JP4347047B2 - ムスカリン作用薬としてのベンゾイミダゾリジノン誘導体 - Google Patents
ムスカリン作用薬としてのベンゾイミダゾリジノン誘導体 Download PDFInfo
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- JP4347047B2 JP4347047B2 JP2003531986A JP2003531986A JP4347047B2 JP 4347047 B2 JP4347047 B2 JP 4347047B2 JP 2003531986 A JP2003531986 A JP 2003531986A JP 2003531986 A JP2003531986 A JP 2003531986A JP 4347047 B2 JP4347047 B2 JP 4347047B2
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- Prior art keywords
- mmol
- propyl
- benzoxazol
- benzothiazol
- butylpiperidin
- 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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- 239000000472 muscarinic agonist Substances 0.000 title description 12
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical class C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 381
- 238000000034 method Methods 0.000 claims description 52
- -1 1- (3- (4-propylpiperidin-1-yl) propyl) -1,3-dihydro-benzimidazol-2-one Chemical compound 0.000 claims description 51
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 44
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 43
- 102000005962 receptors Human genes 0.000 claims description 35
- 108020003175 receptors Proteins 0.000 claims description 35
- 230000000694 effects Effects 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 28
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 18
- 208000028017 Psychotic disease Diseases 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 108010009685 Cholinergic Receptors Proteins 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
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- 229910052717 sulfur Inorganic materials 0.000 claims description 7
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- PTYWMLLHDUYAHN-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-3-methylbenzimidazol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)N(C)C2=CC=CC=C21 PTYWMLLHDUYAHN-UHFFFAOYSA-N 0.000 claims description 3
- YLNXDDFKKOFSHP-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-3h-indol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC=CC=C2CC1=O YLNXDDFKKOFSHP-UHFFFAOYSA-N 0.000 claims description 3
- NQSGHDANINYARP-NYRJJRHWSA-N 3-[(2r)-3-(4-butylpiperidin-1-yl)-3-hydroxy-2-methylpropyl]-1,3-benzothiazol-2-one Chemical compound C1CC(CCCC)CCN1C(O)[C@H](C)CN1C(=O)SC2=CC=CC=C21 NQSGHDANINYARP-NYRJJRHWSA-N 0.000 claims description 3
- FIMVJCWQOSGEOQ-UHFFFAOYSA-N 3-[2-methyl-3-(4-propoxypiperidin-1-yl)propyl]-1,3-benzothiazol-2-one Chemical compound C1CC(OCCC)CCN1CC(C)CN1C(=O)SC2=CC=CC=C21 FIMVJCWQOSGEOQ-UHFFFAOYSA-N 0.000 claims description 3
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- SUQRFEOYHXSOAW-UHFFFAOYSA-N 3-[3-(3-pentyl-8-azabicyclo[3.2.1]octan-8-yl)propyl]-1,3-benzothiazol-2-one Chemical compound C12=CC=CC=C2SC(=O)N1CCCN1C2CCC1CC(CCCCC)C2 SUQRFEOYHXSOAW-UHFFFAOYSA-N 0.000 claims description 3
- XIQUXAZEWBOUON-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)-2-methylpropyl]-1,3-benzothiazol-2-one Chemical compound C1CC(CCCC)CCN1CC(C)CN1C(=O)SC2=CC=CC=C21 XIQUXAZEWBOUON-UHFFFAOYSA-N 0.000 claims description 3
- HTPVCXYIHCDKFE-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)propyl]-1,3-benzothiazol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)SC2=CC=CC=C21 HTPVCXYIHCDKFE-UHFFFAOYSA-N 0.000 claims description 3
- HDMJGRUUPRLGIP-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)propyl]-5-fluoro-1,3-benzoxazol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)OC2=CC=C(F)C=C21 HDMJGRUUPRLGIP-UHFFFAOYSA-N 0.000 claims description 3
- OQUJDVJIXLMDHP-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)propyl]-6-fluoro-1,3-benzoxazol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)OC2=CC(F)=CC=C21 OQUJDVJIXLMDHP-UHFFFAOYSA-N 0.000 claims description 3
- QUOZAWHDCBELDT-UHFFFAOYSA-N 3-[3-(4-propoxypiperidin-1-yl)propyl]-1,3-benzothiazol-2-one Chemical compound C1CC(OCCC)CCN1CCCN1C(=O)SC2=CC=CC=C21 QUOZAWHDCBELDT-UHFFFAOYSA-N 0.000 claims description 3
- GAXCWQHHMWEAQU-UHFFFAOYSA-N 3-[3-[4-(3-methylbutylidene)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C1CC(=CCC(C)C)CCN1CCCN1C(=O)NC2=CC=CC=C21 GAXCWQHHMWEAQU-UHFFFAOYSA-N 0.000 claims description 3
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical group C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
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- UXSCQRDRJCBYLR-UHFFFAOYSA-N 3-[3-(3-hex-1-ynyl-8-azabicyclo[3.2.1]oct-3-en-8-yl)propyl]-1,3-benzothiazol-2-one Chemical compound C12=CC=CC=C2SC(=O)N1CCCN1C2CCC1C=C(C#CCCCC)C2 UXSCQRDRJCBYLR-UHFFFAOYSA-N 0.000 claims description 2
- DFVITWKELPYEPA-UHFFFAOYSA-N 3-[3-(3-pent-1-ynyl-8-azabicyclo[3.2.1]oct-3-en-8-yl)propyl]-1,3-benzothiazol-2-one Chemical compound C12=CC=CC=C2SC(=O)N1CCCN1C2CCC1C=C(C#CCCC)C2 DFVITWKELPYEPA-UHFFFAOYSA-N 0.000 claims description 2
- UCBUAUQILRLLPW-UHFFFAOYSA-N 3-[3-(3-propyl-8-azabicyclo[3.2.1]octan-8-yl)propyl]-1,3-benzothiazol-2-one Chemical compound C12=CC=CC=C2SC(=O)N1CCCN1C2CCC1CC(CCC)C2 UCBUAUQILRLLPW-UHFFFAOYSA-N 0.000 claims description 2
- GTJWABIGHJEDDW-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)-2-hydroxypropyl]-1,3-benzothiazol-2-one Chemical compound C1CC(CCCC)CCN1CC(O)CN1C(=O)SC2=CC=CC=C21 GTJWABIGHJEDDW-UHFFFAOYSA-N 0.000 claims description 2
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- HQDWCNZWECYNAQ-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)propyl]-5,7-dichloro-6-ethyl-1,3-benzoxazol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)OC2=C(Cl)C(CC)=C(Cl)C=C21 HQDWCNZWECYNAQ-UHFFFAOYSA-N 0.000 claims description 2
- KRHOBLMCNVZTHP-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)propyl]-5,7-dichloro-6-methyl-1,3-benzoxazol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)OC2=C(Cl)C(C)=C(Cl)C=C21 KRHOBLMCNVZTHP-UHFFFAOYSA-N 0.000 claims description 2
- HYSYNDBFSUMVIK-UHFFFAOYSA-N 3-[3-(4-butylpiperidin-1-yl)propyl]-5-methoxy-1,3-benzoxazol-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)OC2=CC=C(OC)C=C21 HYSYNDBFSUMVIK-UHFFFAOYSA-N 0.000 claims description 2
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- HYJDVWRLWMGONK-UHFFFAOYSA-N 3-[3-[4-(2-ethoxyethyl)piperidin-1-yl]propyl]-1,3-benzothiazol-2-one Chemical compound C1CC(CCOCC)CCN1CCCN1C(=O)SC2=CC=CC=C21 HYJDVWRLWMGONK-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| US32675401P | 2001-10-02 | 2001-10-02 | |
| PCT/US2002/031308 WO2003028650A2 (en) | 2001-10-02 | 2002-09-30 | Benzimidazolidinone derivatives as muscarinic agents |
Publications (3)
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| JP2005510473A JP2005510473A (ja) | 2005-04-21 |
| JP2005510473A5 JP2005510473A5 (enExample) | 2006-01-05 |
| JP4347047B2 true JP4347047B2 (ja) | 2009-10-21 |
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| RU2288919C2 (ru) * | 2001-10-02 | 2006-12-10 | Акадиа Фармасьютикалз, Инк. | Производные бензимидазолидинона в качестве агентов мускариновых рецепторов |
| US6951849B2 (en) * | 2001-10-02 | 2005-10-04 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| WO2004089942A2 (en) * | 2001-10-02 | 2004-10-21 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| MXPA04010965A (es) * | 2002-05-07 | 2005-01-25 | Neurosearch As | Derivados de etinilo azaciclico novedoso. |
| EP1613321A2 (en) * | 2003-03-28 | 2006-01-11 | Acadia Pharmaceuticals Inc. | Muscarinic m1 receptor agonists for pain management |
| US7157471B2 (en) * | 2003-08-25 | 2007-01-02 | Boehringer Ingelheim International Gmbh | Haloalkyl- and piperidine-substituted benzimidazole-derivatives |
| AR045843A1 (es) * | 2003-10-03 | 2005-11-16 | Solvay Pharm Bv | Derivados de bencimidazolonas y quinazolinonas sustituidas con hidronopol como agonistas en receptores orl 1 humanos |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| US7678363B2 (en) * | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| ATE492537T1 (de) * | 2005-09-30 | 2011-01-15 | Glaxo Group Ltd | Verbindungen mit aktivität am m1-rezeptor und ihre verwendung in der medizin |
| JP5209479B2 (ja) * | 2005-09-30 | 2013-06-12 | グラクソ グループ リミテッド | M1受容体にて活性を有するベンゾイミダゾロン類 |
| WO2007036718A2 (en) * | 2005-09-30 | 2007-04-05 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| EP2377530A3 (en) | 2005-10-21 | 2012-06-20 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| WO2007075297A2 (en) * | 2005-12-27 | 2007-07-05 | University Of Toledo | Muscarinic agonists and methods of use thereof |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| GB0607949D0 (en) * | 2006-04-21 | 2006-05-31 | Minster Res The Ltd | Mono and combination therapy |
| US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| WO2007134136A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| TW200813018A (en) * | 2006-06-09 | 2008-03-16 | Astrazeneca Ab | Novel compounds |
| AU2007292848A1 (en) | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| CL2007002958A1 (es) * | 2006-10-12 | 2008-05-09 | Epix Delaware Inc | Compuestos derivados de heteroaril-carboxamida, antagonistas del receptor de quimioquina; composicion farmaceutica; y uso para el tratamiento o prevencion de enfermedades tales como rechazo de transplante de organos, artritis reumatoidea, lupus, entr |
| GB0718415D0 (en) * | 2007-09-20 | 2007-10-31 | Glaxo Group Ltd | Compounds |
| US8278328B2 (en) * | 2007-09-20 | 2012-10-02 | Glaxo Group Limited | Compounds which have activity at M1 receptor and their uses in medicine |
| JP2010539218A (ja) * | 2007-09-20 | 2010-12-16 | グラクソ グループ リミテッド | M1受容体にて活性を有する化合物および医薬としてのそれらの使用 |
| CA2708364A1 (en) | 2007-12-11 | 2009-06-18 | Efrat Ben-Zeev | Carboxamide compounds and their use as chemokine receptor agonists |
| EP2296471A4 (en) | 2008-05-15 | 2012-03-14 | Univ Toledo | MUSCARIC ACID AGONISTS AS COGNITIVE ENHANCERS |
| US20100158829A1 (en) * | 2008-12-24 | 2010-06-24 | Conopco, Inc., D/B/A Unilever | Method and Composition for Color Modulation |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| WO2010129843A1 (en) * | 2009-05-08 | 2010-11-11 | Cytopathfinder, Inc. | Dihydronaphthyridinyl and related compounds for use in treating ophthalmological disorders |
| PT2624696T (pt) | 2010-10-06 | 2017-03-21 | Glaxosmithkline Llc | Derivados de benzimidazole como inibidores da cinase pi3 |
| US9549928B2 (en) | 2011-04-29 | 2017-01-24 | The University Of Toledo | Muscarinic agonists as enhancers of cognitive flexibility |
| JP6393524B2 (ja) * | 2014-06-05 | 2018-09-19 | ロート製薬株式会社 | 保湿剤 |
| WO2016022644A1 (en) * | 2014-08-06 | 2016-02-11 | Merck Sharp & Dohme Corp. | Heterocyclic cgrp receptor antagonists |
| HUE055763T2 (hu) | 2015-07-20 | 2021-12-28 | Acadia Pharm Inc | Eljárás N-(4-fluorbenzil)-N-(1-metilpiperidin-4-il)-N'-(4-(2-metil-propil-oxi)fenil-metil)karbamid vagy ennek tartarát-sója és C polimorf formája elõállítására |
| WO2017165635A1 (en) | 2016-03-25 | 2017-09-28 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome p450 modulators |
| US10953000B2 (en) | 2016-03-25 | 2021-03-23 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome P450 modulators |
| US20190117636A1 (en) * | 2016-03-29 | 2019-04-25 | Acadia Pharmaceuticals Inc. | 5-ht2a serotonin receptor inverse agonists or antagonists for use in reducing amyloid-beta peptides and accumulation of amyloid plaques |
| US11464768B2 (en) | 2016-12-20 | 2022-10-11 | Acadia Pharmaceuticals Inc. | Pimavanserin alone or in combination for use in the treatment of Alzheimer's disease psychosis |
| WO2018200977A1 (en) | 2017-04-28 | 2018-11-01 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating impulse control disorder |
| EP3675827A1 (en) | 2017-08-30 | 2020-07-08 | Acadia Pharmaceuticals Inc. | Formulations of pimavanserin |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| PE20230680A1 (es) | 2020-05-06 | 2023-04-21 | Merck Sharp And Dohme Llc | Inhibidores de il4i1 y metodos de uso |
| EP4447953A1 (en) | 2021-12-13 | 2024-10-23 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
| WO2024138108A2 (en) * | 2022-12-22 | 2024-06-27 | University Of Florida Research Foundation, Incorporated | Metabolically stable sigma receptor ligands |
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| CH407121A (de) | 1962-03-30 | 1966-02-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| US4371388A (en) * | 1980-01-25 | 1983-02-01 | Monsanto Company | 3-Substituted aminoalkyl-2-benzothiazolinones as plant growth regulants |
| US4254127A (en) * | 1980-04-03 | 1981-03-03 | Janssen Pharmaceutica, N.V. | 1,3-Dihydro-1-[(1-piperidinyl)alkyl]-2H-benzimidazol-2-one derivatives |
| US4943580A (en) * | 1987-03-09 | 1990-07-24 | Janssen Pharmaceutica N.V. | Anti-histaminic benzimidazole, imidazopyridine and purine derivatives |
| GB8718345D0 (en) * | 1987-08-03 | 1987-09-09 | Fordonal Sa | N-substituted benzamides |
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| JP3916092B2 (ja) | 1993-09-17 | 2007-05-16 | 杏林製薬株式会社 | イミダゾリジノン誘導体とその酸付加塩及び老年性痴呆症の治療薬 |
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| WO1997016192A1 (en) | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Muscarine antagonists |
| AU7478396A (en) | 1995-10-31 | 1997-05-22 | Merck & Co., Inc. | Muscarine agonists |
| WO1997016187A1 (en) | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Muscarine antagonists |
| US5756508A (en) | 1995-10-31 | 1998-05-26 | Merck & Co., Inc. | Muscarine antagonists |
| US5718912A (en) | 1996-10-28 | 1998-02-17 | Merck & Co., Inc. | Muscarine agonists |
| WO1999032481A1 (en) | 1997-12-23 | 1999-07-01 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| US6569956B1 (en) | 1999-12-22 | 2003-05-27 | Basf Corporation | Hyperbranched polyol macromolecule, method of making same, and coating composition including same |
| ATE348808T1 (de) | 2000-03-06 | 2007-01-15 | Acadia Pharm Inc | Azacyclische verbindungen zur verwendung in der behandlung von mit serotonin verwandten krankheiten |
| CN1814596A (zh) | 2000-04-28 | 2006-08-09 | 阿卡蒂亚药品公司 | 毒蕈碱性激动剂 |
| WO2002024662A1 (en) * | 2000-09-19 | 2002-03-28 | Boehringer Ingelheim Pharma Gmbh & Ko. Kg | New benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors |
| US6586435B2 (en) * | 2000-09-19 | 2003-07-01 | Boehringer Ingelheim Pharma Kg | Benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors |
| RU2288919C2 (ru) * | 2001-10-02 | 2006-12-10 | Акадиа Фармасьютикалз, Инк. | Производные бензимидазолидинона в качестве агентов мускариновых рецепторов |
| US6951849B2 (en) * | 2001-10-02 | 2005-10-04 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
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2007
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2010
- 2010-05-07 US US12/776,096 patent/US20100216840A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| RU2288919C2 (ru) | 2006-12-10 |
| US20080009520A1 (en) | 2008-01-10 |
| NZ531550A (en) | 2006-12-22 |
| TWI310034B (en) | 2009-05-21 |
| US20100216840A1 (en) | 2010-08-26 |
| KR20040047877A (ko) | 2004-06-05 |
| WO2003028650A2 (en) | 2003-04-10 |
| US7087593B2 (en) | 2006-08-08 |
| WO2003028650A3 (en) | 2003-06-19 |
| AU2002327810B2 (en) | 2006-11-02 |
| MXPA04003103A (es) | 2004-07-27 |
| BR0213611A (pt) | 2005-12-20 |
| EP1432420A2 (en) | 2004-06-30 |
| CA2457647A1 (en) | 2003-04-10 |
| RU2004113451A (ru) | 2005-09-10 |
| US7273857B2 (en) | 2007-09-25 |
| US20060258707A1 (en) | 2006-11-16 |
| KR20060130271A (ko) | 2006-12-18 |
| JP2005510473A (ja) | 2005-04-21 |
| EP1432420B1 (en) | 2011-07-13 |
| EP1432420A4 (en) | 2005-11-09 |
| US20060205785A1 (en) | 2006-09-14 |
| ATE516030T1 (de) | 2011-07-15 |
| NO20041317L (no) | 2004-06-29 |
| US20030100545A1 (en) | 2003-05-29 |
| KR100809569B1 (ko) | 2008-03-04 |
| US20080070948A1 (en) | 2008-03-20 |
| CN1561212A (zh) | 2005-01-05 |
| ZA200402609B (en) | 2005-05-09 |
| AR036716A1 (es) | 2004-09-29 |
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