AU2005251556B2 - Cationic bacteriochlorophyll derivatives and uses thereof - Google Patents
Cationic bacteriochlorophyll derivatives and uses thereof Download PDFInfo
- Publication number
- AU2005251556B2 AU2005251556B2 AU2005251556A AU2005251556A AU2005251556B2 AU 2005251556 B2 AU2005251556 B2 AU 2005251556B2 AU 2005251556 A AU2005251556 A AU 2005251556A AU 2005251556 A AU2005251556 A AU 2005251556A AU 2005251556 B2 AU2005251556 B2 AU 2005251556B2
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- AU
- Australia
- Prior art keywords
- amide
- compound
- methoxycarbonylmethyl
- rhodobacteriochlorin
- oxo
- 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.)
- Ceased
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- -1 Cationic bacteriochlorophyll derivatives Chemical class 0.000 title claims description 152
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 451
- 229910052763 palladium Inorganic materials 0.000 claims description 184
- 150000001408 amides Chemical class 0.000 claims description 178
- 150000001875 compounds Chemical class 0.000 claims description 157
- 206010028980 Neoplasm Diseases 0.000 claims description 110
- DSJXIQQMORJERS-AGGZHOMASA-M bacteriochlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC([C@H](CC)[C@H]3C)=[N+]4C3=CC3=C(C(C)=O)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 DSJXIQQMORJERS-AGGZHOMASA-M 0.000 claims description 87
- 238000002428 photodynamic therapy Methods 0.000 claims description 79
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
- 229940125898 compound 5 Drugs 0.000 claims description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 230000004962 physiological condition Effects 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 150000001768 cations Chemical class 0.000 claims description 24
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- 125000000524 functional group Chemical group 0.000 claims description 20
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 19
- 108010003118 Bacteriochlorophylls Proteins 0.000 claims description 19
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- 206010064930 age-related macular degeneration Diseases 0.000 claims description 17
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 claims description 17
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- 239000008280 blood Substances 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 15
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
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- 229910052736 halogen Inorganic materials 0.000 claims description 10
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000005286 illumination Methods 0.000 claims description 9
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 241000700605 Viruses Species 0.000 claims description 6
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 6
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 6
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 5
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 claims description 5
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical group [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 claims description 5
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 claims description 5
- 238000000338 in vitro Methods 0.000 claims description 5
- 239000012678 infectious agent Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 5
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 4
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 4
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- 206010072960 Chest wall tumour Diseases 0.000 claims description 4
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- BHPNXACHQYJJJS-UHFFFAOYSA-N bacteriochlorin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)CC2)=CC=C1C=C1CCC4=N1 BHPNXACHQYJJJS-UHFFFAOYSA-N 0.000 claims description 4
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- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 4
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- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims description 4
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- 229930101283 tetracycline Natural products 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 231100000747 viability assay Toxicity 0.000 description 1
- 238000003026 viability measurement method Methods 0.000 description 1
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/409—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- 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
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US57719604P | 2004-06-07 | 2004-06-07 | |
| US60/577,196 | 2004-06-07 | ||
| PCT/IL2005/000602 WO2005120573A2 (en) | 2004-06-07 | 2005-06-07 | Cationic bacteriochlorophyll derivatives and uses thereof |
Publications (2)
| Publication Number | Publication Date |
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| AU2005251556A1 AU2005251556A1 (en) | 2005-12-22 |
| AU2005251556B2 true AU2005251556B2 (en) | 2011-04-14 |
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| AU2005251556A Ceased AU2005251556B2 (en) | 2004-06-07 | 2005-06-07 | Cationic bacteriochlorophyll derivatives and uses thereof |
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| EP (2) | EP1753457B8 (cg-RX-API-DMAC7.html) |
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| AU (1) | AU2005251556B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0511909A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2569675C (cg-RX-API-DMAC7.html) |
| CY (2) | CY1118194T1 (cg-RX-API-DMAC7.html) |
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| ES (2) | ES2602460T3 (cg-RX-API-DMAC7.html) |
| HU (2) | HUE031075T2 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA06014326A (cg-RX-API-DMAC7.html) |
| NO (2) | NO339304B1 (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ551845A (cg-RX-API-DMAC7.html) |
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| WO (1) | WO2005120573A2 (cg-RX-API-DMAC7.html) |
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Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2008665A1 (fr) * | 2007-06-25 | 2008-12-31 | Steba Biotech N.V. | Formulation injectable pour thérapie photodynamique |
| CN102036684B (zh) | 2008-02-27 | 2017-06-09 | 耶达研究及发展有限公司 | 用于光动力疗法和坏死肿瘤成像的rgd‑(细菌)叶绿素缀合物 |
| BR112014004306A2 (pt) * | 2011-08-23 | 2017-03-28 | Yeda Res & Dev | fotossensibilizadores de (bacterio)clorofila para tratamento de doenças e distúrbios do olho |
| JP6517158B2 (ja) | 2013-03-11 | 2019-05-22 | トーカド イーペー エスアーエールエル | バクテリオクロロフィルａの生成方法 |
| RU2548675C9 (ru) * | 2013-05-29 | 2015-11-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет тонких химических технологий имени М.В. Ломоносова" (МИТХТ им. М.В. Ломоносова) | Аминоамиды в ряду бактериохлорофилла a, обладающие фотодинамической активностью, и способ их получения |
| JP6218073B2 (ja) * | 2013-11-26 | 2017-10-25 | 国立大学法人群馬大学 | 細胞・組織内酸素濃度測定のための高感度近赤外りん光イリジウム錯体 |
| RU2549953C2 (ru) * | 2013-12-25 | 2015-05-10 | Федеральное государственное унитарное предприятие Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" (ФГУП "ГНЦ "НИОПИК") | Фотосенсибилизатор для фотодинамической терапии |
| RU2610566C1 (ru) * | 2015-09-17 | 2017-02-13 | Сергей Сергеевич Брусов | Способ фотодинамической терапии локальных очагов инфекции |
| CN105424857A (zh) * | 2015-12-01 | 2016-03-23 | 浙江汇能生物股份有限公司 | 一种二甲基半胱胺盐酸盐的高效液相色谱分析方法 |
| WO2018102252A1 (en) * | 2016-11-30 | 2018-06-07 | North Carolina State University | Methods for making bacteriochlorin macrocycles comprising an annulated isocyclic ring and related compounds |
| WO2020150831A1 (en) * | 2019-01-25 | 2020-07-30 | Suncor Energy Inc. | Photosensitizer compounds, methods of manufacture and application to plants |
| WO2022115443A1 (en) * | 2020-11-24 | 2022-06-02 | The Regents Of The University Of California | Mitochondria targeting quinolinium-drug conjugates and their self-assembling nanoformulations for cancer therapy |
| CN115093422B (zh) * | 2022-06-15 | 2023-06-20 | 西北工业大学 | 一种基于代谢标记策略的新型光敏剂及其制备方法和应用 |
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| US5744598A (en) * | 1992-06-19 | 1998-04-28 | University Of Toledo | Imines of porphyrins, of porphyrin derivatives, and of related compounds, and pharmaceutical compositions containing such imines |
| US5864035A (en) * | 1996-03-08 | 1999-01-26 | Health Research, Inc. | Synthesis of isoimide of chlorins and bacteriochlorins and their use for diagnosis and treatment of cancer |
| WO2001040232A1 (en) * | 1999-12-01 | 2001-06-07 | Yeda Research And Development Co. Ltd. | Chlorophyll and bacteriochlorophyll esters, and their preparation |
| US20030050296A1 (en) * | 2000-09-27 | 2003-03-13 | Frontier Scientific, Inc. | Photodynamic porphyrin antimicrobial agents |
| WO2003055887A1 (en) * | 2001-12-21 | 2003-07-10 | Wellcome Trust Limited | Conjugated porphyrin, chlorin or bacteriochlorin chromophore |
| US20030203888A1 (en) * | 2001-06-06 | 2003-10-30 | Boyle Ross William | Chromophores |
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| US3050296A (en) * | 1960-12-19 | 1962-08-21 | Trimborn Hans | Transport roller for industrial furnaces |
| US3203888A (en) * | 1961-04-24 | 1965-08-31 | Exxon Research Engineering Co | Treating athabaska sands utilizing a flotation gas |
| DE2018970A1 (de) | 1970-04-21 | 1971-11-11 | Badische Anilin- & Soda Fabrik AG, 6700 Ludwigshafen | Verfahren zur Herstellung von beta-Aminoäthylsulfoniumverbindungen |
| US5330741A (en) * | 1992-02-24 | 1994-07-19 | The Regents Of The University Of California | Long-wavelength water soluble chlorin photosensitizers useful for photodynamic therapy and diagnosis of tumors |
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| US6147195A (en) | 1993-07-26 | 2000-11-14 | Yeda Research And Development Co., Ltd. | Chlorophyll and bacteriochlorophyll derivatives, their preparation and pharmaceutical compositions comprising them |
| IL116126A0 (en) * | 1995-11-24 | 1996-01-31 | Yeda Res & Dev | Process for the preparation of bacteriochlorophyllis some novel compounds of this type and pharmaceutical compositions comprising them |
| JP4796227B2 (ja) | 1998-12-09 | 2011-10-19 | イエダ・リサーチ・アンド・デベロツプメント・カンパニー・リミテツド | パラジウム置換バクテリオクロロフィル誘導体およびその用途 |
| DE60213996T2 (de) * | 2001-06-01 | 2007-09-06 | Ceramoptec Gmbh | Wasserlösliche porphyrinderivate für die photodynamische therapie, ihre verwendung und herstellung |
| US20040266748A1 (en) | 2001-10-03 | 2004-12-30 | Robinson Byron C | Photosensitizing carbamate derivatives |
| AU2002336637A1 (en) | 2001-10-03 | 2003-04-14 | Miravant Pharmaceuticals, Inc. | Chlorin photosensitizing agents for use in photodynamic therapy |
| DE10154436A1 (de) | 2001-11-07 | 2003-05-15 | Rodotech Gmbh | pyro-Bakteriopheophorbidderivate |
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| RU2223274C1 (ru) * | 2002-09-04 | 2004-02-10 | ООО "Фотогем" | ГИДРАЗИДЫ В РЯДУ БАКТЕРИОХЛОРОФИЛЛА a, ОБЛАДАЮЩИЕ ФОТОДИНАМИЧЕСКОЙ АКТИВНОСТЬЮ, И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| IL152900A0 (en) | 2002-11-17 | 2003-06-24 | Yeda Res & Dev | Water-soluble bacteriochlorophyll derivatives and their pharmaceutical uses |
-
2005
- 2005-06-07 ES ES10012927.9T patent/ES2602460T3/es not_active Expired - Lifetime
- 2005-06-07 EP EP05749886.7A patent/EP1753457B8/en not_active Expired - Lifetime
- 2005-06-07 ZA ZA200700169A patent/ZA200700169B/en unknown
- 2005-06-07 HU HUE10012927A patent/HUE031075T2/en unknown
- 2005-06-07 MX MXPA06014326A patent/MXPA06014326A/es active IP Right Grant
- 2005-06-07 AU AU2005251556A patent/AU2005251556B2/en not_active Ceased
- 2005-06-07 HU HUE05749886A patent/HUE030586T2/en unknown
- 2005-06-07 EP EP10012927.9A patent/EP2322173B1/en not_active Expired - Lifetime
- 2005-06-07 KR KR1020067025726A patent/KR101191700B1/ko not_active Expired - Fee Related
- 2005-06-07 BR BRPI0511909-0A patent/BRPI0511909A/pt not_active IP Right Cessation
- 2005-06-07 US US11/628,719 patent/US8207154B2/en not_active Expired - Fee Related
- 2005-06-07 PT PT57498867T patent/PT1753457T/pt unknown
- 2005-06-07 RU RU2006146677/04A patent/RU2397172C2/ru not_active IP Right Cessation
- 2005-06-07 WO PCT/IL2005/000602 patent/WO2005120573A2/en not_active Ceased
- 2005-06-07 NZ NZ551845A patent/NZ551845A/en not_active IP Right Cessation
- 2005-06-07 CN CN2005800185365A patent/CN1980661B/zh not_active Expired - Fee Related
- 2005-06-07 DK DK05749886.7T patent/DK1753457T3/en active
- 2005-06-07 PT PT100129279T patent/PT2322173T/pt unknown
- 2005-06-07 JP JP2007526692A patent/JP5372371B2/ja not_active Expired - Fee Related
- 2005-06-07 DK DK10012927.9T patent/DK2322173T3/en active
- 2005-06-07 ES ES05749886.7T patent/ES2602204T3/es not_active Expired - Lifetime
- 2005-06-07 CA CA2569675A patent/CA2569675C/en not_active Expired - Fee Related
-
2007
- 2007-01-05 NO NO20070083A patent/NO339304B1/no not_active IP Right Cessation
-
2016
- 2016-09-19 NO NO20161485A patent/NO20161485A1/no not_active Application Discontinuation
- 2016-10-27 CY CY20161101099T patent/CY1118194T1/el unknown
- 2016-10-27 CY CY20161101097T patent/CY1118203T1/el unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5744598A (en) * | 1992-06-19 | 1998-04-28 | University Of Toledo | Imines of porphyrins, of porphyrin derivatives, and of related compounds, and pharmaceutical compositions containing such imines |
| US5864035A (en) * | 1996-03-08 | 1999-01-26 | Health Research, Inc. | Synthesis of isoimide of chlorins and bacteriochlorins and their use for diagnosis and treatment of cancer |
| WO2001040232A1 (en) * | 1999-12-01 | 2001-06-07 | Yeda Research And Development Co. Ltd. | Chlorophyll and bacteriochlorophyll esters, and their preparation |
| US20030050296A1 (en) * | 2000-09-27 | 2003-03-13 | Frontier Scientific, Inc. | Photodynamic porphyrin antimicrobial agents |
| US20030203888A1 (en) * | 2001-06-06 | 2003-10-30 | Boyle Ross William | Chromophores |
| WO2003055887A1 (en) * | 2001-12-21 | 2003-07-10 | Wellcome Trust Limited | Conjugated porphyrin, chlorin or bacteriochlorin chromophore |
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