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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (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 |
| CN1406233A (zh) * | 2000-02-28 | 2003-03-26 | 拜尔公司 | 用于病毒性疾病的药物 |
| 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 |
| ES2547002T3 (es) * | 2002-09-13 | 2015-09-30 | Novartis Ag | Beta-L-2' desoxinucleósidos para el tratamiento de cepas de VHB resistentes |
| AU2003277208A1 (en) * | 2002-10-01 | 2004-04-23 | Georgetown University | 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 |
| ATE485292T1 (de) * | 2006-04-18 | 2010-11-15 | 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 |
| WO2009037538A2 (en) * | 2007-09-17 | 2009-03-26 | Aurobindo Pharma Ltd | Process for the preparation of lamivudine form i |
| WO2009069013A1 (en) * | 2007-11-29 | 2009-06-04 | Ranbaxy Laboratories Limited | Crystalline form i of lamivudine and its preparation |
| WO2010023676A2 (en) * | 2008-09-01 | 2010-03-04 | Hetero Research Foundation | Process for preparing lamivudine polymorph form |
| US20110282046A1 (en) | 2009-01-19 | 2011-11-17 | Rama Shankar | Process for preparation of cis-nucleoside derivative |
| WO2010137027A1 (en) * | 2009-05-27 | 2010-12-02 | Hetero Research Foundation | Solid oral dosage forms of lamivudine |
| 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 |
| KR101961601B1 (ko) * | 2009-11-16 | 2019-03-25 | 유니버시티 오브 조지아 리서치 파운데이션, 인코포레이티드 | 바이러스 감염 치료를 위한 ２＇―플루오로―６＇―메틸렌 카보사이클릭 뉴클레오사이드 및 방법 |
| 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 |
| 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 |
| US8796452B2 (en) * | 2010-02-12 | 2014-08-05 | 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 |
| CA2835272A1 (en) * | 2011-05-30 | 2012-12-06 | Cipla Limited | Pharmaceutical antiretroviral composition |
| JP2015509524A (ja) * | 2012-03-05 | 2015-03-30 | シプラ・リミテッド | ラミブジン、フェスティナビルおよびネビラピンを含んでなる抗レトロウイルス医薬組成物 |
| 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 EP EP14705933.1A patent/EP2953945A2/en not_active Withdrawn
- 2014-02-06 US US14/766,563 patent/US9688666B2/en not_active Expired - Fee Related
- 2014-02-06 JP JP2015557055A patent/JP2016507569A/ja active Pending
- 2014-02-06 WO PCT/US2014/015024 patent/WO2014124092A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20150368232A1 (en) | 2015-12-24 |
| WO2014124092A3 (en) | 2014-10-23 |
| EP2953945A2 (en) | 2015-12-16 |
| JP2016507569A (ja) | 2016-03-10 |
| WO2014124092A2 (en) | 2014-08-14 |
| US9688666B2 (en) | 2017-06-27 |
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