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Volume 18, Issue 8
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SATOSHI OMURA, AKIRA NAKAGAWA, MICHIKO KATAGIRI, TOJU HATA, MIKIO HIRA ...1970 Volume 18 Issue 8 Pages 1501-1508
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStructural relationship between demycarosyl-leucomycin-A3 proposed through X-ray crystallography by Hiramatsu, et al. and leucomycin-A3 was examined, and it was found that the hydroxyl group at the C-9 position on lactone of the latter underwent allylic rearrangement being transferred to the C-13 position in the former on mild hydrolysis of the latter with dilute hydrochloric acid. On the other hand, isoleucomycin-A3, whose hydroxyl group at the C-13 position was transferred from C-9 in leucomycin-A3 without liberation of mycarose portion, was obtained by warm acid treatment of leucomycin-A3. Configuration on the C-9 position was determined by applying the benzoate or Mills' rule to leucomycin-A3 and, from the present and previously reported results, the absolute structure of leucomycin-A3 was elucidated.View full abstractDownload PDF (822K) -
KOJI ITO1970 Volume 18 Issue 8 Pages 1509-1518
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe low temperature behavior of solutions of simple substances and pharmaceuticals was studied. The authors found noticeable changes in the macroscopic appearance of solutions during freezing of some substances which exhibited the eutectic behavior. Appearance changes were classified into four types : I) no change, II) slight increase in opacity, III) very noticeable formation of clear white spots due to eutectic crystallization with very slow rate of growth of spots, and IV) formation of spots with high rate of growth. The eutectic temperatures (Te) were obtained from the temperature at which spots faded or disappeared. The collapsing temperatures (Tc) were also obtained from the observation during freeze drying, of the temperatures above which the frozen layer of the solution became puffed or collapsed. The electrical resistances of the specimens were measured during cooling and rewarming. These data were compared with each other to discuss the meaning of the changes in appearance during freezing and drying as follows. The formation of spots was due to crowds of eutectic crystal structures. Tc was observed at Te for the substances which exhibited the eutectic behavior, and Tc for the substances which froze solid but in supercooled or super-eutectic states was supposed to be the temperature above which the frozen solution lost solidity.View full abstractDownload PDF (1321K) -
KOJI ITO1970 Volume 18 Issue 8 Pages 1519-1525
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to get useful information regarding the freeze drying process, macroscopic appearance during freezing and drying were observed on solutions of amino acids exhibiting eutectic behavior. The eutectic crystal structures were observed to take the form of white, densely opaque spots. The velocity of the eutectic crystallization was roughly estimated from the increase of the spots' size and number. The electrical resistance of the solution during freezing was also measured. There existed an optimum temperature range to promote the eutectic crystallization for each solute. Freeze drying of these substances produced very characteristic surfaces and interiors leaving behind the solute crystal portion of the eutectic crystal mixtures. The dried sample had a more concentrated shell, namely, considerable differences in concentration occured between the surface layer and the bulk.View full abstractDownload PDF (2155K) -
AKITADA NAKAMURA, SHOZO KAMIYA1970 Volume 18 Issue 8 Pages 1526-1529
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 3, 5, 10-Tetrahydro-1H-pyrazolo[1, 2-b]phthalazine (IVa) and its 2-methyl derivative (IVd), which have two bridgehead nitrogen atoms in a fused ring system, were synthesized by lithium aluminum hydride reduction of the corresponding 2, 3, 5, 10-tetrahydro-1H-pyrazolo[1, 2-b]phthalazine-5, 10-diones (IIIa, IIId). On the other hand sodium borohydride reduction of IIIa and IIId gave 2, 3, 5, 10-tetrahydro-1H-pyrazolo[1, 2-b]phthalazin-5-one (VIa) and its 2-methyl derivative (VId). These compounds afforded the corresponding monomethiodides (Va, Vd, VIIa, VIId).View full abstractDownload PDF (517K) -
MINORU SEKIYA, KUNIO SUZUKI1970 Volume 18 Issue 8 Pages 1530-1534
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTriethylammonium formate, TEAF given by 5HCOOH·2N (C2H5)3 has been introduced as a reagent effective for reduction of carbon-carbon double bond adjacent to carbonyl group, preferably double bond of central methylene carbon of 1, 3-diketone. The reduction is selective at the carbon-carbon double bond. Nitro group, carbonyl group and other carbon-carbon double bond such as cinnamyl of substrate are not affected by the reduction. An improvement in the preparation of substrate compounds, α, β-unsaturated ketones, using boron trioxide as a dehydrating agent, is also given.View full abstractDownload PDF (652K) -
JUN MITSUI1970 Volume 18 Issue 8 Pages 1535-1540
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe apparent specific volume (ASV) and the breaking strength (BS) of mixed systems were investigated in relation to the filling properties of the systems. Two inflection points were given on the BS vs. water content curves and on the ASV vs. water content curves. The air permeability method was adopted to examine the relationship between two inflection points and two critical points C1 and C2. The two inflection points were supported to be two critical points, because they were nearly consistent with those on the mean capillary diameter vs. water content curves. The changes of the extrusion weight and of the properties of mixed systems, with the lapse of time in the process of granulations, were discussed in relation to the changes of the particle compactness and of the breaking strength of mixed systems. In the extrusion type granulator, mixtures may first be compressed between basket wall and extruder, and then the powder bed may be deformed to be pushed out through holes in the basket wall by continued extrusive force.View full abstractDownload PDF (689K) -
JUN MITSUI, RIKIZO AOYAMA, SHINICHIRO KAGA1970 Volume 18 Issue 8 Pages 1541-1547
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of properties of binder solutions on the apparent specific volume and the breaking strength of solid/binder solution mixed systems was investigated in relation to the filling properties of the mixed system. By the effect of additives, the apparent specific volume vs. amount of binder solution curves did not give a characteristic change as compared with the curve of powder/water mixed system. The work of adhesion between powder and binder solution decreased, the minimum apparent specific volume in Funicular-2 region decreased. The breaking strength of mixed systems may be composed of interparticle friction and interparticle adhesion force (tensile strength) by liquid pendular ring. The tensile strength (S) calculated from the equation S=(1-ε)σ AB/dpg was compared with the strength found. It was supposed that the breaking strengths of mixed systems are multiplicable of interparticle friction and tensile strength. The higher the viscosity of binder solution, the larger the tensile strength. The effect of viscosity was minimized efficiently by the addition of detergent. In spite of the effect of properties of binder solutions, the critical points C1 and C2 were determined on the mean capillary diameter vs. amount of binder solution curves. It was also found that the extrusion weight of granules through extrusion type granulator was inversely proportional to the breaking strength of the mixed system.View full abstractDownload PDF (699K) -
MASAKO MAEDA, AKIO TSUJI, HIROSHI IGETA, TAKASHI TSUCHIYA1970 Volume 18 Issue 8 Pages 1548-1552
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3, 3'-Bipyridazine derivatives containing the ferroin group react with iron (II) in a weakly acidic medium to form highly colored red complexes. The spectrophotometric determination method for iron (II), based on this reaction, is moderately selective, the sensitivity being 1.8-2.8×10-3μg Fe (II)/cm2 for log I0/I=0.001 at 520 mμ. The optimum concentration range is 0.5-2.5×10-7 moles of Fe (II)/ml. The complexes are stable at room temperature for 24 hr and contain Fe (II) and the reagents at the ratio of 1 : 3. 3, 3'-Bipyridazine derivatives tested in this examination proved to be superior to 2, 2'-bipyridine.View full abstractDownload PDF (546K) -
IKUO MORIGUCHI, SHIZUO FUSHIMI, NOBUYOSHI KANENIWA1970 Volume 18 Issue 8 Pages 1553-1557
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first ionization potential, IP, of 10 aniline derivatives was estimated from the charge-transfer absorption spectra arizing in the 510-560 mμ region due to their interactions with p-chloranil. The relation of Ip to the rate of enzymatic acetylation, VAc, indicated that VAc, and possibly affinity to the enzyme, increased with an increase in charge-transfer ability of the anilines. But it was also found that VAc became greater with an increase in basicity of the anilines ; this was compatible with the theory for the usual organic acylation. Accordingly, whether or not the charge-transfer was actually concerned with the enzymatic reaction could not be determined from this study, except from the standpoint that organic ionic reactions were generally involved in the transfer of charge. The relation of IP to pKa was theoretically discussed.View full abstractDownload PDF (533K) -
NORIKO KONDO, KYOKO AOKI, HARUMI OGAWA, RYOJI KASAI, JUNZO SHOJI1970 Volume 18 Issue 8 Pages 1558-1562
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structure of chikusetsusaponin III, C40H80O17·2H2O, mp 196-197°, [α]19D+1.5°(MeOH), a crystalline saponin isolated from the rhizome of Panax japonicum was established to be 20 (S)-protopanaxadiol-3-[β-D-glucopyranosyl(1→2)]-[β-D-xylopyranosyl(1→6)]-β-D-glucopyranoside as represented by formula (I). It is very remarkable that the rhizome of Panax japonicum which has been used as the substitute drug of "Ginseng"in Japan, contains the homologous saponin of the ginseng.View full abstractDownload PDF (658K) -
KIICHIRO KAKEMI, HITOSHI SEZAKI, SHOZO MURANISHI, AKEMI YANO1970 Volume 18 Issue 8 Pages 1563-1568
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMechanism of drug absorption from micellar solution was studied through use of drugs which exist predominantly in micellar phase. Particular systems chosen were vitamin A acetate and vitamin A alcohol-Polysorbate-80. Contrary to the notion that the only form in which the drug penetrate the membrane is free drug, both vitamins, entrapped almost completely in micelles, were absorbed fairly well, but not as such, form the rat large intenstine. Disappearance of the vitamins from the perfusate proceeded by two phases, the rapid (initial 15 minutes perfusion period) and the slow phase (follwing 60 minutes period). In the former, extent of the absorption of the vitamins were dependent on the initial concentration of surface-active agent, whereas in the latter, no such tendency was observed. It was demonstrated that in the very early stage of absorption, vitamins solubilized in micelles are absorved onto the membrane, which being favored by the surface-active agent and in the slow phase, absorption now becomes rate-limited by the partition or release of the vitamins from adsorbed micelles to the mucosal layer of the membrane. Despite the large effective surface area, disappearance in the slow absorptive phase of the vitamins from the solution circulated through the small intestine was smaller compared with the large intestine.View full abstractDownload PDF (719K) -
HIROZUMI INOUE, MIKIO TAKEDA, HIROSHI KUGITA1970 Volume 18 Issue 8 Pages 1569-1575
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcetylation and subsequent oxidation of the organoborane intermediate obtained from hydroboration of isoneopine (III) gave (-)-3-methoxy-6β-acetoxy-8α-hydroxy-4, 5α-epoxy-N-methylisomorphinan (IV). Hydroboration of isoneopine-(N-n-butyl)-carbamate (XIV) gave the 6β-(N-n-butyl)-carbamoyloxy-8α-hydroxy derivative (XV). (-)-3-Methoxy-6β-hydroxy-4, 5α-epoxy-Δ7-N-methylisomorphinan (XIII, B/C trans-isocodeine) was synthesized from either IV or XV via elimination of the respective 8α-tosyloxy derivatives (VI and XVI). XIII was also obtained by solvolysis of (+)-3-methoxy-6α-tosyloxy-4, 5α-epoxy-Δ7-N-methylisomorphinan (XIX). Demethylation of XIII gave the title compound (XXII).View full abstractDownload PDF (719K) -
