DE2033357A1 - Palmitoyl-propandiol-(1,3)-phosphoric acid-5-trimethylaminopentyl - ester, immunological adjuvant affecting cell membrane surface activity - Google Patents
Palmitoyl-propandiol-(1,3)-phosphoric acid-5-trimethylaminopentyl - ester, immunological adjuvant affecting cell membrane surface activityInfo
- Publication number
- DE2033357A1 DE2033357A1 DE19702033357 DE2033357A DE2033357A1 DE 2033357 A1 DE2033357 A1 DE 2033357A1 DE 19702033357 DE19702033357 DE 19702033357 DE 2033357 A DE2033357 A DE 2033357A DE 2033357 A1 DE2033357 A1 DE 2033357A1
- Authority
- DE
- Germany
- Prior art keywords
- ester
- phosphoric acid
- palmitoyl
- propanediol
- trimethylaminopentyl
- 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
- 239000000568 immunological adjuvant Substances 0.000 title claims description 3
- 230000000694 effects Effects 0.000 title description 3
- 210000000170 cell membrane Anatomy 0.000 title description 2
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims abstract description 6
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 claims abstract 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 abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 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
- 239000002253 acid Substances 0.000 abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 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 5
- 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
- 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 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
- LQNRENFROWPIRV-UHFFFAOYSA-N 5-bromopentyl dihydrogen phosphate Chemical compound BrCCCCCOP(O)(O)=O LQNRENFROWPIRV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 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
- -1 5-bromopentylphosphoric acid chloride Chemical compound 0.000 description 1
- 206010057248 Cell death Diseases 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 238000009835 boiling Methods 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
- 230000009089 cytolysis Effects 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
- 230000008588 hemolysis Effects 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 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
- 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
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 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
- 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)
Abstract
Description
Palmitoyl-propandiol-(1,3)-phosphorsäure-5-trimethylaminopentylester und Verfahren zu dessen Herstellung Die Erfindung betrifft den pharmakologisch wertvollen Palmitoyl-propandiol-(1,;phosphorsäurew5-trimethylaminopentylester der Formel sowie dessen Herstellung.Palmitoyl-propanediol- (1,3) -phosphoric acid-5-trimethylaminopentyl ester and process for its preparation The invention relates to the pharmacologically valuable palmitoyl-propanediol- (1,; phosphoric acid w5-trimethylaminopentyl ester of the formula as well as its manufacture.
Die erfindungsgemäße neue Verbindung der Formel I wird hergestellt, indem man Propandiol-(l,3) mit Palmitoylchlorid zum Propandiol-(1,3)-monopalmitinsäureester der Formel acyliert, den Ester mit Phosphorsäure-mono-5-brompentylesterdichlorid zum l-ralmitoyl-propandiol-(l, 3)-phosphorsäure-5-brompentylester der Formel umsetzt, mit Trimethylamin aminiert und durch Entfernung er Bromidionen in das innere Salz der Formel I überführt.The novel compound of the formula I according to the invention is prepared by converting propanediol (1,3) with palmitoyl chloride to give the propanediol (1,3) monopalmitic acid ester of the formula acylated, the ester with phosphoric acid mono-5-bromopentyl ester dichloride to l-ralmitoyl-propanediol- (1,3) -phosphoric acid-5-bromopentyl ester of the formula reacted, aminated with trimethylamine and converted into the inner salt of the formula I by removing it.
Die erfindungsgemäße Substanz ist ein amorphes Pulver mit einem uncharakteristischen Schmelzverhalten. Die Charakterisierung erfolgt daher durch die DEnnschichtchromatographie (RF-Wert) und durch Elementaranalyse.The substance of the present invention is an amorphous powder with an uncharacteristic one Melting behavior. Characterization is therefore carried out using thin-layer chromatography (RF value) and by elemental analysis.
Die erfindungsgemäße Substanz weist grenzflächenaktive Eigenschaften auf und führt bei Verabreichung an den tierischen Organismus zu einer Veränderung der Grenzflächenaktivität von Zellmembranen. Höhere Konzentrationen verursachen Zytolyse z.B. Hämolyse, in sublytischen.losen ist dagegen eine dosisabhängige Veränderung der Nembrangrenzflächenaktivität zu beobachten. Die erfindungsgemäße neue Verbindung ist besonders als immunologisches Adjuvans zu verwenden.The substance according to the invention has surface-active properties and leads to a change when administered to the animal organism the interfacial activity of cell membranes. Cause higher concentrations On the other hand, cytolysis, e.g. hemolysis, in sublytic lots is a dose-dependent change to observe the membrane interface activity. The new compound according to the invention is particularly to be used as an immunological adjuvant.
Herstellungsbeispiel a) 5-Brompentylphosphorsäuredichlorid Zu 100 g (0,65 Mol) Phosphoroxychlorid und 25 ml Chloroform tropft man unter Rühren bei 000 eine Lösung von 25 g (0,15 Mol) 5-Brompentanol-(l) in 25 ml Chloroform. Man entfernt das Eisbad und läßt das Reaktionsgemisch 12 Stunden bei Raumtemwratur stehen. Man erwärmt nun für etwa zwei Stunden auf 10000, bis die Chlorwasserstoffentwicklung aufhört, destilliert das Reaktionsgemisch nach Abzug des Lösungsmittels im Vakuum und erhält 15 g (35 %) 5-Brompentylphosphorsäurechlorid (Kp0,05 mm 124-125°C; n20 1.4750). Das Phosphorylierungsmittel ist eine farblose, olige Flüssigkeit, die sich über 15000 zersetzt.Preparation example a) 5-bromopentylphosphoric acid dichloride To 100 g (0.65 mol) of phosphorus oxychloride and 25 ml of chloroform are added dropwise with stirring 000 a solution of 25 g (0.15 mol) of 5-bromopentanol- (l) in 25 ml of chloroform. Man removed the ice bath and left the reaction mixture to stand for 12 hours at room temperature. The mixture is then heated to 10,000 for about two hours until the evolution of hydrogen chloride ends, the reaction mixture is distilled after the solvent has been removed in vacuo and receives 15 g (35%) 5-bromopentylphosphoric acid chloride (boiling point 0.05 mm 124-125 ° C; n20 1.4750). The phosphorylating agent is a colorless, oily liquid that over 15000 decomposed.
b) Propandiol-(1,3)-monopalmitinsäureester Zu 5 g (66 mMol) Propandiol-(1,33, 5 ml Pyridin und 5 ml Chloroform tropft man unter Rühren bei 0°C 5 g (18 mMol) Palmitinsäurechlorid in 20 ml absolutem Chloroform. Nach 30 min.b) Propanediol (1,3) monopalmitic acid ester To 5 g (66 mmol) of propanediol (1,33, 5 ml of pyridine and 5 ml of chloroform are added dropwise with stirring at 0 ° C., 5 g (18 mmol) of palmitic acid chloride in 20 ml of absolute chloroform. After 30 min.
wird das Eisbad entfernt und bei Raumtemperatur 12 Stunden weitergerührt. Man dampft bei 40 bis 50°C (Bad) im Vakuum ein und gießt den öligen Rückstand auf 800 ml eisgekühlte 0,2 n Schwefelsäure. Der weiße Niederschlag wird abgesaugt, gut mit Wasser gewaschen und im Vakuum iber Blaugel getrocknet.the ice bath is removed and the mixture is stirred for a further 12 hours at room temperature. It is evaporated at 40 to 50 ° C (bath) in vacuo and the oily residue is poured on 800 ml ice-cold 0.2N sulfuric acid. The white precipitate is filtered off with suction, good washed with water and dried in vacuo over blue gel.
Umkristallisation aus Petroläther (40 bis 600C) ergibt 4 g Rohprodukt. Nach Chromatographie an Kieselgel und Umkristallisation aus Petroläther erhält man 3 g weiße Blättchen, die bei 43 bis 440 C schmelzen.Recrystallization from petroleum ether (40 to 60 ° C.) gives 4 g of crude product. After chromatography on silica gel and recrystallization from petroleum ether, one obtains 3 g of white flakes that melt at 43 to 440 C.
c) Pa1mitoyl-roandiol-(l' 3)-hoshorsäure-5-trimethvIaminonentylester Man gibt zu 15 ml absolutem Chloroform bei 0°C 4,5 g (4 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)-monopalmitinsäureester in 15 ml absolutem Chloroform zutropfen. Man bringt 6 Stunden auf Raumtemperatur und 12 Stunden auf 40QC.c) Palmitoyl-roanediol- (l '3) -horosic acid-5-trimethvinylaminonentyl ester 4.5 g (4 mmol) of anhydrous triethylamine are added to 15 ml of absolute chloroform at 0 ° C and 5.1 g (18 mmol) of 5-bromopentylphosphoric acid dichloride. While stirring and cooling with ice a solution of 2 g (6.5 mmol) of propanediol (l, 3) monopalmitic acid ester is left add dropwise in 15 ml of absolute chloroform. It is brought to room temperature for 6 hours and 12 hours on 40QC.
Dann kühlt man die dunkelgefärbte Lösung auf 0 0C und gibt zur Hydrolyse der Phosphorsäurechloride 15 ml 0,1 n KCl zu.The dark-colored solution is then cooled to 0 ° C. and added to hydrolysis 15 ml of 0.1 N KCl of the phosphoric acid chlorides.
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 getrocknet.After stirring for one hour and adding 25 ml of methanol, one sets with concentrated hydrochloric acid to about pH 3 and shake. The residue of the organic phase is dried over phosphorus pentoxide in a high vacuum.
Das Phosphorylierungsprodukt wird in 50 ml Butanol mit 10 ml Trimethylamin für 12 Stunden auf 55°C erwärmt, dann auf OOC abgekühlt, das ausgefällte kristalline Produkt abgesaugt, mit Aceton, Wasser und wiederum Aceton gewaschen. Zur vollständigen Reinigung wird nach Behandlung mit 1 g Silberacetat in 90 igem Methanol (30 Min. Rühren) an Kieselgel chromatographiert und danach aus Butanon umkristallisiert. Man erhält 1,4 g (41 Vo der Theorie) Palmitoyl-propandiol-(1,3)-phosphorsäure-5-trimethylaminopentylester.The phosphorylation product is dissolved in 50 ml of butanol with 10 ml of trimethylamine heated to 55 ° C for 12 hours, then cooled to OOC, the precipitated crystalline Sucked off product, washed with acetone, water and again acetone. To complete After treatment with 1 g of silver acetate in 90% methanol (30 min. Stirring) chromatographed on silica gel and then recrystallized from butanone. 1.4 g (41 vol of theory) of 5-trimethylaminopentyl palmitoyl-propanediol (1,3) -phosphoric acid are obtained.
Rf-Wert 0,15 in Chloroform/Methanol/Wasser 65:30:4 C27H58N07P (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 5,51Rf value 0.15 in chloroform / methanol / water 65: 30: 4 C27H58N07P (539.8) 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 (1)
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 true DE2033357A1 (en) | 1972-01-20 |
| DE2033357B2 DE2033357B2 (en) | 1979-06-07 |
| DE2033357C3 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 (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002202A3 (en) * | 1977-11-24 | 1979-10-31 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Phospholipid compounds and process for their preparation; process of peralkylation of organic nitrogen compounds |
| EP0036583A3 (en) * | 1980-03-26 | 1982-01-13 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Glycerine-3-phosphoric acid halogenalkyl ester, process for its preparation and further processing |
| 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 |
| 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 |
| US7595411B2 (en) | 1997-08-18 | 2009-09-29 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. | Phospholipid-analogous compounds |
| 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 (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002202A3 (en) * | 1977-11-24 | 1979-10-31 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Phospholipid compounds and process for their preparation; process of peralkylation of organic nitrogen compounds |
| EP0036583A3 (en) * | 1980-03-26 | 1982-01-13 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Glycerine-3-phosphoric acid halogenalkyl ester, process for its preparation and further processing |
| US5030733A (en) * | 1987-07-23 | 1991-07-09 | Hoechst-Roussel Pharmaceticals Incorporated | Hydroxy-, alkoxy- and benzyloxy-substituted phospholipids |
| 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 |
| US5036152A (en) * | 1988-03-10 | 1991-07-30 | Hoechst-Roussel Pharmaceuticals Incorporated | Alkoxycarbonylalkylphospholipids and alkylaminocarbonylalkylphospholipids |
| US7595411B2 (en) | 1997-08-18 | 2009-09-29 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. | Phospholipid-analogous compounds |
| US7939683B2 (en) | 1997-08-18 | 2011-05-10 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Phospholipid-analogous compounds |
| US8497388B2 (en) | 1997-08-18 | 2013-07-30 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften. E.V. | Phospholipid-analogous compounds |
| WO2021195555A1 (en) * | 2020-03-27 | 2021-09-30 | Travecta Therapeutics, Pte. Ltd. | Palmitoylethanolamide compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2033357C3 (en) | 1980-02-14 |
| DE2033357B2 (en) | 1979-06-07 |
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