ZA200407711B - Process for preparing a finely self-emulsifiable pharmaceutical composition - Google Patents
Process for preparing a finely self-emulsifiable pharmaceutical composition Download PDFInfo
- Publication number
- ZA200407711B ZA200407711B ZA200407711A ZA200407711A ZA200407711B ZA 200407711 B ZA200407711 B ZA 200407711B ZA 200407711 A ZA200407711 A ZA 200407711A ZA 200407711 A ZA200407711 A ZA 200407711A ZA 200407711 B ZA200407711 B ZA 200407711B
- Authority
- ZA
- South Africa
- Prior art keywords
- acid
- pharmaceutically acceptable
- fatty acid
- drug
- pharmaceutical composition
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 88
- 229940079593 drug Drugs 0.000 claims abstract description 86
- 239000000203 mixture Substances 0.000 claims abstract description 54
- 239000002904 solvent Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 25
- 239000000194 fatty acid Substances 0.000 claims abstract description 25
- 229930195729 fatty acid Natural products 0.000 claims abstract description 25
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 23
- 150000001412 amines Chemical class 0.000 claims abstract description 21
- 230000002496 gastric effect Effects 0.000 claims abstract description 11
- 239000012530 fluid Substances 0.000 claims abstract description 9
- -1 linoleic acid triglycerides Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 230000002401 inhibitory effect Effects 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- 229960000590 celecoxib Drugs 0.000 claims description 10
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 10
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 7
- 229960000371 rofecoxib Drugs 0.000 claims description 6
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 6
- 229960002004 valdecoxib Drugs 0.000 claims description 6
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims description 5
- 229960003314 deracoxib Drugs 0.000 claims description 5
- 229960004945 etoricoxib Drugs 0.000 claims description 5
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 claims description 5
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- LLRANSBEYQZKFY-UHFFFAOYSA-N dodecanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCCCC(O)=O LLRANSBEYQZKFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 4
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims 4
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 4
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 239000005642 Oleic acid Substances 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- 125000005456 glyceride group Chemical group 0.000 claims 2
- 150000002334 glycols Chemical class 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 235000020778 linoleic acid Nutrition 0.000 claims 2
- 229960004232 linoleic acid Drugs 0.000 claims 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229960002446 octanoic acid Drugs 0.000 claims 2
- 150000002889 oleic acids Chemical class 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- WJTCHBVEUFDSIK-NWDGAFQWSA-N (2r,5s)-1-benzyl-2,5-dimethylpiperazine Chemical compound C[C@@H]1CN[C@@H](C)CN1CC1=CC=CC=C1 WJTCHBVEUFDSIK-NWDGAFQWSA-N 0.000 claims 1
- ZFKBWSREWJOSSJ-VIFPVBQESA-N (2s)-6,8-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(Cl)=C2O[C@H](C(F)(F)F)C(C(=O)O)=CC2=C1 ZFKBWSREWJOSSJ-VIFPVBQESA-N 0.000 claims 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 claims 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims 1
- XNTLXAUHLBBEKP-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 XNTLXAUHLBBEKP-UHFFFAOYSA-N 0.000 claims 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical group CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 claims 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical group O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical group O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000004359 castor oil Substances 0.000 claims 1
- 235000019438 castor oil Nutrition 0.000 claims 1
- 229960002887 deanol Drugs 0.000 claims 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims 1
- 229940090949 docosahexaenoic acid Drugs 0.000 claims 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims 1
- 229940093471 ethyl oleate Drugs 0.000 claims 1
- 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 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims 1
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- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
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- 239000003549 soybean oil Substances 0.000 claims 1
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- 239000008117 stearic acid Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims 1
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- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37120002P | 2002-04-09 | 2002-04-09 |
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| ZA200407711B true ZA200407711B (en) | 2006-06-28 |
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| ZA200407711A ZA200407711B (en) | 2002-04-09 | 2004-09-23 | Process for preparing a finely self-emulsifiable pharmaceutical composition |
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| EP (1) | EP1492527B1 (pl) |
| JP (1) | JP2005529104A (pl) |
| KR (1) | KR100779285B1 (pl) |
| CN (1) | CN1305470C (pl) |
| AT (1) | ATE410162T1 (pl) |
| AU (1) | AU2003223485B2 (pl) |
| BR (1) | BR0309138A (pl) |
| CA (1) | CA2481677A1 (pl) |
| DE (1) | DE60323953D1 (pl) |
| ES (1) | ES2310653T3 (pl) |
| HK (1) | HK1076382A1 (pl) |
| IL (1) | IL164163A0 (pl) |
| MX (1) | MXPA04009880A (pl) |
| PL (1) | PL372807A1 (pl) |
| RS (1) | RS87004A (pl) |
| RU (1) | RU2299061C2 (pl) |
| WO (1) | WO2003086392A2 (pl) |
| ZA (1) | ZA200407711B (pl) |
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| HRP20211377T1 (hr) | 2011-11-23 | 2022-01-07 | Therapeuticsmd, Inc. | Prirodne kombinirane hormonske supstitucijske formulacije i terapije |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US20150196640A1 (en) | 2012-06-18 | 2015-07-16 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable pk profile |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
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| US10568891B2 (en) | 2012-12-21 | 2020-02-25 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
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| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| CN103965113A (zh) * | 2014-05-06 | 2014-08-06 | 四川大学 | 1-羟乙基-2-取代苯氧甲基苯并咪唑类化合物及其制备方法 |
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| CN117547528A (zh) | 2015-05-28 | 2024-02-13 | 瑞迪博士实验室有限公司 | 用于治疗疼痛的塞来昔布口服组合物 |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| CN105343002B (zh) * | 2015-11-27 | 2019-07-26 | 济南康和医药科技有限公司 | 一种依托考昔口服微乳制剂及其制备方法 |
| WO2017173044A1 (en) | 2016-04-01 | 2017-10-05 | Therapeuticsmd Inc. | Steroid hormone compositions in medium chain oils |
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| CN111729125B (zh) * | 2020-07-31 | 2022-10-04 | 陕西佰傲再生医学有限公司 | 骨止血材料 |
| CN114681470A (zh) * | 2020-12-28 | 2022-07-01 | 雷迪博士实验室有限公司 | 治疗疼痛的方法 |
| CN113750043A (zh) * | 2021-09-18 | 2021-12-07 | 山东省药学科学院 | 一种塞来昔布自乳化口服液及其制备方法 |
| KR102635930B1 (ko) | 2021-10-29 | 2024-02-14 | 단국대학교 천안캠퍼스 산학협력단 | 자가나노유화 약물전달시스템을 이용한 셀레콕시브 함유 경구 투여용 제제 및 이의 제조방법 |
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| FR2385389A1 (fr) * | 1977-03-29 | 1978-10-27 | Capsugel Ag | Capsule emboitee remplie d'une matiere visqueuse telle que, notamment, une preparation pharmaceutique liquide |
| JP2564889B2 (ja) * | 1988-03-07 | 1996-12-18 | 松下電工株式会社 | 軸流フアン |
| US5264223A (en) * | 1990-03-29 | 1993-11-23 | Japan Elanco Company, Ltd. | Hard capsule for pharmaceutical drugs and method for producing the same |
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| US5466823A (en) * | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| US5756123A (en) * | 1994-12-01 | 1998-05-26 | Japan Elanco Co., Ltd. | Capsule shell |
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| US5993858A (en) * | 1996-06-14 | 1999-11-30 | Port Systems L.L.C. | Method and formulation for increasing the bioavailability of poorly water-soluble drugs |
| US5861419A (en) * | 1996-07-18 | 1999-01-19 | Merck Frosst Canad, Inc. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
| US6034256A (en) * | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
| CN1227003C (zh) * | 1998-09-09 | 2005-11-16 | 阿尔萨公司 | 包括液体制剂的剂型 |
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| US20030105141A1 (en) * | 2001-04-17 | 2003-06-05 | Ping Gao | Finely self-emulsifiable pharmaceutical composition |
-
2003
- 2003-03-10 IL IL16416303A patent/IL164163A0/xx unknown
- 2003-04-07 ES ES03719615T patent/ES2310653T3/es not_active Expired - Lifetime
- 2003-04-07 US US10/408,934 patent/US20030235596A1/en not_active Abandoned
- 2003-04-07 RS YU87004A patent/RS87004A/sr unknown
- 2003-04-07 AU AU2003223485A patent/AU2003223485B2/en not_active Ceased
- 2003-04-07 PL PL03372807A patent/PL372807A1/pl not_active Application Discontinuation
- 2003-04-07 BR BR0309138-4A patent/BR0309138A/pt not_active IP Right Cessation
- 2003-04-07 JP JP2003583411A patent/JP2005529104A/ja active Pending
- 2003-04-07 CA CA002481677A patent/CA2481677A1/en not_active Abandoned
- 2003-04-07 CN CNB038133490A patent/CN1305470C/zh not_active Expired - Fee Related
- 2003-04-07 WO PCT/US2003/010526 patent/WO2003086392A2/en active IP Right Grant
- 2003-04-07 DE DE60323953T patent/DE60323953D1/de not_active Expired - Fee Related
- 2003-04-07 KR KR1020047016087A patent/KR100779285B1/ko not_active IP Right Cessation
- 2003-04-07 AT AT03719615T patent/ATE410162T1/de not_active IP Right Cessation
- 2003-04-07 EP EP03719615A patent/EP1492527B1/en not_active Expired - Lifetime
- 2003-04-07 MX MXPA04009880A patent/MXPA04009880A/es not_active Application Discontinuation
- 2003-04-07 RU RU2004130291/15A patent/RU2299061C2/ru not_active IP Right Cessation
-
2004
- 2004-09-23 ZA ZA200407711A patent/ZA200407711B/en unknown
-
2005
- 2005-09-23 HK HK05108386A patent/HK1076382A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2310653T3 (es) | 2009-01-16 |
| WO2003086392A2 (en) | 2003-10-23 |
| DE60323953D1 (de) | 2008-11-20 |
| ATE410162T1 (de) | 2008-10-15 |
| RU2299061C2 (ru) | 2007-05-20 |
| HK1076382A1 (en) | 2006-01-20 |
| KR20070014237A (ko) | 2007-02-01 |
| BR0309138A (pt) | 2005-02-01 |
| IL164163A0 (en) | 2005-12-18 |
| RU2004130291A (ru) | 2005-05-27 |
| EP1492527A2 (en) | 2005-01-05 |
| AU2003223485A1 (en) | 2003-10-27 |
| WO2003086392A3 (en) | 2004-03-25 |
| RS87004A (en) | 2006-12-15 |
| CN1658870A (zh) | 2005-08-24 |
| EP1492527B1 (en) | 2008-10-08 |
| JP2005529104A (ja) | 2005-09-29 |
| MXPA04009880A (es) | 2004-12-07 |
| CA2481677A1 (en) | 2003-10-23 |
| KR100779285B1 (ko) | 2007-11-28 |
| CN1305470C (zh) | 2007-03-21 |
| US20030235596A1 (en) | 2003-12-25 |
| PL372807A1 (pl) | 2005-08-08 |
| AU2003223485B2 (en) | 2007-05-31 |
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