NZ588633A - NOVEL PIPERIDINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE - Google Patents

Info

Publication number

NZ588633A

NZ588633A NZ588633A NZ58863309A NZ588633A NZ 588633 A NZ588633 A NZ 588633A NZ 588633 A NZ588633 A NZ 588633A NZ 58863309 A NZ58863309 A NZ 58863309A NZ 588633 A NZ588633 A NZ 588633A

Authority

NZ

New Zealand

Prior art keywords

compound

oxo

piperidin

phenyl

ethyl

Prior art date

2008-03-20

Links

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• Global Dossier
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• 108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 12
• 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims abstract description 12
• 239000003112 inhibitor Substances 0.000 title claims abstract description 9
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 234
• 208000008589 Obesity Diseases 0.000 claims abstract description 14
• 235000020824 obesity Nutrition 0.000 claims abstract description 14
• 238000002360 preparation method Methods 0.000 claims abstract description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 587
• 229910001868 water Inorganic materials 0.000 claims description 192
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 180
• -1 cyano, nitro, amino Chemical group 0.000 claims description 159
• 239000011541 reaction mixture Substances 0.000 claims description 158
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 149
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 130
• 230000002829 reductive effect Effects 0.000 claims description 128
• 150000003839 salts Chemical class 0.000 claims description 102
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 83
• 229910052938 sodium sulfate Inorganic materials 0.000 claims description 83
• 235000011152 sodium sulphate Nutrition 0.000 claims description 83
• 125000003118 aryl group Chemical group 0.000 claims description 81
• 125000000217 alkyl group Chemical group 0.000 claims description 78
• 125000001072 heteroaryl group Chemical group 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 61
• 239000001257 hydrogen Substances 0.000 claims description 61
• 239000012044 organic layer Substances 0.000 claims description 45
• 239000012453 solvate Substances 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 36
• DCVWMMMKFZVEDP-UHFFFAOYSA-N 1-(cyclobutylmethyl)triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1CCC1 DCVWMMMKFZVEDP-UHFFFAOYSA-N 0.000 claims description 34
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 238000000746 purification Methods 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
• QBPUOAJBMXXBNU-UHFFFAOYSA-N 3-phenyl-1H-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=CC=CC=2)=N1 QBPUOAJBMXXBNU-UHFFFAOYSA-N 0.000 claims description 15
• 125000001769 aryl amino group Chemical group 0.000 claims description 13
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
• 125000003368 amide group Chemical group 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
• 150000004677 hydrates Chemical class 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• ZYFRBEJYRHBUSJ-UHFFFAOYSA-N C1CN(C(=O)CN)CCC1OC1=CC=CC=C1Cl Chemical compound C1CN(C(=O)CN)CCC1OC1=CC=CC=C1Cl ZYFRBEJYRHBUSJ-UHFFFAOYSA-N 0.000 claims description 8
• VZTKTOKASVGDFZ-UHFFFAOYSA-N 4-amino-n-[2-[4-[[4-amino-5-(2,6-difluorobenzoyl)-1,3-thiazol-2-yl]amino]piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound S1C(C(=O)C=2C(=CC=CC=2F)F)=C(N)N=C1NC(CC1)CCN1C(=O)CNC(=O)C1=CC=C(N)C=C1 VZTKTOKASVGDFZ-UHFFFAOYSA-N 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• KERBTFURRLPANO-UHFFFAOYSA-N n-[2-[4-[[4-amino-5-(2,6-difluorobenzoyl)-1,3-thiazol-2-yl]amino]piperidin-1-yl]-2-oxoethyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NCC(=O)N2CCC(CC2)NC=2SC(=C(N)N=2)C(=O)C=2C(=CC=CC=2F)F)=C1 KERBTFURRLPANO-UHFFFAOYSA-N 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 238000002953 preparative HPLC Methods 0.000 claims description 5
• AMBDRXRCOGOEHY-UHFFFAOYSA-N 6-anilino-n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]pyridine-3-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=NC(NC=3C=CC=CC=3)=CC=2)CC1 AMBDRXRCOGOEHY-UHFFFAOYSA-N 0.000 claims description 4
• BVXVSCNTHVGDRU-UHFFFAOYSA-N N-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-5-(2-hydroxyphenyl)-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C(=CC=CC=2)Cl)=NO1 BVXVSCNTHVGDRU-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• DBGFNCYANRRSIL-UHFFFAOYSA-N n-[2-[4-(2,5-dimethylanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=CC=C(C)C(NC2CCN(CC2)C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)=C1 DBGFNCYANRRSIL-UHFFFAOYSA-N 0.000 claims description 4
• NCKQFZBBVWTDSR-UHFFFAOYSA-N n-[2-oxo-2-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-4-phenylbenzamide Chemical compound FC(F)(F)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 NCKQFZBBVWTDSR-UHFFFAOYSA-N 0.000 claims description 4
• KQJNEJZQJRLPPB-UHFFFAOYSA-N 4-anilino-n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=CC(NC=3C=CC=CC=3)=CC=2)CC1 KQJNEJZQJRLPPB-UHFFFAOYSA-N 0.000 claims description 3
• UWKQESXIAZDLGF-UHFFFAOYSA-N CC1=CC=C(C#N)C=C1OC1CCN(C(=O)CN)CC1 Chemical compound CC1=CC=C(C#N)C=C1OC1CCN(C(=O)CN)CC1 UWKQESXIAZDLGF-UHFFFAOYSA-N 0.000 claims description 3
• 229940123980 Desaturase inhibitor Drugs 0.000 claims description 3
• RWKMMQRQJJXJNX-UHFFFAOYSA-N N-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-5-(2-hydroxyphenyl)-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)NC=2C(=CC=CC=2)Cl)=NO1 RWKMMQRQJJXJNX-UHFFFAOYSA-N 0.000 claims description 3
• YBZAZJVFYNOKDB-UHFFFAOYSA-N n-[2-[4-(2,5-difluorophenoxy)piperidin-1-yl]-2-oxoethyl]-1-phenylimidazole-4-carboxamide Chemical compound FC1=CC=C(F)C(OC2CCN(CC2)C(=O)CNC(=O)C=2N=CN(C=2)C=2C=CC=CC=2)=C1 YBZAZJVFYNOKDB-UHFFFAOYSA-N 0.000 claims description 3
• WFAALKOUHKWGCA-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-3-(3-hydroxyphenyl)-1h-pyrazole-5-carboxamide Chemical compound OC1=CC=CC(C=2NN=C(C=2)C(=O)NCC(=O)N2CCC(CC2)NC=2C(=CC=CC=2)Cl)=C1 WFAALKOUHKWGCA-UHFFFAOYSA-N 0.000 claims description 3
• YXWTVUAGHOZUIC-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 YXWTVUAGHOZUIC-UHFFFAOYSA-N 0.000 claims description 3
• BWFZXKALYDFNKM-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-5-phenyl-1,2-oxazole-3-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C2=NOC(=C2)C=2C=CC=CC=2)CC1 BWFZXKALYDFNKM-UHFFFAOYSA-N 0.000 claims description 3
• KEKOLPIGAGGFCH-UHFFFAOYSA-N n-[2-[4-[n-methyl-2-(trifluoromethyl)anilino]piperidin-1-yl]-2-oxoethyl]-4-phenylbenzamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C(CC1)CCN1C(=O)CNC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KEKOLPIGAGGFCH-UHFFFAOYSA-N 0.000 claims description 3
• FUQVEOXNFSKAFB-UHFFFAOYSA-N 2-[1-[2-[(3-phenyl-1h-pyrazole-5-carbonyl)amino]acetyl]piperidin-4-yl]oxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 FUQVEOXNFSKAFB-UHFFFAOYSA-N 0.000 claims description 2
• BPKQAZUPMXCHJJ-UHFFFAOYSA-N 5-(3-hydroxyphenyl)-n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC(C=2ON=C(C=2)C(=O)NCC(=O)N2CCC(CC2)OC=2C=C(C=CC=2)C(F)(F)F)=C1 BPKQAZUPMXCHJJ-UHFFFAOYSA-N 0.000 claims description 2
