IL30932A - Derivatives of kasugamycin antibiotic and their preparation - Google Patents

Derivatives of kasugamycin antibiotic and their preparation

Info

Publication number: IL30932A
Authority: IL; Israel
Prior art keywords: formula; hydrogen; process according; compound; solution
Prior art date: 1967-11-01

Application number

IL30932A

Other languages

English (en)

Other versions

IL30932A0 (en

Original Assignee

Bristol Myers Co

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.)

1967-11-01

Filing date

1968-10-22

Publication date

1973-03-30

1968-10-22 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1968-12-26 Publication of IL30932A0 publication Critical patent/IL30932A0/xx

1973-03-30 Publication of IL30932A publication Critical patent/IL30932A/en

Links

238000002360 preparation method Methods 0.000 title claims description 33
PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical class N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 title description 31
230000003115 biocidal effect Effects 0.000 title description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
239000000243 solution Substances 0.000 claims description 62
238000000034 method Methods 0.000 claims description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 34
BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical group CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
229960000367 inositol Drugs 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 13
231100000252 nontoxic Toxicity 0.000 claims description 13
230000003000 nontoxic effect Effects 0.000 claims description 13
239000002262 Schiff base Substances 0.000 claims description 11
239000007864 aqueous solution Substances 0.000 claims description 11
-1 imidate ester Chemical class 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 7
150000004753 Schiff bases Chemical class 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims description 4
229910001863 barium hydroxide Inorganic materials 0.000 claims description 3
229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000013067 intermediate product Substances 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
239000000920 calcium hydroxide Substances 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
229940074995 bromine Drugs 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 55
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
238000001914 filtration Methods 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
239000000203 mixture Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000005481 NMR spectroscopy Methods 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
238000003556 assay Methods 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000007787 solid Substances 0.000 description 10
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000000523 sample Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000002329 infrared spectrum Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
WHYJXXISOUGFLJ-UHFFFAOYSA-N 1-methoxyethylideneazanium;chloride Chemical compound [Cl-].COC(C)=[NH2+] WHYJXXISOUGFLJ-UHFFFAOYSA-N 0.000 description 4
241000588724 Escherichia coli Species 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 4
230000000903 blocking effect Effects 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 4
239000012453 solvate Substances 0.000 description 4
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 description 3
229920001817 Agar Polymers 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000588722 Escherichia Species 0.000 description 3
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 3
241000588748 Klebsiella Species 0.000 description 3
241000589516 Pseudomonas Species 0.000 description 3
239000008272 agar Substances 0.000 description 3
GXUARMXARIJAFV-UHFFFAOYSA-L barium oxalate Chemical compound [Ba+2].[O-]C(=O)C([O-])=O GXUARMXARIJAFV-UHFFFAOYSA-L 0.000 description 3
229940094800 barium oxalate Drugs 0.000 description 3
229960004279 formaldehyde Drugs 0.000 description 3
239000012458 free base Substances 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000007817 turbidimetric assay Methods 0.000 description 3
238000010792 warming Methods 0.000 description 3
241000607142 Salmonella Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
238000007865 diluting Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
JVQYUNBOIKCLKQ-UHFFFAOYSA-N methyl butanimidate;hydrochloride Chemical compound Cl.CCCC(=N)OC JVQYUNBOIKCLKQ-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
238000001291 vacuum drying Methods 0.000 description 2
IMVONGDWKKLEGD-UHFFFAOYSA-N 2-methylpropyl methanimidate Chemical compound CC(C)COC=N IMVONGDWKKLEGD-UHFFFAOYSA-N 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
241000589562 Brucella Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
CYKFJYVTEREVIY-UHFFFAOYSA-N Cl.C(OCC(C)C)=N Chemical compound Cl.C(OCC(C)C)=N CYKFJYVTEREVIY-UHFFFAOYSA-N 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
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 1
241000124008 Mammalia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000607768 Shigella Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
150000001553 barium compounds Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000005594 diketone group Chemical group 0.000 description 1
239000012470 diluted sample Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
SJFKGZZCMREBQH-UHFFFAOYSA-N methyl ethanimidate Chemical compound COC(C)=N SJFKGZZCMREBQH-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000004689 octahydrates Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/207—Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/848—Escherichia
- Y10S435/849—Escherichia coli

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL30932A 1967-11-01 1968-10-22 Derivatives of kasugamycin antibiotic and their preparation IL30932A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US67963167A	1967-11-01	1967-11-01

Publications (2)

Publication Number	Publication Date
IL30932A0 IL30932A0 (en)	1968-12-26
IL30932A true IL30932A (en)	1973-03-30

Family

ID=24727692

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30932A IL30932A (en)	1967-11-01	1968-10-22	Derivatives of kasugamycin antibiotic and their preparation

Country Status (9)

Country	Link
US (1)	US3480614A (de)
BE (1)	BE723276A (de)
CH (1)	CH516549A (de)
DE (1)	DE1806169A1 (de)
DK (1)	DK123097B (de)
FR (2)	FR1597594A (de)
GB (1)	GB1244026A (de)
IL (1)	IL30932A (de)
NL (1)	NL6815614A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3647779A (en) *	1970-05-01	1972-03-07	Bristol Myers Co	Kasugamycin substituted antibacterial agents
WO2019036566A1 (en)	2017-08-17	2019-02-21	Brown University	METHODS AND COMPOSITIONS RELATING TO THE TREATMENT OF FIBROSIS

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1094566A (en) *	1963-12-28	1967-12-13	Zh Biseibutsu Kagaku Kenkyukai	Kasugamycin and processes for the preparation thereof

1967
- 1967-11-01 US US679631A patent/US3480614A/en not_active Expired - Lifetime
1968
- 1968-10-22 IL IL30932A patent/IL30932A/en unknown
- 1968-10-30 DE DE19681806169 patent/DE1806169A1/de active Pending
- 1968-10-31 FR FR1597594D patent/FR1597594A/fr not_active Expired
- 1968-10-31 BE BE723276D patent/BE723276A/xx unknown
- 1968-11-01 CH CH1637568A patent/CH516549A/de not_active IP Right Cessation
- 1968-11-01 GB GB51855/68A patent/GB1244026A/en not_active Expired
- 1968-11-01 NL NL6815614A patent/NL6815614A/xx unknown
- 1968-11-01 DK DK531068AA patent/DK123097B/da unknown
1969
- 1969-01-30 FR FR183237A patent/FR8337M/fr not_active Expired

Also Published As

Publication number	Publication date
BE723276A (de)	1969-04-30
FR1597594A (de)	1970-06-29
FR8337M (de)	1970-12-14
CH516549A (de)	1971-12-15
DE1806169A1 (de)	1969-07-17
GB1244026A (en)	1971-08-25
NL6815614A (de)	1969-05-05
DK123097B (da)	1972-05-15
IL30932A0 (en)	1968-12-26
US3480614A (en)	1969-11-25

Publication	Publication Date	Title
SU1292668A3 (ru)	1987-02-23	Способ получени кристаллизованных солей цефема
US5574154A (en)	1996-11-12	Process for the preparation of cephalosporanic compounds
US3438968A (en)	1969-04-15	Substituted ammonium basic addition salts of ribonucleic acid
CA1181399A (en)	1985-01-22	Deazapurine derivatives
US4091202A (en)	1978-05-23	N-methanesulfonic acid derivatives of 3',4'-dideoxykanamycin B
SK281178B6 (sk)	2000-12-11	Spôsob prípravy dihydrochloridu azitromycínu
US4370484A (en)	1983-01-25	Sceptrin an antimicrobial agent from Agelas sceptrum
IL30932A (en)	1973-03-30	Derivatives of kasugamycin antibiotic and their preparation
DK162718B (da)	1991-12-02	Analogifremgangsmaade til fremstilling af 7-substitueret-3-vinyl-3-cephemforbindelser
US3865820A (en)	1975-02-11	Acylamino-cephalosporanic acids
YASUDA et al.	1983	Synthesis and antibacterial activity of 6-and 7-[2-(5-carboxyimidazole-4-carboxamido) phenylacetamido]-penicillins and cephalosporins
Ejima et al.	1987	Synthesis and antimicrobial activity of cephalosporins with a 1-pyridinium substituent carrying a 5-membered heterocycle at the C-3 position
CA1171870A (en)	1984-07-31	N-methanesulfonic acid derivatives of istamycin a or b and production thereof
US3759898A (en)	1973-09-18	Synthesis of alpha-(carbo(5-indanyloxy)) benzylpenicillin
US4440767A (en)	1984-04-03	Derivatives of cephalosporanic acid, processes for their production and their use
FI77038C (fi)	1989-01-10	Foerfarande foer framstaellning av en farmaceutiskt effektiv 6'-/2-amino-2-(4-acyloxifenyl)acetamido/ penicillanoyloximetylpenicillanat-1,1-dioxidfoereningar.
EP0294828B1 (de)	1993-08-25	Mitomycinanaloge, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen
US3652535A (en)	1972-03-28	Kasugamycin derivatives
FI59803C (fi)	1981-10-12	Foerfarande foer framstaellning av terapeutiskt anvaendbara penicillansyraderivater
SU1077572A3 (ru)	1984-02-29	Способ получени производных цефалоспорина или их солей с щелочными металлами или их сложных эфиров (его вариант)
US2965634A (en)	1960-12-20	Norleucine derivatives and process for producing same
FI67703C (fi)	1985-05-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla (4-hydroxi-5-pyrimidinyl)-ureidobensylpenicilliner
US4575496A (en)	1986-03-11	Erythromycin salt of the o-carbonyl(1-thiazolidinyl)-benzoic acid and pharmaceutical compositions containing it
US3944580A (en)	1976-03-16	7-[2-(Dithiocarboxylamino)alkanamido]-cephalosporanic acid derivatives
JPS59205382A (ja)	1984-11-20	アミノ２硫化物