5-fluoro-2-methyl-N-[5-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-yl carbonyl)-2-pyridinyl]benzamide (CL-385004) and analogs as orally active arginine vasopressin receptor antagonists

Aranapakam, Venkatesan; Albright, J. Donald; Grosu, G; Santos, Efren G. Delos; Chan, Peter S.; Coupet, Joseph; Ru, Xun; Saunders, Trina; Mazandarani, Hossein

doi:10.1016/s0960-894x(99)00279-6

Cited by 21 publications

(4 citation statements)

References 7 publications

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“…However, some of them do show selectivity for V1b receptors ( Table 1). Most of the compounds were characterized by receptor binding assays, and a few have already Benzazepine-furanilides (YM218) [46] Benzazepine-benzanilides [48] N-Methylbenzanilides [49] Triazoles [49] oxindoles [37][38][39] 2,5-disubstituted benzothiazepines [50] indoloazepines [51] benzodiazepine ring fused to a bridged bicyclic amine [53] quinoxaline (vp-343) [54] benzodiazepines [52,55] benzodiazepine ring fused to a bridged bicyclic amine [53] benzoazepines [22,45,47,55,56] thienoazepines [41] thiazepines and thiazines [57,58] Cell. Mol.…”

Section: Chemical Structure and Selectivity Of In Vivo And In Vitro Tmentioning

confidence: 99%

Vasopressin antagonists

Lemmens‐Gruber

Kamyar

2006

Cell. Mol. Life Sci.

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Effects of vasopressin via V1a- and V2-receptors are closely implicated in a variety of water-retaining diseases and cardiovascular diseases, including heart failure, hyponatraemia, hypertension, renal diseases, syndrome of inappropriate antidiuretic hormone secretion, cirrhosis and ocular hypertension. As vasopressin receptors are found in many different tissues, vasopressin antagonists may benefit the treatment of disorders such as cerebral ischaemia and stroke, Raynaud's disease, dysmenorrhoea and tocolytic treatment. V1b selective vasopressin antagonists are discussed in terms of their usefulness in the treatment of emotional and psychiatric disorders. The vaptans are vasopressin receptor antagonists with V1a (relcovaptan) or V2 (tolvaptan, lixivaptan) selectivity or non-selective activity (conivaptan) which may be advantageous in some disorders. The V1a/V2 non-selective vasopressin antagonist conivaptan is the first vaptan which is approved by the FDA for the treatment of euvolaemic hyponatraemia.

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Section: Chemical Structure and Selectivity Of In Vivo And In Vitro Tmentioning

confidence: 99%

Vasopressin antagonists

Lemmens‐Gruber

Kamyar

2006

Cell. Mol. Life Sci.

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“…(12)], exemplified by the prototype compound VPA-985 (48) [304] and variants thereof, such as 49 [305,306,307], reminiscent of Yamanouchi's YM-086 (42). These compounds are reported to be V1a/V2-antagonists, with varying degrees of V2-specificity, but OT-R activities are claimed and sometimes also disclosed in the corresponding patents [308].…”

Section: Non-peptide Antagonistsmentioning

confidence: 99%

Preterm Labour: An Overview of Current and Emerging Therapeutics

Schwarz¹,

Page²

2003

CMC

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Preterm labour is a major cause of perinatal mortality and morbidity. However, during the past 40 years of clinical studies and despite the use of multiple therapeutic agents, the rate of preterm birth has not drastically declined. In 1991, it was estimated that in the US approximately 116,000 women admitted with acute episodes of preterm labour were treated each year with ritodrine, which is the first drug approved by the US FDA and still remains the standard therapy for treating preterm labour. Ritodrine (Yutopar( trade mark )) stimulates the beta(2)-adrenergic receptor throughout the body, causing an inhibitory action in different tissues that, among other side effects, also leads to an attenuation of uterine contractility. More recently, a new therapeutic agent, atosiban (Tractocile( trade mark )), a peptidic oxytocin receptor antagonist, has been introduced to the market. However, the use of the various pharmacological agents to treat preterm labour remains restricted, due to lack of uterine selectivity, low efficacy and potentially serious side effects for the mother or the foetus. Therefore, there is an urgent need to develop drugs with myometrial selectivity that would allow long-lasting inhibition of labour and prolong pregnancy up to a stage when good foetal maturation raises the chances of survival. One of the major obstacles hampering the development of new therapeutic agents is the marked inter-species difference in terms of preterm labour physiology, which complicates the preclinical evaluation of new candidate molecules in animal models of disease. In this review, the authors will provide a comprehensive update of past, current and new approaches for the management of preterm labour, including beta(2)-adrenergic agonists, calcium channel blockers, oxytocin antagonists, prostaglandin antagonists and other potential therapeutics. For each of the therapies used today, the review will cover the mechanism of action, benefit and adverse effects, and discuss the promise and potential benefits of new emerging therapeutic agents.

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“…8 Some benzodiazepines showed activity as muscle relaxant, 9 anticoagulant, antiobesity, antiulcer, calcium channel blockers, 10 cholecystokinin antagonists, 11 endothelin antagonist, thrombopoietin receptor agonist, and vasopressin receptor antagonist. 12 Pyrimidines are extensively used as anticancer, 13 antiviral, 14 anti-mycobacterial, 15 anti-inflammatory, 16 analgesic, 17 antiallergic, 18 anti-HIV, 19 antimicrobial, anti-avian influenza virus (H5N1), 20 anti-arrhythmic, 21 serotonin 5-HT6 receptor antagonist, 22 hepatitis-A virus (HAV) and herpes simplex virus type-1 (HSV-1) inhibitor, 23 etc. Pyrimidine analogs have been also demonstrated anti-conceptive, platelet aggregation inhibitors, antagonists and anti-parkinson activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and molecular docking of pyrimidine incorporated novel analogue of 1,5-benzodiazepine as antibacterial agent

Misra

Sharma

et al. 2018

J Chem Sci

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A one-pot protocol involving nitrile-derived amidoxime of 1,5-benzodiazepine to synthesize its novel pyrimidine derivatives using DMAD and DABCO catalyst under microwave conditions has been described. The antibacterial activity of the synthesized compounds was examined against Gram-positive S. aureus and Gram-negative E. coli using broth micro-dilution assay. Low IC 50 values for the synthesized compounds indicated their potential as antibacterial agents. Further, field emission scanning electron microscopic study and cell membrane leakage study ascertained that the test compounds have ability to cause cell lysis via bacterial cell membrane rupture and disintegration. In addition, molecular docking studies suggested that test compounds may act through bacterial DHFR inhibition.

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5-fluoro-2-methyl-N-[5-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-yl carbonyl)-2-pyridinyl]benzamide (CL-385004) and analogs as orally active arginine vasopressin receptor antagonists

Cited by 21 publications

References 7 publications

Vasopressin antagonists

Vasopressin antagonists

Preterm Labour: An Overview of Current and Emerging Therapeutics

Synthesis and molecular docking of pyrimidine incorporated novel analogue of 1,5-benzodiazepine as antibacterial agent

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