SK14832002A3 - Kryštalické liečivo - Google Patents

Kryštalické liečivo Download PDF

Info

Publication number: SK14832002A3
Authority: SK; Slovakia
Prior art keywords: lopinavir; crystalline form; type; solid state; absorption band
Prior art date: 2000-03-30

Application number

SK1483-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Daniel A. Dickman

Sanjay Chemburkar

James J. Fort

Rodger F. Henry

David Lechuga-Ballesteros

Yuping Niu

William Porter

Original Assignee

Abbott Laboratories

Priority date (The priority date 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 date listed.)

2000-03-30

Filing date

2001-03-21

Publication date

2003-02-04

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27065762&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK14832002(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-02-27 Priority claimed from US09/793,536 external-priority patent/US6608198B2/en

2001-03-21 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2003-02-04 Publication of SK14832002A3 publication Critical patent/SK14832002A3/sk

Links

KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims abstract description 394
229960004525 lopinavir Drugs 0.000 claims abstract description 394
239000007787 solid Substances 0.000 claims description 111
238000010521 absorption reaction Methods 0.000 claims description 55
238000002329 infrared spectrum Methods 0.000 claims description 40
238000000634 powder X-ray diffraction Methods 0.000 claims description 16
239000012453 solvate Substances 0.000 claims description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 154
238000001228 spectrum Methods 0.000 description 66
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
239000013078 crystal Substances 0.000 description 45
239000000243 solution Substances 0.000 description 43
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
239000002904 solvent Substances 0.000 description 27
238000002360 preparation method Methods 0.000 description 26
238000002411 thermogravimetry Methods 0.000 description 20
239000000203 mixture Substances 0.000 description 18
239000000523 sample Substances 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
-1 2,6-dimethylphenoxyacetyl Chemical group 0.000 description 15
238000002441 X-ray diffraction Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 15
238000001914 filtration Methods 0.000 description 14
239000000843 powder Substances 0.000 description 14
238000010438 heat treatment Methods 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
238000004476 mid-IR spectroscopy Methods 0.000 description 11
230000005855 radiation Effects 0.000 description 11
238000002425 crystallisation Methods 0.000 description 10
230000008025 crystallization Effects 0.000 description 10
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 9
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 9
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 9
239000005642 Oleic acid Substances 0.000 description 9
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
238000000113 differential scanning calorimetry Methods 0.000 description 9
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 9
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
239000003039 volatile agent Substances 0.000 description 9
239000002002 slurry Substances 0.000 description 8
NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 7
239000011521 glass Substances 0.000 description 7
238000005259 measurement Methods 0.000 description 7
239000003921 oil Substances 0.000 description 7
229960000311 ritonavir Drugs 0.000 description 7
NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000006260 foam Substances 0.000 description 6
238000002156 mixing Methods 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
230000010287 polarization Effects 0.000 description 6
239000000725 suspension Substances 0.000 description 6
AMPWQTJNJASABL-UHFFFAOYSA-N 1,6-diphenylhexan-1-amine Chemical compound C=1C=CC=CC=1C(N)CCCCCC1=CC=CC=C1 AMPWQTJNJASABL-UHFFFAOYSA-N 0.000 description 5
208000031886 HIV Infections Diseases 0.000 description 5
208000037357 HIV infectious disease Diseases 0.000 description 5
238000004566 IR spectroscopy Methods 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
238000012937 correction Methods 0.000 description 5
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
238000007670 refining Methods 0.000 description 5
238000001757 thermogravimetry curve Methods 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001938 differential scanning calorimetry curve Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical class OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000725303 Human immunodeficiency virus Species 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229940095564 anhydrous calcium sulfate Drugs 0.000 description 2
239000012296 anti-solvent Substances 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000004030 hiv protease inhibitor Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
229940011051 isopropyl acetate Drugs 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000007614 solvation Methods 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
FIDGQQIVMWAIAD-UHFFFAOYSA-N 2,2,4,4-tetramethyloxolane Chemical compound CC1(C)COC(C)(C)C1 FIDGQQIVMWAIAD-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 description 1
229910016036 BaF 2 Inorganic materials 0.000 description 1
229910004261 CaF 2 Inorganic materials 0.000 description 1
108010010369 HIV Protease Proteins 0.000 description 1
229940122440 HIV protease inhibitor Drugs 0.000 description 1
KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004365 Protease Substances 0.000 description 1
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004320 controlled atmosphere Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
238000005384 cross polarization magic-angle spinning Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000007405 data analysis Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
238000009499 grossing Methods 0.000 description 1
230000000887 hydrating effect Effects 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
230000002209 hydrophobic effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
229960002479 isosorbide Drugs 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
LWXUXIDLCWPHIW-GSDHBNRESA-N n-[(2s,3s,5s)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl]-2-(2,6-dimethylphenoxy)acetamide Chemical compound CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@@H](N)CC=1C=CC=CC=1)CC1=CC=CC=C1 LWXUXIDLCWPHIW-GSDHBNRESA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000003303 reheating Methods 0.000 description 1
229940020848 ritonavir 33.3 mg Drugs 0.000 description 1
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000010583 slow cooling Methods 0.000 description 1
239000007905 soft elastic gelatin capsule Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
- 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)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Virology (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
AIDS & HIV (AREA)
Engineering & Computer Science (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK1483-2002A 2000-03-30 2001-03-21 Kryštalické liečivo SK14832002A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US53825700A	2000-03-30	2000-03-30
US09/793,536 US6608198B2 (en)	2000-03-30	2001-02-27	Crystalline pharmaceutical
PCT/US2001/009112 WO2001074787A2 (en)	2000-03-30	2001-03-21	Crystalline pharmaceutical

Publications (1)

Publication Number	Publication Date
SK14832002A3 true SK14832002A3 (sk)	2003-02-04

Family

ID=27065762

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1483-2002A SK14832002A3 (sk)	2000-03-30	2001-03-21	Kryštalické liečivo

Country Status (22)

Country	Link
EP (1)	EP1268442A2 (pt)
JP (1)	JP2003529592A (pt)
KR (1)	KR100773258B1 (pt)
CN (2)	CN101066952A (pt)
AR (2)	AR033360A1 (pt)
AU (3)	AU5092001A (pt)
BG (1)	BG107165A (pt)
BR (1)	BR0109433A (pt)
CA (1)	CA2403635A1 (pt)
CZ (1)	CZ20023529A3 (pt)
HU (1)	HUP0302675A3 (pt)
IL (1)	IL151551A0 (pt)
MX (1)	MXPA02009559A (pt)
MY (1)	MY128296A (pt)
NO (1)	NO325005B1 (pt)
NZ (1)	NZ521183A (pt)
PE (1)	PE20011232A1 (pt)
PL (1)	PL359727A1 (pt)
SA (2)	SA01220270B1 (pt)
SK (1)	SK14832002A3 (pt)
TW (1)	TWI284640B (pt)
WO (1)	WO2001074787A2 (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6608198B2 (en)	2000-03-30	2003-08-19	Abbott Laboratories	Crystalline pharmaceutical
US8025899B2 (en)	2003-08-28	2011-09-27	Abbott Laboratories	Solid pharmaceutical dosage form
EP2393786B1 (en)	2009-02-06	2014-01-22	Hetero Research Foundation	Novel polymorphs of lopinavir
CA2770338A1 (en) *	2009-08-27	2011-03-03	Merck Sharp & Dohme Corp.	Processes for preparing protease inhibitors of hepatitis c virus
CN112830899A (zh) *	2021-01-18	2021-05-25	合肥华方医药科技有限公司	一种洛匹那韦新晶型及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5914332A (en) *	1995-12-13	1999-06-22	Abbott Laboratories	Retroviral protease inhibiting compounds
AU8145198A (en) *	1997-06-16	1999-01-04	Vertex Pharmaceuticals Incorporated	Methods of increasing the bioavailability of stable crystal polymorphs of a compound

2001
- 2001-03-07 MY MYPI20011034A patent/MY128296A/en unknown
- 2001-03-21 BR BR0109433-5A patent/BR0109433A/pt not_active Application Discontinuation
- 2001-03-21 HU HU0302675A patent/HUP0302675A3/hu unknown
- 2001-03-21 IL IL15155101A patent/IL151551A0/xx unknown
- 2001-03-21 WO PCT/US2001/009112 patent/WO2001074787A2/en not_active Ceased
- 2001-03-21 KR KR1020027012849A patent/KR100773258B1/ko not_active Ceased
- 2001-03-21 AU AU5092001A patent/AU5092001A/xx active Pending
- 2001-03-21 EP EP01924250A patent/EP1268442A2/en not_active Withdrawn
- 2001-03-21 PL PL35972701A patent/PL359727A1/xx not_active Application Discontinuation
- 2001-03-21 CN CNA2007101123988A patent/CN101066952A/zh active Pending
- 2001-03-21 NZ NZ521183A patent/NZ521183A/en not_active IP Right Cessation
- 2001-03-21 CN CNB018076882A patent/CN1330639C/zh not_active Expired - Lifetime
- 2001-03-21 CZ CZ20023529A patent/CZ20023529A3/cs unknown
- 2001-03-21 AU AU2001250920A patent/AU2001250920B2/en not_active Revoked
- 2001-03-21 CA CA002403635A patent/CA2403635A1/en not_active Abandoned
- 2001-03-21 MX MXPA02009559A patent/MXPA02009559A/es active IP Right Grant
- 2001-03-21 SK SK1483-2002A patent/SK14832002A3/sk not_active Application Discontinuation
- 2001-03-21 JP JP2001572482A patent/JP2003529592A/ja active Pending
- 2001-03-29 AR ARP010101522A patent/AR033360A1/es not_active Application Discontinuation
- 2001-03-30 PE PE2001000299A patent/PE20011232A1/es not_active Application Discontinuation
- 2001-05-02 TW TW090107717A patent/TWI284640B/zh active
- 2001-08-07 SA SA01220270A patent/SA01220270B1/ar unknown
- 2001-08-07 SA SA06270303A patent/SA06270303B1/ar unknown
2002
- 2002-09-30 NO NO20024679A patent/NO325005B1/no not_active Application Discontinuation
- 2002-10-03 BG BG107165A patent/BG107165A/bg unknown
2005
- 2005-06-29 AR ARP050102702A patent/AR049560A2/es unknown
2006
- 2006-09-27 AU AU2006222711A patent/AU2006222711A1/en not_active Abandoned

Also Published As

Publication number	Publication date
NO325005B1 (no)	2008-01-14
JP2003529592A (ja)	2003-10-07
CN1422259A (zh)	2003-06-04
MXPA02009559A (es)	2003-05-21
PE20011232A1 (es)	2001-12-08
TWI284640B (en)	2007-08-01
NO20024679D0 (no)	2002-09-30
KR20030011807A (ko)	2003-02-11
HUP0302675A3 (en)	2004-03-29
IL151551A0 (en)	2003-04-10
MY128296A (en)	2007-01-31
PL359727A1 (en)	2004-09-06
AR033360A1 (es)	2003-12-17
AU2001250920B2 (en)	2006-06-29
CA2403635A1 (en)	2001-10-11
CN101066952A (zh)	2007-11-07
BG107165A (bg)	2003-07-31
HUP0302675A2 (hu)	2003-12-29
SA06270303B1 (ar)	2009-08-02
AU2006222711A1 (en)	2006-10-19
WO2001074787A2 (en)	2001-10-11
BR0109433A (pt)	2004-08-10
SA01220270B1 (ar)	2006-11-14
EP1268442A2 (en)	2003-01-02
AU5092001A (en)	2001-10-15
CN1330639C (zh)	2007-08-08
NZ521183A (en)	2004-03-26
KR100773258B1 (ko)	2007-11-05
WO2001074787A3 (en)	2002-02-07
NO20024679L (no)	2002-09-30
AR049560A2 (es)	2006-08-16
CZ20023529A3 (cs)	2003-02-12

Legal Events

Date	Code	Title	Description
2010-03-08	FC9A	Refused patent application

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