著者

松永 康志 大田 涼子 坂東 信行 山田 博章 湯浅 宏 金谷 芳雄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.41, no.4, pp.720-724, 1993-04-15 (Released:2008-03-31)

参考文献数

10

被引用文献数

6 13

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(E)-4-[1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-(4-isopropyl)phenyl]-1-butenyl]phenyl monophosphate (TAT-59) is a new drug for the treatment of breast cancer. Physical and chemical stability of a tablet consisting of TAT-59 powder and a few excipients (Formulated tablet), a tablet consisting of only TAT-59 power (TAT-59 tablet) and TAT-59 powder itself itself was evaluated based on water content, tensile strenght, porosity, the amount of TAT-59 and its hydrolysis product, DP-TAT-59.The water content of Formulated tablet increased with relative humidity (RH), whereas that of TAT-59 tablet and TAT-59 powder scarcely changed. The equilibrium water content of Formulated tablet was much greater than that of the TAT-59 tablet or TAT-59 powder due to adsorbed moisture by the excipients. The tensile strength and porosity of Formulated tablet decreased and increased linearly, respectively, with increasing water content. The degradation rate of TAT-59 decreased in the following order : Formulated tablet>TAT-59 tablet>TAT-59 powder. The relationship between equilibrium water content and degradation rate of the Formulated tablet was determined by the Carstensen equation, in which the interaction order between the durg and water content was 1.9, and the degration of TAT-59 in Formulated tablet was related to water content. Thus, it was found that the degradation of TAT-59 was accelerated by compression and addition of excipients.

著者

Takahiro Uchida Yuka Sugino Mai Hazekawa Miyako Yoshida Tamami Haraguchi

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.60, no.8, pp.949-954, 2012-08-01 (Released:2012-08-01)

参考文献数

13

被引用文献数

4 6

---

The bitterness of 10 different products with ambroxol as active ingredient, the original and nine generics, were evaluated by human gustatory sensation tests in which the tablets were kept in the mouth, with water, at 20 and 37°C. The products all showed different bitterness intensities. The original and some of the generic products had comparatively low bitterness intensities but some of the generic products had comparatively high bitterness intensities. The bitterness intensities of these 10 was found to be significantly correlated with both the disintegration time, as evaluated using the ODT-101 (a recently developed apparatus), and the drug concentration in dissolved medium, as measured in a conventional dissolution test. The bitterness threshold of ambroxol solution was found to increase when the temperature of the water with which the tablets were taken, was raised from 20 to 37°C. The equation was calculated to predict the bitterness intensity of ambroxol, a function based on temperature and the ambroxol concentration using data from a standard ambroxol solution at 4, 20 and 37°C. The bitterness intensities obtained for the 10 ambroxol formulations with water at 20 and 37°C, coincided with the bitterness values predicted by the equation.

著者

伊東 秀之 三宅 陽子 吉田 隆志

出版者

公益社団法人 日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.43, no.7, pp.1260-1262, 1995

被引用文献数

32

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Three new piscicidal triterpenens named irisgermanicals A, B and C along with seven known iridal-type triterpenes including iripallidal and iriflorental were isolated from the bark of Iris germanica rhizome, upon bioassay-guided fractionation using the Medaka (killie-fish; Oryzias latipes), and their bicyclic structures were elucidated based on the spectral analyses. Irisgermanicals B and C were characterized as geometrical iriflorental and iripallidal isomers, respectively, concerning the α, β-unsaturated aldehyde moiety. The piscicidal activity was observed for bicyclic iridals, among which iriflorental exhibited most potent activity.

著者

松田 彰 小尾 紀行 宮坂 貞

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.6, pp.2575-2578, 1985-06-25 (Released:2008-03-31)

参考文献数

21

被引用文献数

13 18

---

Reaction of 2', 3', 5'-tri-O-benzoyluridine (3) with 1-methylimidazole in the presence of phosphoryl chloride in acetonitrile afforded 3-methyl-1-imidazolium intermediate (4), from which a variety of 4-substituted pyrimidin-2 (1H)-one ribosides (5-12) were obtained in a one-pot manner by nucleophilic substitutions under mild conditions. Application of this method to 2'-deoxyriboside of several pyrimidines (13a, b, c) is also described.

著者

宮下 修 松村 興一 笠原 俊彦 島津 浩 橋本 直人

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.30, no.3, pp.887-898, 1982-03-25 (Released:2008-03-31)

参考文献数

6

被引用文献数

3 8

---

Various derivatives of 5-fluoro-5, 6-dihydrouracil with an alkoxycarbonyl, substituted carbamoyl, or cyano group at C-5, and one of a variety of substituents, i.e., alkoxy, substituted mercapto, substituted amino, acyl amino, and alkylidene- and arylideneaminooxy at C-6, have been synthesized as a class of potential pro-drugs of autitumor agents, 5-fluorouracil (5-FU) and 1-(2-tetrahydrofuryl)-5-fluorouracil (Ftorafur). Antitumor activity of these compounds against leukemia P388 or L1210 in mice and antifungal activity against Botrytis cinerea are described.

著者

Kiyofumi Inamoto

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.61, no.10, pp.987-996, 2013-10-01 (Released:2013-10-01)

参考文献数

70

被引用文献数

5 17

---

Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon–hydrogen bond (C–H) functionalization/intramolecular carbon–heteroatom (nitrogen or sulfur) bond formation process. By this C–H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C–H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

著者

Shigeo Yasuda Haruna Yokosawa Chisato Mukai

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.64, no.7, pp.805-810, 2016-07-01 (Released:2016-07-01)

参考文献数

28

被引用文献数

2 3

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Treatment of the allenylazetidine–alkynes with a catalytic amount of [RhCl(CO)dppp]2 (dppp: 1,3-bis(diphenylphosphino)propane) effected the intramolecular hetero-[6+2]-type ring-closing reaction via the C–C bond cleavage of the azetidine ring to produce azabicyclo[6.4.0]dodecatriene derivatives in good to excellent yields. The formation of the oxa analogue could also be achieved.

著者

杉本 和朗 大木 貞雄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.12, no.11, pp.1375-1378, 1964-11-25 (Released:2008-03-31)

被引用文献数

1 1

---

Aromatic nitrogen mustards containing an azo group (VII∼XV), a nitrogen mustard with a carrier and masking group, were synthesized in one step starting from p-amino-phenylalanine or aliphatic p-amino-phenyl acid.

著者

佐々木 正 源 勝麿

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.12, no.11, pp.1329-1338, 1964-11-25 (Released:2008-03-31)

被引用文献数

12 14

---

Im Rahmen der Untersuchungen der Synthesemoglichkeit von as-Triazin-N-oxyden, oxydierten wir 3-Amino- bzw. 3-Amino-5, 6-dimethyl-as-triazin durch Persaure, wobei sich die entsprechenden 5-Oxo-verbindungen und ein Mono-N-oxyd von 3-Amino-5, 6-dimethyl-as-triazin erhalten lieβen, deren Konstitutionen bzw. diejenigen der acetylierten Korpern durch Dipolmoment-Messungen sowie spektroskopisch diskutiert wurden.

著者

津田 恭介 生熊 晋 河村 正朗 太刀川 隆治 酒井 浄 田村 千尋 甘粕 治

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.12, no.11, pp.1357-1374, 1964-11-25 (Released:2008-03-31)

被引用文献数

126 208

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The structures of both tetrodonic acid hydrobromide and 6, 11-diacetylanhydrotetrodotoxin hydroiodide were established by chemical and X-ray crystallographical research. Based upon structures of both these salts and upon other chemical information, we determined that tetrodotoxin and anhydrotetrodotoxin have zwitterionic hemilactal structures.

著者

Kengo Hanaya Kazuaki Matsumoto Yuta Yokoyama Junko Kizu Mitsuru Shoji Takeshi Sugai

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.65, no.2, pp.194-199, 2017-02-01 (Released:2017-02-01)

参考文献数

14

被引用文献数

1

---

Linezolid (1) is an oxazolidinone antibiotic that is partially metabolized in vivo via ring cleavage of its morpholine moiety to mainly form two metabolites, PNU-142300 (2) and PNU-142586 (3). It is supposed that accumulation of 2 and 3 in patients with renal insufficiency may cause thrombocytopenia, one of the adverse effects of linezolid. However, the poor availability of 2 and 3 has hindered further investigation of the clinical significance of the accumulation of these metabolites. In this paper, we synthesized metabolites 2 and 3 via a common synthetic intermediate, 4; this will encourage further exploration of events related to these metabolites and lead to improved clinical use of linezolid.

著者

瀬尾 量 鶴岡 道雄 橋本 強 藤永 稔夫 小田切 優樹 上釜 兼人

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.31, no.1, pp.286-291, 1983-01-25 (Released:2008-03-31)

参考文献数

15

被引用文献数

48 62

---

Inclusion complex formations of spironolactone (SP) with three cyclodextrins (α-, β-, γ-CyDs) in aqueous solution and in the solid state were studied by the solubility method, by spectroscopic methods (UV, CD, IR) and by X-ray diffractometry, and their modes of interaction were assessed. The solid complexes of SP with β- and γ-CyDs were obtained in molar ratios of 1 : 2 and 2 : 3, respectively, and their dissolution, membrane permeation and oral absorption properties were examined. The rates of dissolution and permeation through a cellophane membrane in water were significantly increased by inclusion complexation (γ-CyD complex>β-CyD complex>SP alone), depending upon the solubility of the test samples. The serum levels of SP following oral administration of CyD complexes were found to be greater than those after administration of SP alone. The results indicated that the γ-CyD complex rather than β-CyD complex may have great utility as a faster dissolving form of SP able to produce higher serum levels.

著者

田中 博道 高橋 隆子 富樫 浩之 上田 亨

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.26, no.11, pp.3322-3329, 1978-11-25 (Released:2008-03-31)

被引用文献数

5 8

---

Starting from 1-β-D-ribofuranosyl-2-oxo-4-imidazoline-4-carboxylic acid (1), obtained from uridine, various 2, 5'-O-cycloimidazole nucleosides have been prepared. The 2-oxo function of 1 was also converted to the 2-chloro and 2-thione functions. Whereas the circular dichroism (CD) spectra of 1 and related 2-oxo derivatives exhibited negative bands, their 5-bromo derivatives showed positive bands. All 2, 5'-O-cycloimidazole nucleosides showed strong negative CD bands which were in contrast to the results in the 8, 5'-O-cyclopurine nucleosides. The relationship between the sign of the CD bands and the orientation of the base moieties in imidazole nucleosides was discussed.

著者

宮澤 修平 岡野 和夫 下村 直之 川原 哲也 浅野 修 吉村 寛幸 河合 隆利 左右田 茂 吉田 豊 里 忠 町田 善正 山津 功

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.40, no.2, pp.521-523, 1992-02-25 (Released:2008-03-31)

参考文献数

14

被引用文献数

2 4

---

Optically active platelet-activating factor (PAF) receptor antagonist, (+)-6-(2-chlorophenyl)-3-cyclopropanecarbonyl-8, 11-dimethyl-2, 3, 4, 5-tetrahydro-8H-pyrido[4', 3' : 4, 5]thieno[3, 2-f][1, 2, 4]triazolo[4, 5-a][1, 4]diazepine (E6123), was synthesized on large-scale by optical resolution using (+)-dibenzoyl-D-tartaric acid. An X-ray crystallographic analysis clearly indicated that the absolute configuration of the synthesized E6123 was S.

著者

宮澤 修平 岡野 和夫 下村 直之 / 川原 哲也 浅野 修 吉村 寛幸 宮本 光明 佐久間 義範 村本 賢三 尾葉石 浩 原田 耕吉 梶間 隆 山田 浩司 角田 創 片山 敏 阿部 信也 浅川 直樹 左右田 茂 堀江 透 里 忠 町田 善正 片山 幸一 山津 功 Isao YAMATSU

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.39, no.12, pp.3215-3220, 1991-12-25 (Released:2008-03-31)

参考文献数

27

被引用文献数

6 9

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A series of triazolodiazepines was synthesized and evaluated for anti-platelet activating factor (PAF) activities. Structure-activity relationship (SAR) studies on this series revealed that the introduction of a methyl group into the 8-position of the thienodiazepine nucleus can lead to a lengthening of the duration of action. Introduction of a methyl group produced an asymmetric center and the enantiomers so formed were separated with an optical resolving column. In the in vitro assay system, the (+)-isomers displayed 50-200 times more potent anti-PAF activity than the (-)-isomers. After comparison of toxicology and pharmacokinetics, (+)-6-(2-chlorophenyl)-3-cyclopropanecarbonyl-8, 11-dimethyl-2, 3, 4, 5-tetrahydro-8H-pyrido[4', 3' : 4, 5]thieno[3, 2-f][1, 2, 4]triazolo[4, 3-a][1, 4]diazepine (35(+)-isomer, E6123) was selected from among the compounds synthesized as a candidate for clinical study.

著者

Mio Tange Akino Matsumoto Miyako Yoshida Honami Kojima Tamami Haraguchi Takahiro Uchida

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.65, no.1, pp.36-41, 2017-01-01 (Released:2017-01-01)

参考文献数

28

被引用文献数

2

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The purpose of the study was to evaluate the adsorption of filgrastim on infusion sets (comprising infusion bag, line and filter) and to compare the adsorption of the original filgrastim preparation with biosimilar preparations using HPLC. The inhibitory effect of polysorbate 80 on this adsorption was also evaluated. Filgrastim was mixed with isotonic sodium chloride solution or 5% (w/v) glucose solution in the infusion fluid. Filgrastim adsorption on infusion sets was observed with all preparations and with both types of infusion solution. The adsorption ratio was about 30% in all circumstances. Filgrastim adsorption on all parts of the infusion set (bag, line and filter) was dramatically decreased by the addition of polysorbate 80 solution at concentrations at or over its critical micelle concentration (CMC). The filgrastim adsorption ratio was highest at a solution pH of 5.65, which is the isoelectric point (pI) of filgrastim. This study showed that the degree of filgrastim adsorption on infusion sets is similar for original and biosimilar preparations, but that the addition of polysorbate 80 to the infusion solution at concentrations at or above its CMC is effective in preventing filgrastim adsorption. The addition of a total-vitamin preparation with a polysorbate 80 concentration over its CMC may be an effective way of preventing filgrastim adsorption on infusion sets.

著者

佐々木 琢磨 新井 祥子 池川 哲郎 千原 呉郎 福岡 文子

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.19, no.4, pp.821-826, 1971-04-25 (Released:2008-03-31)

被引用文献数

24 39

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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.

著者

Hideyuki Konishi Fumika Hoshino Kei Manabe

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.64, no.10, pp.1438-1441, 2016-10-01 (Released:2016-10-01)

参考文献数

35

被引用文献数

13

---

We have developed a safe and practical synthetic method for preparing axially chiral diphenyl dicarboxylates using Pd-catalyzed external-CO-free carbonylation with phenyl formate as a CO surrogate. Optimized conditions consisted of axially chiral [1,1′-binaphthalene]-2,2′-diyl ditriflate and its congeners, each easily prepared from commercially available enantiomerically pure diols, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane, ethyldiisopropylamine, and no solvent. To demonstrate the potential utility of these products, this method was conducted on gram-scale and the phenyl ester products were converted to other useful compounds, and both processes were carried out without difficulty.

著者

Jung-Sub Shin Hee-Won Park Gyo In Hyun Kyu Seo Tae Hyung Won Kyoung Hwa Jang Byung-Goo Cho Chang Kyun Han Jongheon Shin

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

pp.c16-00240, (Released:2016-07-05)

参考文献数

17

被引用文献数

14

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Panax ginseng C.A. Meyer is one of the most popular medicinal herbs in Asia and the chemical constituents are changed by processing methods such as steaming or sun drying. Metabolomic analysis was performed to distinguish age discrimination of four- and six-year-old red ginseng using ultra-performance liquid chromatography quadruple time of flight mass spectrometry (UPLC-QToF-MS) with multivariate statistical analysis. Principal component analysis (PCA) showed clear discrimination between extracts of red ginseng of different ages and suggest totally six discrimination markers (two for four-year-old and four for six-year-old red ginseng). Among these, one marker was isolated and the structure determined by NMR spectroscopic analysis was 13-cis-docosenamide (marker 6-1) from six-year-old red ginseng. This is the first report of a metabolomic study regarding the age differentiation of red ginseng using UPLC-QToF-MS and determination of the structure of the marker. These results will contribute to the quality control and standardization as well as provide a scientific basis for pharmacological research on red ginseng.

著者

Yoko Kanazawa Satoru Kuribayashi Masaharu Kojima Terushi Haradahira

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.10, pp.4213-4216, 1988-10-25 (Released:2011-02-08)

参考文献数

9

被引用文献数

9 10

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The metabolic pathway of 2-deoxy-2-fluoro-D-galactose (FDGal) in mice was studied by 19F NMR. Efficient accumulation of FDGal in liver was demonstrated by NMR, which is consistent with the results of Ishiwata et al. using radioactive 18FDGal. The new discovery is that this fluorinated hexose was converted to 2-deoxy-2-fluoro-D-glucose (FDG) through UDP-FDGal and UDP-FDG apparently by the action of UDP-Gal epimerase.