CA2898092A1 - Lamivudine salts - Google Patents
Lamivudine salts Download PDFInfo
- Publication number
- CA2898092A1 CA2898092A1 CA2898092A CA2898092A CA2898092A1 CA 2898092 A1 CA2898092 A1 CA 2898092A1 CA 2898092 A CA2898092 A CA 2898092A CA 2898092 A CA2898092 A CA 2898092A CA 2898092 A1 CA2898092 A1 CA 2898092A1
- Authority
- CA
- Canada
- Prior art keywords
- lamivudine
- crystalline form
- hydrochloride
- sulfate
- peaks
- 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.)
- Abandoned
Links
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical class O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 title claims abstract description 280
- 229960001627 lamivudine Drugs 0.000 claims abstract description 263
- 238000000034 method Methods 0.000 claims abstract description 73
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- LEPNDALFXHAENA-UOERWJHTSA-N 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;hydrochloride Chemical compound Cl.O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 LEPNDALFXHAENA-UOERWJHTSA-N 0.000 claims description 202
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 138
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 131
- 239000000725 suspension Substances 0.000 claims description 68
- 229910019142 PO4 Inorganic materials 0.000 claims description 67
- 239000010452 phosphate Substances 0.000 claims description 67
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 63
- 238000010438 heat treatment Methods 0.000 claims description 47
- 239000002904 solvent Substances 0.000 claims description 47
- 238000001237 Raman spectrum Methods 0.000 claims description 45
- 238000001816 cooling Methods 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- 238000001757 thermogravimetry curve Methods 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 22
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 235000011007 phosphoric acid Nutrition 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 8
- 230000004584 weight gain Effects 0.000 claims description 8
- 235000019786 weight gain Nutrition 0.000 claims description 8
- 208000002672 hepatitis B Diseases 0.000 claims description 7
- 238000001179 sorption measurement Methods 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 208000031886 HIV Infections Diseases 0.000 claims description 3
- 208000037357 HIV infectious disease Diseases 0.000 claims description 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 3
- 208000005074 Retroviridae Infections Diseases 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 12
- 150000003839 salts Chemical group 0.000 abstract description 12
- 241000725303 Human immunodeficiency virus Species 0.000 abstract description 9
- 241000700605 Viruses Species 0.000 abstract description 9
- 208000015181 infectious disease Diseases 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000012458 free base Substances 0.000 description 32
- 238000001035 drying Methods 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 230000004580 weight loss Effects 0.000 description 20
- 238000001069 Raman spectroscopy Methods 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 230000001351 cycling effect Effects 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 201000010099 disease Diseases 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 238000002076 thermal analysis method Methods 0.000 description 7
- 238000001665 trituration Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004164 analytical calibration Methods 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 208000006454 hepatitis Diseases 0.000 description 4
- 231100000283 hepatitis Toxicity 0.000 description 4
- 150000004712 monophosphates Chemical class 0.000 description 4
- 239000013557 residual solvent Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 241000700721 Hepatitis B virus Species 0.000 description 3
- 208000036142 Viral infection Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 238000011067 equilibration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- -1 sachets Substances 0.000 description 2
- 241000711549 Hepacivirus C Species 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 206010038997 Retroviral infections Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940072253 epivir Drugs 0.000 description 1
- 229940074057 epivir hbv Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000005252 hepatitis A Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- ZZIZZTHXZRDOFM-XFULWGLBSA-N tamsulosin hydrochloride Chemical compound [H+].[Cl-].CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-XFULWGLBSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361762018P | 2013-02-07 | 2013-02-07 | |
| US61/762,018 | 2013-02-07 | ||
| PCT/US2014/015024 WO2014124092A2 (en) | 2013-02-07 | 2014-02-06 | Lamivudine salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2898092A1 true CA2898092A1 (en) | 2014-08-14 |
Family
ID=50151399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2898092A Abandoned CA2898092A1 (en) | 2013-02-07 | 2014-02-06 | Lamivudine salts |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9688666B2 (enExample) |
| EP (1) | EP2953945A2 (enExample) |
| JP (1) | JP2016507569A (enExample) |
| CA (1) | CA2898092A1 (enExample) |
| WO (1) | WO2014124092A2 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2898092A1 (en) * | 2013-02-07 | 2014-08-14 | Tobira Therapeutics, Inc. | Lamivudine salts |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6288033B1 (en) * | 1998-09-25 | 2001-09-11 | Sciclone Pharmaceuticals, Inc. | Treatment of hepatitis B infection with thymosin alpha 1 in combination with lamivudine or in combination with lamivudine and famciclovir |
| IL151188A0 (en) * | 2000-02-28 | 2003-04-10 | Bayer Ag | Medicament for viral diseases |
| CA2351049C (en) | 2001-06-18 | 2007-03-13 | Brantford Chemicals Inc. | Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers |
| BR0314259A (pt) * | 2002-09-13 | 2005-07-26 | Idenix Cayman Ltd | ß-l-2'-desoxinucleosìdeos para o tratamento de cepas de hbv resistentes e terapias combinadas |
| US20050053916A1 (en) * | 2002-10-01 | 2005-03-10 | Korba Brent E. | Diagnostic for long term response of HBV carrier to 3TC therapy |
| CN1517347A (zh) * | 2003-01-16 | 2004-08-04 | 北京昭衍新药研究中心 | 抗病毒核苷衍生物 |
| TWI332402B (en) * | 2003-12-19 | 2010-11-01 | Ind Tech Res Inst | An extract for treating hepatitis |
| DE602007009957D1 (de) * | 2006-04-18 | 2010-12-02 | Lupin Ltd | Neue kristalline form von lamivudin |
| KR20080086687A (ko) * | 2007-03-23 | 2008-09-26 | 주식회사 파나진 | 라미부딘 내성 ｂ형 간염바이러스 검출을 위한 ρνα프로브, 키트 및 방법 |
| WO2009031026A2 (en) * | 2007-09-06 | 2009-03-12 | Combino Pharm, S.L. | Novel pharmaceutical compositions |
| US20100190982A1 (en) * | 2007-09-17 | 2010-07-29 | Janardhana Rao Vascuri | Process for the preparation of lamivudine form i |
| BRPI0820222A2 (pt) * | 2007-11-29 | 2015-06-16 | Ranbaxy Lab Ltd | Forma i cristalina estável de lamivudina e processo de preparação |
| US8536151B2 (en) * | 2008-09-01 | 2013-09-17 | Hetero Research Foundation | Process for preparing lamivudine polymorph form |
| WO2010082128A1 (en) * | 2009-01-19 | 2010-07-22 | Aurobindo Pharma Limited | Process for the preparation of cis-nucleoside derivative |
| EP2435052B1 (en) * | 2009-05-27 | 2015-07-15 | Hetero Research Foundation | Solid oral dosage forms of lamivudine with isomalt |
| BRPI0903664B8 (pt) * | 2009-09-22 | 2021-05-25 | Fund De Amparo A Pesquisa Do Estado De Sao Paulo Fapesp | método de obtenção de nova forma cristalina de lamivudina, seu sal cloridrato monoidratado, formulações farmacêuticas e seus usos |
| US8816074B2 (en) * | 2009-11-16 | 2014-08-26 | University of Georgia Foundation, Inc. | 2′-fluoro-6′-methylene carbocyclic nucleosides and methods of treating viral infections |
| MX2012005601A (es) * | 2009-11-16 | 2012-08-01 | Univ Georgia | Nucleosidos carboxiclicos de 2'-fluoro-6'-metileno y metodos para tratar infecciones virales. |
| US9700560B2 (en) * | 2009-11-16 | 2017-07-11 | University Of Georgia Research Foundation, Inc. | 2′-fluoro-6′-methylene carbocyclic nucleosides and methods of treating viral infections |
| AU2011215878A1 (en) * | 2010-02-12 | 2012-08-09 | Merck Sharp & Dohme Corp. | Preparation of lamivudine Form I |
| CN102167696B (zh) * | 2010-02-25 | 2013-09-18 | 南京正大天晴制药有限公司 | 拉米夫定草酸盐及其制备方法 |
| CN103282369A (zh) * | 2011-04-08 | 2013-09-04 | 劳乐斯实验室私营有限公司 | 抗逆转录病毒化合物与抗氧化酸的固体形式、其制备方法以及其药物组合物 |
| CN102225069B (zh) * | 2011-04-29 | 2013-05-08 | 陶珍珠 | 一种耐药性显著降低的药物组合物及其制备方法和其应用 |
| US20140193491A1 (en) * | 2011-05-30 | 2014-07-10 | Cipla Limited | Pharmaceutical antiretroviral composition |
| CA2866133A1 (en) * | 2012-03-05 | 2013-09-12 | Cipla Limited | Pharmaceutical antiretroviral combinations comprising lamivudine, festinavir and nevirapine |
| CA2898092A1 (en) * | 2013-02-07 | 2014-08-14 | Tobira Therapeutics, Inc. | Lamivudine salts |
-
2014
- 2014-02-06 CA CA2898092A patent/CA2898092A1/en not_active Abandoned
- 2014-02-06 US US14/766,563 patent/US9688666B2/en not_active Expired - Fee Related
- 2014-02-06 WO PCT/US2014/015024 patent/WO2014124092A2/en not_active Ceased
- 2014-02-06 EP EP14705933.1A patent/EP2953945A2/en not_active Withdrawn
- 2014-02-06 JP JP2015557055A patent/JP2016507569A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20150368232A1 (en) | 2015-12-24 |
| US9688666B2 (en) | 2017-06-27 |
| EP2953945A2 (en) | 2015-12-16 |
| WO2014124092A2 (en) | 2014-08-14 |
| JP2016507569A (ja) | 2016-03-10 |
| WO2014124092A3 (en) | 2014-10-23 |
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