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AKIRA TAKAMIZAWA, KENTARO HIRAI
1970 Volume 18 Issue 5 Pages
865-870
Published: May 25, 1970
Released on J-STAGE: March 31, 2008
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Investigation of substituent effect of 4-p-substituted phenyl-1, 3-dithiolium cations was undertaken. Determination of pK
R+ values for a series of cations has been carried out and it was found that the electron-donating groups stabilized the cations, while the electron-withdrawing groups destabilized the cations. An excellent correlation between pK
R+ and Hammett's σ
p constants was established. Determination of pK
R'SH has also revealed that there was a linear correlation between pK
R'SH and Hammett's σ
p values. The electronic structures and the molecular diagrams of these cations were given by HMO calculation, and pK
R+ values were linearly related to the π-electron densities at C-2 positions of these cations.
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SACHIO MORI, KOICHI SHUDO, TOMIKO AGETA, TORU KOIZUMI, TOSHIHIKO OKAMO ...
1970 Volume 18 Issue 5 Pages
871-883
Published: May 25, 1970
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Enmein (I) and 12 new constituents were isolated from Isodon trichocarpus KUDO. Among them, isodonol, enmedol, and enmenol, new diterpenoids having full (-)-kauran type carbon skeleton, were examined and V, VI, and VII were assigned respectively to isodonol, enmedol and enmenol from chemical and physical data.
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SACHIO MORI, TORU KOIZUMI, KOICHI SHUDO, TOSHIHIKO OKAMOTO
1970 Volume 18 Issue 5 Pages
884-889
Published: May 25, 1970
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The structures of enmenin, enmelol, and ememodin, new diterpenoids isolated from Isodon trichocarpus KUDO were elucidated as I, II, and III, respectively.
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HISAYUKI MATSUO, YASUO FUJIMOTO, HIROKO KOBAYASHI, TAKASHI TATSUNO, HI ...
1970 Volume 18 Issue 5 Pages
890-895
Published: May 25, 1970
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During the course of further investigation of Method B, which was previously proposed for the tritiation of C-terminal proline in the peptide chain, it was revealed that the C-terminal amino acid was cleaved to some extent under the heat-treatment of peptide in AcOH-Ac
2O solution. This type of C-terminal cleavage was confirmed gas- and paper-chromatographically and further evidences were also obtained by the C-terminal assay of the reaction products. In the present study, it was also revealed that non-C-terminal histidine residue in peptide chain underwent the hydrogen-tritium exchange reaction in its imidazole ring, when the peptide containing histidine residue was heated in a mixture of acetic anhydridetritiated water or acetic anhydride-[carboxy-
3H] acetic acid in the absence of pyridine.
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SABURO ISHIWATA, KEIICHI ITAKURA
1970 Volume 18 Issue 5 Pages
896-900
Published: May 25, 1970
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The Mannich reaction of 1-(3-aminobenzyl) tetrahydroisoquinolines (Va and Vb) with 36% formaldehyde solution in ethanol afforded the corresponding aminoprotoberberines (VIa and IXa, VIb and IXb), formed by the cyclization at the position para and ortho to the amino group and a modified synthesis of 9, 10-disubstituted and 9, 10, 11-trisubstituted protoberberines was accomplished by the reduction or thermal decomposition of the diazonium salts of the aminoprotoberberines.
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MOTOYOSHI YAMAZAKI, KANJI NODA, MASATOMO HAMANA
1970 Volume 18 Issue 5 Pages
901-907
Published: May 25, 1970
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Quinoline 1-oxide (I) was found to react readily with N-acylmethylpyridinium salts (II) in the presence of acetic anhydride to give N-(α-acyl-2-quinolylmethyl) pyridinium salts (III) in good yields, but no reaction was observed without acetic anhydride. Treatment of benzoyl-adduct of quinoline 1-oxide (Ia) with II in the presence of acetic anhydride also afforded III, but the yields of III were somewhat less compared with the former procedure.
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MOTOYOSHI YAMAZAKI, KANJI NODA, MASATOMO HAMANA
1970 Volume 18 Issue 5 Pages
908-915
Published: May 25, 1970
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The reductive cleavage of pyridinium group from N-(α-acyl-2-quinolylmethyl)-pyridinium perchlorate (I) was found to be effected by treatment of I with zinc powder in the presence of potassium acetate in acetic acid under relatively mild conditions to give quinaldyl ketone (II). The tautomeric structures (II-A, II-B and II-C) of aryl quinaldyl ketones (IIb-IIk) were examined by UV, NMR and IR spectroscopies, and it was made clear that II existed chiefly as the enaminic form (II-C) rather than the chelated enolic form (II-B), differently from the case of aryl 2-picolyl ketones (IV).
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MUNEHISA ARISAWA, TOKUTARO TAKAKUWA, TASHICHIRO NAKAOKI
1970 Volume 18 Issue 5 Pages
916-918
Published: May 25, 1970
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The fresh leaves of Sorbaria stellipila SCHNEID (S. sorbifolia A. Br. var. stellipila MAXIM.) was extracted with methanol and the methanolic extract was extracted with ethyl acetate. The ethyl acetate extract afforded sorbarin (scutellarein-7-monorhamnoside) and a new flavonoide (I) as yellow needles, mp 290-292°. I corresponded to the molecular formula of C
16H
12O
6. Complete ethyl ether of I was identified as 7-methoxy-, 5, 6, 4'-triethoxyflavone by direct comparison with the authentic sample, which was produced from sorbarin. Consequently, I was determined as scutellarein-7-methyl ether (5, 6, 4'-trihydroxy-7-methoxyflavone), and named sorbifolin.
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HIROSHI TOMISAWA, MASAO WATANABE, REIKO FUJITA, HIROSHI HONGO
1970 Volume 18 Issue 5 Pages
919-924
Published: May 25, 1970
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The Friedel-Crafts reaction of 1-methyl-2 (1H)-quinolone (I) was carried out. The products identified were 6-acetylated compound (II), 3-propionylated (V) and 6-propionylated (IV), and also 3-and 6-substituted compounds by butyrylation and valerylation.
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HIROSHI TOMISAWA, HIROSHI HONGO
1970 Volume 18 Issue 5 Pages
925-931
Published: May 25, 1970
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The Diels-Alder reaction between 1-methyl-2 (1H)-pyridone (I) and maleic anhydride was successfully carried out in 42% yield. This constitutes a new synthetic route to isoquinuclidine ring. The structure of the adduct (II) so obtained was proved by the synthesis of various derivatives. It was thereby determined that the structure of II is an endo-form IIb, that of dicarboxylic acid (III) is IIIb, that of bromolactone (IV) is IVd, the hydroxy-lactone (V) is Vd, and the dilactone (VI) is VIb.
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HIROSHI TOMISAWA, YUTAKA KOBAYASHI, HIROSHI HONGO, REIKO FUJITA
1970 Volume 18 Issue 5 Pages
932-936
Published: May 25, 1970
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Reaction of 1-methyl-2 (1H)-pyridone with formaldehyde and hydrochloric acid was carried out. The products proved in this reaction were 5-hydroxymethyl-1-methyl-2 (1H)-pyridone (III) in 46% yield from 1-methyl-2 (1H)-pyridone (I), 5-ethyl-3-hydroxymethyl-1-methyl-2 (1H)-pyridone (VIII) from 5-ethyl-1-methyl-2 (1H)-pyridone (VII), and 6-hydroxymethyl-1-methyl-2 (1H)-quinolone (IX) from 1-methyl-2 (1H)-quinolone (II).
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HIROSHI TOMISAWA, KUNIRO SAITO, HIROSHI HONGO, REIKO FUJITA
1970 Volume 18 Issue 5 Pages
937-940
Published: May 25, 1970
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Reaction of 2-methyl-1 (2H)-isoquinolone (I) with formaldehyde and conc. hydrochloric acid was carried out and it was found that the product differed according to reaction conditions. The products obtained and their structure identified were 4-hydroxymethyl-2-methyl-1 (2H)-isoquinolone (II), 4, 4'-methylene-bis [2-methyl-1 (2H)-isoquinolone] (III), and 4-chloromethyl-2-methyl-1 (2H)-isoquinolone (IV).
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HIROSHI TOMISAWA, REIKO FUJITA, KATSUYUKI NOGUCHI, HIROSHI HONGO
1970 Volume 18 Issue 5 Pages
941-946
Published: May 25, 1970
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The Diels-Alder reaction of 1-methyl-2 (1H)-pyridone (I) and fumaronitrile was carried out and the structure of the adduct (II) thereby formed was determined as 5-endo-6-exo-dicyano-2-methyl-3-oxo-2-azabicyclo [2.2.2] oct-7-ene (IIa). IIa was obtained only in a low yield of 3% but the diester compound (Xa) with the same configuration was synthesized in a high yield of 88% by the epimerization of IX, obtained in a quantitative yield from the known VIII.
