ZA200406225B - Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof - Google Patents
Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof Download PDFInfo
- Publication number
- ZA200406225B ZA200406225B ZA200406225A ZA200406225A ZA200406225B ZA 200406225 B ZA200406225 B ZA 200406225B ZA 200406225 A ZA200406225 A ZA 200406225A ZA 200406225 A ZA200406225 A ZA 200406225A ZA 200406225 B ZA200406225 B ZA 200406225B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- trifluoro
- fluoro
- ylmethyl
- methoxyphenyl
- Prior art date
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- 239000003862 glucocorticoid Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 284
- -1 aminocarbonyloxy Chemical group 0.000 claims description 94
- 125000001424 substituent group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000012453 solvate Substances 0.000 claims description 32
- 229940002612 prodrug Drugs 0.000 claims description 31
- 239000000651 prodrug Substances 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 102000003676 Glucocorticoid Receptors Human genes 0.000 claims description 18
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 150000003457 sulfones Chemical class 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- 150000003462 sulfoxides Chemical class 0.000 claims description 16
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003003 spiro group Chemical group 0.000 claims description 6
- 230000000172 allergic effect Effects 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 26
- CHIFTAQVXHNVRW-UHFFFAOYSA-N Nitrile-1H-Indole-3-carboxylic acid Natural products C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 claims 12
- NNBYAHPLGNHESK-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-phenyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 NNBYAHPLGNHESK-UHFFFAOYSA-N 0.000 claims 6
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- HYWDPDGISOPWGZ-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-(3-methylphenyl)pentan-2-ol Chemical compound CC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC=CC=C3C=2)C(F)(F)F)=C1 HYWDPDGISOPWGZ-UHFFFAOYSA-N 0.000 claims 4
- GFYMYOFEBUNRKS-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-phenyl-2-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CN=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 GFYMYOFEBUNRKS-UHFFFAOYSA-N 0.000 claims 4
- OJTDOISCGJSBED-UHFFFAOYSA-N 2-[2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carbonitrile Chemical compound C=1C2=CC(C#N)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 OJTDOISCGJSBED-UHFFFAOYSA-N 0.000 claims 4
- HMVIXMZWCAEUSB-UHFFFAOYSA-N 2-[4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound N1C2=CC=CC=C2C(C#N)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC2=C1OCC2 HMVIXMZWCAEUSB-UHFFFAOYSA-N 0.000 claims 4
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 208000025966 Neurological disease Diseases 0.000 claims 4
- 150000004702 methyl esters Chemical class 0.000 claims 4
- NLSXBFBIPNXUCU-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(1-methoxynaphthalen-2-yl)-4-methylpentan-2-ol Chemical compound C1=CC=C2NC(CC(O)(CC(C)(C)C3=C(C4=CC=CC=C4C=C3)OC)C(F)(F)F)=CC2=C1 NLSXBFBIPNXUCU-UHFFFAOYSA-N 0.000 claims 3
- JGIQIFOAVGJQSZ-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-(2-methylphenyl)pentan-2-ol Chemical compound CC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 JGIQIFOAVGJQSZ-UHFFFAOYSA-N 0.000 claims 3
- PIEOAZCXKHZQBV-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-(4-methylphenyl)pentan-2-ol Chemical compound C1=CC(C)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 PIEOAZCXKHZQBV-UHFFFAOYSA-N 0.000 claims 3
- USMFOMVHIKQVEN-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-(5-methyl-2,3-dihydro-1-benzofuran-7-yl)pentan-2-ol Chemical compound C1=CC=C2NC(CC(O)(CC(C)(C)C=3C=4OCCC=4C=C(C=3)C)C(F)(F)F)=CC2=C1 USMFOMVHIKQVEN-UHFFFAOYSA-N 0.000 claims 3
- UUIWYLMDKKQBJQ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC2=C1OCC2 UUIWYLMDKKQBJQ-UHFFFAOYSA-N 0.000 claims 3
- DJRNAIGSFHOUFL-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=NC=C2N1 DJRNAIGSFHOUFL-UHFFFAOYSA-N 0.000 claims 3
- QPLQDYDXYCUKKE-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=NC=C2N1 QPLQDYDXYCUKKE-UHFFFAOYSA-N 0.000 claims 3
- GCKNMQIBTQCWOW-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-(5-methyl-2,3-dihydro-1-benzofuran-7-yl)-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1=CC=C2C(CC(O)(CC(C)(C)C=3C=4OCCC=4C=C(C=3)C)C(F)(F)F)=CC=NC2=C1 GCKNMQIBTQCWOW-UHFFFAOYSA-N 0.000 claims 3
- DXOQPLYIBQRHNE-UHFFFAOYSA-N 2-[(2,6-dichloropyridin-4-yl)methyl]-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC(Cl)=NC(Cl)=C1 DXOQPLYIBQRHNE-UHFFFAOYSA-N 0.000 claims 3
- GMEQBMRWYQQDNV-UHFFFAOYSA-N 2-[(2-bromopyridin-4-yl)methyl]-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC(Br)=C1 GMEQBMRWYQQDNV-UHFFFAOYSA-N 0.000 claims 3
- SKNXJHVYZREZQE-UHFFFAOYSA-N 2-[2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound C=1C=2C(C)=CC(C#N)=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 SKNXJHVYZREZQE-UHFFFAOYSA-N 0.000 claims 3
- VDIOFMJYOYVMOO-UHFFFAOYSA-N 2-[4-(4-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=C(C#N)C2=CC=CC=C2N1 VDIOFMJYOYVMOO-UHFFFAOYSA-N 0.000 claims 3
- RCHKMEIVQJJPEJ-UHFFFAOYSA-N 2-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C)C=C(C#N)C=C2N1 RCHKMEIVQJJPEJ-UHFFFAOYSA-N 0.000 claims 3
- BQBQHUCHUURBBK-UHFFFAOYSA-N 2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(quinolin-4-ylmethyl)pentan-2-yl]naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C(C)(CC(O)(CC=3C4=CC=CC=C4N=CC=3)C(F)(F)F)C)=CC=C21 BQBQHUCHUURBBK-UHFFFAOYSA-N 0.000 claims 3
- PZOGJBZBKUZEII-UHFFFAOYSA-N 3-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(quinolin-4-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(O)=C1 PZOGJBZBKUZEII-UHFFFAOYSA-N 0.000 claims 3
- YROYMPDJQKBNTG-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CC=NC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 YROYMPDJQKBNTG-UHFFFAOYSA-N 0.000 claims 3
- XHRGPBXBIQZZGI-UHFFFAOYSA-N 4-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C(C=C1Br)=CC2=C1OCC2 XHRGPBXBIQZZGI-UHFFFAOYSA-N 0.000 claims 3
- LTJPVQNAJLSDLD-UHFFFAOYSA-N 5-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(quinolin-4-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1O LTJPVQNAJLSDLD-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- DUPWFLAOXJABMP-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 DUPWFLAOXJABMP-UHFFFAOYSA-N 0.000 claims 2
- ZEVOUDMOXREUQH-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(3-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC=CC=C3C=2)C(F)(F)F)=C1 ZEVOUDMOXREUQH-UHFFFAOYSA-N 0.000 claims 2
- NFZVFCYMIGXGEO-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(4-methoxyphenyl)-4-methylpentan-2-ol Chemical compound C1=CC(OC)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 NFZVFCYMIGXGEO-UHFFFAOYSA-N 0.000 claims 2
- SSXCZELUNHJHQF-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-[3-(trifluoromethyl)phenyl]pentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(C(F)(F)F)=C1 SSXCZELUNHJHQF-UHFFFAOYSA-N 0.000 claims 2
- GEROBJZBAHWBME-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-phenylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 GEROBJZBAHWBME-UHFFFAOYSA-N 0.000 claims 2
- HFWXCPFGOCGJDK-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(5-fluoro-1h-indol-2-yl)methyl]-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(F)=CC=C2N1 HFWXCPFGOCGJDK-UHFFFAOYSA-N 0.000 claims 2
- HMFLWDMRCSPEKE-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-(4-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC(F)=C2N1 HMFLWDMRCSPEKE-UHFFFAOYSA-N 0.000 claims 2
- DQNHEYWVKKTREE-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-methyl-4-phenylpentan-2-ol Chemical compound C=1C2=CC=CC(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 DQNHEYWVKKTREE-UHFFFAOYSA-N 0.000 claims 2
- KZFHKECQQKPSOW-UHFFFAOYSA-N 1,1,1-trifluoro-4-(1-methoxynaphthalen-2-yl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1=CC=C2C(CC(O)(CC(C)(C)C3=C(C4=CC=CC=C4C=C3)OC)C(F)(F)F)=CC=NC2=C1 KZFHKECQQKPSOW-UHFFFAOYSA-N 0.000 claims 2
- BPNWRLGSGVFULW-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-methoxyphenyl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC=CC(C(C)(C)CC(O)(CC=2C3=CC=CC=C3N=CC=2)C(F)(F)F)=C1 BPNWRLGSGVFULW-UHFFFAOYSA-N 0.000 claims 2
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- 2004-09-17 US US10/944,615 patent/US7553966B2/en not_active Expired - Lifetime
- 2004-09-24 NO NO20044031A patent/NO329386B1/no not_active IP Right Cessation
- 2004-09-24 EC EC2004005315A patent/ECSP045315A/es unknown
- 2004-09-24 HR HR20040887A patent/HRP20040887A2/hr not_active Application Discontinuation
- 2004-10-21 CO CO04105799A patent/CO5611110A2/es not_active Application Discontinuation
-
2005
- 2005-07-20 US US11/185,349 patent/US7932392B2/en active Active
-
2006
- 2006-04-25 US US11/410,408 patent/US8212040B2/en not_active Expired - Lifetime
-
2008
- 2008-03-17 CY CY20081100298T patent/CY1107244T1/el unknown
-
2010
- 2010-04-15 CL CL2010000375A patent/CL2010000375A1/es unknown
- 2010-06-10 NO NO20100827A patent/NO20100827L/no not_active Application Discontinuation
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