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TERUHIKO MESHI, YOSHISHIGE SATO
1972 Volume 20 Issue 10 Pages
2079-2090
Published: October 25, 1972
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Absorption, distribution, excretion and metabolism of trimethoprim were studied in rats. Trimethoprim was absorbed rapidly and almost completely from the digestive tract, the half-life for absorption being 18 min. After absorption the drug left the blood rapidly and was taken up by various organs except brain. The highest concentration was found in the kidney. Appreciable levels were found in the bone marrow, thyroid, liver and lung. The lowest drug concentration was noted in the brain. Approximately 95% of the radioactivity after oral administration of
14C-trimethoprim was recovered from the urine and feces within 72 hr. The urinary excretion is the major excretory route since more than 85% of the total radioactivity recovered appeared in the 72 hr urine. About 30% of the radioactivity excerted in 8 hr urine was present as intact
14C-trimethoprim. Metabolic pathways of trimethoprim consisted of O-demethylation, ring N-oxidation and α-hydroxylation. 3-Demethyl-trimethoprim was the largest metabolite which accounted for more than 30% of the radioactivity excreted in 8 hr urine. 4-Demethyltrimethoprim was excerted mainly as glucuronide which accounted for about 19%. Trimethoprim ring N-oxide and α-hydroxy-trimethoprim were excreted in amounts of 7 and 5%, respectively. Simultaneous administration of sulfamethoxazole did not influence the absorption, distribution, excretion and metabolism of trimethoprim in rat.
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MASAO MURAYAMA, HIROMU MURAI, KENJI SEMPUKU, TATSUO SUMINOKURA, MASAKU ...
1972 Volume 20 Issue 10 Pages
2091-2095
Published: October 25, 1972
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Synthetic meranzin (IVa) was treated with dimethylamine or piperidine in methanol at 40-42°(condition A) and in benzene at 150°(condition B). cis-Amides (VII) and (IX) and trans-amides (VIII) and (X) were obtained under conditions A and B, respectively. Re-examination of the reaction of natural IVa with dimethylamine under condition B revealed that the product was not V proposed by Bohme, et al. but one of the optical isomers of VIII. Treatment of natural IVa with dimethylamine under condition A gave one of the optical isomers of racemic VII. VII-VIII or IX-X equilibrium in ethanol induced by diffused light was also described.
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SEIJU KUBOTA, MASAYUKI UDA
1972 Volume 20 Issue 10 Pages
2096-2101
Published: October 25, 1972
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Tautomerism of 3-α-pyridyl-1, 2, 4-triazoline-5-thione (I) and its methyl derivatives has been studied. The infrared spectra of these compounds indicated the presence of strong intermolecular hydrogen bonding in a solid state. Comparison of the ultraviolet (UV) spectrum of 5-methylthio-3-α-pyridyl-1, 2, 4-triazole (II) with those of the fixed compounds revealed that II exists as 2H-5-methylthio-3-α-pyridyl-1, 2, 4-triazole both in ethanol and in cyclohexane. In the same way, it was found 1-, 2-, and 4-methyl-3-α-pyridyl-1, 2, 4-triazoline-5-thiones (III, IV, and V), which are capable of existing in thione-thiol tautomerism, exist in thione form in ethanol. The parent compound I was also found by means of UV spectroscopy to exist in the thione form of 1H, 4H-3-α-pyridyl-1, 2, 4-triazoline-5-thione in ethanol.
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MITSURU FURUKAWA, YOKO KOJIMA, SEIGORO HAYASHI
1972 Volume 20 Issue 10 Pages
2102-2105
Published: October 25, 1972
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1, 1-Dialkylguanidine reacted with benzil in the presence of sodium ethoxide to give 2-dialkylamino-4-oxo-5, 5-diphenylimidazoline, from which N-acetyl compound was successfully obtained by heating with an great excess of acetic anhydride. The structures of these compounds were confirmed by mass spectra and infrared spectra.
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KOTARO TAKAHASHI, KEIKI KANAYAMA, YOSHIHISA TANABE, MASAKO TAKANI
1972 Volume 20 Issue 10 Pages
2106-2111
Published: October 25, 1972
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A new triterpene named astilbic acid (I) has been isolated from the roots of Astilbe Thunbergii var. congests H. BOISSIEU (Saxifragaceae) in addition to β-peltoboykinolic acid and the structure of astilbic acid has now been established as 3β, 6β-dihydroxyolean-12-en-27-oic acid on the basis of chemical and physicochemical evidences.
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KEIICHI ITO, HITOSHI OBA, MINORU SEKIYA
1972 Volume 20 Issue 10 Pages
2112-2116
Published: October 25, 1972
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There has been introduced a new type of formic acid reduction of the compounds in which both amine nitrogen and ether oxygen are bound to the same carbon. With series of N-(α-butoxybenzyl) dialkylamines, N-(butoxymethyl) dialkylamines and 3-methyloxazolidines, the reaction was normally carried out on heating with distillable formate, TMAF given by 5HCO
2H·2N (CH
3)
3, to give tertiary amines, resulting in reductive fission at the carbon-oxygen bond. Mode of the reduction was clarified by the technique of using deuterated formic acids, in which formyl hydrogen of formic acid is transferred to the carbon of the carbon-oxygen bond. On the basis of this result a possible mechanism is described.
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YOSHIHIRO ENDO, MITSURU UCHIYAMA
1972 Volume 20 Issue 10 Pages
2117-2122
Published: October 25, 1972
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Phospholipid extracted with CHCl
3-MeOH (2 : 1 v/v) from the brain and liver of pyrithioxine-treated animals, as compared to that from control animals, was greater in amount. The amount of phospholipid extracted with CHCl
3-MeOH (7 : 1 v/v) saturated with NH
4OH from tissue residue after CHCl
3MeOH (2 : 1) extraction is found to be smaller in pyrithioxine-treated animals. This decrement of phospholipid is represented by phosphatidylserine and phosphatidylinositol, which both account for the increment of CHCl
3-MeOH (2 : 1)-extracted phospholipid.
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TOKUHIRO WATANABE, FUMIKO HAMAGUCHI, SADAO OHKI
1972 Volume 20 Issue 10 Pages
2123-2127
Published: October 25, 1972
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As a new and convenient method for the synthesis of 4-indolecarboxylic acid (1), the synthesis was started with the reduction of 3-nitrophthalimide (4) with sodium borohydride, followed by hydrolysis of the product to obtain 3-hydroxy-4-nitrophthalide (6). Treatment of 6 with 2 moles of diazomethane gave 2-methoxycarbonyl-6-nitrostyrene oxide (7) whose reductive cyclization afforded methyl 4-indolecarboxylate (2) and it was saponified to the desired 1.
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MINORU SEKIYA, YOSHIYASU TERAO
1972 Volume 20 Issue 10 Pages
2128-2133
Published: October 25, 1972
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It has now been found that reduction of 3-aryl-3-hydroxyphthalimidines to 3-arylphthalimidines are easily effected on heating with the formate reagent, TMAF, known as a constant boiling liquid composed of formic acid and trimethylamine. Fashon of the attack of formic acid in this reaction was clarified by means of using deuterated formate reagent.
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YOSHIKAZU KONDO, TSUNEMATSU TAKEMOTO
1972 Volume 20 Issue 10 Pages
2134-2136
Published: October 25, 1972
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Potassium permanganate oxidation of acetoneberberine gave rise to so called neoxyberberine acetone and 2-(2, 3-dimethoxy-6-carboxy-α-acetonyl-benzyl)-1-oxo-6, 7-methylenedioxy-1, 2, 3, 4-tetrahydroisoquinoline (IV). The structure of IV was established by chemical and spectral data.
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MASAFUMI YOSHIMOTO, NOBORU ISHIDA, YUKICHI KISHIDA
1972 Volume 20 Issue 10 Pages
2137-2142
Published: October 25, 1972
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Three 2-propynyl sulfones (VIIIa-c) reacted with methyl acrylate to give the corresponding 2-carbomethoxy-4-ethynyl-4-arylsulfonylcyclohexanones (IXa-c), respectively. Nucleophilic reaction of acetylenic sulfonyl carbanion showed ambident character depending on the nature of electrophiles which were classified into two kinds. Some discussions of the reaction and physical properties of the products are presented.
