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YOSHIHIRO KOSEKI
1969 Volume 17 Issue 4 Pages
633-638
Published: April 25, 1969
Released on J-STAGE: March 31, 2008
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The cryoprotective action of glycerol on the strain L cells was studied. Glycerol, even when present only in the cell interior or only in the surrounding medium, apparently furnishes the cells cryoprotection to some extent, but glycerol in the cell interior seems to be more effective than in the medium. Its presence both in the cell interior and in the medium is a requisite for perfect protection against freezethawing injury.
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TAMIO NISHIMURA, SHINZO TANABE, HIROSHIGE TOKU, TOMOYUKI KONO, YUZURU ...
1969 Volume 17 Issue 4 Pages
639-649
Published: April 25, 1969
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The structural limitation of positive compounds in the Voges-Proskauer Reaction was investigated with guanidines, ureas, thioureas, formamidine and formaldoxime, using the α-naphthol alkaline and diacetyl solution. Only guanidino derivatives showed positive reaction among compounds tested above. Strongly positive compounds were asym-1, 1-dialkylguanidines. Especially, 1, 1-dimethylguanidine, 1-methyl-1-phenylguanidine and 1, 1-pentamethyl-eneguanidine had the highest absorbance at 535 mμ. Creatine which was usually used in this reaction, showed second higher absorbance. Monosubstituted guanidine gave always moderately positive reaction, and unsubstituted one was weakly positive. sym-1, 3-Dialkylguanidines such as 1, 3-dimethylguanidine was negative, suggesting that a free amidino group [chemical formula] would be necessary for the positive V-P reaction. This is further supported by the fact that tri-, tetra- and pentamethylguanidine also gave negative reaction. 8-Hydroxyquinoline could be used in place of α-naphthol in this reaction. Conditions for color development, stability of colored solution and the effect of pH on the wave length of λ
max were studied.
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TADASHI KANAI, MOTONOBU ICHINO, TAKASHI KOJIMA
1969 Volume 17 Issue 4 Pages
650-652
Published: April 25, 1969
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5, 6-Dihydroxy-5, 6-dihydro-2'-deoxyuridine (IIIa) and 5, 6-dihydroxy-5, 6-dihydrouridine (IIIb) were prepared via bromination of 2'-deoxyuridine (Ia) and uridine (Ib) respectively, followed by refluxing these unstable intermediates in the neutral conditions to replace the bromo group with the hydroxyl group. In the case of cytidine, however, the 5, 6-dihydroxy-5, 6-dihydro compound was not obtained by the same procedure as used for preparation of IIIa and IIIb from Ia and Ib.
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KOICHI NAGATA
1969 Volume 17 Issue 4 Pages
653-660
Published: April 25, 1969
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Chemical reactivities of the metal complexes of thiohydroxamic acids was investigated. By alkylation or acylation, all the metal complexes except the nickel complex was dissociated to the corresponding metal ions and derivatives of thiohydroxamic acid. The nickel complex was benzoylated without undergoing the dissociation in chilled sodium hydroxide. Sodium or zinc salts or some derivatives of benzothiohydroxamic acid underwent the Lossen rearrangement, and the rearrangement products were isolated. However, the nickel complex did not give the rearrangement products in alkaline solution because of the stability of the chelated structure. From those results, it was confirmed that the hydroxyimino group of thiohydroxamic acid is in the syn configuration to the sulfur atom and that the transition metal complexes possess the five-membered chelate structure as shown in formular [chemical formula] (M=metal ion) in the solid state.
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KOICHI NAGATA
1969 Volume 17 Issue 4 Pages
661-668
Published: April 25, 1969
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Several compounds possessing both mercapto and hydroxyimino groups, such as 2-mercaptoacetophenone oxime, 3-mercaptopropiophenone oxime and 5-nitro-2-mercapto-benzaldehyde oxime, were prepared, and their reactivities with metal ions were compared with those of the corresponding ketones or aldehyde and those of thiohydroxamic acids. It was found that these compounds did not show any sensitive color reactions with Fe
3+, Ti
4+, UO
2+2 and VO
2+ and did not form stable Fe
3+ and Cu
2+ complexes, differing from thiohydroxamic acids, and that the conversions of the compounds possessing both carbonyl and mercapto group to the corresponding oximes did not give any effect on the sensitivities and selectivities.
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NOBUYASU MIZUNO, MASARU AOKI, AKIRA KAMADA
1969 Volume 17 Issue 4 Pages
669-676
Published: April 25, 1969
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Relations between the properties of pyridoxine and pyridoxine 3, 4-diacylates and the changes of vehicles in percutaneous absorption were studied. a) Depilated skin : PIN is absorbed more rapidly than PIN-HCL. While, PIN showed a rapid change in blood level, PIN-DK, -DIK gave high blood level 24 hours after the application of the drugs. b) Normal skin : The normal skin cases for PIN, PIN-DK and -DIK showed the same blood level as depilated cases 8 or 24 hours after application of the drugs. The blood level of PIN did not decrease within 10 hours unlike the depilated skin.
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AKIRA HANAKI, PRANOD XUMSAENG, TOHRU HINO, SANYA AKABOSHI
1969 Volume 17 Issue 4 Pages
677-681
Published: April 25, 1969
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The effect of N-substituent on the stability in an aqueous solution of AET was studied. By the substitution, both the transguanylation and the cyclization were hindered. The reactive species of N-Et-AET, and probably of N'-Et-AET, for the transguanylation is the monoionic conjugate base. N'-Et-AET, being relatively stable in the presence of less than one equivalent alkali, may be dissociated through the two-steps ionization to the neutral conjugate base, which would be considered as one of the reactive species. The degree of the transformation of N-ethylated AET derivatives was as follows ; the transguanylation in the presence of 0.5 equivalent NaOH for 4 min at 15° : AET ; 0.95, N'-Et-AET ; 0.84, N'-Et-AET ; 0.27. the cyclization in 3 days at 30° : AET ; 0.95, N'-Et-AET ; 0.36, N'-Et-AET ; 0.29. The relationship between the transguanylation and the pH drop in the solution was discussed.
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DAISUKE SATOH, SETSUKO KOBAYASHI, JUNKO MORITA
1969 Volume 17 Issue 4 Pages
682-689
Published: April 25, 1969
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Treatment of gitoxin (I) with alkyl chloroformate in pyridine gave rise to alkoxycar-bonylation of hydroxyl groups in the order of 4'''-, 16- and 3'''-positions analogously to acetylation to afford gitoxin 4'''-mono-, 4''', 16-di-and 3''', 4''', 16-trialkoxycarbonates (II, III, IV), but the further esterification encountered with more difficulties than the acetylation. Gitoxin 3''', 4'''-cyclocarbonate (V) was also prepared and the interconversion between 3'''-mono-and 4'''-monomethoxycarbonates (VIIa, IIa) and V was investigated. Alkyl pyrocarbonates showed a less selectivity in alkoxycarbonylation of I than alkyl chloroformates, resulting in the formation of V, 16-alkoxy-and 3''', 4'''-cyclocarbonyl-16-alkoxycarbonates (IX, VIII) besides II, III and IV. IX was also formed by partial hydrolysis of III and VIII with dilute alkali.
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HIROMU MORI, KENYU SHIBATA, KIYOSHI TSUNEDA, MASANOBU SAWAI
1969 Volume 17 Issue 4 Pages
690-698
Published: April 25, 1969
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A novel synthetic method of preparation of the side chain of ecdysone, 22, 25-dihydroxycholestane side chain was developed. The sequence of this method was summarized as the procedures XI→XII→XIII→XIV→XVI→XVII (Chart 3)→XXV→XXVII→XXIX (Chart 5).
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TORAHIKO KISHIKAWA, YUJI OIKAWA, SHOJI TAKITANI
1969 Volume 17 Issue 4 Pages
699-702
Published: April 25, 1969
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Condensation of methyl (tri-O-acetyl-a-D-glucopyranosyl bromide) uronate with silver 2-pyridyl oxide in toluene gave methyl (2-pyridyl 2, 3, 4-tri-O-acetyl-β-D-glucopyranosid)-uronate (III). Removal of the protecting groups from III afforded the O-glucuronide of 2-hydroxy pyridine (V). The O→N rearrangement of the glucuronosyl residue in III was effected by refluxing the toluene solution of III in the presence of mercuric bromide. An attempt to hydrolyze V and VIII by the β-glucuronidase was made. It was found that whereas the O-glycoside (V) is hydrolysable by this enzyme, the N-glycoside (VIII) is completely inert to it. Acid-and alkali-catalyzed hydrolyses of V and VIII were also investigated.
