ZA200510388B - Foamable pharmaceutical compositions and methods for treating a disorder - Google Patents
Foamable pharmaceutical compositions and methods for treating a disorder Download PDFInfo
- Publication number
- ZA200510388B ZA200510388B ZA200510388A ZA200510388A ZA200510388B ZA 200510388 B ZA200510388 B ZA 200510388B ZA 200510388 A ZA200510388 A ZA 200510388A ZA 200510388 A ZA200510388 A ZA 200510388A ZA 200510388 B ZA200510388 B ZA 200510388B
- Authority
- ZA
- South Africa
- Prior art keywords
- acid
- composition
- surfactant
- pharmaceutically acceptable
- pharmaceutical composition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 119
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 25
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 208000035475 disorder Diseases 0.000 claims abstract description 16
- 229940121375 antifungal agent Drugs 0.000 claims abstract 4
- 239000003429 antifungal agent Substances 0.000 claims abstract 4
- 239000003246 corticosteroid Substances 0.000 claims abstract 2
- 239000004094 surface-active agent Substances 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 61
- -1 polysiloxanes Polymers 0.000 claims description 58
- 229920006395 saturated elastomer Polymers 0.000 claims description 46
- 239000012453 solvate Substances 0.000 claims description 46
- 150000002148 esters Chemical class 0.000 claims description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 31
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 31
- 229930195729 fatty acid Natural products 0.000 claims description 31
- 239000000194 fatty acid Substances 0.000 claims description 31
- 239000006260 foam Substances 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 26
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 24
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 24
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims description 24
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 24
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 24
- 150000004665 fatty acids Chemical class 0.000 claims description 23
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 239000003380 propellant Substances 0.000 claims description 21
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 20
- 229920001296 polysiloxane Polymers 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229940124597 therapeutic agent Drugs 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 15
- 125000006413 ring segment Chemical group 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 12
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- 239000001530 fumaric acid Substances 0.000 claims description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 12
- 239000011976 maleic acid Substances 0.000 claims description 12
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 12
- AZJXQVRPBZSNFN-UHFFFAOYSA-N octane-3,3-diol Chemical compound CCCCCC(O)(O)CC AZJXQVRPBZSNFN-UHFFFAOYSA-N 0.000 claims description 12
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 12
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 12
- 229940081974 saccharin Drugs 0.000 claims description 12
- 235000019204 saccharin Nutrition 0.000 claims description 12
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 12
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000004334 sorbic acid Substances 0.000 claims description 12
- 235000010199 sorbic acid Nutrition 0.000 claims description 12
- 229940075582 sorbic acid Drugs 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 12
- 235000010323 ascorbic acid Nutrition 0.000 claims description 11
- 239000011668 ascorbic acid Substances 0.000 claims description 11
- 229960005070 ascorbic acid Drugs 0.000 claims description 11
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims description 11
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 11
- 229960002703 undecylenic acid Drugs 0.000 claims description 11
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 10
- 239000004327 boric acid Substances 0.000 claims description 10
- 235000010338 boric acid Nutrition 0.000 claims description 10
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 10
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 9
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 8
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 8
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 229940061720 alpha hydroxy acid Drugs 0.000 claims description 8
- 150000001280 alpha hydroxy acids Chemical class 0.000 claims description 8
- 150000004716 alpha keto acids Chemical class 0.000 claims description 8
- 239000002280 amphoteric surfactant Substances 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 150000002195 fatty ethers Chemical class 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002596 lactones Chemical class 0.000 claims description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- 239000003209 petroleum derivative Substances 0.000 claims description 8
- 229960004838 phosphoric acid Drugs 0.000 claims description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 7
- 150000002194 fatty esters Chemical class 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 229940116315 oxalic acid Drugs 0.000 claims description 7
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- 230000000699 topical effect Effects 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 5
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 5
- 210000002919 epithelial cell Anatomy 0.000 claims description 5
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 claims description 5
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- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 4
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 4
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 4
- FZGBADVTTLOFPU-UHFFFAOYSA-N 2-(2-dodecanoyloxyethoxy)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCCOC(=O)CCCCCCCCCCC FZGBADVTTLOFPU-UHFFFAOYSA-N 0.000 claims description 4
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 claims description 4
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 4
- 229920002884 Laureth 4 Polymers 0.000 claims description 4
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- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 4
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001413 amino acids Chemical class 0.000 claims description 2
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- 201000004624 Dermatitis Diseases 0.000 claims 6
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2003
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-
2004
- 2004-05-27 JP JP2006533458A patent/JP4871728B2/ja not_active Expired - Fee Related
- 2004-05-27 EP EP04753550A patent/EP1633368B1/en not_active Revoked
- 2004-05-27 KR KR1020057022487A patent/KR101141220B1/ko not_active IP Right Cessation
- 2004-05-27 CN CNA2004800144040A patent/CN1794998A/zh active Pending
- 2004-05-27 CA CA2527499A patent/CA2527499C/en not_active Expired - Fee Related
- 2004-05-27 ES ES04753550T patent/ES2377064T3/es active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1633368B1 (en) | 2011-11-16 |
| WO2004105702A2 (en) | 2004-12-09 |
| MXPA05012842A (es) | 2006-05-17 |
| ATE533493T1 (de) | 2011-12-15 |
| JP2007500235A (ja) | 2007-01-11 |
| PL1633368T3 (pl) | 2012-04-30 |
| JP4871728B2 (ja) | 2012-02-08 |
| IL172082A0 (en) | 2009-02-11 |
| CA2527499A1 (en) | 2004-12-09 |
| AU2004242963A1 (en) | 2004-12-09 |
| US7186416B2 (en) | 2007-03-06 |
| CA2527499C (en) | 2012-01-24 |
| US7829107B2 (en) | 2010-11-09 |
| KR101141220B1 (ko) | 2012-05-07 |
| US20070059253A1 (en) | 2007-03-15 |
| EP1633368A2 (en) | 2006-03-15 |
| ES2377064T3 (es) | 2012-03-22 |
| BRPI0410721A (pt) | 2006-06-20 |
| EP1633368A4 (en) | 2007-03-14 |
| CN1794998A (zh) | 2006-06-28 |
| AU2004242963B2 (en) | 2009-05-28 |
| US20040241099A1 (en) | 2004-12-02 |
| WO2004105702A3 (en) | 2005-05-06 |
| KR20060023972A (ko) | 2006-03-15 |
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