NZ264063A

NZ264063A - N-(2-phenylpyrid-3-yl)- and n-(4-phenylpyrimidin-5-yl)-n'-phenylurea derivatives and pharmaceutical compositions

N-(2-phenylpyrid-3-yl)- and n-(4-phenylpyrimidin-5-yl)-n'-phenylurea derivatives and pharmaceutical compositions

Info

Publication number: NZ264063A
Authority: NZ; New Zealand
Prior art keywords: group; groups; lower alkyl; compound; hydrogen atom
Prior art date: 1993-08-13

Application number

NZ264063A

Other languages

English (en)

Inventor

Masashi Nagamine

Kenji Yamamoto

Kenji Horiuchi

Yoshimitsu Matsui

Masanori Yoshida

Original Assignee

Nihon Nohyaku Co Ltd

Priority date

1993-08-13

Filing date

1994-07-22

Publication date

1995-11-27

1994-07-22 Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd

1995-11-27 Publication of NZ264063A publication Critical patent/NZ264063A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 97
125000001309 chloro group Chemical group Cl* 0.000 claims description 55
125000000217 alkyl group Chemical group 0.000 claims description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 20
230000000694 effects Effects 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 13
125000001188 haloalkyl group Chemical group 0.000 claims description 13
150000003222 pyridines Chemical class 0.000 claims description 10
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
230000005764 inhibitory process Effects 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
239000003112 inhibitor Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
201000001320 Atherosclerosis Diseases 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
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 3
201000010099 disease Diseases 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
230000000069 prophylactic effect Effects 0.000 claims description 3
229940124597 therapeutic agent Drugs 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 2
108010022164 acetyl-LDL Proteins 0.000 claims 2
241000282320 Panthera leo Species 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 57
-1 dimethylaminoethyl Chemical group 0.000 description 43
239000000203 mixture Substances 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 32
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
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 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
238000001816 cooling Methods 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 0.000 description 18
239000004202 carbamide Substances 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
239000000243 solution Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
239000012043 crude product Substances 0.000 description 13
239000003480 eluent Substances 0.000 description 13
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
229940093499 ethyl acetate Drugs 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
238000009472 formulation Methods 0.000 description 11
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
235000012000 cholesterol Nutrition 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
UBUFLKCDEQIQNB-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1Cl UBUFLKCDEQIQNB-UHFFFAOYSA-N 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 7
239000008187 granular material Substances 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
239000012258 stirred mixture Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
LBWOQTIEELSESH-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)-6-methyl-2-phenylpyrimidin-5-yl]-3-(2,4-difluorophenyl)urea Chemical compound CC1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC=CC=2)Cl)=C1NC(=O)NC1=CC=C(F)C=C1F LBWOQTIEELSESH-UHFFFAOYSA-N 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
RETGTTCHFSMLOG-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-methylpyrimidine-5-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)C(C=2C(=CC=CC=2)Cl)=N1 RETGTTCHFSMLOG-UHFFFAOYSA-N 0.000 description 4
DWXMVQGVWUKTPO-UHFFFAOYSA-N 4-(2-chlorophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1Cl DWXMVQGVWUKTPO-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001840 cholesterol esters Chemical class 0.000 description 4
235000005911 diet Nutrition 0.000 description 4
230000037213 diet Effects 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 3
VYGXFQGCXOGBOD-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)-2-ethoxypyrimidin-5-yl]-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound C=1C=CC=C(Cl)C=1C1=NC(OCC)=NC=C1NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C VYGXFQGCXOGBOD-UHFFFAOYSA-N 0.000 description 3
DZRNHFJSCYBKCC-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)-2-phenylpyrimidin-5-yl]-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1Cl DZRNHFJSCYBKCC-UHFFFAOYSA-N 0.000 description 3
PADZXGJCJIBCRU-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)-2-phenylpyrimidin-5-yl]-3-phenylurea Chemical compound ClC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC=C1NC(=O)NC1=CC=CC=C1 PADZXGJCJIBCRU-UHFFFAOYSA-N 0.000 description 3
FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 3
YULLKGTUPIXYQU-UHFFFAOYSA-N 2,6-diphenylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 YULLKGTUPIXYQU-UHFFFAOYSA-N 0.000 description 3
GLLBWARPFIORKT-UHFFFAOYSA-N 2-(2-chlorophenyl)-6-heptylpyridine-3-carboxylic acid Chemical compound CCCCCCCC1=CC=C(C(O)=O)C(C=2C(=CC=CC=2)Cl)=N1 GLLBWARPFIORKT-UHFFFAOYSA-N 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
239000005695 Ammonium acetate Substances 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
239000002775 capsule Substances 0.000 description 3
208000026106 cerebrovascular disease Diseases 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000002156 mixing Methods 0.000 description 3
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000008096 xylene Substances 0.000 description 3
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 2
WHAKRDLFMCQGFK-UHFFFAOYSA-N 1-(2,4-diphenylpyrimidin-5-yl)-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NC1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 WHAKRDLFMCQGFK-UHFFFAOYSA-N 0.000 description 2
PPHZFXBKQAQVRD-UHFFFAOYSA-N 1-(2,6-diethylphenyl)-3-[4-(2-methylsulfanylphenyl)-2-phenylpyrimidin-5-yl]urea Chemical compound CCC1=CC=CC(CC)=C1NC(=O)NC1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1SC PPHZFXBKQAQVRD-UHFFFAOYSA-N 0.000 description 2
MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 2
GLIPVPWXLDCYJM-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)-6-cyclohexylpyridin-3-yl]-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NC1=CC=C(C2CCCCC2)N=C1C1=CC=CC=C1Cl GLIPVPWXLDCYJM-UHFFFAOYSA-N 0.000 description 2
ZIRGGRHGJBUXHQ-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)-6-methylpyridin-3-yl]-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NC1=CC=C(C)N=C1C1=CC=CC=C1Cl ZIRGGRHGJBUXHQ-UHFFFAOYSA-N 0.000 description 2
KLCLCWSRUBLBLA-UHFFFAOYSA-N 1-[2-tert-butyl-4-(2-chlorophenyl)pyrimidin-5-yl]-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NC1=CN=C(C(C)(C)C)N=C1C1=CC=CC=C1Cl KLCLCWSRUBLBLA-UHFFFAOYSA-N 0.000 description 2
BBMSVNZLZCIJPZ-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)-2-phenylpyrimidin-5-yl]-3-(2,6-diethylphenyl)urea Chemical compound CCC1=CC=CC(CC)=C1NC(=O)NC1=CN=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1Cl BBMSVNZLZCIJPZ-UHFFFAOYSA-N 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
208000035150 Hypercholesterolemia Diseases 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
102000001494 Sterol O-Acyltransferase Human genes 0.000 description 2
108010054082 Sterol O-acyltransferase Proteins 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 2
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