TW201138832A - Salicylate fatty acid derivatives - Google Patents
Salicylate fatty acid derivatives Download PDFInfo
- Publication number
- TW201138832A TW201138832A TW100102111A TW100102111A TW201138832A TW 201138832 A TW201138832 A TW 201138832A TW 100102111 A TW100102111 A TW 100102111A TW 100102111 A TW100102111 A TW 100102111A TW 201138832 A TW201138832 A TW 201138832A
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- Prior art keywords
- group
- compound
- alkyl
- ethyl
- alkenyl
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 title description 9
- 229960001860 salicylate Drugs 0.000 title description 9
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 441
- 239000000203 mixture Substances 0.000 claims abstract description 85
- -1 e.g. Chemical class 0.000 claims abstract description 68
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims abstract description 36
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 29
- 230000004054 inflammatory process Effects 0.000 claims abstract description 23
- 206010061218 Inflammation Diseases 0.000 claims abstract description 21
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 20
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 20
- 235000012000 cholesterol Nutrition 0.000 claims abstract description 18
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 12
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 12
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 7
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 7
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 7
- 210000004369 blood Anatomy 0.000 claims abstract description 7
- 239000008280 blood Substances 0.000 claims abstract description 7
- 230000002093 peripheral effect Effects 0.000 claims abstract description 6
- 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 203
- 125000000217 alkyl group Chemical group 0.000 claims description 182
- 239000005711 Benzoic acid Substances 0.000 claims description 98
- 235000010233 benzoic acid Nutrition 0.000 claims description 98
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 81
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 57
- 229960004889 salicylic acid Drugs 0.000 claims description 56
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 47
- 125000003342 alkenyl group Chemical group 0.000 claims description 46
- 238000002360 preparation method Methods 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 150000001412 amines Chemical class 0.000 claims description 38
- 125000004494 ethyl ester group Chemical group 0.000 claims description 38
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 37
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 37
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000004414 alkyl thio group Chemical group 0.000 claims description 35
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 35
- 239000000651 prodrug Substances 0.000 claims description 34
- 229940002612 prodrug Drugs 0.000 claims description 34
- 239000012453 solvate Substances 0.000 claims description 34
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 32
- 125000003277 amino group Chemical group 0.000 claims description 31
- 125000006612 decyloxy group Chemical group 0.000 claims description 31
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 27
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 150000003973 alkyl amines Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000001273 butane Substances 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 230000002159 abnormal effect Effects 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 7
- 230000000968 intestinal effect Effects 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 5
- 125000006309 butyl amino group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 229960000581 salicylamide Drugs 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002355 alkine group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 3
- 150000002602 lanthanoids Chemical class 0.000 claims description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
- 238000008214 LDL Cholesterol Methods 0.000 claims description 2
- 108010069201 VLDL Cholesterol Proteins 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 17
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 11
- 150000002923 oximes Chemical class 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004913 2-ethylbutylamino group Chemical group C(C)C(CN*)CC 0.000 claims 1
- SNFLTPWPGDPHFR-UHFFFAOYSA-N C(C=1C(O)=CC=CC1)(=O)O.C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound C(C=1C(O)=CC=CC1)(=O)O.C1=CC=CC=2C3=CC=CC=C3CC12 SNFLTPWPGDPHFR-UHFFFAOYSA-N 0.000 claims 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 1
- 241000239226 Scorpiones Species 0.000 claims 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 235000021286 stilbenes Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 76
- 150000003873 salicylate salts Chemical class 0.000 abstract description 17
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 11
- 229930195729 fatty acid Natural products 0.000 abstract description 11
- 239000000194 fatty acid Substances 0.000 abstract description 11
- 150000004665 fatty acids Chemical class 0.000 abstract description 11
- 108010010234 HDL Lipoproteins Proteins 0.000 abstract description 9
- 150000002632 lipids Chemical class 0.000 abstract description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 abstract description 4
- 150000003626 triacylglycerols Chemical class 0.000 abstract description 4
- 108010023302 HDL Cholesterol Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
- 229960004365 benzoic acid Drugs 0.000 description 91
- 125000006239 protecting group Chemical group 0.000 description 81
- 235000019439 ethyl acetate Nutrition 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 53
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 41
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- 238000000132 electrospray ionisation Methods 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000011734 sodium Substances 0.000 description 30
- 239000002585 base Substances 0.000 description 29
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 27
- 210000004027 cell Anatomy 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000003818 flash chromatography Methods 0.000 description 22
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 235000019253 formic acid Nutrition 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 19
- 239000007788 liquid Substances 0.000 description 18
- 101150041968 CDC13 gene Proteins 0.000 description 17
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000002757 inflammatory effect Effects 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 201000010099 disease Diseases 0.000 description 14
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 14
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229940024606 amino acid Drugs 0.000 description 12
- 235000001014 amino acid Nutrition 0.000 description 12
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 12
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 238000007429 general method Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 9
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- 102000015779 HDL Lipoproteins Human genes 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 208000008589 Obesity Diseases 0.000 description 7
- 239000012317 TBTU Substances 0.000 description 7
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 235000020824 obesity Nutrition 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 230000037361 pathway Effects 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 150000004677 hydrates Chemical class 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- 229910052727 yttrium Inorganic materials 0.000 description 6
- VHBSECWYEFJRNV-UHFFFAOYSA-N 2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.OC(=O)C1=CC=CC=C1O VHBSECWYEFJRNV-UHFFFAOYSA-N 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 229940050390 benzoate Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 208000037976 chronic inflammation Diseases 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- MXUHMQZOATZRIK-UHFFFAOYSA-N methyl 5-amino-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1O MXUHMQZOATZRIK-UHFFFAOYSA-N 0.000 description 5
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 4
- 208000032843 Hemorrhage Diseases 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/60—Unsaturated compounds containing ether groups, groups, groups, or groups the non-carboxylic part of the ether being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
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- Engineering & Computer Science (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29671710P | 2010-01-20 | 2010-01-20 |
Publications (1)
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| TW201138832A true TW201138832A (en) | 2011-11-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100102111A TW201138832A (en) | 2010-01-20 | 2011-01-20 | Salicylate fatty acid derivatives |
Country Status (7)
| Country | Link |
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| US (1) | US20130046013A1 (enExample) |
| EP (1) | EP2526084A1 (enExample) |
| JP (1) | JP2013517322A (enExample) |
| CN (1) | CN102822141A (enExample) |
| AR (1) | AR079957A1 (enExample) |
| TW (1) | TW201138832A (enExample) |
| WO (1) | WO2011089529A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2217224B1 (en) | 2007-11-09 | 2019-05-08 | Basf As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| US9085527B2 (en) | 2008-07-08 | 2015-07-21 | Catabasis Pharmaceuticals, Inc. | Fatty acid acylated salicylates and their uses |
| NZ590179A (en) | 2008-07-08 | 2012-12-21 | Catabasis Pharmaceuticals Inc | Fatty acid acetylated salicylates, diflunisal or triflusal and their uses |
| EP2147910A1 (en) | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| PL2427415T3 (pl) | 2009-05-08 | 2019-09-30 | Basf As | Wielonienasycone kwasy tłuszczowe do leczenia chorób związanych z dziedziną chorób sercowo-naczyniowych, metabolicznych i zapalnych |
| NZ610705A (en) * | 2010-11-05 | 2014-10-31 | Pronova Biopharma Norge As | Methods of treatment using lipid compounds |
| KR102213143B1 (ko) | 2013-02-28 | 2021-02-08 | 바스프 에이에스 | 지방질 화합물, 트리글리세리드 및 계면활성제를 포함하는 조성물 및 이를 이용하는 방법 |
| EP2889286B1 (en) * | 2013-12-30 | 2016-05-18 | Pax Forschung GmbH | Pharmaceutically active compound for use as anti-inflammatory agent |
| BR112017023164A2 (en) | 2015-04-28 | 2018-07-24 | Pronova Biopharma Norge As | and method of preventing and / or treating non-alcoholic steatohepatitis in an individual in need thereof |
| BR112020011431A2 (pt) | 2017-12-06 | 2020-11-24 | Basf As | derivados de ácido graxo para o tratamento de esteato-hepatite não alcoólica |
| WO2019224602A2 (en) | 2018-05-23 | 2019-11-28 | Northsea Therapeutics B.V. | Structurally modified fatty acids for improving glycemic control and treating inflammatory bowel disease |
| CN116829139A (zh) | 2020-12-22 | 2023-09-29 | 北海医疗私人有限公司 | 用于治疗非酒精性脂肪性肝炎的包含含氧的结构增强的脂肪酸的联合治疗剂 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036951A (en) * | 1973-03-12 | 1977-07-19 | Synergistics, Inc. | Ultra-violet filtration with certain aminosalicylic acid esters |
| US4264517A (en) * | 1978-12-11 | 1981-04-28 | G.D. Searle & Co. | Alkylphenyl 5Z,8Z,11Z,14Z,17Z-eicosapentaenoates |
| GB9403857D0 (en) * | 1994-03-01 | 1994-04-20 | Scotia Holdings Plc | Fatty acid derivatives |
| US20090286803A1 (en) * | 2006-04-07 | 2009-11-19 | Manley Paul W | Combination comprising a) a pyrimidylaminobenzamide compound, and b) a thr315lle kinase inhibitor |
| US8987329B2 (en) * | 2006-04-12 | 2015-03-24 | Conopco, Inc. | Oral composition comprising a polyunsaturated fatty acid and salicylic acid for obtaining an antiinflammatory effect in skin |
| NZ590179A (en) * | 2008-07-08 | 2012-12-21 | Catabasis Pharmaceuticals Inc | Fatty acid acetylated salicylates, diflunisal or triflusal and their uses |
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- 2011-01-20 JP JP2012549443A patent/JP2013517322A/ja not_active Withdrawn
- 2011-01-20 TW TW100102111A patent/TW201138832A/zh unknown
- 2011-01-20 CN CN2011800145715A patent/CN102822141A/zh active Pending
- 2011-01-20 EP EP11734428A patent/EP2526084A1/en not_active Withdrawn
- 2011-01-20 WO PCT/IB2011/000250 patent/WO2011089529A1/en not_active Ceased
Also Published As
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| US20130046013A1 (en) | 2013-02-21 |
| CN102822141A (zh) | 2012-12-12 |
| EP2526084A1 (en) | 2012-11-28 |
| JP2013517322A (ja) | 2013-05-16 |
| AR079957A1 (es) | 2012-02-29 |
| WO2011089529A1 (en) | 2011-07-28 |
| WO2011089529A4 (en) | 2011-10-27 |
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