SE462653B - Substituerade karbamider, foerfarande foer framstaellning daerav, naemnda karbamider foer farmaceutisk anvaendning samt farmaceutisk komposition innehaallande naemnda karbamider - Google Patents
Substituerade karbamider, foerfarande foer framstaellning daerav, naemnda karbamider foer farmaceutisk anvaendning samt farmaceutisk komposition innehaallande naemnda karbamiderInfo
- Publication number
- SE462653B SE462653B SE8300370A SE8300370A SE462653B SE 462653 B SE462653 B SE 462653B SE 8300370 A SE8300370 A SE 8300370A SE 8300370 A SE8300370 A SE 8300370A SE 462653 B SE462653 B SE 462653B
- Authority
- SE
- Sweden
- Prior art keywords
- urea
- benzyl
- butyl
- alkyl
- dimethylphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000003672 ureas Chemical class 0.000 title description 10
- -1 phenoxy, mercapto Chemical class 0.000 claims description 141
- 150000001875 compounds Chemical class 0.000 claims description 79
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 201000001320 Atherosclerosis Diseases 0.000 claims description 12
- 150000003335 secondary amines Chemical class 0.000 claims description 12
- 210000004204 blood vessel Anatomy 0.000 claims description 11
- 230000003902 lesion Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 230000003143 atherosclerotic effect Effects 0.000 claims description 7
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
- 150000001840 cholesterol esters Chemical class 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000006277 halobenzyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 2
- 101150084750 1 gene Proteins 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000003921 oil Substances 0.000 description 89
- 235000019198 oils Nutrition 0.000 description 89
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 46
- 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 46
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 235000013877 carbamide Nutrition 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000004202 carbamide Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 229920001971 elastomer Polymers 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 235000012000 cholesterol Nutrition 0.000 description 21
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000543 intermediate Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 235000005911 diet Nutrition 0.000 description 8
- 230000037213 diet Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- GKEHHLJOYZDXMI-UHFFFAOYSA-N (2,4-dimethylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C(C)=C1 GKEHHLJOYZDXMI-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229930182558 Sterol Natural products 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 5
- 150000003432 sterols Chemical class 0.000 description 5
- 235000003702 sterols Nutrition 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 4
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 4
- 239000004380 Cholic acid Substances 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 4
- 108010054082 Sterol O-acyltransferase Proteins 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 4
- 235000019416 cholic acid Nutrition 0.000 description 4
- 229960002471 cholic acid Drugs 0.000 description 4
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- DGWIPMVOWWLJMU-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-1-(2,4-dimethylphenyl)methanimine Chemical compound CC1=CC(C)=CC=C1C=NC1=CC=C(Cl)C=C1Cl DGWIPMVOWWLJMU-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- JKXLTTZJKQMKLA-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-chlorophenyl)-3-phenylurea Chemical compound C=1C=CC=CC=1N(C=1C=C(Cl)C=CC=1)C(=O)N(CCCC)CC1=CC=CC=C1 JKXLTTZJKQMKLA-UHFFFAOYSA-N 0.000 description 3
- JLKZDESEPHIECO-UHFFFAOYSA-N 2,4-dichloro-n-[(2,4-dimethylphenyl)methyl]aniline Chemical compound CC1=CC(C)=CC=C1CNC1=CC=C(Cl)C=C1Cl JLKZDESEPHIECO-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000035508 accumulation Effects 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 3
- 210000001367 artery Anatomy 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000001906 cholesterol absorption Effects 0.000 description 3
- 208000029078 coronary artery disease Diseases 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 208000031225 myocardial ischemia Diseases 0.000 description 3
- VLJJFRIHSLTXSI-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NCC=2C(=CC=CC=2)Cl)=C1 VLJJFRIHSLTXSI-UHFFFAOYSA-N 0.000 description 3
- PUEUFOKKVOOXEW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]butan-1-amine Chemical compound CCCCNCC1=CC=CC=C1Cl PUEUFOKKVOOXEW-UHFFFAOYSA-N 0.000 description 3
- IWFYZVFKBNNZHX-UHFFFAOYSA-N n-benzyl-n-butylcarbamoyl chloride Chemical compound CCCCN(C(Cl)=O)CC1=CC=CC=C1 IWFYZVFKBNNZHX-UHFFFAOYSA-N 0.000 description 3
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical class C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- YJCRBEVLZYABKY-UHFFFAOYSA-N 1-(furan-2-yl)-1-heptyl-3-(2,4,5-trimethylphenyl)urea Chemical compound C=1C=COC=1N(CCCCCCC)C(=O)NC1=CC(C)=C(C)C=C1C YJCRBEVLZYABKY-UHFFFAOYSA-N 0.000 description 2
- NTYXLLWDIQECGO-UHFFFAOYSA-N 1-(furan-2-yl)-1-heptyl-3-(2,4,6-trichlorophenyl)urea Chemical compound C=1C=COC=1N(CCCCCCC)C(=O)NC1=C(Cl)C=C(Cl)C=C1Cl NTYXLLWDIQECGO-UHFFFAOYSA-N 0.000 description 2
- PYEPKUCONNKFRK-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-1-heptyl-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)N(CCCCCCC)CC1=CC=C(OCCCC)C=C1 PYEPKUCONNKFRK-UHFFFAOYSA-N 0.000 description 2
- NVZUFXOWFUBQKJ-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-3-(2,4-difluorophenyl)-1-heptylurea Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CC1=CC=C(OCCCC)C=C1 NVZUFXOWFUBQKJ-UHFFFAOYSA-N 0.000 description 2
- YVEYRNZPUHVECU-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-3-(4-chloro-2-methylphenyl)-1-heptylurea Chemical compound C=1C=C(Cl)C=C(C)C=1NC(=O)N(CCCCCCC)CC1=CC=C(OCCCC)C=C1 YVEYRNZPUHVECU-UHFFFAOYSA-N 0.000 description 2
- KBPGXZOKJALMHF-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-3-[4-chloro-2-(trifluoromethyl)phenyl]-1-heptylurea Chemical compound C(CCCCCC)N(C(=O)NC1=C(C=C(C=C1)Cl)C(F)(F)F)CC1=CC=C(C=C1)OCCCC KBPGXZOKJALMHF-UHFFFAOYSA-N 0.000 description 2
- QDWYQFLKWCSOMI-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-1-heptyl-3-(2,4,5-trichlorophenyl)urea Chemical compound C=1C(Cl)=C(Cl)C=C(Cl)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 QDWYQFLKWCSOMI-UHFFFAOYSA-N 0.000 description 2
- PTGMAUVPFRYLJY-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-1-heptyl-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 PTGMAUVPFRYLJY-UHFFFAOYSA-N 0.000 description 2
- RIHOKGMNKUVAET-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-1-octadec-9-enyl-3-(2,4,5-trimethylphenyl)urea Chemical compound C(CCCCCCCC=CCCCCCCCC)N(C(=O)NC1=C(C=C(C(=C1)C)C)C)CC1=CC=C(C=C1)CCCC RIHOKGMNKUVAET-UHFFFAOYSA-N 0.000 description 2
- BQIRPLYKNRXSMI-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-3-(2,4-dichlorophenyl)-1-heptylurea Chemical compound C=1C=C(Cl)C=C(Cl)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 BQIRPLYKNRXSMI-UHFFFAOYSA-N 0.000 description 2
- SXQGNUGRBWBVOI-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-[4-chloro-2-(trifluoromethyl)phenyl]-1-(naphthalen-1-ylmethyl)urea Chemical compound ClC1=CC=C(CN(C(=O)NC2=C(C=C(C=C2)Cl)C(F)(F)F)CC2=CC=CC3=CC=CC=C23)C=C1 SXQGNUGRBWBVOI-UHFFFAOYSA-N 0.000 description 2
- BJHWYBZFDHPWAV-UHFFFAOYSA-N 1-benzyl-1-[(4-butoxyphenyl)methyl]-3-(2,4,5-trimethylphenyl)urea Chemical compound C1=CC(OCCCC)=CC=C1CN(C(=O)NC=1C(=CC(C)=C(C)C=1)C)CC1=CC=CC=C1 BJHWYBZFDHPWAV-UHFFFAOYSA-N 0.000 description 2
- BUMHDFJNNRIEDS-UHFFFAOYSA-N 1-benzyl-1-[(4-butoxyphenyl)methyl]-3-[4-chloro-2-(trifluoromethyl)phenyl]urea Chemical compound C(C1=CC=CC=C1)N(C(=O)NC1=C(C=C(C=C1)Cl)C(F)(F)F)CC1=CC=C(C=C1)OCCCC BUMHDFJNNRIEDS-UHFFFAOYSA-N 0.000 description 2
- ZSUBZLUMQRVHST-UHFFFAOYSA-N 1-benzyl-1-butyl-3,3-diphenylurea Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)N(CCCC)CC1=CC=CC=C1 ZSUBZLUMQRVHST-UHFFFAOYSA-N 0.000 description 2
- SXXGWNNIVJZDPD-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(2-methylphenyl)urea Chemical compound C=1C=CC=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 SXXGWNNIVJZDPD-UHFFFAOYSA-N 0.000 description 2
- YBJJTIBZTOKFLF-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-chloro-2-hydroxyphenyl)urea Chemical compound C=1C=CC(Cl)=C(O)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 YBJJTIBZTOKFLF-UHFFFAOYSA-N 0.000 description 2
- SAPLBENRNUWLDZ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-chlorophenyl)urea Chemical compound C=1C=CC(Cl)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 SAPLBENRNUWLDZ-UHFFFAOYSA-N 0.000 description 2
- XYSIADNGRMHABQ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 XYSIADNGRMHABQ-UHFFFAOYSA-N 0.000 description 2
- GCUUBNPJKKKFBD-UHFFFAOYSA-N 1-benzyl-3-(2,4-dimethylphenyl)-1-octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCN(CC1=CC=CC=C1)C(=O)NC1=C(C)C=C(C)C=C1 GCUUBNPJKKKFBD-UHFFFAOYSA-N 0.000 description 2
- FYJZIEOXIUJYPE-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-[(4-fluorophenyl)methyl]urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=C(F)C=C1 FYJZIEOXIUJYPE-UHFFFAOYSA-N 0.000 description 2
- QUOBVYPFBJUOAJ-UHFFFAOYSA-N 1-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1 QUOBVYPFBJUOAJ-UHFFFAOYSA-N 0.000 description 2
- GISVICWQYMUPJF-UHFFFAOYSA-N 2,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(C)=C1 GISVICWQYMUPJF-UHFFFAOYSA-N 0.000 description 2
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 2
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- LEGPZHPSIPPYIO-UHFFFAOYSA-N 3-Methoxyphenylacetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1 LEGPZHPSIPPYIO-UHFFFAOYSA-N 0.000 description 2
- OHHIBZKYXJDQEU-UHFFFAOYSA-N 3-chloro-n-phenylaniline Chemical compound ClC1=CC=CC(NC=2C=CC=CC=2)=C1 OHHIBZKYXJDQEU-UHFFFAOYSA-N 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SWMKYKLAXXADCY-UHFFFAOYSA-N 4-[[benzyl(butyl)carbamoyl]amino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 SWMKYKLAXXADCY-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- PERRBGDAOVSLIV-UHFFFAOYSA-N n-butyl-2-chlorobenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1Cl PERRBGDAOVSLIV-UHFFFAOYSA-N 0.000 description 2
- 230000004903 negative regulation of intestinal cholesterol absorption Effects 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- ODRCCNDEGWDDGA-UHFFFAOYSA-N phenyl n-(3-chlorophenyl)carbamate Chemical compound ClC1=CC=CC(NC(=O)OC=2C=CC=CC=2)=C1 ODRCCNDEGWDDGA-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DMSHKWHLXNDUST-UHFFFAOYSA-N (4-methylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C=C1 DMSHKWHLXNDUST-UHFFFAOYSA-N 0.000 description 1
- YDJQZYQGJJCDEA-UHFFFAOYSA-N 1,1-dibutyl-3-(2,4-dimethylphenyl)urea Chemical compound CCCCN(CCCC)C(=O)NC1=CC=C(C)C=C1C YDJQZYQGJJCDEA-UHFFFAOYSA-N 0.000 description 1
- XKAFKUGMXFMRCC-UHFFFAOYSA-N 1,1-diphenylurea Chemical compound C=1C=CC=CC=1N(C(=O)N)C1=CC=CC=C1 XKAFKUGMXFMRCC-UHFFFAOYSA-N 0.000 description 1
- NQYIWBNNPHOSSX-UHFFFAOYSA-N 1,3-dibenzyl-1-butyl-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=CC=CC=1CN(C=1C(=CC(C)=CC=1)C)C(=O)N(CCCC)CC1=CC=CC=C1 NQYIWBNNPHOSSX-UHFFFAOYSA-N 0.000 description 1
- WZCYLQNSCSKXFA-UHFFFAOYSA-N 1,3-dibenzyl-1-butyl-3-(3-nitrophenyl)urea Chemical compound C=1C=CC=CC=1CN(C=1C=C(C=CC=1)[N+]([O-])=O)C(=O)N(CCCC)CC1=CC=CC=C1 WZCYLQNSCSKXFA-UHFFFAOYSA-N 0.000 description 1
- WHHRTWFORQAQNP-UHFFFAOYSA-N 1,3-dibenzyl-1-butyl-3-phenylurea Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C(=O)N(CCCC)CC1=CC=CC=C1 WHHRTWFORQAQNP-UHFFFAOYSA-N 0.000 description 1
- XJTIVCLQTFHBDG-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)-1-butyl-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C2OCOC2=CC=1CN(CCCC)C(=O)NC1=CC=C(C)C=C1C XJTIVCLQTFHBDG-UHFFFAOYSA-N 0.000 description 1
- DEQVMPSQJBXWJG-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-1-heptyl-3-(2,4,5-trimethylphenyl)urea Chemical compound C=1C(C)=C(C)C=C(C)C=1NC(=O)N(CCCCCCC)CC1=CC=C(OCCCC)C=C1 DEQVMPSQJBXWJG-UHFFFAOYSA-N 0.000 description 1
- OFDKKNMPXBLFMN-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-1-heptyl-3-(2,4,6-trichlorophenyl)urea Chemical compound ClC=1C=C(Cl)C=C(Cl)C=1NC(=O)N(CCCCCCC)CC1=CC=C(OCCCC)C=C1 OFDKKNMPXBLFMN-UHFFFAOYSA-N 0.000 description 1
- BFOPLSIIQVFPGC-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-3-(2,4-dichlorophenyl)-1-heptylurea Chemical compound C=1C=C(Cl)C=C(Cl)C=1NC(=O)N(CCCCCCC)CC1=CC=C(OCCCC)C=C1 BFOPLSIIQVFPGC-UHFFFAOYSA-N 0.000 description 1
- YWIWLPCTXRTJHW-UHFFFAOYSA-N 1-[(4-butoxyphenyl)methyl]-3-(2,4-dimethylphenyl)-1-heptylurea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCCCCC)CC1=CC=C(OCCCC)C=C1 YWIWLPCTXRTJHW-UHFFFAOYSA-N 0.000 description 1
- WXIZNHAOABRKPH-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-1-heptyl-3-(2,4,6-trichlorophenyl)urea Chemical compound ClC=1C=C(Cl)C=C(Cl)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 WXIZNHAOABRKPH-UHFFFAOYSA-N 0.000 description 1
- YNYFIWZHVCWOQM-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-1-heptyl-3-(2-methylphenyl)urea Chemical compound C=1C=CC=C(C)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 YNYFIWZHVCWOQM-UHFFFAOYSA-N 0.000 description 1
- UGHXDJIFWDEVGF-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-1-heptyl-3-(3-methylphenyl)urea Chemical compound C=1C=CC(C)=CC=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 UGHXDJIFWDEVGF-UHFFFAOYSA-N 0.000 description 1
- RHZPLSCNTZDZFL-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-3-(2,4-difluorophenyl)-1-heptylurea Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 RHZPLSCNTZDZFL-UHFFFAOYSA-N 0.000 description 1
- LCVIPSFXSDQQON-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-3-(2,4-dimethylphenyl)-1-octadec-9-enylurea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCCCCCCC=CCCCCCCCC)CC1=CC=C(CCCC)C=C1 LCVIPSFXSDQQON-UHFFFAOYSA-N 0.000 description 1
- AZHKELKHBWQIMI-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-3-(4-chloro-2-methylphenyl)-1-heptylurea Chemical compound C=1C=C(Cl)C=C(C)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCCC)C=C1 AZHKELKHBWQIMI-UHFFFAOYSA-N 0.000 description 1
- FGSBERTZWTZVHB-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-3-(4-chloro-2-methylphenyl)urea Chemical compound C(CCC)C1=CC=C(CNC(=O)NC2=C(C=C(C=C2)Cl)C)C=C1 FGSBERTZWTZVHB-UHFFFAOYSA-N 0.000 description 1
- IJBHBTJBBNENLV-UHFFFAOYSA-N 1-[(4-butylphenyl)methyl]-3-[4-chloro-2-(trifluoromethyl)phenyl]-1-heptylurea Chemical compound C(CCCCCC)N(C(=O)NC1=C(C=C(C=C1)Cl)C(F)(F)F)CC1=CC=C(C=C1)CCCC IJBHBTJBBNENLV-UHFFFAOYSA-N 0.000 description 1
- YXCLZQGGADBQKE-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-1-(naphthalen-1-ylmethyl)-3-(2,4,5-trichlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C(=CC(Cl)=C(Cl)C=1)Cl)CC1=CC=CC2=CC=CC=C12 YXCLZQGGADBQKE-UHFFFAOYSA-N 0.000 description 1
- BDWAJHSDXIBOEN-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-1-(naphthalen-1-ylmethyl)-3-(2,4,6-trichlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C(=CC(Cl)=CC=1Cl)Cl)CC1=CC=CC2=CC=CC=C12 BDWAJHSDXIBOEN-UHFFFAOYSA-N 0.000 description 1
- AOVYPIGKUGUNGI-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-1-(naphthalen-1-ylmethyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound ClC1=CC=C(CN(C(=O)NC2=CC(=CC=C2)C(F)(F)F)CC2=CC=CC3=CC=CC=C23)C=C1 AOVYPIGKUGUNGI-UHFFFAOYSA-N 0.000 description 1
- BKOZZERQLGDVDM-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-(2,4-dichlorophenyl)-1-(naphthalen-1-ylmethyl)urea Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C(=CC(Cl)=CC=1)Cl)CC1=CC=CC2=CC=CC=C12 BKOZZERQLGDVDM-UHFFFAOYSA-N 0.000 description 1
- KIOZZICXWLXDJG-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-(2,4-difluorophenyl)-1-(naphthalen-1-ylmethyl)urea Chemical compound FC1=CC(F)=CC=C1NC(=O)N(CC=1C2=CC=CC=C2C=CC=1)CC1=CC=C(Cl)C=C1 KIOZZICXWLXDJG-UHFFFAOYSA-N 0.000 description 1
- HRMLUHNJIQPFJM-UHFFFAOYSA-N 1-[(4-pentoxyphenyl)methyl]-1-[(4-pentylphenyl)methyl]-3-(2,4,5-trichlorophenyl)urea Chemical compound C(CCCC)C1=CC=C(CN(C(=O)NC2=C(C=C(C(=C2)Cl)Cl)Cl)CC2=CC=C(C=C2)OCCCCC)C=C1 HRMLUHNJIQPFJM-UHFFFAOYSA-N 0.000 description 1
- WMLXRMRVZOULNK-UHFFFAOYSA-N 1-[(4-pentoxyphenyl)methyl]-1-[(4-pentylphenyl)methyl]-3-(2,4,6-trichlorophenyl)urea Chemical compound C(CCCC)C1=CC=C(CN(C(=O)NC2=C(C=C(C=C2Cl)Cl)Cl)CC2=CC=C(C=C2)OCCCCC)C=C1 WMLXRMRVZOULNK-UHFFFAOYSA-N 0.000 description 1
- XOKJHLYETJPJSR-UHFFFAOYSA-N 1-[(4-pentoxyphenyl)methyl]-1-[(4-pentylphenyl)methyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C(CCCC)C1=CC=C(CN(C(=O)NC2=CC(=CC=C2)C(F)(F)F)CC2=CC=C(C=C2)OCCCCC)C=C1 XOKJHLYETJPJSR-UHFFFAOYSA-N 0.000 description 1
- LAHFGCUHAIAAGH-UHFFFAOYSA-N 1-[2-(1,3-benzodioxol-5-yl)ethyl]-1-butyl-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C2OCOC2=CC=1CCN(CCCC)C(=O)NC1=CC=C(C)C=C1C LAHFGCUHAIAAGH-UHFFFAOYSA-N 0.000 description 1
- CTGNFOBBHRYUMV-UHFFFAOYSA-N 1-benzyl-1-[(4-butoxyphenyl)methyl]-3-(2,4,5-trichlorophenyl)urea Chemical compound C1=CC(OCCCC)=CC=C1CN(C(=O)NC=1C(=CC(Cl)=C(Cl)C=1)Cl)CC1=CC=CC=C1 CTGNFOBBHRYUMV-UHFFFAOYSA-N 0.000 description 1
- LPJWGEOWDOUIHJ-UHFFFAOYSA-N 1-benzyl-1-[(4-butoxyphenyl)methyl]-3-(2,4-dichlorophenyl)urea Chemical compound C1=CC(OCCCC)=CC=C1CN(C(=O)NC=1C(=CC(Cl)=CC=1)Cl)CC1=CC=CC=C1 LPJWGEOWDOUIHJ-UHFFFAOYSA-N 0.000 description 1
- ARNLGZUMKMBXDL-UHFFFAOYSA-N 1-benzyl-1-[(4-butoxyphenyl)methyl]-3-(2,4-dimethylphenyl)urea Chemical compound C1=CC(OCCCC)=CC=C1CN(C(=O)NC=1C(=CC(C)=CC=1)C)CC1=CC=CC=C1 ARNLGZUMKMBXDL-UHFFFAOYSA-N 0.000 description 1
- JXJKOOUNIHTFDJ-UHFFFAOYSA-N 1-benzyl-1-[(4-butylphenyl)methyl]-3-(2,4,5-trimethylphenyl)urea Chemical compound C1=CC(CCCC)=CC=C1CN(C(=O)NC=1C(=CC(C)=C(C)C=1)C)CC1=CC=CC=C1 JXJKOOUNIHTFDJ-UHFFFAOYSA-N 0.000 description 1
- UGBXFKYWIOASDR-UHFFFAOYSA-N 1-benzyl-1-[2-phenyl-1-(4-phenylmethoxyphenyl)ethyl]-3-(2,4,6-trichlorophenyl)urea Chemical compound C(C1=CC=CC=C1)N(C(=O)NC1=C(C=C(C=C1Cl)Cl)Cl)C(CC1=CC=CC=C1)C1=CC=C(C=C1)OCC1=CC=CC=C1 UGBXFKYWIOASDR-UHFFFAOYSA-N 0.000 description 1
- JOUBLGWLPRKRPX-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(2,3-dimethylphenyl)urea Chemical compound C=1C=CC(C)=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 JOUBLGWLPRKRPX-UHFFFAOYSA-N 0.000 description 1
- CQCRPHVZWXLSLZ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 CQCRPHVZWXLSLZ-UHFFFAOYSA-N 0.000 description 1
- UAMMZAIIPBUZOS-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(2,6-dimethylphenyl)urea Chemical compound CC=1C=CC=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 UAMMZAIIPBUZOS-UHFFFAOYSA-N 0.000 description 1
- RTSCWIYJSUSUQX-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C(C)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 RTSCWIYJSUSUQX-UHFFFAOYSA-N 0.000 description 1
- AGYWMLJGOQMPDZ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3,5-dichlorophenyl)urea Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 AGYWMLJGOQMPDZ-UHFFFAOYSA-N 0.000 description 1
- RBQXUXOVVFMJTC-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3,5-dimethylphenyl)urea Chemical compound C=1C(C)=CC(C)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 RBQXUXOVVFMJTC-UHFFFAOYSA-N 0.000 description 1
- RKVHAWULYXIBGC-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-chloro-2-methoxyphenyl)urea Chemical compound C=1C=CC(Cl)=C(OC)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 RKVHAWULYXIBGC-UHFFFAOYSA-N 0.000 description 1
- COJMLDQLJWCYDJ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-chloro-4-methoxyphenyl)urea Chemical compound C=1C=C(OC)C(Cl)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 COJMLDQLJWCYDJ-UHFFFAOYSA-N 0.000 description 1
- DQKVOIDAPGJUPB-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-chloro-4-methylphenyl)urea Chemical compound C=1C=C(C)C(Cl)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 DQKVOIDAPGJUPB-UHFFFAOYSA-N 0.000 description 1
- QUMQURXEFSSGLJ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-methylphenyl)urea Chemical compound C=1C=CC(C)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 QUMQURXEFSSGLJ-UHFFFAOYSA-N 0.000 description 1
- OPXRPBOSFMMZMA-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(4-methylphenyl)urea Chemical compound C=1C=C(C)C=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 OPXRPBOSFMMZMA-UHFFFAOYSA-N 0.000 description 1
- USEVEOOSQPJQBZ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(5-chloro-2-methoxyphenyl)urea Chemical compound C=1C(Cl)=CC=C(OC)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 USEVEOOSQPJQBZ-UHFFFAOYSA-N 0.000 description 1
- IFGCEVZHQPZOMQ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 IFGCEVZHQPZOMQ-UHFFFAOYSA-N 0.000 description 1
- HUVBFGMXRUTCKD-UHFFFAOYSA-N 1-benzyl-3-(2,4-dimethylphenyl)-1-(1,2-diphenylethyl)urea Chemical compound CC1=CC(C)=CC=C1NC(=O)N(C(CC=1C=CC=CC=1)C=1C=CC=CC=1)CC1=CC=CC=C1 HUVBFGMXRUTCKD-UHFFFAOYSA-N 0.000 description 1
- FQTBKJYANOAGHM-UHFFFAOYSA-N 1-benzyl-3-(2,4-dimethylphenyl)-1-hexylurea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCCCC)CC1=CC=CC=C1 FQTBKJYANOAGHM-UHFFFAOYSA-N 0.000 description 1
- DYJLMLFHUUAPES-UHFFFAOYSA-N 1-benzyl-3-(2,4-dimethylphenyl)-1-octylurea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCCCCCC)CC1=CC=CC=C1 DYJLMLFHUUAPES-UHFFFAOYSA-N 0.000 description 1
- SHUQJLWCMWDDQD-UHFFFAOYSA-N 1-benzyl-3-(2,4-dimethylphenyl)-1-pentylurea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCCC)CC1=CC=CC=C1 SHUQJLWCMWDDQD-UHFFFAOYSA-N 0.000 description 1
- LHUQCCGZYKUVEH-UHFFFAOYSA-N 1-benzyl-3-(2,4-dimethylphenyl)-1-tetradecylurea Chemical compound CCCCCCCCCCCCCCN(CC1=CC=CC=C1)C(=O)NC1=C(C)C=C(C)C=C1 LHUQCCGZYKUVEH-UHFFFAOYSA-N 0.000 description 1
- JVNRLCNTRINRBJ-UHFFFAOYSA-N 1-benzyl-3-(2,4-dimethylphenyl)-1-undecylurea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCCCCCCCCC)CC1=CC=CC=C1 JVNRLCNTRINRBJ-UHFFFAOYSA-N 0.000 description 1
- UVUVZVGVIABZQO-UHFFFAOYSA-N 1-butyl-1-(4-cyclohexylbutyl)-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CCCCC1CCCCC1 UVUVZVGVIABZQO-UHFFFAOYSA-N 0.000 description 1
- ZJMVEDDANFALOY-UHFFFAOYSA-N 1-butyl-1-[(2-chlorophenyl)methyl]-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1Cl ZJMVEDDANFALOY-UHFFFAOYSA-N 0.000 description 1
- ONJZIBXDHVUTBK-UHFFFAOYSA-N 1-butyl-1-[(3,4-dichlorophenyl)methyl]-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=C(Cl)C(Cl)=C1 ONJZIBXDHVUTBK-UHFFFAOYSA-N 0.000 description 1
- IFNCOAFUGZBNBC-UHFFFAOYSA-N 1-butyl-1-[(3-chlorophenyl)methyl]-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC(Cl)=C1 IFNCOAFUGZBNBC-UHFFFAOYSA-N 0.000 description 1
- RTNORZQKLFLYFM-UHFFFAOYSA-N 1-butyl-1-[(4-chlorophenyl)methyl]-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=C(Cl)C=C1 RTNORZQKLFLYFM-UHFFFAOYSA-N 0.000 description 1
- NRSZJSHXROTIHT-UHFFFAOYSA-N 1-butyl-1-[(4-heptoxyphenyl)methyl]-3-(2,4,6-trimethylphenyl)urea Chemical compound C1=CC(OCCCCCCC)=CC=C1CN(CCCC)C(=O)NC1=C(C)C=C(C)C=C1C NRSZJSHXROTIHT-UHFFFAOYSA-N 0.000 description 1
- ILPZOQQNYBZHOR-UHFFFAOYSA-N 1-butyl-1-[(4-hexoxyphenyl)methyl]-3-(2,4,6-trimethylphenyl)urea Chemical compound C1=CC(OCCCCCC)=CC=C1CN(CCCC)C(=O)NC1=C(C)C=C(C)C=C1C ILPZOQQNYBZHOR-UHFFFAOYSA-N 0.000 description 1
- YLSLZIODJLABEP-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-(2-phenylethyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CCC1=CC=CC=C1 YLSLZIODJLABEP-UHFFFAOYSA-N 0.000 description 1
- LBJDFZRRSJCULH-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-(3,3-diphenylpropyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 LBJDFZRRSJCULH-UHFFFAOYSA-N 0.000 description 1
- UTBOJIIXRHLWQK-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-[(2-fluorophenyl)methyl]urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1F UTBOJIIXRHLWQK-UHFFFAOYSA-N 0.000 description 1
- ZADGHJDMTWLDJM-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-[(4-methoxyphenyl)methyl]urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=C(OC)C=C1 ZADGHJDMTWLDJM-UHFFFAOYSA-N 0.000 description 1
- ZGBBSERQQNWUKG-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-[(4-methylphenyl)methyl]urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=C(C)C=C1 ZGBBSERQQNWUKG-UHFFFAOYSA-N 0.000 description 1
- WLVVRNRBOFFHAN-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-[(4-methylsulfanylphenyl)methyl]urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=C(SC)C=C1 WLVVRNRBOFFHAN-UHFFFAOYSA-N 0.000 description 1
- JWNGKCAASIFIBY-UHFFFAOYSA-N 1-butyl-3-(2,4-dimethylphenyl)-1-[[4-(trifluoromethyl)phenyl]methyl]urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=C(C(F)(F)F)C=C1 JWNGKCAASIFIBY-UHFFFAOYSA-N 0.000 description 1
- IJOHWWSJWPVBBZ-UHFFFAOYSA-N 1-heptyl-1-(2-phenylethyl)-3-(2,4,5-trichlorophenyl)urea Chemical compound C=1C(Cl)=C(Cl)C=C(Cl)C=1NC(=O)N(CCCCCCC)CCC1=CC=CC=C1 IJOHWWSJWPVBBZ-UHFFFAOYSA-N 0.000 description 1
- QPDUGXKFHNQTOI-UHFFFAOYSA-N 1-heptyl-1-(2-phenylethyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)N(CCCCCCC)CCC1=CC=CC=C1 QPDUGXKFHNQTOI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- VBHCHHNMWNQQRB-UHFFFAOYSA-N 1-phenyl-n-(2,4,6-trimethylphenyl)methanimine Chemical compound CC1=CC(C)=CC(C)=C1N=CC1=CC=CC=C1 VBHCHHNMWNQQRB-UHFFFAOYSA-N 0.000 description 1
- HJWYDVJKSDHDSL-UHFFFAOYSA-N 2,4-dichloro-n-[(2,4-dichlorophenyl)methyl]aniline Chemical compound ClC1=CC(Cl)=CC=C1CNC1=CC=C(Cl)C=C1Cl HJWYDVJKSDHDSL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QJLOCCVVLZHSDX-UHFFFAOYSA-N 2-chloro-n-[(2-chlorophenyl)methyl]aniline Chemical compound ClC1=CC=CC=C1CNC1=CC=CC=C1Cl QJLOCCVVLZHSDX-UHFFFAOYSA-N 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- YPWJMCVFKRDPCA-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-[(4-pentoxyphenyl)methyl]-1-[(4-pentylphenyl)methyl]urea Chemical compound C(CCCC)C1=CC=C(CN(C(=O)NC2=C(C=C(C=C2)Cl)Cl)CC2=CC=C(C=C2)OCCCCC)C=C1 YPWJMCVFKRDPCA-UHFFFAOYSA-N 0.000 description 1
- NNAQFLKCVHUNDF-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-heptyl-1-(2-phenylethyl)urea Chemical compound C=1C=C(Cl)C=C(Cl)C=1NC(=O)N(CCCCCCC)CCC1=CC=CC=C1 NNAQFLKCVHUNDF-UHFFFAOYSA-N 0.000 description 1
- IWFVKXFVJZKUCL-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-[(4-pentoxyphenyl)methyl]-1-[(4-pentylphenyl)methyl]urea Chemical compound C(CCCC)C1=CC=C(CN(C(=O)NC2=C(C=C(C=C2)F)F)CC2=CC=C(C=C2)OCCCCC)C=C1 IWFVKXFVJZKUCL-UHFFFAOYSA-N 0.000 description 1
- ULJCCRYFVUPXEC-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-heptyl-1-(2-phenylethyl)urea Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CCC1=CC=CC=C1 ULJCCRYFVUPXEC-UHFFFAOYSA-N 0.000 description 1
- HYYVICZAAUCPOD-UHFFFAOYSA-N 3-(2,4-dimethylphenyl)-1-(3,3-diphenylpropyl)-1-[(4-fluorophenyl)methyl]urea Chemical compound CC1=CC(C)=CC=C1NC(=O)N(CC=1C=CC(F)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 HYYVICZAAUCPOD-UHFFFAOYSA-N 0.000 description 1
- OAZCCRLKKRZGEC-UHFFFAOYSA-N 3-(2,4-dimethylphenyl)-1-[(2-fluorophenyl)methyl]-1-[(2-methoxyphenyl)methyl]urea Chemical compound COC1=CC=CC=C1CN(C(=O)NC=1C(=CC(C)=CC=1)C)CC1=CC=CC=C1F OAZCCRLKKRZGEC-UHFFFAOYSA-N 0.000 description 1
- HWQPTLQLYWWQJV-UHFFFAOYSA-N 3-(2,4-dimethylphenyl)-1-heptyl-1-(2-phenylethyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCCCCC)CCC1=CC=CC=C1 HWQPTLQLYWWQJV-UHFFFAOYSA-N 0.000 description 1
- GYENWNHQIAPFFZ-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-1-[(4-pentoxyphenyl)methyl]-1-[(4-pentylphenyl)methyl]urea Chemical compound C(CCCC)C1=CC=C(CN(C(=O)NC2=C(C=C(C=C2)Cl)C)CC2=CC=C(C=C2)OCCCCC)C=C1 GYENWNHQIAPFFZ-UHFFFAOYSA-N 0.000 description 1
- YLFZMCLAZHQPFN-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-1-heptyl-1-(2-phenylethyl)urea Chemical compound C=1C=C(Cl)C=C(C)C=1NC(=O)N(CCCCCCC)CCC1=CC=CC=C1 YLFZMCLAZHQPFN-UHFFFAOYSA-N 0.000 description 1
- RHUYZIMLUSAPJY-UHFFFAOYSA-N 3-[4-chloro-2-(trifluoromethyl)phenyl]-1-[(4-pentoxyphenyl)methyl]-1-[(4-pentylphenyl)methyl]urea Chemical compound C(CCCC)C1=CC=C(CN(C(=O)NC2=C(C=C(C=C2)Cl)C(F)(F)F)CC2=CC=C(C=C2)OCCCCC)C=C1 RHUYZIMLUSAPJY-UHFFFAOYSA-N 0.000 description 1
- XOQDDGZBISVUIH-UHFFFAOYSA-N 3-[4-chloro-2-(trifluoromethyl)phenyl]-1-heptyl-1-(2-phenylethyl)urea Chemical compound C=1C=C(Cl)C=C(C(F)(F)F)C=1NC(=O)N(CCCCCCC)CCC1=CC=CC=C1 XOQDDGZBISVUIH-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- ODZRBTUVRQUISV-UHFFFAOYSA-N 3-chloro-4-methyl-n-[(4-methylphenyl)methyl]aniline Chemical compound C1=CC(C)=CC=C1CNC1=CC=C(C)C(Cl)=C1 ODZRBTUVRQUISV-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- HOVRQUHNZHBKKJ-UHFFFAOYSA-N 4-(carbamoylamino)benzoic acid Chemical compound NC(=O)NC1=CC=C(C(O)=O)C=C1 HOVRQUHNZHBKKJ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- JEZWNFUVMREVTR-UHFFFAOYSA-N 4-methyl-n-[(4-methylphenyl)methyl]aniline Chemical compound C1=CC(C)=CC=C1CNC1=CC=C(C)C=C1 JEZWNFUVMREVTR-UHFFFAOYSA-N 0.000 description 1
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- 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 1
- 101100011961 Caenorhabditis elegans ess-2 gene Proteins 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BDCFUHIWJODVNG-UHFFFAOYSA-N Desmosterol Natural products C1C=C2CC(O)C=CC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 BDCFUHIWJODVNG-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- AVSXSVCZWQODGV-DPAQBDIFSA-N desmosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC=C(C)C)C)[C@@]1(C)CC2 AVSXSVCZWQODGV-DPAQBDIFSA-N 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- HLVGAFHZUPLCML-UHFFFAOYSA-N ethyl 4-(carbamoylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(NC(N)=O)C=C1 HLVGAFHZUPLCML-UHFFFAOYSA-N 0.000 description 1
- DFMPHIVKZAUXOK-UHFFFAOYSA-N ethyl 4-[[benzyl(butyl)carbamoyl]amino]benzoate Chemical compound C=1C=C(C(=O)OCC)C=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 DFMPHIVKZAUXOK-UHFFFAOYSA-N 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002185 fatty acyl-CoAs Chemical class 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 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 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000006372 lipid accumulation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- RRFPPNUZXMNIBU-UHFFFAOYSA-N n,1-bis(2,4-dichlorophenyl)methanimine Chemical compound ClC1=CC(Cl)=CC=C1C=NC1=CC=C(Cl)C=C1Cl RRFPPNUZXMNIBU-UHFFFAOYSA-N 0.000 description 1
- FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 description 1
- CCUWEZJBHOXLPA-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-1-phenylmethanimine Chemical compound CC1=CC(C)=CC=C1N=CC1=CC=CC=C1 CCUWEZJBHOXLPA-UHFFFAOYSA-N 0.000 description 1
- BYMDTJKFACBBBD-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-1-(4-methylphenyl)methanimine Chemical compound C1=CC(C)=CC=C1C=NC1=CC=C(C)C(Cl)=C1 BYMDTJKFACBBBD-UHFFFAOYSA-N 0.000 description 1
- VVUAADACTIQHDR-UHFFFAOYSA-N n-(3-chlorophenyl)-n-phenylcarbamoyl chloride Chemical compound C=1C=CC(Cl)=CC=1N(C(=O)Cl)C1=CC=CC=C1 VVUAADACTIQHDR-UHFFFAOYSA-N 0.000 description 1
- HFGFPUPROHHWFT-UHFFFAOYSA-N n-(3-nitrophenyl)-1-phenylmethanimine Chemical compound [O-][N+](=O)C1=CC=CC(N=CC=2C=CC=CC=2)=C1 HFGFPUPROHHWFT-UHFFFAOYSA-N 0.000 description 1
- WWIIUZRDEYPOAR-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)methyl]-2,4-dimethylaniline Chemical compound CC1=CC(C)=CC=C1NCC1=CC=C(Cl)C=C1Cl WWIIUZRDEYPOAR-UHFFFAOYSA-N 0.000 description 1
- YSEGFBXNCKAPKQ-UHFFFAOYSA-N n-[(2,4-dimethylphenyl)methyl]-2,4-dimethylaniline Chemical compound CC1=CC(C)=CC=C1CNC1=CC=C(C)C=C1C YSEGFBXNCKAPKQ-UHFFFAOYSA-N 0.000 description 1
- WFKMKLYNZWOGGA-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]-1-phenylmethanimine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(N=CC=2C=CC=CC=2)=C1 WFKMKLYNZWOGGA-UHFFFAOYSA-N 0.000 description 1
- LRIYKLNPLHUXOO-UHFFFAOYSA-N n-[3-[benzyl-[benzyl(butyl)carbamoyl]amino]phenyl]acetamide Chemical compound C=1C=CC=CC=1CN(C=1C=C(NC(C)=O)C=CC=1)C(=O)N(CCCC)CC1=CC=CC=C1 LRIYKLNPLHUXOO-UHFFFAOYSA-N 0.000 description 1
- JMUDYTLZQVUDLG-UHFFFAOYSA-N n-benzyl-2,4,6-trimethylaniline Chemical compound CC1=CC(C)=CC(C)=C1NCC1=CC=CC=C1 JMUDYTLZQVUDLG-UHFFFAOYSA-N 0.000 description 1
- CIOZTNUIZOLRED-UHFFFAOYSA-N n-benzyl-2,4-dichloroaniline Chemical compound ClC1=CC(Cl)=CC=C1NCC1=CC=CC=C1 CIOZTNUIZOLRED-UHFFFAOYSA-N 0.000 description 1
- QFTNTXCQGYYIEJ-UHFFFAOYSA-N n-benzyl-3,5-bis(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NCC=2C=CC=CC=2)=C1 QFTNTXCQGYYIEJ-UHFFFAOYSA-N 0.000 description 1
- OVZNWAWUJPSLHM-UHFFFAOYSA-N n-benzyl-3-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC(NCC=2C=CC=CC=2)=C1 OVZNWAWUJPSLHM-UHFFFAOYSA-N 0.000 description 1
- MMEIYVXPSXIGET-UHFFFAOYSA-N n-benzyl-4-chloroaniline Chemical compound C1=CC(Cl)=CC=C1NCC1=CC=CC=C1 MMEIYVXPSXIGET-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- MRSYBIDUQWAWBO-UHFFFAOYSA-N naphthalen-2-ylurea Chemical compound C1=CC=CC2=CC(NC(=O)N)=CC=C21 MRSYBIDUQWAWBO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000021195 test diet Nutrition 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/342,698 US4387105A (en) | 1982-01-26 | 1982-01-26 | Methods of treating atherosclerosis with dialkylureas and dialkylthioureas |
| US06/342,693 US4473579A (en) | 1982-01-26 | 1982-01-26 | Antiatherosclerotic tetrasubstituted ureas and thioureas |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8300370D0 SE8300370D0 (sv) | 1983-01-25 |
| SE8300370L SE8300370L (sv) | 1983-07-27 |
| SE462653B true SE462653B (sv) | 1990-08-06 |
Family
ID=26993144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8300370A SE462653B (sv) | 1982-01-26 | 1983-01-25 | Substituerade karbamider, foerfarande foer framstaellning daerav, naemnda karbamider foer farmaceutisk anvaendning samt farmaceutisk komposition innehaallande naemnda karbamider |
Country Status (20)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2138804A (en) * | 1983-04-27 | 1984-10-31 | Sumitomo Chemical Co | Fungicidal N-phenylcarbamates |
| GB2149394B (en) * | 1983-07-19 | 1986-09-24 | American Cyanamid Co | Ureas |
| US4818899A (en) * | 1986-12-03 | 1989-04-04 | Minnesota Mining And Manufacturing Company | Second harmonic generation by carbamic acid derivatives |
| EP0344425B1 (en) * | 1988-03-30 | 1993-12-08 | Warner-Lambert Company | N-[[(2,6-disubstituted)phenyl]-N'- arylalkyl] ureas as antihypercholesterolemic and antiatherosclerotic agents |
| US5116848A (en) * | 1988-03-30 | 1992-05-26 | Warner-Lambert Company | N-(((2,6-disubstituted)phenyl)-n-diarylalkyl)ureas as antihyperlipidemic and antiatherosclerotic agents |
| EP0515684A4 (en) * | 1990-02-14 | 1993-04-21 | Chugai Seiyaku Kabushiki Kaisha | Inhibitor of denatured ldl formation |
| US5668136A (en) * | 1990-09-25 | 1997-09-16 | Eisai Co., Ltd. | Trisubstituted benzene derivatives, composition and methods of treatment |
| HUT62558A (en) * | 1991-07-01 | 1993-05-28 | Sandoz Ag | Process for producing n-phenylthiourea derivaties and pharmaceutical compositions comprising same |
| CA2115915A1 (en) * | 1992-07-20 | 1994-02-03 | Kenji Hayashi | Benzene derivatives |
| AU8534198A (en) * | 1997-08-05 | 1999-03-01 | Novo Nordisk A/S | Derivatives of 2,5- and 3,5-disubstituted anilines, their preparation and use |
| TW415942B (en) * | 1997-09-03 | 2000-12-21 | American Home Prod | Novel substituted 1-aryl-3-heteroaryl-thioureas and substituted 1-aryl-3-heteroaryl-isothioureas as antiatherosclerotic agents |
| US6455566B1 (en) | 1997-09-03 | 2002-09-24 | Wyeth | Substituted 1-aryl-3-heteroaryl-thioureas (or isothioureas) as antiatherosclerotic agents |
| WO1999037604A2 (en) * | 1998-01-21 | 1999-07-29 | Zymogenetics, Inc. | Dialkyl ureas as calcitonin mimetics |
| CA2692598A1 (en) * | 2007-07-10 | 2009-01-15 | Amgen Inc. | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL92838C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1949-12-06 | |||
| US2688039A (en) * | 1952-02-08 | 1954-08-31 | Ciba Pharm Prod Inc | Halogen-containing di-(substituted phenyl)-thioureas |
| US3326663A (en) * | 1964-09-25 | 1967-06-20 | Shell Oil Co | Herbicidal phenylureas |
| US3335142A (en) * | 1965-07-07 | 1967-08-08 | American Cyanamid Co | Process for the preparation of n, n'-disubstituted ureas |
| US3659012A (en) * | 1969-05-26 | 1972-04-25 | Lilly Co Eli | Methods of treating helminth infections with thiourea derivatives |
| US3728386A (en) * | 1970-07-27 | 1973-04-17 | Exxon Research Engineering Co | N-cycloalkylalkyl and n-cycloalkyl substituted phenyl ureas and halo acetamides |
| US3928437A (en) * | 1970-09-02 | 1975-12-23 | Ciba Geigy Corp | Phenoxy-phenyl, phenylthiophenyl, phenylsulfonylphenyl and phenylaminophenyl diaminothioureas |
| US3856952A (en) * | 1973-03-01 | 1974-12-24 | Pennwalt Corp | Synergistic antimicrobial compositions employing certain n-(phenyl-carbamyl)amino-benzene sulfonyl flourides |
| US3903130A (en) * | 1974-05-03 | 1975-09-02 | Stauffer Chemical Co | 1-Trifluormethylphenyl-3-dicyanophenyl urea |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
-
1982
- 1982-12-05 IL IL67417A patent/IL67417A/xx not_active IP Right Cessation
- 1982-12-22 DE DE19823247581 patent/DE3247581A1/de not_active Withdrawn
- 1982-12-28 KR KR8205843A patent/KR890001808B1/ko not_active Expired
-
1983
- 1983-01-14 GR GR70261A patent/GR77186B/el unknown
- 1983-01-21 AU AU10681/83A patent/AU562699B2/en not_active Ceased
- 1983-01-24 GB GB08301863A patent/GB2113684B/en not_active Expired
- 1983-01-25 NL NL8300269A patent/NL8300269A/nl not_active Application Discontinuation
- 1983-01-25 IE IE146/83A patent/IE54683B1/en not_active IP Right Cessation
- 1983-01-25 DK DK028683A patent/DK160869C/da not_active IP Right Cessation
- 1983-01-25 PT PT76138A patent/PT76138A/pt not_active IP Right Cessation
- 1983-01-25 PL PL1983240284A patent/PL143836B1/pl unknown
- 1983-01-25 SE SE8300370A patent/SE462653B/sv not_active IP Right Cessation
- 1983-01-25 NO NO830238A patent/NO158417C/no unknown
- 1983-01-25 FI FI830247A patent/FI85013C/fi not_active IP Right Cessation
- 1983-01-25 CH CH404/83A patent/CH654571A5/de not_active IP Right Cessation
- 1983-01-25 ES ES519246A patent/ES519246A0/es active Granted
- 1983-01-25 HU HU83227A patent/HU200746B/hu not_active IP Right Cessation
- 1983-01-25 AT AT0023983A patent/AT391313B/de not_active IP Right Cessation
- 1983-01-25 FR FR8301082A patent/FR2521134B1/fr not_active Expired
- 1983-01-25 IT IT47605/83A patent/IT1203647B/it active
-
1984
- 1984-04-11 ES ES531508A patent/ES531508A0/es active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4473579A (en) | Antiatherosclerotic tetrasubstituted ureas and thioureas | |
| US4387106A (en) | Method of treating atherosclerosis with di(aralkyl)ureas and di(aralkyl)thioureas | |
| US4387105A (en) | Methods of treating atherosclerosis with dialkylureas and dialkylthioureas | |
| SE462653B (sv) | Substituerade karbamider, foerfarande foer framstaellning daerav, naemnda karbamider foer farmaceutisk anvaendning samt farmaceutisk komposition innehaallande naemnda karbamider | |
| EP0416609B1 (en) | Benzo[b]thiophene-containing lipoxygenase-inhibiting compounds | |
| US5612377A (en) | Method of inhibiting leukotriene biosynthesis | |
| PL117551B1 (en) | Process for preparing novel,optically active phenethanoloaminesaminov | |
| US6215001B1 (en) | Imidazole derivatives as therapeutic agents | |
| US4397868A (en) | Method of treating atherosclerosis with trisubstituted ureas | |
| CS655889A3 (en) | Anti-atherosclerotic active compounds, pharmaceuticals containing suchcompounds and process for preparing thereof | |
| DE2417216A1 (de) | Fungizide | |
| US5003106A (en) | Antiatherosclerotic ureas and thioureas | |
| CA1239150A (en) | Anti-atherosclerotic trisubstituted ureas | |
| US5084457A (en) | Benzoylaminoquinazolinones | |
| DE3415138A1 (de) | N-(azolylcarbamoyl)-hydroxylamine und diese enthaltende fungizide | |
| US3887472A (en) | Cyclic oxime derivatives | |
| EP0557787B1 (de) | Imidazolylphenolderivate, diese enthaltende Arzneimittel sowie ein Verfahren zur Herstellung dieser Verbindungen und Arzneimittel | |
| US4154740A (en) | Substituted tetrahydrobenzothiophenes and method of preparation thereof | |
| CA1291132C (en) | Anti-atherosclerotic trisubstituted ureas and thioureas | |
| RU2090555C1 (ru) | Производные мочевины, способ получения производных мочевины, фармацевтическая композиция, обладающая ингибирующей активностью в отношении coa : холестерин-ацилтрансферазы (асат) | |
| US3994713A (en) | Herbicidal alanine derivatives | |
| DE69528984T2 (de) | Hemmung der leukotrienbiosynthese mittels harnstoffderivaten | |
| US4051183A (en) | 1-benzoyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)-urea, a novel and useful intermediate for the preparation of animal growth promoting agents | |
| CS212231B2 (en) | Acaricide means and method of preparation of the active agent | |
| MXPA97000860A (en) | Inhibition of the biosynthesis of leukotrians with u derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 8300370-7 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8300370-7 Format of ref document f/p: F |