CH674847A5 - - Google Patents
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- Publication number
- CH674847A5 CH674847A5 CH1705/87A CH170587A CH674847A5 CH 674847 A5 CH674847 A5 CH 674847A5 CH 1705/87 A CH1705/87 A CH 1705/87A CH 170587 A CH170587 A CH 170587A CH 674847 A5 CH674847 A5 CH 674847A5
- Authority
- CH
- Switzerland
- Prior art keywords
- clindamycin
- erythromycin
- lincomycin
- trans
- esters
- Prior art date
Links
- 229960003276 erythromycin Drugs 0.000 claims description 56
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 55
- 150000002148 esters Chemical class 0.000 claims description 54
- 229960002227 clindamycin Drugs 0.000 claims description 45
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 claims description 38
- 229960005287 lincomycin Drugs 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 36
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 claims description 34
- OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 claims description 33
- 229930006677 Erythromycin A Natural products 0.000 claims description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 206010000496 acne Diseases 0.000 claims description 20
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 19
- 229960001727 tretinoin Drugs 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- 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 claims description 14
- 229930002330 retinoic acid Natural products 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 208000017520 skin disease Diseases 0.000 claims description 9
- 240000002234 Allium sativum Species 0.000 claims description 8
- 235000004611 garlic Nutrition 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 7
- -1 fatty acid triglycerides Chemical class 0.000 claims description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
- 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 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 229960005280 isotretinoin Drugs 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000000058 anti acne agent Substances 0.000 claims description 2
- 229940124340 antiacne agent Drugs 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000003242 anti bacterial agent Substances 0.000 description 20
- 229940088710 antibiotic agent Drugs 0.000 description 20
- 230000000694 effects Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 238000002955 isolation Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000002609 medium Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 230000036961 partial effect Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000186427 Cutibacterium acnes Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 6
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229940055019 propionibacterium acne Drugs 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000004452 microanalysis Methods 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 235000019271 petrolatum Nutrition 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000002458 infectious effect Effects 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 230000000750 progressive effect Effects 0.000 description 3
- 125000001444 retinoyl group Chemical group O=C([*])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010048768 Dermatosis Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 206010039792 Seborrhoea Diseases 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000003054 hormonal effect Effects 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 208000008742 seborrheic dermatitis Diseases 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 description 1
- FPPBCRLXUHYGHR-UHFFFAOYSA-N 2-tert-butyl-3-hydroxycyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=C(O)C(=O)C=CC1=O FPPBCRLXUHYGHR-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 102000001974 Hyaluronidases Human genes 0.000 description 1
- 108050009363 Hyaluronidases Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000208465 Proteaceae Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000007399 clostridium medium Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 230000004090 etiopathogenesis Effects 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229960001625 furazolidone Drugs 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000001530 keratinolytic effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 239000006152 selective media Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- 239000003871 white petrolatum Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- 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
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Dermatology (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8606528A FR2598420B1 (fr) | 1986-05-06 | 1986-05-06 | Nouveaux esters retinoiques d'antibiotiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH674847A5 true CH674847A5 (enExample) | 1990-07-31 |
Family
ID=9334966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1705/87A CH674847A5 (enExample) | 1986-05-06 | 1987-05-05 |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JP2504990B2 (enExample) |
| BE (1) | BE1004152A4 (enExample) |
| CA (1) | CA1300131C (enExample) |
| CH (1) | CH674847A5 (enExample) |
| DE (1) | DE3714937C2 (enExample) |
| DK (1) | DK169345B1 (enExample) |
| ES (1) | ES2006478A6 (enExample) |
| FR (1) | FR2598420B1 (enExample) |
| GB (1) | GB2191483B (enExample) |
| IT (1) | IT1204556B (enExample) |
| NL (1) | NL193946C (enExample) |
| NO (1) | NO168041C (enExample) |
| SE (1) | SE470379B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU87041A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87035A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters du type etretinique ou apparente d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87040A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters aromatiques polycycliques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87036A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters cycloaliphatiques insatures d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87038A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters aromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87037A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters polyaromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87039A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters biaromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| LU87070A1 (fr) * | 1987-12-10 | 1989-07-07 | Oreal | Association de derives de pyrimidine et d'agents pour induire et stimuler la croissance des cheveux et diminuer leur chute |
| FR2644460A1 (fr) * | 1989-03-16 | 1990-09-21 | Oreal | Esters retinoiques de d-desosamine, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| GB2282596B (en) * | 1993-10-06 | 1998-04-15 | Ciba Geigy Ag | Water-soluble retinoids |
| FR2931661B1 (fr) * | 2008-05-30 | 2010-07-30 | Galderma Res & Dev | Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide. |
| FR2931662B1 (fr) * | 2008-05-30 | 2010-07-30 | Galderma Res & Dev | Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise. |
| EP2723452A2 (en) | 2011-06-22 | 2014-04-30 | Vyome Biosciences Pvt Ltd | Conjugate-based antifungal and antibacterial prodrugs |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2862921A (en) * | 1953-08-13 | 1958-12-02 | Upjohn Co | Erythromycin esters |
| US3598806A (en) * | 1969-04-15 | 1971-08-10 | Upjohn Co | Process for preparing lincomycin-3-monoacylates |
| FR2378523A1 (fr) * | 1977-01-26 | 1978-08-25 | Grupper Charles | Medicament pour le traitement de l'acne |
| FR2582000B1 (fr) * | 1985-05-14 | 1987-06-26 | Oreal | Esters gras bi ou tri-eniques d'erythromycine a, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
-
1986
- 1986-05-06 FR FR8606528A patent/FR2598420B1/fr not_active Expired - Lifetime
-
1987
- 1987-05-02 JP JP62107980A patent/JP2504990B2/ja not_active Expired - Lifetime
- 1987-05-04 NL NL8701054A patent/NL193946C/nl not_active IP Right Cessation
- 1987-05-05 CA CA000536348A patent/CA1300131C/fr not_active Expired - Lifetime
- 1987-05-05 CH CH1705/87A patent/CH674847A5/fr not_active IP Right Cessation
- 1987-05-05 DE DE3714937A patent/DE3714937C2/de not_active Expired - Lifetime
- 1987-05-05 SE SE8701845A patent/SE470379B/sv not_active IP Right Cessation
- 1987-05-05 IT IT20389/87A patent/IT1204556B/it active
- 1987-05-05 NO NO871870A patent/NO168041C/no unknown
- 1987-05-05 DK DK229387A patent/DK169345B1/da not_active IP Right Cessation
- 1987-05-05 ES ES8701603A patent/ES2006478A6/es not_active Expired
- 1987-05-06 BE BE8700486A patent/BE1004152A4/fr not_active IP Right Cessation
- 1987-05-06 GB GB8710673A patent/GB2191483B/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK169345B1 (da) | 1994-10-10 |
| GB2191483A (en) | 1987-12-16 |
| IT8720389A0 (it) | 1987-05-05 |
| JPS62289593A (ja) | 1987-12-16 |
| NO871870D0 (no) | 1987-05-05 |
| ES2006478A6 (es) | 1989-05-01 |
| DE3714937A1 (de) | 1987-11-12 |
| JP2504990B2 (ja) | 1996-06-05 |
| CA1300131C (fr) | 1992-05-05 |
| NL193946C (nl) | 2001-03-02 |
| NO168041B (no) | 1991-09-30 |
| SE8701845D0 (sv) | 1987-05-05 |
| IT1204556B (it) | 1989-03-10 |
| SE8701845L (sv) | 1987-11-07 |
| NL8701054A (nl) | 1987-12-01 |
| DE3714937C2 (de) | 1998-02-26 |
| GB8710673D0 (en) | 1987-06-10 |
| FR2598420A1 (fr) | 1987-11-13 |
| FR2598420B1 (fr) | 1991-06-07 |
| SE470379B (sv) | 1994-02-07 |
| GB2191483B (en) | 1990-05-30 |
| NL193946B (nl) | 2000-11-01 |
| NO168041C (no) | 1992-01-08 |
| NO871870L (no) | 1987-11-09 |
| BE1004152A4 (fr) | 1992-10-06 |
| DK229387D0 (da) | 1987-05-05 |
| DK229387A (da) | 1987-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |