CN103536530A - 盐酸多西环素长效注射剂及制备方法 - Google Patents
盐酸多西环素长效注射剂及制备方法 Download PDFInfo
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- CN103536530A CN103536530A CN201310528303.6A CN201310528303A CN103536530A CN 103536530 A CN103536530 A CN 103536530A CN 201310528303 A CN201310528303 A CN 201310528303A CN 103536530 A CN103536530 A CN 103536530A
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- injection
- saib
- doxycycline
- ethyl oleate
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- 238000002347 injection Methods 0.000 title claims abstract description 55
- 239000007924 injection Substances 0.000 title claims abstract description 55
- PTNZGHXUZDHMIQ-UHFFFAOYSA-N 4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC=C2C(C)C(C(O)C3C(C(O)=C(C(N)=O)C(=O)C3N(C)C)(O)C3=O)C3=C(O)C2=C1O PTNZGHXUZDHMIQ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229960004082 doxycycline hydrochloride Drugs 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract description 102
- UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 claims abstract description 56
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 26
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 claims abstract description 20
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims abstract description 19
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims abstract description 19
- 229940093471 ethyl oleate Drugs 0.000 claims abstract description 19
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229960002903 benzyl benzoate Drugs 0.000 claims abstract description 8
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- 235000019438 castor oil Nutrition 0.000 claims abstract description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims abstract description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 13
- 230000003078 antioxidant effect Effects 0.000 claims description 13
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 8
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 6
- 239000000473 propyl gallate Substances 0.000 claims description 4
- 235000010388 propyl gallate Nutrition 0.000 claims description 4
- 229940075579 propyl gallate Drugs 0.000 claims description 4
- QSHVAZMOLNGWSY-UHFFFAOYSA-N 3-butyl-4-methoxyphenol Chemical group CCCCC1=CC(O)=CC=C1OC QSHVAZMOLNGWSY-UHFFFAOYSA-N 0.000 claims description 3
- -1 Benzyl Benzoate ester Chemical class 0.000 claims description 3
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims 1
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- 238000011065 in-situ storage Methods 0.000 abstract description 7
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- 239000001797 sucrose acetate isobutyrate Substances 0.000 abstract 2
- 238000013268 sustained release Methods 0.000 abstract 2
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- 239000002612 dispersion medium Substances 0.000 abstract 1
- 244000144972 livestock Species 0.000 abstract 1
- 239000012053 oil suspension Substances 0.000 abstract 1
- 229940090044 injection Drugs 0.000 description 44
- 239000002245 particle Substances 0.000 description 19
- 229960003722 doxycycline Drugs 0.000 description 18
- XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
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- 235000019198 oils Nutrition 0.000 description 12
- 239000000084 colloidal system Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 description 7
- 239000008158 vegetable oil Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
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- 238000010255 intramuscular injection Methods 0.000 description 5
- 239000007927 intramuscular injection Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
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- 229940031975 doxycycline injection Drugs 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 4
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
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- NESIVXZOSKKUDP-ARVJLQODSA-N (4r,5s,6s,7r,9r,11e,13e,15r,16r)-6-[(2r,3r,4s,5s,6r)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-7-[2-[(3s,5r)-3,5-dimethylpiperidin-1-yl]ethyl]-16-ethyl-4-hydroxy-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13 Chemical compound OP(O)(O)=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]1CCN1C[C@H](C)C[C@H](C)C1)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)[C@@H](O)[C@H](N(C)C)[C@H]1O NESIVXZOSKKUDP-ARVJLQODSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
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- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 229960001082 trimethoprim Drugs 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
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CN201310528303.6A CN103536530A (zh) | 2013-10-30 | 2013-10-30 | 盐酸多西环素长效注射剂及制备方法 |
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CN201310528303.6A CN103536530A (zh) | 2013-10-30 | 2013-10-30 | 盐酸多西环素长效注射剂及制备方法 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104288162A (zh) * | 2014-05-29 | 2015-01-21 | 郑州百瑞动物药业有限公司 | 一种奶牛用盐酸多西环素子宫注入剂及其制备方法 |
EP3624840A4 (en) * | 2017-05-19 | 2021-03-10 | Lunella Biotech, Inc. | ANTIMITOSCINE: TARGETED INHIBITORS OF MITOCHONDRIAL BIOGENESIS TO DESCRIBE CANCER STEM CELLS |
EP3897659A4 (en) * | 2018-12-17 | 2022-09-07 | Lunella Biotech, Inc. | TRITHERAPIES TO FIGHT AGAINST AGING |
EP3897658A4 (en) * | 2018-12-17 | 2022-10-19 | Lunella Biotech, Inc. | TRITHERAPIES THAT TARGETING MITOCHONDRIA AND KILLING CANCER STEM CELLS |
US11497759B2 (en) | 2017-12-01 | 2022-11-15 | Lunella Biotech, Inc. | Repurposcins: targeted inhibitors of mitochondrial biogenesis for eradicating cancer stem cells |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4086332A (en) * | 1976-01-02 | 1978-04-25 | Pfizer Inc. | Doxycycline compositions |
CN1682693A (zh) * | 2005-03-15 | 2005-10-19 | 沈阳药科大学 | 一种硬化治疗血管瘤和脉管畸形的原位凝胶药物传递*** |
CN101862293A (zh) * | 2010-06-22 | 2010-10-20 | 华南农业大学 | 盐酸多西环素的油混悬液及其制备方法和应用 |
CN102440998A (zh) * | 2010-10-15 | 2012-05-09 | 天津瑞普生物技术股份有限公司 | 一种复方盐酸多西环素混悬注射剂及其制备方法 |
-
2013
- 2013-10-30 CN CN201310528303.6A patent/CN103536530A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4086332A (en) * | 1976-01-02 | 1978-04-25 | Pfizer Inc. | Doxycycline compositions |
CN1682693A (zh) * | 2005-03-15 | 2005-10-19 | 沈阳药科大学 | 一种硬化治疗血管瘤和脉管畸形的原位凝胶药物传递*** |
CN101862293A (zh) * | 2010-06-22 | 2010-10-20 | 华南农业大学 | 盐酸多西环素的油混悬液及其制备方法和应用 |
CN102440998A (zh) * | 2010-10-15 | 2012-05-09 | 天津瑞普生物技术股份有限公司 | 一种复方盐酸多西环素混悬注射剂及其制备方法 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104288162A (zh) * | 2014-05-29 | 2015-01-21 | 郑州百瑞动物药业有限公司 | 一种奶牛用盐酸多西环素子宫注入剂及其制备方法 |
EP3624840A4 (en) * | 2017-05-19 | 2021-03-10 | Lunella Biotech, Inc. | ANTIMITOSCINE: TARGETED INHIBITORS OF MITOCHONDRIAL BIOGENESIS TO DESCRIBE CANCER STEM CELLS |
US11160821B2 (en) | 2017-05-19 | 2021-11-02 | Lunella Biotech, Inc. | Antimitoscins: targeted inhibitors of mitochondrial biogenesis for eradicating cancer stem cells |
US11865130B2 (en) | 2017-05-19 | 2024-01-09 | Lunella Biotech, Inc. | Antimitoscins: targeted inhibitors of mitochondrial biogenesis for eradicating cancer stem cells |
US11497759B2 (en) | 2017-12-01 | 2022-11-15 | Lunella Biotech, Inc. | Repurposcins: targeted inhibitors of mitochondrial biogenesis for eradicating cancer stem cells |
EP3897659A4 (en) * | 2018-12-17 | 2022-09-07 | Lunella Biotech, Inc. | TRITHERAPIES TO FIGHT AGAINST AGING |
EP3897658A4 (en) * | 2018-12-17 | 2022-10-19 | Lunella Biotech, Inc. | TRITHERAPIES THAT TARGETING MITOCHONDRIA AND KILLING CANCER STEM CELLS |
US11918597B2 (en) | 2018-12-17 | 2024-03-05 | Lunella Biotech, Inc. | Triple combination therapies for anti-aging |
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