CA2327393C - Solution pour la preparation d'une substance pharmaceutique pour le diagnostic et/ou le traitement de lesions tissulaires - Google Patents
Solution pour la preparation d'une substance pharmaceutique pour le diagnostic et/ou le traitement de lesions tissulaires Download PDFInfo
- Publication number
- CA2327393C CA2327393C CA002327393A CA2327393A CA2327393C CA 2327393 C CA2327393 C CA 2327393C CA 002327393 A CA002327393 A CA 002327393A CA 2327393 A CA2327393 A CA 2327393A CA 2327393 C CA2327393 C CA 2327393C
- Authority
- CA
- Canada
- Prior art keywords
- ala
- solution
- solution according
- ester
- diagnosis
- 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.)
- Expired - Lifetime
Links
- 239000003814 drug Substances 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 230000007170 pathology Effects 0.000 title 1
- 229960002749 aminolevulinic acid Drugs 0.000 claims abstract description 35
- 238000011282 treatment Methods 0.000 claims abstract description 18
- -1 5-aminolevulinic acid ester Chemical class 0.000 claims abstract description 15
- 238000003745 diagnosis Methods 0.000 claims abstract description 13
- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 claims abstract description 12
- 229950003776 protoporphyrin Drugs 0.000 claims abstract description 12
- 230000005855 radiation Effects 0.000 claims abstract description 6
- 238000001514 detection method Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 230000000295 complement effect Effects 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- UBQYURCVBFRUQT-UHFFFAOYSA-N N-benzoyl-Ferrioxamine B Chemical group CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN UBQYURCVBFRUQT-UHFFFAOYSA-N 0.000 claims description 3
- 230000000536 complexating effect Effects 0.000 claims description 3
- 229940099217 desferal Drugs 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000008055 phosphate buffer solution Substances 0.000 claims description 2
- 230000005779 cell damage Effects 0.000 claims 1
- 208000037887 cell injury Diseases 0.000 claims 1
- 230000000451 tissue damage Effects 0.000 claims 1
- 230000003902 lesion Effects 0.000 abstract description 10
- 238000009826 distribution Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000001413 cellular effect Effects 0.000 abstract description 3
- 231100000419 toxicity Toxicity 0.000 abstract description 3
- 230000001988 toxicity Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 description 23
- 210000003932 urinary bladder Anatomy 0.000 description 14
- 238000001126 phototherapy Methods 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000002964 excitative effect Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 102100035831 Filensin Human genes 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 208000001126 Keratosis Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- OEUUFNIKLCFNLN-LLVKDONJSA-N chembl432481 Chemical compound OC(=O)[C@@]1(C)CSC(C=2C(=CC(O)=CC=2)O)=N1 OEUUFNIKLCFNLN-LLVKDONJSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 108010062616 filensin Proteins 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 231100000760 phototoxic Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicinal Preparation (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9805425A FR2777782B1 (fr) | 1998-04-22 | 1998-04-22 | Solution pour la preparation d'une substance pharmaceutique pour le diagnostic et/ou le traitement de lesions tissulaires |
| FR98/05425 | 1998-04-22 | ||
| PCT/CH1999/000163 WO1999053962A1 (fr) | 1998-04-22 | 1999-04-22 | Solution pour le diagnostic ou le traitement de lesions tissulaires |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2327393A1 CA2327393A1 (fr) | 1999-10-28 |
| CA2327393C true CA2327393C (fr) | 2006-04-04 |
Family
ID=9525850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002327393A Expired - Lifetime CA2327393C (fr) | 1998-04-22 | 1999-04-22 | Solution pour la preparation d'une substance pharmaceutique pour le diagnostic et/ou le traitement de lesions tissulaires |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7348361B2 (enExample) |
| EP (1) | EP1073472B1 (enExample) |
| JP (2) | JP4630395B2 (enExample) |
| AT (1) | ATE228018T1 (enExample) |
| CA (1) | CA2327393C (enExample) |
| DE (1) | DE69904033T2 (enExample) |
| ES (1) | ES2188146T3 (enExample) |
| FR (1) | FR2777782B1 (enExample) |
| WO (1) | WO1999053962A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6992107B1 (en) | 1995-03-10 | 2006-01-31 | Photocure Asa | Esters of 5-aminolevulinic acid and their use as photosensitizing compounds in photochemotherapy |
| US6570001B1 (en) * | 1997-06-20 | 2003-05-27 | Institut Pasteur | Polynucleotides and their use for detecting resistance to streptogramin A or to streptogramin B and related compounds |
| DE10003620A1 (de) * | 2000-01-28 | 2001-08-02 | Asat Ag Applied Science & Tech | 5-Aminolävulinsäure-Formulierung in nichtwässrigen Lösungsmitteln |
| GB0018528D0 (en) | 2000-07-27 | 2000-09-13 | Photocure Asa | Compounds |
| RU2218570C2 (ru) * | 2001-11-01 | 2003-12-10 | Государственное образовательное учреждение высшего профессионального образования Московская медицинская академия им. И.М. Сеченова | Способ флюоресцентной диагностики новообразований |
| EP1312353A1 (en) * | 2001-11-16 | 2003-05-21 | Ecole Polytechnique Federale De Lausanne (Epfl) | Method for hair removal |
| US20090227997A1 (en) * | 2006-01-19 | 2009-09-10 | The Regents Of The University Of Michigan | System and method for photoacoustic imaging and monitoring of laser therapy |
| US20080123083A1 (en) * | 2006-11-29 | 2008-05-29 | The Regents Of The University Of Michigan | System and Method for Photoacoustic Guided Diffuse Optical Imaging |
| JP5472819B2 (ja) * | 2008-04-22 | 2014-04-16 | Ｓｂｉファーマ株式会社 | 膀胱がん検出方法 |
| CN102046817A (zh) * | 2008-05-30 | 2011-05-04 | 杰富意钢铁株式会社 | 生铁制造方法 |
| CN106692122A (zh) | 2008-10-27 | 2017-05-24 | 思佰益药业股份有限公司 | 以5‑氨基乙酰丙酸或其衍生物、或它们的盐作为有效成分的成人病的预防、改善剂 |
| US20100256125A1 (en) * | 2009-04-06 | 2010-10-07 | Zila Pharmaceuticals, Inc. | Use of improved toluidine blue in photodynamic therapy |
| JP2011001307A (ja) * | 2009-06-19 | 2011-01-06 | Sbi Alapromo Co Ltd | ５−アミノレブリン酸による子宮頸がん判定・治療システム |
| WO2011107478A1 (en) | 2010-03-01 | 2011-09-09 | Photocure Asa | Cosmetic compositions |
| KR101723834B1 (ko) | 2010-05-19 | 2017-04-06 | 에스비아이 파마 가부시키가이샤 | ５-아미노레불린산 또는 그 유도체를 유효성분으로 하는 항말라리아약 |
| WO2011161220A1 (en) * | 2010-06-23 | 2011-12-29 | Photocure Asa | Hyperosmotic preparations comprising 5 -amino levulinic acid or derivative as photosensitizing agent |
| US9345904B2 (en) | 2011-07-01 | 2016-05-24 | Sbi Pharmaceuticals Co., Ltd. | Photodynamic therapy using photosensitizing agent or 5-aminolevulinic acid |
| EP2745838B1 (en) | 2011-08-12 | 2017-07-26 | SBI Pharmaceuticals Co., Ltd. | Prophylactic agent and/or therapeutic agent for sepsis |
| US20140067024A1 (en) | 2012-08-30 | 2014-03-06 | Photocure Asa | Dual panel photodynamic therapy lamp |
| GB201221123D0 (en) | 2012-11-23 | 2013-01-09 | Photocure As | Device for photodynamic treatment |
| CN106460447B (zh) * | 2014-06-11 | 2018-12-11 | 日本板硝子株式会社 | 多层玻璃单元以及多层玻璃单元用玻璃板 |
| US9733187B2 (en) | 2015-03-06 | 2017-08-15 | King Saud University | Method of detecting bladder cancer by optical analysis of bodily fluids |
| GB201522398D0 (en) | 2015-12-18 | 2016-02-03 | Photocure As | Device for photodynamic therapy |
| AU2017277626A1 (en) * | 2016-06-08 | 2019-01-24 | Cf Genome, Llc | A chemical composition to stabilize extracellular vesicles in a blood sample and method of use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234940A (en) * | 1989-07-28 | 1993-08-10 | Queen's University | Photochemotherapeutic method using 5-aminolevulinic acid and precursors thereof |
| US5955490A (en) * | 1989-07-28 | 1999-09-21 | Queen's University At Kingston | Photochemotherapeutic method using 5-aminolevulinic acid and other precursors of endogenous porphyrins |
| NZ303251A (en) * | 1995-03-10 | 2000-10-27 | Photocure Asa | Use of esters of 5-aminolevulinic acid as photosensitising agents in photochemotherapy |
| US5856566A (en) * | 1997-09-02 | 1999-01-05 | Dusa Pharmaceuticals, Inc. | Sterilized 5-aminolevulinic acid |
-
1998
- 1998-04-22 FR FR9805425A patent/FR2777782B1/fr not_active Expired - Fee Related
-
1999
- 1999-04-22 EP EP99913060A patent/EP1073472B1/fr not_active Expired - Lifetime
- 1999-04-22 CA CA002327393A patent/CA2327393C/fr not_active Expired - Lifetime
- 1999-04-22 JP JP2000544365A patent/JP4630395B2/ja not_active Expired - Lifetime
- 1999-04-22 AT AT99913060T patent/ATE228018T1/de active
- 1999-04-22 ES ES99913060T patent/ES2188146T3/es not_active Expired - Lifetime
- 1999-04-22 US US09/673,871 patent/US7348361B2/en not_active Expired - Lifetime
- 1999-04-22 DE DE69904033T patent/DE69904033T2/de not_active Expired - Lifetime
- 1999-04-22 WO PCT/CH1999/000163 patent/WO1999053962A1/fr not_active Ceased
-
2010
- 2010-03-09 JP JP2010051284A patent/JP2010163445A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1073472B1 (fr) | 2002-11-20 |
| ES2188146T3 (es) | 2003-06-16 |
| ATE228018T1 (de) | 2002-12-15 |
| FR2777782B1 (fr) | 2001-05-18 |
| EP1073472A1 (fr) | 2001-02-07 |
| DE69904033T2 (de) | 2003-10-09 |
| FR2777782A1 (fr) | 1999-10-29 |
| WO1999053962A1 (fr) | 1999-10-28 |
| DE69904033D1 (de) | 2003-01-02 |
| US7348361B2 (en) | 2008-03-25 |
| JP4630395B2 (ja) | 2011-02-09 |
| US20030158258A1 (en) | 2003-08-21 |
| JP2002512205A (ja) | 2002-04-23 |
| JP2010163445A (ja) | 2010-07-29 |
| CA2327393A1 (fr) | 1999-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20190423 |