CA2536914C - Formes cristallines de l'azithromycine - Google Patents

Formes cristallines de l'azithromycine Download PDF

Info

Publication number: CA2536914C
Authority: CA; Canada
Prior art keywords: azithromycin; ppm; peaks; water; theta
Prior art date: 2001-05-22
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.): Expired - Fee Related

Application number

CA002536914A

Other languages

English (en)

Other versions

CA2536914A1 (fr

Inventor

Zheng Jane Li

Andrew Vincent Trask

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Pfizer Products Inc

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.)

2001-05-22

Filing date

2002-05-01

Publication date

2008-01-15

2002-05-01 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2002-05-01 Priority claimed from CA002391659A external-priority patent/CA2391659C/fr

2002-11-22 Publication of CA2536914A1 publication Critical patent/CA2536914A1/fr

2008-01-15 Application granted granted Critical

2008-01-15 Publication of CA2536914C publication Critical patent/CA2536914C/fr

2022-05-01 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 title claims abstract description 275
229960004099 azithromycin Drugs 0.000 title claims abstract description 274
239000013078 crystal Substances 0.000 title abstract description 80
238000001228 spectrum Methods 0.000 claims description 39
239000000126 substance Substances 0.000 claims description 39
239000012453 solvate Substances 0.000 claims description 21
HQUPLSLYZHKKQT-WVVFQGGUSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-o Chemical compound O.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 HQUPLSLYZHKKQT-WVVFQGGUSA-N 0.000 claims description 12
229960003256 azithromycin monohydrate Drugs 0.000 claims description 12
238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims 8
208000015181 infectious disease Diseases 0.000 abstract description 48
238000011282 treatment Methods 0.000 abstract description 9
239000003242 anti bacterial agent Substances 0.000 abstract description 3
230000003115 biocidal effect Effects 0.000 abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 50
238000000634 powder X-ray diffraction Methods 0.000 description 45
150000001875 compounds Chemical class 0.000 description 35
239000000243 solution Substances 0.000 description 34
239000007787 solid Substances 0.000 description 33
239000002904 solvent Substances 0.000 description 30
239000000843 powder Substances 0.000 description 28
238000000034 method Methods 0.000 description 26
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 25
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
238000001144 powder X-ray diffraction data Methods 0.000 description 16
238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 14
239000002002 slurry Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
239000000523 sample Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 12
208000035143 Bacterial infection Diseases 0.000 description 11
208000022362 bacterial infectious disease Diseases 0.000 description 11
238000004090 dissolution Methods 0.000 description 11
238000001914 filtration Methods 0.000 description 11
229910052760 oxygen Inorganic materials 0.000 description 11
238000003556 assay Methods 0.000 description 10
238000001816 cooling Methods 0.000 description 10
238000002425 crystallisation Methods 0.000 description 10
230000008025 crystallization Effects 0.000 description 10
229960004063 propylene glycol Drugs 0.000 description 10
239000003826 tablet Substances 0.000 description 10
241000283690 Bos taurus Species 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000002447 crystallographic data Methods 0.000 description 9
239000003120 macrolide antibiotic agent Substances 0.000 description 9
238000001556 precipitation Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
241000606856 Pasteurella multocida Species 0.000 description 7
241000194017 Streptococcus Species 0.000 description 7
230000018044 dehydration Effects 0.000 description 7
238000006297 dehydration reaction Methods 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
241000251468 Actinopterygii Species 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
241000124008 Mammalia Species 0.000 description 6
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
241000191967 Staphylococcus aureus Species 0.000 description 6
241000193996 Streptococcus pyogenes Species 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
150000004682 monohydrates Chemical class 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000003828 vacuum filtration Methods 0.000 description 6
241001293418 Mannheimia haemolytica Species 0.000 description 5
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
239000012296 anti-solvent Substances 0.000 description 5
238000004807 desolvation Methods 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
238000009792 diffusion process Methods 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
239000012458 free base Substances 0.000 description 4
-1 isopropanvl Chemical class 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
238000003752 polymerase chain reaction Methods 0.000 description 4
230000008261 resistance mechanism Effects 0.000 description 4
238000013207 serial dilution Methods 0.000 description 4
239000006104 solid solution Substances 0.000 description 4
239000011877 solvent mixture Substances 0.000 description 4
238000002411 thermogravimetry Methods 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000193403 Clostridium Species 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
241000606768 Haemophilus influenzae Species 0.000 description 3
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 3
241000588655 Moraxella catarrhalis Species 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
238000002441 X-ray diffraction Methods 0.000 description 3
239000008272 agar Substances 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
229940041033 macrolides Drugs 0.000 description 3
238000002156 mixing Methods 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000002674 ointment Substances 0.000 description 3
244000052769 pathogen Species 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
230000009467 reduction Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241001148536 Bacteroides sp. Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241001647372 Chlamydia pneumoniae Species 0.000 description 2
108010065152 Coagulase Proteins 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
235000019739 Dicalciumphosphate Nutrition 0.000 description 2
241000194033 Enterococcus Species 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000590002 Helicobacter pylori Species 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
101150052154 MSRA1 gene Proteins 0.000 description 2
238000004497 NIR spectroscopy Methods 0.000 description 2
241000191992 Peptostreptococcus Species 0.000 description 2
206010062255 Soft tissue infection Diseases 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
241000193998 Streptococcus pneumoniae Species 0.000 description 2
108700024076 Streptococcus pyogenes ermB Proteins 0.000 description 2
241001312524 Streptococcus viridans Species 0.000 description 2
241000282898 Sus scrofa Species 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
238000011203 antimicrobial therapy Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000006285 cell suspension Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000005384 cross polarization magic-angle spinning Methods 0.000 description 2
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
229940038472 dicalcium phosphate Drugs 0.000 description 2
229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000000499 gel Substances 0.000 description 2
229940047650 haemophilus influenzae Drugs 0.000 description 2
229940037467 helicobacter pylori Drugs 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
208000028774 intestinal disease Diseases 0.000 description 2
235000015110 jellies Nutrition 0.000 description 2
239000002502 liposome Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
101150021123 msrA gene Proteins 0.000 description 2
101150114366 msrA2 gene Proteins 0.000 description 2
101150006794 msrAB gene Proteins 0.000 description 2
101150109310 msrAB1 gene Proteins 0.000 description 2
101150052209 msrAB2 gene Proteins 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000005855 radiation Effects 0.000 description 2
208000023504 respiratory system disease Diseases 0.000 description 2
206010040872 skin infection Diseases 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 description 2
241000894007 species Species 0.000 description 2
229940031000 streptococcus pneumoniae Drugs 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000000725 suspension Substances 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
239000002691 unilamellar liposome Substances 0.000 description 2
208000019206 urinary tract infection Diseases 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
VQEMDSRIOVZAOM-UHFFFAOYSA-N 4-(4-methylsulfonylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CSC(N)=N1 VQEMDSRIOVZAOM-UHFFFAOYSA-N 0.000 description 1
241000606750 Actinobacillus Species 0.000 description 1
241000588986 Alcaligenes 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
WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.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 WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
241000271566 Aves Species 0.000 description 1
241001518086 Bartonella henselae Species 0.000 description 1
241000588807 Bordetella Species 0.000 description 1
241000180135 Borrelia recurrentis Species 0.000 description 1
241000589969 Borreliella burgdorferi Species 0.000 description 1
241001148534 Brachyspira Species 0.000 description 1
241000589875 Campylobacter jejuni Species 0.000 description 1
241000606161 Chlamydia Species 0.000 description 1
241000606153 Chlamydia trachomatis Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000193468 Clostridium perfringens Species 0.000 description 1
241000224483 Coccidia Species 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
208000031973 Conjunctivitis infective Diseases 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
241001518260 Corynebacterium minutissimum Species 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
208000008953 Cryptosporidiosis Diseases 0.000 description 1
241000605721 Dichelobacter nodosus Species 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000186394 Eubacterium Species 0.000 description 1
208000001860 Eye Infections Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
206010016952 Food poisoning Diseases 0.000 description 1
208000019331 Foodborne disease Diseases 0.000 description 1
241000605909 Fusobacterium Species 0.000 description 1
241000605952 Fusobacterium necrophorum Species 0.000 description 1
201000000628 Gas Gangrene Diseases 0.000 description 1
208000005577 Gastroenteritis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
241000606790 Haemophilus Species 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
244000147568 Laurus nobilis Species 0.000 description 1
235000017858 Laurus nobilis Nutrition 0.000 description 1
241001148567 Lawsonia intracellularis Species 0.000 description 1
241000589242 Legionella pneumophila Species 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241000186781 Listeria Species 0.000 description 1
208000016604 Lyme disease Diseases 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
208000010315 Mastoiditis Diseases 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000588622 Moraxella bovis Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
101100240347 Mus musculus Nectin2 gene Proteins 0.000 description 1
241000186367 Mycobacterium avium Species 0.000 description 1
241000513886 Mycobacterium avium complex (MAC) Species 0.000 description 1
241000186364 Mycobacterium intracellulare Species 0.000 description 1
241000204031 Mycoplasma Species 0.000 description 1
241001138504 Mycoplasma bovis Species 0.000 description 1
241000202934 Mycoplasma pneumoniae Species 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
206010031252 Osteomyelitis Diseases 0.000 description 1
206010033078 Otitis media Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
201000005702 Pertussis Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
241000605894 Porphyromonas Species 0.000 description 1
241000756999 Potamogetonaceae Species 0.000 description 1
241000605861 Prevotella Species 0.000 description 1
102000055027 Protein Methyltransferases Human genes 0.000 description 1
108700040121 Protein Methyltransferases Proteins 0.000 description 1
206010037294 Puerperal pyrexia Diseases 0.000 description 1
206010057190 Respiratory tract infections Diseases 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
208000019802 Sexually transmitted disease Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
101100182276 Staphylococcus aureus ermC gene Proteins 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
241001147691 Staphylococcus saprophyticus Species 0.000 description 1
108700037081 Streptococcus pneumoniae MefE Proteins 0.000 description 1
108010015795 Streptogramin B Proteins 0.000 description 1
108010034396 Streptogramins Proteins 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
235000005212 Terminalia tomentosa Nutrition 0.000 description 1
206010044248 Toxic shock syndrome Diseases 0.000 description 1
231100000650 Toxic shock syndrome Toxicity 0.000 description 1
241000223997 Toxoplasma gondii Species 0.000 description 1
241000589884 Treponema pallidum Species 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
241000202921 Ureaplasma urealyticum Species 0.000 description 1
208000006374 Uterine Cervicitis Diseases 0.000 description 1
206010046793 Uterine inflammation Diseases 0.000 description 1
241000606834 [Haemophilus] ducreyi Species 0.000 description 1
206010000210 abortion Diseases 0.000 description 1
231100000176 abortion Toxicity 0.000 description 1
206010000269 abscess Diseases 0.000 description 1
201000001028 acute contagious conjunctivitis Diseases 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
238000000137 annealing Methods 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229960004924 azithromycin dihydrate Drugs 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
229940092524 bartonella henselae Drugs 0.000 description 1
210000003323 beak Anatomy 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229960003563 calcium carbonate Drugs 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
206010008323 cervicitis Diseases 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000007910 chewable tablet Substances 0.000 description 1
229940068682 chewable tablet Drugs 0.000 description 1
229940038705 chlamydia trachomatis Drugs 0.000 description 1
239000000460 chlorine Chemical group 0.000 description 1
229910052801 chlorine Chemical group 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000004590 computer program Methods 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
201000010251 cutis laxa Diseases 0.000 description 1
235000013365 dairy product Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
229960003276 erythromycin Drugs 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
208000011323 eye infectious disease Diseases 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Chemical group 0.000 description 1
230000009246 food effect Effects 0.000 description 1
235000021471 food effect Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
208000010801 foot rot Diseases 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000001087 glyceryl triacetate Substances 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
150000003278 haem Chemical class 0.000 description 1
YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000012844 infrared spectroscopy analysis Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
206010023332 keratitis Diseases 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
229960001021 lactose monohydrate Drugs 0.000 description 1
229940115932 legionella pneumophila Drugs 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
229940041028 lincosamides Drugs 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
101150111763 mefA gene Proteins 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000004200 microcrystalline wax Substances 0.000 description 1
235000019808 microcrystalline wax Nutrition 0.000 description 1
238000000302 molecular modelling Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
229940013390 mycoplasma pneumoniae Drugs 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
239000001301 oxygen Chemical group 0.000 description 1
238000012856 packing Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
229940051027 pasteurella multocida Drugs 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000008105 phosphatidylcholines Chemical class 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
YGXCETJZBDTKRY-DZCVGBHJSA-N pristinamycin IA Chemical compound N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-DZCVGBHJSA-N 0.000 description 1
CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000011160 research Methods 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
238000004467 single crystal X-ray diffraction Methods 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229940041030 streptogramins Drugs 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108091005703 transmembrane proteins Proteins 0.000 description 1
102000035160 transmembrane proteins Human genes 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
238000012800 visualization Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000004457 water analysis Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002536914A 2001-05-22 2002-05-01 Formes cristallines de l'azithromycine Expired - Fee Related CA2536914C (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
US29256501P	2001-05-22	2001-05-22
US60/292,565		2001-05-22
US29774101P	2001-06-12	2001-06-12
US60/297,741		2001-06-12
US34304101P	2001-12-21	2001-12-21
US60/343,041		2001-12-21
CA002391659A CA2391659C (fr)	2001-05-22	2002-05-01	Formes cristallines de l'azithromycine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002391659A Division CA2391659C (fr)	2001-05-22	2002-05-01	Formes cristallines de l'azithromycine

Publications (2)

Publication Number	Publication Date
CA2536914A1 CA2536914A1 (fr)	2002-11-22
CA2536914C true CA2536914C (fr)	2008-01-15

Family

ID=34577710

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CA002536914A Expired - Fee Related CA2536914C (fr)	2001-05-22	2002-05-01	Formes cristallines de l'azithromycine
CA002536501A Expired - Fee Related CA2536501C (fr)	2001-05-22	2002-05-01	Formes cristallines de l'azithromycine
CA002500217A Expired - Fee Related CA2500217C (fr)	2001-05-22	2002-05-01	Formes cristallines de l'azithromycine

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CA002536501A Expired - Fee Related CA2536501C (fr)	2001-05-22	2002-05-01	Formes cristallines de l'azithromycine
CA002500217A Expired - Fee Related CA2500217C (fr)	2001-05-22	2002-05-01	Formes cristallines de l'azithromycine

Country Status (1)

Country	Link
CA (3)	CA2536914C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119060109A (zh) *	2024-11-01	2024-12-03	德州德药制药有限公司	一种富马酸阿奇霉素晶型及其制备方法

2002
- 2002-05-01 CA CA002536914A patent/CA2536914C/fr not_active Expired - Fee Related
- 2002-05-01 CA CA002536501A patent/CA2536501C/fr not_active Expired - Fee Related
- 2002-05-01 CA CA002500217A patent/CA2500217C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2500217A1 (fr)	2002-11-22
CA2536501A1 (fr)	2002-11-22
CA2536914A1 (fr)	2002-11-22
CA2500217C (fr)	2005-11-29
CA2536501C (fr)	2006-09-26

Legal Events

Date	Code	Title	Description
2006-02-27	EEER	Examination request
2013-06-13	MKLA	Lapsed	Effective date: 20130501

Publication	Publication Date	Title
AU2002256846B2 (en)	2007-04-05	Crystal Forms of Azithromycin
AU2002256846A1 (en)	2003-05-08	Crystal Forms of Azithromycin
US6518251B1 (en)	2003-02-11	Macrolides
US20020052328A1 (en)	2002-05-02	Macrolide antibiotics
CN100354294C (zh)	2007-12-12	阿奇霉素的晶形
CA2536501C (fr)	2006-09-26	Formes cristallines de l'azithromycine
EP1671979B1 (fr)	2008-08-13	Nouvelle forme cristalline de l'azithromycine
US6258785B1 (en)	2001-07-10	Crystalline 9-E-(O-methyl)oxime of 11, 12-dideoxy-3-de(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribohexopyranosyloxy)-6-O-methyl-12,11-(iminocarbonyl-(2-(3-(4-(3-pyridinyl)1H-imadazol-1-yl)propyl)hydrazono))-3-oxoerythromycin