OA12081A - Hygromycin derivatives. - Google Patents

Hygromycin derivatives. Download PDF

Info

Publication number: OA12081A
Authority: OA; OAPI
Prior art keywords: alkyl; groups; aryl; independently; methyl
Prior art date: 1999-10-29

Application number

OA1200200129A

Other languages

English (en)

Inventor

Matthew Merrill Hayward

Takushi Kaneko

Linde Robert Gerald Ii

Katherine Elizabeth Brighty

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.)

1999-10-29

Filing date

2000-10-09

Publication date

2006-05-04

2000-10-09 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-05-04 Publication of OA12081A publication Critical patent/OA12081A/en

Links

YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 title claims description 41
150000001875 compounds Chemical class 0.000 claims abstract description 381
150000003839 salts Chemical class 0.000 claims abstract description 23
208000035143 Bacterial infection Diseases 0.000 claims abstract description 16
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 16
241000124008 Mammalia Species 0.000 claims abstract description 12
206010037075 Protozoal infections Diseases 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims description 199
125000000623 heterocyclic group Chemical group 0.000 claims description 118
125000003118 aryl group Chemical group 0.000 claims description 99
229910052799 carbon Inorganic materials 0.000 claims description 99
-1 riitro Chemical group 0.000 claims description 97
229910052739 hydrogen Inorganic materials 0.000 claims description 78
125000005843 halogen group Chemical group 0.000 claims description 72
239000000203 mixture Substances 0.000 claims description 68
125000001424 substituent group Chemical group 0.000 claims description 66
238000011282 treatment Methods 0.000 claims description 58
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 57
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 49
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 49
208000015181 infectious disease Diseases 0.000 claims description 47
239000000651 prodrug Substances 0.000 claims description 47
229940002612 prodrug Drugs 0.000 claims description 47
125000004043 oxo group Chemical group O=* 0.000 claims description 45
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 44
125000000753 cycloalkyl group Chemical group 0.000 claims description 44
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
YQYJSBFKSSDGFO-FWAVGLHBSA-N hygromycin A Chemical compound O[C@H]1[C@H](O)[C@H](C(=O)C)O[C@@H]1Oc1ccc(\C=C(/C)C(=O)N[C@@H]2[C@@H]([C@H]3OCO[C@H]3[C@@H](O)[C@@H]2O)O)cc1O YQYJSBFKSSDGFO-FWAVGLHBSA-N 0.000 claims description 28
150000001721 carbon Chemical group 0.000 claims description 25
125000004430 oxygen atom Chemical group O* 0.000 claims description 22
125000004434 sulfur atom Chemical group 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 17
MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 15
208000035475 disorder Diseases 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
241000251468 Actinopterygii Species 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
229910052721 tungsten Inorganic materials 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
208000028172 protozoa infectious disease Diseases 0.000 claims description 7
108020004021 3-ketosteroid receptors Proteins 0.000 claims description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
150000003952 β-lactams Chemical class 0.000 claims description 6
DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 claims description 4
108010015899 Glycopeptides Proteins 0.000 claims description 4
102000002068 Glycopeptides Human genes 0.000 claims description 4
108010034396 Streptogramins Proteins 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
230000003115 biocidal effect Effects 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
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 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
TWNWWLGUDWBWPT-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-4,5,7-triol Chemical compound OC1CC(C(C2OCOC21)O)O TWNWWLGUDWBWPT-UHFFFAOYSA-N 0.000 claims 1
125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
101100502522 Mus musculus Fcor gene Proteins 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
229940000425 combination drug Drugs 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
238000000034 method Methods 0.000 abstract description 47
229910052720 vanadium Inorganic materials 0.000 abstract description 8
239000008194 pharmaceutical composition Substances 0.000 abstract description 7
230000001580 bacterial effect Effects 0.000 abstract description 6
239000012453 solvate Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 264
229940117913 acrylamide Drugs 0.000 description 214
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 195
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 151
238000006243 chemical reaction Methods 0.000 description 145
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 140
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 101
239000000243 solution Substances 0.000 description 90
229940093499 ethyl acetate Drugs 0.000 description 88
235000019439 ethyl acetate Nutrition 0.000 description 88
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 76
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
239000002904 solvent Substances 0.000 description 47
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
239000002585 base Substances 0.000 description 41
239000003153 chemical reaction reagent Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
150000002576 ketones Chemical class 0.000 description 34
230000009466 transformation Effects 0.000 description 34
239000002253 acid Substances 0.000 description 31
150000001408 amides Chemical class 0.000 description 29
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 29
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 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
238000010898 silica gel chromatography Methods 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
239000012634 fragment Substances 0.000 description 24
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
230000015572 biosynthetic process Effects 0.000 description 21
235000002639 sodium chloride Nutrition 0.000 description 21
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 20
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 20
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 20
239000012312 sodium hydride Substances 0.000 description 20
229910000104 sodium hydride Inorganic materials 0.000 description 20
238000003786 synthesis reaction Methods 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 19
150000001412 amines Chemical class 0.000 description 19
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 18
238000004587 chromatography analysis Methods 0.000 description 18
239000000543 intermediate Substances 0.000 description 18
239000012044 organic layer Substances 0.000 description 18
238000000746 purification Methods 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
239000012267 brine Substances 0.000 description 17
239000012043 crude product Substances 0.000 description 17
239000000047 product Substances 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 15
239000000010 aprotic solvent Substances 0.000 description 15
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 15
125000006239 protecting group Chemical group 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
238000010511 deprotection reaction Methods 0.000 description 13
229940073584 methylene chloride Drugs 0.000 description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 12
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
230000009471 action Effects 0.000 description 11
229910052700 potassium Inorganic materials 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
125000001246 bromo group Chemical group Br* 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
125000004356 hydroxy functional group Chemical group O* 0.000 description 10
239000011591 potassium Substances 0.000 description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
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 9
POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 9
230000029936 alkylation Effects 0.000 description 9
238000005804 alkylation reaction Methods 0.000 description 9
230000008878 coupling Effects 0.000 description 9
238000010168 coupling process Methods 0.000 description 9
238000005859 coupling reaction Methods 0.000 description 9
150000002243 furanoses Chemical class 0.000 description 9
239000010410 layer Substances 0.000 description 9
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 9
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 9
150000002923 oximes Chemical group 0.000 description 9
150000003141 primary amines Chemical class 0.000 description 9
239000011734 sodium Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000012279 sodium borohydride Substances 0.000 description 9
229910000033 sodium borohydride Inorganic materials 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 8
VLNZUSMTOFYNPS-UHFFFAOYSA-N diethylphosphorylformonitrile Chemical compound CCP(=O)(CC)C#N VLNZUSMTOFYNPS-UHFFFAOYSA-N 0.000 description 8
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 8
125000002524 organometallic group Chemical group 0.000 description 8
230000003647 oxidation Effects 0.000 description 8
238000007254 oxidation reaction Methods 0.000 description 8
239000008055 phosphate buffer solution Substances 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
150000003138 primary alcohols Chemical class 0.000 description 8
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
239000000758 substrate Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
229960004132 diethyl ether Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000005227 gel permeation chromatography Methods 0.000 description 7
239000012442 inert solvent Substances 0.000 description 7
230000004048 modification Effects 0.000 description 7
238000012986 modification Methods 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
239000007787 solid Substances 0.000 description 7
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
241000283690 Bos taurus Species 0.000 description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
241000193996 Streptococcus pyogenes Species 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
244000309464 bull Species 0.000 description 6
239000007822 coupling agent Substances 0.000 description 6
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000004678 hydrides Chemical class 0.000 description 6
229960000367 inositol Drugs 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
229960005235 piperonyl butoxide Drugs 0.000 description 6
239000002243 precursor Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
229960001866 silicon dioxide Drugs 0.000 description 6
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
KQTXIZHBFFWWFW-UHFFFAOYSA-L silver(I) carbonate Inorganic materials [Ag]OC(=O)O[Ag] KQTXIZHBFFWWFW-UHFFFAOYSA-L 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
229960002218 sodium chlorite Drugs 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
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229940115920 streptococcus dysgalactiae Drugs 0.000 description 1
229940076156 streptococcus pyogenes Drugs 0.000 description 1
238000006467 substitution reaction Methods 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
150000003871 sulfonates Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 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
UIYOVVYZPVVUMJ-UHFFFAOYSA-N tert-butyl carbamoyl carbonate Chemical compound CC(C)(C)OC(=O)OC(N)=O UIYOVVYZPVVUMJ-UHFFFAOYSA-N 0.000 description 1
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000001583 thiepanyl group Chemical group 0.000 description 1
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000003354 tissue distribution assay Methods 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229950008187 tosufloxacin Drugs 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

OA1200200129A 1999-10-29 2000-10-09 Hygromycin derivatives. OA12081A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US16258199P	1999-10-29	1999-10-29

Publications (1)

Publication Number	Publication Date
OA12081A true OA12081A (en)	2006-05-04

Family

ID=22586256

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200129A OA12081A (en)	1999-10-29	2000-10-09	Hygromycin derivatives.

Country Status (32)

Country	Link
US (1)	US6562792B1 (fr)
EP (1)	EP1224197A1 (fr)
JP (1)	JP2003512473A (fr)
KR (1)	KR20020063885A (fr)
CN (1)	CN1382150A (fr)
AP (1)	AP2002002494A0 (fr)
AR (1)	AR023282A1 (fr)
AU (1)	AU7549400A (fr)
BG (1)	BG106727A (fr)
BR (1)	BR0015153A (fr)
CA (1)	CA2389191A1 (fr)
CO (1)	CO5261498A1 (fr)
CZ (1)	CZ20021355A3 (fr)
EA (1)	EA200200292A1 (fr)
EE (1)	EE200200228A (fr)
GT (1)	GT200000185A (fr)
HK (1)	HK1049672A1 (fr)
HU (1)	HUP0203525A3 (fr)
IL (1)	IL148577A0 (fr)
IS (1)	IS6311A (fr)
MA (1)	MA26838A1 (fr)
MX (1)	MXPA02004360A (fr)
NO (1)	NO20021850L (fr)
OA (1)	OA12081A (fr)
PA (1)	PA8505801A1 (fr)
PE (1)	PE20010763A1 (fr)
PL (1)	PL357083A1 (fr)
SK (1)	SK5472002A3 (fr)
SV (1)	SV2002000211A (fr)
TN (1)	TNSN00211A1 (fr)
TR (1)	TR200201145T2 (fr)
WO (1)	WO2001030795A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1432019A (zh) *	2000-06-02	2003-07-23	辉瑞产品公司	用于治疗细菌和原生动物感染的潮霉素a衍生物
US6653481B2 (en) *	2000-12-29	2003-11-25	Synthon Bv	Process for making amlodipine
US7923439B2 (en)	2008-10-15	2011-04-12	Tyco Healthcare Group Lp	Hydroxamate compositions
EP3840743A4 (fr)	2018-08-20	2022-08-17	Northeastern University	Composés d'hygromycine a et procédés de traitement de maladies à spirochètes
DK4069691T3 (da)	2019-12-06	2024-10-28	Vertex Pharma	Substituerede tetrahydrofuraner som modulatorer af natriumkanaler
MA64853B1 (fr)	2021-06-04	2025-11-28	Vertex Pharmaceuticals Incorporated	N-(hydroxyalkyl (hétéro)aryl) tétrahydrofuran carboxamides utilisés en tant que modulateurs de canaux sodiques

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PL348063A1 (en) *	1998-12-02	2002-05-06	Pfizer Prod Inc	Hygromycin a derivatives as antibacterial agents

2000
- 2000-10-09 CZ CZ20021355A patent/CZ20021355A3/cs unknown
- 2000-10-09 EA EA200200292A patent/EA200200292A1/ru unknown
- 2000-10-09 SK SK547-2002A patent/SK5472002A3/sk not_active Application Discontinuation
- 2000-10-09 PL PL00357083A patent/PL357083A1/xx not_active Application Discontinuation
- 2000-10-09 JP JP2001533146A patent/JP2003512473A/ja active Pending
- 2000-10-09 OA OA1200200129A patent/OA12081A/en unknown
- 2000-10-09 HU HU0203525A patent/HUP0203525A3/hu unknown
- 2000-10-09 KR KR1020027005533A patent/KR20020063885A/ko not_active Ceased
- 2000-10-09 WO PCT/IB2000/001461 patent/WO2001030795A1/fr not_active Ceased
- 2000-10-09 BR BR0015153-0A patent/BR0015153A/pt not_active IP Right Cessation
- 2000-10-09 CA CA002389191A patent/CA2389191A1/fr not_active Abandoned
- 2000-10-09 AP APAP/P/2002/002494A patent/AP2002002494A0/en unknown
- 2000-10-09 IL IL14857700A patent/IL148577A0/xx unknown
- 2000-10-09 HK HK03101860.2A patent/HK1049672A1/zh unknown
- 2000-10-09 TR TR2002/01145T patent/TR200201145T2/xx unknown
- 2000-10-09 MX MXPA02004360A patent/MXPA02004360A/es active IP Right Grant
- 2000-10-09 EP EP00964572A patent/EP1224197A1/fr not_active Withdrawn
- 2000-10-09 CN CN00814843A patent/CN1382150A/zh active Pending
- 2000-10-09 AU AU75494/00A patent/AU7549400A/en not_active Abandoned
- 2000-10-09 EE EEP200200228A patent/EE200200228A/xx unknown
- 2000-10-20 US US09/693,118 patent/US6562792B1/en not_active Expired - Fee Related
- 2000-10-25 GT GT200000185A patent/GT200000185A/es unknown
- 2000-10-25 CO CO00081374A patent/CO5261498A1/es not_active Application Discontinuation
- 2000-10-26 PA PA20008505801A patent/PA8505801A1/es unknown
- 2000-10-26 PE PE2000001146A patent/PE20010763A1/es not_active Application Discontinuation
- 2000-10-27 SV SV2000000211A patent/SV2002000211A/es unknown
- 2000-10-27 TN TNTNSN00211A patent/TNSN00211A1/fr unknown
- 2000-10-27 AR ARP000105698A patent/AR023282A1/es not_active Application Discontinuation
2002
- 2002-03-19 IS IS6311A patent/IS6311A/is unknown
- 2002-04-19 NO NO20021850A patent/NO20021850L/no not_active Application Discontinuation
- 2002-04-22 MA MA26613A patent/MA26838A1/fr unknown
- 2002-05-20 BG BG106727A patent/BG106727A/bg unknown

Also Published As

Publication number	Publication date
CZ20021355A3 (cs)	2002-11-13
TNSN00211A1 (fr)	2005-11-10
SK5472002A3 (en)	2003-02-04
AU7549400A (en)	2001-05-08
MXPA02004360A (es)	2002-11-07
TR200201145T2 (tr)	2002-09-23
PL357083A1 (en)	2004-07-12
EP1224197A1 (fr)	2002-07-24
CN1382150A (zh)	2002-11-27
GT200000185A (es)	2002-04-18
IS6311A (is)	2002-03-19
PA8505801A1 (es)	2002-08-26
PE20010763A1 (es)	2001-07-25
AP2002002494A0 (en)	2002-06-30
AR023282A1 (es)	2002-09-04
EE200200228A (et)	2003-06-16
CO5261498A1 (es)	2003-03-31
US6562792B1 (en)	2003-05-13
KR20020063885A (ko)	2002-08-05
BR0015153A (pt)	2002-07-16
EA200200292A1 (ru)	2002-10-31
NO20021850D0 (no)	2002-04-19
BG106727A (bg)	2003-01-31
CA2389191A1 (fr)	2001-05-03
HK1049672A1 (zh)	2003-05-23
HUP0203525A3 (en)	2003-08-28
IL148577A0 (en)	2002-09-12
MA26838A1 (fr)	2004-12-20
SV2002000211A (es)	2002-07-16
JP2003512473A (ja)	2003-04-02
HUP0203525A2 (hu)	2003-02-28
NO20021850L (no)	2002-04-19
WO2001030795A1 (fr)	2001-05-03

Publication	Publication Date	Title
KR100396168B1 (ko)	2003-08-27	4″-치환된-9-데옥소-9ａ-아자-9ａ-호모에리트로마이신 Ａ유도체
KR100369959B1 (ko)	2003-02-12	Ｃ-4″-치환된-마크롤리드 유도체
KR100244729B1 (ko)	2000-02-15	5-0-데소사미닐에리쓰로노라이드a유도체
AU1675400A (en)	2000-08-18	Ketolide antibiotics
NO312366B1 (no)	2002-04-29	3,6-ketal- og enoleter-makrolidforbindelser, anvendelse derav samt farmasöytisk preparat og fremgangsmåte for fremstilling derav
SK284607B6 (sk)	2005-07-01	Trinásťčlenné azalidy, spôsob ich výroby, farmaceutická kompozícia obsahujúca tieto azalidy a ich použitie ako antibiotiká
SK5812001A3 (en)	2001-12-03	Novel macrolide antibiotics
CA2328775A1 (fr)	2001-06-29	Derives de la 4-oxo-2-ureido-1,4,5,6-tetrahydro-pyrimidine
OA12081A (en)	2006-05-04	Hygromycin derivatives.
EP1077984B1 (fr)	2003-06-18	Derives 2 ? -desoxy-hygromycine
US6245745B1 (en)	2001-06-12	Hygromycin A derivatives
EP1115732B1 (fr)	2005-06-29	Antibiotiques carbamates et carbazates cetolides
WO2001092280A1 (fr)	2001-12-06	Derives de l'hygromycine a pour le traitement d'infections bacteriennes et protozooses
EP1298138B1 (fr)	2006-11-02	Dérivés anitiobiotiques de Carbamate et de Carbazate Kètolides
EP0515141A1 (fr)	1992-11-25	Procédé pour la préparation de 8A-aza-8A-homoerythromycin lactams cycliques
MXPA01000120A (en)	2002-06-05	4-oxo-2-ureido-1,4,5,6-tetrahydro-pyrimidine derivatives useful as antibacterial and antiprotozoal agents
JPWO1993021199A1 (ja)	1994-05-12	５−０−デソサミニルエリスロノライドａ誘導体
CZ438999A3 (cs)	2000-05-17	C-4"- substituované makrolidové deriváty
CZ20004075A3 (cs)	2001-05-16	Deriváty 2"-deoxy-hygromycinu