AU2010262643B2 - Diazahomoadamantane derivatives and methods of use thereof - Google Patents
Diazahomoadamantane derivatives and methods of use thereof Download PDFInfo
- Publication number
- AU2010262643B2 AU2010262643B2 AU2010262643A AU2010262643A AU2010262643B2 AU 2010262643 B2 AU2010262643 B2 AU 2010262643B2 AU 2010262643 A AU2010262643 A AU 2010262643A AU 2010262643 A AU2010262643 A AU 2010262643A AU 2010262643 B2 AU2010262643 B2 AU 2010262643B2
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- AU
- Australia
- Prior art keywords
- diazatricyclo
- undecane
- pyridin
- alkyl
- haloalkyl
- 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.)
- Ceased
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- 238000000034 method Methods 0.000 title claims abstract description 174
- 150000001875 compounds Chemical class 0.000 claims abstract description 347
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 117
- -1 1,3-thiazolyl Chemical group 0.000 claims description 109
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 42
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- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 2
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- ZCNPITMKMRMZMF-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.13,8]undecane Chemical compound FC1=CC=CC=C1C1=CN=CC(N2C3CC4CC(CN(C4)C3)C2)=C1 ZCNPITMKMRMZMF-UHFFFAOYSA-N 0.000 claims 1
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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
- C07D471/12—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 three hetero rings
- C07D471/18—Bridged 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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| CA2809028C (en) * | 2010-08-20 | 2019-04-09 | Research Triangle Institute | Nicotinic receptor compounds |
| CN103087001A (zh) * | 2011-11-03 | 2013-05-08 | 南京大学 | 香草酸的1，3，4-噁二唑衍生物及其制法和用途 |
| WO2014165090A1 (en) * | 2013-03-13 | 2014-10-09 | The Broad Institute, Inc. | Compounds for the treatment of tuberculosis |
| RU2552649C1 (ru) * | 2013-12-13 | 2015-06-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет тонких химических технологий имени М.В. Ломоносова" (МИТХТ им. М.В. Ломоносова) | Душистые 5-бензил-1,3-диазаадамантан-6-оны |
| WO2015103005A1 (en) * | 2014-01-03 | 2015-07-09 | Research Institute At Nationwide Children's Hospital | Amphiphilic amine compounds and their use as therapeutic agents and nanocarriers |
| WO2016100184A1 (en) | 2014-12-16 | 2016-06-23 | Forum Pharmaceuticals, Inc. | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| JP2018516973A (ja) | 2015-06-10 | 2018-06-28 | フォーラム・ファーマシューティカルズ・インコーポレイテッドＦｏｒｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | α７−ニコチン性アセチルコリン受容体のアゴニストとしてのアミノベンゾイソオキサゾール化合物 |
| EP3334740A4 (en) | 2015-08-12 | 2019-02-06 | Axovant Sciences GmbH | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF ALPHA 7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| CN108697709A (zh) * | 2015-12-10 | 2018-10-23 | Ptc医疗公司 | 用于治疗亨廷顿病的方法 |
| AU2018282154B2 (en) | 2017-06-05 | 2022-04-07 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| WO2019005993A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | METHODS OF TREATING HUNTINGTON'S DISEASE |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| AU2019219678A1 (en) * | 2018-02-08 | 2020-08-27 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Heteroaryl compounds, pharmaceutical compositions thereof, and their therapeutic use |
| BR112020019373A2 (pt) | 2018-03-27 | 2020-12-29 | Ptc Therapeutics, Inc. | Compostos para o tratamento da doença de hutington |
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| IL279688B2 (en) | 2018-06-27 | 2025-01-01 | Ptc Therapeutics Inc | Heterocyclic and heteroaryl compounds for the treatment of Huntington's disease |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1125922A1 (en) * | 1998-11-02 | 2001-08-22 | Welfide Corporation | Pyrrolidine compounds and medicinal utilization thereof |
| WO2008058096A2 (en) * | 2006-11-06 | 2008-05-15 | Abbott Laboratories | Azaadamantane derivatives and their uses as nicotinic acetylcholine receptors ligands |
| WO2008118743A1 (en) * | 2007-03-23 | 2008-10-02 | Abbott Laboratories | Acetamide and carboxamide derivatives of azaadamantane and methods of use thereof |
| WO2008118747A1 (en) * | 2007-03-23 | 2008-10-02 | Abbott Laboratories | Amimomethyl azaadamantane derivatives and use thereof as selective modulators of the alpha7- neuronal nicotinic acetylcholine receptor (nnrs) |
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| US4557865A (en) * | 1984-05-07 | 1985-12-10 | Pennwalt Corporation | Substituted 4-azatricyclo[4.3.1.13,8 ]undecane compounds |
| RU2162469C2 (ru) * | 1995-11-02 | 2001-01-27 | Ньюросерч А/С | Конденсированные тропановые производные в качестве ингибиторов обратного захвата нейромедиаторов |
| EE200100096A (et) * | 1998-08-18 | 2002-06-17 | Ucb, S.A. | Asatsüklilise tüvistruktuuriga tsükliline ühend, seda sisaldav farmatseutiline kompositsioon ning selle kasutamine ravimina |
| CA2450167A1 (en) * | 2001-06-12 | 2002-12-19 | Elan Pharmaceuticals, Inc. | Macrocycles useful in the treatment of alzheimer's disease |
| US20050065178A1 (en) * | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| US7482338B2 (en) * | 2003-09-26 | 2009-01-27 | Astrazeneca Ab | Non-amide nonanes |
| TW200840569A (en) * | 2007-03-13 | 2008-10-16 | Targacept Inc | Sub-type selective amides of diazabicycloalkanes |
| MX2009010174A (es) * | 2007-03-23 | 2009-10-12 | Abbott Lab | Derivados de aza-adamantano ester y carbamato y metodos de uso de los mismos. |
| CA2771885C (en) | 2009-09-14 | 2014-04-08 | Suven Life Sciences Limited | 1,2-dihydro-2-oxoquinoline compounds as 5-ht4receptor ligands |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1125922A1 (en) * | 1998-11-02 | 2001-08-22 | Welfide Corporation | Pyrrolidine compounds and medicinal utilization thereof |
| WO2008058096A2 (en) * | 2006-11-06 | 2008-05-15 | Abbott Laboratories | Azaadamantane derivatives and their uses as nicotinic acetylcholine receptors ligands |
| WO2008118743A1 (en) * | 2007-03-23 | 2008-10-02 | Abbott Laboratories | Acetamide and carboxamide derivatives of azaadamantane and methods of use thereof |
| WO2008118747A1 (en) * | 2007-03-23 | 2008-10-02 | Abbott Laboratories | Amimomethyl azaadamantane derivatives and use thereof as selective modulators of the alpha7- neuronal nicotinic acetylcholine receptor (nnrs) |
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| NZ597511A (en) | 2014-01-31 |
| IL216883A0 (en) | 2012-02-29 |
| AU2010262643A1 (en) | 2012-02-02 |
| CA2765466A1 (en) | 2010-12-23 |
| WO2010145208A1 (en) | 2010-12-23 |
| EP2443122B1 (en) | 2014-03-05 |
| RU2012101784A (ru) | 2013-07-27 |
| CN102459268A (zh) | 2012-05-16 |
| US20100324027A1 (en) | 2010-12-23 |
| MX2011014019A (es) | 2012-02-22 |
| RU2549551C2 (ru) | 2015-04-27 |
| US8846661B2 (en) | 2014-09-30 |
| EP2443122A1 (en) | 2012-04-25 |
| BRPI1015043A2 (pt) | 2019-07-09 |
| SG176921A1 (en) | 2012-01-30 |
| IL236830A0 (en) | 2015-03-31 |
| EP2443122A4 (en) | 2012-12-19 |
| RU2015110025A (ru) | 2015-08-20 |
| IL216883A (en) | 2015-02-26 |
| JP2012530084A (ja) | 2012-11-29 |
| PE20121066A1 (es) | 2012-09-13 |
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