CA1282058C - Derives du diamineplatine a substituants hydroxyles - Google Patents

Derives du diamineplatine a substituants hydroxyles

Info

Publication number: CA1282058C
Authority: CA; Canada
Prior art keywords: alkyl; compound; dideoxy; carbon atoms; diamino
Prior art date: 1986-08-15
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 - Lifetime

Application number

CA000516071A

Other languages

English (en)

Inventor

Stephen Hanessian

Theophile Theophanides

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.)

Individual

Original Assignee

Individual

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.)

1986-08-15

Filing date

1986-08-15

Publication date

1991-03-26

1986-08-15 Application filed by Individual filed Critical Individual

1986-08-15 Priority to CA000516071A priority Critical patent/CA1282058C/fr

1991-03-26 Application granted granted Critical

1991-03-26 Publication of CA1282058C publication Critical patent/CA1282058C/fr

2008-03-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

-1 platinum diamine compounds Chemical class 0.000 title claims description 19
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title description 41
229910052697 platinum Inorganic materials 0.000 title description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 84
125000000217 alkyl group Chemical group 0.000 claims abstract description 57
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 52
238000000034 method Methods 0.000 claims abstract description 34
230000008569 process Effects 0.000 claims abstract description 26
238000002360 preparation method Methods 0.000 claims abstract description 19
125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 13
125000006239 protecting group Chemical group 0.000 claims abstract description 11
150000002243 furanoses Chemical group 0.000 claims abstract description 9
125000001424 substituent group Chemical group 0.000 claims abstract description 9
150000003215 pyranoses Chemical class 0.000 claims abstract 7
239000000203 mixture Substances 0.000 claims description 57
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 20
229910052700 potassium Inorganic materials 0.000 claims description 20
239000011591 potassium Substances 0.000 claims description 20
239000003937 drug carrier Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
230000001476 alcoholic effect Effects 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000004985 diamines Chemical class 0.000 claims description 10
239000003446 ligand Substances 0.000 claims description 9
239000000811 xylitol Substances 0.000 claims description 6
229960002675 xylitol Drugs 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
HPGQGFIGUGXJLA-VPENINKCSA-N (2S,3R,4R)-3,4-diaminopentane-1,2,5-triol Chemical compound N[C@@H](CO)[C@H]([C@H](O)CO)N HPGQGFIGUGXJLA-VPENINKCSA-N 0.000 claims description 3
SAFSJTHXJQHMJJ-ZXXMMSQZSA-N (2S,3R,4R,5S)-3,4-diaminohexane-1,2,5,6-tetrol Chemical compound N[C@@H]([C@@H](CO)O)[C@H]([C@H](O)CO)N SAFSJTHXJQHMJJ-ZXXMMSQZSA-N 0.000 claims description 3
JOINEDRPUPHALH-QWWZWVQMSA-N (2s,3s)-2,3-diaminobutane-1,4-diol Chemical compound OC[C@@H](N)[C@H](N)CO JOINEDRPUPHALH-QWWZWVQMSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
150000002763 monocarboxylic acids Chemical class 0.000 claims 3
229910052801 chlorine Inorganic materials 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
150000001991 dicarboxylic acids Chemical class 0.000 claims 2
239000000376 reactant Substances 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 13
230000000845 anti-microbial effect Effects 0.000 abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 40
229910001868 water Inorganic materials 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
206010028980 Neoplasm Diseases 0.000 description 23
239000012153 distilled water Substances 0.000 description 23
239000013078 crystal Substances 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
201000011510 cancer Diseases 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
239000006188 syrup Substances 0.000 description 14
235000020357 syrup Nutrition 0.000 description 14
238000011282 treatment Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
239000003054 catalyst Substances 0.000 description 8
239000003814 drug Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
238000012360 testing method Methods 0.000 description 8
229940079593 drug Drugs 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
229960001866 silicon dioxide Drugs 0.000 description 7
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
230000000259 anti-tumor effect Effects 0.000 description 5
150000001540 azides Chemical class 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000001990 intravenous administration Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 4
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-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
206010039491 Sarcoma Diseases 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 4
230000008034 disappearance Effects 0.000 description 4
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229940023032 activated charcoal Drugs 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
230000006378 damage Effects 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000003834 intracellular effect Effects 0.000 description 3
208000032839 leukemia Diseases 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
231100000417 nephrotoxicity Toxicity 0.000 description 3
239000004533 oil dispersion Substances 0.000 description 3
235000019345 sodium thiosulphate Nutrition 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
206010029155 Nephropathy toxic Diseases 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
230000009918 complex formation Effects 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000006870 function Effects 0.000 description 2
229930182470 glycoside Natural products 0.000 description 2
150000002338 glycosides Chemical class 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000002609 medium Substances 0.000 description 2
230000007694 nephrotoxicity Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000003057 platinum Chemical class 0.000 description 2
150000003112 potassium compounds Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003214 pyranose derivatives Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
231100001274 therapeutic index Toxicity 0.000 description 2
NCWHFQVVMZXFHI-QZTJIDSGSA-N (2s,3s)-1,4-bis(phenylmethoxy)butane-2,3-diamine Chemical compound C([C@@H](N)[C@H](N)COCC=1C=CC=CC=1)OCC1=CC=CC=C1 NCWHFQVVMZXFHI-QZTJIDSGSA-N 0.000 description 1
229940006015 4-hydroxybutyric acid Drugs 0.000 description 1
208000036832 Adenocarcinoma of ovary Diseases 0.000 description 1
241000588986 Alcaligenes Species 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
208000003174 Brain Neoplasms Diseases 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 1
206010014733 Endometrial cancer Diseases 0.000 description 1
206010014759 Endometrial neoplasm Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000233866 Fungi Species 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
206010025323 Lymphomas Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000588655 Moraxella catarrhalis Species 0.000 description 1
206010061328 Ovarian epithelial cancer Diseases 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
239000012980 RPMI-1640 medium Substances 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
101100162169 Xenopus laevis adrm1-a gene Proteins 0.000 description 1
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229940009456 adriamycin Drugs 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
BNIBNUOPVTZWRT-JTQLQIEISA-N benzyl n-[(3s)-5-oxooxolan-3-yl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)N[C@@H]1COC(=O)C1 BNIBNUOPVTZWRT-JTQLQIEISA-N 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
208000037516 chromosome inversion disease Diseases 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
SGLJYTWMWIAGEU-UHFFFAOYSA-N cyclohexane-1,2-diamine;platinum(2+) Chemical compound [Pt+2].NC1CCCCC1N SGLJYTWMWIAGEU-UHFFFAOYSA-N 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
201000003914 endometrial carcinoma Diseases 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
230000006846 excision repair Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
239000007943 implant Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
150000005217 methyl ethers Chemical class 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000003941 n-butylamines Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
208000013371 ovarian adenocarcinoma Diseases 0.000 description 1
201000006588 ovary adenocarcinoma Diseases 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007248 oxidative elimination reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000009834 selective interaction Effects 0.000 description 1
238000004467 single crystal X-ray diffraction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
206010041823 squamous cell carcinoma Diseases 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000002381 testicular Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000516071A 1986-08-15 1986-08-15 Derives du diamineplatine a substituants hydroxyles Expired - Lifetime CA1282058C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000516071A CA1282058C (fr)	1986-08-15	1986-08-15	Derives du diamineplatine a substituants hydroxyles

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000516071A CA1282058C (fr)	1986-08-15	1986-08-15	Derives du diamineplatine a substituants hydroxyles

Publications (1)

Publication Number	Publication Date
CA1282058C true CA1282058C (fr)	1991-03-26

Family

ID=4133741

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000516071A Expired - Lifetime CA1282058C (fr)	1986-08-15	1986-08-15	Derives du diamineplatine a substituants hydroxyles

Country Status (1)

Country	Link
CA (1)	CA1282058C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP4461293A1 (fr) *	2023-05-12	2024-11-13	Biomedical Research Foundation Academy of Athens	Composés anticancéreux du platine se liant au récepteur de la biotine

1986
- 1986-08-15 CA CA000516071A patent/CA1282058C/fr not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP4461293A1 (fr) *	2023-05-12	2024-11-13	Biomedical Research Foundation Academy of Athens	Composés anticancéreux du platine se liant au récepteur de la biotine

Legal Events

Date	Code	Title	Description
2000-03-27	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 20000327

Publication	Publication Date	Title
EP0155705B1 (fr)	1989-12-13	Complexe antitumeurs de platine
EP0219936B1 (fr)	1989-12-13	Complexes de platine
KR100442096B1 (ko)	2004-07-30	이중 디카르복실산 디아미노플라틴 착체의 항종양 유도체, 그의 제조방법, 그것을 함유하는 약학조성물 및 그 유도체의 적용
HU184922B (en)	1984-11-28	Process for preparing platinum/iv./-diamine complexes and pharma ceutical compositions containing thereof
EP0462980A1 (fr)	1992-01-02	Agents pharmaceutiques a base de platine
EP0231847B1 (fr)	1991-11-06	Complexes de [2,2-bis(aminomethyl)-1,3-propanediol-N,N']platine
EP0282672B1 (fr)	1990-11-28	Complexes de platine
EP0537575A1 (fr)	1993-04-21	Bromhydrate d'un dérivé de DC-89 ayant une activité antitumorale
ITMI940610A1 (it)	1995-10-01	Platino complessi cationici trinucleari ad attivita' antitumorale e composizioni farmaceutiche che li contengono
EP0812852B1 (fr)	2003-04-23	Nouveaux complexes de platine (iv), leur procede de production et agents cancerostatiques les contenant
EP0176005B1 (fr)	1991-01-16	Complexes de platine
EP0163316B1 (fr)	1990-05-16	Complexes de platine intercalatifs pour le traitement du cancer
US4687780A (en)	1987-08-18	Anti-tumor compounds of platinum
CA1282058C (fr)	1991-03-26	Derives du diamineplatine a substituants hydroxyles
CA1265811A (fr)	1990-02-13	Composes du platine, diamines et alcoxy-alcoyles
US5028726A (en)	1991-07-02	Platinum amine sulfoxide complexes
CN100381459C (zh)	2008-04-16	阿霉素的衍生物及其制备方法和用途
US6110907A (en)	2000-08-29	Synthesis of platinum complexes and uses thereof
EP0376076A1 (fr)	1990-07-04	Complexes de platine
ITMI942383A1 (it)	1996-05-24	Platino complessi cationici trinucleari ad attivita' antitumorale
EP0214862B1 (fr)	1991-03-13	Complexes de platine antitumeur, leur préparation et leur utilisation
US4895935A (en)	1990-01-23	Platinum pharmaceuticals
EP0518645B1 (fr)	1997-01-15	Complexe de platine(II) et agent antitumeur
JP2749092B2 (ja)	1998-05-13	白金系医薬品
JPS61249993A (ja)	1986-11-07	新規有機白金錯体及びその製法

CA1282058C - Derives du diamineplatine a substituants hydroxyles - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4133741

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Similar Documents

Legal Events