CA1105454A - PREPARATION OF 1-N-¬.omega.-AMINO-.alpha.- HYDROXYALKANOYL| AMINOGLYCOSIDE ANTIBIOTICS - Google Patents
PREPARATION OF 1-N-¬.omega.-AMINO-.alpha.- HYDROXYALKANOYL| AMINOGLYCOSIDE ANTIBIOTICSInfo
- Publication number
- CA1105454A CA1105454A CA301,968A CA301968A CA1105454A CA 1105454 A CA1105454 A CA 1105454A CA 301968 A CA301968 A CA 301968A CA 1105454 A CA1105454 A CA 1105454A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- amino
- formula xiii
- acylating derivative
- groups
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 46
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 91
- 239000002253 acid Substances 0.000 claims abstract description 84
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 229940126575 aminoglycoside Drugs 0.000 claims description 119
- -1 t-butoxycarbonyl Chemical group 0.000 claims description 74
- 125000003277 amino group Chemical group 0.000 claims description 43
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 37
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 32
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 26
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 20
- 230000000903 blocking effect Effects 0.000 claims description 19
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 18
- 150000008064 anhydrides Chemical class 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- QRAFJHXNLQTXQW-UHFFFAOYSA-N 2-methylpropyl hydrogen carbonate Chemical compound CC(C)COC(O)=O QRAFJHXNLQTXQW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 claims description 12
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 12
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 11
- 235000010233 benzoic acid Nutrition 0.000 claims description 11
- NJAPCAIWQRPQPY-UHFFFAOYSA-N benzyl hydrogen carbonate Chemical compound OC(=O)OCC1=CC=CC=C1 NJAPCAIWQRPQPY-UHFFFAOYSA-N 0.000 claims description 11
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
- 229940126574 aminoglycoside antibiotic Drugs 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 120
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 109
- 229960000318 kanamycin Drugs 0.000 description 104
- 229930182823 kanamycin A Natural products 0.000 description 103
- 238000005917 acylation reaction Methods 0.000 description 62
- 239000000243 solution Substances 0.000 description 60
- 230000010933 acylation Effects 0.000 description 56
- 239000000203 mixture Substances 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- 229910001868 water Inorganic materials 0.000 description 54
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 229960004821 amikacin Drugs 0.000 description 45
- 239000000047 product Substances 0.000 description 40
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- 239000007858 starting material Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 229960001192 bekanamycin Drugs 0.000 description 22
- 229930182824 kanamycin B Natural products 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 230000000875 corresponding effect Effects 0.000 description 19
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 18
- 238000005406 washing Methods 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 238000006884 silylation reaction Methods 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 229930027917 kanamycin Natural products 0.000 description 16
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 14
- 241001558496 Talpa caeca Species 0.000 description 13
- 238000003556 assay Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 description 12
- 229930192786 Sisomicin Natural products 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 229960005456 sisomicin Drugs 0.000 description 12
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 description 12
- SWOHHBNJQHDNFM-WYSMZKEGSA-N (2s)-4-amino-n-[(1s,2r,3r,4s,5r)-5-amino-4-[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2r,3r,4s,5s,6r)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.O([C@H]1[C@H](N)C[C@@H]([C@H]([C@@H]1O)O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O SWOHHBNJQHDNFM-WYSMZKEGSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910017974 NH40H Inorganic materials 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 8
- QPEJHSFTZVMSJH-UHFFFAOYSA-N 3-amino-5-hydroxybenzoic acid Chemical compound NC1=CC(O)=CC(C(O)=O)=C1 QPEJHSFTZVMSJH-UHFFFAOYSA-N 0.000 description 7
- 229930182566 Gentamicin Natural products 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 7
- 230000002906 microbiologic effect Effects 0.000 description 7
- 229930190553 ribostamycin Natural products 0.000 description 7
- 229960003485 ribostamycin Drugs 0.000 description 7
- NSKGQURZWSPSBC-UHFFFAOYSA-N ribostamycin A Natural products NC1C(O)C(O)C(CN)OC1OC1C(OC2C(C(O)C(CO)O2)O)C(O)C(N)CC1N NSKGQURZWSPSBC-UHFFFAOYSA-N 0.000 description 7
- NSKGQURZWSPSBC-VVPCINPTSA-R ribostamycin(4+) Chemical compound [NH3+][C@@H]1[C@@H](O)[C@H](O)[C@@H](C[NH3+])O[C@@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H]([NH3+])C[C@@H]1[NH3+] NSKGQURZWSPSBC-VVPCINPTSA-R 0.000 description 7
- XUSXOPRDIDWMFO-CTMSJIKGSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-[(1s)-1-aminoethyl]-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(O2)[C@H](C)N)N)[C@@H](N)C[C@H]1N XUSXOPRDIDWMFO-CTMSJIKGSA-N 0.000 description 6
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- DNYGXMICFMACRA-XHEDQWPISA-N Gentamicin C2b Chemical compound O1[C@H](CNC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N DNYGXMICFMACRA-XHEDQWPISA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XUSXOPRDIDWMFO-UHFFFAOYSA-N Verdamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(O2)C(C)N)N)C(N)CC1N XUSXOPRDIDWMFO-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229960002518 gentamicin Drugs 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 235000016496 Panda oleosa Nutrition 0.000 description 5
- 240000000220 Panda oleosa Species 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 229930190071 lycoside Natural products 0.000 description 5
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 229930183180 Butirosin Natural products 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 4
- 238000010268 HPLC based assay Methods 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
- 238000005828 desilylation reaction Methods 0.000 description 4
- LKKVGKXCMYHKSL-LLZRLKDCSA-N gentamycin A Chemical compound O[C@H]1[C@H](NC)[C@@H](O)CO[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](N)C[C@H]1N LKKVGKXCMYHKSL-LLZRLKDCSA-N 0.000 description 4
- 229930182470 glycoside Natural products 0.000 description 4
- 150000002338 glycosides Chemical group 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229960000707 tobramycin Drugs 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 239000005051 trimethylchlorosilane Substances 0.000 description 4
- XEQLFNPSYWZPOW-NUOYRARPSA-N (2r)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-[(2r,3r,4r,5s,6r)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-hydroxycyclohexyl]-2-hydroxybutanamide Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O[C@@H]1[C@@H]([C@H](O)[C@@H](CO)O1)O)O)NC(=O)[C@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1N XEQLFNPSYWZPOW-NUOYRARPSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DAKDDLIZULPEFW-UHFFFAOYSA-N 2-[4,6-diamino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-4-(methylamino)oxane-3,5-diol Chemical compound OC1C(NC)C(O)COC1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N DAKDDLIZULPEFW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 229950004527 butirosin Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NSYZCCDSJNWWJL-YXOIYICCSA-N erythromycin ethylsuccinate Chemical compound O1[C@H](C)C[C@H](N(C)C)[C@@H](OC(=O)CCC(=O)OCC)[C@@H]1O[C@H]1[C@@](O)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(OC)C2)[C@@H]1C NSYZCCDSJNWWJL-YXOIYICCSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
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- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- PDNUHAXBKKDGAM-UHFFFAOYSA-N chloro-diethyl-methylsilane Chemical compound CC[Si](C)(Cl)CC PDNUHAXBKKDGAM-UHFFFAOYSA-N 0.000 description 1
- AVDUEHWPPXIAEB-UHFFFAOYSA-N chloro-ethyl-dimethylsilane Chemical compound CC[Si](C)(C)Cl AVDUEHWPPXIAEB-UHFFFAOYSA-N 0.000 description 1
- UPSBFLYYMHIEJB-UHFFFAOYSA-N chloro-methyl-(2-phenylethyl)silane Chemical compound C[SiH](Cl)CCC1=CC=CC=C1 UPSBFLYYMHIEJB-UHFFFAOYSA-N 0.000 description 1
- HPQGAYBKOJXAEZ-UHFFFAOYSA-N chloro-tris(2-methylphenyl)silane Chemical compound CC1=CC=CC=C1[Si](Cl)(C=1C(=CC=CC=1)C)C1=CC=CC=C1C HPQGAYBKOJXAEZ-UHFFFAOYSA-N 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229960003807 dibekacin Drugs 0.000 description 1
- VLNZUSMTOFYNPS-UHFFFAOYSA-N diethylphosphorylformonitrile Chemical compound CCP(=O)(CC)C#N VLNZUSMTOFYNPS-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- UBGXLEFOIVWVRP-UHFFFAOYSA-N fluoro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(F)C1=CC=CC=C1 UBGXLEFOIVWVRP-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- IECPWNUMDGFDKC-MZJAQBGESA-M fusidate Chemical compound O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-M 0.000 description 1
- 229960004675 fusidic acid Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005179 haloacetyl group Chemical group 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical compound OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
- 229960000768 kanamycin a sulfate Drugs 0.000 description 1
- 150000003932 ketenimines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- LMSCAPYDLTUYDG-UHFFFAOYSA-N n-triethylsilylethanamine Chemical compound CCN[Si](CC)(CC)CC LMSCAPYDLTUYDG-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- HJKXMQLJTKUBMG-INVUDJPSSA-N seldomycin Chemical compound N[C@H]1[C@@H](N)[C@H](OC)CO[C@@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)C[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N HJKXMQLJTKUBMG-INVUDJPSSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- AATYKEFFPLPLST-UHFFFAOYSA-N trimethylsilylurea Chemical compound C[Si](C)(C)NC(N)=O AATYKEFFPLPLST-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000007817 turbidimetric assay Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA370,572A CA1105452A (en) | 1977-04-28 | 1981-02-10 | PREPARATION OF 1-N-[.omega.-AMINO-.alpha.- HYDROXYALKANOYL]AMINOGLYCOSIDE ANTIBIOTICS |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79180677A | 1977-04-28 | 1977-04-28 | |
| US791,806 | 1977-04-28 | ||
| US88858578A | 1978-03-20 | 1978-03-20 | |
| US888,585 | 1978-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105454A true CA1105454A (en) | 1981-07-21 |
Family
ID=27121201
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA301,968A Expired CA1105454A (en) | 1977-04-28 | 1978-04-25 | PREPARATION OF 1-N-¬.omega.-AMINO-.alpha.- HYDROXYALKANOYL| AMINOGLYCOSIDE ANTIBIOTICS |
| CA301,962A Expired CA1100953A (en) | 1977-04-28 | 1978-04-25 | PREPARATION OF 1-N¬.omega.-AMINO-.alpha.-HYDROXYALKANOYL| KANAMYCINS |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA301,962A Expired CA1100953A (en) | 1977-04-28 | 1978-04-25 | PREPARATION OF 1-N¬.omega.-AMINO-.alpha.-HYDROXYALKANOYL| KANAMYCINS |
Country Status (27)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8383596B2 (en) | 2007-11-21 | 2013-02-26 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8492354B2 (en) | 2009-05-15 | 2013-07-23 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8524689B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8524675B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8653042B2 (en) | 2009-05-15 | 2014-02-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8658606B2 (en) | 2009-05-15 | 2014-02-25 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55306A (en) * | 1978-04-28 | 1980-01-05 | Bristol Myers Co | Manufacture of 11nn*omegaaaminooalphaahydroxy alkanoyl**aminoglycoside antibiotic |
| JP4621429B2 (ja) * | 2002-02-19 | 2011-01-26 | 学校法人東海大学 | 乳酸誘導体 |
-
1978
- 1978-04-21 AR AR271852A patent/AR218910A1/es active
- 1978-04-25 CA CA301,968A patent/CA1105454A/en not_active Expired
- 1978-04-25 FI FI781288A patent/FI781288A7/fi not_active Application Discontinuation
- 1978-04-25 NO NO781437A patent/NO149635C/no unknown
- 1978-04-25 CA CA301,962A patent/CA1100953A/en not_active Expired
- 1978-04-26 DK DK182978A patent/DK165450C/da not_active IP Right Cessation
- 1978-04-26 DK DK197801830A patent/DK172543B1/da not_active IP Right Cessation
- 1978-04-26 CY CY1241A patent/CY1241A/en unknown
- 1978-04-26 NL NLAANVRAGE7804503,A patent/NL178790C/xx not_active IP Right Cessation
- 1978-04-26 GB GB16571/78A patent/GB1598294A/en not_active Expired
- 1978-04-27 PT PT67959A patent/PT67959B/pt unknown
- 1978-04-27 LU LU79541A patent/LU79541A1/xx unknown
- 1978-04-27 YU YU1024/78A patent/YU41590B/xx unknown
- 1978-04-27 FR FR7812589A patent/FR2388826A1/fr active Granted
- 1978-04-27 YU YU01025/78A patent/YU102578A/xx unknown
- 1978-04-27 CS CS782729A patent/CS207607B2/cs unknown
- 1978-04-27 IE IE841/78A patent/IE46945B1/en not_active IP Right Cessation
- 1978-04-27 FR FR7812591A patent/FR2388827A1/fr active Granted
- 1978-04-27 IE IE842/78A patent/IE47271B1/en not_active IP Right Cessation
- 1978-04-28 JP JP5016078A patent/JPS53149951A/ja active Granted
- 1978-04-28 DE DE19782818822 patent/DE2818822A1/de active Granted
- 1978-04-28 SE SE7804973A patent/SE447259B/sv not_active IP Right Cessation
- 1978-04-28 ES ES469303A patent/ES469303A1/es not_active Expired
- 1978-04-28 DE DE19782818992 patent/DE2818992A1/de active Granted
- 1978-04-28 IT IT49137/78A patent/IT1105500B/it active
- 1978-04-28 IT IT49136/78A patent/IT1156718B/it active
- 1978-04-28 AT AT312778A patent/AT357675B/de not_active IP Right Cessation
- 1978-04-28 CH CH470278A patent/CH639104A5/de not_active IP Right Cessation
- 1978-04-28 PL PL1978206457A patent/PL117307B1/pl unknown
- 1978-04-29 EG EG283/78A patent/EG13710A/xx active
-
1983
- 1983-04-05 NO NO83831197A patent/NO154697C/no unknown
- 1983-10-07 SE SE8305538A patent/SE461148B/sv not_active IP Right Cessation
-
1984
- 1984-03-12 SG SG228/84A patent/SG22884G/en unknown
- 1984-04-12 KE KE3398A patent/KE3398A/xx unknown
- 1984-06-22 HK HK514/84A patent/HK51484A/en not_active IP Right Cessation
-
1985
- 1985-12-30 MY MY528/85A patent/MY8500528A/xx unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8383596B2 (en) | 2007-11-21 | 2013-02-26 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8822424B2 (en) | 2007-11-21 | 2014-09-02 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US9266919B2 (en) | 2007-11-21 | 2016-02-23 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US9688711B2 (en) | 2007-11-21 | 2017-06-27 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US11117915B2 (en) | 2007-11-21 | 2021-09-14 | Cipla USA, Inc. | Antibacterial aminoglycoside analogs |
| US8492354B2 (en) | 2009-05-15 | 2013-07-23 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8524689B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8524675B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8653042B2 (en) | 2009-05-15 | 2014-02-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8658606B2 (en) | 2009-05-15 | 2014-02-25 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| USRE47741E1 (en) | 2009-05-15 | 2019-11-26 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |