JP2009525993A5 - - Google Patents
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- Publication number
- JP2009525993A5 JP2009525993A5 JP2008553621A JP2008553621A JP2009525993A5 JP 2009525993 A5 JP2009525993 A5 JP 2009525993A5 JP 2008553621 A JP2008553621 A JP 2008553621A JP 2008553621 A JP2008553621 A JP 2008553621A JP 2009525993 A5 JP2009525993 A5 JP 2009525993A5
- Authority
- JP
- Japan
- Prior art keywords
- alkynyl
- alkenyl
- alkyl
- cycloalkenyl
- cycloalkyl
- 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
Links
- 125000003342 alkenyl group Chemical group 0.000 claims description 1143
- 125000000304 alkynyl group Chemical group 0.000 claims description 1143
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 1086
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 402
- 229910052739 hydrogen Inorganic materials 0.000 claims description 126
- 239000001257 hydrogen Substances 0.000 claims description 126
- 238000000034 method Methods 0.000 claims description 112
- 150000002431 hydrogen Chemical class 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 94
- 201000000980 schizophrenia Diseases 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 125000002252 acyl group Chemical group 0.000 claims description 54
- 208000024891 symptom Diseases 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 51
- 229910052760 oxygen Inorganic materials 0.000 claims description 48
- 125000005842 heteroatom Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 238000012360 testing method Methods 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 102000012359 KCNQ Potassium Channels Human genes 0.000 claims description 18
- 108010022282 KCNQ Potassium Channels Proteins 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- 208000013403 hyperactivity Diseases 0.000 claims description 14
- 150000002500 ions Chemical class 0.000 claims description 14
- 208000009668 Neurobehavioral Manifestations Diseases 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 230000000561 anti-psychotic effect Effects 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000000164 antipsychotic agent Substances 0.000 claims description 8
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 7
- -1 -CO-NR6R6 ' Chemical group 0.000 claims description 7
- 206010012239 Delusion Diseases 0.000 claims description 7
- 102000004980 Dopamine D2 Receptors Human genes 0.000 claims description 7
- 108090001111 Dopamine D2 Receptors Proteins 0.000 claims description 7
- 230000001154 acute effect Effects 0.000 claims description 7
- 229940025084 amphetamine Drugs 0.000 claims description 7
- 231100000868 delusion Toxicity 0.000 claims description 7
- 238000010304 firing Methods 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000009182 swimming Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 238000012216 screening Methods 0.000 claims description 6
- 230000002269 spontaneous effect Effects 0.000 claims description 6
- 229940005529 antipsychotics Drugs 0.000 claims description 5
- IAAITAGXZWCRTQ-UHFFFAOYSA-N 2-cyclopentyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCCC1 IAAITAGXZWCRTQ-UHFFFAOYSA-N 0.000 claims description 3
- JNWPEEJRMRBMPA-UHFFFAOYSA-N 2-cyclopentyl-n-(2-methoxy-6-methyl-4-morpholin-4-ylphenyl)acetamide Chemical compound COC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1CCCC1 JNWPEEJRMRBMPA-UHFFFAOYSA-N 0.000 claims description 3
- IMOFGKWQMCCNKF-UHFFFAOYSA-N 2-cyclopentyl-n-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)acetamide Chemical compound CC1=NC(N2CCOCC2)=NC(C)=C1NC(=O)CC1CCCC1 IMOFGKWQMCCNKF-UHFFFAOYSA-N 0.000 claims description 3
- 229940127315 Potassium Channel Openers Drugs 0.000 claims description 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 3
- SCOOTUMXCXKEAD-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,4,6-trimethylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=C(C)C=C1C SCOOTUMXCXKEAD-UHFFFAOYSA-N 0.000 claims description 3
- PCOBBVZJEWWZFR-UHFFFAOYSA-N ezogabine Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1 PCOBBVZJEWWZFR-UHFFFAOYSA-N 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- BKFDFCVASNKPOA-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(N2CCOCC2)=N1 BKFDFCVASNKPOA-UHFFFAOYSA-N 0.000 claims description 3
- BPFWCATXXHFMHU-UHFFFAOYSA-N n-(2,6-difluoro-4-morpholin-4-ylphenyl)hexanamide Chemical compound C1=C(F)C(NC(=O)CCCCC)=C(F)C=C1N1CCOCC1 BPFWCATXXHFMHU-UHFFFAOYSA-N 0.000 claims description 3
- OVEJXWFUXCATFY-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(N2CCOCC2)=C1 OVEJXWFUXCATFY-UHFFFAOYSA-N 0.000 claims description 3
- DKKUESYXEUWVTR-UHFFFAOYSA-N n-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)-2-(4-fluorophenyl)acetamide Chemical compound CC1=NC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=C(F)C=C1 DKKUESYXEUWVTR-UHFFFAOYSA-N 0.000 claims description 3
- WOVDEFIGDUUBDM-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]propanamide Chemical compound C1=C(C(F)(F)F)C(NC(=O)CC)=C(Br)C=C1N1CCOCC1 WOVDEFIGDUUBDM-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 108091006146 Channels Proteins 0.000 claims description 2
- 108020003175 receptors Proteins 0.000 claims description 2
- 102000005962 receptors Human genes 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 337
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 18
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910005965 SO 2 Inorganic materials 0.000 description 36
- 230000004907 flux Effects 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 0 *CN(*)c(cc1N*)ccc1N* Chemical compound *CN(*)c(cc1N*)ccc1N* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000004036 potassium channel stimulating agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77130406P | 2006-02-07 | 2006-02-07 | |
| DKPA200600175 | 2006-02-07 | ||
| PCT/DK2007/050013 WO2007090409A1 (en) | 2006-02-07 | 2007-02-02 | Use of kcnq-openers for threating or reducing the symptoms of schizophrenia |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009525993A JP2009525993A (ja) | 2009-07-16 |
| JP2009525993A5 true JP2009525993A5 (enExample) | 2010-03-25 |
Family
ID=38055396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008553621A Ceased JP2009525993A (ja) | 2006-02-07 | 2007-02-02 | 統合失調症の症状を治療または軽減するためにｋｃｎｑ開口薬を使用する方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20090118285A1 (enExample) |
| EP (2) | EP2554162A1 (enExample) |
| JP (1) | JP2009525993A (enExample) |
| KR (1) | KR20080096659A (enExample) |
| CN (1) | CN101378742B (enExample) |
| AR (1) | AR059319A1 (enExample) |
| AU (1) | AU2007214128B2 (enExample) |
| BR (1) | BRPI0707495A2 (enExample) |
| CA (1) | CA2641564C (enExample) |
| EA (1) | EA017915B1 (enExample) |
| IL (1) | IL192745A0 (enExample) |
| MX (1) | MX2008009655A (enExample) |
| NO (1) | NO20083838L (enExample) |
| NZ (1) | NZ569517A (enExample) |
| TW (1) | TWI453013B (enExample) |
| WO (1) | WO2007090409A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011513196A (ja) * | 2007-08-01 | 2011-04-28 | ハー・ルンドベック・アクチエゼルスカベット | ドーパミン作動系が破壊された障害もしくは状態の症状を軽減するためまたはその障害もしくは状態を処置するためのｋｃｎｑカリウムチャネル開口薬の使用 |
| CA2804165C (en) | 2010-07-08 | 2015-02-24 | Pfizer Inc. | Piperidinyl pyrimidine amides as kv7 potassium channel openers |
| WO2016077724A1 (en) * | 2014-11-13 | 2016-05-19 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | (2-amino-4(arylamino)phenyl) carbamates |
| US10590067B2 (en) | 2018-02-20 | 2020-03-17 | H. Lundbeck A/S | Alcohol derivatives of carboxamides as Kv7 potassium channel openers |
| MA51881B1 (fr) | 2018-02-20 | 2023-08-31 | H Lundbeck As | Dérivés d'alcool utilisés en tant qu'agents d'ouverture du canal potassique kv7 |
| WO2019203951A1 (en) | 2018-04-20 | 2019-10-24 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Selective potassium channel agonists |
| RS66130B1 (sr) | 2019-08-02 | 2024-11-29 | H Lundbeck As | Derivati alkohola kao otvarači kv7 kalijumovih kanala |
| CN119490430A (zh) | 2019-08-02 | 2025-02-21 | H.隆德贝克有限公司 | 用于在癫痫或癫痫发作中使用的作为Kv7钾通道开放剂的醇衍生物 |
| AR119521A1 (es) | 2019-08-02 | 2021-12-22 | H Lundbeck As | DERIVADOS DE ALCOHOL COMO ABRIDORES DEL CANAL DE POTASIO Kv7 |
| US20230015539A1 (en) * | 2019-12-06 | 2023-01-19 | Icahn School Of Medicine At Mount Sinai | Method of treatment with kcnq channel openers |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4200259A1 (de) * | 1992-01-08 | 1993-07-15 | Asta Medica Ag | Neue 1,2,4-triaminobenzol-derivate und verfahren zu deren herstellung |
| JP4294142B2 (ja) | 1999-02-02 | 2009-07-08 | 株式会社日立製作所 | ディスクサブシステム |
| GB9915414D0 (en) * | 1999-07-01 | 1999-09-01 | Glaxo Group Ltd | Medical use |
| US6472165B1 (en) * | 1999-08-03 | 2002-10-29 | Arzneimittelwerk Dresden Gmbh | Modulatory binding site in potassium channels for screening and finding new active ingredients |
| US6495550B2 (en) * | 1999-08-04 | 2002-12-17 | Icagen, Inc. | Pyridine-substituted benzanilides as potassium ion channel openers |
| CA2438868A1 (en) * | 2001-02-20 | 2002-09-19 | Valentin K. Gribkoff | Modulators of kcnq potassium channels and use thereof in treating migraine and mechanistically related diseases |
| US6469042B1 (en) * | 2001-02-20 | 2002-10-22 | Bristol-Myers Squibb Company | Fluoro oxindole derivatives as modulators if KCNQ potassium channels |
| JP2004535413A (ja) * | 2001-05-31 | 2004-11-25 | ブリストル−マイヤーズ スクイブ カンパニー | Ｋｃｎｑカリウムチャンネルモジュレーターとしてのシンナミド誘導体 |
| DE10228103A1 (de) | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| AU2003294442A1 (en) * | 2002-11-22 | 2004-06-18 | Bristol-Myers Squibb Company | 3-heterocyclic benzylamide derivatives as potassium channel openers |
| US6933308B2 (en) * | 2002-12-20 | 2005-08-23 | Bristol-Myers Squibb Company | Aminoalkyl thiazole derivatives as KCNQ modulators |
| NZ540446A (en) * | 2002-12-27 | 2008-03-28 | Lundbeck & Co As H | 1,2,4-Triaminobenzene derivatives useful for treating disorders of the central nervous system |
| EP1603858A2 (en) * | 2003-03-11 | 2005-12-14 | NeuroSearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| JP2006520333A (ja) * | 2003-03-14 | 2006-09-07 | ハー・ルンドベック・アクチエゼルスカベット | 置換されたアニリン誘導体 |
| AU2004222626B2 (en) * | 2003-03-21 | 2010-06-24 | H. Lundbeck A/S | Substituted p-diaminobenzene derivatives |
| EP1631546A1 (en) | 2003-04-25 | 2006-03-08 | H. Lundbeck A/S | Sustituted indoline and indole derivatives |
| US7563748B2 (en) | 2003-06-23 | 2009-07-21 | Cognis Ip Management Gmbh | Alcohol alkoxylate carriers for pesticide active ingredients |
| WO2005025293A2 (en) * | 2003-09-10 | 2005-03-24 | Icagen, Inc. | Fused ring heterocycles as potassium channel modulators |
| ATE423128T1 (de) * | 2004-02-20 | 2009-03-15 | Nat Ct For Biolog Sciences | Neues kaliumkanalmodulierendes peptid |
| TWI349666B (en) * | 2004-03-12 | 2011-10-01 | Lundbeck & Co As H | Substituted morpholine and thiomorpholine derivatives |
| WO2006000020A1 (en) | 2004-06-29 | 2006-01-05 | European Nickel Plc | Improved leaching of base metals |
| UA89503C2 (uk) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Заміщені похідні аніліну |
| US7812020B2 (en) * | 2005-03-03 | 2010-10-12 | H. Lundbeck A/S | Substituted pyridine derivatives |
| WO2007063418A2 (en) * | 2005-04-13 | 2007-06-07 | Neuraxon, Inc. | Substituted indole compounds having nos inhibitory activity |
-
2007
- 2007-02-02 EP EP12190206A patent/EP2554162A1/en not_active Withdrawn
- 2007-02-02 EP EP07702527A patent/EP1983974A1/en not_active Withdrawn
- 2007-02-02 BR BRPI0707495-6A patent/BRPI0707495A2/pt not_active IP Right Cessation
- 2007-02-02 JP JP2008553621A patent/JP2009525993A/ja not_active Ceased
- 2007-02-02 CA CA2641564A patent/CA2641564C/en not_active Expired - Fee Related
- 2007-02-02 KR KR1020087019396A patent/KR20080096659A/ko not_active Ceased
- 2007-02-02 AU AU2007214128A patent/AU2007214128B2/en not_active Ceased
- 2007-02-02 TW TW096103826A patent/TWI453013B/zh not_active IP Right Cessation
- 2007-02-02 CN CN2007800046484A patent/CN101378742B/zh not_active Expired - Fee Related
- 2007-02-02 EA EA200870232A patent/EA017915B1/ru not_active IP Right Cessation
- 2007-02-02 WO PCT/DK2007/050013 patent/WO2007090409A1/en not_active Ceased
- 2007-02-02 MX MX2008009655A patent/MX2008009655A/es active IP Right Grant
- 2007-02-02 NZ NZ569517A patent/NZ569517A/en not_active IP Right Cessation
- 2007-02-02 US US12/278,394 patent/US20090118285A1/en not_active Abandoned
- 2007-02-05 AR ARP070100469A patent/AR059319A1/es not_active Application Discontinuation
-
2008
- 2008-07-10 IL IL192745A patent/IL192745A0/en unknown
- 2008-09-05 NO NO20083838A patent/NO20083838L/no not_active Application Discontinuation
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