KR100486053B1 - 신규에리트로마이신유도체,그의제조방법및약제로서의그의용도 - Google Patents
신규에리트로마이신유도체,그의제조방법및약제로서의그의용도 Download PDFInfo
- Publication number
- KR100486053B1 KR100486053B1 KR10-1998-0706733A KR19980706733A KR100486053B1 KR 100486053 B1 KR100486053 B1 KR 100486053B1 KR 19980706733 A KR19980706733 A KR 19980706733A KR 100486053 B1 KR100486053 B1 KR 100486053B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- radical
- compound
- methyl
- dideoxy
- 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
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class 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 title claims description 10
- 238000000034 method Methods 0.000 title claims description 10
- 239000003814 drug Substances 0.000 title description 7
- 229940079593 drug Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 150000003254 radicals Chemical class 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- -1 oxycarbonyl (2- (3- (4-quinolinyl) propyl) hydrazono) Chemical class 0.000 claims description 34
- 229960003276 erythromycin Drugs 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 208000035109 Pneumococcal Infections Diseases 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 206010041925 Staphylococcal infections Diseases 0.000 claims 1
- 206010061372 Streptococcal infection Diseases 0.000 claims 1
- 150000005840 aryl radicals Chemical group 0.000 abstract description 4
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
- 229940088710 antibiotic agent Drugs 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 241000194017 Streptococcus Species 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000191940 Staphylococcus Species 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241001134658 Streptococcus mitis Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- GTJNQHWEJNBLLS-UHFFFAOYSA-N n,n-diethylethanamine;methanol;2-propan-2-yloxypropane Chemical compound OC.CCN(CC)CC.CC(C)OC(C)C GTJNQHWEJNBLLS-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 238000004454 trace mineral analysis Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- MWBJRTBANFUBOX-SQYJNGITSA-N (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/O)/[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MWBJRTBANFUBOX-SQYJNGITSA-N 0.000 description 1
- OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 description 1
- RVHOBHMAPRVOLO-UHFFFAOYSA-N 2-ethylbutanedioic acid Chemical compound CCC(C(O)=O)CC(O)=O RVHOBHMAPRVOLO-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 201000004813 Bronchopneumonia Diseases 0.000 description 1
- 206010007882 Cellulitis Diseases 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000589248 Legionella Species 0.000 description 1
- 208000007764 Legionnaires' Disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000202934 Mycoplasma pneumoniae Species 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000606701 Rickettsia Species 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 206010066409 Staphylococcal skin infection Diseases 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000223996 Toxoplasma Species 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 241000202898 Ureaplasma Species 0.000 description 1
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000005638 hydrazono group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9602472A FR2745290B1 (fr) | 1996-02-28 | 1996-02-28 | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR96/02472 | 1996-02-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR19990087324A KR19990087324A (ko) | 1999-12-27 |
| KR100486053B1 true KR100486053B1 (ko) | 2005-06-16 |
Family
ID=9489659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-1998-0706733A Expired - Lifetime KR100486053B1 (ko) | 1996-02-28 | 1997-02-27 | 신규에리트로마이신유도체,그의제조방법및약제로서의그의용도 |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6096714A (enExample) |
| EP (1) | EP0885234B1 (enExample) |
| JP (1) | JP4102440B2 (enExample) |
| KR (1) | KR100486053B1 (enExample) |
| CN (1) | CN1168734C (enExample) |
| AP (1) | AP952A (enExample) |
| AR (1) | AR005999A1 (enExample) |
| AT (1) | ATE217633T1 (enExample) |
| AU (1) | AU716204B2 (enExample) |
| BG (1) | BG63207B1 (enExample) |
| BR (1) | BR9707709B1 (enExample) |
| CZ (1) | CZ293893B6 (enExample) |
| DE (1) | DE69712610T2 (enExample) |
| DK (1) | DK0885234T3 (enExample) |
| EA (1) | EA001376B1 (enExample) |
| EE (1) | EE9800265A (enExample) |
| ES (1) | ES2176698T3 (enExample) |
| FR (1) | FR2745290B1 (enExample) |
| HU (1) | HU227567B1 (enExample) |
| IL (1) | IL125622A (enExample) |
| NO (1) | NO983955D0 (enExample) |
| NZ (1) | NZ331600A (enExample) |
| OA (1) | OA10845A (enExample) |
| PL (1) | PL191736B1 (enExample) |
| PT (1) | PT885234E (enExample) |
| SK (1) | SK118498A3 (enExample) |
| TR (1) | TR199801713T2 (enExample) |
| UA (1) | UA58504C2 (enExample) |
| WO (1) | WO1997031929A1 (enExample) |
| YU (1) | YU37098A (enExample) |
| ZA (1) | ZA971659B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999021870A1 (en) * | 1997-10-29 | 1999-05-06 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a 11, 12-carbamate derivatives |
| JP2003527301A (ja) * | 1997-10-29 | 2003-09-16 | 大正製薬株式会社 | エリスロマイシンａ誘導体 |
| FR2792637B1 (fr) * | 1999-04-26 | 2001-06-01 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2780977B1 (fr) * | 1998-07-09 | 2000-09-01 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| JP4573925B2 (ja) * | 1998-07-09 | 2010-11-04 | アベンティス・ファーマ・ソシエテ・アノニム | 新規のエリスロマイシン誘導体、その製造方法及びその薬剤としての使用 |
| FR2781484B1 (fr) * | 1998-07-21 | 2001-08-10 | Hoechst Marion Roussel Inc | Nouveaux derives de la 6-deoxy erythromycine, leur procede de preparation et leur application comme medicaments |
| OA11753A (en) | 1999-01-27 | 2005-07-19 | Pfizer Prod Inc | Ketolide antibiotics. |
| KR20020016799A (ko) * | 1999-05-24 | 2002-03-06 | 데이비드 존 우드 | 13-메틸-에리트로마이신 유도체 |
| AU6183800A (en) * | 1999-08-06 | 2001-03-05 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
| WO2001010879A1 (fr) * | 1999-08-06 | 2001-02-15 | Taisho Pharmaceutical Co., Ltd. | Derives d'erythromycine a |
| WO2001010878A1 (fr) * | 1999-08-06 | 2001-02-15 | Taisho Pharmaceutical Co., Ltd. | Derives d'erythromycine a |
| EP1146051A3 (en) * | 2000-04-10 | 2001-10-31 | Pfizer Products Inc. | Erythromycin A derivatives |
| US20020115621A1 (en) * | 2000-08-07 | 2002-08-22 | Wei-Gu Su | Macrolide antibiotics |
| ITMI20021726A1 (it) | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| CA2529817C (en) | 2003-03-10 | 2013-02-12 | Optimer Pharmaceuticals, Inc. | Novel antibacterial agents |
| US20050014706A1 (en) * | 2003-07-14 | 2005-01-20 | Kanakeshwari Falzari | Method of treating tuberculosis |
| WO2007069264A2 (en) * | 2005-12-15 | 2007-06-21 | Alembic Limited | Reference standards for determining the purity of telithromycin and processes therefor |
| AU2008316830B2 (en) * | 2007-10-25 | 2016-03-17 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| WO2010048600A1 (en) * | 2008-10-24 | 2010-04-29 | Cempra Pharmaceuticals, Inc. | Methods for treating resistant diseases using triazole containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| US9480679B2 (en) | 2009-09-10 | 2016-11-01 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and MAC diseases |
| HRP20160168T1 (hr) | 2010-03-22 | 2016-03-25 | Cempra Pharmaceuticals Inc | Kristalne forme makrolida i njihova uporaba |
| EP2571506B1 (en) | 2010-05-20 | 2017-05-10 | Cempra Pharmaceuticals, Inc. | Processes for preparing macrolides and ketolides and intermediates therefor |
| KR20130120458A (ko) | 2010-09-10 | 2013-11-04 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| WO2013148891A1 (en) | 2012-03-27 | 2013-10-03 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| EP2968801B1 (en) | 2013-03-14 | 2018-09-26 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| MX356772B (es) | 2013-03-15 | 2018-06-13 | Cempra Pharmaceuticals Inc | Procesos convergentes para la preparacion de agentes antibacterianos macrolidos. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5444051A (en) * | 1990-11-21 | 1995-08-22 | Roussel Uclaf | Erythromycin compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US487411A (en) * | 1892-12-06 | Island | ||
| US5444031A (en) * | 1993-01-21 | 1995-08-22 | Calgon Carbon Corporation | Process for making catalytic carbon |
| FR2727969B1 (fr) * | 1994-12-09 | 1997-01-17 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
-
1996
- 1996-02-28 FR FR9602472A patent/FR2745290B1/fr not_active Expired - Lifetime
-
1997
- 1997-02-25 AR ARP970100760A patent/AR005999A1/es unknown
- 1997-02-26 ZA ZA9701659A patent/ZA971659B/xx unknown
- 1997-02-27 DK DK97907141T patent/DK0885234T3/da active
- 1997-02-27 BR BRPI9707709-7A patent/BR9707709B1/pt not_active IP Right Cessation
- 1997-02-27 CN CNB971926255A patent/CN1168734C/zh not_active Expired - Lifetime
- 1997-02-27 EP EP97907141A patent/EP0885234B1/fr not_active Expired - Lifetime
- 1997-02-27 UA UA98095031A patent/UA58504C2/uk unknown
- 1997-02-27 IL IL12562297A patent/IL125622A/xx not_active IP Right Cessation
- 1997-02-27 DE DE69712610T patent/DE69712610T2/de not_active Expired - Lifetime
- 1997-02-27 TR TR1998/01713T patent/TR199801713T2/xx unknown
- 1997-02-27 PL PL328608A patent/PL191736B1/pl unknown
- 1997-02-27 US US09/125,959 patent/US6096714A/en not_active Ceased
- 1997-02-27 CZ CZ19982587A patent/CZ293893B6/cs not_active IP Right Cessation
- 1997-02-27 EA EA199800768A patent/EA001376B1/ru not_active IP Right Cessation
- 1997-02-27 WO PCT/FR1997/000351 patent/WO1997031929A1/fr not_active Ceased
- 1997-02-27 JP JP53067197A patent/JP4102440B2/ja not_active Expired - Lifetime
- 1997-02-27 AT AT97907141T patent/ATE217633T1/de active
- 1997-02-27 EE EE9800265A patent/EE9800265A/xx unknown
- 1997-02-27 ES ES97907141T patent/ES2176698T3/es not_active Expired - Lifetime
- 1997-02-27 KR KR10-1998-0706733A patent/KR100486053B1/ko not_active Expired - Lifetime
- 1997-02-27 SK SK1184-98A patent/SK118498A3/sk unknown
- 1997-02-27 AU AU19298/97A patent/AU716204B2/en not_active Expired
- 1997-02-27 HU HU9902576A patent/HU227567B1/hu unknown
- 1997-02-27 AP APAP/P/1998/001318A patent/AP952A/en active
- 1997-02-27 PT PT97907141T patent/PT885234E/pt unknown
- 1997-02-27 NZ NZ331600A patent/NZ331600A/xx unknown
-
1998
- 1998-08-12 BG BG102691A patent/BG63207B1/bg unknown
- 1998-08-27 NO NO983955A patent/NO983955D0/no not_active Application Discontinuation
- 1998-08-28 YU YU37098A patent/YU37098A/sh unknown
- 1998-08-28 OA OA9800150A patent/OA10845A/fr unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5444051A (en) * | 1990-11-21 | 1995-08-22 | Roussel Uclaf | Erythromycin compounds |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100486053B1 (ko) | 신규에리트로마이신유도체,그의제조방법및약제로서의그의용도 | |
| JP2992540B2 (ja) | 新規なエリスロマイシン誘導体、それらの製造法及び薬剤としての使用 | |
| JP3140703B2 (ja) | 新規なエリスロマイシン、それらの製造法及び薬剤としての用途 | |
| KR100371473B1 (ko) | 신규한에리스로마이신유도체,그의제조방법및의약으로서의용도 | |
| KR20010080970A (ko) | 에리쓰로마이신의 신규 유도체, 그의 제조 방법 및의약으로서 그의 용도 | |
| JP4573925B2 (ja) | 新規のエリスロマイシン誘導体、その製造方法及びその薬剤としての使用 | |
| JP5188520B2 (ja) | 新規なエリスロマイシン誘導体、製造方法及び医薬としての利用 | |
| AP997A (en) | Novel erythromycin derivatives, method for preparing them and their use as medicine. | |
| KR100529980B1 (ko) | 신규 에리트로마이신 유도체, 그의 제조 방법 및 의약으로서의용도 | |
| KR20000068014A (ko) | 신규 에리트로마이신 유도체, 그의 제조방법 및 의약으로서의용도 | |
| USRE38520E1 (en) | Erythromycin derivatives, method for preparing same, and use thereof as drugs | |
| AU761551B2 (en) | Novel 6-deoxy erythromycin derivatives, method for preparing same and use as medicines | |
| MXPA99005226A (en) | Novel erythromycin derivatives, method for preparing them and their use as medicine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19980827 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20020225 Comment text: Request for Examination of Application |
|
| N231 | Notification of change of applicant | ||
| PN2301 | Change of applicant |
Patent event date: 20040127 Comment text: Notification of Change of Applicant Patent event code: PN23011R01D |
|
| E801 | Decision on dismissal of amendment | ||
| PE0801 | Dismissal of amendment |
Patent event code: PE08012E01D Comment text: Decision on Dismissal of Amendment Patent event date: 20040330 Patent event code: PE08011R01I Comment text: Amendment to Specification, etc. Patent event date: 20020225 |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20040630 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20050131 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20050420 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20050421 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20080411 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20090410 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20100414 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20110318 Start annual number: 7 End annual number: 7 |
|
| FPAY | Annual fee payment | ||
| PR1001 | Payment of annual fee |
Payment date: 20120409 Start annual number: 8 End annual number: 8 |
|
| FPAY | Annual fee payment | ||
| PR1001 | Payment of annual fee |
Payment date: 20130403 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20140331 Start annual number: 10 End annual number: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20150323 Start annual number: 11 End annual number: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20160318 Year of fee payment: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20160318 Start annual number: 12 End annual number: 12 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |