PL53651B1 - - Google Patents

Info

Publication number

PL53651B1

PL53651B1 PL107542A PL10754265A PL53651B1 PL 53651 B1 PL53651 B1 PL 53651B1 PL 107542 A PL107542 A PL 107542A PL 10754265 A PL10754265 A PL 10754265A PL 53651 B1 PL53651 B1 PL 53651B1

Authority

PL

Poland

Prior art keywords

formula

piperazine

tetracycline

dimethyltetracycline

chlortetracycline

Prior art date

1965-02-20

Links

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• 239000004098 Tetracycline Substances 0.000 claims description 8
• 229960002180 tetracycline Drugs 0.000 claims description 8
• 235000019364 tetracycline Nutrition 0.000 claims description 8
• 229930101283 tetracycline Natural products 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 7
• 150000003522 tetracyclines Chemical class 0.000 claims description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
• 239000004099 Chlortetracycline Substances 0.000 claims description 5
• 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 5
• 229960004475 chlortetracycline Drugs 0.000 claims description 5
• 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 5
• 235000019365 chlortetracycline Nutrition 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 4
• 150000004885 piperazines Chemical class 0.000 claims description 4
• 125000000565 sulfonamide group Chemical group 0.000 claims description 4
• 125000001931 aliphatic group Chemical group 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 150000003949 imides Chemical class 0.000 claims description 2
• 239000003960 organic solvent Substances 0.000 claims description 2
• 150000003839 salts Chemical class 0.000 claims description 2
• 230000003115 biocidal effect Effects 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 239000000047 product Substances 0.000 description 9
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• 229960005141 piperazine Drugs 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
• LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical group CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 2
• FEFMTWYKZOVFMX-UHFFFAOYSA-N 4-methyl-N-[[4-[[(4-methylphenyl)sulfonylamino]methyl]piperazin-1-yl]methyl]benzenesulfonamide Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NCN1CCN(CC1)CNS(=O)(=O)C1=CC=C(C)C=C1 FEFMTWYKZOVFMX-UHFFFAOYSA-N 0.000 description 1
• 239000012296 anti-solvent Substances 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 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
• 239000013078 crystal Substances 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 150000002391 heterocyclic compounds Chemical class 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 229960003506 piperazine hexahydrate Drugs 0.000 description 1
• AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 1
• 239000013557 residual solvent Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
• -1 tetracycline piperazine derivatives Chemical class 0.000 description 1