JP2005538111A5 - - Google Patents
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- Publication number
- JP2005538111A5 JP2005538111A5 JP2004525191A JP2004525191A JP2005538111A5 JP 2005538111 A5 JP2005538111 A5 JP 2005538111A5 JP 2004525191 A JP2004525191 A JP 2004525191A JP 2004525191 A JP2004525191 A JP 2004525191A JP 2005538111 A5 JP2005538111 A5 JP 2005538111A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- substituted
- group
- membered
- 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.)
- Granted
Links
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 25
- -1 1-azabicyclo [2.2.2] oct-3-yl Chemical group 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 4
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- 230000008447 perception Effects 0.000 claims 4
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001804 chlorine Chemical class 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 0 *C(c(cc1)c(*2)cc1N(*)C(N(*)S)=*)=C2C(N(*)*)=O Chemical compound *C(c(cc1)c(*2)cc1N(*)C(N(*)S)=*)=C2C(N(*)*)=O 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10234424A DE10234424A1 (de) | 2002-07-29 | 2002-07-29 | Benzothiophen-, Benzofuran- und Indolharnstoffe |
| PCT/EP2003/007588 WO2004013136A1 (de) | 2002-07-29 | 2003-07-14 | Benzothiophen-, benzofuran- und indolharnstoffe und deren verwendung als alpha7-achr agonisten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005538111A JP2005538111A (ja) | 2005-12-15 |
| JP2005538111A5 true JP2005538111A5 (enExample) | 2006-08-31 |
| JP4601424B2 JP4601424B2 (ja) | 2010-12-22 |
Family
ID=30128473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004525191A Expired - Fee Related JP4601424B2 (ja) | 2002-07-29 | 2003-07-14 | ベンゾチオフェン尿素、ベンゾフラン尿素およびインドール尿素、並びにアルファ７−ＡｃｈＲアゴニストとしてのそれらの使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (6) | US7795453B2 (enExample) |
| EP (1) | EP1527073B1 (enExample) |
| JP (1) | JP4601424B2 (enExample) |
| AU (1) | AU2003254343A1 (enExample) |
| CA (1) | CA2494352C (enExample) |
| DE (2) | DE10234424A1 (enExample) |
| ES (1) | ES2291694T3 (enExample) |
| WO (1) | WO2004013136A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| ATE344262T1 (de) | 2002-06-10 | 2006-11-15 | Bayer Healthcare Ag | 2-heteroarylcarbonsäureamide |
| DE10234424A1 (de) * | 2002-07-29 | 2004-02-12 | Bayer Ag | Benzothiophen-, Benzofuran- und Indolharnstoffe |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| AR049401A1 (es) | 2004-06-18 | 2006-07-26 | Novartis Ag | Aza-biciclononanos |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| 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 |
| ES2541528T3 (es) | 2008-11-19 | 2015-07-21 | Forum Pharmaceuticals Inc. | Tratamiento de trastornos cognitivos con (R)-7-cloro-N-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida y sales farmacéuticamente aceptables de la misma |
| WO2010132423A1 (en) * | 2009-05-11 | 2010-11-18 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with certain alpha-7 nicotinic acid receptors in combination with acetylcholinesterase inhibitors |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| JP5749797B2 (ja) | 2010-05-17 | 2015-07-15 | フォルム ファーマシューティカルズ、インコーポレイテッド | （ｒ）−７−クロロ−ｎ−（キヌクリジン−３−イル）ベンゾ［ｂ］チオフェン−２−カルボキサミド塩酸塩一水和物の結晶形 |
| US20140171448A1 (en) | 2011-01-27 | 2014-06-19 | Novartis Ag | Use of nicotinic acetylcholine receptor alpha 7 activators |
| US20140228398A1 (en) | 2011-03-18 | 2014-08-14 | Novartis Ag | COMBINATIONS OF ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTOR ACTIVATORS AND mGluR5 ANTAGONISTS FOR USE IN DOPAMINE INDUCED DYSKINESIA IN PARKINSON'S DISEASE |
| BR112014007485B1 (pt) | 2011-10-20 | 2022-05-31 | Novartis Ag | Métodos para prever responsividade terapêutica de um indivíduo a tratamento com um ativador do receptor de acetilcolina nicotínico alfa 7, e usos do referido ativador |
| CA2872005A1 (en) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| CN104837499B (zh) | 2012-12-11 | 2018-02-23 | 诺华有限公司 | 预测对α7烟碱型乙酰胆碱受体激活剂治疗响应性的生物标志物 |
| EP3623371A1 (en) | 2014-12-16 | 2020-03-18 | Axovant Sciences GmbH | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| CA2988968A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmaceuticals, Inc. | Aminobenzisoxazole compounds as agonists of a7-nicotinic acetylcholine receptors |
| JP2018523707A (ja) | 2015-08-12 | 2018-08-23 | アクソバント サイエンシズ ゲーエムベーハー | 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ジェミナル置換アミノベンゾイソオキサゾール化合物 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605652A (en) | 1985-02-04 | 1986-08-12 | A. H. Robins Company, Inc. | Method of enhancing memory or correcting memory deficiency with arylamido (and arylthioamido)-azabicycloalkanes |
| NL8701682A (nl) | 1986-07-30 | 1988-02-16 | Sandoz Ag | Werkwijze voor het therapeutisch toepassen van serotonine antagonisten, aktieve verbindingen en farmaceutische preparaten die deze verbindingen bevatten. |
| DE3841313A1 (de) | 1988-12-08 | 1990-06-13 | Bayer Ag | Schwarzes pigment, verfahren zu seiner herstellung sowie dessen verwendung |
| US5189041A (en) | 1990-11-16 | 1993-02-23 | Syntex (U.S.A.) Inc. | Tricyclic 5-ht3 receptor antagonists |
| GB9201749D0 (en) | 1992-01-28 | 1992-03-11 | Smithkline Beecham Plc | Medicaments |
| US6169759B1 (en) | 1999-03-22 | 2001-01-02 | Golden Bridge Technology | Common packet channel |
| SE9903997D0 (sv) * | 1999-11-03 | 1999-11-03 | Astra Ab | New compounds |
| GB0010955D0 (en) | 2000-05-05 | 2000-06-28 | Novartis Ag | Organic compounds |
| JP4616971B2 (ja) | 2000-07-18 | 2011-01-19 | 田辺三菱製薬株式会社 | １−アザビシクロアルカン化合物およびその医薬用途 |
| US6492385B2 (en) | 2000-08-18 | 2002-12-10 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
| JP2004506734A (ja) * | 2000-08-21 | 2004-03-04 | ファルマシア・アンド・アップジョン・カンパニー | 疾患治療用のキヌクリド置換ヘテロアリール部分 |
| US6599916B2 (en) | 2000-08-21 | 2003-07-29 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
| DE10164139A1 (de) * | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| DE10234424A1 (de) * | 2002-07-29 | 2004-02-12 | Bayer Ag | Benzothiophen-, Benzofuran- und Indolharnstoffe |
| JP5749797B2 (ja) * | 2010-05-17 | 2015-07-15 | フォルム ファーマシューティカルズ、インコーポレイテッド | （ｒ）−７−クロロ−ｎ−（キヌクリジン−３−イル）ベンゾ［ｂ］チオフェン−２−カルボキサミド塩酸塩一水和物の結晶形 |
-
2002
- 2002-07-29 DE DE10234424A patent/DE10234424A1/de not_active Withdrawn
-
2003
- 2003-07-14 WO PCT/EP2003/007588 patent/WO2004013136A1/de not_active Ceased
- 2003-07-14 CA CA2494352A patent/CA2494352C/en not_active Expired - Fee Related
- 2003-07-14 AU AU2003254343A patent/AU2003254343A1/en not_active Abandoned
- 2003-07-14 DE DE50308015T patent/DE50308015D1/de not_active Expired - Lifetime
- 2003-07-14 EP EP03766162A patent/EP1527073B1/de not_active Expired - Lifetime
- 2003-07-14 ES ES03766162T patent/ES2291694T3/es not_active Expired - Lifetime
- 2003-07-14 JP JP2004525191A patent/JP4601424B2/ja not_active Expired - Fee Related
- 2003-07-14 US US10/522,611 patent/US7795453B2/en not_active Expired - Fee Related
-
2010
- 2010-08-30 US US12/871,495 patent/US8153799B2/en not_active Expired - Fee Related
-
2012
- 2012-04-06 US US13/441,407 patent/US8772511B2/en not_active Expired - Fee Related
-
2014
- 2014-06-09 US US14/299,750 patent/US9714242B2/en not_active Expired - Fee Related
-
2017
- 2017-06-15 US US15/624,227 patent/US10196388B2/en not_active Expired - Fee Related
-
2018
- 2018-12-20 US US16/228,182 patent/US20190367504A1/en not_active Abandoned
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