NO331477B1 - Etanolat pseudopolymorfe former av en HIV-proteaseinhibitor, fremgangsmate ved fremstilling derav samt anvendelse derav - Google Patents
Etanolat pseudopolymorfe former av en HIV-proteaseinhibitor, fremgangsmate ved fremstilling derav samt anvendelse derav Download PDFInfo
- Publication number
- NO331477B1 NO331477B1 NO20045409A NO20045409A NO331477B1 NO 331477 B1 NO331477 B1 NO 331477B1 NO 20045409 A NO20045409 A NO 20045409A NO 20045409 A NO20045409 A NO 20045409A NO 331477 B1 NO331477 B1 NO 331477B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- ethanol
- formula
- pseudopolymorph
- ethanolate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 title claims description 15
- 239000004030 hiv protease inhibitor Substances 0.000 title description 2
- 229940122440 HIV protease inhibitor Drugs 0.000 title 1
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 14
- 108010010369 HIV Protease Proteins 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 30
- 239000013078 crystal Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 21
- 239000000523 sample Substances 0.000 description 16
- 239000012453 solvate Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 230000036571 hydration Effects 0.000 description 11
- 238000006703 hydration reaction Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 10
- 230000003595 spectral effect Effects 0.000 description 9
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- 239000006185 dispersion Substances 0.000 description 8
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- 238000002336 sorption--desorption measurement Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 229940088679 drug related substance Drugs 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
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- 239000012535 impurity Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000010899 nucleation Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000001237 Raman spectrum Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 208000016261 weight loss Diseases 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- -1 hydroxyethylamino Chemical group 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 208000020442 loss of weight Diseases 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000007614 solvation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 102000014961 Protein Precursors Human genes 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229940124522 antiretrovirals Drugs 0.000 description 2
- 239000003903 antiretrovirus agent Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000011194 good manufacturing practice Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
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- 239000003381 stabilizer Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 238000005079 FT-Raman Methods 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 108010078762 Protein Precursors Proteins 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 108700022715 Viral Proteases Proteins 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
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- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000012442 analytical experiment Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
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- 239000002775 capsule Substances 0.000 description 1
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- 230000004087 circulation Effects 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
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- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- 239000012047 saturated solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001839 systemic circulation Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000006514 viral protein processing Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02076929 | 2002-05-16 | ||
PCT/EP2003/050176 WO2003106461A2 (en) | 2002-05-16 | 2003-05-16 | Pseudopolymorphic forms of a hiv protease inhibitor |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20045409L NO20045409L (no) | 2004-12-10 |
NO331477B1 true NO331477B1 (no) | 2012-01-16 |
Family
ID=29724454
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20045409A NO331477B1 (no) | 2002-05-16 | 2004-12-10 | Etanolat pseudopolymorfe former av en HIV-proteaseinhibitor, fremgangsmate ved fremstilling derav samt anvendelse derav |
Country Status (26)
Country | Link |
---|---|
US (8) | US7700645B2 (ru) |
EP (4) | EP2314591B2 (ru) |
JP (1) | JP4864320B2 (ru) |
KR (2) | KR20100119906A (ru) |
CN (1) | CN100475819C (ru) |
AP (1) | AP2052A (ru) |
AU (2) | AU2003271740B2 (ru) |
BR (1) | BRPI0311176B8 (ru) |
CA (1) | CA2485834C (ru) |
CY (3) | CY1115665T1 (ru) |
DK (3) | DK1567529T4 (ru) |
EA (1) | EA007120B8 (ru) |
ES (4) | ES2638412T3 (ru) |
HK (1) | HK1081969A1 (ru) |
HR (1) | HRP20041061B1 (ru) |
HU (1) | HUE034389T2 (ru) |
IL (1) | IL165140A0 (ru) |
LT (1) | LT2767539T (ru) |
MX (1) | MXPA04011427A (ru) |
NO (1) | NO331477B1 (ru) |
NZ (1) | NZ536497A (ru) |
PL (1) | PL215151B1 (ru) |
PT (3) | PT2314591E (ru) |
SI (3) | SI2767539T1 (ru) |
WO (1) | WO2003106461A2 (ru) |
ZA (1) | ZA200410154B (ru) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2336160C (en) | 1998-06-23 | 2015-02-17 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Use of compounds for treating hiv |
SI2767539T1 (sl) | 2002-05-16 | 2017-10-30 | Janssen Sciences Ireland Uc | Psevdopolimorfne oblike inhibitorja proteaze HIV |
HRP20020614A2 (en) * | 2002-07-22 | 2004-06-30 | PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. | Rhombic pseudopolymorph of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin a |
US7772411B2 (en) | 2003-12-23 | 2010-08-10 | Tibotec Pharmaceuticals Ltd. | Process for the preparation of (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate |
ES2331257T3 (es) | 2005-02-25 | 2009-12-28 | Tibotec Pharmaceuticals | Sintesis de precursores de inhibidores de proteasas. |
US8153829B2 (en) * | 2006-11-09 | 2012-04-10 | Janssen Pharmaceutica N.V. | Methods for the preparation of hexahydrofuro[2,3-B]furan-3-ol |
AR073248A1 (es) | 2008-09-01 | 2010-10-20 | Tibotec Pharm Ltd | Proceso para la preparacion de (1s, 2r)-3- ((4-aminofenil) sulfonil) ( isobutil) amino)-1- bencil-2- hidroxipropilcarbamato de (3r, 3as,6ar)- hexahidrofuro-(2,3-b) furan-3- ilo (darunavir) y compuestos intermediarios utiles en dicho proceso. |
US8921415B2 (en) | 2009-01-29 | 2014-12-30 | Mapi Pharma Ltd. | Polymorphs of darunavir |
PL2381786T3 (pl) | 2009-01-29 | 2015-06-30 | Mapi Pharma Ltd | Dimetylosulfotlenkowy solwat darunawiru |
CA2776807C (en) * | 2009-09-17 | 2018-10-16 | Mylan Laboratories Limited | An improved process for the preparation of darunavir |
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