JPS58144317A - Carcinostatic agent - Google Patents

Carcinostatic agent

Info

Publication number
JPS58144317A
JPS58144317A JP2454382A JP2454382A JPS58144317A JP S58144317 A JPS58144317 A JP S58144317A JP 2454382 A JP2454382 A JP 2454382A JP 2454382 A JP2454382 A JP 2454382A JP S58144317 A JPS58144317 A JP S58144317A
Authority
JP
Japan
Prior art keywords
formula
carcinostatic agent
compound
integer
bond
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP2454382A
Other languages
Japanese (ja)
Other versions
JPH0229653B2 (en
Inventor
Isao Yamatsu
功 山津
Yuichi Inai
稲井 裕一
Takeshi Suzuki
鈴木 赳
Shinya Abe
信也 阿部
Shoji Kajiwara
彰治 梶原
Toru Sugitani
杉谷 透
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eisai Co Ltd
Original Assignee
Eisai Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eisai Co Ltd filed Critical Eisai Co Ltd
Priority to JP2454382A priority Critical patent/JPH0229653B2/en
Publication of JPS58144317A publication Critical patent/JPS58144317A/en
Publication of JPH0229653B2 publication Critical patent/JPH0229653B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Abstract

PURPOSE:A carcinostatic agent for remedying cancers by destroying properties of a cancerous cell through its differentiation and induction, comprising a specific polyprenyl compound as an active ingredient. CONSTITUTION:A polyprenyl compound, e.g., 3,7-dimethyl-2,6-octadiene-1-ol, shown by the formula[X is CH2OH, COOR (R is lower alkyl); a and b are H or a bond; n is integer of 1-10; with the proviso that n is integer of 1-4 or 8-10 when X is CH2OH and a=b=1, and n is 9 when X is COOR and a and b are each a bond]is used as an active ingredient for a carcinostatic agent. The carcinostatic agent can be administered continuously for a long time since it has extremely low toxicity and extremely high safety. Its dose varies greatly with kinds of cancers, degrees of symptoms, sorts of compounds, etc., a daily dose for an adult is about 10-4,000mg, preferably about 5-500mg, and it is administered orally or parenterally.

Description

【発明の詳細な説明】 本発明は、制癌剤に関する。更に詳しくは述べれば1次
の一般式 〔式中 Xは式−C)(、OHで示される基、または式
−coui−t (式中比は低級アルキル基を意味する
)で示される基を示し、a、bは水素原子またはa。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an anticancer agent. More specifically, a group represented by the first general formula [wherein X is the formula -C] (, OH, or a group represented by the formula -coui-t (the ratio in the formula means a lower alkyl group)) where a and b are hydrogen atoms or a.

bで結合手を形成し、nは1〜10の整数を示す。b forms a bond, and n represents an integer of 1 to 10.

〜4または8〜10の整数を示す。またXが式−coo
aで示される基を意味する場合は、a、bは互に結合手
を形成し、且つnは9を示す〕で示されるポリプレニル
系化合物を有効成分とする制癌剤に関する。
~4 or an integer from 8 to 10. Also, X is the formula −coo
When referring to the group represented by a, a and b form a bond with each other, and n represents 9.] The present invention relates to an anticancer agent containing a polyprenyl compound as an active ingredient.

癌は9人類が完全に克服しえないで戦い続けている残さ
れた数少ない医療上の頑敵である。わが国の癌による死
亡者は年間15万人を越え、最近の統計によれば脳血管
疾患を抜いて死因の第−位になっている。この死に至る
病にかかった患者の肉体的苦痛はいうにおよばず、精神
的苦痛は他にたとえようがない。そして癌に侵される人
達の年令層は、40〜50代の働き盛りの年令層に最も
多り、シたがって、家族の精神的、経済的苦痛ははかり
知れないものがある。
Cancer is one of the few remaining medical enemies that humanity continues to fight against and cannot completely overcome. More than 150,000 people die from cancer each year in Japan, and according to recent statistics, cancer has become the leading cause of death, surpassing cerebrovascular diseases. Not to mention the physical pain suffered by patients affected by this deadly disease, the mental pain is incomparable. The age group of people affected by cancer is most often in their 40s and 50s, who are in their prime working age, and the mental and economic suffering for their families is therefore immeasurable.

このような死に至る病に対する根本的な原因解明や治療
法、治療薬の開発は未だない。
There is still no elucidation of the fundamental cause, treatment, or development of therapeutic drugs for these deadly diseases.

そこで、今や癌に対する戦いは人類の幸福と平和に向か
っての第3次世界大戦ともいわれているが、この戦いに
むかって世界各地で多くの人が。
Therefore, the fight against cancer is now being called the third world war towards happiness and peace for mankind, and many people around the world are fighting this battle.

種々の研究方向から研究を重ねている。We are conducting research from various research directions.

本発明者等も、このような実情に鑑み、新しい効果のあ
る制癌剤を開発すべく次のような研究方向で長年研究を
継続してきた。すなわち、癌細胞の生化学的な表現形質
に関する研究から癌細胞の造腫瘍性を喪失する現象、い
わゆる脱癌現象に注目し、このような脱癌現象を人為的
に誘導して新しい癌の治療法を開発しよう、換言すれば
癌細胞の分化誘導により癌細胞としての性質を失わせし
めることにより新しい癌治療法を開発しようという方向
から研究を進めてきた。
In view of these circumstances, the present inventors have continued research for many years in the following research directions in order to develop new and effective anticancer agents. In other words, from research on the biochemical phenotypes of cancer cells, we focus on the phenomenon in which cancer cells lose their tumorigenicity, the so-called decancer phenomenon, and aim to artificially induce this decancer phenomenon to develop new cancer treatments. In other words, we have been conducting research with the aim of developing a new cancer treatment method by inducing cancer cells to differentiate and cause them to lose their cancerous properties.

本発明者等は、一つのモデル実験系として白血病細胞の
一つとしてマウス骨髄性白血病M1細抱を用いて実験を
試みた。白血病細胞の発生機序についての今日有力な見
解として、その由来する幹細胞の分化成熟が何らかの原
因で阻止され、未熟な段階のまま腫瘍性に増殖していく
ためであるとされている。そしである種の白血病細胞は
、生体因子や薬物処理により、正常細胞の方向に分化誘
導されることも報告されている。
The present inventors attempted an experiment using mouse myeloid leukemia M1 cells as one of the leukemia cells as a model experimental system. The current prevailing opinion regarding the mechanism of development of leukemia cells is that the differentiation and maturation of the stem cells from which they are derived is blocked for some reason, resulting in neoplastic proliferation at an immature stage. It has also been reported that certain leukemic cells can be induced to differentiate into normal cells by treatment with biological factors or drugs.

本発明者等は、上述の如き研究方向によりマウス骨髄性
白血病M1細胞を用いて、その分化誘導物質を探索した
結果1次の一般式(I)〔式中 Xは式−Cl(、(J
l(で示される基、または式−C(J(JR(式中几は
低級アルキル基を意味する)で示される基を示し、a、
bは水素原子またはa。
The present inventors searched for differentiation-inducing substances using mouse myeloid leukemia M1 cells in accordance with the above-mentioned research direction. As a result, the following general formula (I) [wherein X is the formula -Cl (, (J
A group represented by l( or a group represented by the formula -C(J(JR (in the formula 几 means a lower alkyl group), a,
b is a hydrogen atom or a.

bで結合手を形成し、nは1〜10の整数を示す。b forms a bond, and n represents an integer of 1 to 10.

〜4または8〜10の整数を示す。またXが式−C(J
U)Lで示される基を意味する場合は、a、bは互に結
合手を形成し、且つnは9を示す〕で表わされるポリプ
レニル系化合物が有効であることを見い出し本発明を完
成した。
~4 or an integer from 8 to 10. Also, X is of the formula -C(J
U) When referring to the group represented by L, a and b form a bond with each other, and n represents 9] We discovered that a polyprenyl compound represented by the following is effective, and completed the present invention. .

したがって1本発明の目的は、新規な制癌剤を提供する
ことにある。
Therefore, one object of the present invention is to provide a novel anticancer agent.

本発明による制癌剤を患者に投与する投与量は癌の種類
、症状の程度、化合物の種類などにより大きく異なり特
に限定されないが、成人1日あ、たり約10TI!9〜
4,000■、好ましくは約50〜〜500ηを経口若
しくは非経口的に投与する。投与剤型としては2例えば
散剤、細粒剤、・賄粒剤。
The dose of the anticancer agent of the present invention to be administered to a patient varies greatly depending on the type of cancer, the degree of symptoms, the type of compound, etc., and is not particularly limited, but is approximately 10 TI per day for adults! 9~
4,000 η, preferably about 50 to 500 η, is administered orally or parenterally. Examples of dosage forms include powders, fine granules, and granules.

錠剤、カプセル剤、注射剤などがあげられる。製剤化の
際は1通常の製剤担体を用い、常法により製造する。
Examples include tablets, capsules, and injections. When preparing a formulation, it is produced by a conventional method using a conventional pharmaceutical carrier.

本発明化合物を、制癌剤として用いる場合は。When the compound of the present invention is used as an anticancer agent.

従来用いられている抗癌物質と併用し癌を治療すること
はもちろんさしつかえない。−例をあげれば白血病に用
いる場合は1例えばビンクリスチン。
Of course, it may be used in combination with conventionally used anticancer substances to treat cancer. - For example, for use in leukemia, eg vincristine.

プレドニソロン、プスルファン、ニスキノン、アドリア
マイシン、など各種の抗癌剤と同時に併用することはも
ちろんさしつかえない。特にプレドニソロンなどのステ
ロイドホルモンと併用することにより、より一層効果が
ある。
It goes without saying that it can be used in combination with various anticancer drugs such as prednisolone, psulfan, nisquinone, and adriamycin. It is especially effective when used in combination with steroid hormones such as prednisolone.

本発明化合物の代表的化合物を列挙すれば次のとおりで
ある。
Representative compounds of the present invention are listed below.

0 3、7.11.15.19.23.27.31−才
クタメチル−2,6,10,14,18,22,26,
30−ドトリアコンタオクタエン−1−オール○  3
.7. 11. 15. 19.23.27.31.3
5−ノナメチル−2,6,10,14,18,22,2
6,30゜34−ヘキサトリコンタノナエン−1−オー
ルo  3.7.11.15.19.23.27.31
.35.39−デカメチル−2,6,10,14,18
,22,26゜30.34.38−テトラコンタデカエ
ン−1−オール o  3.7.11.15.19.23.27.31.
35.39゜43  ” ’7 h メチk  2,6
+ 10,14,18゜22.26.30,34,38
.42−テトラテトラコンタウンデカエン−1−オール o  3.7.11.’15.19.23.27−ヘプ
タメチル−2,6,10,14,18,22,26−オ
クタコサへブタエン−1−オール o  3.7.11.15.19.23−へキサメチル
−2゜6.10,14.18.22−テトラコサへキサ
エン−1−オール o  3.7.11.15.19−ペンタメチル−2,
6゜10.14.18−エイコサペンタエン−1−オー
ル(ケラニルファルネソール) o  3.7. IL 15−テ)ラメチル−2,6,
[。
0 3, 7.11.15.19.23.27.31-year-old kutamethyl-2,6,10,14,18,22,26,
30-dotriacontaoctaen-1-ol○ 3
.. 7. 11. 15. 19.23.27.31.3
5-nonamethyl-2,6,10,14,18,22,2
6,30゜34-hexatricontanonaen-1-ol o 3.7.11.15.19.23.27.31
.. 35.39-decamethyl-2,6,10,14,18
,22,26°30.34.38-tetracontadecaen-1-ol o 3.7.11.15.19.23.27.31.
35.39゜43 ” '7 h Mechik 2,6
+ 10, 14, 18° 22. 26. 30, 34, 38
.. 42-Tetratecontaunedecaen-1-ol o 3.7.11. '15.19.23.27-heptamethyl-2,6,10,14,18,22,26-octacosahebbutaen-1-ol o 3.7.11.15.19.23-hexamethyl-2° 6.10,14.18.22-Tetracosahexaen-1-ol o 3.7.11.15.19-pentamethyl-2,
6゜10.14.18-eicosapentaen-1-ol (keranyl farnesol) o 3.7. IL 15-te)ramethyl-2,6,
[.

14−へキサデカテトラエン−1−オール(ゲラニルゲ
ラニオール) 0 3.7.11−トリメチル−2,6,10−ドデカ
トリエン−1−オール(ファルネソール)O3,7−シ
メチルー2.6−オクタシエンー1−オール(ゲラニオ
ール) O3,7−シメチルー6−オクタエンー1−オール 03.7.11−)リメf−に−6,10−ドデカジエ
ン−1−オール 0 3、7.11.15−fト5メfk−6,10,1
4−ヘキサデカトリエン−1−オール 0 3、7.11.15.19−ペンタメチル−6,1
0゜14.18−エイコサテトラエン−オール○ 3.
7.11.15.19.23.27.31.35−ノナ
メチル−6、10,14,18,22,26,30,3
4−ヘキサトリコンタオクタエン−1−オールo   
3. 7. 11. 15. 19. 23. 27.
 31. 35. 39−デカメチル−6、10,14
,18,22,26,30゜34.38−fトラコンタ
ノナエン−1−オール0 3、7.11.15.19.
23.27.31.35.39゜43−ウンデカメチル
−6、10,14,18,22,26、30,34,3
8,42−テトラテトラコンタデカエン−1−オール 01−エトキシカルボニル−2,6,10,14゜18
.22,26,30.34.38−デカメチル−1゜5
、9.13.17.21.25.29.33.37−ノ
ナトリアコンタデカエン 01−メトキシカルボニル−2,6,10,14゜18
.22,26,30,34.38−デカメチル−1゜5
、9.13.17.21.25.29.33.37−ノ
ナトリアコンタデカエン また本発明で使用する化合物は、極めて毒性の低いもの
であり、安全性は非常に高いものであり。
14-hexadecatetraen-1-ol (geranylgeraniol) 0 3.7.11-trimethyl-2,6,10-dodecatrien-1-ol (farnesol) O3,7-dimethyl-2,6-octacyen-1 -ol(geraniol) fk-6,10,1
4-hexadecatrien-1-ol 0 3,7.11.15.19-pentamethyl-6,1
0゜14.18-eicosatetraen-ol ○ 3.
7.11.15.19.23.27.31.35-nonamethyl-6,10,14,18,22,26,30,3
4-hexatriconetaoctaen-1-ol o
3. 7. 11. 15. 19. 23. 27.
31. 35. 39-decamethyl-6,10,14
, 18, 22, 26, 30° 34. 38-f tracontanonaen-1-ol 0 3, 7.11.15.19.
23.27.31.35.39゜43-undecamethyl-6, 10,14,18,22,26,30,34,3
8,42-Tetratetracontadecaen-1-ol 01-ethoxycarbonyl-2,6,10,14゜18
.. 22,26,30.34.38-decamethyl-1°5
, 9.13.17.21.25.29.33.37-nonatriacontadecaene 01-methoxycarbonyl-2,6,10,14°18
.. 22,26,30,34.38-decamethyl-1°5
, 9.13.17.21.25.29.33.37-nonatriacontadecaene The compound used in the present invention has extremely low toxicity and is extremely safe.

したがって長期連用投与が可能であり、この意味でも本
発明の価値は高い。
Therefore, long-term continuous administration is possible, and the value of the present invention is high in this sense as well.

次に本発明の代表化合物の効果を実施例にて詳細に説明
する。
Next, the effects of representative compounds of the present invention will be explained in detail in Examples.

実施例1 Fcl  レセプターの測定 下記に示す検体化合物の、マウス骨髄性白血病M1細胞
(Ichikawa、 y;J、 Ce11. Phy
siol、 。
Example 1 Measurement of Fcl receptor The test compound shown below was applied to mouse myeloid leukemia M1 cells (Ichikawa, y; J, Ce11. Phys.
siol, .

74、223 (1969))に及ぼす分化誘導効果を
検討した。上記のM1細胞を5 X L(f’/rdの
濃度でlO%FC8添加R,PMI 1640 培養液
中に浮遊し、検体化合物Iff’ Mの濃度で加えた。
74, 223 (1969)) was investigated. The above M1 cells were suspended in 10% FC8-supplemented R, PMI 1640 culture medium at a concentration of 5 XL (f'/rd) and added at a concentration of the test compound Iff'M.

これを37℃、5%CU2下、2〜下口2〜3後。This was heated at 37°C under 5% CU2 after 2 to 3 minutes.

Fcγレセプターを測定し、マクロファージや鮪粒球へ
の分化誘導効果を検討した。
Fcγ receptor was measured and the effect of inducing differentiation into macrophages and tuna granulocytes was examined.

検体化合物 化合物A 二3.7−ジメチル−2,6−オクタジエン
−1−オール 化合物B : 3.7.11.15−テトラメチル−2
゜6、10.14 −ヘキサデカテトラエン−1=オー
ル 化合物C: 3.7.11.15.19−ペンタメチル
ー2、6.10.14.18−エイコサペンタエン−1
−オール 化合物D : 3.7.11.15.19.23.27
−へブタメチル−2,6,10,14,18,22,2
6−オクタコサへブタエン−1−オール 化合物g : 3.7.11.15.19.23.27
.31゜35−ノナメチル−2,6,10,14,18
,22゜26.30.34−ヘキサトリコンタノナエン
−1−オール 化合物F : 3.7.11.15.19.23.27
.31゜35.39−デカメチル−6、10,14,1
8゜22.26,30,34.38−テトラコンタノナ
エン−1−オール 化合物G:l−エトキシカルボニル−2,6,10゜1
4.18,22,26,30,34.38−デカメチル
−1,5,9,13,1,7,21,25,29,33
゜37−ノナトリアコンタデカエン 培養条件は、化合物A、 B、Cについては3日間。
Test compound Compound A 23.7-dimethyl-2,6-octadien-1-ol Compound B: 3.7.11.15-tetramethyl-2
゜6,10.14-hexadecatetraen-1=ol Compound C: 3.7.11.15.19-pentamethyl-2,6.10.14.18-eicosapentaene-1
-ol Compound D: 3.7.11.15.19.23.27
-hebutamethyl-2,6,10,14,18,22,2
6-octacosahebbutaen-1-ol compound g: 3.7.11.15.19.23.27
.. 31゜35-nonamethyl-2,6,10,14,18
,22゜26.30.34-hexatricontanonaen-1-ol Compound F: 3.7.11.15.19.23.27
.. 31゜35.39-decamethyl-6,10,14,1
8゜22.26,30,34.38-Tetracontanonaen-1-ol Compound G: l-ethoxycarbonyl-2,6,10゜1
4.18,22,26,30,34.38-decamethyl-1,5,9,13,1,7,21,25,29,33
゜37-nonatriacontadecaene culture conditions were 3 days for compounds A, B, and C.

1o” Mでおこない、化合物1)、 E、F、Gにつ
いては2日間、 10−’Mでおこなった。その結果を
それぞれ表1および表2に示す。
Compounds 1), E, F, and G were tested at 10-'M for 2 days. The results are shown in Tables 1 and 2, respectively.

表1  培養条件:3日、 10″″′M対照25%表
2  培養条件: 2 日、 10−’M実験例2 実験例1の方法に準じて検体化合物として化合物Cを選
び濃度IQ−slV、  2X1叶IM、および5×1
0−’MでのFcrを測定した。結果を図1に示す。
Table 1 Culture conditions: 3 days, 10'''M control 25% Table 2 Culture conditions: 2 days, 10-'M Experimental example 2 Compound C was selected as a test compound according to the method of Experimental example 1, and the concentration IQ-slV , 2X1 leaf IM, and 5×1
Fcr at 0-'M was measured. The results are shown in Figure 1.

図1において横軸は反応開始後の時間を示し、縦軸はF
cr(95j を示す。
In Figure 1, the horizontal axis shows the time after the start of the reaction, and the vertical axis shows F
cr (indicates 95j).

実験例3 形態学的観察 実験例1の処理をおこなった後の細胞を形態学的に観察
した。形態学的にみれば細胞全体は大きくなって、咳胞
体比が小さくなった。モして核小体は消失し、その結果
Ml細胞は成熟単球様の形態を示すようになった。開時
に!i球細胞の特徴といわれる非特異的エステラーゼ活
性の増加が細胞化学的に証明された。
Experimental Example 3 Morphological Observation Cells treated in Experimental Example 1 were morphologically observed. Morphologically, the cells as a whole became larger and the cough cell ratio became smaller. As a result, the nucleolus disappeared, and as a result, the Ml cells began to exhibit a mature monocyte-like morphology. At opening time! An increase in nonspecific esterase activity, which is said to be a characteristic of i-cells, was cytochemically demonstrated.

に記の点は本発明化合物を添IJT+すると1′4.細
胞が弔球細抱、マクロファージへの分化が誘導されたこ
とを示唆する現象である。
The points mentioned above are 1'4. when the compound of the present invention is added to IJT+. This phenomenon suggests that cells have been induced to differentiate into leukocytes and macrophages.

【図面の簡単な説明】[Brief explanation of the drawing]

図1は化合物Cの種々の濃度におけるFcr(q6)を
示す。横軸は反応開始後の時間を示し、縦軸はFcrレ
セプター(96)を示す。
FIG. 1 shows Fcr(q6) at various concentrations of Compound C. The horizontal axis shows time after the start of the reaction, and the vertical axis shows Fcr receptor (96).

Claims (1)

【特許請求の範囲】[Claims] (1)次の一般式 〔式中 Xは式−CH,OHで示される基、または式−
COOR(式中Rは低級アルキル基を意味する)で示さ
れる基を示し、a、bは水素原子またはa、bで結合手
を形成し、nは1〜10の整数を示す。 はnは1〜4または8〜10の整数を示す。 またXが式−cuuttで示される基を意味する場合は
、a、bは互に結合手を形成し、且つnは9を示す〕 で示されるポリプレニル系化合物を有効成分とする制癌
剤。
(1) The following general formula [wherein X is a group represented by the formula -CH, OH, or the formula -
It represents a group represented by COOR (in the formula, R means a lower alkyl group), a and b are hydrogen atoms or a and b form a bond, and n represents an integer of 1 to 10. n represents an integer of 1 to 4 or 8 to 10. When X means a group represented by the formula -cuutt, a and b mutually form a bond, and n represents 9.] An anticancer agent containing a polyprenyl compound represented by the following as an active ingredient.
JP2454382A 1982-02-19 1982-02-19 SEIGANZAI Expired - Lifetime JPH0229653B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2454382A JPH0229653B2 (en) 1982-02-19 1982-02-19 SEIGANZAI

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2454382A JPH0229653B2 (en) 1982-02-19 1982-02-19 SEIGANZAI

Publications (2)

Publication Number Publication Date
JPS58144317A true JPS58144317A (en) 1983-08-27
JPH0229653B2 JPH0229653B2 (en) 1990-07-02

Family

ID=12141060

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2454382A Expired - Lifetime JPH0229653B2 (en) 1982-02-19 1982-02-19 SEIGANZAI

Country Status (1)

Country Link
JP (1) JPH0229653B2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0211513A (en) * 1988-06-30 1990-01-16 Nisshin Flour Milling Co Ltd Carcinostatic agent
JPH0225415A (en) * 1988-07-13 1990-01-26 Nisshin Flour Milling Co Ltd Agent for suppressing metastasis of cancer
JP2011228264A (en) * 2009-01-20 2011-11-10 Panasonic Corp Illuminating apparatus

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3003296U (en) * 1994-04-18 1994-10-18 乾卯本家有限会社 Bag type cleaning tool

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0211513A (en) * 1988-06-30 1990-01-16 Nisshin Flour Milling Co Ltd Carcinostatic agent
JPH0225415A (en) * 1988-07-13 1990-01-26 Nisshin Flour Milling Co Ltd Agent for suppressing metastasis of cancer
JP2011228264A (en) * 2009-01-20 2011-11-10 Panasonic Corp Illuminating apparatus
US8727572B2 (en) 2009-01-20 2014-05-20 Panasonic Corporation Illuminating apparatus
US8858039B2 (en) 2009-01-20 2014-10-14 Panasonic Corporation Illuminating apparatus
USRE48790E1 (en) 2009-01-20 2021-10-26 Panasonic Corporation Illuminating apparatus

Also Published As

Publication number Publication date
JPH0229653B2 (en) 1990-07-02

Similar Documents

Publication Publication Date Title
DE60117046T2 (en) COMBINATION OF FENOFIBRATE AND COENZYME Q10 FOR THE TREATMENT OF ENDOTHELIAL MISSING FUNCTION
US6063814A (en) Phorbol esters as anti-neoplastic and white blood cell elevating agents
HUE032100T2 (en) A pharmaceutical composition comprising a hdac inhibitor and a steroid and the use thereof.
CN113274342B (en) Colchicine external composition
JPH0296523A (en) Platinum chemical remedy product
JPH05506451A (en) antiviral composition
EP1595536B1 (en) Pharmaceuticals comprising shikonins as active constituent
JPS58144317A (en) Carcinostatic agent
JPH04507249A (en) new treatment
WO2003072124A1 (en) Induction method for cell differentiation
KR100615537B1 (en) Ferrous l-threonate, its medical composition and use thereof for improving and treating the anemia diseases in human beings
Ceder et al. Treatment of psoriasis with massive doses of crystalline vitamin D and irradiated ergosterol: a preliminary report
Levey et al. A study to determine the toxicity of fumaric acid
Mead The metabolism of the essential fatty acids
Hughes et al. The influence of sex and age on the deposition of L-xyloascorbic acid in tissues of guinea-pigs
DE4127469A1 (en) Compsn. contg. chemotherapeutic agent and lithium salt - for treatment of bacterial or viral infection e.g. HSV and HIV, malaria, leishmaniasis, trypanosoma infection and Candida albicans
Clamon et al. Phase I study and pharmacokinetics of weekly high-dose 13-cis-retinoic acid
AU604226B2 (en) Method of modifying the lipid structure function and expression of cell membranes and pharmaceutical compositions for use therein
DE2625220C3 (en) Medicines used to treat liver disease
Li et al. Action of ketene on the pituitary lactogenic hormone
US20030040541A1 (en) Use of bismuth subgallate in inhibition of production of nitric oxide synthase
DE1667892A1 (en) Hypotensive and spasmolytic agent
CN111358806A (en) Anti-ovarian cancer pharmaceutical composition with synergistic effect and application thereof
CN115414343B (en) Application of alpha-ketoglutaric acid and derivatives thereof and medicine for preventing and treating skin tumor
JP2003137776A (en) Use of bismuth subgallate for inhibiting production of nitric oxide