ES2254723T3 - Fracciones azabiciclicas sustituidas para el tratamiento de enfermedades (agonistas de receptores de acetilcolina nicolitica). - Google Patents
Fracciones azabiciclicas sustituidas para el tratamiento de enfermedades (agonistas de receptores de acetilcolina nicolitica).Info
- Publication number
- ES2254723T3 ES2254723T3 ES02764140T ES02764140T ES2254723T3 ES 2254723 T3 ES2254723 T3 ES 2254723T3 ES 02764140 T ES02764140 T ES 02764140T ES 02764140 T ES02764140 T ES 02764140T ES 2254723 T3 ES2254723 T3 ES 2254723T3
- Authority
- ES
- Spain
- Prior art keywords
- azabicyclo
- chlorobenzamide
- mmol
- mixture
- int
- 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.)
- Expired - Lifetime
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 20
- 201000010099 disease Diseases 0.000 title claims abstract description 19
- 239000000556 agonist Substances 0.000 title description 8
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- 238000002360 preparation method Methods 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 241000124008 Mammalia Species 0.000 claims abstract description 13
- 230000001953 sensory effect Effects 0.000 claims abstract description 9
- 230000006735 deficit Effects 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims abstract description 4
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 230000006870 function Effects 0.000 claims description 4
- UHDQINDMOBTIRD-UHFFFAOYSA-N 4-chloro-n-(2-ethyl-1-azabicyclo[3.2.2]nonan-3-yl)benzamide Chemical compound C1C(CC2)CCN2C(CC)C1NC(=O)C1=CC=C(Cl)C=C1 UHDQINDMOBTIRD-UHFFFAOYSA-N 0.000 claims description 3
- SAUBMRFYKTVXTL-UHFFFAOYSA-N 4-chloro-n-(2-methyl-1-azabicyclo[3.2.2]nonan-3-yl)benzamide Chemical compound C1C(CC2)CCN2C(C)C1NC(=O)C1=CC=C(Cl)C=C1 SAUBMRFYKTVXTL-UHFFFAOYSA-N 0.000 claims description 3
- NUKXVOISSGXHQT-UHFFFAOYSA-N 4-chloro-n-(4-ethyl-1-azabicyclo[3.2.2]nonan-3-yl)benzamide Chemical compound CCC1C(CC2)CCN2CC1NC(=O)C1=CC=C(Cl)C=C1 NUKXVOISSGXHQT-UHFFFAOYSA-N 0.000 claims description 3
- MEBUSTMEOOOFPF-UHFFFAOYSA-N 4-chloro-n-(4-methyl-1-azabicyclo[3.2.2]nonan-3-yl)benzamide Chemical compound CC1C(CC2)CCN2CC1NC(=O)C1=CC=C(Cl)C=C1 MEBUSTMEOOOFPF-UHFFFAOYSA-N 0.000 claims description 3
- KNJUGEIFWKPDKA-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1CN(CC2)CCC2C1 KNJUGEIFWKPDKA-UHFFFAOYSA-N 0.000 claims description 3
- BPSDHAWUPGCJDN-UHFFFAOYSA-N 4-chloro-n-(2-ethyl-1-azabicyclo[2.2.1]heptan-3-yl)benzamide Chemical compound C1C2CCN1C(CC)C2NC(=O)C1=CC=C(Cl)C=C1 BPSDHAWUPGCJDN-UHFFFAOYSA-N 0.000 claims description 2
- DETWCCIEYHOSGZ-UHFFFAOYSA-N 4-chloro-n-(2-ethyl-1-azabicyclo[2.2.2]octan-3-yl)benzamide Chemical compound C1CC2CCN1C(CC)C2NC(=O)C1=CC=C(Cl)C=C1 DETWCCIEYHOSGZ-UHFFFAOYSA-N 0.000 claims description 2
- KSZHGSSRKLSRFJ-UHFFFAOYSA-N 4-chloro-n-(2-methyl-1-azabicyclo[2.2.1]heptan-3-yl)benzamide Chemical compound C1C2CCN1C(C)C2NC(=O)C1=CC=C(Cl)C=C1 KSZHGSSRKLSRFJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001149 cognitive effect Effects 0.000 claims description 2
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- 230000037396 body weight Effects 0.000 claims 2
- HUUVVFQCMQBKND-UHFFFAOYSA-N 4-chloro-n-(2-methyl-1-azabicyclo[2.2.2]octan-3-yl)benzamide Chemical compound C1CC2CCN1C(C)C2NC(=O)C1=CC=C(Cl)C=C1 HUUVVFQCMQBKND-UHFFFAOYSA-N 0.000 claims 1
- 230000028252 learning or memory Effects 0.000 claims 1
- BMAIWQXUJRNDQG-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1C(C2)CCN2C1 BMAIWQXUJRNDQG-UHFFFAOYSA-N 0.000 claims 1
- HUPXCGVVHXZUCO-UHFFFAOYSA-N n-(2-benzyl-1-azabicyclo[2.2.2]octan-3-yl)-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1C(CC=2C=CC=CC=2)N2CCC1CC2 HUPXCGVVHXZUCO-UHFFFAOYSA-N 0.000 claims 1
- WECKJONDRAUFDD-UHFFFAOYSA-N pnu-282,987 Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1C(CC2)CCN2C1 WECKJONDRAUFDD-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 109
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 125000001424 substituent group Chemical group 0.000 description 27
- 239000010410 layer Substances 0.000 description 26
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- -1 hexafluorophosphate Chemical compound 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 238000003795 desorption Methods 0.000 description 13
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- 239000002904 solvent Substances 0.000 description 13
- 238000010828 elution Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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- 102100024954 5-hydroxytryptamine receptor 3A Human genes 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 description 10
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- 229910052763 palladium Inorganic materials 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 8
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- ZKMZPXWMMSBLNO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2C(=O)CN1CC2 ZKMZPXWMMSBLNO-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged 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
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- 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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- 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
-
- 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
- C07D487/08—Bridged systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28495001P | 2001-04-19 | 2001-04-19 | |
| US284950P | 2001-04-19 | ||
| US34890401P | 2001-10-26 | 2001-10-26 | |
| US348904P | 2001-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2254723T3 true ES2254723T3 (es) | 2006-06-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02764140T Expired - Lifetime ES2254723T3 (es) | 2001-04-19 | 2002-04-18 | Fracciones azabiciclicas sustituidas para el tratamiento de enfermedades (agonistas de receptores de acetilcolina nicolitica). |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6869946B2 (enExample) |
| EP (1) | EP1389208B1 (enExample) |
| JP (1) | JP2004526788A (enExample) |
| AR (1) | AR035817A1 (enExample) |
| AT (1) | ATE314367T1 (enExample) |
| CA (1) | CA2439960A1 (enExample) |
| DE (1) | DE60208366T2 (enExample) |
| ES (1) | ES2254723T3 (enExample) |
| MX (1) | MXPA03009644A (enExample) |
| PE (1) | PE20021019A1 (enExample) |
| WO (1) | WO2002085901A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| US6852716B2 (en) * | 2002-02-15 | 2005-02-08 | Pfizer Inc | Substituted-aryl compounds for treatment of disease |
| JP2005523288A (ja) | 2002-02-19 | 2005-08-04 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 疾病治療用の縮合した二環式−ｎ−架橋−複素環式芳香族カルボキサミド |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| CA2499128C (en) | 2002-09-25 | 2012-07-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| WO2004052889A1 (en) * | 2002-12-06 | 2004-06-24 | Pharmacia & Upjohn Company Llc | Compounds as radioligands for the diagnosis of disease |
| MXPA05007689A (es) * | 2003-01-22 | 2005-09-30 | Pharmacia & Upjohn Co Llc | Tratamiento de enfermedades con agonistas completos del receptor alfa-7 de nach. |
| GB0310867D0 (en) * | 2003-05-12 | 2003-06-18 | Novartis Ag | Organic compounds |
| PL1697378T3 (pl) | 2003-12-22 | 2008-04-30 | Memory Pharm Corp | Indole, 1h-indazole, 1,2-benzoizoksazole i 1,2-benzoizotiazole oraz ich wytwarzanie i zastosowania |
| WO2005092890A2 (en) | 2004-03-25 | 2005-10-06 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| EP1736156A4 (en) * | 2004-04-15 | 2010-06-16 | Eisai R&D Man Co Ltd | COMPOSITION CONTAINING 4-AMINO-5-CHLORO-N-¬ (1R, 3R, 5S) -8-METHYL-8-AZABICYCLO-3.2.1 OCT-3-YL-2-β-methyl-2-ynyloxy BENZAMIDE STABILIZED |
| DE602005024677D1 (de) * | 2004-04-22 | 2010-12-23 | Memory Pharm Corp | Indole, 1h-indazole, 1,2-benzisoxazole, 1,2-benzoisothiazole, deren herstellung und verwendungen |
| RU2386633C2 (ru) | 2004-05-07 | 2010-04-20 | Мемори Фармасьютиклз Корпорейшн | 1h-индазолы, бензотиазолы, 1, 2-бензоизоксазолы, 1, 2-бензоизотиазолы и хромоны и их получение и применения |
| 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 |
| GB0424564D0 (en) * | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
| JP2008525464A (ja) | 2004-12-22 | 2008-07-17 | メモリー・ファーマシューティカルズ・コーポレイション | α−７ニコチン性受容体リガンド並びにその製造及び使用 |
| US7732607B2 (en) * | 2005-08-22 | 2010-06-08 | Anatoly Mazurov | Heteroaryl-substituted diazatricycloalkanes and methods of use thereof |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| 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 |
| EP2271344A4 (en) | 2008-03-31 | 2011-04-27 | Univ South Florida | METHOD FOR TREATING ILLNESS-RELATED ATAXIA AND NON-ATTACHIC IMBALANCE |
| JP2011520964A (ja) * | 2008-05-23 | 2011-07-21 | ユニバーシティ・オブ・サウス・フロリダ | ニコチン性アセチルコリン受容体活性を有する化合物を用いる末梢感覚神経喪失の治療方法 |
| 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 |
| TWI519532B (zh) | 2010-05-17 | 2016-02-01 | 艾維沃製藥公司 | （Ｒ）－７－氯－Ｎ－（啶－３－基）苯並［b］噻吩－２－羧醯胺鹽酸鹽單水合物之結晶形體 |
| WO2012177263A1 (en) * | 2011-06-24 | 2012-12-27 | Intra-Cellular Therapies, Inc. | Compounds and methods of prophylaxis and treatment regarding nictonic receptor antagonists |
| RU2017136693A (ru) | 2012-05-08 | 2019-02-08 | Форум Фармасьютикалз, Инк. | Способы поддержания, лечения или улучшения когнитивной функции |
| CA2971413A1 (en) * | 2014-12-16 | 2016-06-23 | Axovant Sciences Gmbh | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| CN109320510B (zh) * | 2018-11-27 | 2021-04-27 | 江苏慧聚药业有限公司 | 一种马罗匹坦游离碱的制备方法 |
| CN111793017B (zh) * | 2019-04-04 | 2024-01-16 | 广东东阳光药业股份有限公司 | 一种内酰胺化合物的制备方法 |
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-
2002
- 2002-04-05 PE PE2002000274A patent/PE20021019A1/es not_active Application Discontinuation
- 2002-04-09 AR ARP020101299A patent/AR035817A1/es unknown
- 2002-04-17 US US10/124,145 patent/US6869946B2/en not_active Expired - Fee Related
- 2002-04-18 WO PCT/US2002/008268 patent/WO2002085901A1/en not_active Ceased
- 2002-04-18 AT AT02764140T patent/ATE314367T1/de not_active IP Right Cessation
- 2002-04-18 DE DE60208366T patent/DE60208366T2/de not_active Expired - Fee Related
- 2002-04-18 JP JP2002583428A patent/JP2004526788A/ja not_active Withdrawn
- 2002-04-18 MX MXPA03009644A patent/MXPA03009644A/es unknown
- 2002-04-18 CA CA002439960A patent/CA2439960A1/en not_active Abandoned
- 2002-04-18 ES ES02764140T patent/ES2254723T3/es not_active Expired - Lifetime
- 2002-04-18 EP EP02764140A patent/EP1389208B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1389208B1 (en) | 2005-12-28 |
| DE60208366D1 (de) | 2006-02-02 |
| US6869946B2 (en) | 2005-03-22 |
| MXPA03009644A (es) | 2004-01-29 |
| ATE314367T1 (de) | 2006-01-15 |
| AR035817A1 (es) | 2004-07-14 |
| JP2004526788A (ja) | 2004-09-02 |
| EP1389208A1 (en) | 2004-02-18 |
| US20030055043A1 (en) | 2003-03-20 |
| PE20021019A1 (es) | 2002-11-13 |
| DE60208366T2 (de) | 2006-07-06 |
| WO2002085901A8 (en) | 2003-12-24 |
| CA2439960A1 (en) | 2002-10-31 |
| WO2002085901A1 (en) | 2002-10-31 |
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