DE2033357C3 - Palmitoyl-propandioKl 3) -phosphoric acid-S-trimethylaminophenyl ester and process for its preparation - Google Patents
Palmitoyl-propandioKl 3) -phosphoric acid-S-trimethylaminophenyl ester and process for its preparationInfo
- Publication number
- DE2033357C3 DE2033357C3 DE19702033357 DE2033357A DE2033357C3 DE 2033357 C3 DE2033357 C3 DE 2033357C3 DE 19702033357 DE19702033357 DE 19702033357 DE 2033357 A DE2033357 A DE 2033357A DE 2033357 C3 DE2033357 C3 DE 2033357C3
- Authority
- DE
- Germany
- Prior art keywords
- ester
- palmitoyl
- phosphoric acid
- propanediol
- formula
- 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.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- LVIHWUBDCDLTKO-UHFFFAOYSA-N OP(O)(OCCCCCBr)=O.Cl.Cl Chemical compound OP(O)(OCCCCCBr)=O.Cl.Cl LVIHWUBDCDLTKO-UHFFFAOYSA-N 0.000 claims description 3
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 239000000568 immunological adjuvant Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WJVQJXVMLRGNGA-UHFFFAOYSA-N 5-bromopentan-1-ol Chemical compound OCCCCCBr WJVQJXVMLRGNGA-UHFFFAOYSA-N 0.000 description 1
- LQNRENFROWPIRV-UHFFFAOYSA-N 5-bromopentyl dihydrogen phosphate Chemical compound BrCCCCCOP(O)(O)=O LQNRENFROWPIRV-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 239000002904 solvent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Die Erfindung betrifft den pharmakologisch wertvollen Palmitoyl-propandiol-(l,3)-phosphorsäure-5-lrimethylaminopentylester der FormelThe invention relates to the pharmacologically valuable palmitoyl-propanediol- (1,3) -phosphoric acid-5-trimethylaminopentyl ester the formula
CH2-O-CO-(CH2I14-CH,CH 2 -O-CO- (CH 2 I 14 -CH,
CH2 (I)CH 2 (I)
CH2-O-PO2-(CH2I5-N(CH3).,CH 2 -O-PO 2 - (CH 2 I 5 -N (CH 3 ).,
sowie dessen Herstellung.as well as its manufacture.
Die erfindungsgemäßc neue Verbindung der Formel I wird hergestellt, indem man Propandiol-(l,3) mit Palmitoylchlorid zum Propandiol-(l,3)-monopalmitinsäureesterder FormelThe novel compound of the formula I according to the invention is prepared by adding propanediol- (1,3) with Palmitoyl chloride to propanediol (1,3) monopalmitic acid ester formula
CH2—O—CO—(CH2)14—CH3 CH 2 -O-CO- (CH 2 ) 14 -CH 3
CH2 (II)CH 2 (II)
CH2OHCH 2 OH
acyliert, den Ester mit Phosphorsäure-mono-5-brompentylesterdichlorid zum 1-Palmitoyl-prcpandiol-(l,3)-phosphorsäure-5-brompentylester der Formelacylated, the ester with phosphoric acid mono-5-bromopentyl ester dichloride to the 1-palmitoyl-prcpandiol- (1,3) -phosphoric acid-5-bromopentyl ester of the formula
CH3-O—CO-(CH2)M—CH, CH2 (111)CH 3 -O-CO- (CH 2 ) M -CH, CH 2 (111)
CH,—O—PO2—(CH2)5 — Br OHCH, - O - PO 2 - (CH 2 ) 5 - Br OH
umsetzt, mit Trimethylamin aminiert und durch Entfernung der Bromidionen in das innere Salz der Formel I überführt.reacted, aminated with trimethylamine and by removing the bromide ions in the inner salt of the Formula I transferred.
Die erfindungsgemäße Substanz ist ein amorphes Pulver mit einem uncharakteristischen Schniclz.verhalten. Die Charakterisierung erfolgt daher durch die Dünnschichtchromatographic (RF-Wcrt) und durch Elementaranalyse.The substance according to the invention is an amorphous powder with an uncharacteristic Schniclz.behavior. The characterization is therefore carried out by thin-layer chromatography (RF-Wcrt) and by Elemental analysis.
Die erfindungsgemäße Substanz weist grenzflächenaktive Eigenschaften auf und führt bei Verabreichung an den tierischen Organismus zu einer Veränderung dor Grenzflächenaktivität von Zellmembranen. Höhere Konzentrationen verursachen Zytolysc z. B. Hämolysc, Vi in sublytischen Dosen ist dagegen eine dosisabhängige Veränderung der Membrangrcnzflächenaktivität zu beobachten. Die erfindungsgemäße neue Verbindung ist besonders als immunologisches Adjuvans zu verwenden. The substance according to the invention has surface-active properties and, when administered to the animal organism, leads to a change in the surface activity of cell membranes. Higher concentrations cause Zytolysc z. B. Hemolysc, Vi in sublytic doses, however, a dose-dependent change in membrane surface activity can be observed. The novel compound of the invention is particularly useful as an immunological adjuvant.
40 Herstellungsbeispiel a)5-Brompentylphosphorsäurcdichlorid 40 Preparation example a) 5-bromopentylphosphoric acid dichloride
Zu 100 g (0,65MoI) Phosphoroxychlorid und 25 ml Chloroform tropft man unter Rühren bei O0C eine Lösung von 25 g (0,15 Mol) 5-Brompentanol (I) in 25 ml Chloroform. Man entfernt das Eisbad und läßt das Reaktionsgemisch 12 Stunden bei Raumtemperatur stehen. Man erwärmt nun für etwa zwei Stunden auf 10O0C, bis die Chlorwasserstoffentwicklung aufhört, destilliert das Reaktionsgemisch nach Abzug des Lösungsmittels im Vakuum und erhält 15 g (35%)A solution of 25 g (0.15 mol) of 5-bromopentanol (I) in 25 ml of chloroform is added dropwise to 100 g (0.65 mol) of phosphorus oxychloride and 25 ml of chloroform while stirring at 0 ° C. The ice bath is removed and the reaction mixture is left to stand at room temperature for 12 hours. Is then heated for about two hours at 10O 0 C until the evolution of hydrogen chloride ceases, the reaction mixture is distilled after subtraction of the solvent in vacuo to give 15 g (35%)
S-Brompentylphosphorsäurechlorid (Kpo.os mmS-bromopentyl phosphoric acid chloride (Kpo.os mm
124-125-C; η 1.4750). Das Phosphorylierungsmittel ist eine farblose, ölige Flüssigkeit, die sich über 15O0C zersetzt.124-125-C; η 1.4750). The phosphorylating agent is a colorless, oily liquid which decomposes about 15O 0 C.
b) Propandiol-(l,3)-monopalmitinsäureeslerb) Propanediol (1,3) monopalmitic acid ester
Zu 5 g (66mMol) Propandiol-(1,3), 5 ml Pyridin undTo 5 g (66 mmol) of propanediol (1.3), 5 ml of pyridine and
W) 5 ml Chloroform tropft man unter Rühren bei 00C 5 g (ISmMoI) Palmitinsäurechlorid in 20 ml absolutem Chloroform. Nach 30 min wird das Eisbad entfernt und bei Raumtemperatur 12 Stunden weitergerührt. Man dampft bei 40 bis 500C (Bad) im Vakuum ein und gießtW) 5 ml of chloroform is added dropwise with stirring at 0 0 C 5 g (ISmMoI) of palmitoyl chloride in 20 ml of absolute chloroform. After 30 minutes, the ice bath is removed and stirring is continued for 12 hours at room temperature. It is evaporated at 40 to 50 0 C (bath) in a vacuum and poured
h5 den öligen Rückstand auf 800 ml eisgekühlte 0,2 n-Schwefelsäure. Der weiße Niederschlag wird abgesaugt, gut mit Wasser gewaschen und im Vakuum über Blaugel getrocknet.h5 the oily residue to 800 ml of ice-cold 0.2 N sulfuric acid. The white precipitate is filtered off with suction, washed well with water and in vacuo over blue gel dried.
Umkristailisation aus Petroläther (40 bis 600C) ergibt 4 g Rohprodukt Nach Chromatographie an Kieselgel und Umkristailisation aus Petroläther erhält man 3 g weiße Blättchen, die bei 43 bis 44° C schmelzen.Umkristailisation from petroleum ether (40 to 60 0 C) yields 4 g of crude product Chromatography on silica gel and Umkristailisation from petroleum ether obtained 3 g of white leaflets, melting at 43 to 44 ° C.
c) Palmitoyl-propandiol-( 1,3)-phosphorsäure-5-trimethylaminopentyIester c) Palmitoyl-propanediol- (1,3) -phosphoric acid-5-trimethylaminopentyl ester
Man gibt zu 15 ml absolutem Chloroform bei 00C 4,5 g (45 mMol) wasserfreies Triäthylamin und 5,1 g (18 mMol) 5-Brompentylphosphorsäuredichlorid. Unter Rühren und Eiskühlung läßt man eine Lösung von 2 g (6,5 mMol) Propandiol-(l,3)-monopa!mitinsäureester in 15 ml absolutem Chloroform zutropfen. Man bringt 6 Stunden auf Raumtemperatur und 12 Siunden auf 40°C. Dann kühlt man die dunkelgefärbte Lösung auf 00C und gibt zur Hydrolyse der Phosphorsäurechloride 15 ml 0,1 n-KCl zu. Nach einstündigem Rühren und Zugabe von 25 ml Methanol stellt man mit konzentrierter Salzsäure auf etwa pH 3 ein und schüttelt. Der Rückstand der organischen Phase wird im Hochvakuum über Phosphorpentoxyd getrocknetAre added to 15 ml of absolute chloroform at 0 0 C 4.5 g (45 mmol) of anhydrous triethylamine and 5.1 g (18 mmol) of 5-Brompentylphosphorsäuredichlorid. A solution of 2 g (6.5 mmol) of propanediol- (1,3) -monopa-mitic acid ester in 15 ml of absolute chloroform is added dropwise with stirring and ice-cooling. It is brought to room temperature for 6 hours and to 40 ° C. for 12 hours. The dark-colored solution is then cooled to 0 ° C. and 15 ml of 0.1 n-KCl are added to hydrolyze the phosphoric acid chlorides. After stirring for one hour and adding 25 ml of methanol, the pH is adjusted to about 3 with concentrated hydrochloric acid and the mixture is shaken. The residue of the organic phase is dried over phosphorus pentoxide in a high vacuum
Das Phosphorylierurigsprodukt wird in 50 ml Butanol mit 10 ml Trimethylarnin für 12 Stunden auf 55° C erwärmt, dann auf 00C abgekühlt, das ausgefällte kristalline Produkt abgesaugt, mit Aceton, Wasser und wiederum Aceton gewaschen. Zur vollständigen Reinigung wird nach Behandlung mit 1 g Silberacetat in 9O°/oigem Methanol (30 Min. Rühren) an Kieselgel Chromatographien und danach aus Butanon umkristallisiert. Man erhält 1,4 g (41% der Theorie) Palmitoyl-pro-The Phosphorylierurigsprodukt is heated in 50 ml of butanol with 10 ml Trimethylarnin for 12 hours at 55 ° C, then cooled to 0 0 C, filtered off with suction the precipitated crystalline product, washed with acetone, water and acetone again. For complete purification, after treatment with 1 g of silver acetate in 90% methanol (stirring for 30 minutes), it is chromatographed on silica gel and then recrystallized from butanone. 1.4 g (41% of theory) of palmitoyl-pro-
pandiol-(l,3)-phosphorsäure-5-trimethylaminopentylester. 5-trimethylaminopentyl pandiol (1,3) phosphoric acid.
Rf-Wert
65 : 30 : 4.Rf value
65: 30: 4.
0,150.15
inin
Chloroform/Methanol/WasserChloroform / methanol / water
C27H58NO7P (539.8)C 27 H 58 NO 7 P (539.8)
Ber.: C 60,0, H 10,83, N 2,59, P 5,74,
gef.: C 59.1. H 10,99, N 2.58. P 5.51.Calc .: C 60.0, H 10.83, N 2.59, P 5.74,
found: C 59.1. H 10.99, N 2.58. P 5.51.
Claims (3)
CH2 (I)CH 2 -O-CO- (CH 2 I 1+ -CH 3
CH 2 (I)
OCH 2 -O-PO, - (CH 2 ) 5 -N (CH 3 ) 3
O
CH2 (II)CH 2 -O-CO- (CH 2 I 14 -CH 3
CH 2 (II)
CH2 (III)CH 2 -O-CO- (CH 2 J 14 -CH 3
CH 2 (III)
OHCH 2 -O-PO 2 - (CH 2 I 5 -Br
OH
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702033357 DE2033357C3 (en) | 1970-07-06 | 1970-07-06 | Palmitoyl-propandioKl 3) -phosphoric acid-S-trimethylaminophenyl ester and process for its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702033357 DE2033357C3 (en) | 1970-07-06 | 1970-07-06 | Palmitoyl-propandioKl 3) -phosphoric acid-S-trimethylaminophenyl ester and process for its preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2033357A1 DE2033357A1 (en) | 1972-01-20 |
| DE2033357B2 DE2033357B2 (en) | 1979-06-07 |
| DE2033357C3 true DE2033357C3 (en) | 1980-02-14 |
Family
ID=5775898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702033357 Expired DE2033357C3 (en) | 1970-07-06 | 1970-07-06 | Palmitoyl-propandioKl 3) -phosphoric acid-S-trimethylaminophenyl ester and process for its preparation |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2033357C3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382035A (en) | 1980-03-26 | 1983-05-03 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Glycerol-3-phosphoric acid halogenoalkyl esters and processes for their preparation and further conversion |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2752553C2 (en) * | 1977-11-24 | 1985-07-25 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Novel phospholipid-like compounds, their use in the manufacture of plant hybrids and processes for their manufacture |
| US5145844A (en) * | 1987-07-23 | 1992-09-08 | Hoechst-Roussel Pharmaceuticals Incorporated | Methods of using hydroxy-, alkoxy- and benzyloxy-substituted phospholipids to treat phospholipase A2 -mediated conditions and to alleviate pain |
| US5030733A (en) * | 1987-07-23 | 1991-07-09 | Hoechst-Roussel Pharmaceticals Incorporated | Hydroxy-, alkoxy- and benzyloxy-substituted phospholipids |
| US5036152A (en) * | 1988-03-10 | 1991-07-30 | Hoechst-Roussel Pharmaceuticals Incorporated | Alkoxycarbonylalkylphospholipids and alkylaminocarbonylalkylphospholipids |
| JP4550271B2 (en) | 1997-08-18 | 2010-09-22 | マックス−プランク−ゲゼルシャフト・ツア・フェルデルング・デア・ヴィッセンシャフテン・エー・ファオ | Phospholipid analog |
| WO2021195555A1 (en) * | 2020-03-27 | 2021-09-30 | Travecta Therapeutics, Pte. Ltd. | Palmitoylethanolamide compounds |
-
1970
- 1970-07-06 DE DE19702033357 patent/DE2033357C3/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382035A (en) | 1980-03-26 | 1983-05-03 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Glycerol-3-phosphoric acid halogenoalkyl esters and processes for their preparation and further conversion |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2033357B2 (en) | 1979-06-07 |
| DE2033357A1 (en) | 1972-01-20 |
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