015-04-22 EP EP15721086.5A patent/EP3134413B1/en active Active
- 2015-04-22 ES ES15721086T patent/ES2759246T3/es active Active
- 2015-04-22 RU RU2016143387A patent/RU2659070C9/ru active
- 2015-04-23 TW TW104113093A patent/TWI664181B/zh active
-
2016
- 2016-10-10 IL IL248292A patent/IL248292A/en active IP Right Grant
-
2017
- 2017-08-30 IL IL254224A patent/IL254224B/en active IP Right Grant
-
2018
- 2018-02-26 US US15/905,672 patent/US10501465B2/en active Active
-
2019
- 2019-11-25 US US16/694,869 patent/US11186582B2/en active Active
- 2019-12-20 AU AU2019283994A patent/AU2019283994C1/en active Active
-
2022
- 2022-06-27 US US17/850,668 patent/US20230192698A1/en not_active Abandoned
-
2024
- 2024-03-22 US US18/613,695 patent/US20250092047A1/en active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6626449B2 (ja) | PDE2阻害剤としての置換[1,2,4]トリアゾロ[1,5−a]ピリミジン−7−イル化合物 | |
| KR102776114B1 (ko) | 무스카린성 아세틸콜린 수용체 m4의 길항제 | |
| JP7097373B2 (ja) | キナーゼ阻害剤としてのアミノトリアゾロピリジン | |
| KR102292433B1 (ko) | Gsk-3 억제제로서 유용한 치환된 피리딘 유도체 | |
| US20200347071A1 (en) | Aminopyrrolotriazines as kinase inhibitors | |
| TWI568737B (zh) | 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 | |
| AU2010291199A1 (en) | Pyrazinylpyridines useful for the treatment of proliferative diseases | |
| US9708334B2 (en) | Substituted 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole and 4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine compounds as GlyT1 inhibitors | |
| KR102590848B1 (ko) | Pde2 억제제로서 치환된 피라졸로피리미디논 화합물 | |
| HK1228895A1 (en) | Substituted [1,2,4]triazolo [1,5-a]pyrimidin-7-yl compounds as pde2 inhibitors | |
| HK1228895B (en) | Substituted [1,2,4]triazolo [1,5-a]pyrimidin-7-yl compounds as pde2 inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161019 Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161004 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170306 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180403 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180403 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20181203 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20181206 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190304 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190401 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190603 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20191105 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20191129 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6626449 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |