OA11226A - C-4" substituted macrolide derivatives - Google Patents

C-4" substituted macrolide derivatives Download PDF

Info

Publication number: OA11226A
Authority: OA; OAPI
Prior art keywords: compound; hydroxy; formula; groups; alkyl
Prior art date: 1997-06-11

Application number

OA9900270A

Other languages

English (en)

Inventor

Brian Scott Bronk

Hengmiao Cheng

Takushi Kaneko

Vera Yang Bingwei

Edward Alan Glazer

Michael Anthony Letavic

Original Assignee

Pfizer Prod Inc

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.)

1997-06-11

Filing date

1999-12-03

Publication date

2003-07-16

1999-12-03 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2003-07-16 Publication of OA11226A publication Critical patent/OA11226A/en

Links

239000003120 macrolide antibiotic agent Substances 0.000 title description 18
150000001875 compounds Chemical class 0.000 claims abstract description 254
238000000034 method Methods 0.000 claims abstract description 52
208000015181 infectious disease Diseases 0.000 claims abstract description 48
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 12
208000035143 Bacterial infection Diseases 0.000 claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
-1 3-methoxypropyl Chemical group 0.000 claims description 80
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
229920006395 saturated elastomer Polymers 0.000 claims description 30
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
241000251468 Actinopterygii Species 0.000 claims description 13
241000124008 Mammalia Species 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000012312 sodium hydride Substances 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000002346 iodo group Chemical group I* 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Chemical group 0.000 claims description 3
125000006019 1-methyl-1-propenyl group Chemical group 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
125000003367 polycyclic group Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 17
239000003242 anti bacterial agent Substances 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
239000000243 solution Substances 0.000 description 77
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
239000012267 brine Substances 0.000 description 29
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 28
235000019439 ethyl acetate Nutrition 0.000 description 27
239000000203 mixture Substances 0.000 description 24
235000011114 ammonium hydroxide Nutrition 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
229910001868 water Inorganic materials 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
239000007787 solid Substances 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
239000002585 base Substances 0.000 description 16
239000007832 Na2SO4 Substances 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 15
235000011152 sodium sulphate Nutrition 0.000 description 15
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 14
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
239000008186 active pharmaceutical agent Substances 0.000 description 13
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000284 extract Substances 0.000 description 12
239000010410 layer Substances 0.000 description 12
229960001407 sodium bicarbonate Drugs 0.000 description 12
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 11
239000002253 acid Substances 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000000377 silicon dioxide Substances 0.000 description 11
229960001866 silicon dioxide Drugs 0.000 description 11
238000003756 stirring Methods 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 10
238000003556 assay Methods 0.000 description 10
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 10
229910052681 coesite Inorganic materials 0.000 description 10
229910052906 cristobalite Inorganic materials 0.000 description 10
229940093499 ethyl acetate Drugs 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
235000012239 silicon dioxide Nutrition 0.000 description 10
229910052682 stishovite Inorganic materials 0.000 description 10
238000012360 testing method Methods 0.000 description 10
229910052905 tridymite Inorganic materials 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
241000193996 Streptococcus pyogenes Species 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
235000015320 potassium carbonate Nutrition 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
101100119095 Enterococcus faecalis (strain ATCC 700802 / V583) ermB gene Proteins 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
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 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
241000606856 Pasteurella multocida Species 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
241000191967 Staphylococcus aureus Species 0.000 description 6
241000193998 Streptococcus pneumoniae Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000012986 modification Methods 0.000 description 6
230000004048 modification Effects 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
229940031000 streptococcus pneumoniae Drugs 0.000 description 6
241000271566 Aves Species 0.000 description 5
241000283690 Bos taurus Species 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000606768 Haemophilus influenzae Species 0.000 description 4
241001293418 Mannheimia haemolytica Species 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
229960003276 erythromycin Drugs 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012467 final product Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
238000004949 mass spectrometry Methods 0.000 description 4
230000007246 mechanism Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
229910003446 platinum oxide Inorganic materials 0.000 description 4
238000013207 serial dilution Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 3
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 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
101150052154 MSRA1 gene Proteins 0.000 description 3
241000588655 Moraxella catarrhalis Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
241000193985 Streptococcus agalactiae Species 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
229960004099 azithromycin Drugs 0.000 description 3
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
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238000010511 deprotection reaction Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
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239000000975 dye Substances 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
IJMOMMSECUQUFV-UHFFFAOYSA-N ethyl thiophene-2-carboximidate Chemical compound CCOC(=N)C1=CC=CS1 IJMOMMSECUQUFV-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
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125000001153 fluoro group Chemical group F* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
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239000008273 gelatin Substances 0.000 description 1
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239000007903 gelatin capsule Substances 0.000 description 1
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229940050410 gluconate Drugs 0.000 description 1
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150000003278 haem Chemical class 0.000 description 1
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IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
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238000010255 intramuscular injection Methods 0.000 description 1
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238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
206010023332 keratitis Diseases 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229940041028 lincosamides Drugs 0.000 description 1
239000002502 liposome Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
101150111763 mefA gene Proteins 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000006525 methoxy ethyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])OC([H])([H])[H] 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
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235000019813 microcrystalline cellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
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235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
229960005141 piperazine Drugs 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
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229920002721 polycyanoacrylate Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004626 polylactic acid Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
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229940041030 streptogramins Drugs 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
239000005720 sucrose Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000003831 tetrazolyl 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
206010044008 tonsillitis Diseases 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108091005703 transmembrane proteins Proteins 0.000 description 1
102000035160 transmembrane proteins Human genes 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
208000000143 urethritis Diseases 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Tropical Medicine & Parasitology (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

OA9900270A 1997-06-11 1999-12-03 C-4" substituted macrolide derivatives OA11226A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4998097P	1997-06-11	1997-06-11

Publications (1)

Publication Number	Publication Date
OA11226A true OA11226A (en)	2003-07-16

Family

ID=21962765

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900270A OA11226A (en)	1997-06-11	1999-12-03	C-4" substituted macrolide derivatives

Country Status (39)

Country	Link
EP (1)	EP0988309B1 (fr)
JP (1)	JP3262806B2 (fr)
KR (1)	KR100369959B1 (fr)
CN (1)	CN1145636C (fr)
AP (1)	AP1189A (fr)
AR (1)	AR013085A1 (fr)
AT (1)	ATE310742T1 (fr)
AU (1)	AU745006C (fr)
BG (1)	BG64357B1 (fr)
BR (1)	BR9810097A (fr)
CA (1)	CA2293397C (fr)
CO (1)	CO4950584A1 (fr)
DE (1)	DE69832486T2 (fr)
DZ (1)	DZ2515A1 (fr)
EA (1)	EA002440B1 (fr)
ES (1)	ES2251081T3 (fr)
GT (1)	GT199800075A (fr)
HN (1)	HN1998000074A (fr)
HR (1)	HRP980315A2 (fr)
HU (1)	HUP0004076A3 (fr)
ID (1)	ID24530A (fr)
IL (1)	IL132808A (fr)
IS (1)	IS1979B (fr)
MA (1)	MA24563A1 (fr)
MY (1)	MY133027A (fr)
NO (1)	NO315560B1 (fr)
NZ (1)	NZ500652A (fr)
OA (1)	OA11226A (fr)
PA (1)	PA8452001A1 (fr)
PE (1)	PE79999A1 (fr)
PL (1)	PL337497A1 (fr)
SK (1)	SK168299A3 (fr)
TN (1)	TNSN98084A1 (fr)
TW (2)	TW200418871A (fr)
UA (1)	UA70298C2 (fr)
UY (1)	UY25041A1 (fr)
WO (1)	WO1998056801A1 (fr)
YU (1)	YU62999A (fr)
ZA (1)	ZA985016B (fr)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6339063B1 (en)	1997-09-10	2002-01-15	Merck & Co., Inc.	9a-azalides as veterinary antimicrobial agents
ES2281136T3 (es) *	1997-09-10	2007-09-16	Merial Ltd.	Uso de 9a-azalidos como agentes antimicrobiales veterinarios.
EP1779853A3 (fr) *	1997-09-10	2010-01-27	Merial Ltd.	9a-azalides en tant qu'agents anti-microbiens à usage vétérinaire
AP9801420A0 (en) *	1998-01-02	1998-12-31	Pfizer Prod Inc	Novel macrolides.
EP1437360A3 (fr) *	1998-08-19	2005-04-06	Pfizer Products Inc.	C11-carbamates des macrolides antibactériens
US6043227A (en) *	1998-08-19	2000-03-28	Pfizer Inc.	C11 carbamates of macrolide antibacterials
US6100240A (en) *	1998-10-09	2000-08-08	Pfizer Inc	Macrolide derivatives
TR200101241T2 (tr)	1998-11-03	2001-09-21	Pfizer Products Inc.	Yeni makrolit antibiyotikler
CA2411293A1 (fr) *	1999-01-28	2000-07-28	Pfizer Products Inc.	Nouveaux azalides et procede de fabrication
DK1206476T3 (da) *	1999-08-24	2006-05-15	Abbott Lab	9a-azalider med antibakteriel virkning
US6764996B1 (en)	1999-08-24	2004-07-20	Abbott Laboratories	9a-azalides with antibacterial activity
BRPI0017013B1 (pt)	2000-01-27	2015-07-14	Zoetis P Llc	Composição de antibiótico azalídeo e método para sua obtenção
RU2263117C2 (ru) *	2001-04-27	2005-10-27	Пфайзер Продактс Инк.	Способ получения 4"-замещенных производных 9-деоксо-9а-аза-9а-гомоэритромицина а
JP2003040782A (ja) *	2001-05-31	2003-02-13	Pfizer Prod Inc	アザリド抗生物質組成物
AU2003264917A1 (en)	2002-07-08	2004-01-23	Pliva - Istrazivacki Institut D.O.O.	Hybrid molecules of macrolides with steroid/non-steroid anti-inflammatory, antineoplastic and antiviral active molecules
EP1521763A2 (fr) *	2002-07-08	2005-04-13	Pliva - Istrazivacki Institut d.o.o.	Substances anti-inflammatoires non steroidiennes, compositions et procedes d'utilisation de celles-ci
RS20050008A (sr)	2002-07-08	2007-06-04	Pliva-Istraživački Institut D.O.O.,	Nova jedinjenja,kompozicije i metode za lečenje inflamatornih oboljenja i stanja
TW200420573A (en)	2002-09-26	2004-10-16	Rib X Pharmaceuticals Inc	Bifunctional heterocyclic compounds and methods of making and using same
EP1638549A4 (fr) *	2003-03-10	2011-06-15	Optimer Pharmaceuticals Inc	Nouveaux agents antibacteriens
WO2005030227A1 (fr)	2003-09-23	2005-04-07	Enanta Pharmaceuticals, Inc.	Derives 9a-azalide 11-3c-bicycliques
EP1723159B1 (fr)	2004-02-27	2019-06-12	Melinta Therapeutics, Inc.	Composes macrocycliques et leurs procedes de fabrication et d'utilisation
JPWO2009019868A1 (ja)	2007-08-06	2010-10-28	大正製薬株式会社	１０ａ、１２位架橋型１０ａ−アザライド化合物
EP2214484A4 (fr)	2007-10-25	2013-01-02	Cempra Pharmaceuticals Inc	Procédé pour la préparation d'agents antibactériens macrolides
US8299035B2 (en)	2008-05-15	2012-10-30	Taisho Pharmaceutucal Co., Ltd.	10a-azalide compound having 4-membered ring structure
JP5711135B2 (ja)	2008-10-24	2015-04-30	センプラファーマシューティカルズ，インコーポレイテッド	胃腸疾患を治療するための方法
US9937194B1 (en)	2009-06-12	2018-04-10	Cempra Pharmaceuticals, Inc.	Compounds and methods for treating inflammatory diseases
WO2012038372A1 (fr) *	2010-09-20	2012-03-29	Novartis Ag	Nouveau procédé de préparation de 9-déoxo-9a-aza-9a-homoérythromycine a modifiée dans le c-4'' du cycle cladinose par un groupe époxyde
AR085286A1 (es) *	2011-02-21	2013-09-18	Taisho Pharmaceutical Co Ltd	Derivado de macrolido sustituido en la posicion c-4
NZ700182A (en)	2012-03-27	2017-02-24	Cempra Pharmaceuticals Inc	Parenteral formulations for administering macrolide antibiotics
JP5857008B2 (ja) *	2012-08-20	2016-02-10	大正製薬株式会社	Ｃ−４”位置換マクロライド誘導体を含有する医薬
JP6437523B2 (ja)	2013-04-04	2018-12-12	プレジデントアンドフェローズオブハーバードカレッジ	マクロライドならびにそれらの調製および使用の方法
CN103965273B (zh) *	2013-08-23	2016-05-25	普莱柯生物工程股份有限公司	一种大环内酯类化合物
CN105669798B (zh) *	2013-08-23	2019-07-26	普莱柯生物工程股份有限公司	一种大环内酯类化合物
AR102810A1 (es)	2014-08-18	2017-03-29	Taisho Pharmaceutical Co Ltd	Derivado de macrólido sustituido en la posición c-4
CN106998685A (zh)	2014-10-08	2017-08-01	哈佛大学的校长及成员们	14‑元酮内酯及其制备和使用方法
EP3273969A4 (fr)	2015-03-25	2018-11-21	President and Fellows of Harvard College	Macrolides à sucres modifiés de type désosamine et utilisations de ceux-ci
CN108003207B (zh)	2017-12-19	2019-05-10	海门慧聚药业有限公司	制备泰拉霉素的方法
TWI830987B (zh) *	2020-03-12	2024-02-01	美商碩騰服務公司	免疫調節脲氮雜內酯

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4150220A (en) *	1977-02-04	1979-04-17	Pfizer Inc.	Semi-synthetic 4"-erythromycin A derivatives
SE445223B (sv) *	1977-02-04	1986-06-09	Pfizer	Sett att framstella 4"-amino-erytomylin-a-derivat
SI8110592A8 (en) *	1981-03-06	1996-06-30	Pliva Pharm & Chem Works	Process for preparing of n-methyl-11-aza-10-deoxo-10-dihydroerythromycine a and derivatives thereof
US4474768A (en) *	1982-07-19	1984-10-02	Pfizer Inc.	N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor
DE3475073D1 (en) *	1983-09-06	1988-12-15	Pfizer	Azahomoerythromycin b derivatives and intermediates thereof
US4512982A (en) *	1984-04-13	1985-04-23	Pfizer Inc.	9α-Aza-9α-homoerythromycin compounds, pharmaceutical composition and therapeutic method
CA2064634C (fr) *	1991-04-04	1998-08-04	James V. Heck	Derives de 9-desoxo-8a-aza-8a-homoerythromycine a modifies en positions 4"- et 8a
US5441939A (en) *	1994-03-04	1995-08-15	Pfizer Inc.	3"-desmethoxy derivatives of erythromycin and azithromycin
US5412982A (en) *	1994-03-10	1995-05-09	Potts; James K.	Windsock support

1998
- 1998-05-20 HN HN1998000074A patent/HN1998000074A/es unknown
- 1998-05-22 PA PA19988452001A patent/PA8452001A1/es unknown
- 1998-05-25 SK SK1682-99A patent/SK168299A3/sk unknown
- 1998-05-25 UA UA99126737A patent/UA70298C2/uk unknown
- 1998-05-25 DE DE69832486T patent/DE69832486T2/de not_active Expired - Fee Related
- 1998-05-25 NZ NZ500652A patent/NZ500652A/en unknown
- 1998-05-25 AT AT98919414T patent/ATE310742T1/de not_active IP Right Cessation
- 1998-05-25 JP JP50192999A patent/JP3262806B2/ja not_active Expired - Fee Related
- 1998-05-25 PL PL98337497A patent/PL337497A1/xx unknown
- 1998-05-25 KR KR10-1999-7011643A patent/KR100369959B1/ko not_active Expired - Fee Related
- 1998-05-25 CA CA002293397A patent/CA2293397C/fr not_active Expired - Fee Related
- 1998-05-25 ES ES98919414T patent/ES2251081T3/es not_active Expired - Lifetime
- 1998-05-25 CN CNB988060493A patent/CN1145636C/zh not_active Expired - Fee Related
- 1998-05-25 EP EP98919414A patent/EP0988309B1/fr not_active Expired - Lifetime
- 1998-05-25 YU YU62999A patent/YU62999A/sh unknown
- 1998-05-25 EA EA199901014A patent/EA002440B1/ru not_active IP Right Cessation
- 1998-05-25 AU AU72281/98A patent/AU745006C/en not_active Ceased
- 1998-05-25 IL IL13280898A patent/IL132808A/en not_active IP Right Cessation
- 1998-05-25 HU HU0004076A patent/HUP0004076A3/hu unknown
- 1998-05-25 WO PCT/IB1998/000799 patent/WO1998056801A1/fr not_active Ceased
- 1998-05-25 BR BR9810097-1A patent/BR9810097A/pt not_active IP Right Cessation
- 1998-05-25 ID IDW991565A patent/ID24530A/id unknown
- 1998-06-04 AP APAP/P/1998/001254A patent/AP1189A/en active
- 1998-06-08 TW TW093111859A patent/TW200418871A/zh unknown
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- 1998-06-08 TW TW087109085A patent/TWI224106B/zh active
- 1998-06-08 PE PE1998000469A patent/PE79999A1/es not_active Application Discontinuation
- 1998-06-09 AR ARP980102704A patent/AR013085A1/es active IP Right Grant
- 1998-06-09 MY MYPI98002563A patent/MY133027A/en unknown
- 1998-06-10 ZA ZA9805016A patent/ZA985016B/xx unknown
- 1998-06-10 DZ DZ980125A patent/DZ2515A1/fr active
- 1998-06-10 CO CO98033231A patent/CO4950584A1/es unknown
- 1998-06-10 TN TNTNSN98084A patent/TNSN98084A1/fr unknown
- 1998-06-10 MA MA25106A patent/MA24563A1/fr unknown
- 1998-06-11 UY UY25041A patent/UY25041A1/es not_active IP Right Cessation
- 1998-06-11 HR HR60/049,980A patent/HRP980315A2/hr not_active Application Discontinuation
1999
- 1999-11-16 IS IS5250A patent/IS1979B/is unknown
- 1999-12-03 OA OA9900270A patent/OA11226A/en unknown
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Also Published As

Publication number	Publication date
NZ500652A (en)	2001-10-26
UA70298A (uk)	2004-10-15
CO4950584A1 (es)	2000-09-01
KR100369959B1 (ko)	2003-02-12
CA2293397A1 (fr)	1998-12-17
IS1979B (is)	2005-01-14
EA002440B1 (ru)	2002-04-25
TW200418871A (en)	2004-10-01
IL132808A0 (en)	2001-03-19
JP2000514097A (ja)	2000-10-24
PE79999A1 (es)	1999-08-25
JP3262806B2 (ja)	2002-03-04
EA199901014A1 (ru)	2000-06-26
ZA985016B (en)	1999-12-10
SK168299A3 (en)	2000-09-12
UY25041A1 (es)	2000-09-29
HK1025974A1 (en)	2000-12-01
EP0988309B1 (fr)	2005-11-23
AU745006B2 (en)	2002-03-07
ATE310742T1 (de)	2005-12-15
ES2251081T3 (es)	2006-04-16
DZ2515A1 (fr)	2003-02-01
NO996107L (no)	2000-02-10
CN1145636C (zh)	2004-04-14
AP1189A (en)	2003-07-16
CN1259955A (zh)	2000-07-12
KR20010013633A (ko)	2001-02-26
IL132808A (en)	2004-08-31
AP9801254A0 (en)	1998-06-30
NO315560B1 (no)	2003-09-22
CA2293397C (fr)	2004-08-31
HUP0004076A3 (en)	2003-05-28
MA24563A1 (fr)	1998-12-31
MY133027A (en)	2007-10-31
ID24530A (id)	2000-07-20
DE69832486D1 (de)	2005-12-29
YU62999A (sh)	2002-10-18
HN1998000074A (es)	1999-01-08
IS5250A (is)	1999-11-16
GT199800075A (es)	1999-11-30
HRP980315A2 (en)	1999-04-30
AR013085A1 (es)	2000-12-13
PA8452001A1 (es)	2000-05-24
WO1998056801A1 (fr)	1998-12-17
AU745006C (en)	2006-02-23
HUP0004076A2 (hu)	2001-04-28
NO996107D0 (no)	1999-12-10
TWI224106B (en)	2004-11-21
EP0988309A1 (fr)	2000-03-29
AU7228198A (en)	1998-12-30
PL337497A1 (en)	2000-08-28
DE69832486T2 (de)	2006-07-27
BG64357B1 (bg)	2004-11-30
UA70298C2 (uk)	2004-10-15
TNSN98084A1 (fr)	2005-03-15
BG103969A (en)	2000-07-31
BR9810097A (pt)	2000-08-08

Publication	Publication Date	Title
OA11226A (en)	2003-07-16	C-4" substituted macrolide derivatives
US6420536B1 (en)	2002-07-16	4″-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives
US6300316B1 (en)	2001-10-09	C-4 substituted macrolide antibiotics
US6407074B1 (en)	2002-06-18	C-4″-substituted macrolide derivatives
CA2293335A1 (fr)	1998-12-17	Derives de 9-oxime erythromycine
US6043227A (en)	2000-03-28	C11 carbamates of macrolide antibacterials
US6162794A (en)	2000-12-19	Erythromycin derivatives
US20020025937A1 (en)	2002-02-28	9-oxime erythromycin derivatives
WO1999062920A1 (fr)	1999-12-09	Derives 3-keto tricycliques de 6-o-methylerythromycine
MXPA99011496A (en)	2000-07-01	C-4''-substituted macrolide derivatives
CZ438999A3 (cs)	2000-05-17	C-4"- substituované makrolidové deriváty
MXPA99011495A (en)	2001-05-17	4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives