BG108486A - Самоемулгиращи се препарати на инхибитори на протеин, пренасящ холестеролестер - Google Patents

Самоемулгиращи се препарати на инхибитори на протеин, пренасящ холестеролестер Download PDF

Info

Publication number: BG108486A
Authority: BG; Bulgaria
Prior art keywords: substituted; optionally; trifluoromethyl; carbon atoms; alkyl
Prior art date: 2001-06-21

Application number

BG108486A

Other languages

Bulgarian (bg)

English (en)

Inventor

Michael GUMKOWSKI

Sharad Murdande

Michael Perlman

Franco LOMBARDO

Original Assignee

Pfizer Products 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

2003-12-22

Publication date

2005-03-31

2003-12-22 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2005-03-31 Publication of BG108486A publication Critical patent/BG108486A/bg

Links

239000000203 mixture Substances 0.000 title claims abstract description 55
150000002148 esters Chemical class 0.000 title claims description 8
238000009472 formulation Methods 0.000 title description 6
238000012546 transfer Methods 0.000 title description 3
229940121649 protein inhibitor Drugs 0.000 title 1
239000012268 protein inhibitor Substances 0.000 title 1
239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims abstract description 99
239000004094 surface-active agent Substances 0.000 claims abstract description 91
229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims abstract description 49
239000006184 cosolvent Substances 0.000 claims abstract description 31
239000002904 solvent Substances 0.000 claims abstract description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 320
-1 transutol Natural products 0.000 claims description 308
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 258
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 240
125000000217 alkyl group Chemical group 0.000 claims description 233
229910052757 nitrogen Inorganic materials 0.000 claims description 229
229920006395 saturated elastomer Polymers 0.000 claims description 218
125000004043 oxo group Chemical group O=* 0.000 claims description 215
229910052736 halogen Inorganic materials 0.000 claims description 195
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 183
229910052717 sulfur Inorganic materials 0.000 claims description 175
229910052799 carbon Inorganic materials 0.000 claims description 173
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 172
150000002367 halogens Chemical class 0.000 claims description 165
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 154
239000011593 sulfur Substances 0.000 claims description 154
150000001721 carbon Chemical group 0.000 claims description 153
229910052760 oxygen Inorganic materials 0.000 claims description 149
125000005842 heteroatom Chemical group 0.000 claims description 141
229910052739 hydrogen Inorganic materials 0.000 claims description 139
125000003118 aryl group Chemical group 0.000 claims description 137
239000001257 hydrogen Substances 0.000 claims description 137
239000001301 oxygen Substances 0.000 claims description 136
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 125
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 122
125000000623 heterocyclic group Chemical group 0.000 claims description 115
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 111
150000002431 hydrogen Chemical class 0.000 claims description 105
125000004093 cyano group Chemical group *C#N 0.000 claims description 100
125000003545 alkoxy group Chemical group 0.000 claims description 98
125000000753 cycloalkyl group Chemical group 0.000 claims description 96
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 84
125000004414 alkyl thio group Chemical group 0.000 claims description 79
125000001072 heteroaryl group Chemical group 0.000 claims description 78
125000003342 alkenyl group Chemical group 0.000 claims description 77
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 67
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
125000005843 halogen group Chemical group 0.000 claims description 66
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 64
125000000304 alkynyl group Chemical group 0.000 claims description 64
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 63
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 58
125000001424 substituent group Chemical group 0.000 claims description 58
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 57
125000001153 fluoro group Chemical group F* 0.000 claims description 53
239000003921 oil Substances 0.000 claims description 43
125000002252 acyl group Chemical group 0.000 claims description 42
235000019198 oils Nutrition 0.000 claims description 42
125000002947 alkylene group Chemical group 0.000 claims description 33
125000001188 haloalkyl group Chemical group 0.000 claims description 32
125000000392 cycloalkenyl group Chemical group 0.000 claims description 31
125000002619 bicyclic group Chemical group 0.000 claims description 30
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 29
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
150000003254 radicals Chemical class 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 29
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical group CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 28
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
235000013305 food Nutrition 0.000 claims description 26
125000000262 haloalkenyl group Chemical group 0.000 claims description 25
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
125000003710 aryl alkyl group Chemical group 0.000 claims description 24
125000004104 aryloxy group Chemical group 0.000 claims description 24
125000004429 atom Chemical group 0.000 claims description 23
125000003282 alkyl amino group Chemical group 0.000 claims description 21
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 20
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
125000005553 heteroaryloxy group Chemical group 0.000 claims description 18
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 18
125000004434 sulfur atom Chemical group 0.000 claims description 18
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 17
125000005164 aryl thioalkyl group Chemical group 0.000 claims description 17
125000000232 haloalkynyl group Chemical group 0.000 claims description 17
125000005110 aryl thio group Chemical group 0.000 claims description 16
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 16
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
229910001868 water Inorganic materials 0.000 claims description 15
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 14
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
239000008157 edible vegetable oil Substances 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
235000019000 fluorine Nutrition 0.000 claims description 14
239000001087 glyceryl triacetate Substances 0.000 claims description 14
235000013773 glyceryl triacetate Nutrition 0.000 claims description 14
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
229960002622 triacetin Drugs 0.000 claims description 14
125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 13
125000005368 heteroarylthio group Chemical group 0.000 claims description 13
125000004468 heterocyclylthio group Chemical group 0.000 claims description 12
125000001145 hydrido group Chemical group *[H] 0.000 claims description 12
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 12
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 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
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 11
125000002837 carbocyclic group Chemical group 0.000 claims description 11
125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 11
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 10
125000005108 alkenylthio group Chemical group 0.000 claims description 10
125000005109 alkynylthio group Chemical group 0.000 claims description 10
125000005518 carboxamido group Chemical group 0.000 claims description 10
125000005216 haloheteroaryl group Chemical group 0.000 claims description 10
125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 10
229920000053 polysorbate 80 Polymers 0.000 claims description 10
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 8
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
239000004359 castor oil Substances 0.000 claims description 8
235000019438 castor oil Nutrition 0.000 claims description 8
125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
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 8
235000014113 dietary fatty acids Nutrition 0.000 claims description 8
239000000194 fatty acid Substances 0.000 claims description 8
229930195729 fatty acid Natural products 0.000 claims description 8
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 8
239000003112 inhibitor Substances 0.000 claims description 8
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 8
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 8
229940068968 polysorbate 80 Drugs 0.000 claims description 8
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
239000004698 Polyethylene Substances 0.000 claims description 7
229940116333 ethyl lactate Drugs 0.000 claims description 7
125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
229920000573 polyethylene Polymers 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
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000004450 alkenylene group Chemical group 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
150000003222 pyridines Chemical class 0.000 claims description 6
125000005353 silylalkyl group Chemical group 0.000 claims description 6
150000003536 tetrazoles Chemical group 0.000 claims description 6
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 5
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
125000002102 aryl alkyloxo group Chemical group 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
125000003003 spiro group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
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 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
125000006700 (C1-C6) alkylthio group Chemical group 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
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 4
125000001769 aryl amino group Chemical group 0.000 claims description 4
GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 claims description 4
GZVVNAWGGPWOOK-UHFFFAOYSA-N ethyl 2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)CC=CC2=C1 GZVVNAWGGPWOOK-UHFFFAOYSA-N 0.000 claims description 4
125000003106 haloaryl group Chemical group 0.000 claims description 4
125000005241 heteroarylamino group Chemical group 0.000 claims description 4
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
239000000126 substance Substances 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
125000006526 (C1-C2) alkyl group Chemical group 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
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
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
150000001204 N-oxides Chemical class 0.000 claims description 3
229920001213 Polysorbate 20 Polymers 0.000 claims description 3
229930003427 Vitamin E Natural products 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000005055 alkyl alkoxy group Chemical group 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 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
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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 3
TUPKOWFPVAXQFP-OFNKIYASSA-N propan-2-yl (2r,4s)-4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound CC(=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 TUPKOWFPVAXQFP-OFNKIYASSA-N 0.000 claims description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
235000019165 vitamin E Nutrition 0.000 claims description 3
239000011709 vitamin E Substances 0.000 claims description 3
229940046009 vitamin E Drugs 0.000 claims description 3
125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 2
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
ICRAPXISGUIWEQ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-pentadecyl-1h-1,2,4-triazole-3-thione Chemical compound S=C1NC(CCCCCCCCCCCCCCC)=NN1C1=CC=C(OC)C=C1 ICRAPXISGUIWEQ-UHFFFAOYSA-N 0.000 claims description 2
CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 claims description 2
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 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
BHIZVZJETFVJMJ-UHFFFAOYSA-N 2-hydroxypropyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)O BHIZVZJETFVJMJ-UHFFFAOYSA-N 0.000 claims description 2
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 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
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 description 2
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 claims description 2
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 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
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 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
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 claims description 2
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 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
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
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 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
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 description 2
KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-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
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 claims description 2
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 claims description 2
125000002373 5 membered heterocyclic 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
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
YURJTVFZVDRKSG-UHFFFAOYSA-N CC(C)CCC1(CCCCC1)C(NC(C=CC=C1)=C1SSNC(C1(CCC(C)C)CCCCC1)=O)=O Chemical compound CC(C)CCC1(CCCCC1)C(NC(C=CC=C1)=C1SSNC(C1(CCC(C)C)CCCCC1)=O)=O YURJTVFZVDRKSG-UHFFFAOYSA-N 0.000 claims description 2
OZCAQIJAKIDEGP-XIKOKIGWSA-N C[C@@H]1C[C@@H](C2=C(N1C(=O)O)C=C(C=C2)OC)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC Chemical compound C[C@@H]1C[C@@H](C2=C(N1C(=O)O)C=C(C=C2)OC)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC OZCAQIJAKIDEGP-XIKOKIGWSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-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
DTMOUJISRPBQGZ-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]methanol 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 DTMOUJISRPBQGZ-UHFFFAOYSA-N 0.000 claims description 2
LOTCVJJDZFMQGB-UHFFFAOYSA-N [N].[O].[S] Chemical group [N].[O].[S] LOTCVJJDZFMQGB-UHFFFAOYSA-N 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
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
125000005157 alkyl carboxy group Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000006319 alkynyl amino 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
125000005014 aminoalkynyl group Chemical group 0.000 claims description 2
125000005001 aminoaryl group Chemical group 0.000 claims description 2
125000005097 aminocarbonylalkyl 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
239000010477 apricot oil Substances 0.000 claims description 2
125000005333 aroyloxy group Chemical group 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
239000002285 corn oil Substances 0.000 claims description 2
235000005687 corn oil Nutrition 0.000 claims description 2
125000005366 cycloalkylthio 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
QCLAORQMXJANRH-KUHUBIRLSA-N ethyl (2r,4s)-4-[(3,5-dinitrophenyl)methyl-methoxycarbonylamino]-6,7-dimethoxy-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@@H](C)N(C2=CC(OC)=C(OC)C=C21)C(=O)OCC)CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 QCLAORQMXJANRH-KUHUBIRLSA-N 0.000 claims description 2
MXLOXILUGNJLGC-NQIIRXRSSA-N ethyl (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](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 MXLOXILUGNJLGC-NQIIRXRSSA-N 0.000 claims description 2
DNJMFCZWWVGPOM-XCLFUZPHSA-N ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-methyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@@H](C)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 DNJMFCZWWVGPOM-XCLFUZPHSA-N 0.000 claims description 2
YDYPPBOEOSFVMJ-QRQCRPRQSA-N ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-6-ethyl-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@@H](C)N(C2=CC=C(CC)C=C21)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YDYPPBOEOSFVMJ-QRQCRPRQSA-N 0.000 claims description 2
SADYHVWUBBDBHL-SZNDQCEHSA-N ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-6-methoxy-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@@H](C)N(C2=CC=C(OC)C=C21)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SADYHVWUBBDBHL-SZNDQCEHSA-N 0.000 claims description 2
GFDFJQTUTGZGHQ-YJYMSZOUSA-N ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-chloro-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound COC(=O)N([C@H]1C[C@@H](C)N(C2=CC(Cl)=CC=C21)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GFDFJQTUTGZGHQ-YJYMSZOUSA-N 0.000 claims description 2
ORGSRPIMIWRJBM-KNQAVFIVSA-N ethyl (2r,4s)-4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound CC(=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 ORGSRPIMIWRJBM-KNQAVFIVSA-N 0.000 claims description 2
BMGCDMZWMQQHMI-UHFFFAOYSA-N ethyl 2h-triazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNN=1 BMGCDMZWMQQHMI-UHFFFAOYSA-N 0.000 claims description 2
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 2
229940074046 glyceryl laurate Drugs 0.000 claims description 2
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
125000005226 heteroaryloxycarbonyl 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
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 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
125000005254 oxyacyl group Chemical group 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
229940113116 polyethylene glycol 1000 Drugs 0.000 claims description 2
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 description 2
CDLJRBVRQWDUIO-SZNDQCEHSA-N propan-2-yl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-methyl-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](C)C1)C(F)(F)F)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDLJRBVRQWDUIO-SZNDQCEHSA-N 0.000 claims description 2
YDDNDOKFOFRXJC-PEBXRYMYSA-N propan-2-yl (2r,4s)-4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-methyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound CC(=O)N([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 YDDNDOKFOFRXJC-PEBXRYMYSA-N 0.000 claims description 2
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 description 2
229940026235 propylene glycol monolaurate Drugs 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
239000012453 solvate Substances 0.000 claims description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
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 description 2
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 2
125000005106 triarylsilyl group Chemical group 0.000 claims description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
125000005429 oxyalkyl group Chemical group 0.000 claims 2
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 1
125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
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 1
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 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 claims 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 claims 1
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 1
KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 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
VTILWYBQQRECER-UHFFFAOYSA-N 5-sulfonylcyclohexa-1,3-diene Chemical class O=S(=O)=C1CC=CC=C1 VTILWYBQQRECER-UHFFFAOYSA-N 0.000 claims 1
XETDPUMMPYEMCF-ZMZPIMSZSA-N C[C@@H]1C[C@@H](C2=C(N1C(=O)O)C=CC(=C2)OC(F)(F)F)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC Chemical compound C[C@@H]1C[C@@H](C2=C(N1C(=O)O)C=CC(=C2)OC(F)(F)F)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC XETDPUMMPYEMCF-ZMZPIMSZSA-N 0.000 claims 1
101100512078 Caenorhabditis elegans lys-1 gene Proteins 0.000 claims 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 1
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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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- 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
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- 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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Biophysics (AREA)
Molecular Biology (AREA)
Dispersion Chemistry (AREA)
Emergency Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Diabetes (AREA)
Hematology (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Quinoline Compounds (AREA)
Pyridine Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Steroid Compounds (AREA)

BG108486A 2001-06-21 2003-12-22 Самоемулгиращи се препарати на инхибитори на протеин, пренасящ холестеролестер BG108486A (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US30002801P	2001-06-21	2001-06-21

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BG108486A true BG108486A (bg)	2005-03-31

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BG108486A BG108486A (bg)	2001-06-21	2003-12-22	Самоемулгиращи се препарати на инхибитори на протеин, пренасящ холестеролестер

Country Status (33)

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

Families Citing this family (76)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ512599A (en) *	1998-12-30	2003-10-31	Dexcel Ltd	Formulation for cyclosporin administration featuring a hydrophilic solvent and a surfactant with a HLB of less than 5
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
BR0307344A (pt)	2002-02-01	2004-12-14	Pfizer Prod Inc	Composições farmacêuticas de dispersões amorfas de fármacos e materiais formadores de microfase lipofìlica
CA2478433C (en) *	2002-03-01	2009-12-08	Cesi Chemical, A Flotek Company	Composition and process for well cleaning
US20040175341A1 (en) *	2003-03-04	2004-09-09	Manning Monna Marie	Microemulsion for cosmetic or pharmaceutical use containing an active ingredient
US7276536B2 (en)	2003-03-17	2007-10-02	Japan Tobacco Inc.	Method for increasing the bioavailability of the active form of S-[2-([[1-(2-ethylbutyl)cyclohexyl]carbonyl]amino) phenyl] 2-methylpropanethioate
ZA200508159B (en) *	2003-03-17	2007-03-28	Japan Tobacco Inc	Pharmaceutical compositions of CETP inhibitors
ATE534381T1 (de) *	2003-03-17	2011-12-15	Japan Tobacco Inc	Pharmazeutische cetp-inhibitor-zusammensetzungen
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
US7749992B2 (en) *	2003-10-08	2010-07-06	Eli Lilly And Company	Compounds and methods for treating dislipidemia
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
US8604055B2 (en)	2004-12-31	2013-12-10	Dr. Reddy's Laboratories Ltd.	Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors
CN103102303B (zh)	2004-12-31	2015-10-28	雷迪博士实验室有限公司	作为cetp抑制剂的苄胺衍生物
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
ATE516016T1 (de) *	2005-12-05	2011-07-15	Merck Sharp & Dohme	Selbstemulgierende formulierungen von cetp- hemmern
JP5844954B2 (ja) *	2005-12-31	2016-01-20	天士力製薬集団株式会社	アリタソウの抽出物を含有する医薬組成物、それらの製造方法
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
WO2010066593A1 (en) *	2008-12-08	2010-06-17	F. Hoffmann-La Roche Ag	Combined drug administration
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
KR20140037876A (ko) *	2011-05-20	2014-03-27	아벤티스 파마슈티칼스 인크.	펙소페나딘을 포함하는 약학적 조성물
JP5964965B2 (ja)	2011-08-18	2016-08-03	ドクターレディズラボラトリーズリミテッド	コレステリルエステル転送タンパク質（ｃｅｔｐ）インヒビターとしての置換複素環式アミン化合物
CN103958511A (zh)	2011-09-27	2014-07-30	雷迪博士实验室有限公司	作为胆固醇酯转移蛋白(CETP)抑制剂用于治疗动脉粥样硬化的5-苄基氨基甲基-6-氨基吡唑并[3,4-b]吡啶衍生物
EP2768486B1 (en) *	2011-10-21	2018-10-03	First Tech International Limited	Tocotrienol compositions
DK2838970T3 (en)	2012-04-15	2017-03-20	Flotek Chemistry Llc	Density formulations for foam filling
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
US9321955B2 (en)	2013-06-14	2016-04-26	Flotek Chemistry, Llc	Methods and compositions for stimulating the production of hydrocarbons from subterranean formations
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
US9464223B2 (en)	2013-03-14	2016-10-11	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
US11254856B2 (en)	2013-03-14	2022-02-22	Flotek Chemistry, Llc	Methods and compositions for use in oil and/or gas wells
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
US9868893B2 (en)	2013-03-14	2018-01-16	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
US10717919B2 (en)	2013-03-14	2020-07-21	Flotek Chemistry, Llc	Methods and compositions 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
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
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
US9428683B2 (en)	2013-03-14	2016-08-30	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
US10577531B2 (en)	2013-03-14	2020-03-03	Flotek Chemistry, Llc	Polymers and emulsions 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
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
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
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
CA2891278C (en)	2014-05-14	2018-11-06	Cesi Chemical, Inc.	Methods and compositions for use in oil and / or gas wells
US10294757B2 (en)	2014-07-28	2019-05-21	Flotek Chemistry, Llc	Methods and compositions related to gelled layers in oil and/or gas wells
WO2016071756A1 (en)	2014-11-04	2016-05-12	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
US9572819B2 (en)	2015-05-28	2017-02-21	Dr. Reddy's Laboratories, Ltd.	Oral composition of celecoxib for treatment of pain
EP3848026A1 (en)	2016-04-15	2021-07-14	Novira Therapeutics Inc.	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
WO2019108971A1 (en)	2017-12-01	2019-06-06	Flotek Chemistry, Llc	Methods and compositions for stimulating the production of hydrocarbons from subterranean formations
KR102833016B1 (ko)	2018-03-14	2025-07-14	칸디 테라퓨틱스 리미티드	이중 nk-1/nk-3 수용체 길항제를 포함하는 신규한 제약 제제
WO2019175657A1 (en)	2018-03-14	2019-09-19	Janssen Sciences Ireland Unlimited Company	Capsid assembly modulator dosing regimen
PL3886813T3 (pl) *	2018-11-26	2023-06-19	Hepion Pharmaceuticals, Inc.	Postacie farmaceutyczne analogów cyklosporyny
MX2021012356A (es)	2019-04-11	2021-11-04	Scherer Technologies Llc R P	Formulación para suministro oral de proteínas, péptidos y moléculas pequeñas con poca permeabilidad.
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
EP4267132A1 (en)	2020-12-28	2023-11-01	Dr. Reddy's Laboratories Ltd.	Celecoxib for treating pain
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
FI65914C (fi) *	1978-03-07	1984-08-10	Sandoz Ag	Foerfarande foer framstaellning av farmaceutiska kompositionerinnehaollande cyklosporin a
GB9208712D0 (en)	1992-04-22	1992-06-10	Sandoz Ltd	Pharmaceutical compositions containing cyclosporin derivates
AU2517095A (en)	1994-05-19	1995-12-18	R.P. Scherer International Corporation	Solutions of aryl or heteroaryl substituted alkanoic acids in lipophilic solvents and soft gelatin capsules containing such solutions
WO1996033697A1 (fr) *	1995-04-24	1996-10-31	Yissum Research Development Company Of The Hebrew University Of Jerusalem	Formulation auto-emulsionnable formant une emulsion huile dans l'eau
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
CZ292378B6 (cs)	1996-06-19	2003-09-17	Novartis Ag	Přípravek obsahující cyklosporin a způsob jeho přípravy
US5958876A (en) *	1996-06-19	1999-09-28	Novartis Ag	Cyclosporin-containing pharmaceutical compositions
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
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.
US6147090A (en) *	1998-09-17	2000-11-14	Pfizer Inc.	4-carboxyamino-2-methyl-1,2,3,4,-tetrahydroquinolines
JP2002525350A (ja) *	1998-09-25	2002-08-13	モンサントカンパニー	コレステロールエステル輸送タンパク質活性阻害に有効な置換されたｎ−脂肪族−ｎ−芳香族第三級ヘテロアルキルアミン
NZ512599A (en)	1998-12-30	2003-10-31	Dexcel Ltd	Formulation for cyclosporin administration featuring a hydrophilic solvent and a surfactant with a HLB of less than 5
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
EP1269994A3 (en) *	2001-06-22	2003-02-12	Pfizer Products Inc.	Pharmaceutical compositions comprising drug and concentration-enhancing polymers
CA2448864C (en) *	2001-06-22	2008-04-22	Pfizer Products Inc.	Pharmaceutical compositions containing a solid dispersion of a poorly-soluble drug in a matrix and a solubility-enhancing polymer
CA2450957A1 (en) *	2001-06-22	2003-01-03	Pfizer Products Inc.	Pharmaceutical compositions of dispersions of drugs and neutral polymers
JP2004534811A (ja) *	2001-06-22	2004-11-18	ファイザー・プロダクツ・インク	ポリマーと薬剤の集合体を含む医薬組成物
BR0307344A (pt) *	2002-02-01	2004-12-14	Pfizer Prod Inc	Composições farmacêuticas de dispersões amorfas de fármacos e materiais formadores de microfase lipofìlica
PL373914A1 (en) *	2002-02-01	2005-09-19	Pfizer Products Inc.	Immediate release dosage forms containing solid drug dispersions
KR20050088190A (ko) *	2002-12-20	2005-09-02	화이자 프로덕츠 인코포레이티드	콜레스테릴 에스터 전달 단백질 억제제 및 ｈｍｇ-ｃｏａ환원 효소 억제제를 포함하는 투약 형태
US20040132771A1 (en) *	2002-12-20	2004-07-08	Pfizer Inc	Compositions of choleseteryl ester transfer protein inhibitors and HMG-CoA reductase inhibitors

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Also Published As

Publication number	Publication date
EE200400024A (et)	2004-06-15
SV2003001103A (es)	2003-03-18
WO2003000295A2 (en)	2003-01-03
US6962931B2 (en)	2005-11-08
PE20030128A1 (es)	2003-02-28
UY27344A1 (es)	2003-01-31
CN1635911A (zh)	2005-07-06
AR034599A1 (es)	2004-03-03
IS7014A (is)	2003-10-31
MXPA04000014A (es)	2004-05-21
EA200301139A1 (ru)	2004-12-30
KR20040015746A (ko)	2004-02-19
CZ20033341A3 (cs)	2004-10-13
PL368850A1 (en)	2005-04-04
TNSN03139A1 (fr)	2005-12-23
HN2002000153A (es)	2002-11-05
NO20035632D0 (no)	2003-12-17
GT200200124A (es)	2003-09-22
HUP0400263A2 (hu)	2005-03-29
NO20035632L (no)	2004-02-18
SK15172003A3 (en)	2004-11-03
EP1453544A2 (en)	2004-09-08
JP2005500314A (ja)	2005-01-06
ZA200308561B (en)	2004-11-17
WO2003000295A3 (en)	2004-05-27
US20030022944A1 (en)	2003-01-30
IL158765A0 (en)	2004-05-12
CR7163A (es)	2004-02-23
AP2002002559A0 (en)	2002-06-30
BR0210505A (pt)	2004-05-18
MA27034A1 (fr)	2004-12-20
OA12619A (en)	2006-06-12
US20060014788A1 (en)	2006-01-19
CA2455288A1 (en)	2003-01-03
ECSP034875A (es)	2004-01-28
PA8548601A1 (es)	2003-09-05

Publication	Publication Date	Title
BG108486A (bg)	2005-03-31	Самоемулгиращи се препарати на инхибитори на протеин, пренасящ холестеролестер
US8197848B2 (en)	2012-06-12	Pharmaceutical compositions 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
EP1581210B1 (en)	2008-03-19	Dosage forms comprising a cetp inhibitor and an hmg-coa reductase inhibitor
US20050038007A1 (en)	2005-02-17	Dosage forms of cholesteryl ester transfer protein inhibitors and HMG-CoA reductase inhibitors
US20030170309A1 (en)	2003-09-11	Pharmaceutical compositions containing polymer and drug assemblies
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
KR20050025578A (ko)	2005-03-14	Ｃｅｔｐ 억제제 및 임의로 ｈｍｇｃｏａ 환원효소억제제 및(또는) 항고혈압제의 용도
KR20040011549A (ko)	2004-02-05	저용해도 및(또는) 산-민감성 약물 및 중화된 산성중합체를 포함하는 제약 조성물
WO2004056396A1 (en)	2004-07-08	DOSAGE FORMS OF CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITORS AND HMG-CoA REDUCTASE INHIBITORS WITH IMPROVED PERFORMANCE
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