JPS59139360A - Novel organo-platinum complex and its preparation - Google Patents

Abstract

NEW MATERIAL:The organo-platinum complex of formula I [R<1> is H or CH3; Y<1> and Y<2> are halogen, NO3, R<2>COO- (R<2> is OH-substituted lower alkyl, carbamoyl, or acetyl) or Y<1> and Y<2> together form the group of formula II, formula III or formula IV (R<3> is H or lower alkyl; m and n are 0-2, 0<=m+n<=2)]. EXAMPLE:cis-Malonato(2-aminomethylpyridine) platinum (II). USE:Antitumor agent. It has low toxicity and high safety. It is administered preferably parenterally, and is useful as a remedy for prostatic cancer, orchioncus, ovarioncus, malignant lymphoma, leukemia, mammary cancer and other malignant tumor. PROCESS:The compound of formula I wherein Y<1> and Y<2> are halogen can be prepared by reacting the compound of formula V (M is alkali metal; X is halogen) with the compound of formula VI in a solvent at room temperature. The product can be converted to another compound of formula I wherein Y<1> and Y<2> are NO3 or group of formula II by reacting with silver sulfate or silver nitrate.

Description

[Detailed description of the invention]

The present invention relates to a novel organic platinum complex and a method for producing the same, and more specifically, it has the general formula (1 (where nl represents a hydrogen atom or a methyl group, yl and Y2 are the same or different from each other, a halogen atom,
NO3 or a group represented by the formula R"COO- is present, or Yl and Y2 together form the formula: SO4゜'::P
O5OH or H1-0CO-(CHOFI)rn-CCH
R'') n-Coo - represents an indicator group, R2 represents a hydroxy-substituted lower alkyl group, carbamoyl group or acetyl group, R' represents a hydrogen atom or lower alkyl group + m and n represent an integer of 0.1 or 2 .However, 2m and n are O'
It is assumed that the relationship -ru + n <, -2 is satisfied. ] The present invention relates to an organic platinum wire, a body, and a manufacturing method thereof. The platinum complex (2) of the present invention has an excellent antitumor effect and is a promising compound as an antitumor agent. Many organoplatinum complexes using various diamines as ligands have been synthesized and their antitumor effects have been investigated (for example, Ros
enberg et al+, Nature, 2
2, 385 (1969J).
. Cancer and ChaITIotherap
y, dan, 133. (1981)]. As a result of various studies, the present inventors discovered that an organic platinum complex using 2-aminomethylpyridine or its derivative as a ligand has an excellent anti-IMK tumor effect9, and completed the present invention. . Preferred examples of the organoplatinum complexes of the present invention include: For example, in the general formula II), R1 is a hydrogen atom or a methyl group, and yl and Y2 are the same or different from each other and are chlorine sources.
a halogen atom such as a bromine atom or an iodine atom, N
Os, or the formula HOCHzCf)0-. Cf1sCH(OH)Coo-, HOCHzCH<0H
) COIJ −, HOCH之CHzCOO−, (CHa
9CHCH (OR3Coo-, H2NC0COO- or CHsC (a group represented by ICOO-, or Y゛1 and Y2 together form the formula] SOa, :PO
50) 1, -0CO-COD-. -0CO-CHz-COO-, -000-CH(CH3
)-Coo-. -0CO-CH(CHzCHs)-COO-, -0(:
0-CH(OH)-000-. -O(:0-C1((01()CH2-C:OO-,-
0CO-CH2CH2-COO- or -0CO-CH(
Examples include compounds forming a group represented by 0H)CI(OH)(00-. Among these compounds, more preferable compounds include 1, for example, in the general formula (R3,
R1 is a hydrogen atom or a methyl group, yl and Y2 are the same or different from each other, and are a chlorine atom or a bromine atom -N03.
MoL<Ha formula 1(OCH2(100-, Hz+(CUCU
O- or CH3Co Co O-), or Yl and Y2 together form the formula SO4, -
0CO-COQ-. -0CO-CH2-C00-, -0CO-CH(CH3
)-COO-. -0CO-CH(0J-C:Oo- or -〇〇〇-(J
Compounds forming a group represented by l((H2CHs)-COO- are mentioned. More preferable compounds include 1, for example, in the general formula (U), 'R1 is a hydrogen atom, and yl and Y2 are the same or Different atom, bromine atom, N03, or 2〇〇〇HzGOO-, HzNCOCOO- or C
A group represented by HseOCCO-, or Yl and Y2 taken together to form the formula '::S04, -0CO-C
oo-. -〇〇〇-CH2-COO-, -0CO-CH(CH3
)-COO-. -000-CH(OH)-COO- or -CIcO-C
Examples include compounds forming a group represented by H(CH2(Us)-COO-). Preferred compounds include compounds in which R' is a hydrogen atom in the general formula ['l]. Yes yl and Y2 are the same or different, chlorine atom, N03 or formula HO (
lH2cOo- or H2NC0C00-, or Yl and Y2 together i:S
04゜-0CO-(:OO-, -0CO-CH2-GO
+3-, -0CO-fj ((CH3)-COD- or -
〇Compounds forming a group represented by GO-CH(0H)-COO- are mentioned, and even more preferred compounds include those in which R1 is a hydrogen atom and yl and Y2 have the formula H2N
Is it a group represented by GOCOO-, or:! Y1 and Y
2 together form the formula -0CO-cuu-, -QCO-
(:R2-COO-. -0CO-CH(Cfh)-(100- or -〇GO
-(J(OF! 1-+:00-)? Compounds that form a group represented by: A compound represented by the formula % ([) (where 0M represents an alkali metal and X represents a halogen atom) and a compound represented by the general formula (R' has the same meaning as above). to form an organic platinum complex represented by the general formula (provided that R1 and or have the same meaning as above). The general formula (where Y3 and Y4 are the same and represent NOa, or Y3 and - together represent a group represented by the formula -8O4, and R1 is the above-mentioned ), and a compound represented by the general formula (wherein R1 has the same meaning as above) and an alkali metal/X ride, IJ Nialkali metal hydrogen phosphate 9 Formula 82COOM' (However, 1M' represents an alkali metal, and R2 has the same meaning as above.)
or M”-CICO-(GHOH)m-(CHR3)n
-COOIJ" (however, 5M" represents an alkali metal, and R3+ m and ni have the same meaning as above) to form a compound represented by the general formula (however, y5 and Y6 are the same as each other, b or different)
10 Gen atoms, N03 or a group represented by the formula R"COO- 73) + or Y5 and Y6 taken together to form the formula ZP030fi or bar 0(:0-(CHOF]1m
-(CHR')n-COO- represents a group shown,
R'', R'', R3, m and n have the same meanings as above. ) It can be obtained by producing an organic platinum complex shown in the following. The reaction between compound (old) and (IK) can be carried out by dissolving compound (') in an appropriate solvent, adding compound (III) to the solution, and stirring.Starting material IR+I
I) is 0, for example Kz[Pt(II)C:14 J
h Ruiha Na2[Pt(II)C1'J etc. can be obtained. Compound (III is compound (11)
It is preferable to use 0.8 to 1.0 times the amount by mole. Water is suitable as a solvent and one reaction can be carried out at room temperature F. Further, in the reaction of compound (, [-a) with silver sulfate or silver nitrate, it is preferable to dissolve compound (I-a) in a suitable solvent VC, add silver sulfate or silver nitrate to the solution, and stir. Silver sulfate is approximately equimolar to compound (I-a). It is preferable to use silver nitrate in an amount of about twice the molar amount of the compound (I-alj).Water is suitable as a solvent, and the reaction can be carried out at room temperature and shielded from light.Alkali metal halide/ethyl potassium hydrogen phosphate or Formula R4C00IJ' or M”-OCO-(CHOH
)m-(CHR")n-COOM' can also be carried out according to a conventional method. For example, the reaction can be carried out by dissolving the compound (■) in an appropriate solvent and adding an alkali metal bromide to the solution. , alkali metal halides such as alkali metal iodides, ethyl potassium hydrogen phosphates or the formula R”C0
0M/MoshihaM"-0CO7(C1'lOH)m-
(CHR3In-000) J" (However, R", R3, M', M', m and n have the same meaning as in @)] It can be carried out by adding and stirring the compound shown. As the alkali metal halides, for example, alkali metal bromides such as sodium bromide and potassium bromide, sodium iodide, and alkali metal iodides such as potassium iodide are preferably used; 7R compounds include lt'l! For example, R2 is a hydroxymethyl group,
■-Hydroxy-substituted lower alkyl group such as hydrocow diethyl group, 1,2-dihydroxyethyl group/2-hydroxyethyl group, l-hydroxy-2-methylp-avir group, carbamoyl group, acenal g, etc., and M' is For example, compounds that are alkali metals such as sodium and potassium can be mentioned, and these compounds have a ratio of 1.0 to
It is preferable to use 1.5 or 2.0 to 2.5 times the mole. On the other hand, examples of dialkali gold hydrogen phosphate 14 include 1, for example, disodium hydrogen phosphate, dipotassium hydrogen phosphate, etc.; Examples include sodium salts or potassium salts of ethylmalonic acid, 2-1:I'roximalonic acid, D,L-malic acid, D,L-tartaric acid or succinic acid. These compounds are preferably used in an amount of 1 to 1.5 times mole relative to compound (IV)K. Water is suitable as a solvent. The dissolution of compound (ff) is preferably carried out under heating, and one reaction can be carried out at room temperature. The target compound (I) obtained by the above method can be isolated by a conventional method such as counting the precipitated target compound. If necessary, the reaction mixture may be concentrated prior to filtration, or the reaction mixture may be subjected to column chromatography for further concentration. In addition, if silver chloride is produced as a by-product in the above reaction, remove the silver chloride by filtration, and add 5% potassium chloride aqueous solution to the diluted solution (4%
It is desirable to remove the unreacted silver compound in the form of silver chloride by filtration and then convert the target compound to simple MiT. The organic platinum complex (I) thus obtained is Ehrlichgan, Sarcoma 180. Anti-I against various types of tumor cells such as Shiromen disease L-121O9 Yoshida sarcoma and rat ascites liver cancer.
l! can exhibit tumorigenic effects, prolong the survival of animals afflicted with these tumors, and/or suppress the proliferation of tumor cells in the warm-blooded animals. For example, the compounds of the present invention, cis-oxalato(2-aminomethylpyridine)platinum(It) and cis-malonato(2-aminomethylpyridine)platinum(I) complexes, are 50·'9/9
/day by intraperitoneal administration of leukemia L-121.
It shows an excellent survival effect, extending the survival time of mice transplanted with 0 cells by more than 745%. In addition, when the growth-inhibiting effect of the above compound on Ehrlisohi ascites carcinoma was investigated, it was found that its minimal effect (i.e., it inhibited the growth of Ehrlisohi ascites carcinoma by 1%).
Minimum dose for 00% inhibition @J is 3.12”S'/1li
1/day. The compound of the present invention has an excellent anti-tumor effect, low toxicity and is therefore a highly safe anti-tumor agent, and is effective against prostate cancer, cancerous cancer, ovarian cancer, malignant lymphoma),
It can also be used to treat white men's disease, breast cancer, and other malignant tumors. When organic platinum complex (I) is used for pharmaceutical purposes, it may be used in any dosage form suitable for oral or parenteral administration, but parenteral administration is particularly preferred. It can also be used in combination with a diluted excipient. Suitable excipients include gelatin, lactose/curcose,
Salt, Denzo, magnesium stearate, talc,
Mention may be made of vegetable oils and other pharmaceutical excipients. The preparation may be a solid preparation such as a tablet, gunpowder, or capsule, or a liquid preparation such as a solution, suspension, or emulsion. Further, when compound (1) is administered parenterally, it can be used as an injection or a suppository, with injections being particularly preferred. For injections, compound (1) can be used in the form of an isotonic solution. As the tonicity agent in this case, for example, mannitol, sodium chloride, glucose, nrubitol, chrycerol, xyctol, fructose, maltose, mannose, etc. can all be suitably used. The preparation may also be sterilized and (or contain adjuvants such as preservatives and stabilizers).
) The pharmaceutical dosage depends on the method of administration and the age of the patient. The preferred daily dosage is usually about 20-1000"9, depending on the holiday, condition and disease being treated.
/yyl', especially about 50 to 500''P/rre. The present invention will be explained in more detail with reference to experimental examples and examples. In the specification of this application, the term "lower alkyl group" refers to the number of carbon atoms. This term refers to an alkyl group of 1 to 4.Example The therapeutic effect of the organic platinum complex of the present invention was tested using the following methods and compounds using mice transplanted with various cancer cells. [Experimental Method] A) Ehrlich ascites cancer cells (IXI) (1' J) were implanted into the intraperitoneal cavity of the mice in 4 groups of 5 female mice (ICR strain 0, body weight 19-23 years). A physiological saline solution of the specimen was administered once a day for 5 consecutive days. After 7 days from the first administration, ascites was measured. Effect of prolonging survival of mice transplanted with CB + leukemia L-1210 cells. One group of 4 male mice ( BDF'l series 0 weight 19-23g]
Leukemia L-1210 cells <1 x O'cells> are intraperitoneally transplanted. Starting 24 hours after transplantation, a physiological saline solution of the specimen was administered intraperitoneally to mice once a day for 5 consecutive days, and the effects were determined by comparing the average survival days of the specimen-administered group and the non-administered group. [Specimen 1, cis-oxerado (2-amino/methylpyridine) platinum (In2, cis-malonato (2-aminomethylpyridine) platinum trr) 3, cis-dioxamado (2-amino/methylpyridine) platinum (II) [Results j The experimental results are shown in Tables 1 and 2 below. Table 1 Effect of suppressing the proliferation of Ehrlich ascites carcinoma [Experimental method (AJ
J〈Note〉 (al;'P-Average storage amount of sample administration group C = Average storage amount of sample non-administration group (b): Suppression rate (%l = --X 100 (cl:
M, T, D, = Tolerable dose for adults (maximum dose that suppresses the growth of ascites cancer by 100 sounds without killing the mouse implanted with Ehrlich condensate cancer) (di: M, h:, Q, = minimum Effective margin (minimum dose ff1 that inhibits the growth of Ehrlich ascites carcinoma by 100%) (8): Therapeutic index = M, 'I', T), / M, B,
D. Gold: Number of dead C mice/Number of mice used Table 2 Survival prolonging effect of leukemia L-121Q's cell transplanted mice (Experimental method (B)) (Note) (al: 'f = Average survival days of sample administration group C- Average survival days of sample non-administered group (bl: I, L, S, (survival rate J = -X 1
00 (cl 2 Number of surviving mice for 60 days/number of mice surviving for 60 days/number of mice used (di: O, D, = optimal dose It (dose per day that shows the maximum survival effect on mice transplanted with the tumor cells) Example: 4 doses per day required to increase the average survival days of mice implanted with the tumor cells by 30% compared to non-administered group I. Add 1.20F of 2-aminomethylpyridine to 50+n1g solution and stir the mixture overnight at room temperature.The precipitated crystals are separated, washed with a small amount of cold water, and dried to form cis-dichloro(2-aminomethyl Pyridine] Platinum (n) 3.19
F is obtained as yellowish brown crystals. Elemental analysis value (Ca Hz Iiz Cl2F't 1 actual measured value (c: C, 19,26; H, 2, 15; N, 7.
48 calculated value (width): C, 19-41;) 1.2.22
;N, 7.44 The labor charge for this product is 6 pek) J is as shown in Figure 1. Example 2 To the cis-dichloro(2-aminomethylpyridine)platinum (II 33.74 M (/J 200-ml suspension in water) obtained in Example 1, a 40-♂ solution of water containing 3.40 F of silver nitrate was added. The mixture was stirred for two days and nights at room temperature under next light conditions.The precipitated silver chloride was removed, and a small amount of 5% salt (Hika IJ + Kum water extract) was added to the F3 solution to remove unreacted nitric acid. The ρ solution 2 is dried to solidity under reduced pressure, and further dried to give cis-dinitrato(2-methylbi+1-dine)platinum CI[3
3-9 g are obtained as a pale yellow powder. Elemental analysis value (C6E1* N406 Pt) Actual measurement value (
Curse): C, 16, 86; H, 1, B7; N, 13.1
1 calculated value (c, 16,95; l(, 1,761,
12,96 0.71 F was added, and the mixture was stirred overnight at room temperature. The precipitated crystals were separated and dried to form cis-dibromo(2-amino/methylpyridine) platinum (IF) 0.431 into a yellowish brown powder. Elemental analysis value I Cs HlI Nt , Br2Pt )
Actual value (%): C, 15,55; H, 1,73iμ・
6, Os Ikukeine (Direct: C, 15, 73; H, 1, 68; N
, 6.28 IR spectrum: FIG. 3 Example 4 Cis-digloro(2-aminomethylpyridine) platinum(II) obtained in Example 1 0.37 P and silver sulfate 0.31
Cis-sulfato(2-amino/methylpyridine)platinum (III O, 32F) is obtained as a pale yellow powder by carrying out the same procedure as in Example 2 using 100 m/solution of water of 7. Nt 04 SPt, )
IRuNujol(a'i'): 3320.3180
．． 3100.1615ax Example 5 Cisudinitrato(2-aminomethylpyridine)platinum (formerly 0.43 y) obtained in Example 2 was dissolved in 40 ml of water under heating, and 0.16 y of disodium mono70phosphate was added to the solution. Add 20F JIS solution of water of 100ml and leave the mixture at room temperature for 3 days. Concentrate the reaction solution and count the precipitated crystals. After washing with a small amount of cold water and drying, cis-malonat ( 2-aminomethylpyridine] platinum 1.II) 0
．． 339 is obtained as a white powder. Elemental analysis value (Go Filo-Nt 04 Pt) Actual value (<): C, 26,66; H, 2,46; N, 6
．． 91 Calculated value (%): c, 26.78;) 1.2.2
8; N, 7.12 IR spectrum: Fig. 4 Examples 6 to 13 The cis-dinitrato (2-aminomethyl bi-IJ di-nitroplatinum) obtained in Example 2 and the corresponding organic acid sodium salt,
The following compound is obtained by processing in the same manner as in Example 5. (6) Cis-dibilbat (2-aminomethylpyridine) platinum (old, pale yellow powder, yield 75 elemental analysis value (C
12N14 N20@Pt) Actual value T%l: C
, 30, 18; H, 2, 93: N, 5.87 Calculated value (curse): C, 30, 14; H, 2, 78: N, 5.69 I
RyNujO1(arr1): 3300,3210
．． 1760゜na
,24,55;H,2,04;N,7.16 Calculated value (%
): c, 24.72; H, 2,31; N, 6.98I
R spectrum 2 Figure 5 (8) Cis-diglycolate (2-amino/methylpyridine) platinum + I [), white powder, yield 77% Elemental analysis value (C10N14 Na Os Pt) Actual value (%):
C, 26,49; H, 3,09; N, 6.18 calculated value (
%): C, 26,35; H, 3,26i N,
6.011R spectrum: Figure 6 (9) cis-(glycorad) to tho)(2-aminomethylpyridine)platinum (■), pale yellow powder - yield 70
% Elemental analysis value (C3H11N30S Pt) Cow actual measurement value (%): C, 21,81; H, 2,50; N,
9.58 - Calculated value C<): C, 21,73; H, 2,
33;N, 9.711 RWNuj0' (ail)
: 3210, 3120.1600 ((■ cis-
Dioxamad (2-aminomethylpyridine) platinum (■)
, pale yellow powder, yield 5B% elemental analysis (C1DH12N
4011L? Also) Actual value (dark): C, 24, 97;
H, 2,56; N, 11.75 Calculated value (width): C,
25,05; H, 2,51; N, 11.69 IR spectrum: Figure 7ill Cis-(2-methylmalonato)

[2-Aminomethylpyridine] Platinum (II), colorless powder, yield 83
% Elemental analysis value (CION12 N20a Pt) Actual value (%): c, 28.60; H, 2,82; N, 6.7
2 Calculated value (%): C, 28,64; Ii, 2.86;
6-68 IR spectrum: Figure 8 (121 cis-(2-hydroxymalonato) (2-amino/methylpyridinone platinum (JI), colorless powder, yield 83
% Elemental analysis value + Go HION20 s Pt) Actual measurement value f%): C, 25,71; H, 2, 36; N, 6
．． 54 needle count (%J: C, 25, 65; H, 2, 3
8; N, 6.65 IR spectrum: Fig. 9 Cis-(2-ethylmalonato](2-amino/methylpyridine) platinum (TL), colorless powder, yield 79 Elemental analysis value (CIl N14 N404 Pt) Actual measurement Value (()2G, 30.48; H, 3,23; N, 6.4
7 Calculated value (%): c, 30.35; H, 3,20; N
, 6.381R Spectrum II Figure 1o Example 14 (1) 5.4F of pyridine-2--r-rudehyde, 0.57% of methylamine hydrochloride and 3g of methylamine were added to 100rn of methanol! , and the solution was dissolved in palladium-
Hydrogenation in the presence of a carbon catalyst gives 2-(methylaminomethyl"pyridine 4.57. b, p, 79~b IRν Nujol (crii"'): 3
340.1590.1570? Jasg m/e:
121 (f -11, 92 (M+-30 (NHC
I(3)) NMR (CD0 hair 3) δ: 2.47 (3H,
s, NCHi). 2.20(II(, NH, NH), 3.87<2Fi, e
, cHz). 7.05-7.80 (3H, m, pyridine ring (1)
H). 8.56 (IH, d, J=3.7Hz, H of pyridine ring) (212-(methylaminomethyl)pyridine 1
．． 347 and potassium monoplatinate chloride 4.15 F were treated in the same manner as in Example 1 to obtain cis-dichloro(2
-(methylaminomethylJpyridine)platinum(II)3.
35' is obtained as pale yellow crystals. Elemental fraction value (Cy HloNz Ulz Pt) Actual value (%): C, 21,65: [(,2,59;N
, 7.21 Calculated value (%): C, 21,59; H,
2,59; N, 7.19 IR spectrum: Figure 11 Example 15 Cis-dichloro(2-(methylaminomethyl)pyridine J platinum(II) obtained in Example 14) 0.39
By treating m and nitrate #silver 0.341 in the same manner as in Example 2, cysudinitrato(2-(methylamythyl)pyridine) platinum(II) 0.40 fj was made into a pale yellow powder. Elemental analysis value (C7Hto N406Pt') actual measurement value t
ri: C, 19,04; H, 2,26, N, 12
．． 69 calculated value (%J: C, 19, 26: H, 2, 4
1;! Ij, 12.811 RI/”;;;!', 1(
cs”): 3190.1620.1520°280 Example 16 The cis-dinitrato(2-(methylamino/methyl)pyridine)platinum(II) 0.44 F and sodium oxalate 0.13 F obtained in Example 15 were used as an example. By processing in the same manner as in step 5, 0.377 of Sisuogyuzarat(2-(methylaminomethyl)pyridine)platinum (I[) is obtained as a white powder. Original XW analytical value (C9[10N204 pt, ') Actual value (% ): C, 26, 66: H, 2, 46; N, 6.9
1 bullet value t%): C, 2G, 52; H, 2, 61
;N, 6.78I R":N';'(og')
Two 3160. 1720. 1650

[Brief explanation of the drawing]

Figures 1 to 11 show the infrared spectra of the following compounds.
, t. Figure 1: Cis-dibromo (2-ami/methylpyridine) platinum III Figure 2: Cis-dibromo (2-ami/methylpyridine) platinum (n) Figure 3: Cis-dibromo (2-ami/methylpyridine) platinum (n)
Platinum (■n Figure 4: cis-malonato(2-amino/methylpyridine)
Platinum (former No. 571: Cis-oxalate (2-aminomethylpyridine) Platinum (■) Figure 6: Cis-diglycolate (2-dimethylpyridine) Platinum (II) No. 71J: Cis-dioxamato (2-aminomethylpyridine) pyridine] platinum (!L) @8 figure: cis-(2-methylmalonato) (2-aminomethylpyridine) platinum(II) $9m cis-(2-hydroxymalonato J(2-
aminomethylpyridine) platinum (III Figure 10: cis-
(2-ethylmalonato) (2-aminomethylpyridine)
Platinum (formerly?

Claims (1)

[Claims] ■ General formula (wherein R1 represents a hydrogen atom or a methyl group, Yl and Y2 are the same - t>L< are different, and a halogen atom,
N03 or a group represented by the formula R"COO-, or Yl and Y2 taken together to form an acid diSOa. :p030H or -○CIJ-+CHOH)m-fc
HR31z-〇〇〇- R2 is a hydroxyftt 4% lower alkyl group, carbamoyl group or acetyl41 R3 is a hydrogen atom or a lower alkyl group 1m and n represent an integer of 0.1 or 2. However, it is assumed that vm and n satisfy the relationship 0≦+n+n≦2. ] An organic platinum complex represented by . 2. General formula % formula %) (However, 1M represents alkali gold 1^, and X represents l\\rogen atom.) A compound represented by the general formula and the general formula (However, R1 represents a hydrogen atom or a methyl group.) By reacting with a compound represented by the general formula (where R and X have the same meanings as above. and a compound represented by the general formula (where y3 and Y4 are the same and represent NOs), or Y3 and Y4 together represent a group represented by the formula ':SO4, and R1 has the same meaning as above) or a compound represented by the general formula (wherein R1 has the same meaning as above) and an alkali metal halide/hydrogen phosphate dialkali metal 0 formula R"C00M" (however, R2 is a hydroxy-substituted lower alkyl group, represents a carbamoyl group or acetyl group, M/ represents an alkali metal.] or M", -
0CO-(CHOH)a+-(CHR”)n-COO
M' (However, RF represents a hydrogen atom or a lower alkyl group, M" represents an alkali metal, and 1m and n are 0.l.
or represents an integer of 2. However, m and n are 06m -)-
It is assumed that the relationship n≦2 is satisfied. ] by reacting with a compound represented by the general formula [however, y5 and Y6 are different from each other] 1
0 Gen atom, N03, or a group represented by the formula R2COO-, or a group in which Y5 and Y6 are combined into the formula %, R", R",, R3, m and n
has the same meaning as above and 14-. ) (where yl and Y2 are the same or different from each other, represent a halogen atom, N03 or a group represented by the formula R2C0o-, or Y' and Y2 are integral represents a group represented by the formula %, and Fl', R" a R3+
m and n have the same meanings as above. A method for producing an organic platinum complex represented by J.