TWI262181B - Florfenicol prodrug having improved water solubility - Google Patents
Florfenicol prodrug having improved water solubility Download PDFInfo
- Publication number
- TWI262181B TWI262181B TW093139689A TW93139689A TWI262181B TW I262181 B TWI262181 B TW I262181B TW 093139689 A TW093139689 A TW 093139689A TW 93139689 A TW93139689 A TW 93139689A TW I262181 B TWI262181 B TW I262181B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- group
- phosphate
- chloramphenicol
- acid
- Prior art date
Links
- 239000000651 prodrug Substances 0.000 title claims abstract description 47
- 229940002612 prodrug Drugs 0.000 title claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract description 20
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 title abstract description 6
- 229960003760 florfenicol Drugs 0.000 title abstract 3
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 68
- 229960005091 chloramphenicol Drugs 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 52
- 229910019142 PO4 Inorganic materials 0.000 claims description 50
- 235000021317 phosphate Nutrition 0.000 claims description 50
- 239000010452 phosphate Substances 0.000 claims description 48
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 44
- -1 fluoromethanesulfonyl Chemical group 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 31
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- 150000001768 cations Chemical class 0.000 claims description 23
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/094—Esters of phosphoric acids with arylalkanols
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US53222703P | 2003-12-23 | 2003-12-23 |
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| PE20050386A1 (es) | 2003-05-29 | 2005-06-23 | Schering Plough Ltd | Composiciones farmaceuticas de florfenicol |
| US7439268B2 (en) | 2003-07-18 | 2008-10-21 | Idexx Laboratories | Compositions containing prodrugs of florfenicol and methods of use |
| CA2550660C (en) * | 2003-12-23 | 2011-03-15 | Schering-Plough Ltd. | Florfenicol prodrug having improved water solubility |
| WO2005066119A2 (en) * | 2003-12-31 | 2005-07-21 | Schering-Plough Ltd. | Antibacterial 1-(4-mono-and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoropropanols and preparation thereof |
| KR20070054691A (ko) | 2004-09-23 | 2007-05-29 | 쉐링-프라우 리미티드 | 신규한 트리플루오로메탄설폰아미드 옥심 에테르 유도체를사용하여 동물의 기생충 방제 |
| EP1811841B1 (en) | 2004-11-19 | 2009-10-28 | Schering-Plough Ltd. | Control of parasites in animals by the use of parasiticidal 2-phenyl-3-(1h-pyrrol-2-yl) acrylonitrile derivatives |
| MX2007015729A (es) * | 2005-06-09 | 2008-02-21 | Schering Plough Ltd | Control de parasitos en animales con derivados de n-[(feniloxi)fenil]-1,1,1-trifluorometansulfonamida y de n[(fenilsulfanil)fenil]-1,1,1-trifluorometansulfonamida. |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| EP2091909A1 (en) | 2006-12-13 | 2009-08-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
| MX2009006468A (es) * | 2006-12-13 | 2009-08-20 | Schering Plough Ltd | Profarmacos de fenicol solubles en agua en un sistema de vehiculo lipofilico. |
| WO2008076256A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| CA2971008A1 (en) | 2007-06-27 | 2008-12-31 | E. I. Du Pont De Nemours And Company | Animal pest control method |
| US20090170954A1 (en) * | 2007-12-14 | 2009-07-02 | Schering-Plough Ltd. | Process for Recovering Florfenicol and Florfenicol Analogs |
| CN102131772B (zh) * | 2008-07-30 | 2015-03-11 | 英特威国际有限公司 | 用作氟苯尼考的中间体的*唑啉-保护的氨基二醇化合物的制备方法 |
| EP2462125A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
| CN102686570A (zh) | 2009-08-05 | 2012-09-19 | 杜邦公司 | 介离子杀虫剂 |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| CN103649097A (zh) | 2011-05-02 | 2014-03-19 | 佐蒂斯有限责任公司 | 用作抗菌剂的新型头孢菌素类 |
| BR112013032813A2 (pt) | 2011-06-20 | 2016-08-16 | Du Pont | composto de fórmula, composição e método para o tratamento, controle, prevenção ou proteção dos animais contra a infecção por helmintos |
| AU2012346433A1 (en) | 2011-11-28 | 2014-05-08 | E. I. Du Pont De Nemours And Company | N- (4 -quinolinylmethyl) sulfonamide derivatives and their use as anthelmintics |
| WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
| WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
| CN103242363B (zh) * | 2013-04-18 | 2015-10-28 | 湖北龙翔药业有限公司 | 氟苯尼考磷酸二酯及盐及其制备方法 |
| CN103923118A (zh) * | 2014-04-08 | 2014-07-16 | 张家港威胜生物医药有限公司 | 一种水溶性氟苯尼考衍生物的合成方法 |
| CN105111234B (zh) * | 2015-09-23 | 2017-05-17 | 河北远征禾木药业有限公司 | 一种氟苯尼考磷酸酯的合成方法 |
| CN110078729A (zh) * | 2019-06-11 | 2019-08-02 | 石家庄学院 | 一种水溶性氟苯尼考前药及其制备方法 |
| CN115286544A (zh) * | 2022-10-08 | 2022-11-04 | 世华合创生物技术开发(山东)有限公司 | 一种氟苯尼考衍生物、制备方法及其在抗细菌感染的应用 |
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|---|---|---|---|---|
| US2776992A (en) * | 1956-03-14 | 1957-01-08 | Du Pont | Trifluoromethylsulfonylphenyldichloracetamidopropandiol |
| US4235892A (en) * | 1979-02-05 | 1980-11-25 | Schering Corporation, Patent Dept. | 1-Aryl-2-acylamido-3-fluoro-1-propanols, methods for their use as antibacterial agents and compositions useful therefor |
| FR2562543B1 (fr) * | 1984-04-10 | 1987-09-25 | Elf Aquitaine | Nouveaux phosphonites cycliques, leur preparation et applications |
| US5352832A (en) * | 1992-12-18 | 1994-10-04 | Schering Corporation | Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates |
| US6864240B1 (en) * | 1999-06-15 | 2005-03-08 | Elan Pharmaceuticals, Inc. | Dipeptide inhibitors of β-secretase |
| US6670344B2 (en) | 2000-09-14 | 2003-12-30 | Bristol-Myers Squibb Company | Combretastatin A-4 phosphate prodrug mono- and di-organic amine salts, mono- and di- amino acid salts, and mono- and di-amino acid ester salts |
| EP1395265A4 (en) | 2001-06-15 | 2005-08-10 | Univ Arizona | COMBRETASTATIN A-3 PRO MEDICINE |
| TW200406372A (en) * | 2002-03-08 | 2004-05-01 | Schering Plough Ltd | Novel florfenicol-type antibiotics |
| US7439268B2 (en) * | 2003-07-18 | 2008-10-21 | Idexx Laboratories | Compositions containing prodrugs of florfenicol and methods of use |
| CA2550660C (en) | 2003-12-23 | 2011-03-15 | Schering-Plough Ltd. | Florfenicol prodrug having improved water solubility |
| WO2005066119A2 (en) | 2003-12-31 | 2005-07-21 | Schering-Plough Ltd. | Antibacterial 1-(4-mono-and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoropropanols and preparation thereof |
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2004
- 2004-12-20 CA CA2550660A patent/CA2550660C/en not_active Expired - Fee Related
- 2004-12-20 AR ARP040104805A patent/AR046970A1/es not_active Application Discontinuation
- 2004-12-20 US US11/016,794 patent/US7153842B2/en not_active Expired - Lifetime
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- 2004-12-20 BR BRPI0418133-6A patent/BRPI0418133A2/pt not_active IP Right Cessation
- 2004-12-20 JP JP2006547183A patent/JP4719160B2/ja not_active Expired - Fee Related
- 2004-12-20 KR KR1020067012460A patent/KR20060111605A/ko not_active Withdrawn
- 2004-12-20 CN CN200480038867A patent/CN100579532C/zh not_active Expired - Lifetime
- 2004-12-20 MX MXPA06007215A patent/MXPA06007215A/es active IP Right Grant
- 2004-12-20 EP EP04814736.7A patent/EP1696934B1/en not_active Expired - Lifetime
- 2004-12-20 NZ NZ547592A patent/NZ547592A/xx not_active IP Right Cessation
- 2004-12-20 WO PCT/US2004/042591 patent/WO2005063257A1/en not_active Ceased
- 2004-12-20 TW TW093139689A patent/TWI262181B/zh not_active IP Right Cessation
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2005
- 2005-01-03 PE PE2005000020A patent/PE20050822A1/es not_active Application Discontinuation
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2006
- 2006-06-15 IL IL176342A patent/IL176342A/en not_active IP Right Cessation
- 2006-06-22 EC EC2006006670A patent/ECSP066670A/es unknown
- 2006-06-22 ZA ZA200605165A patent/ZA200605165B/xx unknown
- 2006-07-12 NO NO20063244A patent/NO20063244L/no not_active Application Discontinuation
- 2006-08-29 US US11/511,810 patent/US7572777B2/en not_active Expired - Lifetime
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2009
- 2009-07-23 IL IL200041A patent/IL200041A0/en unknown
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2011
- 2011-02-23 JP JP2011037689A patent/JP2011148804A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
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| CA2550660C (en) | 2011-03-15 |
| ZA200605165B (en) | 2007-12-27 |
| IL200041A0 (en) | 2010-04-15 |
| JP4719160B2 (ja) | 2011-07-06 |
| US20050182031A1 (en) | 2005-08-18 |
| MXPA06007215A (es) | 2006-08-18 |
| PE20050822A1 (es) | 2005-10-01 |
| CA2550660A1 (en) | 2005-07-14 |
| WO2005063257A1 (en) | 2005-07-14 |
| AU2004308913A1 (en) | 2005-07-14 |
| NZ547592A (en) | 2009-07-31 |
| TW200533640A (en) | 2005-10-16 |
| RU2006126519A (ru) | 2008-01-27 |
| AR046970A1 (es) | 2006-01-04 |
| US7153842B2 (en) | 2006-12-26 |
| IL176342A0 (en) | 2006-10-05 |
| KR20060111605A (ko) | 2006-10-27 |
| CN100579532C (zh) | 2010-01-13 |
| ECSP066670A (es) | 2006-10-25 |
| BRPI0418133A2 (pt) | 2009-03-24 |
| IL176342A (en) | 2011-08-31 |
| CN1897954A (zh) | 2007-01-17 |
| JP2007516286A (ja) | 2007-06-21 |
| US7572777B2 (en) | 2009-08-11 |
| US20070021387A1 (en) | 2007-01-25 |
| EP1696934B1 (en) | 2013-05-29 |
| NO20063244L (no) | 2006-09-20 |
| EP1696934A1 (en) | 2006-09-06 |
| JP2011148804A (ja) | 2011-08-04 |
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