JPS60260557A - モノヒドロキシ−ベンゾイルパ−オキシドとざそう治療用組成物 - Google Patents
モノヒドロキシ−ベンゾイルパ−オキシドとざそう治療用組成物Info
- Publication number
- JPS60260557A JPS60260557A JP59160312A JP16031284A JPS60260557A JP S60260557 A JPS60260557 A JP S60260557A JP 59160312 A JP59160312 A JP 59160312A JP 16031284 A JP16031284 A JP 16031284A JP S60260557 A JPS60260557 A JP S60260557A
- Authority
- JP
- Japan
- Prior art keywords
- acne
- monohydroxy
- acnes
- skin
- benzoylperoxide
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 206010000496 acne Diseases 0.000 title claims abstract description 13
- 208000002874 Acne Vulgaris Diseases 0.000 title claims abstract description 11
- MIKBSSUPPHVGGC-UHFFFAOYSA-N (4-hydroxybenzoyl) 4-hydroxybenzenecarboperoxoate Chemical compound C1=CC(O)=CC=C1C(=O)OOC(=O)C1=CC=C(O)C=C1 MIKBSSUPPHVGGC-UHFFFAOYSA-N 0.000 title claims abstract 5
- 230000001225 therapeutic effect Effects 0.000 title 1
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims description 9
- 239000006210 lotion Substances 0.000 claims description 6
- 230000000699 topical effect Effects 0.000 claims description 6
- 239000006071 cream Substances 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 9
- 230000002995 comedolytic effect Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 208000020154 Acnes Diseases 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000004342 Benzoyl peroxide Substances 0.000 description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000186427 Cutibacterium acnes Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- 244000005714 skin microbiome Species 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- VWIQHHBCAQFZCF-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.Cl Chemical compound C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.Cl VWIQHHBCAQFZCF-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 230000003780 keratinization Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- -1 monohydroxy-benzyl peroxide Chemical compound 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229930002330 retinoic acid Natural products 0.000 description 2
- 210000001732 sebaceous gland Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- SFQULWLSPKHJMW-UHFFFAOYSA-N (4-hydroxybenzoyl) 4-hydroxybenzoate Chemical class C1=CC(O)=CC=C1C(=O)OC(=O)C1=CC=C(O)C=C1 SFQULWLSPKHJMW-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- LGEZTMRIZWCDLW-UHFFFAOYSA-N 14-methylpentadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC(C)C LGEZTMRIZWCDLW-UHFFFAOYSA-N 0.000 description 1
- DVIHKVWYFXLBEM-UHFFFAOYSA-N 2-hydroxybenzoyl chloride Chemical compound OC1=CC=CC=C1C(Cl)=O DVIHKVWYFXLBEM-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 108010076119 Caseins Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 244000148064 Enicostema verticillatum Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010025421 Macule Diseases 0.000 description 1
- 206010027626 Milia Diseases 0.000 description 1
- 206010033733 Papule Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940078545 isocetyl stearate Drugs 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- SHGAZHPCJJPHSC-XFYACQKRSA-N isotretinoin Chemical compound OC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-XFYACQKRSA-N 0.000 description 1
- 229960005280 isotretinoin Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001819 pancreatic juice Anatomy 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 238000003756 stirring Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/38—Percompounds, e.g. peracids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
- C07C409/34—Peroxy compounds the —O—O— group being bound between two >C=O groups both belonging to carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/522,207 US4520133A (en) | 1983-08-11 | 1983-08-11 | Monohydroxy-benzoyl peroxide and compositions for treating acne |
| US522207 | 1983-08-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60260557A true JPS60260557A (ja) | 1985-12-23 |
| JPH0420427B2 JPH0420427B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-02 |
Family
ID=24079910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59160312A Granted JPS60260557A (ja) | 1983-08-11 | 1984-08-01 | モノヒドロキシ−ベンゾイルパ−オキシドとざそう治療用組成物 |
Country Status (10)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013513580A (ja) * | 2009-12-10 | 2013-04-22 | ガルデルマ・リサーチ・アンド・デヴェロップメント | 新規の過酸化物誘導体、その調製方法、ならびにざ瘡の治療または予防のためのヒト医薬品および化粧品へのその使用 |
| JP2013513581A (ja) * | 2009-12-10 | 2013-04-22 | ガルデルマ・リサーチ・アンド・デヴェロップメント | 新規過酸化物の誘導体、その調製方法、および、ニキビを治療または予防するためのヒト用医薬品および化粧品における使用 |
| JP2013515759A (ja) * | 2009-12-29 | 2013-05-09 | ガルデルマ・リサーチ・アンド・デヴェロップメント | ジベンゾイルペルオキシド誘導体、それらの調製方法、およびそれらを含有する化粧品または皮膚科学的組成物 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2604357B1 (fr) * | 1986-09-30 | 1988-12-02 | Oreal | Composition pharmaceutique et cosmetique anti-acneique |
| KR20020043627A (ko) | 1999-10-13 | 2002-06-10 | 샬크비즈크 피이터 코르넬리스; 페트귄터 | 혼합된 무수물을 사용하여 퍼옥시드를 제조하는 방법 |
| EP1220837B1 (en) * | 1999-10-13 | 2004-08-18 | Akzo Nobel N.V. | Process for preparing peroxides using mixed anhydrides |
| HUE052401T2 (hu) * | 2005-03-10 | 2021-04-28 | Obagi Cosmeceuticals Llc | Stabil szerves peroxid-készítmények |
| WO2006099187A2 (en) * | 2005-03-10 | 2006-09-21 | Jr Chem, Llc | Benzoyl peroxide compositions and methods of use |
| US20090306023A1 (en) * | 2005-06-29 | 2009-12-10 | Ramirez Jose E | Stable organic peroxide compositions |
| US7556820B2 (en) | 2005-06-29 | 2009-07-07 | Jr Chem, Llc | Stable organic peroxide compositions |
| WO2007002880A2 (en) * | 2005-06-29 | 2007-01-04 | Jr Chem, Llc | Method of enhanced drug application |
| US20070001145A1 (en) * | 2005-06-29 | 2007-01-04 | Faryniarz Joseph R | Stable organic peroxide compositions |
| WO2020261704A1 (ja) * | 2019-06-26 | 2020-12-30 | 浜松ホトニクス株式会社 | 光電陰極、電子管、及び、光電陰極の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643989A1 (de) * | 1967-07-27 | 1971-10-07 | Faltusz Elemer Dipl Chem Dr | Verfahren zur Herstellung von organischen Diacylperoxyden |
| US4355028A (en) * | 1978-04-04 | 1982-10-19 | Westwood Pharmaceuticals, Inc. | Composition for treating acne vulgaris |
| US4318907A (en) * | 1978-04-04 | 1982-03-09 | Westwood Pharmaceuticals, Inc. | Method for treating acne vulgaris and compositions useful for that purpose |
| US4279831A (en) * | 1979-08-10 | 1981-07-21 | Argus Chemical Corporation | 2-Chloro-2-alkyl substituted asymmetrical diacyl peroxides |
| US4364940A (en) * | 1981-02-23 | 1982-12-21 | Usv Pharmaceutical Corporation | Compositions for treating acne |
-
1983
- 1983-08-11 US US06/522,207 patent/US4520133A/en not_active Expired - Fee Related
-
1984
- 1984-08-01 JP JP59160312A patent/JPS60260557A/ja active Granted
- 1984-08-01 ZA ZA845967A patent/ZA845967B/xx unknown
- 1984-08-02 AT AT84109184T patent/ATE31530T1/de not_active IP Right Cessation
- 1984-08-02 EP EP84109184A patent/EP0133554B1/en not_active Expired
- 1984-08-02 DE DE8484109184T patent/DE3468212D1/de not_active Expired
- 1984-08-03 AU AU31469/84A patent/AU569102B2/en not_active Ceased
- 1984-08-03 NZ NZ209109A patent/NZ209109A/en unknown
- 1984-08-07 CA CA000460488A patent/CA1241342A/en not_active Expired
- 1984-08-08 IL IL72620A patent/IL72620A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013513580A (ja) * | 2009-12-10 | 2013-04-22 | ガルデルマ・リサーチ・アンド・デヴェロップメント | 新規の過酸化物誘導体、その調製方法、ならびにざ瘡の治療または予防のためのヒト医薬品および化粧品へのその使用 |
| JP2013513581A (ja) * | 2009-12-10 | 2013-04-22 | ガルデルマ・リサーチ・アンド・デヴェロップメント | 新規過酸化物の誘導体、その調製方法、および、ニキビを治療または予防するためのヒト用医薬品および化粧品における使用 |
| JP2013515759A (ja) * | 2009-12-29 | 2013-05-09 | ガルデルマ・リサーチ・アンド・デヴェロップメント | ジベンゾイルペルオキシド誘導体、それらの調製方法、およびそれらを含有する化粧品または皮膚科学的組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1241342A (en) | 1988-08-30 |
| EP0133554A3 (en) | 1985-05-08 |
| US4520133A (en) | 1985-05-28 |
| ZA845967B (en) | 1985-03-27 |
| JPH0420427B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-02 |
| NZ209109A (en) | 1987-08-31 |
| DE3468212D1 (en) | 1988-02-04 |
| IL72620A (en) | 1987-10-30 |
| IL72620A0 (en) | 1984-11-30 |
| AU569102B2 (en) | 1988-01-21 |
| ATE31530T1 (de) | 1988-01-15 |
| AU3146984A (en) | 1985-02-14 |
| EP0133554A2 (en) | 1985-02-27 |
| EP0133554B1 (en) | 1987-12-23 |
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