PL51624B1 - - Google Patents

Info

Publication number

PL51624B1

PL51624B1 PL103238A PL10323863A PL51624B1 PL 51624 B1 PL51624 B1 PL 51624B1 PL 103238 A PL103238 A PL 103238A PL 10323863 A PL10323863 A PL 10323863A PL 51624 B1 PL51624 B1 PL 51624B1

Authority

PL

Poland

Prior art keywords

oxytetracycline

temperature

tetracycline

ester chloride

acetic acid

Prior art date

1963-12-12

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 claims description 8
• 239000004100 Oxytetracycline Substances 0.000 claims description 7
• 150000001875 compounds Chemical class 0.000 claims description 7
• 229960000625 oxytetracycline Drugs 0.000 claims description 7
• 235000019366 oxytetracycline Nutrition 0.000 claims description 7
• IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims description 7
• 239000004099 Chlortetracycline Substances 0.000 claims description 5
• 239000004098 Tetracycline 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
• 229960002180 tetracycline Drugs 0.000 claims description 5
• 235000019364 tetracycline Nutrition 0.000 claims description 5
• 229930101283 tetracycline Natural products 0.000 claims description 5
• 150000003522 tetracyclines Chemical class 0.000 claims description 5
• 239000003242 anti bacterial agent Substances 0.000 claims description 4
• 229940088710 antibiotic agent Drugs 0.000 claims description 4
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 4
• 230000003115 biocidal effect Effects 0.000 claims description 3
• 238000006243 chemical reaction Methods 0.000 claims description 3
• 229930193140 Neomycin Natural products 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 229960004927 neomycin Drugs 0.000 claims description 2
• 239000003960 organic solvent Substances 0.000 claims description 2
• 229960005322 streptomycin Drugs 0.000 claims description 2
• 150000001412 amines Chemical class 0.000 claims 1
• IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[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 IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• 239000012153 distilled water Substances 0.000 description 7
• IMLJLCJZQLGHJS-JEKSYDDFSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;dihydrate Chemical compound O.O.C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[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 IMLJLCJZQLGHJS-JEKSYDDFSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• DKFKPFUBEFVEPF-UHFFFAOYSA-N [Cl-].[NH+]1=CC=CC=C1.C(CCCCCCCCCCC)OC(C)=O Chemical compound [Cl-].[NH+]1=CC=CC=C1.C(CCCCCCCCCCC)OC(C)=O DKFKPFUBEFVEPF-UHFFFAOYSA-N 0.000 description 5
• -1 dodecylacetic acid chloride ester Chemical class 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• 239000000908 ammonium hydroxide Substances 0.000 description 3
• 238000000354 decomposition reaction Methods 0.000 description 3
• YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
• 244000005700 microbiome Species 0.000 description 3
• DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• 241000588724 Escherichia coli Species 0.000 description 2
• 241000191967 Staphylococcus aureus Species 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 230000036765 blood level Effects 0.000 description 2
• 239000003814 drug Substances 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 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 1
• QYAPHLRPFNSDNH-MRFRVZCGSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.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)C3=C(O)C2=C1O QYAPHLRPFNSDNH-MRFRVZCGSA-N 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 241000191940 Staphylococcus Species 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 231100000053 low toxicity Toxicity 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229960004368 oxytetracycline hydrochloride Drugs 0.000 description 1
• 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000002688 persistence Effects 0.000 description 1
• DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
• 210000002381 plasma Anatomy 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
• 150000003839 salts Chemical group 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1