JP2000516636A - 新規なクラスのベンゾポルフィリン誘導体光活性化合物 - Google Patents
新規なクラスのベンゾポルフィリン誘導体光活性化合物Info
- Publication number
- JP2000516636A JP2000516636A JP10547570A JP54757098A JP2000516636A JP 2000516636 A JP2000516636 A JP 2000516636A JP 10547570 A JP10547570 A JP 10547570A JP 54757098 A JP54757098 A JP 54757098A JP 2000516636 A JP2000516636 A JP 2000516636A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- compounds
- vinyl
- carboxyl
- group
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 118
- 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 title description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- -1 polycyclic amines Chemical class 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 25
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 229920002554 vinyl polymer Polymers 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000001212 derivatisation Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000002372 labelling Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 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
- 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
- 125000000597 dioxinyl group Chemical group 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 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
- 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 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004926 indolenyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000005438 isoindazolyl group Chemical group 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000003585 oxepinyl group Chemical group 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001806 thionaphthenyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 238000001465 metallisation Methods 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
- 239000012080 ambient air Substances 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 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 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000007257 deesterification reaction Methods 0.000 claims 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 abstract description 16
- 238000002428 photodynamic therapy Methods 0.000 abstract description 14
- 150000002148 esters Chemical class 0.000 abstract description 13
- 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 3
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 208000030963 borderline personality disease Diseases 0.000 description 14
- 206010006475 bronchopulmonary dysplasia Diseases 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IRKHFYZGVKPLBN-UHFFFAOYSA-N carboxy propanoate Chemical class CCC(=O)OC(O)=O IRKHFYZGVKPLBN-UHFFFAOYSA-N 0.000 description 12
- 210000001519 tissue Anatomy 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 238000005698 Diels-Alder reaction Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 125000001475 halogen functional group Chemical group 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000906 photoactive agent Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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 3
- 239000000243 solution Substances 0.000 description 3
- 238000006467 substitution reaction Methods 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-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
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 229960003569 hematoporphyrin Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 210000001165 lymph node Anatomy 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 208000017983 photosensitivity disease Diseases 0.000 description 2
- 231100000434 photosensitization Toxicity 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 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
- 241001465754 Metazoa Species 0.000 description 1
- 239000004727 Noryl Substances 0.000 description 1
- 229920001207 Noryl Polymers 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 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
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000007398 colorimetric assay Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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- 150000004702 methyl esters Chemical class 0.000 description 1
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- 210000003205 muscle Anatomy 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- 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
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- 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
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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)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.以下の式の化合物、ならびにこれらの塩および/または金属化および/または 標識化および/または結合体形態: ここで、R1は、アルキル(1〜6C)であり; Yは、−OHまたは−NR2 2または−NHNR2 2(ここで各R2は独立してH または1〜10Cの置換もしくは非置換炭化水素基であるか、あるいは両方のR2 は一緒になって、1〜20Cの単環式または多環式アミンを与える)であるか;あ るいは、−OR3(ここでR3は少なくとも1つのヘテロ原子含有置換基で置換さ れたアルキル(1〜10C)である)であり; nは、0〜6の整数であり、 各Xは、独立して、−OH;または−OR4(ここでR4は、1〜10Cの非置換 炭化水素基である)であるか;または−NR2 2もしくは−NHNR2 2(R2は、 上記で定義したとおりである)であるか;または−OR3(ここでR3は、上記で 定義したとおりである)であり;そして R5は、ビニルまたはその誘導体である。 2.請求項1に記載の化合物であって、nは2であり;および/あるいは ここで、R5は、ビニル、-CHOR'、-CHO、-COOR'、-CH(OR')CH3、-CH(OR')CH2O R'、-CH(SR')CH3、-CH(NR')2CH3、-CH(CN)CH3、-CH(COOR')CH3、-CH(OOCR')CH3 、-CH(NR'COR')CH3、-CH(CONR'2)CH3、-CH(ハロ)CH3、もしくは-CH(ハロ)CH2(ハ ロ)であり、ここでR'がHであるかもしくは必要に応じてヘテロ原子含有置換基 で置換された炭化水素基(1〜6C)であるか、またはR5は、該ビニル基の直 接もしくは間接誘導体化から得られる12C未満の有機基であるか、またはR5は 、1〜3個のテトラピロール型核を含む基を含み;および/あるいは Yおよび両方のXは-OHである、化合物。 3.R5がビニルであり、かつYおよび両方のXが-OHであり;そしてnが2であ る、請求項2に記載の化合物。 4.以下の式の「三酸(triacid)」である、請求項3に記載の化合物:5.Yが-NR2 2である、請求項1または2に記載の化合物。 6.各-NR2 2が独立して以下を含む、請求項5に記載の化合物:メチル、エチ ル、プロピル、ブチル、イソブチル、ヘキシル、ヒドロキシアルキル(1〜6C )、シクロペンチル、シクロペンタジエニル、フリル、チエニル、ピロリル、イ ソピロリル、ピリジル、ピラゾリル、インドリル、イソインドリル、イミダゾリ ル、イソイミダゾリル、トリアゾリル、フラザニル、イソキサゾリル、オキサゾ リル、チアゾリル、イソチアゾリル、オキサジアゾリル、オキサトリアゾリル、 ジオキサゾリル、フェニル、シクロヘキシル、ピラニル、ジオキシニル、ピリジ ニル、ピリダジニル、ピリミジニル、ピラジニル、ピペラジニル、インドリジニ ル、ピロリジニル、トリアジニル、オキサジニル、イソキサジニル、オキサチア ジニル、オキサジアジニル、モルホリニル、アゼピニル、オキセピニル、チエピ ニル、ジアゼピニル、インデニル、イソインデニル、ベンゾフラニル、イソベン ゾフラニル、チオナフテニル、イソチオナフテニル、インドレニル、イソベンザ ゾリル、ピラノーピロリル、インダゾリル、イソインダゾリル、インドキサジニ ル、ベンゾキサゾリル、クロメニル、アンタニル、ナフチル、テトラリニル、デ カリニル、ベンゾチエニル、ベンゾピラニル(benzyopyranyl)、クマリニル、シ ノリニル、ベンゾピロニル、キノリニル、イソキノリニル、ベンゾジアジニル、 キノリル、イソキノリル、キナゾリニル、キノリジニル、キノキサリニル、ナフ チリジニル、ピリド-ピリジニル、ベンゾキサジニル、ベンズイソキサジニル、 プリニル、フタラジニル、ナフチリジニル、プテリジニル、またはベンジル。 7.両方のXが-NR2 2である、請求項1〜2または5〜6のいずれかに記載の 化合物。 8.XおよびYの両方が-OCH2CH2OHである、請求項1〜2のいずれかに記載の化 合物。 9.YがOHであり、両方のXが-OR6であり、ここでR6が低級アルキル(1〜 4C)である、請求項1または2に記載の化合物。 10.以下の式の請求項9に記載の化合物: ここで、nは2であり、R5はビニルである。 11.以下の式の製品化合物、ならびにこれらの塩および/または金属化および/ または標識化および/または結合体形態を調製する方法であって: ここで、R1が、アルキル(1〜6C)であり; nが、1〜6の整数であり;そして ここで、R5が、ビニルまたはその誘導体であり、 該方法は、該製品化合物のより高度にエステル化された形態、またはその塩、 金属化形態、標識化形態、もしくは結合体形態を、 脱エステルを生じるのに十分な時間、塩基および溶媒で処理して、該製品化合 物を得る工程を包含する、方法。 