ES2357159T3 - Forma cristalina novedosa de lamivudina. - Google Patents
Forma cristalina novedosa de lamivudina. Download PDFInfo
- Publication number
- ES2357159T3 ES2357159T3 ES07706193T ES07706193T ES2357159T3 ES 2357159 T3 ES2357159 T3 ES 2357159T3 ES 07706193 T ES07706193 T ES 07706193T ES 07706193 T ES07706193 T ES 07706193T ES 2357159 T3 ES2357159 T3 ES 2357159T3
- Authority
- ES
- Spain
- Prior art keywords
- lamivudine
- crystalline form
- cis
- oxathiolan
- hydroxymethyl
- 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.)
- Active
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 claims abstract description 105
- 229960001627 lamivudine Drugs 0.000 claims abstract description 94
- 239000013078 crystal Substances 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 3
- 239000003937 drug carrier Substances 0.000 claims abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 19
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 9
- 230000004580 weight loss Effects 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 7
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 238000002411 thermogravimetry Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000009331 sowing Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 3
- -1 aliphatic alcohols Chemical class 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 abstract description 6
- 239000000725 suspension Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 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
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 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
- 229940023144 sodium glycolate Drugs 0.000 description 3
- 229940079832 sodium starch glycolate Drugs 0.000 description 3
- 229920003109 sodium starch glycolate Polymers 0.000 description 3
- 239000008109 sodium starch glycolate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229940032147 starch Drugs 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 3
- 229960002555 zidovudine Drugs 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940075614 colloidal silicon dioxide Drugs 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
- 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
- 239000008213 purified water Substances 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
- LHCOVOKZWQYODM-CPEOKENHSA-N 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical group O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1.O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 LHCOVOKZWQYODM-CPEOKENHSA-N 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940124411 anti-hiv antiviral agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000000576 coating method Methods 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
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229940072253 epivir Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 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
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 238000007670 refining Methods 0.000 description 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN347KO2006 | 2006-04-18 | ||
| INKA0347/06 | 2006-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2357159T3 true ES2357159T3 (es) | 2011-04-19 |
Family
ID=37969898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07706193T Active ES2357159T3 (es) | 2006-04-18 | 2007-02-09 | Forma cristalina novedosa de lamivudina. |
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 |
| CA2649796A1 (en) | 2007-10-25 |
| WO2007119248A1 (en) | 2007-10-25 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2357159T3 (es) | Forma cristalina novedosa de lamivudina. | |
| ES2527768T5 (es) | Sales cristalinas de sitagliptina | |
| US8637535B2 (en) | Polymorphic and other crystalline forms of cis-FTC | |
| ES2351958T3 (es) | 5-cloro-3-(4-metanosulfonilfenil)-6'-metil-[2,3'] bipiridinil en forma cristalina pura y procedimiento de síntesis. | |
| JP2009534373A5 (https=) | ||
| US7893076B2 (en) | Crystalline form F of Imatinib mesylate | |
| ES2814499T3 (es) | Formas en estado sólido de sales de Nilotinib | |
| WO2013115535A1 (ko) | 트리사이클로 유도체 화합물의 신규한 결정형 산부가염 또는 이의 수화물 및 이의 제조방법 | |
| KR100830002B1 (ko) | 시부트라민의 무기산염 | |
| AU2002335489A1 (en) | Polymorphic and other crystalline forms of cis-FTC | |
| US8389722B2 (en) | Adefovir dipivoxil crystalline monohydrate form | |
| KR20060080818A (ko) | 시부트라민의 술폰산염 | |
| TW201609780A (zh) | 泰諾福韋之固體形式 | |
| JP7809725B2 (ja) | 三環式誘導体化合物の結晶形及びその製造方法並びにそれを含む薬学的組成物 | |
| CN113072583A (zh) | 一种替诺福韦艾拉酚胺半富马酸盐的结晶及其制备方法 | |
| WO2009116055A1 (en) | Lamivudine : zidovudine : water 1 : 1 : 1 cocrystal | |
| AU2008202336B2 (en) | Polymorphic and other crystalline forms of cis-FTC | |
| KR20260049277A (ko) | 5-((3R,55)-3-아미노-5-트리플루오로메틸-피페리딘-1-일)-퀴놀린-8-카르보니트릴HCl 결정형 A1 | |
| KR20130033243A (ko) | 아데포비어 디피복실의 공결정 |