DE3229169A1 - Use of 5-alkylpyrimidine nucleosides and their derivatives as cytostatics - Google Patents
Use of 5-alkylpyrimidine nucleosides and their derivatives as cytostaticsInfo
- Publication number
- DE3229169A1 DE3229169A1 DE19823229169 DE3229169A DE3229169A1 DE 3229169 A1 DE3229169 A1 DE 3229169A1 DE 19823229169 DE19823229169 DE 19823229169 DE 3229169 A DE3229169 A DE 3229169A DE 3229169 A1 DE3229169 A1 DE 3229169A1
- Authority
- DE
- Germany
- Prior art keywords
- branched
- carbon atoms
- nucleosides
- derivatives
- radical
- 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.)
- Withdrawn
Links
- 239000002777 nucleoside Substances 0.000 title claims abstract description 9
- 125000003835 nucleoside group Chemical group 0.000 title claims abstract description 9
- 230000001085 cytostatic effect Effects 0.000 title abstract description 12
- 239000000824 cytostatic agent Substances 0.000 title abstract description 8
- 239000002215 arabinonucleoside Substances 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 230000003211 malignant effect Effects 0.000 claims description 3
- 230000003389 potentiating effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- -1 alkyl radical Chemical class 0.000 claims 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 description 5
- 206010022998 Irritability Diseases 0.000 description 3
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 206010043275 Teratogenicity Diseases 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002718 pyrimidine nucleoside Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Verwendung von 5-Alkylpyrimidinnukleosiden und derenUse of 5-alkylpyrimidine nucleosides and their
Derivate als Zytostatika Die vorliegende Erfindung betrifft die Verwendung von 5-Alkylpyrimidinnukleosiden und deren Derivate als Zytostatika bei der Bekämpfung von malignen Erkrankungen in Kombination mit Arabinonukleosiden und zur Potenzierung der zytostatischen wirkung von Arabinonukleosiden sowie Arzneimittel mit zytostatischer Wirkung, welche als Wirkstoffe aiese Nukleoside in Kombination enthalten.Derivatives as cytostatics The present invention relates to the use of 5-alkylpyrimidine nucleosides and their derivatives as cytostatics in combating malignancies in combination with arabinonucleosides and to potentiate the cytostatic effects of arabinonucleosides and drugs with cytostatic effect, which as active ingredients aese nucleosides in combination contain.
Es ist bekannt, daß verschiedene Pyrimidinnukleoside und einige von ihren Derivaten eine zytostatische wirkung aufweisen (DE - OS 29 18 260, DE - OS 29 20 738, DE - OS 29 30 904, Dr - OS 30 10 397, DE - OS 30 10 399, Ungar. Pat.It is known that various pyrimidine nucleosides and some of their derivatives have a cytostatic effect (DE-OS 29 18 260, DE-OS 29 20 738, DE - OS 29 30 904, Dr - OS 30 10 397, DE - OS 30 10 399, Ungar. Patient
171 306).171 306).
Außerdem ist bekannt, daß einige Arabinonukleoside, z.B.It is also known that some arabinonucleosides, e.g.
Cytosinarabinosid (AraC) zytostatisch wirksam sind.Cytosine arabinoside (AraC) are cytostatically effective.
Ein Nachteil dieser Verbindungen ist jedoch ihre teilweise hohe Toxizität, so daß der therapeutische Index gering ist und eine Anwendung der Mittel nicht ohne Probleme ist, besonders wenn sie hoch dosiert werden müssen. Weitere Nachteile sind unerwünschte Nebenwirkungen, wie z.E. Mutagenität und Teratogenitöt sowie ungünstiges pharmakokinetisches Verhalten.However, a disadvantage of these compounds is their sometimes high toxicity, so that the therapeutic index is low and an application of the means is not without it Problems, especially when they have to be dosed in high doses. Other disadvantages are undesirable side effects, such as Mutagenicity and teratogenicity as well as unfavorable pharmacokinetic behavior.
Es wurden daher immer wieder Versuche unternommen, durch Kombination der bekannten Zytostatika mit anderen zytostatisch wirksamen Stoffen oder gänzlich anderen Wirkstoffen, diese Nachteile zu beseitigen. Die zytostatische Wirkung der Kombination sollte durch Synergismus (Wirkungsaddition oder Potenzierung) bei geringerer Toxizitöt wesentlich stärker sein als die der Einzelkomponenten.Attempts have therefore been made again and again, by combination the known cytostatic agents with other cytostatic substances or completely other active ingredients to eliminate these disadvantages. The cytostatic effect of the Combination should be achieved through synergism (addition of effects or potentiation) with less Toxicity must be much stronger than that of the individual components.
Untersuchun3en mit solchen Kombinationen wurden verschiedentlich beschrieben z.B. in Arzneim. Forsch. 20 (6), 781 (1970), Arzneim. Forsch. 22 (7), 1184 (1972), 4rzneim. Fcrsch. 22 (8), 1421 (1972), Arzneim. Forsch. 28 (9), 1564 (1978) oder sind Gegenstand von Patentanmeldungen, z.B.Studies with such combinations have been described variously e.g. in medic. Forsch. 20 (6), 781 (1970), Arzneimittel. Forsch. 22 (7), 1184 (1972), 4rzneim. Fcrsch. 22 (8), 1421 (1972), Medic. Forsch. 28 (9), 1564 (1978) or are the subject of patent applications, e.g.
- OS 29 20 738, DE - OS 30 10 397 und DE - OS 20 30 904.- OS 29 20 738, DE - OS 30 10 397 and DE - OS 20 30 904.
Die bekannten Nachteile der zytostatisch wirksamen Mittel konnten jedoch durch aie beschriebenen Kombinationen bisher noch nicht zufriedenstellend beseitigt werden. So sind die Kombinotionsmittel beispielsweise immer noch zu wenig wirksam. Die Mittel müssen aaher hoch dosiert werden, wodurch der Organismus durch die toxische iirkung stark belastet wird.The known disadvantages of the cytostatic agents could however, by means of all the combinations described, it has not yet been satisfactory be eliminated. For example, the combination lotions are still too few effective. The means have to be dosed aaher high, whereby the organism through the toxic effect is heavily burdened.
Überraschenderweise wurde nun gefunden, daj die er,induncsgemäßen Kombinationen von 5-«lkvlpyrimidinnukleosiden und deren Derivate der allgemeinen Formel I worin R1 ein Wasserstoffatom, ein Halogenatom, einen geraden oder verzweighten Alkylrest mit 1 bis 10 C-Atomen, einen geraden oder verzweigten Alkenylrest mit 2-6 C-Atomen, einen geradkettigen oder verzweigten (C2- C6)-Halogenalkyl-oder (C2 - C6)-Halogenalkenylrest, einen gegebenenfalls substituierten Fhenyl- oder Eenzylrest bedeuten, H H oder Halogen bedeuten, Y -H, wobei R³ - (C# - C#)-Alkyl 6 n = 1 - 4 ist, wobei R = H, geradkerttig ocer verzweigt (C1 - C6) - Alkyl ist, R5 und R6, die gleich oder verschieden sein können, ein Wasserstoffatom, eine gerade oder verzweigte Alkylgruppe mit 1 bis 6 C-Atomen, eine Phenyl-, Benzyl- oder Perfluoralkylgruppe mit 1 bis 6 C-Atomen sind, n = 0 - 8 ist, wobei Hal = F und Cl ist, bedeuten, in Kombination mit Arabinonukleosiden, z.B.Surprisingly, it has now been found that the indunksgemliche combinations of 5- «olpyrimidine nucleosides and their derivatives of the general formula I wherein R1 is a hydrogen atom, a halogen atom, a straight or branched alkyl radical with 1 to 10 carbon atoms, a straight or branched alkenyl radical with 2-6 carbon atoms, a straight-chain or branched (C2-C6) haloalkyl or (C2 - C6) haloalkenyl radical, an optionally substituted phenyl or eenzyl radical, HH or halogen, Y is -H, where R³ is - (C # - C #) - alkyl 6 n = 1 - 4, where R = H, straight or branched (C1 - C6) - alkyl, R5 and R6, which can be the same or different, a hydrogen atom, a straight or branched alkyl group with 1 to 6 carbon atoms, a phenyl, benzyl or perfluoroalkyl groups with 1 to 6 carbon atoms, n = 0 - 8, where Hal = F and Cl are, in combination with arabinonucleosides, for example
AraO (Cytosin-arabinosid) 5-Fluor-AraC 5-Ohloromercuri-AraC 5-Chloro-AraC eine starke zytostatische Wirkung ausüben, welche die Summe der Wirkungen der Einzelkomponenten weit übertrifft. Die synergistische Wirkung der beiden Komponenten läSt sich in vitro, z.B. in Zellkultur an L-1210-Mäuseleukämiezellen nachweisen.AraO (cytosine arabinoside) 5-fluoro-AraC 5-Ohloromercuri-AraC 5-chloro-AraC one have a strong cytostatic effect, which is the sum of the effects of the individual components far exceeds. The synergistic effect of the two components can be seen in in vitro, e.g. in cell culture on L-1210 mouse leukemia cells.
Die Verbindungen der allgemeinen Formel I sind entweder bekannt oder können in an sich bekannter Weise hergestellt werden, z.B. noch DE-PS 1 620 185, DE - OS 30 10 397, DE - Pat.Anm. 31 41 199.The compounds of the general formula I are either known or can be produced in a manner known per se, e.g. also DE-PS 1 620 185, DE - OS 30 10 397, DE - Pat. Ann. 31 41 199.
Diese Verbindungen können in der oC und/oder B-Form vorliegen. Besonders bevorzugte Verbindungen der Formel I sind: worin R eine Ethylgruppe und R2 ein Wasserstoffatom bedeuten und 1. Y für -H - Cl steht.These compounds can be in the oC and / or B form. Particularly preferred compounds of formula I are: wherein R denotes an ethyl group and R2 denotes a hydrogen atom and 1. Y denotes -H - Cl stands.
Die erfindungsgemäßen Arzneimittelzubereitungen mit einem Gehalt an mindestens einer der Verbindungen noch Anspruch 1 in Kombination mit einem Arabinonuklesid können in rorn von Pulver, Puder, Suspensionen, Lösungen, Emulsionen, Sprays, Pasten, Salben, Cremen, Tabletten una Dragees vrliegen und parenteral (intravenös, intradermal, intramusku lär, intrathecal u.ä.), oral, rektal, intravaginal, intranasal oder lokal verabreicht werden.The pharmaceutical preparations according to the invention with a content of at least one of the compounds according to claim 1 in combination with an arabinonucleside can be used in powder, powder, suspensions, solutions, emulsions, sprays, pastes, Ointments, creams, tablets and coated tablets are available and parenteral (intravenous, intradermal, intramuscular, intrathecal, etc.), oral, rectal, intravaginal, intranasal or local administered.
Die Zubereitung der erfindungsgemößen Arzneimittel erfolgt durch Vermischen oder Auflösen der Wirkstoffe zusammen mit oder in pharmazeutisch üblichen vertraglichen Hilfs-, Zusatz-und/oder Trägerstoffen, wie z.B. waßrigen oder nichtwäßrigen Lösungsmitteln, Stabilisatoren, Emulgatoren, Suspensions-, Dispersions- und Netzmitteln und dgl. sowie geeianeten Additiven und erforderlichenfalls auch Farb- und Aromastoffen.The pharmaceuticals according to the invention are prepared by mixing or dissolving the active ingredients together with or in pharmaceutically customary contractual Auxiliaries, additives and / or carriers, such as aqueous or non-aqueous solvents, Stabilizers, emulsifiers, suspending agents, dispersing agents and wetting agents and the like. as well as suitable additives and, if necessary, coloring and flavoring substances.
Die erfindungsgemäßen Arzneimittel sind als Zytostatlko zur Behandlung von malignen Erkrankungen vorteilhaft verwendbar.The medicaments according to the invention are used as cytostatics for treatment can be used advantageously for malignant diseases.
Durch die Kombination der beschriebenen Nukleoside und deren Derivate mit Arabinonukleosiden ergibt sich durch Potenzierung eine starke zytostatische Wirkung, welche die Summe der Wirkungen der Einzelkomponenten weit übertrifft. Die Belastung des Organismus durch toxische Verbindungen sowie unerwunschte Nebenwirkungen konnen durch aie geringere Dosierung herabgesetzt werden. kuerdem lassen sich kl eine Mengen hochwIrksamer Arzneimittel vorteilhafter verabreichen als größere Gaben schwach wirksamer Mittel.By combining the described nucleosides and their derivatives with arabinonucleosides potentiation results in a strong cytostatic Effect that far exceeds the sum of the effects of the individual components. the Exposure to the organism through toxic compounds and undesirable side effects can be reduced by a lower dosage. kuerdem can be kl give a large number of potent drugs more advantageously than larger doses weakly effective means.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823229169 DE3229169A1 (en) | 1982-08-05 | 1982-08-05 | Use of 5-alkylpyrimidine nucleosides and their derivatives as cytostatics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823229169 DE3229169A1 (en) | 1982-08-05 | 1982-08-05 | Use of 5-alkylpyrimidine nucleosides and their derivatives as cytostatics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3229169A1 true DE3229169A1 (en) | 1984-02-09 |
Family
ID=6170143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823229169 Withdrawn DE3229169A1 (en) | 1982-08-05 | 1982-08-05 | Use of 5-alkylpyrimidine nucleosides and their derivatives as cytostatics |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3229169A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988008001A1 (en) * | 1987-04-16 | 1988-10-20 | Aktiebolaget Astra | Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds |
| US5215970A (en) * | 1987-04-16 | 1993-06-01 | Medivir Ab | Nucleosides and nucleotide analogues, pharmaceutical composition and processes for the preparation of the compounds |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| US7419968B1 (en) | 1999-07-22 | 2008-09-02 | Celmed Oncology (Usa), Inc. | Methods for treating therapy-resistant tumors |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| US7465734B2 (en) | 1997-08-08 | 2008-12-16 | Celmed Oncology (Usa), Inc. | Methods and compositions for overcoming resistance to biologic and chemotherapy |
| US7601703B2 (en) | 1998-01-23 | 2009-10-13 | Celmed Oncology (Usa), Inc. | Enzyme catalyzed therapeutic agents |
-
1982
- 1982-08-05 DE DE19823229169 patent/DE3229169A1/en not_active Withdrawn
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988008001A1 (en) * | 1987-04-16 | 1988-10-20 | Aktiebolaget Astra | Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds |
| US5215970A (en) * | 1987-04-16 | 1993-06-01 | Medivir Ab | Nucleosides and nucleotide analogues, pharmaceutical composition and processes for the preparation of the compounds |
| US7465734B2 (en) | 1997-08-08 | 2008-12-16 | Celmed Oncology (Usa), Inc. | Methods and compositions for overcoming resistance to biologic and chemotherapy |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| US7601703B2 (en) | 1998-01-23 | 2009-10-13 | Celmed Oncology (Usa), Inc. | Enzyme catalyzed therapeutic agents |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| US7419968B1 (en) | 1999-07-22 | 2008-09-02 | Celmed Oncology (Usa), Inc. | Methods for treating therapy-resistant tumors |
| US7605144B2 (en) | 1999-07-22 | 2009-10-20 | Celmed Oncology (Usa), Inc. | Enzyme catalyzed therapeutic compounds |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |