ES2339430T3 - Agentes antitumorales y procedimiento de produccion de los mismos. - Google Patents
Agentes antitumorales y procedimiento de produccion de los mismos. Download PDFInfo
- Publication number
- ES2339430T3 ES2339430T3 ES02758880T ES02758880T ES2339430T3 ES 2339430 T3 ES2339430 T3 ES 2339430T3 ES 02758880 T ES02758880 T ES 02758880T ES 02758880 T ES02758880 T ES 02758880T ES 2339430 T3 ES2339430 T3 ES 2339430T3
- Authority
- ES
- Spain
- Prior art keywords
- protoporphyrin
- peg
- formula
- znpp
- compound
- Prior art date
- 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
Links
- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 33
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 31
- 229950003776 protoporphyrin Drugs 0.000 claims abstract description 24
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000004032 porphyrins Chemical class 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 12
- 239000011701 zinc Substances 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004246 zinc acetate Substances 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 35
- 229920003169 water-soluble polymer Polymers 0.000 abstract description 9
- 230000002401 inhibitory effect Effects 0.000 abstract description 8
- 230000001093 anti-cancer Effects 0.000 abstract description 6
- 238000010253 intravenous injection Methods 0.000 abstract description 3
- 102000016761 Haem oxygenases Human genes 0.000 abstract 1
- 108050006318 Haem oxygenases Proteins 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 18
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 12
- 230000021615 conjugation Effects 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 7
- 201000011510 cancer Diseases 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 150000004033 porphyrin derivatives Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000011135 tin Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- -1 hydroxypropyl Chemical group 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 230000036542 oxidative stress Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- GWZYPXHJIZCRAJ-UHFFFAOYSA-N Biliverdin Natural products CC1=C(C=C)C(=C/C2=NC(=Cc3[nH]c(C=C/4NC(=O)C(=C4C)C=C)c(C)c3CCC(=O)O)C(=C2C)CCC(=O)O)NC1=O GWZYPXHJIZCRAJ-UHFFFAOYSA-N 0.000 description 3
- RCNSAJSGRJSBKK-NSQVQWHSSA-N Biliverdin IX Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(\C=C/2C(=C(C)C(=C/C=3C(=C(C=C)C(=O)N=3)C)/N\2)CCC(O)=O)N1 RCNSAJSGRJSBKK-NSQVQWHSSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000035508 accumulation Effects 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- QBUVFDKTZJNUPP-UHFFFAOYSA-N biliverdin-IXalpha Natural products N1C(=O)C(C)=C(C=C)C1=CC1=C(C)C(CCC(O)=O)=C(C=C2C(=C(C)C(C=C3C(=C(C=C)C(=O)N3)C)=N2)CCC(O)=O)N1 QBUVFDKTZJNUPP-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000007123 defense Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000684 flow cytometry Methods 0.000 description 2
- 238000001641 gel filtration chromatography Methods 0.000 description 2
- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 2
- 229940025294 hemin Drugs 0.000 description 2
- 229920001477 hydrophilic polymer Polymers 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000008728 vascular permeability Effects 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004020 Oxygenases Human genes 0.000 description 1
- 108090000417 Oxygenases Proteins 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241001415846 Procellariidae Species 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 238000009924 canning Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 150000003278 haem Chemical group 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000002601 intratumoral effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 210000005265 lung cell Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical class Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000036326 tumor accumulation Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- FUTVBRXUIKZACV-UHFFFAOYSA-J zinc;3-[18-(2-carboxylatoethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoate Chemical compound [Zn+2].[N-]1C2=C(C)C(CCC([O-])=O)=C1C=C([N-]1)C(CCC([O-])=O)=C(C)C1=CC(C(C)=C1C=C)=NC1=CC(C(C)=C1C=C)=NC1=C2 FUTVBRXUIKZACV-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001264918A JP5000050B2 (ja) | 2001-08-31 | 2001-08-31 | 抗腫瘍剤及びその製造方法 |
| JP2001-264918 | 2001-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2339430T3 true ES2339430T3 (es) | 2010-05-20 |
Family
ID=19091449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02758880T Expired - Lifetime ES2339430T3 (es) | 2001-08-31 | 2002-08-29 | Agentes antitumorales y procedimiento de produccion de los mismos. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7026488B2 (enExample) |
| EP (1) | EP1421938B1 (enExample) |
| JP (1) | JP5000050B2 (enExample) |
| KR (1) | KR100876343B1 (enExample) |
| CN (1) | CN100406010C (enExample) |
| AT (1) | ATE456951T1 (enExample) |
| CA (1) | CA2458744C (enExample) |
| DE (1) | DE60235279D1 (enExample) |
| DK (1) | DK1421938T3 (enExample) |
| ES (1) | ES2339430T3 (enExample) |
| WO (1) | WO2003018007A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004196770A (ja) * | 2002-10-24 | 2004-07-15 | Effector Cell Institute Inc | 樹状細胞前駆体の血中レベル上昇剤 |
| GB2397067B (en) | 2002-12-23 | 2005-05-11 | Destiny Pharma Ltd | Porphin & azaporphin derivatives with at least one cationic-nitrogen-containing meso-substituent for use in photodynamic therapy & in vitro sterilisation |
| GB2408265A (en) * | 2003-11-21 | 2005-05-25 | Univ Sheffield | Water-soluble hyperbranched polymer porphyrins |
| GB2415372A (en) | 2004-06-23 | 2005-12-28 | Destiny Pharma Ltd | Non photodynamical or sonodynamical antimicrobial use of porphyrins and azaporphyrins containing at least one cationic-nitrogen-containing substituent |
| JPWO2006112362A1 (ja) * | 2005-04-18 | 2008-12-11 | 前田 浩 | 高分子型癌治療用医薬の製造方法 |
| AU2007276763B2 (en) * | 2006-07-24 | 2011-03-17 | University Of Maryland, Baltimore | Heme oxygenase inhibitors and methods of therapeutic use |
| WO2009015274A2 (en) * | 2007-07-24 | 2009-01-29 | University Of Florida Research Foundation, Inc. | Polyethylene based bioactive agents |
| JP2010024170A (ja) * | 2008-07-17 | 2010-02-04 | Hiroshi Maeda | 抗悪性腫瘍剤の腫瘍組織への局所送達増強剤 |
| CN102000070B (zh) * | 2009-07-08 | 2012-05-23 | 山东弘立医学动物实验研究有限公司 | 用于治疗肿瘤的锰卟啉-氯尼达明联合用药物 |
| KR101164138B1 (ko) | 2009-12-24 | 2012-07-11 | 재단법인대구경북과학기술원 | 광역학 치료용 수용성 나노구조체 |
| CN101948566B (zh) * | 2010-06-23 | 2012-09-19 | 中国科学院化学研究所 | 一种用于抗真菌、抗癌及细胞成像的多功能聚合物及其制备方法 |
| EP2774625B1 (en) * | 2011-09-05 | 2017-04-12 | Hiroshi Maeda | Polymer-type fluorescent molecule probe |
| CN104069492B (zh) * | 2014-01-24 | 2019-05-28 | 中国科学院福建物质结构研究所 | 靶向表达尿激酶受体的肿瘤的光敏剂及其制备方法和用途 |
| CN108610346B (zh) * | 2018-04-02 | 2020-06-02 | 杭州至重医药科技有限公司 | 一种光敏酞菁固体材料及其制备方法与应用 |
| CN114262442B (zh) * | 2021-12-24 | 2023-05-02 | 厦门金达威生物科技有限公司 | 一种两亲聚合物和脂溶性营养素纳米颗粒及其制备方法 |
| CN119456038A (zh) * | 2025-01-14 | 2025-02-18 | 浙江工业大学 | 一种金属卟啉基柔性共轭有机聚合物-卤氧铋复合材料及制备方法和光催化co2还原应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2645079A1 (de) * | 1976-10-06 | 1978-04-13 | Bayer Ernst | Polymere sauerstofftraeger und verfahren zu ihrer herstellung |
| JPS584061B2 (ja) * | 1979-04-27 | 1983-01-24 | 森六株式会社 | ブロック共重合体金属錯体 |
| ATE206395T1 (de) * | 1990-05-15 | 2001-10-15 | Hyperion Inc | Fluoreszierende porphyrin- und fluoreszierende phthalocyanin-polyethylenglykol-, polyol- und saccharidderivate als fluoreszierende sonden |
| US5622685A (en) * | 1990-05-30 | 1997-04-22 | Deutches Krebsforchunszentrum Stiftung Des Offentlichen Rechts | Polyether-substituted porphyrin anti-tumor agents |
| EP0502723B1 (en) | 1991-03-05 | 1996-10-09 | Hitachi Chemical Co., Ltd. | Water-soluble tetraazaporphins and fluorochrome for labeling |
| US6362175B1 (en) * | 1991-09-20 | 2002-03-26 | The Trustees Of The University Of Pennsylvania | Porphyrin compounds for imaging tissue oxygen |
| DE69129150T2 (de) * | 1991-10-14 | 1998-10-08 | The Procter & Gamble Co., Cincinnati, Ohio | Waschmittelzusammensetzungen mit Zusätzen zur Verhinderung der Farbstoffübertragung |
| DE4232925A1 (de) * | 1992-09-28 | 1994-03-31 | Diagnostikforschung Inst | 3-,8-substituierte Deuteroporphyrinderivate, diese enthaltende pharmazeutische Mittel und Verfahren zu ihrer Herstellung |
| GB9408746D0 (en) * | 1994-05-03 | 1994-06-22 | Scotia Holdings Plc | Tumour locallising photosensitising compounds |
| US5756726A (en) * | 1995-06-02 | 1998-05-26 | Pharmacyclics, Inc. | Methods of producing singlet oxygen using compounds having improved functionalization |
| US20020155999A1 (en) * | 1998-04-30 | 2002-10-24 | Han In Suk | Method of using a porphyrin-like molecule conjugated with an anti-cancer drug for the treatment of cancer |
| GB0001455D0 (en) * | 2000-01-21 | 2000-03-15 | Scotia Holdings Plc | Porphyrins and related compounds |
-
2001
- 2001-08-31 JP JP2001264918A patent/JP5000050B2/ja not_active Expired - Fee Related
-
2002
- 2002-08-29 KR KR1020047001975A patent/KR100876343B1/ko not_active Expired - Fee Related
- 2002-08-29 DE DE60235279T patent/DE60235279D1/de not_active Expired - Lifetime
- 2002-08-29 WO PCT/JP2002/008707 patent/WO2003018007A1/ja not_active Ceased
- 2002-08-29 CN CNB028171373A patent/CN100406010C/zh not_active Expired - Fee Related
- 2002-08-29 CA CA2458744A patent/CA2458744C/en not_active Expired - Fee Related
- 2002-08-29 US US10/484,726 patent/US7026488B2/en not_active Expired - Lifetime
- 2002-08-29 ES ES02758880T patent/ES2339430T3/es not_active Expired - Lifetime
- 2002-08-29 EP EP02758880A patent/EP1421938B1/en not_active Expired - Lifetime
- 2002-08-29 AT AT02758880T patent/ATE456951T1/de active
- 2002-08-29 DK DK02758880.5T patent/DK1421938T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1421938A1 (en) | 2004-05-26 |
| US20040234495A1 (en) | 2004-11-25 |
| US7026488B2 (en) | 2006-04-11 |
| EP1421938B1 (en) | 2010-02-03 |
| JP5000050B2 (ja) | 2012-08-15 |
| EP1421938A4 (en) | 2005-11-23 |
| KR100876343B1 (ko) | 2008-12-29 |
| DK1421938T3 (da) | 2010-05-17 |
| CN100406010C (zh) | 2008-07-30 |
| WO2003018007A1 (en) | 2003-03-06 |
| JP2003073273A (ja) | 2003-03-12 |
| CA2458744A1 (en) | 2003-03-06 |
| KR20040030951A (ko) | 2004-04-09 |
| CA2458744C (en) | 2010-09-14 |
| DE60235279D1 (de) | 2010-03-25 |
| CN1549712A (zh) | 2004-11-24 |
| ATE456951T1 (de) | 2010-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Ji et al. | Toward carbon monoxide–based therapeutics: critical drug delivery and developability issues | |
| EP1421938B1 (en) | Antitumor agents and process for producing the same | |
| US20040186087A1 (en) | Siderophore conjugates of photoactive dyes for photodynamic therapy | |
| CN1741801B (zh) | 水溶性阴离子型细菌叶绿素衍生物及其用途 | |
| Cowled et al. | Pharmacological modulation of photodynamic therapy with hematoporphyrin derivative and light | |
| US8664382B2 (en) | Antibacterial compositions comprising metal phthalocyanine analogues | |
| JP4981031B2 (ja) | 化学発光およびリガンド−光感作物質コンジュゲートを使用する光力学的療法 | |
| Schaffer et al. | Porphyrins as radiosensitizing agents for solid neoplasms | |
| CN112334158B (zh) | 用于硼中子俘获疗法的能够在短时间内选择性地或局部地靶向肿瘤组织的聚集性硼10药剂 | |
| RU2323722C2 (ru) | Фармацевтическая композиция для фотодинамической терапии и способ лечения онкологического заболевания с ее использованием | |
| EP0539960B1 (en) | Hematoporphyrin derivatives complex salts and their use in the detection and treatment of neoplasms | |
| Mody et al. | Porphyrin-and expanded porphyrin-based diagnostic and therapeutic agents | |
| ES2202704T3 (es) | Agente antitumoral que comprende un complejo de una oxidorreductasa de un polimero y un substrato del enzima. | |
| WO2006078713A2 (en) | Methotrexate combinations for treating inflammatory diseases | |
| US8163796B1 (en) | Treatment of cancer by oxidation-reduction potentiation of cancerostatic dicarbonyls | |
| JP2012087141A (ja) | 抗腫瘍剤及びその製造方法 | |
| CN114558148B (zh) | 一种肿瘤“开关型”纳米光疗系统的制备方法及应用 | |
| JP3425111B2 (ja) | イオン性ポルフィリン化合物 | |
| EP0810866A1 (en) | Use of acid-sensitive organo- transition metal compounds in cancer treatment | |
| JPH04103538A (ja) | 制癌剤副作用抑制剤 | |
| WO2023283732A1 (en) | Porphyrin nanovesicle with fatty acid conjugate | |
| WO2014071138A1 (en) | Disease detection and treatment through activation of compounds using external energy | |
| JP2008303197A (ja) | 細胞内プロトポルフィリンｉｘ集積量増加剤及びそれを含有した光線力学的診断用又は治療用組成物 | |
| WO1998015271A1 (en) | 9-substituted porphycenes |