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Volume 99, Issue 12
Displaying 1-15 of 15 articles from this issue
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KATSUHIKO KIMURA, MASAHUMI YOSHIDA, MASAO NAGAOKA, SHOZABURO OHGIYA1979 Volume 99 Issue 12 Pages 1155-1160
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAcute toxicity and depressive effect on spontaneous motor activity were examined on N-derivatives of piperidine as a model compound for piperidine and peperazine series analgesics, using untreated mice and mice pretreated with phenobarbital or SKF-525A. Acute toxicity of the derivatives with facile N-C cleavage by liver monooxygenase due to enzyme induction became weak but the depressive action became stronger, approaching close to that of piperidine, while acute toxicity and depressive action inversely changed into other direction on enzyme inhibition. Derivatives with difficult N-C cleavage showed hardly any change by derivation and inhibition. These results suggest that N-C cleavage is related to the depressive action of the derivatives, and this was also supported by the results of quantitative assay of piperidine in the blood and brain of mice given the derivatives. These results also suggest a correlation between acute toxicity and N-C cleavage but the toxicity is rapid-acting and central, so that this correlation cannot be definitely concluded.View full abstractDownload PDF (725K) -
HISAYOSHI SUGIHARA, TOSHIAKI NIKAI, HIROSHI UMEDA, TETSUNOSUKE TANAKA1979 Volume 99 Issue 12 Pages 1161-1167
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAc3-Proteinase was purified from the lyophilized venom of Agkistrodon acutus using gel filtration on a Sephadex G-75 column, followed by chromatography on diethylaminoethyl (DEAE)-Sephadex A-50, DEAE-Sephacel and DEAE-Sephacel rechromatography. By these procedures, 22.7 mg of purified preparation was obtained from 1 g of crude venom. The purified preparation was homogeneous as judged by disc electrophoresis over polyacrylamide gel at pH 8.3 and isoelectric focusing. Ac3-Proteinase possessed both lethal and hemorrhagic activities. These and proteolytic activities were inhibited by ethylenediaminetetraacetic acid (EDTA), cysteine or antiserum, but not by soybean trypsin inhibitor (SBTI), p-chloromercuribenzoate (PCMB) or diisopropyl fluorophosphate (DFP). The molecular weight of Ac3-proteinase was estimated to be about 57000 by SDS-polyacrylamide gel electrophoresis, and the isoelectric point was found to be pH 4.7, indicating that the protein was acidic. The minimum hemorrhagic dose, LD50 and proteolytic activities of the purified preparation were 0.95μg, 108μg/mouse, and 0.253 unit/mg, respectively. Both Ac1- and Ac2-proteinases were simple proteins, while Ac3-proteinase was a glycoprotein.View full abstractDownload PDF (810K) -
SHIKIFUMI KITAZAWA, IKUO JOHNO, HIDEO OBATA, ATSUSHI MAEDA, ICHIRO MIZ ...1979 Volume 99 Issue 12 Pages 1168-1175
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSRecent advances in pharmaceutical technology and instruments have made it possible to manufacture more uniform preparations. However, the Japanese pharmacopoeia have not kept in step with these developments. For example, the weight variation test for uncoated tablets has not been revised since publication of the 7th edition in 1961. Fifty four brands of commercial, uncoated and coated tablets were selected at random and subjected to the weight variation test of the J.P.IX. For comparison purposes, four uncoated tablets, formulated in our laboratory, were included in this study. All uncoated tablets complied with the requirements of the J. P. IX. Variations in tablet weight, presented as standard deviation and/or range, increased with the average weight increase of the tablets. However, the variations were found to be considerably less than the requirements. This suggests that the requirements should be updated since they do not adapt to present status of tablet formulations. More than 80% of the coated tablets complied with the requirements which are applied only to uncoated tablets in the J.P.IX. It was apparent that the variations in coated tablets were not as small as those of uncoated tablets ; however, the fact that more than 80% of the coated tablets complied with the J. P. requirements suggests that some requirement should be established for the coated preparations.View full abstractDownload PDF (822K) -
JOJU HAGINIWA, YOSHIHIRO HIGUCHI, YASUO HIRAWATA, NAOKI HOSHINO, HIROO ...1979 Volume 99 Issue 12 Pages 1176-1180
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSynthesis of asymmetric compounds having a ferroin or cuproin group, such as 2, 2'-dipyridyls (III) like 3, 4'-dimethyl-2, 2'-dipyridyl, derivatives of 2-(2-pyridyl) quinoline (VI) and asymmetric 2, 2'-diquinolinyl (XIII), and derivatives of pyridylpyridazine (XII), pyridylpyrazine, and pyridylquinoxaline may be carried out by dehydrogenative condensation of aromatic amine N-oxides using a platinized palladium-carbon catalyst, and examinations were made to see which of I and II should be derived to their N-oxide. In the syntheses of III and XIII, reaction should be carried out by derivation of a more reactive compound to its N-oxide. For the synthesis of VI, better yield is obtained by derivation of pyridine to its N-oxide rather than quinoline, although reaction of quinoline N-oxide gives VI preferencially but in a small yield, with little formation of other by-products. XII is obtained by the reaction of pyridine with pyridazine N-oxides but, in the case of pyrazine and quinoxaline, the objective compound is obtained only when quinoxaline is reacted with pyridine N-oxide.View full abstractDownload PDF (585K) -
JOJU HAGINIWA, YOSHIHIRO HIGUCHI, SHIGEO IKEDA1979 Volume 99 Issue 12 Pages 1181-1185
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDehydrogenative condensation of two molecules of pyridine 1-oxide or N-oxides of benzo [f] quinoline (I), benzo [h] quinoline (IV), benzo [g] quinoline (VIII), and acridine (XIII) by hydrogenation using a platinized palladium-carbon catalyst affords respective dimers bonded at 2-position of the ring nitrogen, except in XIII which cannot undergo dehydrogenation at 2-position of the ring nitrogen. I and IV also afforded the corresponding pyridylbenzoquinoline, although in a small quantity. Dimerization of these compounds is extremely poor compared to pyridine and quinoline. IV formed its dimer only when 10-hydroxybenzo [h] quinoline was reacted as its N-oxide. VIII was synthesized by dehydrogenative aromatization of 6, 7, 8, 9-tetrahydrobenzo [g] quinoline with DDQ and VIII was not formed when palladium-carbon was used, resulting in the formation of a dimer.View full abstractDownload PDF (592K) -
TAKASHI SHINDO, YUKIHIRO YASUDA, KAZUKI TAIRA, NARUO MITANI, ATSUHIRO ...1979 Volume 99 Issue 12 Pages 1186-1200
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe biological fate of 4-butyl-4-(β-carboxypropionyl-oxymethyl)-1, 2-diphenyl-3, 5-pyrazolidinedione (Suxibuzone, SB) was compared with that of phenylbutazone (PB) in rats, rabbits, beagle dogs and rhesus monkeys. The results obtained were as follows ; 1) When SB was administered orally, the main metabolites in the plasma were PB, oxyphenbutazone (Oxy-PB) and γ-hydroxyphenylbutazone (γ-Hydroxy-PB) in all species, though species differences were observed in the maximum plasma levels of the respective metabolites. Only in dogs and monkeys, was a small amount of SB detected in the plasma during the early time of dosing. 2) The metabolites and their maximum levels in plasma after the administration of SB were almost identical with those observed after the administration of PB. 3) After administration of SB, the main metabolites found in urine were PB, Oxy-PB, γ-Hydroxy-PB and their conjugates in all species, while species differences were observed in the percent excreted. In the dogs and monkeys, urinary excretion as the form of SB and 4-hydroxymethylphenylbutazone (4-HM-PB) glucuronides was observed in small amount for 0-12 hours. 4) There were no significant differences in the metabolites and their excreted percent in urine between SB and PB administration. 5) Differences between male and female in maximum plasma levels of PB and γ-Hydroxy-PB and in urinary excreted percent of γ-Hydroxy-PB were observed only in rats. 6) Species differences were observed in esterase activity on SB in vitro. 7) SB was bound to the albumin fraction as in the case of PB, but its binding percent was about 1/2 lower than that of PB. 8) SB showed anti-edematous action on carrageenin-induced edema and its activity was almost similar to that of PB. Anti-edematous activity of Oxy-PB was weaker than that of SB and γ-Hydroxy-PB had no effect on its action.View full abstractDownload PDF (1269K) -
SEIJI KATAYAMA, SHIGEKI TANI, YUKIO AKAHORI, SHIGEYUKI YAMADA1979 Volume 99 Issue 12 Pages 1201-1206
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSNMR spectra of N-(2-hydroxy-3-methoxybenzylideneaniline in various solvents were observed. The dilution curves were estimated from proton chemical shifts of all the resonance signals observed. The dilution coefficients (Δδ/Δc) were obtained from the dilution curves. Correlations for the dilution coefficients between protons and between solvents were examined in detail. A discussion of the nature of the solvents and solute is presented and it is suggested that correlation analysis is one of available methods for discussing the solvent effect.View full abstractDownload PDF (567K) -
ISAMU SAIKAWA, KAISHU MOMONOI, HIROSHI SAKAI, YUTAKA TAKASHITA, TOSHIN ...1979 Volume 99 Issue 12 Pages 1207-1218
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe stability, degradation pattern and structure of degradation products of sodium 7-[D (-)-α-(4-ethyl-2, 3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl) acetamido]-3-[(1-methyl-1H-tetrazol-5-yl) thiomethyl]-3-cephem-4-carboxylate (T-1551) in aqueous solution were investigated. T-1551 was kept in various solutions in pH and μ=0.5 at 35°, its degradation was followed by HPLC. T-1551 was stable at the range of pH 4.0-7.0, slightly unstable at acid and markedly unstable at alkaline. It was confirmed that in alkaline solution, 7-[D (-)-α-[3-[2-(N-ethyl-N-oxaloamino)-ethyl] ureido]-α-(4-hydroxyphenyl) acetamido]-3-(1-methyl-1H-tetrazol-5-yl) thiomethyl-3-cephem-4-carboxylic acid (T-1551A) was produced, and that in acidic solution, 7-[D (-)-α-(4-ethyl-2, 3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl) acetamido]-3-hydroxy-methyl-3-cephem-4-carboxylic acid γ-lactone (T-1551B), 7-[D (-)-α-(4-ethyl-2, 3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl) acetamido]-3-hydroxymethyl-3-cephem-4-carboxylic acid (T-1551C), 5-mercapto-1-methyl-1H-tetrazole (T-1551F), 2-[2-(4-ethyl-2, 3-dioxo-1-piperazinecarboxamido)-2-(4-hydroxyphenyl) acetamido]-2-[1, 2, 5, 7-tetrahydro-7-oxo-4H-furo [3, 4-d] [1, 3] thiazin-2-yl] acetic acid (T-1551G), 2-[α-(4-ethyl-2, 3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl) acetamidomethyl]-2, 3-dihydro-5-hydroxy-methyl-6H-thiazine-4-carboxylic acid γ-lactone (T-1551H) and N-formylmethyl-D-(-)-α-(4-ethyl-2, 3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl) acetamide (T-1551D) were produced, respectively.View full abstractDownload PDF (1155K) -
MASAO OKAMOTO, SHUNSAKU OHTA, SHINICHIRO TERADA1979 Volume 99 Issue 12 Pages 1219-1224
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS2, 3-Dichloronaphthoquinone (3) easily reacted with active methylene compounds such as dimethyl malonate, ethyl acetoacetate, diethyl oxalacetate and a Schiff base, prepared from dimethyl β-ketoglutarate and aminoacetal, in the presence of potassium succinimidate to give the corresponding substituted monochloroquinones (5a-c and 17, respectively). The chloroquinone (5a) was converted to N-substituted 2-hydroxy-3-methoxycarbonylbenz [f] indole-4, 9-diones (9a-e) by the reaction with ammonia or various primary amines, and 5b was converted to N-substituted 3-ethoxycarbonyl-2-methylbenz [f] indole-4, 9-diones (11a-c) in the same manner.View full abstractDownload PDF (685K) -
YOSHIKI HAMADA, KENTARO SHIGEMURA1979 Volume 99 Issue 12 Pages 1225-1228
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS1, 6-Naphthyridine-5-carboxamide (VI), 1, 6-naphthyridine-5-carboxylic acid (VII), and benzaldehyde were obtained by acid hydrolysis of 5-benzoyl-5, 6-dihydro-1, 6-naphthyridine-5-carbonitrile (III). Reaction of III with a Grignard reagent (CH3MgBr, PhMgBr) gave 1, 6-naphthyridine-5-carbonitrile (IX) by reaction with methylmagnesium bromide, and IX, VI, and α, α-diphenyl-5-(1, 6-naphthyridine) methanol (X) by reaction with phenylmagnesium bromide. Alkylation of III with methyl iodide, using a phasetransfer catalyst, gave 6-benzoyl-5, 6-dihydro-1, 6-naphthyridine-5-carbonitrile (XIII), and alkaline hydrolysis of XIII afforded 5-methyl-1, 6-naphthyridine (II). Reaction of III with 3, 4-dimethyoxbenzyl chloride gave 5-(3, 4-dimethoxybenzyl)-1, 6-naphthyridine (XV).View full abstractDownload PDF (529K) -
MICHIHARU SUGIURA, YOSHIKI HAMADA1979 Volume 99 Issue 12 Pages 1229-1233
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSApplication of dichlorocarbene to 2-methylisoquinolinium iodides (3), derived from isoquinoline (1), in the presence of a phase-shifting catalyst, resulted in the formation of 1, 1-dichloro-2-methyl-3-(trichloromethyl)-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c] isoquinoline derivatives (4). Application of dichlorocarbene to I in the presence of ethanol gave 1, 1-dichloro-3-ethoxy-2-formyl-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c] isoquinoline derivative (s) (7). Both 4 and 7 were labile and were obtained in a low yield. Application of dichloro-or dibromo-carbene to 1-alkyl-2-benzoyl-1-cyano-1, 2-dihydroisoquinolines (10), obtained from 1 in two steps, afforded stable 2-benzoyl-3-cyano-1, 1-dichloro (or -1, 1-dibromo)-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c] isoquinoline derivatives (11) in a high yield. Since there has been no published report on the syntheses of cyclopropa [c] isoquinoline derivatives from 1, this method of synthesis via 10 seems to be useful.View full abstractDownload PDF (545K) -
SHOZO HIDAKI, YOSHINORI TOMINAGA, YOSHIRO MATSUDA, GORO KOBAYASHI, KAN ...1979 Volume 99 Issue 12 Pages 1234-1239
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSulfonyl ketenethioacetals (IIa-e), 1-substituted (R1) 2, 2-bis (methylthio)-1-sulfonyl-(R2) ethene (a : R1=SO2-Ph, R2=COMe ; b : R1=SO2-Ph-Me (p), R2=CN ; c : R1=SO2-Ph-Me (p), R2=CN ; d : R1=SO2-Ph-Me (p), R2=COOMe) reacted with active methylene compounds (dimethyl malonate, malononitrile, 1-methyloxindole, 3-methyl-5-oxo-1-phenyl-2-pyrazoline, 3-ethylrhodanine) to give the displacement products of a methylthio group in good yields. The reaction of IIb, c, d with malonitrile, nitromethane, 1, 2, 3, 4-tetrahydroisoquinoline-1, 4-dione, 2, 3-dihydrobenzo [b] thiophen-3-one 1, 1-dioxide, and 1, 3-indadione gave the corresponding heterocyclic compounds, 2-hydroximino-5-oxopyrroline (X), 2-pyridone (VII), pyrrolo [1, 2-b] isoquinoline (XIIIa, b), pyrido [2, 3-b] benzo [b] thiophene 5, 5-dioxide (XVIa, b), and indeno [1, 2-b] pyridine (XVIII), derivatives in good yields.View full abstractDownload PDF (718K) -
ATSUKO NOSE, TADAHIRO KUDO1979 Volume 99 Issue 12 Pages 1240-1244
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSReaction of quinoline (I) and isoquinoline (VI) with diborane, followed by treatment with hydrochloric acid, afforded the corresponding 1, 2, 3, 4-tetrahydro compounds. However, quinaldine (III) gave traces of 1, 2, 3, 4-tetrahydroquinaldine, and neither lepidine (V) nor 3-methylisoquinoline (VIII) were reduced under similar conditions. On the other hand, quinoxaline derivatives reacted with diborane alone to give the corresponding 1, 2, 3, 4-tetrahydro derivatives in quantitative yields. It is interesting that the reduction of heteroaromatic compounds proceeded with diborane.View full abstractDownload PDF (559K) -
KOJI MIURA, YASUYUKI SUZUKI, NOBORU TAKAGAWA, YUKITAKA HAMATANI, KENJU ...1979 Volume 99 Issue 12 Pages 1245-1249
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAcylated lactoylcholine derivatives were synthesized and their contracting activity on smooth muscle of isolated rat stomach, was examined by the Magnus method. Structure-activity relationship of these compounds was discussed. Acetyllactoylcholine, propionyllactoylcholine and butyryllactoylcholine were found to have strong activity.View full abstractDownload PDF (513K) -
KAZUHISA HAYASHI, SATOSHI KAWAI, TAKEO OHNO, YOSHIFUMI MAKI1979 Volume 99 Issue 12 Pages 1250-1253
Published: December 25, 1979
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSolutions of DL-alanine, DL-valine, DL-leucine and DL-isoleucine in water containing mercury (II) chloride were irradiated for 4 hr by an 8W low-pressure mercury arc lamp. The alkylmercury (II) chlorides produced in the irradiated solutions were analysed quantitatively by gas chromatography. It was observed that methylmercury unrelated to the alkyl residues in the α-amino acid was formed almost exclusively, although DL-leucine yielded an undetermined organomercury compound in addition to methylmercury. The use of a 20W blacklight lamp (300-400 nm) as a light source resulted in the formation of a much lower yield of methylmercury after irradiation for 150 or 300 hr. A white solid deposited as the reaction proceeded showed some properties of a mercurous compound. Photolysis of glycine and phenylglycine did not yield alkylmercury compounds, indicating that the formation of methylmercury was due to the apparent fragmentation of the alkyl residues of the α-amino acid during photolysis.View full abstractDownload PDF (532K)
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