AKIRA TAKAMIZAWA, YOSHIO HAMASHIMA, HISAO SATO, YOSHIHIRO MATSUMOTO1970 Volume 18 Issue 8 Pages 1576-1588
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 1, 3-disubstituted benzimidazolium halides (1a-d, 16) with diethyl- and dimethyl acylphosphonates (2a-b, 12a-b) were investigated. 1 : 1 adducts (3a-b) were obtained from the reactions of 1a and 2a-b. From the reactions of 1a with 12a-b, 1b-d with 2a, and 1b-d with 12a-b were obtained betaines (13a-b, 3c-e, 13c-f), respectively. The adduct 3a was synthesized by an alternative method. Alkaline treatment of both 3a and 3b afforded 1, 3-dimethyl-2-(1-hydroxy)benzyl- and ethylbenzimidazolium iodides (8a-b) as major products. Alkaline treatment of betaines (13a-d, 3c-e) gave only corresponding 2-imidazolinones and/or ring-opened N-formates. Neither of the adducts gave corresponding quinoxaline derivatives. In the case of the reactions of 1, 3-dimethyl-5-nitrobenzimidazolium iodide (16) with 2a-b were obtained 1 : 1 adducts (17a-b) accompanied by ring-opened phosphates (18a-b). The reactions of 16 with 12a-b gave betaines (23a-b). Neither of 17a-b, 18a-b, or 23a-b gave corresponding quinoxaline derivatives. Treatment of 17a with dimethylsulfoxide afforded 1, 4-dimethyl-3-hydroxy-3-phenyl-7-nitro-1, 2, 3, 4-tetrahydro-2-quinoxalinone (25) in moderate yield. The mechanisms of these reactions are discussed briefly.View full abstractDownload PDF (1277K) -
YASUHIRO YAMANE, MOTOICHI MIYAZAKI, SHIGERU IKEDA, NOBUYUKI YAMAJI1970 Volume 18 Issue 8 Pages 1589-1594
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCu-α, α'-dipyridyl (Cu-Dip) has two unoccupied coordination sites, and when acetylacetone, benzoylacetone, dibenzoylmethane, p-carboxydibenzoylmethane, trifluoroacetylacetone, benzoyltrifluoroacetone and salicylaldehyde were reacted on Cu-Dip respectively, the presence of two different equilibria in Chart 1 was suggested spectrophotometrically according to the ratio of Cu-Dip and β-diketone. These equilibria are : Cu-Dip+β-diketone⇄β-diketone-Cu-Dip, β-diketone-Cu-Dip+β-diketone⇄Cu (β-diketone)2+Dip. The isosbestic points which indicate the presence of the above equilibria respectively, were observed in the spectra of the mixed complexes. Furthermore, the study of the relation between the isosbestic points and β-diketone concentration to Cu-Dip revealed the relative reactivity for the formation of Cu(β-diketone)2 which was shown in the order : dibenzoylmethane>benzoylacetone>acetylacetone>salicylaldehyde>p-carboxydibenzoylmethane»trifluoroacetylacetone, benzoyltrifluoroacetone. Mixed complexes of Cu (II) with α, α'-dipyridyl and β-diketone (1 : 1 : 1) were synthesized by reacting β-diketone to Cu-Dip in 50% dioxane solution containing 0.1M NaHCO3.View full abstractDownload PDF (669K) -
TAIICHIRO WATANABE, NOBUO SOMA1970 Volume 18 Issue 8 Pages 1595-1603
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions between tropylium cations and enamines were examined. The reaction of tropylium bromide (I) with pyrrolidine enamine of cyclohexanone in benzene produced 2-tropylcyclohexanone (V) and 2, 6-ditropyl-1-cyclohexylidene pyrrolidinium bromide (IV), whereas the reaction of tropylium fluoroborate (II) with morpholine enamine of the same ketone in aqueous dioxane gave V in almost quantitative yields. Table I summarizes the production of 2-tropyl-substituted ketones by the reaction of II with enamines carried out in aqueous dioxane. The reaction of 7-ethoxy-1, 3, 5-cycloheptatriene (XIII) with enamines in the presence of acetic acid also examined, and participation of two moles of enamine in the reaction was observed on the reaction of XIII with aldehyde enamines. Namely, the reaction of XIII with propionaldehyde enamine and butyraldehyde enamine gave respectively 2-methyl-4-tropyl-2-pentenal (XIV) and 2-ethyl-4-tropyl-2-hexenal (XVII).View full abstractDownload PDF (1107K) -
TAIICHIRO WATANABE, NOBUO SOMA1970 Volume 18 Issue 8 Pages 1604-1609
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of tropylium fluoroborate (I) with morpholine dienamine derived from 4, 4a, 5, 6, 7, 8-hexahydro-2 (3H)-naphthalenone (II) resulted in the hitherto unreported attack of the electrophile at the δ-position of the dienamine, and 8-tropyl- (VI) and 4a-tropyl-4, 4a, 5, 6, 7, 8-hexahydro-2 (3H)-naphthalenone (VII) were obtained. Pyrrolidine dienamines of Δ4-3-oxosteroids (VIII, IX, and X) similarly gave the corresponding 6-tropyl-Δ4-3-oxosteroids (XI, XII, and XIII) with I. Reaction of 7-ethoxy-1, 3, 5-cycloheptatriene (XVIII) with dienamines in the presence of acetic acid was also examined and 6-benzylidenetestosterone (XIX) and 6-benzylidenecholest-4-en-3-one (XX) were obtained respectively by the reaction of XVIII with dienamine of testosterone (VIII) and with that of cholest-4-en-3-one (IX).View full abstractDownload PDF (768K) -
ITIRO YOSIOKA, TADASHI NISHIMURA, AKIKO MATSUDA, ISAO KITAGAWA1970 Volume 18 Issue 8 Pages 1610-1620
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of theasapogenol B, one of seeds sapogenols of Thea sinensis L. (Theaceae) has been established as 3β, 16α, 21β, 22α, 28-pentahydroxy-olean-12-ene (II). Based on the identity of theasapogenol B with barringtogenol C, a sapogenol of Barringtonia acutangula GAERTN. (Lecythidaceae) and its structure by the previous workers being (I), the structure of barringtogenol C has been revised to II incidentally along with the revision of the structure of barringtogenol D from (2) to XVI. In addition, the designations of seeds sapogenols of Thea sinensis L. have been proposed to be theasapogenol A (I), barringtogenol C (II), camelliagenin C (III), dihydropriverogenin A (IV), and theasapogenol E (V) respectively.View full abstractDownload PDF (1219K) -
ITIRO YOSIOKA, TADASHI NISHIMURA, AKIKO MATSUDA, ISAO KITAGAWA1970 Volume 18 Issue 8 Pages 1621-1632
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of theasapogenol A, one of seeds sapogenols of Thea sinensis L. has been established as 3β, 16α, 21β, 22α, 23, 28-hexahydroxy-olean-12-ene (II), and some additional investigations on the oxide ring formation between C-21 and C-16 of barringtogenol C (I) and II have been summarized. In addition, the evidence concerning to the anisotropic effect caused by the trityl function has been presented.View full abstractDownload PDF (1348K) -
SHIGERU TAKANASHI, ZENZO TAMURA1970 Volume 18 Issue 8 Pages 1633-1635
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyanide produces a fluorescent compound from pyridoxal (PAL) by a catalytic action. The velocity of the reaction could be measured by measuring the fluorescence intensity. For a concentration of cyanide below 10-5M, the apparent initial velocity of the reaction was maintained for 60 min at a concentration of 6×10-4M of PAL, and the initial velocity was proportional to the concentration of cyanide. A simple and sensitive fluorometric method for the determination of cyanide was devised based on the above findings. Cyanide was treated with PAL at pH 7.5 and the fluorescence intensity was measured at pH 10.View full abstractDownload PDF (404K) -
EIICHI FUJIHIRA, HISAHIDE TAKAHASHI, MASAO NAKAZAWA1970 Volume 18 Issue 8 Pages 1636-1642
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1) Feeding of 5% taurine diet for 14 weeks caused marked reduction of the body weight increase in young mice of a hereditary hyperglycemic obese strain (KK). Exchange of the diet for control accelerated gain of the body weight in these animals for the subsequent 6 weeks. 2) Adult KK mice fed 5% taurine diet for 10 weeks demonstrated a slight but significant decrease of the initial body weight, mainly due to a reduction of the size of the abdominal fat pads, whereas such effects of long-term feeding of taurine were not observed in adult lean (BALB/C) and experimentally obese (GTG) mice. 3) Suppression of development of obesity was also produced in young KK mice by adding taurine to tap water in 1.0 and 0.5% for 20 weeks. The abdominal fat pads were decreased markedly in size at the high dose of taurine, as compared to those of controls. There was no difference in blood sugar and liver cholesterol between the treated and untreated groups. The long-term feeding of taurine did not cause any change in the fatty acid composition of lipid in the abdominal fat pads, but this treatment served to liver lipid pattern of composition similar to that from BALB/C mice. 4) Whole body macroautoradiography demonstrated that administered taurine-S35 was accumulated largely in the liver, gall bladder, gastrointestinal walls, kidney and spleen. There was no significant difference in distribution pattern of taurine-S35 between KK and BALB/C mice.View full abstractDownload PDF (784K) -
HISASHI NOGAMI, TSUNEJI NAGAI, NAOKI NAMBU1970 Volume 18 Issue 8 Pages 1643-1652
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs an approach to an understanding of the membrane action of phenothiazines, the adsorption from solution was investigated using such adsorbents as carbon black (CB), graphite (GP), silica gel (SG) and polyethylene (PE), and relating the results with other physico-chemical and biological activities of the drugs. The adsorption isotherms by CB and GP were in accordance with Langmuir equation. In the case of SG, the phenomenon looked like a multilayer adsorption. Phenothiazines were considered to be classified into three groups according to the adsorbability by PE. The adsorbed amount was influenced by the molecular volume of R10'N at 9-position, sulfoxide group at 5-position, and the bulkiness of substituent at 2-position. The adsorbed amount increased with pH of buffer solution between 5 and 8, and it was considered that pH had influence on the hydrophobic and hydrophilic balance of the molecule. The decrease in adsorption with addition of urea demonstrated that the adsorption of phenothiazines proceeded on the hydrophobic interaction. The adsorbability of phenothiazines by CB increased with the surface tension lowering of solution and also with the partition coefficient in CHCl3-0.2N HCl. It was shown that the adsorbability have relation to the neuroleptic and the haemolytic activities.View full abstractDownload PDF (909K) -
AKIRA HANAKI1970 Volume 18 Issue 8 Pages 1653-1657
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe transformation reactions, i.e., transguanylation and cyclization, of AET and APT were investigated with the potentiometric titration technique. Both reactions, which proceed probably through the similar intermediate, were promoted with the increasing amounts of alkali added initially. In the initial stage of the reaction, the transguanylation occupied larger part in the transformation of AET, as well as in APT. The half life of the conjugate base, which is an active species for the transguanylation, was increased linearly with the reciprocal of the initial concentration of the conjugate base. From the concentration dependence of the half life, measured in the addition of 0.5 equivalent alkali, it was deduced that the transguanylation is second order with respect to the isothiuronium salt. The Arrhenius plots of the rates in AET and in APT gave straight and parallel lines.View full abstractDownload PDF (551K) -
TOSHIO NAMBARA, KAZUTAKE SHIMADA, TOSHIYUKI NEMOTO, SHUJIRO GOYA1970 Volume 18 Issue 8 Pages 1658-1662
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs the key intermediates leading to the titled compounds 17β-(5-isoxazolyl)androst-14-ene (IIb) and 17β-(3-pyrazolyl) androst-14-ene (VIa) were prepared from 20-ethoxy-21-formyl-17β-pregna-14, 20-diene (Ib) with hydroxylamine and hydrazine hydrate, respectively. Epoxidation of IIb with monoperphthalic acid did take place from the α-side of the Δ14-double bond to yield the 14α, 15α-oxido compounds (III). Reaction with N-bromoacetamide followed by treatment with alumina resulted in formation of the epimeric β-epoxides (V). Similar elaborations with the 17β-(3-pyrazolyl)-Δ14-steroid gave the epimeric 14, 15-epoxides (VII, IX) with success, when VIa was previously converted into the N-acetate (VIb).View full abstractDownload PDF (726K) -
TAKAICHI ARITA, RYOHEI HORI, KEIJI ITO, KAZUO ICHIKAWA, TAKASHI UESUGI1970 Volume 18 Issue 8 Pages 1663-1669
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to understand the transformation metoclopramide, 4-amino-5-chloro-N-[2-(diethylamino)-ethyl]-2-methoxybenzamide (M), in the body, the excrements in the urine of rabbits after the oral administration were examined. As a result, the five transformation products were revealed together with the parent compound. The urine was adjusted to pH 11-12, followed by extracting with ethylene dichloride ; thus, unchanged M and the two transformation products were found in the organic layer : One of the transformates was an oxidation product of the primary amino group so that the reduction of this product resulted in the parent compond. The other was identified to be 4-amino-5-chloro-N-[2-(ethylamino)-ethyl]-2-methoxybenzamide corresponding to M deethylated. At pH 4-5, a compound which was preferably extracted into ethylene dichloride was confirmed as 4-amino-5-chloro-2-methoxy benzoic acid resulting form rupture of the acid amide bond. Water-soluble products, on the other hand, were established as N4-glucuronide and N4-sulfonate of M. These two conjugates and unchanged M were detected to be the major urinary constituents on the thin-layer chromatogram. However, no evidence was obtained for the presence of N4-acetyl conjugate.View full abstractDownload PDF (769K) -
TAKAICHI ARITA, RYOHEI HORI, KEIJI ITO, KAZUO ICHIKAWA1970 Volume 18 Issue 8 Pages 1670-1674
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe method of separatory determination of metoclopramide and its N4-glucuronide and N4-sulfonate, which are the major excrements in the urine and the bile of rabbits receiving metoclopramide, was established. Metoclopramide in the sample solution was extracted with chloroform under the condition of alkaline pH, and back-extracted with 1/15M KH2PO4 (pH 4.5). Metoclopramide in the aqueous layer was diazo-coupled in a brown test-tube which was used with a view to taking away the influence of light ; thus, a developed color was measured at 540 mμ. On the other hand, the separation of the glucuronide and the sulfonate from each other was carried out by utilizing the difference in stability between them, which are hydrolysed in an acid medium. Resulting metoclopramide was isolated and determined as above-mentioned. This method was applied to the urine and the bile of rabbits administered metoclopramide intravenously.View full abstractDownload PDF (596K) -
TAKAICHI ARITA, RYOHEI HORI, KEIJI ITO, HITOSHI SEKIKAWA1970 Volume 18 Issue 8 Pages 1675-1679
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOf metoclopramide-N4-glucuronide and -N4-sulfonate, both of which were found as the major constituents in the bile after metoclopramide administration to rabbits, reabsorption from the intestine was studied to explore the possibility of the entero-hepatic circulation. Following the administration of the N4-conjugates into the rabbit duodenum, the urinary constituents were quantitatively measured at various times over a period of 12 hours. In the case of the sulfonate, all recovered in the urine was found to be the sulfonate. The result suggests that this conjugate itself may be absorbed from the intestine without being hydrolysed. On the other hand, when the glucuronide was intraduodenally given, at least two features of urinary excretion were observed : One showed that the glucuronide accounts for more than 90% of the total recovered in 8 hours, and the other did that the proportion of it to the total decreases with time. From the examinations for the stability in the aqueous solution and for the urinary excretion after the intravenous administration, it was concluded that the glucuronide may be absorbed from the intestine not only in the parent compound, namely, metoclopramide resulting from the hydrolysis but in the intact form as well as the sulfonate.View full abstractDownload PDF (636K) -
MITSUJI YANAI, TOSHIO KINOSHITA, SHIGEKO TAKEDA, HIROSHI SADAKI, HIROS ...1970 Volume 18 Issue 8 Pages 1680-1684
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (628K) -
MITSUJI YANAI, TOSHIO KINOSHITA, SHIGEKO TAKEDA, MASATO MORI, HIROSHI ...1970 Volume 18 Issue 8 Pages 1685-1692
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
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HISAYUKI MATSUO, HIROKO KOBAYASHI, TAKASHI TATSUNO1970 Volume 18 Issue 8 Pages 1693-1695
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
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SEIJU KUBOTA, YOSHIYUKI KOIDA, TAKAYUKI KOSAKA, OSAMU KIRINO1970 Volume 18 Issue 8 Pages 1696-1698
Published: August 25, 1970
Released on J-STAGE: March 31, 2008
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