AU2002343086C1 - Double esters - Google Patents
Double esters Download PDFInfo
- Publication number
- AU2002343086C1 AU2002343086C1 AU2002343086A AU2002343086A AU2002343086C1 AU 2002343086 C1 AU2002343086 C1 AU 2002343086C1 AU 2002343086 A AU2002343086 A AU 2002343086A AU 2002343086 A AU2002343086 A AU 2002343086A AU 2002343086 C1 AU2002343086 C1 AU 2002343086C1
- Authority
- AU
- Australia
- Prior art keywords
- group
- ester
- compound
- optionally substituted
- optionally
- 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.)
- Ceased
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- 150000002148 esters Chemical class 0.000 title claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000003814 drug Substances 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 4
- 230000000069 prophylactic effect Effects 0.000 claims abstract description 3
- -1 1-(acetyloxy) ethyl nonanedioate Chemical compound 0.000 claims description 97
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 238000011282 treatment Methods 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 229940088679 drug related substance Drugs 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 10
- 206010000496 acne Diseases 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 208000000069 hyperpigmentation Diseases 0.000 claims description 8
- 230000003810 hyperpigmentation Effects 0.000 claims description 8
- 208000035143 Bacterial infection Diseases 0.000 claims description 7
- 206010017533 Fungal infection Diseases 0.000 claims description 7
- 208000031888 Mycoses Diseases 0.000 claims description 7
- 208000036142 Viral infection Diseases 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 230000001580 bacterial effect Effects 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 230000029663 wound healing Effects 0.000 claims description 6
- 206010004146 Basal cell carcinoma Diseases 0.000 claims description 5
- 208000009621 actinic keratosis Diseases 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000009385 viral infection 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
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000002538 fungal effect Effects 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
- 241000894007 species Species 0.000 claims description 3
- 230000003612 virological effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 239000000203 mixture Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 25
- 229960002255 azelaic acid Drugs 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 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
- 239000002253 acid Substances 0.000 description 15
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 15
- 101150041968 CDC13 gene Proteins 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- 229960004132 diethyl ether Drugs 0.000 description 13
- WLJVNTCWHIRURA-UHFFFAOYSA-L pimelate(2-) Chemical compound [O-]C(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-L 0.000 description 13
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- BDJRBEYXGGNYIS-UHFFFAOYSA-L azelaate(2-) Chemical compound [O-]C(=O)CCCCCCCC([O-])=O BDJRBEYXGGNYIS-UHFFFAOYSA-L 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 150000001991 dicarboxylic acids Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 7
- VVWPSAPZUZXYCM-UHFFFAOYSA-N 9-methoxy-9-oxononanoic acid Chemical compound COC(=O)CCCCCCCC(O)=O VVWPSAPZUZXYCM-UHFFFAOYSA-N 0.000 description 6
- 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
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 6
- 239000002674 ointment Substances 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 230000000844 anti-bacterial effect Effects 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
- TVIDDXQYHWJXFK-UHFFFAOYSA-L dodecanedioate(2-) Chemical compound [O-]C(=O)CCCCCCCCCCC([O-])=O TVIDDXQYHWJXFK-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-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
- 239000013543 active substance Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 150000001535 azelaic acid derivatives Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 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
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000011734 sodium 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
- 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
- YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-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
- YJXXJQBXZYMNIA-UHFFFAOYSA-N 9-o-(1-ethoxycarbonyloxyethyl) 1-o-methyl nonanedioate Chemical compound CCOC(=O)OC(C)OC(=O)CCCCCCCC(=O)OC YJXXJQBXZYMNIA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 208000000453 Skin Neoplasms Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- KOBGCLDFHALTFW-UHFFFAOYSA-N bis(benzoyloxymethyl) nonanedioate Chemical compound C=1C=CC=CC=1C(=O)OCOC(=O)CCCCCCCC(=O)OCOC(=O)C1=CC=CC=C1 KOBGCLDFHALTFW-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- BOXZXICVMMSYPE-UHFFFAOYSA-N chloromethyl benzoate Chemical compound ClCOC(=O)C1=CC=CC=C1 BOXZXICVMMSYPE-UHFFFAOYSA-N 0.000 description 2
- BDPZFQLKFUONAG-UHFFFAOYSA-N chloromethyl butanoate Chemical compound CCCC(=O)OCCl BDPZFQLKFUONAG-UHFFFAOYSA-N 0.000 description 2
- HNUBMUSOXKDQIN-UHFFFAOYSA-N chloromethyl hexanoate Chemical compound CCCCCC(=O)OCCl HNUBMUSOXKDQIN-UHFFFAOYSA-N 0.000 description 2
- JRCUJOMLYAQHDP-UHFFFAOYSA-N chloromethyl octanoate Chemical compound CCCCCCCC(=O)OCCl JRCUJOMLYAQHDP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 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
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 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
- 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
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000002829 reductive effect Effects 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000003826 tablet 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
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-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
- 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
- 125000004169 (C1-C6) alkyl 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
- 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
- WMEOLZWYNYCSPY-UHFFFAOYSA-N 11-o-(1-ethoxycarbonyloxyethyl) 1-o-methyl undecanedioate Chemical compound CCOC(=O)OC(C)OC(=O)CCCCCCCCCC(=O)OC WMEOLZWYNYCSPY-UHFFFAOYSA-N 0.000 description 1
- MPHQJALYFXXXGG-UHFFFAOYSA-N 12-(1-butanoyloxyethoxy)-12-oxododecanoic acid Chemical compound CCCC(=O)OC(C)OC(=O)CCCCCCCCCCC(O)=O MPHQJALYFXXXGG-UHFFFAOYSA-N 0.000 description 1
- GLWMPDJJIHGQMQ-UHFFFAOYSA-N 12-(benzoyloxymethoxy)-12-oxododecanoic acid Chemical compound OC(=O)CCCCCCCCCCC(=O)OCOC(=O)C1=CC=CC=C1 GLWMPDJJIHGQMQ-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- REGGDLIBDASKGE-UHFFFAOYSA-N 12-methoxy-12-oxododecanoic acid Chemical compound COC(=O)CCCCCCCCCCC(O)=O REGGDLIBDASKGE-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
- FVWNZPYOCVUKQI-UHFFFAOYSA-N 12-oxo-12-(propanoyloxymethoxy)dodecanoic acid Chemical compound CCC(=O)OCOC(=O)CCCCCCCCCCC(O)=O FVWNZPYOCVUKQI-UHFFFAOYSA-N 0.000 description 1
- XRMYUQMWGXOOJL-UHFFFAOYSA-N 12-oxo-12-[(2,2,2-trifluoroacetyl)oxymethoxy]dodecanoic acid Chemical compound OC(=O)CCCCCCCCCCC(=O)OCOC(=O)C(F)(F)F XRMYUQMWGXOOJL-UHFFFAOYSA-N 0.000 description 1
- QTUZLIDZMITBNU-UHFFFAOYSA-N 12-oxo-12-[1-(2,2,2-trifluoroacetyl)oxyethoxy]dodecanoic acid Chemical compound FC(F)(F)C(=O)OC(C)OC(=O)CCCCCCCCCCC(O)=O QTUZLIDZMITBNU-UHFFFAOYSA-N 0.000 description 1
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- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/50—Sebacic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/44—Adipic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/48—Azelaic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Toxicology (AREA)
- Virology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Tires In General (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0128052.8 | 2001-11-22 | ||
| GBGB0128052.8A GB0128052D0 (en) | 2001-11-22 | 2001-11-22 | Compounds |
| PCT/GB2002/005305 WO2003045893A1 (en) | 2001-11-22 | 2002-11-22 | Double esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2002343086A1 AU2002343086A1 (en) | 2003-06-10 |
| AU2002343086B2 AU2002343086B2 (en) | 2008-01-03 |
| AU2002343086C1 true AU2002343086C1 (en) | 2008-06-26 |
Family
ID=9926289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002343086A Ceased AU2002343086C1 (en) | 2001-11-22 | 2002-11-22 | Double esters |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7629383B2 (https=) |
| EP (1) | EP1448508B1 (https=) |
| JP (1) | JP4426298B2 (https=) |
| KR (1) | KR20040071138A (https=) |
| CN (1) | CN100516018C (https=) |
| AT (1) | ATE443695T1 (https=) |
| AU (1) | AU2002343086C1 (https=) |
| CA (1) | CA2467773C (https=) |
| DE (1) | DE60233819D1 (https=) |
| GB (1) | GB0128052D0 (https=) |
| HU (1) | HUP0402122A2 (https=) |
| MX (1) | MXPA04004763A (https=) |
| NO (1) | NO20042603L (https=) |
| RU (1) | RU2350599C2 (https=) |
| WO (1) | WO2003045893A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0018528D0 (en) | 2000-07-27 | 2000-09-13 | Photocure Asa | Compounds |
| DE102006004804A1 (de) * | 2006-01-23 | 2007-07-26 | Intendis Gmbh | Verwendung von Alkandicarbonsäuren und Retinoiden zur Behandlung entzündlicher Hauterkrankungen |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4462934A (en) | 1983-03-31 | 1984-07-31 | Pfizer Inc. | Bis-esters of dicarboxylic acids with amoxicillin and certain hydroxymethylpenicillanate 1,1-dioxides |
| EP0125781B1 (en) | 1983-04-14 | 1987-08-12 | Interox Chemicals Limited | Peroxygen compounds |
| GB8310080D0 (en) | 1983-04-14 | 1983-05-18 | Interox Chemicals Ltd | Bleach composition |
| ATE74359T1 (de) * | 1987-01-27 | 1992-04-15 | Pfizer | 6-beta(substituierte)-(s)hydroxymethylpenicillans|ure und deren derivate. |
| LU86918A1 (fr) * | 1987-06-12 | 1989-03-08 | Oreal | Nouveaux diesters de l'acide azelaique,leur procede de preparation,les compositions topiques les contenant et leur utilisation dans le traitement de l'acne |
| CA2107106A1 (en) | 1991-03-28 | 1992-09-29 | Jo Klaveness | Cross-linking agent |
| LV10396B (en) | 1992-03-06 | 1996-02-20 | Nycomed Imaging As | Novel contrast agents |
| GB9504948D0 (en) * | 1995-03-10 | 1995-04-26 | Norwegian Radium Hospital Rese | Compounds |
| JP4029440B2 (ja) | 1997-07-09 | 2008-01-09 | 大日本インキ化学工業株式会社 | 側鎖型ラジカル重合性化合物及びそれを用いた液晶デバイス |
-
2001
- 2001-11-22 GB GBGB0128052.8A patent/GB0128052D0/en not_active Ceased
-
2002
- 2002-11-22 US US10/496,328 patent/US7629383B2/en not_active Expired - Fee Related
- 2002-11-22 EP EP02779748A patent/EP1448508B1/en not_active Expired - Lifetime
- 2002-11-22 HU HU0402122A patent/HUP0402122A2/hu unknown
- 2002-11-22 RU RU2004118713/04A patent/RU2350599C2/ru not_active IP Right Cessation
- 2002-11-22 AT AT02779748T patent/ATE443695T1/de not_active IP Right Cessation
- 2002-11-22 JP JP2003547347A patent/JP4426298B2/ja not_active Expired - Fee Related
- 2002-11-22 CA CA2467773A patent/CA2467773C/en not_active Expired - Fee Related
- 2002-11-22 CN CNB028232739A patent/CN100516018C/zh not_active Expired - Fee Related
- 2002-11-22 AU AU2002343086A patent/AU2002343086C1/en not_active Ceased
- 2002-11-22 WO PCT/GB2002/005305 patent/WO2003045893A1/en not_active Ceased
- 2002-11-22 KR KR10-2004-7007220A patent/KR20040071138A/ko not_active Withdrawn
- 2002-11-22 DE DE60233819T patent/DE60233819D1/de not_active Expired - Lifetime
- 2002-11-22 MX MXPA04004763A patent/MXPA04004763A/es unknown
-
2004
- 2004-06-21 NO NO20042603A patent/NO20042603L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002343086B2 (en) | 2008-01-03 |
| ATE443695T1 (de) | 2009-10-15 |
| CN1589254A (zh) | 2005-03-02 |
| KR20040071138A (ko) | 2004-08-11 |
| US7629383B2 (en) | 2009-12-08 |
| CA2467773A1 (en) | 2003-06-05 |
| GB0128052D0 (en) | 2002-01-16 |
| JP4426298B2 (ja) | 2010-03-03 |
| AU2002343086A1 (en) | 2003-06-10 |
| RU2004118713A (ru) | 2005-03-27 |
| DE60233819D1 (de) | 2009-11-05 |
| EP1448508A1 (en) | 2004-08-25 |
| CA2467773C (en) | 2011-08-16 |
| WO2003045893A1 (en) | 2003-06-05 |
| JP2005510556A (ja) | 2005-04-21 |
| MXPA04004763A (es) | 2004-07-30 |
| US20050203181A1 (en) | 2005-09-15 |
| CN100516018C (zh) | 2009-07-22 |
| NO20042603L (no) | 2004-06-21 |
| HUP0402122A2 (hu) | 2005-02-28 |
| RU2350599C2 (ru) | 2009-03-27 |
| EP1448508B1 (en) | 2009-09-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA2 | Applications for amendment section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 24 DEC 2007. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: DRUG DISCOVERY LABORATORY AS Free format text: FORMER OWNER WAS: PHOTOCURE ASA |
|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 24 DEC 2007 |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |