WO1998019677A1 - Traitement de maladies auto-immunes par photochimiotherapie - Google Patents
Traitement de maladies auto-immunes par photochimiotherapie Download PDFInfo
- Publication number
- WO1998019677A1 WO1998019677A1 PCT/JP1997/003769 JP9703769W WO9819677A1 WO 1998019677 A1 WO1998019677 A1 WO 1998019677A1 JP 9703769 W JP9703769 W JP 9703769W WO 9819677 A1 WO9819677 A1 WO 9819677A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mono
- chlorin
- aspartyl
- compound
- salt
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
-
- 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
- A61K31/395—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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
Definitions
- the present invention relates to a novel pharmaceutical composition for treating an autoimmune disease used for photochemotherapy or photodynamic therapy.
- the present invention also relates to a novel photochemotherapy method for treating autoimmune diseases.
- Photochemotherapy or photodynamic therapy is a method of treating a disease by administering a photosensitizer that can exert a therapeutic effect only when excited by irradiation with ultraviolet light or laser light.
- the pre-administered photosensitizer is accumulated in one or more sites of the living tissue where the photosensitizer accumulates, or in the body blood flow containing the photosensitizer, or the blood is extracorporeally circulated.
- This is a chemotherapy in which a photosensitizer is photochemically excited by irradiating the bloodstream with light or the like to exert a therapeutic effect of the photosensitizer to treat a disease.
- Photofrin which has the ability to destroy a wide variety of tumors. Therefore, it is mainly used for cancer treatment.
- the mechanism of action of the photofrin is that it administers an inactive, but not tumor-friendly, photofrin to the body, followed by the formation of a photofluorin around the neovasculature of the tumor.
- To accumulate tofrin When the accumulated photofrin is irradiated with a laser beam of a specific wavelength, the substance absorbs light energy, and the energy of the substance excites oxygen in tumor cells to excite oxygen. It is said to consist of producing active oxygen, which damages tumor cells and causes tumor tissue to die.
- Japanese Patent Publication Nos. 6-88902 and 6-89,000 and U.S. Pat. No. 4,675,338 disclose a certain type having a carboxyl group and a plurality of side chains of a carboxylic acid form.
- At least one carboxyl group of the tetrapyrroyl compound of the formula (1) has one or more amino groups of an aminodicarboxylic acid having 4 to 10 carbon atoms, for example, aspartic acid or glutamic acid.
- Fluorescent tetrapyrrole derivatives such as mono-L-aspartyl-chlorin e6 and mono-L-glutamyl-chlorin e6 or their salts, which are condensed by further amide bonds And methods for preparing these compounds.
- Photochemotherapy is not only a cancer treatment as described above, but also monotherapy.
- L-aspartyl chlorin e6 or mono-L-glutamyl chlorin e6 or its sodium salt is used, it is used to occlude new blood vessels such as the choroid of the eye. (See US Pat. No. 5,633,275).
- US Pat. No. 5,028,594 discloses that photochemotherapy is applied to a method for selectively removing hematopoietic cells involved in rheumatoid arthritis.
- Kenies et al. Have published a treatment method for proliferative joint disease characterized by causing synovial cell destruction by using photochemotherapy for proliferative joint disease (PCT International Publication W094Z). 17797).
- An object of the present invention is to include, for example, systemic lupus erythematosus, systemic scleroderma, polymyositis, dermatomyositis or polyarteritis nodosa, and autoimmune hemolytic anemia and Hashimoto's thyroiditis.
- An object of the present invention is to provide a novel pharmaceutical composition for treating various autoimmune diseases.
- Another object of the present invention is to provide a novel photochemotherapy treatment for an autoimmune disease.
- the present inventors searched for a therapeutic agent for an autoimmune disease such as systemic erythematosus for the above-mentioned purpose, and found that the above-mentioned JP-B-6-88902, JP-B-6-899000 and U.S. Pat. , 675, 338, a photosensitizer mono-L-aspartyl chlorin e6 (Mono-L-Asparty 1 Chl) which is undergoing clinical trials as a photochemotherapy for malignant tumors.
- a therapeutic agent for an autoimmune disease such as systemic erythematosus
- JP-B-6-88902, JP-B-6-899000 and U.S. Pat. , 675, 338 a photosensitizer mono-L-aspartyl chlorin e6 (Mono-L-Asparty 1 Chl) which is undergoing clinical trials as a photochemotherapy for malignant tumors.
