BE628142A - - Google Patents

Info

Publication number

BE628142A

BE628142A BE628142DA BE628142A BE 628142 A BE628142 A BE 628142A BE 628142D A BE628142D A BE 628142DA BE 628142 A BE628142 A BE 628142A

Authority

BE

Belgium

Prior art keywords

process according

tetracycline

separated

mixture

solution

Prior art date

Links

• Espacenet
• Global Dossier
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• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 34
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
• 238000010438 heat treatment Methods 0.000 claims description 10
• 239000000203 mixture Substances 0.000 claims description 10
• 229930101283 tetracycline Natural products 0.000 claims description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
• 239000004098 Tetracycline Substances 0.000 claims description 9
• 150000001875 compounds Chemical class 0.000 claims description 9
• 235000019364 tetracycline Nutrition 0.000 claims description 9
• 150000003522 tetracyclines Chemical class 0.000 claims description 9
• 229960002180 tetracycline Drugs 0.000 claims description 8
• 238000001556 precipitation Methods 0.000 claims description 6
• 239000003960 organic solvent Substances 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 4
• 239000004099 Chlortetracycline Substances 0.000 claims description 3
• 238000006243 chemical reaction Methods 0.000 claims description 3
• 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 3
• 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 3
• 229960004475 chlortetracycline Drugs 0.000 claims description 3
• 235000019365 chlortetracycline Nutrition 0.000 claims description 3
• 238000000034 method Methods 0.000 claims 14
• GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=C(Cl)C=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 claims 1
• 101100021570 Caenorhabditis elegans lon-3 gene Proteins 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 239000007900 aqueous suspension Substances 0.000 claims 1
• QVFWZNCVPCJQOP-UHFFFAOYSA-N chloralodol Chemical compound CC(O)(C)CC(C)OC(O)C(Cl)(Cl)Cl QVFWZNCVPCJQOP-UHFFFAOYSA-N 0.000 claims 1
• 229960002398 demeclocycline Drugs 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 239000000243 solution Substances 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 235000019441 ethanol Nutrition 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 4
• NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide 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)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• -1 aliphatic alcohols Chemical class 0.000 description 3
• 150000001298 alcohols Chemical class 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
• 241000132092 Aster Species 0.000 description 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
• 101100469268 Caenorhabditis elegans rpl-1 gene Proteins 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 229930040373 Paraformaldehyde Natural products 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 239000008098 formaldehyde solution Substances 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical class COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
• 229920002866 paraformaldehyde Polymers 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
• 229940040944 tetracyclines Drugs 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1

Cited By (2)