WO2003011340A1 - Medicament formulation for topical application in the therapy and prophylaxis of hyperhidrosis - Google Patents
Medicament formulation for topical application in the therapy and prophylaxis of hyperhidrosis Download PDFInfo
- Publication number
- WO2003011340A1 WO2003011340A1 PCT/EP2002/008101 EP0208101W WO03011340A1 WO 2003011340 A1 WO2003011340 A1 WO 2003011340A1 EP 0208101 W EP0208101 W EP 0208101W WO 03011340 A1 WO03011340 A1 WO 03011340A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hyperhidrosis
- glycopyrrolate
- salts
- derivatives
- enantiomers
- Prior art date
Links
- 208000008454 Hyperhidrosis Diseases 0.000 title claims abstract description 33
- 230000037315 hyperhidrosis Effects 0.000 title claims abstract description 32
- 238000002560 therapeutic procedure Methods 0.000 title claims abstract description 15
- 230000000699 topical effect Effects 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title claims abstract description 9
- 238000011321 prophylaxis Methods 0.000 title claims abstract description 9
- 238000009472 formulation Methods 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 title abstract description 4
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 229940015042 glycopyrrolate Drugs 0.000 claims abstract description 17
- 229960002462 glycopyrronium bromide Drugs 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 10
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 10
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 4
- 230000035515 penetration Effects 0.000 claims description 4
- 235000020752 sage extract Nutrition 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000084 colloidal system Substances 0.000 claims description 2
- 240000007164 Salvia officinalis Species 0.000 claims 1
- 241000411545 Punargentus Species 0.000 abstract description 5
- 208000004041 Gustatory Sweating Diseases 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 201000001678 Frey syndrome Diseases 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 206010059237 Auriculotemporal syndrome Diseases 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000005589 hyperhidrosis palmaris ET plantaris Diseases 0.000 description 4
- 108030001720 Bontoxilysin Proteins 0.000 description 3
- 229940053031 botulinum toxin Drugs 0.000 description 3
- 239000000812 cholinergic antagonist Substances 0.000 description 3
- 238000001543 one-way ANOVA Methods 0.000 description 3
- 238000005457 optimization Methods 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 2
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000013583 drug formulation Substances 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 229940126602 investigational medicinal product Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 238000012313 Kruskal-Wallis test Methods 0.000 description 1
- 241000014040 Melitta Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000036617 axillary hyperhidrosis Effects 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- -1 cyclopentylhydroxyphenyl-acetoxy Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000892 gravimetry Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 210000001138 tear Anatomy 0.000 description 1
- 238000011870 unpaired t-test Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
Definitions
- the invention relates to a pharmaceutical formulation for topical use for the therapy and prophylaxis of hyperhidrosis axillary, palmaris et plantaris and other forms of hyperhidrosis.
- This pharmaceutical formulation is based on the use of glycopyrrolate, its salts and / or its derivatives.
- glycopyrronium bromide with the chemical formula 3- (cyclopentylhydroxyphenyl-acetoxy) -1, 1-dimethylpyrronium bromide is a spasmolytic, anticholinergic (parasympatholytic)
- GPB has an effect.
- the mechanism of action is due to a blockade of the muscarinic receptors.
- the strong hydrophilicity of GPB prevents passage through the blood-brain barrier and thus central effects.
- the molar mass of the glycopyrronium bromide is 398.36 g / mol and the melting point of the compound is 193-198 ° C.
- GPB is a white powder.
- the stability of this compound is pH-dependent, the stability decreasing at a pH> 6.
- GPB is a slightly water-soluble compound.
- GPB has so far been used primarily as a secretion-inhibiting and spasmolytic substance in adjuvant therapy with special anesthetic or surgical procedures.
- BTX botulinum toxin
- a pharmaceutical formulation for topical use for the therapy and prophylaxis of hyperhidrosis axillary, palamaris et plantaris and / or other forms of hyperhidrosis is provided.
- This pharmaceutical formulation contains a glycopyrrolate, its salts and / or its derivatives and / or its enantiomers in an amount between 0.05 and 20% by weight.
- a gel and / or colloid-containing carrier system is used as the vehicle system.
- the application is not locally restricted here; rather, these vehicle systems enable the pharmaceutical formulation according to the invention to can be easily applied in the armpit area, for example, and even with increased sweat secretion, the penetration of the active ingredient can be ensured over a longer period of time compared to aqueous solutions.
- glycopyrrolate, its salts and / or its derivatives are preferably used in a concentration of between 0.5 and 5% by weight.
- Glycopyrronium bromide is preferably used as the salt of the glycopyrrolate.
- hydroxyethyl cellulose gel is preferably used.
- glycopyrrolate, its salts and / or its derivatives and / or its enantiomers for the manufacture of a medicament for topical use for the therapy and prophylaxis of hyperhidrosis axillaris, palmaris et plantaris and / or other forms of hyperhidrosis is also used according to the invention taught.
- the compound is used in a concentration between 0.05 to 20% by weight, preferably between 0.5 and 5% by weight.
- Three concentrations were placebo-controlled with GPB (0.5; 2.0; 4.0%) in hydroxyethyl cellulose gel (hydroxyethyl cellulose 10000 2.5 parts; glycerol 85% 10.0 parts; water (cons.) 87, 5 parts) examined for their effectiveness.
- the hyperhidrosis was objectified using quantitative hidroiuetry.
- Group 1 1 week 3 times a day + 3 weeks 1 time a day
- Group 2 2 weeks 2 times a day + 2 weeks 1 time a day
- Group 3 1 week 3 times a day + 1 week 2 times a day + 2 weeks 1 time a day
- Group 4 4 weeks 3 times a day
- the hyperhidrosis was objectified using quantitative hydrometry.
- the analysis of variance was used to analyze three and more samples (treatment groups) from normally distributed populations with the same variance. Since only one factor, the influence of the investigational medicinal product, was to be examined in the various mean value groups, the one-way analysis of variance (one-way ANOVA) was used. Here random samples with unknown common variance are examined. In addition, the differences between the individual groups will be examined using the Scheffe assessment of linear contrasts. For comparison of three or more independent groups, the Kruskal-Wallis-Test (H-Test) was offered, which tests the analog hypotheses of the one-way analysis of variance as a non-parametric test. The unpaired t-test was used to compare two samples with the same variance. Differences with an error probability of p ⁇ 0.05 were rated as statistically significant.
- H-Test Kruskal-Wallis-Test
- test preparations were stored in 75 ml glass jars with a ball attachment.
- hydroxyethyl cellulose gel as a vehicle system is only suitable for the therapy of hyperhidrosis axillaris, but not for hyperhidrosis palmaris (FIG. 2).
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2001136404 DE10136404A1 (en) | 2001-07-26 | 2001-07-26 | Topical medicament for treating or preventing hyperhidrosis, e.g. hyperhidrosis axillaris, comprises glycopyrrolate compound in gel and/or colloid-containing vehicle system |
DE10136404.0 | 2001-07-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003011340A1 true WO2003011340A1 (en) | 2003-02-13 |
Family
ID=7693160
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/008101 WO2003011340A1 (en) | 2001-07-26 | 2002-07-19 | Medicament formulation for topical application in the therapy and prophylaxis of hyperhidrosis |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE10136404A1 (en) |
WO (1) | WO2003011340A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004084905A3 (en) * | 2003-03-24 | 2005-04-28 | Univ Florida | Use of 5-ht2c receptor activity affecting compounds for treating idiopathic hyperhidrosis and associated conditions |
WO2006069998A2 (en) | 2004-12-27 | 2006-07-06 | Beiersdorf Ag | Glycopyrrolate in cosmetic preparations |
US8558008B2 (en) | 2013-02-28 | 2013-10-15 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
WO2014134510A1 (en) * | 2013-02-28 | 2014-09-04 | Dermira, Inc. | Glycopyrrolate salts |
US9006462B2 (en) | 2013-02-28 | 2015-04-14 | Dermira, Inc. | Glycopyrrolate salts |
MD4369C1 (en) * | 2011-03-04 | 2016-04-30 | Sosei R&D Ltd | Use of glycopyrrolate for treating tachycardia, unit dose, delivery device, method of treatment and prophylaxis of tachycardia |
KR20180091361A (en) | 2017-02-06 | 2018-08-16 | 주식회사 퍼슨 | UV blocking cosmetic composition having an antiperspirant function and preparing process for UV blocking agents using the same |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005029390A1 (en) * | 2005-06-23 | 2007-01-04 | Beiersdorf Ag | Drug combinations of glycopyrronium bromide and polyols |
DE102005029387B4 (en) | 2005-06-23 | 2018-12-27 | Beiersdorf Ag | Drug combinations of glycopyrronium bromide and polyglyceryl (3) -methylglucose distearate |
DE102005029388B4 (en) * | 2005-06-23 | 2018-12-27 | Beiersdorf Ag | Active ingredient combinations of glycopyrronium bromide and one or more partially neutralized esters of monoglycerides and / or diglycerides of saturated fatty acids with citric acid |
DE102005029389A1 (en) * | 2005-06-23 | 2007-01-04 | Beiersdorf Ag | Combination, useful as cosmetic deodorant and antitranspirants, comprises glycopyrronium bromide and active materials e.g. boundary surface-active substances, polyols and hydrocolloids |
DE102005029386A1 (en) * | 2005-06-23 | 2007-01-11 | Beiersdorf Ag | Combination, useful as cosmetic deodorant and antitranspirants, comprises glycopyrronium bromide and active materials e.g. boundary surface-active substances, polyols and hydrocolloids |
DE102004063726A1 (en) * | 2004-12-27 | 2006-07-06 | Beiersdorf Ag | Combination, useful as cosmetic deodorant and antitranspirants, comprises glycopyrronium bromide and active materials e.g. boundary surface-active substances, polyols and hydrocolloids |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5962505A (en) * | 1998-08-31 | 1999-10-05 | Bobrove; Arthur M. | Method for treating hot flashes in humans |
WO2000012087A1 (en) * | 1998-08-31 | 2000-03-09 | Bobrove Arthur M | Method for treating hot flashes in humans |
WO2001008681A1 (en) * | 1999-08-02 | 2001-02-08 | First Horizon Pharmaceutical Corporation | Methods of administration of glycopyrrolate compositions |
-
2001
- 2001-07-26 DE DE2001136404 patent/DE10136404A1/en not_active Ceased
-
2002
- 2002-07-19 WO PCT/EP2002/008101 patent/WO2003011340A1/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5962505A (en) * | 1998-08-31 | 1999-10-05 | Bobrove; Arthur M. | Method for treating hot flashes in humans |
WO2000012087A1 (en) * | 1998-08-31 | 2000-03-09 | Bobrove Arthur M | Method for treating hot flashes in humans |
WO2001008681A1 (en) * | 1999-08-02 | 2001-02-08 | First Horizon Pharmaceutical Corporation | Methods of administration of glycopyrrolate compositions |
Non-Patent Citations (2)
Title |
---|
MAY J S ET AL: "Frey's syndrome: treatment with topical glycopyrrolate.", HEAD & NECK. UNITED STATES 1989 JAN-FEB, vol. 11, no. 1, January 1989 (1989-01-01), pages 85 - 89, XP008009263, ISSN: 1043-3074 * |
SEUKERAN D C ET AL: "The use of topical glycopyrrolate in the treatment of hyperhidrosis.", 1998, CLINICAL AND EXPERIMENTAL DERMATOLOGY, VOL. 23, NR. 5, PAGE(S) 204-205, ISSN: 0307-6938, XP001122802 * |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004084905A3 (en) * | 2003-03-24 | 2005-04-28 | Univ Florida | Use of 5-ht2c receptor activity affecting compounds for treating idiopathic hyperhidrosis and associated conditions |
WO2006069998A2 (en) | 2004-12-27 | 2006-07-06 | Beiersdorf Ag | Glycopyrrolate in cosmetic preparations |
MD4369C1 (en) * | 2011-03-04 | 2016-04-30 | Sosei R&D Ltd | Use of glycopyrrolate for treating tachycardia, unit dose, delivery device, method of treatment and prophylaxis of tachycardia |
US8859610B2 (en) | 2013-02-28 | 2014-10-14 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
US10004717B2 (en) | 2013-02-28 | 2018-06-26 | Dermira, Inc. | Glycopyrrolate salts |
US9006462B2 (en) | 2013-02-28 | 2015-04-14 | Dermira, Inc. | Glycopyrrolate salts |
US9006461B2 (en) | 2013-02-28 | 2015-04-14 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
US9259414B2 (en) | 2013-02-28 | 2016-02-16 | Dermira, Inc. | Glycopyrrolate salts |
US8558008B2 (en) | 2013-02-28 | 2013-10-15 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
US9610278B2 (en) | 2013-02-28 | 2017-04-04 | Dermira, Inc. | Glycopyrrolate salts |
WO2014134510A1 (en) * | 2013-02-28 | 2014-09-04 | Dermira, Inc. | Glycopyrrolate salts |
US11291652B2 (en) | 2013-02-28 | 2022-04-05 | Journey Medical Corporation | Glycopyrrolate salts |
EP3473615A1 (en) * | 2013-02-28 | 2019-04-24 | Dermira, Inc. | Glycopyrrolate salts |
US10543192B2 (en) | 2013-02-28 | 2020-01-28 | Dermira, Inc. | Glycopyrrolate salts |
US10548875B2 (en) | 2013-02-28 | 2020-02-04 | Dermira, Inc. | Glycopyrrolate salts |
US11291651B2 (en) | 2013-02-28 | 2022-04-05 | Journey Medical Corporation | Glycopyrrolate salts |
KR20180091361A (en) | 2017-02-06 | 2018-08-16 | 주식회사 퍼슨 | UV blocking cosmetic composition having an antiperspirant function and preparing process for UV blocking agents using the same |
Also Published As
Publication number | Publication date |
---|---|
DE10136404A1 (en) | 2003-02-20 |
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