CA2649796A1 - A novel crystalline form of lamivudine - Google Patents
A novel crystalline form of lamivudine Download PDFInfo
- Publication number
- CA2649796A1 CA2649796A1 CA002649796A CA2649796A CA2649796A1 CA 2649796 A1 CA2649796 A1 CA 2649796A1 CA 002649796 A CA002649796 A CA 002649796A CA 2649796 A CA2649796 A CA 2649796A CA 2649796 A1 CA2649796 A1 CA 2649796A1
- Authority
- CA
- Canada
- Prior art keywords
- lamivudine
- crystals
- crystalline form
- pharmaceutical composition
- cis
- 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 compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 title claims abstract description 102
- 229960001627 lamivudine Drugs 0.000 title claims abstract description 97
- 239000013078 crystal Substances 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000000843 powder Substances 0.000 claims abstract description 13
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 4
- 239000003937 drug carrier Substances 0.000 claims abstract 4
- 239000007787 solid Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 238000010438 heat treatment Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 8
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims description 8
- 230000004580 weight loss Effects 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000002411 thermogravimetry Methods 0.000 claims description 5
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims 6
- -1 aliphatic alcohols Chemical class 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 239000012452 mother liquor Substances 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 238000000646 scanning calorimetry Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 24
- 239000000725 suspension Substances 0.000 description 22
- 238000000634 powder X-ray diffraction Methods 0.000 description 18
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 9
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 208000016261 weight loss Diseases 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 4
- 229940079832 sodium starch glycolate Drugs 0.000 description 4
- 229920003109 sodium starch glycolate Polymers 0.000 description 4
- 239000008109 sodium starch glycolate Substances 0.000 description 4
- 229960002555 zidovudine Drugs 0.000 description 4
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical class C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 229940080313 sodium starch Drugs 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
- 229910002483 Cu Ka Inorganic materials 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 229940124411 anti-hiv antiviral agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940072253 epivir Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000000373 single-crystal X-ray diffraction data Methods 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN347/KOL/2006 | 2006-04-18 | ||
| IN347KO2006 | 2006-04-18 | ||
| PCT/IN2007/000047 WO2007119248A1 (en) | 2006-04-18 | 2007-02-09 | A novel crystalline form of lamivudine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2649796A1 true CA2649796A1 (en) | 2007-10-25 |
Family
ID=37969898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002649796A Abandoned CA2649796A1 (en) | 2006-04-18 | 2007-02-09 | A novel crystalline form of lamivudine |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8158607B2 (https=) |
| EP (1) | EP2007758B1 (https=) |
| JP (1) | JP5184511B2 (https=) |
| AT (1) | ATE485292T1 (https=) |
| AU (1) | AU2007237818B2 (https=) |
| CA (1) | CA2649796A1 (https=) |
| DE (1) | DE602007009957D1 (https=) |
| ES (1) | ES2357159T3 (https=) |
| WO (1) | WO2007119248A1 (https=) |
| ZA (1) | ZA200809820B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009037538A2 (en) * | 2007-09-17 | 2009-03-26 | Aurobindo Pharma Ltd | Process for the preparation of lamivudine form i |
| WO2009069014A1 (en) * | 2007-11-29 | 2009-06-04 | Ranbaxy Laboratories Limited | Amorphous lamivudine and its preparation |
| AU2008331168A1 (en) * | 2007-11-29 | 2009-06-04 | Ranbaxy Laboratories Limited | Crystalline form I of lamivudine and its preparation |
| WO2009116055A1 (en) * | 2008-03-17 | 2009-09-24 | Lupin Limited | Lamivudine : zidovudine : water 1 : 1 : 1 cocrystal |
| WO2009127996A1 (en) * | 2008-04-17 | 2009-10-22 | Ranbaxy Laboratories Limited | Novel crystalline form of lamivudine |
| US8536151B2 (en) | 2008-09-01 | 2013-09-17 | Hetero Research Foundation | Process for preparing lamivudine polymorph form |
| US8481554B2 (en) | 2009-05-27 | 2013-07-09 | Hetero Research Foundation | Solid oral dosage forms of lamivudine |
| ES2540074T3 (es) | 2009-10-14 | 2015-07-08 | Mylan Laboratories Limited | Proceso para la preparación de lamivudina y nuevas sales en la fabricación de la misma |
| EP2536715A1 (en) | 2010-02-12 | 2012-12-26 | Merck Sharp & Dohme Corp. | Preparation of lamivudine form i |
| WO2013168066A1 (en) | 2012-05-05 | 2013-11-14 | Lupin Limited | An improved process for the manufacture of lamivudine form i. |
| EP2953945A2 (en) * | 2013-02-07 | 2015-12-16 | Tobira Therapeutics, Inc. | Lamivudine salts |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047407A (en) * | 1989-02-08 | 1991-09-10 | Iaf Biochem International, Inc. | 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties |
| US5204466A (en) * | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
| GB9009861D0 (en) | 1990-05-02 | 1990-06-27 | Glaxo Group Ltd | Chemical compounds |
| GB9111902D0 (en) * | 1991-06-03 | 1991-07-24 | Glaxo Group Ltd | Chemical compounds |
| WO2003027106A1 (en) * | 2001-09-25 | 2003-04-03 | Cadila Healthcar Limited | Process for the preparation of crystalline polymorph ii of lamivudine |
-
2007
- 2007-02-09 EP EP07706193A patent/EP2007758B1/en not_active Not-in-force
- 2007-02-09 CA CA002649796A patent/CA2649796A1/en not_active Abandoned
- 2007-02-09 AT AT07706193T patent/ATE485292T1/de not_active IP Right Cessation
- 2007-02-09 ES ES07706193T patent/ES2357159T3/es active Active
- 2007-02-09 DE DE602007009957T patent/DE602007009957D1/de active Active
- 2007-02-09 WO PCT/IN2007/000047 patent/WO2007119248A1/en not_active Ceased
- 2007-02-09 JP JP2009506041A patent/JP5184511B2/ja not_active Expired - Fee Related
- 2007-02-09 AU AU2007237818A patent/AU2007237818B2/en not_active Ceased
- 2007-02-09 US US12/297,174 patent/US8158607B2/en not_active Expired - Fee Related
-
2008
- 2008-11-18 ZA ZA2008/09820A patent/ZA200809820B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE602007009957D1 (de) | 2010-12-02 |
| JP2009534373A (ja) | 2009-09-24 |
| WO2007119248A1 (en) | 2007-10-25 |
| ES2357159T3 (es) | 2011-04-19 |
| ZA200809820B (en) | 2010-02-24 |
| EP2007758B1 (en) | 2010-10-20 |
| AU2007237818B2 (en) | 2012-09-27 |
| JP5184511B2 (ja) | 2013-04-17 |
| ATE485292T1 (de) | 2010-11-15 |
| EP2007758A1 (en) | 2008-12-31 |
| US20090281053A1 (en) | 2009-11-12 |
| US8158607B2 (en) | 2012-04-17 |
| AU2007237818A1 (en) | 2007-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20150210 |