Nonpeptide Arginine Vasopressin Antagonists for Both V1A and V2 Receptors: Synthesis and Pharmacological Properties of 2-Phenyl-4'-(2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carbonyl)benzanilide Derivatives.

Matsuhisa, Akira; Koshio, Hiroyuki; Sakamoto, Kenichiro; Taniguchi, Nobuaki; Yatsu, Takeyuki; Tanaka, Akihiro

doi:10.1248/cpb.46.1566

Cited by 36 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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“…Dual V1a/V2 antagonistic behaviour was found in a series of tricyclic benzazepines, with the most prominent representative being YM-086 (42), reported to bind to V1a, V2 and OT-R with affinities of 1.2nM, 2.2nM, and 44nM, respectively [291]. Precursor compounds of YM-086 include 1,5-benzodiazepines, such as 43, again reported to bind also to OT-R in the low nanomolar range [292], and other related compounds [293,294,295], some of which have indeed been claimed as OT-R antagonists in one of the Yamanouchi patents [296]. V1a-specific antagonism was reported for a series of triazole compounds, exemplified by compound 44 [297,298], and although no specific data are disclosed, one would assume that several compounds of this series do exhibit activity at OT-R as well.…”

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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“…[2][3][4][5][6][7][8][9] Different triazepine derivatives have exhibited significant biological activities. [10][11][12][13] The area of biological interest of this family of compounds have been extended to various diseases such as cancer, 7 viral infections (HIV) 8 and cardiovascular disorders. 9,10 It is known that the pharmacological activity appears to be enhanced when a further heterocyclic ring is linked to the heptatomic nucleus.…”

Section: Introductionmentioning

confidence: 99%

“…[10][11][12][13] The area of biological interest of this family of compounds have been extended to various diseases such as cancer, 7 viral infections (HIV) 8 and cardiovascular disorders. 9,10 It is known that the pharmacological activity appears to be enhanced when a further heterocyclic ring is linked to the heptatomic nucleus. 14,15 They are reported as excellent ligands with transition metals inducing a large application in organometallic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Formation of pyrazol‐1,3,4‐thiadiazoles through 1,3‐dipolar cycloadditions of 3‐thioxo‐[1,2,4]‐triazepin‐5‐one with nitrilimines: an experimental and computational study

Esseffar¹,

Messaoudi²,

Azzouzi³

et al. 2008

J of Physical Organic Chem

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In this work the results of experimental and computational study of the title compounds and some ancillary compounds are reported. Two bicyclic pyrazol-1,3,4-thiadiazole derivatives were synthesized by reaction between 6-dimethylaminomethylene-3-thioxo-[1,2,4]-triazepin-5-one 1 and several nitrilimines 2a-f to give corresponding spirocycloadducts 3a-f, which undergo a rapid rearrangement leading to the new bicyclic compounds, 4a-f and 5a-f.These obtained bicyclic products were characterized by 1 H and 13 C NMR spectroscopy and finally by X-ray crystallography. Theoretical calculations have been carried out using DFT methods to rationalize the formation of the two new bicyclic compounds. Two reaction types are involved in the formation of the compounds 4a-f and 5a-f. The first one is a 1,3-dipolar cycloaddition reaction between 1 acting as dipolarophile and 2a-f as dipoles. The results indicate that the cycloaddition between 1 and 2g, as model of 2a-c, takes place via a high asynchronous bond-formation process. The regioselectivity obtained from the calculations is in complete agreement with the formation of the unique spirocycloadducts 3a-f. The second reaction leading to the formation of the final products is a domino process that is initiated by the quick and irreversible cleavage in a catalytic acid environment of triazepenic ring. Messaoudi 1975Messaoudi -2003 2 ¤ dedicated to the memory of Tourya El

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Nonpeptide Arginine Vasopressin Antagonists for Both V1A and V2 Receptors: Synthesis and Pharmacological Properties of 2-Phenyl-4'-(2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carbonyl)benzanilide Derivatives.

Cited by 36 publications

References 0 publications

Vasopressin antagonists

Vasopressin antagonists

Preterm Labour: An Overview of Current and Emerging Therapeutics

Formation of pyrazol‐1,3,4‐thiadiazoles through 1,3‐dipolar cycloadditions of 3‐thioxo‐[1,2,4]‐triazepin‐5‐one with nitrilimines: an experimental and computational study

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