SU927122A3 - Способ получени производных 4"-деокси-4"-амино-эритромицина А или их солей - Google Patents

Способ получени производных 4"-деокси-4"-амино-эритромицина А или их солей Download PDF

Info

Publication number: SU927122A3
Authority: SU; USSR - Soviet Union
Prior art keywords: deoxy; product; adjusted; water; chloroform
Prior art date: 1977-02-04

Application number

SU782573754A

Other languages

English (en)

Russian (ru)

Inventor

Кристиан Сиаволино Фрэнк

Original Assignee

Пфайзер Инк(Фирма)

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.)

1977-02-04

Filing date

1978-02-03

Publication date

1982-05-07

1977-12-01 Priority claimed from US05/856,479 external-priority patent/US4150220A/en

1978-02-03 Application filed by Пфайзер Инк(Фирма) filed Critical Пфайзер Инк(Фирма)

1982-05-07 Application granted granted Critical

1982-05-07 Publication of SU927122A3 publication Critical patent/SU927122A3/ru

Links

150000003839 salts Chemical class 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims abstract description 25
238000002360 preparation method Methods 0.000 claims abstract description 4
229960003276 erythromycin Drugs 0.000 claims abstract 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 107
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 66
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 57
239000000047 product Substances 0.000 claims description 53
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
239000010410 layer Substances 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 33
239000006260 foam Substances 0.000 claims description 31
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 24
229910052938 sodium sulfate Inorganic materials 0.000 claims description 24
235000011152 sodium sulphate Nutrition 0.000 claims description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000000243 solution Substances 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 18
238000003756 stirring Methods 0.000 claims description 18
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 16
239000005695 Ammonium acetate Substances 0.000 claims description 16
229940043376 ammonium acetate Drugs 0.000 claims description 16
235000019257 ammonium acetate Nutrition 0.000 claims description 16
238000012360 testing method Methods 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
230000000694 effects Effects 0.000 claims description 11
230000002829 reductive effect Effects 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
-1 alkali metal cyanoborohydride Chemical class 0.000 claims description 9
239000000284 extract Substances 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
241000699670 Mus sp. Species 0.000 claims description 8
239000002024 ethyl acetate extract Substances 0.000 claims description 8
238000000605 extraction Methods 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 8
244000005700 microbiome Species 0.000 claims description 8
239000012452 mother liquor Substances 0.000 claims description 8
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239000007787 solid Substances 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 6
230000008025 crystallization Effects 0.000 claims description 6
239000000706 filtrate Substances 0.000 claims description 6
238000000338 in vitro Methods 0.000 claims description 6
238000001727 in vivo Methods 0.000 claims description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
230000035484 reaction time Effects 0.000 claims description 6
238000001953 recrystallisation Methods 0.000 claims description 6
238000006722 reduction reaction Methods 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 4
239000006227 byproduct Substances 0.000 claims description 4
FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 claims description 4
238000000354 decomposition reaction Methods 0.000 claims description 4
239000012467 final product Substances 0.000 claims description 4
239000011521 glass Substances 0.000 claims description 4
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150000002466 imines Chemical class 0.000 claims description 4
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239000002244 precipitate Substances 0.000 claims description 4
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
239000000600 sorbitol Substances 0.000 claims description 4
239000012258 stirred mixture Substances 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
241000191967 Staphylococcus aureus Species 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
238000010531 catalytic reduction reaction Methods 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
239000002026 chloroform extract Substances 0.000 claims description 3
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
238000007790 scraping Methods 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
239000000741 silica gel Substances 0.000 claims description 3
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239000011734 sodium Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
238000007920 subcutaneous administration Methods 0.000 claims description 3
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 2
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
108010003272 Hyaluronate lyase Proteins 0.000 claims description 2
102000001974 Hyaluronidases Human genes 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
241000588645 Neisseria sicca Species 0.000 claims description 2
235000019483 Peanut oil Nutrition 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
239000003242 anti bacterial agent Substances 0.000 claims description 2
239000008346 aqueous phase Substances 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
239000003125 aqueous solvent Substances 0.000 claims description 2
235000003704 aspartic acid Nutrition 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000012267 brine Substances 0.000 claims description 2
239000002775 capsule Substances 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
238000001816 cooling Methods 0.000 claims description 2
235000005687 corn oil Nutrition 0.000 claims description 2
239000002285 corn oil Substances 0.000 claims description 2
235000012343 cottonseed oil Nutrition 0.000 claims description 2
239000002385 cottonseed oil Substances 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
239000008121 dextrose Substances 0.000 claims description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
238000009826 distribution Methods 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
235000012208 gluconic acid Nutrition 0.000 claims description 2
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230000007062 hydrolysis Effects 0.000 claims description 2
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239000007924 injection Substances 0.000 claims description 2
238000011081 inoculation Methods 0.000 claims description 2
238000007912 intraperitoneal administration Methods 0.000 claims description 2
239000003589 local anesthetic agent Substances 0.000 claims description 2
229960005015 local anesthetics Drugs 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000002609 medium Substances 0.000 claims description 2
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230000008018 melting Effects 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
239000012457 nonaqueous media Substances 0.000 claims description 2
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230000003000 nontoxic effect Effects 0.000 claims description 2
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239000002674 ointment Substances 0.000 claims description 2
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239000001301 oxygen Substances 0.000 claims description 2
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238000007911 parenteral administration Methods 0.000 claims description 2
239000003182 parenteral nutrition solution Substances 0.000 claims description 2
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OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims description 2
230000000717 retained effect Effects 0.000 claims description 2
230000035945 sensitivity Effects 0.000 claims description 2
238000013207 serial dilution Methods 0.000 claims description 2
239000008159 sesame oil Substances 0.000 claims description 2
235000011803 sesame oil Nutrition 0.000 claims description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 2
230000001954 sterilising effect Effects 0.000 claims description 2
238000004659 sterilization and disinfection Methods 0.000 claims description 2
239000007929 subcutaneous injection Substances 0.000 claims description 2
238000001308 synthesis method Methods 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
231100000331 toxic Toxicity 0.000 claims description 2
230000002588 toxic effect Effects 0.000 claims description 2
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238000002255 vaccination Methods 0.000 claims description 2
230000001018 virulence Effects 0.000 claims description 2
239000002023 wood Substances 0.000 claims description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 8
229910052759 nickel Inorganic materials 0.000 claims 4
229920001855 polyketal Polymers 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
229930006677 Erythromycin A Natural products 0.000 claims 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 claims 1
DPZHKLJPVMYFCU-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)acetonitrile Chemical compound BrC1=CC=C(CC#N)N=C1 DPZHKLJPVMYFCU-UHFFFAOYSA-N 0.000 claims 1
NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 claims 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 claims 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims 1
RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
244000000231 Sesamum indicum Species 0.000 claims 1
241000194017 Streptococcus Species 0.000 claims 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
206010043458 Thirst Diseases 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
230000000845 anti-microbial effect Effects 0.000 claims 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
239000000872 buffer Substances 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
230000002526 effect on cardiovascular system Effects 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
239000007928 intraperitoneal injection Substances 0.000 claims 1
231100000518 lethal Toxicity 0.000 claims 1
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239000007788 liquid Substances 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
239000003921 oil Substances 0.000 claims 1
235000019198 oils Nutrition 0.000 claims 1
239000008063 pharmaceutical solvent Substances 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
238000010898 silica gel chromatography Methods 0.000 claims 1
239000011780 sodium chloride Substances 0.000 claims 1
239000011550 stock solution Substances 0.000 claims 1
229910021653 sulphate ion Inorganic materials 0.000 claims 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
235000015112 vegetable and seed oil Nutrition 0.000 claims 1
239000008158 vegetable oil Substances 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 abstract 1
229940126601 medicinal product Drugs 0.000 abstract 1
239000007868 Raney catalyst Substances 0.000 description 3
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NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
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230000000747 cardiac effect Effects 0.000 description 1
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238000010254 subcutaneous injection Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- 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

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

SU782573754A 1977-02-04 1978-02-03 Способ получени производных 4"-деокси-4"-амино-эритромицина А или их солей SU927122A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76548077A	1977-02-04	1977-02-04
US05/856,479 US4150220A (en)	1977-02-04	1977-12-01	Semi-synthetic 4"-erythromycin A derivatives

Publications (1)

Publication Number	Publication Date
SU927122A3 true SU927122A3 (ru)	1982-05-07

Family

ID=27117613

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782573754A SU927122A3 (ru)	1977-02-04	1978-02-03	Способ получени производных 4"-деокси-4"-амино-эритромицина А или их солей

Country Status (30)

Country	Link
JP (1)	JPS5827798B2 (el)
AR (1)	AR222147A1 (el)
AU (1)	AU501298B1 (el)
BG (2)	BG32718A3 (el)
CA (1)	CA1106367A (el)
CH (1)	CH628906A5 (el)
CS (1)	CS221801B2 (el)
DD (1)	DD140048A5 (el)
DE (1)	DE2804507C2 (el)
DK (1)	DK148036C (el)
ES (2)	ES466057A1 (el)
FI (1)	FI780354A7 (el)
FR (2)	FR2379550A1 (el)
GB (2)	GB1585316A (el)
GR (1)	GR68691B (el)
HU (1)	HU182559B (el)
IE (1)	IE46661B1 (el)
IL (2)	IL53968A0 (el)
IT (1)	IT1094209B (el)
LU (1)	LU79004A1 (el)
NL (1)	NL176174C (el)
NO (2)	NO146472C (el)
NZ (1)	NZ186385A (el)
PH (2)	PH14421A (el)
PL (1)	PL116228B1 (el)
PT (1)	PT67568B (el)
RO (4)	RO81622B (el)
SE (2)	SE445223B (el)
SU (1)	SU927122A3 (el)
YU (3)	YU40913B (el)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4133950A (en) *	1978-01-03	1979-01-09	Pfizer Inc.	4"-Deoxy-4"-carbamate and dithiocarbamate derivatives of oleandomycin and its esters
US4124755A (en) *	1978-01-03	1978-11-07	Pfizer Inc.	11-Alkanoyl-4"-deoxy-4"-isonitrilo-oleandomycin derivatives
US4382085A (en) *	1982-03-01	1983-05-03	Pfizer Inc.	4"-Epi erythromycin A and derivatives thereof as useful antibacterial agents
US4518590A (en) *	1984-04-13	1985-05-21	Pfizer Inc.	9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method
HN1998000074A (es) *	1997-06-11	1999-01-08	Pfizer Prod Inc	Derivados de macrolidos c-4 sustituidos
US6407074B1 (en)	1997-06-11	2002-06-18	Pfizer Inc	C-4″-substituted macrolide derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3836519A (en) *	1973-05-04	1974-09-17	Abbott Lab	Sulfonyl derivatives of erythromycin
US3884903A (en) *	1973-06-21	1975-05-20	Abbott Lab	4{41 -Deoxy-4{41 -oxoerythromycin B derivatives

1978
- 1978-01-10 SE SE7800270A patent/SE445223B/sv not_active IP Right Cessation
- 1978-01-13 PH PH20662A patent/PH14421A/en unknown
- 1978-01-17 ES ES466057A patent/ES466057A1/es not_active Expired
- 1978-01-18 YU YU73/78A patent/YU40913B/xx unknown
- 1978-01-18 AR AR270752A patent/AR222147A1/es active
- 1978-01-23 PT PT67568A patent/PT67568B/pt unknown
- 1978-01-31 CH CH106178A patent/CH628906A5/fr not_active IP Right Cessation
- 1978-02-02 CA CA296,037A patent/CA1106367A/en not_active Expired
- 1978-02-02 DE DE2804507A patent/DE2804507C2/de not_active Expired
- 1978-02-02 GB GB34309/79A patent/GB1585316A/en not_active Expired
- 1978-02-02 RO RO105255A patent/RO81622B/ro unknown
- 1978-02-02 GB GB4165/78A patent/GB1585315A/en not_active Expired
- 1978-02-02 CS CS78703A patent/CS221801B2/cs unknown
- 1978-02-02 RO RO78101650A patent/RO79686A7/ro unknown
- 1978-02-02 RO RO78101651A patent/RO79687A7/ro unknown
- 1978-02-02 RO RO7893080A patent/RO77345A/ro unknown
- 1978-02-02 GR GR55330A patent/GR68691B/el unknown
- 1978-02-03 JP JP53011352A patent/JPS5827798B2/ja not_active Expired
- 1978-02-03 PL PL1978204428A patent/PL116228B1/pl unknown
- 1978-02-03 BG BG038579A patent/BG32718A3/xx unknown
- 1978-02-03 HU HU78PI611A patent/HU182559B/hu not_active IP Right Cessation
- 1978-02-03 DK DK51878A patent/DK148036C/da not_active IP Right Cessation
- 1978-02-03 AU AU32990/78A patent/AU501298B1/en not_active Expired
- 1978-02-03 NZ NZ186385A patent/NZ186385A/xx unknown
- 1978-02-03 FI FI780354A patent/FI780354A7/fi not_active Application Discontinuation
- 1978-02-03 IL IL53968A patent/IL53968A0/xx not_active IP Right Cessation
- 1978-02-03 IT IT20005/78A patent/IT1094209B/it active
- 1978-02-03 DD DD78203547A patent/DD140048A5/de unknown
- 1978-02-03 BG BG040069A patent/BG33159A3/xx unknown
- 1978-02-03 NL NLAANVRAGE7801262,A patent/NL176174C/xx not_active IP Right Cessation
- 1978-02-03 FR FR7803066A patent/FR2379550A1/fr active Granted
- 1978-02-03 LU LU79004A patent/LU79004A1/xx unknown
- 1978-02-03 NO NO780389A patent/NO146472C/no unknown
- 1978-02-03 SU SU782573754A patent/SU927122A3/ru active
- 1978-02-03 IE IE239/78A patent/IE46661B1/en not_active IP Right Cessation
- 1978-07-07 FR FR7820334A patent/FR2385735A1/fr active Granted
- 1978-08-08 ES ES472429A patent/ES472429A1/es not_active Expired
- 1978-09-01 PH PH21555A patent/PH16675A/en unknown
1981
- 1981-01-27 IL IL61997A patent/IL61997A0/xx unknown
- 1981-06-05 NO NO811913A patent/NO150484C/no unknown
1983
- 1983-02-07 YU YU265/83A patent/YU40798B/xx unknown
- 1983-02-16 SE SE8300870A patent/SE457086B/xx not_active IP Right Cessation
- 1983-11-21 YU YU2279/83A patent/YU40799B/xx unknown

Also Published As

Publication number	Publication date
DK148036B (da)	1985-02-11
GB1585316A (en)	1981-02-25
BG32718A3 (bg)	1982-09-15
DE2804507A1 (de)	1978-08-10
GB1585315A (en)	1981-02-25
CA1106367A (en)	1981-08-04
AU501298B1 (en)	1979-06-14
NO780389L (no)	1978-08-07
SE8300870L (sv)	1983-02-16
PT67568A (en)	1978-02-01
YU40799B (en)	1986-06-30
IE780239L (en)	1978-08-04
DK51878A (da)	1978-08-05
AR222147A1 (es)	1981-04-30
RO81622B (ro)	1983-04-30
RO77345A (ro)	1981-08-17
HU182559B (en)	1984-02-28
SE457086B (sv)	1988-11-28
YU26583A (en)	1984-02-29
IT1094209B (it)	1985-07-26
ES466057A1 (es)	1978-10-01
IT7820005A0 (it)	1978-02-03
RO81622A (ro)	1983-04-29
PL204428A1 (pl)	1979-06-04
NL176174C (nl)	1985-03-01
FR2385735B1 (el)	1980-10-24
ES472429A1 (es)	1979-04-01
YU227983A (en)	1984-04-30
NO150484C (no)	1984-10-24
IL61997A0 (en)	1981-02-27
PL116228B1 (en)	1981-05-30
JPS5827798B2 (ja)	1983-06-11
NO146472C (no)	1982-10-06
DD140048A5 (de)	1980-02-06
RO79686A7 (ro)	1982-08-17
FR2379550A1 (fr)	1978-09-01
GR68691B (el)	1982-02-01
DE2804507C2 (de)	1982-11-04
NO150484B (no)	1984-07-16
RO79687A7 (ro)	1982-08-17
PH16675A (en)	1983-12-13
PH14421A (en)	1981-07-10
SE7800270L (sv)	1978-08-05
NL176174B (nl)	1984-10-01
NL7801262A (nl)	1978-08-08
YU7378A (en)	1983-04-30
YU40913B (en)	1986-08-31
FI780354A7 (fi)	1978-08-05
IL53968A0 (en)	1978-04-30
JPS53101337A (en)	1978-09-04
CH628906A5 (en)	1982-03-31
SE8300870D0 (sv)	1983-02-16
SE445223B (sv)	1986-06-09
NO146472B (no)	1982-06-28
DK148036C (da)	1985-07-15
BG33159A3 (bg)	1982-12-15
FR2385735A1 (fr)	1978-10-27
LU79004A1 (fr)	1979-09-06
IE46661B1 (en)	1983-08-24
CS221801B2 (en)	1983-04-29
NZ186385A (en)	1980-10-08
PT67568B (en)	1979-06-18
YU40798B (en)	1986-06-30
NO811913L (no)	1978-08-07
FR2379550B1 (el)	1980-07-04

Publication	Publication Date	Title
RU2192427C2 (ru)	2002-11-10	Производные эритромицина, обладающие антибактериальной активностью, способ их получения (варианты), фармацевтическая композиция и способ регулирования бактериальной инфекции у млекопитающего
DK172636B1 (en)	1999-03-22	6-o-methylerythromycin a derivative
DE69211845T2 (de)	1997-01-23	Macrozyklische laktam-prokinetika
JPS58159499A (ja)	1983-09-21	抗菌剤として有用な４″−エピエリスロマイシンａおよびその誘導体
SU886749A3 (ru)	1981-11-30	Способ получени 4-дезокси-4-амино-эритромицина а
DK158357B (da)	1990-05-07	9-deoxo-9a-(ethyl eller n-propyl)-9a-aza-9a-homoerythromycin a og farmaceutisk acceptable syreadditionssalte deraf samt farmaceutiske praeparater indeholdende disse forbindelser
SU927122A3 (ru)	1982-05-07	Способ получени производных 4"-деокси-4"-амино-эритромицина А или их солей
JPH04504259A (ja)	1992-07-30	エリスロマイシン誘導体
JPH0142275B2 (el)	1989-09-11
DE2953969C2 (el)	1987-09-03
DE69217398T2 (de)	1997-07-10	Verfahren zur Herstellung von 9-deoxo-9(z)-hydroxyiminoerythromycin A
DE3878835T2 (de)	1993-06-09	Antibakterielle 9-deoxy-9a-allyl und propargyl-9a-aza-9a-homoerythromycin-a-derivate.
DE68921719T2 (de)	1995-07-13	Amphotericin B Derivate.
SU1020004A3 (ru)	1983-05-23	Способ получени производных олеандомицина
EP0114486B1 (en)	1989-10-18	Alkylation of oleandomycin
DE69418715T2 (de)	1999-12-16	Erythromycinderivate
DE60115851T2 (de)	2006-08-10	Anti-infektionsmittel, die gegen gegenüber mehreren arzneimitteln resistente bakterienstämme nützlich sind
DE3628486A1 (de)	1988-02-25	Piperidinderivate
DE69626040T2 (de)	2004-01-22	3-deoxy-3-descladinosederivate von erythromycin a und b
KR820001218B1 (ko)	1982-07-02	반합성 4"-아미노-올레안도 마이신 유도체의 제조방법
AT371481B (de)	1983-06-27	Verfahren zur herstellung von neuen 4''-deoxy-4''-acylamidoderivaten von erythromycin
AT361629B (de)	1981-03-25	Verfahren zur herstellung von neuen 4''- -erythromycin-a-derivaten
DE2900119A1 (de)	1979-07-05	4''-desoxy-4''-carbamat- und -dithiocarbamat-derivate des oleandomycins und seine ester, verfahren zu deren herstellung und solche derivate enthaltende arzneimittel
KR820000742B1 (ko)	1982-05-03	올레안도 마이신의 4"-데옥시-4"-아릴글리옥사미도 및 아로일티오포름아미도 유도체와 그의 에스테르의 제법
DK153761B (da)	1988-08-29	Analogifremgangsmaade til fremstilling af 4ae-deoxo-4ae-acylamidoderivater af erythromycylamin og erythromycyliminderivater til anvendelse som udgangsmateriale ved denne fremgangsmaade