SK285536B6 - 6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy - Google Patents

6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy Download PDF

Info

Publication number: SK285536B6
Authority: SK; Slovakia
Prior art keywords: formula; compound; substituted; defined above; alkyl
Prior art date: 1996-09-04

Application number

SK5085-2006A

Other languages

English (en)

Slovak (sk)

Inventor

Yat Sun Or

Zhenkun Ma

Richard F. Clark

Daniel T. Chu

Jacob J. Plattner

Original Assignee

Abbott Laboratories

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.)

1996-09-04

Filing date

1997-09-02

Publication date

2007-03-01

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27107953&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK285536(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-07-03 Priority claimed from US08/888,350 external-priority patent/US5866549A/en

1997-09-02 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2007-03-01 Publication of SK285536B6 publication Critical patent/SK285536B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 141
238000002360 preparation method Methods 0.000 title claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
239000003835 ketolide antibiotic agent Substances 0.000 title description 11
230000000844 anti-bacterial effect Effects 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 1097
150000003839 salts Chemical class 0.000 claims abstract description 15
-1 4-quinolyl Chemical group 0.000 claims description 460
125000001072 heteroaryl group Chemical group 0.000 claims description 107
238000006243 chemical reaction Methods 0.000 claims description 80
229910052739 hydrogen Inorganic materials 0.000 claims description 64
125000003118 aryl group Chemical group 0.000 claims description 62
125000003107 substituted aryl group Chemical group 0.000 claims description 48
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
125000001424 substituent group Chemical group 0.000 claims description 40
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 32
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 29
125000006239 protecting group Chemical group 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
150000001412 amines Chemical class 0.000 claims description 20
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 16
239000003153 chemical reaction reagent Substances 0.000 claims description 16
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 16
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
239000003795 chemical substances by application Substances 0.000 claims description 14
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
239000002585 base Substances 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 8
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
208000035143 Bacterial infection Diseases 0.000 claims description 6
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 6
150000008046 alkali metal hydrides Chemical class 0.000 claims description 6
208000022362 bacterial infectious disease Diseases 0.000 claims description 6
125000001843 C4-C10 alkenyl group Chemical group 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 4
125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 3
238000006114 decarboxylation reaction Methods 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims 3
230000000845 anti-microbial effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 261
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 253
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 172
239000000243 solution Substances 0.000 description 141
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 122
239000011541 reaction mixture Substances 0.000 description 116
239000000203 mixture Substances 0.000 description 104
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 81
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 79
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 67
239000012267 brine Substances 0.000 description 64
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 64
125000000217 alkyl group Chemical group 0.000 description 63
235000019439 ethyl acetate Nutrition 0.000 description 60
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 59
239000007787 solid Substances 0.000 description 56
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 52
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
239000002904 solvent Substances 0.000 description 50
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 48
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 48
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 45
238000010898 silica gel chromatography Methods 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
238000004896 high resolution mass spectrometry Methods 0.000 description 41
230000002829 reductive effect Effects 0.000 description 41
ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 description 37
239000000460 chlorine Substances 0.000 description 36
229910052757 nitrogen Inorganic materials 0.000 description 36
239000012074 organic phase Substances 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
239000011734 sodium Substances 0.000 description 34
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 32
238000004587 chromatography analysis Methods 0.000 description 31
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
239000006260 foam Substances 0.000 description 27
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 26
235000017557 sodium bicarbonate Nutrition 0.000 description 26
229910000030 sodium bicarbonate Inorganic materials 0.000 description 26
229910052938 sodium sulfate Inorganic materials 0.000 description 26
235000011152 sodium sulphate Nutrition 0.000 description 26
229910004298 SiO 2 Inorganic materials 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
235000019441 ethanol Nutrition 0.000 description 24
150000002923 oximes Chemical class 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
238000003756 stirring Methods 0.000 description 23
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 19
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 19
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
235000002639 sodium chloride Nutrition 0.000 description 18
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 17
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 description 17
238000010511 deprotection reaction Methods 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000000010 aprotic solvent Substances 0.000 description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
239000000908 ammonium hydroxide Substances 0.000 description 15
229920006395 saturated elastomer Polymers 0.000 description 15
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000012299 nitrogen atmosphere Substances 0.000 description 14
229910000029 sodium carbonate Inorganic materials 0.000 description 13
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
239000002168 alkylating agent Substances 0.000 description 12
229940100198 alkylating agent Drugs 0.000 description 12
125000004122 cyclic group Chemical group 0.000 description 12
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical group O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 11
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 11
238000003786 synthesis reaction Methods 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
239000002253 acid Substances 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
229940079593 drug Drugs 0.000 description 10
229960003276 erythromycin Drugs 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 10
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
229910000104 sodium hydride Inorganic materials 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
HYTACLVSJIFYBY-UHFFFAOYSA-N azane;dichloromethane;methanol Chemical compound N.OC.ClCCl HYTACLVSJIFYBY-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 8
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
229940125797 compound 12 Drugs 0.000 description 8
239000003120 macrolide antibiotic agent Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
229930006677 Erythromycin A Natural products 0.000 description 7
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 7
241000191967 Staphylococcus aureus Species 0.000 description 7
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
238000000576 coating method Methods 0.000 description 7
239000012043 crude product Substances 0.000 description 7
229960001760 dimethyl sulfoxide Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
150000007524 organic acids Chemical class 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 6
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000003282 alkyl amino group Chemical group 0.000 description 6
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 6
125000002619 bicyclic group Chemical group 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
229940125773 compound 10 Drugs 0.000 description 6
125000004663 dialkyl amino group Chemical group 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000000284 extract Substances 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 6
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 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
230000008520 organization Effects 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
238000000746 purification Methods 0.000 description 6
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 6
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
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235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 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
GTAVEQBEFSJELB-GFCCVEGCSA-N tert-butyl n-[(2r)-1-azido-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CN=[N+]=[N-])CC1=CC=CC=C1 GTAVEQBEFSJELB-GFCCVEGCSA-N 0.000 description 1
LDKDMDVMMCXTMO-GFCCVEGCSA-N tert-butyl n-[(2r)-1-hydroxy-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CO)CC1=CC=CC=C1 LDKDMDVMMCXTMO-GFCCVEGCSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 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
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 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
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
239000003039 volatile agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Cephalosporin Compounds (AREA)
Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

SK5085-2006A 1996-09-04 1997-09-02 6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy SK285536B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US70777696A	1996-09-04	1996-09-04
US08/888,350 US5866549A (en)	1996-09-04	1997-07-03	6-O-substituted ketolides having antibacterial activity
PCT/US1997/015506 WO1998009978A1 (en)	1996-09-04	1997-09-02	6-o-substituted ketolides having antibacterial activity

Publications (1)

Publication Number	Publication Date
SK285536B6 true SK285536B6 (sk)	2007-03-01

Family

ID=27107953

Family Applications (5)

Application Number	Title	Priority Date	Filing Date
SK286-99A SK285533B6 (sk)	1996-09-04	1997-09-02	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
SK5084-2006A SK285535B6 (sk)	1996-09-04	1997-09-02	6-O-Substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
SK5085-2006A SK285536B6 (sk)	1996-09-04	1997-09-02	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
SK5083-2006A SK285534B6 (sk)	1996-09-04	1997-09-02	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
SK5086-2006A SK286181B6 (sk)	1996-09-04	1997-09-02	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
SK286-99A SK285533B6 (sk)	1996-09-04	1997-09-02	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
SK5084-2006A SK285535B6 (sk)	1996-09-04	1997-09-02	6-O-Substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
SK5083-2006A SK285534B6 (sk)	1996-09-04	1997-09-02	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
SK5086-2006A SK286181B6 (sk)	1996-09-04	1997-09-02	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy

Country Status (27)

Country	Link
US (4)	US6028181A (de)
EP (5)	EP1291352B1 (de)
JP (1)	JP4597274B2 (de)
KR (5)	KR100523679B1 (de)
CN (4)	CN100441591C (de)
AT (5)	ATE296832T1 (de)
BG (1)	BG63547B1 (de)
BR (1)	BR9711661A (de)
CA (1)	CA2263972C (de)
CZ (1)	CZ300106B6 (de)
DE (5)	DE69733422T2 (de)
DK (5)	DK1291352T3 (de)
ES (5)	ES2242811T3 (de)
HR (5)	HRP970473B1 (de)
HU (1)	HU230166B1 (de)
ID (1)	ID19406A (de)
IL (1)	IL128681A0 (de)
NO (1)	NO314230B1 (de)
NZ (1)	NZ334274A (de)
PL (1)	PL188173B1 (de)
PT (5)	PT1291351E (de)
RO (1)	RO121473B1 (de)
RU (1)	RU2192427C2 (de)
SI (1)	SI20023B (de)
SK (5)	SK285533B6 (de)
TR (1)	TR199901127T2 (de)
WO (1)	WO1998009978A1 (de)

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FR2702480B1 (fr) *	1993-03-09	1995-04-28	Roussel Uclaf	Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments.
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FR2732023B1 (fr) *	1995-03-22	1997-04-30	Roussel Uclaf	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
FR2732684B1 (fr) *	1995-04-06	1997-04-30	Roussel Uclaf	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
FR2738571B1 (fr) *	1995-09-11	1997-10-17	Roussel Uclaf	Nouveaux derives de la 5-0-desosaminyl 6-0-methyl- erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs
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US6171807B1 (en) *	1996-11-13	2001-01-09	Associates Of Cape Cod, Inc.	Detection and quantitation of endotoxin by fluorescence polarization

1997
- 1997-09-02 DE DE69733422T patent/DE69733422T2/de not_active Expired - Lifetime
- 1997-09-02 PT PT02024558T patent/PT1291351E/pt unknown
- 1997-09-02 DE DE69733369T patent/DE69733369T2/de not_active Expired - Lifetime
- 1997-09-02 DK DK02024559T patent/DK1291352T3/da active
- 1997-09-02 JP JP51285898A patent/JP4597274B2/ja not_active Expired - Lifetime
- 1997-09-02 RU RU99106778/04A patent/RU2192427C2/ru active
- 1997-09-02 DK DK02024560T patent/DK1291353T3/da active
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- 1997-09-02 DK DK97939765T patent/DK0929563T3/da active
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- 1997-09-02 KR KR1020057007117A patent/KR100576988B1/ko not_active Expired - Lifetime
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- 1997-09-02 DK DK02024557T patent/DK1291350T3/da active
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- 1997-09-02 DK DK02024558T patent/DK1291351T3/da active
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- 1997-09-02 EP EP97939765A patent/EP0929563B1/de not_active Expired - Lifetime
- 1997-09-02 DE DE69733439T patent/DE69733439T2/de not_active Expired - Lifetime
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- 1997-09-02 SK SK5085-2006A patent/SK285536B6/sk not_active IP Right Cessation
- 1997-09-02 AT AT02024560T patent/ATE296832T1/de active
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- 1997-09-02 AT AT97939765T patent/ATE296831T1/de active
- 1997-09-02 KR KR1020057007118A patent/KR20050044816A/ko not_active Ceased
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- 1997-09-02 AT AT02024557T patent/ATE296307T1/de active
- 1997-09-02 CN CNB2005100674151A patent/CN100441591C/zh not_active Expired - Lifetime
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- 1997-09-02 AT AT02024558T patent/ATE299508T1/de active
- 1997-09-02 CN CNA2005100674147A patent/CN1680419A/zh active Pending
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- 1997-09-02 AT AT02024559T patent/ATE296308T1/de active
- 1997-09-02 WO PCT/US1997/015506 patent/WO1998009978A1/en not_active Ceased
- 1997-09-02 SK SK5083-2006A patent/SK285534B6/sk not_active IP Right Cessation
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- 1997-09-02 NZ NZ334274A patent/NZ334274A/en not_active IP Right Cessation
- 1997-09-03 HR HR970473A patent/HRP970473B1/xx not_active IP Right Cessation
- 1997-09-04 ID IDP973095A patent/ID19406A/id unknown
1998
- 1998-11-04 US US09/186,395 patent/US6028181A/en not_active Expired - Lifetime
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1999
- 1999-03-02 NO NO19991022A patent/NO314230B1/no not_active IP Right Cessation
- 1999-03-26 BG BG103292A patent/BG63547B1/bg unknown
2004
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2006
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- 2006-08-11 HR HRP20060277AA patent/HRP20060277B1/hr not_active IP Right Cessation
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Also Published As

Publication number	Publication date
ID19406A (id)	1998-07-09
DE69733369D1 (de)	2005-06-30
DE69733439D1 (de)	2005-07-07
CN1680419A (zh)	2005-10-12
DK1291353T3 (da)	2005-10-03
HK1021537A1 (en)	2000-06-16
SI20023A (sl)	2000-02-29
ES2242983T3 (es)	2005-11-16
HRP20060275A2 (en)	2007-10-31
DK1291350T3 (da)	2005-09-26
KR20050043994A (ko)	2005-05-11
EP1291351A1 (de)	2003-03-12
DE69733370T2 (de)	2006-02-02
ATE296308T1 (de)	2005-06-15
NZ334274A (en)	2001-02-23
HRP20060276B1 (hr)	2014-04-25
HRP20060278A2 (en)	2007-10-31
EP1291350B1 (de)	2005-05-25
HRP970473B1 (en)	2007-02-28
PL332009A1 (en)	1999-08-16
USRE39591E1 (en)	2007-04-24
ES2242812T3 (es)	2005-11-16
NO991022D0 (no)	1999-03-02
CZ68599A3 (cs)	1999-08-11
WO1998009978A1 (en)	1998-03-12
NO991022L (no)	1999-05-03
US6147197A (en)	2000-11-14
NO314230B1 (no)	2003-02-17
DE69733723T2 (de)	2006-04-20
CN1680418A (zh)	2005-10-12
KR20000068435A (ko)	2000-11-25
TR199901127T2 (xx)	1999-07-21
SI20023B (en)	2001-02-28
DE69733422D1 (de)	2005-07-07
BR9711661A (pt)	1999-08-24
ES2242813T3 (es)	2005-11-16
EP1291352A1 (de)	2003-03-12
DE69733723D1 (de)	2005-08-18
EP1291352B1 (de)	2005-05-25
HRP20060275B1 (hr)	2014-04-11
PT1291350E (pt)	2005-09-30
DE69733370D1 (de)	2005-06-30
HRP20060277B1 (hr)	2014-04-11
KR20050043993A (ko)	2005-05-11
DK1291351T3 (da)	2005-10-24
KR20050044816A (ko)	2005-05-12
ATE299508T1 (de)	2005-07-15
US6028181A (en)	2000-02-22
DE69733422T2 (de)	2006-05-04
HRP20060277A2 (en)	2007-10-31
ATE296831T1 (de)	2005-06-15
KR100576988B1 (ko)	2006-05-10
SK285533B6 (sk)	2007-03-01
CA2263972C (en)	2008-01-29
PT1291353E (pt)	2005-10-31
ATE296832T1 (de)	2005-06-15
SK285535B6 (sk)	2007-03-01
CA2263972A1 (en)	1998-03-12
BG63547B1 (bg)	2002-04-30
AU729348B2 (en)	2001-02-01
IL128681A0 (en)	2000-01-31
EP1291353A1 (de)	2003-03-12
HUP9902869A3 (en)	2001-04-28
SK28699A3 (en)	2000-03-13
EP0929563B1 (de)	2005-06-01
HRP970473A2 (en)	1998-08-31
ES2242811T3 (es)	2005-11-16
CN100441591C (zh)	2008-12-10
US6075133A (en)	2000-06-13
RU2192427C2 (ru)	2002-11-10
PT929563E (pt)	2005-10-31
DE69733369T2 (de)	2006-01-26
CN1237183A (zh)	1999-12-01
DK0929563T3 (da)	2005-10-03
DK1291352T3 (da)	2005-09-19
CZ300106B6 (cs)	2009-02-11
EP1291353B1 (de)	2005-06-01
HRP20060276A2 (en)	2007-10-31
JP2001500855A (ja)	2001-01-23
HU230166B1 (hu)	2015-09-28
AU4178097A (en)	1998-03-26
PT1291352E (pt)	2005-09-30
ES2244716T3 (es)	2005-12-16
KR100523679B1 (ko)	2005-10-26
RO121473B1 (ro)	2007-06-29
JP4597274B2 (ja)	2010-12-15
KR20050044815A (ko)	2005-05-12
HRP20060278B1 (hr)	2014-04-11
DE69733439T2 (de)	2006-05-04
KR100610043B1 (ko)	2006-08-08
CN1273475C (zh)	2006-09-06
PT1291351E (pt)	2005-11-30
HUP9902869A2 (hu)	2000-02-28
ATE296307T1 (de)	2005-06-15
CN100460415C (zh)	2009-02-11
KR100568455B1 (ko)	2006-04-07
EP1291351B1 (de)	2005-07-13
EP0929563A1 (de)	1999-07-21
EP1291350A1 (de)	2003-03-12
PL188173B1 (pl)	2004-12-31
SK285534B6 (sk)	2007-03-01
CN1680420A (zh)	2005-10-12
BG103292A (en)	1999-12-30
SK286181B6 (sk)	2008-04-07

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2014-12-04

PC4A

Assignment and transfer of rights

Owner name: ABBVIE INC., NORTH CHICAGO, IL, US

Free format text: FORMER OWNER: ABBOTT LABORATORIES, ABBOTT PARK, IL, US

Effective date: 20120801

2017-11-03

MK4A

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Expiry date: 20170902

Publication	Publication Date	Title
SK285536B6 (sk)	2007-03-01	6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy
JP5222913B2 (ja)	2013-06-26	抗菌活性を有する６−ｏ−置換ケトリド
AU729348C (en)	2010-02-11	6-O-substituted ketolides having antibacterial activity