JP2000513026A - ９−オキシム エリスロマイシン誘導体 - Google Patents
９−オキシム エリスロマイシン誘導体Info
- Publication number
- JP2000513026A JP2000513026A JP11501928A JP50192899A JP2000513026A JP 2000513026 A JP2000513026 A JP 2000513026A JP 11501928 A JP11501928 A JP 11501928A JP 50192899 A JP50192899 A JP 50192899A JP 2000513026 A JP2000513026 A JP 2000513026A
- Authority
- JP
- Japan
- Prior art keywords
- deoxy
- hydrazo
- desosaminol
- deoxo
- carbamate
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 292
- 150000003839 salts Chemical class 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 60
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 25
- 230000001580 bacterial effect Effects 0.000 claims abstract description 23
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 Cl-CIO alkanoyl Chemical group 0.000 claims description 297
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 31
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 23
- 241000251468 Actinopterygii Species 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- 206010037075 Protozoal infections Diseases 0.000 claims description 15
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 241000271566 Aves Species 0.000 claims description 13
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 2
- 241001553014 Myrsine salicina Species 0.000 claims 1
- 208000010362 Protozoan Infections Diseases 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- 239000000243 solution Substances 0.000 description 67
- 208000015181 infectious disease Diseases 0.000 description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000007787 solid Substances 0.000 description 43
- 239000012267 brine Substances 0.000 description 33
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
- 239000012044 organic layer Substances 0.000 description 32
- 239000010410 layer Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 239000012043 crude product Substances 0.000 description 27
- 238000012360 testing method Methods 0.000 description 25
- 238000003556 assay Methods 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 24
- 239000003120 macrolide antibiotic agent Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- 241000283690 Bos taurus Species 0.000 description 17
- 241000606856 Pasteurella multocida Species 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 16
- 241000606860 Pasteurella Species 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 12
- 241001293418 Mannheimia haemolytica Species 0.000 description 12
- 241000193996 Streptococcus pyogenes Species 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 150000001447 alkali salts Chemical class 0.000 description 12
- 229960002626 clarithromycin Drugs 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 241000191967 Staphylococcus aureus Species 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 150000001768 cations Chemical class 0.000 description 10
- 238000010790 dilution Methods 0.000 description 10
- 239000012895 dilution Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 241000588724 Escherichia coli Species 0.000 description 9
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 241000282472 Canis lupus familiaris Species 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 241000194017 Streptococcus Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 150000007514 bases Chemical class 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 230000000763 evoking effect Effects 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 231100000252 nontoxic Toxicity 0.000 description 8
- 230000003000 nontoxic effect Effects 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241000606125 Bacteroides Species 0.000 description 7
- 241000282326 Felis catus Species 0.000 description 7
- 241000606768 Haemophilus influenzae Species 0.000 description 7
- 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 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 230000002265 prevention Effects 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- 241001647372 Chlamydia pneumoniae Species 0.000 description 6
- 241000193403 Clostridium Species 0.000 description 6
- 241000590002 Helicobacter pylori Species 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 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 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 229940047650 haemophilus influenzae Drugs 0.000 description 6
- 150000007522 mineralic acids Chemical class 0.000 description 6
- 239000002674 ointment Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000006187 pill Substances 0.000 description 6
- 238000003752 polymerase chain reaction Methods 0.000 description 6
- 208000028172 protozoa infectious disease Diseases 0.000 description 6
- 230000008261 resistance mechanism Effects 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 230000000638 stimulation Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 108010065152 Coagulase Proteins 0.000 description 5
- 229910004373 HOAc Inorganic materials 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 229940037467 helicobacter pylori Drugs 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 241000606750 Actinobacillus Species 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241001148534 Brachyspira Species 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- 206010010741 Conjunctivitis Diseases 0.000 description 4
- 241000186216 Corynebacterium Species 0.000 description 4
- 241000223935 Cryptosporidium Species 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 241000605909 Fusobacterium Species 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 208000016604 Lyme disease Diseases 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 206010035664 Pneumonia Diseases 0.000 description 4
- 241000605894 Porphyromonas Species 0.000 description 4
- 206010037660 Pyrexia Diseases 0.000 description 4
- 206010062255 Soft tissue infection Diseases 0.000 description 4
- 241000295644 Staphylococcaceae Species 0.000 description 4
- 241000191963 Staphylococcus epidermidis Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 241000193998 Streptococcus pneumoniae Species 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 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 4
- 241000589884 Treponema pallidum Species 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000015110 jellies Nutrition 0.000 description 4
- 239000002502 liposome Substances 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
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 208000023504 respiratory system disease Diseases 0.000 description 4
- 206010040872 skin infection Diseases 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- 208000019206 urinary tract infection Diseases 0.000 description 4
- 241000588832 Bordetella pertussis Species 0.000 description 3
- 241000589875 Campylobacter jejuni Species 0.000 description 3
- 241000193464 Clostridium sp. Species 0.000 description 3
- 241000194033 Enterococcus Species 0.000 description 3
- 208000007764 Legionnaires' Disease Diseases 0.000 description 3
- 241000191992 Peptostreptococcus Species 0.000 description 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241001080173 Ridens Species 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- 238000011203 antimicrobial therapy Methods 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical compound Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 description 2
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 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 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 241000606660 Bartonella Species 0.000 description 2
- 241001518086 Bartonella henselae Species 0.000 description 2
- 241000588807 Bordetella Species 0.000 description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000606153 Chlamydia trachomatis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000193468 Clostridium perfringens Species 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241001453844 Dipteris Species 0.000 description 2
- 101100119095 Enterococcus faecalis (strain ATCC 700802 / V583) ermB gene Proteins 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
- 241000186394 Eubacterium Species 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- 206010016952 Food poisoning Diseases 0.000 description 2
- 208000019331 Foodborne disease Diseases 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- 241000605952 Fusobacterium necrophorum Species 0.000 description 2
- 208000005577 Gastroenteritis Diseases 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000243251 Hydra Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 101150052154 MSRA1 gene Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 240000003183 Manihot esculenta Species 0.000 description 2
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 2
- 208000010315 Mastoiditis Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 241000588621 Moraxella Species 0.000 description 2
- 241000588655 Moraxella catarrhalis Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000186367 Mycobacterium avium Species 0.000 description 2
- 241000513886 Mycobacterium avium complex (MAC) Species 0.000 description 2
- 241000186364 Mycobacterium intracellulare Species 0.000 description 2
- 241000204031 Mycoplasma Species 0.000 description 2
- 241001138504 Mycoplasma bovis Species 0.000 description 2
- 241000202934 Mycoplasma pneumoniae Species 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 206010048685 Oral infection Diseases 0.000 description 2
- 206010031252 Osteomyelitis Diseases 0.000 description 2
- 206010033078 Otitis media Diseases 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 241000192033 Peptostreptococcus sp. Species 0.000 description 2
- 201000007100 Pharyngitis Diseases 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- 229920000331 Polyhydroxybutyrate Polymers 0.000 description 2
- 229920001710 Polyorthoester Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000605861 Prevotella Species 0.000 description 2
- 206010057190 Respiratory tract infections Diseases 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- 244000000231 Sesamum indicum Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 241000191984 Staphylococcus haemolyticus Species 0.000 description 2
- 241000191980 Staphylococcus intermedius Species 0.000 description 2
- 241001147691 Staphylococcus saprophyticus Species 0.000 description 2
- 241000194054 Streptococcus uberis Species 0.000 description 2
- 108010015795 Streptogramin B Proteins 0.000 description 2
- 208000033809 Suppuration Diseases 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 229920002807 Thiomer Polymers 0.000 description 2
- 206010044248 Toxic shock syndrome Diseases 0.000 description 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 2
- 241000202921 Ureaplasma urealyticum Species 0.000 description 2
- 208000006374 Uterine Cervicitis Diseases 0.000 description 2
- 206010046793 Uterine inflammation Diseases 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
- 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 2
- 241000606834 [Haemophilus] ducreyi Species 0.000 description 2
- 206010000210 abortion Diseases 0.000 description 2
- 231100000176 abortion Toxicity 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 238000002814 agar dilution Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 244000037640 animal pathogen Species 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229940072107 ascorbate Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 229940092524 bartonella henselae Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 206010008323 cervicitis Diseases 0.000 description 2
- 201000004308 chancroid Diseases 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 229940038705 chlamydia trachomatis Drugs 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229940001468 citrate Drugs 0.000 description 2
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([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 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 201000010251 cutis laxa Diseases 0.000 description 2
- 201000003146 cystitis Diseases 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229920006237 degradable polymer Polymers 0.000 description 2
- 238000001514 detection method 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
- 238000003113 dilution method Methods 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 101150016744 ermC gene Proteins 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 208000010801 foot rot Diseases 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000003278 haem Chemical class 0.000 description 2
- 244000052637 human pathogen Species 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 208000028774 intestinal disease Diseases 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 230000009545 invasion Effects 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 230000033001 locomotion Effects 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 208000004396 mastitis Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 101150111763 mefA gene Proteins 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012544 monitoring process 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
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 201000008383 nephritis Diseases 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000008203 oral pharmaceutical composition Substances 0.000 description 2
- 150000002923 oximes Chemical group 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000002948 pantothenic acids Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229940051027 pasteurella multocida Drugs 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 239000005015 poly(hydroxybutyrate) Substances 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000004633 polyglycolic acid Substances 0.000 description 2
- 239000004626 polylactic acid Substances 0.000 description 2
- 229920000656 polylysine Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 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 2
- 230000008569 process Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 244000079416 protozoan pathogen Species 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 201000003068 rheumatic fever Diseases 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000012163 sequencing technique Methods 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 201000009890 sinusitis Diseases 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- 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 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 229940115922 streptococcus uberis Drugs 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 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
- 206010044008 tonsillitis Diseases 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 108091005703 transmembrane proteins Proteins 0.000 description 2
- 102000035160 transmembrane proteins Human genes 0.000 description 2
- 239000002691 unilamellar liposome Substances 0.000 description 2
- 208000000143 urethritis Diseases 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SAHOBIBQRTZUGB-UHFFFAOYSA-N 3-quinolin-4-ylpropanal Chemical compound C1=CC=C2C(CCC=O)=CC=NC2=C1 SAHOBIBQRTZUGB-UHFFFAOYSA-N 0.000 description 1
- 241000606748 Actinobacillus pleuropneumoniae Species 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- 241001148536 Bacteroides sp. Species 0.000 description 1
- 241000589968 Borrelia Species 0.000 description 1
- 241000180135 Borrelia recurrentis Species 0.000 description 1
- 241000908522 Borreliella Species 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 241000605721 Dichelobacter nodosus Species 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 241000147019 Enterobacter sp. Species 0.000 description 1
- 241001495410 Enterococcus sp. Species 0.000 description 1
- 241000588754 Klebsiella sp. Species 0.000 description 1
- 241001469654 Lawsonia <weevil> Species 0.000 description 1
- 241000589248 Legionella Species 0.000 description 1
- 241000589242 Legionella pneumophila Species 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 241001084338 Listeria sp. Species 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 241000588622 Moraxella bovis Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 208000001203 Smallpox Diseases 0.000 description 1
- 241001575049 Sonia Species 0.000 description 1
- 241001312524 Streptococcus viridans Species 0.000 description 1
- 241000429524 Strophosoma sus Species 0.000 description 1
- 241000870995 Variola Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- YVTFLQUPRIIRFE-QUMKBVJLSA-N erythronolide A Chemical compound CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O YVTFLQUPRIIRFE-QUMKBVJLSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000005255 gram-positive cell Anatomy 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 229940115932 legionella pneumophila Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
Classifications
-
- 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
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4934997P | 1997-06-11 | 1997-06-11 | |
| US60/049,349 | 1997-06-11 | ||
| PCT/IB1998/000741 WO1998056800A1 (en) | 1997-06-11 | 1998-05-15 | 9-oxime erythromycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000513026A true JP2000513026A (ja) | 2000-10-03 |
Family
ID=21959341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11501928A Pending JP2000513026A (ja) | 1997-06-11 | 1998-05-15 | ９−オキシム エリスロマイシン誘導体 |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0988308A1 (cs) |
| JP (1) | JP2000513026A (cs) |
| KR (1) | KR20010013660A (cs) |
| CN (1) | CN1259135A (cs) |
| AP (1) | AP9801253A0 (cs) |
| AR (1) | AR012244A1 (cs) |
| AU (1) | AU7226798A (cs) |
| BG (1) | BG103947A (cs) |
| BR (1) | BR9810021A (cs) |
| CA (1) | CA2293335A1 (cs) |
| CO (1) | CO4940506A1 (cs) |
| CZ (1) | CZ9904388A3 (cs) |
| EA (1) | EA199901016A1 (cs) |
| GT (1) | GT199800074A (cs) |
| HN (1) | HN1998000073A (cs) |
| HR (1) | HRP980316A2 (cs) |
| HU (1) | HUP0002252A3 (cs) |
| ID (1) | ID24529A (cs) |
| IL (1) | IL132767A0 (cs) |
| IS (1) | IS5251A (cs) |
| MA (1) | MA26505A1 (cs) |
| NO (1) | NO996108L (cs) |
| OA (1) | OA11225A (cs) |
| PA (1) | PA8451801A1 (cs) |
| PE (1) | PE79899A1 (cs) |
| PL (1) | PL337606A1 (cs) |
| TN (1) | TNSN98083A1 (cs) |
| TR (1) | TR199902995T2 (cs) |
| TW (1) | TW448174B (cs) |
| WO (1) | WO1998056800A1 (cs) |
| ZA (1) | ZA985018B (cs) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HN1998000159A (es) * | 1997-10-29 | 1999-02-09 | Monsanto Co | Derivados de 9- amino - 3 ceto eritromicina |
| DE69926005T2 (de) * | 1998-09-22 | 2006-05-18 | Pfizer Products Inc., Groton | Carbamat- und carbazatketolidantibiotika |
| FR2786188B1 (fr) * | 1998-11-24 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
| US6258785B1 (en) | 1998-12-02 | 2001-07-10 | Pfizer Inc. | 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 |
| EP1298138B1 (en) * | 1998-12-10 | 2006-11-02 | Pfizer Products Inc. | Carbamate and Carbazate Ketolide Antibiotics |
| US6284732B1 (en) * | 1998-12-18 | 2001-09-04 | Bio-Rad Laboratories, Inc. | Peptides and peptide analogues designed from HFE protein and their uses in the treatment of iron overload diseases |
| NZ515027A (en) * | 1999-04-16 | 2004-01-30 | Kosan Biosciences Inc | Erythromycin derivatives as antibiotics |
| OA11945A (en) | 1999-05-24 | 2006-04-13 | Pfizer Prod Inc | 13-Methyl erythromycin derivatives. |
| ES2208334T3 (es) * | 1999-06-07 | 2004-06-16 | Abbott Laboratories | Derivados cetolida de 6-0 carbamato. |
| ID27331A (id) * | 1999-09-29 | 2001-03-29 | Pfizer Prod Inc | Pembuatan antibiotik-antibiotik ketolida karbamat |
| EP1439186A3 (en) * | 1999-12-29 | 2004-11-03 | Pfizer Products Inc. | Intermediates for novel antibacterial and prokinetic macrolides |
| EP1114826A3 (en) * | 1999-12-29 | 2001-10-31 | Pfizer Products Inc. | Novel antibacterial and prokinetic macrolides |
| US6946446B2 (en) | 2000-02-24 | 2005-09-20 | Abbott Laboratories | Anti-infective agents useful against multidrug-resistant strains of bacteria |
| US6403776B1 (en) | 2000-07-05 | 2002-06-11 | Pfizer Inc. | Synthesis of carbamate ketolide antibiotics |
| WO2003090761A1 (en) * | 2002-04-25 | 2003-11-06 | Abbott Laboratories | 9-oxime macrolide antibacterials |
| AR043050A1 (es) | 2002-09-26 | 2005-07-13 | Rib X Pharmaceuticals Inc | Compuestos heterociclicos bifuncionales y metodos para preparar y usar los mismos |
| CA2529817C (en) * | 2003-03-10 | 2013-02-12 | Optimer Pharmaceuticals, Inc. | Novel antibacterial agents |
| WO2005085266A2 (en) | 2004-02-27 | 2005-09-15 | Rib-X Pharmaceuticals, Inc. | Macrocyclic compounds and methods of making and using the same |
| WO2009055557A1 (en) | 2007-10-25 | 2009-04-30 | 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 |
| CN108310000A (zh) | 2009-09-10 | 2018-07-24 | 森普拉制药公司 | 治疗疟疾、结核病和mac疾病的方法 |
| CN102146085B (zh) * | 2010-02-09 | 2014-03-26 | 北京理工大学 | 一种9-肟醚酮内酯衍生物、制备方法及其药物组合物 |
| CA2793884C (en) | 2010-03-22 | 2019-09-10 | Cempra Pharmaceuticals, Inc. | Crystalline forms of a macrolide, and uses therefor |
| US9051346B2 (en) | 2010-05-20 | 2015-06-09 | Cempra Pharmaceuticals, Inc. | Process for preparing triazole-containing ketolide antibiotics |
| EP2613630A4 (en) | 2010-09-10 | 2014-01-15 | Cempra Pharmaceuticals Inc | HYDROGEN BOND FOR THE PREPARATION OF FLUOROCHETOLIDES FOR THE TREATMENT OF DISEASES |
| IN2014DN08939A (cs) | 2012-03-27 | 2015-05-22 | Cempra Pharmaceuticals Inc | |
| RU2015138796A (ru) | 2013-03-14 | 2017-04-19 | Семпра Фармасьютикалс, Инк. | Способы и составы для лечения респираторных заболеваний |
| WO2014145210A1 (en) | 2013-03-15 | 2014-09-18 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| FR2718450B1 (fr) * | 1994-04-08 | 1997-01-10 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
-
1998
- 1998-05-15 JP JP11501928A patent/JP2000513026A/ja active Pending
- 1998-05-15 AU AU72267/98A patent/AU7226798A/en not_active Abandoned
- 1998-05-15 BR BR9810021-1A patent/BR9810021A/pt not_active IP Right Cessation
- 1998-05-15 EA EA199901016A patent/EA199901016A1/ru unknown
- 1998-05-15 KR KR1019997011672A patent/KR20010013660A/ko not_active Ceased
- 1998-05-15 CZ CZ19994388A patent/CZ9904388A3/cs unknown
- 1998-05-15 CN CN98805848A patent/CN1259135A/zh active Pending
- 1998-05-15 CA CA002293335A patent/CA2293335A1/en not_active Abandoned
- 1998-05-15 PL PL98337606A patent/PL337606A1/xx unknown
- 1998-05-15 TR TR1999/02995T patent/TR199902995T2/xx unknown
- 1998-05-15 ID IDW991570A patent/ID24529A/id unknown
- 1998-05-15 IL IL13276798A patent/IL132767A0/xx unknown
- 1998-05-15 EP EP98919394A patent/EP0988308A1/en not_active Withdrawn
- 1998-05-15 WO PCT/IB1998/000741 patent/WO1998056800A1/en not_active Ceased
- 1998-05-15 HU HU0002252A patent/HUP0002252A3/hu unknown
- 1998-05-19 HN HN1998000073A patent/HN1998000073A/es unknown
- 1998-05-21 PA PA19988451801A patent/PA8451801A1/es unknown
- 1998-06-04 AP APAP/P/1998/001253A patent/AP9801253A0/en unknown
- 1998-06-05 GT GT199800074A patent/GT199800074A/es unknown
- 1998-06-08 TW TW087109086A patent/TW448174B/zh active
- 1998-06-08 PE PE1998000470A patent/PE79899A1/es not_active Application Discontinuation
- 1998-06-09 AR ARP980102703A patent/AR012244A1/es unknown
- 1998-06-10 MA MA25105A patent/MA26505A1/fr unknown
- 1998-06-10 TN TNTNSN98083A patent/TNSN98083A1/fr unknown
- 1998-06-10 ZA ZA9805018A patent/ZA985018B/xx unknown
- 1998-06-11 HR HR60/049,349A patent/HRP980316A2/hr not_active Application Discontinuation
- 1998-06-11 CO CO98033538A patent/CO4940506A1/es unknown
-
1999
- 1999-11-16 IS IS5251A patent/IS5251A/is unknown
- 1999-12-03 BG BG103947A patent/BG103947A/xx unknown
- 1999-12-03 OA OA9900269A patent/OA11225A/en unknown
- 1999-12-10 NO NO996108A patent/NO996108L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0002252A2 (hu) | 2000-12-28 |
| ZA985018B (en) | 1999-12-10 |
| BR9810021A (pt) | 2000-09-19 |
| TW448174B (en) | 2001-08-01 |
| TNSN98083A1 (fr) | 2005-03-15 |
| AR012244A1 (es) | 2000-09-27 |
| HUP0002252A3 (en) | 2002-01-28 |
| PE79899A1 (es) | 1999-08-25 |
| AP9801253A0 (en) | 1999-12-04 |
| PL337606A1 (en) | 2000-08-28 |
| KR20010013660A (ko) | 2001-02-26 |
| TR199902995T2 (xx) | 2000-02-21 |
| EP0988308A1 (en) | 2000-03-29 |
| GT199800074A (es) | 1999-11-27 |
| IS5251A (is) | 1999-11-16 |
| CO4940506A1 (es) | 2000-07-24 |
| ID24529A (id) | 2000-07-20 |
| HRP980316A2 (en) | 1999-04-30 |
| MA26505A1 (fr) | 2004-12-20 |
| NO996108L (no) | 2000-02-10 |
| CZ9904388A3 (cs) | 2002-10-16 |
| EA199901016A1 (ru) | 2000-06-26 |
| HN1998000073A (es) | 1999-01-08 |
| NO996108D0 (no) | 1999-12-10 |
| BG103947A (en) | 2000-07-31 |
| PA8451801A1 (es) | 2000-05-24 |
| AU7226798A (en) | 1998-12-30 |
| WO1998056800A1 (en) | 1998-12-17 |
| CA2293335A1 (en) | 1998-12-17 |
| CN1259135A (zh) | 2000-07-05 |
| OA11225A (en) | 2003-07-17 |
| IL132767A0 (en) | 2001-03-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2000513026A (ja) | ９−オキシム エリスロマイシン誘導体 | |
| KR100396168B1 (ko) | 4″-치환된-9-데옥소-9ａ-아자-9ａ-호모에리트로마이신 Ａ유도체 | |
| EP0988309B1 (en) | C-4''-substituted macrolide derivatives | |
| EP0941998B1 (en) | 3,6-ketal macrolide antibiotics | |
| JP3842973B2 (ja) | １３員アザリド類および抗生物質としてのそれらの使用 | |
| US6576749B2 (en) | C-4″-substituted macrolide derivatives | |
| EP0984019B1 (en) | C11 carbamates of macrolide antibacterials | |
| US6518251B1 (en) | Macrolides | |
| US6162794A (en) | Erythromycin derivatives | |
| US6248719B1 (en) | Tricyclic 3-keto derivatives of 6-O-methylerthromycin | |
| US20020151507A1 (en) | 9-oxime erythromycin derivatives | |
| US6482801B2 (en) | 9a, 11b-dehydro derivatives of 9-oxime-3-keto-6-O- methylerythromycin | |
| MXPA99011494A (en) | 9-oxime erythromycin derivatives | |
| HK1127924A (en) | 13-membered azalides and their use as antibiotic agents | |
| MXPA01005055A (en) | 13-membered azalides and their use as antibiotic agents | |
| EP1437360A2 (en) | C11 Carbamates of macrolide antibacterials | |
| MXPA99011495A (en) | 4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives |