ES2548575T3 - Procedimiento para la síntesis de 4,5,6,7-tetracloro-3',6'-dihidroxi-2',4',5',7'-tetrayodo-3H-espiro[isobenzofuran-1,9'-xanten]-3-ona (Rosa de Bengala) y xantenos relacionados - Google Patents
Procedimiento para la síntesis de 4,5,6,7-tetracloro-3',6'-dihidroxi-2',4',5',7'-tetrayodo-3H-espiro[isobenzofuran-1,9'-xanten]-3-ona (Rosa de Bengala) y xantenos relacionados Download PDFInfo
- Publication number
- ES2548575T3 ES2548575T3 ES10817918.5T ES10817918T ES2548575T3 ES 2548575 T3 ES2548575 T3 ES 2548575T3 ES 10817918 T ES10817918 T ES 10817918T ES 2548575 T3 ES2548575 T3 ES 2548575T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- independently
- impurities
- xanten
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000003732 xanthenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 4
- 239000012535 impurity Substances 0.000 abstract 4
- 150000002500 ions Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24370109P | 2009-09-18 | 2009-09-18 | |
| US243701P | 2009-09-18 | ||
| PCT/US2010/049341 WO2011035161A1 (en) | 2009-09-18 | 2010-09-17 | Process for the synthesis of 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5'7'-tetraiodo-3h-spiro[isobenzofuran-1,9'-xanthen]-3-one (rose bengal) and related xanthenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2548575T3 true ES2548575T3 (es) | 2015-10-19 |
Family
ID=43757167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10817918.5T Active ES2548575T3 (es) | 2009-09-18 | 2010-09-17 | Procedimiento para la síntesis de 4,5,6,7-tetracloro-3',6'-dihidroxi-2',4',5',7'-tetrayodo-3H-espiro[isobenzofuran-1,9'-xanten]-3-ona (Rosa de Bengala) y xantenos relacionados |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8530675B2 (en:Method) |
| EP (1) | EP2464225B8 (en:Method) |
| JP (1) | JP5671040B2 (en:Method) |
| KR (1) | KR101494055B1 (en:Method) |
| CN (1) | CN102548406B (en:Method) |
| CA (1) | CA2771988C (en:Method) |
| ES (1) | ES2548575T3 (en:Method) |
| MX (1) | MX2012003063A (en:Method) |
| WO (1) | WO2011035161A1 (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2828940C (en) | 2011-03-10 | 2024-04-16 | Provectus Pharmaceuticals, Inc. | Combination of local and systemic immunomodulative therapies for enhanced treatment of cancer |
| US9470610B2 (en) * | 2013-10-22 | 2016-10-18 | The United States Of America As Represented By The Secretary Of The Air Force | Methods for using rose bengal for detection of oxidative decomposition of contaminants |
| JP7015232B2 (ja) * | 2018-11-21 | 2022-02-02 | 東レ・ファインケミカル株式会社 | 高純度のフルオレセイン類化合物の製造方法 |
| WO2020173891A1 (en) * | 2019-02-26 | 2020-09-03 | F. Hoffmann-La Roche Ag | Process for the preparation of (6s)-3-[(4s)-4-cyano-2-oxo-pyrrolidin-1-yl]-6-methyl-n-(3,4,5-trifluorophenyl)-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazine-5-carboxamide |
| JP7512409B6 (ja) | 2020-03-26 | 2024-07-23 | プロヴェクタス ファーマテック，インク． | 腫瘍学及びウイルス学におけるハロゲン化キサンテンの新規の使用 |
| US11938182B2 (en) | 2020-03-26 | 2024-03-26 | Provectus Pharmatech, Inc. | Halogenated xanthenes as vaccine adjuvants |
| US20240325341A1 (en) * | 2023-03-29 | 2024-10-03 | Provectus Pharmatech, Inc. | Anti-bacterial effect of halogenated fluoresceins against colistin-resistant gram-negative bacteria |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE108838C (en:Method) | ||||
| US1965842A (en) * | 1931-11-21 | 1934-07-10 | Nat Aniline & Chem Co Inc | Production of hydroxybenzenephthaleins |
| US1931049A (en) * | 1931-11-21 | 1933-10-17 | Nat Aniline & Chem Co Inc | Process of making dihydroxyfluoranes |
| US3829440A (en) * | 1972-12-21 | 1974-08-13 | Richardson Merrell Inc | Xanthene derivatives |
| SU517222A1 (ru) | 1974-10-25 | 1977-06-25 | Институт Биофизики Министерства Здравохранения Ссср | Способ получени препарата бенгальска роза, меченного радиоизотопами йода |
| SU792878A1 (ru) | 1978-08-29 | 1982-02-07 | Ленинградский институт ядерной физики им. Б.П.Константинова | Способ получени галогенированных производных флуоресцеина,меченных радиоизотопом йода |
| EP0050684B1 (en) | 1980-10-27 | 1986-01-22 | Syva Company | Novel ether substituted fluorescein compounds as fluorescers and quenchers |
| SU992516A1 (ru) | 1981-06-11 | 1983-01-30 | Ленинградский Институт Ядерной Физики Им.Б.П.Константинова | Способ получени галогенированных производных флуоресцеина,меченных радиоизотопом иода -123 |
| ES8606451A1 (es) | 1985-10-28 | 1986-04-16 | Zoster Sa | Procedimiento para la obtencion de la eritrosina sodica |
| IN168346B (en:Method) | 1987-09-07 | 1991-03-16 | Council Scient Ind Res | |
| US5637733A (en) * | 1995-09-27 | 1997-06-10 | Warner-Jenkinson Company, Inc. | Syntheses of fluorescein compounds with excess resorcinol as a solvent |
| US6252024B1 (en) * | 1995-10-23 | 2001-06-26 | Novartis Ag | Fluorescent N-alkylated acrylamide copolymers and optical pH sensors |
| US6162931A (en) * | 1996-04-12 | 2000-12-19 | Molecular Probes, Inc. | Fluorinated xanthene derivatives |
| US5945526A (en) * | 1996-05-03 | 1999-08-31 | Perkin-Elmer Corporation | Energy transfer dyes with enhanced fluorescence |
| US6331286B1 (en) | 1998-12-21 | 2001-12-18 | Photogen, Inc. | Methods for high energy phototherapeutics |
| US7648695B2 (en) | 1998-08-06 | 2010-01-19 | Provectus Pharmatech, Inc. | Medicaments for chemotherapeutic treatment of disease |
| US6372907B1 (en) * | 1999-11-03 | 2002-04-16 | Apptera Corporation | Water-soluble rhodamine dye peptide conjugates |
| US6448407B1 (en) | 2000-11-01 | 2002-09-10 | Pe Corporation (Ny) | Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis |
| WO2002062333A1 (en) | 2001-02-05 | 2002-08-15 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Use of 9h-xanthenes in a method of inhibiting viral replication targeting the nucleocapsid protein |
| US6800765B2 (en) * | 2001-08-02 | 2004-10-05 | Molecular Devices Corporation | Fluorescent pH indicators for intracellular assays |
| CA2490961A1 (en) * | 2002-07-01 | 2004-01-08 | Guava Technologies, Inc. | Fluorescent dyes, energy transfer couples and methods |
| FR2846331B1 (fr) * | 2002-10-29 | 2006-11-17 | Synth Innove Lab | Phtaleines de purete elevee et leur procede de preparation |
| KR100853969B1 (ko) * | 2003-02-28 | 2008-08-25 | 징크 이메징, 엘엘씨 | 이미징 시스템 |
| EP1753467B1 (en) * | 2004-06-10 | 2013-01-09 | Provectus Pharmatech, Inc. | Diagnostic agents for positron emission imaging using radiolabeled halogenated xanthenes and methods for positron emission imaging with radiolabeled halogenated xanthene diagnostic agents |
| CA2657691A1 (en) * | 2006-06-19 | 2007-12-27 | Vanderbilt University | Methods and compositions for diagnostic and therapeutic targeting of cox-2 |
| GB0613287D0 (en) * | 2006-07-05 | 2006-08-16 | Ge Healthcare Ltd | Dye imaging agents |
| ITMI20061713A1 (it) * | 2006-09-08 | 2008-03-09 | St Microelectronics Srl | Procedimento per la sintesi di derivati alogenati della fluoresceina utili nella produzione di dispositivi di memoria non volatile |
-
2010
- 2010-09-17 EP EP10817918.5A patent/EP2464225B8/en active Active
- 2010-09-17 MX MX2012003063A patent/MX2012003063A/es unknown
- 2010-09-17 CN CN201080041506.7A patent/CN102548406B/zh active Active
- 2010-09-17 WO PCT/US2010/049341 patent/WO2011035161A1/en active Application Filing
- 2010-09-17 ES ES10817918.5T patent/ES2548575T3/es active Active
- 2010-09-17 KR KR1020127009834A patent/KR101494055B1/ko active Active
- 2010-09-17 JP JP2012529937A patent/JP5671040B2/ja active Active
- 2010-09-17 CA CA2771988A patent/CA2771988C/en active Active
- 2010-09-17 US US12/884,833 patent/US8530675B2/en active Active
-
2013
- 2013-06-12 US US13/916,408 patent/US9422260B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011035161A1 (en) | 2011-03-24 |
| CA2771988A1 (en) | 2011-03-24 |
| HK1172212A1 (zh) | 2013-04-19 |
| EP2464225A1 (en) | 2012-06-20 |
| KR101494055B1 (ko) | 2015-02-16 |
| US9422260B2 (en) | 2016-08-23 |
| HK1172501A1 (en) | 2013-04-26 |
| JP5671040B2 (ja) | 2015-02-18 |
| JP2013505261A (ja) | 2013-02-14 |
| US20130274322A1 (en) | 2013-10-17 |
| US8530675B2 (en) | 2013-09-10 |
| CN102548406A (zh) | 2012-07-04 |
| EP2464225B1 (en) | 2015-09-16 |
| MX2012003063A (es) | 2012-07-25 |
| US20110071217A1 (en) | 2011-03-24 |
| KR20120091088A (ko) | 2012-08-17 |
| EP2464225A4 (en) | 2013-03-27 |
| EP2464225B8 (en) | 2017-08-23 |
| CN102548406B (zh) | 2015-04-08 |
| CA2771988C (en) | 2016-07-05 |
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