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KUNIO KOBAYASHI, MIKIO HONJO
1969 Volume 17 Issue 4 Pages
703-708
Published: April 25, 1969
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The reaction of chloroform with liq. ammonia in a sealed vessel at high temperatures furnished adenine, purine, and 8-aminopurine in 5, 7 and 1% yields, respectively. Similarly, the reaction between ethyl orthoformate and liq. ammonia yielded adenine (21%), purine (14%) and 8-aminopurine (3%), A possible mechanism has been proposed for the reaction, which involves a polymerization of formimidoyl derivative rather than an intermediary formation of aminomalononitrile.
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TETSUJI KAMETANI, HIDEO IIDA, TOYOHIKO KIKUCHI, MASAKATSU MIZUSHIMA, K ...
1969 Volume 17 Issue 4 Pages
709-713
Published: April 25, 1969
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Dienone-phenol rearrangement of dienone (II) with concentrated sulfuric acid gave a cularine-type compound, 9-hydroxy-5, 6, 10-trimethoxy-1-methyl-1, 2, 3, 12, 12a-pentahydrobenzoxepino [2, 3, 4-i, j] isoquinoline (III), whose structure was assigned by spectroscopic method and its alternative synthesis of III from 1-(2-bromo-4-hydroxy-5-methoxybenzyl)-1, 2, 3, 4-tetrahydro-8-hydroxy-6, 7-dimethoxy-2-methylisoquinoline (XI). Moreover, this paper described the preparation of XI.
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SHOSHIRO NAKAMURA, YASUKO MARUMOTO, HIROSHI YAMAKI, TOSHIO NISHIMURA, ...
1969 Volume 17 Issue 4 Pages
714-721
Published: April 25, 1969
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NOBORU NAKAI, JUN-ICHI HASE
1969 Volume 17 Issue 4 Pages
722-728
Published: April 25, 1969
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1. Four to six moles of sulfhydryl groups of yeast alcohol dehydrogenase were found to be high sensitivity for 5, 5'-dithiobis (2-nitrobenzoic acid) (DTNB). 2. There were two types of sulfhydryl groups in the active site of yeast alcohol dehydrogenase. Sulfhydryl groups of two of four active sites were easily modified by DTNB at 0°and the other were not. 3. Yeast alcohol dehydrogenase which was modified sulfhydryl groups of two of four active sites by DTNB, was fully restored in its enzyme activity by cysteine and was found to be the same conformation as the native enzyme. On the other hand, the enzyme which was modified more than two sulfhydryl groups in the active sites, was partially restored by cysteine, probably due to irreversibly conformational change. 4. DTNB competed with NAD for sulfhydryl group in the active site of yeast alcohol dehydrogenase.
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TAMOTSU SAITOH, SHOJI SHIBATA
1969 Volume 17 Issue 4 Pages
729-734
Published: April 25, 1969
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From the root of licorice (Glycyrrhiza spp., Leguminosae) three new coumestan derivatives, named glycyrol, 5-O-methylglycyrol and isoglycyrol, have been isolated, whose structures have been established to be Ia, IIa and IIIa, respectively. Betulic acid was also obtained.
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TAKUO OKUDA, KUNIHIRO KONISHI
1969 Volume 17 Issue 4 Pages
735-737
Published: April 25, 1969
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Coriose (D-altro-3-heptulose) (I) was synthesized by the lead tetraacetate oxidation of hydrolyzate of the mother liquor of 1, 3 : 5, 7-di-O-ethylidene-3-C-formyl-D-glycero-D-talo-heptitol-3 (1), 6-pyranose (IV) which was derived from 2, 4-O-ethylidene-D-erythrose (V) by the aldol condensation.
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MINORU SEKIYA, CHIZUKO YANAIHARA
1969 Volume 17 Issue 4 Pages
738-746
Published: April 25, 1969
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It has been found that after heating with a reagent, given by 5HCO
2H·2N (C
2H
5)
3, several barbituric acid derivatives were methylated at the 5-position. The reaction was revealed to proceed through an intermediate, 5, 5'-methylidynebis (barbituric acid), which had been previously known as the usual reaction product obtained by heating with formic acid. The reaction course was found to involve an interesting aspect that the reagent carries out a saturation of the carbon-carbon double bond at the 5-position followed by a reductive fission of the bond.
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MINORU SEKIYA, CHIZUKO YANAIHARA, JIRO SUZUKI
1969 Volume 17 Issue 4 Pages
747-751
Published: April 25, 1969
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By means of heating in triethylammonium formate given by 5HCO
2H·2N (C
2H
5)
3, hydrogenation of 5-methylidene bond attached to barbituric acids was effected in general. The method was found to be convenient for preparation of 5-arylmethylbarbituric acids and some other 5-alkylbarbituric acids with certain advantages : good yield of the products and selectivity at the double bond of 5-position.
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MINORU SEKIYA, CHIZUKO YANAIHARA, JIRO SUZUKI
1969 Volume 17 Issue 4 Pages
752-755
Published: April 25, 1969
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Investigation on the thermal TEAF reaction with 5-(3-indolylmethylene) barbituric acid is described in view of the courses of the product formations. With such a compound, not only the previously reported reduction of its methylidyne but also the succeeding reductive fission of the resulting methylene was revealed to occur in the reaction.
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HIROSHI IGETA, TAKASHI TSUCHIYA, MUTSUMI NAKAJIMA, TOSHIKO SEKIYA, YOK ...
1969 Volume 17 Issue 4 Pages
756-762
Published: April 25, 1969
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3-Hydroxypyridazine 1-oxide (I) and its methyl homologs (II), (III), and (IV) were submitted to electrophilic substitutions such as nitration and halogenation. Due to the additional polar effect of both N-oxide and hydroxyl groups, introduction of nitro group and halogen in 4-and/or 6-positions was successfully concluded. By heating with potassium hydrosulfide, nucleophilic substitution of the brominated compounds (XXXI and XXXVI) was also carried out, affording mercapto compounds (XXXII and XXXVII).
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HIROSHI IGETA, TAKASHI TSUCHIYA, MUTSUMI NAKAJIMA, HIDEHARU YOKOGAWA
1969 Volume 17 Issue 4 Pages
763-769
Published: April 25, 1969
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NMR spectra of 3-hydroxypyridazine 1-oxides and their monomethylated derivatives were examined and structural propriety of their nitrated and halogenated products was confirmed by the analyses of the NMR spectra. Furthermore, in 3-hydroxypyridazine 1-oxides, predominance of enol form tautomer was proved by NMR data. The conclusion was also drawn by other spectral data (UV and IR).
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AKIE NAKAMURA, MASAKO MAEDA, TOSHIO KINOSHITA, AKIO TSUJI
1969 Volume 17 Issue 4 Pages
770-774
Published: April 25, 1969
Released on J-STAGE: March 31, 2008
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It was found that glucosamine-HCl reacted with p-nitrobenzaldehyde in pyridinemethanol solution to yield Schiff base and gave a blue color by addition of tetraethylammonium hydroxide solution. This new color reaction is selective for 2-amino-2-deoxy sugars and α-amino carbonyl compounds, such as aminoacetaldehyde, δ-aminolevulinic acid and α-aminoacetophenone. The microdetection methods for 2-amino-2-deoxy sugars and their derivatives were proposed and the reaction mechanism was investigated.
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KIYOMI KIKUGAWA, TYUNOSIN UKITA
1969 Volume 17 Issue 4 Pages
775-784
Published: April 25, 1969
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2, 3'-Anhydro-1-(β-D-xylofuranosyl) uracil (IV) was allowed to react with sodium iodide in the presence of acetic acid. The major product isolated was proved to be 1-(5'-iodo-5'-deoxy-β-D-xylofuranosyl) uracil (V) whose structure was unambiguously established. The reaction of other halide ions on the anhydronucleoside (IV) furnished the same type of compounds, 1-(5'-chloro-5'-deoxy-β-D-xylofuranosyl) uracil (XVI) and 1-(5'-bromo-5'-deoxy-β-D-xylofuranosyl) uracil (XVII). By treatment of the compound (V) with silver acetate, 2, 3'-anhydro compound (IV) was recovered, and it was supposed that 2, 5'-anhydro-1-(β-D-xylofuranosyl) uracil (XII) initially produced was rearranged to the 2, 3'-anhydro compound (IV) by a nucleophilic attack of 3'-up hydroxyl function of XII at C
2 carbon of the uracil moiety.
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KIYOMI KIKUGAWA, MOTONOBU ICHINO, TYUNOSHIN UKITA
1969 Volume 17 Issue 4 Pages
785-797
Published: April 25, 1969
Released on J-STAGE: March 31, 2008
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The reactions of methyl iodide with 2, 2'-anhydro-1-(β-D-arabinofuranosyl) uracil (I) and 2, 3'-anhydro-1-(β-D-xylofuranosyl) uracil (VIII) afforded the products (II and IX) containing methyl and iodo groups, respectively. The structure of the product (II) was firmly established to be N
3-methyl-2'-iodo-2'-deoxyuridine, and that of the product (IX) to be N
3-methyl-1-(5'-iodo-5'-deoxy-β-D-xylofuranosyl) uracil. The reaction mechanism to afford the compound (IX) from VIII was assumed to proceed via an initial intermediate, quaternary salt (XXI), and followed by the second intermediate of a quaternary 2, 5'-anhydro compound (XXIII), which was formed by an intramolecular attack by 5'-hydroxyl function at the C
2 carbon atom of the base moiety in XXI.
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KIYOMI KIKUGAWA, MOTONOBU ICHINO, TSUNEO KUSAMA, TYUNOSHIN UKITA
1969 Volume 17 Issue 4 Pages
798-803
Published: April 25, 1969
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1-(5'-Amino-5'-deoxy-β-D-xylofuranosyl) uracil (VIII) and N
3-methyl-1-(5'-amino-5'-deoxy-β-D-xylofuranosyl) uracil (IX) were synthesized by catalytic reduction of the respective 5'-azido nucleosides, which were obtained by nucleophilic attack of 1-(3, '5'-epoxy-β-D-xylofuranosyl) uracil (IV) or 1-(5'-halogeno-5'-deoxy-β-D-xylofuranosyl) uracils (II) and N
3-methyl-1-(3', 5'-epoxy-β-D-xylofuranosyl) uracil (V) or N
3-methyl-1-(5'-iodo-5'-deoxy-β-D-xylofuranosyl) uracil (III) by lithium azide in dimethylformamide. The structures of the products (VIII and XI) were firmly established.
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MASUMI KOISHI, NAOKO FUKUHARA, TAMOTSU KONDO
1969 Volume 17 Issue 4 Pages
804-809
Published: April 25, 1969
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Polyphthalamide microcapsules were prepared by the interfacial polycondensation reactions between each of 1, 6-hexamethylenediamine and diethylenediamine and each of o-, m-, and p-phthaloyl dichlorides under various conditions. The size and size distribution of the microcapsules formed were determined and the factors affecting them were of studied. Favorable conditions were suggested to obtain the microcapsules of uniform size in a high yield.
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MINORU SEKIYA, CHIZUKO YANAIHARA
1969 Volume 17 Issue 4 Pages
810-814
Published: April 25, 1969
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TETSUJI KAMETANI, FUMIO SATOH
1969 Volume 17 Issue 4 Pages
814-818
Published: April 25, 1969
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KOJI KURODA, GENZO HASHIZUME, FUKIKO KUME
1969 Volume 17 Issue 4 Pages
818-821
Published: April 25, 1969
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SHUNICHI NAITO, MITSUO MIZUTANI
1969 Volume 17 Issue 4 Pages
822-826
Published: April 25, 1969
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AKIKO IKEKAWA, NOBUYOSHI KANENIWA
1969 Volume 17 Issue 4 Pages
827-834
Published: April 25, 1969
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KUNIO NAKAGAWA, HIROSHI ONOUE, KYOJI MINAMI
1969 Volume 17 Issue 4 Pages
835-837
Published: April 25, 1969
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SHIGERU GOTO, OSAMI TSUZUKI, SADAO IGUCHI
1969 Volume 17 Issue 4 Pages
837-840
Published: April 25, 1969
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MITSURU UCHIYAMA, MASAOKI SHIBUYA
1969 Volume 17 Issue 4 Pages
841-843
Published: April 25, 1969
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HARUO OGURA, TSUNEO ITOH, TAKASHI OKAMOTO, SATOSHI OMURA
1969 Volume 17 Issue 4 Pages
844-846
Published: April 25, 1969
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ZENICHI HORII, KOICHI MORIKAWA, ICHIYA NINOMIYA
1969 Volume 17 Issue 4 Pages
846-848
Published: April 25, 1969
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AKIO HOSHI, FUMIHIKO KANZAWA, KAZUO KURETANI
1969 Volume 17 Issue 4 Pages
848-850
Published: April 25, 1969
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HIROSHI HIKINO, KUNIO ITO, TSUNEMATSU TAKEMOTO
1969 Volume 17 Issue 4 Pages
854-855
Published: April 25, 1969
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ITIRO YOSIOKA, TAKEATSU KIMURA
1969 Volume 17 Issue 4 Pages
856-857
Published: April 25, 1969
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TSUTOMU MOMOSE, YOSUKE OHKURA, KAZUYA KOHASHI
1969 Volume 17 Issue 4 Pages
858-859
Published: April 25, 1969
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