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MINORU SEKIYA, YOSHIYASU TERAO
1970 Volume 18 Issue 5 Pages
947-956
Published: May 25, 1970
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An investigation of Grignard reaction of N-(N', N'-dialkylaminomethyl) amides (N-Mannich base) revealed that the phthalimide and succinimide derivatives underwent nucleophilic attack by Grignard reagent resulting in substitution of the amide residue with alkyls of Grignard reagent, to give tertiary amines in fair yields. These reactions have provided an practical means for preparation of tertiary amines from secondary amines through the N-Mannich bases. In these reactions it was also found that, when more than one molar equivalent amount of Grignard reagent was used, attacks to the amide moieties intially formed proceeded to give phthalimidine derivatives and γ-ketoamide respectively in the case of using N-(N', N'-dialkylaminomethyl) phthalimide and N-(N', N'-dialkylaminomethyl) succinimide. For identities of a series of the γ-ketoamides obtained discussions of their spectral data are also described.
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HIDENOBU OHMORI, MASAICHIRO MASUI
1970 Volume 18 Issue 5 Pages
957-963
Published: May 25, 1970
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It has been found that cupric ion retards the rates of hydrolysis of Girard T hydrazones formed from aliphatic carbonyl compounds. The reduced rates approach to the magnitude expected for the rate-determining hydronium ion catalyzed decomposition of the intermediate amino-alcohols. Cupric ion has almost no effect of the hydrolysis of the Girard T hydrazone of acetophenone or the Girard D hydrazone of acetone. The results are interpreted in terms of an inhibition of hydrolysis through the dipolar form of amino-alcohol intermediate by cupric ion.
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MASARU OGATA, HIROSHI MATSUMOTO, SHIRO TAKAHASHI, HIDEO KANO
1970 Volume 18 Issue 5 Pages
964-969
Published: May 25, 1970
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It is suggested that photolysis of 1-benzyl-2-ethylbenzimidazole 3-oxide (I) involves two different pathways ; one goes via an oxaziridine intermediate (VI) formed from the excited singlet state ; and the other is deoxygenated via the excited triplet state, enhanced by the presence of benzophenone or anthraquinone. Deoxygenation of several aromatic N-oxides is shown to be effected by anthraquinone.
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KENJI KAJI, MASAYUKI KUZUYA
1970 Volume 18 Issue 5 Pages
970-981
Published: May 25, 1970
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4, 5-Dimercapto-3 (2H)-pyridazinones (7, 8, 9), 3, 4-dichloropyridazine-5-thiol (11), which must have been produced during the debenzylation reaction of 3, 4-dichloro-5-benzylthiopyridazine (10), and 4-chloro-5-mercapto-3 (2H)-pyridazinethiones (13, 14) furnished the concurrent formation of the corresponding pairs of dipyridazo [4, 5-b : 4', 5'-e]-1, 4-dithiin derivatives, respectively. On the other hand, 3-methylthio- (15) and 3-morpholino-4-chloropyridazine-5-thiol (16) formed the corresponding 1, 6-disubstituted dipyridazo [4, 5-b : 4', 5'-e]-1, 4-dithiin alone, however, 3-methylthio- (17) and 3-morpholinopyridazine-4, 5-dithiol (18) concurrently formed the corresponding pairs of 1, 6- and 1, 9-disubstituted derivatives. For the interpretation of these reactions, the formation mode was proposed to be divided in two classes according to the characters of the thioketo carbene species as active intermediates. The former reactions proceed through the corresponding thioketo carbene species which is so reversibly interconvertible, that subsequently dimerizes per se in 1, 3-dipolar fashion to concurrently form a pair of the corresponding derivatives. The latter reactions also proceed through the relevant thioketo carbene species in the same fashion of dimerization as described in the former reactions, however, existence of any reversible interconversion between the counterpart one is scarcely infered. So the relevant carbene species of the cyclization started with 15 and 16, independently exist as a pair in a definite mixing proportion, subsequently they combine by the two dimerization mode.
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HIDEYO SHINDO, KOICHI OKAMOTO, JUNICHI TOTSU
1970 Volume 18 Issue 5 Pages
982-990
Published: May 25, 1970
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The cell permeability was compared for a series of O-acyl-S-benzoylthiamine in human red cell suspensions. On varying the length of straight chain alkyl group in the acyl part, it was found that i) at the earliest stage of the transport, the red cells showed a rapid and high uptake of the molecules due to the adsorption at the cell membranes, and ii) an equilibrium state was reached within 120 minutes of incubation and the intracellular concentration of total thiamine was in the following order : acetate<propionate<butyrate>valerate>caproate>capryrate, showing a maximum intracellular accumulation (the cell to medium concentration ratio of 2.9) with 4 carbon acyl group. In order to elucidate the mechanism, the followings were compared for the series of compounds : i) the partition coefficient from aqueous to organic phases, ii) the rate of debenzoylation in the cells and at the membrane site, and iii) the rate of conversion of the corresponding O-acylthiamine to thiamine in the cells and at the membrane site. The results indicated that the hydrolytic enzyme systems associated with the cell membrane (acetylcholinesterase) and the cytoplasm (carboxylesterase) play the most important role in determining the intracellular accumulation rather than the lipid solubility of the compound and that the butyrate with the highest rate of conversion to thiamine in the cells results in the highest intracellular accumulation.
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ATSUSUKE TERADA, YUKICHI KISHIDA
1970 Volume 18 Issue 5 Pages
991-996
Published: May 25, 1970
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Treatment of dimethyl 3-phenyl-2-propynylsulfonium bromide (I) with cyclohexanone in the presence of sodium hydride gave methyl 2-phenyl-4-(1-hydroxycyclohexyl)-2, 3-butadienyl sulfide (II), which accompanied with the rearrangement of S
Ni' type. Similarly, I reacted with cyclopentanone to give a mixture of methyl 2-phenyl-4-(1-hydroxycyclopentyl)-2, 3-butadienyl sulfide (III) and methyl 2-phenyl-4-(1-hydroxycyclopentyl)-3-butynyl sulfide (IV). Dimethyl 2-butynylsulfonium bromide (V), likewise, reacted with cyclohexanone and cyclopentanone to afford methyl 2-methyl-4-(1-hydroxycyclohexyl)-2, 3-butadienyl sulfide (VI) and methyl 2-methyl-4-(1-hydroxycyclopentyl)-2, 3-butadienyl sulfide (VII), respectively. On the other hand, treatment of dimethyl 2-propynylsulfonium bromide (VIII) with cyclohexanone and cyclopentanone gave methyl 4-(1-hydroxycyclohexyl)-3-butynyl sulfide (X) and methyl 4-(1-hydroxycyclopentyl)-3-butynyl sulfide (XIII), respectively.
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SADAO NISHIGAKI, KEITARO SENGA, KAZUKO OGIWARA, FUMIO YONEDA
1970 Volume 18 Issue 5 Pages
997-1002
Published: May 25, 1970
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The reaction of 4-amino-6-hydroxy-2-methylpyrimidine with phosphorus oxychloride at 220-230° gave 6, 6'-dichloro-2, 2'-dimethyl-4, 4'-iminodipyrimidine (I) in good yield. I was also obtained from 4-amino-6-chloro-2-methylpyrimidine under these conditions. The reaction was extended successfully to some other 4-aminopyrimidine derivatives to form the corresponding iminodipyrimidines. Reaction of either 4-amino-6-methoxy (or ethoxy)-2-methylpyrimidine or 6, 6'-dimethoxy (or diethoxy)-2, 2'-dimethyl-4, 4'-iminodipyrimidine with phosphorus oxychloride at 220-230° proceeds anomalously to give I in quantitative yields. Replacement of the chlorine atoms in I by nucleophiles was carried out. Direct synthesis of 4, 4'-dichloro-6, 6'-dimethyl-2, 2'-iminodipyrimidine was realized in the reaction of 2-amino-4-hydroxy-6-methylpyrimidine or 2-amino-4-chloro-6-methylpyrimidine with phosphorus oxychloride.
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SADAO NISHIGAKI, KEITARO SENGA, KYOKO AIDA, TOYOMI TAKABATAKE, FUMIO Y ...
1970 Volume 18 Issue 5 Pages
1003-1007
Published: May 25, 1970
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The pyrimidine synthesis from ethyl ethoxymethylenecyanoacetate (EMCE) and amidines is significantly influenced by the mole ratios of reacting components. In general the use of excess amidine gives better yields. Condensation of EMCE with excess acetamidine gives 4-hydroxy-2-methyl-5-pyrimidinecarbonitrile acetamidinate as the main product in good yield. Reaction between EMCE and excess 2-ethyl-2-thiopseudourea gives 2-ethylthio-4-hydroxy-5-pyrimidinecarbonitrile 2-ethyl-2-thiopseudoureate rather than 3-{3-{[amino (ethylthio) methylene] amino}-2-cyanoacryloyl}-2-ethyl-2-thiopseudourea originally claimed. The condensation reactions of EMCE with other amidines such as guanidine and benzamidine have been studied.
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HIROYASU TAGUCHI, TOKURO OHISHI, HIROSHI KUGITA
1970 Volume 18 Issue 5 Pages
1008-1014
Published: May 25, 1970
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Some mesembrine type (3a-aryl-cis-octahydroindol-6-one) compounds (VIII-X) were synthesized from benzyl nitriles (I) by the six-step sequence of the reactions involving an acid-catalyzed cyclization of 3a-aryl-[2-(2-methyl-1, 3-dioxolan-2-yl) ethyl]-1-pyrroline (VI). Pictet-Spengler reaction of XVIII and XIX, which were derived from N-benzyl derivative (Xb), gave dihydrocrinine models (XX and XXI) in good yields. The stereochemistry of two epimeric 3a-phenyl-cis-octahydroindol-6-ols (XIVa and XVIa) was determined on the basis of infrared and nuclear magnetic resonance spectral data.
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HISASHI TANAKA, HIROMU SAKURAI, AKIRA YOKOYAMA
1970 Volume 18 Issue 5 Pages
1015-1020
Published: May 25, 1970
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Selenocysteamine (2-aminoethaneselenol) hydrochloride was prepared by three methods. Compositive acid dissociation constants of selenocysteamine were determined by potentiometric titration. Microscopic dissociation constants of cationic, anionic, zwitterionic and neutral forms, and tautomeric constant between zwitterionic and neutral forms were calculated, in selenocysteamine and cysteamine. Selenocysteamine was found to present completely as zwitter-ionic form at pH 7-10, whereas cysteamine was found to present about 60% as zwitter-ionic form at pH 10.
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AKIRA YOKOYAMA, HIROMU SAKURAI, HISASHI TANAKA
1970 Volume 18 Issue 5 Pages
1021-1025
Published: May 25, 1970
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In the reaction of selenocysteamine with nickel ion, formation of cationoid complex was confirmed by pH titration, elemental analysis, molar-ratio method and infrared spectra. On the basis of the formation of the cationoid complex, stability constants of cobalt, zinc, palladium and cadmium complexes of selenocysteamine were determined. In selenocysteamine, formations of the complexes were observed in more acid medium than in cysteamine.
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YOSHIKI HAMADA, ISAO TAKEUCHI, HIDEKO MATSUOKA
1970 Volume 18 Issue 5 Pages
1026-1033
Published: May 25, 1970
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(1) By the application of potassium cyanide and the corresponding acyl chloride to 1, 6-naphthyridine (II) in methylene chloride-water or in aqueous solvent, Reissert compounds (V-VII) were obtained. Reaction of II with potassium cyanide and benzoyl chloride afforded a Reissert compound (VIII) not possessing a cyano group. (2) Application of benzenesulfonyl chloride or methylsulfonyl chloride and potassium cyanide to II afforded desulfonylated compound (IV) in either case. (3) Reaction of II with potassium cyanide and N, N-diphenylcarbamoyl chloride gave IX. Structure of these Reissert compounds (IV to IX) was examined through nuclear magnetic resonance and ultraviolet spectra, and their antibacterial activity was tested.
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KIICHIRO KAKEMI, HITOSHI SEZAKI, RYOJI KONISHI, TOSHIKIRO KIMURA, ATSU ...
1970 Volume 18 Issue 5 Pages
1034-1039
Published: May 25, 1970
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The mechanism of the enhancement of the intestinal absorption of sulfaguanidine by bile salts, sodium taurocholate and sodium glycocholate, together with the poor absorbability of the drug itself was investigated, using the in situ single loop preparations. It was found that the cause of the poor absorbability of sulfaguanidine could be attributed neither to its dimer formation nor to the iceberg formation in aqueous solution. Since bile salts did not affect its physico-chemical properties such as apparent partition coefficient and diffusion constant, and did not form micellar complex with the sulfa drug, it became evident that the absorption enhancement was not caused by their intraluminal effect. On the absorptive surface, bile salts did not increase the affinity of the sulfa drug to the intestinal mucosal surface. The exsorption study demonstrated that such enhancement was caused by the direct action of bile salts to the structure of the absorptive surface. This effect was reversible and could not be explained only by the calcium depletion.
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JONGYOON KIM, TAKAO KWAN
1970 Volume 18 Issue 5 Pages
1040-1044
Published: May 25, 1970
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Interaction of pentacyanocobalt hydride, HCo (CN)
63-, with epoxides such as propylene oxide, cyclohexene oxide, and styrene oxide has been investigated in aqueous solutions. While hydrogenation of epoxides to alcohols took place, it appeared to give way, to some extent, to isomerization to form ketones especially when excess alkali was added. This newly discovered isomerization reaction is assumed to take place via the interaction of epoxides with univalent pentacyanocobalt complex, Co(CN)
54-, that is formed in alkaline solution according to HCo (CN)
52-+OH
-→Co (CN)
54-+H
2O.
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TAKAICHI ARITA, RYOHEI HORI, TOSHIO ANMO, MITSUNORI WASHITAKE, MAKOTO ...
1970 Volume 18 Issue 5 Pages
1045-1049
Published: May 25, 1970
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YASUHIRO YAMANE, KAZUO SAKAI, MIYOKO HAYASHI, MIDORI MATSUZAKI, AKIRA ...
1970 Volume 18 Issue 5 Pages
1050-1052
Published: May 25, 1970
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YASUHIRO HOSOKAWA, YASUHIKO YOTSUI, OSAMU NAGASE, MASAO SHIMIZU
1970 Volume 18 Issue 5 Pages
1052-1055
Published: May 25, 1970
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KAZUHIRO IMAI, ZENZO TAMURA
1970 Volume 18 Issue 5 Pages
1055-1057
Published: May 25, 1970
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HIROKO TODA
1970 Volume 18 Issue 5 Pages
1057-1060
Published: May 25, 1970
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BUNJI SHIMIZU, FUSAAKI SHIMIZU
1970 Volume 18 Issue 5 Pages
1060-1062
Published: May 25, 1970
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YOSHIHISA OKAMOTO, TAKEHIKO KATO, ATSUSHI TAKADA, TAKEO UEDA, TADAKAZU ...
1970 Volume 18 Issue 5 Pages
1064-1066
Published: May 25, 1970
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TOHRU ENDO, HEIHACHIRO TAGUCHI
1970 Volume 18 Issue 5 Pages
1066-1067
Published: May 25, 1970
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TAKUO KOSUGE, HIROSHI ZENDA, YOSHINORI SUZUKI
1970 Volume 18 Issue 5 Pages
1068-1071
Published: May 25, 1970
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HIROSHI HIKINO, MASARU OGURA, TOMIHISA OHTA, TSUNEMATSU TAKEMOTO
1970 Volume 18 Issue 5 Pages
1071-1073
Published: May 25, 1970
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TADAHIRO TAKEDA, YOSHIHIRO NISHIKAWA, SHOJI SHIBATA
1970 Volume 18 Issue 5 Pages
1074-1075
Published: May 25, 1970
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TOHRU UEDA, SUSUMU SHIBUYA
1970 Volume 18 Issue 5 Pages
1076-1078
Published: May 25, 1970
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HIROSHI HIKINO, KYOSUKE NOMOTO, RITSUKO INO, TSUNEMATSU TAKEMOTO
1970 Volume 18 Issue 5 Pages
1078-1080
Published: May 25, 1970
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TSUTOMU FURUYA, MASAO HIROTANI, TOMOKO SHINOHARA
1970 Volume 18 Issue 5 Pages
1080-1081
Published: May 25, 1970
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HIROSHI HIKINO, TOMIHISA OHTA, TSUNEMATSU TAKEMOTO
1970 Volume 18 Issue 5 Pages
1082
Published: May 25, 1970
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