RU2350599C2 - Двойные сложные эфиры - Google Patents

Info

Publication number

RU2350599C2

RU2350599C2 RU2004118713/04A RU2004118713A RU2350599C2 RU 2350599 C2 RU2350599 C2 RU 2350599C2 RU 2004118713/04 A RU2004118713/04 A RU 2004118713/04A RU 2004118713 A RU2004118713 A RU 2004118713A RU 2350599 C2 RU2350599 C2 RU 2350599C2

Authority

RU

Russia

Prior art keywords

bis

group

methyl

ethyl

formula

Prior art date

2001-11-22

Links

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• Global Dossier
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• 150000002148 esters Chemical class 0.000 title claims abstract description 21
• 150000001875 compounds Chemical class 0.000 claims abstract description 53
• -1 acyloxymethyl ester Chemical class 0.000 claims abstract description 31
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 239000003814 drug Substances 0.000 claims abstract description 24
• 208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 11
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 11
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
• 206010000496 acne Diseases 0.000 claims abstract description 11
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• 238000000034 method Methods 0.000 claims abstract description 11
• 239000001257 hydrogen Substances 0.000 claims abstract description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 7
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 7
• 208000000069 hyperpigmentation Diseases 0.000 claims abstract description 7
• 230000003810 hyperpigmentation Effects 0.000 claims abstract description 7
• 201000004700 rosacea Diseases 0.000 claims abstract description 7
• 206010004146 Basal cell carcinoma Diseases 0.000 claims abstract description 6
• 125000003118 aryl group Chemical group 0.000 claims abstract description 6
• 230000029663 wound healing Effects 0.000 claims abstract description 6
• QQVBQUHUJXHTEG-UHFFFAOYSA-N bis(1-acetyloxyethyl) nonanedioate Chemical compound CC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC(C)OC(C)=O QQVBQUHUJXHTEG-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical group 0.000 claims abstract 2
• 229940079593 drug Drugs 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 229940088679 drug related substance Drugs 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004185 ester group Chemical group 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 230000000069 prophylactic effect Effects 0.000 claims description 2
• 208000009621 actinic keratosis Diseases 0.000 claims 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 37
• 239000000126 substance Substances 0.000 abstract description 6
• 238000004519 manufacturing process Methods 0.000 abstract description 4
• 230000000694 effects Effects 0.000 abstract description 3
• 206010020649 Hyperkeratosis Diseases 0.000 abstract description 2
• 208000001126 Keratosis Diseases 0.000 abstract description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 44
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 239000000243 solution Substances 0.000 description 24
• 239000002253 acid Substances 0.000 description 22
• 229960002255 azelaic acid Drugs 0.000 description 21
• 230000015572 biosynthetic process Effects 0.000 description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
• 239000006071 cream Substances 0.000 description 17
• 238000005160 1H NMR spectroscopy Methods 0.000 description 15
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
• 238000001704 evaporation Methods 0.000 description 12
• 230000008020 evaporation Effects 0.000 description 12
• 239000000047 product Substances 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• 239000012230 colorless oil Substances 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 8
• VVWPSAPZUZXYCM-UHFFFAOYSA-N 9-methoxy-9-oxononanoic acid Chemical compound COC(=O)CCCCCCCC(O)=O VVWPSAPZUZXYCM-UHFFFAOYSA-N 0.000 description 7
• 150000001991 dicarboxylic acids Chemical class 0.000 description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• 239000002674 ointment Substances 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
• 229930040373 Paraformaldehyde Natural products 0.000 description 5
• 125000005042 acyloxymethyl group Chemical group 0.000 description 5
• 238000009835 boiling Methods 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• LWBHHRRTOZQPDM-UHFFFAOYSA-N Undecanedioic acid Natural products OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 4
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
• 239000003242 anti bacterial agent Substances 0.000 description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
• GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 206010017533 Fungal infection Diseases 0.000 description 3
• 208000031888 Mycoses Diseases 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 208000036142 Viral infection Diseases 0.000 description 3
• 238000010521 absorption reaction Methods 0.000 description 3
• 239000013543 active substance Substances 0.000 description 3
• 230000000844 anti-bacterial effect Effects 0.000 description 3
• 150000001535 azelaic acid derivatives Chemical class 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• BOXZXICVMMSYPE-UHFFFAOYSA-N chloromethyl benzoate Chemical compound ClCOC(=O)C1=CC=CC=C1 BOXZXICVMMSYPE-UHFFFAOYSA-N 0.000 description 3
• BDPZFQLKFUONAG-UHFFFAOYSA-N chloromethyl butanoate Chemical compound CCCC(=O)OCCl BDPZFQLKFUONAG-UHFFFAOYSA-N 0.000 description 3
• HNUBMUSOXKDQIN-UHFFFAOYSA-N chloromethyl hexanoate Chemical compound CCCCCC(=O)OCCl HNUBMUSOXKDQIN-UHFFFAOYSA-N 0.000 description 3
• JRCUJOMLYAQHDP-UHFFFAOYSA-N chloromethyl octanoate Chemical compound CCCCCCCC(=O)OCCl JRCUJOMLYAQHDP-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
• 238000005886 esterification reaction Methods 0.000 description 3
• 235000019441 ethanol Nutrition 0.000 description 3
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 239000013589 supplement Substances 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• 230000000699 topical effect Effects 0.000 description 3
• GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
• MTRYLAXNDGUFAK-UHFFFAOYSA-N 9-ethoxy-9-oxononanoic acid Chemical compound CCOC(=O)CCCCCCCC(O)=O MTRYLAXNDGUFAK-UHFFFAOYSA-N 0.000 description 2
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• 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 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• 241001303601 Rosacea Species 0.000 description 2
• 208000000453 Skin Neoplasms Diseases 0.000 description 2
• 241000191967 Staphylococcus aureus Species 0.000 description 2
• 239000004098 Tetracycline Substances 0.000 description 2
• 206010052428 Wound Diseases 0.000 description 2
• 208000027418 Wounds and injury Diseases 0.000 description 2
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
• 125000002252 acyl group Chemical group 0.000 description 2
• 125000004423 acyloxy group Chemical group 0.000 description 2
• 239000001361 adipic acid Substances 0.000 description 2
• 229960000250 adipic acid Drugs 0.000 description 2
• 235000011037 adipic acid Nutrition 0.000 description 2
• 229940088710 antibiotic agent Drugs 0.000 description 2
• 229940121375 antifungal agent Drugs 0.000 description 2
• 239000003429 antifungal agent Substances 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 125000004429 atom Chemical class 0.000 description 2
• 230000001580 bacterial effect Effects 0.000 description 2
• 230000009286 beneficial effect Effects 0.000 description 2
• ZGMKAGLKMYQEAS-UHFFFAOYSA-N bis(1-ethoxycarbonyloxyethyl) dodecanedioate Chemical compound CCOC(=O)OC(C)OC(=O)CCCCCCCCCCC(=O)OC(C)OC(=O)OCC ZGMKAGLKMYQEAS-UHFFFAOYSA-N 0.000 description 2
• KWYYRKXVCJMOEH-UHFFFAOYSA-N bis(1-ethoxycarbonyloxyethyl) nonanedioate Chemical compound CCOC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC(C)OC(=O)OCC KWYYRKXVCJMOEH-UHFFFAOYSA-N 0.000 description 2
• VIZVLPZQRVYRKQ-UHFFFAOYSA-N bis(2,2-dimethylpropanoyloxymethyl) dodecanedioate Chemical compound CC(C)(C)C(=O)OCOC(=O)CCCCCCCCCCC(=O)OCOC(=O)C(C)(C)C VIZVLPZQRVYRKQ-UHFFFAOYSA-N 0.000 description 2
• GLQNWJPLECTESO-UHFFFAOYSA-N bis(2,2-dimethylpropanoyloxymethyl) nonanedioate Chemical compound CC(C)(C)C(=O)OCOC(=O)CCCCCCCC(=O)OCOC(=O)C(C)(C)C GLQNWJPLECTESO-UHFFFAOYSA-N 0.000 description 2
• RGRPTPCDRBTWHF-UHFFFAOYSA-N bis(butanoyloxymethyl) nonanedioate Chemical compound CCCC(=O)OCOC(=O)CCCCCCCC(=O)OCOC(=O)CCC RGRPTPCDRBTWHF-UHFFFAOYSA-N 0.000 description 2
• VQBKJEPAVHPNFG-UHFFFAOYSA-N bis(hexanoyloxymethyl) nonanedioate Chemical compound CCCCCC(=O)OCOC(=O)CCCCCCCC(=O)OCOC(=O)CCCCC VQBKJEPAVHPNFG-UHFFFAOYSA-N 0.000 description 2
• FFXWOWIBGNGUDM-UHFFFAOYSA-N bis(octanoyloxymethyl) nonanedioate Chemical compound CCCCCCCC(=O)OCOC(=O)CCCCCCCC(=O)OCOC(=O)CCCCCCC FFXWOWIBGNGUDM-UHFFFAOYSA-N 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 210000004027 cell Anatomy 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
• 201000010099 disease Diseases 0.000 description 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
• 239000003623 enhancer Substances 0.000 description 2
• 230000032050 esterification Effects 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 150000004820 halides Chemical group 0.000 description 2
• ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
• 229940088597 hormone Drugs 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
• 229960000282 metronidazole Drugs 0.000 description 2
• VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 2
• 239000004570 mortar (masonry) Substances 0.000 description 2
• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
• 239000012044 organic layer Substances 0.000 description 2
• 238000007911 parenteral administration Methods 0.000 description 2
• ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 2
• 238000002428 photodynamic therapy Methods 0.000 description 2
• WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
• 230000002265 prevention Effects 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
• 201000000849 skin cancer Diseases 0.000 description 2
• 208000017520 skin disease Diseases 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
• 235000019364 tetracycline Nutrition 0.000 description 2
• 150000003522 tetracyclines Chemical class 0.000 description 2
• 229940040944 tetracyclines Drugs 0.000 description 2
• HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000009385 viral infection Effects 0.000 description 2
• XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
• ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
• OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 description 1
• VQEZDLXEVJCRMO-UHFFFAOYSA-N 1-chloroethyl 2,2-dimethylpropanoate Chemical compound CC(Cl)OC(=O)C(C)(C)C VQEZDLXEVJCRMO-UHFFFAOYSA-N 0.000 description 1
• LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
• DLZCDMPHHUODDO-UHFFFAOYSA-N 10-ethoxy-10-oxodecanoic acid Chemical compound CCOC(=O)CCCCCCCCC(O)=O DLZCDMPHHUODDO-UHFFFAOYSA-N 0.000 description 1
• JRAJFOOHBONEIT-UHFFFAOYSA-N 12-o-(1-ethoxycarbonyloxyethyl) 1-o-methyl dodecanedioate Chemical compound CCOC(=O)OC(C)OC(=O)CCCCCCCCCCC(=O)OC JRAJFOOHBONEIT-UHFFFAOYSA-N 0.000 description 1
• YFMCDZHMTTZHJN-UHFFFAOYSA-N 12-o-(2,2-dimethylpropanoyloxymethyl) 1-o-methyl dodecanedioate Chemical compound COC(=O)CCCCCCCCCCC(=O)OCOC(=O)C(C)(C)C YFMCDZHMTTZHJN-UHFFFAOYSA-N 0.000 description 1
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• NFHACVZNHAOSIG-UHFFFAOYSA-N bis(1-butanoyloxyethyl) nonanedioate Chemical compound CCCC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC(C)OC(=O)CCC NFHACVZNHAOSIG-UHFFFAOYSA-N 0.000 description 1
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• JCGWCCLZOJZVJY-UHFFFAOYSA-N bis(1-butanoyloxyethyl) undecanedioate Chemical compound CCCC(=O)OC(C)OC(=O)CCCCCCCCCC(=O)OC(C)OC(=O)CCC JCGWCCLZOJZVJY-UHFFFAOYSA-N 0.000 description 1
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• VEPXHAQQOJFEQM-UHFFFAOYSA-N bis(1-ethoxycarbonyloxyethyl) hexanedioate Chemical compound CCOC(=O)OC(C)OC(=O)CCCCC(=O)OC(C)OC(=O)OCC VEPXHAQQOJFEQM-UHFFFAOYSA-N 0.000 description 1
• SERBYSKHDHPOBQ-UHFFFAOYSA-N bis(1-ethoxycarbonyloxyethyl) octanedioate Chemical compound CCOC(=O)OC(C)OC(=O)CCCCCCC(=O)OC(C)OC(=O)OCC SERBYSKHDHPOBQ-UHFFFAOYSA-N 0.000 description 1
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• ISZKAEHTVQGFJL-UHFFFAOYSA-N bis(1-methoxycarbonyloxyethyl) decanedioate Chemical compound COC(=O)OC(C)OC(=O)CCCCCCCCC(=O)OC(C)OC(=O)OC ISZKAEHTVQGFJL-UHFFFAOYSA-N 0.000 description 1
• GWUKFJUKWIRIJA-UHFFFAOYSA-N bis(1-methoxycarbonyloxyethyl) dodecanedioate Chemical compound COC(=O)OC(C)OC(=O)CCCCCCCCCCC(=O)OC(C)OC(=O)OC GWUKFJUKWIRIJA-UHFFFAOYSA-N 0.000 description 1
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• RLFTUZWNMWZOAF-UHFFFAOYSA-N bis(1-methoxycarbonyloxyethyl) hexanedioate Chemical compound COC(=O)OC(C)OC(=O)CCCCC(=O)OC(C)OC(=O)OC RLFTUZWNMWZOAF-UHFFFAOYSA-N 0.000 description 1
• GUVCTGDBMYAGLD-UHFFFAOYSA-N bis(1-methoxycarbonyloxyethyl) nonanedioate Chemical compound COC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC(C)OC(=O)OC GUVCTGDBMYAGLD-UHFFFAOYSA-N 0.000 description 1
• SZPMDXDAYKMSIP-UHFFFAOYSA-N bis(1-methoxycarbonyloxyethyl) octanedioate Chemical compound COC(=O)OC(C)OC(=O)CCCCCCC(=O)OC(C)OC(=O)OC SZPMDXDAYKMSIP-UHFFFAOYSA-N 0.000 description 1
• XRBCSBJZKRYRCP-UHFFFAOYSA-N bis(1-methoxycarbonyloxyethyl) undecanedioate Chemical compound COC(=O)OC(C)OC(=O)CCCCCCCCCC(=O)OC(C)OC(=O)OC XRBCSBJZKRYRCP-UHFFFAOYSA-N 0.000 description 1
• XCLAKRCREMDPQE-UHFFFAOYSA-N bis(1-octadecanoyloxyethyl) decanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)OC(=O)CCCCCCCCC(=O)OC(C)OC(=O)CCCCCCCCCCCCCCCCC XCLAKRCREMDPQE-UHFFFAOYSA-N 0.000 description 1
• QNQNJVSSDVVCMC-UHFFFAOYSA-N bis(1-octadecanoyloxyethyl) dodecanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)OC(=O)CCCCCCCCCCC(=O)OC(C)OC(=O)CCCCCCCCCCCCCCCCC QNQNJVSSDVVCMC-UHFFFAOYSA-N 0.000 description 1
• JDRQZNPLZGALAX-UHFFFAOYSA-N bis(1-octadecanoyloxyethyl) heptanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)OC(=O)CCCCCC(=O)OC(C)OC(=O)CCCCCCCCCCCCCCCCC JDRQZNPLZGALAX-UHFFFAOYSA-N 0.000 description 1
• QEVAVGINWMTAHB-UHFFFAOYSA-N bis(1-octadecanoyloxyethyl) hexanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)OC(=O)CCCCC(=O)OC(C)OC(=O)CCCCCCCCCCCCCCCCC QEVAVGINWMTAHB-UHFFFAOYSA-N 0.000 description 1
• AFRSXVBVNJHWAN-UHFFFAOYSA-N bis(1-octadecanoyloxyethyl) nonanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC(C)OC(=O)CCCCCCCCCCCCCCCCC AFRSXVBVNJHWAN-UHFFFAOYSA-N 0.000 description 1
• HIIXFSRFUFJQGY-UHFFFAOYSA-N bis(1-octadecanoyloxyethyl) octanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)OC(=O)CCCCCCC(=O)OC(C)OC(=O)CCCCCCCCCCCCCCCCC HIIXFSRFUFJQGY-UHFFFAOYSA-N 0.000 description 1
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• IAHPOJPPZUOETA-UHFFFAOYSA-N bis(1-phenylmethoxycarbonyloxyethyl) heptanedioate Chemical compound C=1C=CC=CC=1COC(=O)OC(C)OC(=O)CCCCCC(=O)OC(C)OC(=O)OCC1=CC=CC=C1 IAHPOJPPZUOETA-UHFFFAOYSA-N 0.000 description 1
• ULPCJNAMCGQNQZ-UHFFFAOYSA-N bis(1-phenylmethoxycarbonyloxyethyl) nonanedioate Chemical compound C=1C=CC=CC=1COC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC(C)OC(=O)OCC1=CC=CC=C1 ULPCJNAMCGQNQZ-UHFFFAOYSA-N 0.000 description 1
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• OPFZZLAORDBVMX-UHFFFAOYSA-N bis(1-propanoyloxyethyl) dodecanedioate Chemical compound CCC(=O)OC(C)OC(=O)CCCCCCCCCCC(=O)OC(C)OC(=O)CC OPFZZLAORDBVMX-UHFFFAOYSA-N 0.000 description 1
• CZCHSSPHBGGNPM-UHFFFAOYSA-N bis(1-propanoyloxyethyl) heptanedioate Chemical compound CCC(=O)OC(C)OC(=O)CCCCCC(=O)OC(C)OC(=O)CC CZCHSSPHBGGNPM-UHFFFAOYSA-N 0.000 description 1
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• LYRBHYYPDPKSRB-UHFFFAOYSA-N bis(1-propanoyloxyethyl) nonanedioate Chemical compound CCC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC(C)OC(=O)CC LYRBHYYPDPKSRB-UHFFFAOYSA-N 0.000 description 1
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• RJDDMZMOBUXUED-UHFFFAOYSA-N bis(1-propanoyloxyethyl) undecanedioate Chemical compound CCC(=O)OC(C)OC(=O)CCCCCCCCCC(=O)OC(C)OC(=O)CC RJDDMZMOBUXUED-UHFFFAOYSA-N 0.000 description 1
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• LPGIISCUQDIEFM-UHFFFAOYSA-N bis(2,2-dimethylpropanoyloxymethyl) octanedioate Chemical compound CC(C)(C)C(=O)OCOC(=O)CCCCCCC(=O)OCOC(=O)C(C)(C)C LPGIISCUQDIEFM-UHFFFAOYSA-N 0.000 description 1
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• FHMSRJSXZKYXMX-UHFFFAOYSA-N bis(acetyloxymethyl) octanedioate Chemical compound CC(=O)OCOC(=O)CCCCCCC(=O)OCOC(C)=O FHMSRJSXZKYXMX-UHFFFAOYSA-N 0.000 description 1
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• CLVICYYERAJNHK-UHFFFAOYSA-N bis(octadecanoyloxymethyl) decanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCOC(=O)CCCCCCCCC(=O)OCOC(=O)CCCCCCCCCCCCCCCCC CLVICYYERAJNHK-UHFFFAOYSA-N 0.000 description 1
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• QZCUADBRCKDFHJ-UHFFFAOYSA-N bis(octadecanoyloxymethyl) hexanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCOC(=O)CCCCC(=O)OCOC(=O)CCCCCCCCCCCCCCCCC QZCUADBRCKDFHJ-UHFFFAOYSA-N 0.000 description 1
• BUDHRBODNRRTGD-UHFFFAOYSA-N bis(octadecanoyloxymethyl) nonanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCOC(=O)CCCCCCCC(=O)OCOC(=O)CCCCCCCCCCCCCCCCC BUDHRBODNRRTGD-UHFFFAOYSA-N 0.000 description 1
• JKNFZWWSHKFNJN-UHFFFAOYSA-N bis(octadecanoyloxymethyl) octanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCOC(=O)CCCCCCC(=O)OCOC(=O)CCCCCCCCCCCCCCCCC JKNFZWWSHKFNJN-UHFFFAOYSA-N 0.000 description 1
• XTJXLFOEDDXZTA-UHFFFAOYSA-N bis(octadecanoyloxymethyl) undecanedioate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCOC(=O)CCCCCCCCCC(=O)OCOC(=O)CCCCCCCCCCCCCCCCC XTJXLFOEDDXZTA-UHFFFAOYSA-N 0.000 description 1
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• HEBIXKONUKIERF-UHFFFAOYSA-N bis(octanoyloxymethyl) hexanedioate Chemical compound CCCCCCCC(=O)OCOC(=O)CCCCC(=O)OCOC(=O)CCCCCCC HEBIXKONUKIERF-UHFFFAOYSA-N 0.000 description 1
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• PTTIGCNOGZPKAR-UHFFFAOYSA-N bis(octanoyloxymethyl) undecanedioate Chemical compound CCCCCCCC(=O)OCOC(=O)CCCCCCCCCC(=O)OCOC(=O)CCCCCCC PTTIGCNOGZPKAR-UHFFFAOYSA-N 0.000 description 1
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