- NPe6 tetrasodium salt
- the present invention provides a pharmaceutical composition for treating an autoimmune disease by photochemotherapy, which comprises a salt as an active ingredient.
- Chlorine e6 or mono-L-glutamyl-chlorin e6 can be obtained from the following equation (A) by precise analysis of various NMR spectra.
- the above mono-L-aspartyl chlorin e6 has a side chain of a tetrapyrrole ring represented by the above formula (A), and L-aspateginic acid is one of the carboxylic acid groups. This is a compound in which the amino group is amide bonded.
- Mono-L-aspartyl, chlorin e6 is used in its four carboxyl groups in the form of tetrasodium salt Is preferred.
- the compound in which L-glutamic acid is amide-bonded instead of L-aspartic acid is mono-L-daltamino chlorin e6.
- Mono-L-aspartyl-chlorin e6 or mono-L-glutamyl-chlorin e6 used as a photosensitizer in the present invention is a pharmacologically acceptable salt thereof. And can generally be in the form of a salt formed by reaction with a pharmacologically acceptable base.
- Such salts include, for example, salts with sodium, potassium, calcium, magnesium, ammonium, triethylammonium, trimethylammonium, morpholine and pyridin.
- mono-L-aspartyl-chlorin e6 or mono-L-daltamyl-chlorin e6 or mono-L-aspartyl chlorin e6 is administered to a patient having an autoimmune disease to be treated.
- the mono-L-aspartyl chlorin e6 or the mono-L-daltamyl quinone e6 still contained in the bloodstream, and then irradiated the salt with ultraviolet light or laser light.
- mono-L-aspartyl chlorin e6 or mono-L-glutamyl'chlorin e6 or a salt thereof is administered parenterally. It can be administered by intravenous or intramuscular injection. Alternatively, they can be administered orally or rectally.
- the dose is determined by measuring the number of autoantibodies present in the bloodstream when subsequently irradiated with ultraviolet light or laser light. It is an effective amount sufficient to reduce aspartyl chlorin e6 or mono-L-glutamyl, chlorin e6 or its salt. This effective amount can be administered once, twice or more.
- the ultraviolet or laser light to be irradiated may be emitted as a beam from the whole body or various parts of the patient, such as the abdomen, the legs, the skin of the hands, and thereby the ultraviolet or laser light.
- the skin and the vascular wall layer so that they can reach the vascular blood flow under the skin. It can be carried out. Irradiation may be performed on the blood flow circulated extracorporeally.
- the number of UV or laser irradiations can be one or more times, independent of the number of doses of the administered compound.
- the combination of the number of administrations of the administered compound and the number of irradiations of ultraviolet light or laser light may be sufficient to significantly reduce the antibody level of autoantibodies in the bloodstream.
- the total number of doses of mono-L-aspartyl or mono-L-daltamisolle chlorin e6 or a salt thereof is, for example, one.
- the number of times of irradiation with ultraviolet rays or laser light can be 100 times, for example, 5 times to 100 times.
- the required number of compound doses and the required number of light exposures can be readily determined by expert pilot studies, depending on the specifics of the treatment.
- the ultraviolet light or laser light to be irradiated is preferably light having a wavelength of 620 to 760 nm, and can be irradiated at an irradiation intensity of 10 to 100 mW Zcnf.
- the first pharmaceutical composition according to the present invention and the photochemotherapeutic treatment method according to the second present invention include: systemic erythematosus, systemic scleroderma, polymyositis, dermatomyositis or multiple nodular arteries It is effective in treating or preventing systemic autoimmune diseases such as inflammation.
- the present invention is also useful for treating autoimmune diseases such as autoimmune hemolytic anemia and Hashimoto's thyroiditis. Can be expected to be effective.
- Mono-L-aspartyl or mono-L-glutamyl lactone e6 or a salt thereof which is an active ingredient used in the first pharmaceutical composition of the present invention, is orally or intravenously or intramuscularly. It can also be administered parenterally, such as by injection. It can also be administered transdermally.
- mono-L-aspartyl or mono-L-glutamyl chlorin e6 or a salt thereof contains this in the form of a tetrasodium salt, and is freeze-dried, sterile and pyrogen. It is preferable to administer it by formulating it as a pharmaceutical composition containing no.
- the first pharmaceutical composition of the present invention comprises, as an active ingredient, mono-L-aspartyl or mono-L-daltamyl'chlorin e6 or a salt thereof. It can be mixed with conventional pharmaceutically acceptable solid or liquid carriers and can be formulated in the form of tablets, buccal, troches, capsules, suspensions, syrups, etc. it can.
- the content ratio of the above compound as the active ingredient in the first pharmaceutical composition of the present invention varies depending on the dosage form, but the preferred content ratio is in the range of about 2 to 6% by weight of the dosage unit. There should be.
- a desirable formulation is a sterile aqueous solution or dispersion containing the compound as an active ingredient, or sterile freezing.
- a desiccant There is a desiccant.
- liquid carriers used here include water, ethanol, glycerol, propylene glycol, Vegetable oils and the like are preferred.
- the compound as an active ingredient should have a desired particle size and a viscosity modifier such as lecithin should be compounded. Thereby, the dispersed state of the compound of the active ingredient can be favorably maintained.
- a viscosity modifier such as lecithin
- isotonic agents for example, sugars or sodium chloride.
- the first composition of the present invention is an injectable preparation
- an agent which delays absorption of the compound as an active ingredient for example, aluminum monostearate or gelatin may be added. it can.
- the dose of mono-L-aspartyl or mono-L-daltamyl chlorin e6 or a salt thereof used in the present invention depends on the type of the disease to be treated, the purpose of the treatment and the degree of the symptom. Although different, in general, for adults, 0.2 to 10 mg per day is administered once or in several divided doses. Optimal dosage can be determined by appropriate preliminary tests by a specialist.
- an intense laser continuous light source having an optical filter, an excited dye, or another laser transmitting system is used.
- a radiation source of the record one The first light, at a wavelength of six hundred and twenty to seven hundred and sixty nm, the irradiation intensity of 10 ⁇ 100 mWZ cm 2, desired laser source can oscillate laser at least for the total output of even 500 mW It is.
- Current, Some commercially available laser oscillators meet the laser-oscillation criteria described above.
- NP e 6 which is used in an example of a light-sensitive compound administered in the present invention was tested acute toxicity Male mice CD- 1, the value of its The LD 50 Atsuta at 164 mg ZKG. In a phototoxicity test, NPe6 did not show any reaction such as erythema or edema, and was confirmed to be a highly safe compound.
- the MRL / 1pr mouse which is known as a spontaneous systemic autoimmune disease model, has the unique property of spontaneously developing a systemic autoimmune disease by 1pr-gene.
- the characteristic findings of the developed autoimmune disease are the formation of lymphoma and splenomegaly due to the proliferation of atypical lymphocyte cells, the production of anti-ds-DNA antibodies as autoantibodies, and / or immunity.
- This is the development of lupus nephritis due to complex deposition, which leads to spontaneous early death of MR LZ1r mice.
- untreated MR LZ 1 pr mice have the property of generally reaching 50% mortality at the age of 25 weeks.
- NPe6 tetra-sodium salt
- NPe6 tetra-sodium salt
- NPe6 contained in the bloodstream in the blood vessels under the skin of the mouse abdomen was exposed to laser light, and as a result, was photochemically excited.
- Each mouse was administered eight times a 10-day period of photochemotherapy consisting of such intravenous administration of NPe6 and irradiation with laser light. Twenty-four hours after the end of the last laser-irradiated treatment of the mice in the treatment group, ie, at the age of 19 weeks of the mice, the therapeutic effect observed in the treated mice was determined. In addition, the survival benefit obtained with the treated mice was observed after the administration of this treatment until the 49th week.
- MRLZ 1 pr mice in the untreated group (10 mice per group, 18 weeks old) received intravenous administration of the same amount of saline (containing no NPe6) as the mice in the treatment group and were administered in the same manner as in the treatment group.
- saline containing no NPe6
- anti-ds-DNA antibody shows disease specificity characteristic of systemic erythematosus and reflects disease activity.
- Significant reduction of anti-ds-DNA antibody levels suggests that the above-mentioned photochemotherapy alleviated the symptoms of systemic lupus erythematosus, that is, that lupus erythematosus was successfully treated. Is what you do.
- Blood and urine were collected from 19-week-old mice 24 hours after the eighth laser irradiation.
- Blood urea nitrogen and urinary protein levels which are indicators of renal function, were measured using the collected blood samples.
- Blood urea nitrogen and urinary protein levels were 36.4 ⁇ 5.3 mg / dl and 246.2 ⁇ 24.0 mg / dl in the untreated group, and 22.3 ⁇ 1.4 mg / dl and 85.2 ⁇ in the treatment group, respectively. The value was 5.0 mg / dl.
- Both blood urea nitrogen and urinary protein levels were reduced in the treated group compared to the untreated group. This indicates that the photochemotherapy in this example ameliorated the reduced renal function in MRL / 1pr mice.
- mice were bred up to the 49th week after completion of the above-described treatment with photochemotherapy, and the survival rate (%) of the mice was measured for each week.
- the results obtained are summarized in Table 1. ⁇ table 1 ⁇
- a mono-L-aspartyl chlorin e6 or a mono-L-one for producing a pharmaceutical composition for photochemotherapeutic treatment of an autoimmune disease.
- the use of daltamyl chlorin e6 or a pharmaceutically acceptable salt thereof is provided.
- the mono-over L- ⁇ scan Paruchiru-click b Li down e 6 or mono one L Guruta Mi Honoré-click b Li down e 6, or a pharmaceutically acceptable salt thereof Provided is a method for preparing a pharmaceutical composition for photochemotherapeutic treatment of an autoimmune disease, comprising admixing with a pharmaceutically acceptable carrier.
- FIG. 1 is a graph showing the life-span curves of a treated group of MRLZ lpr mice treated with NP e6 according to the present invention and subjected to photochemotherapy treatment by irradiating a laser beam, and an untreated group of the mice. is there.
- NPE6 200 mg was dissolved in saline to a final concentration of 20 mgZml.
- the injection composition obtained by sterilizing this solution was suitable for intravenous administration and intramuscular administration.
- the present invention relates to a blood stream containing the compound after administration of mono-L-aspartyl or mono-L-glutamyl-chlorin e6 or a salt thereof to a patient with an autoimmune disease.
- the method of irradiating the patient with ultraviolet or laser light can significantly reduce the amount of autoantibodies in the patient's blood. Therefore, the present invention is effective in treating various autoimmune diseases such as systemic erythematosus, systemic sclerosis, polymyositis, dermatomyositis and polyarteritis nodosa by photochemotherapy.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002270558A CA2270558C (en) | 1996-11-06 | 1997-10-17 | Treatment of autoimmune diseases by photochemotherapy |
US09/297,810 US6350772B1 (en) | 1996-11-06 | 1997-10-17 | Treatment of auto-immune diseases by photochemotherapy |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP29306196 | 1996-11-06 | ||
JP8/293061 | 1996-11-06 | ||
JP9/204711 | 1997-07-30 | ||
JP20471197 | 1997-07-30 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/056,410 Continuation US6653337B2 (en) | 1996-11-06 | 2002-01-23 | Therapy of auto-immune disease by a photochemotherapeutical method |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998019677A1 true WO1998019677A1 (fr) | 1998-05-14 |
Family
ID=26514606
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1997/003769 WO1998019677A1 (fr) | 1996-11-06 | 1997-10-17 | Traitement de maladies auto-immunes par photochimiotherapie |
Country Status (3)
Country | Link |
---|---|
US (2) | US6350772B1 (ja) |
CA (1) | CA2270558C (ja) |
WO (1) | WO1998019677A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003510372A (ja) * | 1999-10-05 | 2003-03-18 | ユニヴェルスィテ・ドゥ・モントリオール | 光力学診断及び治療のためのローダミン誘導体 |
WO2006112379A1 (ja) * | 2005-04-14 | 2006-10-26 | Takafumi Ohshiro | 光照射による皮膚又は皮下軟部組織の血管性病変治療又は診断用薬剤 |
JP2019533635A (ja) * | 2016-10-26 | 2019-11-21 | リウ, フゥイLIU, Hui | 新規なジヒドロポルフィンe6誘導体及びその薬学的に許容される塩、その調製方法並びに使用 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN2885311Y (zh) | 2006-01-18 | 2007-04-04 | 郑成福 | 经尿道光动力疗法前列腺治疗仪 |
US20080269846A1 (en) * | 2003-03-14 | 2008-10-30 | Light Sciences Oncology, Inc. | Device for treatment of blood vessels using light |
US10376711B2 (en) * | 2003-03-14 | 2019-08-13 | Light Sciences Oncology Inc. | Light generating guide wire for intravascular use |
ATE498426T1 (de) * | 2003-06-20 | 2011-03-15 | Univ Keio | Photodynamisches therapiegerät |
US20100087534A1 (en) * | 2005-07-05 | 2010-04-08 | Maria-Anna Ortner | Use of a Photosensitizing Agent in the Treatment or Prevention of an Inflammation-Associated Disorder in the Gastrointestinal Tract of a Mammal |
US8057464B2 (en) | 2006-05-03 | 2011-11-15 | Light Sciences Oncology, Inc. | Light transmission system for photoreactive therapy |
US7993640B2 (en) | 2008-08-06 | 2011-08-09 | Light Sciences Oncology, Inc. | Enhancement of light activated therapy by immune augmentation using anti-CTLA-4 antibody |
US20110008372A1 (en) * | 2009-07-08 | 2011-01-13 | Light Sciences Oncology, Inc. | Enhancement of light activated drug therapy through combination with other therapeutic agents |
US11251635B2 (en) | 2017-12-19 | 2022-02-15 | Welch Allyn, Inc. | Vital signs monitor with a removable and dischargable battery |
Citations (3)
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---|---|---|---|---|
JPS6183186A (ja) * | 1984-07-18 | 1986-04-26 | Nippon Petrochem Co Ltd | 新規なテトラピロ−ル医薬用組成物 |
JPS625986A (ja) * | 1985-04-30 | 1987-01-12 | Nippon Petrochem Co Ltd | 新規なテトラピロ−ル化合物 |
JPH02138280A (ja) * | 1988-07-14 | 1990-05-28 | Toyo Hatsuka Kogyo Kk | ポルフィリン誘導体 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5028594A (en) * | 1988-12-27 | 1991-07-02 | Naxcor | Use of photodynamic compositions for cytotoxic effects |
JP3565442B2 (ja) * | 1993-04-22 | 2004-09-15 | 新日本石油化学株式会社 | 哺乳類の関節炎の診断剤および/または治療剤 |
-
1997
- 1997-10-17 CA CA002270558A patent/CA2270558C/en not_active Expired - Lifetime
- 1997-10-17 US US09/297,810 patent/US6350772B1/en not_active Expired - Lifetime
- 1997-10-17 WO PCT/JP1997/003769 patent/WO1998019677A1/ja active Application Filing
-
2002
- 2002-01-23 US US10/056,410 patent/US6653337B2/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6183186A (ja) * | 1984-07-18 | 1986-04-26 | Nippon Petrochem Co Ltd | 新規なテトラピロ−ル医薬用組成物 |
JPS625986A (ja) * | 1985-04-30 | 1987-01-12 | Nippon Petrochem Co Ltd | 新規なテトラピロ−ル化合物 |
JPH02138280A (ja) * | 1988-07-14 | 1990-05-28 | Toyo Hatsuka Kogyo Kk | ポルフィリン誘導体 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003510372A (ja) * | 1999-10-05 | 2003-03-18 | ユニヴェルスィテ・ドゥ・モントリオール | 光力学診断及び治療のためのローダミン誘導体 |
JP4859319B2 (ja) * | 1999-10-05 | 2012-01-25 | ユニヴェルスィテ・ドゥ・モントリオール | 光力学診断及び治療のためのローダミン誘導体 |
WO2006112379A1 (ja) * | 2005-04-14 | 2006-10-26 | Takafumi Ohshiro | 光照射による皮膚又は皮下軟部組織の血管性病変治療又は診断用薬剤 |
JP5265186B2 (ja) * | 2005-04-14 | 2013-08-14 | 貴史 大城 | 光照射による皮膚又は皮下軟部組織の血管性病変治療又は診断用薬剤 |
JP2019533635A (ja) * | 2016-10-26 | 2019-11-21 | リウ, フゥイLIU, Hui | 新規なジヒドロポルフィンe6誘導体及びその薬学的に許容される塩、その調製方法並びに使用 |
Also Published As
Publication number | Publication date |
---|---|
US6350772B1 (en) | 2002-02-26 |
CA2270558C (en) | 2006-08-15 |
US6653337B2 (en) | 2003-11-25 |
US20020137735A1 (en) | 2002-09-26 |
CA2270558A1 (en) | 1998-05-14 |
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