JPS58146595A - マクロライド系抗生物質 - Google Patents
マクロライド系抗生物質Info
- Publication number
- JPS58146595A JPS58146595A JP57029480A JP2948082A JPS58146595A JP S58146595 A JPS58146595 A JP S58146595A JP 57029480 A JP57029480 A JP 57029480A JP 2948082 A JP2948082 A JP 2948082A JP S58146595 A JPS58146595 A JP S58146595A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- tylosin
- pharmacologically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 11
- -1 gropionyl Chemical group 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 48
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 29
- 239000004182 Tylosin Substances 0.000 abstract description 23
- 229960004059 tylosin Drugs 0.000 abstract description 23
- 229930194936 Tylosin Natural products 0.000 abstract description 22
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 abstract description 22
- 235000019375 tylosin Nutrition 0.000 abstract description 22
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 15
- 241000894006 Bacteria Species 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 4
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 29
- 241000192125 Firmicutes Species 0.000 description 13
- 239000002994 raw material Substances 0.000 description 12
- BVJLPHPIQOZHNQ-JOOIDHKUSA-N 2-[(11e,13e)-6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[(5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl)oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde Chemical compound O=CCC1CC(C)C(=O)\C=C\C(\C)=C\C(COC2C(C(OC)C(O)C(C)O2)OC)C(CC)OC(=O)CC(O)C(C)C1OC1OC(C)CC(N(C)C)C1O BVJLPHPIQOZHNQ-JOOIDHKUSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000000862 absorption spectrum Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- IEMDOFXTVAPVLX-YWQHLDGFSA-N Leucomycin A1 Chemical group CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 IEMDOFXTVAPVLX-YWQHLDGFSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000194017 Streptococcus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000187480 Mycobacterium smegmatis Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- JYAQWANEOPJVEY-LYFYHCNISA-N mycarose Chemical compound C[C@H](O)[C@H](O)[C@](C)(O)CC=O JYAQWANEOPJVEY-LYFYHCNISA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QRPHLEPFYLNRDA-NLGRAQRVSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15r,16r)-6-[(2r,3r,4s,5s,6r)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,1 Chemical compound O([C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)[C@@H](O)[C@H](N(C)C)[C@H]1O QRPHLEPFYLNRDA-NLGRAQRVSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical group OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- YQLFLCVNXSPEKQ-UHFFFAOYSA-N Mycarose Natural products CC1OC(O)CC(C)(O)C1O YQLFLCVNXSPEKQ-UHFFFAOYSA-N 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- ZVOOGERIHVAODX-UHFFFAOYSA-N O-demycinosyltylosin Natural products O=CCC1CC(C)C(=O)C=CC(C)=CC(CO)C(CC)OC(=O)CC(O)C(C)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(O)C(C)(O)C2)C(C)O1 ZVOOGERIHVAODX-UHFFFAOYSA-N 0.000 description 1
- KFRIFCPXKRVUOZ-UHFFFAOYSA-N Tylosin B Natural products CCC1OC(=O)CC(O)C(C)C(OC2OC(C)C(O)C(C2O)N(C)C)C(CC(C)C(=O)C=CC(=CC1COC3OC(C)C(O)C(OC)C3OC)C)C=O KFRIFCPXKRVUOZ-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar 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
-
- 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)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57029480A JPS58146595A (ja) | 1982-02-25 | 1982-02-25 | マクロライド系抗生物質 |
| CS831163A CS235309B2 (en) | 1982-02-25 | 1983-02-21 | Method of 20-aminotylosine derivatives production |
| FI830585A FI72322C (fi) | 1982-02-25 | 1983-02-22 | Foerfarande foer framstaellning av terapeutiskt anvaendbara makrolider. |
| NZ203365A NZ203365A (en) | 1982-02-25 | 1983-02-22 | 20-amino-tylosin derivatives and pharmaceutical and veterinary compositions |
| PT76272A PT76272B (en) | 1982-02-25 | 1983-02-22 | Process for preparing 20-amino tylosin derivatives |
| PH28552A PH18435A (en) | 1982-02-25 | 1983-02-22 | 20-amino tylosin derivatives |
| IL67973A IL67973A0 (en) | 1982-02-25 | 1983-02-22 | 20-amino tylosin derivatives |
| DE8383300953T DE3360951D1 (en) | 1982-02-25 | 1983-02-23 | 20-amino tylosin derivatives |
| EP83300953A EP0087921B1 (en) | 1982-02-25 | 1983-02-23 | 20-amino tylosin derivatives |
| KR1019830000732A KR850000962B1 (ko) | 1982-02-25 | 1983-02-23 | 20-아미노 틸로신 유도체의 제조방법 |
| SU833555405A SU1360588A3 (ru) | 1982-02-25 | 1983-02-23 | Способ получени производных 20-аминодезмикозина |
| CA000422205A CA1202022A (en) | 1982-02-25 | 1983-02-23 | 20-amino tylosin derivatives |
| PL1983240735A PL138759B1 (en) | 1982-02-25 | 1983-02-23 | Method of obtaining new derivatives of thilosine |
| GB08305005A GB2115813B (en) | 1982-02-25 | 1983-02-23 | 20-amino tylosin derivatives |
| ZA831206A ZA831206B (en) | 1982-02-25 | 1983-02-23 | 20-amino tylosin derivatives |
| GR70585A GR78112B (en, 2012) | 1982-02-25 | 1983-02-23 | |
| DD83248168A DD210283A5 (de) | 1982-02-25 | 1983-02-23 | Verfahren zur herstellung von 20-aminotylosin-derivaten |
| AT83300953T ATE16008T1 (de) | 1982-02-25 | 1983-02-23 | 20-amino-tylosin-derivate. |
| ES520037A ES520037A0 (es) | 1982-02-25 | 1983-02-24 | Un procedimiento para la preparacion de una macrolida. |
| AU11801/83A AU555979B2 (en) | 1982-02-25 | 1983-02-24 | 20-amino tylosin derivatives |
| RO110152A RO85833B (ro) | 1982-02-25 | 1983-02-24 | Procedeu pentru prepararea unor derivati de 20-aminotilozina |
| US06/469,535 US4440759A (en) | 1982-02-25 | 1983-02-24 | 20-Amino tylosin derivatives and pharmaceutical compositions containing same |
| DK087783A DK153795C (da) | 1982-02-25 | 1983-02-24 | Analogifremgangsmaade til fremstilling af 20-deoxo-tylosin-macrolid-derivater eller farmaceutisk acceptable salte |
| HU83642A HU194269B (en) | 1982-02-25 | 1983-02-24 | Process for producing new 20-amino-tylosine derivatives |
| ES526529A ES526529A0 (es) | 1982-02-25 | 1983-10-17 | Un procedimiento para la preparacion de una macrolida |
| CS838673A CS235343B2 (cs) | 1982-02-25 | 1983-11-22 | Způsob výroby derivátů 20-aminotylosinu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57029480A JPS58146595A (ja) | 1982-02-25 | 1982-02-25 | マクロライド系抗生物質 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3237889A Division JPH03115293A (ja) | 1989-02-10 | 1989-02-10 | マクロライド系抗生物質 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58146595A true JPS58146595A (ja) | 1983-09-01 |
| JPH0142277B2 JPH0142277B2 (en, 2012) | 1989-09-11 |
Family
ID=12277244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57029480A Granted JPS58146595A (ja) | 1982-02-25 | 1982-02-25 | マクロライド系抗生物質 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4440759A (en, 2012) |
| EP (1) | EP0087921B1 (en, 2012) |
| JP (1) | JPS58146595A (en, 2012) |
| KR (1) | KR850000962B1 (en, 2012) |
| AT (1) | ATE16008T1 (en, 2012) |
| AU (1) | AU555979B2 (en, 2012) |
| CA (1) | CA1202022A (en, 2012) |
| CS (1) | CS235309B2 (en, 2012) |
| DD (1) | DD210283A5 (en, 2012) |
| DE (1) | DE3360951D1 (en, 2012) |
| DK (1) | DK153795C (en, 2012) |
| ES (2) | ES520037A0 (en, 2012) |
| FI (1) | FI72322C (en, 2012) |
| GB (1) | GB2115813B (en, 2012) |
| GR (1) | GR78112B (en, 2012) |
| HU (1) | HU194269B (en, 2012) |
| IL (1) | IL67973A0 (en, 2012) |
| NZ (1) | NZ203365A (en, 2012) |
| PH (1) | PH18435A (en, 2012) |
| PL (1) | PL138759B1 (en, 2012) |
| PT (1) | PT76272B (en, 2012) |
| RO (1) | RO85833B (en, 2012) |
| SU (1) | SU1360588A3 (en, 2012) |
| ZA (1) | ZA831206B (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5973598A (ja) * | 1982-09-13 | 1984-04-25 | イーライ・リリー・アンド・カンパニー | ２０−アミノマクロライド誘導体 |
| JPS59167598A (ja) * | 1983-02-28 | 1984-09-21 | イーライ・リリー・アンド・カンパニー | Ｃ−２０−およびｃ−２３−修飾マクロライド誘導体類 |
| JPH08501526A (ja) * | 1993-07-14 | 1996-02-20 | フィリップス エレクトロニクス ネムローゼ フェン ノートシャップ | 単結晶基板上における▲ｉｉ▼−▲ｖｉ▼化合物の窒素ドープエピタキシャル層の成長 |
| US5607595A (en) * | 1993-03-31 | 1997-03-04 | Toto Ltd. | Process for purifying water |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443436A (en) * | 1982-09-13 | 1984-04-17 | Eli Lilly And Company | C-20-Modified macrolide derivatives of the macrolide antibiotics tylosin, desmycosin, macrocin, and lactenocin |
| US4820695A (en) * | 1982-09-13 | 1989-04-11 | Eli Lilly And Company | C-20-dihydro-deoxy-(cyclic amino)-derivatives of macrolide antibiotics |
| IL71032A0 (en) * | 1983-02-28 | 1984-05-31 | Lilly Co Eli | C-20 and c-23-modified macrolide derivatives |
| US4629786A (en) * | 1983-02-28 | 1986-12-16 | Eli Lilly And Company | C-20- and C-23 modified macrolide derivatives |
| US4801721A (en) * | 1984-08-16 | 1989-01-31 | Ryan James W | Stereospecific synthesis of carboxyalkyl peptides |
| US4921947A (en) * | 1986-03-31 | 1990-05-01 | Eli Lilly And Company | Process for preparing macrolide derivatives |
| FR2638458A1 (fr) * | 1988-10-27 | 1990-05-04 | Adir | Nouveaux derives de la tylosine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU3121095A (en) * | 1994-09-22 | 1996-04-09 | Pfizer Inc. | Antibiotic macrolides |
| EP0778283A3 (en) * | 1995-12-05 | 1998-01-28 | Pfizer Inc. | Antibiotic macrolides |
| CN110590885A (zh) * | 2019-09-30 | 2019-12-20 | 郑州大学 | 20-取代-5-o-碳霉胺糖基-泰乐内酯衍生物 |
| CN117304241B (zh) * | 2023-11-30 | 2024-03-01 | 中国农业科学院饲料研究所 | 一种大环内酯类化合物及其制备方法与应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53132584A (en) * | 1977-04-26 | 1978-11-18 | Toyo Jozo Co Ltd | 18-cyano-18-substituted amino-18-deoxy-macrolide anibiotic substance derivative |
| JPS5732300A (en) * | 1980-06-23 | 1982-02-20 | Schering Corp | Organic compound, manufacture and medicinal composition containing same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178341A (en) * | 1960-06-27 | 1965-04-13 | Lilly Co Eli | Antibiotics tylosin and desmycosin and derivatives thereof |
| GB1587685A (en) * | 1977-03-09 | 1981-04-08 | Microbial Chem Res Found | Macrolactone derivatives and their production |
| NL8004922A (nl) * | 1979-09-19 | 1981-03-23 | Toyo Jozo Kk | Deformyltylosinederivaten. |
-
1982
- 1982-02-25 JP JP57029480A patent/JPS58146595A/ja active Granted
-
1983
- 1983-02-21 CS CS831163A patent/CS235309B2/cs unknown
- 1983-02-22 IL IL67973A patent/IL67973A0/xx unknown
- 1983-02-22 PH PH28552A patent/PH18435A/en unknown
- 1983-02-22 FI FI830585A patent/FI72322C/fi not_active IP Right Cessation
- 1983-02-22 PT PT76272A patent/PT76272B/pt unknown
- 1983-02-22 NZ NZ203365A patent/NZ203365A/en unknown
- 1983-02-23 DE DE8383300953T patent/DE3360951D1/de not_active Expired
- 1983-02-23 ZA ZA831206A patent/ZA831206B/xx unknown
- 1983-02-23 CA CA000422205A patent/CA1202022A/en not_active Expired
- 1983-02-23 EP EP83300953A patent/EP0087921B1/en not_active Expired
- 1983-02-23 PL PL1983240735A patent/PL138759B1/pl unknown
- 1983-02-23 GR GR70585A patent/GR78112B/el unknown
- 1983-02-23 AT AT83300953T patent/ATE16008T1/de not_active IP Right Cessation
- 1983-02-23 SU SU833555405A patent/SU1360588A3/ru active
- 1983-02-23 DD DD83248168A patent/DD210283A5/de not_active IP Right Cessation
- 1983-02-23 KR KR1019830000732A patent/KR850000962B1/ko not_active Expired
- 1983-02-23 GB GB08305005A patent/GB2115813B/en not_active Expired
- 1983-02-24 DK DK087783A patent/DK153795C/da not_active IP Right Cessation
- 1983-02-24 HU HU83642A patent/HU194269B/hu not_active IP Right Cessation
- 1983-02-24 US US06/469,535 patent/US4440759A/en not_active Expired - Lifetime
- 1983-02-24 RO RO110152A patent/RO85833B/ro unknown
- 1983-02-24 AU AU11801/83A patent/AU555979B2/en not_active Ceased
- 1983-02-24 ES ES520037A patent/ES520037A0/es active Granted
- 1983-10-17 ES ES526529A patent/ES526529A0/es active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53132584A (en) * | 1977-04-26 | 1978-11-18 | Toyo Jozo Co Ltd | 18-cyano-18-substituted amino-18-deoxy-macrolide anibiotic substance derivative |
| JPS5732300A (en) * | 1980-06-23 | 1982-02-20 | Schering Corp | Organic compound, manufacture and medicinal composition containing same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5973598A (ja) * | 1982-09-13 | 1984-04-25 | イーライ・リリー・アンド・カンパニー | ２０−アミノマクロライド誘導体 |
| JPS59167598A (ja) * | 1983-02-28 | 1984-09-21 | イーライ・リリー・アンド・カンパニー | Ｃ−２０−およびｃ−２３−修飾マクロライド誘導体類 |
| US5607595A (en) * | 1993-03-31 | 1997-03-04 | Toto Ltd. | Process for purifying water |
| JPH08501526A (ja) * | 1993-07-14 | 1996-02-20 | フィリップス エレクトロニクス ネムローゼ フェン ノートシャップ | 単結晶基板上における▲ｉｉ▼−▲ｖｉ▼化合物の窒素ドープエピタキシャル層の成長 |
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