NO851006L - Glyceroleterfosfatider - Google Patents

Glyceroleterfosfatider

Info

Publication number: NO851006L
Authority: NO; Norway
Prior art keywords: residues; mmol; alkyl; multiplet; oxy
Prior art date: 1984-03-15

Application number

NO851006A

Other languages

English (en)

Norwegian (no)

Inventor

Manfred Breuninger

Dieter Schmidt

Original Assignee

Hoffmann La Roche

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.)

1984-03-15

Filing date

1985-03-14

Publication date

1985-09-16

1985-03-14 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1985-09-16 Publication of NO851006L publication Critical patent/NO851006L/no

Links

150000003839 salts Chemical class 0.000 claims description 33
150000001875 compounds Chemical class 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 14
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 claims description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical class N* 0.000 claims description 4
125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
150000003973 alkyl amines Chemical class 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims 4
238000000034 method Methods 0.000 claims 2
239000007789 gas Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 44
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
238000000921 elemental analysis Methods 0.000 description 24
239000000243 solution Substances 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000007858 starting material Substances 0.000 description 11
-1 ether phosphates Chemical class 0.000 description 10
SVUVFGHFDMIFFC-UHFFFAOYSA-M 4-hydroxybutyl(trimethyl)azanium;4-methylbenzenesulfonate Chemical compound C[N+](C)(C)CCCCO.CC1=CC=C(S([O-])(=O)=O)C=C1 SVUVFGHFDMIFFC-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
FCOWNQVKIMIEOR-UHFFFAOYSA-M (4-hydroxycyclohexyl)-trimethylazanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C[N+](C)(C)C1CCC(O)CC1 FCOWNQVKIMIEOR-UHFFFAOYSA-M 0.000 description 8
AJAKLDUGVSKVDG-UHFFFAOYSA-N 3,7,11,15-tetramethylhexadecan-1-ol Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)CCO AJAKLDUGVSKVDG-UHFFFAOYSA-N 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002502 liposome Substances 0.000 description 7
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
229940075419 choline hydroxide Drugs 0.000 description 6
239000012043 crude product Substances 0.000 description 5
239000000693 micelle Substances 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000002314 glycerols Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
229960003529 diazepam Drugs 0.000 description 3
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000787 lecithin Substances 0.000 description 3
235000010445 lecithin Nutrition 0.000 description 3
MDUMHXNWZBLANE-UHFFFAOYSA-M 1,1-dimethylpiperidin-1-ium-4-ol;4-methylbenzenesulfonate Chemical compound C[N+]1(C)CCC(O)CC1.CC1=CC=C(S([O-])(=O)=O)C=C1 MDUMHXNWZBLANE-UHFFFAOYSA-M 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 2
MRNWDGJVCQLVOX-UHFFFAOYSA-N 4,4,4-triphenylbutane-1,2,3-triol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(O)C(O)CO)C1=CC=CC=C1 MRNWDGJVCQLVOX-UHFFFAOYSA-N 0.000 description 2
ZUZBODJLJGEMTC-UHFFFAOYSA-N 4-(4,8,12-trimethyltridecyl)benzenesulfonic acid Chemical compound CC(C)CCCC(C)CCCC(C)CCCc1ccc(cc1)S(O)(=O)=O ZUZBODJLJGEMTC-UHFFFAOYSA-N 0.000 description 2
IRXMLDJNNSNHDO-UHFFFAOYSA-N 4-(4,8-dimethylnonyl)benzenesulfonic acid Chemical compound CC(C)CCCC(C)CCCC1=CC=C(S(O)(=O)=O)C=C1 IRXMLDJNNSNHDO-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000007928 solubilization Effects 0.000 description 2
238000005063 solubilization Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
235000007586 terpenes Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
SBMUNILHNJLMBF-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound ClP1(=O)OCCO1 SBMUNILHNJLMBF-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
HDPUXESLSOZSIB-UHFFFAOYSA-N 3,7,11-trimethyldodecan-1-ol Chemical compound CC(C)CCCC(C)CCCC(C)CCO HDPUXESLSOZSIB-UHFFFAOYSA-N 0.000 description 1
LWCIBYRXSHRIAP-UHFFFAOYSA-N 3-phenylmethoxypropane-1,2-diol Chemical compound OCC(O)COCC1=CC=CC=C1 LWCIBYRXSHRIAP-UHFFFAOYSA-N 0.000 description 1
QCTOLMMTYSGTDA-UHFFFAOYSA-N 4-(dimethylamino)butan-1-ol Chemical compound CN(C)CCCCO QCTOLMMTYSGTDA-UHFFFAOYSA-N 0.000 description 1
IPEPLPGOLSCCNI-UHFFFAOYSA-M 4-methylbenzenesulfonate;2-(1-methylpiperidin-1-ium-1-yl)ethanol Chemical compound OCC[N+]1(C)CCCCC1.CC1=CC=C(S([O-])(=O)=O)C=C1 IPEPLPGOLSCCNI-UHFFFAOYSA-M 0.000 description 1
VTDOEFXTVHCAAM-UHFFFAOYSA-N 4-methylpent-3-ene-1,2,3-triol Chemical compound CC(C)=C(O)C(O)CO VTDOEFXTVHCAAM-UHFFFAOYSA-N 0.000 description 1
125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
VMIYHDSEFNYJSL-UHFFFAOYSA-N Bromazepam Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=N1 VMIYHDSEFNYJSL-UHFFFAOYSA-N 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
239000004380 Cholic acid Substances 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108010007979 Glycocholic Acid Proteins 0.000 description 1
108010035713 Glycodeoxycholic Acid Proteins 0.000 description 1
WVULKSPCQVQLCU-UHFFFAOYSA-N Glycodeoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 WVULKSPCQVQLCU-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
YLCXGBZIZBEVPZ-UHFFFAOYSA-N Medazepam Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=CC=CC=C1 YLCXGBZIZBEVPZ-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
RFDAIACWWDREDC-UHFFFAOYSA-N Na salt-Glycocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 RFDAIACWWDREDC-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 1
WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000003613 bile acid Substances 0.000 description 1
229960002729 bromazepam Drugs 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
229960001091 chenodeoxycholic acid Drugs 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
229960002471 cholic acid Drugs 0.000 description 1
235000019416 cholic acid Nutrition 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
229960003964 deoxycholic acid Drugs 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
150000002016 disaccharides Chemical class 0.000 description 1
229940079593 drug Drugs 0.000 description 1
229960002200 flunitrazepam Drugs 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
239000008103 glucose Substances 0.000 description 1
RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 description 1
229940099347 glycocholic acid Drugs 0.000 description 1
WVULKSPCQVQLCU-BUXLTGKBSA-N glycodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 WVULKSPCQVQLCU-BUXLTGKBSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
229960002225 medazepam Drugs 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
150000002772 monosaccharides Chemical class 0.000 description 1
KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 1
229960001454 nitrazepam Drugs 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
IZSBVVGANRHKEE-UHFFFAOYSA-N octadecyl 4-methylbenzenesulfonate Chemical compound CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 IZSBVVGANRHKEE-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000004079 stearyl 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])([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])C([H])([H])[H] 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000010409 thin film Substances 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1
235000010447 xylitol Nutrition 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
- C07F9/10—Phosphatides, e.g. lecithin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/135—Saturated ethers containing hydroxy or O-metal groups having more than one ether bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Dispersion Chemistry (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Saccharide Compounds (AREA)
Steroid Compounds (AREA)

NO851006A 1984-03-15 1985-03-14 Glyceroleterfosfatider NO851006L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH128784		1984-03-15
CH49185		1985-02-04

Publications (1)

Publication Number	Publication Date
NO851006L true NO851006L (no)	1985-09-16

Family

ID=25684726

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO851006A NO851006L (no)	1984-03-15	1985-03-14	Glyceroleterfosfatider

Country Status (16)

Country	Link
US (1)	US4694084A (fr)
EP (1)	EP0154977B1 (fr)
AR (1)	AR241022A1 (fr)
AU (1)	AU574440B2 (fr)
CA (1)	CA1264162A (fr)
DE (1)	DE3570239D1 (fr)
DK (1)	DK117985A (fr)
ES (2)	ES8606233A1 (fr)
FI (1)	FI78299C (fr)
HU (1)	HU195828B (fr)
IL (1)	IL74540A (fr)
MC (1)	MC1649A1 (fr)
NO (1)	NO851006L (fr)
NZ (1)	NZ211368A (fr)
PH (1)	PH20750A (fr)
PT (1)	PT80112B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1319886C (fr)	1987-02-03	1993-07-06	Alberto Ferro	Solutions de micelles mixtes
CN1017435B (zh) *	1987-03-24	1992-07-15	日本化学医药株式会社	新的甘油衍生物的制备方法
CA2033725C (fr) *	1990-01-24	2001-05-29	Folker Pittrof	Compositions pharmaceutiques et cosmetiques
FR2687314A1 (fr) *	1992-02-18	1993-08-20	Oreal	Dispersion de vesicules lipidiques, composition cosmetique et/ou pharmaceutique la contenant et procede de preparation de ladite dispersion.
AU2245295A (en) *	1994-04-15	1995-11-10	Hemagen/Pfc	Fluorochemical emulsions containing 1,3-dialkylglycerophosphoryl choline surfactants and methods of use
JP2740153B2 (ja) *	1995-03-07	1998-04-15	エフ・ホフマン−ラロシユアーゲー	混合ミセル
EP1415648B1 (fr) *	2001-07-13	2006-11-22	NanoCarrier Co., Ltd.	Composition de lyophilisation de micelle polymere d'encapsulation de medicaments et procede de preparation associe
AU2002951216A0 (en) *	2002-09-05	2002-09-19	Dbl Australia Pty Ltd	Surfactants and lyotropic phases formed therefrom
JP2007504256A (ja) *	2003-09-01	2007-03-01	メイン・ファ−マ・インタ−ナショナル・プロプライエタリ−・リミテッド	生物活性剤の送達のための組成物及び方法
DE102005016152A1 (de) *	2005-04-07	2006-10-12	Basf Ag	Herstellung von (Co)Tensiden durch Umsetzung von Polyolen mit Olefinen
ES3065854T3 (en)	2011-12-07	2026-05-08	Alnylam Pharmaceuticals Inc	Biodegradable lipids for the delivery of active agents
US12071516B2 (en)	2014-09-04	2024-08-27	Nano Precision Medical, Inc.	Polymeric stabilizing formulations
WO2016037128A1 (fr)	2014-09-04	2016-03-10	Nano Precision Medical, Inc.	Formulations stabilisantes polymères

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1202370B (it) *	1976-07-12	1989-02-09	Hoffmann La Roche	Soluzioni inietabili in cui l'atti vita' emolitica degli agenti di formazione di micelle naturali e' evitata mediante l'aggiunta di lipoidi e relativi prodotti
DE2820893C2 (de) *	1978-05-12	1986-02-20	A. Nattermann & Cie GmbH, 5000 Köln	Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen
CA1173360A (fr) *	1979-06-22	1984-08-28	Jurg Schrank	Produits pharmaceutiques
DE3011738A1 (de) *	1980-03-26	1981-10-01	Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen	Neue glycerin-3-phosphorsaeurehalogenalkylester
IL64397A0 (en) *	1981-01-07	1982-02-28	Weder Hans G	Process for the preparation of liposomal medicaments
US4493832A (en) *	1981-07-03	1985-01-15	Fujisawa Pharmaceutical Co., Ltd.	Certain glycerol-phosphoryl choline derivatives, compositions containing same and method of using same
US4562179A (en) *	1982-04-19	1985-12-31	Fujisawa Pharmaceutical Co., Ltd.	Phospholipid derivatives, and pharmaceutical composition of the same
JPS59163389A (ja) *	1983-03-07	1984-09-14	Takeda Chem Ind Ltd	リン脂質
JPS59184195A (ja) *	1983-04-04	1984-10-19	Takeda Chem Ind Ltd	グリセロ−ル誘導体

1985
- 1985-02-25 CA CA000475022A patent/CA1264162A/fr not_active Expired - Lifetime
- 1985-03-07 IL IL74540A patent/IL74540A/xx unknown
- 1985-03-08 US US06/709,871 patent/US4694084A/en not_active Expired - Fee Related
- 1985-03-08 NZ NZ211368A patent/NZ211368A/xx unknown
- 1985-03-11 AU AU39710/85A patent/AU574440B2/en not_active Ceased
- 1985-03-12 FI FI850972A patent/FI78299C/fi not_active IP Right Cessation
- 1985-03-12 DE DE8585102830T patent/DE3570239D1/de not_active Expired
- 1985-03-12 EP EP85102830A patent/EP0154977B1/fr not_active Expired
- 1985-03-13 HU HU85923A patent/HU195828B/hu not_active IP Right Cessation
- 1985-03-13 AR AR299731A patent/AR241022A1/es active
- 1985-03-13 MC MC851758A patent/MC1649A1/fr unknown
- 1985-03-14 PH PH31985A patent/PH20750A/en unknown
- 1985-03-14 PT PT80112A patent/PT80112B/pt not_active IP Right Cessation
- 1985-03-14 NO NO851006A patent/NO851006L/no unknown
- 1985-03-14 DK DK117985A patent/DK117985A/da not_active Application Discontinuation
- 1985-03-14 ES ES541242A patent/ES8606233A1/es not_active Expired
1986
- 1986-01-16 ES ES550920A patent/ES8703481A1/es not_active Expired

Also Published As

Publication number	Publication date
FI850972L (fi)	1985-09-16
FI78299C (fi)	1989-07-10
AU574440B2 (en)	1988-07-07
PT80112A (en)	1985-04-01
FI850972A0 (fi)	1985-03-12
ES541242A0 (es)	1986-04-16
ES550920A0 (es)	1987-02-16
HU195828B (en)	1988-07-28
EP0154977A2 (fr)	1985-09-18
HUT36824A (en)	1985-10-28
ES8703481A1 (es)	1987-02-16
EP0154977B1 (fr)	1989-05-17
US4694084A (en)	1987-09-15
DK117985D0 (da)	1985-03-14
NZ211368A (en)	1988-11-29
AR241022A1 (es)	1991-04-30
CA1264162A (fr)	1990-01-02
AR241022A2 (es)	1991-04-30
DK117985A (da)	1985-09-16
PT80112B (en)	1987-03-24
FI78299B (fi)	1989-03-31
EP0154977A3 (en)	1986-02-19
ES8606233A1 (es)	1986-04-16
IL74540A0 (en)	1985-06-30
DE3570239D1 (en)	1989-06-22
AU3971085A (en)	1985-09-19
IL74540A (en)	1989-02-28
MC1649A1 (fr)	1986-04-07
PH20750A (en)	1987-04-02

Publication	Publication Date	Title
DE69431596T2 (de)	2003-06-26	(phospho)lipide zum bekämpfen einer hepatitis b-infektion
DE3689369T2 (de)	1994-05-19	Terpen-amino-Alkohole und deren medizinische Verwendung.
EP0699655B1 (fr)	1997-09-24	Procédé pour la préparation de diesters quaternaires
US4562179A (en)	1985-12-31	Phospholipid derivatives, and pharmaceutical composition of the same
US4694084A (en)	1987-09-15	Glycerol ether phosphatides
JPS60100544A (ja)	1985-06-04	新規なグリセリン誘導体，その製造方法及びその誘導体を含有する薬剤
NO152899B (no)	1985-09-02	Analogifremgangsmaate for fremstilling av terapeutisk aktive glycerolderivater
EP0418716A1 (fr)	1991-03-27	Esters aminoalcohol d'acide thienylcarboxyliques leurs produits quaternaires, leur préparation et l'utilisation de ces composés
DE3307925A1 (de)	1984-09-06	Neue 0-acyl-alkandiol-phospholipide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
EP0184905B1 (fr)	1989-03-01	Dérivés d'acétoacétyl-2 glycérol, leur production et utilisation
DE2203837C3 (de)	1981-07-23	Verfahren zur Herstellung von Benzylphosphonaten
DD294265A5 (de)	1991-09-26	Substituierte aminoalkylphosphinsaeuren und verfahren zu deren herstellung
EP0112872A1 (fr)	1984-07-11	Nouveaux derives de la glycerine pour la synthese de phospholipides
US6531614B2 (en)	2003-03-11	Method of prostaglandin synthesis
EP0002062B1 (fr)	1982-05-05	Composés cycliques organophosphorés, procédé pour leur préparation et leur utilisation
EP0579939B1 (fr)	1999-02-03	Dérivés de phospholipide
AT400333B (de)	1995-12-27	3-(n-methyl-n-alkyl)-amino-2-methoxymethylenpro an-1-ol-derivate, verfahren zu deren herstellung und sie enthaltende therapeutische zusammensetzungen
EP0229128B1 (fr)	1990-05-30	Derives de glycero-3(2)-phospho-l-serine et preparations pharmaceutiques les contenant
DE69300011T2 (de)	1995-05-11	Diacylglycerol-Nicotinate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen.
DE3535766A1 (de)	1986-04-17	Neue 5-fluor-2'-desoxyuridin-derivate und salze derselben, verfahren zur herstellung derselben und anti-tumormittel mit einem gehalt derselben
DD294945A5 (de)	1991-10-17	Verfahren zur herstellung von p-substituierten propanphosphinsaeureverbindungen
DD236731B3 (de)	1992-12-10	Verfahren zur herstellung von neuen in 5-stellung substituierten 5,10-dihydro-11h-dibenzo\|b,e¨\|1,4¨diazepin-11-onen
EP0391850A2 (fr)	1990-10-10	Dérivés amino-dicarboxyliques insaturés
US4703130A (en)	1987-10-27	Antihypertensive phosphate derivatives
JPS6123178B2 (fr)	1986-06-04