GB2053217A - Rh(III)-amine complexes - Google Patents
Rh(III)-amine complexes Download PDFInfo
- Publication number
- GB2053217A GB2053217A GB8020986A GB8020986A GB2053217A GB 2053217 A GB2053217 A GB 2053217A GB 8020986 A GB8020986 A GB 8020986A GB 8020986 A GB8020986 A GB 8020986A GB 2053217 A GB2053217 A GB 2053217A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclo
- alkenyl
- matter
- composition
- carboxylate
- 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.)
- Granted
Links
- 239000003446 ligand Substances 0.000 claims abstract description 31
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 18
- 239000010948 rhodium Substances 0.000 claims abstract description 18
- 201000011510 cancer Diseases 0.000 claims abstract description 15
- 125000002577 pseudohalo group Chemical group 0.000 claims abstract description 15
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 11
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 alkenyl carboxylates Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 6
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- ASVKKRLMJCWVQF-UHFFFAOYSA-N 3-buten-1-amine Chemical compound NCCC=C ASVKKRLMJCWVQF-UHFFFAOYSA-N 0.000 claims description 3
- ALRHLSYJTWAHJZ-UHFFFAOYSA-M 3-hydroxypropionate Chemical compound OCCC([O-])=O ALRHLSYJTWAHJZ-UHFFFAOYSA-M 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 claims description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 claims description 3
- 229940089960 chloroacetate Drugs 0.000 claims description 3
- UQFFSTQNDQYSAT-UHFFFAOYSA-N cyclobut-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC=C1 UQFFSTQNDQYSAT-UHFFFAOYSA-N 0.000 claims description 3
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 claims description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 229940114081 cinnamate Drugs 0.000 claims description 2
- 229930016911 cinnamic acid Natural products 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- 231100001274 therapeutic index Toxicity 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/418—Preparation of metal complexes containing carboxylic acid moieties
-
- 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
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
New co-ordination complexes of rhodium for the treatment of cancer have the formula Rh(NH3)3(X<1>)a(X<2>)b in which X<1> is a carboxylate monodentate or bidentate ligand, X<2> is a halogen or pseudohalogen, a has the value 1 or 2 and b has the value 1, 2 or 3, such that a + b = 3.
Description
SPECIFICATION
Compositions containing rhodium
This invention relates to co-ordination compounds of rhodium, to pharmaceutical compositions containing them and to their use in the treatment of malignant tumours or malignant neoplasms.
According to a first aspect of the invention, a composition of matter comprises a co-ordination compound of rhodium having the formula Rh(NH3)3(X')a(X2)b in which X1 is a carboxylate monodentate or bidentate ligand, X2 is a halogen or pseudohalogen (as hereinafter defined), a is the number of bonding carboxyl groups and is an integer having the value 1 or 2 or can be equal to zero and b is an integer having the value 1,2 or 3, such that a + b = 3.
When X1 represents a monodentate carboxylate ligand, or when two of such ligands, either the same or different, are present, X1 may be selected from substituted and unsubstituted straight-chain alkyl or alkenyl carboxylates, cycloalkyl or cycloalkenyl carboxylates and aryl carboxylates.
When X1 represents a bidentate carboxylate ligand, it may be selected from substituted and unsubstituted straight-chain alkyl or alkenyl dicar boxylates, cycloalkyl or cycloalkenyl dicarboxylates and aryl dicarboxylates.
Substituent groups may be selected from straightor branched- chain alkyl, aryl, alkaryl, alkenyl, aralkyl, cyclo alkyl and cyclo alkenyl, halogen, pseudohalogen (as hereinafter defined), hydroxy, carbonyl, nitro, amido, amino, alkoxy, aryloxy, carboxylic acids and salts thereof, sulphonic acid and sulphonic acid salts, oxygen and sulphur.
Preferably the substituent groups are solubilizing groups such as hydroxy, methoxy and carboxylate which may itself be substituted or unsubstituted.
Suitable monodentate carboxylate ligands include acetate, chloroacetate, bromoacetate, 3 hydroxypropionate, cis- or trans- cinnamate, and benzoate.
A suitable dicarboxylate ligand is the bidentate malonate ligand which may be substituted or unsubstituted. The malonate ligand may contain substituents selected from the group consisting of lower alkyl, (e.g. methyl, ethyl, n-propyl, isopropyl, nbutyl); aryl, (e.g. phenyl, lower alkyl-, lower alkenyl-, halo-, nitro-, lower alkoxy-su bstituted phenyl and naphthyl); aralkyl, (e.g. phenylmethyl (benzyl), 2-(1naphthyl)methyl); alkenyl, (e.g. 4-amino-1-butene, allyl); cyclo-alkyl, (e.g. cyclopropyl, cyclohexyl); cyclo-alkenyl, (e.g. 2-cyclo-penten-1-yl), 2-cyclohexen-1 - yl); alkoxy, (e.g. methoxy, ethoxy), and hydroxy.
Also suitable are the 1,1-cyclo-alkanedicarboxylic acids, (e.g. 1,1-cyclo-propanedicarboxylicacid, 1,1cyclobutanedicarboxylic acid) and the 1,1-cycloalkenyldicarboxylic acids, (e.g. 1,1 -cyclo-propeno- dicarboxylic acid, 1,1 -cyclobutenedicarboxylic acid).
Other suitable dicarboxylate ligands are the succinato, glutarato (pentanedioato), adipato (hexanedioato), pimelato (heptane-dioato), malato (cisbutenedioato) and phthalato (obenzenedicarboxylate) ligands and these may be either substituted or unsubstituted.
The term "pseudohalogen" in this specification has the meaning given on p.560 of "Advanced
Inorganic Chemistry" by Cotton and Wilkinson,
Interscience Publishers, 1966, as being "a molecule consisting of more than two electronegative atoms which, in the free state, resembles the halogens; these pseudohalogens give rise to anions which resemble the halide ions in behaviour". Examples of suitable pseudohalogens are cyanide, cyanate, thiocyanate and azide.
We have found that compounds of the present invention are active against cancer, or malignant tumours or malignant neoplasms. Normally the compound is used in association with a pharmaceutically acceptable carrier therefor. Accordingly, in a second aspect, the present invention provides a pharmaceutical composition which comprises a compound according to the first aspect of the invention and a pharmaceutically-acceptable carrier for said compound; these compositions can be formulated so as to be suitable, for example, for parenteral or oral administration to animals affected with a malignant tumour or neoplasm.
Example
One compound according to the invention, namely rhodium triammine tris-cinnamate, was prepared by reacting Rh(NH3)3CI3 with AgNO3 to yield the corresponding tris-aquo species which was further reacted with cinnamic acid to yield the desired product. The therapeutic index (i.e. LD50/lD50 when tested against ADJ/PC6 tumour was 2.6.
1. A composition of matter comprising a coordination compound of rhodium having the formula Rh(NH3)3(X1)a(X2)b in which X1 is a carboxylate monodentate or bidentate ligand, X2 is a halogen or pseudohalogen (as hereinbefore defined) a is the number of bonding carboxyl groups and is an integer having the value 1 or 2 or can be equal to zero and b is an integer having the value 1, 2 or 3, such that a + b = 3.
2. A composition of matter as claimed in Claim 1 in which, when X1 represents a monodentate carboxylate ligand, or when two of such ligands, either the same or different, are present, X1 is a substituted or unsubstituted straight-chain alkyl or alkenyl carboxylate, cycloalkyl or cycloalkenyl carboxylate or aryl carboxylate.
3. A composition of matter as claimed in Claim 1 in which, when X1 represents a bidentate carboxylate ligand, it is a substituted or unsubstituted straight-chain alkyl or alkenyl dicarboxylate, cycloalkyl or cycloalkenyl dicarboxylate or aryl dicarboxylate.
4. A composition of matter as claimed in Claim 2 or 3, in which the substituent group or groups is or are selected from straight- or branched-chain alkyl, aryl, alkaryl, alkenyl, aralkyl, cyclo alkyl and cyclo alkenyl, halogen, pseudohalogen (as hereinbefore defined), hydroxy, carbonyl, nitro, amido, amino, alkoxy, aryloxy, carboxylic acids and salts thereof,
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (11)
1. A composition of matter comprising a coordination compound of rhodium having the formula Rh(NH3)3(X1)a(X2)b in which X1 is a carboxylate monodentate or bidentate ligand, X2 is a halogen or pseudohalogen (as hereinbefore defined) a is the number of bonding carboxyl groups and is an integer having the value 1 or 2 or can be equal to zero and b is an integer having the value 1, 2 or 3, such that a + b = 3.
2. A composition of matter as claimed in Claim 1 in which, when X1 represents a monodentate carboxylate ligand, or when two of such ligands, either the same or different, are present, X1 is a substituted or unsubstituted straight-chain alkyl or alkenyl carboxylate, cycloalkyl or cycloalkenyl carboxylate or aryl carboxylate.
3. A composition of matter as claimed in Claim 1 in which, when X1 represents a bidentate carboxylate ligand, it is a substituted or unsubstituted straight-chain alkyl or alkenyl dicarboxylate, cycloalkyl or cycloalkenyl dicarboxylate or aryl dicarboxylate.
4. A composition of matter as claimed in Claim 2 or 3, in which the substituent group or groups is or are selected from straight- or branched-chain alkyl, aryl, alkaryl, alkenyl, aralkyl, cyclo alkyl and cyclo alkenyl, halogen, pseudohalogen (as hereinbefore defined), hydroxy, carbonyl, nitro, amido, amino, alkoxy, aryloxy, carboxylic acids and salts thereof, sulphonic acid and sulphonic acid salts, oxygen and sulphur.
5. A composition of matter as claimed in Claim 4, in which a substituent group is a solubilising group.
6. A composition of matter as claimed in Claim 5 in which the solubilising group is hydroxy, methoxy or carboxylate group which may itself be substituted or unsubstituted.
7. A composition of matter as claimed in Claim 2 or in any one of Claims 4,5 or 6 as dependent thereon in which X' is acetate, chloro-acetate, bromoacetate, 3-hydroxypropionate, cis- or transcinnamate, or benzoate.
8. A compositiion of matter as claimed in Claim 3 or in any one of Claims 4,5 or 6 as dependent thereon in which X1 is a bidentate malonate ligand which may be substituted or unsubstituted, any substituent being selected from lower alkyl, (eg.
methyl, ethyl, n-propyl, isopropyl, n-butyl); aryl, (e.g.
phenyl, lower alkyl- lower alkenyl-, halo-, nitro-, lower alkoxy-substituted phenyl and naphthyl); aralkyl, (e.g. phenylmethyl (benzyl), 2-(1naphthyi)methyl); alkenyl, (e.g. 4-amino-1-butene, allyl); cyclo- alkyl, (e.g. cyclopropyl, cyclohexyl); cyclo-alkenyl, (e.g. 2-cyclo-penten-1-yl), 2cyclohexen-1-yl); alkoxy, (e.g. methoxy, ethoxy), and hyd roxy.
9. A composition of matter as claimed in Claim 3 or in any one of Claims 4, 5 or 6 as dependent thereon in which X' is a 1,1-cyclo-alkanedicarboxylic acid such as 1,1 -cyclo-propanedicarboxylic acid, 1,1-cyclobutanedicarboxylic acid, or a 1,1 -cyclo- alkenyldicarboxylic acid such as 1,1 -cyclo- propenodicarboxylic acid, 1,1cyclobutenedicarboxylic acid.
10. A composition of matter as claimed in Claim 3 or in any one of Claims 4, 5 or 6 as dependent thereon in which X1 is a succinato, glutarato (pentanedioato), adipato (hexanedioato), pimelato (heptane-dioato), malato (cis-butenedioato) or phthalato (o-benzenedicarboxylate) ligand and which may be substituted or unsubstituted.
11. A pharmaceutical composition comprising a composition of matter as claimed in any one of
Claims 1 to 10 and a pharmaceutically-acceptable carrierforthe composition of matter.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8020986A GB2053217B (en) | 1979-06-29 | 1980-06-26 | Rh(iii) amine complexes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7922619 | 1979-06-29 | ||
| GB8020986A GB2053217B (en) | 1979-06-29 | 1980-06-26 | Rh(iii) amine complexes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2053217A true GB2053217A (en) | 1981-02-04 |
| GB2053217B GB2053217B (en) | 1983-07-13 |
Family
ID=26272001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8020986A Expired GB2053217B (en) | 1979-06-29 | 1980-06-26 | Rh(iii) amine complexes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2053217B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0171984A3 (en) * | 1984-08-03 | 1987-10-14 | Johnson Matthey Public Limited Company | Combination modality cancer therapy |
-
1980
- 1980-06-26 GB GB8020986A patent/GB2053217B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0171984A3 (en) * | 1984-08-03 | 1987-10-14 | Johnson Matthey Public Limited Company | Combination modality cancer therapy |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2053217B (en) | 1983-07-13 |
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|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |