SK5472002A3 - Hygromycin derivatives - Google Patents

Hygromycin derivatives Download PDF

Info

Publication number: SK5472002A3
Authority: SK; Slovakia
Prior art keywords: alkyl; aryl; groups; group; independently
Prior art date: 1999-10-29

Application number

SK547-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Katherine Elizabeth Brighty

Robert Gerald Ii Linde

Matthew Merrill Hayward

Takushi Kaneko

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

2003-02-04

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

2003-02-04 Publication of SK5472002A3 publication Critical patent/SK5472002A3/sk

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 40
150000001875 compounds Chemical class 0.000 claims abstract description 494
238000000034 method Methods 0.000 claims abstract description 60
150000003839 salts Chemical class 0.000 claims abstract description 44
208000035143 Bacterial infection Diseases 0.000 claims abstract description 26
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 26
241000124008 Mammalia Species 0.000 claims abstract description 18
230000001580 bacterial effect Effects 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
239000012453 solvate Substances 0.000 claims abstract description 6
-1 4 - ((2 S, 3 S, 5 S) -5- (1 - ((E) -3,4-Difluoro-benzyloxyimino) -ethyl) -3-hydroxytetrahydrofuran-2-yloxy) -3-hydroxy-phenyl Chemical group 0.000 claims description 513
229910052739 hydrogen Inorganic materials 0.000 claims description 211
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 184
125000003118 aryl group Chemical group 0.000 claims description 176
125000000623 heterocyclic group Chemical group 0.000 claims description 169
229910052799 carbon Inorganic materials 0.000 claims description 161
125000000217 alkyl group Chemical group 0.000 claims description 130
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 93
125000005843 halogen group Chemical group 0.000 claims description 89
125000001424 substituent group Chemical group 0.000 claims description 88
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 79
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 78
229910052721 tungsten Inorganic materials 0.000 claims description 74
125000000753 cycloalkyl group Chemical group 0.000 claims description 61
125000004043 oxo group Chemical group O=* 0.000 claims description 56
238000011282 treatment Methods 0.000 claims description 56
239000000651 prodrug Substances 0.000 claims description 52
229940002612 prodrug Drugs 0.000 claims description 52
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
229910052760 oxygen Inorganic materials 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 38
150000001721 carbon Chemical group 0.000 claims description 35
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 32
208000015181 infectious disease Diseases 0.000 claims description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
125000005842 heteroatom Chemical group 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
201000010099 disease Diseases 0.000 claims description 24
125000004430 oxygen atom Chemical group O* 0.000 claims description 18
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000004434 sulfur atom Chemical group 0.000 claims description 18
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 17
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
241000251468 Actinopterygii Species 0.000 claims description 16
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
208000028172 protozoa infectious disease Diseases 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 14
MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical group [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
239000003242 anti bacterial agent Substances 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
229940088710 antibiotic agent Drugs 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 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
239000003120 macrolide antibiotic agent Substances 0.000 claims description 6
150000003952 β-lactams Chemical class 0.000 claims description 6
239000004098 Tetracycline Substances 0.000 claims description 5
235000019364 tetracycline Nutrition 0.000 claims description 5
150000003522 tetracyclines Chemical class 0.000 claims description 5
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
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
108010015899 Glycopeptides Proteins 0.000 claims description 4
102000002068 Glycopeptides Human genes 0.000 claims description 4
229940126575 aminoglycoside Drugs 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
230000015556 catabolic process Effects 0.000 claims description 4
238000006731 degradation reaction Methods 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
229960002180 tetracycline Drugs 0.000 claims description 4
229930101283 tetracycline Natural products 0.000 claims description 4
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
238000011260 co-administration Methods 0.000 claims description 3
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 claims description 2
UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
108010034396 Streptogramins Proteins 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
229910052720 vanadium Inorganic materials 0.000 abstract description 23
206010037075 Protozoal infections Diseases 0.000 abstract description 8
229910052727 yttrium Inorganic materials 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 243
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 156
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 126
239000011541 reaction mixture Substances 0.000 description 85
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
238000002360 preparation method Methods 0.000 description 81
239000000243 solution Substances 0.000 description 79
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 78
238000006243 chemical reaction Methods 0.000 description 69
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 52
239000002904 solvent Substances 0.000 description 48
239000002585 base Substances 0.000 description 46
239000000203 mixture Substances 0.000 description 43
239000003153 chemical reaction reagent Substances 0.000 description 42
125000006239 protecting group Chemical group 0.000 description 42
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
230000009466 transformation Effects 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
150000002576 ketones Chemical class 0.000 description 35
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 34
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 33
238000010898 silica gel chromatography Methods 0.000 description 31
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 30
239000002253 acid Substances 0.000 description 28
150000001408 amides Chemical class 0.000 description 27
239000000047 product Substances 0.000 description 26
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 26
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 25
230000015572 biosynthetic process Effects 0.000 description 25
239000012312 sodium hydride Substances 0.000 description 25
229910000104 sodium hydride Inorganic materials 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
239000012044 organic layer Substances 0.000 description 22
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
238000003786 synthesis reaction Methods 0.000 description 22
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 20
239000000460 chlorine Substances 0.000 description 20
239000000543 intermediate Substances 0.000 description 20
229910052943 magnesium sulfate Inorganic materials 0.000 description 20
235000019341 magnesium sulphate Nutrition 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
150000001412 amines Chemical group 0.000 description 19
238000004587 chromatography analysis Methods 0.000 description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
239000012634 fragment Substances 0.000 description 19
150000002431 hydrogen Chemical class 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 17
238000000746 purification Methods 0.000 description 17
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 17
PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 16
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 16
239000000010 aprotic solvent Substances 0.000 description 16
239000003480 eluent Substances 0.000 description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 15
239000012043 crude product Substances 0.000 description 15
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
229910052794 bromium Inorganic materials 0.000 description 14
229910052801 chlorine Inorganic materials 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 14
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
150000001299 aldehydes Chemical class 0.000 description 12
229940125904 compound 1 Drugs 0.000 description 12
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
238000010511 deprotection reaction Methods 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 11
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 10
150000003138 primary alcohols Chemical class 0.000 description 10
150000001540 azides Chemical class 0.000 description 9
150000002243 furanoses Chemical class 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
150000003141 primary amines Chemical class 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
239000007787 solid Substances 0.000 description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
230000029936 alkylation Effects 0.000 description 8
238000005804 alkylation reaction Methods 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
238000009833 condensation Methods 0.000 description 8
230000005494 condensation Effects 0.000 description 8
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
VLNZUSMTOFYNPS-UHFFFAOYSA-N diethylphosphorylformonitrile Chemical compound CCP(=O)(CC)C#N VLNZUSMTOFYNPS-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 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
239000002243 precursor Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 8
QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 7
241000283690 Bos taurus Species 0.000 description 7
238000006751 Mitsunobu reaction Methods 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
239000012267 brine Substances 0.000 description 7
229940127573 compound 38 Drugs 0.000 description 7
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 7
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 7
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 7
239000010410 layer Substances 0.000 description 7
230000004048 modification Effects 0.000 description 7
238000012986 modification Methods 0.000 description 7
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 7
125000002524 organometallic group Chemical group 0.000 description 7
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 7
229910000105 potassium hydride Inorganic materials 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
239000000758 substrate Substances 0.000 description 7
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125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 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
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000003876 thiosemicarbazone group Chemical group 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
229950008187 tosufloxacin Drugs 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
201000008827 tuberculosis Diseases 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
239000003981 vehicle Substances 0.000 description 1
239000000080 wetting agent Substances 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)

SK547-2002A 1999-10-29 2000-10-09 Hygromycin derivatives SK5472002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US16258199P	1999-10-29	1999-10-29
PCT/IB2000/001461 WO2001030795A1 (fr)	1999-10-29	2000-10-09	Derives d'hygromycine

Publications (1)

Publication Number	Publication Date
SK5472002A3 true SK5472002A3 (en)	2003-02-04

Family

ID=22586256

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK547-2002A SK5472002A3 (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)	NO20021850D0 (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
BR0111242A (pt) *	2000-06-02	2003-06-03	Pfizer Prod Inc	Derivados de higromicina para o tratamento de infecções por bactérias e protozoários
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
WO2020041179A1 (fr) *	2018-08-20	2020-02-27	Northeastern University	Composés d'hygromycine a et procédés de traitement de maladies à spirochètes
CA3164134A1 (fr)	2019-12-06	2021-06-10	Vertex Pharmaceuticals Incorporated	Tetrahydrofuranes substitues en tant que modulateurs de canaux sodiques
SI4347031T1 (sl)	2021-06-04	2026-01-30	Vertex Pharmaceuticals Incorporated	N-(hidroksialkil (hetero)aril) tetrahidrofuran karboksamidi kot modulatorji natrijevih kanalčkov

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 EE EEP200200228A patent/EE200200228A/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 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 CZ CZ20021355A patent/CZ20021355A3/cs unknown
- 2000-10-09 HK HK03101860.2A patent/HK1049672A1/zh unknown
- 2000-10-09 JP JP2001533146A patent/JP2003512473A/ja active Pending
- 2000-10-09 OA OA1200200129A patent/OA12081A/en unknown
- 2000-10-09 CN CN00814843A patent/CN1382150A/zh active Pending
- 2000-10-09 WO PCT/IB2000/001461 patent/WO2001030795A1/fr not_active Ceased
- 2000-10-09 HU HU0203525A patent/HUP0203525A3/hu unknown
- 2000-10-09 AU AU75494/00A patent/AU7549400A/en not_active Abandoned
- 2000-10-09 SK SK547-2002A patent/SK5472002A3/sk not_active Application Discontinuation
- 2000-10-09 KR KR1020027005533A patent/KR20020063885A/ko not_active Ceased
- 2000-10-09 AP APAP/P/2002/002494A patent/AP2002002494A0/en unknown
- 2000-10-09 EA EA200200292A patent/EA200200292A1/ru unknown
- 2000-10-09 TR TR2002/01145T patent/TR200201145T2/xx unknown
- 2000-10-09 PL PL00357083A patent/PL357083A1/xx not_active Application Discontinuation
- 2000-10-09 IL IL14857700A patent/IL148577A0/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 PE PE2000001146A patent/PE20010763A1/es not_active Application Discontinuation
- 2000-10-26 PA PA20008505801A patent/PA8505801A1/es unknown
- 2000-10-27 AR ARP000105698A patent/AR023282A1/es not_active Application Discontinuation
- 2000-10-27 TN TNTNSN00211A patent/TNSN00211A1/fr unknown
- 2000-10-27 SV SV2000000211A patent/SV2002000211A/es unknown
2002
- 2002-03-19 IS IS6311A patent/IS6311A/is unknown
- 2002-04-19 NO NO20021850A patent/NO20021850D0/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
EE200200228A (et)	2003-06-16
CN1382150A (zh)	2002-11-27
EP1224197A1 (fr)	2002-07-24
AU7549400A (en)	2001-05-08
BR0015153A (pt)	2002-07-16
PE20010763A1 (es)	2001-07-25
CZ20021355A3 (cs)	2002-11-13
HUP0203525A3 (en)	2003-08-28
HK1049672A1 (zh)	2003-05-23
PL357083A1 (en)	2004-07-12
HUP0203525A2 (hu)	2003-02-28
GT200000185A (es)	2002-04-18
EA200200292A1 (ru)	2002-10-31
SV2002000211A (es)	2002-07-16
IL148577A0 (en)	2002-09-12
MA26838A1 (fr)	2004-12-20
CA2389191A1 (fr)	2001-05-03
MXPA02004360A (es)	2002-11-07
KR20020063885A (ko)	2002-08-05
JP2003512473A (ja)	2003-04-02
TNSN00211A1 (fr)	2005-11-10
TR200201145T2 (tr)	2002-09-23
OA12081A (en)	2006-05-04
IS6311A (is)	2002-03-19
AR023282A1 (es)	2002-09-04
NO20021850L (no)	2002-04-19
CO5261498A1 (es)	2003-03-31
BG106727A (bg)	2003-01-31
WO2001030795A1 (fr)	2001-05-03
US6562792B1 (en)	2003-05-13
NO20021850D0 (no)	2002-04-19
AP2002002494A0 (en)	2002-06-30
PA8505801A1 (es)	2002-08-26

Legal Events

Date	Code	Title	Description
2010-06-07	FC9A	Refused patent application

Publication	Publication Date	Title
JPH11315093A (ja)	1999-11-16	３，６―ケタ―ル及びエノ―ルエ―テルマクロライド抗生物質
SK5812001A3 (en)	2001-12-03	Novel macrolide antibiotics
SK284607B6 (sk)	2005-07-01	Trinásťčlenné azalidy, spôsob ich výroby, farmaceutická kompozícia obsahujúca tieto azalidy a ich použitie ako antibiotiká
SK5472002A3 (en)	2003-02-04	Hygromycin derivatives
KR20010043303A (ko)	2001-05-25	하이그로마이신 에이 유도체
EP1077984B1 (fr)	2003-06-18	Derives 2 ? -desoxy-hygromycine
US6245745B1 (en)	2001-06-12	Hygromycin A derivatives
SK16612002A3 (sk)	2004-04-06	Deriváty hygromycínu A na použitie na liečenie bakteriálnych a protozoálnych infekcií
SK5322002A3 (en)	2003-01-09	Hygromycin A prodrugs
CZ20004075A3 (cs)	2001-05-16	Deriváty 2"-deoxy-hygromycinu
MXPA00010822A (es)	2001-07-31	Derivados de 2"-desoxi higromicina
AU2004201309A1 (en)	2004-04-29	Hygromycin A Derivatives as Antibacterial Agents
CZ20004074A3 (cs)	2001-05-16	Deriváty hygromycinu A
MXPA01005554A (en)	2001-12-04	Hygromycin a derivatives as antibacterial agents