NO844029L - Fremgangsmaate ved fremstilling av antineoplastisk virkende preparater - Google Patents

Fremgangsmaate ved fremstilling av antineoplastisk virkende preparater

Info

Publication number: NO844029L
Authority: NO; Norway
Prior art keywords: phenyl; titanium; alkyl; butanedionato; solution
Prior art date: 1983-02-09

Application number

NO844029A

Other languages

English (en)

Norwegian (no)

Inventor

Heimo J Keller

Bernhard Keppler

Uwe Krueger

Rudolf Linder

Original Assignee

Byk Gulden Lomberg Chem Fab

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.)

1983-02-09

Filing date

1984-10-08

Publication date

1984-10-08

1984-10-08 Application filed by Byk Gulden Lomberg Chem Fab filed Critical Byk Gulden Lomberg Chem Fab

1984-10-08 Publication of NO844029L publication Critical patent/NO844029L/no

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title claims description 15
230000000118 anti-neoplastic effect Effects 0.000 title description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 45
239000000243 solution Substances 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 27
-1 C1-C4- alkyl Chemical group 0.000 claims description 18
239000010936 titanium Substances 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
229910052719 titanium Inorganic materials 0.000 claims description 16
LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
239000003513 alkali Substances 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
239000000460 chlorine Chemical group 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
229920001477 hydrophilic polymer Polymers 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
239000002244 precipitate Substances 0.000 claims description 11
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 10
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
238000001704 evaporation Methods 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 9
229910052735 hafnium Inorganic materials 0.000 claims description 9
239000002504 physiological saline solution Substances 0.000 claims description 9
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
YLQPQLYVHPRJKH-FHPZIRFBSA-J (e)-3-oxo-1-phenylbut-1-en-1-olate;titanium(4+);dichloride Chemical compound [Cl-].[Cl-].[Ti+4].CC(=O)\C=C(\[O-])C1=CC=CC=C1.CC(=O)\C=C(\[O-])C1=CC=CC=C1 YLQPQLYVHPRJKH-FHPZIRFBSA-J 0.000 claims description 6
CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 6
239000002202 Polyethylene glycol Substances 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
239000008389 polyethoxylated castor oil Substances 0.000 claims description 6
229920001223 polyethylene glycol Polymers 0.000 claims description 6
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 6
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 6
229910052726 zirconium Inorganic materials 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
230000008020 evaporation Effects 0.000 claims description 5
JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000002270 dispersing agent Substances 0.000 claims description 4
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 4
239000000080 wetting agent Substances 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229920001214 Polysorbate 60 Polymers 0.000 claims description 3
150000003973 alkyl amines Chemical class 0.000 claims description 3
125000005594 diketone group Chemical group 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
229920000136 polysorbate Polymers 0.000 claims description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
230000007717 exclusion Effects 0.000 claims description 2
WFDHLKUQFQCHKF-UHFFFAOYSA-N n-[[4-[5-(3-acetamidophenyl)-2-(2-aminopyridin-3-yl)imidazo[4,5-b]pyridin-3-yl]phenyl]methyl]-3-fluorobenzamide Chemical compound CC(=O)NC1=CC=CC(C=2N=C3N(C=4C=CC(CNC(=O)C=5C=C(F)C=CC=5)=CC=4)C(C=4C(=NC=CC=4)N)=NC3=CC=2)=C1 WFDHLKUQFQCHKF-UHFFFAOYSA-N 0.000 claims description 2
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
229910052845 zircon Inorganic materials 0.000 claims description 2
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
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 claims 3
229910052802 copper Inorganic materials 0.000 claims 2
239000010949 copper Substances 0.000 claims 2
239000002253 acid Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
229910052799 carbon Inorganic materials 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
241001465754 Metazoa Species 0.000 description 18
239000012299 nitrogen atmosphere Substances 0.000 description 18
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
239000002904 solvent Substances 0.000 description 16
206010028980 Neoplasm Diseases 0.000 description 13
238000009835 boiling Methods 0.000 description 13
238000010992 reflux Methods 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
239000013543 active substance Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000004083 survival effect Effects 0.000 description 6
208000006268 Sarcoma 180 Diseases 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 5
238000001816 cooling Methods 0.000 description 5
210000004881 tumor cell Anatomy 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
229960004316 cisplatin Drugs 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
238000011785 NMRI mouse Methods 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
239000000824 cytostatic agent Substances 0.000 description 3
230000001085 cytostatic effect Effects 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
NROOHYGFTHTDFF-UHFFFAOYSA-N 1-phenylpentane-2,4-dione Chemical compound CC(=O)CC(=O)CC1=CC=CC=C1 NROOHYGFTHTDFF-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
206010003445 Ascites Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000013078 crystal Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
239000002050 international nonproprietary name Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
238000005245 sintering Methods 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
239000011780 sodium chloride Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
WIPDJSMZXOYFOO-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)butane-1,3-dione Chemical compound COC1=CC=C(C(=O)CC(C)=O)C=C1OC WIPDJSMZXOYFOO-UHFFFAOYSA-N 0.000 description 1
WBMJETLNTZLTFE-UHFFFAOYSA-N 1-phenylhexane-1,3-dione Chemical compound CCCC(=O)CC(=O)C1=CC=CC=C1 WBMJETLNTZLTFE-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
YIWTXSVNRCWBAC-UHFFFAOYSA-N 3-phenylpentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)C1=CC=CC=C1 YIWTXSVNRCWBAC-UHFFFAOYSA-N 0.000 description 1
HORVLKADAZQYRS-UHFFFAOYSA-N 4,4-dimethyl-1-phenylpentane-1,3-dione Chemical compound CC(C)(C)C(=O)CC(=O)C1=CC=CC=C1 HORVLKADAZQYRS-UHFFFAOYSA-N 0.000 description 1
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229910015900 BF3 Inorganic materials 0.000 description 1
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206010039491 Sarcoma Diseases 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
208000024313 Testicular Neoplasms Diseases 0.000 description 1
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239000007900 aqueous suspension Substances 0.000 description 1
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125000004122 cyclic group Chemical group 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
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229910052736 halogen Inorganic materials 0.000 description 1
230000002012 hematotoxic effect Effects 0.000 description 1
RVRCFVVLDHTFFA-UHFFFAOYSA-N heptasodium;tungsten;nonatriacontahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] RVRCFVVLDHTFFA-UHFFFAOYSA-N 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
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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
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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
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 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
239000010414 supernatant solution Substances 0.000 description 1
239000002700 tablet coating Substances 0.000 description 1
238000009492 tablet coating Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
229940087291 tridecyl alcohol Drugs 0.000 description 1
230000007306 turnover Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005303 weighing Methods 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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

NO844029A 1983-02-09 1984-10-08 Fremgangsmaate ved fremstilling av antineoplastisk virkende preparater NO844029L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/EP1983/000031 WO1984003042A1 (fr)	1983-02-09	1983-02-09	Procede pour la fabrication de preparations therapeutiques antineoplastiques

Publications (1)

Publication Number	Publication Date
NO844029L true NO844029L (no)	1984-10-08

Family

ID=8164872

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO844029A NO844029L (no)	1983-02-09	1984-10-08	Fremgangsmaate ved fremstilling av antineoplastisk virkende preparater

Country Status (5)

Country	Link
DK (1)	DK481584D0 (da)
FI (1)	FI75171C (da)
HU (1)	HU199679B (da)
NO (1)	NO844029L (da)
WO (1)	WO1984003042A1 (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2344820B (en) *	1997-05-14	2002-05-08	Secr Defence	Chemical vapour deposition precursors
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)

* Cited by examiner, † Cited by third party
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 HU HU831172A patent/HU199679B/hu not_active IP Right Cessation
- 1983-02-09 WO PCT/EP1983/000031 patent/WO1984003042A1/de not_active Ceased
1984
- 1984-09-24 FI FI843745A patent/FI75171C/fi 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
FI843745A0 (fi)	1984-09-24
DK481584A (da)	1984-10-08
FI75171C (fi)	1988-05-09
HUT33968A (en)	1985-01-28
DK481584D0 (da)	1984-10-08
WO1984003042A1 (fr)	1984-08-16
HU199679B (en)	1990-03-28
FI75171B (fi)	1988-01-29
FI843745L (fi)	1984-09-24

Publication	Publication Date	Title
Borkowsky et al.	1993	Generation and reactivity of titanocene benzyl Cp2Ti (CH2Ph)(L)+ complexes. Oxidation and protonolysis chemistry of Cp2Ti (CH2Ph) 2
AU777685B2 (en)	2004-10-28	An antitumor derivative of double dicarboxylic acid diaminoplatin complex and the pharmaceutical composition thereof
NO844029L (no)	1984-10-08	Fremgangsmaate ved fremstilling av antineoplastisk virkende preparater
JP2004510778A (ja)	2004-04-08	抗腫瘍剤としての白金錯体
KR101700734B1 (ko)	2017-01-31	아미노산과 카르복실산을 포함한 게르마늄의 착체 및 이를 제조하는 방법
WO2001076569A2 (en)	2001-10-18	An improved pt(iv) antitumor agent
US4578401A (en)	1986-03-25	Mental complexes having an antineoplastic action, and medicaments containing these complexes
JPH0694471B2 (ja)	1994-11-24	薬理学的に認容性の錯化合物およびその製造法
EP1294732B1 (en)	2004-08-18	Ruthenium (ii) compounds for use in the therapy of cancer
WO2008070557A2 (en)	2008-06-12	Organometallic complexes as therapeutic agents
CN117229304B (zh)	2026-04-28	一种去甲斑蝥素衍生物、制备方法及应用
JPH0160471B2 (da)	1989-12-22
NZ198545A (en)	1985-02-28	Metal complexes and pharmaceutical compositions
TW200521126A (en)	2005-07-01	Chroman carboxylic acid derivatives for the treatment of diabetes and lipid disorders
EP0442663A1 (en)	1991-08-21	Improvements in chemical compounds
JPH02108694A (ja)	1990-04-20	白金（２）ジアミン錯体
JP4267447B2 (ja)	2009-05-27	細胞増殖抑制作用を有するランタン化合物
US20040223915A1 (en)	2004-11-11	Cytostatic cerium compounds
JPH0633242B2 (ja)	1994-05-02	有機ゲルマニウム化合物を有効成分とする肝炎の治療剤
JPH0248569A (ja)	1990-02-19	１−〔（２−フルオロフェニル）（４−フルオロフェニル）フェニルメチル〕−１ｈ−イミダゾール
KR0162639B1 (ko)	1998-12-01	퀴놀릴-및 이소퀴놀릴옥사졸-2-온의 당단백질 외막 바이러스 감염 치료 용도
WO1984002272A1 (fr)	1984-06-21	Composition antitumorale, procede de traitement des tumeurs et utilisation de la composition pour le traitement des tumeurs
US4758589A (en)	1988-07-19	Tetraphosphine-coordinated gold(I) complexes
JPS6254430B2 (da)	1987-11-14
NO853448L (no)	1985-09-02	Antineoplastisk virkende platina-kroneter-komplekser og legemidler inneholdende disse