DK2509569T3 - Derivater af hidtil ukendte peroxider, fremgangsmåde til fremstilling deraf og anvendelse deraf i humanmedicin og i kosmetik til behandling eller forebyggelse af akne - Google Patents
Derivater af hidtil ukendte peroxider, fremgangsmåde til fremstilling deraf og anvendelse deraf i humanmedicin og i kosmetik til behandling eller forebyggelse af akne Download PDFInfo
- Publication number
- DK2509569T3 DK2509569T3 DK10790768.5T DK10790768T DK2509569T3 DK 2509569 T3 DK2509569 T3 DK 2509569T3 DK 10790768 T DK10790768 T DK 10790768T DK 2509569 T3 DK2509569 T3 DK 2509569T3
- Authority
- DK
- Denmark
- Prior art keywords
- benzoyl
- peroxide
- bis
- methoxy
- benzoyl peroxide
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 12
- 239000002537 cosmetic Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 28
- 150000002978 peroxides Chemical class 0.000 title description 26
- 238000002360 preparation method Methods 0.000 title description 2
- 230000002265 prevention Effects 0.000 title 1
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 22
- 206010000496 acne Diseases 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 13
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 11
- -1 2,2-dimethyl-propionyloxymethoxy Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- QJDZIPBBMHTXQE-UHFFFAOYSA-N (2-benzoylperoxycarbonylphenoxy)methyl acetate Chemical compound CC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 QJDZIPBBMHTXQE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- AYZDWHBGZYAABH-UHFFFAOYSA-N benzoyl 2-(1-ethoxycarbonyloxyethoxy)benzenecarboperoxoate Chemical compound CCOC(=O)OC(C)OC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 AYZDWHBGZYAABH-UHFFFAOYSA-N 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- RRGYGNGVGBBCAK-UHFFFAOYSA-N (2-benzoylperoxycarbonylphenoxy)methyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 RRGYGNGVGBBCAK-UHFFFAOYSA-N 0.000 claims description 2
- JNWLCUOQWNMCKL-UHFFFAOYSA-N (2-benzoylperoxycarbonylphenoxy)methyl butanoate Chemical compound CCCC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 JNWLCUOQWNMCKL-UHFFFAOYSA-N 0.000 claims description 2
- ZUFGCKNSNTXAAN-UHFFFAOYSA-N (2-benzoylperoxycarbonylphenoxy)methyl propanoate Chemical compound CCC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 ZUFGCKNSNTXAAN-UHFFFAOYSA-N 0.000 claims description 2
- IXYQHBUHWUIEQP-UHFFFAOYSA-N 1-(2-benzoylperoxycarbonylphenoxy)ethyl acetate Chemical compound CC(=O)OC(C)OC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 IXYQHBUHWUIEQP-UHFFFAOYSA-N 0.000 claims description 2
- STNYBJZGPAMPAF-UHFFFAOYSA-N [2,3-bis(butan-2-yloxycarbonyloxymethoxy)benzoyl] 2,3-bis(butan-2-yloxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CCC(C)OC(=O)OCOC1=CC=CC(C(=O)OOC(=O)C=2C(=C(OCOC(=O)OC(C)CC)C=CC=2)OCOC(=O)OC(C)CC)=C1OCOC(=O)OC(C)CC STNYBJZGPAMPAF-UHFFFAOYSA-N 0.000 claims description 2
- PZEGZHAGBDCZFB-UHFFFAOYSA-N [2,3-bis(ethoxycarbonyloxymethoxy)benzoyl] 2,3-bis(ethoxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CCOC(=O)OCOC1=CC=CC(C(=O)OOC(=O)C=2C(=C(OCOC(=O)OCC)C=CC=2)OCOC(=O)OCC)=C1OCOC(=O)OCC PZEGZHAGBDCZFB-UHFFFAOYSA-N 0.000 claims description 2
- RUGPJAVPUCUYGY-UHFFFAOYSA-N benzoyl 2-(butoxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CCCCOC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 RUGPJAVPUCUYGY-UHFFFAOYSA-N 0.000 claims description 2
- HFCNDAGQRCDJOL-UHFFFAOYSA-N benzoyl 2-(propoxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CCCOC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 HFCNDAGQRCDJOL-UHFFFAOYSA-N 0.000 claims description 2
- BMISPIHNXHHLJW-UHFFFAOYSA-N benzoyl 2-[(ethoxycarbonylamino)methoxy]benzenecarboperoxoate Chemical compound CCOC(=O)NCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 BMISPIHNXHHLJW-UHFFFAOYSA-N 0.000 claims description 2
- NCBTYJYHTBRHKC-UHFFFAOYSA-N benzoyl 2-[[butoxycarbonyl(methyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCCCOC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 NCBTYJYHTBRHKC-UHFFFAOYSA-N 0.000 claims description 2
- KYJTXHBFJHDUBA-UHFFFAOYSA-N benzoyl 2-[[ethoxycarbonyl(ethyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCOC(=O)N(CC)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 KYJTXHBFJHDUBA-UHFFFAOYSA-N 0.000 claims description 2
- ABYRHARRMGYGBA-UHFFFAOYSA-N benzoyl 2-[[methyl(propoxycarbonyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCCOC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 ABYRHARRMGYGBA-UHFFFAOYSA-N 0.000 claims description 2
- LCECEGQYKBFRQI-UHFFFAOYSA-N benzoyl 2-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methoxy]benzenecarboperoxoate Chemical compound CC(C)(C)OC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 LCECEGQYKBFRQI-UHFFFAOYSA-N 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000007170 pathology Effects 0.000 claims description 2
- 229960003328 benzoyl peroxide Drugs 0.000 claims 4
- MKVDAKQTHGYRMS-UHFFFAOYSA-N 1-[2-[2-(1-acetyloxyethoxy)benzoyl]peroxycarbonylphenoxy]ethyl acetate Chemical compound CC(=O)OC(C)OC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OC(C)OC(C)=O MKVDAKQTHGYRMS-UHFFFAOYSA-N 0.000 claims 1
- 241000186429 Propionibacterium Species 0.000 claims 1
- DGBYEIBFJIIFBF-UHFFFAOYSA-N [2-(1-ethoxycarbonyloxyethoxy)benzoyl] 2-(1-ethoxycarbonyloxyethoxy)benzenecarboperoxoate Chemical compound CCOC(=O)OC(C)OC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OC(C)OC(=O)OCC DGBYEIBFJIIFBF-UHFFFAOYSA-N 0.000 claims 1
- MTDNOQPGYQJYBQ-UHFFFAOYSA-N [2-(propan-2-yloxycarbonyloxymethoxy)benzoyl] 2-(propan-2-yloxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CC(C)OC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCOC(=O)OC(C)C MTDNOQPGYQJYBQ-UHFFFAOYSA-N 0.000 claims 1
- CUVNMXCUOZMABN-UHFFFAOYSA-N [2-[(ethoxycarbonylamino)methoxy]benzoyl] 2-[(ethoxycarbonylamino)methoxy]benzenecarboperoxoate Chemical compound CCOC(=O)NCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCNC(=O)OCC CUVNMXCUOZMABN-UHFFFAOYSA-N 0.000 claims 1
- JLKIQFBMIIQDFX-UHFFFAOYSA-N [2-[2-(2,2-dimethylpropanoyloxymethoxy)benzoyl]peroxycarbonylphenoxy]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCOC(=O)C(C)(C)C JLKIQFBMIIQDFX-UHFFFAOYSA-N 0.000 claims 1
- KSYZPWVHUROCCC-UHFFFAOYSA-N [2-[2-(acetyloxymethoxy)benzoyl]peroxycarbonylphenoxy]methyl acetate Chemical compound CC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCOC(C)=O KSYZPWVHUROCCC-UHFFFAOYSA-N 0.000 claims 1
- AUSCNOZABULPDS-UHFFFAOYSA-N [2-[2-(butanoyloxymethoxy)benzoyl]peroxycarbonylphenoxy]methyl butanoate Chemical compound CCCC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCOC(=O)CCC AUSCNOZABULPDS-UHFFFAOYSA-N 0.000 claims 1
- GHHKRUDGDDPFOA-UHFFFAOYSA-N [2-[2-(propanoyloxymethoxy)benzoyl]peroxycarbonylphenoxy]methyl propanoate Chemical compound CCC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCOC(=O)CC GHHKRUDGDDPFOA-UHFFFAOYSA-N 0.000 claims 1
- LZSWVPIKTWOSDY-UHFFFAOYSA-N [2-[[butoxycarbonyl(methyl)amino]methoxy]benzoyl] 2-[[butoxycarbonyl(methyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCCCOC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCN(C)C(=O)OCCCC LZSWVPIKTWOSDY-UHFFFAOYSA-N 0.000 claims 1
- XERFPBLVEYGRPZ-UHFFFAOYSA-N [2-[[ethoxycarbonyl(ethyl)amino]methoxy]benzoyl] 2-[[ethoxycarbonyl(ethyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCOC(=O)N(CC)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCN(CC)C(=O)OCC XERFPBLVEYGRPZ-UHFFFAOYSA-N 0.000 claims 1
- RPPYOXYROMQMNI-UHFFFAOYSA-N [2-[[ethoxycarbonyl(methyl)amino]methoxy]benzoyl] 2-[[ethoxycarbonyl(methyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCOC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCN(C)C(=O)OCC RPPYOXYROMQMNI-UHFFFAOYSA-N 0.000 claims 1
- NYZMYRVMEUDCBI-UHFFFAOYSA-N [2-[[methyl(propan-2-yloxycarbonyl)amino]methoxy]benzoyl] 2-[[methyl(propan-2-yloxycarbonyl)amino]methoxy]benzenecarboperoxoate Chemical compound CC(C)OC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCN(C)C(=O)OC(C)C NYZMYRVMEUDCBI-UHFFFAOYSA-N 0.000 claims 1
- KYKZYPCRAATNQK-UHFFFAOYSA-N [2-[[methyl(propoxycarbonyl)amino]methoxy]benzoyl] 2-[[methyl(propoxycarbonyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCCOC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCN(C)C(=O)OCCC KYKZYPCRAATNQK-UHFFFAOYSA-N 0.000 claims 1
- MUIMPPCDPJUSMM-UHFFFAOYSA-N [2-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methoxy]benzoyl] 2-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methoxy]benzenecarboperoxoate Chemical compound CC(C)(C)OC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OCN(C)C(=O)OC(C)(C)C MUIMPPCDPJUSMM-UHFFFAOYSA-N 0.000 claims 1
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- 240000001307 Myosotis scorpioides Species 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 206010054107 Nodule Diseases 0.000 description 1
- 206010033733 Papule Diseases 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- 101100122755 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) NPA3 gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 206010043275 Teratogenicity Diseases 0.000 description 1
- IXVMKIYFTWADAM-UHFFFAOYSA-N [2,3-bis(propan-2-yloxycarbonyloxymethoxy)benzoyl] 2,3-bis(propan-2-yloxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CC(C)OC(=O)OCOC1=CC=CC(C(=O)OOC(=O)C=2C(=C(OCOC(=O)OC(C)C)C=CC=2)OCOC(=O)OC(C)C)=C1OCOC(=O)OC(C)C IXVMKIYFTWADAM-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000058 anti acne agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940124340 antiacne agent Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- SVRJLOGXOBAZDW-UHFFFAOYSA-N benzoyl 2-(ethoxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CCOC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 SVRJLOGXOBAZDW-UHFFFAOYSA-N 0.000 description 1
- WDJQGPCHRIPPEJ-UHFFFAOYSA-N benzoyl 2-(propan-2-yloxycarbonyloxymethoxy)benzenecarboperoxoate Chemical compound CC(C)OC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 WDJQGPCHRIPPEJ-UHFFFAOYSA-N 0.000 description 1
- LQKBDERFSLMETP-UHFFFAOYSA-N benzoyl 2-[(2-methylpropan-2-yl)oxycarbonyloxymethoxy]benzenecarboperoxoate Chemical compound CC(C)(C)OC(=O)OCOC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 LQKBDERFSLMETP-UHFFFAOYSA-N 0.000 description 1
- YQVQYLAJZJSSNH-UHFFFAOYSA-N benzoyl 2-[[ethoxycarbonyl(methyl)amino]methoxy]benzenecarboperoxoate Chemical compound CCOC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 YQVQYLAJZJSSNH-UHFFFAOYSA-N 0.000 description 1
- PBGUIZYFYSTHMY-UHFFFAOYSA-N benzoyl 2-[[methyl(propan-2-yloxycarbonyl)amino]methoxy]benzenecarboperoxoate Chemical compound CC(C)OC(=O)N(C)COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1 PBGUIZYFYSTHMY-UHFFFAOYSA-N 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036074 healthy skin Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NZDJTVSTIFYISQ-UHFFFAOYSA-N iodomethyl acetate Chemical compound CC(=O)OCI NZDJTVSTIFYISQ-UHFFFAOYSA-N 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 229960005280 isotretinoin Drugs 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 208000003265 stomatitis Diseases 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- 150000004901 trioxanes Chemical class 0.000 description 1
- 150000002266 vitamin A derivatives Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/40—Peroxy compounds containing nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Claims (6)
1. Forbindelser med den følgende almene formel (I):
hvor: - Z repræsenterer et oxygen eller den følgende sekvens:
- Y repræsenterer et hydrogen eller den følgende sekvens:
- V repræsenterer et oxygen eller den følgende sekvens: -^-N-R6 - R3 og R6 repræsenterer, identisk eller uafhængigt, et hydrogen eller et C-i- 4-alkyl - R1 og R4 repræsenterer, identisk eller uafhængigt, et hydrogen eller et C-i- 4-alkyl - R2 og R5 repræsenterer, identisk eller uafhængigt, et C-Mo-alkyl eller et C-i-10-alkoxy.
2. Forbindelser ifølge krav 1, kendetegnet ved, at: a. Z repræsenterer et oxygen eller den følgende sekvens:
b. Y repræsenterer et hydrogen eller den følgende sekvens:
c. V repræsenterer et oxygen eller den følgende sekvens: —N—R6 d. R3 og R6 repræsenterer, identisk eller uafhængigt, et hydrogen, et methyl eller et ethyl e. R1 og R4 repræsenterer, identisk eller uafhængigt, et hydrogen eller et methyl f. R2 og R5 repræsenterer, identisk eller uafhængigt, et Ci-4-alkyl eller et C-i-4-alkoxy.
3. Forbindelse ifølge et af kravene 1 eller 2, valgt fra listen, der omfatter de følgende forbindelser: bis(2-acetoxymethoxy)-benzoylperoxid, (2-acetoxymethoxy-benzoyl)-benzoylperoxid, bis(2-propionyloxymethoxy)-benzoylperoxid, (2-propionyloxymethoxy-benzoyl)-benzoylperoxid, bis(2-butyryloxymethoxy)-benzoylperoxid, (2-butyryloxymethoxy-benzoyl)-benzoylperoxid, bis(2-pentanoyloxymethoxy)-benzoylperoxid (2-pentanoyloxymethoxy-benzoyl)-benzoylperoxid, bis(2-isobutyryloxymethoxy)-benzoylperoxid, (2-isobutyryloxymethoxy-benzoyl)-benzoylperoxid, bis[2-(2,2-dimethyl-propionyloxymethoxy)]-benzoylperoxid, [2-(2,2-dimethyl-propionyloxymethoxy)-benzoyl]-benzoylperoxid, bis[2-(1-acetoxy-ethoxy)]-benzoylperoxid, [2-(1-acetoxy-ethoxy)-benzoyl]benzoylperoxid, bis(2-ethoxycarbonyloxymethoxy)-benzoylperoxid, (2-ethoxycarbonyloxymethoxy-benzoyl)-benzoylperoxid bis(2-propoxycarbonyloxymethoxy)-benzoylperoxid, (2-propoxycarbonyloxymethoxy-benzoyl)-benzoylperoxid, bis (2-butoxycarbonyloxymethoxy)-benzoylperoxid, (2-butoxycarbonyloxymethoxy-benzoyl)-benzoylperoxid, bis(2-isopropoxycarbonyloxymethoxy)-benzoylperoxid, (2-isopropoxycarbonyloxymethoxy-benzoyl)-benzoylperoxid, bis (2-tert-butoxycarbonyloxymethoxy)-benzoylperoxid, (2-tert-butoxycarbonyloxymethoxy-benzoyl)-benzoylperoxid, bis[2-(ethoxycarbonylamino-methoxy)]-benzoylperoxid, [2-(ethoxycarbonylamino-methoxy)-benzoyl]-benzoylperoxid, bis (2-[(ethoxycarbonyl-ethyl-amino)-methoxy])-benzoylperoxid, (2-[(ethoxycarbonyl-ethyl-amino)-methoxy]-benzoyl)-benzoylperoxid, bis(2-[(ethoxycarbonyl-methyl-amino)-methoxy])-benzoylperoxid, (2-[(ethoxycarbonyl-methyl-amino)-methoxy]-benzoyl)-benzoylperoxid, bis(2-[(methyl-propoxycarbonyl-amino)-methoxy])-benzoylperoxid, (2-[(methyl-propoxycarbonyl-amino)-methoxy]-benzoyl)-benzoylperoxid, bis(2-[(butoxycarbonyl-methyl-amino)-methoxy])-benzoylperoxid, (2-[(butoxycarbonyl-methyl-amino)-methoxy]-benzoyl)-benzoylperoxid, bis(2-[(isopropoxycarbonyl-methyl-amino)-methoxy])-benzoylperoxid, (2-[(isopropoxycarbonyl-methyl-amino)-methoxy]-benzoyl)-benzoylperoxid, bis(2-[(tert-butoxycarbonyl-methyl-amino)-methoxy])-benzoylperoxid, (2-[(tert-butoxycarbonyl-methyl-amino)-methoxy]-benzoyl)-benzoylperoxid, bis[2-(1-ethoxycarbonyloxy-ethoxy)]-benzoylperoxid, [2-(1-ethoxycarbonyloxy-ethoxy)-benzoyl]-benzoylperoxid.
4. Forbindelse ifølge et af kravene 1 til 3 som et medicinsk produkt.
5. Forbindelse ifølge et af kravene 1 til 4 til behandling af patologier eller lidelser, der er forbundet med forekomsten af Propionibacterium aenes.
6. Forbindelse ifølge et af kravene 1 til 5 til inkorporering i en kosmetiksammensætning, kendetegnet ved, at den hæmmer udbredelsen af patogene bakterier, som er involveret i udviklingen af hudlidelser af akne-typen, især P. aenes.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0958847A FR2953833B1 (fr) | 2009-12-10 | 2009-12-10 | Derives de nouveaux peroxydes, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique pour le traitement ou la prevention de l'acne |
PCT/EP2010/069421 WO2011070171A1 (en) | 2009-12-10 | 2010-12-10 | Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne |
Publications (1)
Publication Number | Publication Date |
---|---|
DK2509569T3 true DK2509569T3 (da) | 2014-03-03 |
Family
ID=42358641
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK10790768.5T DK2509569T3 (da) | 2009-12-10 | 2010-12-10 | Derivater af hidtil ukendte peroxider, fremgangsmåde til fremstilling deraf og anvendelse deraf i humanmedicin og i kosmetik til behandling eller forebyggelse af akne |
Country Status (21)
Country | Link |
---|---|
US (1) | US8729312B2 (da) |
EP (1) | EP2509569B1 (da) |
JP (1) | JP5613776B2 (da) |
KR (1) | KR101566065B1 (da) |
CN (1) | CN102740826B (da) |
AU (1) | AU2010329841B2 (da) |
BR (1) | BR112012013396A2 (da) |
CA (1) | CA2782927C (da) |
CY (1) | CY1115204T1 (da) |
DK (1) | DK2509569T3 (da) |
ES (1) | ES2449471T3 (da) |
FR (1) | FR2953833B1 (da) |
HR (1) | HRP20140190T1 (da) |
MX (1) | MX2012006213A (da) |
PL (1) | PL2509569T3 (da) |
PT (1) | PT2509569E (da) |
RS (1) | RS53229B (da) |
RU (1) | RU2552110C2 (da) |
SI (1) | SI2509569T1 (da) |
SM (1) | SMT201400049B (da) |
WO (1) | WO2011070171A1 (da) |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE587389A (da) | 1959-02-11 | |||
GB1054124A (da) | 1964-03-31 | |||
US4355028A (en) * | 1978-04-04 | 1982-10-19 | Westwood Pharmaceuticals, Inc. | Composition for treating acne vulgaris |
US4505896A (en) | 1979-04-19 | 1985-03-19 | Elorac, Ltd. | Method of treating acne vulgaris and composition |
GB2068228B (en) | 1980-01-24 | 1984-02-29 | Janssen Pharmaceutica Nv | Anti-microbial compositions for the topical treatment of acne vulgaris |
IT1210608B (it) | 1980-12-08 | 1989-09-14 | Rorer Int Overseas | Composizione per il trattamento topico dell'acne |
US4364940A (en) * | 1981-02-23 | 1982-12-21 | Usv Pharmaceutical Corporation | Compositions for treating acne |
US4514385A (en) | 1981-10-05 | 1985-04-30 | Alcon Laboratories, Inc. | Anti-acne compositions |
US4520133A (en) * | 1983-08-11 | 1985-05-28 | Richardson-Vicks Inc. | Monohydroxy-benzoyl peroxide and compositions for treating acne |
FR2581542B1 (fr) | 1985-05-07 | 1988-02-19 | Oreal | Compositions topiques destinees au traitement de la peau a base de derives de l'acide salicylique |
US4762945A (en) * | 1985-09-12 | 1988-08-09 | Usv Pharmaceutical Corporation | Process for the preparation of aspirin peroxide |
FR2607498B1 (fr) | 1986-12-01 | 1991-04-05 | Oreal | Nouveaux salicylates lipophiles d'ammoniums quaternaires, leur utilisation en cosmetique et en dermopharmacie |
US5409917A (en) | 1991-03-05 | 1995-04-25 | Marvin S. Towsend | Topical treatment of acne with cephalosporins |
TW203552B (en) * | 1992-02-18 | 1993-04-11 | J Baroody Lloyd | Compositions of clindamycin and benzoyl peroxide for acne treatment |
TW224048B (da) * | 1992-03-30 | 1994-05-21 | Hoechst Roussel Pharma | |
US5439923A (en) | 1993-12-21 | 1995-08-08 | Eli Lilly And Company | Method of inhibiting seborrhea and acne |
CN1145585A (zh) * | 1994-03-03 | 1997-03-19 | 普罗克特和甘保尔公司 | 抗痤疮组合物 |
US5445823A (en) * | 1994-10-20 | 1995-08-29 | The Procter & Gamble Company | Dermatological compositions and method of treatment of skin lesions therewith |
DE50001223D1 (de) * | 2000-12-21 | 2003-03-13 | Ilford Imaging Ch Gmbh | Monoazofarbstoffe, deren Herstellung und Verwendung |
GB0505909D0 (en) * | 2005-03-23 | 2005-04-27 | Univ Leeds | Formulations |
-
2009
- 2009-12-10 FR FR0958847A patent/FR2953833B1/fr not_active Expired - Fee Related
-
2010
- 2010-12-10 CA CA2782927A patent/CA2782927C/en active Active
- 2010-12-10 EP EP10790768.5A patent/EP2509569B1/en active Active
- 2010-12-10 CN CN201080063560.1A patent/CN102740826B/zh active Active
- 2010-12-10 WO PCT/EP2010/069421 patent/WO2011070171A1/en active Application Filing
- 2010-12-10 DK DK10790768.5T patent/DK2509569T3/da active
- 2010-12-10 SI SI201030543T patent/SI2509569T1/sl unknown
- 2010-12-10 BR BR112012013396A patent/BR112012013396A2/pt active IP Right Grant
- 2010-12-10 US US13/514,262 patent/US8729312B2/en active Active
- 2010-12-10 MX MX2012006213A patent/MX2012006213A/es active IP Right Grant
- 2010-12-10 RU RU2012128866/04A patent/RU2552110C2/ru active
- 2010-12-10 PT PT107907685T patent/PT2509569E/pt unknown
- 2010-12-10 PL PL10790768T patent/PL2509569T3/pl unknown
- 2010-12-10 ES ES10790768.5T patent/ES2449471T3/es active Active
- 2010-12-10 AU AU2010329841A patent/AU2010329841B2/en active Active
- 2010-12-10 KR KR1020127017819A patent/KR101566065B1/ko active IP Right Grant
- 2010-12-10 RS RS20140087A patent/RS53229B/en unknown
- 2010-12-10 JP JP2012542569A patent/JP5613776B2/ja active Active
-
2014
- 2014-02-28 CY CY20141100168T patent/CY1115204T1/el unknown
- 2014-03-03 HR HRP20140190AT patent/HRP20140190T1/hr unknown
- 2014-04-11 SM SM201400049T patent/SMT201400049B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
MX2012006213A (es) | 2012-06-19 |
PL2509569T3 (pl) | 2014-06-30 |
US8729312B2 (en) | 2014-05-20 |
CN102740826B (zh) | 2014-12-31 |
JP5613776B2 (ja) | 2014-10-29 |
US20130178648A1 (en) | 2013-07-11 |
CA2782927C (en) | 2014-09-09 |
RS53229B (en) | 2014-08-29 |
KR20120091448A (ko) | 2012-08-17 |
BR112012013396A2 (pt) | 2016-03-08 |
HRP20140190T1 (hr) | 2014-04-11 |
KR101566065B1 (ko) | 2015-11-04 |
WO2011070171A1 (en) | 2011-06-16 |
SI2509569T1 (sl) | 2014-04-30 |
RU2552110C2 (ru) | 2015-06-10 |
FR2953833A1 (fr) | 2011-06-17 |
AU2010329841B2 (en) | 2015-02-05 |
SMT201400049B (it) | 2014-05-07 |
ES2449471T3 (es) | 2014-03-19 |
CN102740826A (zh) | 2012-10-17 |
AU2010329841A1 (en) | 2012-07-12 |
CA2782927A1 (en) | 2011-06-16 |
FR2953833B1 (fr) | 2012-01-13 |
JP2013513581A (ja) | 2013-04-22 |
CY1115204T1 (el) | 2017-01-04 |
PT2509569E (pt) | 2014-03-10 |
EP2509569A1 (en) | 2012-10-17 |
RU2012128866A (ru) | 2014-01-20 |
EP2509569B1 (en) | 2013-12-04 |
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