CAS: 51037-30-0; 5-Carboxy-2-Methylpyrazine 1-Oxide

该化合物是一种主要用作脂质低效剂的药物化合物,特别是在管理糖尿病方面,它属于被称为乙酰衍生物和功能的药物类别,禁止从脂肪组织释放免费脂肪酸,从而减少肝脏中三甘酸和低密度脂蛋白胆固醇的合成;Acipimox的特征是它能够改进脂质特征,从而减少心血管疾病的风险;该化合物一般是口服的,并因其相对其他脂质低效剂而言相对有利的副作用而著称;其行动机制还包括加强脂质脂质脂质的活性,这种活性能有助于三甘油酸分解; 氮质经常与生活方式的改变(如饮食和锻炼)相结合,以取得最佳的治疗结果; 与任何药物一样,病人必须咨询保健专业人员,以便适当施用和可能与其他药物相互作用.

结构式图片

相似化合物

2423-65-6 94777-24-9 58091-57-9

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

5-methyl-pyrazin-2-carboxamide-4-oxide 5‐methylpyrazine-2-carboxamide 2-methylpyrazin-5-carboxylic acid dihydrogen peroxide 5-Methyl-4-oxy-pyrazine-2-carboxylic acid 2,2-dimethyl-6-[4-(4-phenyl-butyl)-phenoxy]-hexyl ester 2-methoxymethyl-5-methylpyrazine-4-oxide

合成工艺路线路线简述

  • 合成目标产物 Acipimox 主要起始原料 5-Methyl-2-Pyrazinecarboxylic Acid
  • (文献来源)合成步骤主要原料 5-Methyl-2-Pyrazinecarboxylic Acid
5-Methylpyrazinecarboxylic Acid-4-Oxide Ethyl Ester置于sodium Hydroxide体系中,用 乙酸乙酯 作为反应溶剂,化学反应生成 阿西莫司
参考文献:Pyrazine 4-Oxide Derivatives And Process For Their Preparation
标题:Pyrazine 4-Oxide Derivatives And Process For Their Preparation
摘要:公式(i)##str1##的化合物已被披露,其中至少有一个r.Sup.1,R.Sup.2和r.Sup.3是c.Sub.1.Sub.-6烷基,其他是氢原子;r.Sup.4是羟基或c.Sub.1.Sub.-6烷氧基,或者是化合物的盐,其中r.Sup.4是羟基,与药用上可接受的碱.一个典型的化合物是,例如,2-羧基-5-甲基吡嗪-4-氧化物.这些化合物表现出降糖和降脂活性.

海关参考信息

专利信息


专利号:US-5091066-A
优先权日:1987-11-19
标 题 :Electrochemical synthesis of 2-methyl-5-pyrazinoic acid
发明人:FOA MARCO; FORLINI FABRIZIO; GATTI NORBERTO; BORSOTTI GIAMPIERO
权利人:MINI RICERCA SCIENT TECNOLOG
摘要:There is disclosed a process for the preparation of 2-methyl-5-pyrazinoic acid consisting of electrochemically oxidizing a compound having formula: ##STR1## wherein X is --OH, Cl, Br, --O--CO--R, --O--SO 2 --R, in which R is a C 1 -C 5 alkyl radical, optionally substituted with F or Cl, or it is a C 6 -C 12 aryl radical, in an aqueous alkaline medium, at a temperature ranging from 20° C. to 90° C., using anodes coated with nickel oxide-hydroxide.

专利号:US-7956214-B2
优先权日:2001-11-02
标题 :Process for the preparation of aniline-derived thyroid receptor ligands
发明人:CHIDAMBARAM RAMAKRISHNAN; KANT JOYDEEP; WEAVER RAYMOND E; YU JURONG; GHOSH ARUN
权利人:KAROBIO AB; BRISTOL MYERS SQUIBB CO
摘要:Provided are processes for the synthesis of aniline derivatives, specifically certain aniline derivatives which have activity as thyroid receptor ligands.

专利号:US-7612106-B2
优先权日:2004-12-23
标题 :Fused pyrazole derivatives and methods of treatment of metabolic-related disorders thereof
发明人:BOATMAN P DOUGLAS; SCHRADER THOMAS O; SEMPLE GRAEME; SKINNER PHILIP J; JUNG JAE-KYU
权利人:ARENA PHARM INC
摘要:The present invention relates to certain fused pyrazole derivatives of Formula (Ia), and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists for the RUP25 receptor. n nAlso provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of α-glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers, DP receptor antagonists, and the like.

专利号:US-8637555-B2
优先权日:2003-10-31
标题:Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof
发明人:SEMPLE GRAEME; SCHRADER THOMAS; SKINNER PHILIP J; COLLETTI STEVEN L; GHARBAOUI TAWFIK; IMBRIGLIO JASON E; JUNG JAE-KYU; LIANG RUI; RAGHAVAN SUBHAREKHA; SCHMIDT DARBY; TATA JAMES R
权利人:SEMPLE GRAEME; SCHRADER THOMAS; SKINNER PHILIP J; COLLETTI STEVEN L; GHARBAOUI TAWFIK; IMBRIGLIO JASON E; JUNG JAE-KYU; LIANG RUI; RAGHAVAN SUBHAREKHA; SCHMIDT DARBY; TATA JAMES R; ARENA PHARM INC; MERCK & CO INC
摘要:The present invention relates to certain tetrazole derivatives of Formula (I), and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists for the RUP25 receptor. n nAlso provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of α-glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like.

专利号:US-10968192-B2
优先权日:2018-09-26
标题:Crystalline solid forms of N-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)butanamide and methods of their synthesis
发明人:BEDNARZ MARK STEPHEN; Dai Kuangchu; ECKERT JEFFREY MANNING; LIM NGIAP-KIE; SIROIS LAUREN; WU WENXUE; ZHAO MATTHEW MANGZHU
权利人:LEXICON PHARMACEUTICALS INC
摘要:Methods of preparing, and solid forms of N-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)butanamide, and salts, solvates and cocrystals thereof, are disclosed.

专利号:EP-1551403-B1
优先权日:2002-10-10
标 题 :5-substituted 2h-pyrazone-3-carboxylic acid derivatives as antilipolytic agents for the treatment of metabolic-related disorders such as dyslipidemia
发明人:SEMPLE GRAEME; AVERBUJ CLAUDIA; SKINNER PHILIP; GHARBAOUI TAWFIK; SHIN YOUNG-JUN
权利人:ARENA PHARM INC
摘要:The present invention relates to certain pyrazole carboxylic acid derivatives of Formula (Ia), and pharmaceutically acceptable salts thereof, as antilipolytic agents and against for the receptor RUP25, wherein: R2 is H, halogen, C1-12 alkyl or C1-12 haloalkyl; and R3 is C3-6 cycloalkyl, C1-12 alkyl, C1-12 haloalkyl, C3-6 cycloalkyl-C1-4-alkylene, aryl-C1-4-alkylene or heteroaryl-C1-4-alkylene, wherein said aryl-C1-4-alkylene and heteroaryl-C1-4-alkylene can be optionally substituted 1 to 5 substituents selected from the substituents listed in the claims. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for pharmaceutical compositions in combination with other active agents, for example, those agents belonging to the class of alpha-glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers, thiazolidinedione and the like.
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主要参考文献


1: Mori M, Supuran CT. Acipimox inhibits human carbonic anhydrases. J Enzyme Inhib Med Chem. 2022 Dec;37(1):672-679. doi: 10.1080/14756366.2022.2037579.
2: Acipimox--a nicotinic acid analogue for hyperlipidaemia. Drug Ther Bull. 1991 Jul 22;29(15):57-9. 115(48):12158-12163. doi: 10.1073/pnas.1808855115. Epub 2018 Nov 14.
4: Vestergaard ET, Hjelholt AJ, Kuhre RE, Møller N, Larraufie P, Gribble FM, Reimann F, Jessen N, Holst JJ, Jørgensen JOL. Acipimox Acutely Increases GLP-1 Concentrations in Overweight Subjects and Hypopituitary Patients. J Clin Endocrinol Metab. 2019 Jul 1;104(7):2581-2592. doi: 10.1210/jc.2018-02503.

合成参考文献


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参考文献:10.1002/(sici)1099-0895(199603)12:1<15::aid-dmr153>3.0.co;2-0|10.1002/(sici)1099-0895(199603)12:1<15::aid-dmr153>3.3.co;2-s|10.1002/(sici)1099-0895(199603)12:1<15::aid-dmr155>3.0.co;2-0
摘要:Saloranta C, Groop L. Interactions between glucose and FFA metabolism in man. Diabetes Metab Rev. 1996 Apr;12(1):15–36. doi: 10.1002/(sici)1099-0895(199603)12:1<15::aid-dmr153>3.0.co;2-0.
参考文献:10.1007/bf03349871
摘要:Maccario M, Grottoli S, Procopio M, Oleandri SE, Barberis A, Ciccarelli E, Camanni F, Ghigo E. Effect of bromocriptine on insulin, growth hormone and prolactin responses to arginine in obesity. Journal of Endocrinological Investigation. 1996 Apr;19(4):219–23. doi: 10.1007/bf03349871.
参考文献:10.2165/00128071-200203010-00007|10.2165/00128071-200203020-00006|10.2165/00128071-200203030-00008|10.2165/00128071-200203040-00007|10.2165/00128071-200203050-00008|10.2165/00128071-200203060-00007|10.2165/00128071-200203070-00009|10.2165/00128071-200203080-00010|10.2165/00128071-200203090-00006
摘要:Cutaneous drug reaction case reports: from the world literature. Am J Clin Dermatol. 2002;3(9):637–43. doi: 10.2165/00128071-200203090-00006.
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