WO2006085517A1 - Preparation d’onguent ou suppositoire pour pdt a base de derive de chlorine ou de porphyrine - Google Patents

Preparation d’onguent ou suppositoire pour pdt a base de derive de chlorine ou de porphyrine Download PDF

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Publication number
WO2006085517A1
WO2006085517A1 PCT/JP2006/302031 JP2006302031W WO2006085517A1 WO 2006085517 A1 WO2006085517 A1 WO 2006085517A1 JP 2006302031 W JP2006302031 W JP 2006302031W WO 2006085517 A1 WO2006085517 A1 WO 2006085517A1
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Prior art keywords
ointment
base
suppository
derivative
pdt
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PCT/JP2006/302031
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English (en)
Japanese (ja)
Inventor
Yoshinori Nakae
Isao Sakata
Susumu Nakajima
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Photochemical Co., Ltd.
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Application filed by Photochemical Co., Ltd. filed Critical Photochemical Co., Ltd.
Priority to JP2007502601A priority Critical patent/JPWO2006085517A1/ja
Publication of WO2006085517A1 publication Critical patent/WO2006085517A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • 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
    • 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
    • A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to an ointment preparation and a suppository for a chlorin derivative or a porphyrin derivative used as photodynamic therapy (PDT).
  • PDT photodynamic therapy
  • PDT photodynamic therapy
  • certain porphyrin derivatives are administered by intravenous injection, etc., and these porphyrin derivatives are selectively accumulated in cancer cells and then irradiated with laser light to destroy only the cancer cells. It is a therapy that utilizes the two properties of porphyrin derivatives: selectivity for cancer cells and photosensitization.
  • porphyrin derivative used clinically for this PDT is porfimer sodium.
  • Non-Patent Document 1 Sales name: Photofrin Note
  • Porfimer sodium which first appeared, is a mixture of 2- to 6-mer polymers consisting of ether and Z or ester of a hematoporphyrin derivative. Porfimer sodium is known to cause temporary photosensitivity as a side effect when administered to the human body. In addition, the selective accumulation of porfimer sodium in cancer cells was still not sufficient, but it was confirmed that it was accumulated in normal cells.
  • NPe6 which has recently appeared, is a chlorin derivative and has attracted attention as a therapeutic agent for PDT that has solved the above-mentioned problems.
  • the present inventors have also described the above porfimana.
  • Various porphyrin derivatives have been proposed to solve the problems of thorium.
  • chlorin derivatives or porphyrin derivatives that have been used in the PDT proposed so far are administered to a living body by intravenous administration and then receive a single laser irradiation. It is effective for the treatment of cancer in some parts.
  • these chlorin derivatives or Borfilin compounds are absorbed through the skin. Therefore, it is desirable to selectively accumulate only in the affected area.
  • the present inventors should obtain accumulation by transdermal absorption for diseases formed in the skin epidermis such as actinic keratosis, inflammatory keratosis, V, ivy, and epidermis cancer.
  • diseases formed in the skin epidermis such as actinic keratosis, inflammatory keratosis, V, ivy, and epidermis cancer.
  • the application of an ointment preparation or suppository of a chlorin derivative or a porphyrin derivative was considered. Therefore, we investigated ointments based on the hydrophilic ointment base listed in the Japanese Pharmacopoeia, but the chlorin derivative or porphyrin derivative, which is an active ingredient contained in the base, decomposed over time, I could't get the desired result.
  • Non-patent document 1 Susumu Nakajima et al .: New drugs and clinical practice, 48 (1): 26 (1999)
  • Non-Patent Document 2 Saito K., et al: Jpn. J. Cancer Res., 91: 560, 2000
  • the present invention provides an ointment preparation and a suppository for a chlorin derivative or a porphyrin derivative used for PDT that can be applied to skin diseases such as actinic keratosis, inflammatory keratosis, warts, and epidermis cancer.
  • the task is to do.
  • the present invention for solving the problem to be solved is, as a basic aspect thereof, a non-aqueous solution for PDT containing 0.01 to 10.0% by weight of a chlorin derivative or a porphyrin derivative as an active ingredient. Ointment formulation or suppository.
  • the chlorin derivative or porphyrin derivative may be 13, 17-bis [( 1, 2 dicarboxyethyl) rubamoylethyl] 8 etyr-2-hydroxy 3 hydroxyiminoethylidene 1, 7, 12, 18-tetramethylchlorine tetrasodium [hereinafter abbreviated as ATX-S10 ⁇ Na ( ⁇ ) MOR], (2S, 3S) —18 Carboxy-20—Carboxymethyl-13 Ethyl 3, 7, 12, 17—Tetramethyl-8 Vinylchlorin — 2— [N— (1S)-(1, 2-Dicarboxy ) Ethyl] propionamide tetrasodium [hereinafter sometimes referred to as NPe6 or talaporphyrin sodium], protoporphyrin IX, hematoporphyrinka is a nonaqueous ointment or suppository for PDT as described above. .
  • the non-aqueous ointment base is FAPG (H) ointment base, FA PG (K) ointment base, PEG ointment base, PEG-PG ointment base, Vaseline ointment base, SR ⁇ serine ointment base, SR petrolatum IPM ointment base, plastibase ointment base force The nonaqueous ointment for PDT as described above.
  • the suppository base is a hydrophobic (lipophilic) base or a hydrophilic base, preferably cocoa butter, wittebuzole or macrogol. Suppository.
  • a non-aqueous ointment preparation and a suppository for PDT which contains a chlorin derivative or a porphyrin derivative having excellent pharmacological stability and good skin permeability as an active ingredient.
  • the ointment preparation provided by the present invention has an extremely good skin permeability (percutaneous absorbability), so that it is effective for cancer cells when applied to a diseased site such as epidermis cancer, for example, squamous cell carcinoma.
  • chlorin derivatives or voruline derivatives are accumulated, and by irradiating with laser light, only cancer cells can be selectively destroyed. Therefore, the present invention has great medical value in that it provides an ointment for use in a treatment method based on the concept of a single DDS (drug 'delivery' system).
  • chlorin derivatives or porphyrin derivatives used in the ointments and suppositories provided in the present invention include various derivatives that have been used in PDT so far. wear.
  • these chlorin derivatives or porphyrin derivatives include 13, 17-bis [(1, 2 dicarboxyethyl) force rubermoylethyl] 8 etyl 2 hydroxyl 3 hydroxyiminoethylidene 1, 2, 12 , 18-Tetramethylchlorine tetrasodium [ATX— S10'Na (II)], (2S, 3S) — 18-carboxy-20-carboxymethyl — 13 ethyl 3, 7, 12, 17-tetramethyl mono 8
  • Examples include bulchlorine 1- [N— (1S)-(1,2 dicarboxy) ethyl] propionamide tetrasodium [NPe6], protoporphyrin IX or hematoporphyrin.
  • ATX-SlO-Na (ll) is a chlorin derivative proposed by the present inventors, which reduces temporary photosensitivity as a side effect of porfimer sodium. It is a chlorin derivative for PDT that does not show accumulation in normal cells compared to Mer sodium and is excellent in selection and accumulation only in cancer cells.
  • NPe6 (Talaporphyrin Sodium) is a chlorin derivative and is a compound that has recently attracted attention as a therapeutic agent for PDT following Porfimanatrium. It is clinically known as Meiji Seika Co., Ltd. under the name of Rezafilin. More provided!
  • protoporphyrin IX or hematoporphyrin is a porphyrin derivative and is not very effective as a therapeutic agent for PDT.
  • the treatment based on the DDS theory of the present invention has a certain effect. It is a compound that can.
  • aminolevulinic acid (ALA) which is a protoporphyrin precursor, which is not limited to these chlorin derivatives or porphyrin derivatives, and benzoborphyrin as a new chlorin derivative whose structure has been converted from porphyrin derived from hemoglobin.
  • Derivatives (BPD) and metatetrahydroxyphenol chloride (m-THPC) can also be mentioned.
  • ATX-SlO'Na (II) or NPe6 can be preferably used.
  • non-aqueous ointment base can be a very good ointment.
  • non-aqueous ointment bases include FAPG (H) ointment base, FAPG (K) ointment base, PEG ointment base, PEG-PG ointment base, petrolatum ointment base, SR Vaseline ointment base, SR petrolatum IPM ointment base, and plastibase ointment base.
  • the FAPG (H) ointment base is an ointment base that also has stearyl alcohol, stearic acid, and propylene glycol.
  • the FAPG (K) ointment base is an ointment base composed of stearic alcohol, stearic acid and polyethylene glycol 400.
  • the PEG ointment base is an ointment base made of polyethylene glycol 400 and polyethylene glycol 4000
  • the PEG-PG ointment base is an ointment base made of propylene glycol and polyethylene glycol 4000.
  • Vaseline ointment base is an ointment base with petrolatum and liquid paraffin
  • SR petrolatum ointment base is an ointment base with SR petrolatum (5% salicylic acid-petrolatum) and liquid paraffin
  • SR petrolatum — IP M ointment base is an ointment base with SR petrolatum and isopropyl myristate
  • plastibase ointment base is an ointment base that also has a plastibase (95% liquid paraffin and 5% polyethylene oil) strength.
  • non-aqueous ointment base used in the present invention is not limited to those described above, and it goes without saying that an ointment base used pharmaceutically as a non-aqueous ointment can be used. Absent . It is also acceptable to add other stabilizers or transdermal absorption enhancers pharmacologically or pharmacologically.
  • the chlorin derivative or Borf contained in these non-aqueous ointment bases The chlorin derivative or the porphyrin derivative, which is a compounded active ingredient, is absorbed percutaneously and accumulates at the diseased site, and if the compound is added in an amount sufficient to kill the target cell by laser irradiation. Good. According to the study by the present inventors, it was found that a sufficient effect can be obtained if the blending amount is 0.01 to LO weight% based on the formulation weight.
  • the blending amount is less than 0.01% by weight, the intended therapeutic effect cannot be improved, and even if it is blended more than 10.0% by weight, no further effect can be obtained.
  • the compounding amount cannot be specified in general depending on the type of active ingredient to be contained, and the stability of the active ingredient to be contained is not greatly affected by the concentration of the active ingredient and the ointment base to be used. It is possible to make various changes according to the application within the range of the amount. Among them, when ATX-SlO'Na (II) is used as an active ingredient, a particularly preferable preparation with good pharmacological stability can be obtained by adding about 0.5% by weight. There was found.
  • a chlorin derivative or a porphyrin derivative which is an active ingredient, may be uniformly mixed in an ointment base.
  • the ointment preparation of the present invention obtained as described above is used for PDT therapy, skin diseases such as actinic keratosis, inflammatory keratosis, warts, epidermis cancer, for example, squamous epithelium
  • skin diseases such as actinic keratosis, inflammatory keratosis, warts, epidermis cancer, for example, squamous epithelium
  • the chlorin derivative or porphyrin derivative is effectively accumulated, and then the site can be effectively treated by light irradiation with a laser beam or the like.
  • Various laser lights, LEDs, and lamps can be used for light irradiation at a diseased site after the ointment of the present invention is applied.
  • a titanium sapphire laser, a semiconductor laser, an OPO-YAG laser, a xenon lamp, a halogen lamp, a methanolenolide lamp, or the like can be used.
  • the absorption wavelength is around 670 nm. It is more effective to use a semiconductor laser or LED for the chlorin derivative.
  • suppository bases that are widely used in pharmaceutics, preferably hydrophobic (lipophilic) bases, hydrophilic
  • a suppository can be prepared by applying a general suppository preparation using, for example, cacao butter, wittebuzole, or macrogol, such as a base.
  • Thea 25.0 g Thea 250 0 g Stearate 5-0 g Stearate 5 0 g Propylene glycol 69.5 g PEG 4 0 0 69 5 g Active ingredient 0.5 g Active ingredient 0 5 g Total 100. Og Total Amount 100 g
  • Example 2 Stable test of ointment preparation
  • the ointment preparation obtained above was sealed in an aluminum tube, stored at 40 ° CZ for 2 weeks, and the purity of the active ingredient was measured by HPLC to evaluate its stability.
  • the purity was determined by the area percentage by HPLC, and the purity before the start of storage and the purity after storage at 40 ° CZ for 2 weeks were determined. The results are shown in Tables 2 to 5 below.
  • Table 2 shows the purity of ATX-S10 ⁇ Na ( ⁇ ) stored at 40 ° CZ for 2 weeks
  • Table 3 shows the purity of NPe6 stored at 40 ° CZ for 2 weeks
  • Table 4 shows the protocol for storage at 40 ° CZ for 2 weeks.
  • the purity of porphyrin IX was shown
  • Table 5 shows the purity of hematoporphyrin stored at 40 ° CZ for 2 weeks.
  • Example 3 Long-term stability test of ointment preparation
  • Table 6 shows the results at room temperature and constant temperature (25 ° C), and Table 7 shows the results in a cold place (4 ° CZ refrigerator).
  • ointment preparations [Prescription 103 (PEG ointment) and Prescription 104 (PEG-PG ointment)] were applied to the injured and normal areas of the skin, and the application site was kept sealed for 4 hours. The ointment on the back surface was wiped off. A frozen skin section of the site was prepared and observed with fluorescence (excitation wavelength: 400 nm, fluorescence wavelength: 670 nm).
  • Fig. 1 is a fluorescence photograph of a frozen section of the skin when prescription 103 (PEG ointment) is applied at the injury site
  • Fig. 2 is the skin when prescription 104 (PEG-PG ointment) is applied at the injury site. It is a fluorescence photograph of a frozen section.
  • Fig. 3 is a fluorescent photograph of a frozen section of the skin when prescription 103 (PEG ointment) is applied at the normal site
  • Fig. 4 is a case when prescription 104 (PEG-PG ointment) is applied at the normal site. It is a fluorescence photograph of a skin frozen section.
  • the ointment preparation containing ATX—SlO—Na (II) as an active ingredient was tested for skin permeability in the ointment of Formula 103 (PE G ointment).
  • UV-B (apparatus: DMR—1, Toshiba—Eizai, fluorescent lamp: FL—20—SE—30, Toshiba) is irradiated 3 times in Z week for 1 month for 1 month on the hairless mouse.
  • Actinic keratosis model: Fig. 5 An image similar to actinic keratosis was observed (Actinic keratosis model: Fig. 5).
  • SCC model Fig. 6
  • squamous cell carcinoma develops (Fig. 7).
  • TPA (12-O-tetradecanol phorbol 13-acetate) was applied to the back of hairless mice to cause inflammation (psoriasis model).
  • An ointment of Formula 103 (PEG ointment) was applied to the affected area of these model animals in a red bean size, the application site was kept sealed for 4 hours, and then the surface ointment was wiped off. A frozen section of the skin at the site was prepared and observed with fluorescence (excitation wavelength: 400 nm, fluorescence wavelength: 670 nm).
  • Fig. 8 is a fluorescence photograph of a frozen skin section of the affected area of an Actinic keratosis model animal when prescription 103 (PEG ointment) is applied
  • Fig. 9 is a prescription 103 (PEG ointment) of an affected area of an SCC model animal.
  • FIG. 10 is a fluorescent photograph of a frozen skin section when a preparation of Formula 103 (PEG ointment) is applied in an affected area of a psoriasis model animal.
  • fe5ATX-S10'Na (II) is an active ingredient of the present invention in any model animal, that is, in the affected area of the Actinic ke ratosis model, the SCC model, and the psoriasis model. ) Permeates to the dermis.
  • the SCC model mouse prepared in Example 5 was used, and an ointment of prescription 103 (PEG ointment) was applied to the affected area in a red bean size, and the application site was kept sealed for 4 hours. Next, the ointment on the affected surface was wiped off, and a semiconductor laser (wavelength: 670 nm; energy: lOOjZcm 2) was irradiated from above.
  • PEG ointment prescription 103
  • Fig. 11 shows an SCC model animal before the semiconductor laser irradiation
  • Fig. 12 shows the state one day after the semiconductor laser irradiation
  • Fig. 13 shows the state three days after the semiconductor laser irradiation
  • Figs. This shows the situation after 6 days of semiconductor laser irradiation.
  • the arrow in the figure indicates the affected area of SCC, but it seems that the tumor area of the affected area disappears over time after irradiation. It is understood that the tumor site disappears completely 6 days after irradiation.
  • the present invention provides an ointment preparation for a chlorin derivative or a porphyrin derivative used as photodynamic therapy (PDT), and the ointment preparation provided by the present invention is a skin permeation preparation.
  • the property (percutaneous absorption) is very good. Therefore, chlorin derivatives or porphyrin derivatives can be effectively applied to cancer cells by applying to skin diseases such as actinic keratosis, inflammatory keratosis, warts, epidermoid cancer, eg squamous cell carcinoma. Are accumulated.
  • the chlorin derivative or porphyrin derivative accumulated at the tumor site can selectively destroy only cancer cells by light irradiation. Therefore, the present invention has great medical value in that it provides an ointment for use in a treatment method based on the concept of a single DDS (Drug 'Delivery System).
  • FIG. 1 is a fluorescence photograph of a frozen skin section when a preparation of Formula 103 (PEG ointment) is applied to an injury site in Example 4.
  • Formula 103 PEG ointment
  • FIG. 2 is a fluorescence photograph of a frozen skin section when a preparation of Formula 104 (PEG-PG ointment) is applied to an injury site in Example 4.
  • a preparation of Formula 104 PEG-PG ointment
  • FIG. 3 is a fluorescence photograph of a frozen skin section when a preparation of Formula 103 (PEG ointment) is applied to a normal site in Example 4.
  • Formula 103 PEG ointment
  • FIG. 4 is a fluorescence photograph of a frozen skin section when a preparation of Formula 104 (PEG-PG ointment) is applied to a normal site in Example 4.
  • FIG. 5 is a photograph of an actinic keratosis model animal in Example 5.
  • FIG. 6 is a photograph of an SCC model animal in Example 5.
  • FIG. 7 is a photograph of a squamous cell carcinoma model animal in Example 5.
  • FIG. 9 is a fluorescence photograph of a frozen skin section when a preparation of Formula 103 (PEG ointment) is applied to an affected area of an SCC model animal in Example 5.
  • a preparation of Formula 103 PEG ointment
  • Example 5 In Example 5, the formulation 103 (PEG ointment) was applied to the affected area of psoriasis model animals. It is the fluorescence photograph of the skin frozen section at the time of applying.
  • FIG. 11 is a photograph of an SCC model animal before irradiation with a semiconductor laser in Example 6.
  • FIG. 12 is a photograph of an SCC model animal one day after irradiation with a semiconductor laser in Example 6.
  • FIG. 13 is a photograph of an SCC model animal 3 days after irradiation with a semiconductor laser in Example 6.
  • FIG. 14 is a photograph of an SCC model animal 6 days after irradiation with a semiconductor laser in Example 6.

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Abstract

L’invention concerne des préparations d'onguent à base d’un dérivé de chlorine ou d’un dérivé de porphyrine, destinées à une utilisation dans une thérapie photodynamique (PDT) applicable aux maladies de la peau, telles que la kératose solaire, la kératose inflammatoire, une verrue et le cancer de la peau. L’invention fournit des préparations d'onguent non aqueuses pour PDT, comprenant de 0,01 à 10,0 % en poids d’un dérivé de chlorine ou d’un dérivé de porphyrine en tant que substance active. En particulier, l’invention fournit un onguent ou un suppositoire où le dérivé de chlorine ou le dérivé de porphyrine contenu dans celui-ci est ATX-S10 ⋅ Na (II), Npe6, la protoporphyrine IX ou l’hématoporphyrine.
PCT/JP2006/302031 2005-02-08 2006-02-07 Preparation d’onguent ou suppositoire pour pdt a base de derive de chlorine ou de porphyrine WO2006085517A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2702030A1 (fr) * 2011-04-27 2014-03-05 Northshore University Healthsystem Compositions et procédés
KR101623553B1 (ko) 2013-07-23 2016-05-23 동성제약주식회사 여드름 치료, 예방 또는 개선에 유효한 클로린 e6

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998014453A1 (fr) * 1996-10-01 1998-04-09 Wyeth Lederle Japan, Ltd. Derives d'acide iminochlorinaspartique
JP2004026717A (ja) * 2002-06-25 2004-01-29 Photochemical Co 脈管病に関する光物理化学的診断・治療薬

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998014453A1 (fr) * 1996-10-01 1998-04-09 Wyeth Lederle Japan, Ltd. Derives d'acide iminochlorinaspartique
JP2004026717A (ja) * 2002-06-25 2004-01-29 Photochemical Co 脈管病に関する光物理化学的診断・治療薬

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2702030A1 (fr) * 2011-04-27 2014-03-05 Northshore University Healthsystem Compositions et procédés
EP2702030A4 (fr) * 2011-04-27 2014-09-10 Univ Northshore Healthsystem Compositions et procédés
KR101623553B1 (ko) 2013-07-23 2016-05-23 동성제약주식회사 여드름 치료, 예방 또는 개선에 유효한 클로린 e6

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