SK6342000A3 - 6,11-bridged erythromycin derivatives - Google Patents

6,11-bridged erythromycin derivatives Download PDF

Info

Publication number: SK6342000A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; heteroarylene; arylene; group
Prior art date: 1997-10-29

Application number

SK634-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Yat Sun Or

George Griesgraber

Leping Li

Daniel T Chu

Original Assignee

Abbott Lab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-10-29

Filing date

1998-10-29

Publication date

2000-09-12

1998-10-29 Application filed by Abbott Lab filed Critical Abbott Lab

2000-09-12 Publication of SK6342000A3 publication Critical patent/SK6342000A3/sk

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 abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 379
238000000034 method Methods 0.000 claims abstract description 77
230000008569 process Effects 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 14
150000002148 esters Chemical class 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
208000035143 Bacterial infection Diseases 0.000 claims abstract description 8
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 8
239000003937 drug carrier Substances 0.000 claims abstract description 8
241000124008 Mammalia Species 0.000 claims abstract description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 60
239000003153 chemical reaction reagent Substances 0.000 claims description 39
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
239000002243 precursor Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 25
229910052770 Uranium Inorganic materials 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 17
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000000732 arylene group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
125000005549 heteroarylene group Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
229910052740 iodine Inorganic materials 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000004450 alkenylene group Chemical group 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
HGBVWMHWNOZFMV-UHFFFAOYSA-N 2-[(2-iodophenyl)methoxy]ethanamine Chemical compound NCCOCC1=CC=CC=C1I HGBVWMHWNOZFMV-UHFFFAOYSA-N 0.000 claims description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
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239000000203 mixture Substances 0.000 abstract description 45
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 103
239000000243 solution Substances 0.000 description 60
-1 n-octyl Chemical group 0.000 description 50
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000000543 intermediate Substances 0.000 description 41
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
239000002904 solvent Substances 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
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238000006243 chemical reaction Methods 0.000 description 30
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
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QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 15
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
125000003277 amino group Chemical group 0.000 description 13
235000019441 ethanol Nutrition 0.000 description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012043 crude product Substances 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000003814 drug Substances 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 11
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 10
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
239000000010 aprotic solvent Substances 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
229960003276 erythromycin Drugs 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
241000191967 Staphylococcus aureus Species 0.000 description 7
238000000576 coating method Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
238000000746 purification Methods 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
125000003282 alkyl amino group Chemical group 0.000 description 6
239000002585 base Substances 0.000 description 6
238000010511 deprotection reaction Methods 0.000 description 6
125000004663 dialkyl amino group Chemical group 0.000 description 6
125000000592 heterocycloalkyl group Chemical group 0.000 description 6
150000002430 hydrocarbons Chemical class 0.000 description 6
239000008101 lactose Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
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TZKBVRDEOITLRB-UHFFFAOYSA-N 4-methyl-n-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-3-[2-(1h-pyrazolo[3,4-b]pyridin-5-yl)ethynyl]benzamide Chemical compound C1CN(C)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(C#CC=2C=C3C=NNC3=NC=2)=C1 TZKBVRDEOITLRB-UHFFFAOYSA-N 0.000 description 5
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239000007922 nasal spray Substances 0.000 description 1
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
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239000008363 phosphate buffer Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
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229910052697 platinum Inorganic materials 0.000 description 1
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229920001296 polysiloxane Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
229940043349 potassium metabisulfite Drugs 0.000 description 1
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WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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125000003373 pyrazinyl group Chemical group 0.000 description 1
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125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
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230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
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239000001509 sodium citrate Substances 0.000 description 1
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235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives

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)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

SK634-2000A 1997-10-29 1998-10-29 6,11-bridged erythromycin derivatives SK6342000A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US96040097A	1997-10-29	1997-10-29
US15826998A	1998-09-22	1998-09-22
PCT/US1998/022941 WO1999021864A1 (fr)	1997-10-29	1998-10-29	Derives d'erythromycine a pont 6,11

Publications (1)

Publication Number	Publication Date
SK6342000A3 true SK6342000A3 (en)	2000-09-12

Family

ID=26854886

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK634-2000A SK6342000A3 (en)	1997-10-29	1998-10-29	6,11-bridged erythromycin derivatives

Country Status (23)

Country	Link
EP (1)	EP1027361B1 (fr)
JP (1)	JP2001521038A (fr)
KR (1)	KR20010031591A (fr)
CN (1)	CN1278266A (fr)
AR (1)	AR015986A1 (fr)
AT (1)	ATE239750T1 (fr)
AU (1)	AU1286799A (fr)
BG (1)	BG104425A (fr)
BR (1)	BR9813317A (fr)
CA (1)	CA2307828A1 (fr)
CO (1)	CO4990972A1 (fr)
DE (1)	DE69814441T2 (fr)
DK (1)	DK1027361T3 (fr)
ES (1)	ES2198766T3 (fr)
HU (1)	HUP0004323A2 (fr)
IL (1)	IL134996A0 (fr)
NO (1)	NO20002099L (fr)
PL (1)	PL340253A1 (fr)
PT (1)	PT1027361E (fr)
SK (1)	SK6342000A3 (fr)
TR (1)	TR200001140T2 (fr)
TW (1)	TW486485B (fr)
WO (1)	WO1999021864A1 (fr)

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WO2003024986A1 (fr)	2001-09-17	2003-03-27	Ortho-Mcneil Pharmaceutical, Inc.	Agents antimicrobiens 6-o-carbamate-11,12-lacto-cetolide
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WO2003095466A1 (fr) *	2002-05-13	2003-11-20	Enanta Pharmaceuticals, Inc.	Derives de l'erythromycine 6,11 bicyclique
US6841664B2 (en)	2002-07-25	2005-01-11	Enanra Pharmaceuticals, Inc.	6,11-4-carbon bridged ketolides
US7129221B2 (en)	2002-05-13	2006-10-31	Enanta Pharmaceuticals, Inc.	6,11-bicyclic erythromycin derivatives
US7273853B2 (en)	2002-05-13	2007-09-25	Enanta Pharmaceuticals, Inc.	6-11 bicyclic ketolide derivatives
US6645941B1 (en) *	2003-03-26	2003-11-11	Enanta Pharmaceuticals, Inc.	6,11-3C-bicyclic 9a-azalide derivatives
US7414030B2 (en)	2004-01-07	2008-08-19	Enanta Pharmaceuticals, Inc.	6-11 Bicyclic erythromycin derivatives
WO2005070113A2 (fr)	2004-01-09	2005-08-04	Enanta Pharmaceuticals, Inc.	Derives d'erythromycine bicycliques 9-n substitues en c6-c11
WO2005080408A1 (fr) *	2004-01-23	2005-09-01	Enanta Pharmaceuticals, Inc.	Composes macrocycliques pontes et procedes de preparation desdits composes
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US7384922B2 (en)	2005-05-04	2008-06-10	Enanta Pharmaceuticals, Inc.	6-11 bridged oxime erythromycin derivatives
US7589067B2 (en)	2005-10-12	2009-09-15	Enanta Pharmaceuticals, Inc.	6, 11-bridged tricyclic macrolides
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WO2018201076A2 (fr) *	2017-04-28	2018-11-01	Macrolide Pharmaceuticals Inc.	Macrolides à sucres modifiés de type désosamine et utilisations de ceux-ci

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- 1998-10-29 BR BR9813317-9A patent/BR9813317A/pt not_active IP Right Cessation
- 1998-10-29 IL IL13499698A patent/IL134996A0/xx unknown
- 1998-10-29 KR KR1020007004641A patent/KR20010031591A/ko not_active Withdrawn
- 1998-10-29 TR TR2000/01140T patent/TR200001140T2/xx unknown
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- 1998-10-29 PT PT98956314T patent/PT1027361E/pt unknown
- 1998-10-29 SK SK634-2000A patent/SK6342000A3/sk unknown
- 1998-10-29 DK DK98956314T patent/DK1027361T3/da active
- 1998-10-29 CA CA002307828A patent/CA2307828A1/fr not_active Abandoned
- 1998-10-29 CN CN98810785A patent/CN1278266A/zh active Pending
- 1998-10-29 AT AT98956314T patent/ATE239750T1/de not_active IP Right Cessation
- 1998-10-29 EP EP98956314A patent/EP1027361B1/fr not_active Expired - Lifetime
- 1998-10-29 ES ES98956314T patent/ES2198766T3/es not_active Expired - Lifetime
- 1998-10-29 PL PL98340253A patent/PL340253A1/xx unknown
- 1998-10-29 AU AU12867/99A patent/AU1286799A/en not_active Abandoned
- 1998-10-29 JP JP2000517973A patent/JP2001521038A/ja not_active Withdrawn
- 1998-10-29 DE DE69814441T patent/DE69814441T2/de not_active Expired - Fee Related
- 1998-10-29 WO PCT/US1998/022941 patent/WO1999021864A1/fr not_active Ceased
- 1998-11-30 TW TW087117981A patent/TW486485B/zh active
2000
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Also Published As

Publication number	Publication date
CO4990972A1 (es)	2000-12-26
DE69814441T2 (de)	2004-04-08
EP1027361B1 (fr)	2003-05-07
CA2307828A1 (fr)	1999-05-06
CN1278266A (zh)	2000-12-27
BR9813317A (pt)	2000-08-22
NO20002099D0 (no)	2000-04-25
EP1027361A1 (fr)	2000-08-16
TW486485B (en)	2002-05-11
KR20010031591A (ko)	2001-04-16
NO20002099L (no)	2000-06-29
TR200001140T2 (tr)	2001-05-21
AU1286799A (en)	1999-05-17
HUP0004323A2 (hu)	2001-02-28
ES2198766T3 (es)	2004-02-01
BG104425A (bg)	2001-01-31
DK1027361T3 (da)	2003-08-25
PL340253A1 (en)	2001-01-29
AR015986A1 (es)	2001-05-30
ATE239750T1 (de)	2003-05-15
IL134996A0 (en)	2001-05-20
DE69814441D1 (de)	2003-06-12
PT1027361E (pt)	2003-09-30
JP2001521038A (ja)	2001-11-06
WO1999021864A1 (fr)	1999-05-06

Publication	Publication Date	Title
US6046171A (en)	2000-04-04	6,11-bridged erythromycin derivatives
SK6342000A3 (en)	2000-09-12	6,11-bridged erythromycin derivatives
SK285535B6 (sk)	2007-03-01	6-O-Substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
CZ303573B6 (cs)	2012-12-12	6-O-substituovaný ketolidový derivát erythromycinu, jeho použití, farmaceutická kompozice ho obsahující a zpusob jeho výroby
AU737310B2 (en)	2001-08-16	3'-n-modified 6-o-substituted erythromycin ketolide derivatives having antibacterial activity
SK3032000A3 (en)	2000-07-11	6,9-bridged erythromycin derivatives
SK286397B6 (sk)	2008-09-05	2-Halogén-6-O-substituované ketolidové deriváty, ich použitie, spôsob ich prípravy a farmaceutické kompozície s ich obsahom
US6420535B1 (en)	2002-07-16	6-O-carbamate ketolide derivatives
US6034069A (en)	2000-03-07	3-'N-modified 6-O-substituted erythromycin ketolide derivatives having antibacterial activity
US6946446B2 (en)	2005-09-20	Anti-infective agents useful against multidrug-resistant strains of bacteria
CA2301642A1 (fr)	1999-03-11	Derives d'erythromycine 3-descladinose 6-o-substituee
EP1181300B1 (fr)	2003-09-17	Derives ketolide de 6-o-carbamate
JP2003501439A5 (fr)	2007-06-21
EP1259923B1 (fr)	2005-12-14	Agents anti-infectieux utiles contre des souches de bacteries resistant a l'action de plusieurs medicaments
CZ20001394A3 (cs)	2000-09-13	Erythromycinové deriváty s 6,11-přemostěním
AU714176B2 (en)	1999-12-23	3-deoxy-3-descladinose derivatives of erythromycins A and B
SK160299A3 (en)	2000-06-12	Multicyclic erythromycin derivatives
MXPA00004227A (en)	2001-05-07	6,11-bridged erythromycin derivatives
MXPA00002216A (en)	2001-03-05	3-descladinose 6-o-substituded erythromycin derivatives
CZ20001045A3 (cs)	2000-07-12	3-N-módilikováné 6-O-substituované ketolidové deriváty erytromycinu
CZ2000811A3 (cs)	2000-06-14	6,9-můstkové erythromycinové deriváty a způsob jejich přípravy
MXPA00003117A (en)	2001-07-09	3'-n-modified 6-o-substituted erythromycin ketolide derivatives having antibacterial activity
CZ407399A3 (cs)	2000-02-16	Multicyklické deriváty erythromycinu