cas 461-72-3, Hydantoin | Articles data

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Regioselective reactions of N-(carboxyalkyl)- and N-(aminoethyl)ureas with glyoxal and 1,2-dioxo-1,2-diphenylethane
Regioselective reactions of N-(carboxyalkyl)ureas (ureido acids) and N-(aminoethyl)ureas with 1,2-dioxo-1,2-diphenylethane (benzyl) and glyoxal are studied in detail. The structure of the reactants affects the reaction regioselectivity. Acid-catalyzed rea
Kravchenko,Baranov,Gazieva,Chikunov,Nelyubina
(2014)
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Synthesis of (S)-N-hydantoinoalkylglycoluriles by one-pot double cyclisation of chiral α,ω-diureido acids under the action of 4,5-dihydroxyimidazolidin-2-ones
The reaction of 4,5-dihydroxyimidazolidin-2-ones with chiral (S)-N, N'-dicarbamoyl-α,ω,-amino acids occurs as one-pot double cyclisation under acid catalysis to give the corresponding glycoluriles with (S)-N-hydantoinoalkyl substituents.
Chikunov, Il'ya E.,Kravchenko, Angelina N.,Belyakov, Pavel A.,Lebedev, Oleg V.,Makhova, Nina N.
p. 67 - 69
(2005)
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The first synthesis of assemblies of imidazolidine rings by α-ureidoalkylation of imidazolidin-2-one with 4,5-dihydroxyimidazolidin-2- ones
The synthesis of assemblies of imidazolidine rings has been developed based on the α-ureidoalkylation of imidazolidin-2-one with 4,5- dihydroxyimidazolidin-2-ones.
Sigachev, Andrey S.,Kravchenko, Angelina N.,Maksareva, Elena Yu.,Lozhkin, Boris V.,Lyssenko, Konstantin A.,Makhova, Nina N.
p. 80 - 82
(2006)
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α-Ureidoalkylation of thiosemicarbazide and aminoguanidine
Optimum conditions for the targeted synthesis of 5,7-dialkyl-3- thioxoperhydroimid-azo[4,5-e][1,2,4]triazin-6-ones, 4,5-bis(3- thiosemicarbazido(guanidinoamino))imidazolidin-2-ones, and 1,3-dialkyl-4- (guanidinoimino)imidazolidin-2-ones by α-ureidoalkylation of thiosemicarbazide or aminoguanidine were found. A novel conglomerate in the series of imidazolidin-2-one derivatives was detected: 4,5-bis(guanidinoamino)- 1,3-dimethylimid-azolidin-2-one dihydrochloride dihydrate. Springer Science+Business Media, Inc. 2006.
Sigachev,Kravchenko,Belyakov,Lebedev,Makhova
p. 865 - 872
(2006)
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Efficient Synthesis of Tetraacetylglycoluril in the Presence of Phosphorus-Containing Catalysts
Abstract: The effect of phosphorus-containing catalysts, namely phosphorous acid, phosphoric acid, diethyl hydrogen phosphite, and 1-hydroxyethane-1,1-diyldiphosphonic acid (HEDP), in the synthesis of tetraacetylglycoluril by acylation of glycoluril with acetic anhydride at 140°C has been studied. The use of 4 equiv of phosphorous or phosphoric acid with respect to glycoluril has been found to be the most appropriate for achieving the maximum yield (95–98%), and specific effect of HEDP leads to N-acetylation–deacetylation of substrates. The positive effect of phosphorus acids on the formation of tetraacetylglycoluril may be related to not only their catalytic action but also the ability to solubilize the substrate.
Bakibaev,Panshina, S. Yu.,Hoang,Kurgachev,Ukhov,Malkov,Zhumanov
p. 58 - 63
(2021/03/03)

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2-dicarbonyl compounds using etidronic acid as a “green catalyst”
Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as “Green catalyst.” So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80°C-90°C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.
Bakibaev, Abdigali A.,Uhov, Artur,S. Malkov, Victor,Yu. Panshina, Svetlana
p. 4262 - 4270
(2020/10/02)

Method for continuous co-production of glycine and hydantoin
A method for continuous co-production of glycine and hydantoin is provided. The method includes subjecting an amino source, a carbon source, water and hydroxyacetonitrile to a hydantoin synthesizing reaction in a shell-and-tube reactor to obtain a first reaction product; feeding the first reaction product into a flash column for treatment to obtain a first treatment product; dividing the first treatment product into a first portion and a second portion; subjecting the first portion to first concentration treatment in an evaporator to obtain a first concentrate; reacting the first concentrate with concentrated sulfuric acid to obtain a second reaction product including hydantoin; subjecting the second portion to hydantoin decomposition in a tank series reactor to obtain a third reaction product including glycine. Compared with the prior art, the method realizes the continuous co-production of the glycine and the hydantoin.
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Paragraph 0047-0052

(2019/07/16)

Method for synthesizing 1-isopropyl benzamide-3-(3,5-dichlorophenyl)hydantoin
The invention discloses a method for synthesizing 1-isopropyl benzamide-3-(3,5-dichlorophenyl)hydantoin. The method comprises the following steps: reacting by virtue of chloroacetyl chloride and urea in the presence of a catalyst, so as to prepare hydantoin; reacting by virtue of hydantoin and 1,3,5-trichlorobenzene in the presence of triethylamine, so as to prepare 3,5-dichlorophenyl-hydantoin; and reacting by virtue of 3,5-dichlorophenyl-hydantoin and isopropyl isocyanate in the presence of a catalyst, so as to prepare 1-isopropyl benzamide-3-(3,5-dichlorophenyl)hydantoin. According to a reaction route utilized in the method, an expensive raw material 3,5-dichloroaniline and a highly toxic raw material phosgene are not adopted, and the method has the characteristics of few reaction steps, less waste gas, wastewater and industrial residue, high product yield and good product quality as well as obvious economic and social benefits.
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Paragraph 0021; 0023

(2016/11/14)

Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound
The invention belongs to the field of medicines and in particular relates to a compound with the structure of a formula I, a stereomer of the compound or pharmaceutically acceptable salts of the compound as well as a preparation method of the compound and application of the compound to preparation of anti-tumor medicines. A pharmacological experiment result shows that the compound can be used for inhibiting the activity of NEDD8 kinase and has the inhibition effect on proliferation of a plurality of types of tumor cells, so that the compound can be used as an NEDD8 kinase activity inhibitor for preparing the anti-tumor medicines. The formula I is shown in the description.
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Paragraph 0095; 0096; 0097

(2016/10/10)

Meteorites as catalysts for prebiotic chemistry
From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.
Saladino, Raffaele,Botta, Giorgia,Delfino, Michela,Di Mauro, Ernesto
p. 16916 - 16922
(2014/01/06)

Dibutylphosphate (DBP) mediated synthesis of cyclic N,N′- disubstituted urea derivatives from amino esters: A comparative study
The N,N′-disubstituted urea derivatives such as amino acid hydantoins and dihydrouracil derivatives were prepared starting from natural and unnatural amino acid esters using dibutylphosphate (DBP). During the attempted synthesis of N-heterocycles with larger than six-membered rings containing the N,N′-disubstituted urea functionalities, three unexpected products namely squamolone, N-methyl pyrrolidine-2-one, and diketopiperazine were isolated.
Agrawal, Sumit K.,Sathe, Manisha,Kaushik, M. P.,Halve, A. K.
supporting information
p. 5996 - 5999,4
(2020/08/20)

Synthesis and evaluation of anti-inflammatory and antitussive activity of hydantion derivatives
1-Methylhydantion is a compound, which was isolated from Oviductus Ranae for the first time. In our study, we found that it showed good antitussive and anti-inflammatory activity. It is also the first report which illustrates the antitussive activity of hydantion derivative. A series of hydantion derivatives were synthesized and evaluated for their anti-inflammatory and antitussive activity in vivo. The pharmacological tests showed that compounds 7a, 7c and 7d have good anti-inflammatory and antitussive activity compared to Ibuprofen and codeine. Compound 7a in particular showed two-fold stronger anti-inflammatory activity than Ibuprofen.
Lu, Haibin,Kong, Dejuan,Wu, Bin,Wang, Shihan,Wang, Yongsheng
experimental part
p. 638 - 642
(2012/08/28)

α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols
Acid-catalyzed reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5- dihydroxy-4,5-diphenylimidazolidine- 2-thiones in methanol or propan-2-ol led to the formation of previously unknown ω-(4,6-dialkyl- 2-oxo-3a,6a-diphenyl- 5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)alkanoic acids and their methyl and isopropyl esters. The structure of some esters was proved by X-ray analysis. Methyl (4,6-diethyl-2-oxo-3a,6adiphenyl- 5-thioxooctahydroimidazo[4,5-d] imidazol-1-yl)acetate showed anxiolytic effect. Pleiades Publishing, Ltd., 2011.
Baranov,Gazieva,Nelyubina,Kravchenko,Makhova
experimental part
p. 1564 - 1571
(2012/03/10)

Facile synthesis of hydantoins and thiohydantoins in aqueous solution
A series of hydantoins and thiohydantoins have been synthesized in water at room temperature from urea (or N-methylurea, or thiourea) and simple aldehydes (as glyoxal, and its simple derivatives) in the presence of phosphoric anhydride. The reaction time is 10 min using an equimolar amount of P 4O10 with respect to the other reagents, but the reaction occurs also, even if with longer reaction times, with very small amounts of P4O10. In addition, this method provides a clean and 'green' approach to hydantoins, compounds of great interest in biological and pharmacological fields.
Baccolini, Graziano,Boga, Carla,Delpivo, Camilla,Micheletti, Gabriele
experimental part
p. 1713 - 1717
(2011/05/05)

4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxyalkyl-, N-hydroxyalkyl-, and N-(aminoalkyl)ureas 4.* α-Ureidoalkylation of N-(2-acetylaminoethyl)ureas
α-Ureidoalkylation of N-(2-acetylaminoethyl)ureas with various 4,5-dihydroxyimidazoli- din-2-ones was systematically studied. Novel N-(2-acetylaminoethyl)glycolurils were obtained. Their yields were found to decrease both when moving from 1,3-H2- to 1,3-Alk2-4,5- dihydroxy- imidazolidin-2-ones and when increasing the size of the substituent at the second N atom in the starting acetylaminoethylurea. The higher yields were achieved with 4,5-diphenyl-4,5- dihydroxyimidazolidin-2-one as the starting compound. 2-(2-Acetylaminoethyl)-4-methylgly- coluril exhibits nootropic activity.
Gazieva,Lozhkin,Baranov,Kravchenko,Makhova
experimental part
p. 642 - 646
(2011/02/16)

Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction
Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)- diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly; beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199.62%) for (M14) Melanoma cells was observed at the tested concentration (10?μM). ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.
El-Deeb, Ibrahim M.,Bayoumi, Said M.,El-Sherbeny, Magda A.,Abdel-Aziz, Alaa A.-M.
scheme or table
p. 2516 - 2530
(2010/07/05)

New polyamides based on 1,3-bis(4-carboxy phenoxy) propane and hydantoin derivatives: Synthesis and properties
Six new polyamides 5a-f containing flexible trimethylene segments in the main chain were synthesized through the direct polycondensation reaction of 1,3-bis(4-carboxy phenoxy) propane 3 with six derivatives of hydantoins 4a-f in a medium consisting of N-methyl-2-pyrrolidone, triphenyl phosphite, calcium chloride and pyridine. The polycondensation reaction produced a series of novel polyamides in high yield with inherent viscosities between 0.30-0.47 dL/g. The resulted polymers were fully characterized by means of FT-IR, 1H-NMR spectroscopy, elemental analyses, inherent viscosity, solubility tests and gel permeation chromatography (GPC). Thermal properties of these polymers were investigated by using thermal gravimetric analysis (TGA) and differential thermal gravimetry (DTG). The glass-transition temperatures of these polyamides were recorded between 130 and 155 °C by differential scanning catorimetry (DSC), and the 5% weight loss temperatures were ranging from 325 to 415 °C under nitrogen. 1,3-bis(4-Carboxy phenoxy) propane 3 was prepared from the reaction of 4-hydroxy benzoic acid 1 with 1,3-dibromo propane 2 in the presence of NaOH solution.
Faghihi, Khalil,Valikhani, Nasim
experimental part
p. 77 - 83
(2010/12/19)

Assembly/disassembly of drug conjugates using imide ligation
A strategy is described that allows the easy assembly and controlled disassembly of drug conjugates. Imide ligation, that is, the reaction of a peptide thioacid with an azidoformate, is used for conjugate assembly. The imide bond participates also with an endopeptidase-triggered cyclization-based disassembly mechanism.
Mhidia, Reda,Beziere, Nicolas,Blanpain, Annick,Pommery, Nicole,Melnyk, Oleg
supporting information; experimental part
p. 3982 - 3985
(2010/11/02)

4,5-Dihydroxyimidazolidin-2-ones in a-ureidoalkylation of N-carboxy-, N-hydroxy-, and N-aminoalkylureas 2. α-Ureidoalkylation of N-(hydroxyalkyl)ureas
sThe a-ureidoalkylation of N-(hydroxyalkyl)ureas (ureido alcohols) with 1,3-H3-and 1,3-Me2-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils decrease both in going from 1,3-H2-to 1,3-Me2-4,5-dihydroxyimidazolidin-2-one and with increasing length (or with branching) of the hydroxyalkyl chain in ureido alcohols. The optimal reaction time for ureido alcohols is 1 h. The X-ray diffraction study showed that 2-(2-hydroxy-1,1-dimethylethyl)glycoluril crystallizes as a conglomerate. The enantiomeric analysis of 2-(2-hydroxyethyl)glycoluril was carried out by chiral-phase HPLC. ; 2009 Springer Science+Business Media, Inc.
Kravchenko,Sigachev,Belyakov,Ilyin,Lyssenko,Davankov,Lebedev,Makhova,Tartakovsky
experimental part
p. 1264 - 1269
(2010/10/04)

Synthesis of pyrimidines and triazines in ice: Implications for the prebiotic chemistry of nucleobases
Herein, we report the efficient synthesis of RNA bases and func-tionalized s-triazines from 0.1 M urea solutions in water after subjection to freeze-thaw cycles for three weeks. The icy solution was under a reductive, methane-based atmosphere, which was s
Menor-Salvan, Cesar,Ruiz-Bermejo, Dra. Marta,Guzman, Marcelo I.,Osuna-Esteban, Susana,Veintemillas-Verdaguer, Sabino
experimental part
p. 4411 - 4418
(2009/12/07)

4,5-dihydroxyimidazolidin-2-ones in an α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 3. * α-Ureidoalkylation of N-[2-(dimethylamino)ethyl]urea
α-Ureidoalkylation of N-[2-(dimethylamino)ethyl]urea with 1,3-unsubstituted, 1,3-dialkyl-, and 1,3-dimethyl-4,5-diphenyl-4,5- dihydroxyimidazolidin-2-ones(thiones) was systematically studied. Hitherto unknown N-[2-(dimethylamino)ethyl]glycolurils and their hydrochlorides were synthesized. The yields of the target glycoluril hydrochlorides decreased on going from 1,3-H2- to 1,3-dialkyl-4,5-dihydroxyimidazolidin-2-ones and increased with the introduction of phenyl groups at the positions 4 and 5 of the starting 4,5-dihydroxyimidazolidin-2-one. X-ray diffraction study showed that 2-[2-(dimethylamino)ethyl]glycoluril crystallizes in the form of a conglomerate.
Gazieva,Lozhkin,Baranov,Nelyubina,Kravchenko,Makhova
p. 2488 - 2493
(2014/05/06)

Synthesis and structures of 5(3H)-oxotetrahydro-1H-imidazo[4,5-c][1,2,5] thiadiazole 2,2-dioxides
The reactions of sulfamides with 4,5-dihydroxyimidazolidin-2-ones were studied at ambient and high pressure. The previously unknown derivatives of 5(3H)-oxotetrahydro-1H-imidazo-[4,5-c][1,2,5]thiadiazole 2,2-dioxide, viz., sulfo analogs of tetrahydroimidazo[4,5-d]imidazole-2,5-(1H,3H) diones (glycolurils), were synthesized. The structures of some of these compounds were established by X-ray diffraction. The high-pressure reactions performed under conditions of solvent phase transitions afforded also N-(1,3-diethyl-5-hydroxy- 2-oxoimidazolidin-4-yl)-N,N′-dialkylsulfamides. Among these compounds, a new conglomerate was found.
Gazieva,Kravchenko,Lyssenko,Gaziev,Lebedev,Makhova
scheme or table
p. 1744 - 1753
(2011/04/23)

2,3,4,5-TETRAHYDRO-1H-1,5-BENZODIAZEPINE DERIVATIVE AND MEDICINAL COMPOSITION
The present invention has its object to provide a 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine derivative represented with the Formula (1) , or the pharmaceutically acceptable salt, which is effective as a therapeutic and prophylactic agent for diabetes, diabetic nephropathy, or glomerulosclerosis.
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(2008/06/13)

Two-step α-ureidoalkylation of ureas with 4,5-dihydroxyimidazolidin- 2-ones
Two-step α-ureidoalkylation of ureas with various 4,5-dihydroxyimidazolidin-2-ones gave novel 1,3-dialkyl-4,5-bis(3-alkylureido)-, 1,3-dialkyl-4,5-bis[3-(2-pyrimidyl)ureido]-, or 1,3-dialkyl-4,5-bis(3,3- dialkylureido)imidazolidin-2-ones and ensembles of three imidazolidine rings. The structure of 4,5-bis(2-oxoimidazolidin-1-yl)imidazolidin-2-one was confirmed by X-ray diffraction data. Springer Science+Business Media, Inc. 2007.
Kravchenko,Gazieva,Sigachev,Maksareva,Lyssenko,Makhova
p. 148 - 153
(2008/02/08)

Facile desulfurization of thioamides and thioureas with tetrabutylammonium periodate under mild conditions
Thioamides and thioureas were reacted with tetrabutylammonium periodate at room temperature to afford the corresponding amides and ureas, respectively, under aprotic conditions. Springer-Verlag 2005.
Pourali, Ali Reza
p. 733 - 737
(2007/10/03)

Hydantoin derivsatives with affinity for somatostatin receptors
The invention provides compounds of formula (I) wherein X, Y, R1, R2, R3 and R4 are as defined in the description, and the preparation thereof. The compounds of the formula bind to somatostatin receptors and are useful as pharmaceuticals.
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(2008/06/13)

Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE)
The present application describes novel hydantoin derivatives of formula (I): or pharmaceutically acceptable salt or prodrug forms thereof, wherein L, Z0, R1, R4, R5, and R11 are defined in the present specification, which are useful as inhibitors of matrix metalloproteinases (MMP), TNF-α converting enzyme (TACE), aggrecanase, or a combination thereof.
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(2008/06/13)

Synthesis of 1S,5R- and 1R,5S-glycoluriles by diastereospecific α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one
A diastereospecific method for the synthesis of individual enantiomers of 1S,5R- and 1R,5S-glycoluriles has been developed based on the α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one.
Chikunov, Il'ya E.,Kravchenko, Angelina N.,Belyakov, Pavel A.,Lyssenko, Konstantin A.,Baranov, Vladimir V.,Lebedev, Oleg V.,Makhova, Nina N.
p. 253 - 255
(2007/10/03)

Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE)
The present application describes novel hydantoin derivatives of formula (I): or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, R1, R2, R3, R4, R5, R6, R7, R11, and n are defined in the present specification, which are useful as inhibitors of matrix metalloproteinases (MMP), TNF-α converting enzyme (TACE), aggrecanase, or a combination thereof.
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(2008/06/13)

Bridged tricyclid analogs of 2-(carboxycyclopropyl)glycine
This invention provides processes for preparing a group of novel bridged tricyclic compounds having the formula: wherein X is (CH2)n, O, S, SO, SO2 or CR1R2; n is 1 or 2; and R1 and R2 are, independently, hydrogen, halogen, hydroxy, alkyl of one to six carbon atoms, alkoxy of one to six carbon atoms, or R1 and R2, taken together with the carbon to which they are attached, form cycloalkyl of three to six carbon atoms, an alkylidene of up to six carbon atoms or a carbonyl.
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(2008/06/13)

Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids
The reactions of 4,5-dihydroxyimidazolidin-2-one with chiral S- and R-N-carbamoyl-α-amino acids occur diastereoselectively with the formation of corresponding 1R,5S(1S,5R)-glycoluriles as predominant diastereomers; the absolute configuration is determined
Kravchenko, Angelina N.,Chegaev, Konstantin Yu.,Chikunov, Il'ya E.,Belyakov, Pavel A.,Maksareva, Elena Yu.,Lyssenko, Konstantin A.,Lebedev, Oleg V.,Makhova, Nina N.
p. 269 - 271
(2007/10/03)

Selective cyclic peptides with melanocortin-4 receptor (MC4-R) agonist activity
Peptides cyclized via disulfide or lactam bridges having melanocortin-4 receptor (MC4-R) agonist activity useful for treatment of obesity.
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(2008/06/13)

NOVEL BICYCLIC AND TRICYCLIC PYRROLIDINE DERIVATIVES AS GNRH ANTAGONISTS
Bicyclic and tricyclic pyrrolidine derivatives are disclosed that are useful as antagonists of the GnRH receptor. Methods for using the novel compounds to treat GnRH-related disorders are also provided, as are pharmaceutical compositions and novel synthetic methods.
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(2008/06/13)

Selective linear peptides with melanocortin-4 receptor (MC4-R) agonist activity
Peptides of formulae I, II and III selectively activate melanocortin-4 (MC-4) receptor activity.
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(2008/06/13)

Reaction of 2-thiohydantoins with some diazoalkanes and some amines
Reaction of 2-thiohydantoin derivatives with diazoalkanes as diazomethane, diphenyldiazomethane and/or 9-diazofluorene was investigated. Several 2-thio- and 2-methylthiohydantoins (IIa,b), (IIIa,b) (XI) and (XII) were prepared via the reaction of 2-thiohydantoins (Ia,b) and (X) with diazomethane. 2-Morpholino- and/or 2-piperidino- glycocyamidines (VIIa,b) and (XVa,b) were prepared by reacting 2-alkylthiohydantoins (IIIa) and (XII), respectively, with morpholine and/or piperidine. Moreover, treating of two equivalents of XIVa-d with one equivalent of piperazine afforded 1,4[di-(5-phenylmethylene-hydantoinyl)]-piperazines (XVIa,b). The hehaviour of 2-alkylthiohydantoins towards alanine and arthranilic acid was also investigated. The structure of the products was established by correct analytical and spectral data as well as by chemical evidencies.
El-Barbary, Ahmed A.,Aly, Youssef L.,Hashem, Abdel-Fatah M.,El-Shehawy, Ashraf A.
p. 77 - 91
(2007/10/03)

Polymeric hydantoin quaternary compounds, methods of making
The present invention relates to a class of novel polymeric hydantoin quaternary compounds, obtained either via a reaction of a hydantoin diamine and an organic dihalide or epichlorohydrin or via a reaction of hydantoin dichloride with an organic diamine. These polymeric hydantoin quaternary compounds have unexpected properties which make them very useful as low foaming biocidal, fungicidal and algicidal agents.
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(2008/06/13)

N-SUBSTITUTED HETEROCYCLIC DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS IN WHICH THEY ARE PRESENT
The invention relates to N-substituted heterocyclic derivatives and its salts. These derivatives have the formula (I) in which the substituents are as defined in the specification. Application: Angiotensin II antagonists
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(2008/06/13)

N-SUBSTITUTED HETEROCYCLIC DERIVATIVES USEFUL IN THE TREATMENT OF CARDIOVASCULAR DISORDERS
The present invention relates to N-substituted heterocyclic derivatives of formula: STR1 processes for their preparation, and pharmaceutical compositions which contain them. The compounds according to the invention are non-peptide compounds which oppose the action of angiotensin II. The compounds according to the invention are thus useful in the treatment of cardiovascular disorders such as hypertension and heart failure.
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(2008/06/13)

Dinitrogen heterocyclic derivatives N-substituted by a biphenylmethyl group, and the pharmaceutical compositions in which they are present
This invention relates to compounds of formula STR1 in which: R1 and R2 are similar or different and are each independently hydrogen or a group selected from CO2 N=C(NH2)2, CONHNHCONH2, CONHNHCSNH2, C(OC2 H5)=NCO2 CH3, COCH2 CO2 H5, N(OH)-CONHCOOC2 NCO2 CH3, COCH2 CO2 H5, N(OH)-CONHCOOC2 H5, C(OC2 H5)=NH or a nitrogen heterocycle; with the proviso that at least one of the substituents R1 or R2 is other than hydrogen; R3 is a hydrogen, a C1 -C6 alkyl, a C2 -C6 alkenyl, a C3 -C7 cycloalkyl, a phenyl, a phenylalkyl, or a phenylalkenyl; R4 and R5 are each independently a C1 -C6 alkyl, a C3 -C7 cycloalkyl, a phenyl or a phenylalkyl; or R4 and R5, bonded together, are either a group of the formula (CH2)n or a group of the formula (CH2)p Y (CH2)q, in which Y is either an oxygen atom, or a sulfur atom, or a substituted carbon atom, or a group N-R6, in which R6 is a hydrogen, a C1 -C4 alkyl, a phenylalkyl, a C1 -C4 alkylcarbonyl, a C1 -C4 halogenoalkylcarbonyl, a C1 -C4 polyhalogenoalkylcarbonyl, a benzolyl, an α-aminoacyl or a N-protecting group, or R4 and R5, together with the carbon atom to which they are bonded, form an indane or an adamantine; p+q=m; n is an integer between 2 and 11; m is an integer between 2 and 5; X is an oxygen or a sulfur atom; and z and t are zero or z+t=1; and its salts.
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(2008/06/13)

Aryl substituted nitrogen heterocyclic antidepressants
Antidepressant agents having the formula STR1 wherein R1 is a polycycloalkyl group; R2 is methyl or ethyl, X is O; and Y comprises a 5-membered heterocyclic ring having one or two nitrogens.
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(2008/06/13)

Process for preparing 5-arylhydantoin
A process for preparing a 5-arylhydantoin having the formula (II): STR1 which comprises: reacting methyl 2-hydroxy-2-methoxyacetate, urea and an aryl compound having the formula (I): STR2 in the presence of an acid. According to the process, the 5-arylhydantoin which is a very effective intermediate for preparing D-arylglycines can be easily prepared from inexpensive raw materials in a high purity.
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(2008/06/13)

Synthesis and antimicrobial activity of chlorobenzyl benzylidene imidazolidinediones and substituted thiazolidinediones
The synthesis of five chlorobenzyl benzylidene imidazolidinediones and four fluorobenzyl benzylidene thiazolidinediones is described. In order to investigate their antimicrobial activity they are evaluated against microorganism such as Candida albicans, Neurospora crassa, Staphylococcus aureus, Myocobacterium smegmatis and Escherichia coli.
Lima,Costa,Goes,Galdino,Pitta,LuU-Duc
p. 182 - 184
(2007/10/02)

Oxidative Cyclization of Diamides by Phenyliodoso Acetate
Carboxamides containing a suitably situated nucleophilic group (carboxamide, N-substituted carboxamide, or hydroxymethyl) undergo oxidation by phenyliodoso acetate to afford heterocyclic products through internal attack on the initially formed isocyanate.N-Substituted carboxamido groups are the least effective of these internal traps.Phenyliodoso acetate is much superior to lead(IV) acetate for oxidative cyclization of maleamide and various substituted propanediamides, but is not suitable for butanediamide.
Beckwith, Athelstan L. J.,Dyall, Leonard K.
p. 451 - 461
(2007/10/02)

Olefinic aryl oxime derivatives of hydantoins
This invention relates to new compounds of the formula: STR1 where each of R1, R2, R3, R4 and R5 has zero to 10 C atoms, and no acetylenic unsaturation; each of R1, R2 and R3 is independently selected from H and hydrocarbyl; each of R4 and R5 is independently selected from H, hydrocarbyl and hydrocarbyl substituted with a group selected from: hydrocarbylcarbonylamino, di(hydrocarbylcarbonyl)amino, N-hydrocarbylcarbonyl(N-hydrocarbyl)amino, formylamino, diformylamino, and formyl(N-hydrocarbyl)amino, hydrocarbyloxy, hydrocarbylthio, formyl, formylthio, hydrocarbylcarbonyloxy, hydrocarbylcarbonylthio, hydrocarbyl carboxyl, hydrocarbyl thiocarboxyl, hydrocarbylamino, dihydrocarbylamino, hydrocarbylcarbonyl, 3-indolyl, 3-(1-hydrocarbyl)indolyl, 3-(1-hydrocarbylcarbonyl)indolyl, 3-(1-formyl)indolyl, carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, 5-imidazolyl, 5-(3-hydrocarbyl)imidazolyl, 5-(3-hydrocarbylcarbonyl)imidazolyl, and 5-(3-formyl)imidazolyl, and where at least one of R1, R2, R3, R4 and R5 contains olefinic unsaturation. The invention also relates to addition polymers of such compounds.
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(2008/06/13)

KINETICS AND MECHANISM OF BASE-CATALYZED CYCLIZATION OF SUBSTITUTED AMIDES AND NITRILES OF HYDANTOIC ACID
Rates of base-catalyzed cyclizations of 8 substituted derivatives of hydantoic acid amide type R3-NH(5)-CO(4)-NR2(3)-CH2(2)-CO(1)-NHR1 and 9 nitriles type R3-NH(5)-CO(4)-NR2(3)-CHR1(2)-CN have been measured in aqueous and methanolic media.The cyclization of the amides in aqueous medium is also accompanied by hydrolysis of the hydantoins formed.In some cases the hydrolysis rate constant is greater than the corresponding cyclization reaction rate constant.With the least reactive amides, the cyclization is also accompanied by hydrolysis of the amide group.The ra te of the cyclization reactions in water is higher than that in methanol (at the same concentration of the lyate ions) by the factor of 10 - 100.Substitution of hydrogen at 3 and 5 positions by methyl or phenyl groups causes an acceleration of the cyclization reaction, whereas a substitution in the amide group causes a considerable retardation.The greatest acceleration of the cyclization (by as much as 4 orders) is caused by introduction of phenyl group to the N(5) position, which is due to a substantial increase of concentration of the reactive anion.
Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
p. 140 - 155
(2007/10/02)

KINETICS OF ACID-CATALYZED CYCLIZATION OF SUBSTITUTED HYDANTOINAMIDES TO SUBSTITUTED HYDANTOINS
The kinetics of acid-catalyzed cyclization of the hydantoinamides type R3-N(5)H-CO-N(3)R2-CH2-CO-N(1)HR1 (R1,R2,R3=H and/or CH3) has been studied in 0.5 to 5 mol/l hydrochloric acid.The cyclization rate is limited by the rate of the attack of nitrogen atom N(5) on the carbon atom of the protonated amide group.The dissociation constants of the protonated hydantoinamides and rate constants of their cyclizations have been determined.Replacement of hydrogen atom by methyl group at the N(5) nitrogen atom accelerates the cyclization about two times, the same substitution at N(3) accelerates about 50x, whereas at N(1) it results in a 300 fold retardation.With the hydantoinamides having R3=CH3, the cyclization rate of the protonated hydantoinamide increases with increasing concentration of hydrochloric acid, whereas with the other derivatives this value is independent of the acid concentration.
Kavalek, Jaromir,Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
p. 1999 - 2004
(2007/10/02)

Process for the preparation of D1-β-aryl amino acids
The invention relates to a process for the preparation of DL-β-aryl-amino acids of the general Formula STR1 wherein R, R1 and R2 stand for hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, nitro or C1-4 dialkylamino; whereby in the case of monosubstituted derivatives R and R1 are hydrogen and R2 has the same meaning as stated above and can be attached to position 2, 3 or 4 related to the methylene group; in the case of disubstituted derivatives R is hydrogen and R1 and R2 have the same meaning as stated above and are attached to positions 2,3; 2,4; 2,5; 2,6; 3,4 or 3,5 related to the methylene group; in the case of trisubstituted derivatives R, R1 and R2 have the same meaning as stated above and are attached to positions 2,3,4; 2,3,5; 2,3,6; 3,4,5 or 3,4,6 related to the methylene group.
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(2008/06/13)

BASE CATALYZED CYCLIZATION OF SUBSTITUTED ESTERS OF HYDANTOIC AND THIOHYDANTOIC ACID
Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol.The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place.Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions.The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30percent of the starting ester.In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis.Substituents always accelerate the cyclization.The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium.The cyclizations are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.
Kavalek, Jaromir,Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
p. 375 - 390
(2007/10/02)

Photochemical Cyclisation of 3-N-(Dialkylaminomethyl)imidazole-2,4-diones to 1,3,7-Triazabicyclooctanes
Ultraviolet irradiation of N-3 Mannich bases derived from hydantoin or from 5,5-disubstituted hydantoins (imidazole-2,4-diones), provides an efficient route to 1,3,7-triazabicyclooctane derivatives by photocyclisation to the C-4 carbonyl group.
Coyle, John D.,Bryant, Laurence R.B.
p. 531 - 534
(2007/10/02)

Thiosubstituted amino acids
This invention relates to thiosubstituted cyclic amino acids, to a process for their preparation and to pharmaceutical compositions containing them together with an inert non toxic pharmaceutical carrier.
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(2008/06/13)