Showing papers on "Pyrazole published in 1994"

Substituted n-piperidino-pyrazole-3-carboxamide

Abstract: N-Piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyra zole-3-carboxamide of formula: its salts and solvates are powerful antagonists of central cannabinoid receptors. They are prepared by reaction of a functional derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxyli c acid with 1-aminopiperidine and then optional salification.

Substituierte N,N-Chelat-Liganden - Anwendungen in der Molybdän-katalysierten Olefin-Epoxidation

Abstract: Substituted N,N-Chelate Ligands - Applications in Molybdenum-Catalyzed Epoxidation of Olefins* Oxodiperoxomolybdenum complexes 4 of substituted 2-[3(5)-pyrazolyl]pyridines (2a-g) were synthesized in order to control the solubility of these complexes in organic solvents. Alkyl side chains (butyl, octyl, octadecyl) increase the solubility of the complexes and enable spectroscopic investigations in solution. Due to the symmetry of the ligands the peroxo complexes 4 appear in two isomeric forms, with the terminal oxo ligand in the trans position either to pyridine or to pyrazole. The latter isomer of (C5H4NC3H2N2CH2COOEt)MoO(O2)2 (4f) was characterized by an X-ray structure analysis. The alkyl-substituted peroxo complexes are active catalysts for the epoxidation of olefins with tert-butyl hydroperoxide.

Pentafluorosulphanylphenyl and pentafluorosulphanylpyridil substituted heteroaromatic compounds with insecticidal or acaricidal activity

Abstract: Compounds with insecticidal or acaricidal activity have formula (IA) or (IB), wherein Ra represents hydrogen or from 1 to 4 optional substituents and Rb represents from 1 to 3 optional substituents and wherein A represents an optionally substituted N-linked nitrogen-containing five or six membered aromatic heterocyclic ring, for example imidazole, pyrrole, pyrazole, pyrimidinone and pyridone.

Pyrazoles—A novel class of blocking agents for isocyanates

Abstract: Pyrazoles were found as a novel class of blocking groups for isocyanates. Adhesive mixtures of pyrazole blocked isocyanates and amine terminated prepolymers like Jeffamines® (Texaco Chem. Co.) combine excellent reactivities (gelation times within minutes at 100–120°C), good latencies (more than 170 days at 40°C), and good adhesion properties on many substrates. The reactivity of pyrazole blocked isocyanates toward nucleophiles increases with the number of electron donor substituents on the pyrazole nucleus and, thus, can be fine tuned by the appropriate substitution pattern. This behavior contrasts sharply with that of phenolic blocked isocyanates, where reactivities with the same nucleophiles decrease with more and stronger electron donor substituents on the phenol nucleus. Therefore, different deblocking reaction mechanisms were proposed for pyrazole vs. phenol blocked isocyanates. The excellent latency of pyrazole blocked isocyanate/Jeffamine® mixtures is due to the insolubility of the two components at ambient temperature and the slow endothermic dissolution process at higher temperature. The good adhesion of formulations with pyrazole blocked isocyanates as reactive components on most plastic and metal substrates is ascribed to the primer action of the released blocking group. © 1994 John Wiley & Sons, Inc.

Pyrazole-3-carboxamide derivatives, process for their preparation and pharmaceutical compositions in which they are present

Abstract: The present invention relates to novel pyrazole-3-carboxamide derivatives of the formula ##STR1## in which the substituents are as defined in the specification. The present invention further relates to a process for the preparation of these novel derivatives and to the pharmaceutical compositions in which they are present.

1,5-diphenyl pyrazole compounds for treatment of inflammation

Abstract: A class of 1,5-diphenyl pyrazoles is described for the treatment of inflammation, including treatment of pain and disorders such as arthritis. Compounds of particular interest are of formula (I), wherein R1 is methylsulfonyl; wherein R2 is selected from -CF?3?, -CF2Cl, -CF2H, -CF2CF3 and -CF2CF2CF3; and wherein R?3? is fluoro or chloro; or a pharmaceutically-acceptable salt thereof.

Synthesis, characterization and molecular structure of the hydroperoxo complex [(η5C5Me5)Ir(µ-pz)3Rh(OOH)(dppe)][BF4]; Hpz = pyrazole, dppe β 1,2-bis(diphenylphosphino)ethane

Abstract: The synthesis and structural characterization of the title hydroperoxide complex is described.

The influence of the nitro group on the solid-state structure of 4-nitropyrazoles : the cases of pyrazole, 3,5-dimethylpyrazole, 3,5-di-tert-butylpyrazole and 3,5-diphenylpyrazole. I: Static aspects (crystallography and thermodynamics)

Abstract: We have determined the enthalpies of sublimation of 3,5-di-tert-butylpyrazole (3), 3,5-diphenylpyrazole (4), 4-nitropyrazo1e (5), 3,5-dimethyl-4-nitropyrazole (6), 3,5-di-tert-butyl-4-nitropyrazole (7) and 3,5-diphenyl-4-nitropyrazole (8); those of pyrazole (1) and 3,5-dimethylpyrazole (2) were already known. the effect of the C-substituents (Me, Bu t , Ph and NO 2 ) on the enthalpies of sublimation of pyrazoles and benzenes are additive and linearly related. Moreover, we report the structure of three of these 4-nitropyrazole derivatives, (5), (7) and (8), which have been solved by X-ray crystallography; those of the remaining five compounds were already known

Argentotropism in (pentamethylcyclopentadienyl)iridium complexes with pyrazole ligands : multinuclear DNMR esperiments

Abstract: The dynamic behavior of the heterobimetallic compounds [(η 5 -C 5 Me 5 )Ir(Pz) 3 Ag(PPh 3 )], [(η 5 -C 5 Me 5 )Ir(μpz) 3 {Ag(PPh 3 )} 2 ]BF 4 , [(η 5 -C 5 Me 5 )Ir(pz) 2 PPh 3 ], and [(η 5 -C 5 Me 5 )Ir(PPh 3 )(μ-pz) 2 Ag(PPh 3 )]BF 4 has been studied by multinuclear ( 1 H, 13 C, 15 N, 31 P, and 109 Ag) NMR

Adenosine deaminase inhibitors: synthesis and structure-activity relationships of 2-hydroxy-3-nonyl derivatives of azoles.

Abstract: A series of erythro-1-(2-hydroxy-3-nonyl)azole derivatives have been synthesized and evaluated for adenosine deaminase (ADA) inhibitory activity, in order to introduce simplifications in the ADA inhibitor erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA, 1a). The synthesis of most of the reported compounds was achieved by reaction of 2-bromo-3-nonanone with the suitable azole followed by reduction of the carbonyl group to give a diastereoisomeric mixture of N-substituted (2-hydroxy-3-nonyl)azoles. Separation of diastereoisomers was achieved by HPLC or by preparative TLC plates. The results of the enzymatic test indicate that the nitrogen in the 3-position, and secondly, the nitrogen in the 5-position are very important for the interaction of the azole ring with the inhibitory site on the enzyme. In fact, the pyrazole and the 2-substituted 1,2,3-triazole derivatives (10 and 15, respectively) are nearly inactive, whereas the erythro-1-(2- hydroxy-3-nonyl)-1,2,4-triazole (18e) was the most potent ADA inhibitor in the series with Ki = 0.3 microM.

Evaluation of pyrazole and ethanol induced S9 fraction in bacterial mutagenicity testing.

Abstract: A major constitutive enzyme in the liver of the uninduced rat is cytochrome P450-2E1. This isozyme has been shown to metabolize a number of carcinogens, including low molecular weight nitrosamines and a number of compounds normally regarded as non-mutagenic in the Ames test, e.g. aniline, urethane and benzene. Using the standard induction procedures [Aroclor 1254 or a combination of phenobarbitone (PB) and beta-naphthoflavone (beta-NF)] the level of CYP2E1 in rat liver is actually suppressed and it has been suggested that this may account for the negative findings with these compounds in the Ames test. S9 fractions were prepared from rats pre-treated with pyrazole or ethanol (inducers of CYP2E1) and then used in the Ames test (or pre-incubation modification) with urethane, acetaminophen, aniline, benzene, procarbazine and N-nitrosopyrrolidine. Both pyrazole and ethanol induced S9 were superior to PB/beta-NF-S9 and uninduced-S9 for the activation of N-nitrosopyrrolidine, a known CYP2E1 substrate. However, there was no evidence of mutagenic activity with urethane, aniline, benzene, procarbazine or acetaminophen. As these compounds have demonstrated genotoxicity in vivo, additional important metabolic pathways must be required which are not present in rat liver S9 fraction.

Chelation-Controlled Regioselectivity in the Synthesis of Substituted Pyrazolylpyridine Ligands. 2. Tridentates

Abstract: A new, more reliable synthesis of tetraketone 4 was found. With t BuNHNH 2 , PhNHNH 2 , and 4-hydrazinobenzoic acid, it condensed to give mostly in,in-disubstituted derivatives (7ii-9ii) of the parent, C-linked 2,6-bis(pyrazol-3-yl)pyridine 5, along with some in,out materials. MeNHNH 2 also provided some out,out isomer (6oo). This same derivative was also produced by NaH-mediated methylation of 5 with CH 3 I, presumably via a Na + chelate that disallowed access to the inner pyrazole nitrogens, and was able, as a tridentate, to solubilize solid sodium picrate (NaPic) into CDCl 3 , with 1 H-NMR detection of the complex.(...)

Fused tricyclic heteroaromatic derivatives as dopamine receptor subtype ligands

Abstract: A class of fused tricyclic heteroaromatic compounds of formula (I), or a salt thereof or a prodrug thereof containing a fused pyrazole ring are ligands for dopamine receptor subtypes within the body and are therefore of use in the treatment and/or prevention of disorders of the dopamine system, such as schizophrenia.

Leukotriene B4 (LTB4) receptor antagonists: a series of (hydroxyphenyl)pyrazoles.

Abstract: A series of (hydroxyphenyl)pyrazoles was designed by molecular modeling comparison with the LTB4 structure and prepared for evaluation as LTB4 receptor antagonists, culminating in 4-ethyl-5-[[6-methyl-6-(1H-tetrazol-5-yl)heptyl]oxy]-2-(1H-pyrazol -3- yl)phenol (2). Using an assay for inhibition of specific [3H]LTB4 binding to human PMN, it was found that the pyrazole ring could be methylated at N(1) with little loss of activity while methylation at N(2) reduced activity significantly. The structure-activity relationship of the terminal acid group was investigated. Good activity was found with o- and m-phenylalkanoic acids, chromane carboxylic acid, and tetrazole groups. The best in vitro activity was realized with the pyrazole nitrogen unsubstituted and with a six-carbon chain linking the phenyl ether oxygen to the tetrazole group. Compound 2, having an IC50 of 6.4 +/- 0.8 nM in the binding assay, was selected for further preclinical evaluation.

Synthesis of Ferrocenyl-Substituted Heterocycles: The Beneficial Effect of the Microwave Irradiation

Abstract: The synthesis of ferrocenyl-substituted thiophenes, furans, pyrroles, pyrimidine and pyrazole has been studied. 2-Ferrocenylpyrroles were prepared from ferrocenyl ketoximes and acetylene in DMSO - KOH mixture whereas 3-chloro-3-ferrocenylacrylaldehydes and thioglycolic or glycolic acids were the starting materials for the synthesis of the thiophene and furan derivatives. The yields were significantly enhanced when the reactions were carried out in a microwave oven. The lower stability of 2-ferrocenylfuran in comparison with 2-ferrocenylthiophene is discussed on the basis of semiempirical quantum chemistry calculations.

Synthesis of new chiral heterocycles of the pyrazole and 2-isoxazoline types from (+)-3-carene.

Abstract: Preparation of chiral heterocyclic compounds of the pyrazole and 2-isoxazoline types starting from natural monoterpene hydrocarbon (+)-3-carene is described. Stereochemical assignment of the compounds synthesized is made by NMR spectroscopy and X-ray analysis together with the data obtained by molecular mechanics and quantum chemical calculations.

Aldoxime derivative and agrohorticultural bactericide

Abstract: An aldoxime derivative represented by general formula (I), wherein A represents pyrazole, thiazole, etc.; B represents pyridine, pyrazole, thiazole, etc.; and X represents halogen or S(O)nR24. This compound is novel, has an excellent agrohorticultural bactericidal effect, and does not injure useful crops, thus being useful as an agrohorticultural bactericide.

Pyrazole fungicides 3-substituted by a heterocyclic ring

Abstract: Pyrazoles 3-substituted by a heterocyclic ring These pyrazoles are of formulae (I) and (Ibis) wherein Het = an optionally substituted heterocyclic ring; Y1, Y2 = hal, nitro, CN, alkyl, alkoxy, acyl; Z = H, nitro, CN, (halo)alkyl, alkylS(O)n, wherein n = 1 or 2, optionally substitued aminoalkyl, acyl, aminocarbonyl, alkoxycarbonyl Fungicides for agricultural use

Bicyclic heterocycle-containing sulfonamide and sulfonic acid ester derivative

Abstract: PURPOSE:To obtain a new sulfoneamide derivative having excellent antineoplastic activity and having a low-toxicity bicyclic hetero ring, and a new sulfonic acid ester derivative. CONSTITUTION:A compound of formula I [A ring is a monocyclic aromatic ring or a bicyclic aromatic ring; B ring is a 6-membered ring type unsaturated hydrocarbon or an unsaturated 6-membered heterocyclic ring containing one N as a hetero atom; C ring is a 5-membered heterocyclic ring containing 1 or 2 nitrogen atoms, wherein A to C rings may have substituent groups; W is a single bond or CH=CH; X is NR or 0; Y is C or N; Z is NR or N; R and R are each H or a lower alkyl, except (1) combination of A ring = m- ethylbenzene, W = a single bond, X=NH, B ring = methoxybenzene and C ring: an unsaturated pyrazole and (2) combination of A ring=4-(acetamide) benzene or 4-aminobenzene, W: a single bond, X=NH, B ring= an unsaturated benzene and C ring= an unsaturated pyrazole], e.g. 4-amino-N-(3-chloro-1H- indol-7-yl)benzenesulfonamide of formula II.