NO131988B - - Google Patents
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- Publication number
- NO131988B NO131988B NO2557/71A NO255771A NO131988B NO 131988 B NO131988 B NO 131988B NO 2557/71 A NO2557/71 A NO 2557/71A NO 255771 A NO255771 A NO 255771A NO 131988 B NO131988 B NO 131988B
- Authority
- NO
- Norway
- Prior art keywords
- ester
- phosphoric acid
- propanediol
- formula
- acylpropanediol
- Prior art date
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 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
- 241001465754 Metazoa Species 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001506 immunosuppresive effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 210000000952 spleen Anatomy 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010062016 Immunosuppression Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical class CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- 206010057248 Cell death Diseases 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229960001231 choline Drugs 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
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 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
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 230000004727 humoral immunity Effects 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 239000007928 intraperitoneal injection 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
- 150000004682 monohydrates Chemical class 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate 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
- 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
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2033361A DE2033361C3 (de) | 1970-07-06 | 1970-07-06 | Acylpropandiol-(13)-phosphorsäurecholinester und Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131988B true NO131988B (OSRAM) | 1975-05-26 |
| NO131988C NO131988C (OSRAM) | 1975-09-03 |
Family
ID=5775903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2557/71A NO131988C (OSRAM) | 1970-07-06 | 1971-07-05 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3694474A (OSRAM) |
| KR (1) | KR780000027B1 (OSRAM) |
| AT (1) | AT300837B (OSRAM) |
| BE (1) | BE769533A (OSRAM) |
| BG (1) | BG17813A3 (OSRAM) |
| CA (1) | CA979918A (OSRAM) |
| DE (1) | DE2033361C3 (OSRAM) |
| ES (1) | ES392735A1 (OSRAM) |
| FR (1) | FR2100867B1 (OSRAM) |
| GB (1) | GB1319402A (OSRAM) |
| HU (1) | HU163186B (OSRAM) |
| IE (1) | IE35441B1 (OSRAM) |
| IL (1) | IL37224A (OSRAM) |
| NL (1) | NL7109243A (OSRAM) |
| NO (1) | NO131988C (OSRAM) |
| PH (1) | PH9282A (OSRAM) |
| RO (1) | RO62390A (OSRAM) |
| SE (1) | SE382062B (OSRAM) |
| SU (1) | SU517261A3 (OSRAM) |
| ZA (1) | ZA714374B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163748A (en) * | 1973-09-06 | 1979-08-07 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Propane-1,3-diol phosphatides and method of preparing the same |
| DE2619686C2 (de) * | 1976-05-04 | 1986-08-07 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Verwendung eines Lysolecithins zur Tumorbehandlung |
| US5030733A (en) * | 1987-07-23 | 1991-07-09 | Hoechst-Roussel Pharmaceticals Incorporated | Hydroxy-, alkoxy- and benzyloxy-substituted phospholipids |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542820A (en) * | 1968-10-08 | 1970-11-24 | American Home Prod | Alpha,omega - alkanediolphosphorylalkanolamine derivatives and process for preparing thereof |
-
1970
- 1970-07-06 DE DE2033361A patent/DE2033361C3/de not_active Expired
-
1971
- 1971-06-17 BG BG017836A patent/BG17813A3/xx unknown
- 1971-06-30 ES ES392735A patent/ES392735A1/es not_active Expired
- 1971-07-02 SU SU1680403A patent/SU517261A3/ru active
- 1971-07-02 US US159552A patent/US3694474A/en not_active Expired - Lifetime
- 1971-07-05 RO RO7100067557A patent/RO62390A/ro unknown
- 1971-07-05 IL IL37224A patent/IL37224A/en unknown
- 1971-07-05 BE BE769533A patent/BE769533A/xx unknown
- 1971-07-05 NO NO2557/71A patent/NO131988C/no unknown
- 1971-07-05 SE SE7108672A patent/SE382062B/xx unknown
- 1971-07-05 NL NL7109243A patent/NL7109243A/xx not_active Application Discontinuation
- 1971-07-05 ZA ZA714374A patent/ZA714374B/xx unknown
- 1971-07-05 HU HUTO855A patent/HU163186B/hu unknown
- 1971-07-05 GB GB3144771A patent/GB1319402A/en not_active Expired
- 1971-07-06 AT AT584171A patent/AT300837B/de not_active IP Right Cessation
- 1971-07-06 CA CA117,464A patent/CA979918A/en not_active Expired
- 1971-07-06 IE IE865/71A patent/IE35441B1/xx unknown
- 1971-07-06 FR FR7124656A patent/FR2100867B1/fr not_active Expired
- 1971-07-06 KR KR7100926A patent/KR780000027B1/ko not_active Expired
- 1971-07-06 PH PH12606*UA patent/PH9282A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU163186B (OSRAM) | 1973-06-28 |
| NO131988C (OSRAM) | 1975-09-03 |
| IE35441B1 (en) | 1976-02-18 |
| IE35441L (en) | 1972-01-06 |
| ES392735A1 (es) | 1973-08-01 |
| SU517261A3 (ru) | 1976-06-05 |
| IL37224A0 (en) | 1971-10-20 |
| GB1319402A (en) | 1973-06-06 |
| BE769533A (fr) | 1971-11-16 |
| BG17813A3 (bg) | 1973-12-25 |
| CA979918A (en) | 1975-12-16 |
| NL7109243A (OSRAM) | 1972-01-10 |
| DE2033361B2 (de) | 1979-06-07 |
| FR2100867A1 (OSRAM) | 1972-03-24 |
| DE2033361C3 (de) | 1980-02-21 |
| DE2033361A1 (de) | 1972-01-20 |
| KR780000027B1 (en) | 1978-03-10 |
| FR2100867B1 (OSRAM) | 1975-08-01 |
| US3694474A (en) | 1972-09-26 |
| ZA714374B (en) | 1972-04-26 |
| RO62390A (fr) | 1978-02-15 |
| SE382062B (sv) | 1976-01-12 |
| IL37224A (en) | 1974-12-31 |
| PH9282A (en) | 1975-08-05 |
| AT300837B (de) | 1972-08-10 |
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