IL263167B - An antifungal composition comprising 2-(1,5-dimethyl-3-phenyl-1h-pyrrol-2-yl)-n-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2-oxoacetamide for oral administration - Google Patents
An antifungal composition comprising 2-(1,5-dimethyl-3-phenyl-1h-pyrrol-2-yl)-n-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2-oxoacetamide for oral administrationInfo
- Publication number
- IL263167B IL263167B IL263167A IL26316718A IL263167B IL 263167 B IL263167 B IL 263167B IL 263167 A IL263167 A IL 263167A IL 26316718 A IL26316718 A IL 26316718A IL 263167 B IL263167 B IL 263167B
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- pharmaceutical composition
- phenyl
- pharmaceutically acceptable
- Prior art date
Links
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- 229940121375 antifungal agent Drugs 0.000 title description 6
- 230000000843 anti-fungal effect Effects 0.000 title 1
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
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- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 claims description 40
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- DSDAICPXUXPBCC-MWDJDSKUSA-N trimethyl-β-cyclodextrin Chemical compound COC[C@H]([C@H]([C@@H]([C@H]1OC)OC)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)OC)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)OC)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)OC)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)OC)O3)[C@H](OC)[C@H]2OC)COC)O[C@@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@@H]3O[C@@H]1COC DSDAICPXUXPBCC-MWDJDSKUSA-N 0.000 description 1
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Classifications
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- C—CHEMISTRY; METALLURGY
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1609222.3A GB201609222D0 (en) | 2016-05-25 | 2016-05-25 | Pharmaceutical formulation |
| PCT/GB2017/051494 WO2017203270A1 (en) | 2016-05-25 | 2017-05-25 | Pharmaceutical formulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL263167A IL263167A (en) | 2018-12-31 |
| IL263167B true IL263167B (en) | 2022-07-01 |
Family
ID=56369959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL263167A IL263167B (en) | 2016-05-25 | 2017-05-25 | An antifungal composition comprising 2-(1,5-dimethyl-3-phenyl-1h-pyrrol-2-yl)-n-(4-(4-(5-fluoropyrimidin-2-yl)piperazin-1-yl)phenyl)-2-oxoacetamide for oral administration |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US10973821B2 (OSRAM) |
| EP (1) | EP3463365B1 (OSRAM) |
| JP (1) | JP7141108B2 (OSRAM) |
| KR (1) | KR102464150B1 (OSRAM) |
| CN (1) | CN109982704B (OSRAM) |
| AU (1) | AU2017270942B2 (OSRAM) |
| CA (1) | CA3024771A1 (OSRAM) |
| CY (1) | CY1124733T1 (OSRAM) |
| DK (1) | DK3463365T3 (OSRAM) |
| ES (1) | ES2888951T3 (OSRAM) |
| GB (1) | GB201609222D0 (OSRAM) |
| HR (1) | HRP20211795T1 (OSRAM) |
| HU (1) | HUE056129T2 (OSRAM) |
| IL (1) | IL263167B (OSRAM) |
| LT (1) | LT3463365T (OSRAM) |
| MA (1) | MA45126A (OSRAM) |
| MX (1) | MX382199B (OSRAM) |
| MY (1) | MY197663A (OSRAM) |
| PL (1) | PL3463365T3 (OSRAM) |
| PT (1) | PT3463365T (OSRAM) |
| RU (1) | RU2760681C2 (OSRAM) |
| SG (1) | SG11201810323RA (OSRAM) |
| SI (1) | SI3463365T1 (OSRAM) |
| WO (1) | WO2017203270A1 (OSRAM) |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201609222D0 (en) * | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
| US20230338294A1 (en) * | 2020-04-26 | 2023-10-26 | Apollomics Inc. | Novel pharmaceutical formulation for c-met inhibitor |
| CN113429396A (zh) * | 2021-06-08 | 2021-09-24 | 深圳市祥根生物医药有限公司 | 一种五元杂芳环衍生物及其制备方法和用途 |
Family Cites Families (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1051723A (OSRAM) | 1962-04-27 | |||
| US3202654A (en) | 1962-04-27 | 1965-08-24 | Bristol Myers Co | 6-[alpha-hydroxy-and alpha-amino-alpha-pyrrolylacetamido] penicillanic acids and salts thereof |
| US3252970A (en) | 1963-02-27 | 1966-05-24 | Ciba Geigy Corp | Aromatization |
| BE631632A (OSRAM) | 1963-04-26 | |||
| US3268558A (en) | 1964-11-05 | 1966-08-23 | Ortho Pharma Corp | 1-r-2, 4-dinitropyrroles |
| US3458515A (en) | 1966-07-21 | 1969-07-29 | American Home Prod | Piperazine substituted pyrroles |
| GB1208014A (en) | 1967-03-23 | 1970-10-07 | Glaxo Lab Ltd | Cephalosporins |
| US3573294A (en) | 1968-03-14 | 1971-03-30 | Glaxo Lab Ltd | 7 - (arylglyoxamido)cephalosporanic acids and their salts and alpha-carbonyl derivatives |
| BE790747A (fr) | 1971-10-30 | 1973-02-15 | Whitefin Holding Sa | Stereo-isomeres du 1-(1'-(0-chloro-benzyl)-pyrrol-2'-yl) -2-dibutyl sec.-amino-ethanol et procede pour leur preparation |
| GB1476503A (en) | 1973-06-21 | 1977-06-16 | Sterling Drug Inc | 1-arylamino-and 1-arylimino-pyrroles and preparation thereof |
| BE848465A (fr) | 1976-11-18 | 1977-03-16 | Stereo-isomeres de 1-(1'-benzyl-2' pyrryl)-2-disec.butylaminoethanols a activite analgesique et preparations pharmaceutiques qui les contiennent | |
| US4316900A (en) | 1977-10-05 | 1982-02-23 | Ciba-Geigy Corporation | Piperazinopyrrolobenzodiazepines |
| JPS57142966A (en) | 1981-02-27 | 1982-09-03 | Sagami Chem Res Center | (1-alkyl-2-pyrrolyl)glyoxylic acid amide derivative |
| JPS57144255A (en) | 1981-03-03 | 1982-09-06 | Sagami Chem Res Center | Alpha-methylthio(1-alkyl-2-pyrrolyl)acetamide derivative |
| US4761424A (en) | 1985-10-01 | 1988-08-02 | Warner-Lambert Company | Enolamides, pharmaceutical compositions and methods for treating inflammation |
| FR2601368B1 (fr) | 1986-07-08 | 1989-04-07 | Synthelabo | Derives de nitrofuranne, leur preparation et leur application en therapeutique. |
| AU650953B2 (en) | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| US5637592A (en) | 1994-07-12 | 1997-06-10 | Janssen Pharmaceutica N.V. | Acyl derivatives of azolones |
| CA2195570A1 (en) | 1994-07-21 | 1996-02-08 | Robert Delane Dillard | Indolizine spla2 inhibitors |
| KR19990008109A (ko) | 1995-04-28 | 1999-01-25 | 나가사까 겐지로 | 1,4-이치환 피페리딘 유도체 |
| EP0747756B1 (en) | 1995-06-06 | 2000-05-24 | Agfa-Gevaert N.V. | Photographic materials |
| JPH09249669A (ja) | 1996-03-13 | 1997-09-22 | Ono Pharmaceut Co Ltd | 縮合ピロール誘導体、およびそれらを有効成分として含有する薬剤 |
| PT986403E (pt) | 1997-06-13 | 2004-04-30 | Cydex Inc | Composicao com um tempo de vida de armazenagem prolongado compreendendo a ciclodextrina e drogas ou prodrogas que se decompoem em compostos insoluveis em agua |
| DE69837903T2 (de) | 1997-08-11 | 2008-02-14 | Pfizer Products Inc., Groton | Feste pharmazeutische Dispersionen mit erhöhter Bioverfügbarkeit |
| US6331537B1 (en) | 1998-06-03 | 2001-12-18 | Gpi Nil Holdings, Inc. | Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds |
| WO1999062881A1 (en) | 1998-06-03 | 1999-12-09 | Gpi Nil Holdings, Inc. | Aza-heterocyclic compounds used to treat neurological disorders and hair loss |
| EP1027887B1 (en) | 1999-02-10 | 2008-08-13 | Pfizer Products Inc. | Matrix controlled release device |
| MXPA01011117A (es) | 1999-05-04 | 2002-06-04 | Janssen Pharmaceutica Nv | Eteres antifungicos. |
| AU6438800A (en) | 1999-07-30 | 2001-02-19 | Norbert Heske | Cannula system for introducing endoscopic tools in a human or animal body |
| CZ20022047A3 (cs) | 1999-12-23 | 2003-09-17 | Pfizer Products Inc. | Farmaceutické kompozice poskytující zvýšenou koncentraci léčiva |
| GB0011089D0 (en) | 2000-05-08 | 2000-06-28 | Black James Foundation | Gastrin and cholecystokinin receptor ligands (11) |
| US7202239B2 (en) | 2001-04-12 | 2007-04-10 | Wyeth | Cyclohexylphenyl carboxamides tocolytic oxytocin receptor antagonists |
| US6825201B2 (en) | 2001-04-25 | 2004-11-30 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic amidopiperazine derivatives |
| EP1399442B1 (en) | 2001-06-06 | 2006-08-09 | Vertex Pharmaceuticals Incorporated | Cak inhibitors and uses thereof |
| ES2389027T3 (es) | 2001-06-20 | 2012-10-22 | Daiichi Sankyo Company, Limited | Derivados de diamina |
| TW200306819A (en) | 2002-01-25 | 2003-12-01 | Vertex Pharma | Indazole compounds useful as protein kinase inhibitors |
| JP4865989B2 (ja) | 2002-02-01 | 2012-02-01 | ベンド・リサーチ・インコーポレーテッド | 改良された噴霧乾燥装置を使用する均質な噴霧乾燥された固体の非晶質薬物分散物を製造する方法 |
| BR0307515A (pt) | 2002-02-01 | 2004-12-07 | Pfizer Prod Inc | Método para fabricar dispersões de drogas amorfas sólidas secas por aspersão homogêneas usando bicos de pressão |
| US20040162298A1 (en) | 2002-02-23 | 2004-08-19 | Hsu-Tso Ho | Method of treating HIV infection by preventing interaction of CD4 and gp120 |
| KR20060021278A (ko) | 2002-08-15 | 2006-03-07 | 윤킹 리우 | 고체 나노미터 의약 및 이의 제조방법 |
| US20050032871A1 (en) | 2002-09-03 | 2005-02-10 | Sugen, Inc. | Sulfonylated pyrrole-2-indolinone derivatives as kinase inhibitors |
| WO2004082606A2 (en) | 2003-03-13 | 2004-09-30 | Synta Pharmaceuticals Corp. | Fused pyrrole compounds |
| FR2854079B1 (fr) | 2003-04-25 | 2007-11-30 | Pf Medicament | Procede de preparation de complexes moleculaires |
| CL2004001884A1 (es) | 2003-08-04 | 2005-06-03 | Pfizer Prod Inc | Procedimiento de secado por pulverizacion para la formacion de dispersiones solidas amorfas de un farmaco y polimeros. |
| BRPI0415773A (pt) | 2003-10-24 | 2006-12-26 | Schering Ag | derivados de indolinona e sua aplicação no tratamento de estados de doença tais como cáncer |
| EP1753402B1 (en) | 2004-05-28 | 2008-10-01 | Pfizer Products Incorporated | Pharmaceutical compositions with enhanced performance comprising a hpmca polymer |
| US20060058286A1 (en) | 2004-09-16 | 2006-03-16 | Mark Krystal | Methods of treating HIV infection |
| WO2006082518A1 (en) | 2005-02-03 | 2006-08-10 | Pfizer Products Inc. | Pharmaceutical compositions with enhanced performance |
| US7842810B2 (en) | 2005-03-31 | 2010-11-30 | Janssen Pharmaceutica, Nv | Bicyclic pyrazole compounds as antibacterial agents |
| AR053713A1 (es) | 2005-04-20 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos heterociclicos y sus usos como agentes terapeuticos |
| US8486962B2 (en) | 2005-05-18 | 2013-07-16 | F2G Ltd. | Antifungal agents |
| US20090176837A1 (en) | 2005-07-12 | 2009-07-09 | Sony Corporation | Compounds with activity at retinoic acid receptors |
| WO2007015866A2 (en) | 2005-07-20 | 2007-02-08 | Kalypsys, Inc. | Inhibitors of p38 kinase and methods of treating inflammatory disorders |
| NZ571934A (en) | 2006-03-20 | 2012-05-25 | Vertex Pharma | Methods of spray drying formulations of vx-950 (telaprevir) |
| US8343548B2 (en) | 2006-08-08 | 2013-01-01 | Shin-Etsu Chemical Co., Ltd. | Solid dosage form comprising solid dispersion |
| US20080118500A1 (en) | 2006-11-16 | 2008-05-22 | Taiwan Liposome Company | Sustained releasing composition via local injection for treating eye diseases |
| GB0623209D0 (en) | 2006-11-21 | 2007-01-03 | F2G Ltd | Antifungal agents |
| CN101622302B (zh) | 2007-01-26 | 2013-01-23 | Isp投资公司 | 生产喷雾干燥产品的制剂工艺方法 |
| CN101260086B (zh) | 2007-03-06 | 2011-08-10 | 中国科学院上海药物研究所 | 蛋白酪氨酸磷酸酯酶1b抑制剂及其制备方法和用途 |
| GB0710121D0 (en) | 2007-05-25 | 2007-07-04 | F2G Ltd | Antifungal agents |
