DK2999476T3 - Morfiske former af hexadecyloxypropyl-phosphonatestere - Google Patents
Morfiske former af hexadecyloxypropyl-phosphonatestere Download PDFInfo
- Publication number
- DK2999476T3 DK2999476T3 DK14861700.4T DK14861700T DK2999476T3 DK 2999476 T3 DK2999476 T3 DK 2999476T3 DK 14861700 T DK14861700 T DK 14861700T DK 2999476 T3 DK2999476 T3 DK 2999476T3
- Authority
- DK
- Denmark
- Prior art keywords
- compound
- morphic
- methanol
- composition
- ray diffraction
- Prior art date
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Classifications
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- 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
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Claims (16)
1. Morfisk Form II af phosphonsyre, [[(S)-2-(4-amino-2-oxo-l(2H)-pyrimidinyl)-l-(hydroxymethyl)ethoxy]methyl]mono[3-(hexade cyloxy)propyl] ester (Forbindelse 1) kendetegnet ved: (i) et røntgendiffraktionsmønster med seks peaks udtrykt i grader 20 ved 2,81, 5,63, 19,00, 19,57, 22,76 og 24,70 ± 0,2; og (ii) et differentiel scanningskalorimetritermogram, der viser en endoterm ved 41-43 °C; overlappende endotermer ved 90 og 95 °C og en endoterm ved 196 °C.
2. Morfisk Form II ifølge krav 1 kendetegnet ved et røntgendiffraktionsmønster med syv eller flere peaks udtrykt i grader 20 (±0,2) valgt fra 2,81, 5,63, 11,30, 12,05, 13,22, 13,45, 13,81, 14,32, 14,92, 15,64, 16,25, 16,41, 17,00, 17,67, 17,87, 18,15, 18,35, 18,50, 19,00, 19,57, 19,85, 20,22, 20,96, 21,06, 21,89, 22,76, 23,70, 23,95, 24,32, 24,70, 25,54, 26,12, 26,52, 26,81, 27,07, 27,48, 27,71, 29,11, 29,36 og 29,61.
3. Morfisk Form II ifølge krav 1 fremstillet ved en oprensningsproces, der omfatter rekrystallisering af et præparat af phosphonsyre, [[(S)-2-(4-amino-2-oxo-l(2H)-pyrimidinyl)-l-(hydroxymethyl)ethoxy]methyl]mono[3-(hexade cyloxy)propyl] ester (Forbindelse 1) fra methanol-vand med et methanol: vand-forhold på mellem 97:3 og 99:1.
4. Fremgangsmåde til fremstilling af Form II af phosphonsyre, [[(S)-2-(4-amino-2-oxo-l(2H)-pyrimidinyl)-l-(hydroxymethyl)ethoxy]methyl]mono[3-(hexade cyloxy)propyl] ester ifølge krav 1, der omfatter trinnet med kombinering af (S) -N1 - [ (2-hydroxy- 3 -triphenylmethoxy)propyl] cyto sin (Forbindelse 2), P- [ [ [4-methylphenyl) sulfonyl] oxy] methyl] -, mono [3-(hexadecyloxy)propyl] ester, natriumsalt (Forbindelse 4) med magnesiumtert-butoxid og et egnet organisk opløsningsmiddel og krystallisering fra methanol-vand med et methanokvand-forhold på mellem 97:3 og 99:1.
5. Fremgangsmåde ifølge krav 4, hvor Form II er mere eller svarende til 91 % vægt/vægt ren.
6. Fremgangsmåde ifølge krav 4, hvor den morfiske Form II er kendetegnet ved et røntgendiffraktionsmønster med syv eller flere peaks udtrykt i grader 20 (±0,2) valgt fra 2,81, 5,63, 11,30, 12,05, 13,22, 13,45, 13,81, 14,32, 14,92, 15,64, 16,25, 16,41, 17,00, 17,67, 17,87, 18,15, 18,35, 18,50, 19,00, 19,57, 19,85, 20,22, 20,96, 21,06, 21,89, 22,76, 23,70, 23,95, 24,32, 24,70, 25,54, 26,12, 26,52, 26,81, 27,07, 27,48, 27,71, 29,11, 29,36 og 29,61.
7. Fremgangsmåde ifølge krav 4, der endvidere omfatter podning med 0,5 % vægt/vægt, 3 % vægt/vægt eller 7 % vægt/vægt podekrystal ifølge Forbindelse 1.
8. Fremgangsmåde ifølge krav 7, hvor podekrystallet er Form II ifølge krav 1 eller en morfisk Form I med et røntgendiffraktionspeak ved 15,6° 20.
9. Morfisk Form II ifølge krav 1, kendetegnet ved et DSC-termogram ifølge FIG. 15 eller FIG. 16.
10. Fremgangsmåde ifølge krav 4, hvor den morfiske Form II er kendetegnet ved et DSC-termogram ifølge FIG. 15 eller FIG. 16.
11. Sammensætning, der omfatter morfisk Form II ifølge krav 1, kendetegnet ved, at den indeholder mindre end 1,5 % vægt/vægt af amorfe former eller en morfisk Form H med et røntgendiffraktionspeak ved 12,6° 20 eller en morfisk Form I med et røntgendiffraktionspeak ved 15,6° 20.
12. Sammensætning, der omfatter morfisk Form II ifølge krav 1, kendetegnet ved, at sammensætningen indeholder mindre end 2 % vægt/vægt af en hvilken som helst af følgende forbindelser:
og kombinationer deraf.
13. Sammensætning, der omfatter morfisk form II ifølge krav 1, kendetegnet ved, at den indeholder mindre end 2 % vægt/vægt samlede urenheder.
14. Sammensætning af forbindelse 1, der omfatter Form II ifølge krav 1 og morfisk Form H med et røntgendiffraktionspeak at 12,6° 20 og morfisk Form I med et røntgendiffraktionspeak at 15,6° 20.
15. Sammensætning ifølge krav 14, der omfatter mere end 90 % vægt/vægt af Form II.
16. Sammensætning ifølge krav 14, der omfatter mindre end 10 % vægt/vægt af Form H med et røntgendiffraktionspeak ved 12,6° 20 eller Form I med et røntgendiffraktionspeak ved 15,6° 20.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361904857P | 2013-11-15 | 2013-11-15 | |
| PCT/US2014/060185 WO2015073148A1 (en) | 2013-11-15 | 2014-10-10 | Morphic forms of hexadecyloxypropyl-phosphonate esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2999476T3 true DK2999476T3 (da) | 2018-09-03 |
Family
ID=52472937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK14861700.4T DK2999476T3 (da) | 2013-11-15 | 2014-10-10 | Morfiske former af hexadecyloxypropyl-phosphonatestere |
Country Status (15)
| Country | Link |
|---|---|
| US (8) | US8962829B1 (da) |
| EP (1) | EP2999476B1 (da) |
| JP (3) | JP6150949B2 (da) |
| KR (3) | KR20170143010A (da) |
| CN (2) | CN105899215A (da) |
| AU (3) | AU2014349103B2 (da) |
| BR (1) | BR112016010862B1 (da) |
| CA (1) | CA2929593C (da) |
| DK (1) | DK2999476T3 (da) |
| EA (1) | EA031861B1 (da) |
| ES (1) | ES2685819T3 (da) |
| IL (3) | IL302520B1 (da) |
| MX (1) | MX362752B (da) |
| UA (1) | UA116825C2 (da) |
| WO (1) | WO2015073148A1 (da) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012031045A2 (en) * | 2010-08-31 | 2012-03-08 | Chimerix, Inc. | Phosphonate ester derivatives and methods of synthesis thereof |
| SG10201800188SA (en) | 2013-03-15 | 2018-02-27 | Univ California | Acyclic nucleoside phosphonate diesters |
| US8962829B1 (en) * | 2013-11-15 | 2015-02-24 | Chimerix, Inc. | Morphic forms of hexadecyloxypropyl-phosphonate esters and methods of synthesis thereof |
| CN111808136B (zh) | 2014-09-15 | 2024-06-11 | 加利福尼亚大学董事会 | 核苷酸类似物 |
| EP3350191B9 (en) | 2015-09-15 | 2021-12-22 | The Regents of the University of California | Nucleotide analogs |
| AU2017290703B2 (en) * | 2016-06-28 | 2023-03-30 | Emergent Biodefense Operations Lansing Llc | Formulations of brincidofovir |
| WO2020006050A1 (en) | 2018-06-26 | 2020-01-02 | Tsrl, Inc. | Metabolically stable prodrugs |
| US20220135653A1 (en) * | 2020-11-05 | 2022-05-05 | Bravado Pharmaceuticals, LLC | Intranasal Antiviral Therapy for Mucosal Protection Against Virus Infections |
| KR20250052378A (ko) | 2022-07-21 | 2025-04-18 | 안티바 바이오사이언시즈, 인크. | Hpv 감염 및 hpv-유도 신생물의 치료를 위한 조성물 및 투여 형태 |
| CN119462754B (zh) * | 2024-09-30 | 2025-11-07 | 武汉大学中南医院 | 一种布林西多福韦化合物及其制备方法 |
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| JP3116079B2 (ja) * | 1990-08-10 | 2000-12-11 | インスティチュート オブ オーガニック ケミストリ アンド バイオケミストリ アカデミー オブ サイエンス オブ ザ チェコ リパブリック | ヌクレオチドの新規な製法 |
| JP2002528461A (ja) * | 1998-10-23 | 2002-09-03 | ダーウィン・ディスカバリー・リミテッド | 公知ペプチドメタロプロテイナーゼインヒビターの単一形態型 |
| CA2747954C (en) * | 1999-12-03 | 2014-02-25 | The Regents Of The University Of California | Phosphonate compounds |
| US20020022659A1 (en) * | 2000-07-19 | 2002-02-21 | Harris Gregory D. | Crystalline and salt forms of an HIV protease inhibitor |
| EP1667524A4 (en) * | 2003-09-23 | 2009-01-14 | Merck & Co Inc | NEW CRYSTALLINE FORM OF A PHOSPHORIC ACID SALT OF A DIPEPTIDYLPEPTIDASE IV INHIBITOR |
| WO2005087788A2 (en) | 2004-03-04 | 2005-09-22 | The Regents Of The University Of California | Methods for preparation of nucleoside phosphonate esters |
| WO2006014429A2 (en) * | 2004-07-02 | 2006-02-09 | University Of Southern California (La) | Cidofovir peptide conjugates as prodrugs |
| EP1796671A4 (en) * | 2004-09-15 | 2009-01-21 | Merck & Co Inc | AMORPHIC FORM OF A PHOSPHORIC ACID SALT OF A DIPEPTIDYL-PEPTIDASE IV HEMMER |
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| US20090156545A1 (en) * | 2005-04-01 | 2009-06-18 | Hostetler Karl Y | Substituted Phosphate Esters of Nucleoside Phosphonates |
| EP2842559A3 (en) | 2005-04-08 | 2015-03-18 | Chimerix, Inc. | Compounds, compositions and methods for the treatment of viral infections and other medical disorders |
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| GB0605344D0 (en) * | 2006-03-17 | 2006-04-26 | Pliva Istrazivanje I Razvoj D | Pharmaceutically acceptable salts and polymorphic forms |
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| US8962829B1 (en) * | 2013-11-15 | 2015-02-24 | Chimerix, Inc. | Morphic forms of hexadecyloxypropyl-phosphonate esters and methods of synthesis thereof |
| EP3077403A4 (en) * | 2013-12-05 | 2017-08-02 | Chimerix, Inc. | Branched chain acyclic nucleoside phosphonate esters and methods of synthesis and uses thereof |
| AU2017290703B2 (en) * | 2016-06-28 | 2023-03-30 | Emergent Biodefense Operations Lansing Llc | Formulations of brincidofovir |
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2014
- 2014-10-10 US US14/512,335 patent/US8962829B1/en active Active
- 2014-10-10 MX MX2016006241A patent/MX362752B/es active IP Right Grant
- 2014-10-10 BR BR112016010862-0A patent/BR112016010862B1/pt active IP Right Grant
- 2014-10-10 EA EA201691006A patent/EA031861B1/ru not_active IP Right Cessation
- 2014-10-10 KR KR1020177036326A patent/KR20170143010A/ko not_active Withdrawn
- 2014-10-10 JP JP2016543558A patent/JP6150949B2/ja active Active
- 2014-10-10 IL IL302520A patent/IL302520B1/en unknown
- 2014-10-10 DK DK14861700.4T patent/DK2999476T3/da active
- 2014-10-10 EP EP14861700.4A patent/EP2999476B1/en active Active
- 2014-10-10 CN CN201480071309.8A patent/CN105899215A/zh active Pending
- 2014-10-10 CA CA2929593A patent/CA2929593C/en active Active
- 2014-10-10 KR KR1020177036324A patent/KR20170143009A/ko not_active Withdrawn
- 2014-10-10 UA UAA201606498A patent/UA116825C2/uk unknown
- 2014-10-10 WO PCT/US2014/060185 patent/WO2015073148A1/en not_active Ceased
- 2014-10-10 CN CN202010453121.7A patent/CN111777639A/zh active Pending
- 2014-10-10 KR KR1020167015513A patent/KR101812433B1/ko active Active
- 2014-10-10 AU AU2014349103A patent/AU2014349103B2/en active Active
- 2014-10-10 ES ES14861700.4T patent/ES2685819T3/es active Active
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2015
- 2015-01-23 US US14/604,334 patent/US9371344B2/en active Active
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2016
- 2016-05-10 IL IL245576A patent/IL245576B/en unknown
- 2016-05-20 US US15/160,885 patent/US9862687B2/en active Active
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2017
- 2017-04-11 AU AU2017202386A patent/AU2017202386A1/en not_active Abandoned
- 2017-05-17 AU AU2017203315A patent/AU2017203315A1/en not_active Abandoned
- 2017-05-23 JP JP2017101970A patent/JP6401820B2/ja active Active
- 2017-05-23 JP JP2017101971A patent/JP2017200920A/ja active Pending
- 2017-12-01 US US15/828,935 patent/US10112909B2/en active Active
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2018
- 2018-09-19 US US16/135,171 patent/US10487061B2/en active Active
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2019
- 2019-10-11 US US16/599,392 patent/US11066373B2/en active Active
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2020
- 2020-12-08 IL IL279291A patent/IL279291A/en unknown
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2021
- 2021-06-16 US US17/348,831 patent/US11912667B2/en active Active
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2024
- 2024-01-16 US US18/414,198 patent/US20240217938A1/en active Pending
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