BE890209A - PLATINUM COORDINATION COMPOUND - Google Patents
PLATINUM COORDINATION COMPOUND Download PDFInfo
- Publication number
- BE890209A BE890209A BE0/205862A BE205862A BE890209A BE 890209 A BE890209 A BE 890209A BE 0/205862 A BE0/205862 A BE 0/205862A BE 205862 A BE205862 A BE 205862A BE 890209 A BE890209 A BE 890209A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- coordination compound
- platinum coordination
- compound
- adduct
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title description 9
- 229910052697 platinum Inorganic materials 0.000 title description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000002424 x-ray crystallography 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
JOHNSON MATTHEY PUBLIC LIMITED COMPANY
Inventeurs:Paul Cedric HYDES et Derek Ronald HEPBURN <EMI ID=1.1>
composé de coordination du platiné possédant la structure suivante :
<EMI ID=2.1>
<EMI ID=3.1>
<EMI ID=4.1>
<EMI ID=5.1>
<EMI ID=6.1>
<EMI ID=7.1>
B sont identiques ou différents et représentent chacun des groupes d'aminés aliphatiques à chaîne ramifiée coordonnés avec Pt par l'intermédiaire de leurs atomes d'azote.
Dans ce brevet britannique, on décrit et revendique également une composition pour le traitement du cancer ou d'un néoplasme malin,, cette composition comprenant un composé de coordination du platine possédant la structure suivante :
<EMI ID=8.1>
<EMI ID=9.1>
tiques ou différents mais, de préférence ils représentent tous deux un groupe chlorure.9 cependant qu'ils peuvent également représenter un autre halogénure ou
<EMI ID=10.1> <EMI ID=11.1>
<EMI ID=12.1>
<EMI ID=13.1>
<EMI ID=14.1>
<EMI ID=15.1>
cependant qu'ils peuvent également être choisis panai
<EMI ID=16.1>
ques, de même que les groupes alkyle, aryle., alcaryle et. aralkyle substitués.
De préférence, le platine est présent sous
<EMI ID=17.1>
deux coordinats hydroxy et deux coordinats halogénure.-.
Bien que des groupes R autres que 1[deg.] atome d'hydrogène ne soient normalement pas préférés, on peut
<EMI ID=18.1>
kyle inférieurs tels que le groupe méthyle ou le groupe éthyle, ou un groupe solubilisant tel qu'un groupe d'acide suif oni que. Des groupes solubilisants tels que
<EMI ID=19.1>
et de leurs sels, par exemple les sels de /sodium, 'de potassium ou de lithium sont parfois appropriés comme substituants lorsque les conditions cliniques exigent une haute solubilité,
<EMI ID=20.1>
<EMI ID=21.1>
<EMI ID=22.1> génure (un chlorure, un bromure, un iodure ou un fluoru-
<EMI ID=23.1>
<EMI ID=24.1>
<EMI ID=25.1>
<EMI ID=26.1>
<EMI ID=27.1>
<EMI ID=28.1>
<EMI ID=29.1>
filtrer, laver le résidu avec de l'eau et de l'éther, puis séchiez. l'air. On recristallise le produit brut
<EMI ID=30.1>
<EMI ID=31.1>
cristallographie radiographique d'un seul cristal, on
<EMI ID=32.1>
Des travaux ultérieurs ont démontré que le complexe préparé comme décrit ci-
<EMI ID=33.1>
<EMI ID=34.1>
<EMI ID=35.1>
<EMI ID=36.1>
est désavantageuse point. de vue pharmacologique*
<EMI ID=37.1> <EMI ID=38.1>
<EMI ID=39.1>
En conséquence, jusqu'à présenta on a considéré qu'il
<EMI ID=40.1>
<EMI ID=41.1>
quantités décelables de peroxyde d'hydrogène ou d'autres molécules de solvatatioh.
<EMI ID=42.1>
<EMI ID=43.1>
Le compose suivant la présente invention est
<EMI ID=44.1>
sous une forme pratiquement pure et possédant -la $truc-
<EMI ID=45.1>
<EMI ID=46.1>
ce procédé comprenant les étapes consistant
<EMI ID=47.1> <EMI ID=48.1>
acétamide dans le procédé de l'invention en vue d'obtenir le produit d'addition intermédiaire 1:1 permettait
<EMI ID=49.1>
des recristallisations directes effectuées en utilisant
<EMI ID=50.1>
<EMI ID=51.1>
<EMI ID=52.1>
<EMI ID=53.1>
<EMI ID=54.1>
<EMI ID=55.1>
<EMI ID=56.1>
<EMI ID=57.1>
Le produit d'addition intermédiaire 1:1 de
<EMI ID=58.1>
<EMI ID=59.1>
risée, cette composition étant également stable*
<EMI ID=60.1>
sation de l'invention en se référant à l'exemple de
<EMI ID=61.1>
<EMI ID=62.1> <EMI ID=63.1>
peroxyde d'hydrogène aqueux* ;fait' bouillir
<EMI ID=64.1>
<EMI ID=65.1>
<EMI ID=66.1> <EMI ID=67.1>
<EMI ID=68.1>
Analyse élémentaire :
<EMI ID=69.1>
spectre d'absorption des rayons infra- <EMI ID=70.1>
ours:
<EMI ID=71.1> <EMI ID=72.1>
dessus) à travers un lit de gel de silice (70-230 mail-
<EMI ID=73.1>
éventuellement présentes,
<EMI ID=74.1>
<EMI ID=75.1>
<EMI ID=76.1>
quels : <EMI ID=77.1>
<EMI ID=78.1>
d'hydrogène suivant la technique antérieure ; la figure 2 est un spectre d'absorption des rayons infrarouges du nouveau produit d'addition de diméthylacétamide ; la figure 3 est un spectre d'absorption des rayons infrarouges du composé suivant l'invention la figure 4 est un diagramme de diffraction radiographique de poudre du produit d'addition de peroxyde d'hydrogène suivant la technique antérieure; la figure 5 est un diagramme de diffraction radiographique de poudre du nouveau produit d'addition <EMI ID=79.1> la figure 6 est un diagramme de diffraction radiographique de poudre du composé suivant 1[deg.] invention <EMI ID=80.1> de différents composés la figure 8 représente les résultats de l'analyse gravimétrique -thermique de différents composes la figure 9 est une vue stéréoscopique du <EMI ID=81.1>
<EMI ID=82.1>
<EMI ID=83.1>
<EMI ID=84.1>
<EMI ID=85.1>
<EMI ID=86.1>
Forme physique : Poudre jaune (pour toutes les charges)
<EMI ID=87.1> <EMI ID=88.1>
Analyse élémentaire :
<EMI ID=89.1>
<EMI ID=90.1>
en masse) : Pureté (%)
<EMI ID=91.1>
Teneurs en impuretés :
<EMI ID=92.1>
<EMI ID=93.1>
sorption des rayons infrarouges de différents composés, <EMI ID=94.1> figures 4; 5 et 6, on aboutit à la même conclus ions-, <EMI ID=95.1>
<EMI ID=96.1>
<EMI ID=97.1>
0
<EMI ID=98.1> <EMI ID=99.1>
<EMI ID=100.1>
<EMI ID=101.1>
gaz/liquide.
Pour un intervalle donnée une réponse sem-
<EMI ID=102.1>
<EMI ID=103.1>
<EMI ID=104.1>
En figure 8 qui illustre les résultats de l'analyse gravimétrique thermique de différents composés, les légendes ont les significations suivantes
La ligne 1 se rapporte à un composé d'un produit d'addi-
<EMI ID=105.1>
la ligne 3 se rapporte à un composé suivant l'invention.
Pour faciliter la présentation, les tracés
<EMI ID=106.1>
poids".
On constate que la ligne 1 indique une plus
<EMI ID=107.1>
<EMI ID=108.1>
2 et 3 indiquent pratiquement la même perte. de. poids
<EMI ID=109.1> <EMI ID=110.1>
<EMI ID=111.1>
duit d'addition de peroxyde d'hydrogène de la technique antérieure <EMI ID=112.1>
<EMI ID=113.1>
<EMI ID=114.1>
<EMI ID=115.1>
<EMI ID=116.1>
<EMI ID=117.1>
<EMI ID=118.1>
<EMI ID=119.1>
<EMI ID=120.1>
<EMI ID=121.1>
<EMI ID=122.1>
JOHNSON MATTHEY PUBLIC LIMITED COMPANY
Inventors: Paul Cedric HYDES and Derek Ronald HEPBURN <EMI ID = 1.1>
platinum coordination compound with the following structure:
<EMI ID = 2.1>
<EMI ID = 3.1>
<EMI ID = 4.1>
<EMI ID = 5.1>
<EMI ID = 6.1>
<EMI ID = 7.1>
B are the same or different and each represents groups of branched chain aliphatic amines coordinated with Pt via their nitrogen atoms.
This British patent also describes and claims a composition for the treatment of cancer or of a malignant neoplasm, this composition comprising a platinum coordination compound having the following structure:
<EMI ID = 8.1>
<EMI ID = 9.1>
ticks or different but, preferably, they both represent a chloride group. 9 however they can also represent another halide or
<EMI ID = 10.1> <EMI ID = 11.1>
<EMI ID = 12.1>
<EMI ID = 13.1>
<EMI ID = 14.1>
<EMI ID = 15.1>
however they can also be chosen panai
<EMI ID = 16.1>
as well as the alkyl, aryl, alkaryl and. substituted aralkyl.
Preferably, platinum is present in
<EMI ID = 17.1>
two hydroxy and two halide ligands.
Although R groups other than 1 [deg.] Hydrogen atom are not normally preferred, it is possible to
<EMI ID = 18.1>
lower kyle such as methyl group or ethyl group, or a solubilizing group such as a sulfuric acid group. Solubilizing groups such as
<EMI ID = 19.1>
and their salts, for example the sodium, potassium or lithium salts are sometimes suitable as substituents when the clinical conditions require high solubility,
<EMI ID = 20.1>
<EMI ID = 21.1>
<EMI ID = 22.1> genide (a chloride, a bromide, an iodide or a fluoride-
<EMI ID = 23.1>
<EMI ID = 24.1>
<EMI ID = 25.1>
<EMI ID = 26.1>
<EMI ID = 27.1>
<EMI ID = 28.1>
<EMI ID = 29.1>
filter, wash the residue with water and ether, then dry. the air. We recrystallize the raw product
<EMI ID = 30.1>
<EMI ID = 31.1>
x-ray crystallography of a single crystal, we
<EMI ID = 32.1>
Subsequent work has demonstrated that the complex prepared as described above
<EMI ID = 33.1>
<EMI ID = 34.1>
<EMI ID = 35.1>
<EMI ID = 36.1>
is disadvantageous point. pharmacological *
<EMI ID = 37.1> <EMI ID = 38.1>
<EMI ID = 39.1>
Consequently, until now it has been considered that
<EMI ID = 40.1>
<EMI ID = 41.1>
detectable amounts of hydrogen peroxide or other solvate molecules.
<EMI ID = 42.1>
<EMI ID = 43.1>
The compound according to the present invention is
<EMI ID = 44.1>
in a practically pure form and possessing -the $ thing-
<EMI ID = 45.1>
<EMI ID = 46.1>
this process comprising the steps of
<EMI ID = 47.1> <EMI ID = 48.1>
acetamide in the process of the invention in order to obtain the intermediate adduct 1: 1 allowed
<EMI ID = 49.1>
direct recrystallizations performed using
<EMI ID = 50.1>
<EMI ID = 51.1>
<EMI ID = 52.1>
<EMI ID = 53.1>
<EMI ID = 54.1>
<EMI ID = 55.1>
<EMI ID = 56.1>
<EMI ID = 57.1>
The 1: 1 intermediate adduct of
<EMI ID = 58.1>
<EMI ID = 59.1>
laughing, this composition also being stable *
<EMI ID = 60.1>
sation of the invention with reference to the example of
<EMI ID = 61.1>
<EMI ID = 62.1> <EMI ID = 63.1>
aqueous hydrogen peroxide *; boiled
<EMI ID = 64.1>
<EMI ID = 65.1>
<EMI ID = 66.1> <EMI ID = 67.1>
<EMI ID = 68.1>
Elementary analysis:
<EMI ID = 69.1>
infrared ray absorption spectrum <EMI ID = 70.1>
bear:
<EMI ID = 71.1> <EMI ID = 72.1>
above) through a bed of silica gel (70-230 mail-
<EMI ID = 73.1>
possibly present,
<EMI ID = 74.1>
<EMI ID = 75.1>
<EMI ID = 76.1>
which: <EMI ID = 77.1>
<EMI ID = 78.1>
hydrogen according to the prior art; Figure 2 is an infrared ray absorption spectrum of the new dimethylacetamide adduct; Figure 3 is an infrared ray absorption spectrum of the compound according to the invention Figure 4 is a radiographic powder diffraction diagram of the hydrogen peroxide adduct according to the prior art; Figure 5 is a radiographic powder diffraction diagram of the new adduct <EMI ID = 79.1> Figure 6 is a radiographic powder diffraction diagram of the following compound 1 [deg.] invention <EMI ID = 80.1> of different compounds figure 8 represents the results of the gravimetric-thermal analysis of different compounds figure 9 is a stereoscopic view of <EMI ID = 81.1>
<EMI ID = 82.1>
<EMI ID = 83.1>
<EMI ID = 84.1>
<EMI ID = 85.1>
<EMI ID = 86.1>
Physical form: Yellow powder (for all charges)
<EMI ID = 87.1> <EMI ID = 88.1>
Elementary analysis:
<EMI ID = 89.1>
<EMI ID = 90.1>
by mass): Purity (%)
<EMI ID = 91.1>
Impurity content:
<EMI ID = 92.1>
<EMI ID = 93.1>
sorption of infrared rays from different compounds, <EMI ID = 94.1> Figures 4; 5 and 6, we arrive at the same conclusion ions-, <EMI ID = 95.1>
<EMI ID = 96.1>
<EMI ID = 97.1>
0
<EMI ID = 98.1> <EMI ID = 99.1>
<EMI ID = 100.1>
<EMI ID = 101.1>
gas / liquid.
For a given interval a sem-
<EMI ID = 102.1>
<EMI ID = 103.1>
<EMI ID = 104.1>
In Figure 8 which illustrates the results of the thermal gravimetric analysis of different compounds, the legends have the following meanings
Line 1 refers to a compound of an additive product.
<EMI ID = 105.1>
line 3 relates to a compound according to the invention.
To facilitate the presentation, the plots
<EMI ID = 106.1>
weight".
We can see that line 1 indicates a more
<EMI ID = 107.1>
<EMI ID = 108.1>
2 and 3 indicate practically the same loss. of. weight
<EMI ID = 109.1> <EMI ID = 110.1>
<EMI ID = 111.1>
prior art hydrogen peroxide addition product <EMI ID = 112.1>
<EMI ID = 113.1>
<EMI ID = 114.1>
<EMI ID = 115.1>
<EMI ID = 116.1>
<EMI ID = 117.1>
<EMI ID = 118.1>
<EMI ID = 119.1>
<EMI ID = 120.1>
<EMI ID = 121.1>
<EMI ID = 122.1>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8028484 | 1980-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE890209A true BE890209A (en) | 1982-01-04 |
Family
ID=10515824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/205862A BE890209A (en) | 1980-09-03 | 1981-09-03 | PLATINUM COORDINATION COMPOUND |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5777694A (en) |
| KR (1) | KR890000640B1 (en) |
| BE (1) | BE890209A (en) |
| SU (2) | SU1256698A3 (en) |
| ZA (1) | ZA815852B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL71804A (en) * | 1983-05-10 | 1989-06-30 | Andrulis Res Corp | Bis-(platinum diamine)complexes and antitumor pharmaceutical compositions containing the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1578323A (en) * | 1976-02-26 | 1980-11-05 | Rustenburg Platinum Mines Ltd | Compositions containing platinum |
-
1981
- 1981-08-25 ZA ZA815852A patent/ZA815852B/en unknown
- 1981-09-02 KR KR1019810003274A patent/KR890000640B1/en active
- 1981-09-03 JP JP56137856A patent/JPS5777694A/en active Granted
- 1981-09-03 BE BE0/205862A patent/BE890209A/en not_active IP Right Cessation
-
1982
- 1982-05-03 SU SU823434800A patent/SU1256698A3/en active
- 1982-09-20 SU SU3495252A patent/SU1188179A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5777694A (en) | 1982-05-15 |
| ZA815852B (en) | 1982-08-25 |
| KR890000640B1 (en) | 1989-03-22 |
| JPH0349916B2 (en) | 1991-07-31 |
| KR830008543A (en) | 1983-12-10 |
| SU1188179A1 (en) | 1985-10-30 |
| SU1256698A3 (en) | 1986-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI87792B (en) | Tigogenin cellubioside octaacetate | |
| Arduengo III et al. | Electronic stabilization of nucleophilic carbenes | |
| CH651840A5 (en) | PLATINUM COORDINATION COMPOUND AND PREPARATION METHOD. | |
| FR2421884A1 (en) | PROCESS FOR THE PREPARATION OF MALEIMIDES SUBSTITUTES FOR NITROGEN | |
| US5399757A (en) | Process for the preparation of N-(4-hydroxyphenyl)-retinamide | |
| KR830001263A (en) | Method for preparing the compound | |
| US4705869A (en) | Preparation of fatty acid esters of ascorbic acid | |
| BE890209A (en) | PLATINUM COORDINATION COMPOUND | |
| US4699925A (en) | Biphenylylpropionic acid derivative and pharmaceutical composition containing the same | |
| US4218446A (en) | Substituted steroid-spiro-oxazolidinone derivatives and a process for the preparation thereof | |
| EP0135432B1 (en) | Derivatives of benzoic acid, process for their preparation and their use in disinfecting and conserving medicaments | |
| KR950006866B1 (en) | A process for ergoline esters preparation | |
| US2454747A (en) | Mixed alkyl esters of ascorbic acid | |
| Herkes et al. | Mono-and disubstituted vinyltrialkylammonium compounds. Synthesis and stereochemistry | |
| US4053624A (en) | Indole-2-carbaldehyde compounds and blood sugar reducing compositions | |
| EP0017420A1 (en) | New dihydroxy-acylanthrones having anti-psoriatic activity, process for preparing them, pharmaceutical compositions comprising them, and their use as anti-psoriatic agents | |
| DE2532069A1 (en) | ACYLATED PYRAZOFURINE DERIVATIVES AND METHOD FOR THEIR PRODUCTION | |
| FR2366311A1 (en) | PROCESS FOR THE PREPARATION OF POLYHALOGENIC STEROIDS USEFUL AS MEDICINAL PRODUCTS | |
| DE1445950B2 (en) | 2,6-BIS- (HYDROXYMETHYL) -PYRIDINDICARBAMATE DERIVATIVES AND METHOD FOR THEIR PRODUCTION | |
| FR2462444A1 (en) | 25-HALOGENO-5-CHOLESTENE-3B, 22-DIOLS AND THEIR USEFUL ESTERS, IN PARTICULAR AS HYPOCHOLESTEROLEMIANTS | |
| FR2399417A1 (en) | NEW DIBENZO (D, G) (1,3,6) DIOXAZOCINE DERIVATIVES, PROCESSES FOR THE PREPARATION OF THESE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING THEM | |
| Pinza et al. | Convenient Synthesis of (RS)-4-Amino-3-hydroxybutyri Acid | |
| EP0082040B1 (en) | 3,7a-diazacyclohepta(j,k)fluorene derivatives, their preparation and therapeutical use | |
| US4094988A (en) | Method of treating gastric ulcers using 5,6-dihydro-1,4-dithiinoxides | |
| US2655510A (en) | Water-soluble mono-betaine hydrazones of the aminochromes and process of preparing same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: JOHNSON MATTHEY PUBLIC LTD CY Effective date: 19940930 |