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Showing papers on "Piperidine published in 1989"


Journal ArticleDOI
TL;DR: While members of this series of compounds demonstrate antitumor activity in vivo, these new agents are not classical analogues of cisplatin, as they contain three nitrogen donors and only one leaving group.
Abstract: A series of 32 cationic platinum(II) complexes of the form cis-[PtA2(Am)Cl]+, where A is a monodentate (NH3 or i-PrNH2) or A2 is a bidentate (ethylenediamine or 1,2-diaminocyclohexane) amine and Am is either a heterocyclic amine based on a pyridine, pyrimidine, purine, piperidine, or a saturated amine (RNH2) ligand, was prepared and screened against in vivo murine tumor models. Each compound was tested against Sarcoma 180 ascites (S180a) in mice, with 20 members of the series showing activity (ILS greater than 50%). Antitumor activity also was demonstrated in 4 of 16 compounds tested in the L1210 murine leukemia model (ILS greater than 25%) and in 3 of 3 tested in the P388 murine leukemia model (ILS greater than 30%). The most active and potent analogues of the series were obtained when A was NH3 and Am was N1-pyridine, N1-4-methylpyridine, N1-4-bromopyridine, N1-4-chloropyridine, N3-cytosine, or N7-2'-deoxyguanosine. Complexes containing chelating and saturated amine ligands (A), as well as two trans isomers of active cis analogues (trans-[Pt(NH3)2(Am)Cl]+, where Am = N1-pyridine or N1-4-methylpyridine), were inactive in the S180a screen. All complexes were characterized by means of elemental analysis, HPLC, and 195Pt NMR spectroscopy, and the structure of one analogue, cis-[Pt(NH3)2(N3-cytosine)Cl](NO3), was determined by using single-crystal X-ray diffraction methods. While members of this series of compounds demonstrate antitumor activity in vivo, these new agents are not classical analogues of cisplatin (i.e. cis-[PtA2X2] complexes), as they contain three nitrogen donors and only one leaving group. The results of these studies suggest that further work should be conducted to better define the limits of the structure-activity relationships among platinum(II) complexes.

246 citations



Journal ArticleDOI
TL;DR: In this paper, the authors evaluated the behavior of protected H-Val-Lys-Asp-Gly-Tyr-Ile-OH towards imide formation and found that the use of a carboxylic acid temporary protecting group is not a safe strategy for avoiding aspartimide formation during HF treatment.

104 citations



Journal ArticleDOI
TL;DR: Norbornene and norbornadiene derivatives have been shown to react with aryl and vinyl halides in the presence of a palladium catalyst, formic acid, and tributylamine or piperidine to give hydroarylated and hydrovinylated derivatives in good to high yield as mentioned in this paper.

61 citations


Journal ArticleDOI
TL;DR: In this paper, the influence of tributylphosphine, diethyl ether, carbon monoxide and tert-butyl chloride on the hydrogenation of 1-butene and 1-3-butadiene on platinum catalysts was studied.

44 citations


Journal ArticleDOI
TL;DR: In this article, a cyclization of amino alcohols over copper supported on γ-alumina and magnesia was found to be an efficient method for the synthesis of cyclic amines, their alkyl derivatives and in some instances also their dehydro derivatives.

32 citations


Journal ArticleDOI
TL;DR: Compounds described herein, with free 5'-hydroxyl function, are potential inhibitors of the HIV-reverse transcriptase promoted c-DNA synthesis.

31 citations


Journal ArticleDOI
TL;DR: Several mixed nickel(II) nitrate complexes with 1,2-dipiperidinoethane (dipe) and β-diketonate ions (dike) have been obtained and characterized by X-ray crystallography as discussed by the authors.
Abstract: Several new mixed nickel(II) nitrate complexes with 1,2-dipiperidinoethane (dipe) and β-diketonate ions (dike), [Ni(NO3)(dike)(dipe)], have been obtained and characterized. The crystal structure of one of them, [Ni(NO3)(acac)(dipe)], was determined by X-ray crystallography. The crystal is monoclinic with the space group Cc, Z=4, a=9.0517(4), b=21.932(1), c=9.8814(6) A, β=88.151°. Block-diagonal least-squares refinements have led to a final R value of 0.036 for 2471 reflections. It was confirmed that the nitrate ion in the octahedral complex acts as a bidentate ligand and that the conformation of the piperidine ring in dipe is a chair form. The spectral behaviors of these complexes in various organic solvents are discussed in comparison with those of similar complexes with other N,N′-alkylated ethylenediamine ligands (diam). It was concluded that, in a solvent with low polarity, the complexes are dissolved unchanged; in a more polar solvent, however, dissociation of NO3− takes place, producing solvated or ...

