CA2317025A1 - Pyridyl-bridgehead derivatives and their analogues, pharmaceutical compositions and their use as inhibitors of nicotinic cholinergic receptors - Google Patents
Pyridyl-bridgehead derivatives and their analogues, pharmaceutical compositions and their use as inhibitors of nicotinic cholinergic receptors Download PDFInfo
- Publication number
- CA2317025A1 CA2317025A1 CA002317025A CA2317025A CA2317025A1 CA 2317025 A1 CA2317025 A1 CA 2317025A1 CA 002317025 A CA002317025 A CA 002317025A CA 2317025 A CA2317025 A CA 2317025A CA 2317025 A1 CA2317025 A1 CA 2317025A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- alkyl
- bond
- cycloalkyl
- azabicyclo
- 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.)
- Abandoned
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 38
- 108010009685 Cholinergic Receptors Proteins 0.000 title abstract description 7
- 102000034337 acetylcholine receptors Human genes 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 207
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 57
- 125000003118 aryl group Chemical group 0.000 claims abstract description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 40
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 33
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000003107 substituted aryl group Chemical group 0.000 claims description 21
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 7
- 239000003367 nicotinic antagonist Substances 0.000 claims description 7
- 230000003957 neurotransmitter release Effects 0.000 claims description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000006260 foam Substances 0.000 claims 1
- -1 amine compounds Chemical class 0.000 abstract description 54
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- RFDPHKHXPMDJJD-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one;hydron;chloride Chemical compound Cl.C1CC2C(=O)CN1CC2 RFDPHKHXPMDJJD-UHFFFAOYSA-N 0.000 description 14
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- NGUVGKAEOFPLDT-UHFFFAOYSA-N 5-bromopyridine-3-carbaldehyde Chemical compound BrC1=CN=CC(C=O)=C1 NGUVGKAEOFPLDT-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 10
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- 150000003839 salts Chemical group 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
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- 239000000460 chlorine Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 230000003993 interaction Effects 0.000 description 7
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 description 7
- 239000002858 neurotransmitter agent Substances 0.000 description 7
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 7
- WKYVGBPCXOPWEA-UHFFFAOYSA-N 4-bromopyridine-3-carbaldehyde Chemical compound BrC1=CC=NC=C1C=O WKYVGBPCXOPWEA-UHFFFAOYSA-N 0.000 description 6
- PVUKGNBRJFTFNJ-UHFFFAOYSA-N 6-bromopyridine-3-carbaldehyde Chemical compound BrC1=CC=C(C=O)C=N1 PVUKGNBRJFTFNJ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 208000003098 Ganglion Cysts Diseases 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 4
- CKDDUULIRPQPSS-UHFFFAOYSA-N 2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound OC1C(CC2)CCN2C1CC1=CC=CN=C1 CKDDUULIRPQPSS-UHFFFAOYSA-N 0.000 description 4
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
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- HMSCOZSAWDRPQV-UHFFFAOYSA-N 2-(pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octane Chemical compound C1CN2CCC1CC2=CC1=CC=CN=C1 HMSCOZSAWDRPQV-UHFFFAOYSA-N 0.000 description 3
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/210,113 US6432975B1 (en) | 1998-12-11 | 1998-12-11 | Pharmaceutical compositions and methods for use |
| US09/210,113 | 1998-12-11 | ||
| PCT/US1999/019906 WO2000034276A1 (en) | 1998-12-11 | 1999-08-31 | Pyridyl-bridgehead derivatives and their analogues, pharmaceutical compositions and their use as inhibitors of nicotinic cholinergic receptors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2317025A1 true CA2317025A1 (en) | 2000-06-15 |
Family
ID=22781623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002317025A Abandoned CA2317025A1 (en) | 1998-12-11 | 1999-08-31 | Pyridyl-bridgehead derivatives and their analogues, pharmaceutical compositions and their use as inhibitors of nicotinic cholinergic receptors |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6432975B1 (https=) |
| EP (1) | EP1053236A1 (https=) |
| JP (1) | JP2002531564A (https=) |
| AU (1) | AU5699399A (https=) |
| BR (1) | BR9907169A (https=) |
| CA (1) | CA2317025A1 (https=) |
| WO (1) | WO2000034276A1 (https=) |
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|---|---|---|---|---|
| US8569354B2 (en) | 2008-11-19 | 2013-10-29 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8710227B2 (en) | 2010-05-17 | 2014-04-29 | Envivo Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US8884017B2 (en) | 2001-12-27 | 2014-11-11 | Bayer Intellectual Property Gmbh | 2-heteroarylcarboxylic acid amides |
| US9585877B2 (en) | 2012-05-08 | 2017-03-07 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
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| US6953855B2 (en) | 1998-12-11 | 2005-10-11 | Targacept, Inc. | 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof |
| EP1212301A1 (en) * | 1999-08-31 | 2002-06-12 | Targacept, Inc. | Arylalkyloxyalkylamines and arylalkylthioalkylamines, pharmaceutical compositions containing them and their use as inhibitors of nicotinic cholinergic receptors |
| US6890935B2 (en) * | 1999-11-01 | 2005-05-10 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| JP2003513054A (ja) * | 1999-11-01 | 2003-04-08 | ターガセプト，インコーポレイテッド | アリールオレフィンアザ環式化合物及びアリールアセチレンアザ環式化合物、それらを含有する薬剤組成物、及び、ニコチンコリン作動性受容体の阻害薬としてのそれらの使用 |
| WO2002024692A1 (en) * | 2000-09-20 | 2002-03-28 | Karolinska Innovations Ab | 1-azabicyclo[2.2.2]octan-3-one derivatives and maleimide derivatives and their use for treating cancer tumors |
| US7659278B2 (en) | 2002-02-21 | 2010-02-09 | Aprea Ab | Use of low molecular weight compounds for preparing a medicament useful in treating mutant p53 mediated diseases |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| WO2004039815A2 (en) * | 2002-11-01 | 2004-05-13 | Pharmacia & Upjohn Company Llc | Compounds having both alpha7 nachr agonist and 5ht antagonist activity for treatment of cns diseases |
| WO2004052365A2 (en) * | 2002-12-06 | 2004-06-24 | North Shore-Long Island Jewish Research Institute | Inhibition of inflamation using alpha 7 receptor-binding cholinergic agonists |
| US7238715B2 (en) * | 2002-12-06 | 2007-07-03 | The Feinstein Institute For Medical Research | Treatment of pancreatitis using alpha 7 receptor-binding cholinergic agonists |
| SE0400708D0 (sv) * | 2004-03-22 | 2004-03-22 | Aprea Ab | New compounds and use thereof |
| PE20060437A1 (es) | 2004-06-18 | 2006-06-08 | Novartis Ag | COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| US8316104B2 (en) | 2005-11-15 | 2012-11-20 | California Institute Of Technology | Method and apparatus for collaborative system |
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| JP5172124B2 (ja) | 2006-09-29 | 2013-03-27 | 関東化学株式会社 | ２位に置換基を有する光学活性キヌクリジノール類の製造方法 |
| JP5232374B2 (ja) * | 2006-09-29 | 2013-07-10 | 関東化学株式会社 | ２位に置換基を有する光学活性キヌクリジノール類の製造方法 |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| TW201031664A (en) * | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
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| GEP201706757B (en) | 2012-12-21 | 2017-10-25 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| EA201790376A1 (ru) * | 2014-09-05 | 2017-08-31 | Селджен Квонтисел Рисёрч, Инк. | Ингибиторы лизин-специфической деметилазы-1 |
| US9724340B2 (en) | 2015-07-31 | 2017-08-08 | Attenua, Inc. | Antitussive compositions and methods |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
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| EP0402056A3 (en) | 1989-06-06 | 1991-09-04 | Beecham Group p.l.c. | Azabicyclic compounds, process for their preparation and pharmaceutical compositions containing them |
| EP0412798A3 (en) | 1989-08-08 | 1992-07-01 | Merck Sharp & Dohme Ltd. | Substituted pyridines, their preparation, formulations and use in dementia |
| EP0492903A1 (en) | 1990-12-21 | 1992-07-01 | MERCK SHARP & DOHME LTD. | Substituted pyrazines, pyrimidines and pyridazines for use in the treatment of glaucoma |
| US5212188A (en) | 1992-03-02 | 1993-05-18 | R. J. Reynolds Tabacco Company | Method for treatment of neurodegenerative diseases |
| US5276043A (en) | 1992-04-10 | 1994-01-04 | R. J. Reynolds Tobacco Company | Method for treatment of neurodegenerative diseases |
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| AU7474794A (en) | 1993-07-22 | 1995-02-20 | E.I. Du Pont De Nemours And Company | Arthropodicidal azacyclic heterocycles |
| US5510355A (en) | 1994-09-06 | 1996-04-23 | Bencherif; Merouane | Depolarizing skeletal muscle relaxants |
| US5998404A (en) | 1994-10-24 | 1999-12-07 | Eli Lilly And Company | Heterocyclic compounds and their use |
| US5616707A (en) | 1995-01-06 | 1997-04-01 | Crooks; Peter A. | Compounds which are useful for prevention and treatment of central nervous system disorders |
| US5604231A (en) | 1995-01-06 | 1997-02-18 | Smith; Carr J. | Pharmaceutical compositions for prevention and treatment of ulcerative colitis |
| US5597919A (en) | 1995-01-06 | 1997-01-28 | Dull; Gary M. | Pyrimidinyl or Pyridinyl alkenyl amine compounds |
| US5824692A (en) | 1995-01-06 | 1998-10-20 | Lippiello; Patrick Michael | Pharmaceutical compositions for prevention and treatment of central nervous system disorders |
| US5859004A (en) | 1995-02-17 | 1999-01-12 | Novo Nordisk A/S | Use of heterocyclic compounds for the treatment of conditions caused by malfunctioning of the nicotinic cholinergic system |
| US5583140A (en) | 1995-05-17 | 1996-12-10 | Bencherif; Merouane | Pharmaceutical compositions for the treatment of central nervous system disorders |
| EP0842172A1 (en) | 1995-06-29 | 1998-05-20 | Novo Nordisk A/S | Novel substituted azacyclic or azabicyclic compounds |
| JPH11512443A (ja) | 1995-09-22 | 1999-10-26 | ノボ ノルディスク アクティーゼルスカブ | 新規な置換アザ環式またはアザ二環式化合物 |
| US5616716A (en) | 1996-01-06 | 1997-04-01 | Dull; Gary M. | (3-(5-ethoxypyridin)yl)-alkenyl 1 amine compounds |
| US5663356A (en) | 1996-04-23 | 1997-09-02 | Ruecroft; Graham | Method for preparation of aryl substituted alefinic secondary amino compounds |
| ZA9711092B (en) | 1996-12-11 | 1999-07-22 | Smithkline Beecham Corp | Novel compounds. |
| US5861423A (en) | 1997-02-21 | 1999-01-19 | Caldwell; William Scott | Pharmaceutical compositions incorporating aryl substituted olefinic amine compounds |
| US5811442A (en) | 1997-02-21 | 1998-09-22 | Bencherif; Merouane | Pharmaceutical compositions for the treatment of conditions associated with decreased blood flow |
| CA2289574C (en) | 1997-05-30 | 2007-04-24 | Neurosearch A/S | 8-azabicyclo(3,2,1)oct-2-ene and octane derivatives as cholinergic ligands at nicotinic ach receptors |
| PT994875E (pt) | 1997-06-30 | 2004-06-30 | Targacept Inc | Derivados de 3-piridil-1-aza-biciclo-alcano para a prevencao e tratamento de desordens do snc |
| WO1999051602A1 (en) | 1998-04-02 | 1999-10-14 | R.J. Reynolds Tobacco Company | Azatricyclo[3.3.1.1] decane derivatives and pharmaceutical compositions containing them |
| US5952339A (en) | 1998-04-02 | 1999-09-14 | Bencherif; Merouane | Pharmaceutical compositions and methods of using nicotinic antagonists for treating a condition or disorder characterized by alteration in normal neurotransmitter release |
-
1998
- 1998-12-11 US US09/210,113 patent/US6432975B1/en not_active Expired - Lifetime
-
1999
- 1999-08-31 WO PCT/US1999/019906 patent/WO2000034276A1/en not_active Ceased
- 1999-08-31 EP EP99944011A patent/EP1053236A1/en not_active Withdrawn
- 1999-08-31 AU AU56993/99A patent/AU5699399A/en not_active Abandoned
- 1999-08-31 CA CA002317025A patent/CA2317025A1/en not_active Abandoned
- 1999-08-31 JP JP2000586722A patent/JP2002531564A/ja not_active Withdrawn
- 1999-08-31 BR BR9907169-0A patent/BR9907169A/pt not_active Application Discontinuation
-
2002
- 2002-06-04 US US10/162,129 patent/US20030045523A1/en not_active Abandoned
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8884017B2 (en) | 2001-12-27 | 2014-11-11 | Bayer Intellectual Property Gmbh | 2-heteroarylcarboxylic acid amides |
| US8569354B2 (en) | 2008-11-19 | 2013-10-29 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8642638B2 (en) | 2008-11-19 | 2014-02-04 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8815933B2 (en) | 2008-11-19 | 2014-08-26 | Forum Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8710227B2 (en) | 2010-05-17 | 2014-04-29 | Envivo Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US9108961B2 (en) | 2010-05-17 | 2015-08-18 | Forum Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride |
| US9273044B2 (en) | 2010-05-17 | 2016-03-01 | Forum Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US9550767B2 (en) | 2010-05-17 | 2017-01-24 | Forum Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US9585877B2 (en) | 2012-05-08 | 2017-03-07 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000034276A1 (en) | 2000-06-15 |
| US20030045523A1 (en) | 2003-03-06 |
| BR9907169A (pt) | 2000-10-17 |
| EP1053236A1 (en) | 2000-11-22 |
| JP2002531564A (ja) | 2002-09-24 |
| US6432975B1 (en) | 2002-08-13 |
| AU5699399A (en) | 2000-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |