SK15172003A3 - Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors - Google Patents

Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors Download PDF

Info

Publication number: SK15172003A3
Authority: SK; Slovakia
Prior art keywords: carbon atoms; optionally; alkyl; carbon; trifluoromethyl
Prior art date: 2001-06-21

Application number

SK1517-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Michael Jon Gumkowski

Sharad Balasaheb Murdande

Michael Ellis Perlman

Franco LOMBARDO

Original Assignee

Pfizer Prod Inc

Priority date (The priority date 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 date listed.)

2001-06-21

Filing date

2002-05-03

Publication date

2004-11-03

2002-05-03 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-11-03 Publication of SK15172003A3 publication Critical patent/SK15172003A3/sk

Links

239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 title claims abstract description 105
239000000203 mixture Substances 0.000 title claims abstract description 84
238000009472 formulation Methods 0.000 title description 5
239000004094 surface-active agent Substances 0.000 claims abstract description 88
229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims abstract description 52
239000006184 cosolvent Substances 0.000 claims abstract description 30
239000002904 solvent Substances 0.000 claims abstract description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 587
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 363
-1 polyethylene Polymers 0.000 claims description 295
125000000217 alkyl group Chemical group 0.000 claims description 265
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 263
229910052757 nitrogen Inorganic materials 0.000 claims description 257
229920006395 saturated elastomer Polymers 0.000 claims description 225
125000004043 oxo group Chemical group O=* 0.000 claims description 210
229910052799 carbon Inorganic materials 0.000 claims description 207
229910052717 sulfur Inorganic materials 0.000 claims description 207
229910052736 halogen Inorganic materials 0.000 claims description 196
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 189
239000011593 sulfur Substances 0.000 claims description 186
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 185
229910052760 oxygen Inorganic materials 0.000 claims description 165
239000001301 oxygen Substances 0.000 claims description 160
150000002367 halogens Chemical class 0.000 claims description 159
125000003545 alkoxy group Chemical group 0.000 claims description 158
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 150
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 147
229910052739 hydrogen Inorganic materials 0.000 claims description 147
239000001257 hydrogen Substances 0.000 claims description 143
125000005842 heteroatom Chemical group 0.000 claims description 141
125000003118 aryl group Chemical group 0.000 claims description 139
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 132
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 127
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 116
125000000753 cycloalkyl group Chemical group 0.000 claims description 111
150000002431 hydrogen Chemical class 0.000 claims description 109
125000000623 heterocyclic group Chemical group 0.000 claims description 101
125000003342 alkenyl group Chemical group 0.000 claims description 98
125000004093 cyano group Chemical group *C#N 0.000 claims description 96
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 88
125000005843 halogen group Chemical group 0.000 claims description 78
125000001072 heteroaryl group Chemical group 0.000 claims description 77
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 68
125000004414 alkyl thio group Chemical group 0.000 claims description 68
125000000304 alkynyl group Chemical group 0.000 claims description 67
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 66
125000001424 substituent group Chemical group 0.000 claims description 57
150000001875 compounds Chemical class 0.000 claims description 56
239000003921 oil Substances 0.000 claims description 55
235000019198 oils Nutrition 0.000 claims description 55
125000002252 acyl group Chemical group 0.000 claims description 50
125000001153 fluoro group Chemical group F* 0.000 claims description 45
125000002947 alkylene group Chemical group 0.000 claims description 37
125000004429 atom Chemical group 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical group CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
125000002619 bicyclic group Chemical group 0.000 claims description 29
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 28
125000004104 aryloxy group Chemical group 0.000 claims description 25
125000000392 cycloalkenyl group Chemical group 0.000 claims description 25
125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 24
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 22
125000000262 haloalkenyl group Chemical group 0.000 claims description 22
125000003710 aryl alkyl group Chemical group 0.000 claims description 21
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
125000004434 sulfur atom Chemical group 0.000 claims description 18
125000005109 alkynylthio group Chemical group 0.000 claims description 17
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 16
239000001087 glyceryl triacetate Substances 0.000 claims description 16
235000013773 glyceryl triacetate Nutrition 0.000 claims description 16
229960002622 triacetin Drugs 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 15
125000002837 carbocyclic group Chemical group 0.000 claims description 14
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 14
125000005553 heteroaryloxy group Chemical group 0.000 claims description 14
229920000053 polysorbate 80 Polymers 0.000 claims description 14
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 13
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 13
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 13
125000005110 aryl thio group Chemical group 0.000 claims description 12
125000005164 aryl thioalkyl group Chemical group 0.000 claims description 12
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 12
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 12
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 11
125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 11
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 11
229940068968 polysorbate 80 Drugs 0.000 claims description 11
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
239000004698 Polyethylene Substances 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
239000004359 castor oil Substances 0.000 claims description 10
235000019438 castor oil Nutrition 0.000 claims description 10
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 10
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 10
125000003106 haloaryl group Chemical group 0.000 claims description 10
125000005216 haloheteroaryl group Chemical group 0.000 claims description 10
125000004468 heterocyclylthio group Chemical group 0.000 claims description 10
229920000573 polyethylene Polymers 0.000 claims description 10
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
150000001721 carbon Chemical group 0.000 claims description 9
125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
125000005368 heteroarylthio group Chemical group 0.000 claims description 9
125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 9
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 8
125000005108 alkenylthio group Chemical group 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 8
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
239000003981 vehicle Substances 0.000 claims description 8
125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 7
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 7
235000014113 dietary fatty acids Nutrition 0.000 claims description 7
125000004494 ethyl ester group Chemical group 0.000 claims description 7
229940116333 ethyl lactate Drugs 0.000 claims description 7
239000000194 fatty acid Substances 0.000 claims description 7
229930195729 fatty acid Natural products 0.000 claims description 7
235000019000 fluorine Nutrition 0.000 claims description 7
125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 7
125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 7
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004450 alkenylene group Chemical group 0.000 claims description 6
125000005055 alkyl alkoxy group Chemical group 0.000 claims description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
150000002825 nitriles Chemical class 0.000 claims description 6
125000005254 oxyacyl group Chemical group 0.000 claims description 6
125000005353 silylalkyl group Chemical group 0.000 claims description 6
150000003536 tetrazoles Chemical group 0.000 claims description 6
LVHVPFOLBJZHDN-UHFFFAOYSA-N (2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamic acid Chemical class C1=CC=C2NC(C)CC(NC(O)=O)C2=C1 LVHVPFOLBJZHDN-UHFFFAOYSA-N 0.000 claims description 5
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000000232 haloalkynyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229920001223 polyethylene glycol Polymers 0.000 claims description 5
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 5
150000003222 pyridines Chemical class 0.000 claims description 5
125000003003 spiro group Chemical group 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
SHNMAZJVVFUXAQ-UHFFFAOYSA-N 2h-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CC=CC2=C1 SHNMAZJVVFUXAQ-UHFFFAOYSA-N 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
229920001213 Polysorbate 20 Polymers 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
235000005687 corn oil Nutrition 0.000 claims description 4
GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 claims description 4
125000001145 hydrido group Chemical group *[H] 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 claims description 4
125000005389 trialkylsiloxy group Chemical group 0.000 claims description 4
125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 4
MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 3
OVYMWJFNQQOJBU-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl octanoate Chemical compound CCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC OVYMWJFNQQOJBU-UHFFFAOYSA-N 0.000 claims description 3
239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims description 3
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims description 3
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 claims description 3
125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
239000002285 corn oil Substances 0.000 claims description 3
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000005241 heteroarylamino group Chemical group 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
RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims description 3
229960002446 octanoic acid Drugs 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
MLMAJGJPMOWEJB-UHFFFAOYSA-N (2-cyclopentyl-5-hydroxy-7,7-dimethyl-4-thiophen-3-yl-6,8-dihydro-5h-quinolin-3-yl)-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1C(C)(C)CC(O)C(C(=C2C(=O)C=3C=CC(=CC=3)C(F)(F)F)C3=CSC=C3)=C1N=C2C1CCCC1 MLMAJGJPMOWEJB-UHFFFAOYSA-N 0.000 claims description 2
WCHRXPOAPJPGEP-UHFFFAOYSA-N 1-(3-methylbutyl)-n-[2-[[2-[[1-(3-methylbutyl)cyclopentanecarbonyl]amino]phenyl]disulfanyl]phenyl]cyclopentane-1-carboxamide Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)NC(=O)C2(CCC(C)C)CCCC2)C=1NC(=O)C1(CCC(C)C)CCCC1 WCHRXPOAPJPGEP-UHFFFAOYSA-N 0.000 claims description 2
ANRGGUOSHLLQRY-UHFFFAOYSA-N 1-[2,4-bis(4-fluorophenyl)-5-[fluoro-[4-(trifluoromethyl)phenyl]methyl]-6-propan-2-ylpyridin-3-yl]ethanol Chemical compound CC(O)C=1C(C=2C=CC(F)=CC=2)=C(C(F)C=2C=CC(=CC=2)C(F)(F)F)C(C(C)C)=NC=1C1=CC=C(F)C=C1 ANRGGUOSHLLQRY-UHFFFAOYSA-N 0.000 claims description 2
CPHKBJBFYKJFHT-UHFFFAOYSA-N 1-methyl-n-[2-[[2-[(1-methylcyclohexanecarbonyl)amino]phenyl]disulfanyl]phenyl]cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)NC(=O)C2(C)CCCCC2)C=1NC(=O)C1(C)CCCCC1 CPHKBJBFYKJFHT-UHFFFAOYSA-N 0.000 claims description 2
QQKYOVRCWBXJDW-UHFFFAOYSA-N 2-cyclopentyl-3-[fluoro-[4-(trifluoromethyl)phenyl]methyl]-7,7-dimethyl-4-thiophen-3-yl-6,8-dihydro-5h-quinolin-5-ol Chemical compound C1C(C)(C)CC(O)C(C(=C2C(F)C=3C=CC(=CC=3)C(F)(F)F)C3=CSC=C3)=C1N=C2C1CCCC1 QQKYOVRCWBXJDW-UHFFFAOYSA-N 0.000 claims description 2
AQZMNAWNLGAUDN-UHFFFAOYSA-N 2-cyclopentyl-4-(4-fluorophenyl)-7,7-dimethyl-3-[4-(trifluoromethyl)benzoyl]-1,4,6,8-tetrahydroquinolin-5-one Chemical compound C1C(C)(C)CC(=O)C(C(C=2C(=O)C=3C=CC(=CC=3)C(F)(F)F)C=3C=CC(F)=CC=3)=C1NC=2C1CCCC1 AQZMNAWNLGAUDN-UHFFFAOYSA-N 0.000 claims description 2
DIDGMJDNRZOGLE-UHFFFAOYSA-N 2-cyclopentyl-4-(4-fluorophenyl)-7,7-dimethyl-3-[4-(trifluoromethyl)benzoyl]-6,8-dihydroquinolin-5-one Chemical compound C1C(C)(C)CC(=O)C(C(=C2C(=O)C=3C=CC(=CC=3)C(F)(F)F)C=3C=CC(F)=CC=3)=C1N=C2C1CCCC1 DIDGMJDNRZOGLE-UHFFFAOYSA-N 0.000 claims description 2
HMFSKKAMUVIGTI-UHFFFAOYSA-N 2-cyclopentyl-7,7-dimethyl-4-thiophen-3-yl-3-(2,2,2-trifluoro-1-phenylethyl)-6,8-dihydro-5h-quinolin-5-ol Chemical compound C1C(C)(C)CC(O)C(C(=C2C(C=3C=CC=CC=3)C(F)(F)F)C3=CSC=C3)=C1N=C2C1CCCC1 HMFSKKAMUVIGTI-UHFFFAOYSA-N 0.000 claims description 2
SEHSCTOVASUCHD-UHFFFAOYSA-N 2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid Chemical compound CC1N(C2=CC=CC=C2CC1)C(=O)O SEHSCTOVASUCHD-UHFFFAOYSA-N 0.000 claims description 2
LXFBGDVYRAOFPG-UHFFFAOYSA-N 3-tridecyl-4-[3-(trifluoromethyl)phenyl]-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(C(F)(F)F)=C1 LXFBGDVYRAOFPG-UHFFFAOYSA-N 0.000 claims description 2
KARZWFFLADFSJJ-UHFFFAOYSA-N 4-(2,6-dimethylphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=C(C)C=CC=C1C KARZWFFLADFSJJ-UHFFFAOYSA-N 0.000 claims description 2
UVFPUNZVHJMCQM-UHFFFAOYSA-N 4-(2-chlorophenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC=C1Cl UVFPUNZVHJMCQM-UHFFFAOYSA-N 0.000 claims description 2
BVFWWABBHJZROC-UHFFFAOYSA-N 4-(2-ethoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC=C1OCC BVFWWABBHJZROC-UHFFFAOYSA-N 0.000 claims description 2
HAKOVQKISVNQOZ-UHFFFAOYSA-N 4-(2-methoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC=C1OC HAKOVQKISVNQOZ-UHFFFAOYSA-N 0.000 claims description 2
QXDZQZLKZFBCMW-UHFFFAOYSA-N 4-(2-methylsulfanylphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC=C1SC QXDZQZLKZFBCMW-UHFFFAOYSA-N 0.000 claims description 2
NSWWHSXVKSHJOE-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(OC)C(OC)=C1 NSWWHSXVKSHJOE-UHFFFAOYSA-N 0.000 claims description 2
UNQVXTZCFDXMRU-UHFFFAOYSA-N 4-(3-chloro-4-methylphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(C)C(Cl)=C1 UNQVXTZCFDXMRU-UHFFFAOYSA-N 0.000 claims description 2
RDJMWIPWPLTLLP-UHFFFAOYSA-N 4-(3-fluorophenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(F)=C1 RDJMWIPWPLTLLP-UHFFFAOYSA-N 0.000 claims description 2
ARYGZDOADGGOPU-UHFFFAOYSA-N 4-(3-methoxyphenyl)-3-undecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(OC)=C1 ARYGZDOADGGOPU-UHFFFAOYSA-N 0.000 claims description 2
MDAQPWRMEYVZNO-UHFFFAOYSA-N 4-(3-methylphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(C)=C1 MDAQPWRMEYVZNO-UHFFFAOYSA-N 0.000 claims description 2
ZECLWJRIUPEVJU-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(OC)C=C1 ZECLWJRIUPEVJU-UHFFFAOYSA-N 0.000 claims description 2
NGWRJQZPDODVRQ-UHFFFAOYSA-N 4-(4-methylsulfanylphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(SC)C=C1 NGWRJQZPDODVRQ-UHFFFAOYSA-N 0.000 claims description 2
UUHUXSPURVSFIS-UHFFFAOYSA-N 4-(4-phenoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C(C=C1)=CC=C1OC1=CC=CC=C1 UUHUXSPURVSFIS-UHFFFAOYSA-N 0.000 claims description 2
RZHDLZSUFMXUGK-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC(Cl)=CC=C1OC RZHDLZSUFMXUGK-UHFFFAOYSA-N 0.000 claims description 2
TZBZFBNAKUDGIX-UHFFFAOYSA-N 4-(5-sulfanylidene-3-tridecyl-1h-1,2,4-triazol-4-yl)benzenesulfonamide Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(S(N)(=O)=O)C=C1 TZBZFBNAKUDGIX-UHFFFAOYSA-N 0.000 claims description 2
DMCWDPFCDZFGEC-UHFFFAOYSA-N 4-naphthalen-1-yl-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC2=CC=CC=C12 DMCWDPFCDZFGEC-UHFFFAOYSA-N 0.000 claims description 2
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
VVNLIZOGBDPODZ-UHFFFAOYSA-N 6h-quinolin-2-one Chemical class C1C=CC2=NC(=O)C=CC2=C1 VVNLIZOGBDPODZ-UHFFFAOYSA-N 0.000 claims description 2
150000001204 N-oxides Chemical class 0.000 claims description 2
KVZSJDNWQCUMJQ-UHFFFAOYSA-N [2,4-bis(4-fluorophenyl)-6-propan-2-yl-5-[2-[3-(trifluoromethyl)phenyl]ethenyl]pyridin-3-yl]methanol Chemical compound OCC=1C(C=2C=CC(F)=CC=2)=C(C=CC=2C=C(C=CC=2)C(F)(F)F)C(C(C)C)=NC=1C1=CC=C(F)C=C1 KVZSJDNWQCUMJQ-UHFFFAOYSA-N 0.000 claims description 2
UTXCDRWZMZADNL-UHFFFAOYSA-N [2-cyclopentyl-4-(4-fluorophenyl)-5-hydroxy-7,7-dimethyl-6,8-dihydro-5h-quinolin-3-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1C(C)(C)CC(O)C(C(=C2C(=O)C=3C=CC(=CC=3)C(F)(F)F)C=3C=CC(F)=CC=3)=C1N=C2C1CCCC1 UTXCDRWZMZADNL-UHFFFAOYSA-N 0.000 claims description 2
KRBOQHVJZXIDTG-UHFFFAOYSA-N [5-[tert-butyl(dimethyl)silyl]oxy-2-cyclopentyl-4-(4-fluorophenyl)-7,7-dimethyl-6,8-dihydro-5h-quinolin-3-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=O)C=1C(C=2C=CC(F)=CC=2)=C2C(O[Si](C)(C)C(C)(C)C)CC(C)(C)CC2=NC=1C1CCCC1 KRBOQHVJZXIDTG-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
125000006323 alkenyl amino group Chemical group 0.000 claims description 2
125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 2
125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000005021 aminoalkenyl group Chemical group 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000005014 aminoalkynyl group Chemical group 0.000 claims description 2
125000005001 aminoaryl group Chemical group 0.000 claims description 2
125000005214 aminoheteroaryl group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000000732 arylene group Chemical group 0.000 claims description 2
125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
125000000422 delta-lactone group Chemical group 0.000 claims description 2
125000004986 diarylamino group Chemical group 0.000 claims description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
CAPQXUVLEJNCSY-UNMCSNQZSA-N ethyl (2S,4S)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate Chemical compound C(C)OC(=O)N1[C@@H](C[C@@H](C2=CC(=CC=C12)C(F)(F)F)NC(=O)OCCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1CC1 CAPQXUVLEJNCSY-UNMCSNQZSA-N 0.000 claims description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
229940074046 glyceryl laurate Drugs 0.000 claims description 2
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
150000002430 hydrocarbons Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
DDZIFEIGSSYBIV-UHFFFAOYSA-N n-[2-[[2-(2,2-dimethylpropanoylamino)phenyl]disulfanyl]phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC=C1SSC1=CC=CC=C1NC(=O)C(C)(C)C DDZIFEIGSSYBIV-UHFFFAOYSA-N 0.000 claims description 2
229960003512 nicotinic acid Drugs 0.000 claims description 2
239000011664 nicotinic acid Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
HFFFFTQVPXWDLI-KNQAVFIVSA-N propan-2-yl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OC(C)C)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFFFFTQVPXWDLI-KNQAVFIVSA-N 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 2
239000000779 smoke Substances 0.000 claims description 2
239000012453 solvate Substances 0.000 claims description 2
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
UVDGFGGDWPDIIY-UHFFFAOYSA-N 4-cyclohexyl-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1CCCCC1 UVDGFGGDWPDIIY-UHFFFAOYSA-N 0.000 claims 2
RBSSZXNROVUKNX-PXAZEXFGSA-N (2R,4S)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid Chemical compound FC(C=1C=C(CCOC(=O)N[C@H]2C[C@H](N(C3=CC(=C(C=C23)OC)OC)C(=O)O)C)C=C(C=1)C(F)(F)F)(F)F RBSSZXNROVUKNX-PXAZEXFGSA-N 0.000 claims 1
YHVAVVYZKFSPOE-DIFFPNOSSA-N (2R,4S)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-6-chloro-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid Chemical compound FC(C=1C=C(CCOC(=O)N[C@H]2C[C@H](N(C3=CC=C(C=C23)Cl)C(=O)O)C)C=C(C=1)C(F)(F)F)(F)F YHVAVVYZKFSPOE-DIFFPNOSSA-N 0.000 claims 1
SVBFGLBHOKDRAW-ZMZPIMSZSA-N (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-formylamino]-2-methyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound O=CN([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(O)=O)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SVBFGLBHOKDRAW-ZMZPIMSZSA-N 0.000 claims 1
JRBOFAXVGHMLMM-APWZRJJASA-N (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound COC(=O)N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(O)=O)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JRBOFAXVGHMLMM-APWZRJJASA-N 0.000 claims 1
UHVWAIYOKMLROQ-PXAZEXFGSA-N (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound COC(=O)N([C@@H]1C2=CC(OC)=C(OC)C=C2N(C(O)=O)[C@H](C)C1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UHVWAIYOKMLROQ-PXAZEXFGSA-N 0.000 claims 1
CWOUDBOBZZCQFG-UHFFFAOYSA-N 1-(2-ethylbutyl)-n-[2-[[2-[[1-(2-ethylbutyl)cyclohexanecarbonyl]amino]phenyl]disulfanyl]phenyl]cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)NC(=O)C2(CC(CC)CC)CCCCC2)C=1NC(=O)C1(CC(CC)CC)CCCCC1 CWOUDBOBZZCQFG-UHFFFAOYSA-N 0.000 claims 1
SDFLVSQYLLGMKX-UHFFFAOYSA-N 1-(3-methylbutyl)-n-[2-[[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl]disulfanyl]phenyl]cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)NC(=O)C2(CCC(C)C)CCCCC2)C=1NC(=O)C1(CCC(C)C)CCCCC1 SDFLVSQYLLGMKX-UHFFFAOYSA-N 0.000 claims 1
CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 claims 1
IPYXWSIBCVUPBE-UHFFFAOYSA-N 2-cyclopentyl-4-(4-fluorophenyl)-3-[fluoro-[4-(trifluoromethyl)phenyl]methyl]-7,7-dimethyl-6,8-dihydro-5h-quinolin-5-ol Chemical compound C1C(C)(C)CC(O)C(C(=C2C(F)C=3C=CC(=CC=3)C(F)(F)F)C=3C=CC(F)=CC=3)=C1N=C2C1CCCC1 IPYXWSIBCVUPBE-UHFFFAOYSA-N 0.000 claims 1
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
CISJAEWNKCDPLC-NQIIRXRSSA-N 2-hydroxyethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCCO)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CISJAEWNKCDPLC-NQIIRXRSSA-N 0.000 claims 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
CXMYSDLCKRTJIM-UHFFFAOYSA-N 3-dodecyl-4-(3-methoxyphenyl)-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(OC)=C1 CXMYSDLCKRTJIM-UHFFFAOYSA-N 0.000 claims 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
JVWXFZFLEDZACS-UHFFFAOYSA-N 3-tridecyl-4-[4-(trifluoromethyl)phenyl]-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(C(F)(F)F)C=C1 JVWXFZFLEDZACS-UHFFFAOYSA-N 0.000 claims 1
VBYFZWIHXIZTAD-UHFFFAOYSA-N 4-(2,5-dimethoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC(OC)=CC=C1OC VBYFZWIHXIZTAD-UHFFFAOYSA-N 0.000 claims 1
JECNDSVPYREDAK-UHFFFAOYSA-N 4-[[3,5-bis(trifluoromethyl)phenyl]methyl-formylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid Chemical compound FC(C=1C=C(CN(C2CC(N(C3=CC=C(C=C23)C(F)(F)F)C(=O)O)C2CC2)C=O)C=C(C1)C(F)(F)F)(F)F JECNDSVPYREDAK-UHFFFAOYSA-N 0.000 claims 1
JMMYFHCNNAAPNT-UHFFFAOYSA-N 4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(O)=O)C(CC)CC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JMMYFHCNNAAPNT-UHFFFAOYSA-N 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
VAWDDJNOCQTLPA-UHFFFAOYSA-N CC1CC(C2=CC(=C(C=C2N1C(=O)O)OC)OC)NC(=O)OCCC3=CC(=CC(=C3)[N+](=O)[O-])[N+](=O)[O-] Chemical compound CC1CC(C2=CC(=C(C=C2N1C(=O)O)OC)OC)NC(=O)OCCC3=CC(=CC(=C3)[N+](=O)[O-])[N+](=O)[O-] VAWDDJNOCQTLPA-UHFFFAOYSA-N 0.000 claims 1
CGVFRZMQURRQIE-UHFFFAOYSA-N COC1=CC=C(CN(C(CC=2SC=CC=2)=O)C2=CC(=C(C(=C2)OC)OC)OC)C=C1 Chemical compound COC1=CC=C(CN(C(CC=2SC=CC=2)=O)C2=CC(=C(C(=C2)OC)OC)OC)C=C1 CGVFRZMQURRQIE-UHFFFAOYSA-N 0.000 claims 1
KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims 1
244000018633 Prunus armeniaca Species 0.000 claims 1
235000009827 Prunus armeniaca Nutrition 0.000 claims 1
DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims 1
125000005529 alkyleneoxy group Chemical group 0.000 claims 1
125000006319 alkynyl amino group Chemical group 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
239000003245 coal Substances 0.000 claims 1
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 claims 1
JTIHJERAWZTVPK-KUHUBIRLSA-N ethyl (2R,4S)-4-[2-(3,5-dichlorophenyl)ethoxycarbonylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylate Chemical compound C(C)OC(=O)N1[C@@H](C[C@@H](C2=CC(=C(C=C12)OC)OC)NC(=O)OCCC1=CC(=CC(=C1)Cl)Cl)C JTIHJERAWZTVPK-KUHUBIRLSA-N 0.000 claims 1
MVQHAPUEVDJZRE-QRWLVFNGSA-N ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-ethoxycarbonylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound CCOC(=O)N([C@@H]1C2=CC(OC)=C(OC)C=C2N(C(=O)OCC)[C@H](C)C1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MVQHAPUEVDJZRE-QRWLVFNGSA-N 0.000 claims 1
QLEFLSNISMMSTB-XCLFUZPHSA-N ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-methyl-6-(trifluoromethoxy)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@@H](C)N(C2=CC=C(OC(F)(F)F)C=C21)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QLEFLSNISMMSTB-XCLFUZPHSA-N 0.000 claims 1
AMKXGYCDXWPFLQ-UHFFFAOYSA-N ethyl 3,3a,4,4a-tetrahydro-2H-furo[2,3-g]quinoline-5-carboxylate Chemical compound CCOC(=O)N1C=CC=C2C1CC3CCOC3=C2 AMKXGYCDXWPFLQ-UHFFFAOYSA-N 0.000 claims 1
XCTLDQQOHIEUCJ-UHFFFAOYSA-N ethyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CC=CC2=C1 XCTLDQQOHIEUCJ-UHFFFAOYSA-N 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 1
YPDZILMBVDNXMP-QRWLVFNGSA-N methyl n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[(2r,4s)-1-butanoyl-6,7-dimethoxy-2-methyl-3,4-dihydro-2h-quinolin-4-yl]carbamate Chemical compound COC(=O)N([C@H]1C[C@@H](C)N(C2=CC(OC)=C(OC)C=C21)C(=O)CCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YPDZILMBVDNXMP-QRWLVFNGSA-N 0.000 claims 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
239000002574 poison Substances 0.000 claims 1
231100000614 poison Toxicity 0.000 claims 1
229920000056 polyoxyethylene ether Polymers 0.000 claims 1
CDGFMQZDFNJUCP-DHIUTWEWSA-N propan-2-yl (2r,4r)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C2=CC(=CC=C2N(C(=O)OC(C)C)[C@@H](C2CC2)C1)C(F)(F)F)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDGFMQZDFNJUCP-DHIUTWEWSA-N 0.000 claims 1
ZNTRESFNIULONU-SZNDQCEHSA-N propan-2-yl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-formylamino]-2-methyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound O=CN([C@H]1C[C@@H](C)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZNTRESFNIULONU-SZNDQCEHSA-N 0.000 claims 1
SZMQFZQLZHMRMT-UGKGYDQZSA-N propan-2-yl (2s,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-(methoxymethyl)-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OC(C)C)COC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SZMQFZQLZHMRMT-UGKGYDQZSA-N 0.000 claims 1
RRPVNLZHOJXQAR-ZEQRLZLVSA-N propan-2-yl (2s,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-cyclobutyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@@H]1C2=CC(=CC=C2N(C(=O)OC(C)C)[C@H](C2CCC2)C1)C(F)(F)F)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RRPVNLZHOJXQAR-ZEQRLZLVSA-N 0.000 claims 1
CDGFMQZDFNJUCP-UHFFFAOYSA-N propan-2-yl 4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C1C(C2CC2)N(C(=O)OC(C)C)C2=CC=C(C(F)(F)F)C=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDGFMQZDFNJUCP-UHFFFAOYSA-N 0.000 claims 1
PZHGQMYUOOPPMV-UHFFFAOYSA-N propyl 2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCCC)CC=CC2=C1 PZHGQMYUOOPPMV-UHFFFAOYSA-N 0.000 claims 1
OOLOIQYOVMCZMC-UHFFFAOYSA-N propyl 4-[[3,5-bis(trifluoromethyl)phenyl]methyl-formylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OCCC)C(C2CC2)CC1N(C=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OOLOIQYOVMCZMC-UHFFFAOYSA-N 0.000 claims 1
UONOGMDIHGCLKG-UHFFFAOYSA-N propyl 4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OCCC)C(C2CC2)CC1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UONOGMDIHGCLKG-UHFFFAOYSA-N 0.000 claims 1
125000004354 sulfur functional group Chemical group 0.000 claims 1
IRYKICKCAXOYHW-UHFFFAOYSA-N tert-butyl-[[2-cyclopentyl-4-(4-fluorophenyl)-3-[fluoro-[4-(trifluoromethyl)phenyl]methyl]-7,7-dimethyl-6,8-dihydro-5h-quinolin-5-yl]oxy]-dimethylsilane Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(F)C=1C(C=2C=CC(F)=CC=2)=C2C(O[Si](C)(C)C(C)(C)C)CC(C)(C)CC2=NC=1C1CCCC1 IRYKICKCAXOYHW-UHFFFAOYSA-N 0.000 claims 1
125000005106 triarylsilyl group Chemical group 0.000 claims 1
239000001069 triethyl citrate Substances 0.000 claims 1
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims 1
235000013769 triethyl citrate Nutrition 0.000 claims 1
FKVMWDZRDMCIAJ-UHFFFAOYSA-N undecanamide Chemical compound CCCCCCCCCCC(N)=O FKVMWDZRDMCIAJ-UHFFFAOYSA-N 0.000 claims 1
239000000839 emulsion Substances 0.000 description 22
229940079593 drug Drugs 0.000 description 14
239000003814 drug Substances 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 12
239000007903 gelatin capsule Substances 0.000 description 11
125000006343 heptafluoro propyl group Chemical group 0.000 description 11
229960004592 isopropanol Drugs 0.000 description 11
102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 10
108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000002775 capsule Substances 0.000 description 10
125000004438 haloalkoxy group Chemical group 0.000 description 10
208000029078 coronary artery disease Diseases 0.000 description 9
239000000499 gel Substances 0.000 description 9
239000002609 medium Substances 0.000 description 9
125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 8
238000002156 mixing Methods 0.000 description 8
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 7
108010036949 Cyclosporine Proteins 0.000 description 7
108010010234 HDL Lipoproteins Proteins 0.000 description 7
102000015779 HDL Lipoproteins Human genes 0.000 description 7
238000010521 absorption reaction Methods 0.000 description 7
125000005452 alkenyloxyalkyl group Chemical group 0.000 description 7
239000008280 blood Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
235000013305 food Nutrition 0.000 description 7
230000009246 food effect Effects 0.000 description 7
125000004994 halo alkoxy alkyl group Chemical group 0.000 description 7
239000007788 liquid Substances 0.000 description 7
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 7
150000003626 triacylglycerols Chemical class 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 6
125000003435 aroyl group Chemical group 0.000 description 6
125000004181 carboxyalkyl group Chemical group 0.000 description 6
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 description 6
210000001035 gastrointestinal tract Anatomy 0.000 description 6
125000005150 heteroarylsulfinyl group Chemical group 0.000 description 6
230000002209 hydrophobic effect Effects 0.000 description 6
150000002632 lipids Chemical class 0.000 description 6
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 5
239000012736 aqueous medium Substances 0.000 description 5
125000005140 aralkylsulfonyl group Chemical group 0.000 description 5
125000005135 aryl sulfinyl group Chemical group 0.000 description 5
125000004391 aryl sulfonyl group Chemical group 0.000 description 5
150000003857 carboxamides Chemical class 0.000 description 5
229960001265 ciclosporin Drugs 0.000 description 5
125000005149 cycloalkylsulfinyl group Chemical group 0.000 description 5
229930182912 cyclosporin Natural products 0.000 description 5
235000021471 food effect Nutrition 0.000 description 5
125000004441 haloalkylsulfonyl group Chemical group 0.000 description 5
125000006769 halocycloalkoxy group Chemical group 0.000 description 5
125000005347 halocycloalkyl group Chemical group 0.000 description 5
125000005143 heteroarylsulfonyl group Chemical group 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
239000002245 particle Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
229930105110 Cyclosporin A Natural products 0.000 description 4
241000282412 Homo Species 0.000 description 4
238000008214 LDL Cholesterol Methods 0.000 description 4
229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 4
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
238000004945 emulsification Methods 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 4
OIQOAYVCKAHSEJ-UHFFFAOYSA-N 2-[2,3-bis(2-hydroxyethoxy)propoxy]ethanol;hexadecanoic acid;octadecanoic acid Chemical compound OCCOCC(OCCO)COCCO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OIQOAYVCKAHSEJ-UHFFFAOYSA-N 0.000 description 3
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
241000640882 Condea Species 0.000 description 3
208000032928 Dyslipidaemia Diseases 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
108010023302 HDL Cholesterol Proteins 0.000 description 3
108010007622 LDL Lipoproteins Proteins 0.000 description 3
102000007330 LDL Lipoproteins Human genes 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
235000012000 cholesterol Nutrition 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 3
125000004440 haloalkylsulfinyl group Chemical group 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000007764 o/w emulsion Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000004255 Butylated hydroxyanisole Substances 0.000 description 2
239000004322 Butylated hydroxytoluene Substances 0.000 description 2
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
VGBYRLQOJLVUTG-UHFFFAOYSA-N CC1CCC2=C(N1C(=O)O)C=CC(=C2)C(F)(F)F Chemical compound CC1CCC2=C(N1C(=O)O)C=CC(=C2)C(F)(F)F VGBYRLQOJLVUTG-UHFFFAOYSA-N 0.000 description 2
108010028554 LDL Cholesterol Proteins 0.000 description 2
102000004895 Lipoproteins Human genes 0.000 description 2
108090001030 Lipoproteins Proteins 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
108010062497 VLDL Lipoproteins Proteins 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
125000005233 alkylalcohol group Chemical group 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
230000008901 benefit Effects 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
235000019282 butylated hydroxyanisole Nutrition 0.000 description 2
235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
229940088679 drug related substance Drugs 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
230000002708 enhancing effect Effects 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
230000004130 lipolysis Effects 0.000 description 2
229940057917 medium chain triglycerides Drugs 0.000 description 2
239000004530 micro-emulsion Substances 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
230000036470 plasma concentration Effects 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000000473 propyl gallate Substances 0.000 description 2
235000010388 propyl gallate Nutrition 0.000 description 2
229940075579 propyl gallate Drugs 0.000 description 2
239000000565 sealant Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
229930003799 tocopherol Natural products 0.000 description 2
235000010384 tocopherol Nutrition 0.000 description 2
229960001295 tocopherol Drugs 0.000 description 2
239000011732 tocopherol Substances 0.000 description 2
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
JICWGDSCRBPTIW-BLVKFPJESA-N (2R,4S)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-2-methyl-3,4,6,8-tetrahydro-2H-thieno[3,4-g]quinoline-1-carboxylic acid Chemical compound FC(C=1C=C(CCOC(=O)N[C@H]2C[C@H](N(C=3C=C4C(=CC2=3)CSC4)C(=O)O)C)C=C(C=1)C(F)(F)F)(F)F JICWGDSCRBPTIW-BLVKFPJESA-N 0.000 description 1
ADTSTVBCJZRZOF-JOCHJYFZSA-N (2r)-1,1,1-trifluoro-3-[n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-3-[[3-(trifluoromethyl)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(C=CC=2)C(F)(F)F)=CC=1N(C[C@@H](O)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1F ADTSTVBCJZRZOF-JOCHJYFZSA-N 0.000 description 1
AMMXMFRACDEDRP-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-(3-methylphenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]propan-2-ol Chemical compound CC1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 AMMXMFRACDEDRP-UHFFFAOYSA-N 0.000 description 1
CLPUWZXVKKDOLP-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-(3-methylphenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]propan-2-ol Chemical compound CC1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 CLPUWZXVKKDOLP-UHFFFAOYSA-N 0.000 description 1
XSHGEXOSXRGAIF-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-(4-fluorophenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 XSHGEXOSXRGAIF-UHFFFAOYSA-N 0.000 description 1
ZHUQKYBEVUVRAV-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-(4-fluorophenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 ZHUQKYBEVUVRAV-UHFFFAOYSA-N 0.000 description 1
HTWHUNGPMGRCDS-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-(4-methylphenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]propan-2-ol Chemical compound C1=CC(C)=CC=C1OC1=CC=CC(N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 HTWHUNGPMGRCDS-UHFFFAOYSA-N 0.000 description 1
JLYOTGQSNHLLQR-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-(4-methylphenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]propan-2-ol Chemical compound C1=CC(C)=CC=C1OC1=CC=CC(N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 JLYOTGQSNHLLQR-UHFFFAOYSA-N 0.000 description 1
JQTUEDYQKJJZSF-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-[3-(1,1,2,2,2-pentafluoroethyl)phenoxy]-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 JQTUEDYQKJJZSF-UHFFFAOYSA-N 0.000 description 1
NYISYXOLBAEGMR-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-[3-(1,1,2,2-tetrafluoroethoxy)phenoxy]-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)(F)C(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 NYISYXOLBAEGMR-UHFFFAOYSA-N 0.000 description 1
AEXSSPBCNZSWAX-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-[3-(furan-2-yl)phenoxy]-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(C=CC=2)C=2OC=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 AEXSSPBCNZSWAX-UHFFFAOYSA-N 0.000 description 1
XNYMOOHZPFZFJE-UHFFFAOYSA-N 1,1,1-trifluoro-3-[3-phenoxy-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 XNYMOOHZPFZFJE-UHFFFAOYSA-N 0.000 description 1
UHVHNUUFXNLDAY-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-3-[3-(1,1,2,2,2-pentafluoroethyl)phenoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1F UHVHNUUFXNLDAY-UHFFFAOYSA-N 0.000 description 1
JKUYQRWIHXRYDW-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]-3-[3-(trifluoromethoxy)phenoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1F JKUYQRWIHXRYDW-UHFFFAOYSA-N 0.000 description 1
OWDYTXAMAKPKMS-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-(3-propan-2-ylphenoxy)anilino]propan-2-ol Chemical compound CC(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 OWDYTXAMAKPKMS-UHFFFAOYSA-N 0.000 description 1
QLKFFVYKPJREMZ-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-(5,6,7,8-tetrahydronaphthalen-2-yloxy)anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C3CCCCC3=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 QLKFFVYKPJREMZ-UHFFFAOYSA-N 0.000 description 1
SHKNMGATJUCZOD-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-[2-(trifluoromethyl)pyridin-4-yl]oxyanilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(N=CC=2)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 SHKNMGATJUCZOD-UHFFFAOYSA-N 0.000 description 1
XUDRRLDKJUIQCV-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)(F)C(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 XUDRRLDKJUIQCV-UHFFFAOYSA-N 0.000 description 1
JXIJYGKAJOIFQA-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-[[3-(trifluoromethoxy)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(OC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 JXIJYGKAJOIFQA-UHFFFAOYSA-N 0.000 description 1
CPAVKQNGAKOYEU-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-[[3-(trifluoromethyl)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(C=CC=2)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 CPAVKQNGAKOYEU-UHFFFAOYSA-N 0.000 description 1
SPUQOIZASZOIHB-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-[[3-(trifluoromethylsulfanyl)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(SC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 SPUQOIZASZOIHB-UHFFFAOYSA-N 0.000 description 1
LSFXNQDEHYDQQU-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-3-phenoxyanilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 LSFXNQDEHYDQQU-UHFFFAOYSA-N 0.000 description 1
JWBURSGRFHLUQI-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-(3-methylphenoxy)anilino]propan-2-ol Chemical compound CC1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)C(F)(F)F)=C1 JWBURSGRFHLUQI-UHFFFAOYSA-N 0.000 description 1
MOYVYFJUYHYWPE-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-(3-propan-2-ylphenoxy)anilino]propan-2-ol Chemical compound CC(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)C(F)(F)F)=C1 MOYVYFJUYHYWPE-UHFFFAOYSA-N 0.000 description 1
GZBPYOXWXVPULN-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-(5,6,7,8-tetrahydronaphthalen-2-yloxy)anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C3CCCCC3=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 GZBPYOXWXVPULN-UHFFFAOYSA-N 0.000 description 1
UAJDNORDBIVCEG-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-[2-(trifluoromethyl)pyridin-4-yl]oxyanilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(N=CC=2)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 UAJDNORDBIVCEG-UHFFFAOYSA-N 0.000 description 1
MHNUUTRSODRFMJ-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-[3-(1,1,2,2,2-pentafluoroethyl)phenoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 MHNUUTRSODRFMJ-UHFFFAOYSA-N 0.000 description 1
RQHYCFJBSJKNPT-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-[[3-(trifluoromethoxy)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(OC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 RQHYCFJBSJKNPT-UHFFFAOYSA-N 0.000 description 1
QLDUCVDVNRHXMQ-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-[[3-(trifluoromethylsulfanyl)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(SC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 QLDUCVDVNRHXMQ-UHFFFAOYSA-N 0.000 description 1
GATIWFIWQIDBRF-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]-3-phenoxyanilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 GATIWFIWQIDBRF-UHFFFAOYSA-N 0.000 description 1
PAYVDVGQXAVUIO-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-3-(5,6,7,8-tetrahydronaphthalen-2-yloxy)anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C3CCCCC3=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 PAYVDVGQXAVUIO-UHFFFAOYSA-N 0.000 description 1
SABWLQWNCVPFQO-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-3-[2-(trifluoromethyl)pyridin-4-yl]oxyanilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(N=CC=2)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 SABWLQWNCVPFQO-UHFFFAOYSA-N 0.000 description 1
RVERDNBQXIQXID-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-3-[3-(trifluoromethoxy)phenoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 RVERDNBQXIQXID-UHFFFAOYSA-N 0.000 description 1
ZMHUYPVJYHUOHI-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-3-[[3-(trifluoromethoxy)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(OC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 ZMHUYPVJYHUOHI-UHFFFAOYSA-N 0.000 description 1
YVQCXJRHKSEPKP-UHFFFAOYSA-N 1,1,1-trifluoro-3-[n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-3-[[3-(trifluoromethylsulfanyl)phenyl]methoxy]anilino]propan-2-ol Chemical compound C=1C=CC(OCC=2C=C(SC(F)(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 YVQCXJRHKSEPKP-UHFFFAOYSA-N 0.000 description 1
150000000178 1,2,4-triazoles Chemical class 0.000 description 1
MGYGLJCPZJNDQK-UHFFFAOYSA-N 1-(2-ethylbutyl)cyclohexane-1-carboxamide Chemical compound CCC(CC)CC1(C(N)=O)CCCCC1 MGYGLJCPZJNDQK-UHFFFAOYSA-N 0.000 description 1
VOICFBFFXOHVTI-UHFFFAOYSA-N 1-(3-methylbutyl)cyclohexane-1-carboxamide Chemical compound CC(C)CCC1(C(N)=O)CCCCC1 VOICFBFFXOHVTI-UHFFFAOYSA-N 0.000 description 1
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
NFIHXTUNNGIYRF-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate Chemical compound CCCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCCC NFIHXTUNNGIYRF-UHFFFAOYSA-N 0.000 description 1
OIIUJCZTDRFUIJ-QUCCMNQESA-N 2-hydroxyethyl (2R,4S)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate Chemical compound OCCOC(=O)N1[C@@H](C[C@@H](C2=CC(=CC=C12)C(F)(F)F)NC(=O)OCCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)CC OIIUJCZTDRFUIJ-QUCCMNQESA-N 0.000 description 1
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
BHIZVZJETFVJMJ-UHFFFAOYSA-N 2-hydroxypropyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)O BHIZVZJETFVJMJ-UHFFFAOYSA-N 0.000 description 1
UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
MEJYDZQQVZJMPP-UHFFFAOYSA-N 3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound COC1COC2C(OC)COC21 MEJYDZQQVZJMPP-UHFFFAOYSA-N 0.000 description 1
YSKSNVMKBCLHTI-UHFFFAOYSA-N 3-[3-(2,3-dichlorophenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C(=C(Cl)C=CC=2)Cl)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 YSKSNVMKBCLHTI-UHFFFAOYSA-N 0.000 description 1
OFAIRANJAQCWOZ-UHFFFAOYSA-N 3-[3-(2,3-dichlorophenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C(=C(Cl)C=CC=2)Cl)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 OFAIRANJAQCWOZ-UHFFFAOYSA-N 0.000 description 1
KNOYGUIIMGUTDN-UHFFFAOYSA-N 3-[3-(3,5-dimethylphenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=CC(C)=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 KNOYGUIIMGUTDN-UHFFFAOYSA-N 0.000 description 1
ZADGVYNGXWIMLX-UHFFFAOYSA-N 3-[3-(3,5-dimethylphenoxy)-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=CC(C)=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)C(F)(F)F)=C1 ZADGVYNGXWIMLX-UHFFFAOYSA-N 0.000 description 1
RJFQDJXPOVZIQX-UHFFFAOYSA-N 3-[3-(3,5-dimethylphenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=CC(C)=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 RJFQDJXPOVZIQX-UHFFFAOYSA-N 0.000 description 1
KGTNCLKLNUUOQF-UHFFFAOYSA-N 3-[3-(3-cyclopropylphenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(C=CC=2)C2CC2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 KGTNCLKLNUUOQF-UHFFFAOYSA-N 0.000 description 1
AMSQTWYXTRJMHM-UHFFFAOYSA-N 3-[3-(3-cyclopropylphenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(C=CC=2)C2CC2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 AMSQTWYXTRJMHM-UHFFFAOYSA-N 0.000 description 1
CBDYIAFHDCVXLZ-UHFFFAOYSA-N 3-[3-(3-ethylphenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CCC1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 CBDYIAFHDCVXLZ-UHFFFAOYSA-N 0.000 description 1
AUMYXTAXBSCUHF-UHFFFAOYSA-N 3-[3-(3-ethylphenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CCC1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 AUMYXTAXBSCUHF-UHFFFAOYSA-N 0.000 description 1
UXROVBKCDMFKNI-UHFFFAOYSA-N 3-[3-(3-tert-butylphenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC(C)(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 UXROVBKCDMFKNI-UHFFFAOYSA-N 0.000 description 1
HIWMGCZZAVMYRS-UHFFFAOYSA-N 3-[3-(3-tert-butylphenoxy)-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC(C)(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)C(F)(F)F)=C1 HIWMGCZZAVMYRS-UHFFFAOYSA-N 0.000 description 1
KBCYRJMHJBESOS-UHFFFAOYSA-N 3-[3-(3-tert-butylphenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC(C)(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 KBCYRJMHJBESOS-UHFFFAOYSA-N 0.000 description 1
JLYPUUAWEGALNC-UHFFFAOYSA-N 3-[3-(4-chloro-3-ethylphenoxy)-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C1=C(Cl)C(CC)=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C(=CC=C(C=2)C(F)(F)F)F)=C1 JLYPUUAWEGALNC-UHFFFAOYSA-N 0.000 description 1
JQHFWEQCSKGWMR-UHFFFAOYSA-N 3-[3-(4-chloro-3-ethylphenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C1=C(Cl)C(CC)=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 JQHFWEQCSKGWMR-UHFFFAOYSA-N 0.000 description 1
ZWAKXZGFUFCBJC-UHFFFAOYSA-N 3-[3-(4-chloro-3-ethylphenoxy)-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C1=C(Cl)C(CC)=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)C(F)(F)F)=C1 ZWAKXZGFUFCBJC-UHFFFAOYSA-N 0.000 description 1
VHSPKQAESIGBIC-UHFFFAOYSA-N 3-[3-(4-chloro-3-ethylphenoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C1=C(Cl)C(CC)=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 VHSPKQAESIGBIC-UHFFFAOYSA-N 0.000 description 1
ZVCLYLDJZUUGCN-UHFFFAOYSA-N 3-[3-(5-bromo-2-fluorophenoxy)-n-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C(=CC=C(Br)C=2)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC(C(F)(F)F)=CC=C1F ZVCLYLDJZUUGCN-UHFFFAOYSA-N 0.000 description 1
OUSOSXJEWGCFOL-UHFFFAOYSA-N 3-[3-(5-bromo-2-fluorophenoxy)-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C(=CC=C(Br)C=2)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 OUSOSXJEWGCFOL-UHFFFAOYSA-N 0.000 description 1
PSNIFYKKHZAJLW-UHFFFAOYSA-N 3-[3-(5-bromo-2-fluorophenoxy)-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C(=CC=C(Br)C=2)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 PSNIFYKKHZAJLW-UHFFFAOYSA-N 0.000 description 1
DYLDZWMOCOMTDK-UHFFFAOYSA-N 3-[3-(cyclohexylmethoxy)-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OCC2CCCCC2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 DYLDZWMOCOMTDK-UHFFFAOYSA-N 0.000 description 1
HAAQJFJWWULHGI-UHFFFAOYSA-N 3-[3-(cyclohexylmethoxy)-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OCC2CCCCC2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 HAAQJFJWWULHGI-UHFFFAOYSA-N 0.000 description 1
AJTZRRKUOPSIAQ-UHFFFAOYSA-N 3-[3-[(3,5-difluorophenyl)methoxy]-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OCC=2C=C(F)C=C(F)C=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)F)=C1 AJTZRRKUOPSIAQ-UHFFFAOYSA-N 0.000 description 1
UXGNQFGMQDSUJY-UHFFFAOYSA-N 3-[3-[(3,5-dimethylphenyl)methoxy]-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=CC(C)=CC(COC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)C(F)(F)F)=C1 UXGNQFGMQDSUJY-UHFFFAOYSA-N 0.000 description 1
PBYLAYANIVCUTQ-UHFFFAOYSA-N 3-[3-[(3,5-dimethylphenyl)methoxy]-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=CC(C)=CC(COC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 PBYLAYANIVCUTQ-UHFFFAOYSA-N 0.000 description 1
RHTRAJZPOSZNCM-UHFFFAOYSA-N 3-[3-[2-(difluoromethoxy)pyridin-4-yl]oxy-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)F)N=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 RHTRAJZPOSZNCM-UHFFFAOYSA-N 0.000 description 1
FQPJXFYFYBYIQM-UHFFFAOYSA-N 3-[3-[2-(difluoromethoxy)pyridin-4-yl]oxy-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)F)N=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 FQPJXFYFYBYIQM-UHFFFAOYSA-N 0.000 description 1
HNLAFPBRFDGEGS-UHFFFAOYSA-N 3-[3-[3-(difluoromethoxy)phenoxy]-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 HNLAFPBRFDGEGS-UHFFFAOYSA-N 0.000 description 1
HBMLOCDGFLWTCM-UHFFFAOYSA-N 3-[3-[3-(difluoromethoxy)phenoxy]-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(OC(F)F)C=CC=2)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 HBMLOCDGFLWTCM-UHFFFAOYSA-N 0.000 description 1
NUXDWLPBDOFOBY-UHFFFAOYSA-N 3-[3-[3-(dimethylamino)phenoxy]-n-[[3-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CN(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)=C1 NUXDWLPBDOFOBY-UHFFFAOYSA-N 0.000 description 1
FCICIXBJFWXPBM-UHFFFAOYSA-N 3-[3-[3-(dimethylamino)phenoxy]-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CN(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(C=CC=2)C(F)(F)C(F)(F)C(F)(F)F)=C1 FCICIXBJFWXPBM-UHFFFAOYSA-N 0.000 description 1
NOVSYOAFPGEWMY-UHFFFAOYSA-N 3-[3-[3-(dimethylamino)phenoxy]-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound CN(C)C1=CC=CC(OC=2C=C(C=CC=2)N(CC(O)C(F)(F)F)CC=2C=C(OC(F)(F)C(F)F)C=CC=2)=C1 NOVSYOAFPGEWMY-UHFFFAOYSA-N 0.000 description 1
BOTFWALRRFIFLJ-UHFFFAOYSA-N 3-[3-[4-chloro-3-(trifluoromethyl)phenoxy]-n-[[3-(1,1,2,2,3,3,3-heptafluoropropyl)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(C(Cl)=CC=2)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(C(F)(F)C(F)(F)C(F)(F)F)=C1 BOTFWALRRFIFLJ-UHFFFAOYSA-N 0.000 description 1
DLUSINDXHKFWLR-UHFFFAOYSA-N 3-[3-[4-chloro-3-(trifluoromethyl)phenoxy]-n-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]anilino]-1,1,1-trifluoropropan-2-ol Chemical compound C=1C=CC(OC=2C=C(C(Cl)=CC=2)C(F)(F)F)=CC=1N(CC(O)C(F)(F)F)CC1=CC=CC(OC(F)(F)C(F)F)=C1 DLUSINDXHKFWLR-UHFFFAOYSA-N 0.000 description 1
OTKLKVYZDAIPKO-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(OCO2)C2=C1 OTKLKVYZDAIPKO-UHFFFAOYSA-N 0.000 description 1
FLWUJPZKXUGSSK-UHFFFAOYSA-N 4-(2-fluorophenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC=C1F FLWUJPZKXUGSSK-UHFFFAOYSA-N 0.000 description 1
SMXIAERFMHCULI-UHFFFAOYSA-N 4-(2-methylphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC=C1C SMXIAERFMHCULI-UHFFFAOYSA-N 0.000 description 1
YVLKJEYJVYBFDD-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(Cl)=C1 YVLKJEYJVYBFDD-UHFFFAOYSA-N 0.000 description 1
RUZXGADUEMYARJ-UHFFFAOYSA-N 4-(3-methoxyphenyl)-3-tetradecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(OC)=C1 RUZXGADUEMYARJ-UHFFFAOYSA-N 0.000 description 1
YULMFDKUAMUBHP-UHFFFAOYSA-N 4-(3-methoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(OC)=C1 YULMFDKUAMUBHP-UHFFFAOYSA-N 0.000 description 1
WMMJYLRTBDJTAX-UHFFFAOYSA-N 4-(3-methylsulfanylphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CC(SC)=C1 WMMJYLRTBDJTAX-UHFFFAOYSA-N 0.000 description 1
PNNZCTKYKGKWTI-UHFFFAOYSA-N 4-(4-phenylmethoxyphenyl)-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C(C=C1)=CC=C1OCC1=CC=CC=C1 PNNZCTKYKGKWTI-UHFFFAOYSA-N 0.000 description 1
UCYSKZXGYSQRHA-UHFFFAOYSA-N 4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound C1C(C2CC2)N(C(O)=O)C2=CC=C(C(F)(F)F)C=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UCYSKZXGYSQRHA-UHFFFAOYSA-N 0.000 description 1
CKSIPHRFKAUYSS-UHFFFAOYSA-N 4-naphthalen-2-yl-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=C(C=CC=C2)C2=C1 CKSIPHRFKAUYSS-UHFFFAOYSA-N 0.000 description 1
DAKIEYCXFYULBC-UHFFFAOYSA-N 4-pyridin-3-yl-3-tridecyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCCCCCCCCCCC1=NNC(=S)N1C1=CC=CN=C1 DAKIEYCXFYULBC-UHFFFAOYSA-N 0.000 description 1
241001133760 Acoelorraphe Species 0.000 description 1
101100406575 Arabidopsis thaliana ORTH4 gene Proteins 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
NDBYTXYSECFVNR-UHFFFAOYSA-N C1CC1C2CC(C3=C(N2C(=O)O)C=CC(=C3)C(F)(F)F)NC(=O)OCCC4=CC(=CC(=C4)Cl)Cl Chemical compound C1CC1C2CC(C3=C(N2C(=O)O)C=CC(=C3)C(F)(F)F)NC(=O)OCCC4=CC(=CC(=C4)Cl)Cl NDBYTXYSECFVNR-UHFFFAOYSA-N 0.000 description 1
MFKBZADYYZUGTD-UHFFFAOYSA-N CC1CC(C2=CC=CC=C2N1N)C(=O)O Chemical class CC1CC(C2=CC=CC=C2N1N)C(=O)O MFKBZADYYZUGTD-UHFFFAOYSA-N 0.000 description 1
JRJMKYSKJZTERI-ZHRRBRCNSA-N CCC(CC)CN([C@H](C)C[C@@H](C1=C2)N(CC3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3)C(O)=O)C1=CC(OC)=C2OC Chemical compound CCC(CC)CN([C@H](C)C[C@@H](C1=C2)N(CC3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3)C(O)=O)C1=CC(OC)=C2OC JRJMKYSKJZTERI-ZHRRBRCNSA-N 0.000 description 1
KVGPFHLJHIRTQB-QRWLVFNGSA-N CCCCN([C@H](C)C[C@@H](C1=C2)N(CC3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3)C(O)=O)C1=CC(OC)=C2OC Chemical compound CCCCN([C@H](C)C[C@@H](C1=C2)N(CC3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3)C(O)=O)C1=CC(OC)=C2OC KVGPFHLJHIRTQB-QRWLVFNGSA-N 0.000 description 1
FKUURZXAFYJAFA-UHFFFAOYSA-N COC(=O)N(CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C2CC(N(C3=C2C=C(C=C3)Cl)C(=O)O)C4CC4 Chemical compound COC(=O)N(CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C2CC(N(C3=C2C=C(C=C3)Cl)C(=O)O)C4CC4 FKUURZXAFYJAFA-UHFFFAOYSA-N 0.000 description 1
WKAGPWWRAVBZDN-UHFFFAOYSA-N COC1=CC=C(C=C1)N1C(NN=C1CCCCCCCCCCCCCCC)=S Chemical compound COC1=CC=C(C=C1)N1C(NN=C1CCCCCCCCCCCCCCC)=S WKAGPWWRAVBZDN-UHFFFAOYSA-N 0.000 description 1
244000020518 Carthamus tinctorius Species 0.000 description 1
108010004103 Chylomicrons Proteins 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
IYTZJVLOPILDDM-UHFFFAOYSA-N FC(C=1C=C(CC(=O)NC2CC(N(C3=CC=C(C=C23)C(F)(F)F)C(=O)O)C2CC2)C=C(C1)C(F)(F)F)(F)F Chemical compound FC(C=1C=C(CC(=O)NC2CC(N(C3=CC=C(C=C23)C(F)(F)F)C(=O)O)C2CC2)C=C(C1)C(F)(F)F)(F)F IYTZJVLOPILDDM-UHFFFAOYSA-N 0.000 description 1
GXTJYZCKUCZXHG-UHFFFAOYSA-N FC(C=1C=C(CCOC(=O)NC2CC(N(C3=CC=C(C=C23)C(F)(F)F)C(=O)O)C2CCC2)C=C(C1)C(F)(F)F)(F)F Chemical compound FC(C=1C=C(CCOC(=O)NC2CC(N(C3=CC=C(C=C23)C(F)(F)F)C(=O)O)C2CCC2)C=C(C1)C(F)(F)F)(F)F GXTJYZCKUCZXHG-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
102000003886 Glycoproteins Human genes 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
235000019484 Rapeseed oil Nutrition 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
101100263687 Xenopus laevis vim4 gene Proteins 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
125000005354 acylalkyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 description 1
125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
125000005422 alkyl sulfonamido group Chemical group 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000005333 aroyloxy group Chemical group 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
125000005018 aryl alkenyl group Chemical group 0.000 description 1
125000001691 aryl alkyl amino group Chemical group 0.000 description 1
125000004659 aryl alkyl thio group Chemical group 0.000 description 1
125000005421 aryl sulfonamido group Chemical group 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
230000027455 binding Effects 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
125000005518 carboxamido group Chemical group 0.000 description 1
230000008859 change Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000005159 cyanoalkoxy group Chemical group 0.000 description 1
125000004465 cycloalkenyloxy group Chemical group 0.000 description 1
125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 1
125000006310 cycloalkyl amino group Chemical group 0.000 description 1
125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000005786 degenerative changes Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
125000004212 difluorophenyl group Chemical group 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000002651 drug therapy Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000002296 dynamic light scattering Methods 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
PUJHHRKYEYYGKZ-YJYMSZOUSA-N ethyl (2R,4S)-4-[2-[3,5-bis(trifluoromethyl)phenyl]ethoxycarbonylamino]-2-methyl-7-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate Chemical compound C(C)OC(=O)N1[C@@H](C[C@@H](C2=CC=C(C=C12)C(F)(F)F)NC(=O)OCCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C PUJHHRKYEYYGKZ-YJYMSZOUSA-N 0.000 description 1
CUSXLPZVXIVBBD-UHFFFAOYSA-N ethyl 4-[(2,6-dichloropyridin-4-yl)methyl-methoxycarbonylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(C(=O)OCC)C(C)CC1N(C(=O)OC)CC1=CC(Cl)=NC(Cl)=C1 CUSXLPZVXIVBBD-UHFFFAOYSA-N 0.000 description 1
YNWDTGFPCVFPJG-UHFFFAOYSA-N ethyl 4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-cyclopropyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OCC)C(C2CC2)CC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YNWDTGFPCVFPJG-UHFFFAOYSA-N 0.000 description 1
AIFUJOZBCJJFNU-UHFFFAOYSA-N ethyl 6,6-dimethyl-4-oxobicyclo[3.1.1]heptane-3-carboxylate Chemical compound O=C1C(C(=O)OCC)CC2C(C)(C)C1C2 AIFUJOZBCJJFNU-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000020937 fasting conditions Nutrition 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
229940125753 fibrate Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000030136 gastric emptying Effects 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 1
101150028517 hlb gene Proteins 0.000 description 1
125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
229960000991 ketoprofen Drugs 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229940063121 neoral Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000012875 nonionic emulsifier Substances 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
229940100688 oral solution Drugs 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
238000005192 partition Methods 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
239000008389 polyethoxylated castor oil Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
229940068977 polysorbate 20 Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
CBESVOBAJBLBBT-KNQAVFIVSA-N propan-2-yl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-formylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound O=CN([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OC(C)C)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CBESVOBAJBLBBT-KNQAVFIVSA-N 0.000 description 1
IMHUVAAQBSIFDC-UHFFFAOYSA-N propan-2-yl 4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-propan-2-yl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C1C(C(C)C)N(C(=O)OC(C)C)C2=CC=C(C(F)(F)F)C=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IMHUVAAQBSIFDC-UHFFFAOYSA-N 0.000 description 1
TUPKOWFPVAXQFP-UHFFFAOYSA-N propan-2-yl 4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)C(CC)CC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 TUPKOWFPVAXQFP-UHFFFAOYSA-N 0.000 description 1
229940032159 propylene carbonate Drugs 0.000 description 1
229940026235 propylene glycol monolaurate Drugs 0.000 description 1
239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
RAYMXZBXQCGRGX-UHFFFAOYSA-N quinoline-5-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-N 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
CCSJXVJLCREWRO-UHFFFAOYSA-N s-[2-[[1-(2-ethylbutyl)cyclohexanecarbonyl]amino]phenyl] ethanethioate Chemical compound C=1C=CC=C(SC(C)=O)C=1NC(=O)C1(CC(CC)CC)CCCCC1 CCSJXVJLCREWRO-UHFFFAOYSA-N 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
229940063122 sandimmune Drugs 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
150000003463 sulfur Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4706—4-Aminoquinolines; 8-Aminoquinolines, e.g. chloroquine, primaquine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biophysics (AREA)
Chemical Kinetics & Catalysis (AREA)
Dispersion Chemistry (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Bioinformatics & Cheminformatics (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Diabetes (AREA)
Oil, Petroleum & Natural Gas (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Cosmetics (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Colloid Chemistry (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Quinoline Compounds (AREA)
Steroid Compounds (AREA)
Peptides Or Proteins (AREA)

SK1517-2003A 2001-06-21 2002-05-03 Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors SK15172003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US30002801P	2001-06-21	2001-06-21
PCT/IB2002/001571 WO2003000295A2 (en)	2001-06-21	2002-05-03	Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors

Publications (1)

Publication Number	Publication Date
SK15172003A3 true SK15172003A3 (en)	2004-11-03

Family

ID=23157363

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1517-2003A SK15172003A3 (en)	2001-06-21	2002-05-03	Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors

Country Status (33)

Country	Link
US (2)	US6962931B2 (cs)
EP (1)	EP1453544A2 (cs)
JP (1)	JP2005500314A (cs)
KR (1)	KR20040015746A (cs)
CN (1)	CN1635911A (cs)
AP (1)	AP2002002559A0 (cs)
AR (1)	AR034599A1 (cs)
BG (1)	BG108486A (cs)
BR (1)	BR0210505A (cs)
CA (1)	CA2455288A1 (cs)
CR (1)	CR7163A (cs)
CZ (1)	CZ20033341A3 (cs)
EA (1)	EA200301139A1 (cs)
EC (1)	ECSP034875A (cs)
EE (1)	EE200400024A (cs)
GT (1)	GT200200124A (cs)
HN (1)	HN2002000153A (cs)
HU (1)	HUP0400263A2 (cs)
IL (1)	IL158765A0 (cs)
IS (1)	IS7014A (cs)
MA (1)	MA27034A1 (cs)
MX (1)	MXPA04000014A (cs)
NO (1)	NO20035632L (cs)
OA (1)	OA12619A (cs)
PA (1)	PA8548601A1 (cs)
PE (1)	PE20030128A1 (cs)
PL (1)	PL368850A1 (cs)
SK (1)	SK15172003A3 (cs)
SV (1)	SV2003001103A (cs)
TN (1)	TNSN03139A1 (cs)
UY (1)	UY27344A1 (cs)
WO (1)	WO2003000295A2 (cs)
ZA (1)	ZA200308561B (cs)

Families Citing this family (78)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE404172T1 (de) *	1998-12-30	2008-08-15	Dexcel Ltd	Dispergierbares konzentrat zur verabreichung von cyclosporin
US7732404B2 (en) *	1999-12-30	2010-06-08	Dexcel Ltd	Pro-nanodispersion for the delivery of cyclosporin
JP4031232B2 (ja) *	2001-11-09	2008-01-09	カプスゲル・ジャパン株式会社	新規カプセル
DE60320940D1 (de)	2002-02-01	2008-06-26	Pfizer Prod Inc	Pharmazeutische zusammensetzungen amorpher dispersionen von wirkstoffen und lipophiler mikrophasenbildender materialien
EP1485442A4 (en) *	2002-03-01	2009-11-11	Cesi Chemical A Flotek Co	COMPOSITION AND METHOD FOR CLEANING A WELL
US20040175341A1 (en) *	2003-03-04	2004-09-09	Manning Monna Marie	Microemulsion for cosmetic or pharmaceutical use containing an active ingredient
PT1603553E (pt) *	2003-03-17	2012-02-03	Japan Tobacco Inc	Composições farmacêuticas de inibidores de cetp
CN1761463A (zh) *	2003-03-17	2006-04-19	日本烟草产业株式会社	提高s－[2－([[1－(2－乙基丁基)环己基]羰基]氨基)苯基]－2－甲基丙硫代酸酯口服生物利用度的方法
WO2004082675A1 (en) *	2003-03-17	2004-09-30	Japan Tobacco Inc.	Method for increasing the oral bioavailability of s-[2- ([[1- (2-ethylbutyl) cyclohexyl] carbonyl] amino) phenyl] 2-methylpropanethioate
TWI494102B (zh) *	2003-05-02	2015-08-01	Japan Tobacco Inc	包含ｓ-〔２（〔〔１-（２-乙基丁基）環己基〕羰基〕胺基）苯基〕２-甲基丙烷硫酯及ｈｍｇ輔酶ａ還原酶抑制劑之組合
BRPI0413277A (pt) *	2003-08-04	2006-10-10	Pfizer Prod Inc	composições farmacêuticas de adsorvatos de medicamentos amorfos e materiais que formam microfases lipofìlicas
WO2005033082A2 (en) *	2003-09-30	2005-04-14	Pfizer Products Inc.	Cetp inhibitors and metabolites thereof
DE602004023100D1 (de) *	2003-10-08	2009-10-22	Lilly Co Eli	Verbindungen und verfahren zur behandlung von dyslipidemie
US20050220866A1 (en) *	2004-04-02	2005-10-06	Dr. Reddy's Laboratories Limited	Novel capsule formulations of etoposide for oral use
US7700774B2 (en)	2004-12-20	2010-04-20	Dr. Reddy's Laboratories Ltd.	Heterocyclic compounds and their pharmaceutical compositions
CA2605214C (en)	2004-12-31	2016-07-12	Reddy Us Therapeutics, Inc.	Benzylamine derivatives as cetp inhibitors
US8604055B2 (en)	2004-12-31	2013-12-10	Dr. Reddy's Laboratories Ltd.	Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors
US20090169583A1 (en) *	2005-02-08	2009-07-02	Pfizer, Inc.	Solid Adsorbates of Hydrophobic Drugs
US7623458B2 (en) *	2005-09-30	2009-11-24	The Boeing Company	System and method for providing integrated services across cryptographic boundaries in a network
US8486983B2 (en)	2005-12-05	2013-07-16	Merck Sharp & Dohme Corp.	Self-emulsifying formulations of CETP inhibitors
EP1982705B8 (en) *	2005-12-31	2012-08-22	Tasly Pharmaceutical Group Co., Ltd.	Pharmaceutical composition containing chenopodium ambrosioides extract and its preparation process and application
WO2008005352A2 (en) *	2006-06-30	2008-01-10	Schering Corporation	Solid dose formulations of a thrombin receptor antagonist
EP1961412A1 (en) *	2006-12-27	2008-08-27	LEK Pharmaceuticals D.D.	Self-microemulsifying drug delivery systems
US9222013B1 (en)	2008-11-13	2015-12-29	Cesi Chemical, Inc.	Water-in-oil microemulsions for oilfield applications
BRPI0922888A2 (pt) *	2008-12-08	2019-09-24	Hoffmann La Roche	administração combinada de fármaco
US20100273730A1 (en) *	2009-04-27	2010-10-28	Innopharmax, Inc.	Self-emulsifying pharmaceutical compositions of hydrophilic drugs and preparation thereof
SMT202000093T1 (it)	2009-06-16	2020-03-13	Pfizer	Forme di dosaggio di apixaban
CA2690490C (en) *	2010-01-19	2012-06-26	Accucaps Industries Limited	Pharmaceutical formulations of loratadine for encapsulation and combinations thereof
BR112013029778A2 (pt) *	2011-05-20	2017-01-17	Aventis Pharma Inc	composição farmacêutica que compreende fexofenadina
EP2744803A2 (en)	2011-08-18	2014-06-25	Dr. Reddy's Laboratories Ltd.	Substituted heterocyclic amine compounds as cholestryl ester-transfer protein (cetp) inhibitors
MX352074B (es)	2011-09-27	2017-11-08	Dr Reddys Laboratories Ltd	Derivados de 5-bencilaminometil-6-aminopirazolo [3,4-b] piridina como inhibidores de proteina de transferencia de ester de colesterilo (cetp) utiles para el tratamiento de aterosclerosis.
US10874635B2 (en)	2011-10-21	2020-12-29	First Tech International Limited	Tocotrienol compositions
US20130292121A1 (en)	2012-04-15	2013-11-07	Cesi Chemical, Inc.	Surfactant formulations for foam flooding
US9200192B2 (en)	2012-05-08	2015-12-01	Cesi Chemical, Inc.	Compositions and methods for enhancement of production of liquid and gaseous hydrocarbons
US11407930B2 (en)	2012-05-08	2022-08-09	Flotek Chemistry, Llc	Compositions and methods for enhancement of production of liquid and gaseous hydrocarbons
WO2014128564A2 (en) *	2013-02-21	2014-08-28	Dr. Reddy's Laboratories Ltd.	Pharmaceutical compositions of cetp inhibitors
US9464223B2 (en)	2013-03-14	2016-10-11	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
US11180690B2 (en)	2013-03-14	2021-11-23	Flotek Chemistry, Llc	Diluted microemulsions with low surface tensions
US9884988B2 (en)	2013-03-14	2018-02-06	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
US10053619B2 (en)	2013-03-14	2018-08-21	Flotek Chemistry, Llc	Siloxane surfactant additives for oil and gas applications
US10421707B2 (en)	2013-03-14	2019-09-24	Flotek Chemistry, Llc	Methods and compositions incorporating alkyl polyglycoside surfactant for use in oil and/or gas wells
US10717919B2 (en)	2013-03-14	2020-07-21	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
US9868893B2 (en)	2013-03-14	2018-01-16	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
US9428683B2 (en)	2013-03-14	2016-08-30	Flotek Chemistry, Llc	Methods and compositions for stimulating the production of hydrocarbons from subterranean formations
US10941106B2 (en)	2013-03-14	2021-03-09	Flotek Chemistry, Llc	Methods and compositions incorporating alkyl polyglycoside surfactant for use in oil and/or gas wells
US9068108B2 (en)	2013-03-14	2015-06-30	Cesi Chemical, Inc.	Methods and compositions for stimulating the production of hydrocarbons from subterranean formations
US11254856B2 (en)	2013-03-14	2022-02-22	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
US10590332B2 (en)	2013-03-14	2020-03-17	Flotek Chemistry, Llc	Siloxane surfactant additives for oil and gas applications
US10577531B2 (en)	2013-03-14	2020-03-03	Flotek Chemistry, Llc	Polymers and emulsions for use in oil and/or gas wells
US10287483B2 (en)	2013-03-14	2019-05-14	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells comprising a terpene alcohol
US9321955B2 (en)	2013-06-14	2016-04-26	Flotek Chemistry, Llc	Methods and compositions for stimulating the production of hydrocarbons from subterranean formations
US10000693B2 (en)	2013-03-14	2018-06-19	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
CN104706689A (zh) *	2013-12-16	2015-06-17	天津迈迪瑞康生物医药科技有限公司	一种鸦胆子油脂肪乳浓缩液、其制备方法及用途
CN104706587A (zh) *	2013-12-16	2015-06-17	天津迈迪瑞康生物医药科技有限公司	一种依托咪酯脂肪乳浓缩液、其制备方法及用途
CN104706586A (zh) *	2013-12-16	2015-06-17	天津迈迪瑞康生物医药科技有限公司	一种丁酸氯维地平脂肪乳浓缩液、其制备方法及用途
US9890625B2 (en)	2014-02-28	2018-02-13	Eclipse Ior Services, Llc	Systems and methods for the treatment of oil and/or gas wells with an obstruction material
US9890624B2 (en)	2014-02-28	2018-02-13	Eclipse Ior Services, Llc	Systems and methods for the treatment of oil and/or gas wells with a polymeric material
CA2891278C (en)	2014-05-14	2018-11-06	Cesi Chemical, Inc.	Methods and compositions for use in oil and / or gas wells
CA2898770C (en)	2014-07-28	2019-05-21	Cesi Chemical, Inc.	Methods and compositions related to gelled layers in oil and/or gas wells
EP3215128B1 (en) *	2014-11-04	2019-09-04	Innopharmax, Inc.	Oral administration of unstable or poorly-absorbed drugs
CN104490775A (zh) *	2014-12-20	2015-04-08	长沙佰顺生物科技有限公司	一种安塞曲匹脂肪乳及其制备方法
CN104546710A (zh) *	2014-12-20	2015-04-29	长沙佰顺生物科技有限公司	一种安塞曲匹纳米乳及其制备方法
KR101590072B1 (ko) *	2014-12-23	2016-01-29	한미약품 주식회사	두타스테라이드를 포함하는 자가유화 약물전달 시스템용 조성물
RU2708254C2 (ru)	2015-05-28	2019-12-05	Др. Редди'С Лабораториз Лтд.	Пероральная композиция целекоксиба для лечения боли
AU2017248828A1 (en)	2016-04-15	2018-11-01	Janssen Sciences Ireland Uc	Combinations and methods comprising a capsid assembly inhibitor
US10934472B2 (en)	2017-08-18	2021-03-02	Flotek Chemistry, Llc	Compositions comprising non-halogenated solvents for use in oil and/or gas wells and related methods
US11053433B2 (en)	2017-12-01	2021-07-06	Flotek Chemistry, Llc	Methods and compositions for stimulating the production of hydrocarbons from subterranean formations
AU2019233606B2 (en)	2018-03-14	2024-10-03	KaNDy Therapeutics Limited	Novel pharmaceutical formulation comprising dual NK-1/NK-3 receptor antagonists
MX2020009531A (es)	2018-03-14	2020-10-05	Janssen Sciences Ireland Unlimited Co	Regimen posologico del modulador del ensamblaje de la capside.
FI3886813T3 (fi) *	2018-11-26	2023-05-04	Hepion Pharmaceuticals Inc	Syklosporiinianalogien farmaseuttisia formulaatioita
EP3952900A1 (en) *	2019-04-11	2022-02-16	R.P. Scherer Technologies, LLC	Formulation for oral delivery of proteins, peptides and small molecules with poor permeability
CN110252395B (zh) *	2019-07-01	2020-10-16	湖北远大生命科学与技术有限责任公司	一种用于制备高纯度牛磺酸的催化剂及其应用
US11104843B2 (en)	2019-10-10	2021-08-31	Flotek Chemistry, Llc	Well treatment compositions and methods comprising certain microemulsions and certain clay control additives exhibiting synergistic effect of enhancing clay swelling protection and persistency
FR3110852B1 (fr) *	2020-05-27	2024-03-15	Centre Nat Rech Scient	Emulsions pour liberation controlee de medicaments
US11512243B2 (en)	2020-10-23	2022-11-29	Flotek Chemistry, Llc	Microemulsions comprising an alkyl propoxylated sulfate surfactant, and related methods
CN114681470A (zh)	2020-12-28	2022-07-01	雷迪博士实验室有限公司	治疗疼痛的方法
CN119259277B (zh) *	2024-11-26	2026-04-03	昆明理工大学	一种氮杂环硫酮类化合物的应用
US12533358B1 (en)	2025-05-14	2026-01-27	Bayer Consumer Care Ag	Methods of treatment with elinzanetant

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2907460A1 (de) *	1978-03-07	1979-09-13	Sandoz Ag	Neue resorbierbare galenische kompositionen
GB9208712D0 (en)	1992-04-22	1992-06-10	Sandoz Ltd	Pharmaceutical compositions containing cyclosporin derivates
WO1995031979A1 (en)	1994-05-19	1995-11-30	R.P. Scherer International Corporation	Solutions of aryl or heteroaryl substituted alkanoic acids in lipophilic solvents and soft gelatin capsules containing such solutions
US5965160A (en) *	1995-04-24	1999-10-12	Yissum Research Development Company Of The Hebrew University Of Jerusalem	Self-emulsifiable formulation producing an oil-in-water emulsion
GB9608719D0 (en)	1996-04-26	1996-07-03	Scherer Ltd R P	Pharmaceutical compositions
US5993858A (en) *	1996-06-14	1999-11-30	Port Systems L.L.C.	Method and formulation for increasing the bioavailability of poorly water-soluble drugs
US5958876A (en) *	1996-06-19	1999-09-28	Novartis Ag	Cyclosporin-containing pharmaceutical compositions
ATE392891T1 (de)	1996-06-19	2008-05-15	Novartis Pharma Gmbh	Cyclosporin enthaltende präparate
JP2894445B2 (ja) *	1997-02-12	1999-05-24	日本たばこ産業株式会社	Ｃｅｔｐ活性阻害剤として有効な化合物
WO1999014204A1 (en) *	1997-09-16	1999-03-25	G.D. Searle & Co.	Substituted 1,2,4-triazoles useful for inhibiting cholesteryl ester transfer protein activity
DE19741399A1 (de) *	1997-09-19	1999-03-25	Bayer Ag	Tetrahydrochinoline
US6063762A (en)	1997-12-05	2000-05-16	Chong Kun Dang Corp.	Cyclosporin-containing microemulsion preconcentrate composition
AU3285499A (en) *	1998-02-13	1999-08-30	G.D. Searle & Co.	Substituted pyridines useful for inhibiting cholesteryl ester transfer protein activity
US6197786B1 (en) *	1998-09-17	2001-03-06	Pfizer Inc	4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines
US6147089A (en) *	1998-09-17	2000-11-14	Pfizer Inc.	Annulated 4-carboxyamino-2-methyl-1,2,3,4,-tetrahydroquinolines
US6147090A (en) *	1998-09-17	2000-11-14	Pfizer Inc.	4-carboxyamino-2-methyl-1,2,3,4,-tetrahydroquinolines
US6140342A (en) *	1998-09-17	2000-10-31	Pfizer Inc.	Oxy substituted 4-carboxyamino-2-methyl-1,2,3,4-tetrahydroquinolines
GT199900147A (es) *	1998-09-17	1999-09-06		1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas.
CA2345108A1 (en) *	1998-09-25	2000-04-06	Monsanto Company	Substituted n-aliphatic-n-aromatic tertiary-heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity
ATE404172T1 (de)	1998-12-30	2008-08-15	Dexcel Ltd	Dispergierbares konzentrat zur verabreichung von cyclosporin
CO5271716A1 (es) *	1999-11-30	2003-04-30	Pfizer Prod Inc	Cristales de 4- carboxamino 1,2,3,4-tetrahidroquinolina 2- sustituida
US6482862B1 (en) *	1999-12-20	2002-11-19	G.D. Searle & Co.	Method of using substituted N-benzyl-N-phenyl aminoalcohols for inhibiting cholesteryl ester transfer protein activity
US7115279B2 (en) *	2000-08-03	2006-10-03	Curatolo William J	Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors
CA2450748A1 (en) *	2001-06-22	2003-01-03	Pfizer Products Inc.	Pharmaceutical compositions containing polymer and drug assemblies
BR0210520A (pt) *	2001-06-22	2004-06-22	Pfizer Prod Inc	Composições farmacêuticas de dispersões de fármacos amorfos misturados com polìmeros
JP2004534812A (ja) *	2001-06-22	2004-11-18	ファイザー・プロダクツ・インク	薬物および中性ポリマーの分散物の医薬組成物
EP1269994A3 (en) *	2001-06-22	2003-02-12	Pfizer Products Inc.	Pharmaceutical compositions comprising drug and concentration-enhancing polymers
WO2003063831A2 (en) *	2002-02-01	2003-08-07	Pfizer Products Inc.	Immediate release dosage forms containing solid drug dispersions
DE60320940D1 (de) *	2002-02-01	2008-06-26	Pfizer Prod Inc	Pharmazeutische zusammensetzungen amorpher dispersionen von wirkstoffen und lipophiler mikrophasenbildender materialien
WO2004056359A1 (en) *	2002-12-20	2004-07-08	Pfizer Products Inc.	Dosage forms comprising a cetp inhibitor and an hmg-coa reductase inhibitor
US20040132771A1 (en) *	2002-12-20	2004-07-08	Pfizer Inc	Compositions of choleseteryl ester transfer protein inhibitors and HMG-CoA reductase inhibitors

2002
- 2002-05-03 EA EA200301139A patent/EA200301139A1/ru unknown
- 2002-05-03 BR BR0210505-5A patent/BR0210505A/pt not_active IP Right Cessation
- 2002-05-03 IL IL15876502A patent/IL158765A0/xx unknown
- 2002-05-03 JP JP2003506937A patent/JP2005500314A/ja active Pending
- 2002-05-03 SK SK1517-2003A patent/SK15172003A3/sk not_active Application Discontinuation
- 2002-05-03 KR KR10-2003-7016651A patent/KR20040015746A/ko not_active Ceased
- 2002-05-03 CN CNA028124820A patent/CN1635911A/zh active Pending
- 2002-05-03 WO PCT/IB2002/001571 patent/WO2003000295A2/en not_active Ceased
- 2002-05-03 PL PL02368850A patent/PL368850A1/xx not_active Application Discontinuation
- 2002-05-03 TN TNPCT/IB2002/001571A patent/TNSN03139A1/fr unknown
- 2002-05-03 MX MXPA04000014A patent/MXPA04000014A/es active IP Right Grant
- 2002-05-03 OA OA1200300317A patent/OA12619A/en unknown
- 2002-05-03 CZ CZ20033341A patent/CZ20033341A3/cs unknown
- 2002-05-03 HU HU0400263A patent/HUP0400263A2/hu unknown
- 2002-05-03 EE EEP200400024A patent/EE200400024A/xx unknown
- 2002-05-03 CA CA002455288A patent/CA2455288A1/en not_active Abandoned
- 2002-05-03 EP EP02732994A patent/EP1453544A2/en not_active Withdrawn
- 2002-06-19 PE PE2002000528A patent/PE20030128A1/es not_active Application Discontinuation
- 2002-06-19 AR ARP020102297A patent/AR034599A1/es unknown
- 2002-06-19 GT GT200200124A patent/GT200200124A/es unknown
- 2002-06-19 US US10/175,643 patent/US6962931B2/en not_active Expired - Fee Related
- 2002-06-20 AP APAP/P/2002/002559A patent/AP2002002559A0/en unknown
- 2002-06-20 UY UY27344A patent/UY27344A1/es not_active Application Discontinuation
- 2002-06-20 HN HN2002000153A patent/HN2002000153A/es unknown
- 2002-06-20 SV SV2002001103A patent/SV2003001103A/es not_active Application Discontinuation
- 2002-06-20 PA PA20028548601A patent/PA8548601A1/es unknown
2003
- 2003-10-31 IS IS7014A patent/IS7014A/is unknown
- 2003-11-03 ZA ZA200308561A patent/ZA200308561B/xx unknown
- 2003-11-24 CR CR7163A patent/CR7163A/es not_active Application Discontinuation
- 2003-12-03 EC EC2003004875A patent/ECSP034875A/es unknown
- 2003-12-10 MA MA27430A patent/MA27034A1/fr unknown
- 2003-12-17 NO NO20035632A patent/NO20035632L/no not_active Application Discontinuation
- 2003-12-22 BG BG108486A patent/BG108486A/bg unknown
2005
- 2005-09-08 US US11/222,908 patent/US20060014788A1/en not_active Abandoned

Also Published As

Publication number	Publication date
HN2002000153A (es)	2002-11-05
AP2002002559A0 (en)	2002-06-30
WO2003000295A2 (en)	2003-01-03
MA27034A1 (fr)	2004-12-20
EP1453544A2 (en)	2004-09-08
US20060014788A1 (en)	2006-01-19
EA200301139A1 (ru)	2004-12-30
BR0210505A (pt)	2004-05-18
TNSN03139A1 (fr)	2005-12-23
CN1635911A (zh)	2005-07-06
OA12619A (en)	2006-06-12
ZA200308561B (en)	2004-11-17
JP2005500314A (ja)	2005-01-06
ECSP034875A (es)	2004-01-28
MXPA04000014A (es)	2004-05-21
NO20035632D0 (no)	2003-12-17
PL368850A1 (en)	2005-04-04
KR20040015746A (ko)	2004-02-19
WO2003000295A3 (en)	2004-05-27
PA8548601A1 (es)	2003-09-05
CZ20033341A3 (cs)	2004-10-13
SV2003001103A (es)	2003-03-18
GT200200124A (es)	2003-09-22
CR7163A (es)	2004-02-23
UY27344A1 (es)	2003-01-31
BG108486A (bg)	2005-03-31
EE200400024A (et)	2004-06-15
NO20035632L (no)	2004-02-18
HUP0400263A2 (hu)	2005-03-29
AR034599A1 (es)	2004-03-03
PE20030128A1 (es)	2003-02-28
IS7014A (is)	2003-10-31
US20030022944A1 (en)	2003-01-30
US6962931B2 (en)	2005-11-08
CA2455288A1 (en)	2003-01-03
IL158765A0 (en)	2004-05-12

Legal Events

Date	Code	Title	Description
2011-01-04	FC9A	Refused patent application

Publication	Publication Date	Title
SK15172003A3 (en)	2004-11-03	Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors
EP2305217B1 (en)	2014-07-30	Method for the preparation of pharmaceutical compositions comprising a solid amorphous dispersion of cholesteryl ester transfer protein inhibitors
DE60220049T2 (de)	2007-08-30	Pharmazeutische Zusammensetzung, umfassend eine feste Dispersion eines im Wasser schwer löslichen Arzneimittels und ein löslichkeitssteigerndes Polymer
US8197848B2 (en)	2012-06-12	Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors
JP2007501217A (ja)	2007-01-25	コレステリルエステル転送タンパク質阻害剤を制御放出し、そしてＨＭＧ−ＣｏＡレダクターゼ阻害剤を即時放出する投薬形態
EP1581210B1 (en)	2008-03-19	Dosage forms comprising a cetp inhibitor and an hmg-coa reductase inhibitor
US20030072801A1 (en)	2003-04-17	Pharmaceutical compositions comprising drug and concentration-enhancing polymers
JP2005522424A (ja)	2005-07-28	コレステリルエステル転移タンパク質インヒビターの制御放出性薬剤投与形態
JP2004534811A (ja)	2004-11-18	ポリマーと薬剤の集合体を含む医薬組成物
US20040185102A1 (en)	2004-09-23	Dosage forms comprising a CETP inhibitor and an HMG-CoA reductase inhibitor
KR20040011549A (ko)	2004-02-05	저용해도 및(또는) 산-민감성 약물 및 중화된 산성중합체를 포함하는 제약 조성물
AU2002304366A1 (en)	2003-01-08	Self-emulsifying formulations of cholesteryl ester transfer protein inhibitors
AU2003201713A1 (en)	2003-09-02	Controlled release pharmaceutical dosage forms of a cholesteryl ester transfer protein inhibitor