DD155169A1 - PROCESS FOR THE PREPARATION OF 0- (1-0-ALKYL-3-DESOXY-3-FLUOR-GLYCER-2-YL) -O '/ OMEGA- (N, N, N-TRIMETHYLAMMONIO) ALKYL / PHOSPHATES - Google Patents
PROCESS FOR THE PREPARATION OF 0- (1-0-ALKYL-3-DESOXY-3-FLUOR-GLYCER-2-YL) -O '/ OMEGA- (N, N, N-TRIMETHYLAMMONIO) ALKYL / PHOSPHATES Download PDFInfo
- Publication number
- DD155169A1 DD155169A1 DD22590480A DD22590480A DD155169A1 DD 155169 A1 DD155169 A1 DD 155169A1 DD 22590480 A DD22590480 A DD 22590480A DD 22590480 A DD22590480 A DD 22590480A DD 155169 A1 DD155169 A1 DD 155169A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- preparation
- deoxy
- phosphates
- fluoro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- -1 N, N, N-TRIMETHYLAMMONIO Chemical class 0.000 title description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000021317 phosphate Nutrition 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229960004956 glycerylphosphorylcholine Drugs 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- LLHRMWHYJGLIEV-UHFFFAOYSA-N desoxy Chemical group COC1=CC(CCN)=CC(OC)=C1C LLHRMWHYJGLIEV-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von O(1-O-Alkyl-3-desoxy-3-fluor-glycer-2-yl)-O'/omega-(N,N,N,-trimethylammonio)alkyl/-phosphaten der allgemeinen Formel I,in der R einen langkettigen gesaettigten oder ungesaettigten Kohlenwasserstoffrest mit mindestens 8 C-Atomen, der auch substituiert sein kann, bedeutet und n = 2 bis 6 ist. Das Ziel der Erfindung besteht darin, ein geeignetes, technisch anwendbares Verfahren zur Herstellung dieser Verbindungen zu entwickeln. Erfindungsgemaess werden 1-O-Alkyl-3-desoxy-3-fluor-glycero-2-phosphorsaeure-omega-halogenalkylester mit Trimethylamin bei Temperaturen zwischen 30 und 90 Grad C umgesetzt.The invention relates to a process for the preparation of O (1-O-alkyl-3-deoxy-3-fluoro-glycer-2-yl) -O '/ omega (N, N, N, -trimethylammonio) alkyl / phosphates of the general formula I in which R is a long-chain saturated or unsatured hydrocarbon radical having at least 8 C atoms, which may also be substituted, and n = 2 to 6. The object of the invention is to develop a suitable, technically applicable process for the preparation of these compounds. According to the invention, 1-O-alkyl-3-deoxy-3-fluoro-glycero-2-phosphoric acid-omega-haloalkyl esters are reacted with trimethylamine at temperatures between 30 and 90.degree.
Description
225904225904
Dr. H. Brachwitz Prof. Dr. P. Langen J. SchildtDr. H. Brachwitz Prof. dr. P. Langen J. Schildt
"Verfahren zur Herstellung von 0-(1-0~Alkyl-3-desoxy-3-fluor~ fflycer-2~yl)~0'-/^)-(N,I,H-$rimethylammonio)alkyl/-phosphaten""Process for the preparation of O- (1-0-alkyl-3-deoxy-3-fluoro-5-fluoro -2-yl) ~ O '- / ^) - (N, I, H-trimethylammonio) alkyl phosphates "
Anwendungsgebiet der Erfindung Applying dungsg ebiet the invention
Die Erfindung betrifft ein Verfahren zur Herstellung von 0-(1-0-Alkyl-3-desoxy-3-fluor-glycer-2-yl)-Ot-/»-(lT,N,I-:liri- methylammoniο)alkyl/-phosphaten der allgemeinen Formel I,The invention relates to a process for the preparation of O- (1-0-alkyl-3-deoxy-3-fluoro-glycer-2-yl) -O t - / »- (1T, N, 1 : 1-methylammonium) alkyl / phosphates of the general formula I,
I 0"I 0 "
CH2-P ICH 2 -PI
in der R einen langkettigen gesättigten oder ungesättigten Kohlenwasserstoffrest mit mindestens 8 C-Atomen, wobei die Reste auch substituiert sein können, bedeutet und η = 2 bis 6 ist.in which R is a long-chain saturated or unsaturated hydrocarbon radical having at least 8 C atoms, where the radicals may also be substituted, and η = 2 to 6.
Die Verbindungen I sind Strukturanaloge der natürlich vorkommenden Diacyl-glycerophosphocholine (Lecithine) bzw, Monoacyl-glycerophosphocholine (Lysolecithine). Sie unterscheiden sich von diesen jedoch in der Stellung der Phosphatgruppierung und im Vorhandensein eines Fluoratoms anstelle einer Acyloxy- bzw* OH-Gruppe.The compounds I are structural analogues of the naturally occurring diacyl-glycerophosphocholine (lecithins) or, respectively, monoacyl-glycerophosphocholines (lysolecithins). However, they differ from these in the position of the phosphate grouping and in the presence of a fluorine atom instead of an acyloxy or * OH group.
Anwendungsgebiet der Erfindung ist die chemische bzw. pharmazeutische Industrie.Field of application of the invention is the chemical or pharmaceutical industry.
Charakteristik der bekannten technischen Lösungen Es ist bekannt, daß durch Umsetzung von 1,3-Di~0~alkylglycerophosphorsäure-w-bromalkylestern mit Trimethylamin 1,3-Di-O-alkyl-glycero-2-phosphocholine entstehen (H. Eibl, D. Characteristic of the Known Technical Solutions It is known that 1,3-di-O-alkyl-glycero-2-phosphocholines are formed by reaction of 1,3-di-O-alkylglycerophosphoric acid W-bromoalkyl esters with trimethylamine (H. Eibl, D ,
- 2 - 22 5 9 O^- 2 - 22 5 9 O ^
Arnold, H. U. Weltzien, 0, Westphal, Liebigs Ann. Chem. 709, 226 - 230 (1967))- Pluorhaltige flycero-^-phosphocholine und. Analoge mit verlängerter Trimethylammonio~*alkyl-Gruppierung vom Typ I sind bisher in der Literatur noch nicht beschrieben worden»Arnold, H.U. Weltzien, 0, Westphal, Liebigs Ann. Chem. 709, 226-230 (1967)) - Pluorhaltige flycero - - - phosphocholines and. Analogs with extended trimethylammonio ~ * alkyl grouping of type I have not yet been described in the literature »
Ziel dergoal of
Ziel der Erfindung ist es, ein geeignetes, technisch anwendbares Verfahren zur Herstellung von 0-(1-0-Alkyl-3-desoxy-3-The aim of the invention is to provide a suitable, industrially applicable process for the preparation of O- (1-0-alkyl-3-deoxy-3-
phösphateh vom Typ I zu entwickelnphösphateh type I to develop
Darlegung; des presentation; of
Das Yifesen der vorliegenden Erfindung besteht darin, daß man 1-0-Alkyl-3™desoxy~3-fluor-glycerophosphorsäure-ii>-halogenalkylester der allgemeinen Formel II,The Yifesen the present invention consists in that 1-0-alkyl-3 ™ desoxy ~ 3-fluoro-glycerophosphoric acid-ii> -halogenalkylester of the general formula II,
CHp-OR j 0CHp OR j 0
CH-I-O(CH^)nXCH-IO (CH 2) n X
[ GH CH2-F . II[GH CH 2 -F. II
in der R einen langkettigen gesättigten oder ungesättigten Kohlenwasserstoffrest mit mindestens 8 C-Atomen, der auch substituiert sein kann, Σ ein Halogenatom, vorzugsweise Cl, Br oder J, bedeutet und η.= 2 bis 6 ist, mit Trimethylamin umsetzt und die entstandenen I-Halogenide in die 0-(1-0-Alkyl-3-desoxy~3-fluor-glycer-2-yl)-0'-/^;-(N,li,U-iörimethylammonio)alkyl/-phosphate vom Typ I überführt. Im allgemeinen wird die Umsetzung in der Weise, durchgeführt, daß man die Verbindung II mit überschüssigem Trimethyl-amin in Anwesenheit von Lösungsmitteln wie Wasser, Chloroform, i-Propanol und Acetonitril oder Gemischen derselben auf Temperaturen zwischen 30 und 12O0C, vorzugsweise 500C,erhitzt. Die Überführung der entstandenen I-Halogenide in die Verbindung I erfolgt nach an sich bekannten Methoden, z. B. durch Ionenaustausch oder Behandlung der quartären Ammoniumsalze mitin which R is a long-chain saturated or unsaturated hydrocarbon radical having at least 8 C atoms, which may also be substituted, Σ is a halogen atom, preferably Cl, Br or J, and η. = 2 to 6, is reacted with trimethylamine and the resulting I Halides in the 0- (1-0-alkyl-3-deoxy-3-fluoro-glycer-2-yl) -0 '- / ^, (N, li, U- i örimethylammonio) alkyl / phosphates of Type I transferred. In general, the reaction is carried out in such a way that the compound II with excess trimethylamine in the presence of solvents such as water, chloroform, i-propanol and acetonitrile or mixtures thereof at temperatures between 30 and 12O 0 C, preferably 50 0 C, heated. The conversion of the resulting I-halides into the compound I is carried out according to known methods, for. B. by ion exchange or treatment of the quaternary ammonium salts with
- 3 - 2 2 5 9 04- 3 - 2 2 5 9 04
Silberacetat. Die Reinigung der Verbindungen erfolgt im allgemeinen durch Säulenchromatographie an Kieselgel. Die erfindungsgemäß hergestellten Substanzen gehören einer biologisch aktiven Verbindungsklasse an.Silver acetate. The purification of the compounds is generally carried out by column chromatography on silica gel. The substances produced according to the invention belong to a biologically active class of compounds.
