SE447118B - 4"-deoxi-4"-acylamido-derivat av oleandomyciner, erytromyciner och erytromycinkarbonat - Google Patents
4"-deoxi-4"-acylamido-derivat av oleandomyciner, erytromyciner och erytromycinkarbonatInfo
- Publication number
- SE447118B SE447118B SE7900028A SE7900028A SE447118B SE 447118 B SE447118 B SE 447118B SE 7900028 A SE7900028 A SE 7900028A SE 7900028 A SE7900028 A SE 7900028A SE 447118 B SE447118 B SE 447118B
- Authority
- SE
- Sweden
- Prior art keywords
- mmm
- deoxy
- hmm
- oleandomycin
- solution
- Prior art date
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title 1
- 229960002351 oleandomycin Drugs 0.000 claims description 48
- 239000004104 Oleandomycin Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000243 solution Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 239000006260 foam Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 229960001701 chloroform Drugs 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 244000005700 microbiome Species 0.000 description 7
- 235000019367 oleandomycin Nutrition 0.000 description 7
- -1 4-methyl-5-thiazolyl Chemical group 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 241000588653 Neisseria Species 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
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- 239000012442 inert solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
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- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000013736 caramel Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- WGXZDYPGLJYBJW-UHFFFAOYSA-N chloroform;propan-2-ol Chemical compound CC(C)O.ClC(Cl)Cl WGXZDYPGLJYBJW-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 238000009833 condensation Methods 0.000 description 1
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- 235000005687 corn oil Nutrition 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
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- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
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- 239000007937 lozenge Substances 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HSDHDEOGCBGOKV-UHFFFAOYSA-N thiadiazole-4-carbonyl chloride Chemical compound ClC(=O)C1=CSN=N1 HSDHDEOGCBGOKV-UHFFFAOYSA-N 0.000 description 1
- HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Substances FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86672278A | 1978-01-03 | 1978-01-03 | |
| US05/937,640 US4180654A (en) | 1978-01-03 | 1978-08-29 | 4"-Deoxy-4"-acylamido derivatives of oleandomycin, erythromycin and erythromycin carbonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7900028L SE7900028L (sv) | 1979-07-04 |
| SE447118B true SE447118B (sv) | 1986-10-27 |
Family
ID=27127966
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7900028A SE447118B (sv) | 1978-01-03 | 1979-01-02 | 4"-deoxi-4"-acylamido-derivat av oleandomyciner, erytromyciner och erytromycinkarbonat |
| SE8304417A SE448385B (sv) | 1978-01-03 | 1983-08-15 | 4"-deoxi-4"-acylamido-derivat av erytromycin-a |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8304417A SE448385B (sv) | 1978-01-03 | 1983-08-15 | 4"-deoxi-4"-acylamido-derivat av erytromycin-a |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4180654A (en, 2012) |
| JP (1) | JPS5495585A (en, 2012) |
| AT (1) | AT364457B (en, 2012) |
| AU (1) | AU506684B2 (en, 2012) |
| CH (1) | CH639972A5 (en, 2012) |
| CS (1) | CS204042B2 (en, 2012) |
| DD (1) | DD141026A5 (en, 2012) |
| DE (2) | DE2953969C2 (en, 2012) |
| DK (1) | DK147943C (en, 2012) |
| ES (2) | ES476544A1 (en, 2012) |
| FI (1) | FI68058C (en, 2012) |
| FR (1) | FR2413403A1 (en, 2012) |
| GB (1) | GB2013181B (en, 2012) |
| GR (1) | GR72779B (en, 2012) |
| HU (1) | HU180276B (en, 2012) |
| IE (1) | IE47642B1 (en, 2012) |
| IL (1) | IL56363A (en, 2012) |
| IN (1) | IN150395B (en, 2012) |
| IT (1) | IT1109925B (en, 2012) |
| LU (1) | LU80747A1 (en, 2012) |
| NL (1) | NL176461C (en, 2012) |
| NO (2) | NO146711C (en, 2012) |
| NZ (1) | NZ189274A (en, 2012) |
| PH (4) | PH14745A (en, 2012) |
| PL (2) | PL117603B1 (en, 2012) |
| PT (1) | PT69014A (en, 2012) |
| SE (2) | SE447118B (en, 2012) |
| YU (2) | YU312278A (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5848285U (ja) * | 1981-09-26 | 1983-04-01 | コナミ工業株式会社 | テ−ブル型テレビゲ−ム機 |
| US4429116A (en) * | 1982-12-27 | 1984-01-31 | Pfizer Inc. | Alkylated oleandomycin containing compounds |
| US4518590A (en) * | 1984-04-13 | 1985-05-21 | Pfizer Inc. | 9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method |
| JPS62240086A (ja) * | 1986-04-12 | 1987-10-20 | 株式会社 エ−ス電研 | 遊技機の前面構造 |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
| YU55690A (en) * | 1990-03-21 | 1990-12-31 | Pliva Pharm & Chem Works | Process for preparing oleandomycin oxime |
| GB0310980D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| WO2004101587A1 (en) * | 2003-05-13 | 2004-11-25 | Glaxo Group Limited | Novel 14 and 15 memberred-ring compounds |
| GB0310992D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| GB0310984D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3869445A (en) * | 1973-05-03 | 1975-03-04 | Abbott Lab | 4{41 -O-sulfonyl erythromycin-9-O-oxime derivatives |
| US3884902A (en) * | 1973-05-04 | 1975-05-20 | Abbott Lab | Sulfonyl derivatives of erythromycin |
| US3884903A (en) * | 1973-06-21 | 1975-05-20 | Abbott Lab | 4{41 -Deoxy-4{41 -oxoerythromycin B derivatives |
| US4063014A (en) * | 1975-06-12 | 1977-12-13 | Abbott Laboratories | 4"-O-sulfonyl erythromycin-9-O-oxime derivatives |
| US4069379A (en) * | 1976-07-08 | 1978-01-17 | Pfizer Inc. | Semi-synthetic oleandomycins |
| IE44509B1 (en) * | 1976-03-03 | 1981-12-30 | Pfizer | Semi-synthetic oleandomycins |
| US4085119A (en) * | 1977-02-04 | 1978-04-18 | Pfizer Inc. | 4-Substituted amino derivatives of oleandomycin |
| US4090017A (en) * | 1977-02-04 | 1978-05-16 | Pfizer Inc. | 4-Deoxy-4-substituted amino derivatives of oleandomycin |
-
1978
- 1978-08-29 US US05/937,640 patent/US4180654A/en not_active Expired - Lifetime
- 1978-11-15 DK DK507778A patent/DK147943C/da not_active IP Right Cessation
- 1978-11-20 IN IN830/DEL/78A patent/IN150395B/en unknown
- 1978-12-20 GB GB7849227A patent/GB2013181B/en not_active Expired
- 1978-12-21 CH CH1303678A patent/CH639972A5/de not_active IP Right Cessation
- 1978-12-21 NZ NZ189274A patent/NZ189274A/xx unknown
- 1978-12-28 JP JP16447078A patent/JPS5495585A/ja active Granted
- 1978-12-28 YU YU03122/78A patent/YU312278A/xx unknown
- 1978-12-29 HU HU78PI660A patent/HU180276B/hu not_active IP Right Cessation
- 1978-12-29 AU AU42985/78A patent/AU506684B2/en not_active Expired
- 1978-12-30 GR GR58008A patent/GR72779B/el unknown
-
1979
- 1979-01-02 FI FI790004A patent/FI68058C/fi not_active IP Right Cessation
- 1979-01-02 PH PH22004A patent/PH14745A/en unknown
- 1979-01-02 LU LU80747A patent/LU80747A1/xx unknown
- 1979-01-02 PT PT69014A patent/PT69014A/pt unknown
- 1979-01-02 IT IT19013/79A patent/IT1109925B/it active
- 1979-01-02 IE IE5/79A patent/IE47642B1/en not_active IP Right Cessation
- 1979-01-02 ES ES476544A patent/ES476544A1/es not_active Expired
- 1979-01-02 FR FR7900014A patent/FR2413403A1/fr active Granted
- 1979-01-02 IL IL56363A patent/IL56363A/xx not_active IP Right Cessation
- 1979-01-02 AT AT0002979A patent/AT364457B/de not_active IP Right Cessation
- 1979-01-02 NO NO790006A patent/NO146711C/no unknown
- 1979-01-02 SE SE7900028A patent/SE447118B/sv not_active IP Right Cessation
- 1979-01-02 NL NLAANVRAGE7900006,A patent/NL176461C/xx not_active IP Right Cessation
- 1979-01-03 DE DE2953969A patent/DE2953969C2/de not_active Expired
- 1979-01-03 DE DE19792900118 patent/DE2900118A1/de active Granted
- 1979-01-03 CS CS79100A patent/CS204042B2/cs unknown
- 1979-01-03 PL PL1979212593A patent/PL117603B1/pl unknown
- 1979-01-03 PL PL1979227812A patent/PL118573B1/pl unknown
- 1979-01-03 DD DD79210317A patent/DD141026A5/de unknown
- 1979-07-11 ES ES482420A patent/ES482420A1/es not_active Expired
- 1979-12-21 PH PH23449A patent/PH15439A/en unknown
- 1979-12-21 PH PH23451A patent/PH15752A/en unknown
- 1979-12-21 PH PH23450A patent/PH15626A/en unknown
-
1982
- 1982-02-26 NO NO820613A patent/NO147716C/no unknown
- 1982-09-24 YU YU02139/82A patent/YU213982A/xx unknown
-
1983
- 1983-08-15 SE SE8304417A patent/SE448385B/sv not_active IP Right Cessation
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