AU2007311019B2 - Diclofenac gel - Google Patents
Diclofenac gel Download PDFInfo
- Publication number
- AU2007311019B2 AU2007311019B2 AU2007311019A AU2007311019A AU2007311019B2 AU 2007311019 B2 AU2007311019 B2 AU 2007311019B2 AU 2007311019 A AU2007311019 A AU 2007311019A AU 2007311019 A AU2007311019 A AU 2007311019A AU 2007311019 B2 AU2007311019 B2 AU 2007311019B2
- Authority
- AU
- Australia
- Prior art keywords
- present
- composition
- diclofenac
- gel
- ethanol
- 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.)
- Ceased
Links
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 title claims description 61
- 229960001259 diclofenac Drugs 0.000 title claims description 55
- 239000000203 mixture Substances 0.000 claims abstract description 275
- 238000009472 formulation Methods 0.000 claims abstract description 152
- 229960001193 diclofenac sodium Drugs 0.000 claims abstract description 88
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 claims abstract description 88
- 230000004907 flux Effects 0.000 claims abstract description 82
- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 208000002193 Pain Diseases 0.000 claims abstract description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 117
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 115
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 114
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 97
- 230000000052 comparative effect Effects 0.000 claims description 73
- 239000002562 thickening agent Substances 0.000 claims description 70
- 239000012669 liquid formulation Substances 0.000 claims description 48
- 229920002125 Sokalan® Polymers 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 238000001035 drying Methods 0.000 claims description 35
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 21
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 20
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 20
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 20
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 20
- 229920002678 cellulose Polymers 0.000 claims description 19
- 239000001913 cellulose Substances 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 9
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 229960001631 carbomer Drugs 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 150000004676 glycans Chemical class 0.000 claims description 5
- 229920001983 poloxamer Polymers 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 238000011160 research Methods 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 2
- 230000000699 topical effect Effects 0.000 abstract description 17
- 239000000499 gel Substances 0.000 description 209
- 210000004027 cell Anatomy 0.000 description 58
- 239000000243 solution Substances 0.000 description 43
- 235000011187 glycerol Nutrition 0.000 description 36
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 20
- 238000010521 absorption reaction Methods 0.000 description 19
- 229940079593 drug Drugs 0.000 description 19
- 239000013543 active substance Substances 0.000 description 18
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 15
- 239000003981 vehicle Substances 0.000 description 15
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 14
- 238000009792 diffusion process Methods 0.000 description 14
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000012535 impurity Substances 0.000 description 12
- 230000035515 penetration Effects 0.000 description 12
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 12
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000000872 buffer Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- JVTIXNMXDLQEJE-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate 2-octanoyloxypropyl octanoate Chemical compound C(CCCCCCC)(=O)OCC(C)OC(CCCCCCC)=O.C(=O)(CCCCCCCCC)OCC(C)OC(=O)CCCCCCCCC JVTIXNMXDLQEJE-UHFFFAOYSA-N 0.000 description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 229940075510 carbopol 981 Drugs 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 230000036470 plasma concentration Effects 0.000 description 7