25 citations


Journal ArticleDOI
TL;DR: In this article, an electron-donating compound, piperidine, was used for hydrogenation of unsaturated hydrocarbons such as 1-butene, 1,3-butadiene and 1-butyne.

23 citations


Journal ArticleDOI
TL;DR: Le chlorhydrate de la [dimethyl-1,3 hydroxy-3' phenyl-4 propyl- 4] piperidine racemique as discussed by the authors synthetise via l'alkylation par lithiation de [methoxy-3', phenyl 4 methyl-1 tetrahydro-1.2,5,6] pyridine
Abstract: Le chlorhydrate de la [dimethyl-1,3 hydroxy-3' phenyl-4 propyl-4] piperidine racemique a ete synthetise via l'alkylation par lithiation de la [methoxy-3' phenyl-4 methyl-1 tetrahydro-1,2,5,6] pyridine

Journal ArticleDOI
TL;DR: In this paper, the solvo intermediate W(CO) 5 S is formed from W( CO) 5 L in less than 10 ps under 355-nm irradiation, which is the same as the result of irradiation for W(Co) 6 S.
Abstract: W(CO) 5 L (L=pyridine, piperidine) undergoes photochemical replacement of L by solvent (S). If the solvent is a poor ligand, W(CO) 5 S can be rapidly converted to an alkene complex to render the primary product observable. Across the region of LF singlet absorption, quantum yields increase with decreasing excitation energy, but quantum yields in the triplet region are smaller. The solvo intermediate W(CO) 5 S is formed from W(CO) 5 L in less than 10 ps under 355-nm irradiation. This contrast with the result of irradiation for W(CO) 6

Journal ArticleDOI
TL;DR: It has been found that introduction of a hydroxyl group into the 4-position of the xanthenespiropiperidine nucleus produces a potent mu-opiate agonist.
Abstract: A series of novel 1'-methylxanthene-9-spiro-4'-piperidines has been prepared in the search for opiate analgesics with improved pharmacological properties. It has been found that introduction of a hydroxyl group into the 4-position of the xanthenespiropiperidine nucleus produces a potent mu-opiate agonist. The structure-activity relationship of the series has been explored by use of isosteric replacements of the phenolic hydroxyl group. Moreover, the effect of altering the conformation of the piperidine ring has been studied. It was interesting to note that, in compounds lacking the phenolic hydroxyl group, opiate activity could be produced by introduction of the (phenylamino)ethyl group instead of methyl at the 1'-position.

Journal ArticleDOI
TL;DR: Alkynylation of S-alkylthioamidium salts of thiolactams with lithium acetylides followed by reduction with LiAIH4 provided α-alkynylazacycloalkanes, which on reduction, or hydroboration followed by oxidation, gave α-substituted pyrrolidine and piperidine alkaloids.
Abstract: Alkynylation of S-alkylthioamidium salts of thiolactams with lithium acetylides followed by reduction with LiAIH4 provided α-alkynylazacycloalkanes, which on reduction, or hydroboration followed by oxidation, gave α-substituted pyrrolidine and piperidine alkaloids.

Journal ArticleDOI
TL;DR: In this paper, the synthesis of pyrylium compounds using cyclohexane-1,2-dione and cycloheptane-2H,7H-1-benzopyranones was studied.
Abstract: Pyrylium Compounds. 42. Benzocycloalkenones and Dihydro-2H,7H-1-benzopyranones from 2,4,6-Triarylpyrylium Salts and Cycloalkane-1,2-diones 2,4,6-Triarylpyrylium salts 1 react with cycloalkane-1,2-diones 2 in the presence of an appropriate condensing agent to yield benzocycloalkenones 3. Thus, sodium acetate and cyclo-hexane-1,2-dione (2a) lead to the dihydro-2H-naphthalenones 3a–i, whereas with cycloheptane-1,2-dione (2b) and piperidine acetate, triethylamine or sodium acetate the tetrahydro-5H-benzo-cyclohepten-5-ones 3j–r are formed. As shown for the example 3a, j 4a, b, benzocycloalkenones of type 3 can be converted into phthalazines 4 on heating with hydrazine in ethanol. By reaction of the dione 2a and an equimolar mixture of triethylamine and acetic acid or morpholine acetate with the salts 1 5,6-dihydro-2H,7H-1-benzopyran-8-ones 5 are obtained as a result of a new type of ring transformation. The pyrans 5 can be cleaved with perchloric acid in ethanol to 5,6,7,8-tetrahydro-8-oxo-1-benzopyrylium perchlorates 6. If the pyrans 5 are heated with sodium acetate in ethanol, a conversion to benzocycloalkenones 3 is achieved (cf. 5a 3a). The structure of the new compounds was established by spectroscopic methods.


Journal ArticleDOI
TL;DR: Bronchodilator potency was related to the extent of steric crowding surrounding the side-chain terminal amine function and addition of a methyl substituent on the carbon alpha to the terminalAmine often increased potency or pulmonary selectivity.
Abstract: A series of 3-(aminoalkyl)benzopyrano[3,4-c]pyridin-5-ones was prepared and tested as potential orally active anticholinergic bronchodilators. Inhibition of methacholine-induced collapse in guinea pigs and inhibition of pilocarpine-induced bronchoconstriction in dogs served as in vivo models. Simultaneous measurement of salivary inhibition in the dog model allowed determination of a pulmonary selectivity ratio. The benzopyrano[3,4-c]pyridin-5-one parent ring system was prepared by Pechman condensation of phenols with a piperidine beta-keto ester. Alkylation with aminoalkyl halides, or with 1-chloro-2-propanone followed by reductive amination, yielded the 3-substituted target compounds. Bronchodilator potency was related to the extent of steric crowding surrounding the side-chain terminal amine function. Addition of a methyl substituent on the carbon alpha to the terminal amine often increased potency or pulmonary selectivity. After secondary pharmacological evaluation, compound 7a, designated CI-923, was selected for clinical trial as a bronchodilator.

Patent
16 Jun 1989
TL;DR: The analogs of nipecotic acid are GABA uptake inhibitors for use to treat epilepsy and thus, thus, the invention is also pharmaceutical compositions and methods of use therefor as mentioned in this paper.
Abstract: Selected analogs of nipecotic acid are the novel compounds of the present invention. The analogs are GABA uptake inhibitors for use to treat epilepsy and, thus, the invention is also pharmaceutical compositions and methods of use therefor.

Patent
11 Dec 1989
TL;DR: In this paper, a novel chemical process for pre-paring 4-phenylpiperidines having calcium overload blocking activity and antidepressant activity was described, and novel interme-diates used in that process.
Abstract: The invention relates to a novel chemical process for pre­paring 4-phenylpiperidines having calcium overload blocking activity and antidepressant activity, and to novel interme­diates used in that process.

Journal ArticleDOI
TL;DR: In this paper, the enthalpies of aliphatic amines with Cr(CO)6 in heptane at ambient temperatures were determined by photoacoustic calorimetry.

Journal ArticleDOI
TL;DR: In this paper, double diastereoselection in the S ulfoxide P iperidine A nd C arbonyl (SPAC) reactions of sulfinyl acetate esters with α-unsubstituted aldehydes was investigated to facilitate asymmetric syntheses of γ-hydroxy-α,β-unsaturated esters.

Patent
18 Oct 1989
TL;DR: A cyclic amine compound is defined by the formula: "STR1## in which J is indanyl, INDANONYL, indanonyl, indenyl, INDENYL, INDANE, indane, indanedionyl, tetralonyl and benzosuberonyl or a divalent group thereof", and the ring including T and Q is piperidine.
Abstract: A cyclic amine compound is defined by the formula: ##STR1## in which J is indanyl, indanonyl, indenyl, indenonyl, indanedionyl, tetralonyl, benzosuberonyl, indanolyl or a divalent group thereof, K is phenyl, an arylalkyl or cynnamyl, B is --(CHR22) r--, R22 being H or methyl, --CO-- (CHR22)r--, ═(CH--CH═CH)b--, ═CH--(CH2)c-- or ═(CH--CH)d═ and the ring including T and Q is piperidine. The compound is useful to treat senile dementia.

Journal ArticleDOI
TL;DR: The 99mTc-BAT complexes prepared by the tin-reduction method proved to be stable under in vitro conditions and the brain uptake values in CD-1 mice were comparably low.

Journal ArticleDOI
TL;DR: The cyclization of Z- and E-hexenyliminomalonates with TMS-OTf stereoselectively affords the cis-annulated piperidine lactones 13/14 and 15, respectively, with complete retention of the double bond geometry as discussed by the authors.
Abstract: The cyclization of Z- and E-hexenyliminomalonates 9 and 10 with TMS-OTf stereoselectively affords the cis-annulated piperidine lactones 13/14 and 15, respectively, with complete retention of the double bond geometry. In contrast, the allylsilane 11 leads exclusively to the vinyl piperidine 12. Cyclization of the imines 19 and 22 gives in high yield preferentially the tetrahydropyridine 20 and the octahydroisoquinoline 23, respectively.

Journal ArticleDOI
TL;DR: In this paper, the crystal structure of the adamantane cage system was determined by X-ray diffraction and several stereoelectronic effects were deduced from the 1H and 13C nmr data.

Patent
26 Jul 1989
TL;DR: The substituted piperidine groups are effective stabilizers for organic materials, especially synthetic polymers, which are subject to the action of light, heat and oxidation as mentioned in this paper, and are used to stabilize polymers.
Abstract: Compounds containing substituted piperidine groups, of the general for­mula (I) in which n is e.g. 1, 2 or 3, R₁ is e.g. hydrogen or methyl, R₂ is e.g. ethylene or trimethylene and if n is 1, A is e.g. hydrogen, -COOC₁₈H₃₇-n or -COC₁₁H₂₃-n, if n is 2, A is e.g. -CO-(CH₂)₄-OC- or and if n is 3, A is e.g. are effective stabilizers for organic materials, especially synthetic polymers, which are subject to the action of light, heat and oxidation.

Journal ArticleDOI
TL;DR: The X-ray and IR spectra of 3-phenethyl-3-azabicyclo[3.2.1] octan-8-α-ol have been studied in several media, and its crystal structure has been determined by Xray diffraction.

Patent
11 Dec 1989
TL;DR: In this paper, a novel chemical process for pre-paring 4-phenylpiperidines having calcium overload blocking activity and antidepressant activity was described, and novel interme-diates used in that process.
Abstract: The invention relates to a novel chemical process for pre­paring 4-phenylpiperidines having calcium overload blocking activity and antidepressant activity, and to novel interme­diates used in that process.

Journal ArticleDOI
TL;DR: In this article, the synthesis of 1-formyl-2-(3-indolyl)-4-piperidone, trans-1-1,2,3,methyl-4, and 4,4-ethyleneacetals is described.
Abstract: The synthesis of 1-formyl-2-(3-indolyl)-4-piperidone, trans-1-formyl-2-(3-indolyl)-3-methyl-4-piperidone, and their 4,4-ethyleneacetals is described. The introduction of a formyl group on the piperidone nitrogen induces a change in the piperidine ring conformation such that the 2-indolyl group is axial. However, in the 1-formyl-2-indolyl-4-piperidone 4,4-ethyleneacetals the indolyl group adopts an equatorial disposition due to a severe steric syn-diaxial interaction with the C-4 substituent. 13 C-Dnmr is used to investigate the amide rotational barriers in a series of 2-aryl-1-formyl-4-piperidones

Patent
16 Mar 1989
TL;DR: In this article, JPO and Japio presented an amine derivative having the above-mentioned amines in part of the structure in an amount of preferably 0.001-1wt.% in a coolant.
Abstract: PURPOSE: To obtain the subject oil, containing an amine (derivative) of morpholine, etc., excellent especially in antimicrobial properties against yeasty fungi, suppressing occurrence of putrefying smell even in use thereof for a long period and sufficiently usable in a small amount. CONSTITUTION: The objective oil obtained by blending one or more amines selected from morpholine, piperidine, piperazine and pyrrolidine or an amine derivative having the above-mentioned amines in part of the structure in an amount of preferably 0.001-1wt.% in a coolant. Furthermore, N-(cyclopentenyl) morpholine, 4'-piperidinoacetophenone, N-(2-aminoethyl)piperazine, N-(2- hydroxyethyl)pyrrolidine, etc., are cited as examples of the aforementioned amine compounds. COPYRIGHT: (C)1990,JPO&Japio