JPH0572914B2 - - Google Patents
Info
- Publication number
- JPH0572914B2 JPH0572914B2 JP85271748A JP27174885A JPH0572914B2 JP H0572914 B2 JPH0572914 B2 JP H0572914B2 JP 85271748 A JP85271748 A JP 85271748A JP 27174885 A JP27174885 A JP 27174885A JP H0572914 B2 JPH0572914 B2 JP H0572914B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- present
- lower alkyl
- alkyl group
- germanium
- 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.)
- Expired - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 7
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 229910052732 germanium Inorganic materials 0.000 description 5
- 150000002291 germanium compounds Chemical class 0.000 description 5
- 102000001490 Opioid Peptides Human genes 0.000 description 4
- 108010093625 Opioid Peptides Proteins 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003399 opiate peptide Substances 0.000 description 4
- XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- -1 organogermanium compound Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 1
- MIAXGDNPGHKUKI-UHFFFAOYSA-N 2-methyl-3-trichlorogermylbutanoic acid Chemical compound OC(=O)C(C)C(C)[Ge](Cl)(Cl)Cl MIAXGDNPGHKUKI-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
〔産業上の利用分野〕
本発明は新規な有機ゲルマニウム化合物に関す
るものである。
〔従来の技術〕
金属の一種であるゲルマニウムGeは、半導体
として旧くから研究の対象になつていたものであ
るが、最近になつてその有機化合物に関する研究
が進んで研究成果の発表が活発に行なわれるよう
になつた結果、ゲルマニウム、とりわけその有機
化合物は種々の技術分野から注目されるようにな
つた。
例えば、式（GeCH2CH2COOH）2O3で表わさ
れるカルボキシエチルゲルマニウムセスキオキサ
イドという化合物が、極めて強力な血圧降下作用
や抗腫瘍作用等の生理活性を示す半面、全く毒性
や副作用が見られないものであることは医薬学会
では周知の事実となつている如くである。
〔発明が解決しようとする問題点〕
而して、前記カルボキシエチルゲルマニウムセ
スキオキサイドの発揮する血圧降下作用や抗腫瘍
作用等のメカニズムは未だ明確には解明されては
いないが、何等かの理由によりゲルマニウム原子
が関与していると予測されるので、前記カルボキ
シエチルゲルマニウムセスキオキサイドに於いて
ゲルマニウムに結合していた酸素とは異なる原子
又は官能基と、ゲルマニウムとの結合を含む新規
な化合物を合成することができれば、当該化合物
は上述した公知化合物に勝るとも劣らない優れた
薬理作用を発揮することが期待される。
〔問題点を解決するための手段〕
本発明は上述した事情を背景として、新規且つ
有用な有機ゲルマニウム化合物を提供することを
目的としてなされたもので、その構成は、一般式
[Industrial Application Field] The present invention relates to a novel organic germanium compound. [Prior art] Germanium Ge, a type of metal, has long been the subject of research as a semiconductor, but recently research into its organic compounds has progressed and research results have been actively published. As a result, germanium, especially its organic compounds, has attracted attention from various technical fields. For example, a compound called carboxyethylgermanium sesquioxide, which is represented by the formula (GeCH 2 CH 2 COOH) 2 O 3 , exhibits extremely strong physiological activities such as hypotensive and antitumor effects, but has no toxicity or side effects. It seems to be a well-known fact in the pharmaceutical academic society that there is no such thing. [Problems to be solved by the invention] Although the mechanisms of the blood pressure lowering effect and antitumor effect exerted by carboxyethyl germanium sesquioxide have not yet been clearly elucidated, for some reason Since it is predicted that germanium atoms are involved, a new compound containing a bond between germanium and an atom or functional group different from the oxygen bonded to germanium in the carboxyethyl germanium sesquioxide is synthesized. If possible, the compound is expected to exhibit pharmacological effects as superior as those of the above-mentioned known compounds. [Means for Solving the Problems] Against the background of the above-mentioned circumstances, the present invention was made for the purpose of providing a novel and useful organic germanium compound, which has a structure having the general formula
【化】
（式中、R1はメチル基、エチル基等の低級ア
ルキル基を、R2はR1と同様の低級アルキル基又
はフエニル基を、R3，R4は水素原子又はR1と同
様の低級アルキル基をそれぞれ表す［但し、R2
が低級アルキル基の場合、R3，R4の少なくとも
一方は低級アルキル基である］）
で表されることを特徴とするものである。
以下に本発明を詳細に説明する。
本発明の化合物は、上記式（）に明らかなよ
うに、三つの置換基R1を有するゲルマニウム原
子に、置換基R2，R3，R4と酸素官能基COYとを
有するプロピオン酸残基の結合したトリアルキル
ゲルミルプロピオン酸誘導体である。
ここで、式（）中の置換基R1はメチル基、
エチル基、プロピル基又はブチル基等の低級アル
キル基を表わし、又、置換基R2，R3，R4は水素
原子又はＲと同様の低級アルキル基若しくは置換
され或いは無置換のフエニル基を表わし、更に酸
素官能基中の置換基Ｙは−OH，OM（Ｍはナトリ
ウムやカリウム等の金属である）又はNH2をそ
れぞれ表わしており、従つて、本発明の有機ゲル
マニウム化合物は、例えば以下に示すような化合
物により代表される。[Formula, R 1 is a lower alkyl group such as a methyl group or ethyl group, R 2 is the same lower alkyl group as R 1 or a phenyl group, R 3 and R 4 are a hydrogen atom or R 1 Each represents a similar lower alkyl group [However, R 2
is a lower alkyl group, at least one of R 3 and R 4 is a lower alkyl group]). The present invention will be explained in detail below. As is clear from the above formula (), the compound of the present invention has a germanium atom having three substituents R 1 and a propionic acid residue having substituents R 2 , R 3 , R 4 and an oxygen functional group COY. It is a trialkylgermylpropionic acid derivative with a combination of Here, the substituent R 1 in formula () is a methyl group,
It represents a lower alkyl group such as an ethyl group, a propyl group or a butyl group, and the substituents R 2 , R 3 and R 4 represent a hydrogen atom or a lower alkyl group similar to R or a substituted or unsubstituted phenyl group. , furthermore, the substituent Y in the oxygen functional group represents -OH, OM (M is a metal such as sodium or potassium) or NH2 , respectively. Therefore, the organogermanium compound of the present invention can be used, for example, as follows. It is represented by the compounds shown below.
【化】[ka]
【化】[ka]
【化】[ka]
【化】[ka]
【化】[ka]
【化】[ka]
【化】[ka]
【化】
このような構造の本発明化合物は種々の方法に
より合成することができるが、例えば上記した一
連の化合物（ａ）は、次の反応式１に示すよう
に、置換基R2，R3，R4を有するトリハロゲノゲ
ルミルプロピオン酸誘導体（ａ）を、置換基
R1を含むグリニヤール試薬（）と反応させれ
ば良いのである。[Chemical formula] Compounds of the present invention having such a structure can be synthesized by various methods. For example, the above-mentioned series of compounds (a) can be synthesized by combining substituents R 2 , R The trihalogenogermylpropionic acid derivative (a) having 3 , R 4 is substituted with a substituent
It is sufficient to react with a Grignard reagent () containing R 1 .
而して、本発明の有機ゲルマニウム化合物は、
前記した公知化合物であるカルボキシエチルゲル
マニウムセスキオキサイドには見られないゲルマ
ニウム−アルキル基結合を三つ含む化合物である
ので、該カルボキシエチルゲルマニウムセスキオ
キサイドに勝るとも劣らない優れた薬理作用を発
揮することが期待される。
事実、本発明化合物を、オピオイドと総称され
るペプタイド（モルヒネ等の投与により生体内に
遊離し当該生体の自己鎮痛作用を営むとされてい
る）を分解してしまうオピオイド分解酵素に対し
作用させてみると、本発明化合物は、極めて低い
濃度であつても、しかも多種類のオピオイド分解
酵素について、強力な阻害作用を示したし、又一
方で、各種の検定菌に対し作用させたところ、極
めて強力な抗菌作用を示したのである。
従つて、本発明化合物は、投与されるモルヒネ
等の生体内での有効利用を図ると共に耽溺性の強
いモルヒネ等の投与量を減ずるためのオピオイド
分解酵素阻害剤若しくは強力な抗菌剤の主たる成
分として使用できるという有用性を具えている。
〔実施例〕
１ 本発明有機ゲルマニウム化合物の合成
２−メチル−３−トリクロルゲルミルブタン酸
（式ａ）においてR2＝Ｈ、R3＝R4＝CH3の化合
物）100ｇ（0.375mol）を無水エチルエーテルに
溶解し、氷冷下メチルマグネシウムヨーダイド
（式（）においてR1＝CH3の化合物）1.61mol
を含有するエーテル溶液を加えた後、30分間加熱
還流した。反応終了後、希塩酸（3.5％）で加水
分解し、エーテル層を分取してから該エーテル層
に無水硫酸ナトリウムを加えて脱水し、エーテル
を留去してから残渣を減圧蒸留に付すと、化合物
（ａ−）の無色透明留分65.7ｇを得た。
他の本発明化合物（ａ−２）乃至（ａ−
８）も上記と略同様の合成操作により得ることが
できたので、これら本発明化合物（ａ）の物理
化学的データを次の表１に示す。
Therefore, the organic germanium compound of the present invention is
Since it is a compound containing three germanium-alkyl group bonds, which are not found in the above-mentioned known compound carboxyethyl germanium sesquioxide, it exhibits excellent pharmacological effects comparable to those of carboxyethyl germanium sesquioxide. Be expected. In fact, the compound of the present invention is made to act on an opioid-degrading enzyme that degrades peptides collectively called opioids (which are released into the body upon administration of morphine, etc., and are said to exert a self-analgesic effect in the body). As a result, even at extremely low concentrations, the compound of the present invention showed strong inhibitory effects on many types of opioid-degrading enzymes. It showed strong antibacterial activity. Therefore, the compound of the present invention can be used as a main component of an opioid-degrading enzyme inhibitor or a strong antibacterial agent to effectively utilize administered morphine, etc. in the body, and to reduce the dose of morphine, etc., which is highly addictive. It has the usefulness of being usable. [Example] 1 Synthesis of the organic germanium compound of the present invention 100 g (0.375 mol) of 2-methyl-3-trichlorogermylbutanoic acid (compound of formula a, where R 2 = H, R 3 = R 4 = CH 3 ) 1.61 mol of methylmagnesium iodide (compound with R 1 = CH 3 in formula ()) dissolved in anhydrous ethyl ether and cooled with ice.
After adding an ether solution containing , the mixture was heated under reflux for 30 minutes. After the reaction is completed, hydrolysis is performed with dilute hydrochloric acid (3.5%), the ether layer is separated, anhydrous sodium sulfate is added to the ether layer to dehydrate it, the ether is distilled off, and the residue is subjected to vacuum distillation. 65.7 g of a colorless transparent fraction of compound (a-) was obtained. Other compounds of the present invention (a-2) to (a-
8) could also be obtained by substantially the same synthetic procedure as above, and the physicochemical data of these compounds (a) of the present invention are shown in Table 1 below.
【表】
２ 本発明有機ゲルマニウム化合物の薬理作用
現在では多種類のオピオイドペプタイド及び対
応するオピオイドペプタイド分解酵素が発見され
ているので、本発明化合物の薬理活性はオピオイ
ドペプタイド分解酵素の阻害効果をin Vitroで検
定することとした。
即ち、本発明化合物の存在下でオピオイドペプ
タイド又はそのモデル化合物にオピオイドペプタ
イド分解酵素を作用させ、本発明化合物の阻害効
果を測定したのであり、この結果、下記の表２に
示すように本発明化合物は低濃度であつても複数
種類のオピオイドペプタイド分解酵素の作用を良
く阻害したのである。
尚、該表２中の数値は本発明化合物を１mg／ml
の濃度で使用した場合の阻止率を％で表示したも
のであり、又、APはアミノペプチデース、ACE
はアンジオテンシン変換酵素をそれぞれ表わして
いる。
更に、当該化合物（ａ−４）について50％阻
止率（IC50）を算出してみると、250μｇ／mlと
良好な値であつた。[Table] 2 Pharmacological action of the organogermanium compound of the present invention At present, many types of opioid peptides and corresponding opioid peptide degrading enzymes have been discovered. I decided to test it. That is, an opioid peptide degrading enzyme was allowed to act on an opioid peptide or its model compound in the presence of the compound of the present invention, and the inhibitory effect of the compound of the present invention was measured. As a result, as shown in Table 2 below, the inhibitory effect of the compound of the present invention Even at low concentrations, it effectively inhibited the effects of multiple opioid peptide-degrading enzymes. Note that the values in Table 2 are for the compound of the present invention at 1 mg/ml.
The inhibition rate is expressed in % when used at a concentration of
represent angiotensin converting enzyme, respectively. Furthermore, when the 50% inhibition rate (IC50) of the compound (a-4) was calculated, it was a good value of 250 μg/ml.
【表】
更に又、本発明化合物を10μｇ含有する溶液を
調製し、これをペーパーデイスクに浸み込ませて
各種の検定菌に作用させることにより、本発明化
合物の抗菌活性を検定したところ、例えば第３表
に示したように、本発明化合物は広く且つ強力な
抗菌活性を示した。[Table] Furthermore, the antibacterial activity of the compound of the present invention was assayed by preparing a solution containing 10 μg of the compound of the present invention and soaking it into a paper disk and allowing it to act on various test bacteria. As shown in Table 3, the compounds of the present invention exhibited broad and strong antibacterial activity.
【表】
尚、上記表３中の検定条件の表示は次のような
意味である。
合Ｓ：Bacillus subtilis（PCI219）／合成培地
M.I：Micrococcus luteus（ATCC9341）／栄養
寒天培地
Sa.C：Staphylococcus aureus（KF26）／栄養寒
天培地
S.a：Saccharomyces sake（FDA209P／ポテト
寒天培地
本発明は以上の通りであるから、有機ゲルマニ
ウム化合物として産業上の利用性大なるものがあ
る。[Table] In addition, the indications of test conditions in Table 3 above have the following meanings. Combined S: Bacillus subtilis (PCI219) / Synthetic medium MI: Micrococcus luteus (ATCC9341) / Nutrient agar medium Sa.C: Staphylococcus aureus (KF26) / Nutrient agar medium Sa: Saccharomyces sake (FDA209P / Potato agar medium The present invention Therefore, it has great industrial applicability as an organic germanium compound.
Claims (1)
ルキル基を、R2はR1と同様の低級アルキル基又
はフエニル基を、R3，R4は水素原子又はR1と同
様の低級アルキル基をそれぞれ表す［但し、R2
が低級アルキル基の場合、R3，R4の少なくとも
一方は低級アルキルである］） で表されることを特徴とする有機ゲルマニウム化
合物。[Scope of Claims] 1 General Formula [Formula] (In the formula, R 1 is a lower alkyl group such as a methyl group or ethyl group, R 2 is a lower alkyl group similar to R 1 or a phenyl group, R 3 , R 4 represents a hydrogen atom or a lower alkyl group similar to R 1 [However, R 2
is a lower alkyl group, at least one of R 3 and R 4 is a lower alkyl group]).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28100384 | 1984-12-29 | ||
| JP59-281003 | 1984-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6292A JPS6292A (en) | 1987-01-06 |
| JPH0572914B2 true JPH0572914B2 (en) | 1993-10-13 |
Family
ID=17632914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60271748A Granted JPS6292A (en) | 1984-12-29 | 1985-12-03 | Organic germanium compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6292A (en) |
-
1985
- 1985-12-03 JP JP60271748A patent/JPS6292A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6292A (en) | 1987-01-06 |
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