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長浜 昇, 高森 勲, 小寺 啓司, 鈴木 真言
1971 年 19 巻 4 号 p.
649-654
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Albocycline, C
18H
28O
4, is a neutral antibiotic produced by Streptomyces sp. The physico-chemical properties indicated that it was one of the macrolide antibiotic consisting of only macrocyclic lactone without any carbohydrate moiety. Analytical and spectral data on albocycline, its acetate and ozonolysis products made it possible to assume that albocycline possessed a hydroxy, a methoxy, a lactone, three olefinc linkages and also four branched-methyl groups. From these data the partial structure of albocycline was suggested as illustrated in Chart 1 and 3.
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長浜 昇, 高森 勲, 鈴木 真言
1971 年 19 巻 4 号 p.
655-659
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
By the catalytic hydrogenation of albocycline at room temperature four hydrogenation products were obtained. Two of them, II and III, were confirmed to have 14-membered lactone and 5-membered lactone structure respectively from infrared (IR) and nuclear magnetic resonance (NMR) spectral data. They were the isomer and correlated to each other. These correlations suggested the position of a hydroxy group in albocycline. II was derived to the corresponding hydrocarbons (IV) by complete hydrogenation, of which mass spectra suggested the carbon skeleton and branching pattern of methyl group. From these results and the 100 MHz NMR spectral data of albocycline and its acetate, the structure of albocycline was finally proposed as Ia.
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長浜 昇, 高森 勲, 鈴木 真言
1971 年 19 巻 4 号 p.
660-666
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
By the catalytic hydrogenation of albocycline in acetic acid under high pressure at elevated temperature, nine reaction products were obtained. They were classified into pairs by their infrared (IR), nuclear magnetic resonance (NMR) and mass spectral data. The eluci dation of structures of these pair products gave the conclusive answers about the positions of O-functions, especially that of a methoxy group, in albocycline molecule. Thus, the structure of albocycline was finally confirmed as Ia.
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佐藤 千代子, 長尾 拓, 河野 武郎, 清本 昭夫
1971 年 19 巻 4 号 p.
667-675
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Racemic Trimetoquinol [dl-1-(3, 4, 5-trimethoxybenzyl)-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline (I)] hydrochloride was administered to rabbits and rats by intravenous injection and the metabolites excreted into the 24 hr urine pools were investigated. Unchanged I and five metabolites, dl-1-(3, 4, 5-trimethoxybenzyl)-6-methoxy-7-hydroxy-1, 2, 3, 4-tetrahydroisoquinoline (II), dl-1-(3, 4, 5-trimethoxybenzyl)-6-hydroxy-7-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (III) and glucuronides of I, II and III were identified. Species differences between rabbit and rat were observed in the capacity of O-methylation and in the ratio of the two O-methylated isomers. In rabbits, a majority of administered I appeared as glucuronide of I, whereas glucuronide of III occupied the highest proportion in rats.
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武田 健一, 森 芳夫, 里 武
1971 年 19 巻 4 号 p.
676-686
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Dehydrogenation of lindenenyl acetate (Ib) by palladium was studied. The reaction was found to proceed directly to a final product (linderazulene (II)) by a main route, and partly to II via a dihydroazulene intermediate (IV), by a concerted mechanism. Dehydrogenation of Ib in deuteropentane showed that palladium has properties of both a dehydrogenation and a hydrogenation catalyst under N
2, at 300°.
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虫鹿 好孝, 米田 直人
1971 年 19 巻 4 号 p.
687-695
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The mixed phosphoric diesters (2) of dl-α-tocopherol and ethylene glycol analogues, such as diethylene glycol, its monomethyl ether, pentaethylene glycol and polyethylene glycol 600, were conveniently prepared by two routes shown in chart 2 and 3 by using 2-chloromethyl-4-nitrophenyl phosphorodichloridate (3). Moreover, diethylene glycol bis (dl-α-tocopheryl hydrogen phosphate) (11) was prepared and the structures of 2 were confirmed by comparison with 11. It was observed that the mixed esters 2 derived from pentaethylene glycol and polyethylene glycol 600 were easily soluble in water.
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虫鹿 好孝, 米田 直人
1971 年 19 巻 4 号 p.
696-704
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
β'-Haloethyl isopropylidene-α-glycerophosphoryl 2-chloromethyl-4-nitrophenyl phosphates (10 and 11) were prepared by the stepwise phosphorylations of ethylene halohydrin and 1, 2-isopropylidene-glycerol with 2-chloromethyl-4-nitrophenyl phosphorodichloridate (3), a phosphorylating reagent having an "activatable" protecting group. The protecting group of 10 and 11 was readily and selectively removed by hydrolysis through an active intermediate 14 derived from the reaction of 10 and 11 with various tertiary amines to afford the corresponding isopropylidene-α-glyceryl β'-haloethylhydrogen phosphate (15) along with 2-hydroxy-5-nitrobenzyl trialkyl ammonium chloride (16), a chip of the active intermediate 14. The halogen atom in the ethyl chain of the phosphate 15 reacted with tertiary amine at the same time to afford the corresponding quaternary ammonium compound 17 which was converted by subsequent hydrolysis into α-glycerophosphoryl choline (1a) and its analogues (1b-d). Thus, DL-α-glycerophosphoryl choline (1a), its L-isomer (1a-L), inner salt of β'-(DL-α-glyceryl hydrogen phosphoroxy) ethyl triethyl ammonium hydroxide (1b), 1-[β'-(DL-α-glyceryl) hydrogen phosphoroxy] ethyl 1-methyl piperidinium hydroxide (1c) and inner salt of 1-[β'-(DL-α-glyceryl) hydrogen phosphoroxy] ethyl 1, 4-diazonia bicyclo [2, 2, 2] octane hydroxide (1d) were prepared in good yield. DL-Myristoyl lecithin (18) was prepared by acylation of 1a with myristoyl chloride to confirm the structure of synthetic 1a.
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中野 純次, 西村 温樹
1971 年 19 巻 4 号 p.
705-713
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Oxidation of thiamine sodium salt (I) with iodine in the presence of amines (II) gave S-aminothiamines (III). When III was treated with weak acids, oxathiolane derivative (VIII) was obtained. From VIII, some new thiamine derivatives, pyrimido [4, 5-c] [1, 2, 6]-10H-thiadiazocine (XIII), S-phosphate (XVI) derivatives and so forth, were derived. An analogue of XVI, cyclic O, S-phosphate (XVIII) was also synthesized.
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亀谷 哲治, 福本 圭一郎, 気賀沢 和雄, 脇坂 菊雄
1971 年 19 巻 4 号 p.
714-717
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Phenol oxidation of (R) (-)-N-methylcoclaurine (V) and (S) (+)-reticuline (VI) with peroxidase was examined in order to get the bisbenzylisoquinoline type compounds, but only the cleaved products were obtained. (±)-O-Benzyl-N-methylcoclaurine (X) also afforded the cleaved one in the same reaction. However, ferricyanide oxidation of VI gave isoboldine (IX) and pallidine (VIII) together with the cleaved products, isovanillin (XIV) and thalifoline (VII). Moreover, phenol oxidation of cuspidaline (XVII) was also described.
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桐野 豊, 管 孝男
1971 年 19 巻 4 号 p.
718-721
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The oxidation of L-ascorbic acid with Ti
3+-H
2O
2 has been investigated by a rapidmixing flow technique coupled with electron spin resonance. Two kinds of spectra were distinguished, one of them being not reported hitherto. To assign these electron spin resonance spectra, the oxidation of hydroxytetronic acid, a simple analog of L-ascorbic acid, was further investigated. In the light of the obtained electron spin resonance parameters possible radical structures were discussed.
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稲葉 茂穂, 石墨 紀久夫, 森 和夫, 山本 久夫
1971 年 19 巻 4 号 p.
722-729
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The synthesis of 1, 3-dihydro-1-methyl-7-nitro-5-phenyl-2H-1, 4-benzodiazepin-2-one (XVII) is described. 5-Nitro-3-phenylindole-2-carboxylic acid (X) was prepared by several methods and one of the most convenient methods was the treatment of p-nitrophenylhydrazine (VIII) with azlactone (V). A by-product isolated from the synthesis of XVII was shown to be 2-(2-benzoyl-4-nitroanilino)-N-methylacetamide (XVIII) by a comparison with an authentic sample prepared by independent synthesis.
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掛見 喜一郎, 瀬崎 仁, 岩本 喜久生, 小林 宏, 乾 賢一
1971 年 19 巻 4 号 p.
730-736
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The effect of cupric ion on the stability and antibacterial activity of penicillins, benzylpenicillin and 2, 6-dimethoxyphenylpenicillin, in phosphate buffer solution and phosphate broth kept at pH 5.0 was investigated. The degradation was found to obey first-order kinetics to produce the corresponding penicillenic acids, though the formation of penicilloic acid analogs have been postulated in other studies. Catalytic and complexing effect of cupric ion on the stability of penicillins was revealed in relatively lower and higher concentrations of the metal ion respectively, where an appreciable difference in the effect was noted between buffer solution and broth. Apparent stability constants for the proposed complex between penicillins and cupric ion were estimated to be log K
app=2.65 and 2.91 with benzylpenicillin and 2, 6-dimethoxyphenylpenicillin, respectively. The antibacterial activity against Staphylococcus aureus was not apparently affected by the addition of cupric ion, which indicates an apparent lack of correlation between the stability and the activity of the drug in broth. This is presumably because the probable enhancing effect of the metal ion on the cell wall permeability of the penicillins outweighs the other effects investigated.
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小島 孝一
1971 年 19 巻 4 号 p.
737-745
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Irradiation of 3α, 5-cyclo-6-oxo-17β-acetoxy-5α-androstan-19-oic acid (1) in tertiary butyl alcohol yielded 4α-tert-butoxy-6, 6-dihydroxy-17β-acetoxy-5α-androstan-19-oic acid 6, 19-lactone (2) and 6-oxo-17β-acetoxyandrost-4-en-19-oic acid (3) in 50% and about 10% yields respectively. The former (2) was found to be formed by photochemical addition of tertiary butyl alcohol to the α, β-unsaturated ketone system in the latter (3). In connection with the mechanism of the above reaction, photolysis of 6-oxo-17β-acetoxy-5α-androstan-19-oic acid (9) in methanol and tertiary butyl alcohol is conducted to yield 5, 6-secocarboxylic acid derivatives (17, 19, 20, 21), and irradiation of methyl 3α, 5-cyclo-6-oxo-17β-acetoxy-5α-androstan-19-oate in tertiary butyl alcohol was also described yielding methyl 4α-tert-butoxy-6-oxo-17β-acetoxy-5α-androstan-19-oate (4) and methyl 6-oxo-17β-acetoxyandrost-4-en-19-oate (14).
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ELI SHEFTER, THOMAS F. BRENNAN, PHYLLIS SACKMAN
1971 年 19 巻 4 号 p.
746-752
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The dominant force of attraction in the 2 : 1 5-chlorosalicylic acid : theobromine crystalline complex is hydrogen bonding. There are three relatively strong hydrogen bonds, all involving a carboxyl group of the salicylate. A substantial degree of π overlap exists between the phenyl ring of the acid and the xanthine nucleus.
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菊池 徹, 豊田 達郎
1971 年 19 巻 4 号 p.
753-758
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The structure of pachysandiol-A, a new triterpenediol isolated from the neutral fraction of Pachysandra terminalis SIEB. et ZUCC. (Buxaceae), was investigated and assigned to the formula I on the basis of chemical and spectroscopic evidences. In this connection, the 2-hydroxyl group of cerin, for which 2β (equatorial)-orientation had been proposed, was proved to have the axial 2α-configuration.
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高見沢 映, 平井 健太郎, 石破 暉之, 牧野 逸男
1971 年 19 巻 4 号 p.
759-763
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Reaction of thiamine sodium salt (III) with carbon dioxide afforded 2, 6a-dimethyl-6a, 8, 9, 9a, 10a, 11-hexahydro-5H-furo [2, 3-h] thiachromine (VI). Further studies to investigate alternative synthetic routes to VI were carried out and the mechanism for the formation of VI was discussed.
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岡本 義久, 高田 純, 上田 武雄
1971 年 19 巻 4 号 p.
764-769
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
1, 2, 3, 4-Tetrahydro-2-oxo-pyrido [1, 2-a] pyrimidinium chloride (IIa) was easily obtained by the condensation of ethyl 3-chloropropionimidate hydrochloride (I) under mild conditions. On the basis of this finding, methyl derivatives of 2-aminopyridine, 2-aminopyrimidine, 2-aminopyrazine, 2-aminothiazole and 2-amino-4-methylthiazole were reacted with the imidate I and the corresponding compounds, methyl derivatives of IIa, VIa, VII, VIIIa and VIIIb, were obtained, respectively. 2-Amino-6-methylpyridine hindered the production of an expected compound. This result was also observed in the case of 2-aminoquinoline and 2-aminobenzothiazole.
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富田 真雄, 岡本 靖子, 菊池 徹, 大崎 健次, 西川 正夫, 神谷 和秀, 佐々木 喜男, 的場 勝英, 後藤 格次
1971 年 19 巻 4 号 p.
770-791
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Structures of acutumine (XXXVIIa) and acutumidine (XXXVIIb), isolated from Menispermum dauricum DC. and Sinomenium acutum REHD. et WILS. (Menispermaceae), were investigated. On the basis of a series of degradative and spectroscopic evidences, their structures including absolute stereochemistry are assigned to the formula XXXVIIa and XXXVIIb, respectively, which are in good agreement with the result obtained from the X-ray analyses of acutumine and acetylacutumine. Apparently, these alkaloids represent a new class of alkaloids with a novel skeleton and also provide rare examples of chlorine-containing alkaloids.
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林 時司, 河合 聰, 大野 武男
1971 年 19 巻 4 号 p.
792-795
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
In the present paper, it has been described on a relationship between the fluorescence emission and the carbonyl stretching frequency of flavone derivatives. Non-fluorescent ligands (type I, III in Chart 1) show their carbonyl frequencies in the 1645-1650 cm
-1 region, while fluorescent ligands (type II, IV) give those in the 1610-1620 cm
-1 region and cause a remarkable increase of the fluorescence intensity by forming of chelates with some metals such as beryllium, aluminum, magnesium, thorium, yttrium. Further evidence is found by examining the chemical shift of 2-proton in several chromone derivatives. That of 3-hydroxychromone is noteworthily lower than those of the other chromone derivatives, indicating the more aromaticity of its pyrone ring. From these data, it is concluded that introduction of a hydroxyl group into 3-position of flavone causes the remarkable lowering of carbonyl frequency and the increase of aromaticity of pyrone ring, which is very likely responsible for the fluorescence emission.
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片岡 正剛, 高畠 英伍
1971 年 19 巻 4 号 p.
796-803
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The N-demethylation of five antihistaminics possessing diemethylaminoalkyl group was compared in in vitro production of formaldehyde by liver 9000 g supernatant fraction from four animal species, rat, mouse, guinea pig and rabbit. Sex difference was observed in only rats but the demethylating activities varied from species to species for a drug and from drug to drug in a species. The high demethylating activities were shown for trimeprazine or diphenhydramine by rats and for fenethazine or chlorpheniramine by rabbits. In adult male rats, castration or SKF 525A reduced the activities and 19-nortestosterone phenylpropionate enhanced the activities without the big change in relative order. Phenobarbital induced the activities of female rat liver in almost same proportion for every drug but 3-methylcholanthrene did not show stimulatory effect. The formaldehyde production from N-oxides was comparatively small and did not show the difference among drugs. No correlation between the lipid solubility and the N-demethylation was found. The significance of investigation of species differences in the drug metabolism was discussed.
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塚本 長太郎, 尾関 昭二, 手島 喜久雄, 安達 清次
1971 年 19 巻 4 号 p.
804-807
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Solubilization of p-dimethylaminoazobenzene, change in color of pinacyanol iodide, and surface tension were measured to determine the critical micelle concentrations (CMC) of ascorbyl monofatty acid esters (AMFE). The CMC is decreased by increasing the length of the fatty acid chain of AMFE. Relationship between log CMC of laurate, myristate, and palmitate which was determined by surface tension method and the numbers of carbon atoms in alkyl groups of these compounds may be represented by the expression, log CMC =-0.584 -0.187 N, where CMC is expressed in molarity, N is number of carbon atoms in the chain.
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南部 直樹, 永井 恒司, 野上 寿
1971 年 19 巻 4 号 p.
808-812
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
The permeation of phenothiazines through cellulose membrane was investigated as a successive study of the adsorption from aqueous solution reported in a previous paper. The permeability decreased with the increase in molecular weight of phenothiazines. The activation energy of permeation was close to those of diffusion of usual organic medicinals in water. Any remarkable effect of pH on the permeation was not observed in the present conditions. It was demonstrated from these results that the permeation of phenothiazines through cellulose membrane proceeds on the basis of a diffusion through pore. In comparison with the diffusion constant of levomepromazine maleate in aqueous solution evaluated from the dissolution rate by the rotating disk method, the interaction coefficient of the diffusion through cellulose membrane was given as 0.453.
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宮崎 利夫, 山田 倫久
1971 年 19 巻 4 号 p.
813-816
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Extracellular major polysaccharide of P. debaryanum is a glucan, [α]
21D -28° (H
2O). Results of periodate oxidation, Smith-degradation, and methylation studies showed that the glucan has a highly branched structure possessing mainly (1→3)-linkage and a small amount of (1→6)-linkage.
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佐藤 利夫, 南波 憲良, 鈴木 周一
1971 年 19 巻 4 号 p.
817-820
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Hydrogenation of unsaturated esters was performed with NaBH
4-transition metal salt systems. Nickel, cobaltous and cupric salts were effective metal salts for reduction of olefinic esters. Hydrogenation of the olefinic bonds proceeded quantitatively to afford the corresponding saturated esters when using one of the following pairs : NiCl
2·6H
2O (0.1 mole)-NaBH
4 (2 moles), CoCl
2·6H
2O (0.25 moles)-NaBH
4 (10 moles) and CuCl
2.2H
2O (0.3 moles)-NaBH
4 (6 moles) per mole of I.
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佐々木 琢磨, 新井 祥子, 池川 哲郎, 千原 呉郎, 福岡 文子
1971 年 19 巻 4 号 p.
821-826
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
Antitumor polysaccharide preparations G-Z and P-Z were fractionated from the water soluble extracts of Ganoderma applanatum (PERS.) PAT and Phellinus linteus (BERK. et CURT) AOSHIMA, basidiomycetes of Polyporaceae, respectively, by fractional precipitation with ethanol and cetyltrimethylammonium hydroxide. The structures of G-Z and P-Z consist of β-(1→3), (1→4) linked D-glucose residue, and β-(1→3) linked D-glucose residue, respectively. These polysaccharide preparations have marked antitumor activity against transplanted sarcoma 180 in mice, and a complete regression of tumors was observed in more than half of animals with no sign of toxicity. Some derivatives of P-Z were synthesized and their antitumor effects were also examined.
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北川 晴雄, 鎌滝 哲也
1971 年 19 巻 4 号 p.
827-830
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
An attempt was made to estimate the activity of microsomal drug-metabolizing enzymes of the human liver at the time of death using post-mortem human livers. The human livers were placed under various conditions, and from the rate of loss of the activities, the activities at the time of death were estimated. The increase in the formation of formaldehyde-like substance in proportion to the period after death was also observed.
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桐野 豊, 管 孝男
1971 年 19 巻 4 号 p.
831-832
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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加藤 鉄三, 新妻 卓逸, 前田 和代
1971 年 19 巻 4 号 p.
832-836
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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佐藤 英助, 小山 行一, 金岡 祐一
1971 年 19 巻 4 号 p.
837-839
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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小林 裕子, 角田 広, 辰野 高司
1971 年 19 巻 4 号 p.
839-842
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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石井 宏, 東条 武彦, 中村 美春
1971 年 19 巻 4 号 p.
842-844
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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南原 利夫, 松木 容彦, 川原田 良彦
1971 年 19 巻 4 号 p.
844-846
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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赤堀 昭, 安田 郁夫, 岩男 徹
1971 年 19 巻 4 号 p.
846-848
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
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義平 邦利, 手塚 美知子, 高橋 千加子, 名取 信策
1971 年 19 巻 4 号 p.
851-854
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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南原 利夫, 沼澤 光輝
1971 年 19 巻 4 号 p.
855-856
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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ヒキノ ヒロシ, 小倉 勝, 藤田 雅子, 伊藤 邦雄, 竹本 常松
1971 年 19 巻 4 号 p.
856-857
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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三木 卓一, 松尾 泰介
1971 年 19 巻 4 号 p.
858-859
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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恩田 政行, 東 敦子
1971 年 19 巻 4 号 p.
859-861
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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木下 俊夫, 飯沼 文夫, 森口 郁生, 辻 章夫
1971 年 19 巻 4 号 p.
861-862
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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吉本 昌文, / 岸田 有吉, YUKICHI KISHIDA
1971 年 19 巻 4 号 p.
863-865
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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枡井 雅一郎, 飯島 千之, 須田 晃治
1971 年 19 巻 4 号 p.
865-866
発行日: 1971/04/25
公開日: 2008/03/31
ジャーナル
フリー
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西部 三省, 久田 末雄, 稲垣 勲
1971 年 19 巻 4 号 p.
866-868
発行日: 1971/04/25
公開日: 2008/03/31
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