JP2007516286A5 - - Google Patents
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- Publication number
- JP2007516286A5 JP2007516286A5 JP2006547183A JP2006547183A JP2007516286A5 JP 2007516286 A5 JP2007516286 A5 JP 2007516286A5 JP 2006547183 A JP2006547183 A JP 2006547183A JP 2006547183 A JP2006547183 A JP 2006547183A JP 2007516286 A5 JP2007516286 A5 JP 2007516286A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- florfenicol
- group
- pharmaceutical composition
- pharmaceutically acceptable
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 229960003760 florfenicol Drugs 0.000 claims 29
- 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 claims 23
- 239000000651 prodrug Substances 0.000 claims 16
- 229940002612 prodrug Drugs 0.000 claims 16
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 229910019142 PO4 Inorganic materials 0.000 claims 14
- 239000010452 phosphate Substances 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 150000001768 cations Chemical class 0.000 claims 10
- -1 florfenicol phosphate ester Chemical class 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000002253 acid Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 5
- 239000007864 aqueous solution Substances 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002091 cationic group Chemical group 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- SIVFIIFHKNSTRW-UHFFFAOYSA-N 2-[amino-[(2-methylpropan-2-yl)oxy]phosphanyl]oxy-2-methylpropane Chemical compound CC(C)(C)OP(N)OC(C)(C)C SIVFIIFHKNSTRW-UHFFFAOYSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 229960005274 benzocaine Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229960003194 meglumine Drugs 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229960004919 procaine Drugs 0.000 claims 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53222703P | 2003-12-23 | 2003-12-23 | |
| US60/532,227 | 2003-12-23 | ||
| PCT/US2004/042591 WO2005063257A1 (en) | 2003-12-23 | 2004-12-20 | Florfenicol prodrug having improved water solubility |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011037689A Division JP2011148804A (ja) | 2003-12-23 | 2011-02-23 | 改善された水溶性を有するフロルフェニコールプロドラッグ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007516286A JP2007516286A (ja) | 2007-06-21 |
| JP2007516286A5 true JP2007516286A5 (enExample) | 2008-02-07 |
| JP4719160B2 JP4719160B2 (ja) | 2011-07-06 |
Family
ID=34738768
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006547183A Expired - Fee Related JP4719160B2 (ja) | 2003-12-23 | 2004-12-20 | 改善された水溶性を有するフロルフェニコールプロドラッグ |
| JP2011037689A Withdrawn JP2011148804A (ja) | 2003-12-23 | 2011-02-23 | 改善された水溶性を有するフロルフェニコールプロドラッグ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011037689A Withdrawn JP2011148804A (ja) | 2003-12-23 | 2011-02-23 | 改善された水溶性を有するフロルフェニコールプロドラッグ |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7153842B2 (enExample) |
| EP (1) | EP1696934B1 (enExample) |
| JP (2) | JP4719160B2 (enExample) |
| KR (1) | KR20060111605A (enExample) |
| CN (1) | CN100579532C (enExample) |
| AR (1) | AR046970A1 (enExample) |
| BR (1) | BRPI0418133A2 (enExample) |
| CA (1) | CA2550660C (enExample) |
| EC (1) | ECSP066670A (enExample) |
| IL (2) | IL176342A (enExample) |
| MX (1) | MXPA06007215A (enExample) |
| NO (1) | NO20063244L (enExample) |
| NZ (1) | NZ547592A (enExample) |
| PE (1) | PE20050822A1 (enExample) |
| RU (1) | RU2006126519A (enExample) |
| TW (1) | TWI262181B (enExample) |
| WO (1) | WO2005063257A1 (enExample) |
| ZA (1) | ZA200605165B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP1696934B1 (en) * | 2003-12-23 | 2013-05-29 | 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 |
| DE602005009381D1 (de) | 2004-09-23 | 2008-10-09 | Schering Plough Ltd | Bekämpfung von parasiten in tieren durch verwendung neuer trifluormethansulfonanilidoximetherderivate |
| JP4750126B2 (ja) | 2004-11-19 | 2011-08-17 | シェーリング−プラウ・リミテッド | 殺寄生虫薬２−フェニル−３−（１ｈ−ピロール−２−イル）アクリロニトリル誘導体の使用による動物における寄生虫の制御 |
| EP1890547A2 (en) * | 2005-06-09 | 2008-02-27 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| WO2008076256A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| WO2008076261A2 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble phenicol prodrugs in a lipophilic vehicle system |
| CN101605756A (zh) * | 2006-12-13 | 2009-12-16 | 先灵-普劳有限公司 | 氟苯尼考及其类似物的水溶性前药 |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| DK2182945T3 (en) | 2007-06-27 | 2015-11-16 | Du Pont | PROCEDURE TO COMBAT PESTS WITH ANIMALS |
| PE20091171A1 (es) * | 2007-12-14 | 2009-08-03 | Schering Plough Ltd | Proceso para recuperar florfenicol y analogos de florfenicol |
| WO2010014566A2 (en) * | 2008-07-30 | 2010-02-04 | Intervet International B.V. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
| AU2010279587A1 (en) | 2009-08-05 | 2012-02-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| EP2461684A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| MX2013012820A (es) | 2011-05-02 | 2014-02-10 | Zoetis Llc | Cefalosporinas novedosas utiles como agentes antibacteriales. |
| US20140113934A1 (en) | 2011-06-20 | 2014-04-24 | E I Du Pont De Nemours And Company | Heterocyclic compounds for treating helminth infections |
| JP2015502936A (ja) | 2011-11-28 | 2015-01-29 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | スルホンアミド駆虫薬 |
| 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 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7547686B2 (en) | 2001-06-15 | 2009-06-16 | Arizona Board of Regents, a body corporate of the State of Arizona, Acting for and on Behalf of the Arizona State University | Combretastatin A-3 prodrug |
| AU2003249503A1 (en) * | 2002-03-08 | 2003-09-29 | 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 |
| EP1696934B1 (en) * | 2003-12-23 | 2013-05-29 | 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 |
-
2004
- 2004-12-20 EP EP04814736.7A patent/EP1696934B1/en not_active Expired - Lifetime
- 2004-12-20 US US11/016,794 patent/US7153842B2/en not_active Expired - Lifetime
- 2004-12-20 CN CN200480038867A patent/CN100579532C/zh not_active Expired - Lifetime
- 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 RU RU2006126519/04A patent/RU2006126519A/ru not_active Application Discontinuation
- 2004-12-20 MX MXPA06007215A patent/MXPA06007215A/es active IP Right Grant
- 2004-12-20 NZ NZ547592A patent/NZ547592A/xx not_active IP Right Cessation
- 2004-12-20 TW TW093139689A patent/TWI262181B/zh not_active IP Right Cessation
- 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 WO PCT/US2004/042591 patent/WO2005063257A1/en not_active Ceased
-
2005
- 2005-01-03 PE PE2005000020A patent/PE20050822A1/es not_active Application Discontinuation
-
2006
- 2006-06-15 IL IL176342A patent/IL176342A/en not_active IP Right Cessation
- 2006-06-22 ZA ZA200605165A patent/ZA200605165B/xx unknown
- 2006-06-22 EC EC2006006670A patent/ECSP066670A/es 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
-
2009
- 2009-07-23 IL IL200041A patent/IL200041A0/en unknown
-
2011
- 2011-02-23 JP JP2011037689A patent/JP2011148804A/ja not_active Withdrawn
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