ZA200602046B - Transdermal pharmaceutical formulation for minimizing skin residues - Google Patents

Transdermal pharmaceutical formulation for minimizing skin residues Download PDF

Info

Publication number: ZA200602046B
Authority: ZA; South Africa
Prior art keywords: glycol; present; ether; drugs; diethylene glycol
Prior art date: 2003-10-10

Application number

ZA200602046A

Other languages

English (en)

Inventor

Dario Norbeto R Carrara

Grenier Arnaud

Bess Celine

Original Assignee

Antares Pharma Ipl Ag

Priority date (The priority date 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 date listed.)

2003-10-10

Filing date

2006-03-10

Publication date

2007-06-27

2006-03-10 Application filed by Antares Pharma Ipl Ag filed Critical Antares Pharma Ipl Ag

2007-06-27 Publication of ZA200602046B publication Critical patent/ZA200602046B/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 180
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 167
238000009472 formulation Methods 0.000 claims abstract description 149
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 132
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 131
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims abstract description 93
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 65
238000000034 method Methods 0.000 claims abstract description 54
239000013543 active substance Substances 0.000 claims abstract description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
239000002904 solvent Substances 0.000 claims abstract description 44
229960003604 testosterone Drugs 0.000 claims abstract description 44
238000002425 crystallisation Methods 0.000 claims abstract description 36
230000008025 crystallization Effects 0.000 claims abstract description 35
150000001346 alkyl aryl ethers Chemical class 0.000 claims abstract description 19
230000002401 inhibitory effect Effects 0.000 claims abstract description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 144
239000003814 drug Substances 0.000 claims description 125
229940079593 drug Drugs 0.000 claims description 120
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 103
-1 proparol Chemical compound 0.000 claims description 93
229960002428 fentanyl Drugs 0.000 claims description 28
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 27
229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 18
239000003961 penetration enhancing agent Substances 0.000 claims description 17
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 15
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 14
238000010521 absorption reaction Methods 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 12
210000004877 mucosa Anatomy 0.000 claims description 12
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 11
238000012546 transfer Methods 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
239000000939 antiparkinson agent Substances 0.000 claims description 9
239000003623 enhancer Substances 0.000 claims description 9
229960005309 estradiol Drugs 0.000 claims description 9
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239000003112 inhibitor Substances 0.000 claims description 7
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239000000872 buffer Substances 0.000 claims description 6
230000002500 effect on skin Effects 0.000 claims description 6
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239000003349 gelling agent Substances 0.000 claims description 6
239000000583 progesterone congener Substances 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 5
229940124326 anaesthetic agent Drugs 0.000 claims description 5
230000003444 anaesthetic effect Effects 0.000 claims description 5
230000007423 decrease Effects 0.000 claims description 5
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239000000014 opioid analgesic Substances 0.000 claims description 5
239000004909 Moisturizer Substances 0.000 claims description 4
230000001088 anti-asthma Effects 0.000 claims description 4
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239000002934 diuretic Substances 0.000 claims description 4
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239000003906 humectant Substances 0.000 claims description 4
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208000017520 skin disease Diseases 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
BDNMABJZSXTKAQ-VCPDFFEISA-N 3-(diethylamino)propyl (1r,4s)-3-phenylbicyclo[2.2.1]heptane-3-carboxylate Chemical compound CCN(CC)CCCOC(=O)C1([C@H]2CC[C@H](C2)C1)C1=CC=CC=C1 BDNMABJZSXTKAQ-VCPDFFEISA-N 0.000 claims description 3
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WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims description 3
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XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 3
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230000001833 anti-estrogenic effect Effects 0.000 claims description 3
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GIJXKZJWITVLHI-PMOLBWCYSA-N benzatropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(C=1C=CC=CC=1)C1=CC=CC=C1 GIJXKZJWITVLHI-PMOLBWCYSA-N 0.000 claims description 3
229960001081 benzatropine Drugs 0.000 claims description 3
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DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 claims description 3
229960005091 chloramphenicol Drugs 0.000 claims description 3
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
239000000328 estrogen antagonist Substances 0.000 claims description 3
229960004675 fusidic acid Drugs 0.000 claims description 3
IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical compound O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 claims description 3
210000001156 gastric mucosa Anatomy 0.000 claims description 3
239000004083 gastrointestinal agent Substances 0.000 claims description 3
229960004502 levodopa Drugs 0.000 claims description 3
239000003120 macrolide antibiotic agent Substances 0.000 claims description 3
MJFJKKXQDNNUJF-UHFFFAOYSA-N metixene Chemical compound C1N(C)CCCC1CC1C2=CC=CC=C2SC2=CC=CC=C21 MJFJKKXQDNNUJF-UHFFFAOYSA-N 0.000 claims description 3
229960005103 metixene Drugs 0.000 claims description 3
239000003158 myorelaxant agent Substances 0.000 claims description 3
QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 claims description 3
229960003941 orphenadrine Drugs 0.000 claims description 3
150000002960 penicillins Chemical class 0.000 claims description 3
229920001184 polypeptide Polymers 0.000 claims description 3
108090000765 processed proteins & peptides Proteins 0.000 claims description 3
102000004196 processed proteins & peptides Human genes 0.000 claims description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
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150000007660 quinolones Chemical class 0.000 claims description 3
229960004136 rivastigmine Drugs 0.000 claims description 3
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
229960001608 teicoplanin Drugs 0.000 claims description 3
229940124597 therapeutic agent Drugs 0.000 claims description 3
OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 claims description 3
229960003053 thiamphenicol Drugs 0.000 claims description 3
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230000002537 thrombolytic effect Effects 0.000 claims description 3
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims description 2
WYDUSKDSKCASEF-LJQANCHMSA-N (1s)-1-cyclohexyl-1-phenyl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound C([C@](O)(C1CCCCC1)C=1C=CC=CC=1)CN1CCCC1 WYDUSKDSKCASEF-LJQANCHMSA-N 0.000 claims description 2
BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 claims description 2
GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 claims description 2
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DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 2
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims description 2
HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 claims description 2
206010021024 Hypolipidaemia Diseases 0.000 claims description 2
WYZDXEKUWRCKOB-YDSAWKJFSA-N Mestanolone Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 WYZDXEKUWRCKOB-YDSAWKJFSA-N 0.000 claims description 2
GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 claims description 2
108010059993 Vancomycin Proteins 0.000 claims description 2
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150000001780 cephalosporins Chemical class 0.000 claims description 2
239000003954 decarboxylase inhibitor Substances 0.000 claims description 2
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 claims description 2
230000001076 estrogenic effect Effects 0.000 claims description 2
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229960001751 fluoxymesterone Drugs 0.000 claims description 2
YLRFCQOZQXIBAB-RBZZARIASA-N fluoxymesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)C[C@@H]2O YLRFCQOZQXIBAB-RBZZARIASA-N 0.000 claims description 2
229940041033 macrolides Drugs 0.000 claims description 2
BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims description 2
229960004640 memantine Drugs 0.000 claims description 2
229950008604 mestanolone Drugs 0.000 claims description 2
229960001390 mestranol Drugs 0.000 claims description 2
IMSSROKUHAOUJS-MJCUULBUSA-N mestranol Chemical compound C1C[C@]2(C)[C@@](C#C)(O)CC[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 IMSSROKUHAOUJS-MJCUULBUSA-N 0.000 claims description 2
OOVXZFCPCSVSEM-NADOGSGZSA-N mytatrienediol Chemical compound C1C[C@]2(C)[C@@H](O)[C@@](C)(O)C[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 OOVXZFCPCSVSEM-NADOGSGZSA-N 0.000 claims description 2
ICMWWNHDUZJFDW-DHODBPELSA-N oxymetholone Chemical compound C([C@@H]1CC2)C(=O)\C(=C/O)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 ICMWWNHDUZJFDW-DHODBPELSA-N 0.000 claims description 2
229960005244 oxymetholone Drugs 0.000 claims description 2
ICMWWNHDUZJFDW-UHFFFAOYSA-N oxymetholone Natural products C1CC2CC(=O)C(=CO)CC2(C)C2C1C1CCC(C)(O)C1(C)CC2 ICMWWNHDUZJFDW-UHFFFAOYSA-N 0.000 claims description 2
230000035699 permeability Effects 0.000 claims description 2
229920000136 polysorbate Polymers 0.000 claims description 2
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229960001424 quinestrol Drugs 0.000 claims description 2
PWZUUYSISTUNDW-VAFBSOEGSA-N quinestrol Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@]4(O)C#C)C)CC2=CC=3OC1CCCC1 PWZUUYSISTUNDW-VAFBSOEGSA-N 0.000 claims description 2
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ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 2
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MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
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AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Inorganic Chemistry (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Nutrition Science (AREA)
Dermatology (AREA)
Physiology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

ZA200602046A 2003-10-10 2006-03-10 Transdermal pharmaceutical formulation for minimizing skin residues ZA200602046B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US51061303P	2003-10-10	2003-10-10

Publications (1)

Publication Number	Publication Date
ZA200602046B true ZA200602046B (en)	2007-06-27

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ID=34520020

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200602046A ZA200602046B (en)	2003-10-10	2006-03-10	Transdermal pharmaceutical formulation for minimizing skin residues

Country Status (15)

Country	Link
US (3)	US7335379B2 (ja)
EP (1)	EP1670433B1 (ja)
JP (1)	JP5619337B2 (ja)
AT (1)	ATE534373T1 (ja)
AU (1)	AU2004283431B2 (ja)
BR (1)	BRPI0414551B8 (ja)
CA (1)	CA2538856C (ja)
DK (1)	DK1670433T3 (ja)
ES (1)	ES2377932T3 (ja)
MX (2)	MXPA06003316A (ja)
NZ (1)	NZ546106A (ja)
PL (1)	PL1670433T3 (ja)
PT (1)	PT1670433E (ja)
WO (1)	WO2005039531A1 (ja)
ZA (1)	ZA200602046B (ja)

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2004
- 2004-10-06 ES ES04790156T patent/ES2377932T3/es not_active Expired - Lifetime
- 2004-10-06 WO PCT/EP2004/011175 patent/WO2005039531A1/en active Application Filing
- 2004-10-06 CA CA2538856A patent/CA2538856C/en not_active Expired - Lifetime
- 2004-10-06 NZ NZ546106A patent/NZ546106A/en not_active IP Right Cessation
- 2004-10-06 AT AT04790156T patent/ATE534373T1/de active
- 2004-10-06 JP JP2006530107A patent/JP5619337B2/ja not_active Expired - Fee Related
- 2004-10-06 BR BRPI0414551A patent/BRPI0414551B8/pt not_active IP Right Cessation
- 2004-10-06 DK DK04790156.6T patent/DK1670433T3/da active
- 2004-10-06 PL PL04790156T patent/PL1670433T3/pl unknown
- 2004-10-06 EP EP04790156A patent/EP1670433B1/en not_active Expired - Lifetime
- 2004-10-06 AU AU2004283431A patent/AU2004283431B2/en not_active Expired
- 2004-10-06 PT PT04790156T patent/PT1670433E/pt unknown
- 2004-10-06 MX MXPA06003316A patent/MXPA06003316A/es active IP Right Grant
2006
- 2006-03-07 US US11/371,042 patent/US7335379B2/en not_active Expired - Lifetime
- 2006-03-10 ZA ZA200602046A patent/ZA200602046B/en unknown
- 2006-03-24 MX MX2011005686A patent/MX343811B/es unknown
2008
- 2008-11-10 US US12/268,301 patent/US20090069364A1/en not_active Abandoned
2011
- 2011-05-12 US US13/106,530 patent/US8980309B2/en active Active

Also Published As

Publication number	Publication date
AU2004283431B2 (en)	2009-09-10
DK1670433T3 (da)	2012-03-12
MX343811B (es)	2016-11-24
US20060153905A1 (en)	2006-07-13
ATE534373T1 (de)	2011-12-15
MXPA06003316A (es)	2006-06-08
US20090069364A1 (en)	2009-03-12
BRPI0414551A8 (pt)	2017-04-11
JP5619337B2 (ja)	2014-11-05
BRPI0414551A (pt)	2006-10-31
WO2005039531A1 (en)	2005-05-06
US7335379B2 (en)	2008-02-26
EP1670433B1 (en)	2011-11-23
PT1670433E (pt)	2012-02-08
US20110257141A1 (en)	2011-10-20
EP1670433A1 (en)	2006-06-21
CA2538856C (en)	2010-06-29
CA2538856A1 (en)	2005-05-06
US8980309B2 (en)	2015-03-17
NZ546106A (en)	2008-10-31
ES2377932T3 (es)	2012-04-03
BRPI0414551B8 (pt)	2021-05-25
AU2004283431A1 (en)	2005-05-06
PL1670433T3 (pl)	2013-03-29
BRPI0414551B1 (pt)	2020-08-18
JP2007508261A (ja)	2007-04-05

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