CA2904327C - Pharmaceuticals for oral delivery - Google Patents
Pharmaceuticals for oral delivery Download PDFInfo
- Publication number
- CA2904327C CA2904327C CA2904327A CA2904327A CA2904327C CA 2904327 C CA2904327 C CA 2904327C CA 2904327 A CA2904327 A CA 2904327A CA 2904327 A CA2904327 A CA 2904327A CA 2904327 C CA2904327 C CA 2904327C
- Authority
- CA
- Canada
- Prior art keywords
- dosage form
- compound
- citric acid
- oral dosage
- solid oral
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000003814 drug Substances 0.000 title claims description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 231100001126 band 3 compound Toxicity 0.000 claims abstract description 45
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 599
- 229960004089 tigecycline Drugs 0.000 claims description 204
- FPZLLRFZJZRHSY-HJYUBDRYSA-N tigecycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O FPZLLRFZJZRHSY-HJYUBDRYSA-N 0.000 claims description 203
- 239000000203 mixture Substances 0.000 claims description 173
- FUJLYHJROOYKRA-QGZVFWFLSA-N O-lauroyl-L-carnitine Chemical compound CCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C FUJLYHJROOYKRA-QGZVFWFLSA-N 0.000 claims description 156
- 238000010521 absorption reaction Methods 0.000 claims description 127
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- 229960000318 kanamycin Drugs 0.000 claims description 81
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 81
- 229930182823 kanamycin A Natural products 0.000 claims description 81
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- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 56
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- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 7
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- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 156
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- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 11
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 10
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical group O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 9
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| US20050282756A1 (en) | 2004-06-18 | 2005-12-22 | Mehta Nozer M | Oral delivery of peptide pharmaceutical compositions |
| US8377863B2 (en) | 2007-05-29 | 2013-02-19 | Unigene Laboratories Inc. | Peptide pharmaceutical for oral delivery |
| EP2964193B1 (en) | 2013-03-05 | 2019-12-11 | Enteris BioPharma, Inc. | Pharmaceuticals for oral delivery |
| CN107427469B (zh) * | 2015-01-12 | 2021-01-26 | 安特里斯生物制药公司 | 固体口服剂型 |
| CA3165460A1 (en) | 2020-01-28 | 2021-08-05 | Genentech, Inc. | Il15/il15r alpha heterodimeric fc-fusion proteins for the treatment of cancer |
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| WO2025240494A1 (en) | 2024-05-13 | 2025-11-20 | Lumen Bioscience, Inc. | Leptin compositions and methods of making and using the same to support weight loss and/or maintenance |
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| US2956926A (en) * | 1958-09-23 | 1960-10-18 | American Cyanamid Co | Coated citric acid particles |
| NZ196348A (en) * | 1980-03-07 | 1984-08-24 | Interx Research Corp | Enhancement of absorption rate of orally administered antibiotics |
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| US4537772A (en) * | 1984-05-02 | 1985-08-27 | Merck & Co., Inc. | Enhancing absorption of drugs from gastrointestinal tract using acylcarnitines |
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| WO2001056594A1 (en) | 2000-02-04 | 2001-08-09 | Unigene Laboratories, Inc. | Nasal calcitonin formulations |
| US6673574B2 (en) | 2000-11-30 | 2004-01-06 | Unigene Laboratories Inc. | Oral delivery of peptides using enzyme-cleavable membrane translocators |
| US7316819B2 (en) | 2001-03-08 | 2008-01-08 | Unigene Laboratories, Inc. | Oral peptide pharmaceutical dosage form and method of production |
| EP1397160A1 (en) | 2001-04-30 | 2004-03-17 | Shire Laboratories Inc. | Pharmaceutical composition including ace/nep inhibitors and bioavailability enhancers |
| US8088734B2 (en) | 2003-01-21 | 2012-01-03 | Unigene Laboratories Inc. | Oral delivery of peptides |
| EP1758927A4 (en) | 2004-01-21 | 2008-09-17 | Unigene Lab Inc | PARATHYROID HORMONE AMIDE FRAGMENTS AND USES THEREOF |
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| WO2006026592A2 (en) | 2004-08-27 | 2006-03-09 | Spherics, Inc. | Oral administration of poorly absorbed drugs, methods and compositions related thereto |
| US7445911B2 (en) | 2004-11-24 | 2008-11-04 | Unigene Laboratories Inc. | Enzymatic reactions in the presence of keto acids |
| EP1907561B1 (en) | 2005-06-24 | 2013-08-28 | Unigene Laboratories, Inc. | Cell lines for expressing enzyme useful in the preparation of amidated products |
| US7449896B2 (en) * | 2005-07-29 | 2008-11-11 | Ixys Corporation | Current sensor using level shift circuit |
| US8093207B2 (en) | 2005-12-09 | 2012-01-10 | Unigene Laboratories, Inc. | Fast-acting oral peptide pharmaceutical products |
| JPWO2007072911A1 (ja) * | 2005-12-22 | 2009-06-04 | アスビオファーマ株式会社 | 塩酸サプロプテリンの生体内吸収性を向上させた製剤 |
| RU2008121238A (ru) * | 2005-12-22 | 2010-01-27 | Вайет (Us) | Способы лечения инфекций желудочно-кишечного тракта с применением тайгециклина |
| AR060355A1 (es) * | 2007-04-04 | 2008-06-11 | Kelly Jose Luis | Aparato para disipar el agua producida por equipos de climatizacion |
| US8377863B2 (en) * | 2007-05-29 | 2013-02-19 | Unigene Laboratories Inc. | Peptide pharmaceutical for oral delivery |
| CN102014878B (zh) * | 2007-11-05 | 2013-10-23 | 夏威夷大学 | 用于口服给药极性药剂的提高生物利用度的制剂 |
| US20100256060A1 (en) * | 2009-04-02 | 2010-10-07 | Unigene Laboratories Inc. | Peptide pharmaceuticals for nasal delivery |
| WO2012040364A1 (en) | 2010-09-21 | 2012-03-29 | Unigene Laboratories Inc. | Calcitonin products and therapies for treating inflammatory or degenerative diseases |
| PT2651398T (pt) | 2010-12-16 | 2018-03-09 | Novo Nordisk As | Composições sólidas compreendendo um agonista de glp-1 e um sal de ácido n-(8-(2-hidroxibenzoil)amino) caprílico |
| US20150118315A1 (en) * | 2011-06-14 | 2015-04-30 | Stealth Peptides International, Inc. | Aromatic-cationic peptides and uses of same |
| PL2720707T3 (pl) | 2011-06-15 | 2019-06-28 | Resother Pharma Aps | Przeciwzapalne produkty farmaceutyczne |
| EP2964193B1 (en) | 2013-03-05 | 2019-12-11 | Enteris BioPharma, Inc. | Pharmaceuticals for oral delivery |
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