JPS6034982A - 1,2-diaminocyclohexane platinum(ii) complex - Google Patents
1,2-diaminocyclohexane platinum(ii) complexInfo
- 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
Links
Abstract
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.
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)
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.
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)
| 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)
| 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 |
-
1983
- 1983-08-05 JP JP14340583A patent/JPS6034982A/en active Granted
Patent Citations (2)
| 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)
| 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 |
|---|---|---|
| Hay et al. | A convenient synthesis of the tetra-aza-macrocyclic ligands trans-[14]-diene, tet a, and tet b | |
| 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'-alkoxy-2,2':6',2"-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 | |
| CN110183494B (en) | Preparation method and application of novel orally-administrable anti-tumor Pt (IV) complex | |
| 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 | |
| JPS61500909A (en) | Mixed carboxylate platinum(2) complexes and their production method | |
| 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 |