CA1063615A - Synthetic phospholipids, a process for their manufacture and their use - Google Patents
Synthetic phospholipids, a process for their manufacture and their useInfo
- Publication number
- CA1063615A CA1063615A CA232,801A CA232801A CA1063615A CA 1063615 A CA1063615 A CA 1063615A CA 232801 A CA232801 A CA 232801A CA 1063615 A CA1063615 A CA 1063615A
- Authority
- CA
- Canada
- Prior art keywords
- phosphoric acid
- reacted
- product
- moisture
- obtained according
- 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
- 238000000034 method Methods 0.000 title claims abstract description 42
- 230000008569 process Effects 0.000 title claims abstract description 37
- 150000003904 phospholipids Chemical class 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 9
- -1 1,2,3,4,5 pentamyristoyl-D-mannitol Chemical compound 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000007717 exclusion Effects 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 16
- 229940067631 phospholipid Drugs 0.000 claims 3
- KAIIJQURNKGJNV-UHFFFAOYSA-N (2-hexadecoxy-3-hydroxypropyl) hexadecanoate Chemical compound CCCCCCCCCCCCCCCCOC(CO)COC(=O)CCCCCCCCCCCCCCC KAIIJQURNKGJNV-UHFFFAOYSA-N 0.000 claims 1
- JEJLGIQLPYYGEE-XIFFEERXSA-N 1,2-dipalmitoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCCCCCC JEJLGIQLPYYGEE-XIFFEERXSA-N 0.000 claims 1
- RBGYBTJRVDFANH-UHFFFAOYSA-N 1,3-dioctoxypropan-2-ol Chemical compound CCCCCCCCOCC(O)COCCCCCCCC RBGYBTJRVDFANH-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- JEJLGIQLPYYGEE-UHFFFAOYSA-N glycerol dipalmitate Natural products CCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCC JEJLGIQLPYYGEE-UHFFFAOYSA-N 0.000 claims 1
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 abstract description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 229910052698 phosphorus Inorganic materials 0.000 description 19
- 239000000787 lecithin Substances 0.000 description 16
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 229940067606 lecithin Drugs 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
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- UDIPIOHLDFSMLR-UHFFFAOYSA-N 2-phenylmethoxypropane-1,3-diol Chemical compound OCC(CO)OCC1=CC=CC=C1 UDIPIOHLDFSMLR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- XOYXELNNPALJIE-UHFFFAOYSA-N trimethylazanium phosphate Chemical compound C[NH+](C)C.C[NH+](C)C.C[NH+](C)C.[O-]P([O-])([O-])=O XOYXELNNPALJIE-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/553—Phospholipids, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2437832A DE2437832C2 (de) | 1974-08-06 | 1974-08-06 | Phospholipide, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063615A true CA1063615A (en) | 1979-10-02 |
Family
ID=5922578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,801A Expired CA1063615A (en) | 1974-08-06 | 1975-08-05 | Synthetic phospholipids, a process for their manufacture and their use |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5143723A (nl) |
| AU (1) | AU8370575A (nl) |
| BE (1) | BE832182A (nl) |
| CA (1) | CA1063615A (nl) |
| CH (1) | CH615191A5 (nl) |
| DE (1) | DE2437832C2 (nl) |
| DK (1) | DK355575A (nl) |
| FR (1) | FR2372631A1 (nl) |
| GB (1) | GB1522664A (nl) |
| IE (1) | IE41597B1 (nl) |
| IT (1) | IT1044020B (nl) |
| LU (1) | LU73148A1 (nl) |
| NL (1) | NL7509359A (nl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE442014B (sv) * | 1976-10-12 | 1985-11-25 | Barry D Sears | Syntetisk fosfatidyl-kvarter ammoniumforening till anvendning for solubilisering eller emulgering av vattenolosliga foreningar |
| DE2752125A1 (de) * | 1977-11-22 | 1979-05-23 | Max Planck Gesellschaft | Neue phosphororganische ringverbindungen, ihre herstellung und verwendung |
| DE3476770D1 (en) * | 1983-04-11 | 1989-03-23 | Meito Sangyo Kk | Production of primary or secondary alcohol derivatives of phospholipids by the enzymatic technique |
| DE3417235A1 (de) * | 1983-12-15 | 1985-06-27 | Rudolf V. Dr.rer.nat Dipl.-Chem. 5024 Pulheim Noronha | Zahnpflegemittel enthaltend phosphatide |
| DE3663255D1 (en) * | 1985-07-26 | 1989-06-15 | Sankyo Co | Phosphate ester derivatives, their preparation and their therapeutic use |
| GB2267033B (en) * | 1992-03-07 | 1996-01-24 | David Garnett | Lysophospholipid Animal Feed Supplement |
| GB9301701D0 (en) * | 1993-01-28 | 1993-03-17 | Biocompatibles Ltd | New zwitterionic materials |
| WO1995028146A1 (en) * | 1994-04-15 | 1995-10-26 | Hemagen/Pfc | Fluorochemical emulsions containing 1,3-dialkylglycerophosphoryl choline surfactants and methods of use |
| WO2002009678A2 (en) | 2000-07-31 | 2002-02-07 | Ottawa Heart Institute Research Corporation | Charged phospholipid compositions and methods for their use |
-
1974
- 1974-08-06 DE DE2437832A patent/DE2437832C2/de not_active Expired
-
1975
- 1975-08-04 IT IT26086/75A patent/IT1044020B/it active
- 1975-08-05 CA CA232,801A patent/CA1063615A/en not_active Expired
- 1975-08-05 LU LU73148A patent/LU73148A1/xx unknown
- 1975-08-05 DK DK355575A patent/DK355575A/da unknown
- 1975-08-05 GB GB32664/75A patent/GB1522664A/en not_active Expired
- 1975-08-05 IE IE1733/75A patent/IE41597B1/en unknown
- 1975-08-06 CH CH1028375A patent/CH615191A5/de not_active IP Right Cessation
- 1975-08-06 NL NL7509359A patent/NL7509359A/nl not_active Application Discontinuation
- 1975-08-06 BE BE158989A patent/BE832182A/xx not_active IP Right Cessation
- 1975-08-06 FR FR7524487A patent/FR2372631A1/fr active Granted
- 1975-08-06 JP JP50095095A patent/JPS5143723A/ja active Pending
- 1975-08-06 AU AU83705/75A patent/AU8370575A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5143723A (en) | 1976-04-14 |
| FR2372631A1 (fr) | 1978-06-30 |
| IE41597B1 (en) | 1980-02-13 |
| GB1522664A (en) | 1978-08-23 |
| NL7509359A (nl) | 1976-02-10 |
| DK355575A (da) | 1976-02-07 |
| AU8370575A (en) | 1977-02-10 |
| CH615191A5 (en) | 1980-01-15 |
| LU73148A1 (nl) | 1977-04-13 |
| IE41597L (en) | 1976-02-06 |
| IT1044020B (it) | 1980-02-29 |
| FR2372631B1 (nl) | 1979-06-22 |
| DE2437832A1 (de) | 1976-02-26 |
| BE832182A (fr) | 1976-02-06 |
| DE2437832C2 (de) | 1986-04-10 |
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