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NOBUO TANAKA, GOICHI HIRATA, ISAMU UTSUMI
1970 Volume 18 Issue 6 Pages
1083-1090
Published: June 25, 1970
Released on J-STAGE: March 31, 2008
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The precipitation reaction of polyacrylic acid (PAA), polymethacrylic acid (PMA), polyvinyl alcohol sulfate (PVS), and polyvinyl alcohol phosphate (PVP) with O-benzoylthiamine disulfide (BTDS) has been investigated as a function of BTDS concentration, molecular weight, acid strength, and neutralization degree of them in aqueous solution. This precipitation reaction was found to be independent of molecular weight as long as the molecular weight is in the high polymer range, but remarkably to vary with BTDS concentration, acid strength, and neutralization degree. The extent of BTDS cation binding increases in the order PMA<PAA<PVP<PVS. On the other hand, the rate of release of BTDS from the polyacid complexes in 0.1N HC1 aqueous solution decreases in the order BTDS-PVP>BTDS-PMA>BTDS-PAA>BTDS-PVS. The blood total thiamine level after oral administration of the BTDS-polyacid complexes into rabbits has also been investigated. The BTDS-PVS complex exhibited sustained blood level, but with the other complexes, sustained blood levels were not observed.
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HISASHI NOGAMI, JUN HASEGAWA, NORIKO IKARI, KACHIKO TAKEUCHI, KYOKO AN ...
1970 Volume 18 Issue 6 Pages
1091-1098
Published: June 25, 1970
Released on J-STAGE: March 31, 2008
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Kinetic studies were made about the exchange reactions between dibenzyl disulfide (I) and cysteine, and between diphenyl disulfide (III) and cysteine, in order to determine the dependence on the reaction rates of the structures of disulfides and of thiols. It was demonstrated that the greater the pK
a of the thiols or the smaller the pK
a of the leaving molecule from disulfides, the greater are the rate constants. It was also shown that these exchange reactions stood in equilibria. Being compared this with the reactions between thiamine derivatives of disulfide type and thils where reverse reaction does not proceed, it may be concluded that the absence of reverse reaction is due to the thiamine's behavior in aqueous solution that the thioaniontype structure readily turn to thiazolium-type one below neutral pH.
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HIKARU OZAWA, MASASHI SATO, SHINSAKU NATORI, HIDEKO OGAWA
1970 Volume 18 Issue 6 Pages
1099-1103
Published: June 25, 1970
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An aminoquinone was isolated from the muscle of Ascaris lumbricoides var. suis and characterized as rhodoquinone-9 (I, n=9) by the spectral data and by the identification with the synthetic specimens from ubiquinone-9 (III, n=9) and from 5-demethoxyubiquinone (IV). Biological significance of occurrence of the quinone in the worm is also discussed.
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ISAO SEKI, HIROMU TAKAGI
1970 Volume 18 Issue 6 Pages
1104-1111
Published: June 25, 1970
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Syntheses and pharmacological observations of the N-substituted-morphinan dihydronormethines and the O-alkyl-isoureas related to morphinan, norpethidine, or phenethylamine with interest to the basic center in the molecules were described.
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TOKISHI HAYASHI, KUNIMITSU HARA, SATOSHI KAWAI, TAKEO OHNO
1970 Volume 18 Issue 6 Pages
1112-1117
Published: June 25, 1970
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The correlation between the structure and fluorescence intensity of flavone derivatives and their beryllium chelates was investigated. The ligands of type I, II in Chart 1 and their beryllium chelates did not produce fluorescence, while the ligands of type III, IV fluoresced by themselves and formed fluorescent chelates with beryllium ion. The ligands of type V which were non-fluorescent ligands formed fluorescent beryllium chelates.
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SHOGO UEMATSU, YUKIO AKAHORI, SEIGO FUKUSHIMA, YASUHISA SAIKI, AKIRA U ...
1970 Volume 18 Issue 6 Pages
1118-1123
Published: June 25, 1970
Released on J-STAGE: March 31, 2008
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The high-resolution proton magnetic resonance spectra of curzerenone observed in 20 mole percent solution in carbon tetrachloride and deuterochloroform were analyzed with the aid of the computation and the double resonance experiments. The relative sign of the coupling constants was determined by the spin-tickling method, and the accurate values of parameters were obtained. It was confirmed the presence of the long-range spin coupling
5J
HH via the ether linkage in the fused furan ring, and the values of nuclear magnetic resonance parameters were shown to be reasonable for the predicted structure.