12.請求項11に記載の方法であって、前記処理が、酸化を防止する不活性雰 囲気下で行われる;および/あるいは 前記塩基が、水酸化ナトリウム、水酸化カリウム、水酸化リチウム、水酸化カ ルシウム、水酸化バリウム、水酸化クロム、もしくはテトラアルキルアンモニウ ムヒドロキシドである;および/あるいは 前記溶媒が、DMSO、低分子量アルコール、DMF、THF、もしくは水、またはこれ らの混合物である;および/あるいは 前記不活性雰囲気が、窒素、ヘリウムもしくはアルゴンガスによって提供され る;および/あるいは 前記処理が、約0〜60℃の温度で行われる;および/あるいは 前記処理が、約2〜48時間、室温で行われる、方法。 13.前記製品化合物、またはその塩、金属化形態、標識化形態、もしくは結合 体化形態を水に溶解する工程、および該製品化合物を沈殿させるのに十分な酸を 添加する工程をさらに包含する、請求項11または12に記載の方法。 14.式1〜4の化合物、またはそれらの塩もしくは金属化もしくは標識化もし くは結合体化形態を調製する方法であって、ここで、R1はアルキル(1〜6C )であり;Yおよび両方のXは-OR3または-NR2 2であり;nは0〜6の整数 であり;そしてR5はビニルまたはその誘導体である、方法であって;該方法は 、以下の式の出発化合物のカルボキシル活性化形態、ならびにこれらの塩および /または金属化および/または標識化および/または結合体化形態: (ここで、R1は、アルキル(1〜6C)であり; nは、1〜6の整数であり;そして ここで、R5は、ビニルまたはその誘導体である)を、 式1〜4の化合物、またはそれらの金属化もしくは標識化もしくは結合体化形 態(ここで、Yおよび両方のXは-OR3またはNR2 2のいずれかである)を形成 するのに十分な条件下で、R3OHまたはHNR2 2で処理する工程を包含する、方法。 15.前記活性化カルボキシルが、前記出発化合物の遊離カルボキシル基を活性 化剤を用いて処理することによって得られる、請求項14に記載の方法。 16.Yおよび両方のXが-OR3であり;そしてここで、-OR3が-OCH2CH2OHで あり、-R3OHがエチレングリコールである、請求項14に記載の方法。 17.前記活性化剤がTSTUまたはBTTUである、請求項15に記載の方法。 18.薬学的に受容可能な賦形剤と混合されている請求項1〜10のいずれかに 記載の化合物を含む、薬学的組成物。 19.PDTを行うための改良された方法であって、該改良が、請求項1〜10の いずれかに記載の化合物を、光活性剤として用いることを包含する、方法。
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US85232697A | 1997-05-07 | 1997-05-07 | |
US08/852,326 | 1997-05-07 | ||
US08/918,840 | 1997-08-26 | ||
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 |
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JP2004088106A Division JP2004217671A (ja) | 1997-05-07 | 2004-03-24 | 新規なクラスのベンゾポルフィリン誘導体光活性化合物 |
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JP2000516636A true JP2000516636A (ja) | 2000-12-12 |
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JP2004088106A Pending JP2004217671A (ja) | 1997-05-07 | 2004-03-24 | 新規なクラスのベンゾポルフィリン誘導体光活性化合物 |
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EP (1) | EP0983272B1 (ja) |
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CN (1) | CN1120166C (ja) |
AT (1) | ATE253068T1 (ja) |
AU (1) | AU749741B2 (ja) |
CA (1) | CA2288045C (ja) |
CZ (1) | CZ299361B6 (ja) |
DE (1) | DE69819318T2 (ja) |
DK (1) | DK0983272T3 (ja) |
ES (1) | ES2210740T3 (ja) |
HK (1) | HK1025324A1 (ja) |
HU (1) | HU224176B1 (ja) |
IL (1) | IL132494A0 (ja) |
NO (1) | NO314806B1 (ja) |
PL (1) | PL202340B1 (ja) |
PT (1) | PT983272E (ja) |
TW (1) | TW474938B (ja) |
WO (1) | WO1998050386A1 (ja) |
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---|---|---|---|---|
JP2008506675A (ja) * | 2004-07-13 | 2008-03-06 | サイメイ ファーマスーティカルズ ピーエルシー | ポルフィリン誘導体及び光子活性化療法におけるその使用 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6756396B1 (en) | 1997-05-07 | 2004-06-29 | Qlt Inc. | Ethylene glycol esters as photoactive agents |
KR100397131B1 (ko) * | 1997-05-07 | 2003-09-13 | 유니버시티 오브 브리티시 콜롬비아 | 광활성제로서 모노하이드로벤조포르피린 유도체의 에틸렌글리콜 에스테르 |
AU4139600A (en) | 1999-04-14 | 2000-11-14 | University Of British Columbia, The | 1,3-dipolar cycloadditions to polypyrrolic macrocycles |
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 |
WO2003037295A2 (en) * | 2001-11-02 | 2003-05-08 | The Governors Of The University Of Alberta | Micelle compositions containing pegylated phospholipids and a photosensitizer |
JP2005514346A (ja) * | 2001-11-09 | 2005-05-19 | キュー エル ティー インク. | 光感作剤及び皮膚浸透エンハンサーを含有する組成物並びに光力学療法におけるそれらの使用 |
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 |
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 |
JP5964322B2 (ja) | 2011-01-13 | 2016-08-03 | キュー エル ティー インク.QLT Inc. | 光増感剤の局所送達用医薬組成物及びその使用 |
MX2015000429A (es) | 2012-07-11 | 2015-07-14 | Dermira Inc | Composiciones farmaceuticas para el suministro topico de fotosesibilizadores y usos de los mismos. |
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US4883790A (en) * | 1987-01-20 | 1989-11-28 | University Of British Columbia | Wavelength-specific cytotoxic agents |
US4920143A (en) * | 1987-04-23 | 1990-04-24 | University Of British Columbia | Hydro-monobenzoporphyrin 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
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- 1998-04-29 JP JP54757098A patent/JP3907212B2/ja not_active Expired - Fee Related
- 1998-04-29 HU HU0003939A patent/HU224176B1/hu not_active IP Right Cessation
- 1998-04-29 PT PT98916765T patent/PT983272E/pt unknown
- 1998-04-29 AT AT98916765T patent/ATE253068T1/de not_active IP Right Cessation
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- 1998-04-29 DE DE69819318T patent/DE69819318T2/de not_active Expired - Fee Related
- 1998-04-29 ES ES98916765T patent/ES2210740T3/es not_active Expired - Lifetime
- 1998-04-29 AU AU70257/98A patent/AU749741B2/en not_active Ceased
- 1998-04-29 WO PCT/CA1998/000425 patent/WO1998050386A1/en active IP Right Grant
- 1998-04-29 EP EP98916765A patent/EP0983272B1/en not_active Expired - Lifetime
- 1998-04-29 PL PL336633A patent/PL202340B1/pl not_active IP Right Cessation
- 1998-04-29 CA CA002288045A patent/CA2288045C/en not_active Expired - Fee Related
- 1998-04-29 CN CN98804869A patent/CN1120166C/zh not_active Expired - Fee Related
- 1998-04-29 CZ CZ0385799A patent/CZ299361B6/cs not_active IP Right Cessation
- 1998-07-21 TW TW087111990A patent/TW474938B/zh not_active IP Right Cessation
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1999
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- 1999-11-05 NO NO19995440A patent/NO314806B1/no not_active IP Right Cessation
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2000
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2004
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008506675A (ja) * | 2004-07-13 | 2008-03-06 | サイメイ ファーマスーティカルズ ピーエルシー | ポルフィリン誘導体及び光子活性化療法におけるその使用 |
Also Published As
Publication number | Publication date |
---|---|
US5990149A (en) | 1999-11-23 |
PT983272E (pt) | 2004-03-31 |
EP0983272A1 (en) | 2000-03-08 |
NO995440D0 (no) | 1999-11-05 |
AU7025798A (en) | 1998-11-27 |
JP2004217671A (ja) | 2004-08-05 |
ES2210740T3 (es) | 2004-07-01 |
CA2288045A1 (en) | 1998-11-12 |
PL336633A1 (en) | 2000-07-03 |
HUP0003939A3 (en) | 2003-06-30 |
NO314806B1 (no) | 2003-05-26 |
CA2288045C (en) | 2007-01-23 |
DK0983272T3 (da) | 2004-03-01 |
HUP0003939A2 (en) | 2001-03-28 |
DE69819318T2 (de) | 2004-08-19 |
IL132494A0 (en) | 2001-03-19 |
WO1998050386A1 (en) | 1998-11-12 |
DE69819318D1 (de) | 2003-12-04 |
NO995440L (no) | 1999-11-05 |
EP0983272B1 (en) | 2003-10-29 |
JP3907212B2 (ja) | 2007-04-18 |
AU749741B2 (en) | 2002-07-04 |
PL202340B1 (pl) | 2009-06-30 |
HK1025324A1 (en) | 2000-11-10 |
TW474938B (en) | 2002-02-01 |
CZ299361B6 (cs) | 2008-07-02 |
CZ385799A3 (cs) | 2000-04-12 |
CN1120166C (zh) | 2003-09-03 |
ATE253068T1 (de) | 2003-11-15 |
HU224176B1 (hu) | 2005-06-28 |
CN1255135A (zh) | 2000-05-31 |
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