NO175620B - - Google Patents

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Publication number: NO175620B
Authority: NO; Norway
Prior art keywords: formula; compound; weight; optionally; group
Prior art date: 1985-12-04

Application number

NO873244A

Other languages

English (en)

Norwegian (no)

Other versions

NO175620C (no

NO873244D0 (no

NO873244L (no

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.)

1985-12-04

Filing date

1987-08-03

Publication date

1994-08-01

1987-08-03 Application filed filed Critical

1987-08-03 Publication of NO873244D0 publication Critical patent/NO873244D0/no

1987-10-01 Publication of NO873244L publication Critical patent/NO873244L/no

1994-08-01 Publication of NO175620B publication Critical patent/NO175620B/no

1994-11-09 Publication of NO175620C publication Critical patent/NO175620C/no

Links

239000003814 drug Substances 0.000 claims abstract description 15
PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 claims abstract description 5
229960003775 miltefosine Drugs 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 66
-1 aliphatic monocarboxylic acids Chemical class 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 34
229910001868 water Inorganic materials 0.000 claims description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
238000000034 method Methods 0.000 claims description 29
125000004432 carbon atom Chemical group C* 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 19
239000003995 emulsifying agent Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
229940079593 drug Drugs 0.000 claims description 10
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 9
239000013543 active substance Substances 0.000 claims description 9
229960005323 phenoxyethanol Drugs 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
230000000699 topical effect Effects 0.000 claims description 9
235000014113 dietary fatty acids Nutrition 0.000 claims description 8
239000000194 fatty acid Substances 0.000 claims description 8
229930195729 fatty acid Natural products 0.000 claims description 8
235000011187 glycerol Nutrition 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
239000002775 capsule Substances 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
230000000259 anti-tumor effect Effects 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
229920002472 Starch Polymers 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000008024 pharmaceutical diluent Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000008107 starch Substances 0.000 claims description 3
235000019698 starch Nutrition 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 claims description 2
206010029098 Neoplasm skin Diseases 0.000 claims description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
208000000453 Skin Neoplasms Diseases 0.000 claims description 2
IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000001400 nonyl 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])[H] 0.000 claims description 2
QSQGNBGEHSFMAA-UHFFFAOYSA-N octane-1,2,3-triol Chemical compound CCCCCC(O)C(O)CO QSQGNBGEHSFMAA-UHFFFAOYSA-N 0.000 claims description 2
239000012188 paraffin wax Substances 0.000 claims description 2
AALKGALVYCZETF-UHFFFAOYSA-N pentane-1,2,3-triol Chemical compound CCC(O)C(O)CO AALKGALVYCZETF-UHFFFAOYSA-N 0.000 claims description 2
229920005862 polyol Polymers 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
235000011071 sorbitan monopalmitate Nutrition 0.000 claims description 2
239000001570 sorbitan monopalmitate Substances 0.000 claims description 2
229940031953 sorbitan monopalmitate Drugs 0.000 claims description 2
239000008347 soybean phospholipid Substances 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
229940099259 vaseline Drugs 0.000 claims description 2
235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
239000008158 vegetable oil Substances 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims 1
229920000053 polysorbate 80 Polymers 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
239000011149 active material Substances 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
239000000243 solution Substances 0.000 description 16
239000002904 solvent Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 14
230000026731 phosphorylation Effects 0.000 description 14
238000006366 phosphorylation reaction Methods 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
206010028980 Neoplasm Diseases 0.000 description 11
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 8
150000001768 cations Chemical class 0.000 description 8
238000004452 microanalysis Methods 0.000 description 8
239000002547 new drug Substances 0.000 description 8
235000002639 sodium chloride Nutrition 0.000 description 8
159000000000 sodium salts Chemical class 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000003513 alkali Substances 0.000 description 7
230000037396 body weight Effects 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000003776 cleavage reaction Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000006140 methanolysis reaction Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
230000007017 scission Effects 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
229940052303 ethers for general anesthesia Drugs 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
206010006187 Breast cancer Diseases 0.000 description 5
208000026310 Breast neoplasm Diseases 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
206010027465 Metastases to skin Diseases 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
150000004292 cyclic ethers Chemical class 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000001514 detection method Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
238000006798 ring closing metathesis reaction Methods 0.000 description 4
238000007142 ring opening reaction Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229960004132 diethyl ether Drugs 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
238000012360 testing method Methods 0.000 description 3
BQISFTKVULMCDX-UHFFFAOYSA-N 2-aminoethyl hexadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCN BQISFTKVULMCDX-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010027476 Metastases Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
SLVOKEOPLJCHCQ-SEYXRHQNSA-N [(z)-octadec-9-enyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C SLVOKEOPLJCHCQ-SEYXRHQNSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000004791 alkyl magnesium halides Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 2
150000003842 bromide salts Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000004113 cell culture Methods 0.000 description 2
230000005757 colony formation Effects 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
XZJFFBYDNVNJCE-UHFFFAOYSA-N dodecane-1,2,3-triol Chemical compound CCCCCCCCCC(O)C(O)CO XZJFFBYDNVNJCE-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
150000002314 glycerols Chemical class 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
XYXCXCJKZRDVPU-UHFFFAOYSA-N hexane-1,2,3-triol Chemical compound CCCC(O)C(O)CO XYXCXCJKZRDVPU-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 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
210000005075 mammary gland Anatomy 0.000 description 2
239000000463 material Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001421 myristyl 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])[H] 0.000 description 2
QMHBZWNZCSNBGU-UHFFFAOYSA-N nonane-1,2,3-triol Chemical compound CCCCCCC(O)C(O)CO QMHBZWNZCSNBGU-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000002674 ointment Substances 0.000 description 2
125000000913 palmityl 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])[H] 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052573 porcelain Inorganic materials 0.000 description 2
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/075—Ethers or acetals
- A61K31/08—Ethers or acetals acyclic, e.g. paraformaldehyde
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Measurement And Recording Of Electrical Phenomena And Electrical Characteristics Of The Living Body (AREA)
Ultra Sonic Daignosis Equipment (AREA)
Medicinal Preparation (AREA)
Electrically Operated Instructional Devices (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Respiratory Apparatuses And Protective Means (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Adhesives Or Adhesive Processes (AREA)
Steroid Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO873244A 1985-12-04 1987-08-03 Fremgangsmåte for fremstilling av et antitumorvirksomt legemiddel NO175620C (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE3542893		1985-12-04
DE3606631		1986-02-28
PCT/EP1986/000706 WO1987003478A2 (fr)	1985-12-04	1986-12-04	Medicaments

Publications (4)

Publication Number	Publication Date
NO873244D0 NO873244D0 (no)	1987-08-03
NO873244L NO873244L (no)	1987-10-01
NO175620B true NO175620B (ja)	1994-08-01
NO175620C NO175620C (no)	1994-11-09

Family

ID=25838509

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO873243A NO174877C (no)	1985-12-04	1987-08-03	Fremgangsmåte for fremstilling av et legemiddel med antitumorvirkning
NO873244A NO175620C (no)	1985-12-04	1987-08-03	Fremgangsmåte for fremstilling av et antitumorvirksomt legemiddel

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
NO873243A NO174877C (no)	1985-12-04	1987-08-03	Fremgangsmåte for fremstilling av et legemiddel med antitumorvirkning

Country Status (15)

Country	Link
US (2)	US4837023A (ja)
EP (4)	EP0248062B1 (ja)
JP (2)	JPH0637393B2 (ja)
AT (2)	ATE75608T1 (ja)
CA (2)	CA1338627C (ja)
DE (4)	DE3641379A1 (ja)
DK (2)	DK172954B1 (ja)
ES (2)	ES2038215T3 (ja)
FI (2)	FI873364A0 (ja)
GR (2)	GR3002487T3 (ja)
HU (2)	HU203201B (ja)
IE (2)	IE59777B1 (ja)
NO (2)	NO174877C (ja)
PT (2)	PT83873B (ja)
WO (2)	WO1987003478A2 (ja)

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JP4708511B2 (ja)	1993-09-09	2011-06-22	エリン・ミルズ・バイオテック・インコーポレーテッド	胆汁由来免疫調節組成物
US7135584B2 (en) *	1995-08-07	2006-11-14	Wake Forest University	Lipid analogs for treating viral infections
US5962437A (en) *	1994-08-29	1999-10-05	Wake Forest University	Lipid analogs for treating viral infections
US5574025A (en) *	1994-10-26	1996-11-12	Merck & Co., Inc.	Inhibitors of prenyl-protein transferases
AU1573495A (en) *	1995-02-10	1996-08-27	University Of British Columbia, The	{4-hexadecyl-3-methoxy-butyl} phosphonic acid and its protienconjugates useful as anti-cancer agents
CA2215339C (en)	1995-03-16	1999-01-19	Imutec Pharma Inc.	Immunomodulating compositions from bile for the treatment of immune system disorders
KR100499190B1 (ko) *	1996-03-29	2006-04-17	교와 핫꼬 고교 가부시끼가이샤	육모제
US20040101569A1 (en) *	1996-05-16	2004-05-27	Lorus Therapeutics Inc.	Immunomodulating compositions from bile
US6121245A (en) *	1997-01-29	2000-09-19	Firshein; Richard N.	Method of treating cancer using alkylglycerols in conjunction with chemotherapy
SE9701912D0 (sv) *	1997-05-22	1997-05-22	Interhealth Ab	Pharmaceutical composition and use thereof
US7582678B2 (en) *	1997-07-09	2009-09-01	D-Pharm Limited	Use of branched-chain fatty acids and derivatives thereof for the treatment of pain
KR100517399B1 (ko) *	1998-01-22	2005-09-28	젠타리스 게엠베하	레슈마니아증의 치료에서 경구 투여를 위한 밀테포신을함유하는 고형 약제학적 조성물
US7026469B2 (en) *	2000-10-19	2006-04-11	Wake Forest University School Of Medicine	Compositions and methods of double-targeting virus infections and cancer cells
IL137672A0 (en)	2000-08-03	2001-10-31	Dpharm Ltd	Derivatives of branched-chain lipophilic molecules and uses thereof
US7309696B2 (en)	2000-10-19	2007-12-18	Wake Forest University	Compositions and methods for targeting cancer cells
US6960738B2 (en) *	2001-05-29	2005-11-01	Koninklijke Philips Electronics N.V.	Metal-ceramic bond
CN100469131C (zh) *	2001-08-31	2009-03-11	汤姆森许可公司	实现条件存取系统和传输、接收及处理内容的方法和设备
WO2003090757A1 (en) *	2002-04-26	2003-11-06	Rudolf Perl	Pharmaceutical compositions of phospholipid derivatives
US20050187191A1 (en) *	2004-02-20	2005-08-25	Kucera Louis S.	Methods and compositions for the treatment of respiratory syncytial virus
EP1962862B1 (en)	2005-12-19	2013-09-04	Æterna Zentaris GmbH	Alkyl phospholipid derivatives with reduced cytotoxicity and uses therof
EP2120873B1 (en) *	2006-12-20	2012-06-27	Alphaptose Gmbh	Topical dosage form comprising tri-substituted glycerol compounds
JP2011057647A (ja) *	2009-09-14	2011-03-24	Adeka Corp	化粧料
KR102164567B1 (ko)	2011-06-24	2020-10-12	쥐알아이 바이오,아이엔씨.	염증 질환의 예방 및 치료
CN102491994B (zh) *	2011-12-07	2014-10-15	宁波九胜创新医药科技有限公司	一种胆碱磷酸烷基酯的制备方法
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US4690935A (en) *	1983-03-31	1987-09-01	Wayne State University	Inhibition of tumor growth and metastasis with calcium channel blocker compounds

1986
- 1986-12-03 CA CA000524478A patent/CA1338627C/en not_active Expired - Fee Related
- 1986-12-03 IE IE317686A patent/IE59777B1/en not_active IP Right Cessation
- 1986-12-03 IE IE317786A patent/IE59778B1/en not_active IP Right Cessation
- 1986-12-03 CA CA000524479A patent/CA1280369C/en not_active Expired - Lifetime
- 1986-12-04 DE DE19863641379 patent/DE3641379A1/de not_active Withdrawn
- 1986-12-04 AT AT87900101T patent/ATE75608T1/de not_active IP Right Cessation
- 1986-12-04 DE DE19863641491 patent/DE3641491A1/de not_active Withdrawn
- 1986-12-04 AT AT86906829T patent/ATE64529T1/de active
- 1986-12-04 EP EP87900101A patent/EP0248062B1/de not_active Expired - Lifetime
- 1986-12-04 WO PCT/EP1986/000706 patent/WO1987003478A2/de active IP Right Grant
- 1986-12-04 HU HU865560A patent/HU203201B/hu unknown
- 1986-12-04 DE DE8686906829T patent/DE3679908D1/de not_active Expired - Lifetime
- 1986-12-04 PT PT83873A patent/PT83873B/pt unknown
- 1986-12-04 EP EP86116860A patent/EP0230575A3/de active Pending
- 1986-12-04 EP EP86116858A patent/EP0225608A3/de active Pending
- 1986-12-04 WO PCT/EP1986/000705 patent/WO1987003480A2/de active IP Right Grant
- 1986-12-04 EP EP86906829A patent/EP0248047B1/de not_active Expired - Lifetime
- 1986-12-04 HU HU87831A patent/HU208143B/hu not_active IP Right Cessation
- 1986-12-04 ES ES198787900101T patent/ES2038215T3/es not_active Expired - Lifetime
- 1986-12-04 PT PT83872A patent/PT83872B/pt not_active IP Right Cessation
- 1986-12-04 DE DE19375061C patent/DE19375061I2/de active Active
- 1986-12-04 JP JP50634086A patent/JPH0637393B2/ja not_active Expired - Lifetime
- 1986-12-04 ES ES198686906829T patent/ES2032755T3/es not_active Expired - Lifetime
- 1986-12-04 US US07/097,960 patent/US4837023A/en not_active Expired - Lifetime
1987
- 1987-07-28 DK DK198703931A patent/DK172954B1/da not_active IP Right Cessation
- 1987-07-30 DK DK398587A patent/DK398587A/da not_active Application Discontinuation
- 1987-08-03 NO NO873243A patent/NO174877C/no not_active IP Right Cessation
- 1987-08-03 NO NO873244A patent/NO175620C/no not_active IP Right Cessation
- 1987-08-03 FI FI873364A patent/FI873364A0/fi not_active Application Discontinuation
- 1987-08-03 FI FI873363A patent/FI873363A0/fi not_active Application Discontinuation
1989
- 1989-02-27 US US07/316,413 patent/US5049552A/en not_active Expired - Lifetime
1991
- 1991-08-16 GR GR91401135T patent/GR3002487T3/el unknown
1992
- 1992-07-15 GR GR920401514T patent/GR3005168T3/el unknown
1995
- 1995-07-24 JP JP7187517A patent/JP2857084B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO175620C (no)	1994-11-09
EP0248062A1 (de)	1987-12-09
JP2857084B2 (ja)	1999-02-10
EP0248062B1 (de)	1992-05-06
HUT44431A (en)	1988-03-28
EP0230575A3 (de)	1987-12-02
PT83873A (de)	1987-01-01
IE59777B1 (en)	1994-04-06
HU208143B (en)	1993-08-30
DK398587D0 (da)	1987-07-30
NO873244D0 (no)	1987-08-03
NO873243L (no)	1987-10-02
CA1338627C (en)	1996-10-01
IE59778B1 (en)	1994-04-06
WO1987003480A3 (fr)	1988-02-25
DE19375061I2 (de)	2008-11-20
DE3679908D1 (de)	1991-07-25
DK393187A (da)	1987-07-28
WO1987003478A2 (fr)	1987-06-18
NO174877C (no)	1994-07-27
JPS63501719A (ja)	1988-07-14
US4837023A (en)	1989-06-06
PT83873B (pt)	1989-01-17
DE3641491A1 (de)	1987-09-17
FI873363A (fi)	1987-08-03
DK398587A (da)	1987-07-30
ES2032755T3 (es)	1993-03-01
PT83872A (de)	1987-01-01
FI873363A0 (fi)	1987-08-03
PT83872B (pt)	1989-01-17
JPH0637393B2 (ja)	1994-05-18
GR3005168T3 (ja)	1993-05-24
IE863177L (en)	1987-06-04
HUT44441A (en)	1988-03-28
US5049552A (en)	1991-09-17
NO174877B (no)	1994-04-18
NO873244L (no)	1987-10-01
EP0225608A2 (de)	1987-06-16
HU203201B (en)	1991-06-28
ES2038215T3 (es)	1993-07-16
DK393187D0 (da)	1987-07-28
GR3002487T3 (en)	1992-12-30
EP0230575A2 (de)	1987-08-05
NO873243D0 (no)	1987-08-03
CA1280369C (en)	1991-02-19
FI873364A (fi)	1987-08-03
WO1987003478A3 (fr)	1987-09-24
FI873364A0 (fi)	1987-08-03
IE863176L (en)	1987-06-04
DE3641379A1 (de)	1987-09-03
EP0248047B1 (de)	1991-06-19
WO1987003480A2 (en)	1987-06-18
EP0225608A3 (de)	1987-10-28
ATE75608T1 (de)	1992-05-15
ATE64529T1 (de)	1991-07-15
DK172954B1 (da)	1999-10-18
JPH0859677A (ja)	1996-03-05
EP0248047A1 (de)	1987-12-09

Publication	Publication Date	Title
NO175620B (ja)	1994-08-01
TWI445539B (zh)	2014-07-21	特定化合物、組合物及方法
DE69704286T2 (de)	2001-10-25	Phosphonat-Nukleotid-Verbindungen
NO170284B (no)	1992-06-22	Analogifremgangsmaate til fremstilling av farmakologisk aktive 4'-fo sfatderivater av 4'-demetylepipodofyllotoksinglukosider
KR20020093824A (ko)	2002-12-16	포스포네이트 뉴클레오티드 화합물
EP0376518A1 (en)	1990-07-04	Phospholipid nucleosides
PT94014B (pt)	1996-12-31	Processo para a preparacao de acidos aminoalquilfosfinicos substituidos
NZ245414A (en)	1995-04-27	Guanidinoalkyl-1,1-bisphosphonic acid derivatives and pharmaceutical compositions
EP0173624A2 (en)	1986-03-05	4-(guanin-9-yl) butanals and antiviral compositions containing them
WO2021150697A1 (en)	2021-07-29	N-substituted-3-tricyclyl piperidine derivatives as anticancer and neuroprotective agents
JPH02189A (ja)	1990-01-05	１‐アミノメチルホスホン酸誘導体、その製造法および医薬組成物
EP3638222B1 (en)	2024-04-03	Enzyme-triggered carbon monoxide releasing molecules
US6172050B1 (en)	2001-01-09	Phospholipid derivatives
US4745233A (en)	1988-05-17	Derivatives of 1,1,2,2-tetramethyl-1,2-bis-(2-fluoro-4-hydroxyphenyl)-ethane
KR950007756B1 (ko)	1995-07-14	피리미딘 화합물 및 그의 약학적으로 허용되는 염류
US7384935B2 (en)	2008-06-10	Phosphate prodrugs of a farnesyl dibenzodiazepinone, processes for their production and their use as pharmaceuticals
US5916884A (en)	1999-06-29	Compositions containing a mixture of phosphorus compounds and alkylglycerols
EP4259148A1 (en)	2023-10-18	Phosphonates as inhibitors of enpp1 and cdnp
CA2792093C (en)	2018-05-22	Inhibitors of intestinal apical membrane sodium/phosphate co-transport
ZA200402626B (en)	2005-06-29	New hydroxyalkylindolocarbazole compounds, a process for their preparation and pharmaceutical compositions containing them
JPH0557277B1 (ja)	1993-08-23
US5091410A (en)	1992-02-25	Thioxanthenone antitumor agents
NO873245L (no)	1987-09-28	Nye fosforbindelser og legemiddel inneholdende disse.
KR100249408B1 (ko)	2000-03-15	(s)-2,3-디하이드로폴리프레놀,(s)-2,3-디하이드로폴리프레닐모노포스-페이트,이들의제조방법및이들을포함한암의성장또는전이억제용약제
PL150330B1 (en)	1990-05-31	Method of obtaining derivatives of 1,3,2-oxazaphosphorinate

Legal Events

Date	Code	Title	Description
2005-09-12	MM1K	Lapsed by not paying the annual fees