OA12079A - Hygromycin a prodrugs. - Google Patents

Hygromycin a prodrugs. Download PDF

Info

Publication number: OA12079A
Authority: OA; OAPI
Prior art keywords: hydrogen; alkyl; hydroxy; compound; propenyl
Prior art date: 1999-10-29

Application number

OA1200200127A

Other languages

English (en)

Inventor

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

2000-09-28

Publication date

2006-05-04

2000-09-28 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-05-04 Publication of OA12079A publication Critical patent/OA12079A/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 description 9
239000000651 prodrug Substances 0.000 title description 5
229940002612 prodrug Drugs 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 100
208000015181 infectious disease Diseases 0.000 claims abstract description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
-1 aminoC(O>· Chemical group 0.000 claims description 38
229910052739 hydrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
125000002252 acyl group Chemical group 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 13
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
241000251468 Actinopterygii Species 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
208000028172 protozoa infectious disease Diseases 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 2
229910014585 C2-Ce Inorganic materials 0.000 claims 2
101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims 1
OCOHZTPDJIANAQ-RBQXGTMLSA-N OC1C2OCOC2C(O)C(O)C1NC(=O)C(C)=CC(C=C1OP(O)(O)=O)=CC=C1OC(O1)CC(O)C1C(\C)=N\OCC1=CC=CC(F)=C1 Chemical compound OC1C2OCOC2C(O)C(O)C1NC(=O)C(C)=CC(C=C1OP(O)(O)=O)=CC=C1OC(O1)CC(O)C1C(\C)=N\OCC1=CC=CC(F)=C1 OCOHZTPDJIANAQ-RBQXGTMLSA-N 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 21
238000000034 method Methods 0.000 abstract description 13
208000035143 Bacterial infection Diseases 0.000 abstract description 12
208000022362 bacterial infectious disease Diseases 0.000 abstract description 12
208000035475 disorder Diseases 0.000 abstract description 10
206010037075 Protozoal infections Diseases 0.000 abstract description 8
230000000844 anti-bacterial effect Effects 0.000 abstract description 6
230000001580 bacterial effect Effects 0.000 abstract description 6
239000008194 pharmaceutical composition Substances 0.000 abstract description 6
239000003242 anti bacterial agent Substances 0.000 abstract description 5
239000003904 antiprotozoal agent Substances 0.000 abstract description 2
239000012453 solvate Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 9
230000000694 effects Effects 0.000 description 8
0 C**=C(C)[C@]([C@](C1*)O)O[C@@]1OC(C=C[C@](C1)C=C(C)C(N)=O)=C1OC(*)=* Chemical compound C**=C(C)[C@]([C@](C1*)O)O[C@@]1OC(C=C[C@](C1)C=C(C)C(N)=O)=C1OC(*)=* 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
238000003556 assay Methods 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
125000001246 bromo group Chemical group Br* 0.000 description 6
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 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
241000193996 Streptococcus pyogenes Species 0.000 description 5
108010059993 Vancomycin Proteins 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 5
229910000105 potassium hydride Inorganic materials 0.000 description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
229960003165 vancomycin Drugs 0.000 description 5
MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 5
MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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 4
241000699670 Mus sp. Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
239000000010 aprotic solvent Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
239000003814 drug Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000003120 macrolide antibiotic agent Substances 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
150000003952 β-lactams Chemical class 0.000 description 4
101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 description 3
241000271566 Aves Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
239000004098 Tetracycline Substances 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229940126575 aminoglycoside Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
150000007514 bases Chemical class 0.000 description 3
239000011575 calcium Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229960005091 chloramphenicol Drugs 0.000 description 3
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 3
229910052681 coesite Inorganic materials 0.000 description 3
229910052906 cristobalite Inorganic materials 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229940041033 macrolides Drugs 0.000 description 3
239000002674 ointment Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
150000007660 quinolones Chemical class 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
241000894007 species Species 0.000 description 3
229910052682 stishovite Inorganic materials 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
235000019364 tetracycline Nutrition 0.000 description 3
229940040944 tetracyclines Drugs 0.000 description 3
150000003522 tetracyclines Chemical class 0.000 description 3
229910052905 tridymite Inorganic materials 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241001647372 Chlamydia pneumoniae Species 0.000 description 2
241000606153 Chlamydia trachomatis Species 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
241000193403 Clostridium Species 0.000 description 2
241000194032 Enterococcus faecalis Species 0.000 description 2
241000194031 Enterococcus faecium Species 0.000 description 2
102000009338 Gastric Mucins Human genes 0.000 description 2
108010009066 Gastric Mucins Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000606768 Haemophilus influenzae Species 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
PQMWYJDJHJQZDE-UHFFFAOYSA-M Methantheline bromide Chemical compound [Br-].C1=CC=C2C(C(=O)OCC[N+](C)(CC)CC)C3=CC=CC=C3OC2=C1 PQMWYJDJHJQZDE-UHFFFAOYSA-M 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
241000191963 Staphylococcus epidermidis Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
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150000004703 alkoxides Chemical class 0.000 description 2
230000000689 aminoacylating effect Effects 0.000 description 2
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229910052791 calcium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
229940038705 chlamydia trachomatis Drugs 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000006071 cream Substances 0.000 description 2
UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
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238000000338 in vitro Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
235000015110 jellies Nutrition 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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159000000001 potassium salts Chemical class 0.000 description 2
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YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
PVPBHKCSQBLDEW-ZQOBQRRWSA-N (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol 4-hydroxybutane-1-sulfonic acid Chemical compound OCCCCS(O)(=O)=O.OC[C@H]1O[C@@H]2O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@@H]6[C@@H](CO)O[C@H](O[C@@H]7[C@@H](CO)O[C@H](O[C@@H]8[C@@H](CO)O[C@H](O[C@H]1[C@H](O)[C@H]2O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O PVPBHKCSQBLDEW-ZQOBQRRWSA-N 0.000 description 1
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229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005306 thianaphthenyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
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
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000003354 tissue distribution assay Methods 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
238000012546 transfer Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

OA1200200127A 1999-10-29 2000-09-28 Hygromycin a prodrugs. OA12079A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US16272299P	1999-10-29	1999-10-29

Publications (1)

Publication Number	Publication Date
OA12079A true OA12079A (en)	2006-05-04

Family

ID=22586880

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200127A OA12079A (en)	1999-10-29	2000-09-28	Hygromycin a prodrugs.

Country Status (32)

Country	Link
US (1)	US6492342B1 (cs)
EP (1)	EP1224194A1 (cs)
JP (1)	JP2003512472A (cs)
KR (1)	KR20020043255A (cs)
CN (1)	CN1382149A (cs)
AP (1)	AP2002002492A0 (cs)
AR (1)	AR026285A1 (cs)
AU (1)	AU7307900A (cs)
BG (1)	BG106635A (cs)
BR (1)	BR0015156A (cs)
CA (1)	CA2389019A1 (cs)
CO (1)	CO5261547A1 (cs)
CZ (1)	CZ20021347A3 (cs)
EA (1)	EA200200413A1 (cs)
EC (1)	ECSP003743A (cs)
EE (1)	EE200200226A (cs)
GT (1)	GT200000178A (cs)
HK (1)	HK1049844A1 (cs)
HU (1)	HUP0203223A2 (cs)
IL (1)	IL148580A0 (cs)
IS (1)	IS6312A (cs)
MA (1)	MA26839A1 (cs)
MX (1)	MXPA02004359A (cs)
NO (1)	NO20021822D0 (cs)
OA (1)	OA12079A (cs)
PE (1)	PE20010757A1 (cs)
PL (1)	PL357080A1 (cs)
SK (1)	SK5322002A3 (cs)
SV (1)	SV2002000210A (cs)
TN (1)	TNSN00209A1 (cs)
TR (1)	TR200201143T2 (cs)
WO (1)	WO2001030793A1 (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12233081B2 (en)	2018-08-20	2025-02-25	Northeastern University	Hygromycin a compounds and methods of treating spirochete diseases

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ511424A (en) *	1998-12-02	2003-08-29	Pfizer Prod Inc	Hygromycin A derivatives as antibacterial agents

2000
- 2000-09-28 KR KR1020027005467A patent/KR20020043255A/ko not_active Ceased
- 2000-09-28 BR BR0015156-4A patent/BR0015156A/pt not_active IP Right Cessation
- 2000-09-28 AU AU73079/00A patent/AU7307900A/en not_active Abandoned
- 2000-09-28 SK SK532-2002A patent/SK5322002A3/sk unknown
- 2000-09-28 EP EP00960929A patent/EP1224194A1/en not_active Withdrawn
- 2000-09-28 EE EEP200200226A patent/EE200200226A/xx unknown
- 2000-09-28 EA EA200200413A patent/EA200200413A1/ru unknown
- 2000-09-28 TR TR2002/01143T patent/TR200201143T2/xx unknown
- 2000-09-28 OA OA1200200127A patent/OA12079A/en unknown
- 2000-09-28 JP JP2001533144A patent/JP2003512472A/ja not_active Withdrawn
- 2000-09-28 WO PCT/IB2000/001390 patent/WO2001030793A1/en not_active Ceased
- 2000-09-28 IL IL14858000A patent/IL148580A0/xx unknown
- 2000-09-28 AP APAP/P/2002/002492A patent/AP2002002492A0/en unknown
- 2000-09-28 PL PL00357080A patent/PL357080A1/xx not_active Application Discontinuation
- 2000-09-28 HU HU0203223A patent/HUP0203223A2/hu unknown
- 2000-09-28 HK HK03101876.4A patent/HK1049844A1/zh unknown
- 2000-09-28 CA CA002389019A patent/CA2389019A1/en not_active Abandoned
- 2000-09-28 CN CN00814799A patent/CN1382149A/zh active Pending
- 2000-09-28 MX MXPA02004359A patent/MXPA02004359A/es active IP Right Grant
- 2000-09-28 CZ CZ20021347A patent/CZ20021347A3/cs unknown
- 2000-10-16 GT GT200000178A patent/GT200000178A/es unknown
- 2000-10-25 PE PE2000001141A patent/PE20010757A1/es not_active Application Discontinuation
- 2000-10-27 CO CO00082085A patent/CO5261547A1/es not_active Application Discontinuation
- 2000-10-27 SV SV2000000210A patent/SV2002000210A/es unknown
- 2000-10-27 AR ARP000105699A patent/AR026285A1/es not_active Application Discontinuation
- 2000-10-27 US US09/698,399 patent/US6492342B1/en not_active Expired - Fee Related
- 2000-10-27 EC EC2000003743A patent/ECSP003743A/es unknown
- 2000-10-27 TN TNTNSN00209A patent/TNSN00209A1/fr unknown
2002
- 2002-03-19 IS IS6312A patent/IS6312A/is unknown
- 2002-04-18 NO NO20021822A patent/NO20021822D0/no unknown
- 2002-04-22 MA MA26614A patent/MA26839A1/fr unknown
- 2002-04-23 BG BG106635A patent/BG106635A/xx unknown

Also Published As

Publication number	Publication date
PE20010757A1 (es)	2001-07-25
HK1049844A1 (zh)	2003-05-30
ECSP003743A (es)	2002-05-23
AP2002002492A0 (en)	2002-06-30
EP1224194A1 (en)	2002-07-24
AU7307900A (en)	2001-05-08
BG106635A (en)	2002-12-29
SV2002000210A (es)	2002-06-07
SK5322002A3 (en)	2003-01-09
TR200201143T2 (tr)	2002-08-21
JP2003512472A (ja)	2003-04-02
HUP0203223A2 (en)	2003-02-28
IL148580A0 (en)	2002-09-12
MA26839A1 (fr)	2004-12-20
BR0015156A (pt)	2002-07-16
EA200200413A1 (ru)	2002-10-31
CN1382149A (zh)	2002-11-27
IS6312A (is)	2002-03-19
AR026285A1 (es)	2003-02-05
CO5261547A1 (es)	2003-03-31
EE200200226A (et)	2003-06-16
NO20021822L (no)	2002-04-18
US6492342B1 (en)	2002-12-10
TNSN00209A1 (fr)	2005-11-10
MXPA02004359A (es)	2002-11-07
NO20021822D0 (no)	2002-04-18
WO2001030793A1 (en)	2001-05-03
CA2389019A1 (en)	2001-05-03
PL357080A1 (en)	2004-07-12
CZ20021347A3 (cs)	2002-11-13
GT200000178A (es)	2002-04-09
KR20020043255A (ko)	2002-06-08

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CA2349338C (en)	2005-12-06	Novel macrolide antibiotics
US20090111776A1 (en)	2009-04-30	Novel tetracycline derivatives as antibacterial agents
KR100402560B1 (ko)	2003-10-17	하이그로마이신 에이 유도체
US20190211003A1 (en)	2019-07-11	Novel 16-member triamilide derivatives and uses thereof
SE448385B (sv)	1987-02-16	4"-deoxi-4"-acylamido-derivat av erytromycin-a
CS272243B2 (en)	1991-01-15	Method of deoxy 9a-allyl-and propargyl-9a-aza-9a homoerythromycin a new derivatives production
US6492342B1 (en)	2002-12-10	Hygromycin A prodrugs
KR100396099B1 (ko)	2003-08-27	2''-데옥시 하이그로마이신 유도체
US6998390B2 (en)	2006-02-14	Oxolide antibacterials
CN104961785B (zh)	2019-01-11	一种新型酰内酯衍生物及其制备方法
US6933283B2 (en)	2005-08-23	11-deoxy azalide antibacterials
US20040014691A1 (en)	2004-01-22	9-Oxime macrolide antibacterials
HU187574B (en)	1986-01-28	Process for producing antibacterial 6-comma above-square bracket-2-amino-2-bracket-4-acyl-oxy-phenyl-bracket closed-acetamido-square bracket closed-pename-3-carbonyl-oxy-methyl-pename-3-carboxylate-1,1-dioxide compounds
CA2410643A1 (en)	2001-12-06	Hygromycin a derivatives for the treatment of bacterial and protozoal infections
AU6362799A (en)	2000-06-19	Hygromycin a derivatives as antibacterial agents
EP1579864A1 (en)	2005-09-28	Oxolide antibacterials
CA2484095A1 (en)	2003-11-13	Tricyclic macrolide antibacterial compounds
US20040014687A1 (en)	2004-01-22	Macrolide antibacterial compounds
CA2483281A1 (en)	2003-11-06	11-deoxy azalide antibacterials
SE446340B (sv)	1986-09-01	Sett att framstella halvsyntetiska 4"-sulfonylamino-oleandomycinderivat
JPS5843398B2 (ja)	1983-09-27	ジアミノサイクリト−ル誘導体の製造方法