JPS62238296A - Novel platinum complex and production thereof - Google Patents
Novel platinum complex and production thereofInfo
- Publication number
- JPS62238296A JPS62238296A JP7985986A JP7985986A JPS62238296A JP S62238296 A JPS62238296 A JP S62238296A JP 7985986 A JP7985986 A JP 7985986A JP 7985986 A JP7985986 A JP 7985986A JP S62238296 A JPS62238296 A JP S62238296A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- platinum
- optically active
- expressed
- water
- 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.)
- Pending
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims abstract 3
- QPINXQCQOKBINJ-UHFFFAOYSA-K potassium;platinum(2+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].[K+].[Pt+2] QPINXQCQOKBINJ-UHFFFAOYSA-K 0.000 claims abstract 3
- 229940116357 potassium thiocyanate Drugs 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- 239000007787 solid Substances 0.000 abstract description 6
- 238000003756 stirring Methods 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 2
- 229910020427 K2PtCl4 Inorganic materials 0.000 abstract 1
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000003058 platinum compounds Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- 239000002246 antineoplastic agent Substances 0.000 description 6
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 229940041181 antineoplastic drug Drugs 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- -1 potassium thionanate Chemical compound 0.000 description 4
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 150000003057 platinum Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- AUKXFNABVHIUAC-RXMQYKEDSA-N (R)-pyrrolidin-2-ylmethylamine Chemical compound NC[C@H]1CCCN1 AUKXFNABVHIUAC-RXMQYKEDSA-N 0.000 description 1
- VYIWZEHRTLSWFL-UHFFFAOYSA-N [Pt+2].NCC1NCCC1 Chemical compound [Pt+2].NCC1NCCC1 VYIWZEHRTLSWFL-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
で表わされる化合物またはその光学活性体は制癌剤の合
成中間体とし゛ζ打用である。DETAILED DESCRIPTION OF THE INVENTION The compound represented by or its optically active form is useful as a synthetic intermediate for anticancer drugs.
従」Jl支術−
ローゼンベルグらによるノスブラチン(CI)1〕P)
の抗腫瘍活性の発見[ネイチャー111385 (19
89)コ以来、抗腫1***性をイrする白金錯体の研究
が盛んに行われるようになり、各種のリガンドを仔する
打機内金錯体か多数合成され、その抗腫瘍活性も検討さ
れている。その中でも、(式1)で表わされる1、
l−/クロブタン/カルホキ/ラド(2−アミツメ千ル
ピロリジン)プラチナム(IN)およびその光学活性体
が特に陵れた抗腫ヌロ話性をイ+’シている。Nosblatin (CI) 1] P) by Rosenberg et al.
Discovery of antitumor activity of [Nature 111385 (19
89) Since then, research on platinum complexes that have antitumor activity has been actively conducted, and many platinum complexes containing various ligands have been synthesized, and their antitumor activity has also been investigated. There is. Among them, 1 expressed by (Equation 1),
1-/Clobutane/Kalhoki/Rado(2-Amitumethylpyrrolidine) Platinum (IN) and its optically active substance exhibit particularly strong antitumor efficacy.
この白金fa 体はジャーナル・オブ・メディ/ナル会
ケミストリー(J、Med、ehem、)2土 131
5 (1978L特開昭59−139]30号、特開昭
54−46752号ぢに記載されている一ドエ(で示さ
れる製造方法により、合成)れていた(特願+1/15
G−189657Y3−)(j(2)(浅3) (
式71)
(戊申N1は、水A;原Yまたはナトリウム原子を人わ
ず。)
光−肌が1n及L−よ3に1A−側必り黒F記のUt来
の製ご方法は以ドに示す妊りの問題点を51’ してい
た。すなわち、
■ (式2)で表わされるノアミンを出発物質乏し゛〔
目的化合物である(式5)で表わされる白金錯体を?i
)るまでに3行程を・易シ1、合成にかなりの1−1数
をグした。This platinum fa body is Journal of Medicine/Narukai Chemistry (J, Med, ahem,) 2 Sat 131
5 (1978L JP-A-59-139) No. 30, JP-A-54-46752 (synthesized according to the manufacturing method shown in JP-A-54-46752) (Patent application +1/15)
G-189657Y3-) (j (2) (shallow 3) (
Formula 71) (Boshin N1 does not include water A; original Y or sodium atom.) Light-skin must be on 1A- side on 1n and L-3, and the manufacturing method since Ut in black F is I identified 51' of the fertility problems listed below. That is, ■ Noamine represented by (Formula 2) is used as a starting material.
What is the target compound, a platinum complex represented by (Formula 5)? i
) It took 3 steps to make it easy to use 1, and a considerable number of 1-1 was added to the synthesis.
■ (弐3)で表オ)されるノウ011体から7ニトラ
ト体を合成する1−i−程において溶媒として用いた水
を低温てlO縮口なければならす、後処理に非常に時間
を“畏した。■ The water used as a solvent in Step 1-i- of synthesizing the 7-nitrato compound from the No. I was in awe.
■ (式3)で表わさオlる/クロロ体から/ニドラド
体を合成するイ1゛稈において生成するj−化t1(は
拉rか小さく、その除去には非常に手間かかかった。(2) The j-formation t1 (formed in the process of synthesizing the nidrado form from the ol/chloro form expressed by formula 3) was very small, and its removal was very time-consuming.
なとである。そこで本発明名らは、′fIi時間で効率
の良い(式5)で表わされる白金錯体の製造方法を見い
出すへく鋭α研究を市ね(式1)で表わされる本発明の
新規白金錯体を中間体とする製造方法が優れていること
を見い出し、−11記の問題点を解決した。It is Nato. Therefore, the inventors of the present invention have conducted intensive research to find a method for producing the platinum complex represented by (Formula 5) that is efficient in 'fIi time. It was discovered that the method for producing an intermediate is superior, and the problem of item -11 was solved.
阻皿立壬l−伏すj力、ガガ手段一
本発明者らはプラチナム(II)ボタンラムクロライド
とチオンアン酸カリウムとの反応液に2−アミ/メチル
ピロリジンまたはその光学活性体を反応させることを特
徴とする製造方法を確Cr−L %その方法によって(
式1)で表わされるンスー、7チオンアナト(2−アミ
ノメチルピロリジン)プラチナム(n)を合成して本発
明を完成するに至った。The present inventors have proposed that 2-amino/methylpyrrolidine or its optically active substance be reacted with a reaction solution of platinum (II) buttonlum chloride and potassium thionanate. The characteristic manufacturing method is to ensure that Cr-L% (
The present invention was completed by synthesizing 7thionanato(2-aminomethylpyrrolidine)platinum (n) represented by formula 1).
なお、目的とする制癌剤として有用な1.1−7クロブ
タン′ジカルボキンラト(2−アミ/メチルピロリジン
)プラチナム(n)およびその光学活性体は、本発明の
化合物であるシスーノチオ/アナト(2−アミノメチル
ピロリジン)ブラ千ナム(II)またはその光学活性体
を水に2g5し、これに1,1−7クロブタンジカルボ
/酸の銀塩を加え、0〜100°Cで反応されることに
より1することかできる。Note that 1,1-7 clobutane' dicarboquine lato (2-amino/methylpyrrolidine) platinum (n) and its optically active form, which are useful as anticancer agents, are cisnotio/anato (2-aminomethyl), which is a compound of the present invention. pyrrolidine) Brasennam (II) or its optically active substance is dissolved in water (2 g5), 1,1-7 clobutane dicarbo/acid silver salt is added thereto, and the mixture is reacted at 0 to 100°C to form 1. I can do it.
本発明の12造力法は、上式に示す通りである。The 12 force building method of the present invention is as shown in the above formula.
(式1)
本発明の製造方法をさらに詳しく述へる。プラチナl、
(n)ボタンラムクロライドと4倍モルのチオンアン酸
カリウt、とを水に溶解し、温度O〜100°C好まし
くは20〜80°Cの範囲で通常0.5〜5時間の範囲
で撹拌不反応させ、これに2−アミノメチルピロリ7ン
またはその光学活性体をプラチナム(n)ボタ7ウムク
ロライドと等モル加え、l…度0〜100°Cの範囲で
通常0.5〜10時間の範囲で撹拌した後、生成した固
体をろ取し、水洗して通常温度O〜80゛Cの範囲で減
圧ド乾燥することにより、(式1)で表わされるシスー
ジチオンアナト(2−アミノメチルピロリシン)プラチ
ナム(■)またはその光学活性体を得る。(Formula 1) The manufacturing method of the present invention will be described in more detail. platinum l,
(n) Buttonram chloride and 4 times the mole of potassium thionanate are dissolved in water and stirred at a temperature of 0 to 100°C, preferably 20 to 80°C, usually for 0.5 to 5 hours. After unreacting, 2-aminomethylpyrroli7 or its optically active form is added in an equimolar amount to platinum (n) chloride, and the mixture is heated at a temperature of 0 to 100°C for usually 0.5 to 10 hours. After stirring in a range of (pyrolysine) platinum (■) or its optically active form.
本発明の化合物を中間体と1.て用いることによって制
癌剤として優れている1、1.−/クロブタンジ力ルポ
キシラト(2−アミ/メチルピロリジン)プラチナム(
II)およびその光学活性体を効)−1,<よ(合成で
きる。すなわち、■ (式2)で表わされるンアミンを
出発物質として目的物質である(式5)で表わされる白
金錯体を得るまでに3行程を要していたものが本発明の
中間体を用いると2行程に短縮され、合成にかなりの日
数を要したものか0.5〜10数時間で行われるように
なった。The compound of the present invention is combined with an intermediate and 1. 1, 1. It is excellent as an anticancer agent when used as -/Clobutane dilupoxylate (2-amino/methylpyrrolidine) platinum (
II) and its optically active substance can be synthesized using (1)-1,<yo (i.e., until the target substance, the platinum complex represented by (Formula 5), is obtained using the amine represented by (Formula 2) as a starting material. By using the intermediate of the present invention, the process that previously required three steps was shortened to two steps, and the synthesis process, which previously required a considerable number of days, can now be completed in 0.5 to 10-odd hours.
■ (弐3)で表わされるノクロロ体からノニトラト体
を合成する行程において溶媒として用いた水を低温で7
0縮しなければならす、後処理に非常に時間を要してい
たものか本発明の中間体を用いることによりこの行程を
経由ぜすに反応が行われるので、この行程の作業か省か
才j、tWする時間が非常に短縮された。■ The water used as a solvent in the process of synthesizing the nonitrato compound from the nochloro compound represented by (23) was heated at a low temperature for 7
However, by using the intermediate of the present invention, the reaction is carried out without passing through this step, so the work and resources of this step can be saved. j, tW time was greatly shortened.
■ (式3)で表わされる/クロロ体かb/ニドラド体
を合成する行程において生成する塩化銀は粒子か小さく
その除去はミリポアフィルターなとて1−Iわなければ
ならす非常に1間のかかる作業であった。しかし、本発
明の中間体を経由した場合には塩化銀が生成する行程が
なく、合成に認する時間か非常に短縮された。■ The silver chloride produced in the process of synthesizing the /chloro compound or b/nidorado compound represented by (Formula 3) has small particles and must be removed using a Millipore filter, which takes a very long time. It was work. However, when the intermediate of the present invention is used, there is no process for producing silver chloride, and the time required for synthesis is greatly shortened.
などのように前記の問題点を解決して、本発明を完成し
た。The present invention was completed by solving the above-mentioned problems.
以下実施例を挙げて説明する。This will be explained below with reference to examples.
スj色」外4−
プラチナム(II)ボタ/ラムクロライド・1.15g
(0,01モル)を水100m1に溶結′シ、これにチ
オ/アン酸カリウム3.88g (0,01モル)を加
λ、室温で30分間撹拌後、:2−了ミツエチルピロリ
/ンi、oog(0,01モル)を加えろ。¥温て1時
間撹(1゛後牛成し、た固体をろ取し、水t)1シた後
、60°Cで3時間減圧1・1:を燥15、を炎黄色の
/スー/チオ/アナ1−(2〜アミ、/メ壬ルビ口リジ
ン)プラ千ナム(11)3.91 >: (収・担95
%)を得る。4- Platinum (II) Buta/Rum Chloride 1.15g
(0.01 mol) was dissolved in 100 ml of water, 3.88 g (0.01 mol) of potassium thio/anate was added thereto, and after stirring at room temperature for 30 minutes: Add i,oog (0.01 mol). ¥ Warm and stir for 1 hour (after 1 hour, the solid is dried, the solid is filtered and water is poured), and then dried at 60°C for 3 hours under reduced pressure 1.1. /Thio/Anna 1-(2~Ami,/Melubikuchirijin) Prasennum (11) 3.91 >: (Collection/Ban 95
%).
融点201〜204°C(分解)
元素分析値 分子式C,H,□N4. P r: SZ
、として実施例1と同様にして(R)−2−アミノメ
チルピロリジン1.OOg (0,01モル)を用いて
淡黄色の(R)−7スー/チオンアナl−(2−了ミツ
メチルピロリジン)ブラチナム(n)3゜95g(収率
96%)を得る。Melting point: 201-204°C (decomposition) Elemental analysis: Molecular formula: C, H, □N4. Pr: SZ
, (R)-2-aminomethylpyrrolidine 1. OOg (0.01 mol) was used to obtain 3.95 g (yield 96%) of pale yellow (R)-7su/thionana l-(2-methylpyrrolidine)bratinum (n).
融点166〜168°C
元素分析値 うr f 1(C7II2 N4 P t
S 2として実施例1と同様にして(S)−2−アミ
ノメチルビロリシ/1.OOg (0,01モル)を用
いてl炎黄色の(S)−7スーンチオンアナト(2−ア
ミノメチルピロリノン)プラチナム(II) 3゜94
g(収率96%)を得る。Melting point 166-168°C Elemental analysis value ur f 1 (C7II2 N4 P t
(S)-2-aminomethylvirolisi/1.S2 was prepared in the same manner as in Example 1. OOg (0,01 mol) of (S)-7 Soonthionanato(2-aminomethylpyrrolinon)platinum(II) 3°94
g (yield 96%).
融点166〜169°C
元素分析値 分子式C7H,2N4 P t Szとし
て本発明の中間体を用いた制癌剤の製造力法を以下に参
考例として示す。Melting point 166-169°C Elemental analysis value Molecular formula C7H,2N4PtSz A method for manufacturing an anticancer drug using the intermediate of the present invention is shown below as a reference example.
髪η阻上
ンスージチオソアナト(2−アミノメチルピロリジン)
プラチナム(II)4.12g (0,01モル)を水
400m1に懸濁させ、これに常法で合成した1、1−
7クロブタンノカルボン酸の銀塩3.58g (0,0
1モル)を加え、90 ’Cで3時間撹拌する。反応液
をろ過して析出したチオ/アン酸銀を除去し得られたろ
液を20m1まで減圧15縮した後、室温で1時間撹拌
すると白色結晶状固体が析出する。生成した固体をろ取
し、水洗後60°Cで3時間減圧上乾燥し、1.1−/
クロブタンンカルボキンラト(2−アミノメチルピロリ
ジン)プラチナム(II)3.46g(収r+・ζ79
%)をjすた。融点248〜257°C(分解)ン−4
」12−
谷考例1と同様にして(R)−;/スー/チオ/アナト
(2−了ミツメチルピロリ/))ブラ千ナム(IN)・
1.12g (0,01モル)を用いて(R)−1,1
−/クロブタンソ力ルポキ/ラド(2−アミツメ千ルビ
ロリ/ン)ブ′う千ナム(II)3.59g(収682
%)を得た。Hair eta-inhibitor dithiothiosoanato (2-aminomethylpyrrolidine)
4.12 g (0.01 mol) of platinum (II) was suspended in 400 ml of water, and 1,1-
3.58 g of silver salt of 7-chlorobutanocarboxylic acid (0,0
1 mol) and stirred at 90'C for 3 hours. The reaction solution was filtered to remove the precipitated silver thio/anate, and the resulting filtrate was concentrated under reduced pressure to 20 ml for 15 minutes, and then stirred at room temperature for 1 hour to precipitate a white crystalline solid. The generated solid was collected by filtration, washed with water, and dried under reduced pressure at 60°C for 3 hours.
Klobutane carboquine lato (2-aminomethylpyrrolidine) platinum (II) 3.46 g (yield r+・ζ79
%). Melting point: 248-257°C (decomposition) -4
” 12- In the same way as Example 1, (R)-;/Sue/Thio/Anato(2-Remitsumethylpylori/)) Brasennum(IN)・
(R)-1,1 using 1.12 g (0,01 mol)
-/Clobutansol Lupoki/Rado (2-Amitsume 1,000 Rubirori/N) Bu'usennam (II) 3.59g (Yield: 682
%) was obtained.
1−例乃−
砂考例1と同様にして(S)−/スーノチオンア+1−
(2−アミノメチルピロリジン)プラチナム(II)4
.12g (0,01モル)を用いて(S)−11−/
クロブタンノカルボキンラト(2−アミノメチルピロリ
ジン)プラチナム(n)3、(3:3g(収率83%)
を得た。1-Example- In the same way as Sunako Example 1, (S)-/Sunochiona+1-
(2-aminomethylpyrrolidine)platinum(II)4
.. (S)-11-/ using 12 g (0.01 mol)
Clobutanenocarboquine lato(2-aminomethylpyrrolidine)platinum (n) 3, (3:3g (yield 83%)
I got it.
光肌■刀果
辺土の様に本発明の化合物は制癌剤の中間体としてa用
であり、この中間体を経由する製造方7表により、[]
的きする制癌剤を短時間で効率良く得ることかできる。The compound of the present invention is used as an intermediate for anticancer drugs, and according to Table 7 of the production method via this intermediate, []
Targeted anticancer drugs can be obtained efficiently in a short time.
出 願 人 中外製薬株式会社Applicant: Chugai Pharmaceutical Co., Ltd.
Claims (1)
ン酸カリウムとの反応液に、2−アミノメチルピロリジ
ンまたはその光学活性体を反応させることを特徴とする
。 式 ▲数式、化学式、表等があります▼(式1) で表わされる化合物またはその光学活性体の製造方法。[Claims] 1) A novel platinum complex represented by the formula ▲ Numerical formula, chemical formula, table, etc. ▼ and an optically active substance thereof. 2) It is characterized in that 2-aminomethylpyrrolidine or its optically active substance is reacted with a reaction solution of platinum (II) potassium chloride and potassium thiocyanate. A method for producing a compound represented by the formula ▲Mathematical formulas, chemical formulas, tables, etc.▼ (Formula 1) or its optically active substance.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7985986A JPS62238296A (en) | 1986-04-07 | 1986-04-07 | Novel platinum complex and production thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7985986A JPS62238296A (en) | 1986-04-07 | 1986-04-07 | Novel platinum complex and production thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS62238296A true JPS62238296A (en) | 1987-10-19 |
Family
ID=13701923
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7985986A Pending JPS62238296A (en) | 1986-04-07 | 1986-04-07 | Novel platinum complex and production thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62238296A (en) |
-
1986
- 1986-04-07 JP JP7985986A patent/JPS62238296A/en active Pending
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