CA1039275A - 2-hydroxy-w-aminoalkyl-derivatives of aminoglycoside antibiotics - Google Patents

2-hydroxy-w-aminoalkyl-derivatives of aminoglycoside antibiotics

Info

Publication number: CA1039275A
Authority: CA; Canada
Prior art keywords: amino; hydroxy; kanamycin; formula; group
Prior art date: 1974-10-26
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

Application number

CA238,246A

Other languages

English (en)

French (fr)

Inventor

James W. Moore

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

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.)

1974-10-26

Filing date

1975-10-24

Publication date

1978-09-26

1975-10-24 Application filed by Pfizer Corp SRL filed Critical Pfizer Corp SRL

1978-09-26 Application granted granted Critical

1978-09-26 Publication of CA1039275A publication Critical patent/CA1039275A/en

Status Expired legal-status Critical Current

Links

239000002647 aminoglycoside antibiotic agent Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000003147 glycosyl group Chemical group 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
229960000318 kanamycin Drugs 0.000 claims description 20
238000000034 method Methods 0.000 claims description 13
229940126575 aminoglycoside Drugs 0.000 claims description 8
229960001192 bekanamycin Drugs 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229960003485 ribostamycin Drugs 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
OCFOTEIMZBKQFS-DGMGPCKZSA-N (2r,3r,4s,5s,6r)-2-[(1r,2s,3s,4r,6s)-6-amino-3-[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[[(2s)-4-amino-2-hydroxybutyl]amino]-2-hydroxycyclohexyl]oxy-6-(aminomethyl)oxane-3,4,5-triol 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[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O OCFOTEIMZBKQFS-DGMGPCKZSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 10
239000000243 solution Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000003242 anti bacterial agent Substances 0.000 description 8
DTFAJAKTSMLKAT-JDCCYXBGSA-N 2-deoxystreptamine Chemical compound N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O DTFAJAKTSMLKAT-JDCCYXBGSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
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 6
229930182823 kanamycin A Natural products 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000001962 electrophoresis Methods 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
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 3
229920001429 chelating resin Polymers 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
244000005700 microbiome Species 0.000 description 3
239000000203 mixture Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
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 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229930183180 Butirosin Natural products 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229950004527 butirosin Drugs 0.000 description 2
239000002775 capsule Substances 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
229930182824 kanamycin B Natural products 0.000 description 2
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 2
230000003287 optical effect Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
ANLMVXSIPASBFL-FAEUDGQSSA-N streptamine Chemical group N[C@H]1[C@H](O)[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O ANLMVXSIPASBFL-FAEUDGQSSA-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
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241001478240 Coccus Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
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 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
150000005323 carbonate salts Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000019628 coolness Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000003795 desorption Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
-1 for example Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004674 formic acids Chemical class 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
WQZGKKKJIJFFOK-UHFFFAOYSA-N hexopyranose Chemical group OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000001665 lethal effect Effects 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
238000004949 mass spectrometry Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
VQOXZBDYSJBXMA-RKEBNKJGSA-N nystatin a1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@@H]1OC1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)CC(O)CC(O)CC(O)CCC(O)C(O)C[C@](O)(CC(O)C2C(O)=O)OC2C1 VQOXZBDYSJBXMA-RKEBNKJGSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229930190553 ribostamycin Natural products 0.000 description 1
NSKGQURZWSPSBC-NLZFXWNVSA-N ribostamycin 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]2[C@@H]([C@@H](O)[C@H](CO)O2)O)[C@H](O)[C@@H](N)C[C@H]1N NSKGQURZWSPSBC-NLZFXWNVSA-N 0.000 description 1
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 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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
- 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
- C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
- C07H15/23—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with only two saccharide radicals in the molecule, e.g. ambutyrosin, butyrosin, xylostatin, ribostamycin
- 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

Landscapes

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

CA238,246A 1974-10-26 1975-10-24 2-hydroxy-w-aminoalkyl-derivatives of aminoglycoside antibiotics Expired CA1039275A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4641274A GB1464401A (en)	1974-10-26	1974-10-26	Aminoglycosides

Publications (1)

Publication Number	Publication Date
CA1039275A true CA1039275A (en)	1978-09-26

Family

ID=10441164

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA238,246A Expired CA1039275A (en)	1974-10-26	1975-10-24	2-hydroxy-w-aminoalkyl-derivatives of aminoglycoside antibiotics

Country Status (28)

Country	Link
JP (1)	JPS5519237B2 (de)
AR (1)	AR205593A1 (de)
AT (1)	AT340051B (de)
BE (1)	BE834864A (de)
BG (1)	BG24821A3 (de)
CA (1)	CA1039275A (de)
CH (1)	CH601339A5 (de)
CS (1)	CS195712B2 (de)
DD (1)	DD122522A5 (de)
DE (1)	DE2547738C3 (de)
DK (1)	DK147075C (de)
EG (1)	EG11975A (de)
ES (1)	ES442051A1 (de)
FI (1)	FI752951A (de)
FR (1)	FR2289202A1 (de)
GB (1)	GB1464401A (de)
HU (1)	HU172060B (de)
IE (1)	IE42452B1 (de)
IL (1)	IL48263A (de)
LU (1)	LU73644A1 (de)
NL (1)	NL162081C (de)
NZ (1)	NZ179050A (de)
PH (1)	PH12782A (de)
PL (1)	PL99933B1 (de)
RO (1)	RO72878A (de)
SE (1)	SE7511945L (de)
SU (1)	SU617017A3 (de)
ZA (1)	ZA756326B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2860513D1 (en) *	1977-06-24	1981-04-09	Scherico Ltd	Process for preparing aminoglycoside derivatives, novel derivatives obtained and pharmaceutical compositions containing such derivatives
JPS5488241A (en) *	1977-12-21	1979-07-13	Kyowa Hakko Kogyo Co Ltd	Novel fortimicin a derivative
JPS57118475U (de) *	1981-01-14	1982-07-22

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH606076A5 (de) *	1973-08-06	1978-10-13	Scherico Ltd

1974
- 1974-10-26 GB GB4641274A patent/GB1464401A/en not_active Expired
1975
- 1975-01-01 AR AR260909A patent/AR205593A1/es active
- 1975-10-06 ZA ZA00756326A patent/ZA756326B/xx unknown
- 1975-10-07 IL IL48263A patent/IL48263A/xx unknown
- 1975-10-16 PH PH17665A patent/PH12782A/en unknown
- 1975-10-22 RO RO7583664A patent/RO72878A/ro unknown
- 1975-10-22 FI FI752951A patent/FI752951A/fi not_active Application Discontinuation
- 1975-10-22 EG EG627/75A patent/EG11975A/xx active
- 1975-10-23 CS CS757161A patent/CS195712B2/cs unknown
- 1975-10-23 AT AT809575A patent/AT340051B/de not_active IP Right Cessation
- 1975-10-24 CA CA238,246A patent/CA1039275A/en not_active Expired
- 1975-10-24 LU LU73644A patent/LU73644A1/xx unknown
- 1975-10-24 BG BG031312A patent/BG24821A3/xx unknown
- 1975-10-24 DE DE2547738A patent/DE2547738C3/de not_active Expired
- 1975-10-24 SE SE7511945A patent/SE7511945L/xx unknown
- 1975-10-24 DK DK481175A patent/DK147075C/da active
- 1975-10-24 NL NL7512465.A patent/NL162081C/xx not_active IP Right Cessation
- 1975-10-24 HU HU75PI00000496A patent/HU172060B/hu unknown
- 1975-10-24 ES ES442051A patent/ES442051A1/es not_active Expired
- 1975-10-24 PL PL1975184233A patent/PL99933B1/pl unknown
- 1975-10-24 CH CH1380675A patent/CH601339A5/xx not_active IP Right Cessation
- 1975-10-24 IE IE2316/75A patent/IE42452B1/en unknown
- 1975-10-24 DD DD189046A patent/DD122522A5/xx unknown
- 1975-10-24 JP JP12823775A patent/JPS5519237B2/ja not_active Expired
- 1975-10-24 NZ NZ179050A patent/NZ179050A/xx unknown
- 1975-10-24 SU SU752184101A patent/SU617017A3/ru active
- 1975-10-24 FR FR7532662A patent/FR2289202A1/fr active Granted
- 1975-10-24 BE BE161248A patent/BE834864A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE2547738B2 (de)	1977-12-01
IE42452B1 (en)	1980-08-13
PL99933B1 (pl)	1978-08-31
RO72878B (ro)	1983-06-30
JPS5168543A (de)	1976-06-14
AU8598175A (en)	1976-12-09
ZA756326B (en)	1976-09-29
SU617017A3 (ru)	1978-07-25
FI752951A (de)	1976-04-27
SE7511945L (sv)	1976-04-27
DK147075B (da)	1984-04-02
PH12782A (en)	1979-08-17
IE42452L (en)	1976-04-26
AR205593A1 (es)	1976-05-14
DK147075C (da)	1984-11-05
NL162081C (nl)	1980-04-15
NL162081B (nl)	1979-11-15
ATA809575A (de)	1977-03-15
AT340051B (de)	1977-11-25
DE2547738A1 (de)	1976-05-06
IL48263A0 (en)	1975-12-31
FR2289202A1 (fr)	1976-05-28
RO72878A (ro)	1983-07-07
BG24821A3 (en)	1978-05-12
CS195712B2 (en)	1980-02-29
DK481175A (da)	1976-04-27
EG11975A (en)	1978-06-30
NZ179050A (en)	1978-03-06
CH601339A5 (de)	1978-07-14
HU172060B (hu)	1978-05-28
JPS5519237B2 (de)	1980-05-24
FR2289202B1 (de)	1978-11-10
DE2547738C3 (de)	1978-08-03
NL7512465A (nl)	1976-04-28
LU73644A1 (de)	1977-05-31
IL48263A (en)	1978-03-10
GB1464401A (en)	1977-02-16
BE834864A (fr)	1976-04-26
ES442051A1 (es)	1977-04-01
DD122522A5 (de)	1976-10-12

