HU188035B - Process for producing new plantinum-diamine complex - Google Patents

Process for producing new plantinum-diamine complex Download PDF

Info

Publication number: HU188035B
Authority: HU; Hungary
Prior art keywords: formula; compound; defined above; cis; platinum
Prior art date: 1982-10-21

Application number

HU833623A

Other languages

English (en)

Hungarian (hu)

Inventor

Francois Berbeek

Jan Berg

Eric J Bulten

Original Assignee

Nederlandse Centrale Organisatie Voor Toegapastnatuurwetenschappelijk Ondorzoek,Nl

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.)

1982-10-21

Filing date

1983-10-20

Publication date

1986-03-28

1983-10-20 Application filed by Nederlandse Centrale Organisatie Voor Toegapastnatuurwetenschappelijk Ondorzoek,Nl filed Critical Nederlandse Centrale Organisatie Voor Toegapastnatuurwetenschappelijk Ondorzoek,Nl

1986-03-28 Publication of HU188035B publication Critical patent/HU188035B/hu

Links

238000000034 method Methods 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 46
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
238000002360 preparation method Methods 0.000 claims description 19
229910052697 platinum Inorganic materials 0.000 claims description 16
-1 platinum diamine Chemical class 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
206010028980 Neoplasm Diseases 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
235000011389 fruit/vegetable juice Nutrition 0.000 description 11
208000032839 leukemia Diseases 0.000 description 11
201000011510 cancer Diseases 0.000 description 9
229910001961 silver nitrate Inorganic materials 0.000 description 9
239000000706 filtrate Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
231100000417 nephrotoxicity Toxicity 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
229910021607 Silver chloride Inorganic materials 0.000 description 5
239000008280 blood Substances 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
210000003734 kidney Anatomy 0.000 description 5
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 5
231100000331 toxic Toxicity 0.000 description 5
230000002588 toxic effect Effects 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
208000028018 Lymphocytic leukaemia Diseases 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
229940045985 antineoplastic platinum compound Drugs 0.000 description 4
208000003747 lymphoid leukemia Diseases 0.000 description 4
150000003058 platinum compounds Chemical class 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 3
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
201000008228 Ependymoblastoma Diseases 0.000 description 2
206010014968 Ependymoma malignant Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
230000001093 anti-cancer Effects 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
208000029340 primitive neuroectodermal tumor Diseases 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
PJIBBTJBVQZPKJ-UHFFFAOYSA-N 1-trimethylsilylpropane-1-sulfonic acid Chemical compound CCC([Si](C)(C)C)S(O)(=O)=O PJIBBTJBVQZPKJ-UHFFFAOYSA-N 0.000 description 1
XZVBUSAPGMMCSW-UHFFFAOYSA-L 2-amino-3-methyl-4h-imidazol-5-one;dichloroplatinum Chemical compound Cl[Pt]Cl.CN1CC(=O)N=C1N.CN1CC(=O)N=C1N XZVBUSAPGMMCSW-UHFFFAOYSA-L 0.000 description 1
JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
206010067482 No adverse event Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010062237 Renal impairment Diseases 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
229910021612 Silver iodide Inorganic materials 0.000 description 1
XZAHJRZBUWYCBM-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1(CN)CCCCC1 XZAHJRZBUWYCBM-UHFFFAOYSA-N 0.000 description 1
PTGRNMGGKQUEGN-UHFFFAOYSA-N [Pt+2].NCC1CCCCC1 Chemical compound [Pt+2].NCC1CCCCC1 PTGRNMGGKQUEGN-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 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
229960004316 cisplatin Drugs 0.000 description 1
125000004367 cycloalkylaryl group Chemical group 0.000 description 1
CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
238000010562 histological examination Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002496 iodine Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100001095 no nephrotoxicity Toxicity 0.000 description 1
230000008520 organization Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000012925 reference material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
229940045105 silver iodide Drugs 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
231100000816 toxic dose Toxicity 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HU833623A 1982-10-21 1983-10-20 Process for producing new plantinum-diamine complex HU188035B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL8204067A NL8204067A (nl)	1982-10-21	1982-10-21	Platina-diaminecomplexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een dergelijk platinadiaminecomplex voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel.

Publications (1)

Publication Number	Publication Date
HU188035B true HU188035B (en)	1986-03-28

Family

ID=19840444

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU833623A HU188035B (en)	1982-10-21	1983-10-20	Process for producing new plantinum-diamine complex

Country Status (28)

Country	Link
JP (1)	JPS5993091A (cs)
KR (1)	KR910002536B1 (cs)
AT (1)	AT390610B (cs)
AU (1)	AU562964B2 (cs)
BE (1)	BE898058A (cs)
CA (1)	CA1229618A (cs)
CH (1)	CH658244A5 (cs)
CS (1)	CS242888B2 (cs)
DD (1)	DD217522A5 (cs)
DE (1)	DE3337333A1 (cs)
DK (2)	DK483083A (cs)
ES (1)	ES526670A0 (cs)
FI (1)	FI76351C (cs)
FR (1)	FR2534907B1 (cs)
GB (1)	GB2128615B (cs)
GR (1)	GR79652B (cs)
HU (1)	HU188035B (cs)
IE (1)	IE56124B1 (cs)
IT (1)	IT1169858B (cs)
LU (1)	LU85054A1 (cs)
NL (1)	NL8204067A (cs)
NO (1)	NO171276C (cs)
NZ (1)	NZ206018A (cs)
PH (1)	PH24077A (cs)
PT (1)	PT77542B (cs)
SE (1)	SE8305783L (cs)
YU (1)	YU43554B (cs)
ZA (1)	ZA837857B (cs)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4786725A (en) *	1982-06-28	1988-11-22	Engelhard Corporation	Solubilized platinum (II) complexes
US4661516A (en) *	1983-06-20	1987-04-28	Research Corporation	Diaminocyclohexane platinum complexes
US4758588A (en) *	1983-06-20	1988-07-19	Research Corporation Technologies	Diaminocyclohexane platinum complexes
EP0169645A1 (en) *	1984-06-27	1986-01-29	Johnson Matthey Public Limited Company	Platinum co-ordination compounds
DE3432320A1 (de) *	1984-09-03	1986-03-13	Behringwerke Ag, 3550 Marburg	Cis-platin-komplexe mit einem pentaerythritderivat als liganden, verfahren zu ihrer herstellung und diese verbindungen enthaltendes pharmazeutisches mittel
HU193809B (en) *	1984-09-12	1987-12-28	Chugai Pharmaceutical Co Ltd	Process for producing new platinum complexes
US4737589A (en) *	1985-08-27	1988-04-12	Nippon Kayaku Kabushiki Kaisha	Platinum Complexes
US4760157A (en) *	1986-01-31	1988-07-26	American Cyanamid Company	(2,2,-bis(aminomethyl)-1,3-propanediol-N,N')platinum complexes
US4880790A (en) *	1986-01-31	1989-11-14	American Cyanamid Company	(Gem-heterocyclodimethanamine-N,N')platinum complexes
DE3630497A1 (de) *	1986-09-08	1988-03-10	Behringwerke Ag	Cis-platin-komplexe, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel
ATE53217T1 (de) *	1986-10-03	1990-06-15	Asta Pharma Ag	Diamin-platin (ii)-komplexverbindungen mit einem hydroxylierten 2-phenyl-indolring.
JPS63203692A (ja) *	1987-02-19	1988-08-23	Nippon Kayaku Co Ltd	新規白金錯体
AT390065B (de) *	1987-10-08	1990-03-12	Behringwerke Ag	Cis-platin-komplexe, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel
NL8802149A (nl) *	1988-08-31	1990-03-16	Tno	Platina-(iv)diaminecomplex, werkwijze voor het bereiden van deze verbinding, preparaat met anti-tumor werking, dat ten minste een platinaverbinding bevat, alsmede gevormde preparaten met anti-tumor werking.
NL8802150A (nl) *	1988-08-31	1990-03-16	Tno	Platina-(ii)-diaminecomplex, werkwijze voor het bereiden van deze verbinding, preparaat met anti-tumor werking, dat deze verbinding bevat, alsmede gevormde preparaten met anti-tumor werking.
CN102924528B (zh) *	2012-10-29	2015-04-15	东南大学	抗肿瘤二价铂配合物以及该配合物和其配体的制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4115418A (en) *	1976-09-02	1978-09-19	Government Of The United States Of America	1,2-diaminocyclohexane platinum (ii) complexes having antineoplastic activity
US4206226A (en) *	1977-08-29	1980-06-03	The United States Of America As Represented By The Department Of Health, Education And Welfare	Use of 4-carboxy-phthalato-(1,2-diaminocyclohexane)-platinum(II) and alkali metal salts thereof in alleviating L1210 murine leukemia
NL189358C (nl) *	1978-07-06	1993-03-16	Tno	Werkwijze voor het bereiden van een geneesmiddel voor de behandeling van kanker, alsmede een van een 1,3-alkaandiamine afgeleid platina-diamminecomplex.
NL7807334A (nl) *	1978-07-06	1980-01-08	Tno	Platina-diaminecomplexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een genees- middel met toepassing van een dergelijk platina-dia- minecomplex voor de behandeling van kanker, alsmede al- dus verkregen gevormd geneesmiddel.
US4322362A (en) *	1980-07-28	1982-03-30	Bristol-Myers Company	Salts of 2-hydroxymalonate platinum complexes
NZ197104A (en) *	1980-05-27	1984-05-31	Bristol Myers Co	Soluble ammonium and sodium salts of 2-hydroxymalonato platinum ii derivatives

1982
- 1982-10-21 NL NL8204067A patent/NL8204067A/nl not_active Application Discontinuation
1983
- 1983-10-13 DE DE19833337333 patent/DE3337333A1/de not_active Ceased
- 1983-10-18 AU AU20275/83A patent/AU562964B2/en not_active Ceased
- 1983-10-19 CA CA000439308A patent/CA1229618A/en not_active Expired
- 1983-10-19 IT IT23359/83A patent/IT1169858B/it active
- 1983-10-20 YU YU2107/83A patent/YU43554B/xx unknown
- 1983-10-20 DK DK483083A patent/DK483083A/da not_active Application Discontinuation
- 1983-10-20 AT AT0373083A patent/AT390610B/de not_active IP Right Cessation
- 1983-10-20 IE IE2459/83A patent/IE56124B1/en not_active IP Right Cessation
- 1983-10-20 GR GR72754A patent/GR79652B/el unknown
- 1983-10-20 SE SE8305783A patent/SE8305783L/ not_active Application Discontinuation
- 1983-10-20 GB GB08328084A patent/GB2128615B/en not_active Expired
- 1983-10-20 DD DD83255826A patent/DD217522A5/de not_active IP Right Cessation
- 1983-10-20 NZ NZ206018A patent/NZ206018A/en unknown
- 1983-10-20 FR FR8316715A patent/FR2534907B1/fr not_active Expired
- 1983-10-20 PT PT77542A patent/PT77542B/pt unknown
- 1983-10-20 FI FI833842A patent/FI76351C/fi not_active IP Right Cessation
- 1983-10-20 LU LU85054A patent/LU85054A1/xx unknown
- 1983-10-20 CH CH5718/83A patent/CH658244A5/de not_active IP Right Cessation
- 1983-10-20 HU HU833623A patent/HU188035B/hu not_active IP Right Cessation
- 1983-10-20 NO NO833825A patent/NO171276C/no unknown
- 1983-10-21 JP JP58196286A patent/JPS5993091A/ja active Granted
- 1983-10-21 PH PH29726A patent/PH24077A/en unknown
- 1983-10-21 KR KR1019830004987A patent/KR910002536B1/ko not_active IP Right Cessation
- 1983-10-21 ES ES526670A patent/ES526670A0/es active Granted
- 1983-10-21 BE BE0/211755A patent/BE898058A/nl not_active IP Right Cessation
- 1983-10-21 CS CS837752A patent/CS242888B2/cs unknown
- 1983-10-21 ZA ZA837857A patent/ZA837857B/xx unknown
1992
- 1992-06-09 DK DK075592A patent/DK75592A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2534907A1 (fr)	1984-04-27
IE832459L (en)	1984-04-21
IE56124B1 (en)	1991-04-24
GB8328084D0 (en)	1983-11-23
LU85054A1 (cs)	1984-03-22
NL8204067A (nl)	1984-05-16
JPS5993091A (ja)	1984-05-29
NO171276C (no)	1993-02-17
DD217522A5 (de)	1985-01-16
AU562964B2 (en)	1987-06-25
GR79652B (cs)	1984-10-31
FR2534907B1 (fr)	1988-08-19
SE8305783D0 (sv)	1983-10-20
DE3337333A1 (de)	1984-04-26
SE8305783L (sv)	1984-04-22
NZ206018A (en)	1986-02-21
ATA373083A (de)	1989-11-15
FI833842A0 (fi)	1983-10-20
FI833842A (fi)	1984-04-22
ES8406498A1 (es)	1984-07-01
PT77542A (en)	1983-11-01
IT1169858B (it)	1987-06-03
DK75592D0 (da)	1992-06-09
IT8323359A0 (it)	1983-10-19
PH24077A (en)	1990-03-05
FI76351B (fi)	1988-06-30
JPH0244479B2 (cs)	1990-10-04
CA1229618A (en)	1987-11-24
KR840006492A (ko)	1984-11-30
KR910002536B1 (ko)	1991-04-23
FI76351C (fi)	1988-10-10
ZA837857B (en)	1984-06-27
ES526670A0 (es)	1984-07-01
CH658244A5 (de)	1986-10-31
YU43554B (en)	1989-08-31
PT77542B (en)	1986-02-12
YU210783A (en)	1986-08-31
NO171276B (no)	1992-11-09
AT390610B (de)	1990-06-11
DK483083D0 (da)	1983-10-20
NO833825L (no)	1984-04-24
CS775283A2 (en)	1985-08-15
DK75592A (da)	1992-06-09
DK483083A (da)	1984-04-22
CS242888B2 (en)	1986-05-15
AU2027583A (en)	1984-05-03
GB2128615A (en)	1984-05-02
GB2128615B (en)	1986-07-16
BE898058A (nl)	1984-04-24

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
US4562275A (en)	1985-12-31	Antitumor platinum complexes
EP0193936B1 (en)	1989-05-31	Liposoluble platinum (ii) complex and preparation thereof
HU188035B (en)	1986-03-28	Process for producing new plantinum-diamine complex
CS239911B2 (en)	1986-01-16	Processing of complexed diamino platinum
JPH036156B2 (cs)	1991-01-29
KR910009823B1 (ko)	1991-11-30	백금착물(白金錯物)
US5132323A (en)	1992-07-21	1,2-diaminocyclohexane-platinum complexes with antitumor activity
US4687780A (en)	1987-08-18	Anti-tumor compounds of platinum
EP0115929A1 (en)	1984-08-15	Novel organic platinum complex and process for the preparation thereof
US5028727A (en)	1991-07-02	Platinum-(IV)-diamine complex
US4739087A (en)	1988-04-19	Antineoplastic platinum complexes
US5008419A (en)	1991-04-16	Novel platinum complex
FI83086C (fi)	1991-05-27	Foerfarande foer framstaellning av komplex med tumormotverkande effekt.
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
GB2134103A (en)	1984-08-08	Novel organic platinum complex and process for the preparation thereof
CA1196004A (en)	1985-10-29	Platinum-diamine complexes, a method for the preparation thereof, a method for the preparation of a medicine using such a platinum-diamine complex for the treatment of cancer as well as a medicine thus formed
KR840000800B1 (ko)	1984-06-12	백금 디아민 착염의 제조방법
JPH08113583A (ja)	1996-05-07	抗腫瘍性白金（ｉｖ）錯体

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1994-07-28	HMM4	Cancellation of final prot. due to non-payment of fee