Nothing Special   »   [go: up one dir, main page]

JPS6034982A - 1,2-diaminocyclohexane platinum(ii) complex - Google Patents

1,2-diaminocyclohexane platinum(ii) complex

Info

Publication number
JPS6034982A
JPS6034982A JP14340583A JP14340583A JPS6034982A JP S6034982 A JPS6034982 A JP S6034982A JP 14340583 A JP14340583 A JP 14340583A JP 14340583 A JP14340583 A JP 14340583A JP S6034982 A JPS6034982 A JP S6034982A
Authority
JP
Japan
Prior art keywords
trans
platinum
diaminocyclohexane
dach
solution
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
JP14340583A
Other languages
Japanese (ja)
Other versions
JPH0479353B2 (en
Inventor
Yoshinori Kitani
喜谷 喜徳
Masahide Nomichi
野路 雅英
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to JP14340583A priority Critical patent/JPS6034982A/en
Priority to US06/637,463 priority patent/US4710577A/en
Priority to EP84305304A priority patent/EP0136012B1/en
Priority to DE8484305304T priority patent/DE3477788D1/en
Publication of JPS6034982A publication Critical patent/JPS6034982A/en
Publication of JPH0479353B2 publication Critical patent/JPH0479353B2/ja
Granted legal-status Critical Current

Links

Landscapes

  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

NEW MATERIAL:To compound of formula I [R<1> and R<2> are NO3, MOOC(CHOH)2 COO<-> (M is alkali metal), group of formula II, or R<1> and R<2> together form <->OOC(COOH)4COO<->, group of formula III, IV, etc. provided that R<1> and R<2> are not NO3 at the same time; the steric configuration of 1,2-diaminocyclohexane is cis, trans-d or trans-l]. EXAMPLE:Mucato(trans-l-1,2-diaminocyclohexane)platinum(II). USE:Antineoplastic agent. PREPARATION:Pt(II)(NO3)2(cis-1,2-diaminocyclohexane), etc. is made to react with mucic acid, malic acid, etc. usually in water to obtain the corresponding mucic acid salt or malic acid salt, etc. of (cis-1,2-diaminocyclohexane)Pt(II) or [trans-d(or l)-1,2-diaminocyclohexane]Pt(II). The product is concentrated and dried to obtain the objective compound.

Description

【発明の詳細な説明】 本発明は1.2−ジアミノシクロヘキサン白金(n)錯
体は関する。本発明により、一般式(1) 〔式中、R1および几2 は同一もしくは異なって、N
Ox 、MOOC(CHOH)2COO−(式中、Mは
アルカリ金属を表わす)または OO− 几1 とR2は一体となって、 −〇〇〇(CHOH) 4GOO−1−000(C:H
OH) 2GOO−、−0OC;(CHOCOGH3)
4 GOO−(ただしmx およびR2は同時にNO3
ではない)を表わし、また1、2−ジアミノシクロヘキ
サン(以下、dachと称ス)の立体配位はシス、トラ
ンス−dJたはトランス−7を表わす〕で表わされる、
1,2−ジアミノシクロヘキサン白金(If)錯体が提
供される。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 1,2-diaminocyclohexane platinum(n) complexes. According to the present invention, general formula (1) [wherein R1 and 几2 are the same or different, N
Ox, MOOC(CHOH)2COO- (in the formula, M represents an alkali metal) or OO-
OH) 2GOO-, -0OC; (CHOCOGH3)
4 GOO- (However, mx and R2 are NO3 at the same time
The configuration of 1,2-diaminocyclohexane (hereinafter referred to as dach) is cis, trans-dJ or trans-7].
A 1,2-diaminocyclohexane platinum (If) complex is provided.

種々の白金錯体が知られていて、それらが抗腫瘍活性を
有することも知られている。優れた抗腫瘍活性を有する
化合物はいつもめられておシ、この目的のため研究の結
果、全く新しい立体配位を有する化合物(I)が抗腫瘍
活性を有することを見出し本発明を完成した。
Various platinum complexes are known and it is also known that they have antitumor activity. Compounds with excellent antitumor activity are always sought after, and as a result of research for this purpose, the present invention was completed by discovering that compound (I) having a completely new steric configuration has antitumor activity.

化合物(1)の製法を以下に示す。The method for producing compound (1) is shown below.

PL(I[)(No3)z (シスdach) 、pt
(旧(NO3)2(トランス−d −dach)または
PC(I[)(NOx)2(トランス−1−dach)
 (これらの化合物の製法は特開昭54−44620号
公報に記載されている)と粘液酸、糖酸カリウム、リン
ゴ酸、グルタル酸、ケトマロ/酸、ジフェン酸、α、β
−ジフェニルコハク酸、テトラ−O−アセチル−D−グ
ルクロン酸、テトラ−0−アセチル粘液酸を水溶媒体中
反応させて、対応する(シスdach)白金(幻、(ト
ラy ス−d −dach)白金(It) iたは(ト
ランス−ノーdach)白金(I[)の粘液酸塩、糖酸
塩、リンゴ酸塩、グルタル酸塩、ケトマロン酸塩、ジフ
ェン酸塩、α、β−ジフェニルコノ1り酸塩、テトラ−
0−アセチル−D−グルクロン酸塩、テトラ−0−アセ
チル−粘液酸塩が得られる。
PL(I[)(No3)z (cisdach), pt
(old(NO3)2(trans-d-dach) or PC(I[)(NOx)2(trans-1-dach)
(The manufacturing method of these compounds is described in JP-A No. 54-44620) and mucilage acid, potassium saccharate, malic acid, glutaric acid, ketomalo/acid, diphenic acid, α, β
-Diphenylsuccinic acid, tetra-O-acetyl-D-glucuronic acid, and tetra-0-acetyl mucic acid are reacted in an aqueous medium to produce the corresponding (cis-dach) platinum (phantom, (trys-d-dach)). Platinum (It) i or (trans-nodach) platinum (I[) mucolate, saccharate, malate, glutarate, ketomalonate, diphenate, α,β-diphenylcono1 phosphate, tetra-
O-acetyl-D-glucuronate, tetra-0-acetyl-mucolate is obtained.

これらの反応は通常水中で!必要に応じて加熱下に行な
われ、目的物は反応稜、通常濃縮乾燥して粉末として、
もしくは結晶の沈殿物として得られる。
These reactions usually take place in water! The reaction is carried out under heating if necessary, and the target product is the reaction mixture, which is usually concentrated and dried as a powder.
Alternatively, it can be obtained as a crystalline precipitate.

本化合物の具体例およびその元素分析値を第1表に示す
Specific examples of this compound and their elemental analysis values are shown in Table 1.

次に本化合物の抗腫瘍作用について以下に示す0 CDFマウス(1群6匹)にl、 1210の105個
の細胞を腹腔内投与し、投与当日、5日目、9日目に供
試化合物を投与し、平均生存期間の延長(T/G%)を
めた。結果を第2表に示す。
Next, regarding the antitumor effect of this compound, 105 cells of 0 CDF mice (6 mice per group) shown below were intraperitoneally administered, and the test compound was administered on the day of administration, on the 5th day, and on the 9th day. was administered to increase the average survival time (T/G%). The results are shown in Table 2.

第 2 表 以下に実施例を示す。なお各実施例で得られた目的物の
元素分析値は第1表に示されている。
Examples are shown below in Table 2. The elemental analysis values of the target products obtained in each example are shown in Table 1.

実施例I Pt(旧(NOsh ()ランス−1−dach) 1
.517(3,5m mol )を水10μに直火で←
加熱溶解し、室温まで冷却する。粘液酸0.73g(3
,5mmol )を水10−に懸濁し、54 NaOH
溶液を添加して攪拌溶解する。両溶液を混合しくpH4
)室温で4日間放置後、生じた白色沈殿を沢取して、5
0〜60℃で減圧乾燥し、ムカト(トランス−l −d
ach)白金(ll) 1.03 19 (収率58%
)を得る。
Example I Pt (old (NOsh () Lance-1-dach) 1
.. 517 (3.5m mol) in 10μ of water over open flame←
Heat to dissolve and cool to room temperature. Mucilage acid 0.73g (3
, 5 mmol) was suspended in water 10-, and 54 NaOH
Add the solution and stir to dissolve. Mix both solutions until pH 4.
) After leaving it at room temperature for 4 days, the white precipitate that formed was collected and
Dry under reduced pressure at 0 to 60°C to obtain Mukato (trans-l-d
ach) Platinum (ll) 1.03 19 (yield 58%
).

実施例2 pt(II)(NOx)2()ランス−A! −dac
h) 1.59(3,5m mol )を水15 ml
に加熱溶解し、室温まで冷却する。D−糖酸カリウムQ
、86g(3,5mmol )を水151!+/に溶解
し、これにPL(II)錯体溶液を加えたのち、溶液の
pHを5チKOHで5とする。4日間室温放置し、生じ
た白色沈殿をP取し、澤゛圧乾燥し、D−サッカラード
(トランス−1−dach)白金(l[) 1.2 g
(収率67チ)を得るn 実施例3 Pt(If)(NO3)z () 5ンスー73− d
ach) 1.0 g(2,3m mol )を水10
mに加熱溶解し、室温に冷却後、L−リンゴ酸0.62
# (4,6m mol )を水151に溶解した溶液
を加える。54NaOHで溶液のpHを4として2か月
間室温放置し、生じた白色沈殿をe取し、減圧乾燥し、
L−マレート(トランス−/ −dach)白金(II
)0.51.9 (収率50チ)を得る。
Example 2 pt(II)(NOx)2() Lance-A! -dac
h) 1.59 (3.5 mmol) in 15 ml of water
Heat to dissolve and cool to room temperature. D-sugar acid potassium Q
, 86g (3.5mmol) of water 151! After adding the PL(II) complex solution to this solution, the pH of the solution is adjusted to 5 with 5% KOH. After leaving at room temperature for 4 days, the resulting white precipitate was collected and dried under high pressure, and 1.2 g of D-saccharide (trans-1-dach) platinum (l[)
Example 3 Pt(If)(NO3)z () 5% 73-d
ach) 1.0 g (2.3 mmol) in 10 ml of water
After heating and dissolving in m, and cooling to room temperature, L-malic acid 0.62
A solution of # (4.6 mmol) dissolved in 151 parts of water is added. The pH of the solution was adjusted to 4 with 54 NaOH and left at room temperature for 2 months, and the resulting white precipitate was collected and dried under reduced pressure.
L-malate (trans-/-dach) platinum(II)
) 0.51.9 (yield: 50 cm).

実施例4 Pt(I[)(NOx)z ()ランス−1−daeh
) 0.51(1,2m mol )を水101に加熱
溶解し、この溶液にグルタル酸0.311i(2,4m
 mol )を水10−に溶解した溶液を加える。得ら
れた溶液のpHを5%NaOHで5に調整し、3週間室
温に放置する。析出した白色沈殿をP取し、減圧乾燥し
、グルタレート(トランス−11−daeh)白金(…
)0.11 (収率21チ)を得る。
Example 4 Pt(I[)(NOx)z()lance-1-daeh
) 0.51 (1.2 m mol) was heated and dissolved in water 101, and glutaric acid 0.311 i (2.4 m mol) was dissolved in this solution.
A solution of 10 mol) of water is added. The pH of the resulting solution is adjusted to 5 with 5% NaOH and left at room temperature for 3 weeks. The precipitated white precipitate was collected and dried under reduced pressure to obtain glutarate (trans-11-daeh) platinum (...
) 0.11 (yield: 21 cm).

実施例5 Pt(If)(No3)2()ランス−ノーdach)
 1.077(2,4m mol )を水10−に加熱
溶解後、室温に冷却した溶液にケトマロン酸1水和物0
.321(2,4m mol )を水5ゴに溶解した溶
液を加える。混合溶液のpHを5%N aOHで5に調
整し、1週間室温放置する。生じた白色沈殿をr取し、
減圧乾燥し、ケトマロネート(トランス−1−dach
)白金(I[) 0.3.91 (収率30%)を得る
Example 5 Pt(If)(No3)2() Lance-No dach)
After heating and dissolving 1.077 (2.4 mmol) in water, 0.0% of ketomalonic acid monohydrate was added to the solution cooled to room temperature.
.. A solution of 321 (2.4 mmol) dissolved in 5 g of water is added. The pH of the mixed solution was adjusted to 5 with 5% NaOH and left at room temperature for one week. Collect the resulting white precipitate,
After drying under reduced pressure, ketomalonate (trans-1-dach
) Platinum (I[) 0.3.91 (yield 30%) is obtained.

実施例6 pt(■)(NOa)z ()ランス−73−dach
) 0.51!(1,2m mol )を水10−に加
熱溶解し、この溶液にジフェン酸0.28Jl (1,
2m mol )を水60コに5チNaOH添加して溶
解(pH<7)した溶液を加える。水を加えて全量15
0コ、pH6〜7に調整し、−昼夜放置後、生じた沈殿
をf取する。沈殿を水、エタノールで洗浄後減圧乾燥し
、ジフエネート(トラフ ス−73−daeh)白金(
If)0.18# (収率28チ)を得る。
Example 6 pt(■)(NOa)z() Lance-73-dach
) 0.51! (1,2 mmol) was heated and dissolved in water 10-1, and 0.28 Jl (1,2 mmol) of diphenic acid was added to this solution.
A solution prepared by adding 2 mmol) of NaOH to 60 cups of water and dissolving it (pH<7) is added. Add water and total amount 15
After adjusting the pH to 6 to 7 and leaving it for day and night, collect the resulting precipitate. The precipitate was washed with water and ethanol, dried under reduced pressure, and diphenate (trough-73-daeh) platinum (
If) 0.18 # (yield 28 cm) is obtained.

実施例7 α、β−ジフェニルコハクfllO,32g (1,2
mmol )を水80コに溶解し、実施例6と同様な操
作でPt([)(NOx)z ()ランス−73−da
eh)と反応させ、α、β−ジフェニルサクシネート(
トランy、 −l −dach)白金(If)0.31
1 (収率48つ)を得る。
Example 7 α,β-diphenylsuccine flIO, 32g (1,2
Pt([)(NOx)z()lance-73-da
eh) to form α,β-diphenylsuccinate (
Tran y, -l -dach) platinum (If) 0.31
1 (yield: 48 pieces).

実施例8 テトラ−0−アセチル−α−D−グルクロン酸3.47
7 (9,2m mol )をエタノール1oo ml
に加温溶解し、この溶液にPt(II)(NOs)2(
)ランス−73−daCh) 2.OJi’ (4,6
m mol )を水2omlに加熱溶解した溶液を加え
る。この混合溶液にNaOH溶液(I J/ / 15
111H20) 5.5 ml (9,2mmol)を
加え、室温で3日間放置後、減圧下40〜50℃で蒸発
乾固する。得られた残留物をベンゼン6011Llで2
回抽出し、べ/ゼン溶液を減圧乾固し、ビス(テトラ−
0−アセチルーα−D−グルクロネート)(トランス−
1−daeh)白金(11) 4.311 (収率89
%)を得る。
Example 8 Tetra-0-acetyl-α-D-glucuronic acid 3.47
7 (9.2m mol) in 1ooml of ethanol
Pt(II)(NOs)2(
) Lance-73-daCh) 2. OJi' (4,6
A solution prepared by heating and dissolving mol) in 2 oml of water is added. Add NaOH solution (I J//15
111H20) 5.5 ml (9.2 mmol) was added, and after standing at room temperature for 3 days, it was evaporated to dryness at 40-50°C under reduced pressure. The obtained residue was diluted with 6011 L of benzene.
After extraction, the be/zene solution was dried under reduced pressure and bis(tetra-
0-acetyl-α-D-glucuronate) (trans-
1-daeh) Platinum (11) 4.311 (yield 89
%).

実施例9 実施例8において、テトラ−0−アセチル−α−D−グ
ルクロン酸の代わシにテトラ−O−アセチル−β−D−
グルクロン酸を用いる以外は実施例8と同様にして、ビ
ス(テトラ−0−( アセチル−β−D−グルクロネート)(トランス−1−
dach)白金(II) 4.3 N (収率89チ)
を得る。
Example 9 In Example 8, tetra-O-acetyl-β-D- was used instead of tetra-0-acetyl-α-D-glucuronic acid.
Bis(tetra-0-(acetyl-β-D-glucuronate)(trans-1-
dach) Platinum(II) 4.3 N (yield 89%)
get.

実施例10 ナトシー0−アセチルーα−D−グルクロンff1lo
、44& (1,2m mol )をエタノール251
dに加温溶解した溶液に、Pt(If)(N(h>2(
トランス−1−dach) 0.509 (1,2m 
mol )を水5dに加熱溶解した溶液を加える。この
溶液にNaOH溶液(11! 715m1り 0.7m
l (1,2mmol )を加え、室温で3日間放置後
、減圧下40〜50℃で蒸発乾固する。得られた残留物
を水1smJに溶解し、濾過後r液を減圧下40〜50
℃で蒸発乾固する。得られた残留物をエタノール15+
++/に溶解し、濾過後P液を減圧下40〜50℃で蒸
発乾固し、残留物をベンゼンxodで洗浄する。得られ
た物質な減圧下100℃で3時間乾燥し、ナイトレート
(テ)7−o−7セチルーα−D−グルクロネート)(
トランス−71−dach)白金(1110,511(
収率60%)を得る。
Example 10 Natosee 0-acetyl-α-D-glucuronff1lo
, 44 & (1,2 m mol) in ethanol 251
Pt(If)(N(h>2(
transformer-1-dach) 0.509 (1,2m
A solution prepared by heating and dissolving mol) in 5 d of water is added. Add NaOH solution (11! 715ml 0.7ml) to this solution.
1 (1.2 mmol) was added, and after standing at room temperature for 3 days, the mixture was evaporated to dryness under reduced pressure at 40-50°C. The obtained residue was dissolved in 1 smJ of water, and after filtration, the r solution was heated under reduced pressure for 40 to 50 min.
Evaporate to dryness at °C. The obtained residue was diluted with ethanol 15+
After filtration, the P solution is evaporated to dryness under reduced pressure at 40-50°C, and the residue is washed with benzene xod. The resulting material was dried under reduced pressure at 100°C for 3 hours to give nitrate (7-o-7 cetyl-α-D-glucuronate) (
trans-71-dach) platinum (1110,511(
Yield: 60%).

実施例11 実施例10において、テトラ−0−アセチル−α−D−
グルクロン酸の代わシにテ)9−0−アセチル−β−D
−グルクロン酸を用いる以外は実施例10と同様にして
、ナイトレート(テトラ−0−アセチル−β−D−グル
クロネート)(トランス−1−dach)白金(If)
o、szy (収率60ヂ)を得る。
Example 11 In Example 10, tetra-0-acetyl-α-D-
9-0-acetyl-β-D instead of glucuronic acid
- Nitrate (tetra-0-acetyl-β-D-glucuronate) (trans-1-dach) platinum (If) in the same manner as in Example 10 except that glucuronic acid was used.
o, szy (yield 60も) was obtained.

実施例12 Pt(If)(NO3)s+ ()ランス−1−cla
eh) 1.29熱 (2,6mmol)を水IQIjに加熱溶解した溶液に
、テトラ−0−アセチル粘液酸1.09 (2,6mm
口1)をエタノール35mに加温溶解した溶液を加え、
5%Na・OHでpHを4に調整する。2日間溶液を室
温放置し、生じた沈殿をr取し、減圧乾燥−し、テトラ
−0−アセチル粘液酸(トラ/スーツ−daeh)白金
(II) 1.2 p (収率65チ)を得る。
Example 12 Pt(If)(NO3)s+ () Lance-1-cla
eh) Tetra-0-acetyl mucic acid 1.09 (2.6 mmol) was added to a solution of 1.29 heat (2.6 mmol) dissolved in water IQIj by heating.
Add a solution of mouth 1) dissolved in 35 m of ethanol by heating,
Adjust pH to 4 with 5% Na.OH. The solution was left at room temperature for 2 days, and the resulting precipitate was collected and dried under reduced pressure to obtain 1.2 p of tetra-0-acetyl mucic acid (tra/suit-daeh) platinum(II) (yield: 65 p). obtain.

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

第1〜10図は次の化合物の赤外線吸収スペクトルを示
す。 第1図:ムカト(トランス−73−dach)白金(f
f)第2図:D−サッカラード(トランス−!−dac
h )白金(II) 第3図::[、−−rレート(トランス−1−dach
)白金(If) 第4図:グルタレート(トランス−7−dach)白金
(It) 第5U:ケトマロネニト(トランス−1−dach)白
金(II) 第6図ニジフェオ、−1−()ランス−1−dach)
白金(It) 97図:α、β−ジフェニルサクシネート(トランス−
ノーdach)白金(n) 館8図:ビス(テトラ−0−アセチル−α−D−ダルク
ロネート)(トランス− 73−dach)白金(II) 第9図:ビス(テトラ−O−アセチル−β−D−グルク
ロネート)(トランス− 1−daeh)白金(II) 第10図:テトラー〇−アセチルムカト(トランス−ノ
ーdach)白金(It) 第11図および第12図は次の化合物の130−N M
 Rスペクトルを示す。溶媒はCDCl sを用いた。 第1i図:ビス(テトラ−O−アセチル−α−D−グル
クロネート)(トランス− 1−dach)白金(II) 倚←姻→89゜92.ppm : csに帰属できるシ
グナル第12図:ビス(テトラ−0−アセチル−β−D
−グルクロネート)(トランス− 73−dach)白金(…)
Figures 1 to 10 show infrared absorption spectra of the following compounds. Figure 1: Mukato (trans-73-dach) platinum (f
f) Figure 2: D-saccharade (trans-!-dac
h) Platinum(II) Figure 3: :[,-r rate (trans-1-dach
) Platinum (If) Figure 4: Glutarate (trans-7-dach) Platinum (It) 5U: Ketomalonenit (trans-1-dach) Platinum (II) Figure 6 Nidifeo, -1-() Lance-1- dach)
Platinum (It) Figure 97: α, β-diphenyl succinate (trans-
No dach) Platinum (n) Figure 8: Bis(tetra-0-acetyl-α-D-dalcuronate) (trans-73-dach) Platinum(II) Figure 9: Bis(tetra-O-acetyl-β- D-glucuronate)(trans-1-daeh)platinum(II) Figure 10: Tetra-acetylmucato(trans-no-dach)platinum(It) Figures 11 and 12 show the 130-N M of the following compounds.
The R spectrum is shown. CDCl s was used as the solvent. Figure 1i: Bis(tetra-O-acetyl-α-D-glucuronate)(trans-1-dach)platinum(II) 〚←conjugation→89°92. ppm: Signal that can be attributed to cs Figure 12: Bis(tetra-0-acetyl-β-D
-glucuronate) (trans-73-dach) platinum (…)

Claims (1)

【特許請求の範囲】 一般式(I) 〔式中、B1 およびR2は同一もしくは異なって、N
Os 、MOOC(CHOH)zCOO−(式中、Mは
アルカリ金属を表わす)または ■ oo− R1とR2は一体となって、 ””OOC;(CHOH) 4GOO−1−00C(C
HOH)2 COO−、−0OC(CHOCOC:Hs
)4GOO−(ただしR1、R2は同時にNO3ではな
い)を表わし、また1、2−ジアミノシクロヘキサンの
立体配位はシス、トランス−d’fたはトランス−1を
表わす〕で表わされる1、2−ジアミノシクロヘキサン
白金(n)錯体。
[Claims] General formula (I) [In the formula, B1 and R2 are the same or different, N
Os, MOOC(CHOH)zCOO- (in the formula, M represents an alkali metal) or ■oo- R1 and R2 are combined to form ""OOC; (CHOH) 4GOO-1-00C
HOH)2 COO-, -0OC(CHOCOC:Hs
)4GOO- (however, R1 and R2 are not NO3 at the same time), and the configuration of 1,2-diaminocyclohexane is cis, trans-d'f or trans-1]. - Diaminocyclohexane platinum(n) complex.
JP14340583A 1983-08-05 1983-08-05 1,2-diaminocyclohexane platinum(ii) complex Granted JPS6034982A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP14340583A JPS6034982A (en) 1983-08-05 1983-08-05 1,2-diaminocyclohexane platinum(ii) complex
US06/637,463 US4710577A (en) 1983-08-05 1984-08-03 Cytostatic platinum organic complexes
EP84305304A EP0136012B1 (en) 1983-08-05 1984-08-03 Cytostatic platinum complexes
DE8484305304T DE3477788D1 (en) 1983-08-05 1984-08-03 Cytostatic platinum complexes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP14340583A JPS6034982A (en) 1983-08-05 1983-08-05 1,2-diaminocyclohexane platinum(ii) complex

Publications (2)

Publication Number Publication Date
JPS6034982A true JPS6034982A (en) 1985-02-22
JPH0479353B2 JPH0479353B2 (en) 1992-12-15

Family

ID=15338004

Family Applications (1)

Application Number Title Priority Date Filing Date
JP14340583A Granted JPS6034982A (en) 1983-08-05 1983-08-05 1,2-diaminocyclohexane platinum(ii) complex

Country Status (1)

Country Link
JP (1) JPS6034982A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03504859A (en) * 1988-05-11 1991-10-24 アンドルリス、ファーマシューチカルズ、コーポレイション Platinum-polymer complexes and their use as antitumor agents
US7608730B2 (en) 2004-02-05 2009-10-27 Fresenius Kabi Oncology Limited Process for the preparation of an anti-tumor platinum (II)—complex
CN105622673A (en) * 2016-01-25 2016-06-01 南开大学 Glycosylated quadrivalent platinum compounds with anticancer activity, and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5444620A (en) * 1977-09-12 1979-04-09 Yoshinori Kitani Novel platinum complex
JPS5470226A (en) * 1977-10-19 1979-06-05 Johnson Matthey Co Ltd Platinum coordination compound

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5444620A (en) * 1977-09-12 1979-04-09 Yoshinori Kitani Novel platinum complex
JPS5470226A (en) * 1977-10-19 1979-06-05 Johnson Matthey Co Ltd Platinum coordination compound

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03504859A (en) * 1988-05-11 1991-10-24 アンドルリス、ファーマシューチカルズ、コーポレイション Platinum-polymer complexes and their use as antitumor agents
US7608730B2 (en) 2004-02-05 2009-10-27 Fresenius Kabi Oncology Limited Process for the preparation of an anti-tumor platinum (II)—complex
CN105622673A (en) * 2016-01-25 2016-06-01 南开大学 Glycosylated quadrivalent platinum compounds with anticancer activity, and preparation method and application thereof
CN105622673B (en) * 2016-01-25 2018-11-06 南开大学 Glycosylation tetravalence platinum-like compounds with active anticancer, preparation method and application

Also Published As

Publication number Publication date
JPH0479353B2 (en) 1992-12-15

Similar Documents

Publication Publication Date Title
Fleischer et al. The detection of a type of reaction intermediate in the combination of metal ions with porphyrins
Icbudak et al. Syntheses, characterization and crystal structures of novel amine adducts of metal saccharinates, orotates and salicylates
US4169846A (en) Cis-platinum (ii) complex of trans-l-1,2-diaminocyclohexane
US5104988A (en) 4&#39;-alkoxy-2,2&#39;:6&#39;,2&#34;-terpyridine derivatives and metal complexes thereof
US4710577A (en) Cytostatic platinum organic complexes
JPS5829957B2 (en) Novel platinum complex
Mendiguchia et al. Non-classical anticancer agents: on the way to water soluble zinc (II) heteroleptic complexes
JPS629115B2 (en)
JPH07500575A (en) Gallium(3) complex, method for producing the same, and pharmaceutical composition containing the same
CN103467528B (en) A kind of preparation method of lobaplatin
US5380897A (en) Tri(platinum) complexes
CN105936636A (en) Preparation methods and application of long chain-containing phenazine derivative gel factor and metal gel thereof
JPS6034982A (en) 1,2-diaminocyclohexane platinum(ii) complex
Broomhead The Preparation and Resolution of the Bis (oxalato)-2, 2'-bipyridinechromate (III) and Bis (oxalato)-1, 10-phenanthrolinechromate (III) Ions
BE898614A (en) Antitumour and antiparasitic platinum complexes - contg. 1,2-di:amino-cyclohexane ligand
US1447501A (en) Process for the preparation of basic salicylate of aluminum
Golovnev et al. Polymeric lithium (I) diaquabarbiturate: Crystal structure
US1893872A (en) Metal complex compound
CN111228276B (en) Bromooxamide binuclear copper complex with antibacterial activity and composition thereof
US2135111A (en) Vanadyl lactate and process of making it
RU2323886C2 (en) Method to manufacture potassium trichloroammineplatinate (ii) or ammonium trichloroammineplatinate (ii) from potassium tetrachloroplatinate (ii)
JPS6097991A (en) 1,2-diaminocyclohexane platinum (ii) complex
JP2773920B2 (en) Method for producing tetraammine palladium (II) chloride
Habu et al. The Stereochemistry of Complex Inorganic Compounds. XXXII. The Stereochemistry of the Ethylenediamine-2, 2'-diaminobiphenylplatinum (II) Ion and the Bis (diaminobiphenyl) platinum (II) Ion
Walton et al. Coordination compounds of silver (II). V. Preparation and characterization of new pyrazine and pyrazine carboxylate complexes and some related silver (I), copper (II), cobalt (II), and nickel (II) derivatives