Das 3-Desoxy-3~fluor-1-0-hezadecyl-glycerophosphocholin (I, R = CjgHoo; η = 2) weist z. B. eine cancerostatische Wirksamkeit auf und bewirkt in einer Konzentration von 2 · 1Cf^ M eine 50 %ige Hemmung des Y/achstums von Ehrlich-Ascites-Tumorsellen in vitroThe 3-deoxy-3-fluoro-1-0-hezadecyl-glycerophosphocholine (I, R = CjgHoo; η = 2) has z. B. a cancerostatic activity and causes in a concentration of 2 · 1Cf ^ M a 50% inhibition of the Y / achstums of Ehrlich ascites tumor cells in vitro
Die Erfindung wird an nachstehendem Beispiel erläutert. The invention will be illustrated by the following example.
Aü^fjihr unggb e i sp i e 1Aj ^ fjih r unggb ei spie 1
3-Desoxy~3-fluor-1-0-hexadecyl~glycero-2-phosphocholin (I; R = Q^H33, η = 2) 3-deoxy-3-fluoro-1-O-hexadecyl-glycero-2-phosphocholine (I; R = Q H 33 , η = 2)
750 mg (1.6 ηπηοΐ) 3-Desoxy~3-flu.or— i-O-hexadeoyl-glycero-2-phosphcrsäure-bromethylester (II, R = Cj^Ho3» x = Br, n= 2) v/erden in 4*5 ml Chloroform gelöst und auf 500C erwärmt· Es werden 7.5 ml i-Propanol und 7.5 ml Acetonitril und anschließend H ml einer 33 &Lgen wäßrigen Trimethylaminlösung zugegeben. Hach lOstündigem Erhitzen auf 500C wird das Lösungsmittel im Vakuum eingeengt; man erhält ein gelbes Öl,"welches säulenchromatographisch an 100 g Kieselgel Mallinckrodt, 100 mesh, gereinigt wird. Elutionsmittel: Chloroform/Methanol/Ammoniak (25 %ige wäßrige Lösung), 65 : 25 : 3 v/v/v. Aus den Fraktionen 24 bis 70 ( je 10 ml) werden 0,42 g (58.5 % d, Th*) 3-Desoxy~3-flßor~1-0-hexadecyl-glycero-2-phosphocholin erhalten. P. 157 - 1590C (Chloroform/Aceton 1 : 1).750 mg (1.6 ηπηοΐ) of 3-deoxy-3-fluoro-1-O-hexadeoyl-glycero-2-phosphorous acid bromoethyl ester (II, R = Cj ^ Ho 3 x = Br, n = 2) are prepared in 4 * 5 ml of chloroform are dissolved and heated to 50 ° C. · 7.5 ml of i-propanol and 7.5 ml of acetonitrile and then H ml of a 33% aqueous trimethylamine solution are added. Hach lOstündigem heating at 50 0 C the solvent was evaporated in vacuo; A yellow oil is obtained, which is purified by column chromatography on 100 g of Mallinckrodt silica gel, 100 mesh, eluent: chloroform / methanol / ammonia (25% aqueous solution), 65: 25: 3 v / v / v From 24 to 70 (10 ml each) 0.42 g (58.5 % d, Th *) of 3-deoxy-3-fluoro-1-O-hexadecyl-glycero-2-phosphocholine are obtained P. 157-159 0 C ( Chloroform / acetone 1: 1).
Claims (1)
CH-O-P-O(CH9) -CH 9 -OR
CH-OPO (CH 9 ) -
IOCH 9 -OR
IO
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD22590480A DD155169A1 (en) | 1980-12-10 | 1980-12-10 | PROCESS FOR THE PREPARATION OF 0- (1-0-ALKYL-3-DESOXY-3-FLUOR-GLYCER-2-YL) -O '/ OMEGA- (N, N, N-TRIMETHYLAMMONIO) ALKYL / PHOSPHATES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD22590480A DD155169A1 (en) | 1980-12-10 | 1980-12-10 | PROCESS FOR THE PREPARATION OF 0- (1-0-ALKYL-3-DESOXY-3-FLUOR-GLYCER-2-YL) -O '/ OMEGA- (N, N, N-TRIMETHYLAMMONIO) ALKYL / PHOSPHATES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD155169A1 true DD155169A1 (en) | 1982-05-19 |
Family
ID=5527769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD22590480A DD155169A1 (en) | 1980-12-10 | 1980-12-10 | PROCESS FOR THE PREPARATION OF 0- (1-0-ALKYL-3-DESOXY-3-FLUOR-GLYCER-2-YL) -O '/ OMEGA- (N, N, N-TRIMETHYLAMMONIO) ALKYL / PHOSPHATES |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD155169A1 (en) |
-
1980
- 1980-12-10 DD DD22590480A patent/DD155169A1/en unknown
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