CA1255673A - Complexes trihalo(amine) or (iii) - Google Patents

Complexes trihalo(amine) or (iii)

Info

Publication number: CA1255673A
Authority: CA; Canada
Prior art keywords: complexes; formula; gold; iii; alkyl
Prior art date: 1985-03-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000476789A

Other languages

English (en)

Inventor

Eric W. Stern

Alan R. Amundsen

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

BASF Catalysts LLC

Original Assignee

Engelhard Corp

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.)

1985-03-18

Filing date

1985-03-18

Publication date

1989-06-13

1985-03-18 Application filed by Engelhard Corp filed Critical Engelhard Corp

1985-03-18 Priority to CA000476789A priority Critical patent/CA1255673A/fr

1989-06-13 Application granted granted Critical

1989-06-13 Publication of CA1255673A publication Critical patent/CA1255673A/fr

Status Expired legal-status Critical Current

Links

150000001412 amines Chemical class 0.000 title abstract description 4
239000004480 active ingredient Substances 0.000 claims abstract description 20
238000011282 treatment Methods 0.000 claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
239000010931 gold Substances 0.000 claims description 39
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 34
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
150000001875 compounds Chemical class 0.000 claims description 30
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 23
235000001968 nicotinic acid Nutrition 0.000 claims description 17
229960003512 nicotinic acid Drugs 0.000 claims description 17
239000011664 nicotinic acid Substances 0.000 claims description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
125000001309 chloro group Chemical group Cl* 0.000 claims description 14
WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 claims description 12
229910052737 gold Inorganic materials 0.000 claims description 11
241001465754 Metazoa Species 0.000 claims description 10
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 10
WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 claims description 9
125000001246 bromo group Chemical group Br* 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
229950007593 homonicotinic acid Drugs 0.000 claims description 9
-1 -C1-4 alkyl imidazole Chemical compound 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
239000002775 capsule Substances 0.000 claims description 6
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
238000007911 parenteral administration Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
150000003973 alkyl amines Chemical class 0.000 claims description 4
150000004982 aromatic amines Chemical class 0.000 claims description 4
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
150000003222 pyridines Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
201000011510 cancer Diseases 0.000 claims 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
CBMIPXHVOVTTTL-UHFFFAOYSA-N gold(3+) Chemical class [Au+3] CBMIPXHVOVTTTL-UHFFFAOYSA-N 0.000 abstract description 27
238000000034 method Methods 0.000 abstract description 16
206010028980 Neoplasm Diseases 0.000 abstract description 12
230000000259 anti-tumor effect Effects 0.000 abstract description 11
239000002246 antineoplastic agent Substances 0.000 abstract description 9
150000002343 gold Chemical class 0.000 abstract description 6
239000003446 ligand Substances 0.000 abstract description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 4
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 abstract description 3
229960004316 cisplatin Drugs 0.000 abstract description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
229940045985 antineoplastic platinum compound Drugs 0.000 abstract 1
206010003246 arthritis Diseases 0.000 abstract 1
150000003058 platinum compounds Chemical class 0.000 abstract 1
239000010970 precious metal Substances 0.000 abstract 1
238000012552 review Methods 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 19
238000012360 testing method Methods 0.000 description 12
241000699670 Mus sp. Species 0.000 description 11
239000003085 diluting agent Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 8
239000003826 tablet Substances 0.000 description 8
239000002552 dosage form Substances 0.000 description 7
231100000636 lethal dose Toxicity 0.000 description 7
239000000843 powder Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
206010003445 Ascites Diseases 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000003708 ampul Substances 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000000796 flavoring agent Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 4
229960002079 calcium pantothenate Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
235000013355 food flavoring agent Nutrition 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
241000124008 Mammalia Species 0.000 description 3
235000019483 Peanut oil Nutrition 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
235000021355 Stearic acid Nutrition 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000000312 peanut oil Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
238000012216 screening Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000008117 stearic acid Substances 0.000 description 3
229960004274 stearic acid Drugs 0.000 description 3
235000020238 sunflower seed Nutrition 0.000 description 3
210000004881 tumor cell Anatomy 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
239000010497 wheat germ oil Substances 0.000 description 3
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000237858 Gastropoda Species 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
229910020252 KAuCl4 Inorganic materials 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
208000006268 Sarcoma 180 Diseases 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
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235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 2
229940079458 niacinamide 50 mg Drugs 0.000 description 2
235000005152 nicotinamide Nutrition 0.000 description 2
239000011570 nicotinamide Substances 0.000 description 2
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239000000454 talc Substances 0.000 description 2
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238000012546 transfer Methods 0.000 description 2
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
229960001763 zinc sulfate Drugs 0.000 description 2
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COTYNDRSENVEFI-UHFFFAOYSA-N 1-pyrimidin-5-ylethanone Chemical compound CC(=O)C1=CN=CN=C1 COTYNDRSENVEFI-UHFFFAOYSA-N 0.000 description 1
PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical compound OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 description 1
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
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238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
208000003747 lymphoid leukemia Diseases 0.000 description 1
208000025036 lymphosarcoma Diseases 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229960003390 magnesium sulfate Drugs 0.000 description 1
229940091250 magnesium supplement Drugs 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000003607 modifier Substances 0.000 description 1
208000025113 myeloid leukemia Diseases 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
230000000050 nutritive effect Effects 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Chemical class 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
208000004259 scirrhous adenocarcinoma Diseases 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001509 sodium citrate Chemical class 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical class O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007905 soft elastic gelatin capsule Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
206010041823 squamous cell carcinoma Diseases 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009747 swallowing Effects 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000476789A 1985-03-18 1985-03-18 Complexes trihalo(amine) or (iii) Expired CA1255673A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000476789A CA1255673A (fr)	1985-03-18	1985-03-18	Complexes trihalo(amine) or (iii)

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Application Number	Priority Date	Filing Date	Title
CA000476789A CA1255673A (fr)	1985-03-18	1985-03-18	Complexes trihalo(amine) or (iii)

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Publication Number	Publication Date
CA1255673A true CA1255673A (fr)	1989-06-13

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CA000476789A Expired CA1255673A (fr)	1985-03-18	1985-03-18	Complexes trihalo(amine) or (iii)

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CA (1)	CA1255673A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2019008013A1 (fr)	2017-07-04	2019-01-10	Szczepaniak Stanislaw	Complexes d'or (iii) solubles dans l'eau, procédés de production de complexes d'or (iii) solubles dans l'eau et leur utilisation

1985
- 1985-03-18 CA CA000476789A patent/CA1255673A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2019008013A1 (fr)	2017-07-04	2019-01-10	Szczepaniak Stanislaw	Complexes d'or (iii) solubles dans l'eau, procédés de production de complexes d'or (iii) solubles dans l'eau et leur utilisation

Legal Events

Date	Code	Title	Description
2006-06-13	MKEX	Expiry

Publication	Publication Date	Title
US4500465A (en)	1985-02-19	Solubilized platinum (II) complexes
CA1134378A (fr)	1982-10-26	Complexes de cis-platine(ii) amino-lactate
US4234500A (en)	1980-11-18	Ethylenediamine platinum(II) and 1,2-diamino-cyclohexane platinum(II) pyrophosphate complexes
EP0164970B1 (fr)	1989-04-19	Compositions pharmaceutiques antitumeurs contenant des complexes phosphinohydrocarbures-or, -argent ou -cuivre
CA1302416C (fr)	1992-06-02	Platine triamine utilisee comme antineoplasique
CA1238854A (fr)	1988-07-05	COMPOSES PHARMACEUTIQUES ANTITUMORAUX ET METHODES DE TRAITEMENT DES TUMEURS A L'AIDE DE DERIVES DIOR (I), DIOR (III), DIARGENT (I) ET DICUIVRE (I) (.alpha.,OMEGA - BIS DISUBSTITUES DE PHOSPHINOHYDROCARBURES)
EP0195147B1 (fr)	1989-11-08	Complexes trihalo(amine) or (III)
US4505928A (en)	1985-03-19	Pharmaceutical composition containing cis-platinum (II) amine lactate and a method of using same
US4921847A (en)	1990-05-01	Trihalo(amine)gold(III) anti-tumor complexes
US4457926A (en)	1984-07-03	Cis-Platinum(II) amine ascorbate complexes
US4291027A (en)	1981-09-22	Method for treating tumors with ethylenediamine platinum (II) and 1,2-diaminocyclohexane-platinum (II) pyrophosphate complexes
US4739087A (en)	1988-04-19	Antineoplastic platinum complexes
EP0041792B1 (fr)	1983-10-26	Composés du platine possédant une activité antitumorale ou antimicrobienne et préparations pharmaceutiques les contenant
US4786725A (en)	1988-11-22	Solubilized platinum (II) complexes
US4783482A (en)	1988-11-08	Bis(thiocyanato)palladium(II)complexes
US4462998A (en)	1984-07-31	Method of using a cis-platinum(II) amine ascorbate
US4578491A (en)	1986-03-25	Bis(thiocyanato)palladium(II) complexes
US5037812A (en)	1991-08-06	Tumor cell growth-inhibiting pharmaceutical compositions containing phosphino-hydrocarbon-gold, silver or copper complexes
EP0098133B1 (fr)	1986-07-23	Complexes de bis(thiocyanato)palladium(II)
EP0098134B1 (fr)	1987-06-03	Bis(carboxylato)palladates(II) ioniques comme agents antitumeur
US4578490A (en)	1986-03-25	Ionic bis(dicarboxylato)palladate(II) anti-tumor agents
EP0191624A2 (fr)	1986-08-20	Agents anti-tumeur or-purine
US4839386A (en)	1989-06-13	Ionic bis (Dicarboxylato) palladate (II)
EP0290169A2 (fr)	1988-11-09	Complexes de diamine platine avec des ligands phosphonocarboxylates ou phosphonocarboxylate substitués comme agents anti-tumeurs
US4970324A (en)	1990-11-13	Aminoalkyl-substituted azetidine platinum(II) complexes

CA1255673A - Complexes trihalo(amine) or (iii) - Google Patents

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Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4130053

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Country Status (1)

Cited By (1)

Cited By (1)

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