BE523407A - - Google Patents

Info

Publication number

BE523407A

BE523407A BE523407DA BE523407A BE 523407 A BE523407 A BE 523407A BE 523407D A BE523407D A BE 523407DA BE 523407 A BE523407 A BE 523407A

Authority

BE

Belgium

Prior art keywords

anhydrotetracycline

addition salts

acids

chlortetracycline

acid

Prior art date

Links

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• Global Dossier
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• 239000002253 acid Substances 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• OFVLGDICTFRJMM-WESIUVDSSA-N tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 claims description 13
• 229930101283 tetracycline Natural products 0.000 claims description 13
• 150000001875 compounds Chemical class 0.000 claims description 12
• 150000007513 acids Chemical class 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 10
• NICZYMKKWKYGHT-BAQLRCJTSA-N Anhydrochlortetracycline Chemical compound C1=CC(O)=C2C(O)=C(C(=O)[C@@]3(O)[C@H]([C@@H](C(=C(C(N)=O)C3=O)O)N(C)C)C3)C3=C(C)C2=C1Cl NICZYMKKWKYGHT-BAQLRCJTSA-N 0.000 claims description 8
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
• 239000004099 Chlortetracycline Substances 0.000 claims description 7
• CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 claims description 7
• 229960004475 chlortetracycline Drugs 0.000 claims description 7
• CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 claims description 7
• 235000019365 chlortetracycline Nutrition 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 5
• 229940071870 hydroiodic acid Drugs 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 2
• 238000006243 chemical reaction Methods 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• OGQYJDHTHFAPRN-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=CC(C(F)(F)F)=C1C#N OGQYJDHTHFAPRN-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 229960003185 chlortetracycline hydrochloride Drugs 0.000 description 2
• 230000000382 dechlorinating effect Effects 0.000 description 2
• 230000002070 germicidal effect Effects 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• SPFAOPCHYIJPHJ-WPJNXPDPSA-N (4s,4as,12ar)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-4a,5-dihydro-4h-tetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(O)=C2C(O)=C(C(=O)[C@@]3(O)[C@H]([C@@H](C(C(C(N)=O)=C3O)=O)N(C)C)C3)C3=C(C)C2=C1 SPFAOPCHYIJPHJ-WPJNXPDPSA-N 0.000 description 1
• ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 239000012024 dehydrating agents‎ Substances 0.000 description 1
• 239000002024 ethyl acetate extract Substances 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1