DK173844B1 - Topiske metronidazol-præparater - Google Patents
Topiske metronidazol-præparater Download PDFInfo
- Publication number
- DK173844B1 DK173844B1 DK198806454A DK645488A DK173844B1 DK 173844 B1 DK173844 B1 DK 173844B1 DK 198806454 A DK198806454 A DK 198806454A DK 645488 A DK645488 A DK 645488A DK 173844 B1 DK173844 B1 DK 173844B1
- Authority
- DK
- Denmark
- Prior art keywords
- approx
- weight
- drug
- metronidazole
- composition according
- Prior art date
Links
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 229960000282 metronidazole Drugs 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims description 29
- 230000000699 topical effect Effects 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims abstract description 61
- 239000004615 ingredient Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 8
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 8
- 230000035515 penetration Effects 0.000 claims description 8
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 5
- 239000003755 preservative agent Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 4
- 229960002216 methylparaben Drugs 0.000 claims description 4
- 230000001737 promoting effect Effects 0.000 claims description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 4
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 4
- 229960003415 propylparaben Drugs 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 230000002335 preservative effect Effects 0.000 claims description 3
- 230000000622 irritating effect Effects 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 239000003961 penetration enhancing agent Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 abstract description 61
- 239000003814 drug Substances 0.000 abstract description 61
- 239000000499 gel Substances 0.000 abstract description 24
- 201000004700 rosacea Diseases 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 14
- 241001303601 Rosacea Species 0.000 abstract description 11
- 201000004624 Dermatitis Diseases 0.000 abstract description 8
- 238000009472 formulation Methods 0.000 abstract 3
- 239000012049 topical pharmaceutical composition Substances 0.000 abstract 2
- 239000002085 irritant Substances 0.000 abstract 1
- 231100000021 irritant Toxicity 0.000 abstract 1
- 239000000902 placebo Substances 0.000 description 35
- 229940068196 placebo Drugs 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000013543 active substance Substances 0.000 description 14
- 230000001225 therapeutic effect Effects 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 208000017520 skin disease Diseases 0.000 description 7
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000002757 inflammatory effect Effects 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 206010015150 Erythema Diseases 0.000 description 4
- 208000003251 Pruritus Diseases 0.000 description 4
- 231100000321 erythema Toxicity 0.000 description 4
- 230000007803 itching Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 206010033733 Papule Diseases 0.000 description 3
- 208000009675 Perioral Dermatitis Diseases 0.000 description 3
- 206010037888 Rash pustular Diseases 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 206010000496 acne Diseases 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 208000029561 pustule Diseases 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 206010011985 Decubitus ulcer Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- XWBADQOPXPRKBX-FMIVXFBMSA-N 1-n,1-n-diethyl-4-n-[6-methoxy-2-[(e)-2-(4-nitrophenyl)ethenyl]quinolin-4-yl]pentane-1,4-diamine Chemical compound N=1C2=CC=C(OC)C=C2C(NC(C)CCCN(CC)CC)=CC=1\C=C\C1=CC=C([N+]([O-])=O)C=C1 XWBADQOPXPRKBX-FMIVXFBMSA-N 0.000 description 1
- 206010000501 Acne conglobata Diseases 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010006784 Burning sensation Diseases 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 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 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- 208000004210 Pressure Ulcer Diseases 0.000 description 1
- 208000003493 Rhinophyma Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 206010043189 Telangiectasia Diseases 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003716 antitrichomonal agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 229940007078 entamoeba histolytica Drugs 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 210000000887 face Anatomy 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000036074 healthy skin Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000005808 skin problem Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 208000009056 telangiectasis Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
-
- 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
- A61K47/30—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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Birds (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Lubrication Of Internal Combustion Engines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8700584 | 1987-03-20 | ||
| PCT/US1987/000584 WO1988006888A1 (fr) | 1987-03-20 | 1987-03-20 | Nouvelles formations topiques a base de metronidazole et leurs utilisations therapeutiques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK645488D0 DK645488D0 (da) | 1988-11-18 |
| DK645488A DK645488A (da) | 1989-01-19 |
| DK173844B1 true DK173844B1 (da) | 2001-12-10 |
Family
ID=22202320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198806454A DK173844B1 (da) | 1987-03-20 | 1988-11-18 | Topiske metronidazol-præparater |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0305380B1 (fr) |
| JP (1) | JPH0825878B2 (fr) |
| KR (1) | KR950003919B1 (fr) |
| AT (1) | ATE67667T1 (fr) |
| AU (1) | AU610495B2 (fr) |
| DE (1) | DE3773383D1 (fr) |
| DK (1) | DK173844B1 (fr) |
| FI (1) | FI88582C (fr) |
| NO (1) | NO175883C (fr) |
| WO (1) | WO1988006888A1 (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837378A (en) * | 1986-01-15 | 1989-06-06 | Curatek Pharmaceuticals, Inc. | Topical metronidazole formulations and therapeutic uses thereof |
| US4859694A (en) * | 1988-02-10 | 1989-08-22 | Pavlich Frederick M | Method for treating hoof thrush and hoof rot |
| GB8910076D0 (en) † | 1989-05-03 | 1989-06-21 | Thackray C F Ltd | Sterilisable lubricant |
| SE506509C2 (sv) * | 1992-04-14 | 1997-12-22 | Bioglan Ab | Användning av imidazoler för framställning av en farmaceutisk formulering för behandling av inflammatoriska och/eller infektiösa hudsjukdomar |
| FR2722098B1 (fr) * | 1994-07-06 | 1996-08-23 | Cird Galderma | Nouveaux medicaments a base de metro-nidazole ou d'un melange synergetique de metronidazole et de clindamycine |
| GB9415290D0 (en) | 1994-07-28 | 1994-09-21 | Zeneca Ltd | Gel formation |
| US5972993A (en) * | 1998-03-20 | 1999-10-26 | Avon Products, Inc. | Composition and method for treating rosacea and sensitive skin with free radical scavengers |
| US6468989B1 (en) * | 2000-07-13 | 2002-10-22 | Dow Pharmaceutical Sciences | Gel compositions containing metronidazole |
| US6387383B1 (en) * | 2000-08-03 | 2002-05-14 | Dow Pharmaceutical Sciences | Topical low-viscosity gel composition |
| US20060093675A1 (en) * | 2004-10-29 | 2006-05-04 | Mathew Ebmeier | Intravaginal treatment of vaginal infections with metronidazole compositions |
| FR2882552B1 (fr) * | 2005-02-25 | 2008-12-26 | Galderma Sa | Gel aqueux de haute stabilite a base de metronidazole et procedes pour leur preparation |
| PT2544532T (pt) | 2010-03-12 | 2017-06-02 | Monsanto Technology Llc | Composições de gel agroquímicas |
| AU2012275292B2 (en) | 2011-06-28 | 2015-11-12 | Chemo Research, S.L. | High dosage mucoadhesive metronidazole aqueous-based gel formulations their use to treat bacterial vaginosis |
| EP3013368A1 (fr) | 2013-06-25 | 2016-05-04 | Mission Pharmacal Company | Nouvelles formulations pour le traitement de troubles vaginaux |
| CN114788791A (zh) | 2017-06-23 | 2022-07-26 | 宝洁公司 | 用于改善皮肤外观的组合物和方法 |
| EP3817717A1 (fr) | 2018-07-03 | 2021-05-12 | The Procter & Gamble Company | Méthode de traitement d'une affection cutanée |
| US10959933B1 (en) | 2020-06-01 | 2021-03-30 | The Procter & Gamble Company | Low pH skin care composition and methods of using the same |
| CN115843238B (zh) | 2020-06-01 | 2025-06-10 | 宝洁公司 | 改善维生素b3化合物渗透到皮肤中的方法 |
| JPWO2022269665A1 (fr) * | 2021-06-21 | 2022-12-29 | ||
| CN115350144A (zh) * | 2022-07-28 | 2022-11-18 | 苏州弘森药业股份有限公司 | 一种甲硝唑水凝胶及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883661A (en) * | 1971-11-09 | 1975-05-13 | Syntex Inc | Acne treatment |
| US4247547A (en) * | 1979-03-19 | 1981-01-27 | Johnson & Johnson | Tretinoin in a gel vehicle for acne treatment |
-
1987
- 1987-03-20 AT AT87902908T patent/ATE67667T1/de not_active IP Right Cessation
- 1987-03-20 EP EP87902908A patent/EP0305380B1/fr not_active Expired - Lifetime
- 1987-03-20 DE DE8787902908T patent/DE3773383D1/de not_active Expired - Lifetime
- 1987-03-20 WO PCT/US1987/000584 patent/WO1988006888A1/fr not_active Ceased
- 1987-03-20 AU AU72337/87A patent/AU610495B2/en not_active Expired
- 1987-03-20 KR KR1019880701486A patent/KR950003919B1/ko not_active Expired - Lifetime
- 1987-03-20 JP JP62502276A patent/JPH0825878B2/ja not_active Expired - Lifetime
-
1988
- 1988-11-18 FI FI885377A patent/FI88582C/fi not_active IP Right Cessation
- 1988-11-18 DK DK198806454A patent/DK173844B1/da not_active IP Right Cessation
- 1988-11-18 NO NO885172A patent/NO175883C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI88582B (fi) | 1993-02-26 |
| AU610495B2 (en) | 1991-05-23 |
| AU7233787A (en) | 1988-10-10 |
| EP0305380A4 (fr) | 1989-06-26 |
| FI885377L (fi) | 1988-11-18 |
| JPH01503061A (ja) | 1989-10-19 |
| ATE67667T1 (de) | 1991-10-15 |
| JPH0825878B2 (ja) | 1996-03-13 |
| KR950003919B1 (ko) | 1995-04-20 |
| FI885377A0 (fi) | 1988-11-18 |
| NO175883B (no) | 1994-09-19 |
| NO885172L (no) | 1988-11-18 |
| WO1988006888A1 (fr) | 1988-09-22 |
| EP0305380B1 (fr) | 1991-09-25 |
| KR890701113A (ko) | 1989-12-19 |
| NO885172D0 (no) | 1988-11-18 |
| DE3773383D1 (de) | 1991-10-31 |
| FI88582C (fi) | 1993-06-10 |
| EP0305380A1 (fr) | 1989-03-08 |
| NO175883C (no) | 1994-12-28 |
| DK645488D0 (da) | 1988-11-18 |
| DK645488A (da) | 1989-01-19 |
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| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |