CH632672A5 - A drug containing a platinum coordination compound - Google Patents
A drug containing a platinum coordination compound Download PDFInfo
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- CH632672A5 CH632672A5 CH187981A CH187981A CH632672A5 CH 632672 A5 CH632672 A5 CH 632672A5 CH 187981 A CH187981 A CH 187981A CH 187981 A CH187981 A CH 187981A CH 632672 A5 CH632672 A5 CH 632672A5
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- Prior art keywords
- formula
- coordination compound
- substituents
- platinum
- acid residue
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title claims abstract description 12
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 8
- 229940079593 drug Drugs 0.000 title abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 16
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000002577 pseudohalo group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 3
- 125000003368 amide group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 4
- -1 hydroxy, formyl Chemical group 0.000 claims description 4
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 claims description 4
- 230000003381 solubilizing effect Effects 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 3
- OINASENMXSWSRL-UHFFFAOYSA-N 2-aminobicyclo[2.2.1]heptan-3-one Chemical compound C1CC2C(=O)C(N)C1C2 OINASENMXSWSRL-UHFFFAOYSA-N 0.000 claims description 2
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 claims description 2
- BVVFUHROAFTSMG-UHFFFAOYSA-N 3-methylbutan-1-amine;pentan-1-amine Chemical compound CCCCCN.CC(C)CCN BVVFUHROAFTSMG-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- 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 claims description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims description 2
- 241000699670 Mus sp. Species 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- WGBBUURBHXLGFM-UHFFFAOYSA-N hexan-2-amine Chemical compound CCCCC(C)N WGBBUURBHXLGFM-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 208000003747 lymphoid leukemia Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 231100001274 therapeutic index Toxicity 0.000 claims description 2
- 208000035269 cancer or benign tumor Diseases 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 238000005259 measurement Methods 0.000 description 2
- IZCBXLKODYZSDJ-UHFFFAOYSA-N 5-methylhexan-2-amine Chemical compound CC(C)CCC(C)N IZCBXLKODYZSDJ-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YAHRDLICUYEDAU-UHFFFAOYSA-N methylhexaneamine Chemical compound CCC(C)CC(C)N YAHRDLICUYEDAU-UHFFFAOYSA-N 0.000 description 1
- 229950000752 methylhexaneamine Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The drug for treating cancer and malign neoplasm contains, as the active component, at least one coordination compound of platinum of the structural formula <IMAGE> in which X and Y, identically or differently, denote halogen or pseudohalogen and A and B, identically or differently, denote a group of the formula CnR2n+1NH2 where the R radicals are all identical or different and represent hydrogen, optionally substituted alkyl, aryl, alkaryl, aralkyl, halogen, pseudohalogen, hydroxyl, formyl, nitro, amido, amino, a sulphonic acid radical or carboxylic acid radical, or a salt thereof, and n represents an integer from 3-9, where the groups A and B are in each case coordinated with the platinum atom via the N atom.
Description
**WARNUNG** Anfang DESC Feld konnte Ende CLMS uberlappen **.
PATENTANSPRÜCHE
1. Arzneimittel für die Behandlung von Krebs und malignem Neoplasma, dadurch gekennzeichnet, dass es als aktive Komponente mindestens eine Koordinationsverbindung von Platin der Formel
EMI1.1
worin X und Y gleich oder verschieden Halogen oder Pseudohalogen und A und B gleich oder verschieden eine Gruppe der Formel
CnR2n+ 1NH2 wobei R alle gleich oder verschieden sind und für Wasserstoff, gegebenenfalls substituiertes Alkyl, Aryl, Alkaryl, Aralkyl, Halogen, Pseudohalogen, Hydroxy, Formyl, Nitro, Amido, Amino, einen Sulfon- oder Carbonsäurerest oder ein Salz davon und n für eine ganze Zahl von 3-9 stehen, wobei die Gruppen A und B jeweils über das N-Atom mit dem Platinatom koordiniert sind, bedeuten, enthält.
2. Arzneimittel nach Anspruch 1, dadurch gekennzeichnet, dass in der angegebenen Formel X und Y beide Chlor bedeuten.
3. Arzneimittel nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass in der angegebenen Formel der Substituenten A und B alle R Wasserstoff bedeuten.
Gegenstand der vorliegenden Erfindung ist das im Patentanspruch 1 definierte, eine Platin-Koordinationsverbindung als aktive Komponente enthaltende Arzneimittel für die Chemotherapie von Krebs und malignem Neoplasma.
In der aktiven Komponente des erfindungsgemässen Arzneimittels liegt Platin vorzugsweise als Pt4 vor, so dass diese Koordinationsverbindung ein neutraler Komplex mit zwei Hydroxyl- und zwei Halogenliganden ist.
Obwohl in der für die Substituenten A und B der beschriebenen Koordinationsverbindung angegebenen Formel alle R vorzugsweise Wasserstoff bedeuten, kommen auch Niederalkyl, wie Methyl oder Äthyl, oder solubilisierende Gruppen, wie ein Sulfonsäurerest, dafür in Frage. Solubilisierende Gruppen als Substituenten, wie ein Carbonsäurerest, Sulfonsäurerest oder deren Salze, z. B. das Natrium-, Kalium- oder Lithiumsalz, sind manchmal besonders geeignet, wenn hohe Löslichkeit der Verbindungen erwünscht ist.
Im folgenden soll unter dem Begriff Halogenoida sowohl Halogenid (Chlorid, Bromid, Jodid oder Fluorid) als auch Pseudohalogenid wie Cyanid, Cyanat, Thiocyanat oder Azid, verstanden werden.
Geeignete Beispiele für verzweigtkettige Aminverbindungen der Substituenten A und B sind Isopropylamin, Isobutylamin, Isoamylamin und 2-Aminohexan.
Bei der Durchführung von Standardtests für ADJ/PC6 und Walker-Tumore bei Zl-9-weissen Mäusen wurden unter Verwendung von trans-Dihydroxo-Komplexen von Pt(IV), bei denen X und Y beide Chlorid bedeuten und A und B die genannten Substituenten waren, die in nachfolgender Tabelle genannten Ergebnisse erhalten:
: Tumor A und B mg/kg Therapeutischer
Index (II) IDgo LDso ADJ/PC6 Oxo-2-amino-norbornan 40,5 660 16,3
ISO-Propylamin (01) 7,5 90 12,0 (Wasser) 4,2 54 12,9
ISO-Butylamin 19,5 410 21
ISO-Pentylamin (Amylamin) 112 800 7,1
19,0 20 37,9 EDgo LDso TI Walker ISO-Propylamin (Ö1) 17 45 2,6 (Wasser) 16 56 3,5
Ferner wurden drei Serien von Standardtests für P 388 (Ascitische) lymphozytische Leukämie unter Verwendung des Isopropylaminkomplexes durchgeführt. Die erhaltenen Ergebnisse waren die folgenden:
Dosis Gewichtsänderung Tiergewichts- Tumormessung Tumormessung Prozentuale mg/kg bei den Kontrollen änderung (Test) (Tage) Kontrolle Verlängerung (T-C) (T) (Tage) (C) der
Lebensdauer (T/C) (i) 200 -1,4 -4,6 6,2 15,5
100 -1,4 -4,0 6,4 15.5
50,0 -1,4 -3,6 24,0 15,5 154
25,0 -1,4 -1,6 23,3 15,5 150
12,5 -1,4 -1,8 21,3 15,5 137 (ii) 200 1,0 -1,0 4,19 11,8
100 1,0 -6,4 6,1 11,8
50,0 1,0 -6,5 8,0 11,8
25,0 1,0 -5,7 15,0 11,8 127 12,5 1,0 -4,2 21,8 1 1,8 184 (iii) 200 1,0 - 1,0 3,0 1 1,8
100 1,0 -6,5 6,8 11,8
50,0 1,0 -5,2 18,0 11,8 152
25,0 1,0 -4,0 16,1 11,8 136
12,5 1,0 -2,5 15,3 11,8 129
Weitere verzweigtkettige Amine, die als Liganden A und B eingesetzt werden können, sind:
2-Amino-5-methylhexan, 2-Amino-4-methylhexan,
2-Amino-heptan, tert.-Butylamin.
Ein bevorzugtes Verfahren zur Herstellung von trans-Dihydroxo-cis-dichlordiamin-Pt(IV)-Komplexen (d. h. worin A und B gleich sind), besteht beispielsweise darin, dass eine Aufschlämmung des entsprechenden cis-Diamindichlorplatin(II)-Komplexes mit einer Wassstoffperoxidlösung erwärmt wird.
** WARNING ** beginning of DESC field could overlap end of CLMS **.
PATENT CLAIMS
1. Medicament for the treatment of cancer and malignant neoplasm, characterized in that it is at least one coordination compound of platinum of the formula as an active component
EMI1.1
wherein X and Y are identical or different halogen or pseudohalogen and A and B are identical or different a group of the formula
CnR2n + 1NH2 where R are all the same or different and represent hydrogen, optionally substituted alkyl, aryl, alkaryl, aralkyl, halogen, pseudohalogen, hydroxy, formyl, nitro, amido, amino, a sulfonic or carboxylic acid residue or a salt thereof and n for one are integers from 3-9, where groups A and B are each coordinated via the N atom with the platinum atom.
2. Medicament according to claim 1, characterized in that in the formula X and Y both represent chlorine.
3. Medicament according to claim 1 or 2, characterized in that in the formula of the substituents A and B all R is hydrogen.
The present invention relates to the medicament for the chemotherapy of cancer and malignant neoplasm, which contains a platinum coordination compound as active component and is defined in claim 1.
Platinum is preferably present as Pt4 in the active component of the medicament according to the invention, so that this coordination compound is a neutral complex with two hydroxyl and two halogen ligands.
Although in the formula given for the substituents A and B of the coordination compound described, all R preferably denote hydrogen, lower alkyl, such as methyl or ethyl, or solubilizing groups, such as a sulfonic acid residue, are also suitable. Solubilizing groups as substituents, such as a carboxylic acid residue, sulfonic acid residue or their salts, e.g. B. the sodium, potassium or lithium salt are sometimes particularly suitable when high solubility of the compounds is desired.
In the following, the term haloida should be understood to mean both halide (chloride, bromide, iodide or fluoride) and pseudohalide such as cyanide, cyanate, thiocyanate or azide.
Suitable examples of branched-chain amine compounds of substituents A and B are isopropylamine, isobutylamine, isoamylamine and 2-aminohexane.
When carrying out standard tests for ADJ / PC6 and Walker tumors in Zl-9 white mice, using trans-dihydroxo complexes of Pt (IV), in which X and Y both mean chloride and A and B said substituents the results given in the table below were obtained:
: Tumor A and B mg / kg therapeutic
Index (II) IDgo LDso ADJ / PC6 Oxo-2-amino-norbornan 40.5 660 16.3
ISO propylamine (01) 7.5 90 12.0 (water) 4.2 54 12.9
ISO butylamine 19.5 410 21
ISO pentylamine (amylamine) 112 800 7.1
19.0 20 37.9 EDgo LDso TI Walker ISO propylamine (Ö1) 17 45 2.6 (water) 16 56 3.5
Three series of standard tests for P 388 (Ascitic) lymphocytic leukemia were also performed using the isopropylamine complex. The results obtained were as follows:
Dose Weight Change Animal Weight Tumor Measurement Tumor Measurement Percentage mg / kg in Control Change (Test) (Days) Control Extension (T-C) (T) (Days) (C) of
Lifetime (T / C) (i) 200 -1.4 -4.6 6.2 15.5
100 -1.4 -4.0 6.4 15.5
50.0 -1.4 -3.6 24.0 15.5 154
25.0 -1.4 -1.6 23.3 15.5 150
12.5 -1.4 -1.8 21.3 15.5 137 (ii) 200 1.0 -1.0 4.19 11.8
100 1.0 -6.4 6.1 11.8
50.0 1.0 -6.5 8.0 11.8
25.0 1.0 -5.7 15.0 11.8 127 12.5 1.0 -4.2 21.8 1 1.8 184 (iii) 200 1.0 - 1.0 3.0 1 1.8
100 1.0 -6.5 6.8 11.8
50.0 1.0 -5.2 18.0 11.8 152
25.0 1.0 -4.0 16.1 11.8 136
12.5 1.0 -2.5 15.3 11.8 129
Other branched chain amines that can be used as ligands A and B are:
2-amino-5-methylhexane, 2-amino-4-methylhexane,
2-amino-heptane, tert-butylamine.
For example, a preferred method of making trans-dihydroxo-cis-dichlorodiamine-Pt (IV) complexes (ie, where A and B are the same) is to slurry the corresponding cis-diamine dichloroplatinum (II) complex with a hydrogen peroxide solution is heated.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH242077A CH629744A5 (en) | 1976-02-26 | 1977-02-25 | METHOD FOR PRODUCING NEW PLATINUM (IV) COORDINATION COMPOUNDS. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH632672A5 true CH632672A5 (en) | 1982-10-29 |
Family
ID=4233388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH187981A CH632672A5 (en) | 1977-02-25 | 1981-03-19 | A drug containing a platinum coordination compound |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH632672A5 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003017993A1 (en) * | 2001-08-24 | 2003-03-06 | The University Court Of The University Of Edinburgh | Photoreactive compounds and compositions |
-
1981
- 1981-03-19 CH CH187981A patent/CH632672A5/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003017993A1 (en) * | 2001-08-24 | 2003-03-06 | The University Court Of The University Of Edinburgh | Photoreactive compounds and compositions |
| US7176327B2 (en) | 2001-08-24 | 2007-02-13 | University Court Of The University Of Edinburgh | Photoreactive compounds and compositions |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: JOHNSON MATTHEY PUBLIC LIMITED COMPANY |
|
| PUE | Assignment |
Owner name: JOHNSON, MATTHEY & CO., LIMITED |
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| PL | Patent ceased | ||
| PL | Patent ceased |