NO314806B1 - Fotoaktive benzoporfyrinderivatforbindelser, fremgangsmåter ved fremstilling og anvendelse derav, samt farmasöytisk blanding inneholdendedisse - Google Patents
Fotoaktive benzoporfyrinderivatforbindelser, fremgangsmåter ved fremstilling og anvendelse derav, samt farmasöytisk blanding inneholdendedisse Download PDFInfo
- Publication number
- NO314806B1 NO314806B1 NO19995440A NO995440A NO314806B1 NO 314806 B1 NO314806 B1 NO 314806B1 NO 19995440 A NO19995440 A NO 19995440A NO 995440 A NO995440 A NO 995440A NO 314806 B1 NO314806 B1 NO 314806B1
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- Norway
- Prior art keywords
- vinyl
- compound
- metallized
- labeled
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 benzoporphyrin derivative compounds Chemical class 0.000 title description 23
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 229920002554 vinyl polymer Polymers 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000906 photoactive agent Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 8
- 238000001212 derivatisation Methods 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 238000002428 photodynamic therapy Methods 0.000 abstract description 12
- 150000001408 amides Chemical class 0.000 abstract description 8
- 150000002148 esters Chemical class 0.000 abstract description 8
- PLVAJLBZYYGQNL-UHFFFAOYSA-N C12CC=C(N1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C3=C(C(N=1)=C2)C=CC=C3 Chemical class C12CC=C(N1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C3=C(C(N=1)=C2)C=CC=C3 PLVAJLBZYYGQNL-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 208000030963 borderline personality disease Diseases 0.000 description 13
- 206010006475 bronchopulmonary dysplasia Diseases 0.000 description 13
- 238000007792 addition Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 238000005698 Diels-Alder reaction Methods 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 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 description 5
- 239000002585 base Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 229950003776 protoporphyrin Drugs 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000008685 targeting Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical compound CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
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- 239000000284 extract Substances 0.000 description 2
- 229960003569 hematoporphyrin Drugs 0.000 description 2
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- 210000001165 lymph node Anatomy 0.000 description 2
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- 238000002844 melting Methods 0.000 description 2
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- 208000017983 photosensitivity disease Diseases 0.000 description 2
- 231100000434 photosensitization Toxicity 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
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- 238000010561 standard procedure Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
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- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- MHIITNFQDPFSES-UHFFFAOYSA-N 25,26,27,28-tetrazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1(25),2,4,6,8(27),9,11,13,15,17,19,21,23-tridecaene Chemical class N1C(C=C2C3=CC=CC=C3C(C=C3NC(=C4)C=C3)=N2)=CC=C1C=C1C=CC4=N1 MHIITNFQDPFSES-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 208000037815 bloodstream infection Diseases 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000022534 cell killing Effects 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 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
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- HXYIQMHXZZPHNJ-UHFFFAOYSA-N protoporphyrin xiii Chemical compound N1C(C=C2C(=C(C=C)C(C=C3C(=C(CCC(=O)OC)C(=C4)N3)C)=N2)C)=C(C)C(C=C)=C1C=C1C(C)=C(CCC(=O)OC)C4=N1 HXYIQMHXZZPHNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910001432 tin ion Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- 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
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85232697A | 1997-05-07 | 1997-05-07 | |
| US08/918,840 US5880145A (en) | 1997-05-07 | 1997-08-26 | Class of benzoporphyrin derivative photoactive compounds |
| PCT/CA1998/000425 WO1998050386A1 (en) | 1997-05-07 | 1998-04-29 | A new class of benzoporphyrin derivative photoactive compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995440D0 NO995440D0 (no) | 1999-11-05 |
| NO995440L NO995440L (no) | 1999-11-05 |
| NO314806B1 true NO314806B1 (no) | 2003-05-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995440A NO314806B1 (no) | 1997-05-07 | 1999-11-05 | Fotoaktive benzoporfyrinderivatforbindelser, fremgangsmåter ved fremstilling og anvendelse derav, samt farmasöytisk blanding inneholdendedisse |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5990149A (pl) |
| EP (1) | EP0983272B1 (pl) |
| JP (2) | JP3907212B2 (pl) |
| CN (1) | CN1120166C (pl) |
| AT (1) | ATE253068T1 (pl) |
| AU (1) | AU749741B2 (pl) |
| CA (1) | CA2288045C (pl) |
| CZ (1) | CZ299361B6 (pl) |
| DE (1) | DE69819318T2 (pl) |
| DK (1) | DK0983272T3 (pl) |
| ES (1) | ES2210740T3 (pl) |
| HK (1) | HK1025324A1 (pl) |
| HU (1) | HU224176B1 (pl) |
| IL (1) | IL132494A0 (pl) |
| NO (1) | NO314806B1 (pl) |
| PL (1) | PL202340B1 (pl) |
| PT (1) | PT983272E (pl) |
| TW (1) | TW474938B (pl) |
| WO (1) | WO1998050386A1 (pl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6756396B1 (en) | 1997-05-07 | 2004-06-29 | Qlt Inc. | Ethylene glycol esters as photoactive agents |
| EP0983273B8 (en) * | 1997-05-07 | 2002-10-09 | QLT Inc. | Ethylene glycol esters of monohydrobenzoporphyrin derivatives as photoactive agents |
| AU4278400A (en) * | 1999-04-14 | 2000-11-14 | University Of British Columbia, The | Improved beta,beta,-dihydroxy meso-substituted chlorins, isobacteriochlorins, and bacteriochlorins |
| US20020022032A1 (en) * | 1999-04-23 | 2002-02-21 | Curry Patrick Mark | Immuno-adjuvant PDT treatment of metastatic tumors |
| US7122568B1 (en) | 1999-11-17 | 2006-10-17 | Qlt, Inc. | Use of low-dose PDT to inhibit restenosis |
| US6984395B2 (en) * | 2001-04-11 | 2006-01-10 | Qlt, Inc. | Drug delivery system for hydrophobic drugs |
| EP1465590B1 (en) * | 2001-11-02 | 2008-03-26 | The Governors Of The University Of Alberta | Micelle compositions containing pegylated phospholipids and a photosensitizer |
| WO2003039596A1 (en) * | 2001-11-09 | 2003-05-15 | Qlt Inc. | Photodynamic therapy for the treatment of hair loss |
| CA2437638A1 (en) * | 2003-08-20 | 2005-02-20 | John Robert North | Photodynamic therapy |
| CA2457214A1 (en) | 2004-02-06 | 2005-08-06 | Qlt Inc. | Photodynamic therapy for the treatment of acne |
| GB0415663D0 (en) * | 2004-07-13 | 2004-08-18 | Psimei Pharmaceuticals Plc | Compound |
| FR2877943B1 (fr) * | 2004-11-16 | 2008-09-05 | Univ De Coimbra | Nouveaux derives de porphyrine, notamment chlorines et/ou bacteriochlorine, et leurs applications en therapie photodynamique |
| EP2663285A2 (en) | 2011-01-13 | 2013-11-20 | Qlt Inc. | Pharmaceutical compositions for topical delivery of photosensitizers and uses thereof |
| BR112015000383A2 (pt) | 2012-07-11 | 2017-06-27 | Dermira Inc | composição farmacêutica, e, métodos para preparação de uma composição farmacêutica, para reduzir a taxa de excreção de sebo das glândulas sebáceas na pele de um indivíduo e para tratamento da acne |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920143A (en) * | 1987-04-23 | 1990-04-24 | University Of British Columbia | Hydro-monobenzoporphyrin wavelength-specific cytotoxic agents |
| US4883790A (en) * | 1987-01-20 | 1989-11-28 | University Of British Columbia | Wavelength-specific cytotoxic agents |
| US5880145A (en) * | 1997-05-07 | 1999-03-09 | The University Of British Columbia | Class of benzoporphyrin derivative photoactive compounds |
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1998
- 1998-04-29 PL PL336633A patent/PL202340B1/pl not_active IP Right Cessation
- 1998-04-29 CZ CZ0385799A patent/CZ299361B6/cs not_active IP Right Cessation
- 1998-04-29 DK DK98916765T patent/DK0983272T3/da active
- 1998-04-29 AT AT98916765T patent/ATE253068T1/de not_active IP Right Cessation
- 1998-04-29 JP JP54757098A patent/JP3907212B2/ja not_active Expired - Fee Related
- 1998-04-29 AU AU70257/98A patent/AU749741B2/en not_active Ceased
- 1998-04-29 ES ES98916765T patent/ES2210740T3/es not_active Expired - Lifetime
- 1998-04-29 WO PCT/CA1998/000425 patent/WO1998050386A1/en active IP Right Grant
- 1998-04-29 CN CN98804869A patent/CN1120166C/zh not_active Expired - Fee Related
- 1998-04-29 HU HU0003939A patent/HU224176B1/hu not_active IP Right Cessation
- 1998-04-29 DE DE69819318T patent/DE69819318T2/de not_active Expired - Fee Related
- 1998-04-29 EP EP98916765A patent/EP0983272B1/en not_active Expired - Lifetime
- 1998-04-29 PT PT98916765T patent/PT983272E/pt unknown
- 1998-04-29 CA CA002288045A patent/CA2288045C/en not_active Expired - Fee Related
- 1998-04-29 IL IL13249498A patent/IL132494A0/xx active IP Right Grant
- 1998-07-21 TW TW087111990A patent/TW474938B/zh not_active IP Right Cessation
-
1999
- 1999-03-09 US US09/265,245 patent/US5990149A/en not_active Expired - Fee Related
- 1999-11-05 NO NO19995440A patent/NO314806B1/no not_active IP Right Cessation
-
2000
- 2000-07-21 HK HK00104515A patent/HK1025324A1/xx not_active IP Right Cessation
-
2004
- 2004-03-24 JP JP2004088106A patent/JP2004217671A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| TW474938B (en) | 2002-02-01 |
| EP0983272A1 (en) | 2000-03-08 |
| HK1025324A1 (en) | 2000-11-10 |
| CN1255135A (zh) | 2000-05-31 |
| CZ299361B6 (cs) | 2008-07-02 |
| WO1998050386A1 (en) | 1998-11-12 |
| PT983272E (pt) | 2004-03-31 |
| HUP0003939A3 (en) | 2003-06-30 |
| DK0983272T3 (da) | 2004-03-01 |
| CZ385799A3 (cs) | 2000-04-12 |
| JP3907212B2 (ja) | 2007-04-18 |
| HU224176B1 (hu) | 2005-06-28 |
| EP0983272B1 (en) | 2003-10-29 |
| PL202340B1 (pl) | 2009-06-30 |
| CA2288045C (en) | 2007-01-23 |
| JP2004217671A (ja) | 2004-08-05 |
| ATE253068T1 (de) | 2003-11-15 |
| JP2000516636A (ja) | 2000-12-12 |
| AU749741B2 (en) | 2002-07-04 |
| DE69819318T2 (de) | 2004-08-19 |
| NO995440D0 (no) | 1999-11-05 |
| CA2288045A1 (en) | 1998-11-12 |
| DE69819318D1 (de) | 2003-12-04 |
| PL336633A1 (en) | 2000-07-03 |
| IL132494A0 (en) | 2001-03-19 |
| CN1120166C (zh) | 2003-09-03 |
| AU7025798A (en) | 1998-11-27 |
| NO995440L (no) | 1999-11-05 |
| ES2210740T3 (es) | 2004-07-01 |
| US5990149A (en) | 1999-11-23 |
| HUP0003939A2 (en) | 2001-03-28 |
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