RU2015141024A - Производные эфиров фосфоновых кислот и способы их синтеза - Google Patents
Производные эфиров фосфоновых кислот и способы их синтеза Download PDFInfo
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- RU2015141024A RU2015141024A RU2015141024A RU2015141024A RU2015141024A RU 2015141024 A RU2015141024 A RU 2015141024A RU 2015141024 A RU2015141024 A RU 2015141024A RU 2015141024 A RU2015141024 A RU 2015141024A RU 2015141024 A RU2015141024 A RU 2015141024A
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- 238000000034 method Methods 0.000 title claims 3
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000002170 ethers Chemical class 0.000 title 1
- 150000003009 phosphonic acids Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 230000000877 morphologic effect Effects 0.000 claims 8
- 238000002441 X-ray diffraction Methods 0.000 claims 6
- 241000700605 Viruses Species 0.000 claims 5
- 241000700584 Simplexvirus Species 0.000 claims 3
- 241000700647 Variola virus Species 0.000 claims 3
- -1 [[(S) -2- (4-amino-2-oxo-1 (2H) -pyrimidinyl) -1- (hydroxymethyl) ethoxy] methyl] mono [3- (hexadecyloxy) propyl] ether phosphonic acid Chemical compound 0.000 claims 3
- 241000282693 Cercopithecidae Species 0.000 claims 2
- 241000701022 Cytomegalovirus Species 0.000 claims 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- 241001137864 Camelpox virus Species 0.000 claims 1
- 201000006082 Chickenpox Diseases 0.000 claims 1
- 241001115402 Ebolavirus Species 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 241000829111 Human polyomavirus 1 Species 0.000 claims 1
- 241000700627 Monkeypox virus Species 0.000 claims 1
- 241001631646 Papillomaviridae Species 0.000 claims 1
- 241001505332 Polyomavirus sp. Species 0.000 claims 1
- 241000700618 Vaccinia virus Species 0.000 claims 1
- 206010046980 Varicella Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 208000002672 hepatitis B Diseases 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 241000701161 unidentified adenovirus Species 0.000 claims 1
- 241000712461 unidentified influenza virus Species 0.000 claims 1
- 230000002477 vacuolizing effect Effects 0.000 claims 1
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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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
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- 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
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- 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
- A61P31/14—Antivirals for RNA viruses
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- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
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- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
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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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- C07—ORGANIC CHEMISTRY
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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
- 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
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- C—CHEMISTRY; METALLURGY
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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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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- 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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Biochemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (9)
1. Морфологическая форма B [[(S)-2-(4-амино-2-оксо-1(2H)-пиримидинил)-1-(гидроксиметил)этокси]метил]моно[3-(гексадецилокси)пропилового]эфира фосфоновой кислоты, характеризующаяся картиной дифракции рентгеновских лучей, включающей пики при углах 2Θ примерно 5,8, 12,5 и 24,0 градусов.
2. Морфологическая форма по п. 1, характеризующаяся картиной дифракции рентгеновских лучей, дополнительно включающей пик при угле 2Θ 11,6 градусов.
3. Морфологическая форма по п. 1, характеризующаяся картиной дифракции рентгеновских лучей, дополнительно включающей пики при углах 2Θ 11,6 и 17,4 градусов.
4. Морфологическая форма по п. 1, характеризующаяся картиной дифракции рентгеновских лучей, дополнительно включающей пики при углах 2Θ 11,6, 17,4, 20,8 и 21,6 градусов.
5. Морфологическая форма по п. 1, характеризующаяся картиной дифракции рентгеновских лучей, в основном аналогичной изображенной на Фиг.6.
6. Морфологическая форма по п. 1, характеризующаяся картиной дифракции рентгеновских лучей, в основном аналогичной изображенной на Фиг.7, лот 6.
7. Фармацевтическая композиция, включающая морфологическую форму B [[(S)-2-(4-амино-2-оксо-1(2H)-пиримидинил)-1-(гидроксиметил)этокси]метил]моно[3-(гексадецилокси)пропилового]эфира фосфоновой кислоты, а также фармацевтически приемлемый носитель.
8. Способ лечения вирусной инфекции у субъекта, включающий введение субъекту, которому это необходимо, эффективного количества морфологической формы B [[(S)-2-(4-амино-2-оксо-1(2H)-пиримидинил)-1-(гидроксиметил)этокси]метил]моно[3-(гексадецилокси)пропилового]эфира фосфоновой кислоты.
9. Способ по п. 8, где вирусная инфекция выбрана из группы, состоящей из: вируса иммунодефицита человека (ВИЧ), вируса гриппа, вируса простого герпеса (HSV), вируса герпеса человека 6 (HHV-6), цитомегаловируса (CMV), вирусов гепатита B и C, вируса Эпштейна-Барра (EBV), вируса ветряной оспы, вируса большой и малой оспы, вируса осповакцины, вируса натуральной оспы, вируса коровьей оспы, вируса оспы верблюдов, вируса оспы обезьян, вируса Эбола, вируса папилломы, аденовируса или вируса полиомы, в т.ч. вируса Джона Каннингема (JCV), вируса BK и вакуолизирующего вируса обезьян 40 или вируса обезьян 40 (SV40).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37874310P | 2010-08-31 | 2010-08-31 | |
| US61/378,743 | 2010-08-31 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013114370/04A Division RU2581045C2 (ru) | 2010-08-31 | 2011-08-31 | Производные эфиров фосфоновых кислот и способы их синтеза |
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| Publication Number | Publication Date |
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| RU2015141024A3 RU2015141024A3 (ru) | 2018-12-26 |
| RU2015141024A true RU2015141024A (ru) | 2018-12-26 |
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| RU2013114370/04A RU2581045C2 (ru) | 2010-08-31 | 2011-08-31 | Производные эфиров фосфоновых кислот и способы их синтеза |
| RU2015141024A RU2015141024A (ru) | 2010-08-31 | 2011-08-31 | Производные эфиров фосфоновых кислот и способы их синтеза |
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| Country | Link |
|---|---|
| US (3) | US8569321B2 (ru) |
| EP (2) | EP2611818B1 (ru) |
| JP (3) | JP2013536865A (ru) |
| CN (3) | CN105218580A (ru) |
| AU (1) | AU2011295937B2 (ru) |
| BR (1) | BR112013004925B1 (ru) |
| CA (1) | CA2809679C (ru) |
| ES (2) | ES2604137T3 (ru) |
| IL (4) | IL224955A (ru) |
| RU (2) | RU2581045C2 (ru) |
| WO (1) | WO2012031045A2 (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2611818B1 (en) * | 2010-08-31 | 2016-08-24 | Chimerix, Inc. | Phosphonate ester derivatives and methods of synthesis thereof |
| KR20150130355A (ko) | 2013-03-15 | 2015-11-23 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | 비환식 뉴클레오사이드 포스포네이트 디에스테르 |
| CN105899215A (zh) * | 2013-11-15 | 2016-08-24 | 奇默里克斯公司 | 十六烷氧基丙基膦酸酯的形态 |
| WO2015085256A1 (en) * | 2013-12-05 | 2015-06-11 | Chimerix, Inc. | Branched chain acyclic nucleoside phosphonate esters and methods of synthesis and uses thereof |
| CN103951703A (zh) * | 2014-04-28 | 2014-07-30 | 中国人民解放军军事医学科学院微生物流行病研究所 | 制备膦酯衍生物的方法 |
| SG11201701957XA (en) | 2014-09-15 | 2017-04-27 | Univ California | Nucleotide analogs |
| EP3212656B1 (en) | 2014-10-27 | 2019-06-05 | Concert Pharmaceuticals Inc. | Pyrimidine phosphonic acid esters bearing at least one deuterium atom |
| US10377782B2 (en) | 2015-09-15 | 2019-08-13 | The Regents Of The University Of California | Nucleotide analogs |
| ES3037596T3 (en) | 2016-06-28 | 2025-10-03 | Emergent Biodefense Operations Lansing Llc | Formulations of brincidofovir |
| JP7465416B2 (ja) | 2018-06-26 | 2024-04-11 | ティーエスアールエル インコーポレイテッド | 代謝安定性プロドラッグ |
| CN109021011A (zh) * | 2018-08-14 | 2018-12-18 | 山东沾化永浩医药科技有限公司 | 一种合成对甲苯磺酰氧甲基膦酸二乙酯的方法 |
| KR20250052378A (ko) | 2022-07-21 | 2025-04-18 | 안티바 바이오사이언시즈, 인크. | Hpv 감염 및 hpv-유도 신생물의 치료를 위한 조성물 및 투여 형태 |
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| EP1123308A1 (en) * | 1998-10-23 | 2001-08-16 | Darwin Discovery Limited | Single morphic forms of known peptide metalloproteinase inhibitors |
| EP1233770B1 (en) | 1999-12-03 | 2008-02-13 | The Regents of The University of California at San Diego | Phosphonate compounds |
| SI1644389T1 (sl) * | 2003-06-16 | 2011-06-30 | Acad Of Science Czech Republic | Pirimidinske spojine s fosfonatnimi skupinami kot antivirusni nukleotidni analogi |
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| WO2005090370A1 (en) * | 2004-02-05 | 2005-09-29 | The Regents Of The University Of California | Pharmacologically active agents containing esterified phosphonates and methods for use thereof |
| WO2005087788A2 (en) * | 2004-03-04 | 2005-09-22 | The Regents Of The University Of California | Methods for preparation of nucleoside phosphonate esters |
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| BR112012002551A2 (pt) * | 2009-08-03 | 2017-06-13 | Chimerix Inc | composição e métodos de tratamento de infecções virais e tumores induzidos por vírus |
| JP2013509433A (ja) * | 2009-10-30 | 2013-03-14 | キメリクス，インコーポレイテッド | ウイルス関連疾患を処置する方法 |
| US20110263536A1 (en) | 2010-04-22 | 2011-10-27 | Chimerix, Inc. | Methods of Treating Orthopox Virus Infections and Associated Diseases |
| EP2611818B1 (en) * | 2010-08-31 | 2016-08-24 | Chimerix, Inc. | Phosphonate ester derivatives and methods of synthesis thereof |
| US20140303092A1 (en) * | 2011-10-26 | 2014-10-09 | Chimerix, Inc | Hexadecyloxypropyl cidofovir for the treatment of double-stranded dna virus infection |
| US20150087619A1 (en) * | 2012-04-27 | 2015-03-26 | Chimerix, Inc. | Method of mitigating virus associated end-organ damage |
| CN105899215A (zh) * | 2013-11-15 | 2016-08-24 | 奇默里克斯公司 | 十六烷氧基丙基膦酸酯的形态 |
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