AU2005225616B2 - Acid addition salts of 5-aminolevulinic acid or its derivatives - Google Patents
Acid addition salts of 5-aminolevulinic acid or its derivatives Download PDFInfo
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- AU2005225616B2 AU2005225616B2 AU2005225616A AU2005225616A AU2005225616B2 AU 2005225616 B2 AU2005225616 B2 AU 2005225616B2 AU 2005225616 A AU2005225616 A AU 2005225616A AU 2005225616 A AU2005225616 A AU 2005225616A AU 2005225616 B2 AU2005225616 B2 AU 2005225616B2
- Authority
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- Australia
- Prior art keywords
- acid
- addition salt
- ala
- acid addition
- amino
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 107
- 150000003839 salts Chemical class 0.000 title claims abstract description 98
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical class NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229960002749 aminolevulinic acid Drugs 0.000 title claims abstract description 42
- -1 5-ALA ester Chemical class 0.000 claims abstract description 64
- 230000005856 abnormality Effects 0.000 claims abstract description 20
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 13
- 238000003745 diagnosis Methods 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 80
- 150000002148 esters Chemical class 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 63
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 30
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 20
- 208000035475 disorder Diseases 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 230000002215 photochemotherapeutic effect Effects 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims description 11
- 238000002428 photodynamic therapy Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000002738 chelating agent Substances 0.000 claims description 9
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 210000001124 body fluid Anatomy 0.000 claims description 6
- 239000010839 body fluid Substances 0.000 claims description 6
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 5
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 4
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 4
- 230000035515 penetration Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000003957 anion exchange resin Substances 0.000 claims description 3
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 14
- 239000003504 photosensitizing agent Substances 0.000 abstract description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract description 6
- 150000007513 acids Chemical class 0.000 abstract description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 48
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 238000009472 formulation Methods 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000006071 cream Substances 0.000 description 20
- 210000003491 skin Anatomy 0.000 description 20
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 18
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical class CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- GHMCTRQKEALPCK-UHFFFAOYSA-N benzyl 5-amino-4-oxopentanoate;hydrochloride Chemical compound Cl.NCC(=O)CCC(=O)OCC1=CC=CC=C1 GHMCTRQKEALPCK-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 150000007524 organic acids Chemical class 0.000 description 10
- RYKLZUPYJFFNRR-UHFFFAOYSA-N 3-hydroxypiperidin-2-one Chemical compound OC1CCCNC1=O RYKLZUPYJFFNRR-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 9
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 9
- ZLHFONARZHCSET-UHFFFAOYSA-N 5-aminolevulinic acid hydrochloride Chemical compound Cl.NCC(=O)CCC(O)=O ZLHFONARZHCSET-UHFFFAOYSA-N 0.000 description 8
- LZYXPFZBAZTOCH-UHFFFAOYSA-N hexyl 5-amino-4-oxopentanoate;hydron;chloride Chemical compound Cl.CCCCCCOC(=O)CCC(=O)CN LZYXPFZBAZTOCH-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000000047 product Substances 0.000 description 8
- 150000003460 sulfonic acids Chemical class 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 230000000699 topical effect Effects 0.000 description 8
- AFFZCQDLQIEQGB-UHFFFAOYSA-N benzyl 5-amino-4-oxopentanoate Chemical compound NCC(=O)CCC(=O)OCC1=CC=CC=C1 AFFZCQDLQIEQGB-UHFFFAOYSA-N 0.000 description 7
- 150000003840 hydrochlorides Chemical class 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229940093915 gynecological organic acid Drugs 0.000 description 6
- 230000001976 improved effect Effects 0.000 description 6
- YUUAYBAIHCDHHD-UHFFFAOYSA-N methyl 5-aminolevulinate Chemical compound COC(=O)CCC(=O)CN YUUAYBAIHCDHHD-UHFFFAOYSA-N 0.000 description 6
- 235000005985 organic acids Nutrition 0.000 description 6
- 238000002203 pretreatment Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RYQOILLJDKPETL-UHFFFAOYSA-N 5-aminolevulinic acid hexyl ester Chemical class CCCCCCOC(=O)CCC(=O)CN RYQOILLJDKPETL-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000002674 ointment Substances 0.000 description 5
- RGECSKBZJORAEB-UHFFFAOYSA-N 5-amino-4-oxopentanoic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.NCC(=O)CCC(O)=O RGECSKBZJORAEB-UHFFFAOYSA-N 0.000 description 4
- 229950000258 5-aminolevulinic acid hexyl ester Drugs 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 239000004037 angiogenesis inhibitor Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000002500 effect on skin Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 230000003211 malignant effect Effects 0.000 description 4
- UJYSYPVQHFNBML-UHFFFAOYSA-N methyl 5-aminolevulinate hydrochloride Chemical compound [Cl-].COC(=O)CCC(=O)C[NH3+] UJYSYPVQHFNBML-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 230000002165 photosensitisation Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- LBKBQPGAPSHJOJ-UHFFFAOYSA-N 5-amino-4-oxopentanoic acid;hydrobromide Chemical compound Br.NCC(=O)CCC(O)=O LBKBQPGAPSHJOJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
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- 150000001450 anions Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- DESMEFBBJJAEQL-UHFFFAOYSA-N hexyl 5-amino-4-oxopentanoate;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCCCCCOC(=O)CCC(=O)CN DESMEFBBJJAEQL-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 230000000149 penetrating effect Effects 0.000 description 3
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- ZFCDJOVFDDEYKY-UHFFFAOYSA-M silver;benzenesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C1=CC=CC=C1 ZFCDJOVFDDEYKY-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZRTYOGWRVLXBDF-UHFFFAOYSA-N (4-methylphenyl)methyl 5-amino-4-oxopentanoate;hydrochloride Chemical compound Cl.CC1=CC=C(COC(=O)CCC(=O)CN)C=C1 ZRTYOGWRVLXBDF-UHFFFAOYSA-N 0.000 description 2
- WKKVBTCDQQMCQB-UHFFFAOYSA-N (4-propan-2-ylphenyl)methyl 5-amino-4-oxopentanoate;hydrochloride Chemical compound Cl.CC(C)C1=CC=C(COC(=O)CCC(=O)CN)C=C1 WKKVBTCDQQMCQB-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 2
- NZJXADCEESMBPW-UHFFFAOYSA-N 1-methylsulfinyldecane Chemical compound CCCCCCCCCCS(C)=O NZJXADCEESMBPW-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- RNMCCPMYXUKHAZ-UHFFFAOYSA-N 2-[3,3-diamino-1,2,2-tris(carboxymethyl)cyclohexyl]acetic acid Chemical compound NC1(N)CCCC(CC(O)=O)(CC(O)=O)C1(CC(O)=O)CC(O)=O RNMCCPMYXUKHAZ-UHFFFAOYSA-N 0.000 description 2
- UVJCZGZHUTXROP-UHFFFAOYSA-N 2-methylpentyl 5-amino-4-oxopentanoate;hydrochloride Chemical compound Cl.CCCC(C)COC(=O)CCC(=O)CN UVJCZGZHUTXROP-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 2
- DVXSBYSVFBCPRS-UHFFFAOYSA-N 4-methylpentyl 5-amino-4-oxopentanoate;hydrochloride Chemical compound Cl.CC(C)CCCOC(=O)CCC(=O)CN DVXSBYSVFBCPRS-UHFFFAOYSA-N 0.000 description 2
- HJKUJIBPAYWXQS-UHFFFAOYSA-N 5-amino-2-benzyl-4-oxopentanoic acid Chemical class NCC(=O)CC(C(O)=O)CC1=CC=CC=C1 HJKUJIBPAYWXQS-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 description 1
- 229940019931 silver phosphate Drugs 0.000 description 1
- 229910000161 silver phosphate Inorganic materials 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- ULQFYBXXHIFWIQ-UHFFFAOYSA-M silver;2-hydroxyethanesulfonate Chemical compound [Ag+].OCCS([O-])(=O)=O ULQFYBXXHIFWIQ-UHFFFAOYSA-M 0.000 description 1
- BHZDYXJJBKYMBQ-DLGLCQKISA-M silver;[(4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonate Chemical compound [Ag+].C1C[C@@]2(CS([O-])(=O)=O)C(=O)CC1C2(C)C BHZDYXJJBKYMBQ-DLGLCQKISA-M 0.000 description 1
- KZCVJSZYZCRFQL-UHFFFAOYSA-M silver;naphthalene-2-sulfonate Chemical compound [Ag+].C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KZCVJSZYZCRFQL-UHFFFAOYSA-M 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001138 tear Anatomy 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000007521 triprotic acids Chemical class 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
- 210000003741 urothelium Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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Classifications
-
- 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
- A61K41/0061—5-aminolevulinic acid-based PDT: 5-ALA-PDT involving porphyrins or precursors of protoporphyrins generated in vivo from 5-ALA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0406917.5A GB0406917D0 (en) | 2004-03-26 | 2004-03-26 | Compounds |
| GB0406917.5 | 2004-03-26 | ||
| PCT/GB2005/001236 WO2005092838A1 (en) | 2004-03-26 | 2005-03-29 | Acid addition salts of 5-aminolevulinic acid or its derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005225616A1 AU2005225616A1 (en) | 2005-10-06 |
| AU2005225616B2 true AU2005225616B2 (en) | 2011-08-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005225616A Ceased AU2005225616B2 (en) | 2004-03-26 | 2005-03-29 | Acid addition salts of 5-aminolevulinic acid or its derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7888526B2 (https=) |
| EP (2) | EP2308830B1 (https=) |
| JP (1) | JP5164565B2 (https=) |
| CN (1) | CN1938264B (https=) |
| AT (1) | ATE514672T1 (https=) |
| AU (1) | AU2005225616B2 (https=) |
| CA (1) | CA2561050C (https=) |
| DK (1) | DK1727786T3 (https=) |
| ES (2) | ES2367789T3 (https=) |
| GB (1) | GB0406917D0 (https=) |
| PL (1) | PL1727786T3 (https=) |
| PT (1) | PT1727786E (https=) |
| RU (1) | RU2392266C2 (https=) |
| SI (1) | SI1727786T1 (https=) |
| WO (1) | WO2005092838A1 (https=) |
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| JP4719483B2 (ja) * | 2004-03-30 | 2011-07-06 | コスモ石油株式会社 | ５−アミノレブリン酸スルホン酸塩の製造方法 |
| CA2562170C (en) | 2004-03-30 | 2013-04-23 | Cosmo Oil Co., Ltd. | 5-aminolevulinic acid salt, process for producing the same and use thereof |
| GB0424833D0 (en) | 2004-11-10 | 2004-12-15 | Photocure Asa | Method |
| JP4934293B2 (ja) * | 2005-07-05 | 2012-05-16 | コスモ石油株式会社 | 植物活力剤組成物 |
| JP4934292B2 (ja) * | 2005-07-05 | 2012-05-16 | コスモ石油株式会社 | ５−アミノレブリン酸エステルリン酸類塩、その製造方法及びその用途 |
| US20070225518A1 (en) * | 2006-03-22 | 2007-09-27 | Zvi Malik | 5-Aminolevulinic acid salts and their use |
| KR100796450B1 (ko) | 2006-06-29 | 2008-01-22 | 전남대학교산학협력단 | 5-아미노레불린산의 불포화 알킬 에스터 및 약학적으로허용되는 그의 염, 이의 제조방법 및 이의 용도 |
| JP4989153B2 (ja) | 2006-08-15 | 2012-08-01 | コスモ石油株式会社 | ５−アミノレブリン酸リン酸塩の新規結晶及びその製造方法 |
| GB0700580D0 (en) * | 2007-01-11 | 2007-02-21 | Photocure Asa | Use |
| WO2008106966A1 (en) * | 2007-03-06 | 2008-09-12 | Christiansen Kaare | A method for non-therapeutic or therapeutic photodynamic skin treatment |
| CN102177146B (zh) * | 2008-10-30 | 2016-02-10 | 阿彻丹尼尔斯米德兰德公司 | 用金属催化剂还原hmf醚 |
| GB0823472D0 (en) | 2008-12-23 | 2009-01-28 | Photocure Asa | Product |
| GB0900461D0 (en) | 2009-01-12 | 2009-02-11 | Photocure Asa | Photodynamic therapy device |
| SI2440199T1 (sl) | 2009-06-11 | 2016-05-31 | Photocure Asa | Poltrdni sestavki in farmacevtski proizvodi |
| WO2011107478A1 (en) | 2010-03-01 | 2011-09-09 | Photocure Asa | Cosmetic compositions |
| EP2394642A1 (en) | 2010-06-10 | 2011-12-14 | Universite De Geneve | 5-ALA ester formulations and use thereof |
| US20130211215A1 (en) | 2010-06-23 | 2013-08-15 | Photocure Asa | Hyperosmotic preparations comprising 5-aminolevulinic acid or derivative as photosensitizing agent |
| CA2804337A1 (en) | 2010-07-09 | 2012-01-12 | Photocure Asa | Dry compositions and devices containing such dry compositions for use in photodynamic therapy or photodynamic diagnosis |
| EP2657346B1 (en) | 2010-12-24 | 2017-08-23 | ARKRAY, Inc. | Method for detecting cancer cell |
| US20140316534A1 (en) | 2011-10-14 | 2014-10-23 | Photocure Asa | Stent |
| EP2766049A1 (en) | 2011-10-14 | 2014-08-20 | Photocure ASA | Photodynamic diagnosis of abnormalities of the epithelial lining of the oesophagus with the means of a 5-ala ester |
| EP2794004B1 (en) | 2011-12-19 | 2020-07-29 | Photocure ASA | Irradiation apparatus |
| ES2908080T3 (es) | 2012-08-03 | 2022-04-27 | Photocure Asa | Compuestos |
| US9387341B2 (en) | 2012-08-10 | 2016-07-12 | Dusa Pharmaceuticals, Inc. | Method for the treatment of acne |
| US20140067024A1 (en) | 2012-08-30 | 2014-03-06 | Photocure Asa | Dual panel photodynamic therapy lamp |
| GB201221123D0 (en) | 2012-11-23 | 2013-01-09 | Photocure As | Device for photodynamic treatment |
| GB201306369D0 (en) | 2013-04-09 | 2013-05-22 | Photocure As | Irradiation device |
| JP6595484B2 (ja) | 2013-12-20 | 2019-10-23 | ガルデルマ・リサーチ・アンド・デヴェロップメント | 光損傷皮膚のパルス光力学的処置 |
| EP3095464A1 (en) | 2015-05-19 | 2016-11-23 | Universite De Geneve | 5-ala derivatives and use thereof |
| GB201522309D0 (en) | 2015-12-17 | 2016-02-03 | Photocure Asa | Use |
| SG11201805000RA (en) | 2015-12-17 | 2018-07-30 | Photocure Asa | Method of photodynamic therapy (pdt) for bladder cancer |
| GB201522311D0 (en) | 2015-12-17 | 2016-02-03 | Photocure Asa | Use |
| GB201522398D0 (en) | 2015-12-18 | 2016-02-03 | Photocure As | Device for photodynamic therapy |
| CN112010772A (zh) * | 2016-01-26 | 2020-12-01 | 赵鸣 | 5-氨基酮戊酸及其衍生物的盐化合物和应用 |
| RU2611441C2 (ru) * | 2016-04-28 | 2017-02-22 | Федеральное государственное бюджетное учреждение "Национальный медицинский исследовательский радиологический центр" Министерства здравоохранения Российской Федерации (ФГБУ "НМИРЦ" Минздрава России) | Способ получения гидрохлорида метилового эфира 5-аминолевулиновой кислоты |
| AU2018216043B2 (en) | 2017-02-06 | 2020-02-27 | 3Skin As | Sunscreen composition |
| CN108088838A (zh) * | 2017-12-13 | 2018-05-29 | 西南大学 | 双[2,4,6-三氯苯基]草酸酯在测定链格孢霉毒素中的应用及方法 |
| CN108440319B (zh) * | 2018-04-26 | 2021-05-18 | 爱斯特（成都）生物制药股份有限公司 | 一种制备盐酸氨基乙酰丙酸的方法 |
| EP3868372A1 (en) | 2020-02-19 | 2021-08-25 | JLP Health GmbH | A pharmaceutical combination of an artemisinin compound and a heme synthesis modulator for treating cancer |
| CN115671059B (zh) * | 2022-11-17 | 2024-06-11 | 兆科药业（合肥）有限公司 | 一种盐酸氨酮戊酸冻干制剂及制备方法 |
| CN116162038A (zh) * | 2023-01-06 | 2023-05-26 | 河南省精细化工研究院有限公司 | 一种5-氨基乙酰丙酸盐酸盐的环保型生产工艺 |
| KR20250154511A (ko) | 2023-03-07 | 2025-10-28 | 포토큐어 에이에스에이 | 방광암 치료 |
| WO2026052815A1 (en) | 2024-09-05 | 2026-03-12 | Photocure Asa | Use of hal in a method for predicting bladder cancer immunotherapy response |
| WO2026084589A1 (en) | 2024-10-14 | 2026-04-23 | Universiteit Van Amsterdam | G4-destabiling small molecules for the treatment of x-linked dystonia-parkinsonism. |
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| EP0483714A1 (en) * | 1990-10-29 | 1992-05-06 | Japan Tobacco Inc. | A method of preparing an acid additional salt of delta-aminolevulinic acid |
| EP0607952A1 (en) * | 1993-01-20 | 1994-07-27 | Cosmo Research Institute | Process for preparing 5-aminolevulinic acid |
| US6034267A (en) * | 1995-03-10 | 2000-03-07 | Photocure As | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| WO2002010120A1 (en) * | 2000-07-27 | 2002-02-07 | Photocure Asa | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
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| US5079262A (en) | 1989-07-28 | 1992-01-07 | Queen's University At Kingston | Method of detection and treatment of malignant and non-malignant lesions utilizing 5-aminolevulinic acid |
| JP2767318B2 (ja) | 1990-04-11 | 1998-06-18 | 株式会社コスモ総合研究所 | ５―アミノレブリン酸アルキルエステル又はその塩及びその製造方法並びにこれを有効成分とする除草剤 |
| US5284973A (en) | 1990-10-29 | 1994-02-08 | Japan Tobacco Inc. | Method of preparing an acid additional salt of delta-aminolevulinic acid |
| JP2613136B2 (ja) * | 1991-05-14 | 1997-05-21 | 株式会社コスモ総合研究所 | 植物成長促進剤 |
| US5489572A (en) | 1993-08-19 | 1996-02-06 | Cosmo Research Institue | Methods for reducing nitrate nitrogen and oxalic acids contents nin plants |
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| JP2896963B2 (ja) | 1994-11-28 | 1999-05-31 | 株式会社コスモ総合研究所 | 植物の耐塩性向上剤 |
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| GB9504948D0 (en) * | 1995-03-10 | 1995-04-26 | Norwegian Radium Hospital Rese | Compounds |
| JPH1112197A (ja) * | 1997-06-18 | 1999-01-19 | Cosmo Sogo Kenkyusho:Kk | 悪性腫瘍診断剤及び治療剤 |
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| GB0018527D0 (en) | 2000-07-27 | 2000-09-13 | Photocure Asa | Composition |
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| CA2562170C (en) * | 2004-03-30 | 2013-04-23 | Cosmo Oil Co., Ltd. | 5-aminolevulinic acid salt, process for producing the same and use thereof |
-
2004
- 2004-03-26 GB GBGB0406917.5A patent/GB0406917D0/en not_active Ceased
-
2005
- 2005-03-29 EP EP10011759.7A patent/EP2308830B1/en not_active Expired - Lifetime
- 2005-03-29 EP EP05732530A patent/EP1727786B1/en not_active Expired - Lifetime
- 2005-03-29 ES ES05732530T patent/ES2367789T3/es not_active Expired - Lifetime
- 2005-03-29 RU RU2006135487/04A patent/RU2392266C2/ru not_active IP Right Cessation
- 2005-03-29 AT AT05732530T patent/ATE514672T1/de active
- 2005-03-29 US US10/594,361 patent/US7888526B2/en not_active Expired - Lifetime
- 2005-03-29 AU AU2005225616A patent/AU2005225616B2/en not_active Ceased
- 2005-03-29 ES ES10011759.7T patent/ES2639021T3/es not_active Expired - Lifetime
- 2005-03-29 CN CN2005800098456A patent/CN1938264B/zh not_active Expired - Fee Related
- 2005-03-29 JP JP2007504487A patent/JP5164565B2/ja not_active Expired - Lifetime
- 2005-03-29 DK DK05732530.0T patent/DK1727786T3/da active
- 2005-03-29 WO PCT/GB2005/001236 patent/WO2005092838A1/en not_active Ceased
- 2005-03-29 CA CA2561050A patent/CA2561050C/en not_active Expired - Fee Related
- 2005-03-29 PT PT05732530T patent/PT1727786E/pt unknown
- 2005-03-29 SI SI200531338T patent/SI1727786T1/sl unknown
- 2005-03-29 PL PL05732530T patent/PL1727786T3/pl unknown
-
2010
- 2010-10-29 US US12/916,326 patent/US8692014B2/en active Active
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| EP0483714A1 (en) * | 1990-10-29 | 1992-05-06 | Japan Tobacco Inc. | A method of preparing an acid additional salt of delta-aminolevulinic acid |
| EP0607952A1 (en) * | 1993-01-20 | 1994-07-27 | Cosmo Research Institute | Process for preparing 5-aminolevulinic acid |
| US6034267A (en) * | 1995-03-10 | 2000-03-07 | Photocure As | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| WO2002010120A1 (en) * | 2000-07-27 | 2002-02-07 | Photocure Asa | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007530523A (ja) | 2007-11-01 |
| WO2005092838A1 (en) | 2005-10-06 |
| ES2367789T3 (es) | 2011-11-08 |
| CN1938264B (zh) | 2012-05-23 |
| ATE514672T1 (de) | 2011-07-15 |
| PL1727786T3 (pl) | 2011-11-30 |
| CA2561050C (en) | 2012-05-08 |
| CA2561050A1 (en) | 2005-10-06 |
| US20110125012A1 (en) | 2011-05-26 |
| AU2005225616A1 (en) | 2005-10-06 |
| US7888526B2 (en) | 2011-02-15 |
| EP2308830B1 (en) | 2017-06-14 |
| RU2006135487A (ru) | 2008-05-10 |
| US20080064752A1 (en) | 2008-03-13 |
| EP2308830A1 (en) | 2011-04-13 |
| GB0406917D0 (en) | 2004-04-28 |
| RU2392266C2 (ru) | 2010-06-20 |
| PT1727786E (pt) | 2011-07-08 |
| EP1727786A1 (en) | 2006-12-06 |
| DK1727786T3 (da) | 2011-08-29 |
| EP1727786B1 (en) | 2011-06-29 |
| ES2639021T3 (es) | 2017-10-25 |
| US8692014B2 (en) | 2014-04-08 |
| JP5164565B2 (ja) | 2013-03-21 |
| CN1938264A (zh) | 2007-03-28 |
| SI1727786T1 (sl) | 2011-09-30 |
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