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 206010040880 Skin irritation Diseases 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 6
- 230000001684 chronic effect Effects 0.000 description 6
- 230000008030 elimination Effects 0.000 description 6
- 238000003379 elimination reaction Methods 0.000 description 6
- 230000036541 health Effects 0.000 description 6
- 230000036556 skin irritation Effects 0.000 description 6
- 231100000475 skin irritation Toxicity 0.000 description 6
- 238000012384 transportation and delivery Methods 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 239000003623 enhancer Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000003002 pH adjusting agent Substances 0.000 description 5
- 239000003961 penetration enhancing agent Substances 0.000 description 5
- 239000000902 placebo Substances 0.000 description 5
- 229940068196 placebo Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229940113048 solaraze Drugs 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 4
- 239000002738 chelating agent Substances 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- 210000003127 knee Anatomy 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 230000008591 skin barrier function Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 239000012049 topical pharmaceutical composition Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 3
- 229920000161 Locust bean gum Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 3
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229960003975 potassium Drugs 0.000 description 3
- 230000003637 steroidlike Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 208000006820 Arthralgia Diseases 0.000 description 2
- 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 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- 229940120146 EDTMP Drugs 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- 208000012659 Joint disease Diseases 0.000 description 2
- 229920003091 Methocel™ Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- -1 Poly(ethylene glycol) Polymers 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 210000001188 articular cartilage Anatomy 0.000 description 2
- 238000010241 blood sampling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000009509 drug development Methods 0.000 description 2
- 229940126534 drug product Drugs 0.000 description 2
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 210000005067 joint tissue Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000711 locust bean gum Substances 0.000 description 2
- 235000010420 locust bean gum Nutrition 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000009522 phase III clinical trial Methods 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 231100000245 skin permeability Toxicity 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 235000010384 tocopherol Nutrition 0.000 description 2
- 229960001295 tocopherol Drugs 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 239000006208 topical dosage form Substances 0.000 description 2
- 230000037317 transdermal delivery Effects 0.000 description 2
- 238000003260 vortexing Methods 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 1
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 1
- YXSJRZBKSLLIOM-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O YXSJRZBKSLLIOM-UHFFFAOYSA-N 0.000 description 1
- QJZYHAIUNVAGQP-UHFFFAOYSA-N 3-nitrobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2(C(O)=O)[N+]([O-])=O QJZYHAIUNVAGQP-UHFFFAOYSA-N 0.000 description 1
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CWSZBVAUYPTXTG-UHFFFAOYSA-N 5-[6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-5-[4-hydroxy-3-(2-hydroxyethoxy)-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OCCO)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 CWSZBVAUYPTXTG-UHFFFAOYSA-N 0.000 description 1
- LXAHHHIGZXPRKQ-UHFFFAOYSA-N 5-fluoro-2-methylpyridine Chemical compound CC1=CC=C(F)C=N1 LXAHHHIGZXPRKQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 1
- 208000007353 Hip Osteoarthritis Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000003947 Knee Osteoarthritis Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 229920000148 Polycarbophil calcium Polymers 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000219061 Rheum Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- PRFQZMITZQNIQW-SAMIYVOISA-N [(2s)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethyl] (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O PRFQZMITZQNIQW-SAMIYVOISA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000012382 advanced drug delivery Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- KQZNFGJQTPAURD-NBWQQBAWSA-N ascorbyl dipalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](OC(=O)CCCCCCCCCCCCCCC)[C@H]1OC(=O)C(O)=C1O KQZNFGJQTPAURD-NBWQQBAWSA-N 0.000 description 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 235000010376 calcium ascorbate Nutrition 0.000 description 1
- 229940047036 calcium ascorbate Drugs 0.000 description 1
- 239000011692 calcium ascorbate Substances 0.000 description 1
- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000007211 cardiovascular event Effects 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 210000000736 corneocyte Anatomy 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- YXVFQADLFFNVDS-UHFFFAOYSA-N diammonium citrate Chemical compound [NH4+].[NH4+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O YXVFQADLFFNVDS-UHFFFAOYSA-N 0.000 description 1
- KYQODXQIAJFKPH-UHFFFAOYSA-N diazanium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [NH4+].[NH4+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O KYQODXQIAJFKPH-UHFFFAOYSA-N 0.000 description 1
- KPHWPUGNDIVLNH-UHFFFAOYSA-M diclofenac sodium Chemical compound [Na+].[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl KPHWPUGNDIVLNH-UHFFFAOYSA-M 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- QLBHNVFOQLIYTH-UHFFFAOYSA-L dipotassium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [K+].[K+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O QLBHNVFOQLIYTH-UHFFFAOYSA-L 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 229940058180 edetate dipotassium anhydrous Drugs 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 238000004520 electroporation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 208000034311 hand osteoarthritis Diseases 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000004021 humic acid Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229920003111 hydroxyethyl cellulose HHX Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 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 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 1
- 229960004705 kojic acid Drugs 0.000 description 1
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010197 meta-analysis Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 231100000435 percutaneous penetration Toxicity 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920001992 poloxamer 407 Polymers 0.000 description 1
- 229940044476 poloxamer 407 Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000955 prescription drug Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 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 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000037067 skin hydration Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- 210000001258 synovial membrane Anatomy 0.000 description 1
- 238000012385 systemic delivery Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000013271 transdermal drug delivery Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- FYZXEMANQYHCFX-UHFFFAOYSA-K tripotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [K+].[K+].[K+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O FYZXEMANQYHCFX-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82975606P | 2006-10-17 | 2006-10-17 | |
| US60/829,756 | 2006-10-17 | ||
| PCT/US2007/081674 WO2008049020A2 (en) | 2006-10-17 | 2007-10-17 | Diclofenac gel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2007311019A1 AU2007311019A1 (en) | 2008-04-24 |
| AU2007311019A8 AU2007311019A8 (en) | 2009-06-18 |
| AU2007311019B2 true AU2007311019B2 (en) | 2013-05-16 |
Family
ID=39023542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007311019A Ceased AU2007311019B2 (en) | 2006-10-17 | 2007-10-17 | Diclofenac gel |
Country Status (14)
| Country | Link |
|---|---|
| US (14) | US8252838B2 (enExample) |
| EP (2) | EP2626063B1 (enExample) |
| JP (1) | JP5432716B2 (enExample) |
| CN (2) | CN101588791A (enExample) |
| AU (1) | AU2007311019B2 (enExample) |
| BR (1) | BRPI0717769A2 (enExample) |
| CA (1) | CA2666398C (enExample) |
| DK (1) | DK2086504T3 (enExample) |
| IL (1) | IL198161A (enExample) |
| MX (1) | MX2009004038A (enExample) |
| NZ (1) | NZ577020A (enExample) |
| RU (1) | RU2463038C2 (enExample) |
| WO (1) | WO2008049020A2 (enExample) |
| ZA (1) | ZA200903135B (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1966229B1 (en) | 2005-09-12 | 2015-10-21 | Abela Pharmaceuticals, Inc. | Systems for removing dimethyl sulfoxide (dmso) or related compounds, or odors associated with same |
| WO2007033082A2 (en) | 2005-09-12 | 2007-03-22 | Abela Pharmaceuticals, Inc. | Compositions comprising dimethyl sulfoxide (dmso) |
| US8480797B2 (en) | 2005-09-12 | 2013-07-09 | Abela Pharmaceuticals, Inc. | Activated carbon systems for facilitating use of dimethyl sulfoxide (DMSO) by removal of same, related compounds, or associated odors |
| WO2007033180A1 (en) | 2005-09-12 | 2007-03-22 | Abela Pharmaceuticals, Inc. | Materials for facilitating administration of dimethyl sulfoxide (dmso) and related compounds |
| BRPI0717769A2 (pt) | 2006-10-17 | 2013-11-05 | Nuvo Res | Formulação de gel, método para o tratamento da osteoartrite em um indivíduo sofrendo de dor articular, e, uso de diclofenac de sódio |
| US20100100060A1 (en) * | 2008-10-17 | 2010-04-22 | Novartis Ag | Applicator for pharmaceutical product and method of using same |
| BRPI0921494A2 (pt) | 2008-11-03 | 2018-10-30 | Prad Reasearch And Development Ltd | método de planejamento de uma operação de amostragem para uma formação subterrãnea, método de contolar uma operação de amostragem de formação subterrânea, método de controlar uma operação de perfuração para uma formação subterrãnea, e método de realizar uma amostragem durante a operação de perfuração. |
| US8546450B1 (en) | 2009-03-31 | 2013-10-01 | Nuvo Research Inc. | Treatment of pain with topical diclofenac compounds |
| US8618164B2 (en) * | 2009-03-31 | 2013-12-31 | Nuvo Research Inc. | Treatment of pain with topical diclofenac compounds |
| EP2482850A2 (en) * | 2009-09-30 | 2012-08-08 | Nuvo Research Inc. | Topical formulations |
| EP2485730A1 (en) | 2009-10-09 | 2012-08-15 | Nuvo Research Inc. | Topical formulation comprising etoricoxib and a zwitterionic surfactant |
| EP2493315B1 (en) | 2009-10-30 | 2018-03-28 | Abela Pharmaceuticals, Inc. | Dimethyl sulfoxide (dmso) or dmso and methylsulfonylmethane (msm) formulations to treat infectious diseases |
| WO2011060195A2 (en) | 2009-11-11 | 2011-05-19 | Nuvo Research Inc. | Topical eutectic formulation |
| EP2329849B1 (en) * | 2009-11-18 | 2015-04-29 | Galderma Research & Development | Combination of alpha-2 adrenergic receptor agonist and non-steroidal anti-inflammatory agent for treating or preventing an inflammatory skin disorder |
| WO2011112875A2 (en) | 2010-03-10 | 2011-09-15 | Nuvo Research Inc. | Foamable formulation |
| EP2575813A1 (en) | 2010-05-28 | 2013-04-10 | Nuvo Research Inc. | Topical etoricoxib formulation |
| RU2013157834A (ru) * | 2011-05-26 | 2015-07-10 | Новартис Аг | Композиции для подкожного введения физиологически активных средств |
| US10813897B2 (en) * | 2011-12-27 | 2020-10-27 | Cmpd Licensing, Llc | Composition and method for compounded therapy |
| CN102525886B (zh) * | 2012-01-13 | 2013-03-13 | 湖北科益药业股份有限公司 | 双氯芬酸二乙胺乳胶剂及其制备方法 |
| FR2990134B1 (fr) * | 2012-05-07 | 2014-11-21 | Anaconda Pharma | Composition pharmaceutique d'un inhibiteur du virus du papillome |
| US8853189B2 (en) * | 2012-05-31 | 2014-10-07 | Prima Innovations, Llc | Antispasmodic 1,2-Diols and 1,2,3-triols |
| ITMI20121205A1 (it) | 2012-07-11 | 2014-01-12 | Glycores 2000 Srl | Composizione con attivita' antinfiammatoria ed analgesica da somministrare per uso esterno mediante vaporizzazione |
| US20140113970A1 (en) * | 2012-10-22 | 2014-04-24 | Mallinckrodt LLC Covidien | Dispensing system |
| EP2742932A1 (en) * | 2012-12-17 | 2014-06-18 | Laboratorios Ojer Pharma S.L. | Gel compositions |
| TW201431572A (zh) | 2012-12-21 | 2014-08-16 | Teikoku Pharma Usa Inc | 荷爾蒙及其它醫藥劑之經皮傳遞的組成物及方法 |
| US9012402B1 (en) | 2014-06-11 | 2015-04-21 | James Blanchard | Gel for topical delivery of NSAIDs to provide relief of musculoskeletal pain and methods for its preparation |
| UA121985C2 (uk) * | 2015-01-23 | 2020-08-25 | Др. Редді'З Лабораторіз Лімітед | Нефарбуюча гелева композиція для місцевого застосування, яка містить німесулід |
| US10716754B2 (en) | 2016-03-28 | 2020-07-21 | Tioga Research, Inc. | Topical formulation |
| BR112018070155B1 (pt) * | 2016-03-30 | 2023-10-24 | Sarudbhava Formulations Private Limited | Composições farmacêuticas de apremilast |
| MX2018011881A (es) * | 2016-03-31 | 2018-12-17 | Smartech Topical Inc | Sistema de administracion. |
| IT201700009711A1 (it) * | 2017-01-30 | 2018-07-30 | Applied Pharma Res | Sodium free Diclofenac potassium oral solutions Soluzioni orali di Diclofenac potassico prive di sodio |
| US20200009157A1 (en) * | 2017-02-28 | 2020-01-09 | John W. Backer | Dimethyl sulfoxide (dmso) and hydrocortisone compositions and methods of use |
| US10821075B1 (en) | 2017-07-12 | 2020-11-03 | James Blanchard | Compositions for topical application of a medicaments onto a mammalian body surface |
| CN117551073A (zh) | 2018-11-20 | 2024-02-13 | 恩福莱克逊治疗有限公司 | 用于治疗皮肤疾病噻吩基苯胺化合物 |
| MA55141A (fr) | 2018-11-20 | 2021-09-29 | Nflection Therapeutics Inc | Composés cyanoaryl-aniline pour le traitement d'affections de la peau |
| WO2020106304A1 (en) * | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Topical formulations |
| JP7393808B2 (ja) | 2018-11-20 | 2023-12-07 | エヌフレクション セラピューティクス インコーポレイテッド | 皮膚障害の処置のためのナフチリジノン－アニリン化合物 |
| WO2021061913A1 (en) * | 2019-09-27 | 2021-04-01 | Encube Ethicals, Pvt. Ltd. | Diclofenac sodium topical solution |
| MX2022005168A (es) | 2019-11-06 | 2022-06-08 | Smartech Topical Inc | Formulaciones topicas de inhibidores de la ciclooxigenasa y su uso. |
| CN110687229A (zh) * | 2019-11-12 | 2020-01-14 | 山东省药学科学院 | 一种双氯芬酸钠原料及其制剂中有关物质的分析方法 |
| WO2022040773A1 (en) | 2020-08-26 | 2022-03-03 | Canadian Nano Pharmaceutical Technology Inc. | Nano-emulsion based compositions, methods for their preparation and their use in delivery of active ingredients |
| WO2022055927A1 (en) * | 2020-09-11 | 2022-03-17 | Ps Therapy Ltd. | Topical compositions and methods of use |
| CN118591373A (zh) | 2021-11-23 | 2024-09-03 | 恩福莱克逊治疗有限公司 | 吡咯并吡啶-苯胺化合物的制剂 |
| CN114259461B (zh) * | 2021-11-29 | 2023-09-12 | 海南全星制药有限公司 | 一种双氯芬酸钠凝胶及其制备方法 |
| US20250195410A1 (en) | 2022-03-25 | 2025-06-19 | Glycores 2000 Srl | Topical pharmaceutical composition with anti-inflammatory and analgesic activity and uses thereof |
| CN116869976A (zh) * | 2023-09-07 | 2023-10-13 | 晶易医药科技(成都)有限公司 | 双氯芬酸二乙胺凝胶贴膏组合物、凝胶贴膏及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543251A (en) * | 1983-12-09 | 1985-09-24 | Toko Yakuhin Industry Co., Ltd. | Gel preparations for external application |
| US4575515A (en) * | 1984-05-14 | 1986-03-11 | Clark Pharmaceutical Laboratories Ltd. | Pharmaceutical solutions comprising dimethyl sulfoxide |
| EP0450123B1 (de) * | 1990-04-05 | 1995-07-05 | Knoll AG | Diclofenac-Natrium enthaltende pharmazeutische Zusammensetzung zur topischen Anwendung |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4342784A (en) * | 1964-10-06 | 1982-08-03 | E. R. Squibb & Sons, Inc. | Chemical compositions and method of utilization |
| US3740421A (en) * | 1966-09-19 | 1973-06-19 | Basf Wyandotte Corp | Polyoxyethylene-polyoxypropylene aqueous gels |
| US3740420A (en) * | 1967-11-28 | 1973-06-19 | Crown Zellerbach Corp | Pharmaceutical compositions with dimethyl sulfoxide |
| US3711602A (en) | 1970-10-30 | 1973-01-16 | Crown Zellerbach Corp | Compositions for topical application for enhancing tissue penetration of physiologically active agents with dmso |
| GB2023000B (en) | 1978-06-17 | 1982-10-13 | Kowa Co | Antinflammatory analgesic gelled ointments |
| US4296104A (en) | 1979-08-30 | 1981-10-20 | Herschler R J | Therapeutic dimethyl sulfoxide composition and methods of use |
| US4441739A (en) * | 1981-08-27 | 1984-04-10 | Cluff Warren S | Booklet |
| US4670254A (en) | 1983-12-09 | 1987-06-02 | Toko Yakuhin Industry Co., Ltd. | Gel preparations for topical application of diclofenac sodium |
| JPS61254519A (ja) * | 1985-05-07 | 1986-11-12 | Nitto Electric Ind Co Ltd | ゲル状医薬製剤 |
| JPS61277613A (ja) * | 1985-05-31 | 1986-12-08 | Nitto Electric Ind Co Ltd | ゲル状外用医薬組成物 |
| US4707354A (en) | 1985-06-17 | 1987-11-17 | Alpen Tau, Inc. | Mature skin treatment and protectant compositions and methods of using same |
| JPH06104624B2 (ja) * | 1986-05-07 | 1994-12-21 | 太郎 小木曽 | 経皮吸収剤 |
| DE3632359A1 (de) * | 1986-09-24 | 1988-04-07 | Troponwerke Gmbh & Co Kg | Arzneimittelzubereitungen |
| US4855294A (en) * | 1988-09-06 | 1989-08-08 | Theratech, Inc. | Method for reducing skin irritation associated with drug/penetration enhancer compositions |
| US5215739A (en) | 1989-04-05 | 1993-06-01 | Toko Yakuhin Kogyo Kabushiki Kaisha | Spray gel base and spray gel preparation using thereof |
| WO1992007561A1 (en) * | 1990-10-30 | 1992-05-14 | Ss Pharmaceutical Co., Ltd. | Antiphlogistic and analgesic gel preparation |
| US5874479A (en) | 1991-03-01 | 1999-02-23 | Warner-Lambert Company | Therapeutic permeation enhanced-wound healing compositions and methods for preparing and using same |
| US5674912A (en) | 1991-03-01 | 1997-10-07 | Warner-Lambert Company | Sunscreen-wound healing compositions and methods for preparing and using same |
| EP0592569A1 (en) * | 1991-07-03 | 1994-04-20 | Sano Corporation | Composition and method for transdermal delivery of diclofenac |
| IL101387A (en) | 1992-03-26 | 1999-11-30 | Pharmos Ltd | Emulsion with enhanced topical and/or transdermal systemic effect utilizing submicron oil droplets |
| JP2523428B2 (ja) | 1992-12-04 | 1996-08-07 | エスエス製薬株式会社 | 消炎鎮痛ゲル製剤 |
| DE4313402A1 (de) | 1993-04-23 | 1994-10-27 | Hexal Pharma Gmbh | Transdermale Wirkstoffzubereitung |
| WO1997013528A1 (en) * | 1995-10-12 | 1997-04-17 | Gs Development Ab | A pharmaceutical composition for administration of an active substance to or through a skin or mucosal surface |
| AUPO379596A0 (en) | 1996-11-22 | 1996-12-19 | Soltec Research Pty Ltd | Percutaneous delivery system |
| JP3291222B2 (ja) | 1997-05-19 | 2002-06-10 | トヨタ自動車株式会社 | 軟質光輝化製品 |
| US5976566A (en) | 1997-08-29 | 1999-11-02 | Macrochem Corporation | Non-steroidal antiinflammtory drug formulations for topical application to the skin |
| US6399093B1 (en) | 1999-05-19 | 2002-06-04 | Advanced Medical Instruments | Method and composition to treat musculoskeletal disorders |
| US6962691B1 (en) | 1999-05-20 | 2005-11-08 | U & I Pharmaceuticals Ltd. | Topical spray compositions |
| KR100433614B1 (ko) | 2000-06-16 | 2004-05-31 | 주식회사 태평양 | 친수성 또는 염의 형태로 된 약물을 함유하는 경피흡수제제 |
| US6387383B1 (en) | 2000-08-03 | 2002-05-14 | Dow Pharmaceutical Sciences | Topical low-viscosity gel composition |
| KR20040033286A (ko) | 2001-05-31 | 2004-04-21 | 파마시아 코포레이션 | 선택적인 사이클로옥시게나제-2 억제제 및 1가 알콜을포함하는 피부-침투성 조성물 |
| US6858200B2 (en) | 2001-06-06 | 2005-02-22 | Schering-Plough Healthcare Healthcare Products Inc. | Sunscreen formulations |
| US6750291B2 (en) | 2002-04-12 | 2004-06-15 | Pacific Corporation | Film-forming agent for drug delivery and preparation for percutaneous administration containing the same |
| ITMI20020986A1 (it) | 2002-05-10 | 2003-11-10 | Acraf | Composizione a base di diclofenac per il trattamento topico di affezioni del cavo orofaringeo |
| PE20040321A1 (es) * | 2002-08-22 | 2004-07-15 | Novartis Consumer Health Sa | Composicion topica que comprende diclofenaco |
| US7138394B2 (en) | 2002-09-27 | 2006-11-21 | Alpharx Inc. | Vehicle for topical delivery of anti-inflammatory compounds |
| US20040175415A1 (en) | 2003-03-05 | 2004-09-09 | Chan Alvin C. | Formulations and methods of delivery of intact tocopheryl succinate to humans |
| US20040222123A1 (en) | 2003-05-06 | 2004-11-11 | Barr Laboratories, Inc. | Kit for pharmaceuticals |
| WO2005009510A2 (en) * | 2003-07-23 | 2005-02-03 | The Regents Of The University Of California | Penetration enhancer combinations for transdermal delivery |
| DE20319986U1 (de) | 2003-12-23 | 2004-04-15 | Merckle Gmbh Chemisch Pharmazeutische Fabrik | Topische Zubereitungen enthaltend Dimethylsulfoxid und Dexpanthenol |
| US8252314B2 (en) | 2004-09-24 | 2012-08-28 | Hill's Pet Nutrition, Inc. | Hypoallergenic composition |
| US20060148903A1 (en) | 2004-11-24 | 2006-07-06 | Algorx Pharmaceuticals, Inc. | Capsaicinoid gel formulation and uses thereof |
| GT200600046A (es) * | 2005-02-09 | 2006-09-25 | Terapia de combinacion | |
| JP2008531693A (ja) * | 2005-03-03 | 2008-08-14 | アイ エス ダブリュ グループ インコーポレイテッド | 局所用ゲル組成物 |
| US20070053984A1 (en) | 2005-03-03 | 2007-03-08 | Monique Spann-Wade | Topical gels compositions |
| EA200800370A1 (ru) | 2005-07-20 | 2008-06-30 | Панацея Биотек Лтд. | Новая фармацевтическая лекарственная форма ингибитора фермента циклооксигеназы с модифицированным высвобождением |
| US20080319092A1 (en) | 2005-08-05 | 2008-12-25 | Nuvo Research Inc. | Transdermal Drug Delivery Formulation |
| US20070141182A1 (en) | 2005-12-20 | 2007-06-21 | Niazi Sarfaraz K | Combination of multiple nonteroidal antiinflammatory drugs and muscle relaxants for local treatment of musculoskeletal pain |
| EP1999626A4 (en) | 2006-01-26 | 2009-11-25 | Combinatorx Inc | METHODS, COMPOSITIONS AND NEEDS FOR TREATING MUSCULOSKELETAL DISORDERS AND SYMPTOMS ASSOCIATED THEREWITH |
| US20070280972A1 (en) * | 2006-04-25 | 2007-12-06 | Zars, Inc. | Adhesive solid gel-forming formulations for dermal drug delivery |
| BRPI0717769A2 (pt) | 2006-10-17 | 2013-11-05 | Nuvo Res | Formulação de gel, método para o tratamento da osteoartrite em um indivíduo sofrendo de dor articular, e, uso de diclofenac de sódio |
| BRPI0806666A8 (pt) | 2007-01-16 | 2018-02-06 | Tyratech Inc | Composições e método para controle de praga |
| US20110275717A1 (en) | 2008-11-28 | 2011-11-10 | Advance Holdings Limited | Pharmaceutical formulation comprising diclofenac |
| US8546450B1 (en) | 2009-03-31 | 2013-10-01 | Nuvo Research Inc. | Treatment of pain with topical diclofenac compounds |
| US8618164B2 (en) | 2009-03-31 | 2013-12-31 | Nuvo Research Inc. | Treatment of pain with topical diclofenac compounds |
| US20140113970A1 (en) | 2012-10-22 | 2014-04-24 | Mallinckrodt LLC Covidien | Dispensing system |
-
2007
- 2007-10-17 BR BRPI0717769 patent/BRPI0717769A2/pt not_active Application Discontinuation
- 2007-10-17 DK DK07863421T patent/DK2086504T3/da active
- 2007-10-17 CN CNA2007800464038A patent/CN101588791A/zh active Pending
- 2007-10-17 CN CN201410667941.0A patent/CN104606126A/zh active Pending
- 2007-10-17 ZA ZA200903135A patent/ZA200903135B/xx unknown
- 2007-10-17 CA CA2666398A patent/CA2666398C/en active Active
- 2007-10-17 AU AU2007311019A patent/AU2007311019B2/en not_active Ceased
- 2007-10-17 EP EP13166999.6A patent/EP2626063B1/en active Active
- 2007-10-17 MX MX2009004038A patent/MX2009004038A/es active IP Right Grant
- 2007-10-17 EP EP20070863421 patent/EP2086504B1/en active Active
- 2007-10-17 WO PCT/US2007/081674 patent/WO2008049020A2/en not_active Ceased
- 2007-10-17 RU RU2009118392/15A patent/RU2463038C2/ru not_active IP Right Cessation
- 2007-10-17 NZ NZ577020A patent/NZ577020A/en not_active IP Right Cessation
- 2007-10-17 JP JP2009533509A patent/JP5432716B2/ja not_active Expired - Fee Related
-
2008
- 2008-06-05 US US12/134,121 patent/US8252838B2/en not_active Expired - Fee Related
-
2009
- 2009-04-16 IL IL198161A patent/IL198161A/en active IP Right Grant
-
2012
- 2012-08-01 US US13/564,688 patent/US8563613B2/en not_active Expired - Fee Related
-
2013
- 2013-09-12 US US14/025,781 patent/US8871809B2/en active Active
-
2014
- 2014-09-25 US US14/497,096 patent/US9066913B2/en not_active Expired - Fee Related
-
2015
- 2015-01-14 US US14/596,813 patent/US20150126606A1/en not_active Abandoned
- 2015-01-14 US US14/596,919 patent/US9101591B2/en not_active Expired - Fee Related
- 2015-05-06 US US14/705,636 patent/US9168305B2/en active Active
- 2015-05-06 US US14/705,649 patent/US9220784B2/en active Active
- 2015-05-06 US US14/705,593 patent/US9339551B2/en not_active Expired - Fee Related
- 2015-05-06 US US14/705,606 patent/US9168304B2/en active Active
- 2015-10-26 US US14/922,903 patent/US9339552B2/en not_active Expired - Fee Related
-
2016
- 2016-04-06 US US15/092,139 patent/US9539335B2/en not_active Expired - Fee Related
- 2016-12-05 US US15/368,781 patent/US20170266296A1/en not_active Abandoned
-
2019
- 2019-09-18 US US16/575,120 patent/US20200237919A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543251A (en) * | 1983-12-09 | 1985-09-24 | Toko Yakuhin Industry Co., Ltd. | Gel preparations for external application |
| US4575515A (en) * | 1984-05-14 | 1986-03-11 | Clark Pharmaceutical Laboratories Ltd. | Pharmaceutical solutions comprising dimethyl sulfoxide |
| EP0450123B1 (de) * | 1990-04-05 | 1995-07-05 | Knoll AG | Diclofenac-Natrium enthaltende pharmazeutische Zusammensetzung zur topischen Anwendung |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2007311019B2 (en) | Diclofenac gel | |
| US8470886B2 (en) | Topical ibuprofen formulations | |
| HK1134024B (en) | Diclofenac gel | |
| HK1188140A (en) | Diclofenac gel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TH | Corrigenda |
Free format text: IN VOL 23, NO 21, PAGE(S) 8421 UNDER THE HEADING PCT APPLICATIONS THAT HAVE ENTERED THE NATIONAL PHASE -NAME INDEX UNDER THE NAME NUVO RESEARCH INC., APPLICATION NO. 2007311019, UNDER INID (71) CORRECT THE APPLICANT NAME TO NUVO RESEARCH |
|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE APPLICANT NAME FROM NUVO RESEARCH TO NUVO RESEARCH INC. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| HB | Alteration of name in register |
Owner name: NUVO PHARMACEUTICALS INC. Free format text: FORMER NAME(S): NUVO RESEARCH INC. |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |