CAS: 249296-44-4; 7,8,9,10-Tetrahydro-6H-6,10-Methanoazepino[4,5-G]Quinoxaline

英文名称7,8,9,10-Tetrahydro-6H-6,10-Methanoazepino[4,5-G]Quinoxaline
中文名称伐伦克林
IUPAC名称7,8,9,10-tetrahydro-6H-6,10-methanoazepino[4,5-g]quinoxaline
其它别名Imidazo(2,1-B)Thiazole, 2,3,5,6-Tetrahydro-6-Phenyl-, (6S)-; 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]Hexadeca-2,4,6,8,10-Pentaene; 5,8,14-Triazatetracyclo[10.3.1.0^{2,11}.0^{4,9}]Hexadeca-2(11),3,5,7,9-Pentaene; 7,8,9,10-Tet
CAS编号249296-44-4
MFCD编号:MFCD10001497
EINECS号:810-384-9
FDA UNII编号:W6HS99O8ZO
分子式:C13H13N3
分子量:211.27
产品CID: 1202702
同类组份化合物CAS375815-87-5 (tartrate)866823-63-4 (HCl)249296-44-4 (free base)
产品分类生物化工 → 生化试剂 → 激动剂抑制剂

相似结构搜索
InChIKey: JQSHBVHOMNKWFT-UHFFFAOYNA-N
InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2…
计算化学: 氢键受体数3.0氢键供体数1.0可旋转键数0.0

物理性质

熔点138.5 °C
沸点400.6±40.0 °C(预测)
闪点196.1°C
密度1.247±0.06 g/cm3(预测)
pKa:9.60±0.20(预测)
PSA:152.87
LogP:0.8
折射率1.667
蒸汽压4.65X10-6 mm Hg at 25 °C (est)
溶解性Soluble In DMSO
外观形态淡黄色至黄色粉末
储存条件储存在 -20°C
产品应用该化合物用作戒烟的尼古丁乙酰胆碱受体部分刺激剂; 通过部分激活Α4Β2乙基乙酰乙酰碱受药体,同时阻塞尼古汀装药,减少尼古提尼的渴望和戒烟症状,从而增加戒烟率,减少复发.

MSDS等安全信息

警示词Danger
危险描述H302-H319-H372-H410-
防范说明P273-P301+P312+P330-P305+P351+P338-P314-
UN编号3077
安全声明IDENTIFICATION AND USE: Varenicline is used as an adjunct in the cessation of cigarette smoking. HUMAN EXPOSURE AND TOXICITY: Safety and efficacy of varenicline as an adjunct for smoking cessation have been established in 6 placebo-controlled or active-comparator studies in 3659 patients (mean age: 43 years; 79-96% white; mean smoking history: about 25 years) who smoked at least 10 cigarettes daily (mean: about 21 cigarettes daily). Safety and efficacy of varenicline also have been evaluated in a randomized, double-blind, placebo-controlled study in 703 patients with stable, documented cardiovascular disease (other than hypertension) who smoked at least 10 cigarettes daily; patients receiving varenicline and placebo were comparable in baseline characteristics, including age (mean age 57 and 55.9 years, respectively), race (80.3 and 80.8% white, respectively), gender (75.2 and 82.2% male, respectively), and mean smoking history (40 and 39 years, and 22.1 and 22.9 cigarettes daily, respectively). Safety and efficacy of varenicline also have been evaluated in a randomized, double-blind, placebo-controlled study in 460 patients (mean age 57 years, 82-84% white, approximately 62% male, mean smoking history of approximately 40 years) with mild to moderate chronic obstructive pulmonary disease (postbronchodilator FEV1/FVC below 70% and FEV1 at least 50% of predicted normal value) who smoked at least 10 cigarettes daily. Serious neuropsychiatric symptoms, including changes in mood (e.g., depression, mania), psychosis, hallucinations, paranoia, delusions, homicidal ideation, hostility, agitation, aggression, anxiety, panic, and suicidality (e.g., suicidal ideation, attempted and completed suicides), have been reported during postmarketing experience in patients receiving varenicline. Hypersensitivity reactions, including angioedema, have been reported during postmarketing experience in patients receiving varenicline. Safety and efficacy of varenicline have not been established in patients younger than 18 years of age and use of the drug in this age group is not recommended. Varenicline was not genotoxic, with or without metabolic activation in vitro in human lymphocytes. ANIMAL STUDIES: Varenicline is distributed into milk in animals. Rats were administered varenicline (1, 5, and 15 mg/kg/day) by oral gavage for 2 years. In male rats (n = 65 per sex per dose group), incidences of hibernoma (tumor of the brown fat) were increased at the mid dose (1 tumor, 5 mg/kg/day, 23 times the maximum recommended human daily exposure based on AUC) and maximum dose (2 tumors, 15 mg/kg/day, 67 times the maximum recommended human daily exposure based on AUC). There was no evidence of carcinogenicity in female rats. Varenicline succinate has been shown to have an adverse effect on the fetus in animal reproduction studies. Administration of varenicline succinate to pregnant rabbits resulted in reduced fetal weights at an oral dose of 30 mg/kg/day (50 times the human AUC); this reduction was not evident following treatment with 10 mg/kg/day (23 times the maximum recommended daily human exposure based on AUC). In addition, in the offspring of pregnant rats treated with varenicline succinate there were decreases in fertility and increases in auditory startle response at an oral dose of 15 mg/kg/day (36 times the maximum recommended human daily exposure based on AUC). Varenicline succinate was not teratogenic in rats and rabbits at oral doses up to 15 and 30 mg/kg/day, respectively (36 and 50 times the maximum recommended human daily exposure based on AUC, respectively). Varenicline was not genotoxic, with or without metabolic activation, in the following assays: Ames bacterial mutation assay; mammalian CHO/HGPRT assay; and tests for cytogenetic aberrations in vivo in rat bone marrow. | Signs and Symptoms of Overdose | Evaluation of prolonged exposure to varenicline in adults has not revealed any alteration of hematological, biochemical, and anatomicopathological parameters. High doses of varenicline, whether ingested intentionally or accidentally, can result in several symptoms. One notable effect is spontaneous vomiting, likely due to the drug's action on gastrointestinal 5-HT3 receptors. Additionally, transient blood pressure and heart rate increases may occur. | Management of Overdose | If there are serious adverse effects, including psychiatric conditions or skin hypersensitivity reaction, discontinue varenicline immediately. Varenicline therapy can be stopped abruptly with no adverse effects, and there is no need for a taper. There are currently no antidotes to varenicline. Varenicline is removed by dialysis in patients with end-stage renal disease; however, there is no experience in dialysis following an overdose. | Varenicline is an alpha-4 beta-2 neuronal nicotinic acetylcholine receptor partial agonist. The drug shows high selectiviyty for this receptor subclass, relative to other nicotinic receptors (>500-fold alpha-3 beta-4, >3500-fold alpha-7, >20,000-fold alpha-1 beta gamma delta) or non-nicotinic receptors and transporters (>2000-fold). The drug competitively inhibits the ability of nicotine to bind to and activate the alpha-4 beta-2 receptor. The drug exerts mild agonistic activity at this site, though at a level much lower than nicotine; it is presumed that this activation eases withdrawal symptoms.

上下游产品

7,8,9,10-四氢-8-(三氟乙酰基)-6,10-甲桥-6H-吡嗪并[2,3-H][3]苯并氮杂卓 1-(9,10-Dihydro-6H-6,10-Methanoazepino[4,5-G]Quinoxaline-8(7H)-yl)-2,2,2,-Trifluoroethanone 230615-70-0

合成工艺路线路线简述

合成目标产物 Varenicline 主要起始原料 Ethanamine, N-[(3,5-Dichlorophenyl)Methylene]-2,2-Diethoxy-
(文献来源)合成步骤主要原料 Ethanamine, N-[(3,5-Dichlorophenyl)Methylene]-2,2-Diethoxy-

N-Benzylvarenicline置于palladium 10% On Activated Carbon,氢气体系中,用甲醇用作溶剂,化学反应 3.0H,以90%的收率获得伐伦克林
参考文献:伐尼克兰的合成方法
标题:伐尼克兰的合成方法
摘要:本发明涉及一种制备伐尼克兰或其药学上可接受的盐的工艺.本发明还涉及在此过程中有用的中间化合物和这种中间化合物的制备.

海关参考信息

2902600000-乙苯
2902700000-异丙基苯
2921199090-其他无环单胺
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详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-7205300-B2
优先权日:1997-12-31
标题:Aryl fused azapolycyclic compounds
发明人：COE JOTHAM WADSWORTH; BROOKS PAIGE ROANNE PALMER
权利人:PFIZER
摘要:This invention is directed to compounds of the formula (I): n nand their pharmaceutically acceptable salts, wherein R 1 , R 2 , and R 3 are as defined herein; intermediates for the synthesis of such compounds, pharmaceutical compositions containing such compounds; and methods of using such compounds in the treatment of neurological and psychological disorders.

专利号:US-2012004239-A1
优先权日:2010-06-11
标题 :Process for Preparing Quinoxaline Derivatives
发明人：SOLDEVILLA MADRID NURIA; VAZQUEZ MARTINEZ MANEL
权利人:SOLDEVILLA MADRID NURIA; VAZQUEZ MARTINEZ MANEL; MEDICHEM SA
摘要:The present invention provides an improved process for preparing a compound of formula (IIIA), an intermediate of the synthesis of varenicline. Also, the present invention provides an improved process for preparing varenicline, or a pharmaceutically acceptable salt or solvate thereof. Furthermore, the present invention provides a process for decolorizing varenicline, or a salt or solvate thereof. Still further, the present invention provides a process of preparing varenicline L-tartrate with improved yield. Still further, the present invention relates to the use of compound of formula (V), or a salt or solvate thereof, as a reference marker and reference standard for assessing the purity of varenicline, or a salt or solvate thereof.

专利号:WO-2009065872-A2
优先权日:2007-11-20
标题 :Improved processes for the synthesis of varenicline l-tartrate

专利号:US-6858624-B2
优先权日:2001-11-30
标题:Aryl fused azapolycyclic compounds
发明人：HAGEN ANNE E; OBACH R SCOTT
权利人:PFIZER; PFIZER PROD INC
摘要:This invention is directed to compounds of the formula (I): n n nand their pharmaceutically acceptable salts, wherein R 1 , R 2 , and R 3 are as defined herein; intermediates for the synthesis of such compounds, pharmaceutical compositions containing such compounds; and methods of using such compounds in the treatment of nicotine addiction/withdrawal and CNS disorders.

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主要参考文献

1: Anthenelli RM, Benowitz NL, West R, St Aubin L, McRae T, Lawrence D, Ascher J, Russ C, Krishen A, Evins AE. Neuropsychiatric safety and efficacy of varenicline, bupropion, and nicotine patch in smokers with and without psychiatric disorders (EAGLES): a double-blind, randomised, placebo-controlled clinical trial. Lancet. 2016 Jun 18;387(10037):2507-20. doi: 10.1016/S0140-6736(16)30272-0. Epub 2016 Apr 22. 333(21):1876-1886. doi: 10.1001/jama.2025.3810.
3: Cinciripini PM, Green CE, Shete S, Minnix JA, Robinson JD, Cui Y, Kim S, Kypriotakis G, Beneventi D, Blalock JA, Versace F, Karam-Hage M. Smoking Cessation After Initial Treatment Failure With Varenicline or Nicotine Replacement: A Randomized Clinical Trial. JAMA. 2024 May 28;331(20):1722-1731. doi: 10.1001/jama.2024.4183.
4: Correia C, Fernandes S, Correia T, Soares-de-Almeida L, Filipe P. Varenicline-induced drug eruption: case and review of the literature. Dermatol Online J. 2023 Feb 15;29(1). doi: 10.5070/D329160217. 2025 Jan–. 82(14):1481-1488. doi: 10.1007/s40265-022-01782-4. Epub 2022 Oct 5.

合成参考文献

参考文献:10.1253/circj.cj-09-0803
摘要:Tsukahara H, Noda K, Saku K. A randomized controlled open comparative trial of varenicline vs nicotine patch in adult smokers: efficacy, safety and withdrawal symptoms (the VN-SEESAW study). Circ J. 2010 Apr;74(4):771–8. doi: 10.1253/circj.cj-09-0803.
参考文献:10.1016/j.genhosppsych.2011.05.008
摘要:Knibbs N, Tsoi DT. Varenicline induces manic relapse in bipolar disorder. Gen Hosp Psychiatry. 2011 Nov;33(6):641.e1–2. doi: 10.1016/j.genhosppsych.2011.05.008.
参考文献:10.2147/clep.s16526
摘要:Mills EJ, Bansback N, Ghement I, Thorlund K, Kelly S, Puhan MA, Wright J. Multiple treatment comparison meta-analyses: a step forward into complexity. Clin Epidemiol. 2011;3():193–202.
参考文献:10.1016/j.pbb.2011.07.001
摘要:Wildeboer-Andrud KM, Stevens KE. The smoking cessation drug varenicline improves deficient P20–N40 inhibition in DBA/2 mice. Pharmacology Biochemistry and Behavior. 2011 Nov;100(1):17–24. doi: 10.1016/j.pbb.2011.07.001.
参考文献:10.1124/jpet.111.185306
摘要:Lummis SCR, Thompson AJ, Bencherif M, Lester HA. Varenicline Is a Potent Agonist of the Human 5-Hydroxytryptamine3 Receptor. The Journal of Pharmacology and Experimental Therapeutics. 2011 Oct;339(1):125–31. doi: 10.1124/jpet.111.185306.