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井上 重治
1968 年 16 巻 4 号 p.
573-579
発行日: 1968/04/25
公開日: 2008/03/31
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Cyclization of the dialdehyde, obtained by periodate oxidation of tetra-N-acetyl-kanamycin, with nitromethane, followed by reduction and hydrazinolysis gave the titled compounds. Structural assignment of these derivatives was accomplished by NMR spectroscopy and degradation to the respective component sugars. Direct treatment of 3'-nitro-3'-deoxyderivative with hydrazine gave, via decomposition of the nitro sugar portion, O-a-D-3-amino-3-deoxyglucopyranosyl (1→6)-2-deoxystreptamine.
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野上 寿, 花野 学, 山田 秀雄
1968 年 16 巻 4 号 p.
580-585
発行日: 1968/04/25
公開日: 2008/03/31
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フリー
When Danielli's model, the transition state theory and the formal treatment on the basis of the extrathermodynamic relationships were applied to the intestinal absorption of foreign organic compounds, it was expected that there should be the following relation between the absorption rate coefficients for the compound (RS) having a substituent group (S) and for the mother compound (RH). log k
RS/k
RH=constant The perfusion experiments through the small intestine of anesthetized rats for a number of benzene derivatives were carried out. The logarithmic plots of the residual ratio against the perfusion time gave straight lines and from the slopes the absorption rate coefficients were obtained. The results indicate that the values of log k
RS/k
RH for a given substituent group (S) have a proper value which is called the substituent constant.
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野上 寿, 花野 学, 山田 秀雄
1968 年 16 巻 4 号 p.
586-591
発行日: 1968/04/25
公開日: 2008/03/31
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It was expected that the absorption rate coefficient of the foreign organic compound was, as a first approximation, a simple additive function of its substituent groups and that the absorption rate coefficient should be predicted from the additivity rule. Furthermore, the following relationship for the intestinal absorption rate of foreign organic compounds was expected from the application of the activated diffusion model, the transition state theory and the formal treatment based on the extrathermodynamic relationships, log k
RS(i)…s(j)/k
RS(i)s(j)=constant where k
RS(i)…s(j) or k
RS(i)s(j) denotes the absorption rate coefficient for the compound with or without the intramolecular interaction, respectively. The perfusion experiments through the small intestine of anesthetized rats for various benzene derivatives with or without intramolecular interaction were carried out. The logarithmic plots of the residual ratio against the perfusion time gave straight lines and from the slopes the absorption rate coefficients were obtained. The results indicate that the absorption rate coefficient can be essentially predicted from the additivity rule and that the values of log k
RS(i)…s(j)/k
RS(i)s(j) for a given combination of interacting groups have a proper value which is called the intramolecular interaction constant.
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森口 郁生, 和田 栄, 佐野 肇
1968 年 16 巻 4 号 p.
592-596
発行日: 1968/04/25
公開日: 2008/03/31
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Binding of anionic dye 2-(4'-hydroxyphenylazo) benzoic acid (HABA) to bovine serum albumin at pH 7.4 was studied spectrophotometrically. The relationship between albuminbound ratio of HABA and concentration of the unbound dye was expressed by a modified Langmuir-type equation involving a repulsing interaction. The binding becomes more difficult with the increasing bonds. The binding constant and the number of binding sites on albumin were evaluated in 0.05 M phosphate buffer solution and in 0.15 M tris. buffer solution at 25°and 37°.
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森口 郁生
1968 年 16 巻 4 号 p.
597-600
発行日: 1968/04/25
公開日: 2008/03/31
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Binding constants for benzoic acid, its monosubstituted derivatives, and pyridine-carboxylic acids with bovine serum albumin were evaluated spectrophotometrically by utilizing the competition with 2-(4'-hydroxyphenylazo) benzoic acid (HABA). A modified Langmuir-type equation which quantitatively represented the binding of HABA to albumin was expanded to express the competitive system in which HABA and a noncolored compound competed for the same binding sites on albumin molecules in the same manner. The values of the binding constant obtained by the use of the expanded equation were irrespective of the three levels of initial concentration of the acids. A linear relation was observed between logarithm of the binding constant and pK
a for the acids except ortho-substituted benzoic acids and pyridine-2-carboxylic acid.
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森口 郁生, 和田 栄, 西沢 孝子
1968 年 16 巻 4 号 p.
601-605
発行日: 1968/04/25
公開日: 2008/03/31
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Binding constant, K, for 19 sulfonamides with bovine serum albumin was evaluated spectrophotometrically utilizing the competition between 2-(4'-hydroxyphenylazo)-benzoic acid and sulfonamides. The values of log K well correlated with degree of the decrease in in vitro bacteriostatic activities by the addition of bovine serum. A linear relationship was also observed between log K and pK
a for the sulfonamides. The relationships between log K and in vitro bacteriostatic activities against Escherichia coli 0-55 and Staphylococcus aureus 209P were expressed with parabolic curves, which indicated the optimum values of log K being 3.5-4.5 for the potent sulfonamides.
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鵜飼 茂夫, 広瀬 一雄
1968 年 16 巻 4 号 p.
606-612
発行日: 1968/04/25
公開日: 2008/03/31
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フリー
Die Reaktion des a-Naphthols mit Dialkylsulfoxid bzw. Methylarylsulfoxid bei Gegenwart der Mischung von Perchlorsaure und Phosphoroxychlorid fuhrte leicht zu Dialkyl-4-oxynaphthylsulfoniumperchlorat (I-IV) sowie Methyl-aryl-4-oxynaphthylsulfoniumperchlorat (V-VII). Auch durch Eintropfen der gerechneten Menge Hydroperoxid ins Reaktionsgemisch in Gegenwart der Mischung von Perchlorsaure und Phosphoroxychlorid ging die Reaktion mit Dialkylsulfid bzw. Methylarylsulfid statt Sulfoxid glatt fort, und dabei wurden gewunschte Sulfoniumsalze (I-VII) leicht mit guter Ausbeute erhalten. Durch Oxydation der von den Sulfoniumsalzen (I-VII) abgeleiteten 4-Alkylthio-oder 4-Arylthio-naphthole (XI-XVII) mit Kaliumnitrosodisulfonat wurden 4-Alkylthio-oder 4-Arylthio-naphthochinone (XVIII-XXIV) am zweckmaBigsten erhalten.
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木村 道也, 服部 保次, 吉沢 逸雄, 藤間 貞彦
1968 年 16 巻 4 号 p.
613-617
発行日: 1968/04/25
公開日: 2008/03/31
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Gas chromatographic determination of monosaccharides such as L-arabinose, L-rhamnose, D-xylose, D-mannose, D-galactose, and D-glucose was studied. The recovery of sugars under hydrolysis condition was examined by GLC (Fig. 1) and was found to be almost quantitative when steroidal glycosides were hydrolyzed with N sulfuric acid in dioxane-water (1 : 3) solution (Table III). A simple and accurate method by GLC was thus presented for the individual determination of sugar components in the micro amounts (5-10 mg) of steroidal saponins. The molar ratios of sugar components were determined on the new convallasaponins by this method (Table V).
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石川 正雄, 藤本 学, 酒井 満喜子, 松本 敦子
1968 年 16 巻 4 号 p.
618-621
発行日: 1968/04/25
公開日: 2008/03/31
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フリー
Les auteurs ont poursuivi des reactions de cyclisation entre l'anhydride cis-perhydrophtalique (I) et de l'hydrazine (libre ou substituee) ou de l'hydrazide carboxylique ou sulfonique. En confirmation de sa structure sur les produits reactionels, ils ont conclu qu'on peut obtenir, apres cette forme de reaction, une systeme pentagonale telle que l'amino-2 cis-perhydroisoindolinedione-1, 3, excepte en cas de la cyclisation par de l'hydrazine N, N'-disubstituee.
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石川 正雄, 藤本 学, 酒井 満喜子, 松本 敦子
1968 年 16 巻 4 号 p.
622-625
発行日: 1968/04/25
公開日: 2008/03/31
ジャーナル
フリー
Les auteurs ont recherche quelques reactions de cyclisation entre l'anhydride cis-perhydrophtalique (I) ou l'anhydride ethano-3, 6 cis-tetrahydro-1, 2, 3, 6 phtalique (VII) et de l'hydroxylamine (libre ou substituee). En confirmation de sa structure sur les produits reactionels, ils ont conclu qu'on peut obtenir, d'apres ce genre de reaction, une systeme pentagonale comme l'hydroxy (libre ou substitue)-2 cis-polyhydroisoindolinedione-1, 3, excepte en cas de la cyclisation par de l'hydroxylamine N-substitutee.
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川村 邦夫
1968 年 16 巻 4 号 p.
626-633
発行日: 1968/04/25
公開日: 2008/03/31
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The mechanism of a new color reaction of aminopyrine has been studied. Aminopyrine gives orange red coloration by the reaction with phenol and potassium ferricyanide in ammonium acetate or ammonium chloride buffer. Colored substance of this reaction has been isolated and determined to be 4-(1', 4'-benzoquinone-4'-imino) antipyrine, which is the same as the reaction product obtained from 4-aminoantipyrine. But in the reaction of aminopyrine it has been found that presence of ammonium ion is essential to the coloration, contrary to the reaction of 4-aminoantipyrine, and in presence of excess aminopyrine intensity of color is proportional to the concentration of ammonium ion. Further investigation of the role of ammonium ion in the color reaction of aminopyrine supports the suggestion that in the first step ammonium ion and phenol are oxydatively condensed to produce 1, 4-benzoquinone imide type intermediate, which reacts with aminopyrine to produce 4-(1', 4'-benzoquinone-4'-imino) antipyrine as the consequence of transdimethylaminaton. On the basis of these experiments, a new colorimetric determination method of ammonia has been established.
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木村 道也, 河田 明治, 中館 正弘, 小尾 陞, 川添 政彦
1968 年 16 巻 4 号 p.
634-640
発行日: 1968/04/25
公開日: 2008/03/31
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The color-substance, C
9H
9O
5N
2K, (III) was successfully isolated from the Janovsky reaction-mixture of acetone, m-dinitrobenzene (I), and potassium hydroxide. The spectral and chemical properties were studied in comparison with the potassium salt of 2, 4-dinitrobenzyl methyl ketone (V), the Meisenheimer-like complex structure of III being thus confirmed : Absorption spectra of III and V in acetone were quite identical with those of the Janovsky and the Zimmermann reaction-mixture, respectively (Fig. 1) ; λ
max of III varied highly in different solvents, in contrast to that of V (Table I). NMR spectrum gave the sextet structure of the proton (Hδ) attached to the ring sp
3 hybridized carbon atom (Table II). When the solution of III was kept at pH 1, diacetonyl-dinitroazoxybenzene, V, and I were isolated. Strong alkali decomposed III to 2, 4-dinitrophenol and unknown substances ; a remarkable difference from V was shown as for the elimination of nitrite ion. Ultra-violet irradiation on III gave the unknown substance, free of carbonyl absorption in IR spectrum.
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相見 則郎, 藤本 治宏, 柴田 承二
1968 年 16 巻 4 号 p.
641-646
発行日: 1968/04/25
公開日: 2008/03/31
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A genuine sapogenin, saikogenin E, was isolated by applying the Smith-type controled degradation procedure for saikoside II fraction, one of the main saponins of Bupleurum falcatum L. It was also obtained by alkaline degradation of the periodate oxidized saponin. The structure of saikogenin E (Ia) was elucidated and saikogenins B and C were proved to be the artifacts derived from it. Saikogenin G, the genuine sapogenin corresponding to saikogenin D, was also obtained by modified de Mayo-type degradation method and its structure was established as (Va).
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山本 久夫, 中尾 勝, 小林 晁
1968 年 16 巻 4 号 p.
647-653
発行日: 1968/04/25
公開日: 2008/03/31
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1) Some novel procedures for syntheses of 1-aroylindole-3-aliphatic acids are developed. 2) According to these methods new 1-benzoylindole-3-aliphatic acid derivatives are prepared for pharmacological test. 3) Some reaction mechanisms on these methods are suggested.
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老田 貞夫, 大木 英二
1968 年 16 巻 4 号 p.
654-662
発行日: 1968/04/25
公開日: 2008/03/31
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It was found that the insertion reaction of a carbene produced at bridged carbon (C
9) of 3-methyl-3-azabicyclo [3. 3. 1] nonane proceeded exclusively into the opposite side to N-methyl group to yield 3-methyl-3-azatricyclo [6. 1. 0. 0
5, 9] nonane (III), while that of a carbene at bridged carbon (C
8) of 3-methyl-3-azabicyclo [3. 2. 1] octane was to the same side of N-methyl group to give 2-methyl-2-azatricyclo [5. 1. 0. 0
4, 8] octane (XV).
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亀谷 哲治, 高野 誠一, 芳賀 清次
1968 年 16 巻 4 号 p.
663-667
発行日: 1968/04/25
公開日: 2008/03/31
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Diastereoisomeric mixture of racemic melanthooioine (I and II), was synthesized by the following procedures. Bischler-Napieralski reaction of the amide (XIII), which was obtained by Schotten-Baumann reaction of 4-hydroxy-3-methoxyphenethylamine zinc chloride (IX) with acid chloride (X), followed by ethoxycarbonylation of the amide (XI) with ethyl chlorocarbonate, afforded the 3, 4-dihydroisoquinoline (XIII). Reduction with sodium borohydride of the methiodide (XIV), which was obtained by methylation of XIII with methyl iodide, gave a mixture of 1, 2, 3, 4-tetrahydroisoquinolines, (XV) and (XVI), whose hydrolysis with an alkaline solution afforded the latter compound (XVI). Secondly, double Ullmann reaction of the preceding compound (XVI) afforded a diastereoisomeric mixture of O, O-dibenzylmelanthioidine, which was debenzylated to give a diastereoisomeric mixture of I and II. Therefore, it is of particular interest that the twentymembered ring system as melanthioidine-type compound has been synthesized.
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Studies on Ergot Alkaloids and Related Compounds. XV. Reductions of cis- and trans-4-Methyl-2-methylen-3-oxo-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo [f] quinolines and Preparation of trans-syn-2, 4-Dimethyl-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo-[f] quinoline
堀井 善一, 栗原 拓史, 二宮 一弥
1968 年 16 巻 4 号 p.
668-671
発行日: 1968/04/25
公開日: 2008/03/31
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The behaviors of cis- and trans-4-methyl-2-methylen-3-oxo-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo [f] quinolines toward catalytic and chemical reductions were examined and thereby the hitherto unknown trans-syn-2, 4-dimethyl-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrobenzo-[f] quinoline was secured.
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為政 脩, 岡田 昌二, 岩崎 節夫, 渡辺 英子
1968 年 16 巻 4 号 p.
672-678
発行日: 1968/04/25
公開日: 2008/03/31
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フリー
4-Fluoro- and 4-nitro-phenylalanines inhibited the phenylalanine incorporation in a cell-free system of Ehrlich mouse ascites tumor cells, and their inhibition occurred in two steps, i.e. amino acid activation and transfer of phenylalanine to microsomes in protein synthesis. In the over-all incorporation experiment of a cell-free system, there was seen an antagonism of incorporation between phenylalanine and 4-fluorophenylalanine. The phenylalanine analogs did not exert their inhibitions on the incorporation of a few tested amino acids other than phenylalanine. Furthermore, the fluoro and nitro analogs behaved differently on the phenylalanine accumulation into "amino acid pool"of intact cells, the former being stimulative and the latter a little inhibitory. Discussions were made on several problems encountered in the inhibition of protein synthesis by the analogs.
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小河原 宏, 前田 謙二, 小山 軍治, 長縄 博, 梅沢 浜夫
1968 年 16 巻 4 号 p.
679-687
発行日: 1968/04/25
公開日: 2008/03/31
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Structural studies on pyridomycin have been performed by chemical degradation such as ozonolysis and hydrolysis in alkaline and acidic media. New acids, α-oxo-β-methylvaleric acid, 4-amino-3-hydroxy-2-methyl-5-(3-pyridyl) pentanoic acid and its dehydration and deamination products are obtained as degradation products. The structure I, 10-hydroxy-6-(3-hydroxypicolinamido)-5, 11-dimethyl-2-(1-methylpropylidene)-9-(3-pyridylmethyl)-8-aza-1, 4-dioxa-cyclododecane-3, 7, 12-trione, has been proposed for pyridomycin. This structure including its stereochemistry was recently determined by X-ray analysis of the crystal of pyridomycin dihydrobromide (C
27H
32O
8N
4·2HBr·H
2O·CH
3CH
2OCOCH
3).
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富田 真雄, 正木 幸雄, 冨士谷 憲徳, 坂谷 芳郎
1968 年 16 巻 4 号 p.
688-694
発行日: 1968/04/25
公開日: 2008/03/31
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Potassium ferricyanide oxidation of dl-4'-O-methyl-N-methylcoclaurine (VII) afforded two species of diphenyl ether derivatives (Base A'and Base B'), which were racemic and diastereoisomeric each to each. The yield was about 15%. Spectrometric studies of the dimerization product and their O-methyl ethers gave proof to their structures. The structures were confirmed by a synthesis of their O-methyl ethers via an alternative route. Configurations of the products were also assigned by the chemical correlation with fangchinoline, having (L, L)-configuration on the two asymmetric carbon atoms.
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畑 俊一
1968 年 16 巻 4 号 p.
695-698
発行日: 1968/04/25
公開日: 2008/03/31
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In previous papers, it was reported that menadione formed complexes with various electron donrs in aqueous systems, and that the driving force of the complex formation was due to the charge transfer force. However, the charge transfer absorption bands of the complexes were not recognized completely in the above systems. In the present paper, the charge transfer absorption bands of the complexes between menadione and either caffeine or ethyl p-aminobenzoate were determined in chloroform, and energies of the charge transfer absorption bands were compared with those between better electron donors and menadione, or between better electron acceptors and either caffeine or ethyl p-aminobenzoate. Consequently, it was concluded that the indistinct charge tranfser absorption bands of the complexes between menadione and either caffeine or ethyl p-aminobenzoate in aqueous system are responsible for lower electronic affinity of menadione, for higher ionization potentials of caffeine or ethyl p-aminobenzoate and for lower solubilities of caffeine or ethyl p-aminobenzoate.
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河合 聰, 田村 善蔵
1968 年 16 巻 4 号 p.
699-701
発行日: 1968/04/25
公開日: 2008/03/31
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Catecholamines were treated with trifluoroacetic anhydride in tetrahydrofuran at a room temperature. The reaction mixture was diluted with n-hexane and was injected directly onto a gas chromatograph. A complete separation of three catecholamines, epinephrine, dopamine and norepinephrine, was achieved on a 2% GE-XF 1105 glass column at 190°. Isodrin was used as an internal standard. The formation of the trifluoro-acetates was rapid and simple. The trifluoroacetates produced were volatile enough to permit the use of selective columns, and satisfactory responses were obtained from several ng of them using an electron capture detector.
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津田 充宥, 川添 豊
1968 年 16 巻 4 号 p.
702-706
発行日: 1968/04/25
公開日: 2008/03/31
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From the IR spectrum in C-D stretching region of 2, 6-dideuterated piperidine, N-methylpiperidine, and N-isopropylpiperidine, quantitative evaluation was made about conformational preference of the non-bonded electron pair of nitrogen, Thirty percent of the lone pair was proved to exist in equatorial position in piperidine molecule in carbon tetrachloride.
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山崎 勝, 青木 大, 鎌田 皎
1968 年 16 巻 4 号 p.
707-714
発行日: 1968/04/25
公開日: 2008/03/31
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Blood levels of 14 sulfonamides in rabbits subjected to intravenous administration were found to decrease following a first-order rate. The rate constants for acetylation and excretion were estimated from the first-order half-life in blood and the degree of acetylation in urine. Relationship between physicochemical properties of sulfonamides and rates of excretion was discussed. Binding of sulfonamides with plasma protein was scarcely correlated with the excretion rate. Rate constant of excretion, k
3, was closely correlated with partition coefficients between chloroform and a buffer solution of pH 8.8.
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川添 豊, 吉岡 佑子
1968 年 16 巻 4 号 p.
715-720
発行日: 1968/04/25
公開日: 2008/03/31
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Acid-catalyzed deuterations of 2-pyridinol, 2-quinolinol, and 1-isoquinolinol were examined and their deuteration reactivities were discussed in connection with their electrophilic substitution reactions other than deuteration.
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山崎 勝, 青木 大, 鎌田 皎
1968 年 16 巻 4 号 p.
721-727
発行日: 1968/04/25
公開日: 2008/03/31
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Rate constants of acetylation, k
1, and excretion, k
3, for 14 sulfonamides have been studied using pure strain rats. The results were compared with those of rabbits. Values of k
3 in rats were closely related with partition coefficients at pH same as of urine. Excretion of sulfonamides was markedly influenced by urinary pH. The urinary pH of rats was modified to 8.6±0.2 by the administration of NaHCO
3. Then, a rate constant for excretion was twice increased. The results suggest that sulfonamides are reabsorbed from the renal tubule in the form of unionized molecules in the filtrate.
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内藤 武男, 岡野 淳二, 門矢 静夫, 三木 藤作, 稲岡 万里, 諸井 黎明, 清水 正夫
1968 年 16 巻 4 号 p.
728-733
発行日: 1968/04/25
公開日: 2008/03/31
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The stereoisomers of 4-aminomethylcyclohexanecarboxylic acid (I) and (II) were completely separated from their mixture, respectively, and it is proved that lowermelting isomer has the cis-configuration and higher-melting isomer whose antiplasmin activity is much potent has the trans-configuration.
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森口 郁生, 和田 栄
1968 年 16 巻 4 号 p.
734-738
発行日: 1968/04/25
公開日: 2008/03/31
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近藤 保, 富沢 みち子
1968 年 16 巻 4 号 p.
738-740
発行日: 1968/04/25
公開日: 2008/03/31
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杉浦 寿美, 鈴木 英次, 内藤 多喜夫, 井上 昭二
1968 年 16 巻 4 号 p.
741-745
発行日: 1968/04/25
公開日: 2008/03/31
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杉浦 寿美, 鈴木 英次, 内藤 多喜夫, 井上 昭二
1968 年 16 巻 4 号 p.
745-750
発行日: 1968/04/25
公開日: 2008/03/31
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鈴木 英次, 杉浦 寿美, 内藤 多喜夫, 井上 昭二
1968 年 16 巻 4 号 p.
750-755
発行日: 1968/04/25
公開日: 2008/03/31
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陣 朝洋, 今成 登志男, 山本 晴彦, 管 孝男
1968 年 16 巻 4 号 p.
755-757
発行日: 1968/04/25
公開日: 2008/03/31
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竹本 常松, 曳野 靖子, 荒井 富雄, 今野 長八, 鍋谷 将, ヒキノ ヒロシ
1968 年 16 巻 4 号 p.
759-760
発行日: 1968/04/25
公開日: 2008/03/31
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有富 正和, 川崎 敏男
1968 年 16 巻 4 号 p.
760-761
発行日: 1968/04/25
公開日: 2008/03/31
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竹本 常松, 在原 重信, 曳野 靖子, ヒキノ ヒロシ
1968 年 16 巻 4 号 p.
762
発行日: 1968/04/25
公開日: 2008/03/31
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馬場 義彦, 美津島 宏, 渡辺 宏
1968 年 16 巻 4 号 p.
763-764
発行日: 1968/04/25
公開日: 2008/03/31
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老田 貞夫, 大木 英二
1968 年 16 巻 4 号 p.
764-767
発行日: 1968/04/25
公開日: 2008/03/31
ジャーナル
フリー
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井下田 浩, 土屋 隆, 山田 むつみ, 新井 平八郎
1968 年 16 巻 4 号 p.
767-769
発行日: 1968/04/25
公開日: 2008/03/31
ジャーナル
フリー
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中島 暉躬
1968 年 16 巻 4 号 p.
769-770
発行日: 1968/04/25
公開日: 2008/03/31
ジャーナル
フリー
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古谷 力, 生田 安喜良
1968 年 16 巻 4 号 p.
771
発行日: 1968/04/25
公開日: 2008/03/31
ジャーナル
フリー