Publication	Publication Date	Title
US3940382A (en)	1976-02-24	1,2'-Di-N-substituted kanamycin B compounds
US4001208A (en)	1977-01-04	1-N-[(S)-α-hydroxy-ω-aminoacyl]
EP0002835A1 (de)	1979-07-11	Aminoglycosydderivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen
US3997524A (en)	1976-12-14	Process for the manufacture of 6'-N-alkyl derivatives of sisomicin and verdamicin; novel intermediates useful therein, and novel 6'-N-alkylverdamicins prepared thereby
US4107424A (en)	1978-08-15	1-N-[(S)-α-hydroxy-ω-aminoacyl] derivatives of 3',4'-dideoxykanamycin B and 3'-deoxykanamycin B antibiotics
CA1129852A (en)	1982-08-17	Aminoglycoside derivatives
US4214074A (en)	1980-07-22	Hydroxyalkyl derivatives of aminoglycoside antibiotics
US4170642A (en)	1979-10-09	Derivatives of kanamycin A
US3784541A (en)	1974-01-08	Polyamine compounds and methods for their production
CA1039275A (en)	1978-09-26	2-hydroxy-w-aminoalkyl-derivatives of aminoglycoside antibiotics
US4104372A (en)	1978-08-01	1-N-(α-hydroxy-ω-aminoalkanoyl) derivatives of 3'-deoxykanamycin A and the production thereof
US4251516A (en)	1981-02-17	2-Deoxy-3-O-Demethylfortimicins
US4283529A (en)	1981-08-11	3-O-Demethyl derivatives of Sannamycin C and antibiotic AX-127B-1
US4009328A (en)	1977-02-22	Aminoglycoside 66-40C, method for its manufacture, method for its use as an intermediate in the preparation of known antibiotics and novel antibacterials
US3939143A (en)	1976-02-17	1-N-isoserylkanamycins and the production thereof
US4330673A (en)	1982-05-18	Process for producing 3-O-demethylaminoglycoside and novel 3-O-demethylfortimicin derivatives
US4217446A (en)	1980-08-12	ωAmino-2-hydroxyalkyl derivatives of aminoglycoside antibiotics
US4140849A (en)	1979-02-20	Kanamycin C derivatives
CA1050975A (en)	1979-03-20	2-HYDROXY-.omega.-AMINOALKYL-DERIVATIVES OF AMINOGLYCOSIDE ANTIBIOTICS
US4205070A (en)	1980-05-27	6'N-Alkyl- and 6',6'-di-N-alkyl derivatives of fortimicins A and B
KR790001020B1 (ko)	1979-08-20	항균물질인 2-데옥시 스트렙타민-아미노 배당체류의 제조방법
US4282211A (en)	1981-08-04	1-Epi-2-deoxyfortimicin B and derivatives
KR790001305B1 (ko)	1979-09-24	2-데옥시스트랲트아민아미노그리코시드류의제조방법
US4108724A (en)	1978-08-22	Method for preparing antibiotic P-2563 using Pseudomonas fluorescens
US4331804A (en)	1982-05-25	2-Epi-fortimicin A and derivatives