CA2583550C - Thienopyridines as allosteric potentiators of the m4 muscarinic receptor - Google Patents
Thienopyridines as allosteric potentiators of the m4 muscarinic receptor Download PDFInfo
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- CA2583550C CA2583550C CA2583550A CA2583550A CA2583550C CA 2583550 C CA2583550 C CA 2583550C CA 2583550 A CA2583550 A CA 2583550A CA 2583550 A CA2583550 A CA 2583550A CA 2583550 C CA2583550 C CA 2583550C
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- Prior art keywords
- compound
- methyl
- chloro
- thieno
- amino
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- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title abstract description 23
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title abstract description 23
- 230000003281 allosteric effect Effects 0.000 title abstract description 20
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- 239000002175 thienopyridine Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
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- 150000001875 compounds Chemical class 0.000 claims description 161
- -1 morpholino, thiazolyl Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- NJBOUQLKCGARJL-UHFFFAOYSA-N 3-amino-5-chloro-n-cyclopropyl-4-methyl-6-oxo-7h-thieno[2,3-b]pyridine-2-carboxamide Chemical compound NC=1C=2C(C)=C(Cl)C(O)=NC=2SC=1C(=O)NC1CC1 NJBOUQLKCGARJL-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000166 1,3-dioxalanyl group Chemical group 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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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
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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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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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
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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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
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- 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
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measurement Of Velocity Or Position Using Acoustic Or Ultrasonic Waves (AREA)
- Peptides Or Proteins (AREA)
- Compression, Expansion, Code Conversion, And Decoders (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62178504P | 2004-10-25 | 2004-10-25 | |
| US60/621,785 | 2004-10-25 | ||
| PCT/US2005/037271 WO2006047124A1 (en) | 2004-10-25 | 2005-10-18 | Thienopyridines as allosteric potentiators of the m4 muscarinic receptor |
Publications (2)
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| CA2583550A1 CA2583550A1 (en) | 2006-05-04 |
| CA2583550C true CA2583550C (en) | 2013-05-14 |
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|---|---|---|---|
| CA2583550A Expired - Fee Related CA2583550C (en) | 2004-10-25 | 2005-10-18 | Thienopyridines as allosteric potentiators of the m4 muscarinic receptor |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8071776B2 (https=) |
| EP (1) | EP1807434B1 (https=) |
| JP (1) | JP4945453B2 (https=) |
| CN (1) | CN100577666C (https=) |
| AT (1) | ATE478876T1 (https=) |
| AU (1) | AU2005299957B2 (https=) |
| BR (1) | BRPI0517438A (https=) |
| CA (1) | CA2583550C (https=) |
| CY (1) | CY1111477T1 (https=) |
| DE (1) | DE602005023197D1 (https=) |
| DK (1) | DK1807434T3 (https=) |
| ES (1) | ES2349416T3 (https=) |
| MX (1) | MX2007004794A (https=) |
| PL (1) | PL1807434T3 (https=) |
| PT (1) | PT1807434E (https=) |
| WO (1) | WO2006047124A1 (https=) |
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| US9493481B2 (en) | 2012-02-23 | 2016-11-15 | Vanderbilt University | Substituted 5-aminothieno[2,3—C]pyridazine-6-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor M4 |
| WO2014035829A1 (en) * | 2012-08-31 | 2014-03-06 | Vanderbilt University | Substituted 3-aminothieno[2,3-c]pyridine-2-carboxamide analogs as positive allosteric modulators |
| US9908893B2 (en) | 2013-06-11 | 2018-03-06 | Latvian Institute Of Organic Synthesis | Thieno [2,3-b] pyridines as multidrug resistance modulators |
| WO2015027214A1 (en) | 2013-08-23 | 2015-02-26 | Vanderbilt University | Substituted thieno[2,3-c]pyridazine-6-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| TW201726675A (zh) | 2015-12-23 | 2017-08-01 | 默沙東藥廠 | M4毒蕈鹼乙醯膽鹼受體之異位調節劑6,7-二氫-5h-吡咯并[3,4-b]吡啶-5-酮 |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| BR112018003417B1 (pt) | 2016-06-22 | 2023-10-24 | Vanderbilt University | Composto modulador alostérico positivo do receptor muscarínico de acetilcolina m4 e composição farmacêutica que o compreende |
| PT3478679T (pt) | 2016-07-01 | 2021-06-30 | Pfizer | Derivados de 5,7-dihidro-pirrolo-piridina para o tratamento de doenças neurológicas e neurodegenerativas |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| WO2018085803A1 (en) | 2016-11-07 | 2018-05-11 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| US10961253B2 (en) | 2016-11-07 | 2021-03-30 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor M4 |
| EP3544961B1 (en) | 2016-11-07 | 2021-08-18 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| WO2018112840A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6, 5-fused heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| IL271290B2 (en) | 2017-06-22 | 2023-11-01 | Pfizer | Dihydro-pyrrolo-pyridine derivatives |
| WO2019000238A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | 5- (PYRIDIN-3-YL) OXAZOLE ALLOSTERIC MODULATORS OF M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000236A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000237A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| US11376254B2 (en) | 2017-12-05 | 2022-07-05 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor M4 |
| TW201930311A (zh) | 2017-12-05 | 2019-08-01 | 泛德比爾特大學 | 蕈毒鹼型乙醯膽鹼受體m4之正向別構調節劑 |
| WO2025201078A1 (zh) * | 2024-03-25 | 2025-10-02 | 四川科伦药物研究院有限公司 | 化合物、包含其的药物组合物及其制备方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3430284A1 (de) * | 1984-08-17 | 1986-02-27 | Troponwerke GmbH & Co KG, 5000 Köln | Neue tryptamin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung |
| HUT76923A (hu) * | 1994-07-27 | 1998-01-28 | Sankyo Company Limited | Muszkarinreceptorokra alloszterikus hatást kifejtő heterociklusos vegyületek |
| US6841684B2 (en) * | 1997-12-04 | 2005-01-11 | Allergan, Inc. | Imidiazoles having reduced side effects |
| GB9924962D0 (en) * | 1999-10-21 | 1999-12-22 | Mrc Collaborative Centre | Allosteric sites on muscarinic receptors |
| AR028385A1 (es) * | 2000-04-28 | 2003-05-07 | Acadia Pharm Inc | Agonistas muscarinicos |
| WO2003072578A1 (en) * | 2002-02-20 | 2003-09-04 | Pharmacia & Upjohn Company | Azabicyclic compounds with alfa7 nicotinic acetylcholine receptor activity |
| US6974870B2 (en) * | 2002-06-06 | 2005-12-13 | Boehringer Ingelheim Phamaceuticals, Inc. | Substituted 3-amino-thieno [2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses |
-
2005
- 2005-10-18 ES ES05812144T patent/ES2349416T3/es not_active Expired - Lifetime
- 2005-10-18 PT PT05812144T patent/PT1807434E/pt unknown
- 2005-10-18 DK DK05812144.3T patent/DK1807434T3/da active
- 2005-10-18 PL PL05812144T patent/PL1807434T3/pl unknown
- 2005-10-18 MX MX2007004794A patent/MX2007004794A/es active IP Right Grant
- 2005-10-18 AT AT05812144T patent/ATE478876T1/de active
- 2005-10-18 AU AU2005299957A patent/AU2005299957B2/en not_active Ceased
- 2005-10-18 JP JP2007537951A patent/JP4945453B2/ja not_active Expired - Fee Related
- 2005-10-18 EP EP05812144A patent/EP1807434B1/en not_active Expired - Lifetime
- 2005-10-18 WO PCT/US2005/037271 patent/WO2006047124A1/en not_active Ceased
- 2005-10-18 CA CA2583550A patent/CA2583550C/en not_active Expired - Fee Related
- 2005-10-18 DE DE602005023197T patent/DE602005023197D1/de not_active Expired - Lifetime
- 2005-10-18 CN CN200580036624A patent/CN100577666C/zh not_active Expired - Fee Related
- 2005-10-18 BR BRPI0517438-4A patent/BRPI0517438A/pt not_active IP Right Cessation
- 2005-10-18 US US11/577,508 patent/US8071776B2/en not_active Expired - Fee Related
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2010
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|---|---|
| AU2005299957B2 (en) | 2011-04-21 |
| JP4945453B2 (ja) | 2012-06-06 |
| PL1807434T3 (pl) | 2011-02-28 |
| CY1111477T1 (el) | 2015-08-05 |
| WO2006047124A1 (en) | 2006-05-04 |
| JP2008517913A (ja) | 2008-05-29 |
| BRPI0517438A (pt) | 2008-10-07 |
| CN100577666C (zh) | 2010-01-06 |
| DE602005023197D1 (de) | 2010-10-07 |
| PT1807434E (pt) | 2010-09-22 |
| US20090105244A1 (en) | 2009-04-23 |
| US8071776B2 (en) | 2011-12-06 |
| CA2583550A1 (en) | 2006-05-04 |
| DK1807434T3 (da) | 2010-11-22 |
| CN101048413A (zh) | 2007-10-03 |
| AU2005299957A1 (en) | 2006-05-04 |
| EP1807434A1 (en) | 2007-07-18 |
| ES2349416T3 (es) | 2011-01-03 |
| MX2007004794A (es) | 2007-07-09 |
| EP1807434B1 (en) | 2010-08-25 |
| ATE478876T1 (de) | 2010-09-15 |
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