JPS6233240B2 - - Google Patents

Info

Publication number

JPS6233240B2

JPS6233240B2 JP54029805A JP2980579A JPS6233240B2 JP S6233240 B2 JPS6233240 B2 JP S6233240B2 JP 54029805 A JP54029805 A JP 54029805A JP 2980579 A JP2980579 A JP 2980579A JP S6233240 B2 JPS6233240 B2 JP S6233240B2

Authority

JP

Japan

Prior art keywords

group

tylosin

alkanoyl group

carbon atoms

production method

Prior art date

1979-03-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Links

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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 32
• 125000002252 acyl group Chemical group 0.000 claims description 24
• -1 isobutyryl Chemical group 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 229910021529 ammonia Inorganic materials 0.000 claims description 4
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 238000010438 heat treatment Methods 0.000 claims description 4
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 238000010992 reflux Methods 0.000 claims description 4
• 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 3
• UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• MLRKYSNODSLPAB-UHFFFAOYSA-N hex-1-yn-1-ol Chemical compound CCCCC#CO MLRKYSNODSLPAB-UHFFFAOYSA-N 0.000 claims 1
• 239000004182 Tylosin Substances 0.000 description 29
• 229960004059 tylosin Drugs 0.000 description 29
• 229930194936 Tylosin Natural products 0.000 description 20
• 235000019375 tylosin Nutrition 0.000 description 20
• 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 description 18
• 238000006243 chemical reaction Methods 0.000 description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
• 238000004809 thin layer chromatography Methods 0.000 description 14
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 5
• 150000001875 compounds Chemical class 0.000 description 5
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 230000010933 acylation Effects 0.000 description 3
• 238000005917 acylation reaction Methods 0.000 description 3
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
• 239000003513 alkali Substances 0.000 description 3
• YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 3
• 230000008034 disappearance Effects 0.000 description 3
• 150000007529 inorganic bases Chemical class 0.000 description 3
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
• 244000025254 Cannabis sativa Species 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 239000003463 adsorbent Substances 0.000 description 2
• 125000003172 aldehyde 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
• 150000008064 anhydrides Chemical class 0.000 description 2
• 238000002306 biochemical method Methods 0.000 description 2
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 2
• WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 239000011347 resin Substances 0.000 description 2
• 229920005989 resin Polymers 0.000 description 2
• 238000001179 sorption measurement Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
• URZYJMFUPBREMV-UHFFFAOYSA-N 4-methylpentanoyl 4-methylpentanoate Chemical compound CC(C)CCC(=O)OC(=O)CCC(C)C URZYJMFUPBREMV-UHFFFAOYSA-N 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• ZWCKECHGNUHVBQ-UHFFFAOYSA-N benzene;ethyl acetate;hexane;methanol;propan-2-one Chemical compound OC.CC(C)=O.CCCCCC.CCOC(C)=O.C1=CC=CC=C1 ZWCKECHGNUHVBQ-UHFFFAOYSA-N 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
• 239000003120 macrolide antibiotic agent Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 238000005406 washing Methods 0.000 description 1