ES2271100T3 - Derivados de pirimidina y su empleo como ligandos del receptor de neuropeptido. - Google Patents

Info

Publication number

ES2271100T3

ES2271100T3 ES01989438T ES01989438T ES2271100T3 ES 2271100 T3 ES2271100 T3 ES 2271100T3 ES 01989438 T ES01989438 T ES 01989438T ES 01989438 T ES01989438 T ES 01989438T ES 2271100 T3 ES2271100 T3 ES 2271100T3

Authority

ES

Spain

Prior art keywords

methyl

vinyl

phenyl

pyrimidine

mmol

Prior art date

2000-11-10

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.)

Expired - Lifetime

Links

• Espacenet
• Global Dossier
• Discuss

• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 104
• -1 hydroxy-alkoxyalkyl Chemical group 0.000 claims abstract description 64
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 17
• 150000002148 esters Chemical class 0.000 claims abstract description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
• 125000001424 substituent group Chemical group 0.000 claims abstract description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
• 239000001257 hydrogen Substances 0.000 claims abstract description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
• 125000003118 aryl group Chemical group 0.000 claims abstract description 9
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 5
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 5
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 85
• 239000000460 chlorine Substances 0.000 claims description 37
• 238000002360 preparation method Methods 0.000 claims description 33
• 238000006243 chemical reaction Methods 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 28
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 15
• 229960001243 orlistat Drugs 0.000 claims description 15
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 13
• 208000008589 Obesity Diseases 0.000 claims description 13
• 235000020824 obesity Nutrition 0.000 claims description 13
• 230000002265 prevention Effects 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 101710151321 Melanostatin Proteins 0.000 claims description 8
• 102100028427 Pro-neuropeptide Y Human genes 0.000 claims description 8
• 206010003246 arthritis Diseases 0.000 claims description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims description 8
• 208000030814 Eating disease Diseases 0.000 claims description 7
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
• 235000014632 disordered eating Nutrition 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• TWQHYKCRVQJUKE-CMDGGOBGSA-N 2-[(e)-2-(3-methoxyphenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound COC1=CC=CC(\C=C\C=2N=C(C=C(C)N=2)N2CCCC2)=C1 TWQHYKCRVQJUKE-CMDGGOBGSA-N 0.000 claims description 6
• BFZWDYCUPULXDR-BQYQJAHWSA-N 3-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]benzonitrile Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(C#N)=C1 BFZWDYCUPULXDR-BQYQJAHWSA-N 0.000 claims description 6
• 102000004882 Lipase Human genes 0.000 claims description 6
• 108090001060 Lipase Proteins 0.000 claims description 6
• 239000004367 Lipase Substances 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 235000019421 lipase Nutrition 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 230000009467 reduction Effects 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• FGGVKULRQBWAKD-FNORWQNLSA-N 2-[(e)-2-(3,4-difluorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=C(F)C(F)=C1 FGGVKULRQBWAKD-FNORWQNLSA-N 0.000 claims description 4
• YRLAKTSBTITNAC-FNORWQNLSA-N 2-[(e)-2-(3-chloro-4-fluorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=C(F)C(Cl)=C1 YRLAKTSBTITNAC-FNORWQNLSA-N 0.000 claims description 4
• UQQDSRUWHUCSDM-BQYQJAHWSA-N 2-[(e)-2-(3-chlorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(Cl)=C1 UQQDSRUWHUCSDM-BQYQJAHWSA-N 0.000 claims description 4
• HHMWYILZARJOIU-BQYQJAHWSA-N 4-methyl-6-pyrrolidin-1-yl-2-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 HHMWYILZARJOIU-BQYQJAHWSA-N 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 239000003112 inhibitor Substances 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• YUYNAUBICMUPDF-FNORWQNLSA-N 2-[(e)-2-(2,4-dichlorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=C(Cl)C=C1Cl YUYNAUBICMUPDF-FNORWQNLSA-N 0.000 claims description 3
• BILMBMKTDXSAQK-BQYQJAHWSA-N [3-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]phenyl]methanol Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(CO)=C1 BILMBMKTDXSAQK-BQYQJAHWSA-N 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• HLYUPLUTAUFOKU-SNAWJCMRSA-N n-methyl-2-[(e)-2-pyridin-4-ylethenyl]-6-pyrrolidin-1-ylpyrimidin-4-amine Chemical compound N=1C(NC)=CC(N2CCCC2)=NC=1\C=C\C1=CC=NC=C1 HLYUPLUTAUFOKU-SNAWJCMRSA-N 0.000 claims description 3
• ZAXOKHLTHPETKE-VOTSOKGWSA-N 3-[(e)-2-[4-methyl-6-(3-methylazetidin-1-yl)pyrimidin-2-yl]ethenyl]benzonitrile Chemical compound C1C(C)CN1C1=CC(C)=NC(\C=C\C=2C=C(C=CC=2)C#N)=N1 ZAXOKHLTHPETKE-VOTSOKGWSA-N 0.000 claims description 2
• 125000002393 azetidinyl group Chemical group 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 201000010099 disease Diseases 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000004001 thioalkyl group Chemical group 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
• 239000007787 solid Substances 0.000 description 96
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 66
• 238000001228 spectrum Methods 0.000 description 60
• 238000001819 mass spectrum Methods 0.000 description 35
• 239000000203 mixture Substances 0.000 description 28
• 239000007858 starting material Substances 0.000 description 26
• UQFHLJKWYIJISA-UHFFFAOYSA-N 2,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(C)=N1 UQFHLJKWYIJISA-UHFFFAOYSA-N 0.000 description 21
• PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• 238000010438 heat treatment Methods 0.000 description 19
• MWUBEFRDHNLYPF-AATRIKPKSA-N 3-[(e)-2-(4-chloro-6-methylpyrimidin-2-yl)ethenyl]benzonitrile Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(C=CC=2)C#N)=N1 MWUBEFRDHNLYPF-AATRIKPKSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
• 239000000243 solution Substances 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 229920002554 vinyl polymer Polymers 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 150000004702 methyl esters Chemical class 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• WSGRCEQBNLCXSZ-AATRIKPKSA-N 4-chloro-2-[(e)-2-(3-chlorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(Cl)C=CC=2)=N1 WSGRCEQBNLCXSZ-AATRIKPKSA-N 0.000 description 7
• 229910019213 POCl3 Inorganic materials 0.000 description 7
• 150000001299 aldehydes Chemical class 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 235000019198 oils Nutrition 0.000 description 7
• 108020003175 receptors Proteins 0.000 description 7
• 102000005962 receptors Human genes 0.000 description 7
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 239000002671 adjuvant Substances 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 235000019439 ethyl acetate Nutrition 0.000 description 6
• URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• IFLHSHGUNSEYTF-AATRIKPKSA-N 4-chloro-2-[(e)-2-(3-fluorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(F)C=CC=2)=N1 IFLHSHGUNSEYTF-AATRIKPKSA-N 0.000 description 5
• ZZDUDKNWIUKWPF-VOTSOKGWSA-N 4-chloro-2-[(e)-2-(3-methoxyphenyl)ethenyl]-6-methylpyrimidine Chemical compound COC1=CC=CC(\C=C\C=2N=C(Cl)C=C(C)N=2)=C1 ZZDUDKNWIUKWPF-VOTSOKGWSA-N 0.000 description 5
• RCIBPRJKTAOXCK-VMPITWQZSA-N 4-chloro-6-methyl-2-[(e)-2-(4-methylsulfanylphenyl)ethenyl]pyrimidine Chemical compound C1=CC(SC)=CC=C1\C=C\C1=NC(C)=CC(Cl)=N1 RCIBPRJKTAOXCK-VMPITWQZSA-N 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 239000007832 Na2SO4 Substances 0.000 description 5
• 239000000872 buffer Substances 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 230000037406 food intake Effects 0.000 description 5
• 239000007903 gelatin capsule Substances 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 239000003446 ligand Substances 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 229920005862 polyol Polymers 0.000 description 5
• 150000003077 polyols Chemical class 0.000 description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 230000009466 transformation Effects 0.000 description 5
• AEDLMXNXPIFFTO-UHFFFAOYSA-N 2-chloro-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound ClC1=NC(C)=CC(N2CCCC2)=N1 AEDLMXNXPIFFTO-UHFFFAOYSA-N 0.000 description 4
• NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 4
• VGULNDSTWNGRSA-BQYQJAHWSA-N 3-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]benzoic acid Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(C(O)=O)=C1 VGULNDSTWNGRSA-BQYQJAHWSA-N 0.000 description 4
• GZWIPMXNMDBVPU-HWKANZROSA-N 4-chloro-2-[(e)-2-(3,4-difluorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(F)C(F)=CC=2)=N1 GZWIPMXNMDBVPU-HWKANZROSA-N 0.000 description 4
• BCPYEMNTAMPHEL-BQYQJAHWSA-N 4-methyl-2-[(e)-2-(3-nitrophenyl)ethenyl]-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC([N+]([O-])=O)=C1 BCPYEMNTAMPHEL-BQYQJAHWSA-N 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 125000004414 alkyl thio group Chemical group 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 239000008298 dragée Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 239000000825 pharmaceutical preparation Substances 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
• COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
• KEBOYHJEUFJZPE-LURJTMIESA-N (3s)-3-ethoxypyrrolidine Chemical compound CCO[C@H]1CCNC1 KEBOYHJEUFJZPE-LURJTMIESA-N 0.000 description 3
• WAYAPARTAQEPAI-HWKANZROSA-N 2-[(e)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C3OCOC3=CC=2)=N1 WAYAPARTAQEPAI-HWKANZROSA-N 0.000 description 3
• WFSPJJMREFDVQQ-UHFFFAOYSA-N 2-bromo-n-methyl-6-pyrrolidin-1-ylpyrimidin-4-amine Chemical compound BrC1=NC(NC)=CC(N2CCCC2)=N1 WFSPJJMREFDVQQ-UHFFFAOYSA-N 0.000 description 3
• YYVWTJIDTBRLER-VMPITWQZSA-N 3-[(e)-2-(4-chloro-6-methylpyrimidin-2-yl)ethenyl]-4-methoxy-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1\C=C\C1=NC(C)=CC(Cl)=N1 YYVWTJIDTBRLER-VMPITWQZSA-N 0.000 description 3
• ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 3
• QQZPARSVWKNPER-RMKNXTFCSA-N 4-[(e)-2-(4-chloro-6-methylpyrimidin-2-yl)ethenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=NC(C)=CC(Cl)=N1 QQZPARSVWKNPER-RMKNXTFCSA-N 0.000 description 3
• JIRCMBXZFRUBHA-VOTSOKGWSA-N 4-[(e)-2-(4-chloro-6-methylpyrimidin-2-yl)ethenyl]benzonitrile Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=CC(=CC=2)C#N)=N1 JIRCMBXZFRUBHA-VOTSOKGWSA-N 0.000 description 3
• SNAORKLLSUUVIU-HWKANZROSA-N 4-chloro-2-[(e)-2-(2,4-dichlorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C(=CC(Cl)=CC=2)Cl)=N1 SNAORKLLSUUVIU-HWKANZROSA-N 0.000 description 3
• KJBHXPKLGXJOAT-HWKANZROSA-N 4-chloro-2-[(e)-2-(3,4-dichlorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(Cl)C(Cl)=CC=2)=N1 KJBHXPKLGXJOAT-HWKANZROSA-N 0.000 description 3
• VDJMVSPBPCIEPS-HWKANZROSA-N 4-chloro-2-[(e)-2-(3-chloro-4-fluorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(Cl)C(F)=CC=2)=N1 VDJMVSPBPCIEPS-HWKANZROSA-N 0.000 description 3
• ZASPVINBHXWFRB-VMPITWQZSA-N 4-chloro-2-[(e)-2-(4-methoxyphenyl)ethenyl]-6-methylpyrimidine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C)=CC(Cl)=N1 ZASPVINBHXWFRB-VMPITWQZSA-N 0.000 description 3
• AOUGTOROKWOZTI-UHFFFAOYSA-N 4-chloro-2-[2-(3,5-dichlorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(C=CC=2C=C(Cl)C=C(Cl)C=2)=N1 AOUGTOROKWOZTI-UHFFFAOYSA-N 0.000 description 3
• ZMGHBGGKJQMWNM-AATRIKPKSA-N 4-chloro-6-methyl-2-[(e)-2-(3-nitrophenyl)ethenyl]pyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(C=CC=2)[N+]([O-])=O)=N1 ZMGHBGGKJQMWNM-AATRIKPKSA-N 0.000 description 3
• FEJSBPGJUIXQIC-ZHACJKMWSA-N 4-chloro-6-methyl-2-[(e)-2-(3-phenylmethoxyphenyl)ethenyl]pyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 FEJSBPGJUIXQIC-ZHACJKMWSA-N 0.000 description 3
• UJKOFJBXJDJAPR-SNAWJCMRSA-N 4-chloro-6-methyl-2-[(e)-2-thiophen-2-ylethenyl]pyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2SC=CC=2)=N1 UJKOFJBXJDJAPR-SNAWJCMRSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• YNXLOPYTAAFMTN-SBUIBGKBSA-N C([C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)C1=CC=C(O)C=C1 Chemical compound C([C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)C1=CC=C(O)C=C1 YNXLOPYTAAFMTN-SBUIBGKBSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 206010020710 Hyperphagia Diseases 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
• 229940127470 Lipase Inhibitors Drugs 0.000 description 3
• SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 description 3
• 102100029909 Peptide YY Human genes 0.000 description 3
• 108010088847 Peptide YY Proteins 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 240000008042 Zea mays Species 0.000 description 3
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 239000005557 antagonist Substances 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 238000009833 condensation Methods 0.000 description 3
• 230000005494 condensation Effects 0.000 description 3
• 235000005822 corn Nutrition 0.000 description 3
• FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 3
• 239000003925 fat Substances 0.000 description 3
• 235000012631 food intake Nutrition 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 230000026030 halogenation Effects 0.000 description 3
• 238000005658 halogenation reaction Methods 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 description 3
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
• 235000019341 magnesium sulphate Nutrition 0.000 description 3
• BPGXUIVWLQTVLZ-OFGSCBOVSA-N neuropeptide y(npy) Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BPGXUIVWLQTVLZ-OFGSCBOVSA-N 0.000 description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
• 229910052760 oxygen Inorganic materials 0.000 description 3
• 229920000642 polymer Polymers 0.000 description 3
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 3
• 150000003230 pyrimidines Chemical class 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 239000008107 starch Substances 0.000 description 3
• 229940032147 starch Drugs 0.000 description 3
• 235000019698 starch Nutrition 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 238000012360 testing method Methods 0.000 description 3
• 238000000844 transformation Methods 0.000 description 3
• 235000015112 vegetable and seed oil Nutrition 0.000 description 3
• 239000008158 vegetable oil Substances 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• 239000001993 wax Substances 0.000 description 3
• 230000004584 weight gain Effects 0.000 description 3
• LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
• DNPRJYOOTGXBKE-UHFFFAOYSA-N 2,4-dimethyl-6-piperidin-1-ylpyrimidine Chemical compound CC1=NC(C)=CC(N2CCCCC2)=N1 DNPRJYOOTGXBKE-UHFFFAOYSA-N 0.000 description 2
• KWNBXYJSCFAYMC-UHFFFAOYSA-N 2,4-dimethyl-6-pyrrolidin-1-ylpyrimidine Chemical compound CC1=NC(C)=CC(N2CCCC2)=N1 KWNBXYJSCFAYMC-UHFFFAOYSA-N 0.000 description 2
• UMUOUCLHEMOZSQ-UHFFFAOYSA-N 2,6-dibromo-n-methylpyrimidin-4-amine Chemical compound CNC1=CC(Br)=NC(Br)=N1 UMUOUCLHEMOZSQ-UHFFFAOYSA-N 0.000 description 2
• YEJSUIGXTMZRSH-UHFFFAOYSA-N 2-(2,6-dimethylpyrimidin-4-yl)-3,4-dihydro-1h-isoquinoline Chemical compound CC1=NC(C)=CC(N2CC3=CC=CC=C3CC2)=N1 YEJSUIGXTMZRSH-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• YKVKMLHHRSEGCJ-FNORWQNLSA-N 2-[(e)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(\C=C\C=2C=C3OCOC3=CC=2)=NC(C)=CC=1N1CCCC1 YKVKMLHHRSEGCJ-FNORWQNLSA-N 0.000 description 2
• VXYOXDWLPQYGPH-HWKANZROSA-N 2-[(e)-2-(1,3-benzodioxol-5-yl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C=C3OCOC3=CC=2)=N1 VXYOXDWLPQYGPH-HWKANZROSA-N 0.000 description 2
• IITBFTRJUCHRRN-HWKANZROSA-N 2-[(e)-2-(2,4-dichlorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C(=CC(Cl)=CC=2)Cl)=N1 IITBFTRJUCHRRN-HWKANZROSA-N 0.000 description 2
• PPJSPPRLBCXVEP-FNORWQNLSA-N 2-[(e)-2-(2,4-difluorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=C(F)C=C1F PPJSPPRLBCXVEP-FNORWQNLSA-N 0.000 description 2
• VPZQDBRXUWLGEA-VQHVLOKHSA-N 2-[(e)-2-(2,4-dimethoxyphenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound COC1=CC(OC)=CC=C1\C=C\C1=NC(C)=CC(N2CCCC2)=N1 VPZQDBRXUWLGEA-VQHVLOKHSA-N 0.000 description 2
• OMKBSOTWXXGNER-FNORWQNLSA-N 2-[(e)-2-(2,4-dimethoxyphenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound COC1=CC(OC)=CC=C1\C=C\C1=NC(C)=CC(O)=N1 OMKBSOTWXXGNER-FNORWQNLSA-N 0.000 description 2
• SIYJDIAWRIPDRA-FNORWQNLSA-N 2-[(e)-2-(3,4-dichlorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=C(Cl)C(Cl)=C1 SIYJDIAWRIPDRA-FNORWQNLSA-N 0.000 description 2
• LBADDUDHAJGXDY-HWKANZROSA-N 2-[(e)-2-(3,4-dichlorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C=C(Cl)C(Cl)=CC=2)=N1 LBADDUDHAJGXDY-HWKANZROSA-N 0.000 description 2
• AUUXJJKDXLEUIA-SNAWJCMRSA-N 2-[(e)-2-(3,5-dichlorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC(Cl)=CC(Cl)=C1 AUUXJJKDXLEUIA-SNAWJCMRSA-N 0.000 description 2
• RHNPKWJUFRZGSR-HWKANZROSA-N 2-[(e)-2-(3-chloro-2,4-difluorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C(=C(Cl)C(F)=CC=2)F)=N1 RHNPKWJUFRZGSR-HWKANZROSA-N 0.000 description 2
• BJTNESHJLSUTTI-AATRIKPKSA-N 2-[(e)-2-(3-chlorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C=C(Cl)C=CC=2)=N1 BJTNESHJLSUTTI-AATRIKPKSA-N 0.000 description 2
• PUWMSJUQJLZQNH-BQYQJAHWSA-N 2-[(e)-2-(3-fluorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(F)=C1 PUWMSJUQJLZQNH-BQYQJAHWSA-N 0.000 description 2
• YYLVRAYYCJTHKB-AATRIKPKSA-N 2-[(e)-2-(3-fluorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C=C(F)C=CC=2)=N1 YYLVRAYYCJTHKB-AATRIKPKSA-N 0.000 description 2
• BSERTZTVYOWKIC-VOTSOKGWSA-N 2-[(e)-2-(3-methoxyphenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound COC1=CC=CC(\C=C\C=2N=C(O)C=C(C)N=2)=C1 BSERTZTVYOWKIC-VOTSOKGWSA-N 0.000 description 2
• OBMYOYUGQGJICQ-JXMROGBWSA-N 2-[(e)-2-(4-methoxyphenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C)=CC(N2CCCC2)=N1 OBMYOYUGQGJICQ-JXMROGBWSA-N 0.000 description 2
• PFPKEBFTHMHILN-VMPITWQZSA-N 2-[(e)-2-(4-methoxyphenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C)=CC(O)=N1 PFPKEBFTHMHILN-VMPITWQZSA-N 0.000 description 2
• HBXXWTCMMZTAGL-UHFFFAOYSA-N 2-[2-(3,5-dichlorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(C=CC=2C=C(Cl)C=C(Cl)C=2)=N1 HBXXWTCMMZTAGL-UHFFFAOYSA-N 0.000 description 2
• BBRSGAOOOWLTTP-MDZDMXLPSA-N 2-[2-methyl-6-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidin-4-yl]-3,4-dihydro-1h-isoquinoline Chemical compound C=1C(N2CC3=CC=CC=C3CC2)=NC(C)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 BBRSGAOOOWLTTP-MDZDMXLPSA-N 0.000 description 2
• PKRFNMFIVQXBAY-MDZDMXLPSA-N 2-[6-methyl-2-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidin-4-yl]-3,4-dihydro-1h-isoquinoline Chemical compound N=1C(C)=CC(N2CC3=CC=CC=C3CC2)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 PKRFNMFIVQXBAY-MDZDMXLPSA-N 0.000 description 2
• QXAZZMCPDFUCLS-CMDGGOBGSA-N 2-methyl-4-[(e)-2-(3-nitrophenyl)ethenyl]-6-piperidin-1-ylpyrimidine Chemical compound C=1C(N2CCCCC2)=NC(C)=NC=1\C=C\C1=CC=CC([N+]([O-])=O)=C1 QXAZZMCPDFUCLS-CMDGGOBGSA-N 0.000 description 2
• RBYVJIIMVDIHOG-BQYQJAHWSA-N 2-methyl-4-[(e)-2-(3-nitrophenyl)ethenyl]-6-pyrrolidin-1-ylpyrimidine Chemical compound C=1C(N2CCCC2)=NC(C)=NC=1\C=C\C1=CC=CC([N+]([O-])=O)=C1 RBYVJIIMVDIHOG-BQYQJAHWSA-N 0.000 description 2
• TUVYIQGYGWNTSM-BQYQJAHWSA-N 2-methyl-4-pyrrolidin-1-yl-6-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidine Chemical compound C=1C(N2CCCC2)=NC(C)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 TUVYIQGYGWNTSM-BQYQJAHWSA-N 0.000 description 2
• KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
• FJZVUUWGRQUPNQ-BQYQJAHWSA-N 3-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]aniline Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(N)=C1 FJZVUUWGRQUPNQ-BQYQJAHWSA-N 0.000 description 2
• KPDQWNAOLQDFMN-AATRIKPKSA-N 3-[(e)-2-(6-methyl-4-oxo-1h-pyrimidin-2-yl)ethenyl]benzoic acid Chemical compound N1C(C)=CC(=O)N=C1\C=C\C1=CC=CC(C(O)=O)=C1 KPDQWNAOLQDFMN-AATRIKPKSA-N 0.000 description 2
• NJOXLWMAEZOGGN-AATRIKPKSA-N 3-[(e)-2-(6-methyl-4-oxo-1h-pyrimidin-2-yl)ethenyl]benzonitrile Chemical compound CC1=CC(O)=NC(\C=C\C=2C=C(C=CC=2)C#N)=N1 NJOXLWMAEZOGGN-AATRIKPKSA-N 0.000 description 2
• VQFJDDNGOQKKGZ-AATRIKPKSA-N 3-[(e)-2-[4-(2-aminoethylamino)-6-methylpyrimidin-2-yl]ethenyl]benzonitrile Chemical compound CC1=CC(NCCN)=NC(\C=C\C=2C=C(C=CC=2)C#N)=N1 VQFJDDNGOQKKGZ-AATRIKPKSA-N 0.000 description 2
• UUEFUBUATNDRJO-CMDGGOBGSA-N 3-[(e)-2-[4-(butylamino)-6-methylpyrimidin-2-yl]ethenyl]benzonitrile Chemical compound CCCCNC1=CC(C)=NC(\C=C\C=2C=C(C=CC=2)C#N)=N1 UUEFUBUATNDRJO-CMDGGOBGSA-N 0.000 description 2
• IXLUUHSGWGKPAB-VMPITWQZSA-N 3-[(e)-2-[4-(cyclopropylamino)-6-methylpyrimidin-2-yl]ethenyl]benzonitrile Chemical compound N=1C(\C=C\C=2C=C(C=CC=2)C#N)=NC(C)=CC=1NC1CC1 IXLUUHSGWGKPAB-VMPITWQZSA-N 0.000 description 2
• WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
• PJZYKEFBRASPSJ-CMDGGOBGSA-N 4-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]benzonitrile Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=C(C#N)C=C1 PJZYKEFBRASPSJ-CMDGGOBGSA-N 0.000 description 2
• HFDCBVMRQLVNJX-VOTSOKGWSA-N 4-[(e)-2-(6-methyl-4-oxo-1h-pyrimidin-2-yl)ethenyl]benzonitrile Chemical compound CC1=CC(O)=NC(\C=C\C=2C=CC(=CC=2)C#N)=N1 HFDCBVMRQLVNJX-VOTSOKGWSA-N 0.000 description 2
• AXKVFVGWVHLEFQ-AATRIKPKSA-N 4-[2-methyl-6-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidin-4-yl]morpholine Chemical compound C=1C(N2CCOCC2)=NC(C)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 AXKVFVGWVHLEFQ-AATRIKPKSA-N 0.000 description 2
• ZKKWAHLVICCANS-HWKANZROSA-N 4-chloro-2-[(e)-2-(2,4-difluorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(\C=C\C=2C(=CC(F)=CC=2)F)=N1 ZKKWAHLVICCANS-HWKANZROSA-N 0.000 description 2
• SSFXEIMIGQSHOJ-FNORWQNLSA-N 4-chloro-2-[(e)-2-(2,4-dimethoxyphenyl)ethenyl]-6-methylpyrimidine Chemical compound COC1=CC(OC)=CC=C1\C=C\C1=NC(C)=CC(Cl)=N1 SSFXEIMIGQSHOJ-FNORWQNLSA-N 0.000 description 2
• SNAORKLLSUUVIU-UHFFFAOYSA-N 4-chloro-2-[2-(2,4-dichlorophenyl)ethenyl]-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(C=CC=2C(=CC(Cl)=CC=2)Cl)=N1 SNAORKLLSUUVIU-UHFFFAOYSA-N 0.000 description 2
• KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 2
• ANAWWFAOICISRA-CMDGGOBGSA-N 4-methyl-2-[(e)-2-(3-nitrophenyl)ethenyl]-6-piperidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCCC2)=NC=1\C=C\C1=CC=CC([N+]([O-])=O)=C1 ANAWWFAOICISRA-CMDGGOBGSA-N 0.000 description 2
• FEWCZBMFSBQJEI-OUKQBFOZSA-N 4-methyl-2-[(e)-2-(3-phenylmethoxyphenyl)ethenyl]-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C(C=1)=CC=CC=1OCC1=CC=CC=C1 FEWCZBMFSBQJEI-OUKQBFOZSA-N 0.000 description 2
• LOVLSELLXWYXGM-JXMROGBWSA-N 4-methyl-2-[(e)-2-(4-methylsulfanylphenyl)ethenyl]-6-pyrrolidin-1-ylpyrimidine Chemical compound C1=CC(SC)=CC=C1\C=C\C1=NC(C)=CC(N2CCCC2)=N1 LOVLSELLXWYXGM-JXMROGBWSA-N 0.000 description 2
• DXMNPJVMQZHAHV-BQYQJAHWSA-N 4-methyl-2-[(e)-2-pyridin-2-ylethenyl]-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC=N1 DXMNPJVMQZHAHV-BQYQJAHWSA-N 0.000 description 2
• XXUUPEZTANEKDD-SNAWJCMRSA-N 4-methyl-2-[(e)-2-pyridin-4-ylethenyl]-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=NC=C1 XXUUPEZTANEKDD-SNAWJCMRSA-N 0.000 description 2
• FBPDTSRDGLZFCO-UHFFFAOYSA-N 4-methyl-2-[2-(4-methylsulfonylphenyl)ethenyl]-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1C=CC1=CC=C(S(C)(=O)=O)C=C1 FBPDTSRDGLZFCO-UHFFFAOYSA-N 0.000 description 2
• CZFXQYPEPFSXJZ-CMDGGOBGSA-N 4-methyl-6-piperidin-1-yl-2-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidine Chemical compound N=1C(C)=CC(N2CCCCC2)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 CZFXQYPEPFSXJZ-CMDGGOBGSA-N 0.000 description 2
• DALWYUBVLVPQGR-BQYQJAHWSA-N 4-methyl-6-pyrrolidin-1-yl-2-[(e)-2-[3-(2h-tetrazol-5-yl)phenyl]ethenyl]pyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C(C=1)=CC=CC=1C=1N=NNN=1 DALWYUBVLVPQGR-BQYQJAHWSA-N 0.000 description 2
• BTXPXVKETLJINT-VOTSOKGWSA-N 4-methyl-6-pyrrolidin-1-yl-2-[(e)-2-thiophen-2-ylethenyl]pyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CS1 BTXPXVKETLJINT-VOTSOKGWSA-N 0.000 description 2
• SWGKOQIDSASFLM-AATRIKPKSA-N 6-methyl-2-[(e)-2-(3-nitrophenyl)ethenyl]-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C=C(C=CC=2)[N+]([O-])=O)=N1 SWGKOQIDSASFLM-AATRIKPKSA-N 0.000 description 2
• ZDWLJCJRAVZOSO-ZHACJKMWSA-N 6-methyl-2-[(e)-2-(3-phenylmethoxyphenyl)ethenyl]-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 ZDWLJCJRAVZOSO-ZHACJKMWSA-N 0.000 description 2
• ZRPDMWCAGQSASA-VMPITWQZSA-N 6-methyl-2-[(e)-2-(4-methylsulfanylphenyl)ethenyl]-1h-pyrimidin-4-one Chemical compound C1=CC(SC)=CC=C1\C=C\C1=NC(C)=CC(O)=N1 ZRPDMWCAGQSASA-VMPITWQZSA-N 0.000 description 2
• KUZBQTBRKHDVGE-SNAWJCMRSA-N 6-methyl-2-[(e)-2-thiophen-2-ylethenyl]-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2SC=CC=2)=N1 KUZBQTBRKHDVGE-SNAWJCMRSA-N 0.000 description 2
• 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 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
• 102100029549 Neuropeptide Y receptor type 5 Human genes 0.000 description 2
• 101710198055 Neuropeptide Y receptor type 5 Proteins 0.000 description 2
• 102000028582 Neuropeptide Y5 receptor Human genes 0.000 description 2
• 108090000189 Neuropeptides Proteins 0.000 description 2
• 102000003797 Neuropeptides Human genes 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• 235000021355 Stearic acid Nutrition 0.000 description 2
• 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 2
• 229930006000 Sucrose Natural products 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 239000007983 Tris buffer Substances 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
• 150000001409 amidines Chemical class 0.000 description 2
• 239000003963 antioxidant agent Substances 0.000 description 2
• 235000021407 appetite control Nutrition 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 150000003934 aromatic aldehydes Chemical class 0.000 description 2
• 238000003556 assay Methods 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 2
• 210000004556 brain Anatomy 0.000 description 2
• 239000012267 brine Substances 0.000 description 2
• 244000309464 bull Species 0.000 description 2
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 125000004432 carbon atom Chemical group C* 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• 230000002860 competitive effect Effects 0.000 description 2
• 239000002299 complementary DNA Substances 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 208000035475 disorder Diseases 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 235000013305 food Nutrition 0.000 description 2
• 235000003599 food sweetener Nutrition 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 230000002452 interceptive effect Effects 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 210000003734 kidney Anatomy 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• 229910001629 magnesium chloride Inorganic materials 0.000 description 2
• 238000002483 medication Methods 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• QCIQZIJOGQGWGP-DHZHZOJOSA-N n,n-dimethyl-4-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]aniline Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=NC(C)=CC(N2CCCC2)=N1 QCIQZIJOGQGWGP-DHZHZOJOSA-N 0.000 description 2
• ZEQNRGZXXNPVJW-XVNBXDOJSA-N n-cyclopropyl-2-[(e)-2-(2,4-dichlorophenyl)ethenyl]-6-methylpyrimidin-4-amine Chemical compound N=1C(\C=C\C=2C(=CC(Cl)=CC=2)Cl)=NC(C)=CC=1NC1CC1 ZEQNRGZXXNPVJW-XVNBXDOJSA-N 0.000 description 2
• 125000001624 naphthyl group Chemical group 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• 230000003204 osmotic effect Effects 0.000 description 2
• 125000002971 oxazolyl group Chemical group 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
• SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
• 230000003389 potentiating effect Effects 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 150000003141 primary amines Chemical class 0.000 description 2
• 108090000765 processed proteins & peptides Proteins 0.000 description 2
• WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 229920005989 resin Polymers 0.000 description 2
• 239000011347 resin Substances 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
• 230000009870 specific binding Effects 0.000 description 2
• 239000003381 stabilizer Substances 0.000 description 2
• 239000008117 stearic acid Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000003765 sweetening agent Substances 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000003831 tetrazolyl group Chemical group 0.000 description 2
• 125000000335 thiazolyl group Chemical group 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
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 229910052723 transition metal Inorganic materials 0.000 description 2
• 150000003624 transition metals Chemical class 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 235000019786 weight gain Nutrition 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• WWYVZTLIFYLZFM-UHFFFAOYSA-N 1-methylazetidine Chemical compound CN1CCC1 WWYVZTLIFYLZFM-UHFFFAOYSA-N 0.000 description 1
• AHEYFWKLKMOHCI-UHFFFAOYSA-N 2,4,6-tribromopyrimidine Chemical compound BrC1=CC(Br)=NC(Br)=N1 AHEYFWKLKMOHCI-UHFFFAOYSA-N 0.000 description 1
• BTLKROSJMNFSQZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(Cl)=N1 BTLKROSJMNFSQZ-UHFFFAOYSA-N 0.000 description 1
• YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
• WCGPCBACLBHDCI-UHFFFAOYSA-N 2,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(F)=C1 WCGPCBACLBHDCI-UHFFFAOYSA-N 0.000 description 1
• GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
• DRBOTJGGUSGMRZ-HWKANZROSA-N 2-[(e)-2-(2,4-difluorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C(=CC(F)=CC=2)F)=N1 DRBOTJGGUSGMRZ-HWKANZROSA-N 0.000 description 1
• DUINQQWKNXEGKI-VOTSOKGWSA-N 2-[(e)-2-(3-chlorophenyl)ethenyl]-4-methyl-6-(3-methylazetidin-1-yl)pyrimidine Chemical compound C1C(C)CN1C1=CC(C)=NC(\C=C\C=2C=C(Cl)C=CC=2)=N1 DUINQQWKNXEGKI-VOTSOKGWSA-N 0.000 description 1
• KUMMRAPMDHJTOV-VMPITWQZSA-N 2-[(e)-2-(3-chlorophenyl)ethenyl]-n-cyclopropyl-6-methylpyrimidin-4-amine Chemical compound N=1C(\C=C\C=2C=C(Cl)C=CC=2)=NC(C)=CC=1NC1CC1 KUMMRAPMDHJTOV-VMPITWQZSA-N 0.000 description 1
• YUYNAUBICMUPDF-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)ethenyl]-4-methyl-6-pyrrolidin-1-ylpyrimidine Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1C=CC1=CC=C(Cl)C=C1Cl YUYNAUBICMUPDF-UHFFFAOYSA-N 0.000 description 1
• CNCYRSSQBBBXOY-UHFFFAOYSA-N 2-[2-(3,4-difluorophenyl)ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(C=CC=2C=C(F)C(F)=CC=2)=N1 CNCYRSSQBBBXOY-UHFFFAOYSA-N 0.000 description 1
• KOKXFRAJKSVBRQ-UHFFFAOYSA-N 2-[2-[4-(dimethylamino)phenyl]ethenyl]-6-methyl-1h-pyrimidin-4-one Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=NC(C)=CC(O)=N1 KOKXFRAJKSVBRQ-UHFFFAOYSA-N 0.000 description 1
• DFZAHLXEMZIVEF-CMDGGOBGSA-N 2-methyl-4-piperidin-1-yl-6-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidine Chemical compound C=1C(N2CCCCC2)=NC(C)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 DFZAHLXEMZIVEF-CMDGGOBGSA-N 0.000 description 1
• ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
• JPHKMYXKNKLNDF-UHFFFAOYSA-N 3,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1F JPHKMYXKNKLNDF-UHFFFAOYSA-N 0.000 description 1
• CASRSOJWLARCRX-UHFFFAOYSA-N 3,5-dichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=CC(C=O)=C1 CASRSOJWLARCRX-UHFFFAOYSA-N 0.000 description 1
• DKMHZMQAJZMZAV-BQYQJAHWSA-N 3-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]phenol Chemical compound N=1C(C)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC(O)=C1 DKMHZMQAJZMZAV-BQYQJAHWSA-N 0.000 description 1
• UDZXPYMMTIKKRU-BQYQJAHWSA-N 3-[(e)-2-[4-(3-ethoxypyrrolidin-1-yl)-6-methylpyrimidin-2-yl]ethenyl]benzonitrile Chemical compound C1C(OCC)CCN1C1=CC(C)=NC(\C=C\C=2C=C(C=CC=2)C#N)=N1 UDZXPYMMTIKKRU-BQYQJAHWSA-N 0.000 description 1
• FRWKGYMTMOWQHQ-AATRIKPKSA-N 3-[(e)-2-[4-(3-hydroxypyrrolidin-1-yl)-6-methylpyrimidin-2-yl]ethenyl]benzonitrile Chemical compound N=1C(C)=CC(N2CC(O)CC2)=NC=1\C=C\C1=CC=CC(C#N)=C1 FRWKGYMTMOWQHQ-AATRIKPKSA-N 0.000 description 1
• UDZXPYMMTIKKRU-SFHVURJKSA-N 3-[2-[4-[(3s)-3-ethoxypyrrolidin-1-yl]-6-methylpyrimidin-2-yl]ethenyl]benzonitrile Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC(C=CC=2C=C(C=CC=2)C#N)=N1 UDZXPYMMTIKKRU-SFHVURJKSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• GVORVQPNNSASDM-UHFFFAOYSA-N 3-chloro-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1Cl GVORVQPNNSASDM-UHFFFAOYSA-N 0.000 description 1
• SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
• PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
• GFMMQESSTPJGDC-UHFFFAOYSA-N 3-formyl-4-methoxy-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1C=O GFMMQESSTPJGDC-UHFFFAOYSA-N 0.000 description 1
• HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 1
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
• 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• JAICGBJIBWDEIZ-UHFFFAOYSA-N 3-phenylmethoxybenzaldehyde Chemical compound O=CC1=CC=CC(OCC=2C=CC=CC=2)=C1 JAICGBJIBWDEIZ-UHFFFAOYSA-N 0.000 description 1
• FNAPOGMKDIXHRC-UHFFFAOYSA-N 4-(2,6-dimethylpyrimidin-4-yl)morpholine Chemical compound CC1=NC(C)=CC(N2CCOCC2)=N1 FNAPOGMKDIXHRC-UHFFFAOYSA-N 0.000 description 1
• QZKRXOFBPYMYFI-BQYQJAHWSA-N 4-(3-ethoxypyrrolidin-1-yl)-2-[(e)-2-(3-fluorophenyl)ethenyl]-6-methylpyrimidine Chemical compound C1C(OCC)CCN1C1=CC(C)=NC(\C=C\C=2C=C(F)C=CC=2)=N1 QZKRXOFBPYMYFI-BQYQJAHWSA-N 0.000 description 1
• WFGYPKGDHJDXRO-CMDGGOBGSA-N 4-(3-ethoxypyrrolidin-1-yl)-2-[(e)-2-(3-methoxyphenyl)ethenyl]-6-methylpyrimidine Chemical compound C1C(OCC)CCN1C1=CC(C)=NC(\C=C\C=2C=C(OC)C=CC=2)=N1 WFGYPKGDHJDXRO-CMDGGOBGSA-N 0.000 description 1
• BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
• QZKRXOFBPYMYFI-KRWDZBQOSA-N 4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-[2-(3-fluorophenyl)ethenyl]-6-methylpyrimidine Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC(C=CC=2C=C(F)C=CC=2)=N1 QZKRXOFBPYMYFI-KRWDZBQOSA-N 0.000 description 1
• WFGYPKGDHJDXRO-SFHVURJKSA-N 4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-[2-(3-methoxyphenyl)ethenyl]-6-methylpyrimidine Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC(C=CC=2C=C(OC)C=CC=2)=N1 WFGYPKGDHJDXRO-SFHVURJKSA-N 0.000 description 1
• UEQULPULFVMZEQ-AATRIKPKSA-N 4-[6-methyl-2-[(e)-2-[3-(trifluoromethyl)phenyl]ethenyl]pyrimidin-4-yl]morpholine Chemical compound N=1C(C)=CC(N2CCOCC2)=NC=1\C=C\C1=CC=CC(C(F)(F)F)=C1 UEQULPULFVMZEQ-AATRIKPKSA-N 0.000 description 1
• GSXFOGXQLRLSKK-UHFFFAOYSA-N 4-chloro-2,6-dimethylpyrimidine Chemical compound CC1=CC(Cl)=NC(C)=N1 GSXFOGXQLRLSKK-UHFFFAOYSA-N 0.000 description 1
• SSFXEIMIGQSHOJ-UHFFFAOYSA-N 4-chloro-2-[2-(2,4-dimethoxyphenyl)ethenyl]-6-methylpyrimidine Chemical compound COC1=CC(OC)=CC=C1C=CC1=NC(C)=CC(Cl)=N1 SSFXEIMIGQSHOJ-UHFFFAOYSA-N 0.000 description 1
• WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
• VVKCRNYPIQQPMF-JXMROGBWSA-N 4-methoxy-n,n-dimethyl-3-[(e)-2-(4-methyl-6-pyrrolidin-1-ylpyrimidin-2-yl)ethenyl]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1\C=C\C1=NC(C)=CC(N2CCCC2)=N1 VVKCRNYPIQQPMF-JXMROGBWSA-N 0.000 description 1
• FMTDADSOIWTSKE-VMPITWQZSA-N 4-methoxy-n,n-dimethyl-3-[(e)-2-(6-methyl-4-oxo-1h-pyrimidin-2-yl)ethenyl]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1\C=C\C1=NC(C)=CC(O)=N1 FMTDADSOIWTSKE-VMPITWQZSA-N 0.000 description 1
• QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 description 1
• AHHHDTLXONDKQF-UHFFFAOYSA-N 6-methyl-1h-pyrimidin-2-one Chemical compound CC1=CC=NC(O)=N1 AHHHDTLXONDKQF-UHFFFAOYSA-N 0.000 description 1
• PGZBQAFJAXGOOW-HWKANZROSA-N 6-methyl-2-[(e)-2-(2,3,4-trifluorophenyl)ethenyl]-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(\C=C\C=2C(=C(F)C(F)=CC=2)F)=N1 PGZBQAFJAXGOOW-HWKANZROSA-N 0.000 description 1
• PGZBQAFJAXGOOW-UHFFFAOYSA-N 6-methyl-2-[2-(2,3,4-trifluorophenyl)ethenyl]-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(C=CC=2C(=C(F)C(F)=CC=2)F)=N1 PGZBQAFJAXGOOW-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• 102000009027 Albumins Human genes 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• 101100460788 Arabidopsis thaliana NPY5 gene Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• QYOVMAREBTZLBT-KTKRTIGZSA-N CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO QYOVMAREBTZLBT-KTKRTIGZSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• 108020004635 Complementary DNA Proteins 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• 108020004414 DNA Proteins 0.000 description 1
• 108010054576 Deoxyribonuclease EcoRI Proteins 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 238000007341 Heck reaction Methods 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 208000031226 Hyperlipidaemia Diseases 0.000 description 1
• XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
• PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• 239000005913 Maltodextrin Substances 0.000 description 1
• 229920002774 Maltodextrin Polymers 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 101100460785 Mus musculus Npy5r gene Proteins 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• 101150111774 NPY5R gene Proteins 0.000 description 1
• 108010046593 Neuropeptide Y5 receptor Proteins 0.000 description 1
• 108070000018 Neuropeptide receptor Proteins 0.000 description 1
• 102000028517 Neuropeptide receptor Human genes 0.000 description 1
• 229940116685 Neuropeptide receptor antagonist Drugs 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 206010033307 Overweight Diseases 0.000 description 1
• 102100026450 POU domain, class 3, transcription factor 4 Human genes 0.000 description 1
• 101710133389 POU domain, class 3, transcription factor 4 Proteins 0.000 description 1
• 108050006759 Pancreatic lipases Proteins 0.000 description 1
• 102000019280 Pancreatic lipases Human genes 0.000 description 1
• 108010002747 Pfu DNA polymerase Proteins 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
• 229960004308 acetylcysteine Drugs 0.000 description 1
• 150000000475 acetylene derivatives Chemical class 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000001336 alkenes Chemical class 0.000 description 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 230000003321 amplification Effects 0.000 description 1
• 235000019789 appetite Nutrition 0.000 description 1
• 230000036528 appetite Effects 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 150000001502 aryl halides Chemical class 0.000 description 1
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 239000012888 bovine serum Substances 0.000 description 1
• 229940098773 bovine serum albumin Drugs 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000001110 calcium chloride Substances 0.000 description 1
• 235000011148 calcium chloride Nutrition 0.000 description 1
• 229910001628 calcium chloride Inorganic materials 0.000 description 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 238000012512 characterization method Methods 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 125000000068 chlorophenyl group Chemical group 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 238000010367 cloning Methods 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 229910052681 coesite Inorganic materials 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 229910052906 cristobalite Inorganic materials 0.000 description 1
• 229960000913 crospovidone Drugs 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 210000000695 crystalline len Anatomy 0.000 description 1
• 125000004802 cyanophenyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 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 description 1
• WJYHCYBNUJVCEH-UHFFFAOYSA-N cyclohexane;ethoxyethane Chemical compound CCOCC.C1CCCCC1 WJYHCYBNUJVCEH-UHFFFAOYSA-N 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000004663 dialkyl amino group Chemical group 0.000 description 1
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
• 125000004188 dichlorophenyl group Chemical group 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004212 difluorophenyl group Chemical group 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
• 230000006806 disease prevention Effects 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
• NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
• 239000013604 expression vector Substances 0.000 description 1
• 235000021149 fatty food Nutrition 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 125000001207 fluorophenyl group Chemical group 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000036571 hydration Effects 0.000 description 1
• 238000006703 hydration reaction Methods 0.000 description 1
• 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 210000003016 hypothalamus Anatomy 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 229960004903 invert sugar Drugs 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 239000011981 lindlar catalyst Substances 0.000 description 1
• 238000012417 linear regression Methods 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229910003002 lithium salt Inorganic materials 0.000 description 1
• 159000000002 lithium salts Chemical class 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 150000002690 malonic acid derivatives Chemical class 0.000 description 1
• 229940035034 maltodextrin Drugs 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 230000000873 masking effect Effects 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• UVSBCUAQEZINCQ-UHFFFAOYSA-N methyl 3-formylbenzoate Chemical compound COC(=O)C1=CC=CC(C=O)=C1 UVSBCUAQEZINCQ-UHFFFAOYSA-N 0.000 description 1
• 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
• 230000000813 microbial effect Effects 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• BDTUHHLQKBCKGF-UHFFFAOYSA-N n-methyl-2-(2-pyridin-2-ylethenyl)-6-pyrrolidin-1-ylpyrimidin-4-amine Chemical compound N=1C(NC)=CC(N2CCCC2)=NC=1C=CC1=CC=CC=N1 BDTUHHLQKBCKGF-UHFFFAOYSA-N 0.000 description 1
• BDTUHHLQKBCKGF-BQYQJAHWSA-N n-methyl-2-[(e)-2-pyridin-2-ylethenyl]-6-pyrrolidin-1-ylpyrimidin-4-amine Chemical compound N=1C(NC)=CC(N2CCCC2)=NC=1\C=C\C1=CC=CC=N1 BDTUHHLQKBCKGF-BQYQJAHWSA-N 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 125000006501 nitrophenyl group Chemical group 0.000 description 1
• HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
• 238000003199 nucleic acid amplification method Methods 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([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
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
• 238000006772 olefination reaction Methods 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 150000003003 phosphines Chemical class 0.000 description 1
• 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 description 1
• 229940081310 piperonal Drugs 0.000 description 1
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
• 229920000053 polysorbate 80 Polymers 0.000 description 1
• 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
• 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011736 potassium bicarbonate Substances 0.000 description 1
• 235000015497 potassium bicarbonate Nutrition 0.000 description 1
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• 239000008057 potassium phosphate buffer Substances 0.000 description 1
• 229940069328 povidone Drugs 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 230000006824 pyrimidine synthesis Effects 0.000 description 1
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 239000002287 radioligand Substances 0.000 description 1
• 238000003653 radioligand binding assay Methods 0.000 description 1
• 229940044551 receptor antagonist Drugs 0.000 description 1
• 239000002464 receptor antagonist Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 239000013049 sediment Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 238000007614 solvation Methods 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 238000003153 stable transfection Methods 0.000 description 1
• 229910052682 stishovite Inorganic materials 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 125000001302 tertiary amino group Chemical group 0.000 description 1
• YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
• 230000035924 thermogenesis Effects 0.000 description 1
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
• 238000001890 transfection Methods 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 229910052905 tridymite Inorganic materials 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 235000013311 vegetables Nutrition 0.000 description 1
• 230000004580 weight loss Effects 0.000 description 1