JP5225287B2 - アミノアルコール誘導体およびその治療用途 - Google Patents
アミノアルコール誘導体およびその治療用途 Download PDFInfo
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Description
R1は任意にR8で置換されたアリールまたはヘテロアリールであり;
R2はHもしくはアルキルまたはCH2(R3、R4またはR5と共に環の一部を形成する場合)であり;
R3はH、アルキル、CH2OHもしくはCH2OR6であるか、R2と共に環の一部であってよく;
R4はH、アルキル、CH2OHもしくはCH2OR6であるか、R2と共に環の一部であってよく;
R5はH、アルキル、CH2OHもしくはCH2OR6であるか、R2と共に環の一部であってよく;
R6はH、アルキル、COH、COOR9、CON(R9)2、COR9、COR10、COR11、P(O)nR9、P(O)nR10、S(O)nR10もしくはS(O)nR9であるか、R2、R3、R4もしくはR5と共に環の一部であってよく;
R7はH、アルキル、COOR9、COOR11、COR9もしくはCON(R9)2であるか、R2、R3、R4、R5もしくはR6と共に環の一部であってよく;
R8はアルキル、CF3、OR9、OCOR9、CONH2、CN、F、Cl、Br、I、N(R9)2、NO2、NHCHO、NHCONH2、NHSO2R9、CON(R9)2、S(O)nR9、CH2OHまたはOCON(R9)2であり;
R9はH、アルキルまたはシクロアルキルであり;
R10はアリールもしくはヘテロアリール(任意にR8で置換されている)または4〜7員環(任意にR8で置換され、O、S(O)nおよびNR9から選択される1以上のさらなるヘテロ原子を含んでよい)であり;
R11は任意にR8またはR10で置換されたアルキルであり、
nはO、1または2であるが、
但しR3、R4またはR5がCH2OHである場合にはR6はHではなく、R7がHでありR3、R4およびR5がアルキルである場合にはR6はHではない]
で表される。
本明細書において使用される場合、「アルキル」、「アリール」、「シクロアルキル」、および「ヘテロアリール」は当業者によって理解される意味を有する。これらは、最大6個または12個の炭素原子および4〜7個の環原子を含み得る。いずれの環も、飽和であっても良いし、不飽和であっても良い。例えば、R1はフェニルまたはハロフェニルであって良い。R6はエステルを形成しても良い。
1H NMR (400 MHz, CDCl3) 0.98 (9H, s), 0.99 (3H, bs), 2.12 (3H, s), 3.01 - 3.02 (1H, m), 5.51 - 5.53 (1H, m), 7.23 - 7.31 (4H, m)。
13C NMR (100MHz, CDCl3) 19.6, 21.3, 30.0, 50.9, 51.4, 77.4, 125.4, 127.3, 127.8, 129.3, 134.1, 140.0, 170.4。
1H NMR (400 MHz, CDCl3) 0.97 (9H, s), 1.05 (3H, d), 1.21 (6H, t), 2.62 - 2.64 (1H, m), 3.02 - 3.03 (1H, m), 5.51 (1H, d), 7.22 - 7.30 (4H, m)。
13C NMR (100 MHz, CDCl3) 19.1, 19.6, 30.0, 34.3, 50.9, 51.6, 79.2, 125.2, 127.1, 127.7, 129.3, 134.1, 141.6, 176.5。
1H NMR(400 MHz, CDCl3) 3.08 (2H, t), 3.33 (3H, s), 3.65 (2H, t)。
1H NMR (400 MHz, CDCl3) 1.02 (9H, s), 1.04 (3H, d), 2.67 (2H, t), 3.00 - 3.03 (1H, m), 3.35 (3H, s), 3.68 - 3.70 (2H, m), 5.58 (1H, d), 7.22 - 7.32 (4H, m)。
13C NMR (100 MHz, CDCl3) 19.4, 30.0, 35.5, 51.0, 51.5, 58.8, 68.1, 79.7, 125.2, 127.1, 127.7, 129.3, 134.1, 141.9, 171.2。
1H NMR (400 MHz, CDCl3) 1.85 - 1.90 (2H, m), 1.91 - 2.0 (2H, m), 2.94 - 2.96 (1H, m), 3.42 - 3.43 (2H, m), 3.97 - 4.00 (2H, s)。
1H NMR (400 MHz, CDCl3) 0.97 (9H, s), 1.04 (3H, d), 1.80- 1.87 (4H, m), 2.62 - 2.64 (1H, m), 3.03 - 3.04 (1H, m), 3.42 - 3.45 (2H, m), 3.95 - 3.96 (2H, m), 5.54 (1H, d), 7.22 - 7.28 (4H, m)。
13C NMR (100 MHz, CDCl3) 19.5, 28.4, 29.9, 40.4, 51.0, 51.6, 67.2, 79.4, 125.2, 127.1, 127.8, 129.4, 134.1, 141.3, 173.7。
絶食させた(18時間)オスのWistarラット(105〜130g)を計量し、肢を脛骨足根骨関節まで水銀中に浸すことによって、水銀足容積測定装置での基礎測定値を、右後肢について測定した。引き続いて、ベヒクル、参照物質および試験物質を、強制経口投与(10ml/kg)によって投与した。処置から30分後に、0.9%生理食塩水中2%のカラギーナン0.1mlを、右後肢の足底部に注射した。カラギーナン投与から1、2、3、4、および5時間後に、足容積測定装置で右肢を再び測定した。足容積効果は、時間に対する足容積についての曲線下面積として表された。活性(足容積の阻害)は、ベヒクル対照に対する抗炎症活性(%)として表された。
Claims (23)
- 単一のエナンチオマーまたはジアステレオマーの形態である請求項1に記載の化合物。
- (+)-(エリトロ)-酢酸2-tert-ブチルアミノ-1-(3-クロロフェニル)-プロピルエステルである請求項1に記載の化合物。
- (+)-(エリトロ)-イソ酪酸2-tert-ブチルアミノ-1-(3-クロロフェニル)-プロピルエステルである請求項1に記載の化合物。
- (+)-(エリトロ)-3-メトキシ-プロピオン酸2-tert-ブチルアミノ-1-(3-クロロフェニル)-プロピルエステルである請求項1に記載の化合物。
- (+)-(エリトロ)-テトラヒドロピラン-4-カルボン酸2-tert-ブチルアミノ-1-(3-クロロフェニル)-プロピルエステルである請求項1に記載の化合物。
- T細胞増殖に関連する病状または前炎症性サイトカインおよび/もしくは抗炎症性サイトカインによって媒介される病状の治療または予防のための、請求項1〜6のいずれか1項に記載の化合物。
- 前記病状が、慢性変性疾患、慢性脱髄性疾患、呼吸器疾患、炎症性腸疾患(IBD)、皮膚疾患、歯の疾患、糖尿病性腎症、ループス腎炎、IgA腎症、糸球体腎炎、全身性紅斑性狼瘡(SLE)、移植片対宿主病、目の疾患、または疼痛状態である、請求項7に記載の化合物。
- 前記慢性脱髄性疾患が、多発性硬化症である、請求項8に記載の化合物。
- 前記呼吸器疾患が、喘息または慢性閉塞性肺疾患である、請求項8に記載の化合物。
- 前記炎症性腸疾患(IBD)が、潰瘍性大腸炎またはクローン病である、請求項8に記載の化合物。
- 前記皮膚疾患が、乾癬、強皮症、またはアトピー性皮膚炎である、請求項8に記載の化合物。
- 前記歯の疾患が、歯周病または歯肉炎である、請求項8に記載の化合物。
- 前記慢性変性疾患が、関節リウマチ、変形性関節症、または骨粗鬆症である、請求項8に記載の化合物。
- 前記目の疾患が、ARMD、ドライアイ、ブドウ膜炎、または緑内障である、請求項8に記載の化合物。
- 前記疼痛状態が、慢性疼痛、急性疼痛、または神経障害性疼痛である、請求項8に記載の化合物。
- 前記慢性疼痛が、慢性背痛、悪性疼痛、慢性頭痛、または関節痛である、請求項16に記載の化合物。
- 前記慢性頭痛が、片頭痛または群発性頭痛である、請求項17に記載の化合物。
- 前記急性疼痛が、術後痛、外傷後疼痛、または急性疾患誘発性疼痛である、請求項16に記載の化合物。
- 請求項1〜6のいずれか1項に記載の化合物、および医薬上許容可能な希釈剤または担体を含む、治療に用いるための医薬組成物。
- 請求項7〜19のいずれか1項に定義された病状の治療または予防のための医薬品を製造するための、請求項1〜6のいずれか1項に記載の化合物の使用。
- 患者が、コルチコステロイド、細胞毒、抗生物質、免疫抑制剤、非ステロイド性抗炎症薬、麻薬性鎮痛薬、局所麻酔薬、NMDAアンタゴニスト、神経遮断薬、抗痙攣薬、鎮痙薬、抗うつ薬、および筋弛緩薬から選択される別の治療剤もまた投与される、請求項21に記載の使用。
- 前記化合物および前記別の治療剤が組み合わせて提供される、請求項22に記載の使用。
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Application Number | Priority Date | Filing Date | Title |
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GB0624757.1 | 2006-12-12 | ||
GBGB0624757.1A GB0624757D0 (en) | 2006-12-12 | 2006-12-12 | Novel compounds |
PCT/GB2007/004752 WO2008071948A2 (en) | 2006-12-12 | 2007-12-12 | Aminoalcohol derivatives and their therapeutic use |
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JP2010512378A JP2010512378A (ja) | 2010-04-22 |
JP5225287B2 true JP5225287B2 (ja) | 2013-07-03 |
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JP2009540849A Expired - Fee Related JP5225287B2 (ja) | 2006-12-12 | 2007-12-12 | アミノアルコール誘導体およびその治療用途 |
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US (1) | US20100076068A1 (ja) |
EP (2) | EP2118050A2 (ja) |
JP (1) | JP5225287B2 (ja) |
KR (1) | KR20090088442A (ja) |
CN (1) | CN101573325A (ja) |
AU (1) | AU2007331337A1 (ja) |
BR (1) | BRPI0720284A2 (ja) |
CA (1) | CA2672238A1 (ja) |
GB (1) | GB0624757D0 (ja) |
IL (1) | IL199178A0 (ja) |
MX (1) | MX2009006246A (ja) |
NO (1) | NO20092359L (ja) |
WO (1) | WO2008071948A2 (ja) |
ZA (1) | ZA200903942B (ja) |
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KR102635931B1 (ko) | 2016-12-14 | 2024-02-13 | 에스케이바이오팜 주식회사 | 가려움증의 예방, 경감 또는 치료를 위한 카바메이트 화합물의 용도 |
GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
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IT1222986B (it) * | 1987-10-23 | 1990-09-12 | Texcontor Ets | Derivati dell'efedrina esterificata aventi attivita' antiulcera prolungata nel tempo |
CA2087449A1 (en) * | 1990-08-13 | 1992-02-14 | Joseph L. Roba | Use of heterocyclic amino-alcohol compounds for treatment of cns diseases |
US5264459A (en) * | 1992-07-13 | 1993-11-23 | Arch Development Corporation | Use of β-adrenergic agonists to treat patients with demyelinating or autoimmune diseases |
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IL166149A0 (en) * | 2005-01-05 | 2006-01-15 | Hadasit Med Res Service | Use of ezetimibe and amiodarone in protection against beta-amyloid neurotoxicity |
EP2374508A1 (en) * | 2005-03-21 | 2011-10-12 | Vicus Therapeutics SPE 1, LLC | Combination of angiotension receptor blockers (ARB) and NSAIDs for use in ameliorating cachexia |
CA2604052C (en) * | 2005-04-06 | 2014-07-08 | Adamas Pharmaceuticals, Inc. | Methods and compositions for the treatment of cns-related conditions |
KR101355422B1 (ko) * | 2005-04-13 | 2014-02-06 | 아스션 팔마 에이/에스 | 피부 결합조직질환 치료용 베타-2 아드레노리셉터 작용제 |
GB0519274D0 (en) * | 2005-09-21 | 2005-11-02 | Arakis Ltd | The treatment of neurodegenerative diseases |
GB0526123D0 (en) * | 2005-12-22 | 2006-02-01 | Univ Gent | Synephrine derivatives useful as anti-inflammatory agents |
GB0604822D0 (en) * | 2006-03-09 | 2006-04-19 | Arakis Ltd | The treatment of inflammatory disorders and pain |
GB0604824D0 (en) * | 2006-03-09 | 2006-04-19 | Arakis Ltd | The treatment of inflammatory disorders |
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2006
- 2006-12-12 GB GBGB0624757.1A patent/GB0624757D0/en not_active Ceased
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2007
- 2007-12-12 BR BRPI0720284-9A patent/BRPI0720284A2/pt not_active IP Right Cessation
- 2007-12-12 US US12/517,272 patent/US20100076068A1/en not_active Abandoned
- 2007-12-12 CA CA002672238A patent/CA2672238A1/en not_active Abandoned
- 2007-12-12 CN CNA2007800458639A patent/CN101573325A/zh active Pending
- 2007-12-12 ZA ZA200903942A patent/ZA200903942B/xx unknown
- 2007-12-12 AU AU2007331337A patent/AU2007331337A1/en not_active Abandoned
- 2007-12-12 KR KR1020097014285A patent/KR20090088442A/ko not_active Application Discontinuation
- 2007-12-12 JP JP2009540849A patent/JP5225287B2/ja not_active Expired - Fee Related
- 2007-12-12 EP EP07848496A patent/EP2118050A2/en not_active Withdrawn
- 2007-12-12 MX MX2009006246A patent/MX2009006246A/es not_active Application Discontinuation
- 2007-12-12 EP EP12174501.2A patent/EP2518049A3/en not_active Withdrawn
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ZA200903942B (en) | 2010-08-25 |
JP2010512378A (ja) | 2010-04-22 |
BRPI0720284A2 (pt) | 2014-01-28 |
CA2672238A1 (en) | 2008-06-19 |
AU2007331337A1 (en) | 2008-06-19 |
EP2118050A2 (en) | 2009-11-18 |
IL199178A0 (en) | 2010-03-28 |
MX2009006246A (es) | 2009-07-16 |
EP2518049A2 (en) | 2012-10-31 |
CN101573325A (zh) | 2009-11-04 |
GB0624757D0 (en) | 2007-01-17 |
US20100076068A1 (en) | 2010-03-25 |
EP2518049A3 (en) | 2013-07-10 |
WO2008071948A3 (en) | 2008-07-31 |
KR20090088442A (ko) | 2009-08-19 |
WO2008071948A2 (en) | 2008-06-19 |
NO20092359L (no) | 2009-07-08 |
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