ES2370901T3 - Nuevos compuestos que modulan los receptores de tipo ppar-gamma y su utilización en composiciones cosméticas o farmacéuticas. - Google Patents
Nuevos compuestos que modulan los receptores de tipo ppar-gamma y su utilización en composiciones cosméticas o farmacéuticas. Download PDFInfo
- Publication number
- ES2370901T3 ES2370901T3 ES04740561T ES04740561T ES2370901T3 ES 2370901 T3 ES2370901 T3 ES 2370901T3 ES 04740561 T ES04740561 T ES 04740561T ES 04740561 T ES04740561 T ES 04740561T ES 2370901 T3 ES2370901 T3 ES 2370901T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- radical
- methyl
- ethoxy
- propanoic acid
- 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.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 75
- 239000002537 cosmetic Substances 0.000 title claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- -1 alkyl radical Chemical class 0.000 claims abstract description 322
- 150000003254 radicals Chemical group 0.000 claims abstract description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 67
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 16
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 230000003287 optical effect Effects 0.000 claims abstract description 4
- BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical compound ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims abstract description 3
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 claims abstract description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims abstract description 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims abstract description 3
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 3
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 3
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 17
- 235000019260 propionic acid Nutrition 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
- 206010000496 acne Diseases 0.000 claims description 14
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical group 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- DKLBEOQXEBZVRM-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[5-[[hexanoyl(methyl)amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCC)=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 DKLBEOQXEBZVRM-NRFANRHFSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- XQFZGGDLIACALE-QHCPKHFHSA-N (2s)-2-ethoxy-3-[6-[3-[heptylcarbamoyl(methyl)amino]phenyl]pyridin-3-yl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2N=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 XQFZGGDLIACALE-QHCPKHFHSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- GCEHHZVUESTTFT-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[5-[[methyl(octanoyl)amino]methyl]thiophen-2-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCCCC)=CC=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 GCEHHZVUESTTFT-QFIPXVFZSA-N 0.000 claims description 5
- ZTTRAMVZDJPERD-QHCPKHFHSA-N (2s)-2-ethoxy-3-[4-[5-[[methyl(octanoyl)amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCCCC)=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 ZTTRAMVZDJPERD-QHCPKHFHSA-N 0.000 claims description 5
- GDJFHIFQAICQJZ-BQAIUKQQSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(2-phenylethylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCC=2C=CC=CC=2)=N1 GDJFHIFQAICQJZ-BQAIUKQQSA-N 0.000 claims description 5
- JAVAALZJVQPEFL-BDQAORGHSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 JAVAALZJVQPEFL-BDQAORGHSA-N 0.000 claims description 5
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 5
- JGTJTOFNJUOALH-UHFFFAOYSA-N n-[[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]thiophen-2-yl]methyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(SC=1)=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O JGTJTOFNJUOALH-UHFFFAOYSA-N 0.000 claims description 5
- MNKDPGREYJFFLM-UHFFFAOYSA-N n-[[5-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]pyridin-3-yl]methyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(C=1)=CN=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O MNKDPGREYJFFLM-UHFFFAOYSA-N 0.000 claims description 5
- LLPFTTRBMMIIDB-UHFFFAOYSA-N n-[[5-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]thiophen-3-yl]methyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)CC(C=1)=CSC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O LLPFTTRBMMIIDB-UHFFFAOYSA-N 0.000 claims description 5
- 230000035755 proliferation Effects 0.000 claims description 5
- RPSSOCFECCTIGG-HKBQPEDESA-N (2s)-2-(2-benzoylanilino)-3-[4-[5-[[hexanoyl(methyl)amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCC)=CC(C=2C=CC(C[C@H](NC=3C(=CC=CC=3)C(=O)C=3C=CC=CC=3)C(O)=O)=CC=2)=C1 RPSSOCFECCTIGG-HKBQPEDESA-N 0.000 claims description 4
- JLGNWCYEVXRWSX-XIFFEERXSA-N (2s)-2-(2-benzoylanilino)-3-[4-[5-[[methyl(octanoyl)amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCCCC)=CC(C=2C=CC(C[C@H](NC=3C(=CC=CC=3)C(=O)C=3C=CC=CC=3)C(O)=O)=CC=2)=C1 JLGNWCYEVXRWSX-XIFFEERXSA-N 0.000 claims description 4
- GUCNDFGZDALOPJ-YTTGMZPUSA-N (2s)-2-(2-benzoylanilino)-3-[4-[6-[heptylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](NC=3C(=CC=CC=3)C(=O)C=3C=CC=CC=3)C(O)=O)=CC=2)=N1 GUCNDFGZDALOPJ-YTTGMZPUSA-N 0.000 claims description 4
- YUADSIXGGNIDKJ-PMERELPUSA-N (2s)-2-(2-benzoylanilino)-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](NC=3C(=CC=CC=3)C(=O)C=3C=CC=CC=3)C(O)=O)=CC=2)=N1 YUADSIXGGNIDKJ-PMERELPUSA-N 0.000 claims description 4
- MVIHOFOEKSKVEH-KRWDZBQOSA-N (2s)-2-ethoxy-3-[4-[2-[methyl(pentylcarbamoyl)amino]-1,3-thiazol-5-yl]phenyl]propanoic acid Chemical compound S1C(N(C)C(=O)NCCCCC)=NC=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 MVIHOFOEKSKVEH-KRWDZBQOSA-N 0.000 claims description 4
- OMOCFSGSCQRQJW-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[5-[heptylcarbamoyl(methyl)amino]thiophen-2-yl]phenyl]propanoic acid Chemical compound S1C(N(C)C(=O)NCCCCCCC)=CC=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 OMOCFSGSCQRQJW-FQEVSTJZSA-N 0.000 claims description 4
- NEHWGUNTBKCTLN-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[6-[heptylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 NEHWGUNTBKCTLN-QFIPXVFZSA-N 0.000 claims description 4
- NPAOPEYTQOLKQT-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 NPAOPEYTQOLKQT-FQEVSTJZSA-N 0.000 claims description 4
- QNVAWPHOKCSZJY-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(phenylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NC=2C=CC=CC=2)=N1 QNVAWPHOKCSZJY-NRFANRHFSA-N 0.000 claims description 4
- SQWFDIPSOKOCER-VWLOTQADSA-N (2s)-3-[4-[5-[[(4-cyclohexyl-2-oxobutyl)amino]methyl]thiophen-3-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CSC(CNCC(=O)CCC2CCCCC2)=C1 SQWFDIPSOKOCER-VWLOTQADSA-N 0.000 claims description 4
- WDUNBCPRACCSKY-IBGZPJMESA-N (2s)-3-[4-[6-[butylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]-2-ethoxypropanoic acid Chemical compound CCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 WDUNBCPRACCSKY-IBGZPJMESA-N 0.000 claims description 4
- CDMVDCVTFZWQSX-DEOSSOPVSA-N (2s)-3-[6-[3-[[4-(dimethylamino)phenyl]carbamoyl-methylamino]phenyl]pyridin-3-yl]-2-ethoxypropanoic acid Chemical compound N1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NC=2C=CC(=CC=2)N(C)C)=C1 CDMVDCVTFZWQSX-DEOSSOPVSA-N 0.000 claims description 4
- XQFZGGDLIACALE-UHFFFAOYSA-N 2-ethoxy-3-[6-[3-[heptylcarbamoyl(methyl)amino]phenyl]pyridin-3-yl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2N=CC(CC(OCC)C(O)=O)=CC=2)=C1 XQFZGGDLIACALE-UHFFFAOYSA-N 0.000 claims description 4
- 201000004384 Alopecia Diseases 0.000 claims description 4
- 206010003645 Atopy Diseases 0.000 claims description 4
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 208000012641 Pigmentation disease Diseases 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000032683 aging Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 231100000360 alopecia Toxicity 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000037356 lipid metabolism Effects 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 4
- 201000010153 skin papilloma Diseases 0.000 claims description 4
- XPHCVYINYHHGPW-FTBISJDPSA-N (2s)-2-ethoxy-3-[4-[6-[heptylcarbamoyl(methyl)amino]pyridin-1-ium-2-yl]phenyl]propanoic acid;chloride Chemical compound [Cl-].CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=[NH+]1 XPHCVYINYHHGPW-FTBISJDPSA-N 0.000 claims description 3
- VSMZWVXCOSVZOV-VWLOTQADSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(naphthalen-2-ylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NC=2C=C3C=CC=CC3=CC=2)=N1 VSMZWVXCOSVZOV-VWLOTQADSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 230000004069 differentiation Effects 0.000 claims description 3
- 210000000987 immune system Anatomy 0.000 claims description 3
- 208000026278 immune system disease Diseases 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 230000003780 keratinization Effects 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 230000009885 systemic effect Effects 0.000 claims description 3
- 230000003612 virological effect Effects 0.000 claims description 3
- BFKHLPFUCFDHEN-MHZLTWQESA-N (2S)-2-ethoxy-3-[4-[5-[[[4-(1H-indol-3-yl)-2-oxobutyl]amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CSC(CNCC(=O)CCC=2C3=CC=CC=C3NC=2)=C1 BFKHLPFUCFDHEN-MHZLTWQESA-N 0.000 claims description 2
- LKKCTBWOIXLGDI-QFIPXVFZSA-N (2s)-2-(cyclopropylmethoxy)-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC3CC3)C(O)=O)=CC=2)=N1 LKKCTBWOIXLGDI-QFIPXVFZSA-N 0.000 claims description 2
- ZCXHZCCVRCJKPU-NRFANRHFSA-N (2s)-2-(ethylamino)-3-[4-[5-[[hexanoyl(methyl)amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCC)=CC(C=2C=CC(C[C@H](NCC)C(O)=O)=CC=2)=C1 ZCXHZCCVRCJKPU-NRFANRHFSA-N 0.000 claims description 2
- UZUKQIUYPJXYJH-QHCPKHFHSA-N (2s)-2-(ethylamino)-3-[4-[5-[[methyl(octanoyl)amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCCCC)=CC(C=2C=CC(C[C@H](NCC)C(O)=O)=CC=2)=C1 UZUKQIUYPJXYJH-QHCPKHFHSA-N 0.000 claims description 2
- BDNRXRUODXGOPV-QFIPXVFZSA-N (2s)-2-(ethylamino)-3-[4-[6-[heptylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](NCC)C(O)=O)=CC=2)=N1 BDNRXRUODXGOPV-QFIPXVFZSA-N 0.000 claims description 2
- PYAJJFASBODLFR-FQEVSTJZSA-N (2s)-2-(ethylamino)-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](NCC)C(O)=O)=CC=2)=N1 PYAJJFASBODLFR-FQEVSTJZSA-N 0.000 claims description 2
- YXOWTLIUVWIVPD-IBGZPJMESA-N (2s)-2-(methylamino)-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](NC)C(O)=O)=CC=2)=N1 YXOWTLIUVWIVPD-IBGZPJMESA-N 0.000 claims description 2
- OFWHTEBBLPELFA-FQEVSTJZSA-N (2s)-2-ethoxy-3-[2-fluoro-4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=C(F)C(C[C@H](OCC)C(O)=O)=CC=2)=N1 OFWHTEBBLPELFA-FQEVSTJZSA-N 0.000 claims description 2
- MTNCIFUPUVMPTF-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[2-[heptylcarbamoyl(methyl)amino]-1,3-thiazol-4-yl]phenyl]propanoic acid Chemical compound S1C(N(C)C(=O)NCCCCCCC)=NC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 MTNCIFUPUVMPTF-FQEVSTJZSA-N 0.000 claims description 2
- FJSQLLOIRWKDJE-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[2-[heptylcarbamoyl(methyl)amino]pyrimidin-4-yl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=NC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 FJSQLLOIRWKDJE-NRFANRHFSA-N 0.000 claims description 2
- KWKPLYWHWKSDSY-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[2-[methyl(pentylcarbamoyl)amino]pyridin-4-yl]phenyl]propanoic acid Chemical compound C1=NC(N(C)C(=O)NCCCCC)=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 KWKPLYWHWKSDSY-FQEVSTJZSA-N 0.000 claims description 2
- IDZOPDFJVSUEAJ-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[2-[methyl(pentylcarbamoyl)amino]pyrimidin-4-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=NC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 IDZOPDFJVSUEAJ-IBGZPJMESA-N 0.000 claims description 2
- IVRWWUMPVQUWEJ-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[3-[heptylcarbamoyl(methyl)amino]phenyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2N=C(C[C@H](OCC)C(O)=O)SC=2)=C1 IVRWWUMPVQUWEJ-FQEVSTJZSA-N 0.000 claims description 2
- RAHJIRWVWXTBBW-SFHVURJKSA-N (2s)-2-ethoxy-3-[4-[3-[methyl(pentylcarbamoyl)amino]phenyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2N=C(C[C@H](OCC)C(O)=O)SC=2)=C1 RAHJIRWVWXTBBW-SFHVURJKSA-N 0.000 claims description 2
- FFZQTVDYQKYFHK-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[4-[2-(1h-imidazol-2-yl)ethylcarbamoyl-methylamino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC(N(C)C(=O)NCCC=2NC=CN=2)=CC=N1 FFZQTVDYQKYFHK-FQEVSTJZSA-N 0.000 claims description 2
- WAKMXOGUYKEFNK-QHCPKHFHSA-N (2s)-2-ethoxy-3-[4-[4-[heptylcarbamothioyl(methyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=S)N(C)C1=CC=NC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 WAKMXOGUYKEFNK-QHCPKHFHSA-N 0.000 claims description 2
- AZCJUDGIIOMXPH-QHCPKHFHSA-N (2s)-2-ethoxy-3-[4-[4-[heptylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=NC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 AZCJUDGIIOMXPH-QHCPKHFHSA-N 0.000 claims description 2
- GGIYXSPSNFVJIT-QHCPKHFHSA-N (2s)-2-ethoxy-3-[4-[4-[methyl(2-piperidin-1-ylethylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC(N(C)C(=O)NCCN2CCCCC2)=CC=N1 GGIYXSPSNFVJIT-QHCPKHFHSA-N 0.000 claims description 2
- ISSIURGHUZINMS-VWLOTQADSA-N (2s)-2-ethoxy-3-[4-[4-[methyl(3-phenylpropylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC(N(C)C(=O)NCCCC=2C=CC=CC=2)=CC=N1 ISSIURGHUZINMS-VWLOTQADSA-N 0.000 claims description 2
- HLGQEPGQGATVLG-SANMLTNESA-N (2s)-2-ethoxy-3-[4-[4-[methyl(4-phenylbutylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC(N(C)C(=O)NCCCCC=2C=CC=CC=2)=CC=N1 HLGQEPGQGATVLG-SANMLTNESA-N 0.000 claims description 2
- VPEVVCGNUUKDSL-SANMLTNESA-N (2s)-2-ethoxy-3-[4-[4-[methyl(naphthalen-2-ylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC(N(C)C(=O)NC=2C=C3C=CC=CC3=CC=2)=CC=N1 VPEVVCGNUUKDSL-SANMLTNESA-N 0.000 claims description 2
- PYWQUDUHWKRSIC-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[4-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=NC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 PYWQUDUHWKRSIC-NRFANRHFSA-N 0.000 claims description 2
- RPTWKPQCFRBBSI-QHCPKHFHSA-N (2s)-2-ethoxy-3-[4-[5-[[methyl(octanoyl)amino]methyl]furan-2-yl]phenyl]propanoic acid Chemical compound O1C(CN(C)C(=O)CCCCCCC)=CC=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 RPTWKPQCFRBBSI-QHCPKHFHSA-N 0.000 claims description 2
- JYVVZXRJLUFZJR-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[5-[[methyl(pentanoyl)amino]methyl]thiophen-3-yl]phenyl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCC)=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 JYVVZXRJLUFZJR-FQEVSTJZSA-N 0.000 claims description 2
- XCRZWOWCAGLTJG-LJAQVGFWSA-N (2s)-2-ethoxy-3-[4-[5-[[methyl-(6-propoxynaphthalene-2-carbonyl)amino]methyl]furan-2-yl]phenyl]propanoic acid Chemical compound C1=CC2=CC(OCCC)=CC=C2C=C1C(=O)N(C)CC(O1)=CC=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 XCRZWOWCAGLTJG-LJAQVGFWSA-N 0.000 claims description 2
- OPNDUSQVMPCEMU-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[5-[heptylcarbamoyl(methyl)amino]-2-methyl-1,2,4-triazol-3-yl]phenyl]propanoic acid Chemical compound CN1N=C(N(C)C(=O)NCCCCCCC)N=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 OPNDUSQVMPCEMU-IBGZPJMESA-N 0.000 claims description 2
- STQQOIFJMDYMIA-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[5-[heptylcarbamoyl(methyl)amino]furan-2-yl]phenyl]propanoic acid Chemical compound O1C(N(C)C(=O)NCCCCCCC)=CC=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 STQQOIFJMDYMIA-NRFANRHFSA-N 0.000 claims description 2
- JNXFRDMODVHYMV-SFHVURJKSA-N (2s)-2-ethoxy-3-[4-[5-[methyl(pentylcarbamoyl)amino]thiophen-2-yl]phenyl]propanoic acid Chemical compound S1C(N(C)C(=O)NCCCCC)=CC=C1C1=CC=C(C[C@H](OCC)C(O)=O)C=C1 JNXFRDMODVHYMV-SFHVURJKSA-N 0.000 claims description 2
- MSLWXONUOOHIMN-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[6-[2-(1h-imidazol-2-yl)ethylcarbamoyl-methylamino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCC=2NC=CN=2)=N1 MSLWXONUOOHIMN-IBGZPJMESA-N 0.000 claims description 2
- LQURYVBPIQDNLU-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[6-[heptylcarbamothioyl(methyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCCCNC(=S)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 LQURYVBPIQDNLU-QFIPXVFZSA-N 0.000 claims description 2
- CPFSOVFIHPYUPD-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(2-piperidin-1-ylethylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCN2CCCCC2)=N1 CPFSOVFIHPYUPD-QFIPXVFZSA-N 0.000 claims description 2
- PBBSFMIFLZNXMI-DEOSSOPVSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(3-phenylpropylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCCC=2C=CC=CC=2)=N1 PBBSFMIFLZNXMI-DEOSSOPVSA-N 0.000 claims description 2
- ALPPMUWZCFUQFB-VWLOTQADSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(4-phenylbutylcarbamoyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCCCC=2C=CC=CC=2)=N1 ALPPMUWZCFUQFB-VWLOTQADSA-N 0.000 claims description 2
- ZDYBNQBXFIGDAP-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[6-[methyl(pentylcarbamothioyl)amino]pyridin-2-yl]phenyl]propanoic acid Chemical compound CCCCCNC(=S)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=N1 ZDYBNQBXFIGDAP-FQEVSTJZSA-N 0.000 claims description 2
- IIHHTOGWEDMEOE-QFIPXVFZSA-N (2s)-2-ethoxy-3-[5-[3-[heptylcarbamoyl(methyl)amino]phenyl]furan-2-yl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2OC(C[C@H](OCC)C(O)=O)=CC=2)=C1 IIHHTOGWEDMEOE-QFIPXVFZSA-N 0.000 claims description 2
- CWEYSLCWLMKDKG-NRFANRHFSA-N (2s)-2-ethoxy-3-[5-[3-[heptylcarbamoyl(methyl)amino]phenyl]thiophen-2-yl]propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2SC(C[C@H](OCC)C(O)=O)=CC=2)=C1 CWEYSLCWLMKDKG-NRFANRHFSA-N 0.000 claims description 2
- IYDQTZLUCAYUIJ-QHCPKHFHSA-N (2s)-2-ethoxy-3-[6-[3-[[heptanoyl(methyl)amino]methyl]phenyl]pyridin-3-yl]propanoic acid Chemical compound CCCCCCC(=O)N(C)CC1=CC=CC(C=2N=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 IYDQTZLUCAYUIJ-QHCPKHFHSA-N 0.000 claims description 2
- QURYMIHGZZOWRM-PMERELPUSA-N (2s)-2-ethoxy-3-[6-[3-[[methyl-(6-propoxynaphthalene-2-carbonyl)amino]methyl]phenyl]pyridin-3-yl]propanoic acid Chemical compound C1=CC2=CC(OCCC)=CC=C2C=C1C(=O)N(C)CC(C=1)=CC=CC=1C1=CC=C(C[C@H](OCC)C(O)=O)C=N1 QURYMIHGZZOWRM-PMERELPUSA-N 0.000 claims description 2
- XOUMQOXLXMCNCP-QHCPKHFHSA-N (2s)-2-ethoxy-3-[6-[3-[heptylcarbamothioyl(methyl)amino]phenyl]pyridin-3-yl]propanoic acid Chemical compound CCCCCCCNC(=S)N(C)C1=CC=CC(C=2N=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 XOUMQOXLXMCNCP-QHCPKHFHSA-N 0.000 claims description 2
- ARFQNSNAONYAKV-QHCPKHFHSA-N (2s)-2-ethoxy-3-[6-[3-[methyl(2-piperidin-1-ylethylcarbamoyl)amino]phenyl]pyridin-3-yl]propanoic acid Chemical compound N1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCN2CCCCC2)=C1 ARFQNSNAONYAKV-QHCPKHFHSA-N 0.000 claims description 2
- UYQJOXFCXUCYFM-VWLOTQADSA-N (2s)-2-ethoxy-3-[6-[3-[methyl(3-phenylpropylcarbamoyl)amino]phenyl]pyridin-3-yl]propanoic acid Chemical compound N1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCCC=2C=CC=CC=2)=C1 UYQJOXFCXUCYFM-VWLOTQADSA-N 0.000 claims description 2
