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)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| FR98/05425 | 1998-04-22 | ||
| 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 |
| 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 (https=) |
| EP (1) | EP1073472B1 (https=) |
| JP (2) | JP4630395B2 (https=) |
| AT (1) | ATE228018T1 (https=) |
| CA (1) | CA2327393C (https=) |
| DE (1) | DE69904033T2 (https=) |
| ES (1) | ES2188146T3 (https=) |
| FR (1) | FR2777782B1 (https=) |
| WO (1) | WO1999053962A1 (https=) |
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 |
| WO2007084981A2 (en) * | 2006-01-19 | 2007-07-26 | The Regents Of The University Of Michigan | System and method for photoacoustic imaging and monitoring of laser therapy |
| WO2008067438A2 (en) * | 2006-11-29 | 2008-06-05 | The Regents Of University Of Michigan | System and method for photoacoustic guided diffuse optical imaging |
| WO2009130893A1 (ja) | 2008-04-22 | 2009-10-29 | Ｓｂｉアラプロモ株式会社 | 膀胱がん検出方法 |
| TWI426133B (zh) * | 2008-05-30 | 2014-02-11 | Jfe Steel Corp | Production method of pig iron |
| EP2340821B1 (en) | 2008-10-27 | 2017-01-25 | SBI Pharmaceuticals Co., Ltd. | Prophylactic/ameliorating agent for adult diseases comprising 5-aminolevulinic acid, derivative of 5-aminolevulinic acid, or salt of 5-aminolevulinic acid or the derivative of 5-aminolevulinic acid as active ingredient |
| 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 |
| CA2790827A1 (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 |
| EP2585111A1 (en) * | 2010-06-23 | 2013-05-01 | 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 |
| JP6052736B2 (ja) | 2011-08-12 | 2016-12-27 | Ｓｂｉファーマ株式会社 | 敗血症の予防剤及び／又は治療剤 |
| 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 |
| EP3567202B1 (en) * | 2014-06-11 | 2023-04-19 | Nippon Sheet Glass Company, Limited | Multiple-glazed glass unit |
| 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 |
| JP2019527363A (ja) * | 2016-06-08 | 2019-09-26 | シーエフ ジーノーム， エルエルシー | 血液サンプルの細胞外小胞を安定化するための化学組成物及びその使用方法 |
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 |
| ATE202076T1 (de) * | 1995-03-10 | 2001-06-15 | Photocure Asa | Ester der 5-aminolevulinsäure als mittel zur photosensibilisierung in der chemotherapie |
| 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 JP JP2000544365A patent/JP4630395B2/ja not_active Expired - Lifetime
- 1999-04-22 US US09/673,871 patent/US7348361B2/en not_active Expired - Lifetime
- 1999-04-22 WO PCT/CH1999/000163 patent/WO1999053962A1/fr not_active Ceased
- 1999-04-22 ES ES99913060T patent/ES2188146T3/es not_active Expired - Lifetime
- 1999-04-22 AT AT99913060T patent/ATE228018T1/de active
- 1999-04-22 DE DE69904033T patent/DE69904033T2/de not_active Expired - Lifetime
- 1999-04-22 EP EP99913060A patent/EP1073472B1/fr not_active Expired - Lifetime
- 1999-04-22 CA CA002327393A patent/CA2327393C/fr not_active Expired - Lifetime
-
2010
- 2010-03-09 JP JP2010051284A patent/JP2010163445A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002512205A (ja) | 2002-04-23 |
| JP2010163445A (ja) | 2010-07-29 |
| FR2777782A1 (fr) | 1999-10-29 |
| EP1073472A1 (fr) | 2001-02-07 |
| DE69904033D1 (de) | 2003-01-02 |
| DE69904033T2 (de) | 2003-10-09 |
| US20030158258A1 (en) | 2003-08-21 |
| WO1999053962A1 (fr) | 1999-10-28 |
| ATE228018T1 (de) | 2002-12-15 |
| EP1073472B1 (fr) | 2002-11-20 |
| JP4630395B2 (ja) | 2011-02-09 |
| CA2327393A1 (fr) | 1999-10-28 |
| US7348361B2 (en) | 2008-03-25 |
| ES2188146T3 (es) | 2003-06-16 |
| FR2777782B1 (fr) | 2001-05-18 |
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| González et al. | The phototoxicity of photodynamic therapy may be suppressed or enhanced by modulation of the cutaneous vasculature |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20190423 |