CA1154785A - Complexes platine(ii)-ascorbate cis-amines - Google Patents

Complexes platine(ii)-ascorbate cis-amines

Info

Publication number: CA1154785A
Authority: CA; Canada
Prior art keywords: cis; ascorbate; integer; value; formula
Prior art date: 1979-06-20
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.): Expired

Application number

CA000353898A

Other languages

English (en)

Inventor

Eric W. Stern

Alan R. Amundsen

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.)

BASF Catalysts LLC

Original Assignee

Engelhard Corp

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.)

1979-06-20

Filing date

1980-06-12

Publication date

1983-10-04

1980-06-12 Application filed by Engelhard Corp filed Critical Engelhard Corp

1983-10-04 Application granted granted Critical

1983-10-04 Publication of CA1154785A publication Critical patent/CA1154785A/fr

Status Expired legal-status Critical Current

Links

-1 Cis-platinum(ii) amine ascorbate complexes Chemical class 0.000 title description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 84
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 44
125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims abstract description 34
150000001412 amines Chemical class 0.000 claims abstract description 18
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims abstract description 17
239000003446 ligand Substances 0.000 claims abstract description 15
150000003973 alkyl amines Chemical class 0.000 claims abstract description 6
229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 94
235000010323 ascorbic acid Nutrition 0.000 claims description 48
239000011668 ascorbic acid Substances 0.000 claims description 48
229940072107 ascorbate Drugs 0.000 claims description 46
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 27
238000000034 method Methods 0.000 claims description 21
229910000069 nitrogen hydride Inorganic materials 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
239000012736 aqueous medium Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 12
150000001449 anionic compounds Chemical class 0.000 claims description 9
229910001412 inorganic anion Inorganic materials 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims 4
229910001868 water Inorganic materials 0.000 abstract description 22
150000001875 compounds Chemical class 0.000 abstract description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
230000000259 anti-tumor effect Effects 0.000 abstract description 9
241001465754 Metazoa Species 0.000 abstract description 5
231100000419 toxicity Toxicity 0.000 abstract description 2
230000001988 toxicity Effects 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 17
241000699670 Mus sp. Species 0.000 description 16
150000000994 L-ascorbates Chemical class 0.000 description 12
206010028980 Neoplasm Diseases 0.000 description 12
229910052697 platinum Inorganic materials 0.000 description 12
239000000047 product Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
230000000694 effects Effects 0.000 description 11
239000000203 mixture Substances 0.000 description 11
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 11
238000012360 testing method Methods 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
235000010378 sodium ascorbate Nutrition 0.000 description 6
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 6
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
238000012216 screening Methods 0.000 description 5
229960005055 sodium ascorbate Drugs 0.000 description 5
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
229910002651 NO3 Inorganic materials 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
150000004985 diamines Chemical class 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
229910001961 silver nitrate Inorganic materials 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
206010003445 Ascites Diseases 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
231100000816 toxic dose Toxicity 0.000 description 3
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
208000006268 Sarcoma 180 Diseases 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229960005070 ascorbic acid Drugs 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
ZYZCZCHRQQZTHI-UHFFFAOYSA-N cyclohexane-1,1-diamine;platinum Chemical compound [Pt].NC1(N)CCCCC1 ZYZCZCHRQQZTHI-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000013641 positive control Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
238000012546 transfer Methods 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
FDMXADMEKAUMIV-NSCUHMNNSA-N (e)-prop-1-ene-1,2-diamine Chemical compound C\C(N)=C/N FDMXADMEKAUMIV-NSCUHMNNSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
239000004260 Potassium ascorbate Substances 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfate Natural products OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
UGQDIOUBRRLHMW-UHFFFAOYSA-N cyclohexane-1,1-diamine;platinum(2+) Chemical compound [Pt+2].NC1(N)CCCCC1 UGQDIOUBRRLHMW-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000003844 furanonyl group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
208000003747 lymphoid leukemia Diseases 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
235000019275 potassium ascorbate Nutrition 0.000 description 1
229940017794 potassium ascorbate Drugs 0.000 description 1
CONVKSGEGAVTMB-RXSVEWSESA-M potassium-L-ascorbate Chemical compound [K+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] CONVKSGEGAVTMB-RXSVEWSESA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
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 1
241000894007 species Species 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)

CA000353898A 1979-06-20 1980-06-12 Complexes platine(ii)-ascorbate cis-amines Expired CA1154785A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5084379A	1979-06-20	1979-06-20
US050,843		1979-06-20

Publications (1)

Publication Number	Publication Date
CA1154785A true CA1154785A (fr)	1983-10-04

Family

ID=21967817

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000353898A Expired CA1154785A (fr)	1979-06-20	1980-06-12	Complexes platine(ii)-ascorbate cis-amines

Country Status (7)

Country	Link
JP (1)	JPS5645468A (fr)
AU (1)	AU534866B2 (fr)
CA (1)	CA1154785A (fr)
DE (1)	DE3022957A1 (fr)
FR (1)	FR2459247A1 (fr)
GB (1)	GB2055377B (fr)
IT (1)	IT1149203B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3108842A1 (de) *	1981-03-09	1982-09-16	Basf Ag, 6700 Ludwigshafen	Cis-platin(ii)-komplexe mit saccharid-derivaten als liganden
DE3405611A1 (de) *	1983-02-18	1984-08-23	Degussa Ag, 6000 Frankfurt	(1,2-diphenyl-ethylendiamin)-platin(ii)-komplexverbindungen
US4598091A (en) *	1983-02-18	1986-07-01	Degussa Aktiengesellschaft	(1,2-diphenyl)-ethylenediamine)-platinum (II) complex compounds
US4758588A (en) *	1983-06-20	1988-07-19	Research Corporation Technologies	Diaminocyclohexane platinum complexes
US4661516A (en) *	1983-06-20	1987-04-28	Research Corporation	Diaminocyclohexane platinum complexes
DK301684A (da) *	1983-06-20	1984-12-21	Research Corp	Diaminocyklohexanplatinkomplekser
NZ214504A (en) *	1984-12-17	1988-07-28	American Cyanamid Co	Platinum/saccharide complexes and pharmaceutical compositions
US4912100A (en) *	1986-10-15	1990-03-27	Toray Industries, Inc.	Platinum complex, process for preparing same and antitumor agent

1980
- 1980-06-12 CA CA000353898A patent/CA1154785A/fr not_active Expired
- 1980-06-14 JP JP7963180A patent/JPS5645468A/ja active Pending
- 1980-06-18 GB GB8019974A patent/GB2055377B/en not_active Expired
- 1980-06-18 IT IT49002/80A patent/IT1149203B/it active
- 1980-06-18 FR FR8013508A patent/FR2459247A1/fr active Granted
- 1980-06-18 AU AU59367/80A patent/AU534866B2/en not_active Ceased
- 1980-06-19 DE DE19803022957 patent/DE3022957A1/de active Granted

Also Published As

Publication number	Publication date
GB2055377B (en)	1983-07-06
JPS5645468A (en)	1981-04-25
AU5936780A (en)	1981-01-08
DE3022957C2 (fr)	1991-03-21
DE3022957A1 (de)	1981-01-22
IT8049002A0 (it)	1980-06-18
FR2459247A1 (fr)	1981-01-09
IT1149203B (it)	1986-12-03
GB2055377A (en)	1981-03-04
AU534866B2 (en)	1984-02-16
FR2459247B1 (fr)	1984-01-20

Legal Events

Date	Code	Title	Description
2000-10-04	MKEX	Expiry

Publication	Publication Date	Title
US4225529A (en)	1980-09-30	Compositions containing platinum
US4115418A (en)	1978-09-19	1,2-diaminocyclohexane platinum (ii) complexes having antineoplastic activity
CA1263867A (fr)	1989-12-12	Complexes de platine (ii) solubilises
CA1134378A (fr)	1982-10-26	Complexes de cis-platine(ii) amino-lactate
Hoeschele et al.	1994	Synthesis, structural characterization, and antitumor properties of a novel class of large-ring platinum (II) chelate complexes incorporating the cis-1, 4-diaminocyclohexane ligand in a unique locked boat conformation
JPH0244838B2 (fr)	1990-10-05
SE439921B (sv)	1985-07-08	Nya platina(iv)diamin-komplex, sett att framstella dessa komplex och ett lekemedel till anvendning for behandling av cancer
US4234500A (en)	1980-11-18	Ethylenediamine platinum(II) and 1,2-diamino-cyclohexane platinum(II) pyrophosphate complexes
US4657927A (en)	1987-04-14	Malonato platinum compounds
KR910002536B1 (ko)	1991-04-23	플라티늄-디아민 착화물의 제조방법
KR910009823B1 (ko)	1991-11-30	백금착물(白金錯物)
EP0111388A2 (fr)	1984-06-20	Composés du platine ou du palladium à propriétés thérapeutiques et leur préparation
JP2749295B2 (ja)	1998-05-13	高分子白金錯化合物、その製造方法及びそれを有効成分とする抗ガン剤
GB2055377A (en)	1981-03-04	Cis-platinum(II) amine ascorbate complexes
US4457926A (en)	1984-07-03	Cis-Platinum(II) amine ascorbate complexes
US4234499A (en)	1980-11-18	Cis-diammireplatinum(II) organophosphate complexes
US4687780A (en)	1987-08-18	Anti-tumor compounds of platinum
US4291027A (en)	1981-09-22	Method for treating tumors with ethylenediamine platinum (II) and 1,2-diaminocyclohexane-platinum (II) pyrophosphate complexes
US4462998A (en)	1984-07-31	Method of using a cis-platinum(II) amine ascorbate
JPH02108693A (ja)	1990-04-20	白金（４）ジアミン錯体
Gill	1984	Structure activity relationship of antitumor palladium complexes
US4291023A (en)	1981-09-22	Method for treating tumors using cis-diammineplatinum (II) organophosphate complexes
KR890004351B1 (ko)	1989-10-31	항 종양성 백금 착체의 제조방법
CA2070497C (fr)	1999-05-25	Complexe a base de platine (ii) et agent antitumoral
EP0290169A2 (fr)	1988-11-09	Complexes de diamine platine avec des ligands phosphonocarboxylates ou phosphonocarboxylate substitués comme agents anti-tumeurs