CA2412116A1 - Biphenylcarboxylic acid amides, the preparation thereof and the use thereof as medicaments - Google Patents

Info

Publication number

CA2412116A1

CA2412116A1 CA002412116A CA2412116A CA2412116A1 CA 2412116 A1 CA2412116 A1 CA 2412116A1 CA 002412116 A CA002412116 A CA 002412116A CA 2412116 A CA2412116 A CA 2412116A CA 2412116 A1 CA2412116 A1 CA 2412116A1

Authority

CA

Canada

Prior art keywords

group

alkyl

phenyl

amino

carbonylamino

Prior art date

2000-07-08

Legal status (The legal status 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 status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000003814 drug Substances 0.000 title claims abstract description 7
• 238000002360 preparation method Methods 0.000 title claims description 6
• GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical class NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 title claims description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 46
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 238000004519 manufacturing process Methods 0.000 claims abstract 3
• -1 C1-3-alkyl-carbonyl Chemical group 0.000 claims description 238
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 60
• 239000000460 chlorine Substances 0.000 claims description 45
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
• 229910052801 chlorine Inorganic materials 0.000 claims description 43
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 40
• 239000011737 fluorine Substances 0.000 claims description 40
• 229910052731 fluorine Inorganic materials 0.000 claims description 40
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 36
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 35
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 32
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 29
• 239000000203 mixture Substances 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 27
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
• 239000001301 oxygen Substances 0.000 claims description 26
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 23
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
• 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 20
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 16
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 15
• 150000001721 carbon Chemical group 0.000 claims description 15
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 14
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 13
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
• 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 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 11
• 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 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 9
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 8
• 125000006267 biphenyl group Chemical group 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 239000004305 biphenyl Substances 0.000 claims description 7
• 235000010290 biphenyl Nutrition 0.000 claims description 7
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 6
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 6
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 5
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
• 108090001030 Lipoproteins Proteins 0.000 claims description 4
• 102000004895 Lipoproteins Human genes 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 125000005001 aminoaryl group Chemical group 0.000 claims description 4
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 4
• 230000000923 atherogenic effect Effects 0.000 claims description 4
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 4
• 230000000694 effects Effects 0.000 claims description 4
• 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 4
• 238000001727 in vivo Methods 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 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 4
• 230000036470 plasma concentration Effects 0.000 claims description 4
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 230000010933 acylation Effects 0.000 claims description 3
• 238000005917 acylation reaction Methods 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 230000029936 alkylation Effects 0.000 claims description 3
• 238000005804 alkylation reaction Methods 0.000 claims description 3
• 230000009435 amidation Effects 0.000 claims description 3
• 238000007112 amidation reaction Methods 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 238000005886 esterification reaction Methods 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 3
• OIVGBQAEAUQSFS-UHFFFAOYSA-N n-[3-[[4-(3-methyl-5-phenylpyrazol-1-yl)phenyl]methylcarbamoyl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C(CNC(=O)C=2C=C(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)C=CC=2)C=CC=1N1N=C(C)C=C1C1=CC=CC=C1 OIVGBQAEAUQSFS-UHFFFAOYSA-N 0.000 claims description 3
• FSWOBSFMVBIXGQ-UHFFFAOYSA-N n-[4-[[[3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoyl]amino]methyl]phenyl]pyridine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=CC(C(=O)NCC=2C=CC(NC(=O)C=3N=CC=CC=3)=CC=2)=C1 FSWOBSFMVBIXGQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 238000005932 reductive alkylation reaction Methods 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 2
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
• 239000005864 Sulphur Substances 0.000 claims description 2
• 125000001769 aryl amino group Chemical group 0.000 claims description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 150000007522 mineralic acids Chemical class 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• UKAVIQNAZUIYQR-UHFFFAOYSA-N n-[3-[3-(4-propan-2-ylphenyl)prop-2-ynylcarbamoyl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(C)C)=CC=C1C#CCNC(=O)C1=CC=CC(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UKAVIQNAZUIYQR-UHFFFAOYSA-N 0.000 claims description 2
• RCRKEYUGBZXZQG-UHFFFAOYSA-N n-[3-[[4-(3,4-dihydro-2h-quinolin-1-yl)phenyl]methylcarbamoyl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=CC(C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3CCC2)=C1 RCRKEYUGBZXZQG-UHFFFAOYSA-N 0.000 claims description 2
• 150000007524 organic acids Chemical class 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 239000000651 prodrug Substances 0.000 claims description 2
• 229940002612 prodrug Drugs 0.000 claims description 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims 2
• 239000000969 carrier Substances 0.000 claims 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
• 125000005214 aminoheteroaryl group Chemical group 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 8
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 2
• 230000003228 microsomal effect Effects 0.000 abstract 1
• 150000004885 piperazines Chemical class 0.000 abstract 1
• 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 620
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 386
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 183
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 152
• 238000001819 mass spectrum Methods 0.000 description 149
• 239000000741 silica gel Substances 0.000 description 148
• 229910002027 silica gel Inorganic materials 0.000 description 148
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 135
• 235000019441 ethanol Nutrition 0.000 description 132
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 126
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
• 239000011734 sodium Substances 0.000 description 98
• NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 63
• GSHHKCGJFNCOQV-UHFFFAOYSA-N 3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 GSHHKCGJFNCOQV-UHFFFAOYSA-N 0.000 description 59
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 51
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 40
• 239000012317 TBTU Substances 0.000 description 38
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 38
• AYWIMKUDWKDPRG-UHFFFAOYSA-N 3-[(2-phenylbenzoyl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 AYWIMKUDWKDPRG-UHFFFAOYSA-N 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• 239000002904 solvent Substances 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
• OIDDXXNLVPTTSN-UHFFFAOYSA-N n-[3-[(4-aminophenyl)methylcarbamoyl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(N)=CC=C1CNC(=O)C1=CC=CC(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 OIDDXXNLVPTTSN-UHFFFAOYSA-N 0.000 description 14
• 239000000243 solution Substances 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 239000005711 Benzoic acid Substances 0.000 description 10
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 10
• 108010038232 microsomal triglyceride transfer protein Proteins 0.000 description 10
• 239000003208 petroleum Substances 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
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