JP2014518272A5 - - Google Patents
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- Publication number
- JP2014518272A5 JP2014518272A5 JP2014519052A JP2014519052A JP2014518272A5 JP 2014518272 A5 JP2014518272 A5 JP 2014518272A5 JP 2014519052 A JP2014519052 A JP 2014519052A JP 2014519052 A JP2014519052 A JP 2014519052A JP 2014518272 A5 JP2014518272 A5 JP 2014518272A5
- Authority
- JP
- Japan
- Prior art keywords
- mtz
- mucoadhesive
- aqueous gel
- item
- composition
- 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.)
- Granted
Links
- 239000000499 gel Substances 0.000 claims description 111
- 230000003232 mucoadhesive effect Effects 0.000 claims description 94
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 90
- 229960000282 metronidazole Drugs 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 50
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 43
- -1 aromatic alcohols Chemical class 0.000 claims description 37
- 229920000642 polymer Polymers 0.000 claims description 25
- 229960004063 propylene glycol Drugs 0.000 claims description 20
- 235000013772 propylene glycol Nutrition 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 17
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 14
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 14
- 210000003491 skin Anatomy 0.000 claims description 14
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 13
- 229920002125 Sokalan® Polymers 0.000 claims description 9
- 239000003755 preservative agent Substances 0.000 claims description 9
- 229920000148 Polycarbophil calcium Polymers 0.000 claims description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 7
- 238000000338 in vitro Methods 0.000 claims description 7
- 229950005134 polycarbophil Drugs 0.000 claims description 7
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 7
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 6
- 229960003415 propylparaben Drugs 0.000 claims description 6
- 210000000434 stratum corneum Anatomy 0.000 claims description 6
- 229920000858 Cyclodextrin Polymers 0.000 claims description 5
- 239000004375 Dextrin Substances 0.000 claims description 5
- 229920001353 Dextrin Polymers 0.000 claims description 5
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 5
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 5
- 235000019425 dextrin Nutrition 0.000 claims description 5
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 5
- 235000001968 nicotinic acid Nutrition 0.000 claims description 5
- 239000011664 nicotinic acid Substances 0.000 claims description 5
- 229960003512 nicotinic acid Drugs 0.000 claims description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 229920002807 Thiomer Polymers 0.000 claims description 4
- 229960001631 carbomer Drugs 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229940071826 hydroxyethyl cellulose Drugs 0.000 claims description 3
- 235000005152 nicotinamide Nutrition 0.000 claims description 3
- 239000011570 nicotinamide Substances 0.000 claims description 3
- 229960003966 nicotinamide Drugs 0.000 claims description 3
- 229960005323 phenoxyethanol Drugs 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229940063189 metrogel Drugs 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims 2
- 238000011282 treatment Methods 0.000 description 3
- 230000035876 healing Effects 0.000 description 2
- 208000004926 Bacterial Vaginosis Diseases 0.000 description 1
- 208000037009 Vaginitis bacterial Diseases 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 229920001484 poly(alkylene) Polymers 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161502285P | 2011-06-28 | 2011-06-28 | |
| US61/502,285 | 2011-06-28 | ||
| US201161508058P | 2011-07-14 | 2011-07-14 | |
| US61/508,058 | 2011-07-14 | ||
| PCT/US2012/044738 WO2013003646A1 (en) | 2011-06-28 | 2012-06-28 | High dosage mucoadhesive metronidazole aqueous-based gel formulations their use to treat bacterial vaginosis |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016154447A Division JP6235087B2 (ja) | 2011-06-28 | 2016-08-05 | 高用量粘膜接着性メトロニダゾール水系ゲル製剤および細菌性膣炎を治療するためのそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014518272A JP2014518272A (ja) | 2014-07-28 |
| JP2014518272A5 true JP2014518272A5 (cg-RX-API-DMAC7.html) | 2015-08-13 |
| JP5986632B2 JP5986632B2 (ja) | 2016-09-06 |
Family
ID=47391265
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014519052A Active JP5986632B2 (ja) | 2011-06-28 | 2012-06-28 | 高用量粘膜接着性メトロニダゾール水系ゲル製剤および細菌性膣炎を治療するためのそれらの使用 |
| JP2016154447A Active JP6235087B2 (ja) | 2011-06-28 | 2016-08-05 | 高用量粘膜接着性メトロニダゾール水系ゲル製剤および細菌性膣炎を治療するためのそれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016154447A Active JP6235087B2 (ja) | 2011-06-28 | 2016-08-05 | 高用量粘膜接着性メトロニダゾール水系ゲル製剤および細菌性膣炎を治療するためのそれらの使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US8946276B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2725904B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5986632B2 (cg-RX-API-DMAC7.html) |
| CN (2) | CN103763925A (cg-RX-API-DMAC7.html) |
| AU (2) | AU2012275292B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112013033759B1 (cg-RX-API-DMAC7.html) |
| CA (2) | CA2840571C (cg-RX-API-DMAC7.html) |
| MX (1) | MX381271B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013003646A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ703203A (en) | 2012-06-13 | 2016-07-29 | Evofem Inc | Compositions and methods for enhancing the efficacy of contraceptive microbicides |
| WO2014210156A1 (en) | 2013-06-25 | 2014-12-31 | Mission Pharmacal Company | Novel formulations for the treatment of vaginal disorders |
| KR102407408B1 (ko) | 2013-12-19 | 2022-06-10 | 에보펨 인코포레이티드 | 알긴산계 항균성 화합물을 사용하는 염증 및 질병을 억제하기 위한 조성물 및 방법 |
| KR20190026962A (ko) * | 2014-09-05 | 2019-03-13 | 심바이오믹스 세러퓨틱스 엘엘씨 | 세균질증 치료에 사용하기 위한 세크니다졸 |
| CA2988082C (en) | 2015-06-01 | 2020-09-29 | Symbiomix Therapeutics, Llc | Novel nitroimidazole formulations and uses thereof |
| US10759740B2 (en) | 2016-03-24 | 2020-09-01 | Rutgers, The State University Of New Jersey | Antibacterial agents |
| CN110225750A (zh) * | 2016-10-04 | 2019-09-10 | 伊沃菲姆股份有限公司 | 细菌性阴道病的治疗和预防方法 |
| SE1750680A1 (en) * | 2017-05-30 | 2018-12-01 | Peptonic Medical Ab | Composition for treating or preventing climacteric disorders |
| US20200126094A1 (en) * | 2018-10-19 | 2020-04-23 | BioIDC, Inc. | Medical research fraud detection system and software |
| US12280037B2 (en) | 2020-09-22 | 2025-04-22 | Evofem Biosciences, Inc. | Method and pharmaceutical composition for treating or preventing trichomoniasis and uses thereof |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837378A (en) | 1986-01-15 | 1989-06-06 | Curatek Pharmaceuticals, Inc. | Topical metronidazole formulations and therapeutic uses thereof |
| ATE67667T1 (de) | 1987-03-20 | 1991-10-15 | Curatek Pharmaceuticals | Neue topische metronidazol-formulierungen. |
| US5536743A (en) | 1988-01-15 | 1996-07-16 | Curatek Pharmaceuticals Limited Partnership | Intravaginal treatment of vaginal infections with buffered metronidazole compositions |
| CA1337279C (en) | 1989-06-06 | 1995-10-10 | Robert J. Borgman | Intravaginal treatment of vaginal infections with buffered metronidazole compositions |
| DE69201547T2 (de) | 1991-10-18 | 1995-08-03 | Dow Corning | Silikon druckempfindliche Klebstoffe mit verbesserter Haftung an Substraten mit niedriger Oberflächenspannung. |
| IT1284874B1 (it) * | 1996-08-02 | 1998-05-22 | Farmigea Spa | Complessi bioadesivi di polycarbophil e farmaci antifungini o antiprotozoari azolici |
| GB9626513D0 (en) | 1996-12-20 | 1997-02-05 | Bioglan Ireland R & D Ltd | A pharmaceutical composition |
| DE69819748T2 (de) | 1997-09-12 | 2004-09-30 | Columbia Laboratories (Bermuda) Ltd. | Arzneimittel zur behandlung von dysmenorrhöe und verfrühten wehen |
| WO1998014768A2 (en) | 1997-10-06 | 1998-04-09 | Schwartz Sorell L | Transdermal chemical monitoring device |
| US6468989B1 (en) * | 2000-07-13 | 2002-10-22 | Dow Pharmaceutical Sciences | Gel compositions containing metronidazole |
| US6881726B2 (en) | 2001-12-24 | 2005-04-19 | Dow Pharmaceutical Sciences | Aqueous compositions containing metronidazole |
| US7368122B1 (en) | 2002-03-08 | 2008-05-06 | Dow Pharmaceutical Sciences | Skin cream |
| US20050186142A1 (en) | 2002-10-25 | 2005-08-25 | Foamix Ltd. | Kit and composition of imidazole with enhanced bioavailability |
| US9211259B2 (en) | 2002-11-29 | 2015-12-15 | Foamix Pharmaceuticals Ltd. | Antibiotic kit and composition and uses thereof |
| US7704518B2 (en) | 2003-08-04 | 2010-04-27 | Foamix, Ltd. | Foamable vehicle and pharmaceutical compositions thereof |
| US7456207B2 (en) * | 2003-09-25 | 2008-11-25 | Teva Pharmaceuticals Usa, Inc. | Vaginal pharmaceutical compositions and methods for preparing them |
| FR2887149B1 (fr) | 2005-06-17 | 2007-08-03 | Galderma Sa | Procede de solubilisation du metronidazole |
| US20060093675A1 (en) | 2004-10-29 | 2006-05-04 | Mathew Ebmeier | Intravaginal treatment of vaginal infections with metronidazole compositions |
| FR2882552B1 (fr) | 2005-02-25 | 2008-12-26 | Galderma Sa | Gel aqueux de haute stabilite a base de metronidazole et procedes pour leur preparation |
| MX2007014101A (es) | 2005-05-09 | 2009-02-13 | Foamix Ltd | Vehiculo espumable y composiciones farmaceuticas del mismo. |
| AU2006339311A1 (en) | 2005-06-07 | 2007-09-07 | Foamix Ltd. | Antibiotic kit and composition and uses thereof |
| FR2890560B1 (fr) | 2005-09-13 | 2011-06-24 | Galderma Sa | Mousses dermatologiques a base de metronidazole et emulsions pour leur preparation |
| FR2890559B1 (fr) | 2005-09-13 | 2011-06-24 | Galderma Sa | Mousses dermatologiques a base de metronidazole et emulsions pour la preparation |
| WO2007086978A2 (en) | 2005-11-09 | 2007-08-02 | Dow Pharmaceutical Sciences | Azithromycin for treatment of granulomatous rosacea |
| EP1968543A2 (en) | 2006-01-05 | 2008-09-17 | Drugtech Corporation | Composition and method of use thereof |
| FR2899475A1 (fr) | 2006-04-10 | 2007-10-12 | Galderma Res & Dev | Composition pharmaceutique pour le traitement de la rosacee |
| WO2008038140A2 (en) | 2006-06-07 | 2008-04-03 | Foamix Ltd. | Foamable vehicle comprising polypropylene glycol alkyl ether and pharmaceutical compositions thereof |
| US20080287513A1 (en) | 2007-05-14 | 2008-11-20 | Jerry Zhang | Topical compositions containing metronidazole |
| US20080287515A1 (en) * | 2007-05-14 | 2008-11-20 | Jerry Zhang | Topical compositions containing metronidazole |
| US20080287514A1 (en) | 2007-05-14 | 2008-11-20 | Jerry Zhang | Topical compositions containing metronidazole |
| US20080312304A1 (en) | 2007-06-13 | 2008-12-18 | Jerry Zhang | Topical compositions containing metronidazole |
| US7893097B2 (en) * | 2008-02-02 | 2011-02-22 | Dow Pharmaceutical Sciences, Inc. | Methods and compositions for increasing solubility of azole drug compounds that are poorly soluble in water |
| US20100105750A1 (en) | 2008-10-23 | 2010-04-29 | Nycomed Us Inc. | Stable metronidazole gel formulations |
| EP2542246A1 (en) | 2010-03-03 | 2013-01-09 | Neocutis SA | Compositions and methods for treatment of skin diseases and disorders using antimicrobial peptide sequestering compounds |
-
2012
- 2012-06-28 MX MX2014000066A patent/MX381271B/es unknown
- 2012-06-28 CA CA2840571A patent/CA2840571C/en active Active
- 2012-06-28 CN CN201280040540.1A patent/CN103763925A/zh active Pending
- 2012-06-28 CA CA3054236A patent/CA3054236A1/en not_active Abandoned
- 2012-06-28 CN CN201710998632.5A patent/CN107823123A/zh active Pending
- 2012-06-28 EP EP12804805.5A patent/EP2725904B1/en active Active
- 2012-06-28 BR BR112013033759-1A patent/BR112013033759B1/pt active IP Right Grant
- 2012-06-28 AU AU2012275292A patent/AU2012275292B2/en active Active
- 2012-06-28 US US13/536,960 patent/US8946276B2/en active Active
- 2012-06-28 WO PCT/US2012/044738 patent/WO2013003646A1/en not_active Ceased
- 2012-06-28 JP JP2014519052A patent/JP5986632B2/ja active Active
- 2012-08-23 US US13/593,386 patent/US9198858B2/en active Active
-
2015
- 2015-10-23 US US14/921,737 patent/US10238634B2/en active Active
-
2016
- 2016-02-09 AU AU2016200825A patent/AU2016200825B2/en active Active
- 2016-08-05 JP JP2016154447A patent/JP6235087B2/ja active Active
-
2019
- 2019-01-14 US US16/247,497 patent/US10596155B2/en active Active
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