GB2085440A - Cis-dichloro-trans-dihydroxy-bis (isopropylamine) platinum (iv) - Google Patents
Cis-dichloro-trans-dihydroxy-bis (isopropylamine) platinum (iv) Download PDFInfo
- Publication number
- GB2085440A GB2085440A GB8126659A GB8126659A GB2085440A GB 2085440 A GB2085440 A GB 2085440A GB 8126659 A GB8126659 A GB 8126659A GB 8126659 A GB8126659 A GB 8126659A GB 2085440 A GB2085440 A GB 2085440A
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- GB
- United Kingdom
- Prior art keywords
- dimethylacetamide
- platinum
- adduct
- cis
- dichloro
- Prior art date
- 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.)
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- 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 System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (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
1
SPECIFICATION
Co-ordination compound of platinum GB 2 085 440A 1 This invention relates to compositions of matter containing platinum, and more particularly to such compositions which are useful for the chemotherapeutic treatment of cancer or malignant neoplasms.
Our British Patent No. 1,578,323 describes and claims a composition of matter comprising a co-ordination compound of platinum having the structure- OH A 1 X i B1-- - 7Y OH pt in which X and Y are halogenoid groups which are the same or different and are preferably both chloride but may be other halide or pseudohaiide such as cyanate, thiocyanate and azide and A 20 and B are the same or different branched chain aliphatic amine groups coordinated to the Pt through their N atoms.
Also described and claimed in the said British Patent is a composition for the treatment of cancer or a malignant neoplasm comprising a co-ordination compound of platinum having the structure:
OH A 1 X \ i Pt / i B 1 Y OH in which X and Y are halogenoid groups which are the same or different and are preferably both 35 chloride but may be other halide or a pseudohalide such as cyanide, cyanate, thiocyanate, or azide or other similar groups and A and B are the same or different branched chain aliphatic amine groups or C- substituted branched chain aliphatic amine groups co-ordinated to the Pt through their N atoms each having the general formula - 40 CnR2n+2 in which N may vary from 3 to 9 and in which all of the R groups are either the same or different and are preferably all hydrogen but may be selected from the group consisting of hydrogen, alkyl, aryi, alkaryl, aralkyl, halogen, pseudohalogen, hydroxy, carbonyl, formyi, nitro, 45 amido, amino, sulphonic acid, sulphonic acid salt, carboxylic acid, carboxylic acid salt, and substituted alkyl, aryi, alkaryl and aralkyl groups.
The platinum is preferably present as Pt', thus producing a neutral complex with two hydroxyl and two halide 5gands.
Although R groups other than hydrogen are not normally preferred, they may be used and may comprise lower alkyl such as methyl or ethyl or a solubilizing group such as a sulphonic acid group. Solubilizing groups, such as carboxylic acid, sulphonic acid, and salts thereof, for example the sodium, potassium or lithium salts, are sometimes appropriate as substituents when the clinical conditions require high solubility.
Throughout the specification and claims of the said British patent, the term -halogenoid- is 55 used to mean halide (chloride, bromide, iodide or fluoride) or pseudohalide such as cyanide, cyanate, thiocyanate or azide.
Suitable branched chain amine compounds which may be used for groups A and B are said to be isopropylamine, isobutylamine, isoamylamine and 2-aminohexane.
One partieular compound failing within the scope of the claims of GB 1578323 is where A 60 and B in the general formula are both isopropylamine and X and Y are both chloride, the complex thus being cis-dichloro-trans-dihydroxy- bis(isopropylamine)platinum(IV). The method of preparation quoted in the specification of the said patent comprises heating a slurry of the corresponding cis-diaminedichloroplatinum(I1) complex with hydrogen peroxide solution, boiling for 0.5 hours until yellow in colour, chilling, filtering, washing the residue with water and ether 65 2 GB2085440A 2 and drying in air. The resulting crude product is recrystallised from a water/hydrogen peroxide solvent mixture and dried in vacuo. From the elemental analysis figures, the infra-red absorption spectrum and X-ray crystallography of a single crystal, the formula of the corresponding 1:1 hydrate was assigned to it.
Subsequent work has shown that the complex as prepared and recrystallised as described above in fact exists as an adduct with hydrogen peroxide in a ratio of 2 molecules complex to 1 molecule H202, but the presence of hydrogen peroxide is considered disadvantageous from the pharmacological viewpoint. However, attempts to remove it by physical means have invariably failed due to decomposition of the complex involving loss of the hydroxy ligands. It has hitherto been considered, therefore, that it is impossible to prepare and isolate the complex in substantially pure form, that is, devoid of detectable amounts of hydrogen peroxide or other solvating molecules.
We have now found that the complex may after all be prepared in substantially pure form.
According to the invention, therefore, we provide a co-ordination compound of platinum in substantially pure form and having the structure:
qi OH NI-12CH(CH1 \ 1 / Pt / 1 \ Cl 1 NI-12CH(CH.)2 OH The compound according to the present invention is useful for the chemotherapeutic treatment of cancer or malignant neoplasms.
The invention also includes a process for the preparation of a coordination compound of platinum in substantially pure form and having the structure.
OH qi NI-12CH(CH1 Pt Cl 1 NH2CH(C1-11 OH TO -1 the process comprising reacting cis-dichloro- di(isopropylamine)platinum(I1) with hydrogen perox ide, isolating the product, dissolving the said product in N,Ndimethylacetamide, isolating the resulting product which comprises a 1:1 adduct of the said compound with N,N-dimethylace- 40 tamide, and thereafter removing the said N,N-dimethylacetamide, under vacuum at a tempera ture less than 8WC, preferably less than 5WC.
We have found that the use of dimethylacetamide in the process according to the invention to provide the intermediate 1:1 adduct is successful in removing hydrogen peroxide where straightforward reerystallisations using general purpose solvents have failed. As indicated above, 45 water is unsuccessful; so too is methanol, despite the vast numerical excess of solvent molecules over hydrogen peroxide molecules, whereas it would have been expected that either of these solvents would have been suitable, due to their polarity and their miscibility with hydrogen peroxide.
The intermediate 1: 1 adduct of cis-dichloro-transdihydroxybis(isopropylamine)piatinum(IV) with dimethylacetamide is itself a novel composition of matter which is isolable, stable and characterisable.
Embodiments of the invention will now be described with reference to the following preparative example, which refers (a) to the preparation of crude cis-dichloro-trans-dihydroxy- bis(isopropyla mine) Pt(IV) and (b) to the preparation of the intermediate adduct with dimethyla- 55 cetamide with subsequent isolation of the substantially pure product.
EXAMPLE (A) Preparation of crude product Recrystallised cis-Pt(i-C,H-,NH,),Cl, (26.8g) was slurried in hot water (50 mi) and aqueous 60 hydrogen peroxide (100 vols; 100 mi) was added with stirring. The slurry was boiled for half an hour until yellow in colour and was then chilled and filtered. The residue was washed with water, then with ether and was then dried in air. The yield was 10.5 g (35%).
Elemental analysis figures were as follows:
1 5.0 -p 3 GB 2 085 440A 3 c H Ca[Culated % 16.55 4.87 Found % 16.59 4.90 N 0 c] 6.43 11.03 16.28 6.48 10.80 16.20 Thr [R hydroxyl stretching absorption (,' 0-H) occurs at 3515 cm - 1.
(b) Preparation of the adduct and isolation of substantially pure product The crude product (11 g) prepared as above was dissolved in N, Ndimethylacetamide (approx 11) and the solution was filtered through a glass sinter (porosity 4) to remove any insoluble material present. The solution was then cooled to 5'C for 2 hours, seeded to prevent supersaturation and stored at - 1 OC for several days. The resulting crystals were filtered off, washed with ether and dried.
Removal of WN-dimethylacetamide to yield substantially pure product was carried out by heating the crystals to a temperature of WC or less at a pressure of 0. 1 torr for several days, or until the absence of N,N-dimethylacetamide was confirmed by thermal gravimetric analysis 15 and/or gas liquid chromatography.
The step of dissolving the crude product from (a) above in N,Ndimethylacetamide may be carried out at ambient temperatures but we prefer to use a slightly elevated temperature, that is, not higher than about 4WC.
Further optional purification steps include recrystaffisation of the crude product (step (a) 20 above) from dilute hydrogen peroxide solution, followed by drying at approximately WC in vacuo, and further filtering the N,N-dimethylacetamide solution (step (b) above) through a silica gel bed (70-230 mesh) to remove any polyhydroxy platinum species.
Analytical data for characterisation of the prior art hydrogen peroxide adduct, the compound according to the invention and the N,N-dimethylacetamide adduct are as described below and as 25 illustrated in the accompanying drawings of which:
Figure 1 is an IR spectrum of the prior art hydrogen peroxide adduct;
Figure 2 is an IR spectrum of the novel dimethylacetamide adduct; Figure 3 is an IR spectrum of the compound according to the invention; Figure 4 is an X-ray powder diffraction pattern of the prior art hydrogen peroxide adduct; 30
Figure 5 is an X-ray powder diffraction pattern of the novel N,Ndimethylacetamide adduct; Figure 6 is an X-ray powder diffraction pattern of the compound according to the invention; Figure 7 shows chromatograms of various compounds; Figure 8 shows the results of thermal gravimetric analysis of various compounds, Figure 9 is a stereoscopic view of the N,N-dimethylacetamide adduct.
In the details which follow, cis,trans,cis-[PtC12(0H)2 (iPrNH2)2]-the compound according to the invention-was prepared as individual batches A, B, C which were then throughly mixed together to give composite batch X. Analytical data was as follows:
Physical form: Yellow powde"r (all batches) 40 Infrared spectrum: See Figures 1-3 Elemental analysis: Batch c H N 0 cl Pt A 17.27 4.84 6.79 8.20 16.58 46.43 B 17.26 4.87 6.76 7.88 16.85 46,47 45 c 17.17 4.80 6.76 7.80 16.86 46.45 X 17.13 4.81 6.71 7.75 16.81 46.45 Theory 17.23 4.82 6.70 7.65 16.95 46.65 HPLC (bulk assay): % purity 50 Batch A 97.31 B 100.17 c 97.63 55 X 98.27 Impurity levels: Batch Wt % Peroxide value DMA 60 A 0.05 <0.06 B 0.03 <0.09 c 0.05 0.15 X 0.06 0.024 Moisture content: <0.25 wt % (all batches) by TGA. 65 4 GB2085440A 4 Referring now to the drawings, Figs. 1, 2 and 3 show infrared spectra of various compounds, the most notable feature being the different absorption patterns for OH stretch in the region of 3500 cm - 1, indicating that the prior art hydrogen peroxide adduct, the novel N, N-dimethylace tamide adduct and the compound according to the invention in substantially pure form are all separately isolable and characterisable compounds. Figs. 4, 5 and 6 are indicative of the same 5 conclusion, the evidence in this case being the X-ray powder diffraction patterns. On each figure the 20. angle is given and also the separation of the planes in A.
Fig. 7 shows the amounds of N,N-dimethylacetamide (DMA) present in batches A, B, C and X as meaured by gas liquid chromatography.
For a given range, a similar response in A, B, C or X compared with the standard would 10 represent a DMA concentration of ca. 1 % by weight.
Referring to Fig. 8, which shows the results of thermal gravimetric analysis of various compounds, the legend is as follows:
Line 1 represents a prior art hydrogen peroxide adduct compound,
Line 2 represents a novel N,N-dimethylacetamide adduct compound; 1 Line 3 represents a compound according to the invention.
The traces have been abitrarily displaced on the -weight (%)- axis for ease of presentation.
It is seen that line 1 indicates a greater weight loss at about 1 WC due to loss of trans OH groups as well as H202, whereas lines 2 and 3 show substantially the same weight loss at that temperature due to the loss of the trans OH groups alone. In line 2, the sloping shoulder up to 20 the temperature of about 1 WC represents loss of N,N-dimethylacetamide and thereafter the compounds represented by lines 2 and 3 are seen to be substantially identical.
Referring to Fig. 9, the stereoscopic view shown was derived by X-ray crystallographic study of a single crystal of the N,N-dimethylacetamide adduct. Attempts to isolate a single crystal of the substantially pure compound according to the invention from a single crystal of the N,Ndimethylacetamide adduct resulted in an agglomeration of microcrystallites, the X-ray powder pattern for which is shown in Fig. 6.
The substantially pure cis-dichloro-transdihydroxybis(isopropylamine)Pt(IV) may be adminis tered in substantially the same manner as described in GB 1578323 with respect to the prior are hydrogen peroxide adduct.
Claims (4)
1. A co-ordination compound of platinum in substantially pure form and having the structure OH qi NI-12CH(C1-1J2 Pt C] 1 NH2CH(CH3)
2 OH 2. A process for the preparation of a co-ordination compound of platinum in substantially pure form and having the structure OH qi NH,CH(C1-1J2 \ 1 / Pt 50 A Cl 1 NH2CH(CH1 OH comprising reacting cis-dichloro-di(isopropylamine)piatinum(I1) with hydrogen peroxide, isolating the product, dissolving the said product in N,N-dimethylacetamide, isolating the resulting product which comprises a 1:1 adduct of the said compound with N,N-dimethylacetamide and thereafter removing the said N,N- dimethylacetamide under vacuum at a temperature less than 801C.
3. A process according to claim 2 in which the N,N-dimethylacetamide is removed under vacuum at a temperature less than WC,
4. A composition of matter comprising a 1:1 adduct of cis-dichloro-trans- dihydroxy-bis(iso-. propylamine)piatinum(IV) with dimethylacetamide.
Printed for Her Majesty's Stationery Office by Burgess Ef Son (Abingdon) Ltd.-1 982. Published at The Patent Office, 25 Southampton Buildings, London, WC2A 1AY, from which copies may be obtained.
A 4 W 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8028484 | 1980-09-03 | ||
| GB8115549 | 1981-05-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2085440A true GB2085440A (en) | 1982-04-28 |
| GB2085440B GB2085440B (en) | 1984-07-25 |
Family
ID=26276771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8126659A Expired GB2085440B (en) | 1980-09-03 | 1981-09-03 | Cis-dichloro-trans-dihydroxy-bis (isopropylamine) platinum (iv) |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4394319A (en) |
| AT (1) | AT375626B (en) |
| AU (1) | AU541255B2 (en) |
| CA (1) | CA1176646A (en) |
| CH (1) | CH651840A5 (en) |
| CS (1) | CS229919B2 (en) |
| CY (1) | CY1384A (en) |
| DE (1) | DE3134671C2 (en) |
| DK (2) | DK150474C (en) |
| ES (1) | ES505090A0 (en) |
| FI (1) | FI68627C (en) |
| FR (1) | FR2489314A1 (en) |
| GB (1) | GB2085440B (en) |
| GR (1) | GR75317B (en) |
| HK (1) | HK97087A (en) |
| HU (1) | HU185951B (en) |
| IE (1) | IE51539B1 (en) |
| IL (1) | IL63658A0 (en) |
| IT (1) | IT1194090B (en) |
| KE (1) | KE3729A (en) |
| LU (1) | LU83599A1 (en) |
| MY (1) | MY8700553A (en) |
| NL (1) | NL190326C (en) |
| PH (1) | PH22094A (en) |
| SE (1) | SE452467B (en) |
| SG (1) | SG42787G (en) |
| WO (1) | WO1982000825A1 (en) |
| YU (1) | YU42726B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8367599B2 (en) | 2001-03-16 | 2013-02-05 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Dishwashing composition with particles |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3305248A1 (en) * | 1983-02-16 | 1984-08-16 | Degussa Ag, 6000 Frankfurt | METHOD FOR PRODUCING PURE CIS-PLATIN (II) DIAMMINE DICHLORIDE |
| GB8328218D0 (en) * | 1983-10-21 | 1983-11-23 | Johnson Matthey Plc | Oral compositions |
| US4772735A (en) * | 1986-08-25 | 1988-09-20 | University Of Delaware | Coordination complexes of platinum with amides |
| CA1339034C (en) * | 1988-08-22 | 1997-04-01 | Paul A. Tremblay | Platinum complexes of single isomer neoalkyl acids |
| GB9105037D0 (en) * | 1991-03-09 | 1991-04-24 | Johnson Matthey Plc | Improvements in chemical compounds |
| CA2385528C (en) | 1999-10-01 | 2013-12-10 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| GB0011903D0 (en) * | 2000-05-18 | 2000-07-05 | Astrazeneca Ab | Combination chemotherapy |
| DE50305768D1 (en) * | 2003-10-13 | 2007-01-04 | Salama Zoser B | Process for the preparation of trans- or cis-diammoniumdichlorodihydroxoplatinum (IV) salts and derivatives and their use for the preparation of pharmaceutical active substances |
| US8168661B2 (en) * | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8178564B2 (en) * | 2006-11-06 | 2012-05-15 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8173686B2 (en) | 2006-11-06 | 2012-05-08 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8168662B1 (en) | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US20110033528A1 (en) * | 2009-08-05 | 2011-02-10 | Poniard Pharmaceuticals, Inc. | Stabilized picoplatin oral dosage form |
| US20100260832A1 (en) * | 2007-06-27 | 2010-10-14 | Poniard Pharmaceuticals, Inc. | Combination therapy for ovarian cancer |
| TW200916094A (en) * | 2007-06-27 | 2009-04-16 | Poniard Pharmaceuticals Inc | Stabilized picoplatin dosage form |
| WO2009011861A1 (en) * | 2007-07-16 | 2009-01-22 | Poniard Pharmaceuticals, Inc. | Oral formulations for picoplatin |
| WO2016025742A1 (en) | 2014-08-13 | 2016-02-18 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Pt(iv) complexes containing 4,4'-disubstituted-2,2'-bipyridyl and their use in cancer therapy |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1578323A (en) * | 1976-02-26 | 1980-11-05 | Rustenburg Platinum Mines Ltd | Compositions containing platinum |
| SE7903359L (en) * | 1978-04-20 | 1979-10-21 | Johnson Matthey Co Ltd | COMPOSITIONS CONTAINING PLATINUM |
-
1981
- 1981-08-25 GR GR65868A patent/GR75317B/el unknown
- 1981-08-25 IL IL63658A patent/IL63658A0/en not_active IP Right Cessation
- 1981-08-26 NL NLAANVRAGE8103954,A patent/NL190326C/en not_active IP Right Cessation
- 1981-08-26 US US06/296,478 patent/US4394319A/en not_active Expired - Fee Related
- 1981-08-28 AU AU74725/81A patent/AU541255B2/en not_active Ceased
- 1981-09-01 FI FI812696A patent/FI68627C/en not_active IP Right Cessation
- 1981-09-01 ES ES505090A patent/ES505090A0/en active Granted
- 1981-09-02 HU HU812536A patent/HU185951B/en not_active IP Right Cessation
- 1981-09-02 FR FR8116703A patent/FR2489314A1/en active Granted
- 1981-09-02 SE SE8105213A patent/SE452467B/en not_active IP Right Cessation
- 1981-09-02 CA CA000385038A patent/CA1176646A/en not_active Expired
- 1981-09-02 DK DK388281A patent/DK150474C/en not_active IP Right Cessation
- 1981-09-02 LU LU83599A patent/LU83599A1/en unknown
- 1981-09-02 DE DE3134671A patent/DE3134671C2/en not_active Expired - Fee Related
- 1981-09-02 IE IE2027/81A patent/IE51539B1/en not_active IP Right Cessation
- 1981-09-02 AT AT0379081A patent/AT375626B/en not_active IP Right Cessation
- 1981-09-03 CY CY138481A patent/CY1384A/en unknown
- 1981-09-03 IT IT23756/81A patent/IT1194090B/en active
- 1981-09-03 CH CH5676/81A patent/CH651840A5/en not_active IP Right Cessation
- 1981-09-03 WO PCT/GB1981/000177 patent/WO1982000825A1/en unknown
- 1981-09-03 GB GB8126659A patent/GB2085440B/en not_active Expired
- 1981-09-03 YU YU2119/81A patent/YU42726B/en unknown
- 1981-09-03 CS CS816539A patent/CS229919B2/en unknown
- 1981-09-04 PH PH26144A patent/PH22094A/en unknown
-
1986
- 1986-07-11 DK DK330086A patent/DK154068C/en not_active IP Right Cessation
-
1987
- 1987-05-08 SG SG42787A patent/SG42787G/en unknown
- 1987-05-18 KE KE3729A patent/KE3729A/en unknown
- 1987-12-17 HK HK970/87A patent/HK97087A/en unknown
- 1987-12-30 MY MY553/87A patent/MY8700553A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8367599B2 (en) | 2001-03-16 | 2013-02-05 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Dishwashing composition with particles |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940903 |