FI75171B - Foerfarande foer framstaellning av vid behandling av kancersjukdomar anvaendbara samutfaellningar. - Google Patents
Foerfarande foer framstaellning av vid behandling av kancersjukdomar anvaendbara samutfaellningar. Download PDFInfo
- Publication number
- FI75171B FI75171B FI843745A FI843745A FI75171B FI 75171 B FI75171 B FI 75171B FI 843745 A FI843745 A FI 843745A FI 843745 A FI843745 A FI 843745A FI 75171 B FI75171 B FI 75171B
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- phenyl
- hydrogen
- titanium
- precipitates
- Prior art date
Links
- 239000002244 precipitate Substances 0.000 claims description 22
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- -1 glycerine-polyethylene glycol ricinoleate Chemical compound 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 229940125797 compound 12 Drugs 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000000243 solution Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 8
- 239000002504 physiological saline solution Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 3
- 208000006268 Sarcoma 180 Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- SWQJEOSBGXJZEA-UHFFFAOYSA-N [Ti+4].C(C1=CC=CC=C1)(=O)CC(C)=O Chemical compound [Ti+4].C(C1=CC=CC=C1)(=O)CC(C)=O SWQJEOSBGXJZEA-UHFFFAOYSA-N 0.000 description 2
- VOUOHABCWPQWNP-UHFFFAOYSA-N [Ti].C1(=CC=CC=C1)C(C(C)=O)C(C)=O Chemical compound [Ti].C1(=CC=CC=C1)C(C(C)=O)C(C)=O VOUOHABCWPQWNP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 125000005002 aryl methyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000002050 international nonproprietary name Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- LLWNRELGVIKAGI-UHFFFAOYSA-N 1-phenylbutane-1,3-dione titanium Chemical compound [Ti].CC(=O)CC(=O)C1=CC=CC=C1.CC(=O)CC(=O)C1=CC=CC=C1 LLWNRELGVIKAGI-UHFFFAOYSA-N 0.000 description 1
- XLMXUUQMSMKFMH-UZRURVBFSA-N 2-hydroxyethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCO XLMXUUQMSMKFMH-UZRURVBFSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- CJCUGTAAUJSNEJ-UHFFFAOYSA-N [Ti+4].C1(=CC=CC=C1)C(CC(C)=O)=O.C1(=CC=CC=C1)C(CC(C)=O)=O.C(CCCCCCCCCCCC)[O-].C(CCCCCCCCCCCC)[O-] Chemical compound [Ti+4].C1(=CC=CC=C1)C(CC(C)=O)=O.C1(=CC=CC=C1)C(CC(C)=O)=O.C(CCCCCCCCCCCC)[O-].C(CCCCCCCCCCCC)[O-] CJCUGTAAUJSNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- UOUDIVQOIUZSDB-UHFFFAOYSA-M chloroplatinum(1+) Chemical compound [Pt+]Cl UOUDIVQOIUZSDB-UHFFFAOYSA-M 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- ZMMRKRFMSDTOLV-UHFFFAOYSA-N cyclopenta-1,3-diene zirconium Chemical compound [Zr].C1C=CC=C1.C1C=CC=C1 ZMMRKRFMSDTOLV-UHFFFAOYSA-N 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002363 hafnium compounds Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection 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
- 210000003734 kidney Anatomy 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000002559 palpation Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- A61K31/74—Synthetic polymeric materials
-
- 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
- A61K31/28—Compounds containing heavy metals
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Claims (5)
1. Förfarande för framställning av vid behandling av kancersjukdomar användbara samutfällningar frän 5 komplexföreningar med formeln /R1(CH_) C(0)CR3C(0)R^)oM(0R4) _ X I ^ 2 m 2 2-n n väri 10 m är titan, zirkonium eller hafnium, R ar väte, C^_g-alkyl eller fenyl, som kan ha 1 eller flera fluor-, klor-, brom-, nitro-, C^_^-alkyl-, C^_4~ alkoxi- eller trifluormetylsubstituenter, 2 R är C^_g-alkyl eller fenyl, som kan ha 1 eller flera 15 fluor-, klor-, brom-, nitro-, C^_4~alkyl-, C^_4~alkoxi- eller trifluormetysubstituenter, 3 R är väte eller fenyl, 4 R är C^_^g-alkyl, som kan vara substituerad med hydr-oxi-, C^_g-alkylamin- eller alkalisulfonatogrupper, el-20 ler Cj._g-cykloalkyl, som kan vara substituerad med C^_^-alkylgrupper, hydroxi- eller alkalisulfonatogrupper, X är fluor, klor eller brom, m är talet 0 eller 1, men kan ej vara 0 ää R är väte, och n är talet 0 eller 1, 4 25 och ifall resten R innehäller en aminogrupp, hydrohalo- genider av dessa föreningar och frän hydrofila polymerer, kännetecknat därav, att en komplexförening 12 3 4 med formeln I, väri M, R,R,R,R,X,m och n betyder 4 samma som ovan, och, ifall R innehäller en aminogrupp, 30 dess hydrohalogenid, löst i ett inert organiskt lösnings-medel, tillsammans med en pä samma sätt löst hydrofil polymer, indunstas.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att den hydrofila polymeren är 35 polyvinylpyrrolidon, polyoxietylensorbitanmonofettsyra- ester eller glycerin-polyetylenglykolricinoleat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP8300031 | 1983-02-09 | ||
| PCT/EP1983/000031 WO1984003042A1 (en) | 1983-02-09 | 1983-02-09 | Process for producing therapeutical antineoplastic preparations |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI843745A0 FI843745A0 (fi) | 1984-09-24 |
| FI843745L FI843745L (fi) | 1984-09-24 |
| FI75171B true FI75171B (fi) | 1988-01-29 |
| FI75171C FI75171C (sv) | 1988-05-09 |
Family
ID=8164872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI843745A FI75171C (sv) | 1983-02-09 | 1984-09-24 | Förfarande för framställning av vid behandling av kancersjukdomar anvä ndbara samutfällningar. |
Country Status (5)
| Country | Link |
|---|---|
| DK (1) | DK481584D0 (sv) |
| FI (1) | FI75171C (sv) |
| HU (1) | HU199679B (sv) |
| NO (1) | NO844029L (sv) |
| WO (1) | WO1984003042A1 (sv) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100548979B1 (ko) * | 1997-05-14 | 2006-02-03 | 키네티큐 리미티드 | 화학 증착용 전구체 |
| GB0119224D0 (en) * | 2001-08-07 | 2001-09-26 | Inorgtech Ltd | Precursors for metalorganic chemical vapour deposition |
| US6562990B1 (en) | 2002-07-03 | 2003-05-13 | E. I. Du Pont De Nemours And Company | Titanium chelates and processes therefor |
| US8471049B2 (en) | 2008-12-10 | 2013-06-25 | Air Product And Chemicals, Inc. | Precursors for depositing group 4 metal-containing films |
| US20110256314A1 (en) | 2009-10-23 | 2011-10-20 | Air Products And Chemicals, Inc. | Methods for deposition of group 4 metal containing films |
| US8952188B2 (en) | 2009-10-23 | 2015-02-10 | Air Products And Chemicals, Inc. | Group 4 metal precursors for metal-containing films |
| CN116262764A (zh) * | 2021-12-14 | 2023-06-16 | 蔡易州 | 新型钛催化剂、其用途以及聚酯树酯的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3134709A1 (de) * | 1981-09-02 | 1983-03-10 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Antineoplastisch wirkende titanverbindung und diese enthaltende arzneimittel |
-
1983
- 1983-02-09 WO PCT/EP1983/000031 patent/WO1984003042A1/de active IP Right Grant
- 1983-02-09 HU HU831172A patent/HU199679B/hu not_active IP Right Cessation
-
1984
- 1984-09-24 FI FI843745A patent/FI75171C/sv not_active IP Right Cessation
- 1984-10-08 DK DK481584A patent/DK481584D0/da not_active Application Discontinuation
- 1984-10-08 NO NO844029A patent/NO844029L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK481584A (da) | 1984-10-08 |
| FI843745A0 (fi) | 1984-09-24 |
| FI843745L (fi) | 1984-09-24 |
| WO1984003042A1 (en) | 1984-08-16 |
| NO844029L (no) | 1984-10-08 |
| FI75171C (sv) | 1988-05-09 |
| DK481584D0 (da) | 1984-10-08 |
| HU199679B (en) | 1990-03-28 |
| HUT33968A (en) | 1985-01-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI75171B (fi) | Foerfarande foer framstaellning av vid behandling av kancersjukdomar anvaendbara samutfaellningar. | |
| JPS5920295A (ja) | 白金−アミン化合物およびその薬学的組成物 | |
| RU2140422C1 (ru) | Трехплатиновые комплексы pt(ii), способ их получения | |
| KR100239787B1 (ko) | 항종양 활성을 지니는 삼핵의 양이온성 백금 착물 및 이를 포함하는 약학적 조성물 | |
| US6548541B1 (en) | Carboplatin analogs for cancer treatment | |
| CA1273935A (en) | Platinum-intercalative complexes for the treatment of cancer | |
| CN1038450A (zh) | 取代的5-嘧啶甲酰胺类衍生物 | |
| RU2319491C1 (ru) | Противоопухолевая, антибактериальная и антивирусная фармацевтическая композиция (ее варианты) | |
| EP0073502B1 (de) | Antineoplastisch wirkende Metallkomplexe und diese enthaltende Arzneimittel | |
| CN110139660A (zh) | 用于制备抗肿瘤剂的组合物以及用于制备基于所述组合物的抗肿瘤剂的方法 | |
| Zhao et al. | Anti-tumoral titanium (IV) complexes stabilized with phenolato ligands and structure-activity relationship | |
| DE2830901A1 (de) | Reaktionsprodukte von methotrexat und divinylaether-maleinsaeureanhydrid- copolymerisaten, verfahren zu ihrer herstellung und ihre verwendung | |
| Nazari et al. | Vanadium Complexes with Maltol and Deferiprone Ligands: Synthesis, Characterization and In vitro Antiproliferative Activity toward Different Cancer Cells | |
| ES2893849T3 (es) | Complejo de oro(III), conjugado del complejo de oro(III), composición farmacéutica que comprende el complejo de oro(III) y usos y un proceso de preparación del complejo de oro(III) | |
| AU2002325863B2 (en) | Organometallic anti-tumour agent | |
| US5037812A (en) | Tumor cell growth-inhibiting pharmaceutical compositions containing phosphino-hydrocarbon-gold, silver or copper complexes | |
| EP1704150A1 (en) | 2,3-dihydroporphine derivatives, processes for their preparation, and pharmaceutical compositions containing them | |
| EP0214862B1 (en) | Anti-tumour platinum complexes, their preparation and their use | |
| WO1990006749A1 (en) | Metal complexes having an antineoplastic action, and medicaments containing these complexes | |
| CN105380951A (zh) | 一种铂类药物制剂及其制备方法和应用 | |
| CN118459491A (zh) | 含氟小分子硼药、其制备方法及其应用和药物组合物 | |
| KR810000876B1 (ko) | 항암작용제 안트라퀴논 화합물의 제법 | |
| Kim et al. | Synthesis and tumor‐inhibiting activity of new heparin‐bound nitrogen mustard analogues | |
| JPS645597B2 (sv) | ||
| KR19990044635A (ko) | 환상 헥사펩티드 화합물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: BYK GULDEN LOMBERG CHEMISCHE FABRIK GMBH |