JP5183808B2 - 置換トリアゾロ−ピリダジン誘導体 - Google Patents
置換トリアゾロ−ピリダジン誘導体 Download PDFInfo
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- 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
- C07D487/04—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/22—Anxiolytics
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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Description
L−838417の有益な活性にもかかわらず、α1−GABA−A受容体アンタゴニストである新たな化合物に対するニーズが依然として存在する。
「治療する」という用語は、疾患(例えば、本明細書に示されている疾患または障害)の発生または進行を減少、抑制、減衰、縮小、停止、または安定させることを意味する。
治療用化合物
(式中、R1はCH3、CDH2、CD2H、またはCD3であり、
R2は、0〜9個の重水素原子を有するt−ブチル基であり、
各Yは独立して、水素または重水素であり、
R1がCH3であり、各Yが水素である場合、R2は1〜9個の重水素原子を有する)
の化合物、またはその薬学的に許容可能な塩を提供する。
代表的合成法
スキーム2.化合物15の合成
組成物
治療法
医薬キット
7−(tert−ブチル−d 9 )−3−(2,5−ジフルオロフェニル)−6−((1−(メチル−d 3 )−1H−1,2,4−トリアゾール−5−イル)−1,1−d 2 −メトキシ)−[1,2,4]トリアゾロ[4,3−b]ピリダジン(化合物105) 15b(0.24g、2.0mmol)をDMF(20mL)に溶解させた溶液に、鉱油中の60%水素化ナトリウム(0.08、2.1mmol)を加えた。この混合物を15分間攪拌し、14a(0.6g、1.8mmol、実施例1参照)を加えた。この混合物を3時間、室温で攪拌してから、水(100mL)で希釈した。その沈殿物をろ過して回収し、水で数回洗浄した。この粗生成物をシリカゲルカラムクロマトグラフィー(5%メタノール/ジクロロメタンで溶出)によって精製した。この生成物を、酢酸エチル/ヘプタン(1:1)からの再結晶によってさらに精製し、0.52g(70%)の化合物105を白色固体として得た。1H−NMR(300MHz、CDCl3):δ7.23−7.28(m、2H)、7.63−7.67(m、1H)、7.92(s、1H)、8.00(s、1H)。13C−NMR(75MHz、CDCl3):35.66および59.37でピークが観測されず。HPLC(方法:ウォーターズ製Atlantis T3 2.1×50mm 3μm C18−RPカラム−勾配法:14分で5〜95%ACN+0.1%ギ酸(1.0mL/分)、95%ACNで4分保持、波長:254nm):保持時間:5.40分、純度99.0%。MS(M+H):414.3。元素分析(C19H5D14F2N7O):計算値:C=55.20、H=4.63、N=23.72、F=9.19、実測値:C=54.88、H=4.45、N=23.46、F=9.59。
(1−(メチル−d 3 )−1H−1,2,4−トリアゾール−5−イル)−メタノール(15c) 17a(5g、58mmol、実施例2参照)とパラホルムアルデヒド(10g、333mmol)との混合物を密閉チューブ内で170℃にて5時間加熱した。この混合物を室温まで冷却し、ジクロロメタン(20mL)で希釈した。その固体をろ過して除去し、そのろ液を減圧下で濃縮した。この粗生成物をシリカゲルショートカラムクロマトグラフィー(5%メタノール/ジクロロメタンで溶出)によって精製し、5.0g(75%)の15cをオフホワイトの固体として得た。
1 H−NMR(300MHz、CDCl 3 ):δ5.55(s、2H)、7.23−7.28(m、2H)、7.62−7.67(m、1H)、7.93(s、1H)、8.00(s、1H)。 13 C−NMR(75MHz、CDCl 3 ):δ34.55、59.36、115.53(dd、J 1 =16.6、J 2 =8.8)、117.63(dd、J 1 =24.4、J 2 =12.8)、117.71(dd、J 1 =24.1、J 2 =8.0)、118.77(dd、J 1 =23.9、J 2 =8.5)、121.75、137.85、143.48、145.00、149.50、151.15、155.76(d、J=163.5)、159.08(d、J=156.9)、158.71。HPLC(方法:ウォーターズ製Atlantis T3 2.1×50mm 3μm C18−RPカラム−勾配法:14分で5〜95%ACN+0.1%ギ酸(1.0mL/分)、95%ACNで4分保持、波長:254nm):保持時間:5.40分、純度99.6%。MS(M+H):412.2。元素分析(C 19 H 7 D 12 F 2 N 7 O):計算値:C=55.47、H=4.67、N=23.83、実測値:C=55.49、H=4.76、N=23.87。
7−tert−ブチル−3−(2,5−ジフルオロフェニル)−6−((1−(メチル−d 3 )−1H−1,2,4−トリアゾール−5−イル)−1,1−d 2 −メトキシ)−[1,2,4]トリアゾロ[4,3−b]ピリダジン(化合物101) 15b(0.24g、4.0mmol、実施例2参照)をDMF(10mL)に溶解させた溶液に、鉱油中の60%水素化ナトリウム(0.08、2.1mmol)を加えた。この混合物を15分間攪拌し、既知の化合物7−tert−ブチル−6−クロロ−3−(2,5−ジフルオロフェニル)−[1,2,4]トリアゾロ[4,3−b]ピリダジン、14b(0.58g、1.8mmol、国際公開第WO1998004559号に記載されているように調製)を加えた。この混合物を3時間、室温で攪拌してから、水(100mL)で希釈した。その沈殿物をろ過して回収し、水で数回洗浄した。この粗生成物をシリカゲルカラムクロマトグラフィー(75%THF/ヘプタンで溶出)によって精製した。この生成物を、酢酸エチル/ヘプタン(1:1)からの再結晶によってさらに精製し、0.53g(72%)の化合物101を白色固体として得た。1H−NMR(300MHz、CDCl3):δ1.41(s、9H)、7.23−7.28(m、2H)、7.62−7.68(m、1H)、7.92(s、1H)、8.00(s、1H)。13C−NMR(75MHz、CDCl3):28.96でピークが観察され、35.66および59.36ではピークは観察されず。HPLC(方法:ウォーターズ製Atlantis T3 2.1×50mm 3μm C18−RPカラム−勾配法:14分で5〜95%ACN+0.1%ギ酸(1.0mL/分)、95%ACNで4分保持、波長:254nm):保持時間:5.42分、純度99.7%。MS(M+H):405.3。元素分析(C19H14D5F2N7O):計算値:C=56.43、H=4.74、N=24.25、F=9.40、実測値:C=56.22、H=4.73、N=23.87、F=9.35。
インビトロt1/2=0.693/k(式中、k=−[親化合物の残存率(%)(ln)とインキュベーション時間との関係の直線回帰の傾斜]
データ解析は、マイクロソフトのソフトウェアExcelを用いて行った。
Claims (9)
- 式中のY1aとY1bが同じである、請求項1に記載の化合物。
- 重水素として指定されていないいずれの原子も、その天然同位体存在度で存在する、請求項1〜3のいずれか一項に記載の化合物。
- 請求項1の化合物と、許容可能な担体とを含む組成物。
- 前記化合物が経口投与用に製剤化されている、請求項6に記載の組成物。
- 医薬投与用に製剤化された請求項6に記載の組成物であって、その担体が、薬学的に許容可能な担体である組成物。
- 不安または痙攣を患う患者を治療するために使用される請求項6に記載の組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9329308P | 2008-08-29 | 2008-08-29 | |
US61/093,293 | 2008-08-29 | ||
PCT/US2009/055427 WO2010025407A1 (en) | 2008-08-29 | 2009-08-28 | Substituted triazolo-pyridazine derivatives |
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JP2013004449A Division JP5373982B2 (ja) | 2008-08-29 | 2013-01-15 | 置換トリアゾロ−ピリダジン誘導体 |
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JP2012501346A JP2012501346A (ja) | 2012-01-19 |
JP2012501346A5 JP2012501346A5 (ja) | 2012-10-18 |
JP5183808B2 true JP5183808B2 (ja) | 2013-04-17 |
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JP2011525250A Expired - Fee Related JP5183808B2 (ja) | 2008-08-29 | 2009-08-28 | 置換トリアゾロ−ピリダジン誘導体 |
JP2013004449A Expired - Fee Related JP5373982B2 (ja) | 2008-08-29 | 2013-01-15 | 置換トリアゾロ−ピリダジン誘導体 |
JP2013194060A Pending JP2014058518A (ja) | 2008-08-29 | 2013-09-19 | 置換トリアゾロ−ピリダジン誘導体 |
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JP2013004449A Expired - Fee Related JP5373982B2 (ja) | 2008-08-29 | 2013-01-15 | 置換トリアゾロ−ピリダジン誘導体 |
JP2013194060A Pending JP2014058518A (ja) | 2008-08-29 | 2013-09-19 | 置換トリアゾロ−ピリダジン誘導体 |
Country Status (17)
Country | Link |
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US (4) | US8003646B2 (ja) |
EP (2) | EP2716158A1 (ja) |
JP (3) | JP5183808B2 (ja) |
KR (1) | KR20110063479A (ja) |
CN (2) | CN104098578A (ja) |
AU (1) | AU2009285533B2 (ja) |
BR (1) | BRPI0912928A2 (ja) |
CA (1) | CA2735549A1 (ja) |
DK (1) | DK2328414T3 (ja) |
EA (1) | EA020071B1 (ja) |
ES (1) | ES2451542T3 (ja) |
HR (1) | HRP20140195T1 (ja) |
MX (1) | MX2011002278A (ja) |
PL (1) | PL2328414T3 (ja) |
PT (1) | PT2328414E (ja) |
WO (1) | WO2010025407A1 (ja) |
ZA (1) | ZA201102123B (ja) |
Cited By (1)
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JP2014058518A (ja) * | 2008-08-29 | 2014-04-03 | Concert Pharmaceuticals Inc | 置換トリアゾロ−ピリダジン誘導体 |
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US20110177468A1 (en) | 2008-10-03 | 2011-07-21 | Fabiola Barbosa Ormiga Galvao | Method and device for removing metallic fragments and metallic elements from dental root canals |
WO2011005520A1 (en) * | 2009-06-23 | 2011-01-13 | Concert Pharmaceuticals, Inc. | Deuterium-modified triazolo-pyridazine derivatives as gaba-a receptor modulators |
JP6073343B2 (ja) | 2011-10-20 | 2017-02-01 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーGlaxoSmithKline LLC | サーチュイン調節因子としての置換された二環式アザ複素環およびアナログ |
EP2768834B1 (en) * | 2011-10-20 | 2016-04-27 | Glaxosmithkline LLC | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
BR112014016930A8 (pt) | 2012-01-11 | 2017-12-26 | Bayer Ip Gmbh | compostos tetrazol-5-il- e triazol-5-il-arila e uso destes como herbicidas |
US20150099753A1 (en) * | 2012-05-11 | 2015-04-09 | Concert Pharmaceuticals Inc. | Form 5 polymorph of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
WO2013170241A1 (en) * | 2012-05-11 | 2013-11-14 | Concert Pharmaceuticals, Inc. | Polymorphs of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolol[4,3b]pyridazine |
JP2015516440A (ja) * | 2012-05-11 | 2015-06-11 | コンサート ファーマシューティカルズ インコーポレイテッド | 7−(tert−ブチル−d9)−3−(2,5−ジフルオロフェニル)−6−((1−メチル−1H−1,2,4−トリアゾール−5−イル)メトキシ)−[1,2,4]トリアゾロ[4,3−b]ピリダジンの2型多形 |
WO2015052178A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
WO2015052173A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Tetrazole and triazole compounds and their use as herbicides |
WO2015095549A1 (en) * | 2013-12-18 | 2015-06-25 | Concert Pharmaceuticals, Inc. | Dosage regimen for gabaa receptor subtype selective drug |
EA201691582A1 (ru) | 2014-02-07 | 2017-01-30 | Оспекс Фармасьютикалз, Инк. | Новые фармацевтические препараты |
CN104353078B (zh) * | 2014-11-24 | 2017-10-24 | 王寿世 | 一种麻醉用药物组合物 |
CN104474549A (zh) * | 2014-11-24 | 2015-04-01 | 王寿世 | 异丙酚和gabaa受体拮抗剂在制备麻醉药物中的用途 |
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WO2023205722A1 (en) * | 2022-04-20 | 2023-10-26 | Engrail Therapeutics, Inc. | Gabaa receptor modulator salts, particles, and uses thereof |
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WO2006061428A2 (en) | 2004-12-10 | 2006-06-15 | Universität Zürich | Gaba-a alpha 2 and alpha 3 receptor agonists for treating neuropathic, inflammatory and migraine associated pain |
CN101309917B (zh) | 2005-10-06 | 2013-09-11 | 奥斯拜客斯制药有限公司 | 具有增强治疗性质的胃h+,k+-atp酶氘代抑制剂 |
US7750168B2 (en) | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
JO2630B1 (en) | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
CN101594870A (zh) * | 2006-08-22 | 2009-12-02 | 康塞特医药品有限公司 | 4-氨基喹唑啉衍生物及其使用方法 |
JP2010502702A (ja) | 2006-09-05 | 2010-01-28 | シェーリング コーポレイション | 脂質管理およびアテローム性動脈硬化症および脂肪肝の治療治療において使用される医薬組成物 |
AU2008232425A1 (en) * | 2007-04-02 | 2008-10-09 | Auspex Pharmaceuticals, Inc. | Substituted pyrimidines |
DK2328414T3 (en) * | 2008-08-29 | 2014-03-10 | Concert Pharmaceuticals Inc | Substituted triazolopyridazine derivatives |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014058518A (ja) * | 2008-08-29 | 2014-04-03 | Concert Pharmaceuticals Inc | 置換トリアゾロ−ピリダジン誘導体 |
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