• SWPMDGGBLXFPOF-UHFFFAOYSA-N C1CN(C(=O)CN)CCC1OC1=CC=CC(C#N)=C1 Chemical compound C1CN(C(=O)CN)CCC1OC1=CC=CC(C#N)=C1 SWPMDGGBLXFPOF-UHFFFAOYSA-N 0.000 claims description 2
• IEDDXSVWWDQSNO-UHFFFAOYSA-N C1N(C(=O)CN)CCC1OC1=CC=CC=C1Cl Chemical compound C1N(C(=O)CN)CCC1OC1=CC=CC=C1Cl IEDDXSVWWDQSNO-UHFFFAOYSA-N 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• WZEUNJRSKJIIHQ-UHFFFAOYSA-N n-[2-[3-(5-cyano-2-methylphenoxy)azetidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=CC=C(C#N)C=C1OC1CN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)C1 WZEUNJRSKJIIHQ-UHFFFAOYSA-N 0.000 claims description 2
• BZDPLIAACVTKNV-UHFFFAOYSA-N n-[2-[3-[3-fluoro-5-(trifluoromethyl)phenoxy]azetidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC(OC2CN(C2)C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)=C1 BZDPLIAACVTKNV-UHFFFAOYSA-N 0.000 claims description 2
• OGWBHUYCALEIPO-UHFFFAOYSA-N n-[2-[4-(2-acetylphenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC(=O)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 OGWBHUYCALEIPO-UHFFFAOYSA-N 0.000 claims description 2
• IMNSGCAUWONPEE-UHFFFAOYSA-N n-[2-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-2-oxoethyl]-2-phenyl-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CNC(=O)C=2NC=3C=C(SC=3C=2)C=2C=CC=CC=2)=C1 IMNSGCAUWONPEE-UHFFFAOYSA-N 0.000 claims description 2
• RJUZKNPHBBGMEE-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-3-(2-fluorophenyl)-1h-pyrazole-5-carboxamide Chemical compound FC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C(=CC=CC=2)Cl)=NN1 RJUZKNPHBBGMEE-UHFFFAOYSA-N 0.000 claims description 2
• LVVXQQDLOJHCDK-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-4-phenylpyrazole-1-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)N2N=CC(=C2)C=2C=CC=CC=2)CC1 LVVXQQDLOJHCDK-UHFFFAOYSA-N 0.000 claims description 2
• PBAACEKUXMTVQN-UHFFFAOYSA-N n-[2-[4-(2-chloropyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-3-(4-fluorophenyl)-1h-pyrazole-5-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C(=NC=CC=2)Cl)=NN1 PBAACEKUXMTVQN-UHFFFAOYSA-N 0.000 claims description 2
• PQLJHGORBYLEKR-UHFFFAOYSA-N n-[2-[4-(2-cyanophenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound C1CC(OC=2C(=CC=CC=2)C#N)CCN1C(=O)CNC(=O)C(=NN1)C=C1C1=CC=CC=C1 PQLJHGORBYLEKR-UHFFFAOYSA-N 0.000 claims description 2
• MCTHOEYUMWNULO-UHFFFAOYSA-N n-[2-[4-(2-hydroxyphenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound OC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 MCTHOEYUMWNULO-UHFFFAOYSA-N 0.000 claims description 2
• VWOSFUOLZVTQLH-UHFFFAOYSA-N n-[2-[4-(2-methylsulfonylphenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 VWOSFUOLZVTQLH-UHFFFAOYSA-N 0.000 claims description 2
• RTNRLPYMJXGTBZ-UHFFFAOYSA-N n-[2-[4-(4-methylpyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=CC=NC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 RTNRLPYMJXGTBZ-UHFFFAOYSA-N 0.000 claims description 2
• GQEVORZFWKDZJE-UHFFFAOYSA-N n-[2-[4-(5-chloropyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-3-(4-fluorophenyl)-1h-pyrazole-5-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C=C(Cl)C=NC=2)=NN1 GQEVORZFWKDZJE-UHFFFAOYSA-N 0.000 claims description 2
• DSLPYHOJHSHWOO-UHFFFAOYSA-N n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CCN(CC2)C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)=C1 DSLPYHOJHSHWOO-UHFFFAOYSA-N 0.000 claims description 2
• LKWPGLCZVNYLPL-UHFFFAOYSA-N n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-4-(pyrrolidine-1-carbonyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(OC2CCN(CC2)C(=O)CNC(=O)C=2C=CC(=CC=2)C(=O)N2CCCC2)=C1 LKWPGLCZVNYLPL-UHFFFAOYSA-N 0.000 claims description 2
• 150000003852 triazoles Chemical group 0.000 claims description 2
• YVDSFJVIPJIDDM-UHFFFAOYSA-N 1-(3-methylphenyl)-n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]triazole-4-carboxamide Chemical compound CC1=CC=CC(N2N=NC(=C2)C(=O)NCC(=O)N2CCC(CC2)OC=2C=C(C=CC=2)C(F)(F)F)=C1 YVDSFJVIPJIDDM-UHFFFAOYSA-N 0.000 claims 1
• 230000004075 alteration Effects 0.000 claims 1
• 230000004048 modification Effects 0.000 claims 1
• 238000012986 modification Methods 0.000 claims 1
• DNSOZZOLYMPPRJ-UHFFFAOYSA-N n-[2-[3-(2-chlorophenoxy)pyrrolidin-1-yl]-2-oxoethyl]-1-pyridin-3-yltriazole-4-carboxamide Chemical compound ClC1=CC=CC=C1OC1CN(C(=O)CNC(=O)C=2N=NN(C=2)C=2C=NC=CC=2)CC1 DNSOZZOLYMPPRJ-UHFFFAOYSA-N 0.000 claims 1
• TUULZIHYKXUNBK-UHFFFAOYSA-N n-[2-[4-(2-chlorophenyl)sulfanylpiperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound ClC1=CC=CC=C1SC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 TUULZIHYKXUNBK-UHFFFAOYSA-N 0.000 claims 1
• UZDOEXMWGAVVBA-UHFFFAOYSA-N n-[2-[4-(2-chloropyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-5-(4-fluorophenyl)-1,2-oxazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C(=NC=CC=2)Cl)=NO1 UZDOEXMWGAVVBA-UHFFFAOYSA-N 0.000 claims 1
• IXIZADTUIXLHKO-UHFFFAOYSA-N n-[2-[4-(3-cyanophenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound C1CC(OC=2C=C(C=CC=2)C#N)CCN1C(=O)CNC(=O)C(=NN1)C=C1C1=CC=CC=C1 IXIZADTUIXLHKO-UHFFFAOYSA-N 0.000 claims 1
• SHFMSQWRLSJMEJ-UHFFFAOYSA-N n-[2-[4-[4-fluoro-3-(trifluoromethyl)phenoxy]piperidin-1-yl]-2-oxoethyl]-1-phenylimidazole-4-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1OC1CCN(C(=O)CNC(=O)C=2N=CN(C=2)C=2C=CC=CC=2)CC1 SHFMSQWRLSJMEJ-UHFFFAOYSA-N 0.000 claims 1
• BTACWTRLUFGORP-UHFFFAOYSA-N n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-3-[2-(trifluoromethyl)phenyl]-1h-pyrazole-5-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CCN(CC2)C(=O)CNC(=O)C2=NNC(=C2)C=2C(=CC=CC=2)C(F)(F)F)=C1 BTACWTRLUFGORP-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 264
• 238000000034 method Methods 0.000 abstract description 39
• 238000011282 treatment Methods 0.000 abstract description 15
• 230000008569 process Effects 0.000 abstract description 8
• 150000003053 piperidines Chemical class 0.000 abstract description 3
• 239000000243 solution Substances 0.000 description 307
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 209
• 235000019439 ethyl acetate Nutrition 0.000 description 195
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 195
• 229940093499 ethyl acetate Drugs 0.000 description 194
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 163
• 230000015572 biosynthetic process Effects 0.000 description 143
• 238000003786 synthesis reaction Methods 0.000 description 141
• 238000005481 NMR spectroscopy Methods 0.000 description 113
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 89
• 239000000047 product Substances 0.000 description 88
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 87
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 81
• 239000012267 brine Substances 0.000 description 80
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 72
• 239000002244 precipitate Substances 0.000 description 67
• 238000001914 filtration Methods 0.000 description 66
• 239000000543 intermediate Substances 0.000 description 65
• 239000010410 layer Substances 0.000 description 60
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
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