ES2896938T3 - Inhibidores de GSK-3 - Google Patents
Inhibidores de GSK-3 Download PDFInfo
- Publication number
- ES2896938T3 ES2896938T3 ES17812187T ES17812187T ES2896938T3 ES 2896938 T3 ES2896938 T3 ES 2896938T3 ES 17812187 T ES17812187 T ES 17812187T ES 17812187 T ES17812187 T ES 17812187T ES 2896938 T3 ES2896938 T3 ES 2896938T3
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- Prior art keywords
- mmol
- mixture
- concentrated
- pyridazine
- esi
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- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 title description 28
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 title description 28
- 239000003112 inhibitor Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims abstract description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims abstract description 3
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims abstract description 3
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 9
- 238000011282 treatment Methods 0.000 claims description 18
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
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- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 201000004810 Vascular dementia Diseases 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
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- 238000000034 method Methods 0.000 description 148
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
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- 238000006243 chemical reaction Methods 0.000 description 18
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
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- 239000002253 acid Substances 0.000 description 12
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- JOTRPRKONYTVBV-UHFFFAOYSA-N 4-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CN=CC=C1Cl JOTRPRKONYTVBV-UHFFFAOYSA-N 0.000 description 10
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- 238000002560 therapeutic procedure Methods 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K31/495—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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662426630P | 2016-11-28 | 2016-11-28 | |
| PCT/US2017/063230 WO2018098411A1 (en) | 2016-11-28 | 2017-11-27 | Gsk-3 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2896938T3 true ES2896938T3 (es) | 2022-02-28 |
Family
ID=60655129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17812187T Active ES2896938T3 (es) | 2016-11-28 | 2017-11-27 | Inhibidores de GSK-3 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10774086B2 (https=) |
| EP (1) | EP3544980B1 (https=) |
| JP (1) | JP6977038B2 (https=) |
| KR (1) | KR102611539B1 (https=) |
| CN (1) | CN110225912B (https=) |
| ES (1) | ES2896938T3 (https=) |
| MA (1) | MA46888A (https=) |
| WO (1) | WO2018098411A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3920885A1 (en) | 2019-02-08 | 2021-12-15 | Frequency Therapeutics, Inc. | Valproic acid compounds and wnt agonists for treating ear disorders |
| CN111620881B (zh) * | 2020-07-08 | 2023-03-31 | 浙江合聚生物医药有限公司 | 拉罗替尼衍生物及其制备方法和应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY29823A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | Derivados sustituidos de 7-cloro-3h-imidazol-(4,5-b) piridina, composiciones farmacéuticas que los contienen, procesos para la preparación de los mismos y aplicaciones |
| US20090170847A1 (en) * | 2006-01-23 | 2009-07-02 | Seung Chul Lee | Imidazopyridine Derivatives Inhibiting Protein Kinase Activity, Method for the Preparation Thereof and Pharmaceutical Composition Containing Same |
| US20100292205A1 (en) * | 2006-08-23 | 2010-11-18 | Pfizer Inc. | Pyrimidone Compounds As GSK-3 Inhibitors |
| US8053574B2 (en) * | 2007-07-18 | 2011-11-08 | Novartis Ag | Organic compounds |
| SI2694510T1 (sl) * | 2011-04-07 | 2016-02-29 | Bayer Intellectual Property Gmbh | Imidazopiridazini kot inhibitorji AKT kinaze |
| RU2014120180A (ru) * | 2011-10-20 | 2015-11-27 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Замещенные бициклические аза-гетероциклы и аналоги в качестве модуляторов сиртуина |
| CN105849098A (zh) * | 2013-11-06 | 2016-08-10 | 百时美施贵宝公司 | Gsk-3抑制剂 |
-
2017
- 2017-11-27 CN CN201780084338.1A patent/CN110225912B/zh active Active
- 2017-11-27 EP EP17812187.7A patent/EP3544980B1/en active Active
- 2017-11-27 WO PCT/US2017/063230 patent/WO2018098411A1/en not_active Ceased
- 2017-11-27 JP JP2019528536A patent/JP6977038B2/ja active Active
- 2017-11-27 KR KR1020197018281A patent/KR102611539B1/ko active Active
- 2017-11-27 US US16/463,451 patent/US10774086B2/en active Active
- 2017-11-27 MA MA046888A patent/MA46888A/fr unknown
- 2017-11-27 ES ES17812187T patent/ES2896938T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019535790A (ja) | 2019-12-12 |
| KR20190085112A (ko) | 2019-07-17 |
| EP3544980A1 (en) | 2019-10-02 |
| US20190276463A1 (en) | 2019-09-12 |
| EP3544980B1 (en) | 2021-10-13 |
| CN110225912B (zh) | 2022-10-21 |
| US10774086B2 (en) | 2020-09-15 |
| CN110225912A (zh) | 2019-09-10 |
| MA46888A (fr) | 2021-06-02 |
| KR102611539B1 (ko) | 2023-12-06 |
| JP6977038B2 (ja) | 2021-12-08 |
| WO2018098411A1 (en) | 2018-05-31 |
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