JPH0236188A - Platinum complex - Google Patents
Platinum complexInfo
- Publication number
- JPH0236188A JPH0236188A JP63185799A JP18579988A JPH0236188A JP H0236188 A JPH0236188 A JP H0236188A JP 63185799 A JP63185799 A JP 63185799A JP 18579988 A JP18579988 A JP 18579988A JP H0236188 A JPH0236188 A JP H0236188A
- Authority
- JP
- Japan
- Prior art keywords
- platinum
- alkyl
- diaminopropane
- formula
- expressed
- 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 description 22
- 229910052697 platinum Inorganic materials 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 4
- HSLUUDBZCZUDIW-UHFFFAOYSA-N 2-propylpropane-1,3-diamine Chemical compound CCCC(CN)CN HSLUUDBZCZUDIW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract description 2
- 239000003456 ion exchange resin Substances 0.000 abstract description 2
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000001093 anti-cancer Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- -1 (dichloro) (2-n-propyl-1,3-diaminopropane) platinum (I) Chemical compound 0.000 description 1
- 238000011765 DBA/2 mouse Methods 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- POQBJIOLWPDPJE-UHFFFAOYSA-N cyclohexane-1,2-diamine;platinum Chemical compound [Pt].NC1CCCCC1N POQBJIOLWPDPJE-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical group CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は白金錯体に関し、更に詳しくは（２−アルキル
マロナト）（２−アルキル−１，３−ジアミノプロパン
）白金（Ｉｆ）に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to platinum complexes, and more particularly to (2-alkylmalonato)(2-alkyl-1,3-diaminopropane)platinum (If).
［従来の技術］
これまで金属錯体について多くの研究がなされ、その制
癌作用や抗腫瘍作用についての報告がある０例えば、（
スルファト）（１、２−ジアミノシクロヘキサン）白金
（■〉（特開昭５４−４４６２０号公報）、（１，１−
シクロブタンジ力ルポナト）（ジアミン）白金（■）［
バイオシミ（Ｂｉｏｃｈｅｍｉｅ）第６０巻、第８３５
〜８５０ページ、１９７８年］及び特願昭６２−４３９
３３号明細書に記載されている化合物がある。[Prior Art] Many studies have been conducted on metal complexes, and there are reports on their anticancer and antitumor effects.
sulfato) (1,2-diaminocyclohexane) platinum (■> (JP-A-54-44620), (1,1-
Cyclobutane (diamine) platinum (■) [
Biochemie Volume 60, No. 835
~850 pages, 1978] and patent application 1986-439
There is a compound described in the specification of No. 33.
［発明が解決しようとする課題］
従来、種々の白金錯体が知られているが、制癌作用ある
いは毒性の点で十分とは言えず、更に優れた化合物が求
められていた０本発明はこのような要請に応えるもので
ある。[Problems to be Solved by the Invention] Various platinum complexes have been known in the past, but they are not sufficient in terms of anticancer activity or toxicity, and a more excellent compound has been sought.The present invention solves this problem. This is in response to such requests.
［課題を解決するための手段］
本発明者らは、金属錯体で制癌作用を有し、毒性が低い
化合物を開発するために鋭意研究を重ねた結果、１，３
−ジアミノプロパンの２位に低級アルキル基を有する側
鎖を配位子とし、２−アルキルマロナトを脱離基とする
白金錯体がその目的に適合し得ることを見いだし、この
知見に基づいて本発明を完成した。[Means for Solving the Problems] As a result of extensive research to develop a metal complex with anticancer activity and low toxicity, the present inventors have discovered 1,3
- It was discovered that a platinum complex having a side chain having a lower alkyl group at the 2-position of diaminopropane as a ligand and a 2-alkylmalonato as a leaving group is suitable for the purpose, and based on this knowledge, the present invention Completed the invention.
本発明の化合物は、式
（式中、Ｒ１は炭素数１〜４のアルキル基を、Ｒ１中水
素原子又は炭素数１〜４のアルキル基を水目
す、）で表される（２−アルキルマロナト）（２−アル
キル−１，３−ジアミノプロパン）白金（Ｉ［）［以下
、化合物Ｉと称する。］である。The compound of the present invention is represented by the formula (2-alkyl malonato)(2-alkyl-1,3-diaminopropane)platinum(I[) [hereinafter referred to as compound I]. ].
式■におけるアルキル基Ｒ′及びＲ８は直鎖状でもよい
し、分枝鎖状でもよい。The alkyl groups R' and R8 in formula (2) may be linear or branched.
化合物■は下記の方法によって合成することができる。Compound (1) can be synthesized by the following method.
■
（式中、Ｒ１及びＲ１は前記と同じ意味である。）すな
わち、式πのくジクロロ）（２−アルキル−１，３−ジ
アミノプロパン）白金（Ｉ［＞を水酸化ナトノウムで再
生したイオン交換樹脂に通すことにより、式■の（ジヒ
ドロキシ）（２−アルキル−１，３−ジアミノプロパン
）白金（Ｉ［＞を得る。これを水に溶かし、式■のマロ
ン酸又は２−アルキルマロン酸を加え、室温で２４時間
撹拌して反応させることにより、本発明の化合物■を得
ることができる。(In the formula, R1 and R1 have the same meanings as above.) That is, the ion of the formula π of dichloro)(2-alkyl-1,3-diaminopropane)platinum (I By passing it through an exchange resin, (dihydroxy)(2-alkyl-1,3-diaminopropane)platinum (I Compound (1) of the present invention can be obtained by adding and reacting by stirring at room temperature for 24 hours.
化合物■は経口又は非経口のいずれでも投与可能である
が、非経口投与の方が好ましい。Compound (1) can be administered either orally or parenterally, but parenterally is preferred.
経口投与の場合、散剤、顆粒剤９錠剤、乳剤。For oral administration, powder, granules, 9 tablets, emulsion.
カプセル剤などの固形製剤、又は内用水剤、懸濁剤、乳
剤、シロップ剤、エリキシル剤などの液状製剤を用いる
ことができる。Solid preparations such as capsules, or liquid preparations such as internal solutions, suspensions, emulsions, syrups, and elixirs can be used.
非経口投与の場合、注射剤又は坐剤として用いることが
できる。For parenteral administration, it can be used as an injection or a suppository.
これらの製剤に用いる賦形剤、保存剤、溶解補助剤、乳
化剤、懸濁化剤、矯味剤２等張化剤、緩衝剤などは、製
剤上常用のものでよい。Excipients, preservatives, solubilizing agents, emulsifiers, suspending agents, flavoring agents, tonicity agents, buffers, etc. used in these preparations may be those commonly used in preparations.
［発明の効果］
本発明の化合物Ｉは、担癌マウスに対して強い延命効果
を示し、かつ毒性が弱いので薬剤耐性の問題が少ない制
癌剤として使用することができる。[Effects of the Invention] Compound I of the present invention exhibits a strong survival effect on cancer-bearing mice and has low toxicity, so it can be used as an anticancer agent with fewer problems of drug resistance.
（実施例）
以下、実施例、参考例および試験例を挙げて本発明を具
体的に説明する。(Examples) Hereinafter, the present invention will be specifically explained with reference to Examples, Reference Examples, and Test Examples.
参考例
（ジクロロ）（２−ｎ−プロピル−１，３−ジアミノプ
ロパン）白金（Ｉ ） ２００ｍｇ（０，５２３ａｓｅ
ｏｌ）を、本釣８００ｍ１！に撹拌しながら溶解させた
。この溶液を２Ｎの水酸化ナトリウムで再生したイオン
交換樹脂（商品名−アンバーライトＩＲＡ−４１０、オ
ルガノ社製）をつめたカラムに通した。この操作を２回
繰り返し、得られた溶出液を減圧下、４０°Ｃ以下で水
を留去し、（ジヒドロキシ）（２−ｎ−プロピル−１，
３−ジアミノプロパン）白金（ＩＩ ） １３０ｍｇを
得た。Reference example (dichloro) (2-n-propyl-1,3-diaminopropane) platinum (I) 200 mg (0,523ase
OL), 800m1 of fishing! Dissolved while stirring. This solution was passed through a column packed with an ion exchange resin (trade name: Amberlite IRA-410, manufactured by Organo Corporation) that had been regenerated with 2N sodium hydroxide. This operation was repeated twice, and water was distilled off from the resulting eluate under reduced pressure at 40°C or below, and (dihydroxy)(2-n-propyl-1,
130 mg of platinum (II) (3-diaminopropane) was obtained.
Ｉ Ｒ（ＫＢｒ）： ３４４０ｃｍ−’、３２００
ｃａ＋−’、３１００ｃｍ−’１６０４ｃｍ−’、１５
００ｃｍ−’、１３４０ｃｍ−’実施例１
５艷の水に溶かした１０６ｍｇ（０，３０７ｍｍｏｌ）
の（ジヒドロキシ）（２−ｎ−プロピル−１，３−ジア
ミノプロパン）白金（Ｉｔ）に、マロン酸３２ｍｇ（０
，３０７ｍｍｏｌ ）を加え、室温で２４時間撹拌した
０反応後、析出した結晶を吸引ろ別し、ろ液を更に減圧
下で水を留去し、析出した結晶を回収した。こうして得
た結晶を生成物６５ｍｇに対し、水２Ｍに溶かし再結晶
することにより（マロナト）（２−ｎ−プロピル−１゜
３−ジアミノプロパン）白金（Ｉｆ ） ３８ｍｇを得
た。IR (KBr): 3440cm-', 3200
ca+-', 3100cm-'1604cm-', 15
00cm-', 1340cm-'Example 1 106mg (0,307mmol) dissolved in 5 liters of water
of (dihydroxy)(2-n-propyl-1,3-diaminopropane)platinum (It), 32 mg of malonic acid (0
, 307 mmol) and stirred at room temperature for 24 hours. After the reaction, the precipitated crystals were filtered off under suction, and the water was further distilled off from the filtrate under reduced pressure to collect the precipitated crystals. 65 mg of the product was dissolved in 2M water and recrystallized to obtain 38 mg of (malonato)(2-n-propyl-1°3-diaminopropane)platinum (If).
元素分析値（ＣｅＨ＋ｓＮ＊ｏａＰｔとして）計算値（
％） Ｃ： ２６，１５ Ｈ： ４．３８ Ｎ ： ６
．７７実測値（％） Ｃ： ２５．８１ Ｈ： ４．４
５ Ｎ ： ７．０４Ｉ Ｒ（ＫＢｒ） ： ３２００
ｃｍ−’、３１１０ｃｍ−’、１６７０ｃｍ−’１６４
０ｃｍ−’
実施例２
２−メチルマロン酸を用いて実施例１に準じて処理して
、（２−メチルマロナト）（２−ｎ−）。Elemental analysis value (as CeH+sN*oaPt) Calculated value (
%) C: 26.15 H: 4.38 N: 6
．． 77 Actual value (%) C: 25.81 H: 4.4
5 N: 7.04IR (KBr): 3200
cm-', 3110cm-', 1670cm-'164
0 cm-' Example 2 Treatment according to Example 1 using 2-methylmalonic acid yielded (2-methylmalonato)(2-n-).
ピル−１，３−ジアミノプロパン）白金（Ｉ［）を収率
１９％で得た。Pyr-1,3-diaminopropane)platinum (I[) was obtained in a yield of 19%.
元素分析値（Ｃ，。Ｈｘ ＊ Ｎ ＊ Ｏａ Ｐ ｔと
して）計算値（％） Ｃ： ２８．１０ Ｈ： ４．７
１ Ｎ ： ６．５５実測値（％） Ｃ： ２Ｂ、４０
Ｈ： ４．７２ Ｎ ： ６．７８Ｉ Ｒ（ＫＢｒ）
： ３２００ｃｍ−’、３１１０ｃｍｍ−’、１６７
５ｃｍ−’１６３５ｃａ＋−’
実施例３
２−エチルマロン酸を用いて実施例１に準じて処理して
、（２−エチルマロナト）（２−ｎ−プロピル−１，３
−ジアミノプロパン）白金（ＩＩ）を収率３６％で得た
。Elemental analysis value (C, as Hx * N * Oa Pt) Calculated value (%) C: 28.10 H: 4.7
1 N: 6.55 Actual value (%) C: 2B, 40
H: 4.72 N: 6.78IR (KBr)
: 3200cm-', 3110cm-', 167
5cm-'1635ca+-' Example 3 Treated according to Example 1 using 2-ethylmalonic acid to obtain (2-ethylmalonato)(2-n-propyl-1,3
-diaminopropane) platinum(II) was obtained in a yield of 36%.
元素分析値（Ｃｌ１ＨｚｘＮｘｏａＰｔとして）計算値
（％） Ｃ： ２９．９３ Ｈ： ５．０２ Ｎ ：
６．３４実測値（％’） Ｃ： ３０．０２ Ｈ： ４
．９６ Ｎ ： ６．３８Ｉ Ｒ（ＫＢｒ） ： ３２
１０ｃｍ−’、３１３０ｃｍ−’、１６７８ｃｍ−’１
６４０ｃｍ−’
（試験例）
リンパ細胞性白血病Ｐ３８８による制癌効果評価試験
［試験方法］
（１）試験動物
ＤＢＡ／２雌性マウスで継代したＰ３８８白血病Ｉ１ｍ
胞を各１×１０′個腹腔内に移植したＣＤＦ、雌性マウ
ス（５〜６週齢９体重：１７〜２０ｇ）を試験に供した
。試料投与群は１群８匹とし、対照群は１群１６匹とし
た。Elemental analysis value (as Cl1HzxNxoaPt) Calculated value (%) C: 29.93 H: 5.02 N:
6.34 Actual value (%') C: 30.02 H: 4
．． 96 N: 6.38I R(KBr): 32
10cm-', 3130cm-', 1678cm-'1
640cm-' (Test Example) Anticancer effect evaluation test using lymphocytic leukemia P388 [Test method] (1) Test animal P388 leukemia I1m passaged in DBA/2 female mice
CDF female mice (5-6 weeks old, 9 weight: 17-20 g) each containing 1×10' cells intraperitoneally implanted were subjected to the test. The sample administration group consisted of 8 mice per group, and the control group consisted of 16 mice per group.
（２）試料
下記化合物１〜３をそれぞれ０．５％アラビアゴム／生
理食塩液に懸濁して試料１〜３とした。(2) Samples The following compounds 1 to 3 were each suspended in 0.5% gum arabic/physiological saline to prepare samples 1 to 3.
第 １ 表
（３）投与方法
Ｐ３８８白血病細胞を試験動物に移植した日を第０日と
し、前項（２）で調製した各試料を１日１回、第１日か
ら第５日ま、で計５回それぞれ別個の群の試験動物に腹
腔的投与した。対照群には０．５％アラビアゴム／生理
食塩液のみを同様に投与した。Table 1 (3) Administration method The day on which P388 leukemia cells were transplanted into the test animal was day 0, and each sample prepared in the previous section (2) was counted once a day from day 1 to day 5. Five doses were administered intraperitoneally to separate groups of test animals. In the same manner, only 0.5% gum arabic/physiological saline was administered to the control group.
（荀評価方法
効果判定は米国国立癌研究所（ＮＣＩ＞の効果判定基準
により行なった。(Xun Evaluation method) Efficacy was evaluated according to the efficacy criteria of the National Cancer Institute (NCI).
各群の生存動物を３０日間記録し、処置群の生存日数中
央値（Ｔ）および対照群の生存日数中央値（Ｃ）から
Ｔ／ Ｃｘ １ｏｏ（％）
を計算した。Surviving animals in each group were recorded for 30 days, and T/Cx 1oo (%) was calculated from the median survival (T) of the treatment group and the median survival (C) of the control group.
Ｔ／ＣＸ１００値が１２５以上を有効とした。また、毒
性の指標として体重の変化を測定した。A T/CX100 value of 125 or higher was considered valid. In addition, changes in body weight were measured as an indicator of toxicity.
この結果を第２表に示す。The results are shown in Table 2.
Claims (1)
は水素原子又は炭素数１〜４のアルキル基を示す。）で
表される白金錯体。(1) Formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1 is an alkyl group having 1 to 4 carbon atoms, R^2
represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ) platinum complex.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63185799A JPH0236188A (en) | 1988-07-26 | 1988-07-26 | Platinum complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63185799A JPH0236188A (en) | 1988-07-26 | 1988-07-26 | Platinum complex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0236188A true JPH0236188A (en) | 1990-02-06 |
Family
ID=16177093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63185799A Pending JPH0236188A (en) | 1988-07-26 | 1988-07-26 | Platinum complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0236188A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5525074A (en) * | 1993-07-12 | 1996-06-11 | Yazaki Corporation | Panel mounted connector |
-
1988
- 1988-07-26 JP JP63185799A patent/JPH0236188A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5525074A (en) * | 1993-07-12 | 1996-06-11 | Yazaki Corporation | Panel mounted connector |
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