| US20100215747A1 (en) | 2007-07-13 | 2010-08-26 | Corey Jay Bloom | Nanoparticles comprising ionizable, poorly water soluble cellulosic polymers |
| EP2626361B1 (en) * | 2008-04-24 | 2014-10-15 | F2G Limited | Pyrrole antifungal agents |
| GB0809773D0 (en) | 2008-05-29 | 2008-07-09 | F2G Ltd | Antifungal combination therapy |
| US20100093872A1 (en) | 2008-10-15 | 2010-04-15 | Erimos Pharmaceuticals Llc | Stable aqueous formulations of water insoluble or poorly soluble drugs |
| US20120196919A1 (en) | 2009-04-28 | 2012-08-02 | New York University | Ex-vivo treatment of immunological disorders with pkc-theta inhibitors |
| EP2579896B1 (en) | 2010-06-14 | 2016-07-20 | Dow Global Technologies LLC | Hydroxypropyl methyl cellulose acetate succinate with enhanced acetate and succinate substitution |
| WO2012031129A2 (en) | 2010-09-03 | 2012-03-08 | Bend Research, Inc. | Spray-drying apparatus and methods of using the same |
| JPWO2012060448A1 (ja) | 2010-11-05 | 2014-05-12 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 抗真菌剤としての併用医薬組成物 |
| US20120308662A1 (en) | 2011-06-01 | 2012-12-06 | Nitto Denko Corporation | Particulate preparation and method for producing the same |
| CA2852716C (en) | 2011-11-29 | 2015-11-17 | Jurox Pty Ltd | Methods of preserving injectable pharmaceutical compositions comprising a cyclodextrin and a hydrophobic drug |
| WO2013154607A1 (en) | 2012-04-11 | 2013-10-17 | Dow Global Technologies Llc | Esterified cellulose ethers having a specific substituent distribution |
| CN104736572B (zh) | 2012-08-24 | 2017-09-05 | 陶氏环球技术有限责任公司 | 部分交联的酯化纤维素醚 |
| JP6215945B2 (ja) | 2012-08-24 | 2017-10-18 | ダウ グローバル テクノロジーズ エルエルシー | 新規ヒドロキシアルキルメチルセルロースアセテートサクシネート |
| AU2014210103B2 (en) | 2013-01-22 | 2018-09-06 | F. Hoffmann-La Roche Ag | Pharmaceutical composition with improved bioavailability |
| WO2015007759A1 (en) | 2013-07-19 | 2015-01-22 | Boehringer Ingelheim Vetmedica Gmbh | Etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition |
| HRP20251029T1 (hr) | 2013-07-19 | 2025-10-24 | Boehringer Ingelheim Vetmedica Gmbh | Konzervirani eterificirani derivati ciklodekstrina koji sadrže tekući vodeni farmaceutski pripravak |
| KR20160093611A (ko) | 2013-12-05 | 2016-08-08 | 알라이즈 바이오시스템즈 게엠베하 | 경구 투여를 위한 약물 제제의 제조 방법 |
| PT107568B (pt) | 2014-03-31 | 2018-11-05 | Hovione Farm S A | Processo de secagem por atomização para a produção de pós com propriedades melhoradas. |
| LT3221308T (lt) | 2014-11-21 | 2018-12-27 | F2G Limited | Priešgrybeliniai agentai |
| GB201609222D0 (en) * | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
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2016
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2017
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- 2017-05-25 HR HRP20211795TT patent/HRP20211795T1/hr unknown
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- 2017-05-25 PL PL17728590T patent/PL3463365T3/pl unknown
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- 2017-05-25 MX MX2018014232A patent/MX382199B/es unknown
- 2017-05-25 DK DK17728590.5T patent/DK3463365T3/da active
- 2017-05-25 LT LTEPPCT/GB2017/051494T patent/LT3463365T/lt unknown
- 2017-05-25 US US16/303,999 patent/US10973821B2/en active Active
- 2017-05-25 CN CN201780046136.8A patent/CN109982704B/zh active Active
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- 2017-05-25 MY MYPI2018002103A patent/MY197663A/en unknown
- 2017-05-25 KR KR1020187037061A patent/KR102464150B1/ko active Active
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- 2017-05-25 EP EP17728590.5A patent/EP3463365B1/en active Active
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