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SHIGEO UKAI, KAZUO HIROSE
1968 Volume 16 Issue 2 Pages
195-201
Published: February 25, 1968
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A new synthetic method of 2-arylthio- or 2-alkylthio-p-benzoquinones (XV-XXI) was established through the application of the reaction of hydroquinone with sulfoxides. The reaction of hydroquinone with methyl aryl sulfoxides in the presence of perchloric acid, or with dialkyl sulfoxides in the presence of both perchloric acid and phosphoryl chloride, progressed easily to afford 2, 5-dihydroxyphenylarylmethylsulfonium perchlorates (I-III) or 2, 5-dihydroxyphenyldialkylsulfonium perchlorates (IV-VII). The treatment of these sulfonium perchlorates (I-VII) with potassium chloride or pyridine gave 2-arylthio- or 2-alkylthio-1, 4-dihydroxybenzenes (VIII-XIV) and alkyl chlorides or N-alkylpyridinium perchlorates, respectively. Thus it was shown that Hofmann's degradation did not take place in this case. Compounds VIII to XIV were easily oxidized by ferric chloride to 2-arylthio- or 2-alkylthio-p-benzoquinones (XV-XXI).
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SHIGEO UKAI, KAZUO HIROSE
1968 Volume 16 Issue 2 Pages
202-210
Published: February 25, 1968
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2-Arylthio- or 2-alkylthio-5-hydroxy-p-benzoquinones (XV-XXI) were easily synthesized by the oxidation of 4-arylthio- or 4-alkylthioresorcinols (VIII-XIV) with potassium nitrosodisulfonate. VIII-XIV were prepared from the sulfonium perchlorates (I-VII) synthesized by the reaction of resorcinol with sulfoxides. The structure of these hydroxybenzoquinones (XV-XXI) was elucidated. Further, the Thiele addition of acetic anhydride to 2-arylthio- or 2-alkylthio-p-benzoquinones was examined. Only in the case of the arylthio compounds, the Thiele reaction progressed smoothly to afford arylthiohydroxhydroquinone triacetates (XXX-XXXII). The position of the acetoxyl group in these compounds XXX-XXXII was determined.
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ATSUO NAGAMATSU, TERUKO OKUMA, TOSHIKO HAYASHIDA, YUICHI YAMAMURA
1968 Volume 16 Issue 2 Pages
211-216
Published: February 25, 1968
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It was shown that dilauroyl- and dimyristoyl-L-lysine were more powerful inhibitors than the other fattyacyl derivatives of L-lysine in the proteolytic system of plasmin. In the case of carbon atom number of fattyacyl radical, upon increasing of carbon atom number the inhibitory activity was enhanced to maximum at the C-12 acyl radical, however, higher homologs decreased the inhibitory activity gradually. The inhibitory effect of dilauroyl-L-lysine given to rabbits intravenously was more remarkable than that of ε-aminocaproic acid when the effect was examined by the streptokinase activation test of blood samples taken at various intervals. Reversal by dilauroyl-L-lysine of the accelerated fibrinolysis in circulatroy rabbit blood produced by streptokinase was demonstrated. Dicarbobenzoxy-L-lysine and dilauroyl-L-lysine were shown to be potent antiinflammatory compounds. These compounds were intravenously active as the inhibitor of extravasation of trypan blue in a localized skin area of the rabbit, where the lung extract was injected intracutaneously.
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MASAO TOMITA, KAZUYOSHI FUJITANI, YOSHIAKI AOYAGI, YASUMICHI KAJITA
1968 Volume 16 Issue 2 Pages
217-226
Published: February 25, 1968
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The first successful synthesis of dl-cepharanthine (XXXI) was described. dl-Cepharanthine was isolated together with its diastereoisomer (XXX) and diastereoisomeric pair of the structural isomer (XXIX), which were anticipated to be formed by Bischler-Napieralski cyclization followed by reduction and N-methylation of the cyclobisamide (IVa) obtained via unambiguous route.
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MASAO ISHIKAWA, MANABU FUJIMOTO, KEIKO OKABE, MAKIKO SAKAI
1968 Volume 16 Issue 2 Pages
227-231
Published: February 25, 1968
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Les auteurs ont poursuivi le mode de cyclisation d'un anhydride cycloaliphatique ayant son noyau rigide, soit endo-cis anhydride ethano-3, 6 tetrahydro-1, 2, 3, 6 phtalique (I), par des hydrazines ou hydrazides. Apres determination des produits de cette reaction, ils ont demontre la formation d'une systeme pentagonale comme l'amino (libre ou substitue)-2 ethano-4, 7 tetrahydro-3a, 4, 7, 7a isoindolinedione-1, 3, excepte en cas de la reaction de N, N'-dimethylhydrazine.
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JUNKI KATSUBE
1968 Volume 16 Issue 2 Pages
232-238
Published: February 25, 1968
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dl-Myxoviromycin and its configurational isomer (epimer) were synthesized by a series of reactions shown in Chart 1. The cis configuration was proposed for myxoviromycin from the configurational analysis.
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SHUNSAKU SHIOTANI, TAKAKO HORI, KEMMOTSU MITSUHASHI
1968 Volume 16 Issue 2 Pages
239-245
Published: February 25, 1968
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A synthetic route of 8, 9-dimethoxy-11-benzoyl-1, 2, 5, 6-tetrahydro-2, 6-imino-3-benzazocin-4 (3H)-one (IX-B) having a new ring system was described. 3-(3, 4-Dimethoxyphenyl) alanine ethyl ester (I) was condensed with diethyl malonate followed by cyclization with phosphoryl chloride to give ethyl 1-carbethoxymethylene-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylate (III), which was reduced to ethyl 3-carbethoxy-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline-1-acetate (IV). N-benzoyl derivative (V) of IV was cyclized by a Dieckmann condensation to a tricyclic β-ketoester (VI), which was derived to 7, 8-dimethoxy-10-benzoyl-4, 5-dihydro-1H-1, 4-iminobenzocyclohepten-3 (2H)-one (VII) by treating with dil. HCl. A Beckmann rearrangement of the oxime (VIII) of VII gave 8, 9-dimethoxy-11-benzoyl-1, 2, 5, 6-tetrahydro-1, 5-imino-3-benzazocin-4 (3H)-one (IX-A) and IX-B.
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HIROYASU KANESHIMA, TAKESHI KITSUTAKA, MASUO AKAGI
1968 Volume 16 Issue 2 Pages
246-250
Published: February 25, 1968
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The spontaneous reduction of methemoglobin was markedly inhibited by borate and this inhibition was recovered by reduced nicotinamide adenine dinucleotide. Also the inhibition of glyceraldehydephosphate dehydrogenase activity in bovine blood by borate was observed. The toxicity of borate to blood was discussed.
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MASAO TOMITA, KAZUYOSHI FUJITANI, YUKIO MASAKI, KUOHSIUNG LEE
1968 Volume 16 Issue 2 Pages
251-256
Published: February 25, 1968
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Ferricyanide oxidation of corypalline (I) and its methosalt (V) yielded solely biphenyl derivatives (II and IX), and alternatively expected diphenyl ethers (IV and XII) were not obtained. The result constitutes an information in discussing steric effects of the substituents on the oxidative coupling reactions.
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MASAO TOMITA, YUKIO MASAKI, KAZUYOSHI FUJITANI
1968 Volume 16 Issue 2 Pages
257-261
Published: February 25, 1968
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Oxidative coupling of dl-N-methylisosalsoline (III) with potassium ferricyanide was carried out, and the structures of the products were determined. It was found that III gives rise both to biphenyl derivatives (VI, VII) and diphenyl ether derivative (IV), and a steric participation of 1-substituent of 2-methyl-6-methoxy-7-hydroxy-1, 2, 3, 4-tetrahydroisoquinoline derivative in the product development in the phenol oxidation reactions was observed.
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YOSHIHISA MIZUNO, TOHRU UEDA, KAZUYOSHI IKEDA, KAZUNOBU MIURA
1968 Volume 16 Issue 2 Pages
262-268
Published: February 25, 1968
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1-(β-D-Arabinofuranosyl)-5-methylcytosine (III) was prepared by amination and subsequent deblocking of 1-(2', 3', 5'-tri-O-benzyl-β-D-arabinofuranosyl)-4-methoxy-5-methyl-1H-pyrimidine-2-one which had been prepared from 2, 4-dimethoxy-5-methylpyrimidine and 1-(2', 3', 5'-tri-O-benzyl-α-D-arabinofuranosyl) chloride. 1-(β-D-2'-Deoxy threopentofuranosyl)-5-methylcytosine (II) was prepared from 1-(β-D-3', 5'-O-isopropyl indene-2'-deoxythreopentofuranosyl)-5-methyluracil (VII) by four-step procedure (thiation, S-methylation, amination, and deblocking). As one of possible approaches to II from thymidine (IV), 1-(3', 5'-anhydro-2'-deoxy-β-D-threopentofuranosyl)-thymine (V) was attempted to convert to 1-(3', 5'-anhydro-2'-deoxythreopentofuranosyl)-4-chloro-2 (1H)-pyrimidine-2-one. However, treatment of the latter with DMF-SOCl
2 (Vilsmeier-Haack reagent) afforded 1-(3', 5'-dideoxy-3', 5'-dichloro-2'-deoxythreo pentofruanosyl)-thymine (XIV) in good yield.
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SADAO OHKI, MOTOYO YOSHINO
1968 Volume 16 Issue 2 Pages
269-274
Published: February 25, 1968
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cis- and trans-1, 2, 5-Trimethylpyrrolidines (IIa and IIb) were synthesized. The two were distinguished by their NMR spectra and from the difference in their rate of quaternization with methyl iodide. This latter method was applied to the two kinds of diastereoisomers of 3-(diphenylmethylene)-1, 2, 5-trimethylpyrrolidine (I), and their cis (Ia) and trans (Ib) isomers were determined. The ethiodide of Ia was found to have antiacetylcholine action 0.5 times that of atropine.
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KENICHI TAKEDA, MITOSHI MINATO, ARIYOSHI SHIMAOKA
1968 Volume 16 Issue 2 Pages
275-279
Published: February 25, 1968
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From the examination of yields of sapogenins isolated from Hosta kiyosumiensis F. MAEK in each season, it was assumed that gitogenin is oxidized to the 12-oxygenated sapogenins in the hypogeous part of the plant in winter. In order to confirm this assumption, [27-
14C]-gitogenin was incubated with the homogenate from the hypogeous part of the plant at 37°for 6 hr. The result from this experiment indicates the conversion of gitogenin into the 12-oxygenated sapogenins by the action of the plant enzyme.
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YUICHI KANAOKA, OSAMU YONEMITSU, EISUKE SATO, YOSHIO BAN
1968 Volume 16 Issue 2 Pages
280-284
Published: February 25, 1968
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Polyphosphate ester (PPE) was shown to be a good reagent for the Beckmann rearrangement of some ketoximes, whereas dehydration took place in the case of benzaldoximes. When some ketoximes were heated with PPE, N, N'-diphenylamidines (IVa, b) were formed as a result of a sequence of condensation reactions.
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TAKEO NAITO, MIYOSHI HIRATA, YOSHIAKI NAKAI, TOSHIHIKO KOBAYASHI, MUNE ...
1968 Volume 16 Issue 2 Pages
285-290
Published: February 25, 1968
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Treatment of 2'-O-tosyl-5'-O-trityluridine (I), 2'-O-tosyluridine (II), or 2', 3'-di-O-tosyluridine (XI) with various alkali chlorides or bromides afforded only 2'-halogenonucleosides, whereas in the reaction of alkali iodides with I or II were isolated 2, 2'-anhydronucleosides accompanied with 2'-deoxy-2'-iodouridine derivatives. And in the reaction of XI with sodium iodide in DMF only 2, 2'-anhydro-1-(3'-O-tosyl-β-D-arabinofuranosyl)-uracil (XIII) was obtained.
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MIYOSHI HIRATA
1968 Volume 16 Issue 2 Pages
291-295
Published: February 25, 1968
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Treatment of 2, 2'-anhydro-1-(3'-O-tosyl-β-D-arabinofuranosyl) uracil (I) with sodium bromide, sodium ethanethiol, or sodium azide afforded 2, 2'-anhydro-1-(3'-substituted-β-D-arabinofuranosyl) uracil (II), (III), or (IV). This result shows that 3'-tosyloxy group of I is displaced by above various nucleophiles without net inversion.
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TETSUJI KAMETANI, KAZUO KIGASAWA, MINEHARU HIIRAGI, NAGATOSHI WAGATSUM ...
1968 Volume 16 Issue 2 Pages
296-303
Published: February 25, 1968
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In order to examine the analgesic action of azamorphinan attempt to synthesize 3-hydroxy-N-methyl-9-azamorphinan (III) which has an additional nitrogen in morphinan ring was carried out successfully. Hydrolysis of 2-ethoxycarbonylmethyl-2-(3-methoxyphenyl) cyclohexanone (IX), which was obtained by condensation of 2-(3-methoxyphenyl) cyclohexanone (VIII) with ethyl bromoacetate in the presence of sodium amide, was first examined to give 2-carboxymethyl-2-(3-methoxyphenyl) cyclohexanone (X), whose methylhydrazination with methyl hydrazine afforded 3, 4, 5, 6, 7, 8-hexahydro-2H, 4aH-4a-(3-methoxyphenyl)-2-methyl-3-oxocinnoline (XI). Secondly, reduction of the preceding compound (XI) with lithium aluminum hydride gave 4a-(3-methoxyphenyl)-2-methyldecahydrocinnoline (XII), which was converted into 3-methoxy-N-methyl-9-azamorphinan (XV) by Pictet-Spengler reaction with formalin and hydrochloric acid. Finally, demethylation of XV with hydrobromic acid afforded 3-hydroxy-9-azamorphinan (III), which was characterized as the picrate of its benzoate (XVI). Furthermore, conformation of XV was discussed.
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YUZURU YAMAMOTO, NORIKI KIRIYAMA, SUSUMU ARAHATA
1968 Volume 16 Issue 2 Pages
304-310
Published: February 25, 1968
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Several new pigments produced by a fungus A spergillus fumigatus (J-4) were studied. The structures were determined as 2-chloro-1, 3, 8-trihydroxy-6-methylanthrone (9) (I), 2-chloro-1, 3, 8-trihydroxy-6-methylanthraquinone (II), 2-chloro-1, 3, 8-trihydroxy-6-hydroxymethylanthraquinone (III) and emodin. The chlorinated monoanthrone derivative is the first case in natural products. When Cl- was replaced by Br-in the medium, the fungus produced corresponding brominated anthrone (IV).
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MITSUO NUMATA, HIKOICHI HAGIWARA
1968 Volume 16 Issue 2 Pages
311-319
Published: February 25, 1968
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An improved synthesis of nereistoxin (VII or XIII ; R
3=CH
3) was achieved via the intermediates VIII (R
3=CH
3), X (R
3=CH
3) and XII (R
3=CH
3) as summarized in Chart 2. Applying the reactions formulated in Chart 1 and Chart 2, a number of amines were prepared, whereby the occurrence of intermediates, cyclic sulfonium (III) in the amination reaction in Chart 1 and cyclic immonium (IX) in the thiolation reaction in Chart 2 respectively, was suggested.
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SADAO OHKI, MOTOYO YOSHINO, FUMIKO HAMAGUCHI
1968 Volume 16 Issue 2 Pages
320-325
Published: February 25, 1968
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The ethobromide (IV) (Pyrodifenium bromide) and methiodide (VI) of N-ethyl-2-methyl-3-diphenylmethylenepyrrolidine (II) and the ethiodide (V) of N-methyl-2-methyl-3-diphenylmethylenepyrrolidine (I) were synthesized. Anti-acetylcholine action of IV, V, and VI was 0.5, 1.95, and 0.25 times, respectively, of that of atropine. A marked difference was found in the intensity of the action of the epimeric N, N-ethylmethyl compounds, V and VI.
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SEIICHI SAKUMA, SACHIKO KAWANISHI, JUNZO SHOJI, SHOJI SHIBATA
1968 Volume 16 Issue 2 Pages
326-331
Published: February 25, 1968
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The chemical constituents of Chinese crude drug "Pei-wujiapi" ( ?? ?? ?? ?? ) were studied. Four out of six steroidal substances which were obtained by hydrolysis of the glycoside fraction with dilute acid were identified as Δ
5-pregnene-3β, 20α-diol, Δ
5-pregnene-3β, 17α, 20α-triol, Δ
5-pregnene-3β, 16α, 20α-triol, and periplogenin. Beside these substances, β-sitosterol, β-sitosterol-β-D-glucoside and 4-methoxysalicylaldehyde were isolated from the benzene soluble fraction.
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SHIGERU GOTO, RIKUO TAKAMATSU, MICHIYO SHIBAO, SADAO IGUCHI
1968 Volume 16 Issue 2 Pages
332-337
Published: February 25, 1968
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The effect of combination of caffeine with a few absorbable drugs (salicylic acid, dehydroacetic acid, aspirin, and ethyl p-hydroxybenzoate) on gastric absorption by rabbit was investigated. It is well-known that these drugs associate with caffeine to form soluble complexes. The experimental results at pH 1.3 showed that there was a proportional relationship between the apparent absorption rate constants for drugs and the existing ratio of complex in administered solution, and the effect of caffeine on drugs absorption was remarkable for more absorbable drug (eg. dehydroacetic acid) but was so little for poorly absorbable drug (eg. aspirin). On the other hand, it bacame clear that the absorption rate of salicylate ion was not affected with caffeine. This fact may be correlated with the different affinity between salicylate ion and caffeine as compared with that of undissociated salicylic acid.
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AKIHIRO YAMAZAKI, IZUMI KUMASHIRO, TADAO TAKENISHI
1968 Volume 16 Issue 2 Pages
338-344
Published: February 25, 1968
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2-Alkylthioinosine 5'-phosphates and N
2-methylated guanosine 5'-phosphates (the minor constituents of transfer RNA) were synthesized via 2', 3'-O-isopropylidene-2-mercaptoinosine (I) from 5-amino-1-β-D-ribofuranosyl-4-imidazolecarboxamide (AICA-riboside). The relationship between their chemical structures and flavoring activity was investigated, and 2-methylthioinosine 5'-phosphate (VII) was found to have an extremely strong flavoring activity.
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MICHIHIRO UEDA, NORIHIKO MURAKAMI, YOSHITO NAKAGAWA
1968 Volume 16 Issue 2 Pages
345-351
Published: February 25, 1968
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The metabolism of sulfaphenazole (SP), i.e. N
1-(1-phenylpyrazole-5-yl) sulfanilamide in the human body was investigated. The main metabolite was isolated and confirmed to be the N-glucuronide of SP. In order to determine the structure of this glucuronide, SP-N
1-[methyl (tri-O-acetyl-β-D-glucopyranosid) uronate] (III) was synthesized from potassium salt of SP and methyl (2, 3, 4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranosid) uronate. Hydrolysis of III with NH
4OH gave both N
1-glucuronide and ring N-glucuronide of SP in the ratio of about 2 to 1. Furthermore, N
1-methyl and ring N-methyl derivatives of SP were prepared with CH
2N
2, and their infrared and ultraviolet spectra were compared with those of the conjugate to confirm the substituted position of the glucuronic acid. These evidences indicated that the extracted compound is an imido-type conjugate, carrying the glucuronic acid attached to the nitrogen in the pyrazole ring while SP itself takes the amido form. Therefore, the main metabolite of SP is a sodium 1-deoxy-[1-phenyl-5-(sulfanilimino)-3-pyrazolin-2-yl]-D-glucopyranosiduronate containing 1 mole of water of crystallization.
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MICHIHIRO UEDA, NORIHIKO MURAKAMI, KAZUKO FURUKI, HARUMI ATSUMURA
1968 Volume 16 Issue 2 Pages
352-356
Published: February 25, 1968
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Metabolic products of sulfamethomidine excreted in human urine were examined by paper chromatography and three metabolites were detected. Unchanged sulfamethomidine and N
4-acetylsulfamethomidine were confirmed by paper chromatography. And, the other one was isolated and identified to be sodium sulfamethomidine-N
1-D-glucopyranosiduronate containing 1 mole of water of crystallization by the comparison of infrared and ultraviolet spectrographic data, and Rf values with the synthetic specimen.
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MASAO SHIMIZU, TAKAAKI AOYAGI, MASAHIRO IWAMOTO, YASUSHI ABIKO, TAKEO ...
1968 Volume 16 Issue 2 Pages
357-363
Published: February 25, 1968
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The new caseinolytic assay method for antiplasmin activity of synthetic compounds was established by introducing the determination of ID
50. trans-Form isomer of 4-aminomethylcyclohexanecarboxylic acid (tranexamic acid) was shown to have very potent antiplasmin activity whereas the cis-form isomer was little effective. The antiplasmin activity of tranexamic acid was 5-7 times greater than that of ε-aminocaproic acid.
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JUNICHI KUNITOMO, ETUKO YUGE, YOSHIKO NAGAI, KAZUYOSHI FUJITANI
1968 Volume 16 Issue 2 Pages
364-367
Published: February 25, 1968
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TETSUJI KAMETANI, HIDEO NEMOTO, SEIICHI TAKANO
1968 Volume 16 Issue 2 Pages
367-370
Published: February 25, 1968
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SHIGENOBU OKUDA, KAORU ABE, SADAO YAMAGUCHI, TOSHIO IBUKA
1968 Volume 16 Issue 2 Pages
370-373
Published: February 25, 1968
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TOSHIO NAMBARA, HIROSHI HOSODA, SHUJIRO GOYA
1968 Volume 16 Issue 2 Pages
374-377
Published: February 25, 1968
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HIROTAKA OTOMASU
1968 Volume 16 Issue 2 Pages
378-380
Published: February 25, 1968
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TOSHIO NAMBARA, MITSUTERU NUMAZAWA
1968 Volume 16 Issue 2 Pages
383-384
Published: February 25, 1968
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SEIICHI OKUI, TADAHIKO OTAKA, MITSURU UCHIYAMA, TSUNEMATSU TAKEMOTO, H ...
1968 Volume 16 Issue 2 Pages
384-387
Published: February 25, 1968
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