- LJYZSBOUUGKWOY-NRFANRHFSA-N (2s)-2-ethoxy-3-[6-[3-[methyl(pentylcarbamoyl)amino]phenyl]pyridin-3-yl]propanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2N=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 LJYZSBOUUGKWOY-NRFANRHFSA-N 0.000 claims description 2
- OYRKPWHAFNFKSU-NRFANRHFSA-N (2s)-2-ethoxy-3-[6-[4-fluoro-3-[methyl(pentylcarbamoyl)amino]phenyl]pyridin-3-yl]propanoic acid Chemical compound C1=C(F)C(N(C)C(=O)NCCCCC)=CC(C=2N=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 OYRKPWHAFNFKSU-NRFANRHFSA-N 0.000 claims description 2
- PCQPDJNFYLEGKY-FQEVSTJZSA-N (2s)-2-ethoxy-3-[6-[5-[[hexanoyl(methyl)amino]methyl]thiophen-3-yl]pyridin-3-yl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCC)=CC(C=2N=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 PCQPDJNFYLEGKY-FQEVSTJZSA-N 0.000 claims description 2
- KDTIMUIWEBZMMV-QFIPXVFZSA-N (2s)-2-ethoxy-3-[6-[5-[[methyl(octanoyl)amino]methyl]thiophen-3-yl]pyridin-3-yl]propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCCCC)=CC(C=2N=CC(C[C@H](OCC)C(O)=O)=CC=2)=C1 KDTIMUIWEBZMMV-QFIPXVFZSA-N 0.000 claims description 2
- XBHQOMRKOUANQQ-BYPYZUCNSA-N (2s)-2-ethoxypropanoic acid Chemical compound CCO[C@@H](C)C(O)=O XBHQOMRKOUANQQ-BYPYZUCNSA-N 0.000 claims description 2
- DLHYTPCXXVOAFJ-FQEVSTJZSA-N (2s)-3-[4-[4-[2-(dimethylamino)ethylcarbamoyl-methylamino]pyridin-2-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC(N(C)C(=O)NCCN(C)C)=CC=N1 DLHYTPCXXVOAFJ-FQEVSTJZSA-N 0.000 claims description 2
- CAZQHGSQOOWRQR-DEOSSOPVSA-N (2s)-3-[4-[4-[[4-(dimethylamino)phenyl]carbamoyl-methylamino]pyridin-2-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC(N(C)C(=O)NC=2C=CC(=CC=2)N(C)C)=CC=N1 CAZQHGSQOOWRQR-DEOSSOPVSA-N 0.000 claims description 2
- HGNFKBIQLFCPPE-QHCPKHFHSA-N (2s)-3-[4-[5-[[(3-cyclopentyl-2-oxopropyl)amino]methyl]thiophen-3-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CSC(CNCC(=O)CC2CCCC2)=C1 HGNFKBIQLFCPPE-QHCPKHFHSA-N 0.000 claims description 2
- GZCIZIBIGCJREB-FQEVSTJZSA-N (2s)-3-[4-[5-[[hexanoyl(methyl)amino]methyl]thiophen-3-yl]phenyl]-2-(methylamino)propanoic acid Chemical compound S1C(CN(C)C(=O)CCCCC)=CC(C=2C=CC(C[C@H](NC)C(O)=O)=CC=2)=C1 GZCIZIBIGCJREB-FQEVSTJZSA-N 0.000 claims description 2
- TZUBLYHJQCWHKD-FQEVSTJZSA-N (2s)-3-[4-[6-[2,1,3-benzothiadiazol-4-ylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NC=2C3=NSN=C3C=CC=2)=N1 TZUBLYHJQCWHKD-FQEVSTJZSA-N 0.000 claims description 2
- LKVXHQZPZVYTFW-IBGZPJMESA-N (2s)-3-[4-[6-[2-(dimethylamino)ethylcarbamoyl-methylamino]pyridin-2-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCN(C)C)=N1 LKVXHQZPZVYTFW-IBGZPJMESA-N 0.000 claims description 2
- KPXKKQCCASKMIO-QHCPKHFHSA-N (2s)-3-[4-[6-[[4-(dimethylamino)phenyl]carbamoyl-methylamino]pyridin-2-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NC=2C=CC(=CC=2)N(C)C)=N1 KPXKKQCCASKMIO-QHCPKHFHSA-N 0.000 claims description 2
- DGTDFVCKHICYQJ-NRFANRHFSA-N (2s)-3-[4-[6-[cyclohexylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NC2CCCCC2)=N1 DGTDFVCKHICYQJ-NRFANRHFSA-N 0.000 claims description 2
- ZMGCCUGWIRZJHH-NRFANRHFSA-N (2s)-3-[4-[6-[heptylcarbamoyl(methyl)amino]pyridin-2-yl]phenyl]-2-(methylamino)propanoic acid Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](NC)C(O)=O)=CC=2)=N1 ZMGCCUGWIRZJHH-NRFANRHFSA-N 0.000 claims description 2
- OMXFLPSNAIRXTN-NRFANRHFSA-N (2s)-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]-2-propan-2-yloxypropanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OC(C)C)C(O)=O)=CC=2)=N1 OMXFLPSNAIRXTN-NRFANRHFSA-N 0.000 claims description 2
- JAHYLBDXODZQAX-NRFANRHFSA-N (2s)-3-[4-[6-[methyl(pentylcarbamoyl)amino]pyridin-2-yl]phenyl]-2-propoxypropanoic acid Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCCC)C(O)=O)=CC=2)=N1 JAHYLBDXODZQAX-NRFANRHFSA-N 0.000 claims description 2
- AXYWHUDMOVYHIS-QHCPKHFHSA-N (2s)-3-[6-[3-[2-(2,1,3-benzothiadiazol-4-yl)ethylcarbamoyl-methylamino]phenyl]pyridin-3-yl]-2-ethoxypropanoic acid Chemical compound N1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(N(C)C(=O)NCCC=2C3=NSN=C3C=CC=2)=C1 AXYWHUDMOVYHIS-QHCPKHFHSA-N 0.000 claims description 2
- BEBICARMVIPACF-ZQCMTOKYSA-N (e)-but-2-enedioate;(2s)-2-ethoxy-3-[4-[6-[heptylcarbamoyl(methyl)amino]pyridin-1-ium-2-yl]phenyl]propanoic acid Chemical compound [O-]C(=O)\C=C\C([O-])=O.CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=[NH+]1.CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=[NH+]1 BEBICARMVIPACF-ZQCMTOKYSA-N 0.000 claims description 2
- BEBICARMVIPACF-VKHKXGSQSA-N (z)-but-2-enedioate;(2s)-2-ethoxy-3-[4-[6-[heptylcarbamoyl(methyl)amino]pyridin-1-ium-2-yl]phenyl]propanoic acid Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=[NH+]1.CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=CC(C[C@H](OCC)C(O)=O)=CC=2)=[NH+]1 BEBICARMVIPACF-VKHKXGSQSA-N 0.000 claims description 2
- JBHMVTWMRRQLME-UHFFFAOYSA-N 1-[3-[2-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]pyrimidin-5-yl]phenyl]-1-methyl-3-pentylurea Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2C=NC(CC3C(NC(=O)S3)=O)=NC=2)=C1 JBHMVTWMRRQLME-UHFFFAOYSA-N 0.000 claims description 2
- GHPQJNQZFBNUCF-UHFFFAOYSA-N 1-[3-[2-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]pyrimidin-5-yl]phenyl]-3-heptyl-1-methylurea Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2C=NC(CC3C(NC(=O)S3)=O)=NC=2)=C1 GHPQJNQZFBNUCF-UHFFFAOYSA-N 0.000 claims description 2
- OUGBNVOLNAGVAG-DEOSSOPVSA-N 1-[3-[2-[(2s)-2-ethoxy-3-(4-methylpiperidin-1-yl)-3-oxopropyl]-1,3-thiazol-4-yl]phenyl]-1-methyl-3-pentylurea Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2N=C(C[C@H](OCC)C(=O)N3CCC(C)CC3)SC=2)=C1 OUGBNVOLNAGVAG-DEOSSOPVSA-N 0.000 claims description 2
- OYWSBQREPWOJHI-DEOSSOPVSA-N 1-[3-[5-[(2s)-2-ethoxy-2-(5-propyl-1,3,4-oxadiazol-2-yl)ethyl]pyrimidin-2-yl]phenyl]-3-heptyl-1-methylurea Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2N=CC(C[C@H](OCC)C=3OC(CCC)=NN=3)=CN=2)=C1 OYWSBQREPWOJHI-DEOSSOPVSA-N 0.000 claims description 2
- YTDPZRGBGPENJW-MHZLTWQESA-N 1-[3-[5-[(2s)-2-ethoxy-3-(4-methylpiperidin-1-yl)-3-oxopropyl]pyridin-2-yl]phenyl]-1-methyl-3-pentylurea Chemical compound CCCCCNC(=O)N(C)C1=CC=CC(C=2N=CC(C[C@H](OCC)C(=O)N3CCC(C)CC3)=CC=2)=C1 YTDPZRGBGPENJW-MHZLTWQESA-N 0.000 claims description 2
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- VBCKTNYWVSYBIU-DEOSSOPVSA-N methyl (2s)-2-ethoxy-3-[6-[3-[heptylcarbamoyl(methyl)amino]phenyl]pyridin-3-yl]propanoate Chemical compound CCCCCCCNC(=O)N(C)C1=CC=CC(C=2N=CC(C[C@H](OCC)C(=O)OC)=CC=2)=C1 VBCKTNYWVSYBIU-DEOSSOPVSA-N 0.000 description 1
- MVYVTZKABLVBCN-QHCPKHFHSA-N methyl (2s)-2-ethoxy-3-[6-[3-[methyl-(4-nitrophenoxy)carbonylamino]phenyl]pyridin-3-yl]propanoate Chemical compound N1=CC(C[C@H](OCC)C(=O)OC)=CC=C1C1=CC=CC(N(C)C(=O)OC=2C=CC(=CC=2)[N+]([O-])=O)=C1 MVYVTZKABLVBCN-QHCPKHFHSA-N 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 description 1
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- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- 238000004321 preservation Methods 0.000 description 1
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- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
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- UQOQENZZLBSFKO-POPPZSFYSA-N prostaglandin J2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O UQOQENZZLBSFKO-POPPZSFYSA-N 0.000 description 1
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- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
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- 102000003702 retinoic acid receptors Human genes 0.000 description 1
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- 102000027483 retinoid hormone receptors Human genes 0.000 description 1
- 108091008679 retinoid hormone receptors Proteins 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
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- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- ZOFJBHYCGASUQK-UHFFFAOYSA-N sodium;trimethylsilylazanide Chemical compound [Na+].C[Si](C)(C)[NH-] ZOFJBHYCGASUQK-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- OOPDICQLTIZXEC-UHFFFAOYSA-N tert-butyl n-(6-bromopyridin-2-yl)-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=CC(Br)=N1 OOPDICQLTIZXEC-UHFFFAOYSA-N 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
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- 239000002076 α-tocopherol Substances 0.000 description 1
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- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/55—Acids; Esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0307487A FR2856401B1 (fr) | 2003-06-20 | 2003-06-20 | Nouveaux composes modulateurs des recepteurs de type ppargamma et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| FR0307487 | 2003-06-20 | ||
| US489672P | 2003-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2370901T3 true ES2370901T3 (es) | 2011-12-23 |
Family
ID=33484606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04740561T Expired - Lifetime ES2370901T3 (es) | 2003-06-20 | 2004-06-16 | Nuevos compuestos que modulan los receptores de tipo ppar-gamma y su utilización en composiciones cosméticas o farmacéuticas. |
Country Status (6)
| Country | Link |
|---|---|
| CN (1) | CN1863800B (de) |
| AR (1) | AR044789A1 (de) |
| AT (1) | ATE517894T1 (de) |
| ES (1) | ES2370901T3 (de) |
| FR (1) | FR2856401B1 (de) |
| ZA (1) | ZA200510217B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2887441A1 (fr) * | 2005-06-26 | 2006-12-29 | Oreal | Utilisation de composes benzyl-1,3-thiazolidine-2,4-diones pour favoriser et/ou induire et/ou stimuler la pigmentation des matieres keratiniques et/ou limiter leur depigmentation et/ou leur blanchiment. |
| FR2887444A1 (fr) * | 2005-06-28 | 2006-12-29 | Oreal | Composes benzylidene-1,3-thiazolidine-2,4-diones, leurs utilisations et compositions pour stimuler ou induire la pousse des fibres keratiniques et/ou freiner leur chute et/ou augmenter leur densite. |
| US10689374B1 (en) | 2019-07-12 | 2020-06-23 | United Arab Emirates University | Pyrimidine-thiazolidinone derivatives |
| US10702525B1 (en) | 2019-09-04 | 2020-07-07 | United Arab Emirates University | Pyrimidine derivatives as anti-diabetic agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2812876B1 (fr) * | 2000-08-08 | 2002-09-27 | Galderma Res & Dev | Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar-gamma et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| AU2002252227A1 (en) * | 2001-03-07 | 2002-09-24 | Maxia Pharmaceuticals, Inc. | Heterocyclic derivatives for the treatment of cancer and other proliferative diseases |
-
2003
- 2003-06-20 FR FR0307487A patent/FR2856401B1/fr not_active Expired - Fee Related
-
2004
- 2004-06-16 CN CN2004800237079A patent/CN1863800B/zh not_active Expired - Fee Related
- 2004-06-16 ES ES04740561T patent/ES2370901T3/es not_active Expired - Lifetime
- 2004-06-16 AT AT04740561T patent/ATE517894T1/de not_active IP Right Cessation
- 2004-06-17 AR ARP040102099A patent/AR044789A1/es unknown
-
2005
- 2005-12-15 ZA ZA200510217A patent/ZA200510217B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2856401A1 (fr) | 2004-12-24 |
| AR044789A1 (es) | 2005-10-05 |
| FR2856401B1 (fr) | 2010-02-12 |
| ATE517894T1 (de) | 2011-08-15 |
| CN1863800A (zh) | 2006-11-15 |
| ZA200510217B (en) | 2006-08-30 |
| CN1863800B (zh) | 2013-07-24 |
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