Chemical and Pharmaceutical Bulletin

Pharmacokinetic Investigation of 17α-Desoxymethasone (A 41 304) in Rats

SHORYO HAYASHI, TAKASHI SAKAGUCHI, HIKARU OZAWA

1974 Volume 22 Issue 12 Pages 2771-2777
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2771

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^3H-A 41 304 ointment in the concentration of 0.27% was applied to the back skin of rats, and its absorption and distribution in the blood and organs and its excretion in the urine and feces were examined in the course of time. 1. Most of the total amount absorbed was excreted in the urine of male and female rats within 1-2 days after the beginning of the application and the excretion in the feces was slightly slower than in the urine. The ratio of the excreted amount in the feces to that in the urine was approximately 1 : 4. 2. There was a sex difference in the total amount of the excreted radioactivity for 7 days after the beginning of the application ; the amount in female rats was only about 60% of that in male ones. The excreted amount was decreased significantly by castration in male rats. The investigation with thin-layer chromatography. revealed that approximately half the absorbed amount of the compound was excreted unchanged in the urine and that the percentage was higher in female rats than in male ones. 3. The radioactivity began to appear in the blood from about 1 hr after the beginning of the application. The maximum radioactivity level was noted in the blood at 24 hr and in main organs at 31 hr. The radioactivity was little detected 7 days after the beginning of the application. 4. The liver and adrenal had higher radioactivity levels than other organs. In each organ the radioactivity reached its maximum 31 hr after the beginning of the application. No sex difference was noted in the distribution of this compound in the organs.

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Synthesis of 5-Membered Heterocycles and Related Compounds

VISHNUJI RAM, HRIDVANAND PANDEY

1974 Volume 22 Issue 12 Pages 2778-2783
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2778

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Some 1-(2, 4-dichlorophenoxy and 2, 4, 5-trichlorophenoxy) acetyl-4-arylthiosemicarbazides were prepared from corresponding chlorophenoxyacetohydrazide. The resulting thiosemicarbazides were cyclised into 1, 3, 4-thiadiazoles and 5-mercapto-1, 2, 4-triazoles under different reaction conditions. The mercapto compounds were converted into sulphides and sulphones. N'-arylidene (2, 4-dichlorophenoxy) acetohydrazides and 5-substituted-1, 3, 4-oxadiazole-2-thiones were also prepared from (2, 4-dichlorophenoxy and 2, 4, 5-trichlorophenoxy) acetohydrazides separately and were subjected to Mannich reaction. Some of these compounds were evaluated as fungicides against Aspergillus niger.

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The Stereochemistry of Diels-Alder Adduct of 5-Methyl-2-cyclohexene-1-one with Butadiene

TAKASHI HARAYAMA, HIDETSURA CHO, MITSUAKI OHTANI, YASUO INUBUSHI

1974 Volume 22 Issue 12 Pages 2784-2787
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2784

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The Diels-Alder reaction of 5-methyl-2-cyclohexene-1-one (I) with butadiene was examined. It was concluded that addition of butadiene to the dienophile (I) took place from the opposite side to a secondary methyl side to give initially the cis adduct (IIb), which then epimerizes mostly to the trans derivative (IIa).

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Flocculation and Deflocculation of Veegum Suspensions by Polyoxyethylene Hydrogenated Castor Oil

YOSHITOMO OHNO, YASUKO SUMIMOTO, MITSUAKI OHSHIMA, MASAYUKI YAMADA, TS ...

1974 Volume 22 Issue 12 Pages 2788-2795
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2788

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The mechanism of the flocculation and deflocculation of Veegum (Montmorillonite) in an aqueous medium by polyoxyethylene hydrogenated castor oil which has a various length of polyoxyethylene chains, has been examined by adsorption isotherm, viscosity, zeta potential and contact angle measurements. Adsorption isotherms for these surfactants on Veegum showed flectional points (S-shaped) at a certain concentration of the surfactants added. The maximum flocculation occurred around the flectional points accompanying high viscosity in the suspension, and the measurement of contact angles showed that the Veegum surface at these points was most hydrophobic. These results suggest that the maximum flocculation occurs when all the Veegum surfaces are covered by surfactants orientating the hydrocarbon chains toward the solution, which renders the surface more hydrophobic. The deflocculation caused by the further addition of the surfactants is interpreted as being due to the bimolecular layer adsorption of the surfactants by van der Waals forces or by hydrophobic bonding between the Veegum particles adsorbed surfactants monomolecularly and the surfactants added.

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Synthesis of Pyrazolone Derivatives. XXIII. Benzo[5, 6]cyclohepta[1, 2-c]pyrazole-3, 10-dione and Related Compounds

ISOO ITO, SHINICHI NAGAI

1974 Volume 22 Issue 12 Pages 2796-2802
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2796

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Syntheses of 1-methyl-2-phenyl-1, 2, 3, 4, 5-pentahydro-10H-benzo[5, 6]cyclohepta[1, 2-c]pyrazole-3, 10-dione (3a) and its aminoalkylidene derivatives (3b-d) were investigated. Treatment of 3a with N-bromosuccinimide gave 4 (5)-bromo-1-methyl-2-phenyl-1, 2, 3-trihydro-10H-benzo[5, 6]cyclohepta[1, 2-c]pyrazole-3, 10-dione (13), while reaction of 3a with N-chlorosuccinimide produced 2-phenyl-2, 3, 3a, 4, 5-pentahydro-10H-benzo[5, 6]cyclohepta[1, 2-c]pyrazole-3, 10-dione (15). Dehydrogenation of 3a at 310°with palladium on carbon catalyst afforded 1-methyl-2-phenyl-1, 2, 3-trihydro-10H-benzo[5, 6]cyclohepta[1, 2-c]pyrazole-3, 10-dione (18) in a trace.

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Mixing of Pharmaceutical Powders examined by Use of Colored Particles : Discussions on Coloration Difference

YOSHIHISA MATSUDA, SUMIKO SHIROMOTO, YOHKO TAKEDA, SHINICHI HAYASHI, J ...

1974 Volume 22 Issue 12 Pages 2803-2811
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2803

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A new mixing index based on Hunter's color difference formula was applied to the three-component mixing of antipyrin, lactose and lactose colored with pigment (tracer powder of antipyrin). The mixing was conducted in a twin-shell mixer. The scale of scrutiny of this index was comparable with that of the mixing index used for the active ingredient. The concept of the uneven coloration is useful to follow the progress of mixing and to confirm the complete mixing. The relationship between the behavior of the active ingredient and tracer powder in the earlier stages of mixing was examined by the separate determination of antipyrin and pigment.

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Studies on the Reactions of Heterocyclic Compounds. XIII. Basicity of 1, 6-Naphthyridine and Its N-Oxides : Correlation to Peracid Oxidation

YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, HARUO SATO

1974 Volume 22 Issue 12 Pages 2812-2817
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2812

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Selective protonation of 1, 6-naphthyridine and its N-oxides was studied from the results of ultraviolet spectra in various concentrations of sulfuric acid. Nitrogen atom in 6-position was protonated preferentially to that in 1-position, which seems to be caused by the stability of 2, 6-quinonoid structure. This point is also supported by the difference in the changes of effective nuclear charges on protonation, which are calculated by SCF-LCAO-MO method. It was also shown that protonation plays an important role in N-oxidation of some heteroaromatic amines with a peracid.

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Studies on Pyrimidine Derivatives and Related Compounds. LXXXVII. Reaction of Thiamine Analogues with Diethyl Benzoylphosphonate

AKIRA TAKAMIZAWA, HIROSHI HARADA

1974 Volume 22 Issue 12 Pages 2818-2823
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2818

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Reaction of thiamine analogues lacking the 5-hydroxyethyl group (6a-e) with diethyl benzoylphosphonate (7) was carried out. Comparison of reactivity in 4'-substituted thiamine analogues and those lacking the hydroxyethyl group suggests the presence of an interaction in the thiamine molecule between the pyrimidine ring and the hydroxyethyl group in an aprotic solvent. Reactivity at the 2 position (the active center in enzymatic decarboxylation) in 4'-substituted thiamine analogues may be affected by this interaction.

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Urinary and Biliary Metabolites of 17α-Acetoxy-6-chloro-4, 6-pregnadiene-3, 20-dione in the Rabbit

TATSUYA ABE, AKIRA KAMBEGAWA

1974 Volume 22 Issue 12 Pages 2824-2829
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2824

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Ten metabolites of 17α-acetoxy-6-chloro-4, 6-pregnadiene-3, 20-dione were isolated from urine and bile of the rabbit and their chemical structures were determined. The urinary main metabolite was 17α-acetoxy-2ξ, 3ξ-dihydroxy-5ξ-pregnan-20-one. The biliary main metabolite was 17α-acetoxy-6-chloro-2ξ, 3ξ-dihydroxy-4, 6-pregnadien-20-one. The administered compound was metabolized through two courses, one was oxidation at C-2 and another was dechlorination at C-6, in the rabbit. A small amount of the metabolite oxidized at C-21 was identified from urine.

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Toxicological Approaches to the Metabolites of Fusaria. VII. Effects of Zearalenone on the Uteri of Mice and Rats

YOSHIO UENO, NORIKO SHIMADA, SHIGEKO YAGASAKI, MAKOTO ENOMOTO

1974 Volume 22 Issue 12 Pages 2830-2835
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2830

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Zearalenone produced by the fungus Fusarium roseum (Gibberella zeae) caused a marked uterotrophic response in mice and rats. Single or repeated administrations to immature mice and rats resulted in an increase of the uterine weight several times higher than the control weight. This effect was specific to the uterus, and oral administration was more effective than other routes. Ovariectomized mice were highly sensitive to zearalenone, and the dose-response curve was linear when daily doses of 1 to 2 mg/kg were given for one week. Zearalenone promoted cellular proliferation and mitosis in the uterine muscle cells.

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Studies on the Oxidation of "Reversed Nucleosides" in Oxygen. III. Synthesis of Eritadenine Analogues of Purines and Pyrimidines

TAKESHI KANNO, MITSUTAKA KAWAZU

1974 Volume 22 Issue 12 Pages 2836-2850
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2836

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Reaction of methyl 5-O-tosyl-2, 3-O-isopropylidene-β-D-ribofuranoside (1) with the sodium salts of purines, (2) and (3), and pyrimidines, (12), (13), and (14) derivatives in DMF afforded the corresponding "reversed nucleosides". 6-Alkylaminopurine analogues were prepared by the reaction of the 6-methylthiopurine derivative (4) with the amines. After removal of the protective groups, the reversed nucleosides were oxidized by oxygen in dilute alkaline solution to afford easily eritadenine analogues as major products.

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Studies on the Oxidation of "Reversed Nucleosides" in Oxygen. IV. Synthesis of 4-(6-Aminopurin-9H-9-yl)-3(R)-hydroxy-2(R)-aminobutyric Acid

TAKESHI KANNO, MITSUTAKA KAWAZU

1974 Volume 22 Issue 12 Pages 2851-2860
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2851

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Reaction of 5-O-tosyl-3-benzyloxycarbonylamido-3-deoxy-1, 2-O-isopropylidene-α-D-ribofuranose (21) or 5-O-tosyl-3-acetamido-3-deoxy-1, 2-O-isopropylidene-α-D-ribofuranose (30) with the sodium salt of adenine afforded the corresponding isomeric "reversed nucleosides" in good yields. Hydrolysis of the masked compound (22) followed by hydrogenolysis afforded 5-(6-aminopurin-9H-9-yl)-3-amino-3, 5-dideoxy-D-ribofuranose (26) hydrochloride in a good yield. After removal of the protective group, oxidation of 5-(6-aminopurin-9H-9-yl)-3-acetamido-3, 5-dideoxy-D-ribofuranose (33) by oxygen in a dilute alkaline solution afforded sodium 4-(6-aminopurin-9H-9-yl)-3(R)-hydroxy-2(R)-acetamidobutyrate (34). To evaluate the biological activities, amino ester (35) and amino acid (38) were also synthesized.

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Metabolism of Quaternary Ammonium Compounds. II. Microautoradiographic Studies on the Effect of CCl₄ on the Intralobular Distribution of Tritiated BTTB in Mice Liver

YOSHIO MATSUMOTO, YOSHIHISA TAKEBE, TETSUYA SUGA, SHINKICHI NIINOBE

1974 Volume 22 Issue 12 Pages 2861-2865
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2861

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The intralobular distribution of ³H-labeled p-biphenylmethyl-(dl-tropyl-α-tropinium)-bromide (³H-BTTB) and the effect of CCl₄-injury on its distribution were studied in mice mainly by means of microautoradiographic technique. It was established that ³H-BTTB was mostly concentrated in the cytoplasm of hepatic parenchymal cells and that this drug distributed homogeneously over whole the intralobular area. In CCl₄-treated mice, uptake of ³H-BTTB was markedly decreased in the liver and, on the other hand, was apparently increased in the kidney. In addition, the decrease in the uptake of this drug by CCl₄-treated liver occurred widely within the liver lobules and more significant decreases were found especially in the central zones of lobule. During the course of preparation of microautoradiographic tissue sections, the degree of released radioactivity in CCl₄-treated livers was inclined to increase than that of the controls.

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Synthesis of 3, 6-Diethoxycarbonyl-3, 6-epidithia-1, 4-dimethyl-2, 5-piperazinedione and Related Compounds. Formation of C-S Bond by the Reaction of Carbanion and Sulfur Monochloride

TOHRU HINO, TADAO SATO

1974 Volume 22 Issue 12 Pages 2866-2874
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2866

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Reaction of 3, 6-diethoxycarbonyl-1, 4-dimethyl-2, 5-piperazinedione (15), prepared by heating of diethyl methylaminomalonate (14), with NaH in dioxane and followed treatment with S₂Cl₂ gave 3, 6-epidithio- and 3, 6-epitetrathio-3, 6-diethoxycarbonyl-1, 4-dimethyl-2, 5-piperazinediones (16b and 16d), which have the skeletone (1) observed in fungal metabolites such as sporidesmin. The reduction of 16 with NaBH₄ in methanol gave the dethio derivative (15) in good yield. The reaction of 16d with triphenylphosphine in tetrahydrofurane gave 16c and 16b. The reaction of diethyl malonate derivatives (23a, b, and c) with NaH and S₂Cl₂ in dioxane gave the corresponding disulfides or trisulfides (24a, b, and c). Some reactions of proline anhydride (5) and sarcosine anhydride (7) with S₂Cl₂ or sulfur were examined.

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Reaction of Biguanides and Related Compounds. XII. Condensations of Arylbiguanides and Amidinoisoureas with Isatins

MITSURU FURUKAWA, TAKATOSHI YOSHIDA, SEIGORO HAYASHI

1974 Volume 22 Issue 12 Pages 2875-2882
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2875

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The reactions of arylbiguanides with isatin and with 1-methylisatin gave 2-oxo-3-arylbiguanidylidene-indoles and 4-amino-6-arylamino-2-(1'-methyl-2'-oxo-3'-indolidene)-1, 2-dihydro-s-triazines, respectively. Analogously, N-amidino-O-alkylisoureas reacted with isatin and 1-methylisatin to afford 2-oxo-3-alkoxyamidinoamidinylidene-indoles and 4-amino-6-alkoxy-2-(1'-methyl-2'-oxo-3'-indolidene)-1, 2-dihydro-s-triazines, respectively. The structures of these compounds were discussed.

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Effects of Some Antiparkinsonism Drugs and centrally Acting Muscle Relaxants on the Intercollicular Decerebrate Rigidity in Rats

HIDEOMI FUKUDA, TSUGUTAKA ITO, MAKOTO KOKUBO

1974 Volume 22 Issue 12 Pages 2883-2888
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2883

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The decerebrate rigidity in rats was prepared by means of transection between the inferior and superior colliculi. The strength of the rigidity was measured as electromyographic (EMG) activity of the rigid gastrocnemius muscle. Because of some similarity between Parkinsonism and intercollicular decerebrate rigidity, the effects of several antiparkinsonism drugs as well as centrally acting muscle relaxants on this type of the rigidity were studied. A small dose of chlorpromazine (125 μg/kg, i.v.) markedly reduced the rigidity. The inhibitory effect of trihexyphenidyl, biperiden, orphenadrine and tigloidine injected intravenously was dose-related. L-Dopa exerted only a little effect on the EMG activity of the rigid muscle. Mephenesin, methocarbamol, tolperisone, phenprobamate and diazepam were all effective in reducing the rigidity. These results are discussed in relation to data on their effects upon the crossed extensor reflexes in spinal chicks.