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SHIRO TERASHIMA, MUNEHIKO NARA, SHUNICHI YAMADA
1970 Volume 18 Issue 6 Pages
1124-1136
Published: June 25, 1970
Released on J-STAGE: March 31, 2008
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In order to determine the spin state of the acyl nitrene (VII) which is thought to intervene in the insertion reaction at the intramolecular aliphatic C-H bond, optically active (R)-5-methyl-6-phenylhexanoyl azide ((R)-XVII) was synthesized from ((S) (+)-2-methyl-3-phenylpropionic acid ((S) (+)-XVIII), and submitted to photochemical decomposition in methylene dichloride solution. (S) (-)-6-Benzyl-6-methyl-2-piperidone ((S) (-)-XIX) was obtained as a reaction product in a 4.3% yield with 98% retention of configuration. These results show that the singlet state acyl nitrene (XXXVIII) produced from (R)-XVII by irradiation, had inserted into the intramolecular optically active C-H bond through the transition state (IL), as in the intramolecular insertion reaction of alkoxycarbonyl nitrene. Independent synthesis of (S) (-)-XIX from (R)-α-methylphenylalanine ethyl ester ((R) (+)-XX), and preliminary experiments on racemic compounds are also reported.
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SHIRO TERASHIMA, MITSUYOSHI WAGATSUMA, SHUNICHI YAMADA
1970 Volume 18 Issue 6 Pages
1137-1144
Published: June 25, 1970
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The following C-C bond formation from C-N bond were stereochemically investigated. The reaction of (S)-XII with Na
2S
2O
4, (S)-XIII with HgO and α-elimination of (S)-XIV, all gave (R)-XV in 50-70% yields with about 30% retention of configuration. Reaction of (R)-XVI with HgO afforded (S)-XVIII with the same degree of retention of configuration. Preliminary experiments on racemic compounds are also reported.
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TAICHIRO KOMENO, HIKARU ITANI, HIKOZO IWAKURA, KIYOKO NABEYAMA
1970 Volume 18 Issue 6 Pages
1145-1160
Published: June 25, 1970
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A number of 3α-substituted (H, OH, OAc or SCN)-2β, 5α-dihydroxycholestanes upon treatment with mesyl chloride and pyridine gave the corresponding 2α, 5α-epoxides. These structures were established by the nuclear magnetic resonance spectra and by chemical conversions. In addition, the reaction of a series of 5α-hydroxy-2α, 3α-epoxysteroids with hydrobromic acid leading to the 3α-hydroxy-2α, 5α-epoxysteroids was studied. The reaction mechanism was also discussed.
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TETSUJI KAMETANI, FUMIO SATOH, HIDEO AGUI, KYOKO UEKI, KAZUO KIGASAWA, ...
1970 Volume 18 Issue 6 Pages
1161-1167
Published: June 25, 1970
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A synthesis of 2-amino-(3-hydroxyphenyl) ethanol (I) was investigated as follow. Hydrolysis of 3-acetoxy-ω-(N, N-dibenzylamino) acetophenone (XVI), which was obtained from 3-acetoxy-ω-bromoacetophenone and dibenzylamine, gave the corresponding 3-hydroxy-derivative, whose catalytic hydrogenolysis with Pd-C afforded the above compound (I) as shown in Chart 1. Phenolic cyclization of I and 1-(3-hydroxyphenyl)-2-methylaminoethanol (II) was studied. Cyclization of I with cyclic ketones afforded three kinds of 1, 2, 3, 4-tetrahydro-1, 1-spiroheterocycloisoquinolines. Cyclization of amine (II) with carbonyl compounds was also carried out successfully to give five kinds of the corresponding 1, 2, 3, 4-tetrahydroisoquinolines. Furthermore, it was found that the cyclization occurred at the para position to phenolic hydroxy group.
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HISASHI NOGAMI, MANABU HANANO, SHOJI AWAZU, TOHRU FUWA
1970 Volume 18 Issue 6 Pages
1168-1175
Published: June 25, 1970
Released on J-STAGE: March 31, 2008
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The processes of uptake of TPD (thiamine propyl disulfide) and formation of thiamine were investigated in detail, using the suspension of rat erythrocytes, since erythrocytes were most effective to form thiamine from TPD in blood. 1) The ratio of amount of thiamine formed in erythrocytes to that in the suspension medium was 1 : 1 after incubation of TPD in erythrocytes suspension. This ratio did not change remarkably, even when amount of erythrocytes was increased by 100 fold. 2) It was verified that TPD was converted to thiamine in the membrane under the influence of reducing compounds in erythrocytes and thiamine, which was formed there, went out and into erythrocytes with equal probability. 3) Process of formation of thiamine from TPD by erythrocytes was expressed by second order rate reaction kinetics, and its rate constant was determined.
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SHIRO TAKAHASHI, SHINICHIRO HASHIMOTO, HIDEO KANO
1970 Volume 18 Issue 6 Pages
1176-1184
Published: June 25, 1970
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Benzothiazole 3-oxide (II) was synthesized, starting from its 2-methyl derivative, via the corresponding aldoxime, carbonitrile, imido ester and carboxylic acid. The reaction of the N-oxide II ; deoxygenations, reactions with various nucleophilic agents (tosyl chloride, Ac
2O, C
6H
5MgBr, NaHSO
3, NH
2NH
2·H
2O and KCN·BzCl) involving some 1, 3-dipolarophiles (benzyne, C
6H
5NCO and tetracyanoethylene), and quaternizations were investigated and compared with those of the corresponding imidazole N-oxide.
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HISASHI NOGAMI, TSUNEJI NAGAI, AKIRA KONDO
1970 Volume 18 Issue 6 Pages
1185-1190
Published: June 25, 1970
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According to the rotating disk method, the dissolution of polyvinylpyrrolidone (PVP) was investigated in acetone-water system to make an approach to an understanding of general dissolution behaviors of synthetic polymers. Three stages of dissolution were observed with the lapse of time, i.e., the initial, the main, and the final stages. The initial stage disappeared upon addition of NaCl in bulk solution. Only the main stage was explained according to Noyes-Nernst equation, and the activation energy of dissolution was close to the data reported for the diffusion controlled dissolution. The initial stage is considered to be concerned with the swelling process of PVP inducing the dissolution, and the final stage may be concerned with the coacervation of PVP. When NaCl was added in bulk solution, the initial stage seemed unessential for the dissolution of PVP, while the whole dissolution rate decreased. This was considered due to a suppression of the swelling of PVP on the surface of disk by the adsorption of Na
+ on PVP.
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TOSHIO NAMBARA, SEIJIRO HONMA
1970 Volume 18 Issue 6 Pages
1191-1195
Published: June 25, 1970
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2-Hydroxyestradiol 2- and 3-monoglucuronides (X, V) were prepared from the suitably protected catechol estrogen derivatives employing Koenigs-Knorr reaction as shown in Chart 1. These synthetic glucuronides underwent readily hydrolysis to furnish 2-hydroxyestradiol and free glucuronic acid when incubated with beef-liver β-glucuronidase preparation.
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MORIO IKEHARA, KEI MUNEYAMA
1970 Volume 18 Issue 6 Pages
1196-1200
Published: June 25, 1970
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2', 3'-O-Isopropylidene-8-bromoguanosine was cyclized to 2', 3'-O-isopropylidene-8, 5'-anhydro-8-oxyguanosine (II) by the cyclization with sodium hydride in dioxane. 8, 5'-Anhydro linkage of the compound II was cleaved by various nucleophiles, such as water, hydrogen sulfide, sodium thiolacetate, sodium acetate, potassium thiocyanate and potassium cyanate in acetic acid to give 5'-substituted 5'-deoxy-8-oxyguanosine. Alkaline hydrolysis of II did not proceed smoothly.
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AKIRA TAKAMIZAWA, HISAO SATO
1970 Volume 18 Issue 6 Pages
1201-1210
Published: June 25, 1970
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The novel reaction of 1, 3, 4-thiadiazolium halides (VIIa-c, VIId-e·HBr) with dialkyl acylphosphonates (IIa-b or IIIa-b) in the presence of triethylamine to give 1, 3, 4-thiadiazine derivatives (VIIIa-e, XIa-d) accompanied by ring expansion was described. In the reaction of VIId-e·HBr with IIa-b or IIIa-b, 10a-(1-dialkylphosphoroyl) benzyl (or ethyl)-10, 10a-dihydro-5H-pyrimido [4, 5-d]-1, 3, 4-thiadiazolo [3, 2-a]-pyrimidines (Xa-e) were isolated as the intermediates. Neutral hydrolysis of Xa-e gave XIa-d, while alkaline hydrolysis of Xa-e gave tricyclic compounds (XIIa-d). Brief reaction mechanisms are discussed.
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MASAHIRO NAKADATE, SHOKO SUEYOSHI, IKUO SUZUKI
1970 Volume 18 Issue 6 Pages
1211-1218
Published: June 25, 1970
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When pyridazine (Ia), 3-methylpyridazine (IIa), 4-methylpyridazine (IIIa), 3, 6-dimethylpyridazine (IVa) and their monoxides were oxidized with hydrogen peroxide in various conditions, the corresponding dioxides (Ib-IVb) were isolated. Although these dioxides were hardly react with PCl
3, the corresponding monoxides were obtained in catalytic reduction. The results of ultraviolet, infrared and nuclear magnetic resonance spectrometries and polarographic reduction were described.
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SABURO ISHIWATA, KEIICHI ITAKURA, KAZUO MISAWA
1970 Volume 18 Issue 6 Pages
1219-1223
Published: June 25, 1970
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Decomposition of the diazonium salts of the amino compounds (Ia and Ib) under alkaline conditions gave respectively two kinds of products, which were intranuclear coupling products, proaporphine type compound (II) and aporphine type compounds (IIIa and IIIb).
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SABURO ISHIWATA, KEIICHI ITAKURA
1970 Volume 18 Issue 6 Pages
1224-1227
Published: June 25, 1970
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The Pschorr reaction of 8-amino-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-1-(3, 4-dimethoxybenzyl)-2-methylisoquinoline (Ia) under alkaline conditions gave three compounds, which were separated by chromatography on silica gel into two components, dl-glaucine and a mixture of two isomeric 2, 5-dienones, the latter of which were separated by fractional recrystallization of their picrolonate into each dienone (Va and VIa).
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HIROSHI IGETA, TAKASHI TSUCHIYA, MUTSUMI NAKAJIMA, CHISATO OKUDA, HIDE ...
1970 Volume 18 Issue 6 Pages
1228-1232
Published: June 25, 1970
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3-Halogenopyridazines (I) were alloued to react with hydrazine hydrate in the presence of Pd-CaCO
3 and alkali to afford the symmetrical 3, 3'-bipyridazines (IIa-IIg). When an equimolar mixture of two kinds of 3-chloropyridazines of different substituents was subjected to this condensation reaction, the unsymmetrical 3, 3'-bipyridazines (VIIa-VIId) were formed. Various 3-chloropyridazine N-oxides (X) were subjected to the condensation reaction and the expected 3, 3'-bipyridazine di-N-oxides (XI) were obtained in low yields.
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MINORU SEKIYA, JIRO SUZUKI, YOSHIHIRO KAKIYA
1970 Volume 18 Issue 6 Pages
1233-1238
Published: June 25, 1970
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Reaction for preparation of a new series of 5-acylaminooxazole-4-carboxamides has been found. 5-Acetamidooxazole-4-carboxamides were obtained by heating 2-acylamino-2-cyanoacetamides with acetic anhydride in the presence of perchloric acid. Analogous 5-form-amido derivatives were also obtained by heating the same substrates with a mixture of formic acid and acetic anhydride in the presence of hydrochloric acid. Trials for synthesis of oxazolo [5, 4-d] pyrimidine-7-ol from the 5-acylaminooxazole-4-carboxamide obtained were also successful in some cases by means of heating with potassium bicarbonate solution.
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DAISUKE SATOH, KIYOMI AOYAMA
1970 Volume 18 Issue 6 Pages
1239-1244
Published: June 25, 1970
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A novel condensation reaction was found to take place between 17β-(3-furyl)-5β, 14β-androstane-3β, 14, 16β-triol (III) and carbonyl compounds in the presence of anhydrous cuppric sulfate or acid to afford 6'-substituted-6'H-5β, 14β-androstano [16, 17-2', 3'] furo [3'', 2''-4', 5'] pyran-3β, 14-diol (IV, IV', IX, X). The structures of these products were elucidated by their spectral data and chemical transformations.
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SABURO ISHIWATA, YOUICHI SHIOKAWA
1970 Volume 18 Issue 6 Pages
1245-1248
Published: June 25, 1970
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The intramolecular Mannich reaction of 2-alkylaminomethylbenzimidazole (II) provided 4-alkyl-1, 3, 4, 5-tetrahydro-1, 3, 6-oxadiazepino [3, 4-a] benzimidazole (III) in a good yield. Moreover, the amine (II) can be regenerated by treatment of III with 15% hydrochloric acid and its mechanism is speculated.
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TOSHIO MIYAZAKI, TOSHIRO YADOMAE
1970 Volume 18 Issue 6 Pages
1249-1253
Published: June 25, 1970
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The oligosaccharide is minimum repeating unit of the type specific polysaccharide, was prepared by the treatments with mild alkali, acid, and then acid phosphatase. The oligosaccharide, [α]
D+20° (H
2O), which was composed of L-rhamnose, D-glucose, and N-acetyl-D-mannosamine=2 : 1 : 1.1. From the results of periodate oxidation and methylation studies, the most probable structure of the tetrasaccharide was discussed.
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KIYOSHI TATSUMI, NORIYUKI ARIMA, CHIYUKI YAMATO, HIDETOSHI YOSHIMURA, ...
1970 Volume 18 Issue 6 Pages
1254-1261
Published: June 25, 1970
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The in vivo metabolism of isoprophenamine was examined following oral administration to mice, rabbits and humans. In mice the drug was metabolized to o-chloromandelic acid which was excreted into urine as one of the main metabolites. Mice excreted also a considerable amount of unchanged compound and its basic metabolites. In rabbits and humans, on the other hand, the drug was converted to o-chlorobenzoic acid and o-chlorohippuric acid as acid metabolites and thus the metabolic patterns were resemble each other. The metabolic pathways of the drug and the relationship between metabolism and pharmacological effect are also discussed.
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TAKEO HIGASHINO, YATSUHIRO TAMURA, KAZUHISA NAKAYAMA, EISAKU HAYASHI
1970 Volume 18 Issue 6 Pages
1262-1268
Published: June 25, 1970
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Ketone carbanion reacted as nucleophilic reagent with 1-chloroisoquinoline (II) and 4-chloroquinazoline (III). The reaction of II in the presence of sodium amide with acetophenone, propiphenone, acetone, 3-pentanone, 2-butanone, 2-pentanone, 3-methyl-2-butanone, 4-methyl-2-pentanone, and cyclopentanone respectively afforded 2-(1-isoquinolinyl) acetophenone (B-1), 2-(1-isoquinolinyl) propiophenone (B-2), 1-(1-isoquinolinyl)-2-propanone (B-3), 2-(1-isoquinolinyl)-3-pentanone (B-4), 2-(1-isoquinolinyl)-2-butanone (B-5), 1-(1-isoquinolinyl)-2-pentanone (B-6), 1-(1-isoquinolinyl)-3-methyl-2-butanone (B-7), 1-(1-isoquinolinyl)-4-methyl-2-pentanone (B-8) and 2-(1-isoquinolinyl) cyclohexanone (B-9). Similarly, the reaction of III with acetophenone, 2-methylpropiophenone, acetone, and cyclopentanone afforded respectively 2-(4-quinazolinyl) acetophenone (C-1), 2-(4-quinazolinyl)-2-methylpropiophenone (C-2), 1-(4-quinazolinyl)-2-propanone (C-3), and 2-(4-quinazolinyl) cyclopentanone (C-6). The reaction with propiophenone and 3-pentanone gave 4-ethylquinazoline (D-1), with butyrophenone and cyclohexanone respectively afforded 4-propylquinazoline (D-2) and 4-quinazolinehexanoic acid (D-3). The reaction with 2-butanone gave 1-(4-quinazolinyl)-2-butanone (C-4) and D-1, with 2-pentanone afforded 1-(4-quinazolinyl)-2-pentanone (C-5) and D-2. It was thereby concluded that the reaction of II and III with ketone carbanion formed the carbon-carbon bond accompanied with the elimination of chloro ion.
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ISAO SEKI
1970 Volume 18 Issue 6 Pages
1269-1273
Published: June 25, 1970
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KAZURO SUGIMOTO, KYOICHIRO OHME, MITUO AKIBA, SADAO OHKI
1970 Volume 18 Issue 6 Pages
1273-1276
Published: June 25, 1970
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HIDEJI ITOKAWA, JUNKO KUSHIDA, MITIITI FUJITA
1970 Volume 18 Issue 6 Pages
1276-1278
Published: June 25, 1970
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HARUAKI YAJIMA, HIROKI KAWATANI, HIDEHIKO WATANABE
1970 Volume 18 Issue 6 Pages
1279-1282
Published: June 25, 1970
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AKIRA OGISO, MASAAKI KURABAYASHI, HITOSHI NAGAHORI, HIROSHI MISHIMA
1970 Volume 18 Issue 6 Pages
1283-1286
Published: June 25, 1970
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MASAHIKO FUJINO, CHITOSHI HATANAKA, OSAMU NISHIMURA
1970 Volume 18 Issue 6 Pages
1288-1291
Published: June 25, 1970
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MASAHIKO FUJINO, OSAMU NISHIMURA, CHITOSHI HATANAKA
1970 Volume 18 Issue 6 Pages
1291-1293
Published: June 25, 1970
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TATSUO OZAWA, NAOHIDE KINAE
1970 Volume 18 Issue 6 Pages
1293-1294
Published: June 25, 1970
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TADASHI WATABE, SHYUKUKO KANEHIRA
1970 Volume 18 Issue 6 Pages
1295-1296
Published: June 25, 1970
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