DE60038610T2 - Neue kristalline formen eines makrolidantibiotikums - Google Patents
Neue kristalline formen eines makrolidantibiotikums Download PDFInfo
- Publication number
- DE60038610T2 DE60038610T2 DE60038610T DE60038610T DE60038610T2 DE 60038610 T2 DE60038610 T2 DE 60038610T2 DE 60038610 T DE60038610 T DE 60038610T DE 60038610 T DE60038610 T DE 60038610T DE 60038610 T2 DE60038610 T2 DE 60038610T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- crystalline form
- crystalline
- form according
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 61
- 239000013078 crystal Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 150000004682 monohydrates Chemical group 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 12
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 11
- 208000035143 Bacterial infection Diseases 0.000 claims description 10
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000001228 spectrum Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 6
- 208000010362 Protozoan Infections Diseases 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000011877 solvent mixture Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 3
- 238000007920 subcutaneous administration Methods 0.000 claims description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 238000010586 diagram Methods 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 description 30
- -1 CP-472,295 monohydrate Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 241000283690 Bos taurus Species 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 241000193996 Streptococcus pyogenes Species 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003120 macrolide antibiotic agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000193403 Clostridium 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 241000606856 Pasteurella multocida Species 0.000 description 3
- 206010037075 Protozoal infections Diseases 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000000386 microscopy Methods 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 208000028172 protozoa infectious disease Diseases 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound 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
- 241001647372 Chlamydia pneumoniae Species 0.000 description 2
- 241000606153 Chlamydia trachomatis Species 0.000 description 2
- 241000194033 Enterococcus Species 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 2
- 241000191992 Peptostreptococcus Species 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- 206010062255 Soft tissue infection Diseases 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241001312524 Streptococcus viridans Species 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000011203 antimicrobial therapy Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229940038705 chlamydia trachomatis Drugs 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
- 229920001577 copolymer Polymers 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229940047650 haemophilus influenzae Drugs 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 239000004633 polyglycolic acid Substances 0.000 description 2
- 239000004626 polylactic acid Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000002691 unilamellar liposome Substances 0.000 description 2
- 208000019206 urinary tract infection Diseases 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241000606750 Actinobacillus Species 0.000 description 1
- 241000251468 Actinopterygii 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
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241001518086 Bartonella henselae Species 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 241000588807 Bordetella Species 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 241000589969 Borreliella burgdorferi Species 0.000 description 1
- 241000589893 Brachyspira hyodysenteriae Species 0.000 description 1
- 241000589875 Campylobacter jejuni Species 0.000 description 1
- 241000193468 Clostridium perfringens Species 0.000 description 1
- 108010065152 Coagulase Proteins 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- 206010010741 Conjunctivitis 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
- 235000019739 Dicalciumphosphate Nutrition 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
- 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
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010019375 Helicobacter infections Diseases 0.000 description 1
- 241000590002 Helicobacter pylori Species 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241001148567 Lawsonia intracellularis Species 0.000 description 1
- 241000589242 Legionella pneumophila Species 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
- 241000588655 Moraxella catarrhalis Species 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
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 206010048685 Oral infection Diseases 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
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 241000605894 Porphyromonas Species 0.000 description 1
- 241000605861 Prevotella Species 0.000 description 1
- 206010037294 Puerperal pyrexia Diseases 0.000 description 1
- 206010037660 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
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 206010041925 Staphylococcal infections Diseases 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 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
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 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
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 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
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940092524 bartonella henselae Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000037396 body weight Effects 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
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 206010008323 cervicitis Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 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
- 230000004927 fusion Effects 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
- 229960002449 glycine Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940037467 helicobacter pylori Drugs 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 208000028774 intestinal disease Diseases 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
- 206010023332 keratitis Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229940115932 legionella pneumophila Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 238000005259 measurement Methods 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
- 229940013390 mycoplasma pneumoniae Drugs 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
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920002721 polycyanoacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920006324 polyoxymethylene 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
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 208000007865 relapsing fever Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 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
- 201000009890 sinusitis Diseases 0.000 description 1
- 206010040872 skin infection Diseases 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 208000015339 staphylococcus aureus infection Diseases 0.000 description 1
- 229940031000 streptococcus pneumoniae 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
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13464499P | 1999-05-18 | 1999-05-18 | |
| US134644P | 1999-05-18 | ||
| PCT/IB2000/000463 WO2000069874A1 (en) | 1999-05-18 | 2000-04-14 | Novel crystalline forms of a macrolide antibiotic |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60038610D1 DE60038610D1 (de) | 2008-05-29 |
| DE60038610T2 true DE60038610T2 (de) | 2009-06-25 |
Family
ID=22464300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60038610T Expired - Lifetime DE60038610T2 (de) | 1999-05-18 | 2000-04-14 | Neue kristalline formen eines makrolidantibiotikums |
Country Status (43)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6465437B1 (en) * | 1999-06-30 | 2002-10-15 | Pfizer Inc. | Diphosphate salt of a 4″-substituted-9-deoxo-9A-AZA-9A- homoerythromycin derivative and its pharmaceutical composition |
| ATE243703T1 (de) * | 2000-01-27 | 2003-07-15 | Pfizer Prod Inc | Antibiotische azalid-zusammensetzungen |
| CA2445306C (en) * | 2001-04-27 | 2008-02-12 | Pfizer Products Inc. | Process for preparing 4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives |
| EP1435359A1 (en) * | 2002-12-31 | 2004-07-07 | Alembic Limited | A process for the purification of roxithromycin |
| US7384921B2 (en) * | 2004-02-20 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | Polymorphic forms of 6-11 bicyclic ketolide derivatives |
| JP5437394B2 (ja) * | 2009-01-30 | 2014-03-12 | グラクソ グループ リミテッド | 抗炎症性マクロライド |
| EP2402355A1 (en) * | 2010-07-01 | 2012-01-04 | Novartis AG | Crystalline anhydrous forms II and III of Tulathromycin |
| EP2736915A1 (en) | 2011-07-27 | 2014-06-04 | Farma GRS, d.o.o. | New crystalline forms of tulathromycin |
| CN106008622A (zh) * | 2016-08-02 | 2016-10-12 | 海门慧聚药业有限公司 | 泰拉霉素新晶型及其制备 |
| CN109942652B (zh) * | 2017-12-21 | 2022-04-26 | 洛阳惠中兽药有限公司 | 一种莱柯霉素晶型ⅰ及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX12213A (es) * | 1987-07-09 | 1993-05-01 | Pfizer | Metodo de preparacion de dihidrato de azitromicina cristalino |
| US5441939A (en) * | 1994-03-04 | 1995-08-15 | Pfizer Inc. | 3"-desmethoxy derivatives of erythromycin and azithromycin |
| US5844105A (en) * | 1996-07-29 | 1998-12-01 | Abbott Laboratories | Preparation of crystal form II of clarithromycin |
| HN1998000086A (es) * | 1997-06-11 | 1999-03-08 | Pfizer Prod Inc | Derivados de 9 - desofo - 9 aza - 9a - homoeritromicina a - c - 4 sustituidos. |
-
2000
- 2000-04-14 DE DE60038610T patent/DE60038610T2/de not_active Expired - Lifetime
- 2000-04-14 KR KR10-2001-7014687A patent/KR100474229B1/ko not_active Expired - Fee Related
- 2000-04-14 HR HR20010849A patent/HRP20010849A2/hr not_active Application Discontinuation
- 2000-04-14 PT PT00914336T patent/PT1189912E/pt unknown
- 2000-04-14 UA UA2001117852A patent/UA67842C2/uk unknown
- 2000-04-14 EA EA200100984A patent/EA003417B1/ru not_active IP Right Cessation
- 2000-04-14 WO PCT/IB2000/000463 patent/WO2000069874A1/en not_active Ceased
- 2000-04-14 AP APAP/P/2001/002325A patent/AP2001002325A0/en unknown
- 2000-04-14 AU AU35729/00A patent/AU772283B2/en not_active Ceased
- 2000-04-14 YU YU76601A patent/YU76601A/sh unknown
- 2000-04-14 CA CA002372206A patent/CA2372206C/en not_active Expired - Lifetime
- 2000-04-14 NZ NZ514765A patent/NZ514765A/en unknown
- 2000-04-14 SK SK1647-2001A patent/SK16472001A3/sk unknown
- 2000-04-14 BR BR0011300-0A patent/BR0011300A/pt not_active Application Discontinuation
- 2000-04-14 HU HU0201341A patent/HUP0201341A3/hu unknown
- 2000-04-14 DK DK00914336T patent/DK1189912T3/da active
- 2000-04-14 EP EP00914336A patent/EP1189912B1/en not_active Expired - Lifetime
- 2000-04-14 HK HK02107017.2A patent/HK1045521B/zh not_active IP Right Cessation
- 2000-04-14 JP JP2000618290A patent/JP3897983B2/ja not_active Expired - Fee Related
- 2000-04-14 AT AT00914336T patent/ATE392427T1/de not_active IP Right Cessation
- 2000-04-14 OA OA1200100283A patent/OA11876A/en unknown
- 2000-04-14 CZ CZ20014120A patent/CZ20014120A3/cs unknown
- 2000-04-14 CN CNB008077029A patent/CN1203084C/zh not_active Expired - Fee Related
- 2000-04-14 MX MXPA01011914A patent/MXPA01011914A/es active IP Right Grant
- 2000-04-14 ES ES00914336T patent/ES2302689T3/es not_active Expired - Lifetime
- 2000-04-14 PL PL00353316A patent/PL353316A1/xx unknown
- 2000-04-14 IL IL14594600A patent/IL145946A0/xx active IP Right Grant
- 2000-04-25 HN HN2000000056A patent/HN2000000056A/es unknown
- 2000-05-02 US US09/563,792 patent/US6583274B1/en not_active Expired - Lifetime
- 2000-05-05 PA PA20008495001A patent/PA8495001A1/es unknown
- 2000-05-12 TW TW089109175A patent/TWI225066B/zh not_active IP Right Cessation
- 2000-05-15 MY MYPI20002125A patent/MY133397A/en unknown
- 2000-05-15 UY UY26144A patent/UY26144A1/es not_active Application Discontinuation
- 2000-05-16 PE PE2000000459A patent/PE20010151A1/es not_active Application Discontinuation
- 2000-05-16 AR ARP000102353A patent/AR020030A1/es not_active Application Discontinuation
- 2000-05-17 TN TNTNSN00103A patent/TNSN00103A1/fr unknown
- 2000-05-17 DZ DZ000086A patent/DZ3043A1/xx active
- 2000-05-17 GT GT200000072A patent/GT200000072A/es unknown
- 2000-05-17 MA MA25979A patent/MA26735A1/fr unknown
-
2001
- 2001-10-15 IL IL145946A patent/IL145946A/en unknown
- 2001-10-26 IS IS6127A patent/IS6127A/is unknown
- 2001-11-15 ZA ZA200109420A patent/ZA200109420B/xx unknown
- 2001-11-16 NO NO20015598A patent/NO320195B1/no unknown
- 2001-11-26 BG BG106150A patent/BG106150A/bg unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60209704T2 (de) | Neue kristallforme von azithromycin | |
| DE69818665T2 (de) | 4"-substitutierte-9-deoxo-9a-aza-9a-homoerythromycin a derivate | |
| DE69919769T2 (de) | 3,6-Ketal-Makrolidantibiotika | |
| DE69915336T2 (de) | 13-gliedrige azalide und ihre verwendung als antibiotika | |
| DE69913738T2 (de) | Ketolid-antibiotika | |
| DE69832486T2 (de) | C-4"-substitutierte macrolid-derivate | |
| TWI425942B (zh) | 巨環性多形物，包含此類多形物之組成物，以及其之使用及製造方法 | |
| DE69933897T2 (de) | Carbamat- und Carbazatketolid-Antibiotika | |
| DE60123277T2 (de) | Makrolidantibiotika | |
| DE69712610T2 (de) | Erythramicin-derivate, ihre verfahren zur herstellung und ihre verwendung als arzneimittel | |
| DE69920362T2 (de) | Neue Makrolidderivate | |
| DE60102171T2 (de) | Ketolidantibiotika | |
| DE69917717T2 (de) | C11-Carbamate von antibakteriellen Makroliden | |
| DE69631609T2 (de) | Tricyclische erythromycinderivate | |
| DE602004003809T2 (de) | Neue 14- und 15-gliedrige ringverbindungen | |
| EP1189912B1 (en) | Novel crystalline forms of a macrolide antibiotic | |
| DE60104240T2 (de) | Makrolid-Antibiotika | |
| DE69926005T2 (de) | Carbamat- und carbazatketolidantibiotika | |
| US20020061856A1 (en) | Novel tricyclic erythromycin derivatives | |
| US20020077302A1 (en) | Tricyclic erythromycin derivatives | |
| DE69908855T2 (de) | 9a, 11b-dehydro Derivative von 9-oxime-3-keto-6-0-methylerythromycin | |
| MXPA01000114A (en) | Novel antibacterial and prokinetic macrolides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |