KR101317519B1 - Ｐｐａｒ 수용체 및 ｅｇｆ 수용체에 특이적인 화합물 및이들의 염, 및 의학 분야에서의 이들의 용도 - Google Patents
Ｐｐａｒ 수용체 및 ｅｇｆ 수용체에 특이적인 화합물 및이들의 염, 및 의학 분야에서의 이들의 용도 Download PDFInfo
- Publication number
- KR101317519B1 KR101317519B1 KR1020087003953A KR20087003953A KR101317519B1 KR 101317519 B1 KR101317519 B1 KR 101317519B1 KR 1020087003953 A KR1020087003953 A KR 1020087003953A KR 20087003953 A KR20087003953 A KR 20087003953A KR 101317519 B1 KR101317519 B1 KR 101317519B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- cooh
- group
- formula
- aminophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 86
- 108060006698 EGF receptor Proteins 0.000 title claims description 13
- 102000001301 EGF receptor Human genes 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 title claims description 7
- 102000005962 receptors Human genes 0.000 title description 14
- 108020003175 receptors Proteins 0.000 title description 14
- 101150014691 PPARA gene Proteins 0.000 title 1
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 24
- 108010016731 PPAR gamma Proteins 0.000 claims abstract description 22
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims abstract description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 9
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 8
- 125000004429 atom Chemical group 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 14
- 239000000203 mixture Substances 0.000 claims description 37
- 238000000034 method Methods 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 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 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 9
- 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 9
- 229940127007 Compound 39 Drugs 0.000 claims description 9
- 229940125810 compound 20 Drugs 0.000 claims description 9
- 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 claims description 9
- 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 8
- 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
- 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
- 229940125833 compound 23 Drugs 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 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 6
- 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 6
- 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 6
- 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 description 6
- 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 claims description 6
- 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 claims description 6
- 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 6
- 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
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 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 claims description 5
- 229940126086 compound 21 Drugs 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
- 210000001072 colon Anatomy 0.000 claims description 4
- 229940125773 compound 10 Drugs 0.000 claims description 4
- 210000003238 esophagus Anatomy 0.000 claims description 4
- 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 claims description 4
- 210000003734 kidney Anatomy 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- 210000000496 pancreas Anatomy 0.000 claims description 4
- 210000002307 prostate Anatomy 0.000 claims description 4
- 210000002784 stomach Anatomy 0.000 claims description 4
- 210000004291 uterus Anatomy 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- -1 wherein R 3 is H Chemical group 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000007787 solid Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 210000004027 cell Anatomy 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 230000000694 effects Effects 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000003032 molecular docking Methods 0.000 description 12
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 11
- 229960004963 mesalazine Drugs 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 9
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 201000011510 cancer Diseases 0.000 description 9
- 230000010261 cell growth Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 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 7
- 206010009944 Colon cancer Diseases 0.000 description 7
- 125000000539 amino acid group Chemical group 0.000 description 7
- 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 6
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000004913 activation Effects 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
- WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 5
- 208000029742 colonic neoplasm Diseases 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 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 4
- WOVKYSAHUYNSMH-UHFFFAOYSA-N BROMODEOXYURIDINE Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000002965 ELISA Methods 0.000 description 4
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003814 drug Substances 0.000 description 4
- 238000002474 experimental method Methods 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
- 239000003446 ligand Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000302 molecular modelling Methods 0.000 description 4
- 239000012044 organic layer Substances 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
- 102100033237 Pro-epidermal growth factor Human genes 0.000 description 3
- 230000001028 anti-proliverative effect Effects 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000002372 labelling Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 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
- 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
- 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 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
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 2
- 0 CCOC(Cc1cc(*)ccc1)C(O)=O Chemical compound CCOC(Cc1cc(*)ccc1)C(O)=O 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000005623 Carcinogenesis Diseases 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
- 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
- 238000002835 absorbance Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000036952 cancer formation Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 231100000504 carcinogenesis Toxicity 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000006020 chronic inflammation Effects 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 101150042537 dld1 gene Proteins 0.000 description 2
- 238000001035 drying Methods 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
- 239000000284 extract Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011534 incubation 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
- 208000002551 irritable bowel syndrome Diseases 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
- 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 2
- 239000003921 oil Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960004586 rosiglitazone Drugs 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
- 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
- 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
- 210000004881 tumor cell Anatomy 0.000 description 2
- 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 description 1
- IQQMLCLWOGLMOY-UHFFFAOYSA-N 2-(3-aminophenyl)-2-methoxyacetic acid Chemical compound COC(C(O)=O)C1=CC=CC(N)=C1 IQQMLCLWOGLMOY-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
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- YADUOOGUTSNPJE-UHFFFAOYSA-N CC(Nc1ccc(C(C(Cl)(Cl)Cl)O)cc1)=O Chemical compound CC(Nc1ccc(C(C(Cl)(Cl)Cl)O)cc1)=O YADUOOGUTSNPJE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 241000282326 Felis catus Species 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
- 102000009465 Growth Factor Receptors Human genes 0.000 description 1
- 108010009202 Growth Factor Receptors Proteins 0.000 description 1
- 101000741790 Homo sapiens Peroxisome proliferator-activated receptor gamma Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin 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
- 108020005497 Nuclear hormone receptor Proteins 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
- 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
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108010052090 Renilla Luciferases Proteins 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
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 230000002001 anti-metastasis Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008236 biological pathway Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 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
- 238000007398 colorimetric assay Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000013104 docking experiment Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 230000008472 epithelial growth Effects 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
- 229960002518 gentamicin Drugs 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010348 incorporation Methods 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
- 230000003993 interaction Effects 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 108020001756 ligand binding domains Proteins 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 102000006255 nuclear receptors Human genes 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 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
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride 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
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture 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
- 230000002103 transcriptional effect Effects 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
- 238000001665 trituration Methods 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
Images
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITRM2005A000389 | 2005-07-22 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| KR20080039428A KR20080039428A (ko) | 2008-05-07 |
| KR101317519B1 true KR101317519B1 (ko) | 2013-10-15 |
Family
ID=37579831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087003953A Active KR101317519B1 (ko) | 2005-07-22 | 2006-07-24 | Ｐｐａｒ 수용체 및 ｅｇｆ 수용체에 특이적인 화합물 및이들의 염, 및 의학 분야에서의 이들의 용도 |
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) | EA014665B3 (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 | |
| AU2010213093B2 (en) * | 2009-02-16 | 2016-01-07 | Nogra Pharma Limited | Alkylamido compounds and uses thereof |
| EP2578573A4 (en) | 2010-05-24 | 2014-08-06 | Toa Eiyo Ltd | CONDENSATE IMIDAZOLE DERIVATIVE |
| CN104254327A (zh) | 2012-02-09 | 2014-12-31 | 诺格拉制药有限公司 | 治疗纤维化的方法 |
| CN104284655B (zh) | 2012-04-18 | 2017-10-27 | 诺格拉制药有限公司 | 治疗乳糖不耐受的方法 |
| 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. |
| US10257875B2 (en) * | 2014-03-20 | 2019-04-09 | Kyocera Corporation | User terminal, communication control method, and base station |
| 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 |
| EP4495101A3 (en) | 2019-02-08 | 2025-04-30 | Nogra Pharma Limited | Process of making 3-(4'-aminophenyl)-2-methoxypropionic acid, and analogs and intermediates thereof |
| WO2025132838A1 (en) | 2023-12-20 | 2025-06-26 | Nogra Pharma Limited | Acne topical formulations |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0055689A1 (de) * | 1980-12-22 | 1982-07-07 | 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 |
| US4348223A (en) * | 1980-12-05 | 1982-09-07 | Ppg Industries, Inc. | N-Alkyl-N-[3-(alkoxyalkyl)phenyl]-2-haloacetamide herbicides |
| EP0279096A2 (en) * | 1987-02-05 | 1988-08-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Benzyl ether compound and process for producing the same |
Family Cites Families (81)
| 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 |
| 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 |
| US4933330A (en) | 1987-04-01 | 1990-06-12 | Dak-Laboratoriet | Benzoic acid derivatives and use thereof |
| ES2065980T3 (es) | 1988-05-05 | 1995-03-01 | Tillotts Pharma Ag | Uso del acido 5-aminosalicilico en el tratamiento de alteraciones dermatologicas. |
| US5519014A (en) | 1990-10-22 | 1996-05-21 | Borody; Thomas J. | Treatment of non-inflammatory and non-infectious bowel disorders |
| JP3425441B2 (ja) | 1990-10-22 | 2003-07-14 | ガストロ サービシイズ ピーティーワイ リミテッド | 非炎症性及び非感染性腸障害の処置 |
| 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 |
| EP0604641B1 (en) | 1992-06-30 | 2002-03-20 | SHAPIRO, Howard, K. | Use of a combination containing an amine or amine-related derivative of benzoic acid and an amino-polysaccharide in the manufacture of a medicament for the treatment of 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 |
| WO1996030016A2 (en) | 1995-03-28 | 1996-10-03 | Janssen Pharmaceutica N.V. | Low dose ridogrel formulations and their use 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 |
| AU6773598A (en) | 1997-03-26 | 1998-10-20 | Institut Pasteur | Treatment of gastrointestinal disease with ppar modulators |
| US7098025B1 (en) | 1997-07-25 | 2006-08-29 | Ligand Pharmaceuticals Incorporated | Human peroxisome proliferator activated receptor gamma (pparγ) 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 |
| JP3854154B2 (ja) | 2000-04-19 | 2006-12-06 | ニューロテック カンパニー リミテッド | 中枢神経系の急性及び慢性的損傷に起因した神経変性を防止するための化合物、組成物及び方法 |
| DK1285908T3 (da) * | 2000-05-29 | 2008-12-01 | Kyorin Seiyaku Kk | Substituerede phenylpropionsyrederivater |
| US7049342B2 (en) | 2000-05-29 | 2006-05-23 | Kyorin Pharmaceutical Co., Ltd. | Substituted phenylpropionic acid derivatives |
| CA2420576C (en) | 2000-08-29 | 2005-06-14 | Nobex Corporation | Immunoregulatory compounds, derivatives thereof and their use |
| WO2002046161A1 (en) | 2000-12-05 | 2002-06-13 | 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 |
| EP1389044A4 (en) | 2001-04-18 | 2006-07-05 | Merck & Co Inc | PPAR ALPHA GAMMA LIGANDS OR AGONISTS FOR THE TREATMENT OF INFLAMMATION |
| CA2354921A1 (en) | 2001-05-24 | 2002-11-24 | Yasuo Konishi | Drug evolution: drug design at hot spots |
| HRP20040350A2 (en) * | 2001-10-16 | 2005-06-30 | Dr. Reddy's Laboratories Limited | NOVEL ?-PHENYL-α-OXYSUBSTITUTED PROPIONIC DERIVATIVES: PROCESS FOR ITS PREPARATION AND THEIR US COMPOUNDS |
| 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 |
| AU2004261400A1 (en) | 2003-07-21 | 2005-02-10 | Laboratoires Serono Sa | Alkynyl aryl carboxamides |
| US7749980B2 (en) | 2003-10-21 | 2010-07-06 | 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 |
| WO2005055933A2 (en) | 2003-12-03 | 2005-06-23 | Smithkline Beecham Corporation | Treatment of psoriasis with rosiglitazone |
| EP1722630A4 (en) | 2004-01-20 | 2009-05-27 | Richard F Harty | COMPOSITIONS AND METHOD FOR THE TREATMENT OF 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 |
| US20090054312A1 (en) | 2007-08-22 | 2009-02-26 | Wolf Dieter A | 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 | |
| AU2010213093B2 (en) | 2009-02-16 | 2016-01-07 | Nogra Pharma Limited | Alkylamido compounds and uses thereof |
| EP2298321A1 (en) | 2009-08-26 | 2011-03-23 | Nordic Pharma | Novel pharmaceutical compositions for treating IBD |
| CA2841358A1 (en) | 2011-07-15 | 2013-01-24 | S.L.A. Pharma Ag | Pharmaceutical compositions for rectal administration |
| US9809557B2 (en) | 2011-10-31 | 2017-11-07 | Claus Selch Larsen | Prodrugs of non-steroid anti-inflammatory agents (NSAIDS) |
| CN104254327A (zh) | 2012-02-09 | 2014-12-31 | 诺格拉制药有限公司 | 治疗纤维化的方法 |
| CN104284655B (zh) | 2012-04-18 | 2017-10-27 | 诺格拉制药有限公司 | 治疗乳糖不耐受的方法 |
| KR20150016377A (ko) | 2012-06-01 | 2015-02-11 | 노그라 파마 리미티드 | T-세포 반응을 조절할 수 있는 비시클릭 헤테로사이클 및 그의 사용 방법 |
| US9013997B2 (en) | 2012-06-01 | 2015-04-21 | Broadcom Corporation | System for performing distributed data cut-through |
| EA201590551A1 (ru) | 2012-09-13 | 2015-06-30 | Ногра Фарма Лимитед | Способы ингибирования роста волос |
| EA035986B1 (ru) | 2012-09-13 | 2020-09-09 | Ногра Фарма Лимитед | Способы лечения или облегчения плоского фолликулярного лишая |
| WO2016154730A1 (en) | 2015-04-02 | 2016-10-06 | University Health Network | Gut anti-inflammatory agents for regulation of high blood glucose levels |
| WO2016202341A1 (en) | 2015-06-15 | 2016-12-22 | Nmd Pharma Aps | Compounds for use in treating neuromuscular disorders |
-
2005
- 2005-07-22 IT IT000389A patent/ITRM20050389A1/it unknown
-
2006
- 2006-07-24 CN CN2010105208008A patent/CN102020577B/zh active Active
- 2006-07-24 MX MX2013012753A patent/MX366596B/es unknown
- 2006-07-24 KR KR1020087003953A patent/KR101317519B1/ko active Active
- 2006-07-24 AU AU2006271165A patent/AU2006271165C1/en active Active
- 2006-07-24 EA EA200800372A patent/EA014665B3/ru active IP Right Maintenance
- 2006-07-24 NZ NZ566045A patent/NZ566045A/en unknown
- 2006-07-24 EP EP06766085.2A patent/EP1910270B3/en active Active
- 2006-07-24 JP JP2008522170A patent/JP5312026B2/ja active Active
- 2006-07-24 NZ NZ592228A patent/NZ592228A/xx unknown
- 2006-07-24 DK DK06766085.2T patent/DK1910270T6/en active
- 2006-07-24 PL PL06766085T patent/PL1910270T6/pl unknown
- 2006-07-24 PT PT67660852T patent/PT1910270E/pt unknown
- 2006-07-24 UA UAA200802141A patent/UA100359C2/uk unknown
- 2006-07-24 CA CA2616146A patent/CA2616146C/en active Active
- 2006-07-24 HR HRP20130549TT patent/HRP20130549T4/hr unknown
- 2006-07-24 CN CN2006800300777A patent/CN101243039B/zh active Active
- 2006-07-24 ES ES06766085.2T patent/ES2421260T7/es active Active
- 2006-07-24 EA EA201000708A patent/EA017566B1/ru not_active IP Right Cessation
- 2006-07-24 US US11/989,090 patent/US8153841B2/en active Active
- 2006-07-24 WO PCT/IE2006/000078 patent/WO2007010516A2/en not_active Ceased
- 2006-07-24 SI SI200631598T patent/SI1910270T1/sl unknown
-
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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348223A (en) * | 1980-12-05 | 1982-09-07 | Ppg Industries, Inc. | N-Alkyl-N-[3-(alkoxyalkyl)phenyl]-2-haloacetamide herbicides |
| EP0055689A1 (de) * | 1980-12-22 | 1982-07-07 | 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 |
| EP0279096A2 (en) * | 1987-02-05 | 1988-08-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Benzyl ether compound and process for producing the same |
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 | |
| CA2334713C (en) | Therapeutic biaryl derivatives | |
| CN101243043B (zh) | Ppar受体和egf受体特异性化合物及其盐以及它们在医药领域中的用途 | |
| BRPI0613396B1 (pt) | Composto, uso do mesmo, e, composição farmacêutica |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20080219 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20110318 Comment text: Request for Examination of Application |
|
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20121030 Patent event code: PE09021S01D |
|
| PE0902 | Notice of grounds for rejection |
Comment text: Final Notice of Reason for Refusal Patent event date: 20130402 Patent event code: PE09021S02D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20130820 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20131004 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20131004 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| J202 | Request for trial for correction [limitation] | ||
| PJ0202 | Trial for correction |
Comment text: Request for Trial Patent event date: 20160401 Patent event code: PJ02022R01D Comment text: Registration of Establishment Patent event date: 20131004 Patent event code: PJ02021E01I Appeal kind category: Correction Decision date: 20170320 Request date: 20160401 Appeal identifier: 2016105000038 |
|
| FPAY | Annual fee payment |
Payment date: 20160923 Year of fee payment: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20160923 Start annual number: 4 End annual number: 4 |
|
| J121 | Written withdrawal of request for trial | ||
| PJ1201 | Withdrawal of trial |
Patent event code: PJ12011R01D Patent event date: 20170320 Comment text: Written Withdrawal of Request for Trial Appeal identifier: 2016105000038 Request date: 20160401 Appeal kind category: Correction Decision date: 20170320 |
|
| PR1001 | Payment of annual fee |
Payment date: 20171011 Start annual number: 5 End annual number: 5 |
|
| FPAY | Annual fee payment |
Payment date: 20180921 Year of fee payment: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20180921 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20191021 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20201006 Start annual number: 8 End annual number: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20211020 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20220922 Start annual number: 10 End annual number: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20230921 Start annual number: 11 End annual number: 11 |
|
| PR1001 | Payment of annual fee |