ES2568603T3 - Pirano[3,2-d][1,3]tiazol como inhibidores de glicosidasas - Google Patents
Pirano[3,2-d][1,3]tiazol como inhibidores de glicosidasas Download PDFInfo
- Publication number
- ES2568603T3 ES2568603T3 ES12753341.2T ES12753341T ES2568603T3 ES 2568603 T3 ES2568603 T3 ES 2568603T3 ES 12753341 T ES12753341 T ES 12753341T ES 2568603 T3 ES2568603 T3 ES 2568603T3
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- Spain
- Prior art keywords
- chiral
- disease
- indicates
- oga
- compound
- 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.)
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- 239000003316 glycosidase inhibitor Substances 0.000 title description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 210000004027 cell Anatomy 0.000 claims description 34
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- 206010012289 Dementia Diseases 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 3
- 201000010374 Down Syndrome Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 102000005744 Glycoside Hydrolases Human genes 0.000 claims 4
- 108010031186 Glycoside Hydrolases Proteins 0.000 claims 4
- 208000027089 Parkinsonian disease Diseases 0.000 claims 3
- 206010034010 Parkinsonism Diseases 0.000 claims 3
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 208000024571 Pick disease Diseases 0.000 claims 2
- 208000018756 Variant Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 208000019715 inherited Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 230000000750 progressive effect Effects 0.000 claims 2
- 206010003694 Atrophy Diseases 0.000 claims 1
- 208000033647 Classic progressive supranuclear palsy syndrome Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims 1
- 208000009093 Diffuse Neurofibrillary Tangles with Calcification Diseases 0.000 claims 1
- 102000002322 Egg Proteins Human genes 0.000 claims 1
- 108010000912 Egg Proteins Proteins 0.000 claims 1
- 208000003736 Gerstmann-Straussler-Scheinker Disease Diseases 0.000 claims 1
- 206010072075 Gerstmann-Straussler-Scheinker syndrome Diseases 0.000 claims 1
- 206010018341 Gliosis Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 1
- 208000014060 Niemann-Pick disease Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 102000029797 Prion Human genes 0.000 claims 1
- 108091000054 Prion Proteins 0.000 claims 1
- 208000024777 Prion disease Diseases 0.000 claims 1
- 208000037065 Subacute sclerosing leukoencephalitis Diseases 0.000 claims 1
- 206010042297 Subacute sclerosing panencephalitis Diseases 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000037444 atrophy Effects 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 210000000349 chromosome Anatomy 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 201000006061 fatal familial insomnia Diseases 0.000 claims 1
- 230000007387 gliosis Effects 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 206010023497 kuru Diseases 0.000 claims 1
- 238000012544 monitoring process Methods 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 210000004681 ovum Anatomy 0.000 claims 1
- 208000032207 progressive 1 supranuclear palsy Diseases 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 description 66
- 108090000790 Enzymes Proteins 0.000 description 35
- 102000004190 Enzymes Human genes 0.000 description 35
- 102100040243 Microtubule-associated protein tau Human genes 0.000 description 15
- 101001120790 Caenorhabditis elegans UDP-N-acetylglucosamine-peptide N-acetylglucosaminyltransferase Proteins 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 230000006951 hyperphosphorylation Effects 0.000 description 5
- 210000002682 neurofibrillary tangle Anatomy 0.000 description 5
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- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 108010077991 O-GlcNAc transferase Proteins 0.000 description 2
- 102000005520 O-GlcNAc transferase Human genes 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 102000001435 Synapsin Human genes 0.000 description 2
- 108050009621 Synapsin Proteins 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 102000010831 Cytoskeletal Proteins Human genes 0.000 description 1
- 108010037414 Cytoskeletal Proteins Proteins 0.000 description 1
- 208000031124 Dementia Alzheimer type Diseases 0.000 description 1
- 102100021238 Dynamin-2 Human genes 0.000 description 1
- 101000817607 Homo sapiens Dynamin-2 Proteins 0.000 description 1
- 101710159527 Maturation protein A Proteins 0.000 description 1
- 101710091157 Maturation protein A2 Proteins 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- 102000008763 Neurofilament Proteins Human genes 0.000 description 1
- 108010088373 Neurofilament Proteins Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- 208000007930 Type C Niemann-Pick Disease Diseases 0.000 description 1
- 230000002547 anomalous effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000005754 cellular signaling Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 102000035118 modified proteins Human genes 0.000 description 1
- 108091005573 modified proteins Proteins 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000004481 post-translational protein modification Effects 0.000 description 1
- 230000001323 posttranslational effect Effects 0.000 description 1
- 230000004063 proteosomal degradation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 208000033556 type C1 Niemann-Pick disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—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
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P25/14—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
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- 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
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- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/056—Triazole or tetrazole radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/06—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing nitrogen as ring hetero atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161527323P | 2011-08-25 | 2011-08-25 | |
| US201161527323P | 2011-08-25 | ||
| PCT/US2012/051785 WO2013028715A1 (en) | 2011-08-25 | 2012-08-22 | Pyrano [3, 2 - d] [1, 3] thiazole as glycosidase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2568603T3 true ES2568603T3 (es) | 2016-05-03 |
Family
ID=46759099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12753341.2T Active ES2568603T3 (es) | 2011-08-25 | 2012-08-22 | Pirano[3,2-d][1,3]tiazol como inhibidores de glicosidasas |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US8884023B2 (https=) |
| EP (1) | EP2748171B1 (https=) |
| JP (1) | JP5893738B2 (https=) |
| KR (1) | KR102008032B1 (https=) |
| CN (1) | CN103930428B (https=) |
| AU (1) | AU2012298949B2 (https=) |
| BR (1) | BR112014004219B1 (https=) |
| CA (1) | CA2845149C (https=) |
| DK (1) | DK2748171T3 (https=) |
| EA (1) | EA022562B1 (https=) |
| ES (1) | ES2568603T3 (https=) |
| HR (1) | HRP20160334T1 (https=) |
| HU (1) | HUE029390T2 (https=) |
| IL (1) | IL231008A (https=) |
| MX (1) | MX358463B (https=) |
| PL (1) | PL2748171T3 (https=) |
| RS (1) | RS54773B1 (https=) |
| SG (1) | SG2014009617A (https=) |
| SI (1) | SI2748171T1 (https=) |
| WO (1) | WO2013028715A1 (https=) |
| ZA (1) | ZA201400387B (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201249848A (en) * | 2010-11-08 | 2012-12-16 | Merck Sharp & Dohme | Selective glycosidase inhibitors and uses thereof |
| RU2609210C2 (ru) | 2010-12-23 | 2017-01-31 | Алектос Терапьютикс Инк. | Селективные ингибиторы гликозидазы и их применение |
| EP2688899B1 (en) | 2011-03-24 | 2017-02-22 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| EP2691407B1 (en) * | 2011-03-31 | 2017-02-22 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| US9701693B2 (en) | 2011-06-27 | 2017-07-11 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| EP2726468B1 (en) | 2011-06-27 | 2017-04-12 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| BR112013033098B8 (pt) | 2011-06-27 | 2021-03-23 | Alectos Therapeutics Inc | inibidores de glicosidade seletivos e usos dos mesmos |
| ES2568603T3 (es) * | 2011-08-25 | 2016-05-03 | Merck Patent Gmbh | Pirano[3,2-d][1,3]tiazol como inhibidores de glicosidasas |
| EP2890676B1 (en) | 2012-08-31 | 2018-12-05 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| EP2890675A4 (en) | 2012-08-31 | 2016-01-13 | Alectos Therapeutics Inc | GLYCOSIDASE INHIBITORS AND USES THEREOF |
| KR20150079711A (ko) | 2012-10-31 | 2015-07-08 | 알렉토스 테라퓨틱스 인크. | 글리코시다아제 저해제 및 이의 용도 |
| WO2014100934A1 (en) * | 2012-12-24 | 2014-07-03 | Merck Sharp & Dohme Corp. | Glycosidase inhibitors and uses thereof |
| KR102043337B1 (ko) | 2014-08-28 | 2019-11-11 | 아셰뉴론 에스아 | 글리코시다제 저해제 |
| CN108029215B (zh) * | 2015-09-18 | 2020-10-27 | 东丽株式会社 | 壳体 |
| CA3014572C (en) | 2016-02-25 | 2023-10-03 | Asceneuron S.A. | Acid addition salts of piperazine derivatives |
| 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 |
| US11213525B2 (en) | 2017-08-24 | 2022-01-04 | Asceneuron Sa | Linear glycosidase inhibitors |
| WO2020039027A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Pyrrolidine glycosidase inhibitors |
| WO2020039029A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Spiro compounds as 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 |
| WO2020039028A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Tetrahydro-benzoazepine glycosidase inhibitors |
| US12565504B2 (en) * | 2019-10-29 | 2026-03-03 | Biogen Ma Inc. | Spirocyclic O-glycoprotein-2-acetamido-2-deoxy-3-d-glucopyranosidase inhibitors |
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| CA2599843C (en) * | 2005-03-01 | 2013-08-27 | Simon Fraser University | Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof |
| EP1979360B1 (en) * | 2006-01-30 | 2009-10-14 | Irm Llc | Compounds and compositions as ppar modulators |
| AU2007291870B2 (en) * | 2006-08-31 | 2012-12-06 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| CN107253970A (zh) * | 2006-08-31 | 2017-10-17 | 西蒙·弗雷瑟大学 | 选择性糖苷酶抑制剂及其用途 |
| WO2011140640A1 (en) | 2010-05-11 | 2011-11-17 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| WO2012061972A1 (en) | 2010-11-08 | 2012-05-18 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| US8933040B2 (en) | 2010-11-08 | 2015-01-13 | Craig A. Coburn | Selective glycosidase inhibitors and uses thereof |
| RU2609210C2 (ru) | 2010-12-23 | 2017-01-31 | Алектос Терапьютикс Инк. | Селективные ингибиторы гликозидазы и их применение |
| ES2568603T3 (es) * | 2011-08-25 | 2016-05-03 | Merck Patent Gmbh | Pirano[3,2-d][1,3]tiazol como inhibidores de glicosidasas |
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