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RYUICHI HIGUCHI, TOSHIO KAWASAKI
1972 Volume 20 Issue 10 Pages
2143-2149
Published: October 25, 1972
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The more polar four triterpenoid saponins, D-G, of the seven, A-G, so far isolated in pure state from the seeds of Akebia quinata DECNE. were characterized as follows : saponin D (mp>225°(decomp.), [α]
D+15°), 3-O-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (IV) ; E (mp 210-214°(decomp.), [α]
D+6°), 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (XI) ; F (mp 211-214°(decomp.), [α]
D-4°), 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (XIV) ; G (mp>218°(decomp.), [α]
D-19°), 3-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (XVI). They are new hederagenin 3, 28-O-bisglycosides and related to each other and to saponins A, B, and C.
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MASAICHIRO MASUI, KOHJI SUDA, CHINO YIJIMA
1972 Volume 20 Issue 10 Pages
2150-2155
Published: October 25, 1972
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N-(1-Cyanoalkyl) alkylideneamine N-oxide reacts with carboxamides to give N-(1-cyanoalkyl)-N-(1'-carboxamido-alkyl) hydroxylamines. The reaction is catalyzed by strong bases. On warming in solvents these adducts readily decompose to the starting nitrones and amides, and the decomposition is accelerated by elevation of temperature.
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TOSHIO NAMBARA, TOSHIHIRO KUDO
1972 Volume 20 Issue 10 Pages
2156-2162
Published: October 25, 1972
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Isomeric 15α- and 17α-bromo-13α-estratrien-16-ones (IX, X) were prepared from the parent 16-ketone (VII) by way of the enol acetate (VIII). The configuration of both bromine atoms introduced was determined by the standard method of Fieser and Ettorre. These positional isomers were readily distinguished by converting into the ⊿
15- and ⊿
16- unsaturated compounds (XIII, XIV), respectively. On the basis of the spectral data listed in Table I the nature of C-bromine bonds and the conformation of ring D have been discussed. Two synthetic routes leading to the 17α-acetoxy-16-ketone (V) have also been described.
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SHUNJI NARUTO, OSAMU YONEMITSU
1972 Volume 20 Issue 10 Pages
2163-2171
Published: October 25, 1972
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The photoreaction of indole with methyl chloroacetate afforded a mixture of seven isomeric methyl indoleacetates, mainly the 4-isomer, whose separation into each component was carried out by repeated column chromatographies. The structues of all of them confirmed by their spectral data and by the unequivocal sysntheses. The unusual reactivity of the 4-position on the indole nucleus was explained on the basis of the calculation data by SCF-CI-MO method.
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YUKIO MAEBAYASHI, KOMEI MIYAKI, MIKIO YAMAZAKI
1972 Volume 20 Issue 10 Pages
2172-2175
Published: October 25, 1972
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Incorporation of L-phenylalanine-U-
14C, Na-acetate-2-
14C into ochratoxin A was demonstrated in Aspergillus ochraceus, suggesting that the biosynthesis of ochratoxin A involves so called "acetate-malonate" and "shikimic acid" pathways. By the aid of
13C-NMR spectrometric method, the participation of Na-formate-
13C for the formation of carboxyl group was confirmed.
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TSUNEHIRO KITAGAWA, TAKAKO MIURA, HYOZO TANIYAMA
1972 Volume 20 Issue 10 Pages
2176-2184
Published: October 25, 1972
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The new purification method, alkylations and acylations of tuberculostatic antibiotic viomycin were performed. The characterizations were conducted with viomycin as well as the derivatives obtained by these reactions. And also it was clarified that the alkylations on the reactive hydroxyl group of tuberactidine function had no significant influence on the antimicrobial activities while, the acylations on the N-terminal amino functions nullified the potency.
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MICHIYA KIMURA, MASAHIKO TOHMA, TSUTOMU TOMITA
1972 Volume 20 Issue 10 Pages
2185-2190
Published: October 25, 1972
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When cholesterol (I) was treated with the hydrogen peroxide-ferrous sulphate system in an acetic acid solution, there were formed 5α-cholestane-3β, 5, 6β-triol (II), 3β-acetoxy-5α-cholestane-5, 6β-diol (III), 5, 6α-epoxy-5α-cholestan-3β-ol (IV), 6β-acetoxy-5α-cholestane-3β, 5-diol (V), and 3β, 6β-diacetoxy-5α-cholestan-5α-ol (VI). Ferrous ions accelerated remarkably the formation of these products (Fig. 2) as well as peracetic acid (Fig. 3). The same ions were, however, likely to be independent of forming the epoxide (IV) from I with peracetic acid (Fig. 4). Hydrogen peroxide and ferrous ions were cooperative in facilitating the formation of II from IV, conrtary to be entirely invalid in their independent use (Fig. 5). Thus, it seemed in the present reaction that the epoxide (IV) is produced heterolytically, as usual, with peracetic acid which can easily be formed in the mixture of acetic acid and hydrogen peroxide (Chart 1) and that the triol (II) as well as the derivatives (III, V, and VI) are formed mainly through IV.
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TERUOMI JOJIMA, HIDEO TAKESHIBA, TAKUO KONOTSUNE
1972 Volume 20 Issue 10 Pages
2191-2203
Published: October 25, 1972
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Heating 3-chloro-6-(2-allylphenoxy) pyridazine (IIIa) with or without a solvent afforded xanthene (Va) by a novel intramolecular cycloaddition reaction followed by elimination of nitrogen and hydrogen chloride. Formation of a fully aromatized product indicated that elimination of both N
2 and HCl has occurred from the initially formed π
4+π
2 cycloadduct (IV). Variously substituted xanthenes were prepared by heating the corresponding 3-chloro-6-(2-allylphenoxy) pyridazines in diethylaniline (DEA). The compound having an allylic group at the para-position of the benzene ring did not give any cyclized product, because the allylic double bond was too far from the pyridazine ring. Similar treatment of 3-chloro-6-(2-propenylphenoxy) pyridazine (XXVI) gave rise to 1-methyldibenzofuran (XXVIII) in a low yield.
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FUMIHIKO UCHIMARU, SEIZABURO OKADA, AKIRA KOSASAYAMA, TSUNEO KONNO
1972 Volume 20 Issue 10 Pages
2204-2208
Published: October 25, 1972
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The nuclear magnetic resonance parameter of disubstituted pyrazines have been correlated with the chemical structure. The coupling constants of 2, 3-, 2, 5-, 2, 6-disubstituted pyrazines are 2.5-3.0, 1.1-1.4, 0 Hz respectively, and these values are not influenced by the kind of the substituents. The calculated chemical shifts which are obtained from the additivity rule of the shielding parameter of the substituents are well agreed with the observed ones.
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YASUSHI NAKAGAWA, OSAMI AKI, KENZO SIRAKAWA
1972 Volume 20 Issue 10 Pages
2209-2214
Published: October 25, 1972
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1-Alkyl-2, 1-benzisoxazolium salts were prepared by the reaction of 2, 1-benzisoxazoles with trialkyl orthoformates in the presence of Lewis acids as well as with Meerwein's reagents or dialkoxycarbonium hexachloroantimonates. Reactions of these quarternary salts with various nucleophilic reagents afforded 3-substituted 1-alkyl-2, 1-benzisoxazoline derivatives.
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TSUNEHIRO KITAGAWA, TAKAKO MIURA, KUNIO FUJIWARA, HYOZO TANIYAMA
1972 Volume 20 Issue 10 Pages
2215-2225
Published: October 25, 1972
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The novel partial hydrolysis of peptide bonds by using N→O acyl migrative reactions followed by the methanolysis of the resulting ester linkages were studied to give the successful application with tetrahydro derivative of viomycin, a tuberculostatic antibiotic. Also, the partial hydrolysis of perhydroacetylviomycin yielded two peptide fragments. The sequential analysis of these fragments by Edman-dansyl procedures and the end group analysis concluded that the primary structure of viomycin is formulated as XXV. The sequence is well compatible to the chemical formula I, the one of recently proposed two structures.
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ISAO KITAGAWA, AKIKO MATSUDA, ITIRO YOSIOKA
1972 Volume 20 Issue 10 Pages
2226-2234
Published: October 25, 1972
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The sapogenol constituents of five Japanese Primulaceous plants : i) Primula sieboldi E. MORREN, roots (Japanese name : sakuraso), ii) P. japonica A, GRAY, roots and fruits (kurinso), iii) Lysimachia mauritiana LAM., Fruits (hamabossu), iv) L. clethroides DUBY, roots (okatoranoo), v) L. japonica THUNB., roots (konasubi), have been investigated. It has been elucidated that the major sapogenols obtained by acid hydrolysis of saponin of each plant material are primulagenin A (VIII) and/or dihydropriverogenin A (XIII), while periodate oxidation followed by alkaline treatment of saponin furnished the inconsistent sapogenol compositions and the genuine sapogenols have been shown to possess a 13β, 28-oxide moiety as seen in protoprimulagenin A (XV), a newly isolated sapogenol from i), ii), iv), and v), and priverogenin B (XII). The structure of protoprimulagenin A (XV) has been established on the basis of chemical and physicochemical evidences.
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TOSHIO NAMBARA, SEIJIRO HONMA, KISEKO KANAYAMA
1972 Volume 20 Issue 10 Pages
2235-2239
Published: October 25, 1972
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The role of the conjugate in the biosynthesis of 2-methoxyestrogen in the living animal has been explored by the double-isotope technique. The isotope ratios of the isomeric catechol estrogen monomethyl ethers excreted in urine after simultaneous administration of estrone-4-
14C and estrone-6, 7-
3H sulfate or estradiol-6, 7-
3H 3-glucuronide were determined. Comparison of the
3H/
14C value with that of the administered steroid implies that the sulfate conjugation may possibly participate in the predominant formation of 2-methoxyestrogen, while the conjugation with glucuronic acid may not. The dimethyl ether of catechol estrogen was metabolized with random O-demethylation yielding two isomeric monomethyl ethers both in the rat and man. Therefore it appears that the selective O-demethylation may not be involved in the preferential formation of 2-methoxyestrogen.
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MASAHIKO TOHMA, AKIHARU FUJINO, KATSUHIKO YAMAZAKI, MICHIYA KIMURA
1972 Volume 20 Issue 10 Pages
2240-2245
Published: October 25, 1972
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The β-axial hydroxylated 5β-spirostan-1- and 3-ones were prepared from the steroidal sapogenins in Convallaria and diosgenin, and the optical rotatory dispersion curves of these ketones were measured in methanol or dioxane. The 5-hydroxy-25 (R), 5β-spirostan-3-one (XIII) showed a weak positive amplitude (a : +16.0) in contrast to the negative one of the parent 3-ketone (I, a : -16.6). The hydroxyl groups substituted on the symmetrical β-axial positions to the carbonyl groups led to marked changes in the amplitude of Cotton effect in the 5β-spirostanones, and opposed to the prediction from the octant rule.
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SHOSHIRO NAKAMURA, KENJI ASANO, HIDEO FUKUDA
1972 Volume 20 Issue 10 Pages
2246-2250
Published: October 25, 1972
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The cultured filtrates of Streptomyces were screened for the anti-thymidine kinase activity using the homogenate of Yoshida sarcoma cells and (methyl-
3H)-thymidine to obtain antitumor antibiotics. The active component produced by Streptomyces yokosukanensis was isolated and determined to be a new acid phosphatase (E.C. 3.1.3.2.). Production, isolation, purification, effect of pH on the activity, stability, effect of temperature on the activity, effect of inhibitors on the activity and substrate specifity are described.
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SHINICHI FUJITA, YASUJI FUJITA
1972 Volume 20 Issue 10 Pages
2251-2255
Published: October 25, 1972
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The essential oils of Magnolia salicifolia MAXIM. gathered at Mt. Ohira and its vicinity, Kawanishi-shi, Hyogo Prefecture have been examined. The characteristics of the shoot oils are abundant existence of methylchavicol (13.5-22.5%), safrole (17.0-24.6%), and methyleugenol (21.0-43.5%).
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TOSHIO NAMBARA, HIROSHI HOSODA, TAKAKO ANJYO, SHIGEO IKEGAWA
1972 Volume 20 Issue 10 Pages
2256-2261
Published: October 25, 1972
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In order to clarify the stereochemistry of hydrogen loss from C-2 and C-4 during the microbial ⊿
1- and ⊿
4-dehydrogenation the titled compounds have been synthesized as the suitable substrates. The key intermediates leading to the desired compounds, ⊿
2- and ⊿
3-olefins (V, VI), were prepared from 5β-androstane-3α, 17β-diol 3-tosylate 17-acetate (IV). Epoxidation with per-acid followed by trans-diaxial opening of the resulting β-epoxides (VII, VIII) with lithium aluminum deuteride gave 2α- and 4α-deuterio-5β-androstane-3β, 17β-diols (X, XIV). On the other hand V and VI were transformed into the 2β- and 4β-deuterio-3β, 17β-diols (XII, XVI) by treatment with deuterated diborane and then with hydrogen peroxide. Upon oxidation with chromium trioxide-pyridine complex these labeled diols were led to the 2- and 4-deuterated 3, 17-diketones (XI, XIII, XV, XVII), respectively.
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MITSURU FURUKAWA, KENJI NAGATO, YOKO KOJIMA, SEIGORO HAYASHI
1972 Volume 20 Issue 10 Pages
2262-2264
Published: October 25, 1972
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MASARU OGATA, HIROSHI MATSUMOTO
1972 Volume 20 Issue 10 Pages
2264-2268
Published: October 25, 1972
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ZENICHI HORII, TAKESHI IMANISHI, MIYOJI HANAOKA, CHUZO IWATA
1972 Volume 20 Issue 10 Pages
2269-2271
Published: October 25, 1972
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SHUNJI NARUTO, OSAMU YONEMITSU
1972 Volume 20 Issue 10 Pages
2272-2274
Published: October 25, 1972
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MIKIO YAMAZAKI, YUKIO MAEBAYASHI, KOMEI MIYAKI
1972 Volume 20 Issue 10 Pages
2274-2276
Published: October 25, 1972
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MIKIO YAMAZAKI, YUKIO MAEBAYASHI, KOMEI MIYAKI
1972 Volume 20 Issue 10 Pages
2276-2278
Published: October 25, 1972
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ISAO KITAGAWA, TSUTOMU NAKANISHI, YOSHIHISA ITO, M.U.S. SULTANBAWA, IT ...
1972 Volume 20 Issue 10 Pages
2278-2281
Published: October 25, 1972
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AKIO HOSHI, MITSUZI YOSHIDA, FUMIHIKO KANZAWA, KAZUO KURETANI, TADASHI ...
1972 Volume 20 Issue 10 Pages
2286-2287
Published: October 25, 1972
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NENOKICHI HIRAO, TOSHIO TOYAMA, AKIRA TAKAHATA, BOMPEI YASUI
1972 Volume 20 Issue 10 Pages
2287-2289
Published: October 25, 1972
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TAKASHI YAMAGISHI, KOJI HAYASHI, HIROSHI MITSUHASHI
1972 Volume 20 Issue 10 Pages
2289-2291
Published: October 25, 1972
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TADAKAZU MURATA, MASAKAZU SHINOHARA, MASUO MIYAMOTO
1972 Volume 20 Issue 10 Pages
2291-2292
Published: October 25, 1972
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SHIGEO UKAI, KAZUO HIROSE, TADASHI KIHO, CHIHIRO HARA, TSUTOMU IRIKURA ...
1972 Volume 20 Issue 10 Pages
2293-2294
Published: October 25, 1972
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