ZA200608886B - Indolyl derivatives as liver-X-receptor modulators - Google Patents
Indolyl derivatives as liver-X-receptor modulators Download PDFInfo
- Publication number
- ZA200608886B ZA200608886B ZA200608886A ZA200608886A ZA200608886B ZA 200608886 B ZA200608886 B ZA 200608886B ZA 200608886 A ZA200608886 A ZA 200608886A ZA 200608886 A ZA200608886 A ZA 200608886A ZA 200608886 B ZA200608886 B ZA 200608886B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- indol
- ylmethyl
- oxazol
- propan
- Prior art date
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- 102000004311 liver X receptors Human genes 0.000 title claims description 34
- 108090000865 liver X receptors Proteins 0.000 title claims description 34
- 125000001041 indolyl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 aminocarbonyloxy, carboxy Chemical group 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical group 0.000 claims description 31
- 150000002431 hydrogen Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 27
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 239000005711 Benzoic acid Substances 0.000 claims description 11
- 108010023302 HDL Cholesterol Proteins 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 7
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 7
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
- 125000005121 aminocarbonylalkoxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 210000004185 liver Anatomy 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 108010028554 LDL Cholesterol Proteins 0.000 claims description 6
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 6
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 230000003143 atherosclerotic effect Effects 0.000 claims description 6
- 239000013256 coordination polymer Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 229940125388 beta agonist Drugs 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 5
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- KYMVFNWUYUFCMK-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(C)=C1 KYMVFNWUYUFCMK-UHFFFAOYSA-N 0.000 claims description 4
- YYAPJXBJDOAVNX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[5-methyl-2-(3-methylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(C)=C1 YYAPJXBJDOAVNX-UHFFFAOYSA-N 0.000 claims description 4
- OGMIHHYRJZNMKR-UHFFFAOYSA-N 2-[4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenoxy]acetic acid Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(OCC(O)=O)C=C1 OGMIHHYRJZNMKR-UHFFFAOYSA-N 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ANHWUBNZUDKNTE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1F ANHWUBNZUDKNTE-UHFFFAOYSA-N 0.000 claims description 3
- CXWHMGXTGAJWJP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[2-[4-(1-hydroxyethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]propan-2-ol Chemical compound C1=CC(C(O)C)=CC=C1C1=NC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 CXWHMGXTGAJWJP-UHFFFAOYSA-N 0.000 claims description 3
- HAUAAJMDPVKBLA-UHFFFAOYSA-N 2-[3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenoxy]acetic acid Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(OCC(O)=O)=C1 HAUAAJMDPVKBLA-UHFFFAOYSA-N 0.000 claims description 3
- IFQBECWMDGNTGI-UHFFFAOYSA-N 2-[4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenoxy]-n,n-dimethylacetamide Chemical compound C1=CC(OCC(=O)N(C)C)=CC=C1C1=NC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 IFQBECWMDGNTGI-UHFFFAOYSA-N 0.000 claims description 3
- UQHHJWIYATWBOD-UHFFFAOYSA-N 3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]benzoic acid Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(C(O)=O)=C1 UQHHJWIYATWBOD-UHFFFAOYSA-N 0.000 claims description 3
- RFRKNWFGKRHMRD-UHFFFAOYSA-N 4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=NC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 RFRKNWFGKRHMRD-UHFFFAOYSA-N 0.000 claims description 3
- LESNQXXMMJWJFI-UHFFFAOYSA-N 4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]benzoic acid Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(O)=O)C=C1 LESNQXXMMJWJFI-UHFFFAOYSA-N 0.000 claims description 3
- 206010008635 Cholestasis Diseases 0.000 claims description 3
- NFCKDWJRKPRLSC-UHFFFAOYSA-N FC(C(C(F)(F)F)(O)C=1C=C2C=CN(C2=CC=1)C(CC)C1=CC=CC=C1)(F)F Chemical compound FC(C(C(F)(F)F)(O)C=1C=C2C=CN(C2=CC=1)C(CC)C1=CC=CC=C1)(F)F NFCKDWJRKPRLSC-UHFFFAOYSA-N 0.000 claims description 3
- 206010016654 Fibrosis Diseases 0.000 claims description 3
- 238000008214 LDL Cholesterol Methods 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- 230000007870 cholestasis Effects 0.000 claims description 3
- 231100000359 cholestasis Toxicity 0.000 claims description 3
- 206010009887 colitis Diseases 0.000 claims description 3
- 230000004761 fibrosis Effects 0.000 claims description 3
- 208000002780 macular degeneration Diseases 0.000 claims description 3
- PAOBFSOYKWMINH-GFCCVEGCSA-N 1,1,1,3,3,3-hexafluoro-2-[(2r)-2-methyl-1-[[5-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound C([C@H]1C)C2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(C(F)(F)F)=C1 PAOBFSOYKWMINH-GFCCVEGCSA-N 0.000 claims description 2
- CNXYRVFERZLJRP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenylethyl)-2-methyl-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1C(CO)C1=CC=CC=C1 CNXYRVFERZLJRP-UHFFFAOYSA-N 0.000 claims description 2
- ZWNHPZGFEIJQKL-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenylethyl)-2-methylindol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1C(CO)C1=CC=CC=C1 ZWNHPZGFEIJQKL-UHFFFAOYSA-N 0.000 claims description 2
- SQYSPXIXKRWRCR-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[2-(2-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-2-methyl-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound COC1=CC=CC=C1C1=NC(CN2C3=CC=C(C=C3CC2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 SQYSPXIXKRWRCR-UHFFFAOYSA-N 0.000 claims description 2
- MBNWVRFWHMEVOH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[2-(2-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]propan-2-ol Chemical compound COC1=CC=CC=C1C1=NC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 MBNWVRFWHMEVOH-UHFFFAOYSA-N 0.000 claims description 2
- HJOVWVKXRIPVAJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[2-[4-(hydroxymethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(CO)C=C1 HJOVWVKXRIPVAJ-UHFFFAOYSA-N 0.000 claims description 2
- WKECRBDKFXLPPM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[3-(4-fluorophenoxy)phenyl]methyl]-2-methyl-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(C=1)=CC=CC=1OC1=CC=C(F)C=C1 WKECRBDKFXLPPM-UHFFFAOYSA-N 0.000 claims description 2
- FJSPKELWCYZBRA-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(naphthalen-1-ylmethyl)-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound C1=CC=C2C(CN3C4=CC=C(C=C4CC3C)C(O)(C(F)(F)F)C(F)(F)F)=CC=CC2=C1 FJSPKELWCYZBRA-UHFFFAOYSA-N 0.000 claims description 2
- RIVQTXCNRDWDCJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[(5-methyl-2-pyridin-3-yl-1,3-oxazol-4-yl)methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CN=C1 RIVQTXCNRDWDCJ-UHFFFAOYSA-N 0.000 claims description 2
- QSOHEEZSVLEVKE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC1=C(C)ON=C1C1=CC=CC=C1 QSOHEEZSVLEVKE-UHFFFAOYSA-N 0.000 claims description 2
- QYCJDQNGCJCRGF-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[2-(2-methyl-5-phenyl-1,3-oxazol-4-yl)ethyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CCC=1N=C(C)OC=1C1=CC=CC=C1 QYCJDQNGCJCRGF-UHFFFAOYSA-N 0.000 claims description 2
- GZLDYUKWQBGONV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CCC(=C(O1)C)N=C1C1=CC=CC=C1 GZLDYUKWQBGONV-UHFFFAOYSA-N 0.000 claims description 2
- IXWANNMIQSYUPM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[2-methyl-5-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(N(N=1)C)=CC=1C1=CC=C(C(F)(F)F)C=C1 IXWANNMIQSYUPM-UHFFFAOYSA-N 0.000 claims description 2
- NSRJDANCJUMBMD-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[3-(morpholin-4-ylmethyl)phenyl]methyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(C=1)=CC=CC=1CN1CCOCC1 NSRJDANCJUMBMD-UHFFFAOYSA-N 0.000 claims description 2
- MDBLIMFGYDRJOW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[5-methyl-2-(2-phenylethenyl)-1,3-oxazol-4-yl]methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C=CC1=CC=CC=C1 MDBLIMFGYDRJOW-UHFFFAOYSA-N 0.000 claims description 2
- KGBMSZUMALSRRZ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[5-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(C(F)(F)F)=C1 KGBMSZUMALSRRZ-UHFFFAOYSA-N 0.000 claims description 2
- FZQFOGNLAOHQAU-UHFFFAOYSA-N 1-benzyl-5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)indole-2-carbaldehyde Chemical compound O=CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC1=CC=CC=C1 FZQFOGNLAOHQAU-UHFFFAOYSA-N 0.000 claims description 2
- JLLJWCUWQJREMW-UHFFFAOYSA-N 2-[1-[[2-(4-tert-butylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-2-methyl-2,3-dihydroindol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(C)(C)C)C=C1 JLLJWCUWQJREMW-UHFFFAOYSA-N 0.000 claims description 2
- GBAGNBJMXYZOKU-UHFFFAOYSA-N 3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]benzoic acid Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(C(O)=O)=C1 GBAGNBJMXYZOKU-UHFFFAOYSA-N 0.000 claims description 2
- ZEUOOYOTVSBQIL-UHFFFAOYSA-N 3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2OC(C)=C(CN3C4=CC=C(C=C4C=C3C)C(O)(C(F)(F)F)C(F)(F)F)N=2)=C1 ZEUOOYOTVSBQIL-UHFFFAOYSA-N 0.000 claims description 2
- KNTKZSTYICOKPY-UHFFFAOYSA-N 3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(O)=C1 KNTKZSTYICOKPY-UHFFFAOYSA-N 0.000 claims description 2
- JBXKLWVRAYTJBG-UHFFFAOYSA-N 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-n-methyl-n-(2-phenylethyl)benzamide Chemical compound C=1C=CC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=CC=1C(=O)N(C)CCC1=CC=CC=C1 JBXKLWVRAYTJBG-UHFFFAOYSA-N 0.000 claims description 2
- POORKPPTCQMBGL-UHFFFAOYSA-N CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1C(C1=C(OC=N1)C)CCC1=CC=CC=C1 Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1C(C1=C(OC=N1)C)CCC1=CC=CC=C1 POORKPPTCQMBGL-UHFFFAOYSA-N 0.000 claims description 2
- QZQWIPUEPJGWPU-UHFFFAOYSA-N [4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenyl] morpholine-4-carboxylate Chemical compound N=1C(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)OC=1C(C=C1)=CC=C1OC(=O)N1CCOCC1 QZQWIPUEPJGWPU-UHFFFAOYSA-N 0.000 claims description 2
- GAGBARLNTMOXMA-UHFFFAOYSA-N [4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenyl] n,n-dimethylcarbamate Chemical compound C1=CC(OC(=O)N(C)C)=CC=C1C1=NC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 GAGBARLNTMOXMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- TYMSGJURMSBLOI-UHFFFAOYSA-N ethyl 2-[[3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]benzoyl]-methylamino]acetate Chemical compound CCOC(=O)CN(C)C(=O)C1=CC=CC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C1 TYMSGJURMSBLOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- STDLOAMRLPQUBX-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)-4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-1,3-oxazole-5-carboxylate Chemical compound N=1C(CN2C3=CC=C(C=C3CC2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C(=O)OC)OC=1C1=CC=CC=C1Cl STDLOAMRLPQUBX-UHFFFAOYSA-N 0.000 claims description 2
- IKGSSAUECRJMMJ-UHFFFAOYSA-N methyl 2-[3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(C=2OC(C)=C(CN3C4=CC=C(C=C4C=C3C)C(O)(C(F)(F)F)C(F)(F)F)N=2)=C1 IKGSSAUECRJMMJ-UHFFFAOYSA-N 0.000 claims description 2
- GASOWTSGOFVNIR-UHFFFAOYSA-N methyl 2-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]-2-phenylacetate Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1C(C(=O)OC)C1=CC=CC=C1 GASOWTSGOFVNIR-UHFFFAOYSA-N 0.000 claims description 2
- OGNPZJUKBYTCPI-UHFFFAOYSA-N methyl 3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-1,3-oxazol-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2OC=C(CN3C4=CC=C(C=C4CC3C)C(O)(C(F)(F)F)C(F)(F)F)N=2)=C1 OGNPZJUKBYTCPI-UHFFFAOYSA-N 0.000 claims description 2
- FSOBSYLCJDOEIE-UHFFFAOYSA-N methyl 3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2OC(C)=C(CN3C4=CC=C(C=C4CC3C)C(O)(C(F)(F)F)C(F)(F)F)N=2)=C1 FSOBSYLCJDOEIE-UHFFFAOYSA-N 0.000 claims description 2
- SNFCQECKHQVLEC-UHFFFAOYSA-N methyl 3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2OC(C)=C(CN3C4=CC=C(C=C4C=C3C)C(O)(C(F)(F)F)C(F)(F)F)N=2)=C1 SNFCQECKHQVLEC-UHFFFAOYSA-N 0.000 claims description 2
- XRBFRBNCGBZABQ-UHFFFAOYSA-N methyl 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C1 XRBFRBNCGBZABQ-UHFFFAOYSA-N 0.000 claims description 2
- FFRKWBNZDOZTLQ-UHFFFAOYSA-N methyl 4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C2=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C2C=C1C FFRKWBNZDOZTLQ-UHFFFAOYSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- ATKHXXPHYQIJFQ-UHFFFAOYSA-N 2-[4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenoxy]-n,n-dimethylacetamide Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(OCC(=O)N(C)C)C=C1 ATKHXXPHYQIJFQ-UHFFFAOYSA-N 0.000 claims 2
- QIWKBONFRPOHIY-UHFFFAOYSA-N 4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(O)C=C1 QIWKBONFRPOHIY-UHFFFAOYSA-N 0.000 claims 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 2
- ZYXQSOPBZDJDLA-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-(1-phenylpropyl)-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound FC(C(C(F)(F)F)(O)C=1C=C2CCN(C2=CC=1)C(CC)C1=CC=CC=C1)(F)F ZYXQSOPBZDJDLA-UHFFFAOYSA-N 0.000 claims 1
- UXKNTLGILLGDPP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[2-[3-(hydroxymethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methyl]-2-methyl-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(CO)=C1 UXKNTLGILLGDPP-UHFFFAOYSA-N 0.000 claims 1
- OLFOKLPGFMUXBS-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[1-[[2-[3-(hydroxymethyl)phenyl]-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(CO)=C1 OLFOKLPGFMUXBS-UHFFFAOYSA-N 0.000 claims 1
- CNFPEEOTHVQVHL-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-(naphthalen-2-ylmethyl)-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound C1=CC=CC2=CC(CN3C4=CC=C(C=C4CC3C)C(O)(C(F)(F)F)C(F)(F)F)=CC=C21 CNFPEEOTHVQVHL-UHFFFAOYSA-N 0.000 claims 1
- FIRCHXGRTDLYPB-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1 FIRCHXGRTDLYPB-UHFFFAOYSA-N 0.000 claims 1
- UJJZRTUOQJLBRF-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC1=C(C)ON=C1C1=CC=CC=C1 UJJZRTUOQJLBRF-UHFFFAOYSA-N 0.000 claims 1
- DUHULEHCZCICPW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[2-(trifluoromethyl)quinolin-6-yl]methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound N1=C(C(F)(F)F)C=CC2=CC(CN3C4=CC=C(C=C4CC3C)C(O)(C(F)(F)F)C(F)(F)F)=CC=C21 DUHULEHCZCICPW-UHFFFAOYSA-N 0.000 claims 1
- BKKNGTGTODMIAT-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[2-methyl-5-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(N(N=1)C)=CC=1C1=CC=C(C(F)(F)F)C=C1 BKKNGTGTODMIAT-UHFFFAOYSA-N 0.000 claims 1
- XTCMZKZLYNFTRG-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(C(=N1)C)=CC=C1C1=CC=C(C(F)(F)F)C=C1 XTCMZKZLYNFTRG-UHFFFAOYSA-N 0.000 claims 1
- BSOKTAHJYLNYIA-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1C BSOKTAHJYLNYIA-UHFFFAOYSA-N 0.000 claims 1
- CUDAKNMRCCWKGN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propan-2-ol Chemical compound C1=CC(OC(C)C)=CC=C1C1=NC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 CUDAKNMRCCWKGN-UHFFFAOYSA-N 0.000 claims 1
- FJYUGWZCSMCOBJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-methyl-1-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methyl]-2,3-dihydroindol-5-yl]propan-2-ol Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(CN2C3=CC=C(C=C3CC2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 FJYUGWZCSMCOBJ-UHFFFAOYSA-N 0.000 claims 1
- CQURMGCAACOQLN-UHFFFAOYSA-N 2-(1-benzyl-2,3-dihydroindol-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC1=CC=CC=C1 CQURMGCAACOQLN-UHFFFAOYSA-N 0.000 claims 1
- GNZMKMULCULQNG-UHFFFAOYSA-N 2-(1-benzylindol-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC1=CC=CC=C1 GNZMKMULCULQNG-UHFFFAOYSA-N 0.000 claims 1
- GKGSIZSOWJMMEQ-UHFFFAOYSA-N 2-[1-[2-(2,5-diphenyl-1,3-oxazol-4-yl)ethyl]-2-methyl-2,3-dihydroindol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CCC=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 GKGSIZSOWJMMEQ-UHFFFAOYSA-N 0.000 claims 1
- UIYVRGDVBFIEFN-UHFFFAOYSA-N 2-[1-[[2-(3-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC(Cl)=C1 UIYVRGDVBFIEFN-UHFFFAOYSA-N 0.000 claims 1
- IZSNYLUTRGYHEX-UHFFFAOYSA-N 2-[1-[[2-(4-chlorophenyl)-5-methyl-1,3-thiazol-4-yl]methyl]-2-methyl-2,3-dihydroindol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(S1)C)N=C1C1=CC=C(Cl)C=C1 IZSNYLUTRGYHEX-UHFFFAOYSA-N 0.000 claims 1
- WRFOTYDZCYNMQC-UHFFFAOYSA-N 2-[1-benzyl-2-(1-hydroxyethyl)indol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound CC(O)C1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC1=CC=CC=C1 WRFOTYDZCYNMQC-UHFFFAOYSA-N 0.000 claims 1
- ZQQMOLCDETXHKM-UHFFFAOYSA-N 2-[2,3-dimethyl-1-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]indol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound N=1C(CN2C3=CC=C(C=C3C(C)=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)OC=1C1=CC=CC=C1 ZQQMOLCDETXHKM-UHFFFAOYSA-N 0.000 claims 1
- PGPZEXJNZRKJPO-UHFFFAOYSA-N 2-[3-chloro-1-[[2-(3-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-2-methylindol-5-yl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound N=1C(CN2C3=CC=C(C=C3C(Cl)=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)OC=1C1=CC=CC(Cl)=C1 PGPZEXJNZRKJPO-UHFFFAOYSA-N 0.000 claims 1
- PRVYGYSXBSKVJD-UHFFFAOYSA-N 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C1 PRVYGYSXBSKVJD-UHFFFAOYSA-N 0.000 claims 1
- QTEOKZOFKZIFHD-UHFFFAOYSA-N 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-n-methyl-n-(pyridin-2-ylmethyl)benzamide Chemical compound C=1C=CC(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=CC=1C(=O)N(C)CC1=CC=CC=N1 QTEOKZOFKZIFHD-UHFFFAOYSA-N 0.000 claims 1
- ILIAISGLRHPVDX-UHFFFAOYSA-N 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]benzoic acid Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC1=CC=CC(C(O)=O)=C1 ILIAISGLRHPVDX-UHFFFAOYSA-N 0.000 claims 1
- FUGTVPTWNSTHQP-UHFFFAOYSA-N 4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]benzoic acid Chemical compound CC1CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(O)=O)C=C1 FUGTVPTWNSTHQP-UHFFFAOYSA-N 0.000 claims 1
- SEEPCFLCVNONOM-UHFFFAOYSA-N [3-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenyl] morpholine-4-carboxylate Chemical compound N=1C(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)OC=1C(C=1)=CC=CC=1OC(=O)N1CCOCC1 SEEPCFLCVNONOM-UHFFFAOYSA-N 0.000 claims 1
- CBGBSHRLEUKFOB-UHFFFAOYSA-N [3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(C=1)=CC=CC=1C(=O)N1CCOCC1 CBGBSHRLEUKFOB-UHFFFAOYSA-N 0.000 claims 1
- JHXZILIJWCVKJD-UHFFFAOYSA-N [3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]phenyl]-piperidin-1-ylmethanone Chemical compound CC1=CC2=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C2N1CC(C=1)=CC=CC=1C(=O)N1CCCCC1 JHXZILIJWCVKJD-UHFFFAOYSA-N 0.000 claims 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims 1
- AFUAOJSYPBKNRB-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)-4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylindol-1-yl]methyl]-1,3-oxazole-5-carboxylate Chemical compound N=1C(CN2C3=CC=C(C=C3C=C2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C(=O)OC)OC=1C1=CC=CC=C1Cl AFUAOJSYPBKNRB-UHFFFAOYSA-N 0.000 claims 1
- DRJWSRXNKUURDA-UHFFFAOYSA-N methyl 2-[4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C1=NC(CN2C3=CC=C(C=C3CC2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 DRJWSRXNKUURDA-UHFFFAOYSA-N 0.000 claims 1
- WQDXJONOVRRJNY-UHFFFAOYSA-N methyl 4-[4-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methyl-2,3-dihydroindol-1-yl]methyl]-5-methyl-1,3-oxazol-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(CN2C3=CC=C(C=C3CC2C)C(O)(C(F)(F)F)C(F)(F)F)=C(C)O1 WQDXJONOVRRJNY-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
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- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
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- C07D413/02—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
- C07D413/10—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 aromatic rings
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- C—CHEMISTRY; METALLURGY
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- 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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EP (1) | EP1756096B1 (ko) |
JP (1) | JP4682192B2 (ko) |
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CN (1) | CN1950365A (ko) |
AR (1) | AR049497A1 (ko) |
AT (1) | ATE439357T1 (ko) |
AU (1) | AU2005238176B2 (ko) |
BR (1) | BRPI0510599A (ko) |
CA (1) | CA2564563C (ko) |
DE (1) | DE602005015962D1 (ko) |
DK (1) | DK1756096T3 (ko) |
ES (1) | ES2329489T3 (ko) |
HR (1) | HRP20090533T1 (ko) |
IL (1) | IL178767A0 (ko) |
MX (1) | MXPA06012683A (ko) |
MY (1) | MY139571A (ko) |
NO (1) | NO20065503L (ko) |
NZ (1) | NZ550447A (ko) |
PL (1) | PL1756096T3 (ko) |
PT (1) | PT1756096E (ko) |
RU (1) | RU2368612C2 (ko) |
SI (1) | SI1756096T1 (ko) |
TW (1) | TWI287537B (ko) |
WO (1) | WO2005105791A1 (ko) |
ZA (1) | ZA200608886B (ko) |
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US20070244128A1 (en) * | 2005-11-04 | 2007-10-18 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein (flap) inhibitors |
US8399666B2 (en) * | 2005-11-04 | 2013-03-19 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
US20070219206A1 (en) * | 2005-11-04 | 2007-09-20 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein (flap) inhibitors |
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US7977359B2 (en) * | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
PL2054049T3 (pl) | 2006-08-24 | 2016-11-30 | Podstawione acyloanilidy i sposoby ich stosowania | |
WO2008042571A2 (en) | 2006-09-29 | 2008-04-10 | Smithkline Beecham Corporation | Substituted indole compounds |
EP2094643B1 (en) | 2006-12-01 | 2012-02-29 | Bristol-Myers Squibb Company | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
PE20090213A1 (es) * | 2007-05-04 | 2009-02-28 | Bristol Myers Squibb Co | Agonistas del receptor acoplado a la proteina g gpr119 [6,5]-biciclicos |
PE20090222A1 (es) * | 2007-05-04 | 2009-03-27 | Bristol Myers Squibb Co | Compuestos [6,6] y [6,7]-biciclicos como agonistas del receptor acoplado a la proteina g gpr119 |
US8003796B2 (en) * | 2007-07-17 | 2011-08-23 | Bristol-Myers Squibb Company | Pyridone GPR119 G protein-coupled receptor agonists |
KR100918814B1 (ko) * | 2007-10-04 | 2009-09-25 | 건국대학교 산학협력단 | 인쇄방법을 이용한 세라믹 전자부품 고속제조방법 |
TW200920369A (en) * | 2007-10-26 | 2009-05-16 | Amira Pharmaceuticals Inc | 5-lipoxygenase activating protein (flap) inhibitor |
WO2009115212A1 (en) * | 2008-03-17 | 2009-09-24 | F. Hoffmann-La Roche Ag | Lxr ligand binding domain (lxr lbd) crystals |
KR20160129109A (ko) * | 2008-05-23 | 2016-11-08 | 아미라 파마슈티칼스 인코포레이티드 | 5-리폭시게나아제 활성화 단백질 억제제 |
TW201006821A (en) | 2008-07-16 | 2010-02-16 | Bristol Myers Squibb Co | Pyridone and pyridazone analogues as GPR119 modulators |
US8546431B2 (en) | 2008-10-01 | 2013-10-01 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
SG184168A1 (en) | 2010-04-08 | 2012-10-30 | Bristol Myers Squibb Co | Pyrimidinylpiperidinyloxypyridinone analogues as gpr119 modulators |
CN102971311B (zh) | 2010-05-06 | 2015-07-08 | 百时美施贵宝公司 | 作为gpr119调节剂的二环杂芳基化合物 |
WO2011140161A1 (en) | 2010-05-06 | 2011-11-10 | Bristol-Myers Squibb Company | Benzofuranyl analogues as gpr119 modulators |
KR20140009291A (ko) * | 2011-01-20 | 2014-01-22 | 머크 샤프 앤드 돔 코포레이션 | 미네랄로코르티코이드 수용체 길항제 |
US9174965B2 (en) | 2012-05-16 | 2015-11-03 | Bristol-Myers Squibb Company | Pyrimidinylpiperidinyloxypyridone analogues as GPR119 modulators |
US9744149B2 (en) | 2012-07-13 | 2017-08-29 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
US9969683B2 (en) | 2012-07-13 | 2018-05-15 | Gtx, Inc. | Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS) |
US10987334B2 (en) | 2012-07-13 | 2021-04-27 | University Of Tennessee Research Foundation | Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs) |
US9622992B2 (en) | 2012-07-13 | 2017-04-18 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
KR102122941B1 (ko) | 2012-07-13 | 2020-06-15 | 지티엑스, 인코포레이티드 | 선택적 안드로겐 수용체 조절자(sarms)를 이용한 안드로겐 수용체(ar) 양성 유방암의 치료 방법 |
WO2014139388A1 (en) * | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
US9580422B2 (en) | 2013-10-22 | 2017-02-28 | Bristol-Myers Squibb Company | Isotopically labeled triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
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JP7025022B2 (ja) | 2016-01-11 | 2022-02-24 | ザ ロックフェラー ユニバーシティー | 骨髄系由来抑制細胞関連障害の治療のための方法 |
CN106187899B (zh) * | 2016-06-28 | 2019-07-16 | 绍兴文理学院 | 一种氟代氮杂芳烃的合成方法 |
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GR63361B (en) * | 1976-06-24 | 1979-10-22 | Du Pont | Preparation process of antihypertensive hexafluorohydroxyisopropyl bicyclic and tricyclic carbostyrils |
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JPH0995482A (ja) | 1995-09-29 | 1997-04-08 | Shionogi & Co Ltd | α−置換酢酸を有する複素環誘導体、その製造用中間体ならびにそれを含有する農薬 |
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RU2278859C2 (ru) | 2001-05-15 | 2006-06-27 | Ф.Хоффманн-Ля Рош Аг | Замещенные карбоновыми кислотами оксазоловые производные в качестве ppar-альфа и гамма-активаторов при лечении диабета |
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GB0216224D0 (en) | 2002-07-12 | 2002-08-21 | Glaxo Group Ltd | Compounds |
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