NZ566045A - Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field - Google Patents
Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical fieldInfo
- Publication number
- NZ566045A NZ566045A NZ566045A NZ56604506A NZ566045A NZ 566045 A NZ566045 A NZ 566045A NZ 566045 A NZ566045 A NZ 566045A NZ 56604506 A NZ56604506 A NZ 56604506A NZ 566045 A NZ566045 A NZ 566045A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- aminophenyl
- cooh
- ethoxy
- propionic acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 92
- 150000003839 salts Chemical class 0.000 title claims description 8
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title claims description 7
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title claims description 7
- 102000001301 EGF receptor Human genes 0.000 title description 11
- 108060006698 EGF receptor Proteins 0.000 title description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 33
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- ZCPQQFGJWFYMDY-UHFFFAOYSA-N 3-(3-aminophenyl)-2-ethoxypropanoic acid Chemical compound CCOC(C(O)=O)CC1=CC=CC(N)=C1 ZCPQQFGJWFYMDY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 11
- 229940127007 Compound 39 Drugs 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- QLJYLJGYIDIJPT-UHFFFAOYSA-N 3-(4-aminophenyl)-2-methoxypropanoic acid Chemical compound COC(C(O)=O)CC1=CC=C(N)C=C1 QLJYLJGYIDIJPT-UHFFFAOYSA-N 0.000 claims description 10
- IIPURNWXORPFKN-UHFFFAOYSA-N 3-(4-aminophenyl)-2-ethoxypropanoic acid Chemical compound CCOC(C(O)=O)CC1=CC=C(N)C=C1 IIPURNWXORPFKN-UHFFFAOYSA-N 0.000 claims description 9
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims description 7
- ZACJOTJQNNJIOJ-UHFFFAOYSA-N 2-(3-aminophenyl)-2-ethoxyacetic acid Chemical compound CCOC(C(O)=O)C1=CC=CC(N)=C1 ZACJOTJQNNJIOJ-UHFFFAOYSA-N 0.000 claims description 7
- ZCGNGYOIRHSOJY-UHFFFAOYSA-N 2-(4-aminophenyl)-2-ethoxyacetic acid Chemical compound CCOC(C(O)=O)C1=CC=C(N)C=C1 ZCGNGYOIRHSOJY-UHFFFAOYSA-N 0.000 claims description 7
- GDWALNQPKHTANB-UHFFFAOYSA-N 2-(4-aminophenyl)-2-methoxyacetic acid Chemical compound COC(C(O)=O)C1=CC=C(N)C=C1 GDWALNQPKHTANB-UHFFFAOYSA-N 0.000 claims description 7
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims description 7
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229940125833 compound 23 Drugs 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 229940126639 Compound 33 Drugs 0.000 claims description 6
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims description 5
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 210000004291 uterus Anatomy 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
- 210000001072 colon Anatomy 0.000 claims description 4
- 210000003734 kidney Anatomy 0.000 claims description 4
- 210000000496 pancreas Anatomy 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 206010036784 proctocolitis Diseases 0.000 claims description 4
- 210000002307 prostate Anatomy 0.000 claims description 4
- 210000002784 stomach Anatomy 0.000 claims description 4
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims description 3
- 229940126208 compound 22 Drugs 0.000 claims description 3
- XZNZTIOSLTZRBY-UHFFFAOYSA-N COC(C)(C(O)=O)C1=CC=CC(N)=C1 Chemical compound COC(C)(C(O)=O)C1=CC=CC(N)=C1 XZNZTIOSLTZRBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 208000037841 lung tumor Diseases 0.000 claims 1
- 230000006020 chronic inflammation Effects 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 210000004027 cell Anatomy 0.000 description 40
- 239000007787 solid Substances 0.000 description 40
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 102000005962 receptors Human genes 0.000 description 22
- 108020003175 receptors Proteins 0.000 description 22
- 230000000694 effects Effects 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 13
- 229960004963 mesalazine Drugs 0.000 description 13
- 238000003032 molecular docking Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000010261 cell growth Effects 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 206010009944 Colon cancer Diseases 0.000 description 8
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000000539 amino acid group Chemical group 0.000 description 7
- 229940125810 compound 20 Drugs 0.000 description 7
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 238000002372 labelling Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000012091 fetal bovine serum Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- FUKCXXJPBOBGMI-YVMONPNESA-N (z)-2-hydroxy-3-(4-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C(\O)=C\C1=CC=C([N+]([O-])=O)C=C1 FUKCXXJPBOBGMI-YVMONPNESA-N 0.000 description 5
- VJUPBWYPUNQPRR-UHFFFAOYSA-N 2-hydroxy-3-(3-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C(O)=CC1=CC=CC([N+]([O-])=O)=C1 VJUPBWYPUNQPRR-UHFFFAOYSA-N 0.000 description 5
- GRTDDRVEWZAQCG-UHFFFAOYSA-N 3-(3-aminophenyl)-2-hydroxypropanoic acid Chemical compound NC1=CC=CC(CC(O)C(O)=O)=C1 GRTDDRVEWZAQCG-UHFFFAOYSA-N 0.000 description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
- 208000029742 colonic neoplasm Diseases 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 229960004586 rosiglitazone Drugs 0.000 description 5
- 238000002965 ELISA Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229940126601 medicinal product Drugs 0.000 description 4
- 238000000302 molecular modelling Methods 0.000 description 4
- 102000006255 nuclear receptors Human genes 0.000 description 4
- 108020004017 nuclear receptors Proteins 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- ODNSPFZFMYOBLW-UXBLZVDNSA-N (4e)-2-methyl-4-[(4-nitrophenyl)methylidene]-1,3-oxazol-5-one Chemical compound O=C1OC(C)=N\C1=C\C1=CC=C([N+]([O-])=O)C=C1 ODNSPFZFMYOBLW-UXBLZVDNSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000005623 Carcinogenesis Diseases 0.000 description 3
- 102000009024 Epidermal Growth Factor Human genes 0.000 description 3
- 108060001084 Luciferase Proteins 0.000 description 3
- 239000005089 Luciferase Substances 0.000 description 3
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 3
- 230000001028 anti-proliverative effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000036952 cancer formation Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 231100000504 carcinogenesis Toxicity 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001890 transfection Methods 0.000 description 3
- 238000010200 validation analysis Methods 0.000 description 3
- CSCYUKHWQGONIX-UHFFFAOYSA-N 2-(3-aminophenyl)-2-hydroxyacetic acid Chemical compound NC1=CC=CC(C(O)C(O)=O)=C1 CSCYUKHWQGONIX-UHFFFAOYSA-N 0.000 description 2
- SWFKDTNBFKVSMG-UHFFFAOYSA-N 2-(4-acetamidophenyl)-2-ethoxyacetic acid Chemical compound CCOC(C(O)=O)C1=CC=C(NC(C)=O)C=C1 SWFKDTNBFKVSMG-UHFFFAOYSA-N 0.000 description 2
- HRNDCXWNDGVALI-UHFFFAOYSA-N 2-(4-acetamidophenyl)-2-methoxyacetic acid Chemical compound COC(C(O)=O)C1=CC=C(NC(C)=O)C=C1 HRNDCXWNDGVALI-UHFFFAOYSA-N 0.000 description 2
- YJGSMLNQLMZMJD-UHFFFAOYSA-N 2-(4-aminophenyl)-2-hydroxyacetic acid Chemical compound NC1=CC=C(C(O)C(O)=O)C=C1 YJGSMLNQLMZMJD-UHFFFAOYSA-N 0.000 description 2
- AWXJEWJXATZZQA-UHFFFAOYSA-N 2-ethoxy-2-(3-nitrophenyl)acetic acid Chemical compound CCOC(C(O)=O)C1=CC=CC([N+]([O-])=O)=C1 AWXJEWJXATZZQA-UHFFFAOYSA-N 0.000 description 2
- AEWNBTNBCVCHPY-UHFFFAOYSA-N 2-ethoxy-3-(3-nitrophenyl)prop-2-enoic acid Chemical compound CCOC(C(O)=O)=CC1=CC=CC([N+]([O-])=O)=C1 AEWNBTNBCVCHPY-UHFFFAOYSA-N 0.000 description 2
- DELMLTLZXGHUGP-UHFFFAOYSA-N 2-ethoxy-3-(4-nitrophenyl)prop-2-enoic acid Chemical compound CCOC(C(O)=O)=CC1=CC=C([N+]([O-])=O)C=C1 DELMLTLZXGHUGP-UHFFFAOYSA-N 0.000 description 2
- GXAHXUKUJSHFEY-UHFFFAOYSA-N 2-hydroxy-3-(3-nitrophenyl)propanoic acid Chemical compound OC(=O)C(O)CC1=CC=CC([N+]([O-])=O)=C1 GXAHXUKUJSHFEY-UHFFFAOYSA-N 0.000 description 2
- MFRVMOQLYRTWQD-UHFFFAOYSA-N 2-methoxy-3-(3-nitrophenyl)prop-2-enoic acid Chemical compound COC(C(O)=O)=CC1=CC=CC([N+]([O-])=O)=C1 MFRVMOQLYRTWQD-UHFFFAOYSA-N 0.000 description 2
- ABNNCLKVUMXLSZ-UHFFFAOYSA-N 2-methyl-4-[(3-nitrophenyl)methylidene]-1,3-oxazol-5-one Chemical compound O=C1OC(C)=NC1=CC1=CC=CC([N+]([O-])=O)=C1 ABNNCLKVUMXLSZ-UHFFFAOYSA-N 0.000 description 2
- LQHYVIJCJOSMCM-UHFFFAOYSA-N 3-(3-aminophenyl)-2-methoxypropanoic acid Chemical compound COC(C(O)=O)CC1=CC=CC(N)=C1 LQHYVIJCJOSMCM-UHFFFAOYSA-N 0.000 description 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 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
- 101800001459 Maximin-2 Proteins 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- 108010052090 Renilla Luciferases Proteins 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 101150042537 dld1 gene Proteins 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- ZONVOBXXYZLZOD-UHFFFAOYSA-N ethyl 2-ethoxy-3-(3-nitrophenyl)prop-2-enoate Chemical compound CCOC(=O)C(OCC)=CC1=CC=CC([N+]([O-])=O)=C1 ZONVOBXXYZLZOD-UHFFFAOYSA-N 0.000 description 2
- OLPIEKHYJZIIEX-UHFFFAOYSA-N ethyl 2-ethoxy-3-(4-nitrophenyl)prop-2-enoate Chemical compound CCOC(=O)C(OCC)=CC1=CC=C([N+]([O-])=O)C=C1 OLPIEKHYJZIIEX-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 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 2
- 230000003993 interaction Effects 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- SBBYXNVCOOGVGX-UHFFFAOYSA-N methyl 2-methoxy-3-(3-nitrophenyl)prop-2-enoate Chemical compound COC(=O)C(OC)=CC1=CC=CC([N+]([O-])=O)=C1 SBBYXNVCOOGVGX-UHFFFAOYSA-N 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000000643 oven drying Methods 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 2
- 238000003146 transient transfection Methods 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- MXHRCPNRJAMMIM-SHYZEUOFSA-N 2'-deoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-SHYZEUOFSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ZADJHIQUZILOBA-UHFFFAOYSA-N 2-methoxy-3-(4-nitrophenyl)prop-2-enoic acid Chemical compound COC(C(O)=O)=CC1=CC=C([N+]([O-])=O)C=C1 ZADJHIQUZILOBA-UHFFFAOYSA-N 0.000 description 1
- UZKSXWXNLHBMHW-UHFFFAOYSA-N 3-(4-aminophenyl)-2-hydroxypropanoic acid Chemical compound NC1=CC=C(CC(O)C(O)=O)C=C1 UZKSXWXNLHBMHW-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 102000005297 Cytochrome P-450 CYP4A Human genes 0.000 description 1
- 108010081498 Cytochrome P-450 CYP4A Proteins 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108090000331 Firefly luciferases Proteins 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001602730 Monza Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- 229910017852 NH2NH2 Inorganic materials 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108700008625 Reporter Genes Proteins 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002001 anti-metastasis Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 102000023732 binding proteins Human genes 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 230000008236 biological pathway Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 238000002701 cell growth assay Methods 0.000 description 1
- 238000002737 cell proliferation kit Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007398 colorimetric assay Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- MXHRCPNRJAMMIM-UHFFFAOYSA-N desoxyuridine Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000013104 docking experiment Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000003003 empirical scoring function Methods 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000005734 heterodimerization reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 108020001756 ligand binding domains Proteins 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- FIRRZCUQSNBXJS-UHFFFAOYSA-N methyl 2-methoxy-3-(4-nitrophenyl)prop-2-enoate Chemical compound COC(=O)C(OC)=CC1=CC=C([N+]([O-])=O)C=C1 FIRRZCUQSNBXJS-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000003614 peroxisome proliferator Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000028503 regulation of lipid metabolic process Effects 0.000 description 1
- 230000022532 regulation of transcription, DNA-dependent Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229950004704 tesaglitazar Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 108091006108 transcriptional coactivators Proteins 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 239000012096 transfection reagent Substances 0.000 description 1
- 102000027257 transmembrane receptors Human genes 0.000 description 1
- 108091008578 transmembrane receptors Proteins 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ592228A NZ592228A (en) | 2005-07-22 | 2006-07-24 | Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000389A ITRM20050389A1 (it) | 2005-07-22 | 2005-07-22 | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| PCT/IE2006/000078 WO2007010516A2 (en) | 2005-07-22 | 2006-07-24 | Compounds and their salts specific to the ppar receptors and the egf receptors and their use in the medical field |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ566045A true NZ566045A (en) | 2012-04-27 |
Family
ID=37579831
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ566045A NZ566045A (en) | 2005-07-22 | 2006-07-24 | Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field |
| NZ592228A NZ592228A (en) | 2005-07-22 | 2006-07-24 | Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ592228A NZ592228A (en) | 2005-07-22 | 2006-07-24 | Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field |
Country Status (23)
| Country | Link |
|---|---|
| US (6) | US8153841B2 (enExample) |
| EP (1) | EP1910270B3 (enExample) |
| JP (1) | JP5312026B2 (enExample) |
| KR (1) | KR101317519B1 (enExample) |
| CN (2) | CN102020577B (enExample) |
| AU (1) | AU2006271165C1 (enExample) |
| CA (1) | CA2616146C (enExample) |
| CY (1) | CY1114294T1 (enExample) |
| DK (1) | DK1910270T6 (enExample) |
| EA (2) | EA017566B1 (enExample) |
| ES (1) | ES2421260T7 (enExample) |
| HR (1) | HRP20130549T4 (enExample) |
| IL (2) | IL188878A (enExample) |
| IT (1) | ITRM20050389A1 (enExample) |
| MX (1) | MX366596B (enExample) |
| NO (1) | NO340680B1 (enExample) |
| NZ (2) | NZ566045A (enExample) |
| PL (1) | PL1910270T6 (enExample) |
| PT (1) | PT1910270E (enExample) |
| SI (1) | SI1910270T1 (enExample) |
| UA (1) | UA100359C2 (enExample) |
| WO (1) | WO2007010516A2 (enExample) |
| ZA (2) | ZA200801671B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITRM20050389A1 (it) | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| ITRM20050390A1 (it) | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| IE20070129A1 (en) * | 2007-02-28 | 2008-12-24 | Giuliani Int Ltd | Ppar-gamma agonists stimulate enteric defensin expression |
| ITMI20072429A1 (it) | 2007-12-24 | 2009-06-25 | Giuliani Int Ltd | Composti per il trattamento selettivo della componente immuno-infiammatoria intestinale della malattia celiaca |
| UA107562C2 (uk) * | 2008-12-05 | 2015-01-26 | Спосіб лікування псоріазу | |
| EP2805746B1 (en) * | 2009-02-16 | 2020-05-06 | Nogra Pharma Limited | Alkylamido compounds and uses thereof |
| CN102906074A (zh) | 2010-05-24 | 2013-01-30 | 东亚荣养株式会社 | 稠合咪唑衍生物 |
| JP6301844B2 (ja) | 2012-02-09 | 2018-03-28 | ノグラ ファーマ リミテッド | 線維症の処置方法 |
| AU2013248397A1 (en) | 2012-04-18 | 2014-10-02 | Nogra Pharma Limited | Methods of treating lactose intolerance |
| FR2996545B1 (fr) | 2012-10-08 | 2016-03-25 | Ecole Polytech | Procede microfluidique de traitement et d'analyse d'une solution contenant un materiel biologique, et circuit microfluidique correspondant. |
| WO2015141851A1 (ja) * | 2014-03-20 | 2015-09-24 | 京セラ株式会社 | ユーザ端末、通信制御方法及び基地局 |
| WO2017093444A1 (en) * | 2015-12-01 | 2017-06-08 | Nogra Pharma Limited | Compositions for oral administration in the treatment of inflammatory bowel disease |
| WO2020152350A1 (en) | 2019-01-25 | 2020-07-30 | Nogra Pharma Limited | Compositions for use in preventing acne |
| SI3921299T1 (sl) | 2019-02-08 | 2025-03-31 | Nogra Pharma Limited | Postopek izdelave 3-(4'-aminofenil)-2-metoksipropionske kisline in njenih analogov in vmesnih proizvodov |
| WO2025132838A1 (en) | 2023-12-20 | 2025-06-26 | Nogra Pharma Limited | Acne topical formulations |
Family Cites Families (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB767788A (en) | 1953-12-28 | 1957-02-06 | Schering Corp | Polyiodinated phenyl fatty acid compounds and process for their manufacture |
| US3211610A (en) | 1961-09-29 | 1965-10-12 | Merck & Co Inc | Benzoic acid ester derivatives for treating coccidiosis and method of using same |
| US3444232A (en) | 1966-05-18 | 1969-05-13 | Squibb & Sons Inc | O-alkyl or phenylalkyl benzohydroxamic acids |
| GB1359560A (en) | 1972-02-25 | 1974-07-10 | Merck & Co Inc | Preparation of pyrrylsalicylic acid |
| US4036951A (en) | 1973-03-12 | 1977-07-19 | Synergistics, Inc. | Ultra-violet filtration with certain aminosalicylic acid esters |
| FR2440353A1 (fr) * | 1978-11-03 | 1980-05-30 | Science Union & Cie | Nouveaux arylethanols, leurs procedes d'obtention et leur emploi comme medicament |
| US4348223A (en) * | 1980-12-05 | 1982-09-07 | Ppg Industries, Inc. | N-Alkyl-N-[3-(alkoxyalkyl)phenyl]-2-haloacetamide herbicides |
| EP0055689B1 (de) * | 1980-12-22 | 1984-07-04 | Schering Aktiengesellschaft | In 3-Stellung substituierte 2,4,6-trihalogenierte Benzamide und deren Salze, deren Herstellung und Verwendung als Ersatzstoffe für natürliche Süssstoffe sowie Süssungsmittel auf Basis dieser Verbindungen |
| JPS58194814A (ja) | 1982-05-11 | 1983-11-12 | Nippon Shinyaku Co Ltd | 免疫調節作用を有する薬剤 |
| IL69282A (en) | 1982-09-02 | 1988-06-30 | Euro Celtique Sa | Method for the carboxylation of potassium phenoxide with carbon dioxide |
| DE3786452T2 (de) * | 1987-02-05 | 1993-10-21 | Kureha Chemical Ind Co Ltd | Benzylether-Verbindungen und Verfahren zu ihrer Herstellung. |
| US4933330A (en) | 1987-04-01 | 1990-06-12 | Dak-Laboratoriet | Benzoic acid derivatives and use thereof |
| ATE113209T1 (de) | 1988-05-05 | 1994-11-15 | Tillotts Pharma Ag | Verwendung von 5-amino-salicylsäure für die behandlung von hautkrankheiten. |
| WO1992006690A1 (en) | 1990-10-22 | 1992-04-30 | Borody Thomas J | Treatment of non-inflammatory and non-infectious bowel disorders |
| US5519014A (en) | 1990-10-22 | 1996-05-21 | Borody; Thomas J. | Treatment of non-inflammatory and non-infectious bowel disorders |
| US5262549A (en) | 1991-05-30 | 1993-11-16 | Polaroid Corporation | Benzpyrylium dyes, and processes for their preparation and use |
| US5302751A (en) | 1992-01-21 | 1994-04-12 | Ethyl Corporation | Profen resolution |
| WO1994000135A1 (en) | 1992-06-30 | 1994-01-06 | Shapiro Howard K | Composition containing amine and amine-related derivatives of benzoic acid and uses therefor including treating inflammatory diseases |
| US5594151A (en) | 1994-01-28 | 1997-01-14 | Prolinx, Inc. | Phenylboronic acid complexing reagents derived from aminosalicylic acid |
| CA2190107A1 (en) | 1994-05-11 | 1995-11-23 | Howard K. Shapiro | Compositions for treatment of chronic inflammatory diseases |
| US5594015A (en) | 1994-06-22 | 1997-01-14 | Regents Of The University Of California | Thiazolidine derivatives for the treatment of psoriasis |
| HUP9900309A3 (en) | 1995-03-28 | 1999-11-29 | Janssen Pharmaceutica Nv | Use of ridogrel for producing pharmaceutical compositions for the treatment of inflammatory bowel diseases |
| US5939442A (en) * | 1995-06-07 | 1999-08-17 | The Salk Institute For Biological Studies | Modulations of peroxisome proliferator activated receptor-γ, and methods for the use thereof |
| GB9600464D0 (en) | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
| GB9617001D0 (en) | 1996-08-13 | 1996-09-25 | Tillotts Pharma Ag | Oral composition |
| DE19647582A1 (de) | 1996-11-18 | 1998-05-20 | Hoechst Ag | Verfahren zur Herstellung von aromatischen Olefinen mittels Katalyse durch Palladaphosphacyclobutane |
| WO1998043081A1 (en) | 1997-03-26 | 1998-10-01 | Ligand Pharmaceuticals Incorporated | Treatment of gastrointestinal disease with ppar modulators |
| WO1999005161A1 (en) | 1997-07-25 | 1999-02-04 | Ligand Pharmaceuticals Incorporated | HUMAN PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA (PPARη) GENE REGULATORY SEQUENCES AND USES THEREFOR |
| AU9002798A (en) * | 1997-09-19 | 1999-04-12 | Ono Pharmaceutical Co. Ltd. | Fused or nonfused benzene compounds |
| FR2773075B1 (fr) | 1997-12-31 | 2000-05-05 | Cird Galderma | Utilisation d'activateurs de ppar-gamma en dermatologie |
| US6114382A (en) | 1998-11-11 | 2000-09-05 | Moretti; Itagiba G. | Methods for treating inflammatory bowel disease |
| US6326364B1 (en) | 1999-02-08 | 2001-12-04 | Cedars-Sinai Medical Center | Use of 5-aminosalicylates as antimicrobial agents |
| FR2791671B1 (fr) | 1999-04-01 | 2001-05-11 | Oreal | Nouveaux composes derives d'esters d'acide benzoique, composition les comprenant et utilisation |
| US20040034067A1 (en) | 1999-04-15 | 2004-02-19 | Macphee Colin Houston | Novel method of treatment |
| GB9908647D0 (en) | 1999-04-15 | 1999-06-09 | Smithkline Beecham Plc | Novel compounds |
| GB9914371D0 (en) | 1999-06-18 | 1999-08-18 | Smithkline Beecham Plc | Novel compounds |
| TWI262185B (en) | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
| CA2656216C (en) | 2000-04-19 | 2012-01-24 | Neurotech Co., Ltd. | Compounds, compositions and methods for preventing neurodegeneration in acute and chronic injuries in the central nervous system |
| US7049342B2 (en) | 2000-05-29 | 2006-05-23 | Kyorin Pharmaceutical Co., Ltd. | Substituted phenylpropionic acid derivatives |
| SI1285908T1 (sl) * | 2000-05-29 | 2008-12-31 | Kyorin Seiyaku Kk | Substituirani fenilpropionski kislinski derivati |
| DE60115465T2 (de) | 2000-08-29 | 2006-08-03 | Nobex Corp. | Immunoregulierende verbindungen, deren derivate und ihre verwendung |
| AU2002222574A1 (en) | 2000-12-05 | 2002-06-18 | Kyorin Pharmaceutical Co. Ltd. | Substituted carboxylic acid derivatives |
| FR2822955B1 (fr) | 2001-03-27 | 2003-10-03 | Chru Lille | Methode de diagnostic de maladies inflammatoires chroniques de l'intestin |
| JP2004528329A (ja) | 2001-04-18 | 2004-09-16 | メルク エンド カムパニー インコーポレーテッド | 炎症を処置するためのＰＰＡＲα〜γのリガンドまたはアゴニスト |
| CA2354921A1 (en) | 2001-05-24 | 2002-11-24 | Yasuo Konishi | Drug evolution: drug design at hot spots |
| CN1589258A (zh) * | 2001-10-16 | 2005-03-02 | 雷迪实验室有限公司 | 新的β－苯基－α－氧取代的丙酸衍生物,它的制备方法和它们制备药学上重要的化合物的应用 |
| GB0127916D0 (en) | 2001-11-21 | 2002-01-16 | Rowett Res Inst | Method |
| UA82835C2 (en) | 2001-12-03 | 2008-05-26 | Reddys Lab Ltd Dr | ?-aryl-?-oxysubstituted propionuc acid derivatives and pharmaceutical composition based thereon |
| US20030113815A1 (en) | 2001-12-19 | 2003-06-19 | Pfizer Inc. | Canine peroxisome proliferator activated receptor gamma |
| US20030220374A1 (en) | 2002-01-14 | 2003-11-27 | Pharmacia Corporation | Compositions and methods of treatment involving peroxisome proliferator-activated receptor-gamma agonists and cyclooxygenase-2 selective inhibitors |
| US20040115127A1 (en) | 2002-04-12 | 2004-06-17 | Wright Samuel D. | Ppar-alpha-gamma ligands or agonists for the treatment of inflammation |
| GB0303609D0 (en) | 2003-02-17 | 2003-03-19 | Glaxo Group Ltd | Novel therapeutic method and compositions |
| US20060159648A1 (en) | 2003-02-17 | 2006-07-20 | Davis Adrian F | Novel therapeutic method and compositions for topical administration |
| JPWO2004082715A1 (ja) | 2003-03-20 | 2006-06-22 | エーザイ株式会社 | 炎症性腸疾患治療剤としての併用医薬 |
| JP5198768B2 (ja) | 2003-07-21 | 2013-05-15 | メルク セローノ ソシエテ アノニム | アルキニルアリールカルボキサミド |
| GB2422782A (en) | 2003-10-21 | 2006-08-09 | Inspire Pharmaceuticals Inc | Non-nucleotide compositions and method for treating pain |
| US20070093476A1 (en) * | 2003-10-28 | 2007-04-26 | Bhunia Debnath | Novel compounds and their use in medicine,as antidiabetic and hypolipidemic agents, process for their preparation and pharmaceutical compositions containing them |
| EP1691806A2 (en) | 2003-12-03 | 2006-08-23 | Smithkline Beecham Corporation | Novel therapeutic method and compositions |
| CA2553775A1 (en) | 2004-01-20 | 2005-08-11 | Richard F. Harty | Compositions and methods of treatment for inflammatory diseases |
| WO2005084658A1 (en) | 2004-03-04 | 2005-09-15 | Arakis Ltd. | Derivatives of actarit and their therapeutic use |
| US20060286046A1 (en) | 2005-01-05 | 2006-12-21 | Haber C Andrew | Skin care compositions |
| US20060270635A1 (en) | 2005-05-27 | 2006-11-30 | Wallace John L | Derivatives of 4- or 5-aminosalicylic acid |
| ITRM20050389A1 (it) * | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| ITRM20050390A1 (it) | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| DE102005061472A1 (de) | 2005-12-22 | 2007-07-05 | Saltigo Gmbh | Verfahren zur Herstellung von enantiomerenangereicherten 2-Alkoxy-3-phenylpropionsäuren |
| WO2007096148A1 (en) | 2006-02-23 | 2007-08-30 | Lipid Nutrition B.V. | Immunoregulation |
| US7645801B2 (en) | 2007-01-29 | 2010-01-12 | Alaven Pharmaceutical Llc | Reduced irritant enema for treatment of inflammatory bowel disease (IBD) |
| IE20070129A1 (en) | 2007-02-28 | 2008-12-24 | Giuliani Int Ltd | Ppar-gamma agonists stimulate enteric defensin expression |
| WO2009025854A1 (en) | 2007-08-22 | 2009-02-26 | Burnham Institute For Medical Research | Smips: small molecule inhibitors of p27 depletion in cancers and other proliferative diseases |
| ITMI20072429A1 (it) | 2007-12-24 | 2009-06-25 | Giuliani Int Ltd | Composti per il trattamento selettivo della componente immuno-infiammatoria intestinale della malattia celiaca |
| US8030520B2 (en) | 2008-03-31 | 2011-10-04 | Saltigo Gmbh | Process for preparing organic compounds by a transition metal-catalysed cross-coupling reaction of an aryl-X, heteroaryl-X, cycloalkenyl-X or alkenyl-X compound with an alkyl, alkenyl, cycloalkyl or cycloalkenyl halide |
| UA107562C2 (uk) | 2008-12-05 | 2015-01-26 | Спосіб лікування псоріазу | |
| EP2805746B1 (en) | 2009-02-16 | 2020-05-06 | Nogra Pharma Limited | Alkylamido compounds and uses thereof |
| EP2298321A1 (en) | 2009-08-26 | 2011-03-23 | Nordic Pharma | Novel pharmaceutical compositions for treating IBD |
| EP2731605A4 (en) | 2011-07-15 | 2015-02-25 | Sla Pharma Ag | PHARMACEUTICAL COMPOSITIONS FOR RECTAL ADMINISTRATION |
| EP2773378B1 (en) | 2011-10-31 | 2016-08-10 | Larsen, Claus Selch | Prodrugs of non-steroid anti-inflammatory agents (nsaids) |
| JP6301844B2 (ja) | 2012-02-09 | 2018-03-28 | ノグラ ファーマ リミテッド | 線維症の処置方法 |
| AU2013248397A1 (en) | 2012-04-18 | 2014-10-02 | Nogra Pharma Limited | Methods of treating lactose intolerance |
| IN2014DN10214A (enExample) | 2012-06-01 | 2015-08-07 | Nogra Pharma Ltd | |
| US9013997B2 (en) | 2012-06-01 | 2015-04-21 | Broadcom Corporation | System for performing distributed data cut-through |
| EP2897603A1 (en) | 2012-09-13 | 2015-07-29 | Nogra Pharma Limited | Methods of inhibiting hair growth |
| NZ705389A (en) | 2012-09-13 | 2018-08-31 | Nogra Pharma Ltd | Methods of treating hair related conditions |
| WO2016154730A1 (en) | 2015-04-02 | 2016-10-06 | University Health Network | Gut anti-inflammatory agents for regulation of high blood glucose levels |
| JP6798075B2 (ja) | 2015-06-15 | 2020-12-09 | エヌエムディー ファーマ エー／エス | 神経筋障害を処置するのにおける使用のための化合物 |
-
2005
- 2005-07-22 IT IT000389A patent/ITRM20050389A1/it unknown
-
2006
- 2006-07-24 US US11/989,090 patent/US8153841B2/en active Active
- 2006-07-24 EA EA201000708A patent/EA017566B1/ru not_active IP Right Cessation
- 2006-07-24 NZ NZ566045A patent/NZ566045A/en unknown
- 2006-07-24 PL PL06766085T patent/PL1910270T6/pl unknown
- 2006-07-24 CA CA2616146A patent/CA2616146C/en active Active
- 2006-07-24 EA EA200800372A patent/EA014665B3/ru active IP Right Maintenance
- 2006-07-24 DK DK06766085.2T patent/DK1910270T6/en active
- 2006-07-24 CN CN2010105208008A patent/CN102020577B/zh active Active
- 2006-07-24 KR KR1020087003953A patent/KR101317519B1/ko active Active
- 2006-07-24 UA UAA200802141A patent/UA100359C2/uk unknown
- 2006-07-24 JP JP2008522170A patent/JP5312026B2/ja active Active
- 2006-07-24 PT PT67660852T patent/PT1910270E/pt unknown
- 2006-07-24 SI SI200631598T patent/SI1910270T1/sl unknown
- 2006-07-24 HR HRP20130549TT patent/HRP20130549T4/hr unknown
- 2006-07-24 CN CN2006800300777A patent/CN101243039B/zh active Active
- 2006-07-24 MX MX2013012753A patent/MX366596B/es unknown
- 2006-07-24 AU AU2006271165A patent/AU2006271165C1/en active Active
- 2006-07-24 NZ NZ592228A patent/NZ592228A/xx unknown
- 2006-07-24 ES ES06766085.2T patent/ES2421260T7/es active Active
- 2006-07-24 EP EP06766085.2A patent/EP1910270B3/en active Active
- 2006-07-24 WO PCT/IE2006/000078 patent/WO2007010516A2/en not_active Ceased
-
2008
- 2008-01-17 IL IL188878A patent/IL188878A/en active IP Right Review Request
- 2008-01-18 NO NO20080325A patent/NO340680B1/no unknown
- 2008-02-20 ZA ZA2008/01671A patent/ZA200801671B/en unknown
-
2010
- 2010-05-26 IL IL205992A patent/IL205992A/en active IP Right Grant
- 2010-11-18 ZA ZA2010/08268A patent/ZA201008268B/en unknown
-
2012
- 2012-02-29 US US13/408,439 patent/US8710100B2/en active Active
-
2013
- 2013-07-05 CY CY20131100562T patent/CY1114294T1/el unknown
-
2014
- 2014-03-10 US US14/202,386 patent/US9133099B2/en active Active
-
2015
- 2015-03-27 US US14/671,585 patent/US9345680B2/en active Active
- 2015-03-27 US US14/671,579 patent/US9561202B2/en active Active
-
2016
- 2016-12-13 US US15/377,013 patent/US10016381B2/en active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10016381B2 (en) | Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field | |
| US8450506B2 (en) | Compounds and their salts specific to the PPAR receptors and the EGF Receptors and their use in the medical field | |
| BRPI0613396B1 (pt) | Composto, uso do mesmo, e, composição farmacêutica |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 24 JUL 2016 BY TOMKINS + CO Effective date: 20130711 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2017 BY COMPUTER PACKAGES INC Effective date: 20160701 |
|
| S38C | Proceedings under section 38 (amendment of specification with leave of commissioner): specification amended | ||
| S38C | Proceedings under section 38 (amendment of specification with leave of commissioner): specification amended | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2018 BY COMPUTER PACKAGES INC Effective date: 20170701 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2019 BY COMPUTER PACKAGES INC Effective date: 20180703 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2020 BY COMPUTER PACKAGES INC Effective date: 20190702 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2021 BY COMPUTER PACKAGES INC Effective date: 20200701 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2022 BY COMPUTER PACKAGES INC Effective date: 20210630 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2023 BY COMPUTER PACKAGES INC Effective date: 20220630 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2024 BY COMPUTER PACKAGES INC Effective date: 20230630 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 24 JUL 2025 BY COMPUTER PACKAGES INC Effective date: 20240630 |