CA1196004A - Complexes de platine-diammine, methode pour les preparer, methode de preparation d'un medicament a base de tels complexes pour le traitement du cancer, et le medicament ainsi forme - Google Patents

Complexes de platine-diammine, methode pour les preparer, methode de preparation d'un medicament a base de tels complexes pour le traitement du cancer, et le medicament ainsi forme

Info

Publication number: CA1196004A
Authority: CA; Canada
Prior art keywords: platinum; cis; formula; aminomethyl; carbon atoms
Prior art date: 1982-10-08
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

CA000413154A

Other languages

English (en)

Inventor

Jan Berg

Eric J. Bulten

Francois Verbeek

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.)

Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO

Original Assignee

Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO

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.)

1982-10-08

Filing date

1982-10-08

Publication date

1985-10-29

1982-10-08 Application filed by Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO filed Critical Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO

1982-10-08 Priority to CA000413154A priority Critical patent/CA1196004A/fr

1985-10-29 Application granted granted Critical

1985-10-29 Publication of CA1196004A publication Critical patent/CA1196004A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 38
206010028980 Neoplasm Diseases 0.000 title abstract description 13
201000011510 cancer Diseases 0.000 title abstract description 11
238000011282 treatment Methods 0.000 title abstract description 11
238000002360 preparation method Methods 0.000 title abstract description 5
239000003814 drug Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 37
229910001868 water Inorganic materials 0.000 claims description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000000460 chlorine Substances 0.000 claims description 22
239000000243 solution Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
ODBLHEXUDAPZAU-UHFFFAOYSA-N isocitric acid Chemical class OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 claims description 8
-1 silver halide Chemical class 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 6
229910021653 sulphate ion Inorganic materials 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
125000000129 anionic group Chemical group 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical group [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
150000007942 carboxylates Chemical group 0.000 claims description 4
150000004985 diamines Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical group [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 4
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 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
229910044991 metal oxide Chemical group 0.000 claims description 3
150000004706 metal oxides Chemical group 0.000 claims description 3
125000005498 phthalate group Chemical class 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
238000009877 rendering Methods 0.000 claims 5
150000001242 acetic acid derivatives Chemical group 0.000 claims 2
125000002346 iodo group Chemical group I* 0.000 claims 2
150000002690 malonic acid derivatives Chemical group 0.000 claims 2
PQTLYDQECILMMB-UHFFFAOYSA-L platinum(2+);sulfate Chemical compound [Pt+2].[O-]S([O-])(=O)=O PQTLYDQECILMMB-UHFFFAOYSA-L 0.000 claims 2
BQBCAHILGYZBQP-UHFFFAOYSA-N sodium;platinum(2+) Chemical compound [Na+].[Pt+2] BQBCAHILGYZBQP-UHFFFAOYSA-N 0.000 claims 2
238000009835 boiling Methods 0.000 claims 1
231100000417 nephrotoxicity Toxicity 0.000 abstract description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 32
208000032839 leukemia Diseases 0.000 description 21
229910052697 platinum Inorganic materials 0.000 description 17
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 17
241000699670 Mus sp. Species 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
229910021607 Silver chloride Inorganic materials 0.000 description 5
239000008280 blood Substances 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
230000001093 anti-cancer Effects 0.000 description 4
125000003963 dichloro group Chemical group Cl* 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
210000003734 kidney Anatomy 0.000 description 4
150000003057 platinum Chemical class 0.000 description 4
231100000331 toxic Toxicity 0.000 description 4
230000002588 toxic effect Effects 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000007788 liquid Substances 0.000 description 3
AYTGUZPQPXGYFS-UHFFFAOYSA-N urea nitrate Chemical compound NC(N)=O.O[N+]([O-])=O AYTGUZPQPXGYFS-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229940079593 drug Drugs 0.000 description 2
ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
208000003747 lymphoid leukemia Diseases 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
238000011160 research Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
206010003445 Ascites Diseases 0.000 description 1
238000011740 C57BL/6 mouse Methods 0.000 description 1
STVKWNWCRXIHBH-UHFFFAOYSA-N NC[Pt]C1CCCCC1 Chemical compound NC[Pt]C1CCCCC1 STVKWNWCRXIHBH-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
206010042674 Swelling Diseases 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
101100162169 Xenopus laevis adrm1-a gene Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
229940045985 antineoplastic platinum compound Drugs 0.000 description 1
238000011888 autopsy Methods 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
101150115304 cls-2 gene Proteins 0.000 description 1
UIESMAIMBNSQQX-UHFFFAOYSA-N cyclohexane platinum Chemical compound [Pt].C1CCCCC1 UIESMAIMBNSQQX-UHFFFAOYSA-N 0.000 description 1
KMEQMZMYKYCLMS-UHFFFAOYSA-N cyclohexane platinum(2+) Chemical compound [Pt+2].C1CCCCC1 KMEQMZMYKYCLMS-UHFFFAOYSA-N 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
238000010562 histological examination Methods 0.000 description 1
231100000268 induced nephrotoxicity Toxicity 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000008520 organization Effects 0.000 description 1
150000003058 platinum compounds Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
229910000367 silver sulfate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000413154A 1982-10-08 1982-10-08 Complexes de platine-diammine, methode pour les preparer, methode de preparation d'un medicament a base de tels complexes pour le traitement du cancer, et le medicament ainsi forme Expired CA1196004A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000413154A CA1196004A (fr)	1982-10-08	1982-10-08	Complexes de platine-diammine, methode pour les preparer, methode de preparation d'un medicament a base de tels complexes pour le traitement du cancer, et le medicament ainsi forme

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000413154A CA1196004A (fr)	1982-10-08	1982-10-08	Complexes de platine-diammine, methode pour les preparer, methode de preparation d'un medicament a base de tels complexes pour le traitement du cancer, et le medicament ainsi forme

Publications (1)

Publication Number	Publication Date
CA1196004A true CA1196004A (fr)	1985-10-29

Family

ID=4123747

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000413154A Expired CA1196004A (fr)	1982-10-08	1982-10-08	Complexes de platine-diammine, methode pour les preparer, methode de preparation d'un medicament a base de tels complexes pour le traitement du cancer, et le medicament ainsi forme

Country Status (1)

Country	Link
CA (1)	CA1196004A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2014028653A1 (fr) *	2012-08-14	2014-02-20	Northwestern University	Agents anti-cancéreux à base d'arsénoplatine
US9499574B2 (en)	2012-08-14	2016-11-22	Northwestern University	Arsenoplatin anti-cancer agents

1982
- 1982-10-08 CA CA000413154A patent/CA1196004A/fr not_active Expired

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2014028653A1 (fr) *	2012-08-14	2014-02-20	Northwestern University	Agents anti-cancéreux à base d'arsénoplatine
US9499574B2 (en)	2012-08-14	2016-11-22	Northwestern University	Arsenoplatin anti-cancer agents
US9725475B2 (en)	2012-08-14	2017-08-08	Northwestern University	Arsenoplatin anti-cancer agents
US10118938B2 (en)	2012-08-14	2018-11-06	Northwestern University	Arsenoplatin anti-cancer agents

Legal Events

Date	Code	Title	Description
2002-10-29	MKEX	Expiry

Publication	Publication Date	Title
US4410544A (en)	1983-10-18	Platinum-diamine complexes, a method for the preparation of a medicine using such a platinum-diamine complex for the treatment of malignant tumor in mice
EP0155705B1 (fr)	1989-12-13	Complexe antitumeurs de platine
CA1154030A (fr)	1983-09-20	Complexes de platine (iv)-diamine; methode pour les preparer; obtention d'un medicament a l'aide de ces complexes, utile dans le traitement du cancer et medicament moule ainsi fabrique
EP0001126B1 (fr)	1982-08-18	Complexes cis de platine (II) et de diamino-1,2-cyclohexane et composition pharmaceutique les contenant
US4466924A (en)	1984-08-21	Platinum-diamine complexes, a process for the preparation thereof, a process for the preparation of a medicine using such a platinum-diamine complex for the treatment of malignant tumors in mice as well as a medicine thus formed
EP0193936B1 (fr)	1989-05-31	Complexe de platine (II) liposoluble et sa préparation
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
US4661516A (en)	1987-04-28	Diaminocyclohexane platinum complexes
US4271085A (en)	1981-06-02	Cis-platinum (II) amine lactate complexes
CA1229618A (fr)	1987-11-24	Complexes platine-diamine, procede de preparation desdits complexes, procede de preparation d'un compose medical contenant ledit complexe platine- diamine pour le traitement ducancer ainsi que ledit compose
JPS6013795A (ja)	1985-01-24	ジアミノシクロヘキサン白金錯体
US4739087A (en)	1988-04-19	Antineoplastic platinum complexes
US4758588A (en)	1988-07-19	Diaminocyclohexane platinum complexes
GB2055377A (en)	1981-03-04	Cis-platinum(II) amine ascorbate complexes
US4831170A (en)	1989-05-16	Pharmaceutically active phospino-hydrocarbon-group VIII-metal complexes, antitumor compositions containing these complexes, and a process for preparing said compounds or antitumor compositions
US5037812A (en)	1991-08-06	Tumor cell growth-inhibiting pharmaceutical compositions containing phosphino-hydrocarbon-gold, silver or copper complexes
KR840000800B1 (ko)	1984-06-12	백금 디아민 착염의 제조방법
CA1218072A (fr)	1987-02-17	Bis(dicarboxylato)-palladates(ii) ioniques, agents anti-tumeurs
CA1219876A (fr)	1987-03-31	Complexes de bis(thiocyanato)palladium(ii)
JPS62246564A (ja)	1987-10-27	（ｇｅｍ−ヘテロシクロジメタンアミン−Ｎ，Ｎ’）白金錯塩
JPS5988499A (ja)	1984-05-22	白金−ジアミン錯体