CA1108177A - Derives de phospholipides - Google Patents

Derives de phospholipides

Info

Publication number: CA1108177A
Authority: CA; Canada
Prior art keywords: oleyl; phosphatidylethanolamine; derivatives; aliphatic acids; milliliters
Prior art date: 1979-06-18
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

Application number

CA329,962A

Other languages

English (en)

Inventor

Herbert Dawidson

Hans Betzing

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

A Natterman und Cie GmbH

Original Assignee

A Natterman und Cie GmbH

Priority date (The priority date 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 date listed.)

1979-06-18

Filing date

1979-06-18

Publication date

1981-09-01

1979-06-18 Application filed by A Natterman und Cie GmbH filed Critical A Natterman und Cie GmbH

1979-06-18 Priority to CA329,962A priority Critical patent/CA1108177A/fr

1981-09-01 Application granted granted Critical

1981-09-01 Publication of CA1108177A publication Critical patent/CA1108177A/fr

Status Expired legal-status Critical Current

Links

150000003904 phospholipids Chemical class 0.000 title claims description 10
150000008104 phosphatidylethanolamines Chemical class 0.000 claims abstract description 22
125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
229940067605 phosphatidylethanolamines Drugs 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 4
229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 7
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
239000005642 Oleic acid Substances 0.000 claims description 4
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 claims 2
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 claims 1
230000002402 anti-lipaemic effect Effects 0.000 abstract description 6
239000008194 pharmaceutical composition Substances 0.000 abstract 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000002775 capsule Substances 0.000 description 8
229940067631 phospholipid Drugs 0.000 description 8
238000003756 stirring Methods 0.000 description 8
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 6
244000068988 Glycine max Species 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
150000002632 lipids Chemical class 0.000 description 5
MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
229910002012 Aerosil® Inorganic materials 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229930003427 Vitamin E Natural products 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
201000005577 familial hyperlipidemia Diseases 0.000 description 3
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
235000019165 vitamin E Nutrition 0.000 description 3
239000011709 vitamin E Substances 0.000 description 3
229940046009 vitamin E Drugs 0.000 description 3
206010003210 Arteriosclerosis Diseases 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
208000011775 arteriosclerosis disease Diseases 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000011049 filling Methods 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000208818 Helianthus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
241000700159 Rattus Species 0.000 description 1
150000004075 acetic anhydrides Chemical class 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000003855 acyl compounds Chemical class 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
229960001214 clofibrate Drugs 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000013345 egg yolk Nutrition 0.000 description 1
210000002969 egg yolk Anatomy 0.000 description 1
238000002481 ethanol extraction Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical class CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000002888 oleic acid derivatives Chemical class 0.000 description 1
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229930004090 phosphatidylinositide Natural products 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
231100000456 subacute toxicity Toxicity 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA329,962A 1979-06-18 1979-06-18 Derives de phospholipides Expired CA1108177A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA329,962A CA1108177A (fr)	1979-06-18	1979-06-18	Derives de phospholipides

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA329,962A CA1108177A (fr)	1979-06-18	1979-06-18	Derives de phospholipides

Publications (1)

Publication Number	Publication Date
CA1108177A true CA1108177A (fr)	1981-09-01

Family

ID=4114477

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA329,962A Expired CA1108177A (fr)	1979-06-18	1979-06-18	Derives de phospholipides

Country Status (1)

Country	Link
CA (1)	CA1108177A (fr)

1979
- 1979-06-18 CA CA329,962A patent/CA1108177A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-09-01	MKEX	Expiry

Publication	Publication Date	Title
US4764508A (en)	1988-08-16	Complexes of flavanolignans with phospholipids, preparation thereof and associated pharmaceutical compositions
DE2820893C2 (de)	1986-02-20	Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen
US5023248A (en)	1991-06-11	Method of treating diabetes with inositol triphosphate
US4970335A (en)	1990-11-13	(Cycloalkylamino)methylenebis(phosphonic acid)
US4564475A (en)	1986-01-14	Compositions containing unsaturated fatty acid compounds and method of stabilizing unsaturated fatty acid compounds
US4254115A (en)	1981-03-03	Phospholipid derivative with an antilipemic and antiarteriosclerotic effect
US9784701B2 (en)	2017-10-10	Phosphatidylalkanols and compositions thereof
US5023249A (en)	1991-06-11	Fertility drug and method of producing the same
GB2046092A (en)	1980-11-12	Pharmaceutical composition containing a lysophospholid and a phospholipid
CA1089485A (fr)	1980-11-11	Procede d'obtention d'amides d'acides 2- aminocarboxyliques
EP0282320B1 (fr)	1991-12-11	Dérivés d'acide bisphosphonique et médicaments les contenant
GB2051069A (en)	1981-01-14	Phospholipid Derivatives Useful in Therapy as Antilepaemics and Antiarteriosclerotics and Compositions Containing Them
US4618685A (en)	1986-10-21	N-homocysteine thiolactonyl retinamide and use thereof as an antineoplastic agent
Yasuhito et al.	1982	Changes in the composition of fatty chains of diacyl, alkylacyl and alkenylacyl ethanolamine and choline phosphoglycerides during the development of chick heart ventricular cells High accumulation of 22. carbon fatty acid in ether phospholipids
KR870001020B1 (ko)	1987-05-23	실리비닌 유도체의 제조방법
EP0338407B1 (fr)	1993-06-09	Nouvelles alkylphosphonoserines, procédés pour leur préparation, et substances pharmaceutiques les contenant
US4725588A (en)	1988-02-16	Alkyl phospholipid antihypertensive agents in method of lowering blood pressure
US4550186A (en)	1985-10-29	Binuclear copper (II) carboxylates formed from amine-carboxyboranes
JPS6241209B2 (fr)	1987-09-02
PL111746B1 (en)	1980-09-30	Method of preparing of novel derivatives of amino acids
EP0329656B1 (fr)	1993-10-27	Principe actif isole a partir de tissus de requin
DE2756866C2 (de)	1985-10-24	N-Oleoyl-Derivate von Phosphatidyläthanolaminen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
JPS6230195B2 (fr)	1987-07-01
EP0299770A2 (fr)	1989-01-18	Dérivés solubles de silybine, procédé pour leur préparation et compositions pharmaceutiques les contenant
SU865127A3 (ru)	1981-09-15	Способ получени спирооксазолидиндионов