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A New Protecting Group. IV. Syntheses of Several (2-Picolyl 1-oxide) thio Derivatives by Use of a New Thiol Group Reagent : 2-Picolylchloride 1-Oxide

YOSHIHISA MIZUNO, KAZUYOSHI IKEDA

1974 Volume 22 Issue 12 Pages 2889-2893
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2889

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Alkylation of the thiols, p-thiocresol, 4-thiouridine, 4-thiouracil, 2-mercaptoinosine, cysteine, and glutathione with 2-picolyl chloride 1-oxide (15) afforded the corresponding 2-picolyl 1-oxide derivatives (6-14) in fair to good yields even in aqueous solution. Especially, this new thiol reagent was found to work well with 4-thiouridine and glutathione. 1-Oxido-2-picolylthio-derivative (8) was subjected to deblocking of the protecting group. Recovery of 2', 3'-O-isopropylidene 4-thiouridine (19) after deblocking was found to be quite satisfactory (79.2% yield).

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Studies on Pyridazines. XXIII. Synthesis of N-Substituted 1, 4-Dihydropyridazines

CHISATO KANEKO, TAKASHI TSUCHIYA, HIROSHI IGETA

1974 Volume 22 Issue 12 Pages 2894-2897
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2894

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1-Methylpyridazinium salts, derived from pyridazines (Ia-f), were reduced with sodium borohydride to give the corresponding 1-methyl-1, 6-dihydropyridazines (IIa-f) in 40-60% yields. Then, pyridazines (I) were reduced with sodium borohydride in the presence of methyl chloroformate to afford 1-methoxycarbonyl-1, 6-dihydropyridazines (IV) and their 1, 4-isomers (V), in total 35-65% yields, ratio of which depended on the kinds of the substituents.

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Separation and Quantitative Analysis of Ephedra Alkaloids by Gas Chromatography and Its Application to Evaluation of Some Ephedra Species collected around Himalaya

KAZUO YAMASAKI, KIKUKO FUJITA, MIHOKO SAKAMOTO, KAZUKO OKADA, MICHIYO ...

1974 Volume 22 Issue 12 Pages 2898-2902
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2898

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Chemical Modifications of Androsta-1, 4-diene-3, 17-dione. I. The Synthesis of 2β- and 1α-Hydroxy Derivatives of 3β-Hydroxyandrosta-5, 7-diene-3, 17-dione 17-Ethylene Ketal

HARUO SAKAMOTO, AKIKO SUGIMOTO, CHIKARA KANEKO

1974 Volume 22 Issue 12 Pages 2903-2909
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2903

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Disintegration Measurement of Sugar Coated Tablets by Thermal Analysis

YOSHINOBU NAKAI, SHINICHIRO NAKAJIMA, HIDENORI KAKIZAWA

1974 Volume 22 Issue 12 Pages 2910-2915
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2910

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Alkaloids from Streptomyces sp. NA-337

MASAYUKI ONDA, YAEKO KONDA, YOSHITSUGU NARIMATSU, HARUO TANAKA, JUICHI ...

1974 Volume 22 Issue 12 Pages 2916-2920
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2916

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Pyrimidine Derivatives and Related Compounds. XXIV. Synthesis of N-Substituted 6-Formyl-2, 4-dioxo-1, 2, 3, 4-tetrahydropyrrolo[2, 3-d]-pyrimidine Derivatives and Related Compounds

SHIGEO SENDA, KOSAKU HIROTA

1974 Volume 22 Issue 12 Pages 2921-2928
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2921

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Application of Quenching of Albumin-Induced Fluorescence of 8-Anilinonaphthalene-1-sulfonate to the Studies on Protein Bindings and Protein-Mucopolysaccharide Interaction

TOSHIO KINOSHITA, FUMIO IINUMA, AKIO TSUJI, IKUO MORIGUCHI

1974 Volume 22 Issue 12 Pages 2929-2934
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2929

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Formation of the Red Neotetrazolium Formazan by Reduced Nicotinamide Adenine Dinucleotide Phosphate-Cytochrome c Reductase in the Presence of Triton X-100

ISAO ISHIGURO, RIKIO SHINOHARA, AKIHIRO ISHIKURA, JUNKO NAITO

1974 Volume 22 Issue 12 Pages 2935-2940
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2935

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Studies on Dextranase. IV. Immobilization of Dextranase from Penicillium funiculosum IAM 7013

MAMORU SUGIURA, AKIRA ITO

1974 Volume 22 Issue 12 Pages 2941-2946
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2941

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Studies on Ketene and Its Derivatives. LXVI. Reaction of Acetoacetamide with α, β-Unsaturated Esters

TETSUZO KATO, MASAKI NODA

1974 Volume 22 Issue 12 Pages 2947-2952
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2947

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Studies on Dextranase. V. Activation of Dextranase from Penicillium funiculosum IAM 7013 by Co²⁺

MAMORU SUGIURA, AKIRA ITO, TARO OGISO, KENJI KATO

1974 Volume 22 Issue 12 Pages 2953-2958
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2953

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Studies on Antianaphylactic Agents. II. Oxidation and Reduction of 4-Oxo-4H-1-benzopyran-3-carboxaldehydes. Synthesis of 4-Oxo-4H-1-benzopyran-3-carboxylic Acids and 3-Hydroxymethylchromones

AKIRA NOHARA, TOMONOBU UMETANI, KIYOSHI UKAWA, YASUSHI SANNO

1974 Volume 22 Issue 12 Pages 2959-2965
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2959

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Determination of Particle Size Distribution of Fluorocarbon Emulsion by Means of Centrifugal Sedimentation : A Proposal for Specifying the Particle Size Distribution

KAZUMASA YOKOYAMA, AKIRA SUZUKI, ISAMU UTSUMI, RYOICHI NAITO

1974 Volume 22 Issue 12 Pages 2966-2971
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2966

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Studies on the Method of Size Reduction of Medicinal Compounds. V. Size Reduction of Several Sulfonamides by Desorption of Ammonia from Their Ammonia Compounds

KEIJI SEKIGUCHI, YASUYUKI TSUDA, MOTOKO KANKE

1974 Volume 22 Issue 12 Pages 2972-2978
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2972

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Heterocycles Related to Nucleotides. VII. Reactions of Dimethyluracil and Dimethylthymine with Benzoyl Peroxide

MASATO AIURA, YUICHI KANAOKA

1974 Volume 22 Issue 12 Pages 2979-2981
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2979

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β-Arylaminoacrolein Derivatives. II. Cyclodehydration of β-Arylaminoacrolein Derivatives

SHINZO TAMURA, EMIKO YABE

1974 Volume 22 Issue 12 Pages 2982-2986
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2982

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Conversion of Bis (β-carbamoylethyl) Disulfides into Bis (β-carbamoylethyl) Trisulfides

MITSURU FURUKAWA, SHOOKO KATO, SEIGORO HAYASHI

1974 Volume 22 Issue 12 Pages 2987-2990
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2987

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Interaction between Iodine and Polyvinylpyrrolidone or α-Pyrrolidone

NOBUYOSHI KANENIWA, AKIKO IKEKAWA

1974 Volume 22 Issue 12 Pages 2990-2998
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2990

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Reduction of O-Alkylated Imides

KATSUHIDE MATOBA, TAKAO YAMAZAKI

1974 Volume 22 Issue 12 Pages 2999-3001
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.2999

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Studies on Steroid Conjugates. XIII. Synthesis of 2, 4, 17α-d₃-Estriol 3-Glucuronoside

TOSHIO NAMBARA, MOTOKO KURATA, JUNICHI GOTO

1974 Volume 22 Issue 12 Pages 3002-3005
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.3002

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Revised Structure of Desacyl-jegosaponin

ISAO KITAGAWA, YASUHIRO IMAKURA, TERUAKI HAYASHI, ITIRO YOSIOKA

1974 Volume 22 Issue 12 Pages 3009-3010
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.3009

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Structures of Three Soybean Saponins : Soyasaponin I, II, and III

ISAO KITAGAWA, MASAYUKI YOSHIKAWA, ITIRO YOSIOKA

1974 Volume 22 Issue 12 Pages 3010-3013
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.3010

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Transformation of Indole Alkaloids. The Chemical Transformation of Corynantheine Type Alkaloids to C-Mavacurine Type Alkaloids

SHINICHIRO SAKAI, NOBUO SHINMA

1974 Volume 22 Issue 12 Pages 3013-3016
Published: December 25, 1974
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.22.3013

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