WO2006088476A2 - Carboranylporphyrins and uses thereof - Google Patents
Carboranylporphyrins and uses thereof Download PDFInfo
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- WO2006088476A2 WO2006088476A2 PCT/US2005/017358 US2005017358W WO2006088476A2 WO 2006088476 A2 WO2006088476 A2 WO 2006088476A2 US 2005017358 W US2005017358 W US 2005017358W WO 2006088476 A2 WO2006088476 A2 WO 2006088476A2
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- WIPO (PCT)
- Prior art keywords
- compound according
- subject
- metal ion
- porphyrin
- boron
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- 0 *C*c(cc1)ccc1C([C@@]1NC(C(c2ccc(*C*)cc2)=C2N=C3C=C2)=CC1)=C(C=C1)N=C1C(c1ccc(*C*)cc1)=C(C=C1)NC1=C3c1ccc(*C*)cc1 Chemical compound *C*c(cc1)ccc1C([C@@]1NC(C(c2ccc(*C*)cc2)=C2N=C3C=C2)=CC1)=C(C=C1)N=C1C(c1ccc(*C*)cc1)=C(C=C1)NC1=C3c1ccc(*C*)cc1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- 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
- 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
- A61K41/009—Neutron capture therapy, e.g. using uranium or non-boron material
- A61K41/0095—Boron neutron capture therapy, i.e. BNCT, e.g. using boronated porphyrins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
Definitions
- Porphyrins in general belong to a class of colored, aromatic tetrapyrrole compounds, some of which are found naturally in plants and animals, e.g., chlorophyll and heme, respectively.
- PDT photodynamic therapy
- the patient is first injected with a photosensitizing drug, typically a porphyrin.
- a photosensitizing drug typically a porphyrin.
- a promising new form of cancer therapy is boron neutron-capture therapy
- BNCT is a bimodal cancer treatment based on the selective accumulation of a
- boron-10 stable nuclide of boron known as boron-10, or 10 B, in the tumor, followed by irradiation
- thermalized neutrons impinge on the boron-
- the boron-containing compound must be non-toxic or of low toxicity
- BPA has the advantage of low chemical toxicity, it
- tumor-to-normal brain and tumor-to-blood boron concentrations are in the ratio of
- a particular class of synthetic porphyrins known as tetraphenyl porphyrins, have
- Tetraphenylporphyrins contain four phenyl groups, typically on the 5, 10, 15, and
- TPPs 20 positions of the porphyrin ring.
- TPPs The solubility of TPPs can be controlled by the substituents, generally on the
- TPPs containing sulfonates or carboxylates are water-soluble.
- hydrolysis results in loss of the carbonyl group before reaching the target.
- Vicente compounds is the attachment of the carboranyl group to the phenyl group by,
- Porphyrins also have the advantage of having the ability to chelate metal ions in
- Such chelated porphyrins can additionally function as visualization tools for
- porphyrins when chelated to paramagnetic metal ions, porphyrins may function as contrast agents in
- MRI magnetic resonance imaging
- porphyrins may function as imaging agents for single photon emission computed
- SPECT positron emission tomography
- PET positron emission tomography
- irradiated treatment volume can be accurately and rapidly determined noninvasively
- porphyrins with long retention times in tumors, and that selectively target and destroy
- the present invention is directed to low toxicity boronated compounds
- the present invention is directed to low toxicity boronated 5, 10, 15, 20-
- BNCT capture therapy
- PDT photodynamic therapy
- the brain head and neck, and surrounding tissue.
- the present invention is directed to boron-containing 5, 10, 15, 20-
- Y 1 , Y 2 , Y 3 , and Y 4 are independently on the ortho, meta or para position on the phenyl
- rings are independently hydrogen, alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl,
- heteroaryl or an alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl, or hete ⁇ oaryl group,
- Y 1 , Y 2 , Y 3 , and Y 4 represents formula (2);
- X is oxygen or sulfur
- R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen and Ci to C 4 alkyl;
- Z is a carborane cluster comprising at least two carbon atoms and at least three boron
- r is 0 or an integer from 1 to 20;
- W 1 , W 2 , W 3 , and W 4 are hydrophilic groups independently selected from hydroxy
- a, b, c, and d independently represent an integer from 1 to 4;
- n, p, and q are independently 0 or an integer from 1 to 4;
- c + p, and d + q independently represents an integer from 1 to 5;
- M is either two hydrogen ions; a single monovalent metal ion; two monovalent metal
- SPECT positron emission tomography
- PET positron emission tomography
- MRI magnetic resonance imaging
- metal ion suitable for boron neutron capture
- BNCT photodynamic therapy
- PDT photodynamic therapy
- Z is preferably selected from the carboranes -C 2 HBgHi 0 or -C 2 HBi 0 Hi 0 , wherein -
- C 2 HBpHi 0 is nido ortho-, meta-, or para-carborane, and -C 2 HBi O Hio is closo ortho, meta-,
- M is preferably vanadium (V), manganese (Mn), iron (Fe), ruthenium (Ru),
- Tc technetium
- Cr chromium
- Pt platinum
- Co cobalt
- Ni nickel
- Cu copper
- M is copper (Cu) or
- Ni nickel (Ni).
- a, b, c, and d are 1, and Y 1 , Y 2 , Y 3 , and Y 4 are
- X is O; R 1 and R 2 are H; r is 1; and m, n, p and
- Y 1 , Y 2 , Y 3 , and Y 4 are in the para position on the phenyl ring
- W 1 , W 2 , W 3 , and W 4 are independently, hydroxy or alkoxy groups. More preferably,
- the hydroxy or alkoxy groups are in the meta position of the phenyl ring.
- W 1 , W 2 , W 3 , and W 4 are methoxy groups. More preferably, the
- methoxy groups are in the meta position of the phenyl ring.
- Y 1 , Y 2 , Y 3 , and Y 4 are represented by
- R 2 are H; r is 1; m, n, p and q are each 1, and W 1 , W 2 , W 3 , and W 4 are hydroxy.
- the counter dianion is a porphyrin compound containing a divalent negative charge.
- porphyrin compound containing a divalent negative charge may be a carborane-
- the present invention also includes methods of tumor imaging by SPECT, PET,
- composition that comprises one or more of the
- the composition is
- the invention relates to boron-containing 5, 10, 15, 20-tetraphenyl porphyrins
- Y 1 , Y 2 , Y 3 , and Y 4 are independently on the ortho, meta or para position on the phenyl rings.
- Y 1 , Y 2 , Y 3 , and V are independently hydrogen, alkyl, cycloalkyl, aryl,
- alkyl is a straight chain or branched alkyl
- group containing 1 to 20 carbon atoms including, optionally, up to three double or triple
- alkyl groups include methyl, ethyl, n-propyl, iso-propyl, n-
- butyl iso-butyl, sec-butyl;, tert-butyl, propenyl, 2-butenyl, 3-butenyl, 3-butynyl, 2-methyl-
- the alkyl group may be unsubstituted or substituted with 1 to 4 hydrophilic
- hydrophilic groups Some examples include hydroxy, alkoxy, -
- R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen and alkyl
- R 5 , R 6 , R 7 , R 8 , and R 9 contain 1
- the carbon atoms of the alkyl group may also be substituted with 1 to 4
- heteroatoms are O, N, or S.
- the heteroatoms are not
- cycloalkyl ring is a 4, 5, 6, or 7
- the ring may be saturated,- or may contain 1 to 4 unsaturated
- saturated cycloalkyl rings include
- cyclobutane cyclopentane, cyclohexane, and cyclopentane rings.
- unsaturated cycloalkyl rings include cyclobutene, cyclopentene, cyclohexene, and 1,3- cycloheptadiene rings.
- the cycloalkyl ring may optionally be substituted with 1 to 4 heteroatoms of O, N,
- cycloalkyl rings substituted with heteroatoms include
- cycloalkyl rings may be optionally substituted with
- alkyl as defined above, or with 1 to 4 hydrophilic groups, also as defined above.
- the cycloalkyl ring may be fused to 1 to 3 additional 4, 5, 6, or 7 member
- cycloalkyl or phenyl rings Some examples of fused cycloalkyl rings are
- aryl is a 5, 6, or 7 member aromatic ring
- aryl rings may be optionally substituted with alkyl as
- groups may be substituted with 1 to 4 hydrophilic groups, as defined above.
- the aryl ring may optionally be substituted with 1 to 4 heteroatoms of O, N, or S,
- heteroaryl rings include thiophene,
- heteroaryl ring may be
- the aryl or heteroaryl ring may also be fused to 1 to 3 additional 5, 6, or 7
- fused aryl and heteroaryl rings include naphthalene, anthracene, phenanthrene, triphenylene, chrysene, indoline,
- At least one of Y 1 , Y 2 , Y 3 , or Y 4 is represented by the formula
- alkyl groups for R 1 and R 2 contain 1 to 4 carbon atoms.
- the subscript r is 0 or an integer
- Z is a carborane cluster comprising at least two carbon atoms and at least three
- boron atoms or at least one carbon atom and at least five boron atoms, within a cage
- carborane clusters include the regular polyhedral carborane
- clusters also known as closo structures, as well as ionized fragments of the polyhedral
- present invention include -C 2 HBgH 10 or -C 2 HB 1O Hi 0 , wherein -C 2 HB 9 Hi 0 is nido ortho-,
- W 1 , W 2 , W 3 , and W 4 are hydrophilic groups independently selected from hydroxy
- an alkoxy group contains an alkyl portion as defined above.
- alkoxy groups include methoxy, ethoxy, propoxy, n-butoxy, t-butoxy,
- a polyalkylene oxide is defined according to the formula -(CH 2 )d-O-[(CH2) e -Q-J x - [(CH 2 )rO-] y -(Cll 2 ) g -OR', wherein, independently, d is 0, or an integer from 1 to 10, e is
- f is 1 to 10
- g is 1 to 10
- x and y are each independently 1 or
- P, and R' is either H or an alkyl group as defined previously, provided that when e is 0,
- x is 0; when f is 0, then y is 0; when e is not 0, then x is I ; and when f is not 0, then
- a preferable polyalkylene oxide of the invention is polyethylene oxide.
- Polyethylene oxide is . defined according to the formula -(CH 2 )d-O-[(CH2) e -O-] x -[(CH2)r O-] y -(CH 2 ) g -OR ⁇ wherein, independently, d is 0 or 2, e is 0 or 2, f is 0 or 2, g is 2, x and y
- R' is either H or an ethyl group, provided that when e
- M may be two hydrogen ions, a single monovalent metal ion, or
- monovalent metal ions include aluminum, copper, magnesium, calcium, magnesium, calcium, magnesium, calcium, magnesium, calcium, magnesium, calcium, magnesium, calcium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium, magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium magnesium
- the resulting porphyrin-metal complex anion is charge-balanced by a counter cation.
- counter cations include any of the foregoing monovalent metal ions,
- ammonium and phosphonium cations such as tetramethylammonium, .
- the counter cation may be either bound or associated in some form with the porphyrin-metal complex.
- M may also be a divalent metal ion.
- ions include V +2 , Mn +2 , Fe +2 , Ru +2 , Co +2 , Ni +2 , Cu +2 , Pd +2 , Pt +2 , Zn +2 , Ca +2 , Mg +2 , Sr +2 ,
- M may be a trivalent, tetravalent, pentavalent, or hexavalent metal
- trivalent metal ions include Gd +3 , Y +3 , In +3 , Cr +3 , Ga +3 ,
- tetravalent metal ions include Tc +4 ,
- Suitable hexavalent metal ions include W +6 , Tc +6 , and Mo +6 . The resulting
- porphyrin-metal complex cation is charge-balanced by an appropriate number of counter
- a trivalent metal ion may be charge-balanced by a single counter anion, and such a
- complex derived from a tetravalent metal ion may, for example, be charge-balanced by a
- Suitable counter anions include chloride, perchlorate, sulfate,
- nitrate nitrate
- tetrafluoroborate nitrate
- suitable counter dianions include oxide,
- porphyrin sulfide, or a porphyrin compound containing a divalent negative charge.
- compound containing a divalent negative charge may be a porphyrin compound of the present invention with the proviso that M is absent.
- trianion includes phosphate.
- the counter anion, dianion, or trianion may be either bound or associated in some
- carborane-containing porphyrin compound may also be bound to or associated with
- neutrally charged molecules such as molecules of solvation, for example, water
- M may be a radioactive metal ion imageable by single photon
- SPECT emission computed tomography
- PET positron emission tomography
- radioactive metals suitable for SPECT are 67 Cu, 99m Tc, 111 In, and those for
- PET include 64 Cu, 55 Co.. M may also be a radioactive metal useful as a
- radiopharmaceutical for therapy.
- radioactive metals suitable for such examples include, but not limited
- M may also be a paramagnetic metal ion detectable by magnetic resonance
- MRI imaging
- metals include Mn, Fe, Co, and Gd.
- M may be a metal ion suitable for boron neutron capture therapy
- BNCT photodynamic therapy
- PDT photodynamic therapy
- suitable for BNCT include those described thus far, with the exclusion of those that are photoactive, such as Zn and Sn.
- photoactive metals and particularly those with
- accumulation of photoactive metal may cause biological damage.
- the invention also relates to methods of treating tumors.
- a preferred tumors In a preferred embodiment
- the method of treating malignant tumors, especially brain tumors is via
- BNCT is a bimodal cancer treatment based on the selective accumulation of a
- boron-10 stable nuclide of boron known as boron-10, or 10 B, in the tumor, followed by irradiation
- thermalized neutrons impinge on the boron-
- a boron-10 nucleus captures a neutron forming the metastable i f . 4 ' ' nuclide B, which spontaneously and nearly instantaneously disintegrates into a He and
- Li particle which together possess an average total kinetic energy of 2.34 MeV.
- Targeted tumor thus receives a large dose of radiation while sparing surrounding normal tissue.
- the patient is first given an infusion of a carborane-containing porphyrin of .
- hemisphere of the brain can accumulate -boronated porphyrins.
- the tumor area is then irradiated with thermalized neutrons (primary irradiation),
- nuclide is high compared to the probability of capture by all of the other nuclides normally present in mammalian tissues, provided that boron- 10 concentrations in tumor
- carborane clusters are highly enriched in boron- 10. Specifically, the boron in the
- carborane cluster is enriched to at least 95 atom% in boron- 10.
- inventions are their increased polarity, imparted through polar groups W 1 , W 2 , W 3 , and W 4 ,
- the microlocalization within the tumor cell may
- present invention are more polar than carbon-carbon linkages and therefore, provide a
- invention includes carborane-containing porphyrin molecules containing 16 carborane
- Such high carborane-containing porphyrin molecules deliver more boron to a target, i.e.,
- porphyrin allows the amount of boron at the target to be significantly increased while
- tumor generally a systemically injected or infused dose of about 10-50 milligrams of
- boron- 10 per kg body weight in a pharmaceutically acceptable carrier is administered to a
- the carrier may include such commercially available solvents as Cremophor EL,
- propylene glycol, Tween 80, polyethylene glycol, or liposomes The compound is administered in one or more doses, the last dose being given between about 1 hour and
- porphyrin in the blood which decreases more rapidly with time than the porphyrin
- the tumor and various other tissues that absorb the compound are the tumor and various other tissues that absorb the compound.
- PDT is a bimodal cancer treatment based on the selective
- ground state singlet it can transfer energy to ground state triplet dioxygen
- Biomolecules that react most readily with singlet oxygen include unsaturated lipids and alpha amino-acid residues, both of which
- Fiber-optic probes are then used to illuminate the tumor tissue.
- a photosensitizing carborane-containing porphyrin of formula (1) Fiber-optic probes are then used to illuminate the tumor tissue.
- the therapeutic treatment of malignant tumors is
- SPECT the,patient is first given an infusion
- the patient's head is then scanned noninvasively and the radionuclide
- zones of equal boron- 10 concentration can thereby be drawn on each image of the brain.
- SPECT of the brain is at least one order of magnitude more sensitive to isotopic
- SPECT scanning can indicate the presence of a tumor in the patient, as well as its location in the brain or elsewhere in the body.
- SPECT scanning is noninvasive, fast, and
- the positron emitting PET-imageable radioisotope Cu-64 is more
- the therapeutic treatment of malignant tumors is
- MRI Magnetic resonance Imaging
- paramagnetic metal ion For a brain tumor, the patient's 'head is then scanned and the
- MRI imaged and quantified.
- MRI utilizing the compounds of the present invention may permit
- tumor tumor, and healthy tissue.
- reaction conditions such as temperature, reaction time, solvents, and extraction and
- tetraphenylporphyrin compounds can be synthesized by using a mixture of different
- solvent A is preferably, a polar non-pro tic
- W 1 is hydroxy, alkoxy, -C(O)OR 5 , -SOR 6 , -SO 2 R 6 , nitro, amido,
- solvent B is preferably a proton scavenger such
- R is an alkyl, cycloalkyl or aryl group.
- the borane cluster is any cluster comprising at least
- the borane cluster can be decaborane, Bi 0 Hi 4 .
- Z represents the carborane -C2HB 10 H 10 .
- Z represents any carborane cluster comprising at least two carbon atoms and at least three
- the carborane cluster may be -C 2 HB 9 Hi 0 or -C 2 HB I 0 H I Q, wherein -C 2 HBgHiO is nido ortho-, meta-, or para-carborane, and -C 2 HBi 0 Hi O is closo ortho-, meta-, or para-carborane.
- the protonating acid is any acid
- the protonating acid is concentrated HCl.
- the protic solvent is concentrated HCl.
- an alcohol such as methanol.
- solvent D is a polar non-protic solvent
- the oxidant is any oxidizing compound capable of selectively converting a primary alcohol to an aldehyde, preferably 2,3-dichloro-5,6-
- DDQ dicyano-1.4-benzoquinone
- PCC pyridiniura chlorochromate
- the coupling system preferably
- Lewis acid such as boron trifluoride (BF 3 ) or
- TFA trifiuoroacetic acid
- Solvent E is a nonpolar non-protic
- solvent preferably dichloromethane.
- M is selected from the group consisting of vanadium (V), manganese (Mn), iron (Fe),
- M is
- the metal salt used contains the metal ion M chelated to the
- porphyrin For example, for the compound where M is desired to be copper, copper
- Solvent F is any solvent or
- solvent mixture capable of at least partially solubilizing the porphyrin and metal salt
- alkynyl 78.5 (alkynyl); 110.2 (aryl); 114.3 (aryl); 119.0 (aryl); 135.2 (aryl); 146.0
- ArCH 2 4.33 (singlet, IH, CH); 4.39 (singlet, 2H, CH 2 CCHB I0 HIO); 6.85 (multiplet, 2H,
- dichloromethane showed the following peaks in nanometers of wavelength: 423, 517,
- porphyrin compound (VI) 130 milligrams, 91 millimoles
- Porphyrin compound (VII) was emulsified in 9% Cremophor EL and 18%
- carcinomas implanted on the dorsal thorax were given a total dose of 110 or 185
- mice were euthanized.
- the blood was first
- Tables 1 and 2 below show the average boron concentrations for different types of
- porphyrin VII 32 mg.B/kg or solvent only (9% Cremophor and 18% propylene glycol in saline) at 2 or 4 days after the last injection. Values are reported as median (and range).
- porphyrin VII 54 mg B/kg or solvent only (9% Cremophor and 18% propylene glycol in
- mice during and after porphyrin administration. At necropsy, all tissues appeared normal.
- Tables 3 and 4 show the weight changes and hematologic parameters in BALB/c mice
- carcinomas implanted on the dorsal thorax were given a total dose of 118 milligrams
- porphyrin compound (IX) per kilogram body weight 36 mg B/kg, respectively.
- mice were euthanized, and tumor, blood, brain, and
- liver were removed for boron analyses.
- the blood was first analyzed for hematologic
- microlocalization properties of porphyrin IX are likely to be different from those of
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
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AU2005327597A AU2005327597B2 (en) | 2004-05-20 | 2005-05-17 | Carboranylporphyrins and uses thereof |
NZ551732A NZ551732A (en) | 2004-05-20 | 2005-05-17 | Carboranylporphyrins and uses thereof |
CA002567468A CA2567468A1 (en) | 2004-05-20 | 2005-05-17 | Carboranylporphyrins and uses thereof |
EP05856727A EP1753468A4 (en) | 2004-05-20 | 2005-05-17 | Carboranylporphyrins and uses thereof |
JP2007527402A JP2008505983A (en) | 2004-05-20 | 2005-05-17 | Carboranyl porphyrins and their use |
IL179497A IL179497A0 (en) | 2004-05-20 | 2006-11-22 | Carboranylporphyrins and uses thereof |
US11/606,864 US20070093463A1 (en) | 2004-05-20 | 2006-12-01 | Radiation enhancement agent for X-ray radiation therapy and boron neutron-capture therapy |
NO20065858A NO20065858L (en) | 2004-05-20 | 2006-12-15 | Carboranylforphyrins and uses thereof |
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US10/848,741 US6995260B2 (en) | 2004-05-20 | 2004-05-20 | Carboranylporphyrins and uses thereof |
US10/848,741 | 2004-05-20 |
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US (1) | US6995260B2 (en) |
EP (1) | EP1753468A4 (en) |
JP (1) | JP2008505983A (en) |
KR (1) | KR20070026552A (en) |
CN (1) | CN1968705A (en) |
AU (1) | AU2005327597B2 (en) |
CA (1) | CA2567468A1 (en) |
IL (1) | IL179497A0 (en) |
NO (1) | NO20065858L (en) |
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WO2008102669A1 (en) * | 2007-02-19 | 2008-08-28 | Rei Medical Co., Ltd. | Novel sugar-linked chlorin derivative and process for production thereof |
US8680265B2 (en) | 2004-12-16 | 2014-03-25 | PSIMEI Pharmaceuticals | Process for the preparation of a boron-substituted porphyrin |
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GB2397067B (en) * | 2002-12-23 | 2005-05-11 | Destiny Pharma Ltd | Porphin & azaporphin derivatives with at least one cationic-nitrogen-containing meso-substituent for use in photodynamic therapy & in vitro sterilisation |
US20070093463A1 (en) * | 2004-05-20 | 2007-04-26 | Brookhaven Science Associates, Llc | Radiation enhancement agent for X-ray radiation therapy and boron neutron-capture therapy |
GB2415372A (en) | 2004-06-23 | 2005-12-28 | Destiny Pharma Ltd | Non photodynamical or sonodynamical antimicrobial use of porphyrins and azaporphyrins containing at least one cationic-nitrogen-containing substituent |
US8287839B2 (en) * | 2006-12-04 | 2012-10-16 | Brookhaven Science Associates, Llc | Carboranylporphyrins and uses thereof |
US8444953B2 (en) * | 2007-03-22 | 2013-05-21 | Brookhaven Science Associates, Llc | Symmetric and asymmetric halogen-containing metallocarboranylporphyrins and uses thereof |
US20080279781A1 (en) * | 2007-05-10 | 2008-11-13 | Brookhaven Science Associates, Llc | Glycosylated Carboranylporphyrins and Uses Thereof |
JP5745415B2 (en) * | 2009-09-17 | 2015-07-08 | 国立大学法人九州大学 | Porphyrin compounds |
US8563712B2 (en) * | 2009-10-28 | 2013-10-22 | The University Of Hong Kong | Hydroxy-substituted gold(III) porphyrin complexes as histone deacetylase inhibitors |
CN102268003B (en) * | 2011-06-16 | 2013-10-30 | 扬州大学 | Unsymmetrical poly-substituted porphyrin gold (III) type anticancer compound and preparation method thereof |
GB201221125D0 (en) * | 2012-11-23 | 2013-01-09 | Morex Dev Partners Llp | Pharmaceutial formulations |
KR20230011080A (en) * | 2021-07-13 | 2023-01-20 | 삼성에스디아이 주식회사 | Dye, composition compring the same, film, optical member and display device |
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2004
- 2004-05-20 US US10/848,741 patent/US6995260B2/en not_active Expired - Fee Related
-
2005
- 2005-05-17 AU AU2005327597A patent/AU2005327597B2/en not_active Ceased
- 2005-05-17 NZ NZ551732A patent/NZ551732A/en not_active IP Right Cessation
- 2005-05-17 CN CNA2005800203414A patent/CN1968705A/en active Pending
- 2005-05-17 KR KR1020067025283A patent/KR20070026552A/en not_active Application Discontinuation
- 2005-05-17 WO PCT/US2005/017358 patent/WO2006088476A2/en active Application Filing
- 2005-05-17 EP EP05856727A patent/EP1753468A4/en not_active Withdrawn
- 2005-05-17 JP JP2007527402A patent/JP2008505983A/en active Pending
- 2005-05-17 CA CA002567468A patent/CA2567468A1/en not_active Abandoned
-
2006
- 2006-11-22 IL IL179497A patent/IL179497A0/en unknown
- 2006-12-15 NO NO20065858A patent/NO20065858L/en not_active Application Discontinuation
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8680265B2 (en) | 2004-12-16 | 2014-03-25 | PSIMEI Pharmaceuticals | Process for the preparation of a boron-substituted porphyrin |
WO2008102669A1 (en) * | 2007-02-19 | 2008-08-28 | Rei Medical Co., Ltd. | Novel sugar-linked chlorin derivative and process for production thereof |
JP5290142B2 (en) * | 2007-02-19 | 2013-09-18 | 三栄源エフ・エフ・アイ株式会社 | Novel sugar-linked chlorin derivatives |
Also Published As
Publication number | Publication date |
---|---|
AU2005327597A1 (en) | 2006-08-24 |
NO20065858L (en) | 2007-02-09 |
EP1753468A2 (en) | 2007-02-21 |
CA2567468A1 (en) | 2006-08-24 |
CN1968705A (en) | 2007-05-23 |
IL179497A0 (en) | 2011-08-01 |
KR20070026552A (en) | 2007-03-08 |
WO2006088476A3 (en) | 2006-12-21 |
US6995260B2 (en) | 2006-02-07 |
JP2008505983A (en) | 2008-02-28 |
EP1753468A4 (en) | 2010-05-26 |
US20050260128A1 (en) | 2005-11-24 |
AU2005327597B2 (en) | 2011-02-24 |
NZ551732A (en) | 2011-03-31 |
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